#------------------------------------------------------------------------------ #$Date: 2020-07-01 04:46:24 +0300 (Wed, 01 Jul 2020) $ #$Revision: 253590 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240805.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240805 loop_ _publ_author_name 'da Silva, Cecilia' 'Owoyemi, Bolaji Charles Dayo' 'Alvarenga-Jr, Benedito R.' 'Alvarez, Natalia' 'Ellena, Javier A.' 'Carneiro, Renato Lajarim' _publ_section_title ; Synthesis and solid-state characterization of diclofenac imidazolium monohydrate: an imidazolium pharmaceutical ionic liquid ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00723D _journal_year 2020 _chemical_formula_moiety 'C14 H10 Cl2 N O2, C3 H5 N2, H2 O' _chemical_formula_sum 'C17 H17 Cl2 N3 O3' _chemical_formula_weight 382.23 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-05-23 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-23 deposited with the CCDC. 2020-06-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.275(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.9975(9) _cell_length_b 9.0067(4) _cell_length_c 10.9126(6) _cell_measurement_reflns_used 19634 _cell_measurement_temperature 273.15 _cell_measurement_theta_max 26.393 _cell_measurement_theta_min 2.983 _cell_volume 1792.38(15) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 273.15 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX2 microsource' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_unetI/netI 0.0312 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 19634 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.393 _diffrn_reflns_theta_min 2.983 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 0.383 _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.416 _exptl_crystal_description prism _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.473 _exptl_crystal_size_mid 0.384 _exptl_crystal_size_min 0.114 _refine_diff_density_max 0.414 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 3656 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0473 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.9198P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1183 _refine_ls_wR_factor_ref 0.1351 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2613 _reflns_number_total 3656 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00723d2.cif _cod_data_source_block dcf_imi_12 _cod_original_cell_volume 1792.37(15) _cod_database_code 7240805 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.958 _shelx_estimated_absorpt_t_min 0.839 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All N(H) groups, All O(H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(O1WA) = Uanis(O1W) 3. Rigid body (RIGU) restrains C15, C16, N3, C17, N2 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 N2, C17, N3, C16, C15 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 4. Others Fixed Sof: O1W(0.85) H1WA(0.85) H1WB(0.85) O1WA(0.15) H1WC(0.15) H1WD(0.15) 5.a Riding coordinates: O1WA(H1WC,H1WD) 5.b Free rotating group: O1W(H1WA,H1WB) 5.c Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 5.d Aromatic/amide H refined with riding coordinates: C13(H13), C4(H4), N1(H1), C11(H11), C7(H7), C5(H5), N2(H2), C6(H6), C12(H12), N3(H3), C17(H17), C15(H15), C16(H16) ; _shelx_res_file ; TITL DCF_IMI_12 in P21/c #14 dcf_imi_12.res created by SHELXL-2018/3 at 16:13:54 on 23-May-2019 CELL 0.71073 18.9975 9.0067 10.9126 90 106.275 90 ZERR 4 0.0009 0.0004 0.0006 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 68 68 8 12 12 RIGU C15 C16 N3 C17 N2 RIGU N2 C17 N3 C16 C15 EADP O1WA O1W L.S. 19 PLAN 20 SIZE 0.114 0.384 0.473 TEMP 0 fmap 2 acta MERG 2 REM REM REM WGHT 0.065500 0.919800 FVAR 0.54576 CL2 3 0.465028 0.542497 0.207178 11.00000 0.05199 0.05090 = 0.06358 0.00091 0.02762 -0.00384 CL1 3 0.244008 0.291557 0.359148 11.00000 0.04868 0.05396 = 0.08248 0.00396 0.02159 -0.01263 C9 1 0.357095 0.418894 0.292997 11.00000 0.04242 0.03079 = 0.04134 -0.00649 0.00924 -0.00272 C3 1 0.265824 0.710226 0.065091 11.00000 0.03462 0.04275 = 0.05028 0.00268 0.01818 -0.00028 C13 1 0.483706 0.354169 0.403041 11.00000 0.04161 0.04192 = 0.05667 -0.00904 0.01038 0.00065 AFIX 43 H13 2 0.533504 0.366938 0.412291 11.00000 -1.20000 AFIX 0 C4 1 0.267974 0.863935 0.050076 11.00000 0.04778 0.04562 = 0.06903 0.01373 0.02075 0.00627 AFIX 43 H4 2 0.242307 0.906053 -0.027367 11.00000 -1.20000 AFIX 0 N1 4 0.304787 0.494208 0.198230 11.00000 0.04362 0.03381 = 0.05015 0.00029 0.00225 -0.00664 AFIX 43 H1 2 0.270561 0.443756 0.146812 11.00000 -1.50000 AFIX 0 C10 1 0.336972 0.318044 0.375093 11.00000 0.04351 0.03489 = 0.04901 -0.00658 0.01330 -0.00726 C11 1 0.386926 0.239829 0.467493 11.00000 0.06028 0.03710 = 0.04998 0.00282 0.01477 -0.00236 AFIX 43 H11 2 0.370962 0.174028 0.519718 11.00000 -1.20000 AFIX 0 C8 1 0.305566 0.650645 0.182913 11.00000 0.03424 0.03723 = 0.04983 -0.00182 0.01660 -0.00020 O2 5 0.147746 0.520014 0.080683 11.00000 0.05057 0.12942 = 0.05606 0.00893 0.01685 -0.02905 C7 1 0.344015 0.742910 0.280249 11.00000 0.04288 0.04554 = 0.05266 -0.00803 0.01582 -0.00369 AFIX 43 H7 2 0.369389 0.702394 0.358557 11.00000 -1.20000 AFIX 0 C14 1 0.432548 0.431001 0.308987 11.00000 0.04510 0.03399 = 0.04707 -0.00737 0.01749 -0.00347 O1 5 0.101998 0.527374 -0.123706 11.00000 0.05225 0.24592 = 0.05029 0.00935 0.00422 -0.04996 C1 1 0.152288 0.551570 -0.026011 11.00000 0.03835 0.06831 = 0.04651 -0.00227 0.01134 -0.00421 C5 1 0.307253 0.955433 0.147261 11.00000 0.05882 0.03587 = 0.09408 0.00290 0.03314 0.00157 AFIX 43 H5 2 0.308006 1.057486 0.134717 11.00000 -1.20000 AFIX 0 N2 4 0.080516 0.988995 -0.064653 11.00000 0.04466 0.13152 = 0.05191 -0.00376 0.01443 0.00559 AFIX 43 H2 2 0.070450 0.953640 -0.140812 11.00000 -1.50000 AFIX 0 C2 1 0.223323 0.614005 -0.042570 11.00000 0.04279 0.05662 = 0.04537 0.00557 0.01659 -0.00068 AFIX 23 H2A 2 0.254291 0.531864 -0.052499 11.00000 -1.20000 H2B 2 0.212027 0.671602 -0.120779 11.00000 -1.20000 AFIX 0 C6 1 0.345020 0.894782 0.262056 11.00000 0.04968 0.04329 = 0.07823 -0.01826 0.02801 -0.00652 AFIX 43 H6 2 0.371336 0.955785 0.327752 11.00000 -1.20000 AFIX 0 C12 1 0.460850 0.258863 0.482872 11.00000 0.05640 0.04281 = 0.05139 0.00005 0.00371 0.00346 AFIX 43 H12 2 0.495045 0.207759 0.546655 11.00000 -1.20000 AFIX 0 N3 4 0.104578 1.009775 0.137263 11.00000 0.05178 0.15184 = 0.04378 -0.00156 0.00834 0.02334 AFIX 43 H3 2 0.113085 0.991743 0.217486 11.00000 -1.50000 AFIX 0 C17 1 0.087511 0.909106 0.042459 11.00000 0.05705 0.08890 = 0.10011 0.00812 0.03218 0.01719 AFIX 43 H17 2 0.081814 0.807164 0.049327 11.00000 -1.20000 AFIX 0 C15 1 0.091648 1.130477 -0.033561 11.00000 0.06695 0.12832 = 0.13102 0.02670 0.02948 -0.01684 AFIX 43 H15 2 0.089146 1.207999 -0.090921 11.00000 -1.20000 AFIX 0 C16 1 0.105902 1.143957 0.083533 11.00000 0.07507 0.11388 = 0.13051 -0.00165 0.00230 -0.01925 AFIX 43 H16 2 0.116011 1.233222 0.127828 11.00000 -1.20000 AFIX 6 PART 1 O1W 5 0.038253 0.576531 0.183353 10.85000 0.06310 0.14564 = 0.05535 -0.01529 0.01883 -0.01479 H1WA 2 -0.004770 0.545512 0.146734 10.85000 -1.50000 H1WB 2 0.062890 0.555607 0.131542 10.85000 -1.50000 AFIX 0 PART 0 PART 2 O1WA 5 0.043152 0.440204 0.184635 10.15000 0.06310 0.14564 = 0.05535 -0.01529 0.01883 -0.01479 AFIX 3 H1WC 2 0.067042 0.482184 0.139055 10.15000 -1.50000 H1WD 2 -0.001568 0.453064 0.143685 10.15000 -1.50000 AFIX 0 HKLF 4 REM DCF_IMI_12 in P21/c #14 REM wR2 = 0.1351, GooF = S = 1.026, Restrained GooF = 1.031 for all data REM R1 = 0.0473 for 2613 Fo > 4sig(Fo) and 0.0739 for all 3656 data REM 232 parameters refined using 30 restraints END WGHT 0.0655 0.9199 REM Highest difference peak 0.414, deepest hole -0.363, 1-sigma level 0.053 Q1 1 0.0943 0.8965 0.1328 11.00000 0.05 0.41 Q2 1 0.2533 0.4600 0.1953 11.00000 0.05 0.40 Q3 1 0.0909 0.6364 -0.1144 11.00000 0.05 0.38 Q4 1 0.1089 0.4854 -0.1160 11.00000 0.05 0.31 Q5 1 0.0478 0.3707 0.1573 11.00000 0.05 0.25 Q6 1 0.1268 0.6110 0.0581 11.00000 0.05 0.25 Q7 1 0.0482 0.4805 0.2135 11.00000 0.05 0.24 Q8 1 0.1508 0.5016 0.1162 11.00000 0.05 0.19 Q9 1 0.0714 0.8618 -0.0115 11.00000 0.05 0.18 Q10 1 0.1148 1.0322 0.1236 11.00000 0.05 0.17 Q11 1 0.0984 1.0452 0.1365 11.00000 0.05 0.16 Q12 1 0.1512 0.4693 0.0419 11.00000 0.05 0.16 Q13 1 0.4529 0.3696 0.3392 11.00000 0.05 0.15 Q14 1 0.2798 0.6827 0.1200 11.00000 0.05 0.15 Q15 1 0.2246 0.3607 0.1541 11.00000 0.05 0.14 Q16 1 0.2211 1.2235 0.1385 11.00000 0.05 0.14 Q17 1 0.0533 0.7257 -0.0299 11.00000 0.05 0.14 Q18 1 0.2820 0.7759 0.0451 11.00000 0.05 0.14 Q19 1 0.3420 0.3723 0.3746 11.00000 0.05 0.13 Q20 1 0.3969 0.4460 0.3248 11.00000 0.05 0.13 ; _shelx_res_checksum 38895 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.46503(4) 0.54250(7) 0.20718(7) 0.0532(2) Uani 1 1 d . . . . . Cl1 Cl 0.24401(4) 0.29156(8) 0.35915(7) 0.0611(2) Uani 1 1 d . . . . . C9 C 0.35709(12) 0.4189(2) 0.2930(2) 0.0387(5) Uani 1 1 d . . . . . C3 C 0.26582(12) 0.7102(3) 0.0651(2) 0.0413(5) Uani 1 1 d . . . . . C13 C 0.48371(13) 0.3542(3) 0.4030(2) 0.0474(6) Uani 1 1 d . . . . . H13 H 0.533504 0.366938 0.412291 0.057 Uiso 1 1 calc R . . . . C4 C 0.26797(14) 0.8639(3) 0.0501(3) 0.0533(7) Uani 1 1 d . . . . . H4 H 0.242307 0.906053 -0.027367 0.064 Uiso 1 1 calc R . . . . N1 N 0.30479(11) 0.4942(2) 0.1982(2) 0.0447(5) Uani 1 1 d . . . . . H1 H 0.270561 0.443756 0.146812 0.067 Uiso 1 1 calc R . . . . C10 C 0.33697(13) 0.3180(2) 0.3751(2) 0.0424(5) Uani 1 1 d . . . . . C11 C 0.38693(14) 0.2398(3) 0.4675(2) 0.0493(6) Uani 1 1 d . . . . . H11 H 0.370962 0.174028 0.519718 0.059 Uiso 1 1 calc R . . . . C8 C 0.30557(12) 0.6506(3) 0.1829(2) 0.0395(5) Uani 1 1 d . . . . . O2 O 0.14775(11) 0.5200(3) 0.0807(2) 0.0783(7) Uani 1 1 d . . . . . C7 C 0.34401(13) 0.7429(3) 0.2802(3) 0.0465(6) Uani 1 1 d . . . . . H7 H 0.369389 0.702394 0.358557 0.056 Uiso 1 1 calc R . . . . C14 C 0.43255(13) 0.4310(2) 0.3090(2) 0.0411(5) Uani 1 1 d . . . . . O1 O 0.10200(12) 0.5274(4) -0.1237(2) 0.1182(12) Uani 1 1 d . . . . . C1 C 0.15229(14) 0.5516(3) -0.0260(3) 0.0512(6) Uani 1 1 d . . . . . C5 C 0.30725(16) 0.9554(3) 0.1473(3) 0.0605(8) Uani 1 1 d . . . . . H5 H 0.308006 1.057486 0.134717 0.073 Uiso 1 1 calc R . . . . N2 N 0.08052(13) 0.9890(4) -0.0647(3) 0.0759(8) Uani 1 1 d . U . . . H2 H 0.070450 0.953640 -0.140812 0.114 Uiso 1 1 calc R . . . . C2 C 0.22332(13) 0.6140(3) -0.0426(2) 0.0474(6) Uani 1 1 d . . . . . H2A H 0.254291 0.531864 -0.052499 0.057 Uiso 1 1 calc R . . . . H2B H 0.212027 0.671602 -0.120779 0.057 Uiso 1 1 calc R . . . . C6 C 0.34502(14) 0.8948(3) 0.2621(3) 0.0550(7) Uani 1 1 d . . . . . H6 H 0.371336 0.955785 0.327752 0.066 Uiso 1 1 calc R . . . . C12 C 0.46085(15) 0.2589(3) 0.4829(3) 0.0525(6) Uani 1 1 d . . . . . H12 H 0.495045 0.207759 0.546655 0.063 Uiso 1 1 calc R . . . . N3 N 0.10458(14) 1.0098(5) 0.1373(2) 0.0835(9) Uani 1 1 d . U . . . H3 H 0.113085 0.991743 0.217486 0.125 Uiso 1 1 calc R . . . . C17 C 0.08751(17) 0.9091(5) 0.0425(4) 0.0800(10) Uani 1 1 d . U . . . H17 H 0.081814 0.807164 0.049327 0.096 Uiso 1 1 calc R . . . . C15 C 0.0916(2) 1.1305(6) -0.0336(6) 0.1084(14) Uani 1 1 d . U . . . H15 H 0.089146 1.207999 -0.090921 0.130 Uiso 1 1 calc R . . . . C16 C 0.1059(2) 1.1440(6) 0.0835(6) 0.1119(15) Uani 1 1 d . U . . . H16 H 0.116011 1.233222 0.127828 0.134 Uiso 1 1 calc R . . . . O1W O 0.03825(15) 0.5765(5) 0.1834(2) 0.0876(9) Uani 0.85 1 d . . P A 1 H1WA H -0.004770 0.545512 0.146734 0.131 Uiso 0.85 1 d G . P A 1 H1WB H 0.062890 0.555607 0.131542 0.131 Uiso 0.85 1 d G . P A 1 O1WA O 0.0432(9) 0.440(2) 0.1846(15) 0.0876(9) Uani 0.15 1 d . . P B 2 H1WC H 0.067042 0.482184 0.139055 0.131 Uiso 0.15 1 d R . P B 2 H1WD H -0.001568 0.453064 0.143685 0.131 Uiso 0.15 1 d R . P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.0520(4) 0.0509(4) 0.0636(4) 0.0009(3) 0.0276(3) -0.0038(3) Cl1 0.0487(4) 0.0540(4) 0.0825(5) 0.0040(3) 0.0216(3) -0.0126(3) C9 0.0424(12) 0.0308(11) 0.0413(13) -0.0065(10) 0.0092(10) -0.0027(9) C3 0.0346(11) 0.0427(13) 0.0503(14) 0.0027(11) 0.0182(11) -0.0003(10) C13 0.0416(13) 0.0419(13) 0.0567(16) -0.0090(12) 0.0104(12) 0.0006(11) C4 0.0478(14) 0.0456(15) 0.0690(18) 0.0137(14) 0.0207(13) 0.0063(12) N1 0.0436(11) 0.0338(10) 0.0502(12) 0.0003(9) 0.0022(9) -0.0066(9) C10 0.0435(12) 0.0349(12) 0.0490(14) -0.0066(11) 0.0133(11) -0.0073(10) C11 0.0603(16) 0.0371(13) 0.0500(15) 0.0028(11) 0.0148(13) -0.0024(12) C8 0.0342(11) 0.0372(12) 0.0498(14) -0.0018(10) 0.0166(10) -0.0002(10) O2 0.0506(11) 0.129(2) 0.0561(13) 0.0089(12) 0.0168(10) -0.0290(12) C7 0.0429(13) 0.0455(14) 0.0527(15) -0.0080(12) 0.0158(11) -0.0037(11) C14 0.0451(13) 0.0340(12) 0.0471(14) -0.0074(10) 0.0175(11) -0.0035(10) O1 0.0523(13) 0.246(4) 0.0503(13) 0.0094(17) 0.0042(11) -0.0500(18) C1 0.0384(13) 0.0683(18) 0.0465(15) -0.0023(13) 0.0113(12) -0.0042(12) C5 0.0588(17) 0.0359(14) 0.094(2) 0.0029(15) 0.0331(17) 0.0016(13) N2 0.0447(13) 0.132(3) 0.0519(15) -0.0038(16) 0.0144(11) 0.0056(15) C2 0.0428(13) 0.0566(15) 0.0454(14) 0.0056(12) 0.0166(11) -0.0007(11) C6 0.0497(14) 0.0433(15) 0.078(2) -0.0183(14) 0.0280(14) -0.0065(12) C12 0.0564(16) 0.0428(14) 0.0514(15) 0.0001(12) 0.0037(13) 0.0035(12) N3 0.0518(14) 0.152(3) 0.0438(14) -0.0016(17) 0.0083(12) 0.0233(17) C17 0.0571(18) 0.089(2) 0.100(3) 0.008(2) 0.0322(18) 0.0172(17) C15 0.067(2) 0.128(4) 0.131(4) 0.027(3) 0.029(3) -0.017(3) C16 0.075(3) 0.114(3) 0.131(4) -0.002(3) 0.002(3) -0.019(2) O1W 0.0631(15) 0.146(3) 0.0554(15) -0.0153(18) 0.0188(12) -0.0148(19) O1WA 0.0631(15) 0.146(3) 0.0554(15) -0.0153(18) 0.0188(12) -0.0148(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C9 C10 121.6(2) . . ? N1 C9 C14 123.2(2) . . ? C14 C9 C10 115.1(2) . . ? C4 C3 C8 117.5(2) . . ? C4 C3 C2 120.5(2) . . ? C8 C3 C2 122.0(2) . . ? C12 C13 C14 120.0(2) . . ? C5 C4 C3 121.8(3) . . ? C9 N1 C8 122.81(19) . . ? C9 C10 Cl1 118.38(18) . . ? C11 C10 Cl1 118.48(18) . . ? C11 C10 C9 123.1(2) . . ? C10 C11 C12 119.9(2) . . ? C3 C8 N1 117.8(2) . . ? C7 C8 C3 120.4(2) . . ? C7 C8 N1 121.7(2) . . ? C6 C7 C8 120.6(3) . . ? C9 C14 Cl2 120.09(19) . . ? C13 C14 Cl2 117.54(18) . . ? C13 C14 C9 122.4(2) . . ? O2 C1 O1 122.4(2) . . ? O2 C1 C2 120.0(2) . . ? O1 C1 C2 117.4(2) . . ? C6 C5 C4 119.6(2) . . ? C15 N2 C17 108.8(4) . . ? C3 C2 C1 114.9(2) . . ? C5 C6 C7 120.0(3) . . ? C13 C12 C11 119.5(2) . . ? C17 N3 C16 107.5(4) . . ? N3 C17 N2 104.5(3) . . ? C16 C15 N2 109.5(5) . . ? C15 C16 N3 109.7(5) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C14 1.734(2) . ? Cl1 C10 1.742(2) . ? C9 N1 1.393(3) . ? C9 C10 1.402(3) . ? C9 C14 1.399(3) . ? C3 C4 1.396(3) . ? C3 C8 1.403(3) . ? C3 C2 1.501(3) . ? C13 C14 1.385(3) . ? C13 C12 1.377(4) . ? C4 C5 1.385(4) . ? N1 C8 1.419(3) . ? C10 C11 1.370(4) . ? C11 C12 1.378(4) . ? C8 C7 1.385(3) . ? O2 C1 1.225(3) . ? C7 C6 1.383(4) . ? O1 C1 1.235(3) . ? C1 C2 1.519(3) . ? C5 C6 1.371(4) . ? N2 C17 1.347(5) . ? N2 C15 1.320(6) . ? N3 C17 1.345(5) . ? N3 C16 1.347(6) . ? C15 C16 1.236(6) . ?