#------------------------------------------------------------------------------ #$Date: 2018-12-06 05:42:30 +0200 (Thu, 06 Dec 2018) $ #$Revision: 212403 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/03/1550336.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_1550336 loop_ _publ_author_name 'Baillargeon, Pierre' 'Rahem, Tarik' 'Amigo, Carl' 'Fortin, Daniel' 'Dory, Yves L.' _publ_section_title ; Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group ; _journal_coeditor_code FY2132 _journal_issue 12 _journal_name_full IUCrData _journal_page_first x181630 _journal_paper_doi 10.1107/S2414314618016309 _journal_volume 3 _journal_year 2018 _chemical_absolute_configuration unk _chemical_formula_moiety 'C9 H11 N1 O3' _chemical_formula_sum 'C9 H11 N O3' _chemical_formula_weight 181.19 _space_group_IT_number 1 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall 'P 1' _symmetry_space_group_name_H-M 'P 1' _atom_sites_solution_hydrogens mixed _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.3 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 93.618(2) _cell_angle_beta 107.044(2) _cell_angle_gamma 95.658(2) _cell_formula_units_Z 1 _cell_length_a 4.8011(2) _cell_length_b 6.5522(3) _cell_length_c 7.5052(3) _cell_measurement_reflns_used 2759 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 70.68 _cell_measurement_theta_min 6.2 _cell_volume 223.575(17) _computing_cell_refinement ; SAINT (Bruker, 2012) ; _computing_data_collection ; APEX2 (Bruker, 2012) ; _computing_data_reduction ; SORTAV (Blessing, 1995) ; _computing_molecular_graphics ; Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008) ; _computing_publication_material ; WinGX (Farrugia, 2012) and Publcif (Westrip, 2010) ; _computing_structure_refinement ; SHELXL-2016/6 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS (Sheldrick, 2008) ; _diffrn_ambient_temperature 173(2) _diffrn_detector 'APEXII CCD' _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.0625 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2726 _diffrn_reflns_theta_full 69.823 _diffrn_reflns_theta_max 69.823 _diffrn_reflns_theta_min 6.196 _diffrn_source 'sealed x-ray tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.85 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.5744 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2012) ; _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 96 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.115 _refine_diff_density_max 0.249 _refine_diff_density_min -0.229 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 123 _refine_ls_number_reflns 1206 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0515 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+0.0525P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1447 _refine_ls_wR_factor_ref 0.154 _reflns_number_gt 1139 _reflns_number_total 1206 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL cu_Bail_A7_7_29F38_0m in P1 shelx.res created by SHELXL-2016/6 at 16:09:52 on 25-Sep-2018 CELL 1.54178 4.8011 6.5522 7.5052 93.618 107.044 95.658 ZERR 1.00 0.0002 0.0003 0.0003 0.002 0.002 0.002 LATT -1 SFAC C H N O UNIT 9 11 1 3 MERG 2 DFIX 0.960 0.020 O3 H3 EQIV $1 x-1, y, z EQIV $2 x, y, z-1 EQIV $3 x-1, y-1, z-1 EQIV $4 x, y+1, z+1 EQIV $5 x-1, y, z-1 HTAB N1 O2_$1 HTAB O3 O1 HTAB C6 O3_$3 HTAB O3 O2_$4 HTAB C5 O3_$2 HTAB C5 O3_$5 FMAP 2 PLAN 2 SIZE 0.115 0.160 0.320 ACTA 140.00 HTAB 2.00000 BOND $H CONF L.S. 20 TEMP -99.94 WGHT 0.091200 0.052500 FVAR 1.73370 O1 4 0.787238 0.752557 0.575425 11.00000 0.05370 0.04523 = 0.03162 -0.00043 0.00624 0.02817 O2 4 1.094349 -0.064557 -0.026991 11.00000 0.02869 0.03925 = 0.04183 -0.00822 0.00942 0.00162 O3 4 1.218890 0.581112 0.805359 11.00000 0.03834 0.03467 = 0.02599 -0.00213 0.00272 0.00642 N1 3 0.693585 0.086325 -0.009129 11.00000 0.02341 0.03602 = 0.03091 -0.00412 0.00470 0.00175 AFIX 43 H1 2 0.506646 0.061900 -0.016887 11.00000 -1.20000 AFIX 0 C1 1 0.581152 0.862203 0.455812 11.00000 0.05393 0.04738 = 0.03817 0.00916 0.01066 0.02371 AFIX 137 H1A 2 0.673811 0.934512 0.373509 11.00000 -1.50000 H1B 2 0.513623 0.962513 0.531259 11.00000 -1.50000 H1C 2 0.413277 0.765528 0.379819 11.00000 -1.50000 AFIX 0 C2 1 0.894804 0.600513 0.495340 11.00000 0.03283 0.02730 = 0.03005 0.00208 0.01048 0.00175 C3 1 0.801620 0.527947 0.306908 11.00000 0.03187 0.03244 = 0.02644 0.00527 0.00250 0.00691 AFIX 43 H3A 2 0.648153 0.586589 0.222842 11.00000 -1.20000 AFIX 0 C4 1 0.928447 0.371867 0.239698 11.00000 0.02808 0.02964 = 0.02854 0.00322 0.00525 0.00166 C5 1 0.831153 0.298538 0.032695 11.00000 0.03769 0.03541 = 0.02437 0.00555 0.00659 0.00405 AFIX 23 H5A 2 0.690774 0.388824 -0.035372 11.00000 -1.20000 H5B 2 1.004057 0.312362 -0.014027 11.00000 -1.20000 AFIX 0 C6 1 0.831450 -0.072830 -0.036350 11.00000 0.03518 0.03254 = 0.02531 -0.00313 0.00959 -0.00450 AFIX 43 H6 2 0.718873 -0.204814 -0.065598 11.00000 -1.20000 AFIX 0 C7 1 1.146764 0.284830 0.362789 11.00000 0.04667 0.03673 = 0.02779 -0.00231 0.00178 0.01507 AFIX 43 H7 2 1.235762 0.177733 0.317846 11.00000 -1.20000 AFIX 0 C8 1 1.238492 0.353133 0.553802 11.00000 0.03968 0.03623 = 0.03221 0.00083 -0.00186 0.01436 AFIX 43 H8 2 1.385838 0.289743 0.638179 11.00000 -1.20000 AFIX 0 C9 1 1.116684 0.511298 0.619961 11.00000 0.03106 0.02923 = 0.02501 -0.00168 0.00594 -0.00049 H3 2 1.143771 0.710536 0.816904 11.00000 0.06061 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM cu_Bail_A7_7_29F38_0m in P1 REM R1 = 0.0515 for 1139 Fo > 4sig(Fo) and 0.0548 for all 1206 data REM 123 parameters refined using 4 restraints END WGHT 0.0912 0.0525 REM Instructions for potential hydrogen bonds HTAB N1 O2_$1 HTAB C5 O3_$2 HTAB C6 O3_$3 HTAB O3 O1 HTAB O3 O2_$4 REM Highest difference peak 0.249, deepest hole -0.229, 1-sigma level 0.058 Q1 1 1.0601 0.1419 0.3001 11.00000 0.05 0.25 Q2 1 0.9851 0.3718 0.5653 11.00000 0.05 0.23 ; _cod_data_source_file fy2132sup1.cif _cod_data_source_block II _cod_database_code 1550336 _shelx_estimated_absorpt_t_min 0.773 _shelx_estimated_absorpt_t_max 0.909 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy O O1 0.7872(8) 0.7526(5) 0.5754(4) 0.0436(9) Uani d 1 O O2 1.0943(7) -0.0646(5) -0.0270(5) 0.0376(8) Uani d 1 O O3 1.2189(6) 0.5811(5) 0.8054(4) 0.0346(8) Uani d 1 N N1 0.6936(8) 0.0863(6) -0.0091(5) 0.0313(8) Uani d 1 H H1 0.506646 0.0619 -0.016887 0.038 Uiso calc 1 C C1 0.5812(13) 0.8622(8) 0.4558(8) 0.0457(12) Uani d 1 H H1A 0.673811 0.934512 0.373509 0.069 Uiso calc 1 H H1B 0.513623 0.962513 0.531259 0.069 Uiso calc 1 H H1C 0.413277 0.765528 0.379819 0.069 Uiso calc 1 C C2 0.8948(9) 0.6005(6) 0.4953(6) 0.0300(10) Uani d 1 C C3 0.8016(9) 0.5279(6) 0.3069(6) 0.0313(9) Uani d 1 H H3A 0.648153 0.586589 0.222842 0.038 Uiso calc 1 C C4 0.9284(9) 0.3719(6) 0.2397(6) 0.0296(9) Uani d 1 C C5 0.8312(9) 0.2985(7) 0.0327(6) 0.0330(10) Uani d 1 H H5A 0.690774 0.388824 -0.035372 0.04 Uiso calc 1 H H5B 1.004057 0.312362 -0.014027 0.04 Uiso calc 1 C C6 0.8314(9) -0.0728(6) -0.0364(6) 0.0318(9) Uani d 1 H H6 0.718873 -0.204814 -0.065598 0.038 Uiso calc 1 C C7 1.1468(11) 0.2848(7) 0.3628(6) 0.0387(11) Uani d 1 H H7 1.235762 0.177733 0.317846 0.046 Uiso calc 1 C C8 1.2385(10) 0.3531(6) 0.5538(6) 0.0382(11) Uani d 1 H H8 1.385838 0.289743 0.638179 0.046 Uiso calc 1 C C9 1.1167(9) 0.5113(6) 0.6200(5) 0.0295(10) Uani d 1 H H3 1.144(16) 0.711(7) 0.817(10) 0.061(18) Uiso d 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.054(2) 0.0452(19) 0.0316(18) 0.0282(16) 0.0062(14) -0.0004(14) O2 0.0287(17) 0.0393(17) 0.0418(19) 0.0016(12) 0.0094(13) -0.0082(14) O3 0.0383(17) 0.0347(16) 0.0260(15) 0.0064(12) 0.0027(12) -0.0021(12) N1 0.0234(16) 0.0360(18) 0.0309(19) 0.0017(13) 0.0047(14) -0.0041(14) C1 0.054(3) 0.047(3) 0.038(3) 0.024(2) 0.011(2) 0.009(2) C2 0.033(2) 0.027(2) 0.030(2) 0.0017(17) 0.0105(19) 0.0021(17) C3 0.032(2) 0.032(2) 0.026(2) 0.0069(17) 0.0025(17) 0.0053(16) C4 0.028(2) 0.030(2) 0.029(2) 0.0017(16) 0.0052(17) 0.0032(17) C5 0.038(2) 0.035(2) 0.024(2) 0.0041(17) 0.0066(18) 0.0056(16) C6 0.035(2) 0.033(2) 0.025(2) -0.0045(17) 0.0096(17) -0.0031(16) C7 0.047(3) 0.037(2) 0.028(2) 0.015(2) 0.0018(19) -0.0023(18) C8 0.040(3) 0.036(3) 0.032(3) 0.014(2) -0.002(2) 0.0008(19) C9 0.031(2) 0.029(2) 0.025(2) -0.0005(17) 0.0059(18) -0.0017(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C2 O1 C1 117.7(3) C9 O3 H3 106(4) C6 N1 C5 124.2(3) C6 N1 H1 117.9 C5 N1 H1 117.9 O1 C1 H1A 109.5 O1 C1 H1B 109.5 H1A C1 H1B 109.5 O1 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 O1 C2 C3 125.9(4) O1 C2 C9 114.6(4) C3 C2 C9 119.5(4) C4 C3 C2 121.1(4) C4 C3 H3A 119.5 C2 C3 H3A 119.5 C7 C4 C3 119.2(4) C7 C4 C5 120.3(4) C3 C4 C5 120.6(4) N1 C5 C4 113.5(3) N1 C5 H5A 108.9 C4 C5 H5A 108.9 N1 C5 H5B 108.9 C4 C5 H5B 108.9 H5A C5 H5B 107.7 O2 C6 N1 125.7(4) O2 C6 H6 117.1 N1 C6 H6 117.1 C4 C7 C8 120.4(4) C4 C7 H7 119.8 C8 C7 H7 119.8 C9 C8 C7 120.4(4) C9 C8 H8 119.8 C7 C8 H8 119.8 O3 C9 C8 119.3(4) O3 C9 C2 121.3(4) C8 C9 C2 119.4(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.352(6) O1 C1 1.415(6) O2 C6 1.239(5) O3 C9 1.364(5) O3 H3 0.96(3) N1 C6 1.325(6) N1 C5 1.453(6) N1 H1 0.88 C1 H1A 0.98 C1 H1B 0.98 C1 H1C 0.98 C2 C3 1.389(6) C2 C9 1.400(6) C3 C4 1.382(6) C3 H3A 0.95 C4 C7 1.376(6) C4 C5 1.516(6) C5 H5A 0.99 C5 H5B 0.99 C6 H6 0.95 C7 C8 1.400(6) C7 H7 0.95 C8 C9 1.374(6) C8 H8 0.95 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 O2 1_455 0.88 2.05 2.910(4) 166.5 O3 H3 O1 . 0.96(3) 2.15(7) 2.672(4) 113(5) C6 H6 O3 1_444 0.95 2.54 3.391(5) 148.6 O3 H3 O2 1_566 0.96(3) 1.90(4) 2.771(4) 149(6) C5 H5B O3 1_554 0.99 2.60 3.374(5) 135 C5 H5A O3 1_454 0.99 2.70 3.676(5) 167 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C1 O1 C2 C3 -6.5(6) C1 O1 C2 C9 174.5(4) O1 C2 C3 C4 179.7(4) C9 C2 C3 C4 -1.3(6) C2 C3 C4 C7 1.2(6) C2 C3 C4 C5 -178.1(3) C6 N1 C5 C4 -97.8(5) C7 C4 C5 N1 65.2(5) C3 C4 C5 N1 -115.5(4) C5 N1 C6 O2 1.3(6) C3 C4 C7 C8 0.2(7) C5 C4 C7 C8 179.6(4) C4 C7 C8 C9 -1.6(7) C7 C8 C9 O3 -177.1(4) C7 C8 C9 C2 1.5(7) O1 C2 C9 O3 -2.3(5) C3 C2 C9 O3 178.5(4) O1 C2 C9 C8 179.0(4) C3 C2 C9 C8 -0.1(6) _cod_database_fobs_code 1550336