#------------------------------------------------------------------------------ #$Date: 2025-09-04 17:25:05 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302020 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519511.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_4519511 loop_ _publ_author_name 'Aaron Gabriel Numez Avila' 'Thierry Maris' 'James D. Wuest' _publ_contact_author_id_orcid 0000-0001-9731-4046 _publ_section_title ; A Workplan for Using Heteroseeded Crystallizations to Produce New Polymorphs, as Illustrated by a Study of Cinnamic Acids ; _journal_name_full 'Crystal Growth & Design' _journal_page_first 6370 _journal_page_last 6381 _journal_paper_doi 10.1021/acs.cgd.5c00774 _journal_volume 25 _journal_year 2025 _chemical_formula_moiety 'C9 H7 Br O2' _chemical_formula_sum 'C9 H7 Br O2' _chemical_formula_weight 227.06 _chemical_name_common '4-bromocinnamic acid' _chemical_name_systematic ' 3-(4-bromophenyl)prop-2-enoic acid' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_contact_author_email thierry.maris@umontreal.ca _audit_contact_author_name 'Thierry Maris' _audit_contact_author_phone '+1 514 340 4711 2579' _audit_creation_date 2022-01-18 _cell_angle_alpha 103.086(1) _cell_angle_beta 93.763(1) _cell_angle_gamma 100.454(1) _cell_formula_units_Z 2 _cell_length_a 3.8274(1) _cell_length_b 7.5328(2) _cell_length_c 14.9381(4) _cell_measurement_reflns_used 8138 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.088 _cell_measurement_theta_min 3.056 _cell_volume 409.965(19) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker APEX2 CCD' _diffrn_measured_fraction_theta_full 0.970 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'nylon loop' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Quazar MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_unetI/netI 0.0111 _diffrn_reflns_Laue_measured_fraction_full 0.970 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10576 _diffrn_reflns_point_group_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.080 _diffrn_reflns_theta_min 3.056 _diffrn_source 'Microfocus Source' _diffrn_source_current 0.43 _diffrn_source_power 0.0106941 _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _diffrn_source_voltage 24.87 _exptl_absorpt_coefficient_mu 6.450 _exptl_absorpt_correction_T_max 0.2750 _exptl_absorpt_correction_T_min 0.1022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1363 before and 0.0316 after correction. The Ratio of minimum to maximum transmission is 0.3716. The \l/2 correction factor is Not present. ; _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 1.839 _exptl_crystal_description needle _exptl_crystal_F_000 224 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.825 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.156 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1516 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.178 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0420 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+1.7092P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.1252 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1515 _reflns_number_total 1516 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 03-4BrCA-jw24094-P-1.cif _cod_data_source_block jw24094 _cod_database_code 4519511 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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 Br1 Br 0.11578(13) 0.12874(7) 0.91814(3) 0.0269(2) Uani 1 1 d . . . . . O1 O 0.8055(9) 0.9701(4) 0.5997(2) 0.0190(7) Uani 1 1 d . . . . . H1 H 0.871680 1.043352 0.566421 0.029 Uiso 0.5 1 calc R U P A 2 C1 C 0.8649(11) 0.8072(6) 0.5625(3) 0.0140(8) Uani 1 1 d . . . . . O2 O 1.0006(9) 0.7699(4) 0.4881(2) 0.0184(6) Uani 1 1 d . . . . . H2 H 1.044501 0.865648 0.467578 0.028 Uiso 0.5 1 calc R U P B 1 C2 C 0.7662(11) 0.6590(6) 0.6111(3) 0.0147(8) Uani 1 1 d . . . . . H2A H 0.793575 0.536512 0.583220 0.018 Uiso 1 1 calc R U . . . C3 C 0.6391(11) 0.6912(6) 0.6932(3) 0.0134(8) Uani 1 1 d . . . . . H3 H 0.620286 0.815826 0.719500 0.016 Uiso 1 1 calc R U . . . C4 C 0.5259(11) 0.5550(6) 0.7470(3) 0.0123(8) Uani 1 1 d . . . . . C5 C 0.4104(11) 0.6151(6) 0.8336(3) 0.0142(8) Uani 1 1 d . . . . . H5 H 0.411597 0.743488 0.856821 0.017 Uiso 1 1 calc R U . . . C6 C 0.2946(11) 0.4907(6) 0.8859(3) 0.0151(8) Uani 1 1 d . . . . . H6 H 0.218318 0.532980 0.944880 0.018 Uiso 1 1 calc R U . . . C7 C 0.2915(11) 0.3033(6) 0.8512(3) 0.0134(8) Uani 1 1 d . . . . . C8 C 0.4077(11) 0.2399(6) 0.7655(3) 0.0155(8) Uani 1 1 d . . . . . H8 H 0.406985 0.111356 0.742723 0.019 Uiso 1 1 calc R U . . . C9 C 0.5238(11) 0.3651(6) 0.7140(3) 0.0137(8) Uani 1 1 d . . . . . H9 H 0.603321 0.322243 0.655577 0.016 Uiso 1 1 calc R U . . . 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 Br1 0.0291(4) 0.0263(3) 0.0283(3) 0.0130(2) 0.0062(2) 0.0042(2) O1 0.0294(18) 0.0123(14) 0.0176(14) 0.0054(11) 0.0076(12) 0.0060(12) C1 0.014(2) 0.0129(19) 0.0144(18) 0.0039(15) -0.0009(15) 0.0016(15) O2 0.0294(18) 0.0151(14) 0.0129(14) 0.0059(11) 0.0079(12) 0.0055(12) C2 0.020(2) 0.0115(18) 0.0133(18) 0.0053(15) 0.0023(15) 0.0013(15) C3 0.015(2) 0.0120(18) 0.0136(18) 0.0037(15) 0.0001(15) 0.0032(15) C4 0.011(2) 0.0149(19) 0.0129(18) 0.0062(15) 0.0000(14) 0.0032(14) C5 0.017(2) 0.0127(19) 0.0134(19) 0.0032(15) 0.0010(15) 0.0045(15) C6 0.017(2) 0.016(2) 0.0135(18) 0.0043(15) 0.0042(15) 0.0044(16) C7 0.013(2) 0.0146(19) 0.0150(19) 0.0087(15) 0.0014(15) 0.0015(15) C8 0.016(2) 0.0143(19) 0.0159(19) 0.0034(15) 0.0009(15) 0.0038(15) C9 0.016(2) 0.0153(19) 0.0105(18) 0.0040(15) 0.0004(15) 0.0051(15) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C1 O1 H1 109.5 . . O1 C1 C2 117.5(4) . . O2 C1 O1 123.6(4) . . O2 C1 C2 118.9(4) . . C1 O2 H2 109.5 . . C1 C2 H2A 119.0 . . C3 C2 C1 122.1(4) . . C3 C2 H2A 119.0 . . C2 C3 H3 116.5 . . C2 C3 C4 127.0(4) . . C4 C3 H3 116.5 . . C5 C4 C3 119.2(4) . . C5 C4 C9 118.6(4) . . C9 C4 C3 122.2(4) . . C4 C5 H5 119.5 . . C6 C5 C4 121.1(4) . . C6 C5 H5 119.4 . . C5 C6 H6 120.5 . . C5 C6 C7 119.1(4) . . C7 C6 H6 120.5 . . C6 C7 Br1 120.2(3) . . C6 C7 C8 121.0(4) . . C8 C7 Br1 118.7(3) . . C7 C8 H8 120.3 . . C9 C8 C7 119.4(4) . . C9 C8 H8 120.3 . . C4 C9 H9 119.6 . . C8 C9 C4 120.8(4) . . C8 C9 H9 119.6 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C7 1.883(4) . O1 H1 0.8400 . O1 C1 1.294(5) . C1 O2 1.254(5) . C1 C2 1.472(6) . O2 H2 0.8400 . C2 H2A 0.9500 . C2 C3 1.336(6) . C3 H3 0.9500 . C3 C4 1.464(6) . C4 C5 1.399(6) . C4 C9 1.401(6) . C5 H5 0.9500 . C5 C6 1.383(6) . C6 H6 0.9500 . C6 C7 1.386(6) . C7 C8 1.393(6) . C8 H8 0.9500 . C8 C9 1.378(6) . C9 H9 0.9500 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O2 0.84 1.79 2.621(4) 170.1 2_776 yes O2 H2 O1 0.84 1.80 2.621(4) 164.2 2_776 yes 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Br1 C7 C8 C9 177.5(3) . . . . O1 C1 C2 C3 -3.9(6) . . . . C1 C2 C3 C4 178.7(4) . . . . O2 C1 C2 C3 176.2(4) . . . . C2 C3 C4 C5 177.8(4) . . . . C2 C3 C4 C9 -3.2(7) . . . . C3 C4 C5 C6 178.7(4) . . . . C3 C4 C9 C8 -178.5(4) . . . . C4 C5 C6 C7 -0.5(6) . . . . C5 C4 C9 C8 0.5(6) . . . . C5 C6 C7 Br1 -177.2(3) . . . . C5 C6 C7 C8 1.0(6) . . . . C6 C7 C8 C9 -0.8(6) . . . . C7 C8 C9 C4 0.0(6) . . . . C9 C4 C5 C6 -0.3(6) . . . . _cod_database_fobs_code 4519511