#------------------------------------------------------------------------------ #$Date: 2025-09-04 17:26:01 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302023 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519514.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_4519514 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 I O2' _chemical_formula_sum 'C9 H7 I O2' _chemical_formula_weight 274.05 _chemical_name_common '4-Iodo-trans-cinnamic acid' _chemical_name_systematic '3-(4-iodophenyl)prop-2-enoic acid' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 2023-10-18 _cell_angle_alpha 90 _cell_angle_beta 96.571(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.7325(11) _cell_length_b 4.0785(6) _cell_length_c 29.139(5) _cell_measurement_reflns_used 3544 _cell_measurement_temperature 296 _cell_measurement_theta_max 53.772 _cell_measurement_theta_min 2.657 _cell_volume 912.9(2) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 4 (2022) 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 296 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_unetI/netI 0.0332 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 7774 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.925 _diffrn_reflns_theta_min 5.033 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.1993706 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 18.693 _exptl_absorpt_correction_T_max 0.1123 _exptl_absorpt_correction_T_min 0.0279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1246 before and 0.0616 after correction. The Ratio of minimum to maximum transmission is 0.2484. 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 1.994 _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_recrystallization_method 'crystallised from THF' _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.948 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1714 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0404 _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^)+(0.0512P)^2^+1.4356P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1081 _refine_ls_wR_factor_ref 0.1177 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1289 _reflns_number_total 1714 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 06-4ICA-jw26047-P21n.cif _cod_data_source_block jw26047 _cod_database_code 4519514 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -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 I1 I -0.08263(5) 0.01715(10) 0.29246(2) 0.0893(2) Uani 1 1 d . . . . . O1 O 0.7845(6) 0.9969(12) 0.50678(17) 0.1023(17) Uani 1 1 d . . . . . H1 H 0.885179 1.047497 0.515943 0.153 Uiso 0.5 1 calc R U P A 1 C1 C 0.7806(8) 0.8492(19) 0.4688(2) 0.0845(17) Uani 1 1 d . . . . . O2 O 0.9187(6) 0.7974(15) 0.44999(16) 0.1086(16) Uani 1 1 d . . . . . H2 H 1.002468 0.873422 0.466353 0.163 Uiso 0.5 1 calc R U P B 2 C2 C 0.6155(7) 0.7354(18) 0.4460(2) 0.0829(17) Uani 1 1 d . . . . . H2A H 0.516233 0.766205 0.460703 0.099 Uiso 1 1 calc R U . . . C3 C 0.5991(8) 0.5896(17) 0.4051(2) 0.0801(16) Uani 1 1 d . . . . . H3 H 0.700285 0.567997 0.390931 0.096 Uiso 1 1 calc R U . . . C4 C 0.4392(8) 0.4583(15) 0.3798(2) 0.0749(16) Uani 1 1 d . . . . . C5 C 0.4425(8) 0.3266(18) 0.3364(2) 0.0841(17) Uani 1 1 d . . . . . H5 H 0.547593 0.319487 0.323748 0.101 Uiso 1 1 calc R U . . . C6 C 0.2966(8) 0.2063(17) 0.3114(2) 0.0834(17) Uani 1 1 d . . . . . H6 H 0.302340 0.123043 0.281885 0.100 Uiso 1 1 calc R U . . . C7 C 0.1404(7) 0.2085(14) 0.3299(2) 0.0712(14) Uani 1 1 d . . . . . C8 C 0.1327(8) 0.3350(17) 0.3733(2) 0.0816(17) Uani 1 1 d . . . . . H8 H 0.028121 0.333410 0.386256 0.098 Uiso 1 1 calc R U . . . C9 C 0.2787(9) 0.4629(16) 0.3974(2) 0.0841(18) Uani 1 1 d . . . . . H9 H 0.271308 0.555350 0.426334 0.101 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 I1 0.0778(3) 0.0794(4) 0.1048(4) -0.0074(2) -0.0143(2) -0.00096(19) O1 0.076(3) 0.150(5) 0.080(3) -0.029(3) 0.004(2) -0.013(3) C1 0.075(4) 0.102(5) 0.076(4) -0.005(4) 0.007(3) -0.005(4) O2 0.069(3) 0.161(5) 0.095(3) -0.036(3) 0.006(2) -0.014(3) C2 0.061(3) 0.108(5) 0.078(4) -0.004(4) -0.002(3) -0.003(3) C3 0.065(3) 0.097(4) 0.076(4) 0.000(3) 0.000(3) 0.002(3) C4 0.065(3) 0.085(4) 0.072(4) 0.002(3) -0.003(3) 0.005(3) C5 0.065(3) 0.107(5) 0.079(4) -0.008(4) 0.005(3) 0.004(3) C6 0.073(4) 0.098(5) 0.077(4) -0.010(3) -0.001(3) 0.003(3) C7 0.062(3) 0.066(3) 0.081(4) -0.001(3) -0.011(3) 0.003(3) C8 0.061(3) 0.098(5) 0.085(4) -0.007(4) 0.006(3) -0.008(3) C9 0.075(4) 0.101(5) 0.076(4) -0.016(3) 0.009(3) -0.010(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' I I 0.0030 5.4350 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 '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 O2 121.4(6) . . O1 C1 C2 119.3(6) . . O2 C1 C2 119.3(6) . . C1 O2 H2 109.5 . . C1 C2 H2A 118.5 . . C3 C2 C1 123.1(6) . . C3 C2 H2A 118.5 . . C2 C3 H3 116.4 . . C2 C3 C4 127.3(6) . . C4 C3 H3 116.4 . . C5 C4 C3 120.1(6) . . C5 C4 C9 117.0(6) . . C9 C4 C3 122.8(6) . . C4 C5 H5 119.0 . . C6 C5 C4 122.0(6) . . C6 C5 H5 119.0 . . C5 C6 H6 120.1 . . C5 C6 C7 119.8(6) . . C7 C6 H6 120.1 . . C6 C7 I1 120.1(4) . . C8 C7 I1 120.2(4) . . C8 C7 C6 119.7(5) . . C7 C8 H8 120.1 . . C9 C8 C7 119.8(6) . . C9 C8 H8 120.1 . . C4 C9 H9 119.2 . . C8 C9 C4 121.5(6) . . C8 C9 H9 119.2 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 I1 C7 2.084(5) . O1 H1 0.8200 . O1 C1 1.258(8) . C1 O2 1.272(8) . C1 C2 1.446(8) . O2 H2 0.8200 . C2 H2A 0.9300 . C2 C3 1.323(8) . C3 H3 0.9300 . C3 C4 1.467(9) . C4 C5 1.376(9) . C4 C9 1.397(9) . C5 H5 0.9300 . C5 C6 1.363(8) . C6 H6 0.9300 . C6 C7 1.378(8) . C7 C8 1.374(8) . C8 H8 0.9300 . C8 C9 1.363(9) . C9 H9 0.9300 . 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 I1 C7 C8 C9 -179.3(5) . . . . O1 C1 C2 C3 177.3(7) . . . . C1 C2 C3 C4 178.3(7) . . . . O2 C1 C2 C3 -2.8(12) . . . . C2 C3 C4 C5 176.9(7) . . . . C2 C3 C4 C9 -2.3(11) . . . . C3 C4 C5 C6 -179.0(7) . . . . C3 C4 C9 C8 -179.1(7) . . . . C4 C5 C6 C7 -1.4(11) . . . . C5 C4 C9 C8 1.7(10) . . . . C5 C6 C7 I1 -178.9(5) . . . . C5 C6 C7 C8 0.7(10) . . . . C6 C7 C8 C9 1.2(10) . . . . C7 C8 C9 C4 -2.4(11) . . . . C9 C4 C5 C6 0.2(10) . . . . _cod_database_fobs_code 4519514