#------------------------------------------------------------------------------ #$Date: 2025-09-04 17:25:51 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302022 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519513.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_4519513 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 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' _cell_angle_alpha 83.820(2) _cell_angle_beta 87.960(2) _cell_angle_gamma 86.382(2) _cell_formula_units_Z 4 _cell_length_a 4.0202(1) _cell_length_b 7.6998(3) _cell_length_c 28.8401(12) _cell_measurement_reflns_used 4846 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.895 _cell_measurement_theta_min 2.683 _cell_volume 885.41(6) _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 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.300 _diffrn_measured_fraction_theta_max 0.302 _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_unetI/netI 0.0237 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 3328 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.938 _diffrn_reflns_theta_min 2.683 _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 _exptl_absorpt_coefficient_mu 19.273 _exptl_absorpt_correction_T_max 0.1122 _exptl_absorpt_correction_T_min 0.026 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. Final HKLF 4 output contains 53132 reflections, Rint = 0.0654 (38903 with I > 3sig(I), Rint = 0.0615) ; _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 2.056 _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_recrystallization_method 'crystallised from THF/MeOH' _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.842 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.109 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3328 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0338 _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^)+(0.0397P)^2^+1.7731P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.0896 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2934 _reflns_number_total 3328 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 05-4ICA-jw26046-P-1-Z4.cif _cod_data_source_block jw26046 _cod_database_code 4519513 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 I1A I 0.47791(19) 0.44014(9) 0.70798(2) 0.0507(3) Uani 1 1 d . . . . . O1A O 1.285(3) 1.4248(10) 0.5520(3) 0.064(2) Uani 1 1 d . . . . . H1A H 1.366478 1.510638 0.536019 0.096 Uiso 1 1 calc R U . . . C1A C 1.346(3) 1.2856(14) 0.5309(4) 0.048(3) Uani 1 1 d . . . . . O2A O 1.498(2) 1.2870(10) 0.4927(3) 0.056(2) Uani 1 1 d . . . . . C2A C 1.223(3) 1.1229(14) 0.5538(4) 0.047(3) Uani 1 1 d . . . . . H2A H 1.252671 1.020671 0.538054 0.057 Uiso 1 1 calc R U . . . C3A C 1.070(3) 1.1103(14) 0.5959(4) 0.047(3) Uani 1 1 d . . . . . H3A H 1.046597 1.213965 0.611148 0.057 Uiso 1 1 calc R U . . . C4A C 0.935(3) 0.9536(14) 0.6209(4) 0.045(2) Uani 1 1 d . . . . . C5A C 0.809(3) 0.9596(14) 0.6662(4) 0.046(3) Uani 1 1 d . . . . . H5A H 0.811822 1.065573 0.680253 0.056 Uiso 1 1 calc R U . . . C6A C 0.678(3) 0.8148(14) 0.6915(4) 0.049(3) Uani 1 1 d . . . . . H6A H 0.594914 0.821119 0.722571 0.059 Uiso 1 1 calc R U . . . C7A C 0.672(3) 0.6606(13) 0.6708(4) 0.043(2) Uani 1 1 d . . . . . C8A C 0.792(3) 0.6517(14) 0.6254(4) 0.047(2) Uani 1 1 d . . . . . H8A H 0.784017 0.546450 0.611197 0.056 Uiso 1 1 calc R U . . . C9A C 0.924(3) 0.7961(14) 0.6012(4) 0.049(3) Uani 1 1 d . . . . . H9A H 1.009667 0.788640 0.570348 0.059 Uiso 1 1 calc R U . . . I1B I -0.00568(18) 1.11008(9) 0.79293(2) 0.0493(3) Uani 1 1 d . . . . . O1B O 0.780(2) 0.0884(10) 0.9502(3) 0.060(2) Uani 1 1 d . . . . . H1B H 0.853705 -0.002476 0.966251 0.091 Uiso 1 1 calc R U . . . C1B C 0.853(3) 0.2248(14) 0.9695(4) 0.048(3) Uani 1 1 d . . . . . O2B O 1.011(2) 0.2152(10) 1.0062(3) 0.054(2) Uani 1 1 d . . . . . C2B C 0.741(3) 0.3958(14) 0.9464(4) 0.047(3) Uani 1 1 d . . . . . H2B H 0.781990 0.497667 0.960666 0.056 Uiso 1 1 calc R U . . . C3B C 0.582(3) 0.4144(14) 0.9062(4) 0.048(3) Uani 1 1 d . . . . . H3B H 0.548047 0.309965 0.892734 0.057 Uiso 1 1 calc R U . . . C4B C 0.454(3) 0.5786(13) 0.8805(3) 0.043(2) Uani 1 1 d . . . . . C5B C 0.306(3) 0.5733(14) 0.8378(4) 0.050(3) Uani 1 1 d . . . . . H5B H 0.291319 0.463711 0.825959 0.059 Uiso 1 1 calc R U . . . C6B C 0.180(3) 0.7243(14) 0.8123(4) 0.049(3) Uani 1 1 d . . . . . H6B H 0.083216 0.719127 0.782944 0.059 Uiso 1 1 calc R U . . . C7B C 0.196(3) 0.8821(14) 0.8304(4) 0.043(2) Uani 1 1 d . . . . . C8B C 0.338(3) 0.8914(13) 0.8728(4) 0.044(2) Uani 1 1 d . . . . . H8B H 0.345228 1.000907 0.885011 0.053 Uiso 1 1 calc R U . . . C9B C 0.468(3) 0.7410(14) 0.8973(4) 0.047(2) Uani 1 1 d . . . . . H9B H 0.570256 0.747896 0.926262 0.056 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 I1A 0.0458(4) 0.0461(4) 0.0581(5) 0.0056(3) -0.0018(3) -0.0043(3) O1A 0.090(7) 0.042(4) 0.059(5) -0.004(4) 0.015(5) -0.010(4) C1A 0.057(7) 0.042(5) 0.043(6) -0.003(4) -0.002(5) -0.003(5) O2A 0.077(6) 0.047(4) 0.045(4) -0.002(3) 0.008(4) -0.009(4) C2A 0.057(7) 0.039(5) 0.046(6) -0.005(4) -0.007(5) -0.003(5) C3A 0.057(7) 0.040(5) 0.044(6) -0.002(4) -0.004(5) -0.001(5) C4A 0.046(6) 0.041(5) 0.046(5) 0.000(4) -0.009(5) 0.000(5) C5A 0.054(7) 0.041(5) 0.043(5) -0.006(4) -0.002(5) -0.001(5) C6A 0.052(7) 0.050(6) 0.043(5) -0.001(5) -0.001(5) -0.001(5) C7A 0.039(6) 0.039(5) 0.048(6) 0.006(4) -0.004(5) -0.002(4) C8A 0.049(7) 0.039(5) 0.053(6) -0.006(5) -0.002(5) -0.005(5) C9A 0.052(7) 0.045(6) 0.050(6) -0.006(5) 0.000(5) -0.003(5) I1B 0.0455(4) 0.0449(4) 0.0558(4) 0.0052(3) -0.0076(3) -0.0035(3) O1B 0.086(7) 0.038(4) 0.058(5) -0.003(3) -0.022(5) 0.001(4) C1B 0.056(7) 0.045(6) 0.042(6) 0.000(4) -0.002(5) -0.002(5) O2B 0.074(6) 0.045(4) 0.044(4) 0.000(3) -0.014(4) -0.003(4) C2B 0.058(7) 0.037(5) 0.046(6) -0.003(4) 0.000(5) -0.002(5) C3B 0.057(7) 0.037(5) 0.048(6) -0.001(4) -0.002(5) -0.005(5) C4B 0.046(7) 0.042(5) 0.039(5) -0.001(4) -0.002(5) -0.003(5) C5B 0.057(7) 0.042(6) 0.050(6) -0.004(5) -0.009(5) -0.005(5) C6B 0.055(7) 0.046(6) 0.046(6) 0.001(5) -0.011(5) -0.006(5) C7B 0.038(6) 0.043(5) 0.046(5) 0.005(4) -0.004(4) -0.004(4) C8B 0.047(6) 0.038(5) 0.047(6) -0.002(4) -0.003(5) -0.001(5) C9B 0.048(6) 0.044(6) 0.050(6) -0.009(5) -0.009(5) -0.001(5) 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' O O 0.0389 0.0241 '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' 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 C1A O1A H1A 109.5 . . O1A C1A C2A 116.9(10) . . O2A C1A O1A 122.8(10) . . O2A C1A C2A 120.3(10) . . C1A C2A H2A 118.3 . . C3A C2A C1A 123.4(10) . . C3A C2A H2A 118.3 . . C2A C3A H3A 116.6 . . C2A C3A C4A 126.8(10) . . C4A C3A H3A 116.6 . . C5A C4A C3A 119.3(10) . . C5A C4A C9A 117.6(10) . . C9A C4A C3A 123.1(10) . . C4A C5A H5A 119.2 . . C6A C5A C4A 121.7(10) . . C6A C5A H5A 119.2 . . C5A C6A H6A 120.5 . . C5A C6A C7A 119.0(10) . . C7A C6A H6A 120.5 . . C6A C7A I1A 120.0(8) . . C6A C7A C8A 120.5(10) . . C8A C7A I1A 119.5(8) . . C7A C8A H8A 120.2 . . C9A C8A C7A 119.5(10) . . C9A C8A H8A 120.2 . . C4A C9A H9A 119.2 . . C8A C9A C4A 121.7(11) . . C8A C9A H9A 119.2 . . C1B O1B H1B 109.5 . . O1B C1B C2B 117.0(10) . . O2B C1B O1B 123.0(10) . . O2B C1B C2B 120.0(10) . . C1B C2B H2B 118.7 . . C3B C2B C1B 122.6(10) . . C3B C2B H2B 118.7 . . C2B C3B H3B 116.4 . . C2B C3B C4B 127.2(10) . . C4B C3B H3B 116.4 . . C5B C4B C3B 119.1(10) . . C5B C4B C9B 118.0(10) . . C9B C4B C3B 122.9(10) . . C4B C5B H5B 119.3 . . C6B C5B C4B 121.4(10) . . C6B C5B H5B 119.3 . . C5B C6B H6B 120.6 . . C7B C6B C5B 118.8(10) . . C7B C6B H6B 120.6 . . C6B C7B I1B 119.1(8) . . C6B C7B C8B 121.2(10) . . C8B C7B I1B 119.7(8) . . C7B C8B H8B 120.3 . . C9B C8B C7B 119.4(10) . . C9B C8B H8B 120.3 . . C4B C9B H9B 119.4 . . C8B C9B C4B 121.2(10) . . C8B C9B H9B 119.4 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 I1A C7A 2.086(10) . O1A H1A 0.8400 . O1A C1A 1.294(14) . C1A O2A 1.240(13) . C1A C2A 1.459(15) . C2A H2A 0.9500 . C2A C3A 1.338(15) . C3A H3A 0.9500 . C3A C4A 1.462(15) . C4A C5A 1.391(15) . C4A C9A 1.397(15) . C5A H5A 0.9500 . C5A C6A 1.385(16) . C6A H6A 0.9500 . C6A C7A 1.387(15) . C7A C8A 1.388(15) . C8A H8A 0.9500 . C8A C9A 1.372(16) . C9A H9A 0.9500 . I1B C7B 2.093(10) . O1B H1B 0.8400 . O1B C1B 1.294(14) . C1B O2B 1.247(13) . C1B C2B 1.463(15) . C2B H2B 0.9500 . C2B C3B 1.332(15) . C3B H3B 0.9500 . C3B C4B 1.468(14) . C4B C5B 1.392(15) . C4B C9B 1.394(15) . C5B H5B 0.9500 . C5B C6B 1.385(15) . C6B H6B 0.9500 . C6B C7B 1.378(15) . C7B C8B 1.379(15) . C8B H8B 0.9500 . C8B C9B 1.375(15) . C9B H9B 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 O1A H1A O2A 0.84 1.79 2.624(11) 171.6 2_886 yes O1B H1B O2B 0.84 1.80 2.635(11) 171.3 2_757 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 I1A C7A C8A C9A -179.1(9) . . . . O1A C1A C2A C3A -3.8(18) . . . . C1A C2A C3A C4A 179.0(11) . . . . O2A C1A C2A C3A 177.0(12) . . . . C2A C3A C4A C5A 174.5(12) . . . . C2A C3A C4A C9A -6(2) . . . . C3A C4A C5A C6A -179.8(11) . . . . C3A C4A C9A C8A -179.3(11) . . . . C4A C5A C6A C7A -0.5(18) . . . . C5A C4A C9A C8A 0.3(18) . . . . C5A C6A C7A I1A 179.9(9) . . . . C5A C6A C7A C8A -0.2(17) . . . . C6A C7A C8A C9A 1.0(17) . . . . C7A C8A C9A C4A -1.1(18) . . . . C9A C4A C5A C6A 0.5(17) . . . . I1B C7B C8B C9B 179.6(9) . . . . O1B C1B C2B C3B -3.0(19) . . . . C1B C2B C3B C4B 179.0(12) . . . . O2B C1B C2B C3B 177.4(12) . . . . C2B C3B C4B C5B 177.4(12) . . . . C2B C3B C4B C9B -4(2) . . . . C3B C4B C5B C6B 179.6(12) . . . . C3B C4B C9B C8B -178.2(11) . . . . C4B C5B C6B C7B -1.3(19) . . . . C5B C4B C9B C8B 0.6(18) . . . . C5B C6B C7B I1B -178.3(9) . . . . C5B C6B C7B C8B 0.5(18) . . . . C6B C7B C8B C9B 0.8(18) . . . . C7B C8B C9B C4B -1.3(18) . . . . C9B C4B C5B C6B 0.8(18) . . . . loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.504(3) 2 0.496(3) _cod_database_fobs_code 4519513