#------------------------------------------------------------------------------ #$Date: 2025-09-04 17:24:52 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302019 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519510.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_4519510 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 'C10 H10 O2' _chemical_formula_sum 'C10 H10 O2' _chemical_formula_weight 162.18 _chemical_name_common 'alpha-p-Methyl-trans-cinnamic acid' _chemical_name_systematic ' 3-(4-methylphenyl)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 mixed _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 2021-04-07 _cell_angle_alpha 90 _cell_angle_beta 91.024(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.9841(2) _cell_length_b 4.91400(10) _cell_length_c 27.9813(7) _cell_measurement_reflns_used 9945 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.597 _cell_measurement_theta_min 5.505 _cell_volume 822.68(4) _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 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 0.993 _diffrn_measured_fraction_theta_max 0.995 _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 0.0286 _diffrn_reflns_av_unetI/netI 0.0192 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 13122 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.613 _diffrn_reflns_theta_min 5.503 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.199914 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.9 _exptl_absorpt_coefficient_mu 0.469 _exptl_absorpt_correction_T_max 0.2103 _exptl_absorpt_correction_T_min 0.1192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0941 before and 0.0489 after correction. The Ratio of minimum to maximum transmission is 0.5668. 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 1.309 _exptl_crystal_description Plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.332 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 116 _refine_ls_number_reflns 1878 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0460 _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^)+(0.0781P)^2^+0.2635P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1389 _refine_ls_wR_factor_ref 0.1408 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1771 _reflns_number_total 1878 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 02-4MeCA-jw23113-P21n.cif _cod_data_source_block jw23113 _cod_database_code 4519510 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 O1 O 1.04766(16) -0.2654(2) 0.45654(3) 0.0387(3) Uani 1 1 d D . . . . H1 H 1.120(7) -0.416(6) 0.4636(15) 0.058 Uiso 0.5 1 d D U P A 2 O2 O 0.73938(17) -0.3358(2) 0.49896(4) 0.0404(3) Uani 1 1 d D . . . . H2 H 0.815(6) -0.464(7) 0.5121(14) 0.061 Uiso 0.5 1 d D U P B 1 C1 C 0.8514(2) -0.2094(3) 0.46646(5) 0.0329(3) Uani 1 1 d . . . . . C2 C 0.7261(2) 0.0074(3) 0.44154(5) 0.0344(3) Uani 1 1 d . . . . . H2A H 0.580560 0.052196 0.452058 0.041 Uiso 1 1 calc R U . . . C3 C 0.8097(2) 0.1428(3) 0.40475(5) 0.0324(3) Uani 1 1 d . . . . . H3 H 0.958209 0.099887 0.395950 0.039 Uiso 1 1 calc R U . . . C4 C 0.6928(2) 0.3523(3) 0.37658(4) 0.0310(3) Uani 1 1 d . . . . . C5 C 0.7896(2) 0.4562(3) 0.33542(5) 0.0342(3) Uani 1 1 d . . . . . H5 H 0.932668 0.392831 0.326310 0.041 Uiso 1 1 calc R U . . . C6 C 0.6802(2) 0.6510(3) 0.30747(5) 0.0345(3) Uani 1 1 d . . . . . H6 H 0.749123 0.717915 0.279494 0.041 Uiso 1 1 calc R U . . . C7 C 0.4709(2) 0.7491(3) 0.32007(5) 0.0320(3) Uani 1 1 d . . . . . C8 C 0.3749(2) 0.6474(3) 0.36137(5) 0.0341(3) Uani 1 1 d . . . . . H8 H 0.232740 0.712977 0.370652 0.041 Uiso 1 1 calc R U . . . C9 C 0.4827(2) 0.4523(3) 0.38925(5) 0.0335(3) Uani 1 1 d . . . . . H9 H 0.413333 0.385817 0.417211 0.040 Uiso 1 1 calc R U . . . C10 C 0.3498(2) 0.9696(2) 0.28971(4) 0.0307(3) Uani 1 1 d . . . . . H10A H 0.394264 1.150431 0.301186 0.046 Uiso 1 1 calc R U . . . H10B H 0.187803 0.948190 0.292610 0.046 Uiso 1 1 calc R U . . . H10C H 0.390782 0.949708 0.256141 0.046 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 O1 0.0373(5) 0.0399(6) 0.0392(5) 0.0073(4) 0.0040(4) 0.0076(4) O2 0.0430(6) 0.0380(6) 0.0404(5) 0.0091(4) 0.0081(4) 0.0060(4) C1 0.0369(7) 0.0302(6) 0.0317(6) 0.0000(5) 0.0003(5) 0.0017(5) C2 0.0351(6) 0.0323(6) 0.0357(6) 0.0017(5) 0.0004(5) 0.0041(5) C3 0.0336(6) 0.0305(6) 0.0332(6) -0.0009(5) -0.0005(5) 0.0025(5) C4 0.0330(6) 0.0282(6) 0.0318(6) -0.0005(5) -0.0011(5) 0.0006(5) C5 0.0309(6) 0.0338(7) 0.0379(7) 0.0017(5) 0.0028(5) 0.0024(5) C6 0.0372(7) 0.0327(7) 0.0336(6) 0.0039(5) 0.0036(5) -0.0004(5) C7 0.0354(6) 0.0276(6) 0.0327(6) -0.0011(5) -0.0035(5) 0.0003(5) C8 0.0321(6) 0.0335(7) 0.0368(7) -0.0008(5) 0.0012(5) 0.0042(5) C9 0.0349(6) 0.0339(7) 0.0320(6) 0.0024(5) 0.0032(5) 0.0021(5) C10 0.0336(6) 0.0273(6) 0.0311(6) -0.0019(5) -0.0021(4) -0.0004(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' 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 127(3) . . C1 O2 H2 112(3) . . O1 C1 O2 123.55(12) . . O1 C1 C2 122.03(12) . . O2 C1 C2 114.42(11) . . C1 C2 H2A 118.9 . . C3 C2 C1 122.21(12) . . C3 C2 H2A 118.9 . . C2 C3 H3 117.1 . . C2 C3 C4 125.74(12) . . C4 C3 H3 117.1 . . C5 C4 C3 119.94(12) . . C5 C4 C9 117.93(11) . . C9 C4 C3 122.12(12) . . C4 C5 H5 119.4 . . C6 C5 C4 121.14(12) . . C6 C5 H5 119.4 . . C5 C6 H6 119.6 . . C5 C6 C7 120.76(12) . . C7 C6 H6 119.6 . . C6 C7 C10 121.14(12) . . C8 C7 C6 118.17(12) . . C8 C7 C10 120.68(12) . . C7 C8 H8 119.3 . . C9 C8 C7 121.32(12) . . C9 C8 H8 119.3 . . C4 C9 H9 119.7 . . C8 C9 C4 120.67(12) . . C8 C9 H9 119.7 . . C7 C10 H10A 109.5 . . C7 C10 H10B 109.5 . . C7 C10 H10C 109.5 . . H10A C10 H10B 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 H1 0.879(19) . O1 C1 1.2425(16) . O2 H2 0.857(19) . O2 C1 1.2977(16) . C1 C2 1.4712(18) . C2 H2A 0.9500 . C2 C3 1.3309(19) . C3 H3 0.9500 . C3 C4 1.4667(18) . C4 C5 1.3951(18) . C4 C9 1.4013(18) . C5 H5 0.9500 . C5 C6 1.3924(18) . C6 H6 0.9500 . C6 C7 1.3933(19) . C7 C8 1.3925(19) . C7 C10 1.5487(17) . C8 H8 0.9500 . C8 C9 1.3880(18) . C9 H9 0.9500 . C10 H10A 0.9800 . C10 H10B 0.9800 . C10 H10C 0.9800 . 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 0.879(19) 1.81(2) 2.6380(14) 157(4) 3_746 yes O2 H2 O1 0.857(19) 1.78(2) 2.6380(14) 175(4) 3_746 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 O1 C1 C2 C3 4.8(2) . . . . O2 C1 C2 C3 -174.67(13) . . . . C1 C2 C3 C4 177.06(12) . . . . C2 C3 C4 C5 -172.49(13) . . . . C2 C3 C4 C9 6.8(2) . . . . C3 C4 C5 C6 178.64(12) . . . . C3 C4 C9 C8 -178.92(12) . . . . C4 C5 C6 C7 0.4(2) . . . . C5 C4 C9 C8 0.4(2) . . . . C5 C6 C7 C8 0.2(2) . . . . C5 C6 C7 C10 178.87(12) . . . . C6 C7 C8 C9 -0.5(2) . . . . C7 C8 C9 C4 0.2(2) . . . . C9 C4 C5 C6 -0.6(2) . . . . C10 C7 C8 C9 -179.18(11) . . . . _cod_database_fobs_code 4519510