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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/75/7207554.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_7207554
loop_
_publ_author_name
'Issa, Nizar'
'Barnett, Sarah A.'
'Mohamed, Sharmarke'
'Braun, Doris E.'
'Copley, Royston C. B.'
'Tocher, Derek A.'
'Price, Sarah L.'
_publ_section_title
;
 Screening for cocrystals of succinic acid and 4-aminobenzoic acid
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2454
_journal_paper_doi               10.1039/c2ce06325e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H10 O, 0.5(C4 H6 O4)'
_chemical_formula_sum            'C17 H13 O3'
_chemical_formula_weight         265.27
_chemical_name_common            '2(Diphenylcyclopropenone)(Succinic Acid)'
_chemical_name_systematic
;
Diphenylcyclopropenone Succinic acid (2/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.471(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.654(4)
_cell_length_b                   5.5540(14)
_cell_length_c                   16.288(4)
_cell_measurement_reflns_used    4236
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.2575
_cell_measurement_theta_min      2.5011
_cell_volume                     1325.6(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10750
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0782P)²+0.2534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                2638
_reflns_number_total             3179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06325e.txt
_cod_data_source_block           SuccinicAcid_diphenylcyclopropenone
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7207554
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.30165(6) 1.02278(18) 0.43259(7) 0.0399(3) Uani 1 1 d
C6 C 0.46878(8) 0.5467(2) 0.37606(7) 0.0231(3) Uani 1 1 d
C5 C 0.53612(9) 0.6634(2) 0.42245(8) 0.0257(3) Uani 1 1 d
C15 C 0.24017(9) 0.3504(2) 0.23722(8) 0.0283(3) Uani 1 1 d
C9 C 0.29192(8) 0.6533(2) 0.34021(8) 0.0249(3) Uani 1 1 d
C10 C 0.22375(8) 0.5558(2) 0.28423(7) 0.0244(3) Uani 1 1 d
C1 C 0.48946(9) 0.3306(2) 0.33626(8) 0.0260(3) Uani 1 1 d
C12 C 0.07719(9) 0.6017(3) 0.21802(8) 0.0319(3) Uani 1 1 d
C8 C 0.31809(8) 0.8365(2) 0.39469(8) 0.0277(3) Uani 1 1 d
C3 C 0.64261(9) 0.3500(2) 0.39048(8) 0.0295(3) Uani 1 1 d
C11 C 0.14106(9) 0.6796(2) 0.27497(8) 0.0280(3) Uani 1 1 d
C2 C 0.57633(9) 0.2332(2) 0.34391(8) 0.0297(3) Uani 1 1 d
C4 C 0.62297(9) 0.5654(3) 0.42946(8) 0.0294(3) Uani 1 1 d
C7 C 0.37861(8) 0.6530(2) 0.37155(7) 0.0246(3) Uani 1 1 d
C14 C 0.17592(10) 0.2740(3) 0.18002(8) 0.0321(3) Uani 1 1 d
C13 C 0.09518(10) 0.4008(3) 0.17016(8) 0.0330(3) Uani 1 1 d
O3 O 0.16956(6) 0.02726(18) 0.99206(6) 0.0347(3) Uani 1 1 d
O2 O 0.12665(7) 0.36814(19) 0.93026(7) 0.0389(3) Uani 1 1 d
C16 C 0.11022(8) 0.1600(2) 0.96652(7) 0.0236(3) Uani 1 1 d
C17 C 0.00964(8) 0.1067(2) 0.97251(8) 0.0269(3) Uani 1 1 d
H2 H 0.5894(11) 0.079(3) 0.3156(10) 0.034(4) Uiso 1 1 d
H5 H 0.5202(11) 0.813(3) 0.4516(10) 0.036(4) Uiso 1 1 d
H4 H 0.6711(14) 0.647(3) 0.4622(12) 0.055(5) Uiso 1 1 d
H1 H 0.4430(11) 0.244(3) 0.3034(10) 0.034(4) Uiso 1 1 d
H3 H 0.7020(11) 0.278(3) 0.3971(10) 0.036(4) Uiso 1 1 d
H7 H 0.0201(12) 0.688(3) 0.2114(10) 0.040(4) Uiso 1 1 d
H6 H 0.1295(11) 0.822(3) 0.3079(10) 0.034(4) Uiso 1 1 d
H8 H 0.0486(13) 0.349(3) 0.1323(11) 0.046(5) Uiso 1 1 d
H10 H 0.2974(11) 0.259(3) 0.2430(10) 0.037(4) Uiso 1 1 d
H9 H 0.1865(11) 0.129(3) 0.1458(10) 0.034(4) Uiso 1 1 d
H12 H -0.0223(11) 0.256(3) 0.9920(11) 0.040(4) Uiso 1 1 d
H13 H -0.0133(12) 0.072(3) 0.9146(12) 0.050(5) Uiso 1 1 d
H11 H 0.1915(17) 0.392(4) 0.9343(15) 0.084(7) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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
C5 C6 C1 119.61(11) . .
C5 C6 C7 118.56(11) . .
C1 C6 C7 121.83(11) . .
C4 C5 C6 120.37(12) . .
C4 C5 H5 120.7(9) . .
C6 C5 H5 118.9(9) . .
C14 C15 C10 119.99(12) . .
C14 C15 H10 118.6(9) . .
C10 C15 H10 121.4(10) . .
C7 C9 C8 61.01(9) . .
C7 C9 C10 150.18(12) . .
C8 C9 C10 148.42(12) . .
C15 C10 C11 119.68(12) . .
C15 C10 C9 121.92(11) . .
C11 C10 C9 118.33(12) . .
C2 C1 C6 119.67(12) . .
C2 C1 H1 119.0(9) . .
C6 C1 H1 121.3(9) . .
C11 C12 C13 119.89(13) . .
C11 C12 H7 120.0(10) . .
C13 C12 H7 120.2(10) . .
O1 C8 C9 151.05(13) . .
O1 C8 C7 150.69(13) . .
C9 C8 C7 58.23(9) . .
C4 C3 C2 120.45(12) . .
C4 C3 H3 119.9(10) . .
C2 C3 H3 119.6(10) . .
C12 C11 C10 119.94(12) . .
C12 C11 H6 120.3(9) . .
C10 C11 H6 119.7(9) . .
C1 C2 C3 120.26(12) . .
C1 C2 H2 118.4(9) . .
C3 C2 H2 121.4(9) . .
C3 C4 C5 119.64(12) . .
C3 C4 H4 119.5(11) . .
C5 C4 H4 120.9(11) . .
C9 C7 C8 60.76(9) . .
C9 C7 C6 149.91(12) . .
C8 C7 C6 149.30(12) . .
C13 C14 C15 119.82(13) . .
C13 C14 H9 119.0(9) . .
C15 C14 H9 121.2(9) . .
C14 C13 C12 120.64(13) . .
C14 C13 H8 121.5(11) . .
C12 C13 H8 117.8(11) . .
C16 O2 H11 106.0(14) . .
O3 C16 O2 123.60(12) . .
O3 C16 C17 123.90(11) . .
O2 C16 C17 112.50(11) . .
C16 C17 C17 112.31(13) . 3_557
C16 C17 H12 108.5(10) . .
C17 C17 H12 111.6(10) 3_557 .
C16 C17 H13 107.0(10) . .
C17 C17 H13 109.7(11) 3_557 .
H12 C17 H13 107.5(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.2298(16) .
C6 C5 1.3974(17) .
C6 C1 1.3982(17) .
C6 C7 1.4485(17) .
C5 C4 1.3881(18) .
C5 H5 0.987(17) .
C15 C14 1.3857(19) .
C15 C10 1.3955(18) .
C15 H10 0.985(17) .
C9 C7 1.3652(18) .
C9 C8 1.4012(18) .
C9 C10 1.4519(17) .
C10 C11 1.4006(18) .
C1 C2 1.3879(18) .
C1 H1 0.988(16) .
C12 C11 1.3818(19) .
C12 C13 1.387(2) .
C12 H7 0.970(17) .
C8 C7 1.4047(17) .
C3 C4 1.386(2) .
C3 C2 1.3884(19) .
C3 H3 0.963(17) .
C11 H6 0.971(16) .
C2 H2 0.990(16) .
C4 H4 0.99(2) .
C14 C13 1.385(2) .
C14 H9 0.994(16) .
C13 H8 0.960(18) .
O3 C16 1.2112(15) .
O2 C16 1.3210(15) .
O2 H11 0.96(3) .
C16 C17 1.5073(17) .
C17 C17 1.514(3) 3_557
C17 H12 1.004(18) .
C17 H13 1.018(19) .
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
O2 H11 O1 0.96(3) 1.68(3) 2.6351(15) 170(2) 4_576
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_4
C1 C6 C5 C4 -0.31(19) .
C7 C6 C5 C4 178.94(11) .
C14 C15 C10 C11 1.85(19) .
C14 C15 C10 C9 -175.09(12) .
C7 C9 C10 C15 7.1(3) .
C8 C9 C10 C15 174.80(19) .
C7 C9 C10 C11 -169.9(2) .
C8 C9 C10 C11 -2.2(3) .
C5 C6 C1 C2 0.64(18) .
C7 C6 C1 C2 -178.58(12) .
C7 C9 C8 O1 177.7(3) .
C10 C9 C8 O1 4.6(4) .
C10 C9 C8 C7 -173.1(2) .
C13 C12 C11 C10 0.0(2) .
C15 C10 C11 C12 -1.60(19) .
C9 C10 C11 C12 175.46(12) .
C6 C1 C2 C3 -0.3(2) .
C4 C3 C2 C1 -0.3(2) .
C2 C3 C4 C5 0.6(2) .
C6 C5 C4 C3 -0.3(2) .
C10 C9 C7 C8 172.7(3) .
C8 C9 C7 C6 -178.0(3) .
C10 C9 C7 C6 -5.3(4) .
O1 C8 C7 C9 -177.7(3) .
O1 C8 C7 C6 0.3(4) .
C9 C8 C7 C6 178.0(2) .
C5 C6 C7 C9 174.9(2) .
C1 C6 C7 C9 -5.9(3) .
C5 C6 C7 C8 -1.7(3) .
C1 C6 C7 C8 177.56(19) .
C10 C15 C14 C13 -0.5(2) .
C15 C14 C13 C12 -1.1(2) .
C11 C12 C13 C14 1.4(2) .
O3 C16 C17 C17 10.6(2) 3_557
O2 C16 C17 C17 -169.37(14) 3_557
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196272
