#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/56/4505643.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_4505643
loop_
_publ_author_name
'Timofeeva, Tatiana V.'
'Kuhn, Genevieve H.'
'Nesterov, Volodymyr V.'
'Nesterov, Vladimir N.'
'Frazier, Donald O.'
'Penn, Benjamin G.'
'Antipin, Mikhail Yu.'
_publ_section_title
;
 Cocrystal of 1,1-Dicyano-2-(4-hydroxyphenyl)-ethene withl-Proline and
 Induced Conformational Polymorphism of 1,1-Dicyano-2-(4-hydroxy-
 3-methoxyphenyl)-ethene
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              383
_journal_paper_doi               10.1021/cg0200513
_journal_volume                  3
_journal_year                    2003
_chemical_formula_moiety         'C11 H8 N2 O2'
_chemical_formula_sum            'C11 H8 N2 O2'
_chemical_formula_weight         200.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   4.8360(10)
_cell_length_b                   13.042(3)
_cell_length_c                   32.438(7)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      11
_cell_volume                     2043.2(8)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4 (Enraf-Nonius, 1989)'
_computing_data_reduction        'Siemens SHELXTL (Sheldrick, 1994)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       θ/2θ
_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  0.2917
_diffrn_reflns_av_sigmaI/netI    0.2518
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            4941
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.3034
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0980P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.2358
_reflns_number_gt                1268
_reflns_number_total             4411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0200513_s3.cif
_cod_data_source_block           IIa
_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_cell_volume        2043.2(7)
_cod_database_code               4505643
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.3362(9) 0.9068(3) 0.18843(13) 0.0795(13) Uani 1 1 d .
O2 O 1.2951(7) 0.7655(3) 0.24658(12) 0.0644(10) Uani 1 1 d .
N1 N 0.7490(10) 0.4434(4) 0.24518(17) 0.0749(14) Uani 1 1 d .
N2 N 0.0892(9) 0.3998(4) 0.15098(15) 0.0731(14) Uani 1 1 d .
C1 C 0.7583(10) 0.6763(4) 0.16951(16) 0.0518(13) Uani 1 1 d .
C2 C 0.9296(9) 0.6791(4) 0.20592(15) 0.0522(13) Uani 1 1 d .
H2A H 0.9130 0.6281 0.2257 0.063 Uiso 1 1 calc R
C3 C 1.1186(9) 0.7550(4) 0.21266(15) 0.0489(13) Uani 1 1 d .
C4 C 1.1509(11) 0.8316(4) 0.18240(18) 0.0615(15) Uani 1 1 d .
C5 C 0.9888(13) 0.8282(5) 0.14671(19) 0.0780(18) Uani 1 1 d .
H5A H 1.0110 0.8774 0.1264 0.094 Uiso 1 1 calc R
C6 C 0.7961(12) 0.7538(5) 0.14066(18) 0.0692(16) Uani 1 1 d .
H6A H 0.6848 0.7542 0.1164 0.083 Uiso 1 1 calc R
C7 C 0.5542(10) 0.5999(4) 0.16014(16) 0.0557(14) Uani 1 1 d .
H7A H 0.4432 0.6132 0.1365 0.067 Uiso 1 1 calc R
C8 C 0.4923(9) 0.5113(4) 0.17943(15) 0.0507(13) Uani 1 1 d .
C9 C 0.6337(10) 0.4741(4) 0.21561(18) 0.0551(14) Uani 1 1 d .
C10 C 0.2675(11) 0.4481(4) 0.16380(16) 0.0593(15) Uani 1 1 d .
C11 C 1.2736(12) 0.6917(5) 0.27832(17) 0.0752(18) Uani 1 1 d .
H11A H 1.4094 0.7060 0.3002 0.113 Uiso 1 1 calc R
H11B H 1.3052 0.6245 0.2674 0.113 Uiso 1 1 calc R
H11C H 1.0918 0.6947 0.2888 0.113 Uiso 1 1 calc R
H1 H 1.459(9) 0.899(4) 0.2093(16) 0.057(16) Uiso 1 1 d .
O1' O 0.7174(7) 0.2309(3) 0.14099(12) 0.0663(11) Uani 1 1 d .
O2' O 0.5997(7) 0.3684(3) 0.08348(11) 0.0666(11) Uani 1 1 d .
N1' N -0.0516(12) 0.3490(4) -0.04413(19) 0.1007(19) Uani 1 1 d .
N2' N -0.6292(10) 0.1006(4) -0.05388(15) 0.0741(14) Uani 1 1 d .
C1' C 0.0992(9) 0.1663(4) 0.05211(15) 0.0489(13) Uani 1 1 d .
C2' C 0.2402(9) 0.2606(4) 0.05147(15) 0.0497(13) Uani 1 1 d .
H2'A H 0.1931 0.3091 0.0313 0.060 Uiso 1 1 calc R
C3' C 0.4472(10) 0.2806(4) 0.08079(16) 0.0496(13) Uani 1 1 d .
C4' C 0.5167(10) 0.2102(4) 0.11159(16) 0.0503(13) Uani 1 1 d .
C5' C 0.3793(10) 0.1181(4) 0.11249(16) 0.0594(14) Uani 1 1 d .
H5'A H 0.4283 0.0696 0.1326 0.071 Uiso 1 1 calc R
C6' C 0.1692(10) 0.0980(4) 0.08351(16) 0.0586(14) Uani 1 1 d .
H6'A H 0.0714 0.0368 0.0851 0.070 Uiso 1 1 calc R
C7' C -0.1208(9) 0.1379(4) 0.02285(16) 0.0549(14) Uani 1 1 d .
H7'A H -0.2100 0.0773 0.0294 0.066 Uiso 1 1 calc R
C8' C -0.2222(10) 0.1823(4) -0.01209(16) 0.0530(13) Uani 1 1 d .
C9' C -0.1229(12) 0.2748(5) -0.02937(17) 0.0642(16) Uani 1 1 d .
C10' C -0.4472(11) 0.1361(4) -0.03556(17) 0.0603(15) Uani 1 1 d .
C11' C 0.5381(14) 0.4482(4) 0.05481(19) 0.087(2) Uani 1 1 d .
H11D H 0.6689 0.5030 0.0592 0.131 Uiso 1 1 calc R
H11E H 0.3545 0.4734 0.0585 0.131 Uiso 1 1 calc R
H11F H 0.5492 0.4224 0.0272 0.131 Uiso 1 1 calc R
H1' H 0.776(16) 0.305(7) 0.134(3) 0.17(4) 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'
N N 0.0061 0.0033 '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
C3 O2 C11 116.9(4)
C6 C1 C2 116.9(5)
C6 C1 C7 118.5(5)
C2 C1 C7 124.7(5)
C3 C2 C1 121.1(5)
C2 C3 O2 126.3(5)
C2 C3 C4 120.0(5)
O2 C3 C4 113.7(4)
O1 C4 C5 120.0(5)
O1 C4 C3 120.9(5)
C5 C4 C3 119.1(5)
C6 C5 C4 120.5(5)
C5 C6 C1 122.4(5)
C8 C7 C1 131.7(5)
C7 C8 C9 124.6(4)
C7 C8 C10 120.5(4)
C9 C8 C10 114.9(5)
N1 C9 C8 179.8(6)
N2 C10 C8 178.7(6)
C3' O2' C11' 118.7(4)
C6' C1' C2' 118.3(5)
C6' C1' C7' 117.7(5)
C2' C1' C7' 123.9(5)
C3' C2' C1' 119.6(5)
O2' C3' C2' 125.3(5)
O2' C3' C4' 113.6(4)
C2' C3' C4' 121.1(5)
O1' C4' C5' 119.3(5)
O1' C4' C3' 121.0(5)
C5' C4' C3' 119.7(5)
C6' C5' C4' 119.6(5)
C5' C6' C1' 121.7(5)
C8' C7' C1' 132.2(5)
C7' C8' C9' 125.6(5)
C7' C8' C10' 120.2(5)
C9' C8' C10' 114.3(5)
N1' C9' C8' 177.6(7)
N2' C10' C8' 178.7(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.336(6)
O2 C3 1.364(6)
O2 C11 1.417(6)
N1 C9 1.156(6)
N2 C10 1.129(6)
C1 C6 1.395(7)
C1 C2 1.408(6)
C1 C7 1.424(7)
C2 C3 1.357(6)
C3 C4 1.415(7)
C4 C5 1.365(7)
C5 C6 1.353(7)
C7 C8 1.354(7)
C8 C9 1.413(8)
C8 C10 1.436(7)
O1' C4' 1.352(5)
O2' C3' 1.363(5)
O2' C11' 1.417(6)
N1' C9' 1.141(7)
N2' C10' 1.135(6)
C1' C6' 1.382(7)
C1' C2' 1.407(6)
C1' C7' 1.438(6)
C2' C3' 1.370(7)
C3' C4' 1.385(7)
C4' C5' 1.375(7)
C5' C6' 1.374(7)
C7' C8' 1.343(6)
C8' C9' 1.424(8)
C8' C10' 1.429(7)
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
C6 C1 C2 C3 1.1(7)
C7 C1 C2 C3 -179.6(5)
C1 C2 C3 O2 -179.9(4)
C1 C2 C3 C4 -1.6(8)
C11 O2 C3 C2 -1.9(7)
C11 O2 C3 C4 179.6(4)
C2 C3 C4 O1 -179.9(5)
O2 C3 C4 O1 -1.3(7)
C2 C3 C4 C5 0.3(8)
O2 C3 C4 C5 178.9(5)
O1 C4 C5 C6 -178.5(6)
C3 C4 C5 C6 1.3(9)
C4 C5 C6 C1 -1.8(10)
C2 C1 C6 C5 0.6(8)
C7 C1 C6 C5 -178.7(6)
C6 C1 C7 C8 171.9(5)
C2 C1 C7 C8 -7.3(9)
C1 C7 C8 C9 -0.7(9)
C1 C7 C8 C10 178.5(5)
C7 C8 C9 N1 -164(100)
C10 C8 C9 N1 17(100)
C7 C8 C10 N2 -8(30)
C9 C8 C10 N2 171(100)
C6' C1' C2' C3' 2.2(7)
C7' C1' C2' C3' 179.9(5)
C11' O2' C3' C2' 2.1(7)
C11' O2' C3' C4' -177.0(5)
C1' C2' C3' O2' 179.7(4)
C1' C2' C3' C4' -1.3(7)
O2' C3' C4' O1' 0.4(7)
C2' C3' C4' O1' -178.7(4)
O2' C3' C4' C5' -179.8(5)
C2' C3' C4' C5' 1.1(8)
O1' C4' C5' C6' 177.9(5)
C3' C4' C5' C6' -1.8(8)
C4' C5' C6' C1' 2.9(8)
C2' C1' C6' C5' -3.1(8)
C7' C1' C6' C5' 179.1(5)
C6' C1' C7' C8' -174.2(5)
C2' C1' C7' C8' 8.1(8)
C1' C7' C8' C9' 0.6(9)
C1' C7' C8' C10' 180.0(5)
C7' C8' C9' N1' -168(16)
C10' C8' C9' N1' 13(17)
C7' C8' C10' N2' 100(32)
C9' C8' C10' N2' -81(32)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145859
