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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/41/7104182.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_7104182
loop_
_publ_author_name
'Friscić, Tomislav'
'Macgillivray, Leonard R'
_publ_section_title
;
 Engineering cocrystal and polymorph architecture via pseudoseeding.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              773
_journal_page_last               775
_journal_paper_doi               10.1039/b820120j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_common
'resorcinol . trans-1,2-bis(4-pyridyl)ethylene 1/2 form 2'
_chemical_name_systematic
;
resorcinol . trans-1,2-bis(4-pyridyl)ethylene 1/2 form 2
;
_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                 94.797(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1465(10)
_cell_length_b                   7.1871(7)
_cell_length_c                   20.042(2)
_cell_measurement_reflns_used    5565
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1456.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10675
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.2458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                2314
_reflns_number_total             3342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820120j.txt
_cod_data_source_block           (RES).(4,4'-BPE)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7104182
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93157(11) 0.62071(16) 0.55378(5) 0.0367(3) Uani 1 1 d . . .
H1 H 1.0081 0.6658 0.5547 0.055 Uiso 1 1 calc R . .
O2 O 0.54331(10) 0.64940(17) 0.66535(5) 0.0365(3) Uani 1 1 d . . .
H2 H 0.5158 0.6725 0.7029 0.055 Uiso 1 1 calc R . .
N1 N 1.17087(13) 0.78252(19) 0.53137(7) 0.0359(4) Uani 1 1 d . . .
N2 N 1.90742(13) 0.80203(18) 0.27599(6) 0.0306(3) Uani 1 1 d . . .
C1 C 1.15543(16) 0.8645(2) 0.47144(8) 0.0351(4) Uani 1 1 d . . .
H1A H 1.0700 0.9093 0.4564 0.042 Uiso 1 1 calc R . .
C2 C 1.25633(16) 0.8879(2) 0.42998(8) 0.0322(4) Uani 1 1 d . . .
H2A H 1.2393 0.9460 0.3876 0.039 Uiso 1 1 calc R . .
C3 C 1.38310(15) 0.8260(2) 0.45078(7) 0.0270(3) Uani 1 1 d . . .
C4 C 1.40052(15) 0.7460(2) 0.51444(8) 0.0311(4) Uani 1 1 d . . .
H4 H 1.4856 0.7049 0.5318 0.037 Uiso 1 1 calc R . .
C5 C 1.29377(16) 0.7271(2) 0.55186(8) 0.0340(4) Uani 1 1 d . . .
H5 H 1.3080 0.6713 0.5948 0.041 Uiso 1 1 calc R . .
C6 C 1.48813(15) 0.8438(2) 0.40523(8) 0.0304(4) Uani 1 1 d . . .
H6 H 1.4646 0.9011 0.3632 0.036 Uiso 1 1 calc R . .
C7 C 1.61244(16) 0.7883(2) 0.41650(8) 0.0301(4) Uani 1 1 d . . .
H7 H 1.6383 0.7370 0.4593 0.036 Uiso 1 1 calc R . .
C8 C 1.71357(15) 0.7994(2) 0.36855(7) 0.0272(3) Uani 1 1 d . . .
C9 C 1.69199(16) 0.8870(2) 0.30627(8) 0.0330(4) Uani 1 1 d . . .
H9 H 1.6104 0.9478 0.2941 0.040 Uiso 1 1 calc R . .
C10 C 1.78984(16) 0.8842(2) 0.26286(8) 0.0336(4) Uani 1 1 d . . .
H10 H 1.7729 0.9445 0.2208 0.040 Uiso 1 1 calc R . .
C11 C 1.83691(15) 0.7178(2) 0.38301(8) 0.0302(4) Uani 1 1 d . . .
H11 H 1.8578 0.6597 0.4251 0.036 Uiso 1 1 calc R . .
C12 C 1.92905(15) 0.7214(2) 0.33612(8) 0.0307(4) Uani 1 1 d . . .
H12 H 2.0122 0.6636 0.3471 0.037 Uiso 1 1 calc R . .
C13 C 0.87414(15) 0.6729(2) 0.61015(7) 0.0268(3) Uani 1 1 d . . .
C14 C 0.74121(14) 0.6320(2) 0.61256(7) 0.0268(3) Uani 1 1 d . . .
H14 H 0.6950 0.5669 0.5766 0.032 Uiso 1 1 calc R . .
C15 C 0.67528(15) 0.6861(2) 0.66745(7) 0.0271(4) Uani 1 1 d . . .
C16 C 0.74410(16) 0.7756(2) 0.72111(8) 0.0321(4) Uani 1 1 d . . .
H16 H 0.7001 0.8120 0.7590 0.039 Uiso 1 1 calc R . .
C17 C 0.87771(16) 0.8109(2) 0.71850(8) 0.0344(4) Uani 1 1 d . . .
H17 H 0.9252 0.8701 0.7555 0.041 Uiso 1 1 calc R . .
C18 C 0.94389(15) 0.7623(2) 0.66353(8) 0.0318(4) Uani 1 1 d . . .
H18 H 1.0353 0.7895 0.6623 0.038 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.29(14) . . ?
C10 N2 C12 116.40(13) . . ?
N1 C1 C2 123.89(15) . . ?
C1 C2 C3 119.58(15) . . ?
C2 C3 C4 116.64(14) . . ?
C2 C3 C6 119.18(14) . . ?
C4 C3 C6 124.17(14) . . ?
C5 C4 C3 119.57(15) . . ?
N1 C5 C4 123.97(15) . . ?
C7 C6 C3 126.83(15) . . ?
C6 C7 C8 125.52(15) . . ?
C11 C8 C9 116.53(14) . . ?
C11 C8 C7 120.52(14) . . ?
C9 C8 C7 122.94(14) . . ?
C10 C9 C8 119.42(15) . . ?
N2 C10 C9 124.17(15) . . ?
C12 C11 C8 119.96(14) . . ?
N2 C12 C11 123.48(14) . . ?
O1 C13 C14 117.04(13) . . ?
O1 C13 C18 122.58(14) . . ?
C14 C13 C18 120.38(14) . . ?
C13 C14 C15 120.19(14) . . ?
O2 C15 C14 117.28(13) . . ?
O2 C15 C16 122.85(14) . . ?
C14 C15 C16 119.86(14) . . ?
C17 C16 C15 119.05(15) . . ?
C18 C17 C16 121.76(15) . . ?
C17 C18 C13 118.71(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.3662(18) . ?
O2 C15 1.3620(17) . ?
N1 C1 1.335(2) . ?
N1 C5 1.340(2) . ?
N2 C10 1.337(2) . ?
N2 C12 1.339(2) . ?
C1 C2 1.382(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.397(2) . ?
C3 C6 1.466(2) . ?
C4 C5 1.375(2) . ?
C6 C7 1.324(2) . ?
C7 C8 1.466(2) . ?
C8 C11 1.390(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.374(2) . ?
C11 C12 1.380(2) . ?
C13 C14 1.385(2) . ?
C13 C18 1.390(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.382(2) . ?
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
_geom_torsion_publ_flag
C5 N1 C1 C2 2.3(2) . . . . ?
N1 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C1 C2 C3 C6 177.24(14) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C6 C3 C4 C5 -176.57(15) . . . . ?
C1 N1 C5 C4 -1.6(2) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C2 C3 C6 C7 -178.33(15) . . . . ?
C4 C3 C6 C7 0.2(3) . . . . ?
C3 C6 C7 C8 176.64(14) . . . . ?
C6 C7 C8 C11 -172.69(16) . . . . ?
C6 C7 C8 C9 6.0(3) . . . . ?
C11 C8 C9 C10 1.6(2) . . . . ?
C7 C8 C9 C10 -177.09(15) . . . . ?
C12 N2 C10 C9 -1.2(2) . . . . ?
C8 C9 C10 N2 -0.1(3) . . . . ?
C9 C8 C11 C12 -1.9(2) . . . . ?
C7 C8 C11 C12 176.86(14) . . . . ?
C10 N2 C12 C11 0.9(2) . . . . ?
C8 C11 C12 N2 0.6(2) . . . . ?
O1 C13 C14 C15 -178.00(13) . . . . ?
C18 C13 C14 C15 2.3(2) . . . . ?
C13 C14 C15 O2 177.04(13) . . . . ?
C13 C14 C15 C16 -2.3(2) . . . . ?
O2 C15 C16 C17 -178.68(14) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
C16 C17 C18 C13 -1.1(2) . . . . ?
O1 C13 C18 C17 179.70(14) . . . . ?
C14 C13 C18 C17 -0.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653103
2 PubChem 139091077
