#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218936.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_7218936
loop_
_publ_author_name
'Harvey, Benjamin G.'
'Guenthner, Andrew J.'
'Meylemans, Heather A.'
'Haines, Shannon R. L.'
'Lamison, Kevin R.'
'Groshens, Thomas J.'
'Cambrea, Lee R.'
'Davis, Matthew C.'
'Lai, William W.'
_publ_section_title
;
 Renewable thermosetting resins and thermoplastics from vanillin
;
_journal_issue                   2
_journal_name_full               'Green Chem.'
_journal_page_first              1249
_journal_paper_doi               10.1039/C4GC01825G
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C18 H16 N2 O4'
_chemical_formula_sum            'C18 H16 N2 O4'
_chemical_formula_weight         324.33
_chemical_name_systematic        1,2-bis(4-cyanato-3-methoxyphenyl)ethane
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_update_record
;
2014-08-28 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.4010(3)
_cell_length_b                   12.3035(9)
_cell_length_c                   14.8314(11)
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.4504
_cell_measurement_theta_min      2.1585
_cell_volume                     796.04(10)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8545
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0350
_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/[σ²(Fo²)+(0.0423P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1097
_reflns_number_total             1399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4gc01825g2.cif
_cod_data_source_block           Compound_7
_cod_depositor_comments
'Adding full bibliography for 7218936--7218937.cif.'
_cod_database_code               7218936
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
O O2 0.5097(3) 0.22252(9) 0.78085(8) 0.0659(4) Uani d . . 1
O O1 0.7308(3) 0.13433(8) 0.64666(8) 0.0629(4) Uani d . . 1
N N1 0.2845(4) 0.28935(14) 0.90921(11) 0.0852(6) Uani d . . 1
C C9 0.3943(4) 0.26189(13) 0.84860(11) 0.0565(4) Uani d . . 1
C C5 0.6558(3) 0.29462(12) 0.72454(10) 0.0453(4) Uani d . . 1
C C4 0.7713(3) 0.24374(12) 0.65310(10) 0.0442(4) Uani d . . 1
C C3 0.9177(3) 0.30816(12) 0.59556(10) 0.0452(4) Uani d . . 1
H H3 0.9961 0.2762 0.5467 0.054 Uiso calc U R 1
C C2 0.9499(3) 0.41944(12) 0.60933(9) 0.0430(4) Uani d . . 1
C C1 1.1051(4) 0.48672(13) 0.54338(10) 0.0509(4) Uani d . . 1
H H1 1.2821 0.4474 0.5279 0.061 Uiso calc U R 1
H H2 1.1775 0.554 0.5728 0.061 Uiso calc U R 1
C C7 0.8328(3) 0.46621(12) 0.68193(10) 0.0490(4) Uani d . . 1
H H5 0.855 0.5406 0.692 0.059 Uiso calc U R 1
C C6 0.6821(4) 0.40362(13) 0.74009(10) 0.0501(4) Uani d . . 1
H H4 0.601 0.4354 0.7886 0.06 Uiso calc U R 1
C C8 0.8705(5) 0.07989(14) 0.57788(13) 0.0696(5) Uani d . . 1
H H7 0.7829 0.1059 0.5191 0.104 Uiso calc U R 1
H H8 0.8357 0.0031 0.5817 0.104 Uiso calc U R 1
H H6 1.0869 0.094 0.5865 0.104 Uiso calc U R 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C9 O2 C5 . . 118.70(12)
C4 O1 C8 . . 116.78(12)
N1 C9 O2 . . 175.05(19)
C6 C5 C4 . . 122.89(13)
C6 C5 O2 . . 123.16(13)
C4 C5 O2 . . 113.95(13)
O1 C4 C5 . . 116.35(12)
O1 C4 C3 . . 126.21(13)
C5 C4 C3 . . 117.44(14)
C4 C3 C2 . . 121.37(13)
C4 C3 H3 . . 119.3
C2 C3 H3 . . 119.3
C7 C2 C3 . . 118.98(13)
C7 C2 C1 . . 121.60(14)
C3 C2 C1 . . 119.40(13)
C2 C1 C1 . 3_766 112.95(15)
C2 C1 H1 . . 109.0
C1 C1 H1 3_766 . 109.0
C2 C1 H2 . . 109.0
C1 C1 H2 3_766 . 109.0
H1 C1 H2 . . 107.8
C2 C7 C6 . . 120.80(14)
C2 C7 H5 . . 119.6
C6 C7 H5 . . 119.6
C5 C6 C7 . . 118.52(14)
C5 C6 H4 . . 120.7
C7 C6 H4 . . 120.7
O1 C8 H7 . . 109.5
O1 C8 H8 . . 109.5
H7 C8 H8 . . 109.5
O1 C8 H6 . . 109.5
H7 C8 H6 . . 109.5
H8 C8 H6 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O2 C9 . 1.2797(18)
O2 C5 . 1.4282(16)
O1 C4 . 1.3596(17)
O1 C8 . 1.4257(19)
N1 C9 . 1.127(2)
C5 C6 . 1.363(2)
C5 C4 . 1.3838(19)
C4 C3 . 1.3845(19)
C3 C2 . 1.389(2)
C3 H3 . 0.93
C2 C7 . 1.380(2)
C2 C1 . 1.5114(19)
C1 C1 3_766 1.518(3)
C1 H1 . 0.97
C1 H2 . 0.97
C7 C6 . 1.388(2)
C7 H5 . 0.93
C6 H4 . 0.93
C8 H7 . 0.96
C8 H8 . 0.96
C8 H6 . 0.96
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
C3 H3 N1 4_665 0.93 2.67 3.587(2) 170.9
C8 H8 N1 2_646 0.96 2.69 3.649(2) 177.8
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_site_symmetry_4
_geom_torsion
C9 O2 C5 C6 . 0.9(2)
C9 O2 C5 C4 . -179.71(15)
C8 O1 C4 C5 . -175.03(15)
C8 O1 C4 C3 . 4.6(2)
C6 C5 C4 O1 . 179.31(15)
O2 C5 C4 O1 . -0.1(2)
C6 C5 C4 C3 . -0.3(2)
O2 C5 C4 C3 . -179.73(13)
O1 C4 C3 C2 . -179.07(15)
C5 C4 C3 C2 . 0.5(2)
C4 C3 C2 C7 . -0.1(2)
C4 C3 C2 C1 . -178.58(14)
C7 C2 C1 C1 3_766 -98.7(2)
C3 C2 C1 C1 3_766 79.8(2)
C3 C2 C7 C6 . -0.6(2)
C1 C2 C7 C6 . 177.87(14)
C4 C5 C6 C7 . -0.3(2)
O2 C5 C6 C7 . 179.03(14)
C2 C7 C6 C5 . 0.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 121360802
