#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:35:05 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301870 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/21/7242144.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_7242144
loop_
_publ_author_name
'Gorginpour, Forough'
'Zali-Boeini, Hassan'
'Rudbari, Hadi Amiri'
_publ_section_title
;
 A quinoxaline-based porous organic polymer containing copper
 nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C--N coupling
 reaction
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3655
_journal_page_last               3665
_journal_paper_doi               10.1039/D0RA10741G
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-09-16 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.05(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7420(19)
_cell_length_b                   16.082(3)
_cell_length_c                   11.405(2)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      48.33
_cell_measurement_theta_min      5.04
_cell_volume                     1618.8(7)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1897
_diffrn_reflns_av_unetI/netI     0.1456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.533
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       flat
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0721
_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)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1394
_reflns_number_total             2860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra10741g2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1618.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242144
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
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_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 -0.2149(2) 0.05199(18) 0.8554(2) 0.0642(7) Uani 1 1 d . . . . .
H1 H -0.301027 0.039467 0.844630 0.096 Uiso 1 1 calc R U . . .
O2 O 0.4965(2) 0.02753(18) 0.8316(3) 0.0632(7) Uani 1 1 d D . . . .
N1 N 0.2882(3) 0.11315(17) 0.8407(3) 0.0524(7) Uani 1 1 d . . . . .
C8 C 0.2161(3) 0.0478(2) 0.8506(3) 0.0436(8) Uani 1 1 d . . . . .
C7 C 0.0698(3) 0.0571(2) 0.8676(3) 0.0442(8) Uani 1 1 d . . . . .
H7 H 0.056023 0.007226 0.910744 0.053 Uiso 1 1 calc R U . . .
C1 C -0.0671(3) 0.06612(19) 0.7376(3) 0.0428(8) Uani 1 1 d . . . . .
C9 C 0.2790(3) -0.0338(2) 0.8456(3) 0.0482(8) Uani 1 1 d . . . . .
N2 N 0.0931(3) 0.12841(18) 0.9542(3) 0.0532(8) Uani 1 1 d . . . . .
C3 C -0.3402(4) 0.0742(2) 0.6241(3) 0.0578(9) Uani 1 1 d . . . . .
H3 H -0.435345 0.072868 0.624672 0.069 Uiso 1 1 calc R U . . .
C2 C -0.2119(3) 0.0641(2) 0.7387(3) 0.0477(8) Uani 1 1 d . . . . .
C6 C -0.0589(3) 0.0783(2) 0.6204(3) 0.0514(9) Uani 1 1 d . . . . .
H6 H 0.035743 0.079744 0.618819 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2398(3) 0.1923(2) 0.8572(3) 0.0521(8) Uani 1 1 d . . . . .
C13 C 0.4839(4) -0.1183(3) 0.8441(3) 0.0647(10) Uani 1 1 d . . . . .
H13 H 0.579494 -0.122422 0.844795 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4215(4) -0.0409(2) 0.8393(3) 0.0528(9) Uani 1 1 d . . . . .
C10 C 0.2028(4) -0.1077(2) 0.8481(3) 0.0579(9) Uani 1 1 d . . . . .
H10 H 0.107737 -0.104622 0.848615 0.069 Uiso 1 1 calc R U . . .
C20 C 0.1424(3) 0.2012(2) 0.9187(3) 0.0499(8) Uani 1 1 d . . . . .
C4 C -0.3283(4) 0.0860(2) 0.5100(4) 0.0640(10) Uani 1 1 d . . . . .
H4 H -0.415603 0.092554 0.433659 0.077 Uiso 1 1 calc R U . . .
C5 C -0.1861(4) 0.0884(3) 0.5068(3) 0.0630(10) Uani 1 1 d . . . . .
H5 H -0.178179 0.096605 0.429153 0.076 Uiso 1 1 calc R U . . .
C16 C 0.2974(4) 0.2628(3) 0.8233(4) 0.0731(12) Uani 1 1 d . . . . .
H16 H 0.361046 0.257315 0.781814 0.088 Uiso 1 1 calc R U . . .
C12 C 0.4087(5) -0.1894(3) 0.8479(4) 0.0744(11) Uani 1 1 d . . . . .
H12 H 0.452198 -0.241041 0.849304 0.089 Uiso 1 1 calc R U . . .
C19 C 0.1122(4) 0.2793(3) 0.9509(4) 0.0719(11) Uani 1 1 d . . . . .
H19 H 0.052764 0.285473 0.996181 0.086 Uiso 1 1 calc R U . . .
C11 C 0.2660(5) -0.1842(2) 0.8498(4) 0.0746(11) Uani 1 1 d . . . . .
H11 H 0.214401 -0.232357 0.852096 0.090 Uiso 1 1 calc R U . . .
C18 C 0.1699(5) 0.3484(3) 0.9162(4) 0.0830(14) Uani 1 1 d . . . . .
H18 H 0.147779 0.401114 0.936867 0.100 Uiso 1 1 calc R U . . .
C17 C 0.2607(5) 0.3400(3) 0.8507(5) 0.0849(14) Uani 1 1 d . . . . .
H17 H 0.296702 0.387004 0.825383 0.102 Uiso 1 1 calc R U . . .
H2A H 0.014(5) 0.143(2) 0.983(4) 0.085(13) Uiso 1 1 d . . . . .
H2 H 0.454(4) 0.0725(13) 0.826(4) 0.087(15) Uiso 1 1 d 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C14 O2 H2 117(3) . . ?
C8 N1 C15 120.1(3) . . ?
N1 C8 C9 118.3(3) . . ?
N1 C8 C7 120.1(3) . . ?
C9 C8 C7 121.6(3) . . ?
N2 C7 C1 113.8(3) . . ?
N2 C7 C8 106.0(2) . . ?
C1 C7 C8 111.5(2) . . ?
N2 C7 H7 108.5 . . ?
C1 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C6 C1 C2 118.4(3) . . ?
C6 C1 C7 124.5(3) . . ?
C2 C1 C7 117.0(3) . . ?
C10 C9 C14 117.8(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 120.6(3) . . ?
C20 N2 C7 115.9(3) . . ?
C20 N2 H2A 108(2) . . ?
C7 N2 H2A 119(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C2 C3 123.9(3) . . ?
O1 C2 C1 116.5(3) . . ?
C3 C2 C1 119.6(3) . . ?
C5 C6 C1 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C16 C15 N1 120.4(3) . . ?
C16 C15 C20 119.5(3) . . ?
N1 C15 C20 119.8(3) . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O2 C14 C13 120.0(3) . . ?
O2 C14 C9 120.4(3) . . ?
C13 C14 C9 119.6(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C19 C20 N2 123.6(3) . . ?
C19 C20 C15 119.5(3) . . ?
N2 C20 C15 116.7(3) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
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 C2 1.358(4) . ?
O1 H1 0.8200 . ?
O2 C14 1.345(4) . ?
O2 H2 0.821(2) . ?
N1 C8 1.295(4) . ?
N1 C15 1.397(4) . ?
C8 C9 1.460(4) . ?
C8 C7 1.525(4) . ?
C7 N2 1.467(4) . ?
C7 C1 1.524(4) . ?
C7 H7 0.9800 . ?
C1 C6 1.387(4) . ?
C1 C2 1.416(4) . ?
C9 C10 1.408(5) . ?
C9 C14 1.425(4) . ?
N2 C20 1.388(4) . ?
N2 H2A 0.99(4) . ?
C3 C4 1.368(5) . ?
C3 C2 1.383(5) . ?
C3 H3 0.9300 . ?
C6 C5 1.372(5) . ?
C6 H6 0.9300 . ?
C15 C16 1.391(5) . ?
C15 C20 1.406(5) . ?
C13 C12 1.368(6) . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C20 C19 1.375(5) . ?
C4 C5 1.402(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C17 1.364(6) . ?
C16 H16 0.9300 . ?
C12 C11 1.402(6) . ?
C12 H12 0.9300 . ?
C19 C18 1.377(6) . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C18 C17 1.384(6) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
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
C15 N1 C8 C9 -174.0(3) . . . . ?
C15 N1 C8 C7 5.7(5) . . . . ?
N1 C8 C7 N2 -38.7(4) . . . . ?
C9 C8 C7 N2 141.0(3) . . . . ?
N1 C8 C7 C1 85.6(4) . . . . ?
C9 C8 C7 C1 -94.7(3) . . . . ?
N2 C7 C1 C6 109.7(3) . . . . ?
C8 C7 C1 C6 -10.1(5) . . . . ?
N2 C7 C1 C2 -68.4(4) . . . . ?
C8 C7 C1 C2 171.8(3) . . . . ?
N1 C8 C9 C10 -176.3(3) . . . . ?
C7 C8 C9 C10 4.0(5) . . . . ?
N1 C8 C9 C14 4.4(5) . . . . ?
C7 C8 C9 C14 -175.3(3) . . . . ?
C1 C7 N2 C20 -70.8(3) . . . . ?
C8 C7 N2 C20 52.1(3) . . . . ?
C4 C3 C2 O1 -179.9(3) . . . . ?
C4 C3 C2 C1 0.0(5) . . . . ?
C6 C1 C2 O1 180.0(3) . . . . ?
C7 C1 C2 O1 -1.8(4) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C7 C1 C2 C3 178.3(3) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C7 C1 C6 C5 -178.1(3) . . . . ?
C8 N1 C15 C16 -167.8(3) . . . . ?
C8 N1 C15 C20 17.7(5) . . . . ?
C12 C13 C14 O2 -177.9(4) . . . . ?
C12 C13 C14 C9 3.5(6) . . . . ?
C10 C9 C14 O2 177.4(3) . . . . ?
C8 C9 C14 O2 -3.2(5) . . . . ?
C10 C9 C14 C13 -4.1(5) . . . . ?
C8 C9 C14 C13 175.3(3) . . . . ?
C14 C9 C10 C11 2.6(5) . . . . ?
C8 C9 C10 C11 -176.8(3) . . . . ?
C7 N2 C20 C19 152.1(3) . . . . ?
C7 N2 C20 C15 -33.9(4) . . . . ?
C16 C15 C20 C19 -3.6(5) . . . . ?
N1 C15 C20 C19 170.9(3) . . . . ?
C16 C15 C20 N2 -177.8(3) . . . . ?
N1 C15 C20 N2 -3.3(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
N1 C15 C16 C17 -173.9(4) . . . . ?
C20 C15 C16 C17 0.6(6) . . . . ?
C14 C13 C12 C11 -1.4(6) . . . . ?
N2 C20 C19 C18 177.6(3) . . . . ?
C15 C20 C19 C18 3.8(5) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C13 C12 C11 C10 -0.2(6) . . . . ?
C20 C19 C18 C17 -1.1(6) . . . . ?
C15 C16 C17 C18 2.1(7) . . . . ?
C19 C18 C17 C16 -1.9(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341945
