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#$Date: 2022-05-11 11:07:33 +0300 (Wed, 11 May 2022) $
#$Revision: 275327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105214.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_8105214
loop_
_publ_author_name
'Li, Pei-Xuan'
'Hui, Wei'
'Jing, Qin-Qin'
_publ_section_title
;
 Crystal structure of methyl
 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate,
 C26H17N5O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              315
_journal_page_last               317
_journal_paper_doi               10.1515/ncrs-2022-0013
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C26 H17 N5 O4'
_chemical_formula_sum            'C26 H17 N5 O4'
_chemical_formula_weight         463.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                104.532(2)
_cell_angle_beta                 96.312(2)
_cell_angle_gamma                112.398(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9297(12)
_cell_length_b                   10.9926(15)
_cell_length_c                   12.6758(18)
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.25
_cell_volume                     1083.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7604
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.705
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0398
_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)+(0.0700P)²+0.0760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2865
_reflns_number_total             3800
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0013_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105214
_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.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.2075(3) 0.9636(2) 0.48804(17) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.2247(3) 0.85162(19) 0.52004(16) 0.0384(5) Uani 1 1 d . . . . .
C3 C 0.1096(3) 0.7784(2) 0.57219(16) 0.0409(5) Uani 1 1 d . . . . .
H3 H 0.0218 0.8009 0.5863 0.049 Uiso 1 1 calc R U . . .
C4 C 0.1272(2) 0.6717(2) 0.60290(16) 0.0399(5) Uani 1 1 d . . . . .
H4 H 0.0517 0.6233 0.6391 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2565(2) 0.63591(19) 0.58034(15) 0.0338(4) Uani 1 1 d . . . . .
C6 C 0.3689(2) 0.7075(2) 0.52555(16) 0.0398(5) Uani 1 1 d . . . . .
H6 H 0.4535 0.6820 0.5081 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3545(3) 0.8161(2) 0.49726(16) 0.0421(5) Uani 1 1 d . . . . .
H7 H 0.4317 0.8659 0.4628 0.050 Uiso 1 1 calc R U . . .
C8 C 0.2721(2) 0.5168(2) 0.60996(16) 0.0352(4) Uani 1 1 d . . . . .
C9 C 0.2368(2) 0.41242(18) 0.76391(15) 0.0306(4) Uani 1 1 d . . . . .
C10 C 0.2532(3) 0.4488(2) 0.87935(16) 0.0390(5) Uani 1 1 d . . . . .
H10 H 0.2806 0.5402 0.9207 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2291(3) 0.35066(19) 0.93276(16) 0.0386(5) Uani 1 1 d . . . . .
H11 H 0.2416 0.3764 1.0100 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1865(2) 0.21431(18) 0.87256(15) 0.0299(4) Uani 1 1 d . . . . .
C13 C 0.1700(2) 0.17780(18) 0.75761(15) 0.0308(4) Uani 1 1 d . . . . .
H13 H 0.1401 0.0858 0.7165 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1974(2) 0.27580(18) 0.70327(15) 0.0309(4) Uani 1 1 d . . . . .
H14 H 0.1894 0.2505 0.6264 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2079(2) 0.01272(18) 0.91373(14) 0.0285(4) Uani 1 1 d . . . . .
C16 C 0.1607(2) -0.20249(19) 0.93002(15) 0.0363(5) Uani 1 1 d . . . . .
H16 H 0.0955 -0.2762 0.9522 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3759(2) -0.10197(19) 0.86383(14) 0.0312(4) Uani 1 1 d . . . . .
C18 C 0.3500(2) 0.01644(18) 0.87303(14) 0.0273(4) Uani 1 1 d . . . . .
C19 C 0.4905(2) 0.10971(18) 0.83988(14) 0.0289(4) Uani 1 1 d . . . . .
C20 C 0.5858(2) 0.03535(19) 0.81361(15) 0.0338(4) Uani 1 1 d . . . . .
C21 C 0.7340(2) 0.0853(2) 0.78159(17) 0.0419(5) Uani 1 1 d . . . . .
H21 H 0.7941 0.0326 0.7659 0.050 Uiso 1 1 calc R U . . .
C22 C 0.7884(2) 0.2173(2) 0.77403(16) 0.0419(5) Uani 1 1 d . . . . .
H22 H 0.8884 0.2553 0.7532 0.050 Uiso 1 1 calc R U . . .
C23 C 0.6967(2) 0.2958(2) 0.79697(15) 0.0352(5) Uani 1 1 d . . . . .
C24 C 0.5483(2) 0.24295(19) 0.83136(14) 0.0310(4) Uani 1 1 d . . . . .
H24 H 0.4889 0.2960 0.8483 0.037 Uiso 1 1 calc R U . . .
C25 C 0.7596(2) 0.4320(2) 0.77734(16) 0.0407(5) Uani 1 1 d . . . . .
C26 C 0.6936(3) 0.6120(2) 0.7482(2) 0.0580(6) Uani 1 1 d . . . . .
H26A H 0.8013 0.6784 0.7937 0.087 Uiso 1 1 calc R U . . .
H26B H 0.6130 0.6483 0.7622 0.087 Uiso 1 1 calc R U . . .
H26C H 0.6971 0.5940 0.6706 0.087 Uiso 1 1 calc R U . . .
N1 N 0.1922(3) 1.0516(2) 0.46162(16) 0.0588(5) Uani 1 1 d . . . . .
N2 N 0.2515(2) 0.51604(15) 0.71448(13) 0.0361(4) Uani 1 1 d . . . . .
H2 H 0.2468 0.5890 0.7560 0.043 Uiso 1 1 calc R U . . .
N3 N 0.15244(19) 0.11254(15) 0.92789(13) 0.0363(4) Uani 1 1 d . . . . .
H3A H 0.0904 0.1148 0.9750 0.044 Uiso 1 1 calc R U . . .
N4 N 0.11724(18) -0.09785(15) 0.94456(13) 0.0326(4) Uani 1 1 d . . . . .
N5 N 0.2863(2) -0.21529(16) 0.88753(13) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.30078(19) 0.42996(15) 0.54474(12) 0.0510(4) Uani 1 1 d . . . . .
O2 O 0.51634(16) -0.09451(13) 0.82680(11) 0.0377(3) Uani 1 1 d . . . . .
O3 O 0.89676(19) 0.49024(17) 0.76328(16) 0.0688(5) Uani 1 1 d . . . . .
O4 O 0.64762(17) 0.48432(14) 0.77534(12) 0.0472(4) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 179.2(2) . .
C3 C2 C7 120.26(18) . .
C3 C2 C1 119.49(19) . .
C7 C2 C1 120.24(18) . .
C4 C3 C2 119.20(19) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 120.70(18) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C4 C5 C6 119.75(18) . .
C4 C5 C8 120.72(17) . .
C6 C5 C8 119.47(18) . .
C7 C6 C5 119.8(2) . .
C7 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C6 C7 C2 120.26(18) . .
C6 C7 H7 119.9 . .
C2 C7 H7 119.9 . .
O1 C8 N2 124.39(18) . .
O1 C8 C5 122.05(17) . .
N2 C8 C5 113.57(17) . .
C14 C9 C10 119.14(16) . .
C14 C9 N2 123.54(16) . .
C10 C9 N2 117.20(16) . .
C11 C10 C9 120.57(17) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C10 C11 C12 120.46(18) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C11 C12 C13 119.10(16) . .
C11 C12 N3 119.86(17) . .
C13 C12 N3 120.98(16) . .
C14 C13 C12 121.03(17) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C13 C14 C9 119.66(17) . .
C13 C14 H14 120.2 . .
C9 C14 H14 120.2 . .
N3 C15 N4 114.85(15) . .
N3 C15 C18 125.76(16) . .
N4 C15 C18 119.37(16) . .
N4 C16 N5 128.10(17) . .
N4 C16 H16 115.9 . .
N5 C16 H16 115.9 . .
N5 C17 O2 118.33(16) . .
N5 C17 C18 129.01(17) . .
O2 C17 C18 112.65(16) . .
C17 C18 C15 113.76(16) . .
C17 C18 C19 105.54(15) . .
C15 C18 C19 140.64(16) . .
C24 C19 C20 117.72(16) . .
C24 C19 C18 137.82(16) . .
C20 C19 C18 104.44(15) . .
C21 C20 O2 123.19(17) . .
C21 C20 C19 124.70(18) . .
O2 C20 C19 112.09(16) . .
C20 C21 C22 116.37(18) . .
C20 C21 H21 121.8 . .
C22 C21 H21 121.8 . .
C21 C22 C23 121.60(18) . .
C21 C22 H22 119.2 . .
C23 C22 H22 119.2 . .
C24 C23 C22 120.55(18) . .
C24 C23 C25 122.23(18) . .
C22 C23 C25 117.14(17) . .
C19 C24 C23 119.03(17) . .
C19 C24 H24 120.5 . .
C23 C24 H24 120.5 . .
O3 C25 O4 122.61(19) . .
O3 C25 C23 124.3(2) . .
O4 C25 C23 113.09(16) . .
O4 C26 H26A 109.5 . .
O4 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
O4 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C8 N2 C9 128.80(16) . .
C8 N2 H2 115.6 . .
C9 N2 H2 115.6 . .
C15 N3 C12 126.32(15) . .
C15 N3 H3A 116.8 . .
C12 N3 H3A 116.8 . .
C16 N4 C15 118.56(16) . .
C17 N5 C16 111.03(16) . .
C17 O2 C20 105.27(14) . .
C25 O4 C26 116.93(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.148(3) .
C1 C2 1.444(3) .
C2 C3 1.388(3) .
C2 C7 1.393(3) .
C3 C4 1.381(3) .
C3 H3 0.9300 .
C4 C5 1.391(3) .
C4 H4 0.9300 .
C5 C6 1.391(3) .
C5 C8 1.499(3) .
C6 C7 1.375(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 O1 1.224(2) .
C8 N2 1.359(2) .
C9 C14 1.389(2) .
C9 C10 1.392(3) .
C9 N2 1.403(2) .
C10 C11 1.374(3) .
C10 H10 0.9300 .
C11 C12 1.379(3) .
C11 H11 0.9300 .
C12 C13 1.386(3) .
C12 N3 1.420(2) .
C13 C14 1.380(2) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 N3 1.348(2) .
C15 N4 1.358(2) .
C15 C18 1.412(2) .
C16 N4 1.325(2) .
C16 N5 1.336(2) .
C16 H16 0.9300 .
C17 N5 1.328(2) .
C17 O2 1.367(2) .
C17 C18 1.386(2) .
C18 C19 1.467(2) .
C19 C24 1.392(2) .
C19 C20 1.400(2) .
C20 C21 1.376(3) .
C20 O2 1.385(2) .
C21 C22 1.376(3) .
C21 H21 0.9300 .
C22 C23 1.401(3) .
C22 H22 0.9300 .
C23 C24 1.397(3) .
C23 C25 1.483(3) .
C24 H24 0.9300 .
C25 O3 1.204(2) .
C25 O4 1.330(2) .
C26 O4 1.446(2) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
N2 H2 0.8600 .
N3 H3A 0.8600 .
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
C7 C2 C3 C4 1.1(3) . . . .
C1 C2 C3 C4 -179.78(18) . . . .
C2 C3 C4 C5 -1.1(3) . . . .
C3 C4 C5 C6 -0.5(3) . . . .
C3 C4 C5 C8 -177.78(18) . . . .
C4 C5 C6 C7 2.1(3) . . . .
C8 C5 C6 C7 179.43(17) . . . .
C5 C6 C7 C2 -2.1(3) . . . .
C3 C2 C7 C6 0.5(3) . . . .
C1 C2 C7 C6 -178.60(18) . . . .
C4 C5 C8 O1 134.5(2) . . . .
C6 C5 C8 O1 -42.9(3) . . . .
C4 C5 C8 N2 -45.6(2) . . . .
C6 C5 C8 N2 137.07(18) . . . .
C14 C9 C10 C11 -0.7(3) . . . .
N2 C9 C10 C11 175.54(18) . . . .
C9 C10 C11 C12 -0.7(3) . . . .
C10 C11 C12 C13 0.7(3) . . . .
C10 C11 C12 N3 -176.31(18) . . . .
C11 C12 C13 C14 0.7(3) . . . .
N3 C12 C13 C14 177.68(15) . . . .
C12 C13 C14 C9 -2.1(3) . . . .
C10 C9 C14 C13 2.0(3) . . . .
N2 C9 C14 C13 -173.91(16) . . . .
N5 C17 C18 C15 0.2(3) . . . .
O2 C17 C18 C15 -178.55(14) . . . .
N5 C17 C18 C19 177.79(17) . . . .
O2 C17 C18 C19 -0.92(19) . . . .
N3 C15 C18 C17 -178.26(17) . . . .
N4 C15 C18 C17 3.2(2) . . . .
N3 C15 C18 C19 5.4(4) . . . .
N4 C15 C18 C19 -173.17(19) . . . .
C17 C18 C19 C24 -178.1(2) . . . .
C15 C18 C19 C24 -1.5(4) . . . .
C17 C18 C19 C20 0.28(18) . . . .
C15 C18 C19 C20 176.9(2) . . . .
C24 C19 C20 C21 1.0(3) . . . .
C18 C19 C20 C21 -177.71(18) . . . .
C24 C19 C20 O2 179.19(15) . . . .
C18 C19 C20 O2 0.43(19) . . . .
O2 C20 C21 C22 -178.88(17) . . . .
C19 C20 C21 C22 -0.9(3) . . . .
C20 C21 C22 C23 -0.5(3) . . . .
C21 C22 C23 C24 1.7(3) . . . .
C21 C22 C23 C25 -175.14(18) . . . .
C20 C19 C24 C23 0.2(2) . . . .
C18 C19 C24 C23 178.46(19) . . . .
C22 C23 C24 C19 -1.6(3) . . . .
C25 C23 C24 C19 175.13(16) . . . .
C24 C23 C25 O3 169.0(2) . . . .
C22 C23 C25 O3 -14.2(3) . . . .
C24 C23 C25 O4 -11.8(3) . . . .
C22 C23 C25 O4 165.05(17) . . . .
O1 C8 N2 C9 -9.0(3) . . . .
C5 C8 N2 C9 171.08(17) . . . .
C14 C9 N2 C8 -17.7(3) . . . .
C10 C9 N2 C8 166.26(19) . . . .
N4 C15 N3 C12 -158.64(17) . . . .
C18 C15 N3 C12 22.8(3) . . . .
C11 C12 N3 C15 -135.5(2) . . . .
C13 C12 N3 C15 47.6(3) . . . .
N5 C16 N4 C15 0.0(3) . . . .
N3 C15 N4 C16 177.95(16) . . . .
C18 C15 N4 C16 -3.4(2) . . . .
O2 C17 N5 C16 175.55(15) . . . .
C18 C17 N5 C16 -3.1(3) . . . .
N4 C16 N5 C17 3.1(3) . . . .
N5 C17 O2 C20 -177.69(16) . . . .
C18 C17 O2 C20 1.18(19) . . . .
C21 C20 O2 C17 177.20(17) . . . .
C19 C20 O2 C17 -0.98(19) . . . .
O3 C25 O4 C26 3.8(3) . . . .
C23 C25 O4 C26 -175.42(17) . . . .
