#------------------------------------------------------------------------------
#$Date: 2025-08-21 01:27:06 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301840 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/58/4345891.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_4345891
loop_
_publ_author_name
'Wang, Yazhen'
'Yu, Feihu'
'Han, Xiao'
'Li, Ming'
'Tong, Yue'
'Ding, Jie'
'Hou, Hongwei'
_publ_section_title
;
 From Surprising Solvothermal Reaction to Uncommon Zinc(II)-Catalyzed
 Aromatic C-H Activation Reaction for Direct Nitroquinoline Synthesis.
;
_journal_issue                   10
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5953
_journal_page_last               5958
_journal_paper_doi               10.1021/acs.inorgchem.7b00653
_journal_volume                  56
_journal_year                    2017
_chemical_formula_sum            'C26 H18 N4 O2'
_chemical_formula_weight         418.44
_space_group_IT_number           14
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1433(18)
_cell_length_b                   6.2477(12)
_cell_length_c                   18.463(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1016.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6904
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9703
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3248
_refine_ls_wR_factor_ref         0.3554
_reflns_number_gt                1447
_reflns_number_total             1799
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic7b00653_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        1016.1(4)
_cod_database_code               4345891
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2677(4) 0.4052(5) 0.47229(18) 0.0670(12) Uani 1 1 d .
N1 N 0.2175(4) 0.4854(5) 0.58241(18) 0.0419(10) Uani 1 1 d .
H14 H 0.1702 0.4389 0.6137 0.050 Uiso 1 1 calc R
N2 N 0.1727(4) 0.6862(6) 0.7000(2) 0.0537(11) Uani 1 1 d .
C1 C 0.1473(6) 0.7865(10) 0.7577(3) 0.0707(16) Uani 1 1 d .
H1 H 0.0792 0.7241 0.7809 0.085 Uiso 1 1 calc R
C2 C 0.2138(6) 0.9784(9) 0.7869(3) 0.0734(17) Uani 1 1 d .
H2 H 0.1908 1.0413 0.8282 0.088 Uiso 1 1 calc R
C3 C 0.3132(6) 1.0722(8) 0.7538(3) 0.0635(15) Uani 1 1 d .
H3 H 0.3582 1.2018 0.7722 0.076 Uiso 1 1 calc R
C4 C 0.3486(5) 0.9759(7) 0.6923(2) 0.0471(12) Uani 1 1 d .
C5 C 0.2726(4) 0.7805(6) 0.6666(2) 0.0408(11) Uani 1 1 d .
C6 C 0.4506(5) 1.0583(7) 0.6544(3) 0.0526(13) Uani 1 1 d .
H6 H 0.4976 1.1894 0.6688 0.063 Uiso 1 1 calc R
C7 C 0.4803(5) 0.9493(8) 0.5976(3) 0.0566(13) Uani 1 1 d .
H7 H 0.5520 1.0036 0.5751 0.068 Uiso 1 1 calc R
C8 C 0.4074(5) 0.7564(7) 0.5707(2) 0.0490(12) Uani 1 1 d .
H8 H 0.4303 0.6851 0.5309 0.059 Uiso 1 1 calc R
C9 C 0.3028(5) 0.6745(7) 0.6034(2) 0.0428(11) Uani 1 1 d .
C10 C 0.2011(5) 0.3686(6) 0.5191(2) 0.0422(11) Uani 1 1 d .
C11 C 0.0963(5) 0.1797(6) 0.5116(2) 0.0406(11) Uani 1 1 d .
C12 C 0.0013(5) 0.1406(7) 0.5566(2) 0.0502(12) Uani 1 1 d .
H12 H -0.0004 0.2371 0.5948 0.060 Uiso 1 1 calc R
C13 C 0.0909(5) 0.0356(7) 0.4529(2) 0.0509(12) Uani 1 1 d .
H13 H 0.1505 0.0598 0.4200 0.061 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
C10 N1 C9 127.9(4) .
C10 N1 H14 116.0 .
C9 N1 H14 116.0 .
C1 N2 C5 116.6(4) .
N2 C1 C2 125.1(5) .
N2 C1 H1 117.4 .
C2 C1 H1 117.4 .
C3 C2 C1 118.4(5) .
C3 C2 H2 120.8 .
C1 C2 H2 120.8 .
C2 C3 C4 120.6(5) .
C2 C3 H3 119.7 .
C4 C3 H3 119.7 .
C3 C4 C6 125.2(4) .
C3 C4 C5 116.2(4) .
C6 C4 C5 118.6(4) .
N2 C5 C4 123.1(4) .
N2 C5 C9 117.9(4) .
C4 C5 C9 119.0(4) .
C7 C6 C4 120.3(4) .
C7 C6 H6 119.8 .
C4 C6 H6 119.8 .
C6 C7 C8 122.5(5) .
C6 C7 H7 118.7 .
C8 C7 H7 118.7 .
C9 C8 C7 119.4(4) .
C9 C8 H8 120.3 .
C7 C8 H8 120.3 .
C8 C9 N1 126.6(4) .
C8 C9 C5 120.0(4) .
N1 C9 C5 113.4(4) .
O1 C10 N1 123.9(4) .
O1 C10 C11 121.0(4) .
N1 C10 C11 115.1(3) .
C12 C11 C13 117.2(4) .
C12 C11 C10 125.1(4) .
C13 C11 C10 117.7(4) .
C13 C12 C11 122.2(4) 3_556
C13 C12 H12 118.9 3_556
C11 C12 H12 118.9 .
C12 C13 C11 120.6(4) 3_556
C12 C13 H13 119.7 3_556
C11 C13 H13 119.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.205(5) .
N1 C10 1.352(5) .
N1 C9 1.411(5) .
N1 H14 0.8600 .
N2 C1 1.309(6) .
N2 C5 1.365(5) .
C1 C2 1.387(8) .
C1 H1 0.9300 .
C2 C3 1.357(8) .
C2 H2 0.9300 .
C3 C4 1.398(7) .
C3 H3 0.9300 .
C4 C6 1.405(7) .
C4 C5 1.422(6) .
C5 C9 1.432(6) .
C6 C7 1.338(7) .
C6 H6 0.9300 .
C7 C8 1.402(7) .
C7 H7 0.9300 .
C8 C9 1.360(6) .
C8 H8 0.9300 .
C10 C11 1.502(6) .
C11 C12 1.375(6) .
C11 C13 1.401(6) .
C12 C13 1.369(6) 3_556
C12 H12 0.9300 .
C13 C12 1.369(6) 3_556
C13 H13 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_4
C5 N2 C1 C2 -0.1(8) .
N2 C1 C2 C3 0.1(9) .
C1 C2 C3 C4 -0.7(8) .
C2 C3 C4 C6 -179.5(5) .
C2 C3 C4 C5 1.3(7) .
C1 N2 C5 C4 0.8(7) .
C1 N2 C5 C9 180.0(4) .
C3 C4 C5 N2 -1.4(6) .
C6 C4 C5 N2 179.4(4) .
C3 C4 C5 C9 179.5(4) .
C6 C4 C5 C9 0.2(6) .
C3 C4 C6 C7 177.7(4) .
C5 C4 C6 C7 -3.1(7) .
C4 C6 C7 C8 3.3(7) .
C6 C7 C8 C9 -0.4(7) .
C7 C8 C9 N1 178.7(4) .
C7 C8 C9 C5 -2.6(6) .
C10 N1 C9 C8 -12.7(7) .
C10 N1 C9 C5 168.5(4) .
N2 C5 C9 C8 -176.6(4) .
C4 C5 C9 C8 2.6(6) .
N2 C5 C9 N1 2.3(5) .
C4 C5 C9 N1 -178.5(3) .
C9 N1 C10 O1 5.0(7) .
C9 N1 C10 C11 -177.4(3) .
O1 C10 C11 C12 -171.3(4) .
N1 C10 C11 C12 11.0(6) .
O1 C10 C11 C13 6.5(6) .
N1 C10 C11 C13 -171.2(4) .
C13 C11 C12 C13 2.6(8) 3_556
C10 C11 C12 C13 -179.6(4) 3_556
C12 C11 C13 C12 -2.6(7) 3_556
C10 C11 C13 C12 179.5(4) 3_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 24646344
