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#$Date: 2020-11-06 14:19:26 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258855 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705252.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_7705252
loop_
_publ_author_name
'Shen, Guodong'
'Wang, Zeyou'
'Huang, Xianqiang'
'Gong, Shuwen'
'Zhang, Jiangong'
'Tang, Zhenfei'
'Sun, Manman'
'Lv, Xin'
_publ_section_title
;
 Bonded- and discreted-Lindqvist hexatungstate-based copper hybrids as
 heterogeneous catalysts for the one-pot synthesis of 2-phenylquinoxalines
 via 2-haloanilines with vinyl azides or
 3-phenyl-2H-azirines.
;
_journal_issue                   40
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13993
_journal_page_last               13998
_journal_paper_doi               10.1039/d0dt02625e
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C15 H12 N2'
_chemical_formula_weight         220.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-09 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.16(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.580(2)
_cell_length_b                   4.8156(10)
_cell_length_c                   12.595(3)
_cell_measurement_reflns_used    508
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8590
_cell_measurement_theta_min      5.3590
_cell_volume                     565.8(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1600
_diffrn_reflns_point_group_measured_fraction_full 0.626
_diffrn_reflns_point_group_measured_fraction_max 0.626
_diffrn_reflns_theta_full        67.144
_diffrn_reflns_theta_max         67.144
_diffrn_reflns_theta_min         3.604
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 102 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1675P)²+0.0044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2276
_refine_ls_wR_factor_ref         0.2693
_reflns_Friedel_coverage         0.131
_reflns_Friedel_fraction_full    0.167
_reflns_Friedel_fraction_max     0.167
_reflns_number_gt                898
_reflns_number_total             1269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02625e2.cif
_cod_data_source_block           exp_8433
_cod_depositor_comments
'Adding full bibliography for 7705251--7705253.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7705252
_shelx_shelxl_version_number     2018/3
_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   0.884
_shelx_estimated_absorpt_t_max   0.899
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.0523(5) 0.7373(10) 0.1951(3) 0.0508(13) Uani 1 1 d . . . . .
N2 N -0.0825(5) 0.5796(13) 0.3627(3) 0.0606(15) Uani 1 1 d . . . . .
C1 C 0.0896(5) 0.8492(13) 0.2930(4) 0.0495(15) Uani 1 1 d . . . . .
C2 C 0.0189(6) 0.7686(15) 0.3766(4) 0.0606(18) Uani 1 1 d . . . . .
H2 H 0.046170 0.854333 0.444298 0.073 Uiso 1 1 calc R U . . .
C3 C -0.1211(6) 0.4613(14) 0.2618(4) 0.0523(15) Uani 1 1 d . . . . .
C4 C -0.2295(6) 0.2545(13) 0.2407(5) 0.0581(17) Uani 1 1 d . . . . .
H4 H -0.273028 0.199415 0.296177 0.070 Uiso 1 1 calc R U . . .
C5 C -0.2706(6) 0.1360(14) 0.1406(5) 0.0580(17) Uani 1 1 d . . . . .
C6 C -0.2029(6) 0.2139(15) 0.0575(5) 0.0605(17) Uani 1 1 d . . . . .
H6 H -0.229803 0.130544 -0.010710 0.073 Uiso 1 1 calc R U . . .
C7 C -0.0972(6) 0.4123(14) 0.0760(4) 0.0576(16) Uani 1 1 d . . . . .
H7 H -0.054058 0.463275 0.019798 0.069 Uiso 1 1 calc R U . . .
C8 C -0.0535(5) 0.5388(13) 0.1781(4) 0.0497(15) Uani 1 1 d . . . . .
C9 C -0.3865(6) -0.0825(16) 0.1166(5) 0.073(2) Uani 1 1 d . . . . .
H9A H -0.419341 -0.121030 0.181703 0.109 Uiso 1 1 calc R U . . .
H9B H -0.348830 -0.249273 0.092121 0.109 Uiso 1 1 calc R U . . .
H9C H -0.465192 -0.016185 0.060923 0.109 Uiso 1 1 calc R U . . .
C10 C 0.2046(6) 1.0621(13) 0.3134(4) 0.0535(15) Uani 1 1 d . . . . .
C11 C 0.2700(6) 1.1373(16) 0.2292(4) 0.0618(17) Uani 1 1 d . . . . .
H11 H 0.240197 1.055542 0.160892 0.074 Uiso 1 1 calc R U . . .
C12 C 0.3791(6) 1.3326(16) 0.2466(5) 0.073(2) Uani 1 1 d . . . . .
H12 H 0.422880 1.377953 0.190206 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4231(6) 1.4596(19) 0.3458(5) 0.074(2) Uani 1 1 d . . . . .
H13 H 0.495192 1.592881 0.356629 0.089 Uiso 1 1 calc R U . . .
C14 C 0.3596(7) 1.3877(16) 0.4290(5) 0.073(2) Uani 1 1 d . . . . .
H14 H 0.389753 1.471888 0.496834 0.088 Uiso 1 1 calc R U . . .
C15 C 0.2503(6) 1.1901(16) 0.4135(5) 0.0655(18) Uani 1 1 d . . . . .
H15 H 0.207983 1.144281 0.470714 0.079 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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 C8 117.6(4) . . ?
C2 N2 C3 116.7(5) . . ?
N1 C1 C2 120.3(5) . . ?
N1 C1 C10 118.4(4) . . ?
C2 C1 C10 121.2(5) . . ?
N2 C2 C1 123.4(5) . . ?
N2 C3 C8 120.9(5) . . ?
N2 C3 C4 119.9(5) . . ?
C8 C3 C4 119.2(5) . . ?
C5 C4 C3 120.9(5) . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 C9 121.5(5) . . ?
C6 C5 C9 118.8(6) . . ?
C7 C6 C5 120.6(6) . . ?
C6 C7 C8 120.9(5) . . ?
N1 C8 C7 120.1(4) . . ?
N1 C8 C3 121.1(5) . . ?
C7 C8 C3 118.8(5) . . ?
C15 C10 C11 118.3(6) . . ?
C15 C10 C1 122.2(5) . . ?
C11 C10 C1 119.5(5) . . ?
C12 C11 C10 120.5(6) . . ?
C13 C12 C11 120.8(6) . . ?
C12 C13 C14 119.1(7) . . ?
C13 C14 C15 121.0(6) . . ?
C10 C15 C14 120.2(6) . . ?
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
N1 C1 1.318(6) . ?
N1 C8 1.374(7) . ?
N2 C2 1.314(8) . ?
N2 C3 1.364(7) . ?
C1 C2 1.428(7) . ?
C1 C10 1.484(7) . ?
C3 C8 1.407(6) . ?
C3 C4 1.420(8) . ?
C4 C5 1.358(8) . ?
C5 C6 1.402(8) . ?
C5 C9 1.510(9) . ?
C6 C7 1.373(9) . ?
C7 C8 1.398(7) . ?
C10 C15 1.382(8) . ?
C10 C11 1.396(7) . ?
C11 C12 1.385(9) . ?
C12 C13 1.368(9) . ?
C13 C14 1.371(9) . ?
C14 C15 1.395(9) . ?
