#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:34:55 +0300 (Fri, 05 May 2023) $
#$Revision: 283120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/14/7131490.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_7131490
loop_
_publ_author_name
'Zhang, Chihong'
'Zhang, Zhen'
'Wang, Deliang'
'Wang, Wenkun'
'Jin, Bo'
'Wen, Tao'
'Ye, Lihua'
'Chen, Zhong-Ning'
'Cai, Hu'
_publ_section_title
;
 DMSO/tBuONa/O₂-mediated efficient syntheses of diverse
 quinoxalines through α-imino radicals.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5217
_journal_page_last               5220
_journal_paper_doi               10.1039/d3cc00086a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-04
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.509(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5545(14)
_cell_length_b                   4.7731(7)
_cell_length_c                   12.5151(18)
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.05
_cell_volume                     554.96(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3399
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.703
_diffrn_reflns_theta_min         3.054
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9253.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             248
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0356
_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)+(0.0448P)²+0.0326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.721
_reflns_number_gt                1989
_reflns_number_total             2250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00086a2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7131490.cif.'
_cod_database_code               7131490
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl01 Cl 0.09563(7) -0.2902(2) 0.60747(6) 0.0522(2) Uani 1 1 d . . . . .
N002 N 0.5525(2) 0.5619(4) 0.69329(15) 0.0290(4) Uani 1 1 d . . . . .
N003 N 0.4189(2) 0.4033(5) 0.86239(16) 0.0380(5) Uani 1 1 d . . . . .
C004 C 0.4464(2) 0.3651(5) 0.67594(18) 0.0279(5) Uani 1 1 d . . . . .
C005 C 0.3782(2) 0.2837(5) 0.76006(19) 0.0292(6) Uani 1 1 d . . . . .
C006 C 0.5910(2) 0.6759(6) 0.79187(17) 0.0290(6) Uani 1 1 d . . . . .
C007 C 0.2693(3) 0.0780(6) 0.7388(2) 0.0354(6) Uani 1 1 d . . . . .
H007 H 0.224740 0.022231 0.793882 0.042 Uiso 1 1 calc R U . . .
C008 C 0.7066(3) 0.8883(5) 0.8119(2) 0.0309(5) Uani 1 1 d . . . . .
C009 C 0.2302(3) -0.0379(5) 0.6371(2) 0.0351(6) Uani 1 1 d . . . . .
C00A C 0.2971(3) 0.0397(6) 0.5525(2) 0.0384(6) Uani 1 1 d . . . . .
H00A H 0.269188 -0.043813 0.483672 0.046 Uiso 1 1 calc R U . . .
C00B C 0.4026(2) 0.2374(7) 0.57188(19) 0.0345(6) Uani 1 1 d . . . . .
H00B H 0.446414 0.288928 0.515800 0.041 Uiso 1 1 calc R U . . .
C00C C 0.7756(3) 0.9565(6) 0.7283(2) 0.0396(6) Uani 1 1 d . . . . .
H00C H 0.748191 0.866737 0.660684 0.048 Uiso 1 1 calc R U . . .
C00D C 0.5206(3) 0.5903(6) 0.87610(19) 0.0369(6) Uani 1 1 d . . . . .
H00D H 0.549606 0.673872 0.944855 0.044 Uiso 1 1 calc R U . . .
C00E C 0.7521(3) 1.0262(6) 0.9127(2) 0.0399(6) Uani 1 1 d . . . . .
H00E H 0.708817 0.984142 0.970037 0.048 Uiso 1 1 calc R U . . .
C00F C 0.8833(3) 1.1545(6) 0.7446(2) 0.0459(7) Uani 1 1 d . . . . .
H00F H 0.927247 1.197928 0.687720 0.055 Uiso 1 1 calc R U . . .
C00G C 0.8606(3) 1.2245(8) 0.9281(2) 0.0474(7) Uani 1 1 d . . . . .
H00G H 0.889075 1.315119 0.995434 0.057 Uiso 1 1 calc R U . . .
C00H C 0.9267(3) 1.2890(6) 0.8445(3) 0.0471(8) Uani 1 1 d . . . . .
H00H H 0.999825 1.421894 0.855322 0.056 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
C006 N002 C004 117.9(2) . . ?
C00D N003 C005 116.6(2) . . ?
N002 C004 C005 121.7(2) . . ?
N002 C004 C00B 119.7(2) . . ?
C00B C004 C005 118.6(2) . . ?
N003 C005 C004 120.0(2) . . ?
N003 C005 C007 120.1(2) . . ?
C007 C005 C004 119.9(2) . . ?
N002 C006 C008 118.42(19) . . ?
N002 C006 C00D 119.5(2) . . ?
C00D C006 C008 122.1(2) . . ?
C005 C007 H007 120.3 . . ?
C009 C007 C005 119.4(2) . . ?
C009 C007 H007 120.3 . . ?
C00C C008 C006 119.8(2) . . ?
C00C C008 C00E 117.6(2) . . ?
C00E C008 C006 122.6(2) . . ?
C007 C009 Cl01 120.7(2) . . ?
C007 C009 C00A 121.6(2) . . ?
C00A C009 Cl01 117.7(2) . . ?
C009 C00A H00A 120.1 . . ?
C00B C00A C009 119.7(2) . . ?
C00B C00A H00A 120.1 . . ?
C004 C00B H00B 119.6 . . ?
C00A C00B C004 120.8(2) . . ?
C00A C00B H00B 119.6 . . ?
C008 C00C H00C 119.5 . . ?
C00F C00C C008 121.0(3) . . ?
C00F C00C H00C 119.5 . . ?
N003 C00D C006 124.2(2) . . ?
N003 C00D H00D 117.9 . . ?
C006 C00D H00D 117.9 . . ?
C008 C00E H00E 119.6 . . ?
C00G C00E C008 120.8(2) . . ?
C00G C00E H00E 119.6 . . ?
C00C C00F H00F 119.7 . . ?
C00C C00F C00H 120.6(3) . . ?
C00H C00F H00F 119.7 . . ?
C00E C00G H00G 119.7 . . ?
C00H C00G C00E 120.6(3) . . ?
C00H C00G H00G 119.7 . . ?
C00F C00H H00H 120.3 . . ?
C00G C00H C00F 119.4(3) . . ?
C00G C00H H00H 120.3 . . ?
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
Cl01 C009 1.737(3) . ?
N002 C004 1.361(3) . ?
N002 C006 1.320(3) . ?
N003 C005 1.373(3) . ?
N003 C00D 1.301(3) . ?
C004 C005 1.416(3) . ?
C004 C00B 1.410(3) . ?
C005 C007 1.410(3) . ?
C006 C008 1.477(4) . ?
C006 C00D 1.436(3) . ?
C007 H007 0.9300 . ?
C007 C009 1.357(3) . ?
C008 C00C 1.399(3) . ?
C008 C00E 1.399(4) . ?
C009 C00A 1.408(4) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.361(4) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00F 1.377(4) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00G 1.384(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.381(4) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.376(4) . ?
C00H H00H 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
Cl01 C009 C00A C00B 179.7(2) . . . . ?
N002 C004 C005 N003 -0.2(3) . . . . ?
N002 C004 C005 C007 -179.7(2) . . . . ?
N002 C004 C00B C00A 179.9(2) . . . . ?
N002 C006 C008 C00C -2.2(4) . . . . ?
N002 C006 C008 C00E 178.2(2) . . . . ?
N002 C006 C00D N003 0.1(4) . . . . ?
N003 C005 C007 C009 179.9(2) . . . . ?
C004 N002 C006 C008 179.6(2) . . . . ?
C004 N002 C006 C00D -0.1(3) . . . . ?
C004 C005 C007 C009 -0.6(3) . . . . ?
C005 N003 C00D C006 -0.1(4) . . . . ?
C005 C004 C00B C00A -0.1(4) . . . . ?
C005 C007 C009 Cl01 -179.55(17) . . . . ?
C005 C007 C009 C00A 0.8(4) . . . . ?
C006 N002 C004 C005 0.2(3) . . . . ?
C006 N002 C004 C00B -179.7(3) . . . . ?
C006 C008 C00C C00F 179.7(2) . . . . ?
C006 C008 C00E C00G -179.8(3) . . . . ?
C007 C009 C00A C00B -0.6(4) . . . . ?
C008 C006 C00D N003 -179.6(3) . . . . ?
C008 C00C C00F C00H 0.5(4) . . . . ?
C008 C00E C00G C00H -0.4(5) . . . . ?
C009 C00A C00B C004 0.2(4) . . . . ?
C00B C004 C005 N003 179.7(2) . . . . ?
C00B C004 C005 C007 0.3(3) . . . . ?
C00C C008 C00E C00G 0.5(4) . . . . ?
C00C C00F C00H C00G -0.3(4) . . . . ?
C00D N003 C005 C004 0.1(3) . . . . ?
C00D N003 C005 C007 179.6(2) . . . . ?
C00D C006 C008 C00C 177.5(2) . . . . ?
C00D C006 C008 C00E -2.1(4) . . . . ?
C00E C008 C00C C00F -0.6(4) . . . . ?
C00E C00G C00H C00F 0.3(5) . . . . ?
