#------------------------------------------------------------------------------
#$Date: 2022-05-26 00:52:41 +0300 (Thu, 26 May 2022) $
#$Revision: 275639 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130143.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_7130143
loop_
_publ_author_name
'Kwon, Na Yeon'
'Mishra, Neeraj Kumar'
'Park, Jung Su'
'Woo, Sang Kook'
'Ghosh, Prithwish'
'Kim, In Su'
_publ_section_title
;
 KOtBu-promoted C3-homocoupling of quinoxalinones through single electron
 transfer from a sp2 carbanion intermediate
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02636H
_journal_year                    2022
_chemical_formula_sum            'C18 H12 Cl2 N4 O2'
_chemical_formula_weight         387.22
_chemical_name_common            YV479
_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
_audit_update_record
;
2022-01-21 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                74.939(2)
_cell_angle_beta                 86.769(2)
_cell_angle_gamma                84.018(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4478(5)
_cell_length_b                   9.0425(6)
_cell_length_c                   12.7861(8)
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      23.3716
_cell_measurement_theta_min      2.3426
_cell_volume                     826.61(9)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0663
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34242
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.65
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.398
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0495
_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)+(0.0721P)²+0.4348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2116
_reflns_number_total             4076
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02636h2.cif
_cod_data_source_block           yy076
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130143
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1334(4) 0.7752(4) -0.0937(2) 0.0534(7) Uani d . . . 1 . .
C C2 0.1878(4) 0.7258(4) 0.0109(2) 0.0540(7) Uani d . . . 1 . .
H H2 0.183016 0.794201 0.054411 0.065 Uiso calc U . R 1 . .
C C3 0.2508(4) 0.5713(3) 0.0521(2) 0.0496(7) Uani d . . . 1 . .
C C4 0.2584(4) 0.4689(3) -0.0135(2) 0.0490(7) Uani d . . . 1 . .
C C5 0.2017(4) 0.5234(4) -0.1203(2) 0.0565(8) Uani d . . . 1 . .
H H5 0.206133 0.45633 -0.164754 0.068 Uiso calc U . R 1 . .
C C6 0.1396(4) 0.6748(4) -0.1599(2) 0.0575(8) Uani d . . . 1 . .
H H6 0.101804 0.710244 -0.230926 0.069 Uiso calc U . R 1 . .
C C7 0.3415(5) 0.2071(4) -0.0379(3) 0.0736(10) Uani d . . . 1 . .
H H7A 0.381433 0.106642 0.005448 0.11 Uiso calc U . R 1 . .
H H7B 0.428334 0.238912 -0.095708 0.11 Uiso calc U . R 1 . .
H H7C 0.226875 0.204189 -0.067637 0.11 Uiso calc U . R 1 . .
C C8 0.3769(4) 0.2650(4) 0.1351(3) 0.0565(8) Uani d . . . 1 . .
C C9 0.3525(4) 0.3814(4) 0.1982(2) 0.0550(8) Uani d . . . 1 . .
C C10 0.3963(4) 0.3268(4) 0.3157(2) 0.0549(8) Uani d . . . 1 . .
C C11 0.2742(4) 0.2192(4) 0.3840(2) 0.0569(8) Uani d . . . 1 . .
C C12 0.2120(5) 0.0479(4) 0.5596(3) 0.0672(9) Uani d . . . 1 . .
H H12A 0.129125 0.096571 0.603411 0.101 Uiso calc U . R 1 . .
H H12B 0.289344 -0.031094 0.605528 0.101 Uiso calc U . R 1 . .
H H12C 0.145657 0.003092 0.515267 0.101 Uiso calc U . R 1 . .
C C13 0.5707(4) 0.3195(3) 0.4591(2) 0.0524(7) Uani d . . . 1 . .
C C14 0.7202(4) 0.3672(4) 0.4970(3) 0.0597(8) Uani d . . . 1 . .
H H14 0.788718 0.438369 0.450359 0.072 Uiso calc U . R 1 . .
C C15 0.7668(4) 0.3095(4) 0.6028(3) 0.0611(8) Uani d . . . 1 . .
C C16 0.6657(5) 0.2045(4) 0.6738(3) 0.0640(9) Uani d . . . 1 . .
H H16 0.698758 0.166502 0.745586 0.077 Uiso calc U . R 1 . .
C C17 0.5171(4) 0.1565(4) 0.6384(2) 0.0588(8) Uani d . . . 1 . .
H H17 0.449 0.086481 0.686373 0.071 Uiso calc U . R 1 . .
C C18 0.4673(4) 0.2126(3) 0.5302(2) 0.0493(7) Uani d . . . 1 . .
Cl Cl1 0.05593(14) 0.96676(10) -0.14668(7) 0.0757(3) Uani d . . . 1 . .
Cl Cl2 0.95708(14) 0.36447(13) 0.64933(8) 0.0842(4) Uani d . . . 1 . .
N N1 0.3011(3) 0.5250(3) 0.15981(19) 0.0552(6) Uani d . . . 1 . .
N N2 0.3232(3) 0.3165(3) 0.0297(2) 0.0536(6) Uani d . . . 1 . .
N N3 0.3219(3) 0.1628(3) 0.48996(19) 0.0525(6) Uani d . . . 1 . .
N N4 0.5318(4) 0.3756(3) 0.3499(2) 0.0586(7) Uani d . . . 1 . .
O O1 0.4432(4) 0.1335(3) 0.1733(2) 0.0770(7) Uani d . . . 1 . .
O O2 0.1402(3) 0.1838(3) 0.34860(19) 0.0765(7) Uani d . . . 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.2(3) ?
C2 C1 Cl1 . . 120.1(3) ?
C6 C1 Cl1 . . 118.7(2) ?
C1 C2 C3 . . 119.4(3) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
N1 C3 C4 . . 122.3(3) ?
N1 C3 C2 . . 117.5(3) ?
C4 C3 C2 . . 120.2(3) ?
N2 C4 C3 . . 118.7(3) ?
N2 C4 C5 . . 122.4(3) ?
C3 C4 C5 . . 118.9(3) ?
C6 C5 C4 . . 120.6(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 119.8(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O1 C8 N2 . . 122.6(3) ?
O1 C8 C9 . . 122.5(3) ?
N2 C8 C9 . . 114.9(3) ?
N1 C9 C8 . . 125.3(3) ?
N1 C9 C10 . . 118.2(3) ?
C8 C9 C10 . . 116.4(3) ?
N4 C10 C11 . . 125.1(3) ?
N4 C10 C9 . . 119.3(3) ?
C11 C10 C9 . . 115.6(3) ?
O2 C11 N3 . . 122.5(3) ?
O2 C11 C10 . . 122.4(3) ?
N3 C11 C10 . . 115.1(3) ?
N3 C12 H12A . . 109.5 ?
N3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 N4 . . 118.5(3) ?
C14 C13 C18 . . 119.6(3) ?
N4 C13 C18 . . 121.8(3) ?
C15 C14 C13 . . 120.1(3) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.9(3) ?
C14 C15 Cl2 . . 120.2(3) ?
C16 C15 Cl2 . . 118.9(3) ?
C17 C16 C15 . . 120.0(3) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.3(3) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
N3 C18 C17 . . 122.1(3) ?
N3 C18 C13 . . 118.7(2) ?
C17 C18 C13 . . 119.1(3) ?
C9 N1 C3 . . 117.1(3) ?
C8 N2 C4 . . 121.5(3) ?
C8 N2 C7 . . 118.1(3) ?
C4 N2 C7 . . 120.4(3) ?
C11 N3 C18 . . 121.5(2) ?
C11 N3 C12 . . 117.2(3) ?
C18 N3 C12 . . 121.2(2) ?
C10 N4 C13 . . 117.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.367(4) ?
C1 C6 . 1.388(4) ?
C1 Cl1 . 1.738(3) ?
C2 C3 . 1.399(4) ?
C2 H2 . 0.93 ?
C3 N1 . 1.392(3) ?
C3 C4 . 1.397(4) ?
C4 N2 . 1.390(4) ?
C4 C5 . 1.399(4) ?
C5 C6 . 1.371(4) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N2 . 1.464(4) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 O1 . 1.224(4) ?
C8 N2 . 1.375(4) ?
C8 C9 . 1.475(5) ?
C9 N1 . 1.288(4) ?
C9 C10 . 1.497(4) ?
C10 N4 . 1.283(4) ?
C10 C11 . 1.480(4) ?
C11 O2 . 1.224(4) ?
C11 N3 . 1.371(4) ?
C12 N3 . 1.468(4) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 C14 . 1.389(4) ?
C13 N4 . 1.392(4) ?
C13 C18 . 1.405(4) ?
C14 C15 . 1.368(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.384(5) ?
C15 Cl2 . 1.734(3) ?
C16 C17 . 1.370(4) ?
C16 H16 . 0.93 ?
C17 C18 . 1.401(4) ?
C17 H17 . 0.93 ?
C18 N3 . 1.388(4) ?
