#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:19:32 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256169 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157644.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_7157644
loop_
_publ_author_name
'Sharma, Suraj'
'Dutta, Nibedita Baruah'
'Bhuyan, Mayurakhi'
'Das, Babulal'
'Baishya, Gakul'
_publ_section_title
;
 tert-Butylhydroperoxide (TBHP) mediated oxidative
 cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with
 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and
 2-hydroxy-1,4-naphthoquinone under metal-free conditions.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6537
_journal_page_last               6548
_journal_paper_doi               10.1039/d0ob01304h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C21 H16 N2 O4'
_chemical_formula_weight         360.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-04 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6367(15)
_cell_length_b                   13.5661(12)
_cell_length_c                   14.5573(13)
_cell_measurement_reflns_used    3074
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      1.894
_cell_volume                     3483.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            134486
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.894
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       plates
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0135(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0559
_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)+(0.0657P)²+2.2232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2524
_reflns_number_total             3074
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01304h2.cif
_cod_data_source_block           SS-199_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7157644.cif.'
_cod_database_code               7157644
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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
O2 O 0.36489(11) 0.69466(14) 0.31892(14) 0.0553(5) Uani 1 1 d . . . . .
O4 O 0.31097(10) 0.40611(14) 0.36994(15) 0.0560(6) Uani 1 1 d . . . . .
O1 O 0.33022(12) 0.55773(15) 0.24961(15) 0.0638(6) Uani 1 1 d . . . . .
O3 O 0.55638(11) 0.57120(15) 0.42222(16) 0.0600(6) Uani 1 1 d . . . . .
H3 H 0.5622 0.5139 0.4058 0.090 Uiso 1 1 calc R U . . .
N1 N 0.38912(11) 0.27377(15) 0.35978(14) 0.0410(5) Uani 1 1 d . . . . .
N2 N 0.51166(12) 0.40198(17) 0.36296(15) 0.0451(6) Uani 1 1 d . . . . .
C6 C 0.30623(13) 0.17077(17) 0.45929(19) 0.0413(6) Uani 1 1 d . . . . .
C15 C 0.37493(14) 0.37407(18) 0.36102(16) 0.0385(6) Uani 1 1 d . . . . .
C14 C 0.44329(14) 0.43843(19) 0.35442(16) 0.0388(6) Uani 1 1 d . . . . .
C16 C 0.43614(14) 0.54556(19) 0.35072(16) 0.0390(6) Uani 1 1 d . . . . .
C1 C 0.31836(15) 0.2278(2) 0.5360(2) 0.0501(7) Uani 1 1 d . . . . .
H1 H 0.3377 0.2913 0.5295 0.060 Uiso 1 1 calc R U . . .
C20 C 0.37440(15) 0.59297(19) 0.30301(18) 0.0453(6) Uani 1 1 d . . . . .
C17 C 0.49218(15) 0.6057(2) 0.38810(17) 0.0450(6) Uani 1 1 d . . . . .
C8 C 0.46216(15) 0.2355(2) 0.36626(18) 0.0454(6) Uani 1 1 d . . . . .
C7 C 0.32237(15) 0.2087(2) 0.36402(18) 0.0463(7) Uani 1 1 d . . . . .
H7A H 0.3304 0.1531 0.3233 0.056 Uiso 1 1 calc R U . . .
H7B H 0.2784 0.2446 0.3420 0.056 Uiso 1 1 calc R U . . .
C13 C 0.52295(15) 0.3015(2) 0.36920(19) 0.0479(7) Uani 1 1 d . . . . .
C5 C 0.27581(16) 0.07712(19) 0.4706(2) 0.0538(7) Uani 1 1 d . . . . .
H5 H 0.2670 0.0375 0.4195 0.065 Uiso 1 1 calc R U . . .
C4 C 0.25850(17) 0.0424(2) 0.5577(3) 0.0645(9) Uani 1 1 d . . . . .
H4 H 0.2370 -0.0198 0.5646 0.077 Uiso 1 1 calc R U . . .
C18 C 0.48147(18) 0.7096(2) 0.3928(2) 0.0565(8) Uani 1 1 d . . . . .
H18 H 0.5189 0.7492 0.4185 0.068 Uiso 1 1 calc R U . . .
C19 C 0.41857(19) 0.7502(2) 0.3607(2) 0.0582(8) Uani 1 1 d . . . . .
C2 C 0.30222(17) 0.1920(2) 0.6223(2) 0.0604(8) Uani 1 1 d . . . . .
H2 H 0.3113 0.2311 0.6737 0.073 Uiso 1 1 calc R U . . .
C3 C 0.27274(17) 0.0986(3) 0.6332(2) 0.0649(9) Uani 1 1 d . . . . .
H3A H 0.2627 0.0742 0.6916 0.078 Uiso 1 1 calc R U . . .
C9 C 0.47643(18) 0.1341(2) 0.3727(2) 0.0635(9) Uani 1 1 d . . . . .
H9 H 0.4364 0.0894 0.3726 0.076 Uiso 1 1 calc R U . . .
C12 C 0.59676(17) 0.2655(3) 0.3763(2) 0.0676(9) Uani 1 1 d . . . . .
H12 H 0.6373 0.3094 0.3781 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5503(2) 0.1010(3) 0.3793(3) 0.0788(11) Uani 1 1 d . . . . .
H10 H 0.5597 0.0337 0.3828 0.095 Uiso 1 1 calc R U . . .
C11 C 0.6101(2) 0.1662(3) 0.3807(3) 0.0796(11) Uani 1 1 d . . . . .
H11 H 0.6596 0.1428 0.3846 0.096 Uiso 1 1 calc R U . . .
C21 C 0.3961(3) 0.8564(3) 0.3645(3) 0.0958(14) Uani 1 1 d . . . . .
H21A H 0.4318 0.8921 0.4014 0.144 Uiso 1 1 calc R U . . .
H21B H 0.3464 0.8620 0.3910 0.144 Uiso 1 1 calc R U . . .
H21C H 0.3955 0.8832 0.3034 0.144 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'
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
_geom_angle_publ_flag
C19 O2 C20 122.4(2) . . ?
C17 O3 H3 109.5 . . ?
C15 N1 C8 122.2(2) . . ?
C15 N1 C7 116.4(2) . . ?
C8 N1 C7 120.9(2) . . ?
C14 N2 C13 120.8(2) . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C7 119.6(2) . . ?
O4 C15 N1 121.4(2) . . ?
O4 C15 C14 123.2(2) . . ?
N1 C15 C14 115.4(2) . . ?
N2 C14 C16 117.3(2) . . ?
N2 C14 C15 121.1(2) . . ?
C16 C14 C15 121.0(2) . . ?
C17 C16 C20 117.6(2) . . ?
C17 C16 C14 120.5(2) . . ?
C20 C16 C14 121.8(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
O1 C20 O2 114.8(2) . . ?
O1 C20 C16 128.6(3) . . ?
O2 C20 C16 116.6(2) . . ?
O3 C17 C16 123.2(3) . . ?
O3 C17 C18 116.5(2) . . ?
C16 C17 C18 120.3(3) . . ?
N1 C8 C13 118.2(2) . . ?
N1 C8 C9 122.5(3) . . ?
C13 C8 C9 119.3(3) . . ?
N1 C7 C6 113.2(2) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N2 C13 C12 119.0(3) . . ?
N2 C13 C8 121.3(2) . . ?
C12 C13 C8 119.6(3) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 O2 120.9(3) . . ?
C18 C19 C21 127.6(3) . . ?
O2 C19 C21 111.5(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
O2 C19 1.354(3) . ?
O2 C20 1.409(3) . ?
O4 C15 1.216(3) . ?
O1 C20 1.200(3) . ?
O3 C17 1.322(3) . ?
O3 H3 0.8200 . ?
N1 C15 1.384(3) . ?
N1 C8 1.392(3) . ?
N1 C7 1.473(3) . ?
N2 C14 1.309(3) . ?
N2 C13 1.381(4) . ?
C6 C1 1.376(4) . ?
C6 C5 1.389(4) . ?
C6 C7 1.506(4) . ?
C15 C14 1.492(3) . ?
C14 C16 1.460(4) . ?
C16 C17 1.392(3) . ?
C16 C20 1.443(4) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9300 . ?
C17 C18 1.424(4) . ?
C8 C13 1.397(4) . ?
C8 C9 1.402(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C12 1.394(4) . ?
C5 C4 1.387(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.361(5) . ?
C4 H4 0.9300 . ?
C18 C19 1.324(4) . ?
C18 H18 0.9300 . ?
C19 C21 1.495(5) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9300 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C12 C11 1.369(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
