#------------------------------------------------------------------------------
#$Date: 2017-04-05 13:05:06 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195165 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/54/7155495.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_7155495
loop_
_publ_author_name
'Gopalaiah, Kovuru'
'Saini, Anupama'
'Chandrudu, Sankala Naga'
'Rao, Devarapalli Chenna'
'Yadav, Harsh'
'Kumar, Binay'
_publ_section_title
;
 Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with
 2-aryl/heteroarylethylamines: direct access to construct quinoxalines.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2259
_journal_page_last               2268
_journal_paper_doi               10.1039/c7ob00122c
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C14 H9 N3 O2'
_chemical_formula_sum            'C14 H9 N3 O2'
_chemical_formula_weight         251.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2016-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 79.702(6)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.3758(4)
_cell_length_b                   12.4522(7)
_cell_length_c                   14.7628(10)
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.9400
_cell_measurement_theta_min      3.5550
_cell_volume                     1153.18(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15229
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.272
_diffrn_reflns_theta_min         3.247
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       Block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0055(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1536
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1405
_reflns_number_total             2853
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob00122c2.cif
_cod_data_source_block           2-4-Nitrophenylquinoxaline
_cod_depositor_comments
'Adding full bibliography for 7155495--7155499.cif.'
_cod_database_code               7155495
_publcif_datablock.id            {434d6885-0acc-4fdb-8c31-148438362a6b}
_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_max   0.998
_shelx_estimated_absorpt_t_min   0.998
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 1.0814(3) 0.23752(18) -0.10178(14) 0.0882(7) Uani 1 1 d .
O2 O 0.9951(3) 0.07137(19) -0.08890(16) 0.1110(9) Uani 1 1 d .
N1 N 0.9568(3) 0.1661(2) -0.07416(14) 0.0670(7) Uani 1 1 d .
N2 N 0.0644(3) 0.37378(15) 0.11122(12) 0.0490(5) Uani 1 1 d .
N3 N -0.1811(3) 0.22869(16) 0.23247(14) 0.0631(6) Uani 1 1 d .
C1 C 0.7464(3) 0.1950(2) -0.02172(16) 0.0517(6) Uani 1 1 d .
C2 C 0.6741(4) 0.2975(2) -0.02602(16) 0.0574(7) Uani 1 1 d .
H2 H 0.757823 0.349301 -0.060662 0.069 Uiso 1 1 calc R
C3 C 0.4748(3) 0.32283(19) 0.02182(16) 0.0548(7) Uani 1 1 d .
H3 H 0.423301 0.392342 0.018763 0.066 Uiso 1 1 calc R
C4 C 0.3496(3) 0.24653(18) 0.07450(14) 0.0445(6) Uani 1 1 d .
C5 C 0.4294(4) 0.1442(2) 0.07787(17) 0.0659(8) Uani 1 1 d .
H5 H 0.347974 0.092199 0.113261 0.079 Uiso 1 1 calc R
C6 C 0.6284(4) 0.1177(2) 0.02953(18) 0.0694(8) Uani 1 1 d .
H6 H 0.681089 0.048298 0.031856 0.083 Uiso 1 1 calc R
C7 C 0.1346(3) 0.27703(18) 0.12528(15) 0.0452(6) Uani 1 1 d .
C8 C 0.0083(4) 0.2056(2) 0.18667(17) 0.0608(7) Uani 1 1 d .
H8 H 0.063569 0.137977 0.194986 0.073 Uiso 1 1 calc R
C9 C -0.1323(3) 0.40106(17) 0.15796(15) 0.0463(6) Uani 1 1 d .
C10 C -0.2160(4) 0.50295(19) 0.14410(18) 0.0650(8) Uani 1 1 d .
H10 H -0.136418 0.551419 0.103963 0.078 Uiso 1 1 calc R
C11 C -0.4137(4) 0.5307(2) 0.18942(18) 0.0676(8) Uani 1 1 d .
H11 H -0.468069 0.598305 0.180091 0.081 Uiso 1 1 calc R
C12 C -0.5358(4) 0.4589(2) 0.24971(17) 0.0612(7) Uani 1 1 d .
H12 H -0.670631 0.478996 0.279974 0.073 Uiso 1 1 calc R
C13 C -0.4597(3) 0.3602(2) 0.26455(16) 0.0565(7) Uani 1 1 d .
H13 H -0.541838 0.313207 0.305273 0.068 Uiso 1 1 calc R
C14 C -0.2561(3) 0.32851(19) 0.21834(15) 0.0458(6) Uani 1 1 d .
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
O1 N1 O2 123.5(2)
O1 N1 C1 118.6(2)
O2 N1 C1 117.9(2)
C7 N2 C9 117.26(19)
C8 N3 C14 116.06(19)
C2 C1 N1 119.4(2)
C2 C1 C6 121.9(2)
C6 C1 N1 118.6(2)
C1 C2 H2 120.6
C1 C2 C3 118.8(2)
C3 C2 H2 120.6
C2 C3 H3 119.4
C2 C3 C4 121.1(2)
C4 C3 H3 119.4
C3 C4 C7 119.6(2)
C5 C4 C3 118.3(2)
C5 C4 C7 122.1(2)
C4 C5 H5 119.5
C4 C5 C6 121.0(2)
C6 C5 H5 119.5
C1 C6 C5 118.8(2)
C1 C6 H6 120.6
C5 C6 H6 120.6
N2 C7 C4 117.62(19)
N2 C7 C8 120.4(2)
C8 C7 C4 122.0(2)
N3 C8 C7 124.1(2)
N3 C8 H8 117.9
C7 C8 H8 117.9
N2 C9 C10 119.4(2)
N2 C9 C14 121.4(2)
C10 C9 C14 119.1(2)
C9 C10 H10 120.0
C11 C10 C9 120.0(2)
C11 C10 H10 120.0
C10 C11 H11 119.6
C10 C11 C12 120.8(2)
C12 C11 H11 119.6
C11 C12 H12 119.7
C13 C12 C11 120.6(2)
C13 C12 H12 119.7
C12 C13 H13 119.9
C12 C13 C14 120.1(2)
C14 C13 H13 119.9
N3 C14 C9 120.69(19)
N3 C14 C13 120.0(2)
C9 C14 C13 119.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.213(3)
O2 N1 1.216(3)
N1 C1 1.469(3)
N2 C7 1.315(3)
N2 C9 1.362(3)
N3 C8 1.307(3)
N3 C14 1.361(3)
C1 C2 1.362(3)
C1 C6 1.364(3)
C2 H2 0.9300
C2 C3 1.376(3)
C3 H3 0.9300
C3 C4 1.386(3)
C4 C5 1.376(3)
C4 C7 1.489(3)
C5 H5 0.9300
C5 C6 1.380(3)
C6 H6 0.9300
C7 C8 1.413(3)
C8 H8 0.9300
C9 C10 1.406(3)
C9 C14 1.407(3)
C10 H10 0.9300
C10 C11 1.362(3)
C11 H11 0.9300
C11 C12 1.396(3)
C12 H12 0.9300
C12 C13 1.353(3)
C13 H13 0.9300
C13 C14 1.411(3)
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
O1 N1 C1 C2 17.5(4)
O1 N1 C1 C6 -163.0(3)
O2 N1 C1 C2 -161.3(3)
O2 N1 C1 C6 18.3(4)
N1 C1 C2 C3 178.6(2)
N1 C1 C6 C5 -179.1(2)
N2 C7 C8 N3 0.2(4)
N2 C9 C10 C11 179.1(2)
N2 C9 C14 N3 0.7(4)
N2 C9 C14 C13 -179.4(2)
C1 C2 C3 C4 0.7(4)
C2 C1 C6 C5 0.4(4)
C2 C3 C4 C5 0.0(4)
C2 C3 C4 C7 -180.0(2)
C3 C4 C5 C6 -0.5(4)
C3 C4 C7 N2 6.0(3)
C3 C4 C7 C8 -174.0(2)
C4 C5 C6 C1 0.3(4)
C4 C7 C8 N3 -179.8(2)
C5 C4 C7 N2 -173.9(2)
C5 C4 C7 C8 6.1(4)
C6 C1 C2 C3 -0.9(4)
C7 N2 C9 C10 -178.9(2)
C7 N2 C9 C14 -0.4(3)
C7 C4 C5 C6 179.4(2)
C8 N3 C14 C9 -0.4(4)
C8 N3 C14 C13 179.7(2)
C9 N2 C7 C4 -179.96(19)
C9 N2 C7 C8 0.0(3)
C9 C10 C11 C12 -0.2(4)
C10 C9 C14 N3 179.1(2)
C10 C9 C14 C13 -0.9(3)
C10 C11 C12 C13 0.2(4)
C11 C12 C13 C14 -0.6(4)
C12 C13 C14 N3 -179.1(2)
C12 C13 C14 C9 0.9(4)
C14 N3 C8 C7 0.0(4)
C14 C9 C10 C11 0.6(4)
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
