#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/26/2222646.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222646
loop_
_publ_author_name
'Leeju, P.'
'Arun, V.'
'Sebastian, Manju'
'Varsha, G.'
'Varghese, Digna'
'Yusuff, K. K. M.'
_publ_section_title
;
 N-[(E)-Quinoxalin-2-ylmethylidene]-1H-indazol-5-amine
;
_journal_coeditor_code           CV2578
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1981
_journal_paper_doi               10.1107/S1600536809027822
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H11 N5'
_chemical_formula_moiety         'C16 H11 N5'
_chemical_formula_sum            'C16 H11 N5'
_chemical_formula_weight         273.30
_chemical_name_systematic
;
N-[(E)-Quinoxalin-2-ylmethylidene]-1H-indazol-5-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.882(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7015(6)
_cell_length_b                   8.0330(6)
_cell_length_c                   20.6034(16)
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.760
_cell_measurement_theta_min      2.60
_cell_volume                     1265.47(17)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16012
_diffrn_reflns_theta_full        29.76
_diffrn_reflns_theta_max         29.76
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0715P)²+0.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                2502
_reflns_number_total             3597
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2578.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222646
_cod_database_fobs_code          2222646
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.25032(15) 0.66502(15) 0.33833(5) 0.0436(3) Uani d . 1 . .
N N2 0.14194(13) 0.77204(14) 0.45776(5) 0.0392(3) Uani d . 1 . .
N N3 0.30313(15) 0.37642(14) 0.50779(5) 0.0413(3) Uani d . 1 . .
N N4 0.38605(15) -0.08636(16) 0.70573(5) 0.0454(3) Uani d . 1 . .
H H4 0.3774 -0.0851 0.7470 0.054 Uiso calc R 1 . .
N N5 0.42455(17) -0.22452(16) 0.67229(6) 0.0515(3) Uani d . 1 . .
C C1 0.18211(15) 0.82051(17) 0.34459(6) 0.0368(3) Uani d . 1 . .
C C2 0.16182(18) 0.9289(2) 0.29041(6) 0.0469(3) Uani d . 1 . .
H H2 0.1980 0.8960 0.2509 0.056 Uiso calc R 1 . .
C C3 0.08916(19) 1.0817(2) 0.29612(7) 0.0507(4) Uani d . 1 . .
H H3 0.0724 1.1511 0.2598 0.061 Uiso calc R 1 . .
C C4 0.03910(19) 1.1364(2) 0.35576(7) 0.0490(4) Uani d . 1 . .
H H4A -0.0073 1.2426 0.3589 0.059 Uiso calc R 1 . .
C C5 0.05790(18) 1.03530(18) 0.40912(7) 0.0440(3) Uani d . 1 . .
H H5 0.0247 1.0724 0.4486 0.053 Uiso calc R 1 . .
C C6 0.12780(16) 0.87452(17) 0.40443(6) 0.0361(3) Uani d . 1 . .
C C7 0.26273(18) 0.57069(18) 0.39027(6) 0.0436(3) Uani d . 1 . .
H H7 0.3088 0.4642 0.3877 0.052 Uiso calc R 1 . .
C C8 0.20879(16) 0.62367(16) 0.45062(6) 0.0374(3) Uani d . 1 . .
C C9 0.22517(17) 0.51440(18) 0.50816(6) 0.0411(3) Uani d . 1 . .
H H9 0.1773 0.5475 0.5455 0.049 Uiso calc R 1 . .
C C10 0.32246(16) 0.27137(17) 0.56339(6) 0.0369(3) Uani d . 1 . .
C C11 0.36804(16) 0.10932(16) 0.55175(6) 0.0375(3) Uani d . 1 . .
H H11 0.3848 0.0756 0.5098 0.045 Uiso calc R 1 . .
C C12 0.38887(16) -0.00418(17) 0.60359(6) 0.0360(3) Uani d . 1 . .
C C13 0.36273(15) 0.04951(17) 0.66654(6) 0.0365(3) Uani d . 1 . .
C C14 0.42856(19) -0.17552(18) 0.61149(6) 0.0460(3) Uani d . 1 . .
H H14 0.4543 -0.2451 0.5778 0.055 Uiso calc R 1 . .
C C15 0.32249(17) 0.21454(18) 0.67939(6) 0.0421(3) Uani d . 1 . .
H H15 0.3096 0.2496 0.7216 0.051 Uiso calc R 1 . .
C C16 0.30258(18) 0.32333(18) 0.62789(6) 0.0427(3) Uani d . 1 . .
H H16 0.2754 0.4339 0.6354 0.051 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 116.38(11) ?
C8 N2 C6 . . 116.81(10) ?
C9 N3 C10 . . 121.52(11) ?
C13 N4 N5 . . 112.15(10) ?
C13 N4 H4 . . 123.9 ?
N5 N4 H4 . . 123.9 ?
C14 N5 N4 . . 105.65(12) ?
N1 C1 C2 . . 119.81(11) ?
N1 C1 C6 . . 121.24(11) ?
C2 C1 C6 . . 118.94(12) ?
C3 C2 C1 . . 119.78(13) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 121.20(13) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 120.49(14) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C4 C5 C6 . . 119.80(13) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
N2 C6 C5 . . 119.47(11) ?
N2 C6 C1 . . 120.78(12) ?
C5 C6 C1 . . 119.75(12) ?
N1 C7 C8 . . 122.85(13) ?
N1 C7 H7 . . 118.6 ?
C8 C7 H7 . . 118.6 ?
N2 C8 C7 . . 121.92(12) ?
N2 C8 C9 . . 116.67(11) ?
C7 C8 C9 . . 121.40(12) ?
N3 C9 C8 . . 121.03(12) ?
N3 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 N3 . . 115.26(11) ?
C11 C10 C16 . . 119.99(12) ?
N3 C10 C16 . . 124.73(12) ?
C10 C11 C12 . . 119.44(11) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C11 C12 C13 . . 119.28(12) ?
C11 C12 C14 . . 136.49(12) ?
C13 C12 C14 . . 104.21(11) ?
N4 C13 C15 . . 131.95(11) ?
N4 C13 C12 . . 106.21(12) ?
C15 C13 C12 . . 121.83(12) ?
N5 C14 C12 . . 111.77(12) ?
N5 C14 H14 . . 124.1 ?
C12 C14 H14 . . 124.1 ?
C16 C15 C13 . . 117.81(11) ?
C16 C15 H15 . . 121.1 ?
C13 C15 H15 . . 121.1 ?
C15 C16 C10 . . 121.58(13) ?
C15 C16 H16 . . 119.2 ?
C10 C16 H16 . . 119.2 ?
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
N1 C7 . 1.3053(17) ?
N1 C1 . 1.3670(17) ?
N2 C8 . 1.3136(17) ?
N2 C6 . 1.3668(16) ?
N3 C9 . 1.2610(18) ?
N3 C10 . 1.4162(16) ?
N4 C13 . 1.3568(17) ?
N4 N5 . 1.3576(17) ?
N4 H4 . 0.8600 ?
N5 C14 . 1.3169(17) ?
C1 C2 . 1.4094(18) ?
C1 C6 . 1.4167(17) ?
C2 C3 . 1.360(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.402(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3605(19) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.4070(19) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.4225(17) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4684(17) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.3768(18) ?
C10 C16 . 1.4185(17) ?
C11 C12 . 1.3989(17) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.4039(16) ?
C12 C14 . 1.4150(19) ?
C13 C15 . 1.3941(19) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.3691(18) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cg1 Cg3 3.7080(2) . 3_575 n
Cg2 Cg3 3.8220(5) . 3_777 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H4 N1 4_566 0.86 2.31 3.1050(15) 152.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742882
