#------------------------------------------------------------------------------
#$Date: 2016-08-12 17:42:17 +0300 (Fri, 12 Aug 2016) $
#$Revision: 185779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119144.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_7119144
loop_
_publ_author_name
'Erchang Shang'
'Junzhi Zhang'
'Jinyi Bai'
'Zhan Wang'
'Xiang Li'
'Bing Zhu'
'Xiaoguang Lei'
_publ_section_title
;
 Syntheses of [1,2,4]triazolo[1,5-a]benzazoles enabled by the
 transition-metal-free oxidative N-N bond formation
;
_journal_name_full               Chem.Commun.
_journal_page_first              7028
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C16 H14 N4'
_chemical_formula_sum            'C16 H14 N4'
_chemical_formula_weight         262.31
_chemical_name_systematic        4a
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-09 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.062(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9753(6)
_cell_length_b                   15.9285(17)
_cell_length_c                   13.4470(13)
_cell_measurement_reflns_used    738
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.3870
_cell_measurement_theta_min      3.7230
_cell_volume                     1279.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details
;
  1 omega  -12.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000   60.0000 67

  2 omega  -69.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000   60.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0065264000
_diffrn_orient_matrix_UB_12      0.0410949000
_diffrn_orient_matrix_UB_13      0.0201594000
_diffrn_orient_matrix_UB_21      -0.1006203000
_diffrn_orient_matrix_UB_22      -0.0070862000
_diffrn_orient_matrix_UB_23      0.0266555000
_diffrn_orient_matrix_UB_31      0.0626007000
_diffrn_orient_matrix_UB_32      -0.0156613000
_diffrn_orient_matrix_UB_33      0.0407982000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.877
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3290
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.642
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83135
_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    1.361
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0502
_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)+(0.0522P)²+0.1388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1365
_reflns_number_total             2023
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc01976e2.cif
_cod_data_source_block           exp_5557
_cod_database_code               7119144
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C16H10N4
_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   0.996
_shelx_estimated_absorpt_t_min   0.992
_reflns_odcompleteness_completeness 87.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7504(4) 0.04119(15) 0.92980(17) 0.0230(6) Uani 1 1 d . . . . .
C2 C 0.9204(4) 0.13294(15) 1.01143(17) 0.0229(6) Uani 1 1 d . . . . .
C3 C 0.9595(4) 0.01340(15) 0.79482(16) 0.0223(6) Uani 1 1 d . . . . .
C4 C 0.7635(4) -0.03567(15) 0.79362(17) 0.0242(6) Uani 1 1 d . . . . .
C5 C 0.7270(4) -0.09100(16) 0.71646(17) 0.0270(6) Uani 1 1 d . . . . .
H5 H 0.5949 -0.1242 0.7147 0.032 Uiso 1 1 calc R . . . .
C6 C 0.8851(4) -0.09772(16) 0.64145(18) 0.0270(6) Uani 1 1 d . . . . .
C7 C 1.0823(4) -0.04892(16) 0.64373(18) 0.0277(6) Uani 1 1 d . . . . .
C8 C 1.1188(4) 0.00725(15) 0.72140(17) 0.0264(6) Uani 1 1 d . . . . .
H8 H 1.2506 0.0405 0.7236 0.032 Uiso 1 1 calc R . . . .
C9 C 0.8449(5) -0.15908(18) 0.5579(2) 0.0387(7) Uani 1 1 d . . . . .
H9A H 0.7009 -0.1873 0.5680 0.058 Uiso 1 1 calc GR . . . .
H9B H 0.9651 -0.2009 0.5571 0.058 Uiso 1 1 calc GR . . . .
H9C H 0.8424 -0.1289 0.4944 0.058 Uiso 1 1 calc GR . . . .
C10 C 1.2536(5) -0.05674(19) 0.56238(19) 0.0382(7) Uani 1 1 d . . . . .
H10A H 1.3796 -0.0191 0.5763 0.057 Uiso 1 1 calc GR . . . .
H10B H 1.1855 -0.0414 0.4986 0.057 Uiso 1 1 calc GR . . . .
H10C H 1.3075 -0.1148 0.5592 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.9699(4) 0.19430(14) 1.08971(18) 0.0230(6) Uani 1 1 d . . . . .
C12 C 1.1744(4) 0.23601(16) 1.09241(19) 0.0306(7) Uani 1 1 d . . . . .
H12 H 1.2849 0.2243 1.0436 0.037 Uiso 1 1 calc R . . . .
C13 C 1.2173(5) 0.29444(16) 1.1660(2) 0.0373(7) Uani 1 1 d . . . . .
H13 H 1.3566 0.3232 1.1673 0.045 Uiso 1 1 calc R . . . .
C14 C 1.0578(5) 0.31118(17) 1.2377(2) 0.0380(7) Uani 1 1 d . . . . .
H14 H 1.0877 0.3514 1.2881 0.046 Uiso 1 1 calc R . . . .
C15 C 0.8549(5) 0.26945(16) 1.2362(2) 0.0357(7) Uani 1 1 d . . . . .
H15 H 0.7458 0.2806 1.2858 0.043 Uiso 1 1 calc R . . . .
C16 C 0.8115(4) 0.21143(15) 1.16227(19) 0.0293(6) Uani 1 1 d . . . . .
H16 H 0.6717 0.1830 1.1611 0.035 Uiso 1 1 calc R . . . .
H1 H 0.494(6) -0.0496(18) 0.906(2) 0.061(9) Uiso 1 1 d . . . . .
N1 N 0.6349(4) -0.01750(13) 0.87747(15) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.7287(3) 0.08514(13) 1.01302(14) 0.0246(5) Uani 1 1 d . . . . .
N3 N 1.0561(3) 0.12131(12) 0.93379(14) 0.0255(5) Uani 1 1 d . . . . .
N4 N 0.9412(3) 0.06068(12) 0.88211(14) 0.0235(5) 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'
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
N2 C1 N1 138.6(2) . .
N2 C1 N4 111.4(2) . .
N4 C1 N1 110.0(2) . .
N2 C2 C11 121.7(2) . .
N3 C2 C11 122.1(2) . .
N3 C2 N2 116.2(2) . .
C8 C3 C4 121.9(2) . .
C8 C3 N4 134.0(2) . .
N4 C3 C4 104.0(2) . .
C5 C4 C3 119.7(2) . .
C5 C4 N1 130.8(2) . .
N1 C4 C3 109.5(2) . .
C4 C5 H5 120.4 . .
C4 C5 C6 119.3(2) . .
C6 C5 H5 120.4 . .
C5 C6 C7 120.7(2) . .
C5 C6 C9 118.9(2) . .
C7 C6 C9 120.4(2) . .
C6 C7 C10 120.5(2) . .
C8 C7 C6 120.0(2) . .
C8 C7 C10 119.5(2) . .
C3 C8 C7 118.4(2) . .
C3 C8 H8 120.8 . .
C7 C8 H8 120.8 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 C2 120.9(2) . .
C16 C11 C2 119.9(2) . .
C16 C11 C12 119.2(2) . .
C11 C12 H12 119.9 . .
C13 C12 C11 120.1(3) . .
C13 C12 H12 119.9 . .
C12 C13 H13 119.9 . .
C14 C13 C12 120.1(3) . .
C14 C13 H13 119.9 . .
C13 C14 H14 119.9 . .
C13 C14 C15 120.1(3) . .
C15 C14 H14 119.9 . .
C14 C15 H15 120.1 . .
C16 C15 C14 119.7(3) . .
C16 C15 H15 120.1 . .
C11 C16 H16 119.7 . .
C15 C16 C11 120.7(2) . .
C15 C16 H16 119.7 . .
C1 N1 C4 106.3(2) . .
C1 N1 H1 123.5(16) . .
C4 N1 H1 129.1(17) . .
C1 N2 C2 101.4(2) . .
C2 N3 N4 100.92(19) . .
C1 N4 C3 110.06(19) . .
C1 N4 N3 110.2(2) . .
N3 N4 C3 139.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.358(3) .
C1 N2 1.327(3) .
C1 N4 1.345(3) .
C2 C11 1.466(3) .
C2 N2 1.375(3) .
C2 N3 1.336(3) .
C3 C4 1.408(3) .
C3 C8 1.376(4) .
C3 N4 1.399(3) .
C4 C5 1.378(3) .
C4 N1 1.396(3) .
C5 H5 0.9500 .
C5 C6 1.387(4) .
C6 C7 1.412(4) .
C6 C9 1.508(3) .
C7 C8 1.392(3) .
C7 C10 1.504(4) .
C8 H8 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.392(3) .
C11 C16 1.387(4) .
C12 H12 0.9500 .
C12 C13 1.382(4) .
C13 H13 0.9500 .
C13 C14 1.382(4) .
C14 H14 0.9500 .
C14 C15 1.383(4) .
C15 H15 0.9500 .
C15 C16 1.382(3) .
C16 H16 0.9500 .
N1 H1 1.05(3) .
N3 N4 1.373(3) .
