#------------------------------------------------------------------------------
#$Date: 2016-11-08 22:14:03 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188270 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/40/1544069.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_1544069
loop_
_publ_author_name
'Cai, Jiawei'
'Li, Zhixin'
'Qiu, Yanxuan'
'OuYang, Zhijian'
'Lin, Wenning'
'Yang, Liu'
'Feng, Weijin'
'Yu, Xinwei'
'Dong, Wen'
_publ_section_title
;
 The syntheses, structures and azo--hydrazone tautomeric studies of three
 triazole/tetrazole azo dyes
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              9370
_journal_paper_doi               10.1039/C5NJ02539G
_journal_volume                  40
_journal_year                    2016
_chemical_formula_sum            'C11 H8 N6 O'
_chemical_formula_weight         240.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-07-27 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.008(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1366(3)
_cell_length_b                   16.9882(6)
_cell_length_c                   9.4410(4)
_cell_measurement_reflns_used    2157
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.40
_cell_volume                     1061.20(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8967
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0017(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0444P)²+0.1523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                1625
_reflns_number_total             2437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj02539g2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544069--1544070.cif.
;
_cod_original_cell_volume        1061.20(7)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1544069
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.90557(17) 1.05971(7) 0.15107(13) 0.0375(3) Uani 1 1 d .
C2 C 0.8361(2) 0.98788(9) 0.12364(16) 0.0358(3) Uani 1 1 d .
C3 C 0.7049(2) 0.97001(8) -0.03383(16) 0.0352(3) Uani 1 1 d .
N2 N 1.02191(19) 1.07970(8) 0.29369(15) 0.0433(3) Uani 1 1 d .
N3 N 1.06212(19) 1.20896(7) 0.21021(15) 0.0444(3) Uani 1 1 d .
H2 H 0.9800 1.2048 0.1167 0.053 Uiso 1 1 calc R
C8 C 0.6291(2) 0.89345(9) -0.07085(17) 0.0393(4) Uani 1 1 d .
C11 C 1.1003(2) 1.15354(9) 0.31621(16) 0.0389(4) Uani 1 1 d .
C1 C 0.8845(2) 0.92534(9) 0.24079(18) 0.0425(4) Uani 1 1 d .
C7 C 0.5009(2) 0.87637(10) -0.21959(19) 0.0490(4) Uani 1 1 d .
H6 H 0.4517 0.8254 -0.2444 0.059 Uiso 1 1 calc R
C10 C 0.8018(3) 0.84866(10) 0.19144(19) 0.0526(4) Uani 1 1 d .
H8 H 0.8309 0.8080 0.2624 0.063 Uiso 1 1 calc R
N6 N 1.2313(2) 1.18000(8) 0.44629(14) 0.0492(4) Uani 1 1 d .
C4 C 0.6478(2) 1.02722(9) -0.14769(17) 0.0429(4) Uani 1 1 d .
H3 H 0.6967 1.0783 -0.1246 0.051 Uiso 1 1 calc R
C9 C 0.6847(3) 0.83415(10) 0.0469(2) 0.0505(4) Uani 1 1 d .
H7 H 0.6363 0.7832 0.0204 0.061 Uiso 1 1 calc R
C5 C 0.5199(2) 1.00906(11) -0.29403(18) 0.0507(4) Uani 1 1 d .
H4 H 0.4831 1.0478 -0.3691 0.061 Uiso 1 1 calc R
C6 C 0.4459(2) 0.93330(11) -0.33006(19) 0.0532(5) Uani 1 1 d .
H5 H 0.3591 0.9212 -0.4290 0.064 Uiso 1 1 calc R
N4 N 1.1739(2) 1.27283(8) 0.27386(16) 0.0552(4) Uani 1 1 d .
N5 N 1.2729(2) 1.25431(8) 0.41425(16) 0.0540(4) Uani 1 1 d .
O1 O 0.99265(18) 0.93869(7) 0.37598(13) 0.0583(4) Uani 1 1 d .
H1 H 1.055(3) 1.0429(12) 0.370(2) 0.077(6) Uiso 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'
Mn Mn 0.3368 0.7283 '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
C2 N1 N2 118.97(12)
N1 C2 C3 116.54(13)
N1 C2 C1 123.94(13)
C3 C2 C1 119.52(13)
C4 C3 C8 118.78(14)
C4 C3 C2 122.07(14)
C8 C3 C2 119.13(13)
N1 N2 C11 117.22(13)
N1 N2 H1 119.9(13)
C11 N2 H1 122.7(13)
C11 N3 N4 108.38(13)
C11 N3 H2 125.8
N4 N3 H2 125.8
C7 C8 C3 119.49(14)
C7 C8 C9 121.35(15)
C3 C8 C9 119.16(14)
N6 C11 N3 109.62(14)
N6 C11 N2 124.76(14)
N3 C11 N2 125.58(14)
O1 C1 C10 121.48(14)
O1 C1 C2 121.30(14)
C10 C1 C2 117.23(14)
C6 C7 C8 121.01(16)
C6 C7 H6 119.5
C8 C7 H6 119.5
C9 C10 C1 121.73(15)
C9 C10 H8 119.1
C1 C10 H8 119.1
C11 N6 N5 104.39(12)
C5 C4 C3 120.74(15)
C5 C4 H3 119.6
C3 C4 H3 119.6
C10 C9 C8 123.21(15)
C10 C9 H7 118.4
C8 C9 H7 118.4
C4 C5 C6 120.25(16)
C4 C5 H4 119.9
C6 C5 H4 119.9
C7 C6 C5 119.74(15)
C7 C6 H5 120.1
C5 C6 H5 120.1
N5 N4 N3 105.51(13)
N4 N5 N6 112.09(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3060(18)
N1 N2 1.3341(16)
C2 C3 1.4615(19)
C2 C1 1.478(2)
C3 C4 1.392(2)
C3 C8 1.402(2)
N2 C11 1.3574(19)
N2 H1 0.912(19)
N3 C11 1.3257(18)
N3 N4 1.3473(17)
N3 H2 0.8600
C8 C7 1.389(2)
C8 C9 1.441(2)
C11 N6 1.3130(18)
C1 O1 1.2401(17)
C1 C10 1.434(2)
C7 C6 1.368(2)
C7 H6 0.9300
C10 C9 1.329(2)
C10 H8 0.9300
N6 N5 1.3565(19)
C4 C5 1.375(2)
C4 H3 0.9300
C9 H7 0.9300
C5 C6 1.384(2)
C5 H4 0.9300
C6 H5 0.9300
N4 N5 1.2857(18)
