The syntheses, structures and azo–hydrazone tautomeric studies of three triazole/tetrazole azo dyes
Cai, Jiawei; Li, Zhixin; Qiu, Yanxuan; OuYang, Zhijian; Lin, Wenning; Yang, Liu; Feng, Weijin; Yu, Xinwei; Dong, Wen; New J. Chem. 40 (2016) 9370–; doi:10.1039/C5NJ02539G

data_1544070
_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_moiety         'C12 H7 N5 O'
_chemical_formula_sum            'C12 H7 N5 O'
_chemical_formula_weight         237.23
_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
_audit_creation_date             2016-07-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5095)
;
_audit_update_record
;
2016-07-24 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.735(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7787(3)
_cell_length_b                   15.4361(13)
_cell_length_c                   17.0098(14)
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.8545
_cell_measurement_theta_min      2.3945
_cell_volume                     991.02(14)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14370
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         1.782
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0640 before and 0.0311 after correction.
The Ratio of minimum to maximum transmission is 0.7005.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488.0
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0505
_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/[\s^2^(Fo^2^)+(0.0658P)^2^+0.0340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1106
_reflns_number_total             2280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02539g2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 1544069--1544070.cif.'
_cod_database_code               1544070
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1A
 0.8 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C11(H11), C6(H6), C5(H5), C1(H1)
;
_shelx_res_checksum              43149
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'