(<i>E</i>)-(4-Hydroxyphenyl)(4-nitrophenyl)diazene, (<i>E</i>)-(4-methoxyphenyl)(4-nitrophenyl)diazene and (<i>E</i>)-[4-(6-bromohexyloxy)phenyl](4-cyanophenyl)diazene
Huang, Xinjiang; Kuhn, Genevieve H.; Nesterov, Vladimir N.; Averkiev, Boris B.; Penn, Benjamin; Antipin, Mikhail Yu.; Timofeeva, Tatiana V.; Acta Crystallographica Section C 58 (2002) o624–o628; doi:10.1107/S010827010201627X

data_2012983
_publ_section_title
;
 (<i>E</i>)-(4-Hydroxyphenyl)(4-nitrophenyl)diazene,
 (<i>E</i>)-(4-methoxyphenyl)(4-nitrophenyl)diazene and
 (<i>E</i>)-[4-(6-bromohexyloxy)phenyl](4-cyanophenyl)diazene
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o624
_journal_page_last               o628
_journal_paper_doi               10.1107/S010827010201627X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C19 H20 Br N3 O'
_chemical_formula_sum            'C19 H20 Br N3 O'
_chemical_formula_weight         386.29
_chemical_melting_point          376
_chemical_name_systematic
;
(E)-[4-(6-bromohexyloxy)phenyl](4-cyanophenyl)diazene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                86.502(5)
_cell_angle_beta                 80.511(5)
_cell_angle_gamma                87.604(5)
_cell_formula_units_Z            4
_cell_length_a                   7.4279(18)
_cell_length_b                   12.009(3)
_cell_length_c                   19.552(5)
_cell_measurement_reflns_used    320
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      4
_cell_volume                     1716.1(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1994)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.083
_diffrn_reflns_av_sigmaI/netI    0.292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20166
_diffrn_reflns_theta_full        30.1
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    2.406
_exptl_absorpt_correction_T_max  0.697
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.676
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         9845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.676
_refine_ls_R_factor_all          0.161
_refine_ls_R_factor_gt           0.047
_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^)+(0.02P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.077
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                3353
_reflns_number_total             9845
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg1133.cif
_cod_data_source_block           IIIc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1716.2(7)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2012983
_cod_database_fobs_code          2012983