Structure and absolute configuration of (+)-6-[(4-chlorophenyl)(1<i>H</i>-1,2,4-triazol-1-yl)methyl]-1-methyl-1<i>H</i>-benzotriazole (vorozole) and its hydrobromide monohydrate
Peeters, O. M.; Schuerman, G. S.; Blaton, N. M.; De Ranter, C. J.; Acta Crystallographica Section C 49 (1993) 1958–1961; doi:10.1107/S0108270193004792

data_2001228
_publ_section_title
;Structure and absolute configuration of
 (+)-6-[(4-chlorophenyl)(1<i>H</i>-1,2,4-triazol-1-yl)methyl]-1-methyl-1<i>H</i>-benzotriazole
 (vorozole) and its hydrobromide monohydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1958
_journal_page_last               1961
_journal_paper_doi               10.1107/S0108270193004792
_journal_volume                  49
_journal_year                    1993
_chemical_formula_analytical     'C16 H16 Br1 Cl1 N6 O1'
_chemical_formula_moiety         'C16 H14 Cl1 N6 , Br1 , H2 O1'
_chemical_formula_sum            'C16 H16 Br Cl N6 O'
_chemical_formula_weight         423.70
_chemical_name_systematic
;
(+)-6-[(4-Chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-
benzotriazole Hydrobromide Monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   6.008(3)
_cell_length_b                   8.401(4)
_cell_length_c                   35.92(2)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    293
_cell_measurement_theta_max      24
_cell_measurement_theta_min      16
_cell_volume                     1813.0(16)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1988)'
_computing_data_reduction        'locally adapted REDU4 (Stoe & Cie, 1988)'
_computing_molecular_graphics    PLUTO
_computing_publication_material  PARST
_computing_structure_refinement  NRCVAX
_computing_structure_solution    'DIRDIF92 (Beurskens et al., 1992)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Stoe STADI4 four-circle diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  'perpendicular mounted graphite 002'
_diffrn_radiation_source         'fine focus Siemens Mo tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0228
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            7547
_diffrn_reflns_reduction_process
;
Decay, Lp and absorption corrected intensities were averaged for
equivalent reflections, except for Friedel pairs.
;
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         1.13
_diffrn_standards_decay_%        4.1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.4088
_exptl_absorpt_correction_T_max  .130
_exptl_absorpt_correction_T_min  .104
_exptl_absorpt_correction_type   'empirical (EMPIR; Stoe & Cie)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      1.53
_exptl_crystal_density_method    'flotation CCl~4~/n-heptane'
_exptl_crystal_description       Parallelipiped
_exptl_crystal_F_000             856
_exptl_crystal_size_max          .55
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .20
_refine_diff_density_max         .26
_refine_diff_density_min         -.38
_refine_ls_abs_structure_details
;
The Bijvoet coefficient was between 0.958(1) and 0.9924(1) for the 261
and 68 most significant Bijvoet pairs, respectively.
;
_refine_ls_extinction_coef       .00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.57
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2269
_refine_ls_R_factor_all          .0617
_refine_ls_R_factor_obs          .0360
_refine_ls_shift/esd_max         .002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(F)+.00040F^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .0484
_refine_ls_wR_factor_obs         .0451
_reflns_number_observed          2269
_reflns_number_total             3183
_reflns_observed_criterion       I>2.0\s(I)
_cod_data_source_file            na1038.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F)+.00040F^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(F)+.00040F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1813(2)
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_original_formula_sum        'C16 H16 Br1 Cl1 N6 O1'
_cod_database_code               2001228