Crystal structure of 2-{(<i>R</i>)-[1-(4-bromophenyl)ethyl]iminomethyl}-4-(phenyldiazenyl)phenol, a chiral photochromic Schiff base
Moriwaki, Ryoji; Akitsu, Takashiro; Acta Crystallographica Section E 71 (2015) o886–o887; doi:10.1107/S2056989015019866

data_2241257
_publ_section_title
;
 Crystal structure of
 2-{(<i>R</i>)-[1-(4-bromophenyl)ethyl]iminomethyl}-4-(phenyldiazenyl)phenol,
 a chiral photochromic Schiff base
;
_journal_coeditor_code           CV5499
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o886
_journal_page_last               o887
_journal_paper_doi               10.1107/S2056989015019866
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C21 H18 Br N3 O'
_chemical_formula_moiety         'C21 H18 Br N3 O'
_chemical_formula_sum            'C21 H18 Br N3 O'
_chemical_formula_weight         408.29
_chemical_name_systematic
;
2-{(<i>R</i>)-[1-(4-Bromophenyl)ethyl]iminomethyl}-4-(phenyldiazenyl)phenol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.271(3)
_cell_length_b                   41.901(15)
_cell_length_c                   5.952(2)
_cell_measurement_reflns_used    10349
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      2.84
_cell_volume                     1813.3(12)
_computing_cell_refinement
;
SAINT (Bruker, 1998)
;
_computing_data_collection
;
APEX2 (Bruker, 1998)
;
_computing_data_reduction
;
SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10349
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    2.282
_exptl_absorpt_correction_T_max  0.8330
_exptl_absorpt_correction_T_min  0.4860
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.399
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0467
_reflns_number_gt                3723
_reflns_number_total             4176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cv5499sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1813.3(11)
_cod_database_code               2241257
_cod_database_fobs_code          2241257
_shelx_hkl_checksum              65283
_shelx_res_checksum              36553