Hierarchical construction of SHG-active polar crystals by using multi-component crystals.
Miyano, Tetsuya; Sakai, Tatsuya; Hisaki, Ichiro; Ichida, Hideki; Kanematsu, Yasuo; Tohnai, Norimitsu; Chemical communications (Cambridge, England) 52 (2016) 13710–13713; doi:10.1039/c6cc07544d

data_7125203
_publ_section_title
;
 Hierarchical construction of SHG-active polar crystals by using
 multi-component crystals.
;
_journal_issue                   94
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13710
_journal_page_last               13713
_journal_paper_doi               10.1039/c6cc07544d
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H28 Cl N5 O4 S'
_chemical_formula_sum            'C23 H28 Cl N5 O4 S'
_chemical_formula_weight         506.02
_chemical_name_systematic
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine/N,N-dimethylformamide'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                83.8975(16)
_cell_angle_beta                 82.0150(15)
_cell_angle_gamma                71.9997(15)
_cell_formula_units_Z            1
_cell_length_a                   5.94757(14)
_cell_length_b                   9.5911(2)
_cell_length_c                   11.4509(3)
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    213
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      3.90
_cell_volume                     613.81(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      213
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6470
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.127
_diffrn_reflns_theta_min         3.907
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_T_max  0.606
_exptl_absorpt_correction_T_min  0.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             266.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/DMF'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.47
_refine_ls_abs_structure_details
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_coef       0.010(5)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0851
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1731P)^2^+0.0945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2281
_refine_ls_wR_factor_ref         0.2643
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.644
_reflns_Friedel_fraction_max     0.639
_reflns_number_gt                3036
_reflns_number_total             3604
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6cc07544d2.cif
_cod_data_source_block           1-DMF
_cod_original_cell_volume        613.82(3)
_cod_database_code               7125203
_shelx_res_checksum              51322