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_7125209
_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         'C25 H33 N5 O4 S'
_chemical_formula_sum            'C25 H33 N5 O4 S'
_chemical_formula_weight         499.63
_chemical_name_systematic
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-phenylethan-1-amine/N,N-diethylformamide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                90.0000
_cell_angle_beta                 99.5040(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   6.21672(11)
_cell_length_b                   26.5810(5)
_cell_length_c                   7.98985(14)
_cell_measurement_reflns_used    12359
_cell_measurement_temperature    213
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.33
_cell_volume                     1302.17(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.1078
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13515
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         3.325
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/DEF'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details
;
 Flack x determined using 1393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_extinction_coef       0.0066(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0405P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3833
_reflns_number_total             4617
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6cc07544d2.cif
_cod_data_source_block           2-DEF
_cod_database_code               7125209
_shelx_res_checksum              89792