Varying the regiochemistry of a [2 + 2] cycloaddition reaction within isostructural hydrogen bonded cocrystals containing 4-stilbazole
Grobelny, Anna L.; Rath, Nigam P.; Groeneman, Ryan H.; CrystEngComm 20 (2018) 3951–; doi:10.1039/C8CE00447A

data_7230854
_publ_section_title
;
 Varying the regiochemistry of a [2 + 2] cycloaddition reaction within
 isostructural hydrogen bonded cocrystals containing 4-stilbazole
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              3951
_journal_paper_doi               10.1039/C8CE00447A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C26 H22 N2, C6 H4 Cl2 O2'
_chemical_formula_sum            'C32 H26 Cl2 N2 O2'
_chemical_formula_weight         541.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-03-14 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9319(13)
_cell_length_b                   9.4899(6)
_cell_length_c                   14.4526(10)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.57
_cell_volume                     2596.6(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.151
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 2149 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         7913
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.6503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5977
_reflns_number_total             7913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00447a2.cif
_cod_data_source_block           r20117
_cod_depositor_comments
'Adding full bibliography for 7230852--7230855.cif.'
_cod_database_code               7230854
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              7100