Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions
Bosch, Eric; Kruse, Samantha J.; Reinheimer, Eric W.; Rath, Nigam P.; Groeneman, Ryan H.; CrystEngComm 21 (2019) 6671–; doi:10.1039/C9CE01379B

data_7234602
_publ_section_title
;
 Regioselective [2 + 2] cycloaddition reaction within a pair of
 polymorphic co-crystals based upon halogen bonding interactions
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              6671
_journal_paper_doi               10.1039/C9CE01379B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C13 H11 N, 0.5(C6 Cl4 I2)'
_chemical_formula_sum            'C16 H11 Cl2 I N'
_chemical_formula_weight         415.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-10-04 deposited with the CCDC.    2019-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                82.9822(14)
_cell_angle_beta                 82.3948(12)
_cell_angle_gamma                77.3857(12)
_cell_formula_units_Z            2
_cell_length_a                   5.6832(2)
_cell_length_b                   11.0865(4)
_cell_length_c                   12.2076(5)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      3.38
_cell_volume                     740.53(5)
_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  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12920
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.427
_diffrn_reflns_theta_min         2.412
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.159
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0157
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0149P)^2^+0.9729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2941
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01379b2.cif
_cod_data_source_block           r3919-mo-100k
_cod_depositor_comments
'Adding full bibliography for 7234601--7234605.cif.'
_cod_database_code               7234602
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.453
_shelx_estimated_absorpt_t_max   0.691
_shelx_res_checksum              51268