Cooperative non-covalent interactions and synthetic feed as driving forces to structural diversity within organic co-crystals containing isosteric perhalobenzenes
Bosch, Eric; Ferrence, Gregory M.; Powell, Conrad; Unruh, Daniel K.; Krueger, Herman R.; Groeneman, Ryan; CrystEngComm  (2022) –; doi:10.1039/D2CE00360K

data_7244920
_publ_section_title
;
 Cooperative non-covalent interactions and synthetic feed as driving
 forces to structural diversity within organic co-crystals containing
 isosteric perhalobenzenes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00360K
_journal_year                    2022
_chemical_formula_moiety         'C15 H13 N O2, 0.5 C6 Cl4 I2'
_chemical_formula_sum            'C18 H13 Cl2 I N O2'
_chemical_formula_weight         473.09
_chemical_name_systematic
'hemikis(1,2,4,5-tetrachloro-3,6-diiodobenzene) methyl 4-[(1E)-2-(pyridin-4-yl)ethenyl]benzoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-04 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                114.5720(10)
_cell_angle_beta                 92.194(2)
_cell_angle_gamma                107.358(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2756(2)
_cell_length_b                   10.2186(3)
_cell_length_c                   11.8757(4)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.72
_cell_measurement_theta_min      2.34
_cell_volume                     856.35(5)
_computing_cell_refinement       'APEX4 & SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
<i>Mercury CSD</i> (Macrae et al., 2020)
;
_computing_publication_material
;
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
 A total of 3672 frames were collected.  
 The total exposure time was 5.10 hours.
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32790
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.927
_diffrn_reflns_theta_min         1.919
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Apex4 v2021.4.0 (Bruker, 2021)

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0162
_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^)+(0.0149P)^2^+0.5237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0377
_refine_ls_wR_factor_ref         0.0388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5711
_reflns_number_total             6056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00360k2.cif
_cod_data_source_block           GMF21028
_cod_original_cell_volume        856.35(4)
_cod_database_code               7244920
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.600
_shelx_estimated_absorpt_t_max   0.735
_shelx_res_checksum              75302