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_7244919
_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         'C36 H26 F4 I2 N2 O4'
_chemical_formula_sum            'C36 H26 F4 I2 N2 O4'
_chemical_formula_weight         880.39
_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     dual
_audit_creation_date             2022-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-04-25 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                76.276(2)
_cell_angle_beta                 83.834(2)
_cell_angle_gamma                83.200(2)
_cell_formula_units_Z            1
_cell_length_a                   6.26700(10)
_cell_length_b                   11.0627(2)
_cell_length_c                   12.1817(3)
_cell_measurement_reflns_used    12277
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9430
_cell_measurement_theta_min      3.7220
_cell_volume                     811.91(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -41.00  25.00   0.50    0.05    --  -47.76  38.00 150.00  132
  2  \w    -25.00  28.00   0.50    0.05    --  -47.76  19.00 -60.00  106
  3  \w    -25.00  28.00   0.50    0.05    --  -47.76  19.00-120.00  106
  4  \w    -25.00  28.00   0.50    0.05    --  -47.76  19.00-150.00  106
  5  \w     25.00 121.00   0.50    0.05    --   47.76  77.00 -60.00  192
  6  \w     25.00 121.00   0.50    0.05    --   47.76  77.00 120.00  192
  7  \w     25.00 121.00   0.50    0.05    --   47.76  77.00  90.00  192
  8  \w     33.00 120.00   0.50    0.05    --   47.76  57.00  30.00  174
  9  \w     25.00 121.00   0.50    0.05    --   47.76  77.00-180.00  192
 10  \w    106.00 178.00   0.50    0.17    --  107.31  98.00-119.00  144
 11  \w     92.00 178.00   0.50    0.17    --  107.31  57.00 -30.00  172
 12  \w     35.00 107.00   0.50    0.17    --  107.31 -77.00 120.00  144
 13  \w     35.00  68.00   0.50    0.17    --  107.31 -57.00  60.00   66
 14  \w     35.00  68.00   0.50    0.17    --  107.31 -57.00 -30.00   66
 15  \w     35.00  68.00   0.50    0.17    --  107.31 -57.00   0.00   66
 16  \w     35.00  68.00   0.50    0.17    --  107.31 -57.00  30.00   66
 17  \w    -27.00  29.00   0.50    0.05    --   47.76 -19.00-120.00  112
 18  \w     35.00  68.00   0.50    0.17    --  107.31 -57.00 -90.00   66
 19  \w     94.00 178.00   0.50    0.17    --  107.31  38.00-150.00  168
 20  \w     35.00  68.00   0.50    0.17    --  107.31 -57.00-180.00   66
 21  \w     35.00 111.00   0.50    0.17    --  107.31-125.00-150.00  152
 22  \w     35.00 106.00   0.50    0.17    --  107.31 -99.00-120.00  142
 23  \w     35.00 111.00   0.50    0.17    --  107.31-125.00   0.00  152
 24  \w     35.00 106.00   0.50    0.17    --  107.31 -99.00   0.00  142
 25  \w     -5.00  81.00   0.50    0.05    --   47.76 -98.00 133.00  172
 26  \w     35.00 111.00   0.50    0.17    --  107.31-125.00 120.00  152
 27  \w     35.00 106.00   0.50    0.17    --  107.31 -99.00  90.00  142
 28  \w     35.00 106.00   0.50    0.17    --  107.31 -98.00 133.00  142
 29  \w    -80.00  25.00   0.50    0.05    --  -47.76  98.00-119.00  210
 30  \w    -85.00 -19.00   0.50    0.17    --  -91.75 125.00 -90.00  132
 31  \w    -80.00 -19.00   0.50    0.17    --  -91.75  98.00-119.00  122
 32  \w   -163.00 -73.00   0.50    0.17    --  -91.75-125.00 120.00  180
 33  \w   -163.00 -86.00   0.50    0.17    --  -91.75 -98.00 133.00  154
 34  \w   -165.00 -78.00   0.50    0.17    --  -91.75 -38.00 150.00  174
 35  \w   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00 120.00  188
 36  \w   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00  30.00  188
 37  \w   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00  60.00  188
 38  \w   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00 -30.00  188
 39  \w   -163.00 -77.00   0.50    0.17    --  -91.75 -77.00 -60.00  172
 40  \w   -165.00 -78.00   0.50    0.17    --  -91.75 -38.00-120.00  174
 41  \w   -163.00 -77.00   0.50    0.17    --  -91.75 -57.00-150.00  172
 42  \w   -120.00 -33.00   0.50    0.05    --  -47.76 -57.00-150.00  174
 43  \w   -120.00 -25.00   0.50    0.05    --  -47.76 -77.00 -60.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0879774000
_diffrn_orient_matrix_UB_12      0.0033091000
_diffrn_orient_matrix_UB_13      0.1224082000
_diffrn_orient_matrix_UB_21      -0.0781862000
_diffrn_orient_matrix_UB_22      -0.1304124000
_diffrn_orient_matrix_UB_23      0.0159238000
_diffrn_orient_matrix_UB_31      0.2187487000
_diffrn_orient_matrix_UB_32      -0.0610154000
_diffrn_orient_matrix_UB_33      0.0427237000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.946
_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       -15
_diffrn_reflns_number            15382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.114
_diffrn_reflns_theta_min         3.748
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.791
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.191
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       plate
_exptl_crystal_F_000             430
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.00122(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     870
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0328P)^2^+0.8973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3062
_reflns_number_total             3231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00360k2.cif
_cod_data_source_block           C6I2F4_2_4-PEBE
_cod_database_code               7244919
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40  H22  F4  I2  N2  O4  '
_shelx_estimated_absorpt_t_max   0.649
_shelx_estimated_absorpt_t_min   0.152
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-C17A \\sim O1B-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.04
 O1A-C18A \\sim O1B-C18B
 with sigma of 0.02
 O2A-C17A \\sim O2B-C17B
 with sigma of 0.02
 N1-C4A \\sim N1-C4B
 with sigma of 0.02
 N1-C8A \\sim N1-C8B
 with sigma of 0.02
 C4A-C5A \\sim C4B-C5B
 with sigma of 0.02
 C11A-C13A \\sim C11B-C13B
 with sigma of 0.04
 C5A-C6A \\sim C5B-C6B
 with sigma of 0.02
 C12A-C16A \\sim C12B-C16B
 with sigma of 0.04
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C6A-C9A \\sim C6B-C9B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.04
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.02
 C10A-C12A \\sim C10B-C12B
 with sigma of 0.04
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 C13A-C17A \\sim C13B-C17B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.02
 C11A-C16A \\sim C11B-C16B
 with sigma of 0.02
 C6A-C10A \\sim C6B-C10B
 with sigma of 0.04
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.02
 C7A-C9A \\sim C7B-C9B
 with sigma of 0.04
 C13A-C14A \\sim C13B-C14B
 with sigma of 0.02
 C10A-C16A \\sim C10B-C16B
 with sigma of 0.04
 C14A-C15A \\sim C14B-C15B
 with sigma of 0.02
 C14A-C17A \\sim C14B-C17B
 with sigma of 0.02
 C11A-C15A \\sim C11B-C15B
 with sigma of 0.04
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C12A-C14A \\sim C12B-C14B
 with sigma of 0.04
 O1A-O2A \\sim O1B-O2B
 with sigma of 0.04
 C13A-C15A \\sim C13B-C15B
 with sigma of 0.04
 O1A-C14A \\sim O1B-C14B
 with sigma of 0.04
 C14A-C16A \\sim C14B-C16B
 with sigma of 0.04
 O2A-C14A \\sim O2B-C14B
 with sigma of 0.04
 N1-C5A \\sim N1-C5B
 with sigma of 0.04
 N1-C7A \\sim N1-C7B
 with sigma of 0.04
 C4A-C6A \\sim C4B-C6B
 with sigma of 0.04
 C5A-C7A \\sim C5B-C7B
 with sigma of 0.04
 C5A-C9A \\sim C5B-C9B
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O1A \\sim O1B \\sim O2A \\sim O2B \\sim N1 \\sim C4A \\sim C4B \\sim C5A \\sim
C5B \\sim C6A \\sim C6B \\sim C7A \\sim C7B \\sim C8A \\sim C8B \\sim C9A \\sim
C9B \\sim C10A \\sim C10B \\sim C11A \\sim C11B \\sim C12A \\sim C12B \\sim
C13A \\sim C13B \\sim C14A \\sim C14B \\sim C15A \\sim C15B \\sim C16A \\sim
C16B \\sim C17A \\sim C17B \\sim C18A \\sim C18B: within 2A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 O1A, O1B, O2A, O2B, N1, C4A, C4B, C5A, C5B, C6A, C6B, C7A, C7B, C8A, C8B, C9A,
  C9B, C10A, C10B, C11A, C11B, C12A, C12B, C13A, C13B, C14A, C14B, C15A, C15B,
 C16A, C16B, C17A, C17B, C18A, C18B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O1B)=Sof(O2B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=
 Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C15B)=Sof(H15B)=
 Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=
 Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=
 Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C4B(H4B), C5A(H5A), C5B(H5B), C7A(H7A), C7B(H7B), C8A(H8A),
 C8B(H8B), C9A(H9A), C9B(H9B), C10A(H10A), C10B(H10B), C12A(H12A), C12B(H12B),
 C13A(H13A), C13B(H13B), C15A(H15A), C15B(H15B), C16A(H16A), C16B(H16B)
6.b Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_shelx_res_checksum              64760
_olex2_exptl_crystal_mounting_method 'MiTeGen 50 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   591
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.967
_oxdiff_exptl_absorpt_empirical_full_min 0.605