Heterocyclic 1,3-diazepine-based thiones and selones as versatile halogen-bond acceptors
Ragusa, Arianna C.; Peloquin, Andrew J.; Shahani, Marjan M.; Dowling, Keri N.; Golen, James A.; McMillen, Colin D.; Rabinovich, Daniel; Pennington, William T.; Acta Crystallographica Section B 78 (2022) –; doi:10.1107/S2052520622008150

data_2109067
_publ_section_title
;
 Heterocyclic 1,3-diazepine-based thiones and selones as versatile
 halogen-bond acceptors
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622008150
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         '5(C6 F5 I), 2(C23 H30 N2 Se)'
_chemical_formula_sum            'C76 H60 F25 I5 N4 Se2'
_chemical_formula_weight         2296.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.037(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   25.9292(14)
_cell_length_b                   8.0709(4)
_cell_length_c                   20.4309(11)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.56
_cell_volume                     3934.6(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material  'Olex2 1.5 (Dolomanov <i>et al.</i>, 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015<i>b</i>)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015<i>a</i>)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            61094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.166
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.006
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2204
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         9058
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0103P)^2^+7.6201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8222
_reflns_number_total             9058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rm5061sup1.cif
_cod_data_source_block           2SDiazMesSe_5F5IB
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               2109067
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.538
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C37 \\sim C37-C38 \\sim C38-C39 \\sim C39-C40 \\sim C40-C41 \\sim C41-C36
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41: within 2A with sigma of
0.003 and sigma for terminal atoms of 0.006 within 2A
4. Others
 Fixed Sof: I3(0.5) F11(0.5) F12(0.5) F13(0.5) F14(0.5) F15(0.5) C36(0.5)
 C37(0.5) C38(0.5) C39(0.5) C40(0.5) C41(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C17(H17), C19(H19)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              2434
_shelx_hkl_checksum              46679
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2109067