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_2109068
_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         'C I2, C23 H30 N2 S'
_chemical_formula_sum            'C24 H30 I2 N2 S'
_chemical_formula_weight         632.36
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                67.358(2)
_cell_angle_beta                 83.953(2)
_cell_angle_gamma                72.067(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9170(6)
_cell_length_b                   11.6457(8)
_cell_length_c                   15.0306(10)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      29.61
_cell_measurement_theta_min      2.70
_cell_volume                     1216.73(15)
_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      99.99
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38610
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.628
_diffrn_reflns_theta_min         2.849
_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    2.684
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5983
_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    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         3.786
_refine_diff_density_min         -3.625
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         6789
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0318
_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^)+5.6607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6164
_reflns_number_total             6789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rm5061sup1.cif
_cod_data_source_block           2SDiazMesS_TIE
_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               2109068
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.582
_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. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C13: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
3. Others
 Sof(N2B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=
 Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(C15B)=Sof(C16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(C21B)=Sof(H21D)=
 Sof(H21E)=Sof(H21F)=Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C23B)=
 Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(N2A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=
 Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C15A)=Sof(C16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C23A)=
 Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(C24B)=1-FVAR(2)
 Sof(C24A)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB), C3A(H3AA,H3AB), C3B(H3BA,H3BB), C4A(H4AA,
 H4AB), C4B(H4BA,H4BB), C5A(H5AA,H5AB), C5B(H5BA,H5BB)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C17A(H17A), C19A(H19A), C17B(H17B), C19B(H19B)
4.c Fitted hexagon refined as free rotating group:
 C15A(C16A,C17A,C18A,C19A,C20A), C15B(C16B,C17B,C18B,C19B,C20B)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21A(H21A,H21B,
 H21C), C21B(H21D,H21E,H21F), C22A(H22A,H22B,H22C), C22B(H22D,H22E,H22F),
 C23A(H23A,H23B,H23C), C23B(H23D,H23E,H23F)
;
_shelx_res_checksum              22696
_shelx_hkl_checksum              25088
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2109068