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_2109046
_publ_section_title
;
 Heterocyclic 1,3-diazepine-based thiones and selones as versatile
 halogen-bond acceptors
;
_journal_coeditor_code           RM5061
_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         'C23 H30 N2 S, C2 H3 N'
_chemical_formula_sum            'C25 H33 N3 S'
_chemical_formula_weight         407.60
_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_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                90
_cell_angle_beta                 113.028(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0884(6)
_cell_length_b                   12.9760(5)
_cell_length_c                   14.4293(7)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.31
_cell_volume                     2255.32(18)
_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      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34671
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.194
_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    0.159
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5148
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0294P)^2^+1.5344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4419
_reflns_number_total             5148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rm5061sup1.cif
_cod_data_source_block           SDiazMesS_MeCN
_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               2109046
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.960
_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. Shared sites
{C3, C3B}
3. Uiso/Uaniso restraints and constraints
C4 \\sim C4B \\sim C5 \\sim C5B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C3) = Uanis(C3B)
4. Others
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=
 Sof(H5BB)=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C3B(H3BA,H3BB), C4B(H4BA,
 H4BB), C5B(H5BA,H5BB)
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), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              44489
_shelx_hkl_checksum              51196
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2109046