High Z’ structures of 1,2,3,5-dithiadiazolyls and of 1,2,3,5-diselenadiazolyls containing the first structurally characterized monomeric diselenadiazolyls
Boeré, René; Hill, Nathan D. D.; CrystEngComm  (2017) –; doi:10.1039/C7CE00863E

data_7228526
_publ_section_title
;
 High Z&#x2019; structures of 1,2,3,5-dithiadiazolyls and of
 1,2,3,5-diselenadiazolyls containing the first structurally characterized
 monomeric diselenadiazolyls
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00863E
_journal_year                    2017
_chemical_formula_moiety         'C12 H12 N3 Se2'
_chemical_formula_sum            'C12 H12 N3 Se2'
_chemical_formula_weight         356.17
_chemical_melting_point          473
_chemical_name_systematic
;
 4-(3-cyano-5-tertbutyl-phenyl)-3H-1,2,3,5-diselenadiazol-3-yl
;
_chemical_properties_physical    ', Oxygen-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-06-19 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                80.562(4)
_cell_angle_beta                 84.783(4)
_cell_angle_gamma                81.218(4)
_cell_formula_units_Z            6
_cell_length_a                   9.379(3)
_cell_length_b                   10.667(4)
_cell_length_c                   20.458(7)
_cell_measurement_reflns_used    7983
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.33
_cell_volume                     1990.8(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 66.06
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
;
 Bruker ApexII CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.1216
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21974
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.430
_diffrn_reflns_theta_min         1.955
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker D8'
_exptl_absorpt_coefficient_mu    5.553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1437 before and 0.0794 after correction.
The Ratio of minimum to maximum transmission is 0.4810.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1038
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.185
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         8884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0532
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5194
_reflns_number_total             8884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00863e2.cif
_cod_data_source_block           4a
_cod_original_cell_volume        1990.9(12)
_cod_database_code               7228526
_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. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C11) = Uanis(C12) = Uanis(C10A) = Uanis(C12A) = Uanis(C11A)
Uanis(C22) = Uanis(C24) = Uanis(C23) = Uanis(C22A) = Uanis(C24A) = Uanis(C23A)
3. Others
 Fixed Sof: C10(0.71) H10A(0.71) H10B(0.71) H10C(0.71) C11(0.71) H11A(0.71)
 H11B(0.71) H11C(0.71) C12(0.71) H12A(0.71) H12B(0.71) H12C(0.71) C10A(0.29)
 H10D(0.29) H10E(0.29) H10F(0.29) C11A(0.29) H11D(0.29) H11E(0.29) H11F(0.29)
 C12A(0.29) H12D(0.29) H12E(0.29) H12F(0.29) C22(0.6) H22A(0.6) H22B(0.6)
 H22C(0.6) C23(0.6) H23A(0.6) H23B(0.6) H23C(0.6) C24(0.6) H24A(0.6) H24B(0.6)
 H24C(0.6) C22A(0.4) H22D(0.4) H22E(0.4) H22F(0.4) C23A(0.4) H23D(0.4)
 H23E(0.4) H23F(0.4) C24A(0.4) H24D(0.4) H24E(0.4) H24F(0.4)
4.a Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C10A(H10D,H10E,
 H10F), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22A(H22D,H22E,H22F), C23A(H23D,H23E,
 H23F), C24A(H24D,H24E,H24F), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C15(H15), C17(H17), C19(H19), C27(H27), C29(H29),
 C31(H31)
;
_shelx_res_checksum              36156
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'