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_7228527
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-26
_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                90
_cell_angle_beta                 93.6610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   21.1972(16)
_cell_length_b                   10.6954(8)
_cell_length_c                   28.994(2)
_cell_measurement_reflns_used    7169
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.23
_cell_volume                     6559.9(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 66.06
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_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  0.0447
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            74801
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.802
_diffrn_reflns_theta_min         1.654
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker D8'
_exptl_absorpt_coefficient_mu    5.617
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_correction_T_min  0.5755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Bruker, 2008)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_description       block
_exptl_crystal_F_000             3460
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     800
_refine_ls_number_reflns         15899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0314P)^2^+8.8058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11452
_reflns_number_total             15899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00863e2.cif
_cod_data_source_block           4b
_cod_original_cell_volume        6559.9(9)
_cod_database_code               7228527
_shelx_estimated_absorpt_t_max   0.662
_shelx_estimated_absorpt_t_min   0.449
_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
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uiso(C22) = Uiso(C22A)
3. Rigid body (RIGU) restrains
 C23, C24, C23A, C24A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) C23(0.5) H23A(0.5)
 H23B(0.5) H23C(0.5) C24(0.5) H24A(0.5) H24B(0.5) H24C(0.5) C22A(0.5) H22D(0.5)
 H22E(0.5) H22F(0.5) C23A(0.5) H23D(0.5) H23E(0.5) H23F(0.5) C24A(0.5)
 H24D(0.5) H24E(0.5) H24F(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C51(H51), C53(H53), C55(H55), C39(H39), C41(H41),
 C43(H43), C15(H15), C17(H17), C19(H19), C27(H27), C29(H29), C31(H31)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C58(H58A,H58B,
 H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C48(H48A,H48B,H48C), 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)
;
_shelx_res_checksum              86485
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'