Spiro-fused six-membered N-heterocyclic carbene: a new scaffold toward unique properties and activities
Bin-Miao Yang; Kai Xiang; Yong-Qiang Tu; Shi-Heng Zhang; Deng-Tao Yang; Shao-Hua Wang; Fu-Ming Zhang; Chem.Commun. 50 (2014) 7163–; doi:10.1039/C4CC01627K

data_7114604
_publ_section_title
;
 Spiro-fused six-membered N-heterocyclic carbene: a new scaffold toward
 unique properties and activities
;
_journal_name_full               Chem.Commun.
_journal_page_first              7163
_journal_paper_doi               10.1039/C4CC01627K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C22 H24 N2 S'
_chemical_formula_sum            'C22 H24 N2 S'
_chemical_formula_weight         348.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5278(6)
_cell_length_b                   14.5993(6)
_cell_length_c                   17.0361(3)
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.3370
_cell_measurement_theta_min      3.6730
_cell_volume                     3613.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9022
_diffrn_measurement_details
;
  1 omega   60.00   94.80   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000   60.0000 29

  2 omega   15.00   95.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000  -60.0000 67

  3 omega    4.00   49.60   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000  120.0000 38

  4 omega   -8.00   18.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000   60.0000 22
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0248933000
_diffrn_orient_matrix_UB_12      0.0385183000
_diffrn_orient_matrix_UB_13      -0.0138515000
_diffrn_orient_matrix_UB_21      -0.0164798000
_diffrn_orient_matrix_UB_22      -0.0083076000
_diffrn_orient_matrix_UB_23      -0.0385138000
_diffrn_orient_matrix_UB_31      -0.0386229000
_diffrn_orient_matrix_UB_32      0.0283389000
_diffrn_orient_matrix_UB_33      0.0074855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10750
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.036
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.3400
_exptl_crystal_size_mid          0.2700
_exptl_crystal_size_min          0.2500
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+3.1797P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3025
_reflns_number_total             3685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01627k2.cif
_cod_data_source_block           yangbm0412
_cod_database_code               7114604
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Fixed Sof: H14A(0.6) H14B(0.6) H14C(0.4) H14D(0.4) C15(0.6) H15A(0.6)
 H15B(0.6) C15B(0.4) H15C(0.4) H15D(0.4) H16A(0.6) H16B(0.6) H16C(0.4) H16D(0.4)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13B,H13A), C14(H14A,H14B), C14(H14C,
 H14D), C15(H15A,H15B), C15B(H15C,H15D), C16(H16A,H16B), C16(H16C,H16D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_shelx_res_checksum              77777
_shelx_hkl_checksum              14824