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_7114607
_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 B F3 N2'
_chemical_formula_sum            'C22 H24 B F3 N2'
_chemical_formula_weight         384.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.474(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8224(2)
_cell_length_b                   14.8677(5)
_cell_length_c                   14.6800(6)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8070
_cell_measurement_theta_min      3.1550
_cell_volume                     1913.28(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8955
_diffrn_measurement_details
;
  1 omega  -53.00   -7.40   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   77.0000  150.0000 38

  2 omega  -17.00   10.60   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000   90.0000 23

  3 omega   -1.00   65.00   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -99.0000    0.0000 55

  4 omega  -29.00   95.80   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  -60.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0537733000
_diffrn_orient_matrix_UB_12      0.0092247000
_diffrn_orient_matrix_UB_13      0.0385003000
_diffrn_orient_matrix_UB_21      0.0155993000
_diffrn_orient_matrix_UB_22      -0.0466401000
_diffrn_orient_matrix_UB_23      0.0051439000
_diffrn_orient_matrix_UB_31      0.0584020000
_diffrn_orient_matrix_UB_32      0.0039665000
_diffrn_orient_matrix_UB_33      -0.0292574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8341
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+0.7615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2937
_reflns_number_total             3903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc01627k2.cif
_cod_data_source_block           tuyq0320
_cod_database_code               7114607
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H22 of C22, H21 of C21, H20 of C20, H19 of C19, {H4A,H4B} of C4, {H3A,H3B}
  of C3, {H2A,H2B} of C2, H1 of C1, {H6A,H6B} of C6, {H7A,H7B} of C7, {H8A,H8B}
  of C8, H9 of C9, H12 of C12, H13 of C13, H14 of C14, H15 of C15, H16 of C16,
  H18 of C18
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
;