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_7114608
_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         'C44 H48 Cu N4, Cl2 Cu, C4 H8 O'
_chemical_formula_sum            'C48 H56 Cl2 Cu2 N4 O'
_chemical_formula_weight         902.94
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-09-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.4845(5)
_cell_length_b                   15.3897(5)
_cell_length_c                   12.7631(3)
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2640
_cell_measurement_theta_min      3.6320
_cell_volume                     4416.4(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
;
SHELXL, 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 0.9972
_diffrn_measured_fraction_theta_max 0.6418
_diffrn_measurement_details
;
  1 omega -100.00  -62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000   60.0000 38

  2 omega  -19.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000   90.0000 48

  3 omega  -48.00   42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -77.0000  -60.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0004266000
_diffrn_orient_matrix_UB_12      0.0384386000
_diffrn_orient_matrix_UB_13      0.0306848000
_diffrn_orient_matrix_UB_21      0.0293479000
_diffrn_orient_matrix_UB_22      -0.0097863000
_diffrn_orient_matrix_UB_23      0.0166201000
_diffrn_orient_matrix_UB_31      0.0115426000
_diffrn_orient_matrix_UB_32      0.0234458000
_diffrn_orient_matrix_UB_33      -0.0432877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12313
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.023
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50497
_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    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.017(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         6372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0565P)^2^+0.4435P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.402
_reflns_Friedel_fraction_full    0.449
_reflns_Friedel_fraction_max     0.441
_reflns_number_gt                5718
_reflns_number_total             6372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01627k2.cif
_cod_data_source_block           yangbm0909
_cod_database_code               7114608
_reflns_odcompleteness_completeness 99.72
_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. Others
 Fixed Sof: H45A(0.5) H45B(0.5) H45C(0.5) H45D(0.5) H47A(0.5) H47B(0.5)
 H47C(0.5) H47D(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) C1B(0.5) H1BA(0.5) H1BB(0.5)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C29(H29), C37(H37)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B),
  C35(H35A,H35B), C36(H36A,H36B), C45(H45A,H45B), C45(H45C,H45D), C47(H47A,
 H47B), C47(H47C,H47D), C48(H48A,H48B), C1A(H1AA,H1AB), C1B(H1BA,H1BB)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C40(H40),
  C41(H41), C42(H42), C43(H43), C44(H44)
;
_shelx_hkl_checksum              41211
_shelx_res_checksum              83956
_shelxl_version_number           2013-2