#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:36:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180229 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/15/7111545.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111545
loop_
_publ_author_name
'Benhamou, Laure'
'César, Vincent'
'Gornitzka, Heinz'
'Lugan, Noël'
'Lavigne, Guy'
_publ_section_title
;
 Imidazol-2-ylidene-4-olate: an anionic N-heterocyclic carbene
 pre-programmed for further derivatization
;
_journal_issue                   31
_journal_name_full               'Chemical Communications'
_journal_page_first              4720
_journal_page_last               4722
_journal_paper_doi               10.1039/b907908d
_journal_year                    2009
_chemical_formula_moiety         'C21 H25 N2 O, Cl'
_chemical_formula_sum            'C21 H25 Cl N2 O'
_chemical_formula_weight         356.88
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-02-26T17:23:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 118.109(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5416(3)
_cell_length_b                   29.645(1)
_cell_length_c                   8.7375(3)
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      38.28
_cell_measurement_theta_min      1.37
_cell_measurement_wavelength     0.71073
_cell_volume                     1951.52(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       'phi and omega 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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32567
_diffrn_reflns_theta_full        29.83
_diffrn_reflns_theta_max         29.83
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'SADABS, Sheldrick, Bruker, 2000'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         5592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+1.2293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                4769
_reflns_number_total             5587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b907908dsup1.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7111545
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3763(2) 0.12515(6) 0.7305(2) 0.0300(3) Uani 1 1 d . A 4
H1 H 0.4831 0.1259 0.8331 0.036 Uiso 1 1 calc R A 4
C2 C 0.1012(2) 0.10836(6) 0.5338(2) 0.0300(3) Uani 1 1 d . A 4
H2 H -0.0111 0.0953 0.4807 0.036 Uiso 0.50 1 calc PR A 4
C3 C 0.1671(2) 0.13856(6) 0.4617(2) 0.0294(3) Uani 1 1 d . A 4
H3 H 0.1081 0.1504 0.3501 0.035 Uiso 0.50 1 calc PR A 4
C11 C 0.2209(2) 0.07296(6) 0.8317(2) 0.0277(3) Uani 1 1 d . A 4
C12 C 0.1734(3) 0.09366(6) 0.9464(2) 0.0385(4) Uani 1 1 d . A 4
C13 C 0.1699(3) 0.06684(8) 1.0750(2) 0.0429(4) Uani 1 1 d . A 4
H13 H 0.1370 0.0797 1.1527 0.051 Uiso 1 1 calc R A 4
C14 C 0.2139(2) 0.02162(7) 1.0910(2) 0.0380(4) Uani 1 1 d . A 4
C15 C 0.2552(2) 0.00200(6) 0.9703(2) 0.0356(4) Uani 1 1 d . A 4
H15 H 0.2815 -0.0286 0.9784 0.043 Uiso 1 1 calc R A 4
C16 C 0.2581(2) 0.02725(6) 0.8372(2) 0.0296(3) Uani 1 1 d . A 4
C17 C 0.1282(5) 0.14296(8) 0.9335(4) 0.0734(9) Uani 1 1 d . A 4
H17A H 0.2315 0.1605 0.9564 0.110 Uiso 1 1 calc R A 4
H17B H 0.0890 0.1503 1.0170 0.110 Uiso 1 1 calc R A 4
H17C H 0.0354 0.1496 0.8189 0.110 Uiso 1 1 calc R A 4
C18 C 0.2191(3) -0.00603(9) 1.2387(3) 0.0561(6) Uani 1 1 d . A 4
H18A H 0.3329 -0.0026 1.3391 0.084 Uiso 1 1 calc R A 4
H18B H 0.2000 -0.0372 1.2056 0.084 Uiso 1 1 calc R A 4
H18C H 0.1279 0.0042 1.2651 0.084 Uiso 1 1 calc R A 4
C19 C 0.2978(3) 0.00523(7) 0.7044(3) 0.0443(5) Uani 1 1 d . A 4
H19A H 0.1904 0.0028 0.5964 0.066 Uiso 1 1 calc R A 4
H19B H 0.3461 -0.0243 0.7439 0.066 Uiso 1 1 calc R A 4
H19C H 0.3824 0.0232 0.6881 0.066 Uiso 1 1 calc R A 4
C21 C 0.4642(2) 0.17729(5) 0.5662(2) 0.0277(3) Uani 1 1 d . A 4
C22 C 0.5796(2) 0.15789(6) 0.5139(2) 0.0330(4) Uani 1 1 d . A 4
C23 C 0.7042(2) 0.18623(6) 0.5033(3) 0.0362(4) Uani 1 1 d . A 4
H23 H 0.7836 0.1742 0.4693 0.043 Uiso 1 1 calc R A 4
C24 C 0.7134(2) 0.23193(6) 0.5418(2) 0.0346(4) Uani 1 1 d . A 4
C25 C 0.5916(2) 0.24992(6) 0.5885(2) 0.0343(4) Uani 1 1 d . A 4
H25 H 0.5957 0.2806 0.6126 0.041 Uiso 1 1 calc R A 4
C26 C 0.4641(2) 0.22320(6) 0.6002(2) 0.0297(3) Uani 1 1 d . A 4
C27 C 0.5739(3) 0.10863(7) 0.4705(4) 0.0513(5) Uani 1 1 d . A 4
H27A H 0.6818 0.0944 0.5528 0.077 Uiso 1 1 calc R A 4
H27B H 0.5614 0.1054 0.3559 0.077 Uiso 1 1 calc R A 4
H27C H 0.4748 0.0947 0.4750 0.077 Uiso 1 1 calc R A 4
C28 C 0.8546(3) 0.26106(8) 0.5355(3) 0.0497(5) Uani 1 1 d . A 4
H28A H 0.9551 0.2627 0.6491 0.075 Uiso 1 1 calc R A 4
H28B H 0.8082 0.2908 0.4972 0.075 Uiso 1 1 calc R A 4
H28C H 0.8905 0.2482 0.4561 0.075 Uiso 1 1 calc R A 4
C29 C 0.3271(3) 0.24351(7) 0.6421(3) 0.0413(4) Uani 1 1 d . A 4
H29A H 0.3646 0.2731 0.6899 0.062 Uiso 1 1 calc R A 4
H29B H 0.3139 0.2248 0.7250 0.062 Uiso 1 1 calc R A 4
H29C H 0.2156 0.2455 0.5381 0.062 Uiso 1 1 calc R A 4
N1 N 0.23389(18) 0.10070(5) 0.70196(17) 0.0286(3) Uani 1 1 d . A 4
N2 N 0.33898(17) 0.14834(5) 0.58645(17) 0.0281(3) Uani 1 1 d . A 4
Cl1 Cl -0.25794(6) 0.121947(16) 0.12556(6) 0.04400(14) Uani 1 1 d . B 4
O1A O -0.0433(3) 0.08635(9) 0.4689(3) 0.0402(6) Uani 0.50 1 d P C 2
O1B O 0.0956(3) 0.15871(8) 0.3151(3) 0.0290(5) Uani 0.50 1 d P D 1
H1A H -0.1117 0.0974 0.3614 0.050 Uiso 0.50 1 d P E 2
H1B H -0.0115 0.1474 0.2552 0.050 Uiso 0.50 1 d P F 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 N1 108.16(13)
N2 C1 H1 125.9
N1 C1 H1 125.9
C3 C2 N1 106.76(14)
C3 C2 O1A 131.23(18)
C3 C2 H2 126.6
N1 C2 H2 126.6
C2 C3 N2 106.85(13)
C2 C3 O1B 131.7(2)
C2 C3 H3 126.6
N2 C3 H3 126.6
C16 C11 C12 123.13(15)
C16 C11 N1 118.78(14)
C12 C11 N1 118.09(15)
C13 C12 C11 117.13(17)
C13 C12 C17 121.02(19)
C11 C12 C17 121.85(18)
C14 C13 C12 121.97(17)
C14 C13 H13 119.0
C12 C13 H13 119.0
C13 C14 C15 118.94(16)
C13 C14 C18 120.69(19)
C15 C14 C18 120.4(2)
C14 C15 C16 121.36(17)
C14 C15 H15 119.3
C16 C15 H15 119.3
C11 C16 C15 117.36(16)
C11 C16 C19 121.94(15)
C15 C16 C19 120.69(16)
C22 C21 C26 123.06(15)
C22 C21 N2 118.32(15)
C26 C21 N2 118.62(14)
C21 C22 C23 117.03(16)
C21 C22 C27 122.71(16)
C23 C22 C27 120.26(17)
C24 C23 C22 121.97(16)
C24 C23 H23 119.0
C22 C23 H23 119.0
C23 C24 C25 118.74(16)
C23 C24 C28 120.32(17)
C25 C24 C28 120.94(17)
C26 C25 C24 121.58(16)
C26 C25 H25 119.2
C24 C25 H25 119.2
C25 C26 C21 117.54(15)
C25 C26 C29 121.04(16)
C21 C26 C29 121.38(15)
C1 N1 C2 109.08(13)
C1 N1 C11 124.18(13)
C2 N1 C11 126.66(13)
C1 N2 C3 109.14(13)
C1 N2 C21 124.03(13)
C3 N2 C21 126.78(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.334(2)
C1 N1 1.335(2)
C1 H1 0.9300
C2 C3 1.360(2)
C2 N1 1.3876(19)
C2 O1A 1.269(3)
C2 H2 0.9300
C3 N2 1.3856(19)
C3 O1B 1.278(3)
C3 H3 0.9300
C11 C16 1.387(2)
C11 C12 1.389(2)
C11 N1 1.446(2)
C12 C13 1.388(3)
C12 C17 1.502(3)
C13 C14 1.381(3)
C13 H13 0.9300
C14 C15 1.388(3)
C14 C18 1.511(3)
C15 C16 1.393(2)
C15 H15 0.9300
C16 C19 1.503(2)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C21 C22 1.391(2)
C21 C26 1.393(2)
C21 N2 1.446(2)
C22 C23 1.393(2)
C22 C27 1.504(3)
C23 C24 1.390(3)
C23 H23 0.9300
C24 C25 1.390(3)
C24 C28 1.505(3)
C25 C26 1.389(2)
C25 H25 0.9300
C26 C29 1.506(2)
C27 H27A 0.9600
C27 H27B 0.9600
C27 H27C 0.9600
C28 H28A 0.9600
C28 H28B 0.9600
C28 H28C 0.9600
C29 H29A 0.9600
C29 H29B 0.9600
C29 H29C 0.9600
O1A H1A 0.902(2)
O1B H1B 0.879(2)
