#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:55:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180202 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/96/7109604.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7109604
loop_
_publ_author_name
'Yun-Ting Wang'
'Meng-Ting Chang'
'Gene-Hsiang Lee'
'Shie-Ming Peng'
'Ching-Wen Chiu'
_publ_section_title
;
 Planar tris-N-heterocyclic carbenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              7258
_journal_paper_doi               10.1039/c3cc43278e
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C75 H90 N6'
_chemical_formula_weight         1075.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9449(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4291(3)
_cell_length_b                   33.6359(11)
_cell_length_c                   11.6153(3)
_cell_measurement_reflns_used    17070
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.21
_cell_volume                     3285.37(18)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17070
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0776P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                3739
_reflns_number_total             5808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43278e.txt
_cod_data_source_block           ic15984
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               7109604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
N1 N 2.23983(16) 0.13591(4) 0.76857(11) 0.0263(4) Uani 1 1 d . . .
N2 N 2.05050(16) 0.10457(4) 0.67092(12) 0.0271(4) Uani 1 1 d . . .
N3 N 1.36666(16) 0.21768(4) 0.36589(12) 0.0308(4) Uani 1 1 d . . .
C1 C 2.1913(2) 0.09852(5) 0.73531(15) 0.0294(4) Uani 1 1 d . . .
C2 C 1.2818(3) 0.2500 0.3235(2) 0.0345(6) Uani 1 2 d S . .
C3 C 2.13351(19) 0.16536(5) 0.72530(14) 0.0248(4) Uani 1 1 d . . .
C4 C 2.01083(19) 0.14501(5) 0.66311(14) 0.0253(4) Uani 1 1 d . . .
C5 C 1.88766(19) 0.16549(5) 0.60636(14) 0.0276(4) Uani 1 1 d . . .
H5 H 1.8047 0.1513 0.5647 0.033 Uiso 1 1 calc R . .
C6 C 1.88406(19) 0.20718(5) 0.60976(14) 0.0258(4) Uani 1 1 d . . .
C7 C 2.00952(19) 0.22808(5) 0.67117(14) 0.0247(4) Uani 1 1 d . . .
C8 C 2.13324(19) 0.20648(5) 0.72939(14) 0.0270(4) Uani 1 1 d . . .
H8 H 2.2169 0.2202 0.7717 0.032 Uiso 1 1 calc R . .
C9 C 1.50399(19) 0.22923(5) 0.43319(14) 0.0277(4) Uani 1 1 d . . .
C10 C 1.62586(19) 0.20845(5) 0.49108(14) 0.0291(4) Uani 1 1 d . . .
H10 H 1.6243 0.1802 0.4915 0.035 Uiso 1 1 calc R . .
C11 C 1.75208(19) 0.22890(5) 0.54933(14) 0.0256(4) Uani 1 1 d . . .
C12 C 2.3887(2) 0.14350(5) 0.84326(14) 0.0293(4) Uani 1 1 d . . .
C13 C 2.5042(2) 0.16759(6) 0.77528(16) 0.0374(5) Uani 1 1 d . . .
H13A H 2.5305 0.1526 0.7069 0.056 Uiso 1 1 calc R . .
H13B H 2.6015 0.1728 0.8241 0.056 Uiso 1 1 calc R . .
H13C H 2.4546 0.1929 0.7513 0.056 Uiso 1 1 calc R . .
C14 C 2.3452(2) 0.16524(6) 0.95259(15) 0.0389(5) Uani 1 1 d . . .
H14A H 2.2938 0.1906 0.9313 0.058 Uiso 1 1 calc R . .
H14B H 2.4418 0.1703 1.0023 0.058 Uiso 1 1 calc R . .
H14C H 2.2720 0.1488 0.9941 0.058 Uiso 1 1 calc R . .
C15 C 2.4657(2) 0.10410(6) 0.87813(17) 0.0420(5) Uani 1 1 d . . .
H15A H 2.3927 0.0886 0.9224 0.063 Uiso 1 1 calc R . .
H15B H 2.5643 0.1090 0.9257 0.063 Uiso 1 1 calc R . .
H15C H 2.4898 0.0893 0.8088 0.063 Uiso 1 1 calc R . .
C16 C 1.9523(2) 0.07147(5) 0.61699(15) 0.0316(4) Uani 1 1 d . . .
C17 C 1.7864(2) 0.07251(6) 0.66350(17) 0.0407(5) Uani 1 1 d . . .
H17A H 1.7966 0.0716 0.7480 0.061 Uiso 1 1 calc R . .
H17B H 1.7248 0.0495 0.6341 0.061 Uiso 1 1 calc R . .
H17C H 1.7319 0.0970 0.6382 0.061 Uiso 1 1 calc R . .
C18 C 2.0301(2) 0.03185(5) 0.64960(17) 0.0420(5) Uani 1 1 d . . .
H18A H 2.1365 0.0309 0.6207 0.063 Uiso 1 1 calc R . .
H18B H 1.9653 0.0101 0.6153 0.063 Uiso 1 1 calc R . .
H18C H 2.0384 0.0290 0.7338 0.063 Uiso 1 1 calc R . .
C19 C 1.9435(2) 0.07611(6) 0.48558(16) 0.0405(5) Uani 1 1 d . . .
H19A H 1.8986 0.1022 0.4644 0.061 Uiso 1 1 calc R . .
H19B H 1.8756 0.0552 0.4501 0.061 Uiso 1 1 calc R . .
H19C H 2.0505 0.0739 0.4582 0.061 Uiso 1 1 calc R . .
C20 C 1.3183(2) 0.17582(5) 0.34155(15) 0.0322(5) Uani 1 1 d . . .
C21 C 1.2898(2) 0.15528(6) 0.45486(16) 0.0436(5) Uani 1 1 d . . .
H21A H 1.3881 0.1556 0.5051 0.065 Uiso 1 1 calc R . .
H21B H 1.2569 0.1277 0.4397 0.065 Uiso 1 1 calc R . .
H21C H 1.2060 0.1693 0.4929 0.065 Uiso 1 1 calc R . .
C22 C 1.4495(2) 0.15527(6) 0.27904(16) 0.0412(5) Uani 1 1 d . . .
H22A H 1.4734 0.1709 0.2112 0.062 Uiso 1 1 calc R . .
H22B H 1.4139 0.1287 0.2545 0.062 Uiso 1 1 calc R . .
H22C H 1.5454 0.1530 0.3313 0.062 Uiso 1 1 calc R . .
C23 C 1.1658(2) 0.17504(6) 0.26394(19) 0.0502(6) Uani 1 1 d . . .
H23A H 1.0807 0.1881 0.3032 0.075 Uiso 1 1 calc R . .
H23B H 1.1359 0.1474 0.2467 0.075 Uiso 1 1 calc R . .
H23C H 1.1825 0.1891 0.1919 0.075 Uiso 1 1 calc R . .
C24 C 0.9187(5) 0.2500 0.1251(4) 0.0658(10) Uani 1 2 d S . .
H24 H 1.0164 0.2500 0.1710 0.079 Uiso 1 2 calc SR . .
C25 C 0.9170(4) 0.2500 0.0068(4) 0.0647(10) Uani 1 2 d S . .
H25 H 1.0147 0.2500 -0.0294 0.078 Uiso 1 2 calc SR . .
C26 C 0.7772(4) 0.2500 -0.0592(3) 0.0597(9) Uani 1 2 d S . .
H26 H 0.7777 0.2500 -0.1410 0.072 Uiso 1 2 calc SR . .
C27 C 0.6378(4) 0.2500 -0.0084(3) 0.0553(9) Uani 1 2 d S . .
H27 H 0.5405 0.2500 -0.0548 0.066 Uiso 1 2 calc SR . .
C28 C 0.6356(4) 0.2500 0.1080(3) 0.0596(9) Uani 1 2 d S . .
H28 H 0.5368 0.2500 0.1427 0.072 Uiso 1 2 calc SR . .
C29 C 0.7754(6) 0.2500 0.1762(3) 0.0672(10) Uani 1 2 d S . .
H29 H 0.7736 0.2500 0.2579 0.081 Uiso 1 2 calc SR . .
C30 C 0.2891(3) 0.04759(7) 0.2618(2) 0.0644(7) Uani 1 1 d . . .
H30 H 0.2033 0.0657 0.2659 0.077 Uiso 1 1 calc R . .
C31 C 0.3954(3) 0.04249(7) 0.3557(2) 0.0619(7) Uani 1 1 d . . .
H31 H 0.3835 0.0571 0.4245 0.074 Uiso 1 1 calc R . .
C32 C 0.5196(3) 0.01599(6) 0.3495(2) 0.0533(6) Uani 1 1 d . . .
H32 H 0.5937 0.0125 0.4141 0.064 Uiso 1 1 calc R . .
C33 C 0.5367(2) -0.00542(6) 0.25014(18) 0.0469(5) Uani 1 1 d . . .
H33 H 0.6221 -0.0237 0.2463 0.056 Uiso 1 1 calc R . .
C34 C 0.4301(3) -0.00034(6) 0.1568(2) 0.0540(6) Uani 1 1 d . . .
H34 H 0.4412 -0.0153 0.0885 0.065 Uiso 1 1 calc R . .
C35 C 0.3061(3) 0.02659(7) 0.1620(2) 0.0611(7) Uani 1 1 d . . .
H35 H 0.2334 0.0305 0.0968 0.073 Uiso 1 1 calc R . .
C36 C -0.1983(5) 0.12751(19) 0.1327(6) 0.0576(17) Uani 0.761(9) 1 d P A 1
H36 H -0.2357 0.1491 0.1763 0.069 Uiso 0.761(9) 1 calc PR A 1
C37 C -0.2321(6) 0.0893(2) 0.1627(4) 0.0629(15) Uani 0.761(9) 1 d P A 1
H37 H -0.2935 0.0843 0.2267 0.075 Uiso 0.761(9) 1 calc PR A 1
C38 C -0.1765(6) 0.05777(18) 0.0993(5) 0.0641(14) Uani 0.761(9) 1 d P A 1
H38 H -0.1974 0.0312 0.1215 0.077 Uiso 0.761(9) 1 calc PR A 1
C39 C -0.0904(7) 0.0651(2) 0.0038(6) 0.0654(16) Uani 0.761(9) 1 d P A 1
H39 H -0.0555 0.0437 -0.0414 0.079 Uiso 0.761(9) 1 calc PR A 1
C40 C -0.0560(9) 0.1039(2) -0.0247(6) 0.067(2) Uani 0.761(9) 1 d P A 1
H40 H 0.0052 0.1093 -0.0886 0.081 Uiso 0.761(9) 1 calc PR A 1
C41 C -0.1110(7) 0.13478(18) 0.0402(5) 0.0562(16) Uani 0.761(9) 1 d P A 1
H41 H -0.0878 0.1614 0.0201 0.067 Uiso 0.761(9) 1 calc PR A 1
C36' C -0.162(2) 0.1366(7) 0.081(2) 0.0576(17) Uani 0.239(9) 1 d P A 2
H36' H -0.1972 0.1634 0.0842 0.069 Uiso 0.239(9) 1 calc PR A 2
C37' C -0.199(3) 0.1096(8) 0.159(2) 0.0629(15) Uani 0.239(9) 1 d P A 2
H37' H -0.2437 0.1188 0.2271 0.075 Uiso 0.239(9) 1 calc PR A 2
C38' C -0.178(3) 0.0714(7) 0.148(2) 0.0641(14) Uani 0.239(9) 1 d P A 2
H38' H -0.2200 0.0527 0.1989 0.077 Uiso 0.239(9) 1 calc PR A 2
C39' C -0.090(3) 0.0598(8) 0.0569(18) 0.0654(16) Uani 0.239(9) 1 d P A 2
H39' H -0.0593 0.0328 0.0474 0.079 Uiso 0.239(9) 1 calc PR A 2
C40' C -0.051(4) 0.0867(9) -0.013(3) 0.067(2) Uani 0.239(9) 1 d P A 2
H40' H -0.0020 0.0778 -0.0798 0.081 Uiso 0.239(9) 1 calc PR A 2
C41' C -0.071(3) 0.1238(7) -0.004(2) 0.0562(16) Uani 0.239(9) 1 d P A 2
H41' H -0.0253 0.1419 -0.0552 0.067 Uiso 0.239(9) 1 calc PR A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C3 112.06(13) . .
C1 N1 C12 122.80(13) . .
C3 N1 C12 125.13(13) . .
C1 N2 C4 111.85(13) . .
C1 N2 C16 123.31(14) . .
C4 N2 C16 124.84(14) . .
C2 N3 C9 111.67(15) . .
C2 N3 C20 123.47(14) . .
C9 N3 C20 124.85(14) . .
N1 C1 N2 104.33(14) . .
N3 C2 N3 104.6(2) . 4_565
C8 C3 C4 120.25(15) . .
C8 C3 N1 134.00(15) . .
C4 C3 N1 105.69(14) . .
C5 C4 C3 120.61(16) . .
C5 C4 N2 133.27(15) . .
C3 C4 N2 106.06(14) . .
C4 C5 C6 120.26(15) . .
C5 C6 C7 119.46(15) . .
C5 C6 C11 120.06(15) . .
C7 C6 C11 120.48(15) . .
C8 C7 C6 119.21(15) . .
C8 C7 C7 121.12(9) . 4_565
C6 C7 C7 119.66(9) . 4_565
C3 C8 C7 120.20(15) . .
C10 C9 C9 120.46(10) . 4_565
C10 C9 N3 133.49(16) . .
C9 C9 N3 106.04(9) 4_565 .
C9 C10 C11 120.13(16) . .
C10 C11 C11 119.40(10) . 4_565
C10 C11 C6 120.76(15) . .
C11 C11 C6 119.83(9) 4_565 .
N1 C12 C15 109.36(14) . .
N1 C12 C13 109.22(13) . .
C15 C12 C13 108.97(14) . .
N1 C12 C14 108.81(14) . .
C15 C12 C14 108.54(14) . .
C13 C12 C14 111.90(15) . .
N2 C16 C18 109.32(14) . .
N2 C16 C19 109.21(14) . .
C18 C16 C19 109.15(15) . .
N2 C16 C17 109.05(14) . .
C18 C16 C17 108.64(15) . .
C19 C16 C17 111.44(16) . .
N3 C20 C23 109.81(14) . .
N3 C20 C21 108.85(14) . .
C23 C20 C21 109.17(16) . .
N3 C20 C22 108.70(14) . .
C23 C20 C22 108.70(15) . .
C21 C20 C22 111.60(16) . .
C25 C24 C29 118.7(3) . .
C26 C25 C24 120.9(3) . .
C27 C26 C25 119.9(3) . .
C26 C27 C28 120.6(3) . .
C27 C28 C29 120.4(3) . .
C28 C29 C24 119.5(3) . .
C35 C30 C31 120.4(2) . .
C30 C31 C32 119.7(2) . .
C33 C32 C31 120.3(2) . .
C34 C33 C32 119.8(2) . .
C33 C34 C35 120.1(2) . .
C30 C35 C34 119.7(2) . .
C37 C36 C41 120.1(4) . .
C36 C37 C38 119.9(3) . .
C39 C38 C37 120.1(4) . .
C40 C39 C38 119.2(5) . .
C39 C40 C41 119.7(5) . .
C36 C41 C40 120.9(4) . .
C37' C36' C41' 117(2) . .
C38' C37' C36' 124(2) . .
C37' C38' C39' 116(2) . .
C40' C39' C38' 117(2) . .
C41' C40' C39' 127(3) . .
C40' C41' C36' 117(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.370(2) .
N1 C3 1.405(2) .
N1 C12 1.498(2) .
N2 C1 1.374(2) .
N2 C4 1.402(2) .
N2 C16 1.498(2) .
N3 C2 1.374(2) .
N3 C9 1.406(2) .
N3 C20 1.487(2) .
C2 N3 1.374(2) 4_565
C3 C8 1.384(2) .
C3 C4 1.399(2) .
C4 C5 1.376(2) .
C5 C6 1.403(2) .
C6 C7 1.420(2) .
C6 C11 1.469(2) .
C7 C8 1.405(2) .
C7 C7 1.475(3) 4_565
C9 C10 1.379(2) .
C9 C9 1.397(3) 4_565
C10 C11 1.401(2) .
C11 C11 1.419(3) 4_565
C12 C15 1.518(2) .
C12 C13 1.527(2) .
C12 C14 1.532(2) .
C16 C18 1.521(2) .
C16 C19 1.531(2) .
C16 C17 1.534(2) .
C20 C23 1.519(2) .
C20 C21 1.520(2) .
C20 C22 1.529(3) .
C24 C25 1.373(5) .
C24 C29 1.381(5) .
C25 C26 1.361(5) .
C26 C27 1.350(4) .
C27 C28 1.354(4) .
C28 C29 1.374(5) .
C30 C35 1.374(3) .
C30 C31 1.374(3) .
C31 C32 1.381(3) .
C32 C33 1.376(3) .
C33 C34 1.370(3) .
C34 C35 1.387(3) .
C36 C37 1.366(6) .
C36 C41 1.366(6) .
C37 C38 1.391(7) .
C38 C39 1.389(7) .
C39 C40 1.382(8) .
C40 C41 1.382(8) .
C36' C37' 1.34(3) .
C36' C41' 1.36(2) .
C37' C38' 1.31(3) .
C38' C39' 1.39(3) .
C39' C40' 1.27(4) .
C40' C41' 1.26(4) .
