#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:14:32 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179717 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/19/7001940.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_7001940
loop_
_publ_author_name
'Lorber, Christian'
'Vendier, Laure'
_publ_section_title
;
 Synthesis and structure of early transition metal NHC complexes
;
_journal_issue                   35
_journal_name_full               'Dalton Transactions'
_journal_page_first              6972
_journal_paper_doi               10.1039/b905056f
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C25 H36 Cl2 N4 Zr1'
_chemical_formula_sum            'C25 H36 Cl2 N4 Zr'
_chemical_formula_weight         554.7
_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
_cell_angle_alpha                90
_cell_angle_beta                 101.690(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5739(3)
_cell_length_b                   16.2577(4)
_cell_length_c                   17.9949(5)
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.0804
_cell_measurement_theta_min      2.5678
_cell_measurement_wavelength     0.71073
_cell_volume                     2742.80(14)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford-Diffraction XCALIBUR'
_diffrn_measurement_method       ω-φ
_diffrn_orient_matrix_UB_11      -0.05591471
_diffrn_orient_matrix_UB_12      0.0212068821
_diffrn_orient_matrix_UB_13      0.0123040534
_diffrn_orient_matrix_UB_21      -0.0502995604
_diffrn_orient_matrix_UB_22      -0.0275568769
_diffrn_orient_matrix_UB_23      -0.0210171857
_diffrn_orient_matrix_UB_31      0.0077684555
_diffrn_orient_matrix_UB_32      -0.0262685396
_diffrn_orient_matrix_UB_33      0.0320340868
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21290
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0316
_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)+(0.0563P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                3900
_reflns_number_total             5606
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b905056f.txt
_cod_data_source_block           4
_cod_original_cell_volume        2742.80(13)
_cod_database_code               7001940
loop_
_symmetry_equiv_pos_as_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 0.1475(3) 0.20083(16) 0.92107(16) 0.0271(6) Uani 1 1 d . . .
C2 C 0.0106(4) 0.1397(2) 0.9934(2) 0.0602(12) Uani 1 1 d . . .
H2 H -0.0362 0.098 1.0161 0.072 Uiso 1 1 calc R . .
C3 C 0.0062(5) 0.2204(2) 1.0059(2) 0.0677(13) Uani 1 1 d . . .
H3 H -0.045 0.2472 1.0389 0.081 Uiso 1 1 calc R . .
C4 C 0.1337(3) 0.04821(16) 0.91868(16) 0.0263(6) Uani 1 1 d . . .
C5 C 0.0463(3) 0.00961(17) 0.85672(16) 0.0276(6) Uani 1 1 d . . .
C6 C 0.0867(3) -0.06823(17) 0.83758(17) 0.0296(7) Uani 1 1 d . . .
H6 H 0.0303 -0.0957 0.7953 0.036 Uiso 1 1 calc R . .
C7 C 0.2077(3) -0.10728(17) 0.87867(16) 0.0279(7) Uani 1 1 d . . .
C8 C 0.2855(3) -0.06761(17) 0.94091(16) 0.0289(7) Uani 1 1 d . . .
H8 H 0.3665 -0.0946 0.9699 0.035 Uiso 1 1 calc R . .
C9 C 0.2513(3) 0.00917(17) 0.96305(16) 0.0279(7) Uani 1 1 d . . .
C10 C -0.0880(3) 0.0490(2) 0.8139(2) 0.0469(9) Uani 1 1 d . . .
H10A H -0.1573 0.0532 0.847 0.07 Uiso 1 1 calc R . .
H10B H -0.128 0.0154 0.7695 0.07 Uiso 1 1 calc R . .
H10C H -0.0662 0.1041 0.7973 0.07 Uiso 1 1 calc R . .
C11 C 0.3316(4) 0.0484(2) 1.03482(17) 0.0428(8) Uani 1 1 d . . .
H11A H 0.4116 0.013 1.0578 0.064 Uiso 1 1 calc R . .
H11B H 0.2675 0.0556 1.0704 0.064 Uiso 1 1 calc R . .
H11C H 0.368 0.1022 1.0229 0.064 Uiso 1 1 calc R . .
C12 C 0.2516(3) -0.19094(18) 0.85607(18) 0.0378(7) Uani 1 1 d . . .
H12A H 0.307 -0.2189 0.9007 0.057 Uiso 1 1 calc R . .
H12B H 0.3101 -0.185 0.8175 0.057 Uiso 1 1 calc R . .
H12C H 0.1664 -0.2234 0.8353 0.057 Uiso 1 1 calc R . .
C13 C 0.1122(4) 0.34380(18) 0.95780(17) 0.0371(8) Uani 1 1 d . . .
C14 C 0.0201(4) 0.38925(19) 0.90234(18) 0.0400(8) Uani 1 1 d . . .
C15 C 0.0488(4) 0.4721(2) 0.8971(2) 0.0490(10) Uani 1 1 d . . .
H15 H -0.0117 0.504 0.8596 0.059 Uiso 1 1 calc R . .
C16 C 0.1601(5) 0.5098(2) 0.9435(2) 0.0506(10) Uani 1 1 d . . .
C17 C 0.2409(4) 0.4643(2) 1.0011(2) 0.0502(10) Uani 1 1 d . . .
H17 H 0.3144 0.4911 1.0361 0.06 Uiso 1 1 calc R . .
C18 C 0.2191(4) 0.38133(19) 1.00987(19) 0.0453(9) Uani 1 1 d . . .
C19 C 0.3066(5) 0.3334(2) 1.0755(2) 0.0651(12) Uani 1 1 d . . .
H19A H 0.2538 0.3296 1.1167 0.098 Uiso 1 1 calc R . .
H19B H 0.3975 0.3616 1.0939 0.098 Uiso 1 1 calc R . .
H19C H 0.3249 0.2779 1.0584 0.098 Uiso 1 1 calc R . .
C20 C 0.1923(5) 0.5988(2) 0.9319(3) 0.0793(15) Uani 1 1 d . . .
H20A H 0.2622 0.6029 0.8991 0.119 Uiso 1 1 calc R . .
H20B H 0.2313 0.6242 0.9811 0.119 Uiso 1 1 calc R . .
H20C H 0.1044 0.6272 0.908 0.119 Uiso 1 1 calc R . .
C21 C -0.1062(4) 0.3494(2) 0.8532(2) 0.0581(10) Uani 1 1 d . . .
H21A H -0.074 0.3054 0.8234 0.087 Uiso 1 1 calc R . .
H21B H -0.1595 0.3905 0.8188 0.087 Uiso 1 1 calc R . .
H21C H -0.1681 0.3262 0.8851 0.087 Uiso 1 1 calc R . .
C22 C 0.3629(4) 0.0580(2) 0.7703(2) 0.0543(10) Uani 1 1 d . . .
H22A H 0.3699 0.0443 0.7181 0.081 Uiso 1 1 calc R . .
H22B H 0.2632 0.0537 0.7755 0.081 Uiso 1 1 calc R . .
H22C H 0.4214 0.0196 0.8054 0.081 Uiso 1 1 calc R . .
C23 C 0.5580(4) 0.1505(3) 0.7777(3) 0.0736(13) Uani 1 1 d . . .
H23A H 0.6218 0.1171 0.8153 0.11 Uiso 1 1 calc R . .
H23B H 0.5856 0.2085 0.7844 0.11 Uiso 1 1 calc R . .
H23C H 0.565 0.1327 0.7265 0.11 Uiso 1 1 calc R . .
C24 C 0.4143(4) 0.4093(2) 0.8464(2) 0.0581(11) Uani 1 1 d . . .
H24A H 0.513 0.4227 0.8438 0.087 Uiso 1 1 calc R . .
H24B H 0.4079 0.3994 0.8993 0.087 Uiso 1 1 calc R . .
H24C H 0.3519 0.4552 0.8261 0.087 Uiso 1 1 calc R . .
C25 C 0.3752(5) 0.3491(2) 0.7238(2) 0.0631(12) Uani 1 1 d . . .
H25A H 0.3054 0.3913 0.7023 0.095 Uiso 1 1 calc R . .
H25B H 0.3525 0.2975 0.6958 0.095 Uiso 1 1 calc R . .
H25C H 0.4709 0.3673 0.7197 0.095 Uiso 1 1 calc R . .
N1 N 0.0960(3) 0.12856(14) 0.94141(14) 0.0319(6) Uani 1 1 d . . .
N2 N 0.0900(3) 0.25722(15) 0.96177(15) 0.0383(7) Uani 1 1 d . . .
N3 N 0.4129(3) 0.14070(16) 0.78753(15) 0.0375(6) Uani 1 1 d . . .
N4 N 0.3705(3) 0.33640(15) 0.80223(14) 0.0349(6) Uani 1 1 d . . .
Cl1 Cl 0.48831(9) 0.23231(5) 0.95448(5) 0.0456(2) Uani 1 1 d . . .
Cl2 Cl 0.08764(8) 0.21359(6) 0.73815(4) 0.0446(2) Uani 1 1 d . . .
Zr1 Zr 0.30934(3) 0.226508(16) 0.835256(15) 0.02398(10) Uani 1 1 d . . .
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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 '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
_geom_angle_publ_flag
N1 C1 N2 103.4(2) . . ?
N1 C1 Zr1 129.34(19) . . ?
N2 C1 Zr1 127.3(2) . . ?
C3 C2 N1 106.8(3) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 106.8(3) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
C9 C4 C5 122.4(3) . . ?
C9 C4 N1 118.1(3) . . ?
C5 C4 N1 119.3(3) . . ?
C6 C5 C4 117.1(3) . . ?
C6 C5 C10 121.0(3) . . ?
C4 C5 C10 121.9(3) . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 118.2(3) . . ?
C8 C7 C12 120.7(3) . . ?
C6 C7 C12 121.1(3) . . ?
C9 C8 C7 122.9(3) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C4 117.4(3) . . ?
C8 C9 C11 121.7(3) . . ?
C4 C9 C11 120.8(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.5(3) . . ?
C18 C13 N2 119.9(3) . . ?
C14 C13 N2 118.5(3) . . ?
C15 C14 C13 117.2(3) . . ?
C15 C14 C21 122.1(3) . . ?
C13 C14 C21 120.7(3) . . ?
C16 C15 C14 122.7(3) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C17 118.1(3) . . ?
C15 C16 C20 120.4(4) . . ?
C17 C16 C20 121.4(4) . . ?
C16 C17 C18 122.5(4) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C17 C18 C13 117.6(3) . . ?
C17 C18 C19 121.3(4) . . ?
C13 C18 C19 121.1(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 H25A 109.5 . . ?
N4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C2 111.7(2) . . ?
C1 N1 C4 125.9(2) . . ?
C2 N1 C4 122.2(2) . . ?
C1 N2 C3 111.4(3) . . ?
C1 N2 C13 124.0(2) . . ?
C3 N2 C13 124.6(3) . . ?
C22 N3 C23 111.3(3) . . ?
C22 N3 Zr1 124.8(2) . . ?
C23 N3 Zr1 123.2(2) . . ?
C25 N4 C24 111.1(3) . . ?
C25 N4 Zr1 119.2(2) . . ?
C24 N4 Zr1 129.7(2) . . ?
N3 Zr1 N4 107.07(11) . . ?
N3 Zr1 C1 125.91(10) . . ?
N4 Zr1 C1 126.98(10) . . ?
N3 Zr1 Cl1 94.74(8) . . ?
N4 Zr1 Cl1 91.76(7) . . ?
C1 Zr1 Cl1 82.76(7) . . ?
N3 Zr1 Cl2 93.82(8) . . ?
N4 Zr1 Cl2 97.27(8) . . ?
C1 Zr1 Cl2 82.41(7) . . ?
Cl1 Zr1 Cl2 165.17(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.353(3) . ?
C1 N2 1.357(4) . ?
C1 Zr1 2.435(3) . ?
C2 C3 1.332(5) . ?
C2 N1 1.373(4) . ?
C2 H2 0.95 . ?
C3 N2 1.375(4) . ?
C3 H3 0.95 . ?
C4 C9 1.394(4) . ?
C4 C5 1.400(4) . ?
C4 N1 1.437(3) . ?
C5 C6 1.387(4) . ?
C5 C10 1.501(4) . ?
C6 C7 1.395(4) . ?
C6 H6 0.95 . ?
C7 C8 1.373(4) . ?
C7 C12 1.504(4) . ?
C8 C9 1.370(4) . ?
C8 H8 0.95 . ?
C9 C11 1.504(4) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C18 1.382(5) . ?
C13 C14 1.401(4) . ?
C13 N2 1.427(4) . ?
C14 C15 1.381(4) . ?
C14 C21 1.494(5) . ?
C15 C16 1.359(5) . ?
C15 H15 0.95 . ?
C16 C17 1.376(5) . ?
C16 C20 1.503(5) . ?
C17 C18 1.379(4) . ?
C17 H17 0.95 . ?
C18 C19 1.518(5) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 N3 1.440(4) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 N3 1.444(4) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 N4 1.441(4) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 N4 1.437(4) . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
N3 Zr1 2.003(2) . ?
N4 Zr1 2.007(2) . ?
Cl1 Zr1 2.4614(8) . ?
Cl2 Zr1 2.4698(8) . ?
