#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:34:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178571 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/81/4068154.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_4068154
loop_
_publ_author_name
'Gierz, Verena'
'Maichle-Mössmer, Cäcilia'
'Kunz, Doris'
_publ_section_title
;
 1,10-Phenanthroline Analogue Pyridazine-Based N-Heterocyclic Carbene
 Ligands
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              739
_journal_paper_doi               10.1021/om2011547
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C32 H46 Cl F18 N10 P3'
_chemical_formula_weight         1041.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 119.486(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.2056(18)
_cell_length_b                   7.9758(4)
_cell_length_c                   27.112(2)
_cell_measurement_reflns_used    17864
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      61.33
_cell_measurement_theta_min      4.77
_cell_volume                     4556.3(6)
_computing_cell_refinement       X-AREA
_computing_data_collection       X-AREA
_computing_data_reduction        X-AREA
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       omega-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  0.0892
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17854
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+17.4666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                3145
_reflns_number_total             3871
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2011547_si_002.cif
_cod_data_source_block           vgorg
_cod_original_cell_volume        4556.3(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4068154
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C11 C 0.13923(14) 0.9596(4) 0.12087(13) 0.0306(7) Uani 1 1 d . . .
H11 H 0.0972 0.9835 0.0918 0.037 Uiso 1 1 calc R . .
C13 C 0.22331(16) 0.9099(4) 0.20480(15) 0.0379(8) Uani 1 1 d . . .
H13 H 0.2485 0.8939 0.2445 0.046 Uiso 1 1 calc R . .
C14 C 0.24422(14) 0.9013(4) 0.16684(14) 0.0324(7) Uani 1 1 d . . .
C15 C 0.30358(15) 0.8724(4) 0.16864(15) 0.0386(8) Uani 1 1 d . . .
H15 H 0.3402 0.8450 0.2036 0.046 Uiso 1 1 calc R . .
C16 C 0.30770(15) 0.8839(4) 0.12124(15) 0.0364(8) Uani 1 1 d . . .
H16 H 0.3472 0.8654 0.1226 0.044 Uiso 1 1 calc R . .
C17 C 0.25243(14) 0.9241(4) 0.06857(15) 0.0318(7) Uani 1 1 d . . .
C18 C 0.23946(15) 0.9537(4) 0.01456(15) 0.0350(8) Uani 1 1 d . . .
H18 H 0.2691 0.9497 0.0013 0.042 Uiso 1 1 calc R . .
C20 C 0.14843(15) 0.9846(4) 0.01446(13) 0.0327(7) Uani 1 1 d . . .
H20 H 0.1050 1.0050 0.0027 0.039 Uiso 1 1 calc R . .
C121 C 0.11846(18) 0.9683(5) 0.20164(16) 0.0463(9) Uani 1 1 d . . .
H11A H 0.0908 1.0671 0.1843 0.056 Uiso 0.727(8) 1 calc PR A 1
H11B H 0.1451 0.9899 0.2427 0.056 Uiso 0.727(8) 1 calc PR A 1
H11C H 0.0779 1.0196 0.1733 0.056 Uiso 0.273(8) 1 calc PR A 2
H11D H 0.1393 1.0464 0.2341 0.056 Uiso 0.273(8) 1 calc PR A 2
C122 C 0.0785(4) 0.8186(10) 0.1931(4) 0.0673(15) Uani 0.727(8) 1 d P A 1
H12C H 0.0519 0.7973 0.1519 0.081 Uiso 0.727(8) 1 calc PR A 1
H12D H 0.0498 0.8410 0.2086 0.081 Uiso 0.727(8) 1 calc PR A 1
C123 C 0.1176(4) 0.6639(10) 0.2213(3) 0.0673(15) Uani 0.727(8) 1 d P A 1
H12E H 0.0893 0.5684 0.2145 0.101 Uiso 0.727(8) 1 calc PR A 1
H12F H 0.1435 0.6835 0.2621 0.101 Uiso 0.727(8) 1 calc PR A 1
H12G H 0.1454 0.6396 0.2054 0.101 Uiso 0.727(8) 1 calc PR A 1
C23A C 0.0776(10) 0.665(3) 0.1841(9) 0.0673(15) Uani 0.273(8) 1 d P A 2
H23A H 0.0717 0.5663 0.2025 0.101 Uiso 0.273(8) 1 calc PR A 2
H23B H 0.1059 0.6371 0.1691 0.101 Uiso 0.273(8) 1 calc PR A 2
H23C H 0.0364 0.7012 0.1530 0.101 Uiso 0.273(8) 1 calc PR A 2
C22A C 0.1039(11) 0.793(3) 0.2231(11) 0.0673(15) Uani 0.273(8) 1 d P A 2
H22A H 0.1443 0.7518 0.2550 0.081 Uiso 0.273(8) 1 calc PR A 2
H22B H 0.0750 0.8172 0.2384 0.081 Uiso 0.273(8) 1 calc PR A 2
C191 C 0.14207(18) 1.0321(5) -0.07870(15) 0.0452(9) Uani 1 1 d . . .
H19A H 0.1061 0.9535 -0.0989 0.054 Uiso 1 1 calc R . .
H19B H 0.1713 1.0172 -0.0941 0.054 Uiso 1 1 calc R . .
C192 C 0.1175(3) 1.2075(6) -0.08943(18) 0.0712(14) Uani 1 1 d . . .
H19C H 0.1525 1.2852 -0.0655 0.085 Uiso 1 1 calc R . .
H19D H 0.0842 1.2185 -0.0786 0.085 Uiso 1 1 calc R . .
C193 C 0.0903(3) 1.2558(6) -0.15120(19) 0.0736(14) Uani 1 1 d . . .
H19E H 0.0744 1.3711 -0.1568 0.110 Uiso 1 1 calc R . .
H19F H 0.0554 1.1797 -0.1749 0.110 Uiso 1 1 calc R . .
H19G H 0.1235 1.2478 -0.1618 0.110 Uiso 1 1 calc R . .
N12 N 0.15970(13) 0.9456(3) 0.17617(12) 0.0347(7) Uani 1 1 d . A .
N19 N 0.17602(13) 0.9904(4) -0.01744(12) 0.0358(7) Uani 1 1 d . . .
N21 N 0.19404(11) 0.9444(3) 0.06625(11) 0.0277(6) Uani 1 1 d . . .
N22 N 0.19022(11) 0.9329(3) 0.11484(11) 0.0279(6) Uani 1 1 d . . .
N100 N 0.39088(18) 0.8591(5) 0.05057(16) 0.0595(9) Uani 1 1 d . B .
C102 C 0.4391(2) 0.8830(7) 0.0588(2) 0.0686(11) Uani 1 1 d . . .
C103 C 0.4947(5) 0.9417(16) 0.0501(6) 0.0686(11) Uani 0.452(10) 1 d P B 1
H10A H 0.5351 0.9134 0.0838 0.103 Uiso 0.452(10) 1 calc PR B 1
H10B H 0.4921 1.0633 0.0443 0.103 Uiso 0.452(10) 1 calc PR B 1
H10C H 0.4920 0.8855 0.0169 0.103 Uiso 0.452(10) 1 calc PR B 1
C10A C 0.5091(4) 0.8959(13) 0.0850(5) 0.0686(11) Uani 0.548(10) 1 d P B 2
H10D H 0.5198 0.9561 0.0593 0.103 Uiso 0.548(10) 1 calc PR B 2
H10E H 0.5275 0.7832 0.0920 0.103 Uiso 0.548(10) 1 calc PR B 2
H10F H 0.5261 0.9570 0.1209 0.103 Uiso 0.548(10) 1 calc PR B 2
P1 P 0.19392(4) 0.42167(11) 0.11432(4) 0.0357(3) Uani 1 1 d . . .
P2 P 0.0000 0.24296(17) 0.2500 0.0405(3) Uani 1 2 d S . .
F11 F 0.21617(12) 0.5277(3) 0.07814(10) 0.0674(7) Uani 1 1 d . . .
F12 F 0.14092(12) 0.3273(3) 0.06092(11) 0.0719(8) Uani 1 1 d . . .
F13 F 0.14478(13) 0.5664(3) 0.10506(14) 0.0779(9) Uani 1 1 d . . .
F14 F 0.17126(15) 0.3206(3) 0.15237(13) 0.0822(9) Uani 1 1 d . . .
F15 F 0.24651(14) 0.5137(3) 0.16950(10) 0.0767(9) Uani 1 1 d . . .
F16 F 0.24252(12) 0.2767(3) 0.12413(15) 0.0854(10) Uani 1 1 d . . .
F21 F 0.0000 0.0553(13) 0.2500 0.170(9) Uani 0.497(16) 2 d SP C 1
F22 F 0.0529(4) 0.2566(13) 0.2324(5) 0.107(4) Uani 0.497(16) 1 d P C 1
F23 F -0.0478(5) 0.254(2) 0.1865(3) 0.150(7) Uani 0.497(16) 1 d P C 1
F24 F 0.0000 0.4370(13) 0.2500 0.190(13) Uani 0.497(16) 2 d SP C 1
F21A F -0.0485(4) 0.3729(12) 0.2195(6) 0.152(7) Uani 0.503(16) 1 d P C 2
F22A F -0.0580(7) 0.1181(15) 0.2218(5) 0.166(7) Uani 0.503(16) 1 d P C 2
F23A F 0.0053(8) 0.220(2) 0.1961(5) 0.184(9) Uani 0.503(16) 1 d P C 2
Cl1 Cl 0.0000 0.0000 0.0000 0.0590(5) Uani 1 2 d S . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
N12 C11 N22 105.6(3) . .
C14 C13 N12 108.4(3) . .
C13 C14 N22 104.1(3) . .
C13 C14 C15 136.6(3) . .
N22 C14 C15 119.3(3) . .
C16 C15 C14 120.2(3) . .
C15 C16 C17 119.8(3) . .
C18 C17 N21 103.9(3) . .
C18 C17 C16 136.1(3) . .
N21 C17 C16 120.0(3) . .
C17 C18 N19 108.2(3) . .
N19 C20 N21 105.9(3) . .
N12 C121 C122 111.5(4) . .
N12 C121 C22A 112.3(8) . .
C122 C121 C22A 28.3(8) . .
C121 C122 C123 112.4(7) . .
C23A C22A C121 117.6(18) . .
N19 C191 C192 112.1(3) . .
C191 C192 C193 111.6(4) . .
C11 N12 C13 110.3(3) . .
C11 N12 C121 123.6(3) . .
C13 N12 C121 126.1(3) . .
C20 N19 C18 110.2(3) . .
C20 N19 C191 123.9(3) . .
C18 N19 C191 125.9(3) . .
C20 N21 N22 128.2(2) . .
C20 N21 C17 111.9(3) . .
N22 N21 C17 119.8(3) . .
C11 N22 N21 127.6(3) . .
C11 N22 C14 111.5(3) . .
N21 N22 C14 120.8(2) . .
N100 C102 C10A 164.6(7) . .
N100 C102 C103 160.6(8) . .
C10A C102 C103 34.7(5) . .
F12 P1 F16 90.40(16) . .
F12 P1 F11 93.32(15) . .
F16 P1 F11 92.49(17) . .
F12 P1 F13 89.69(16) . .
F16 P1 F13 179.21(18) . .
F11 P1 F13 88.29(15) . .
F12 P1 F15 177.98(16) . .
F16 P1 F15 89.69(17) . .
F11 P1 F15 88.69(14) . .
F13 P1 F15 90.19(16) . .
F12 P1 F14 88.24(16) . .
F16 P1 F14 89.21(17) . .
F11 P1 F14 177.69(16) . .
F13 P1 F14 90.01(17) . .
F15 P1 F14 89.74(16) . .
F21A P2 F21A 90.8(8) . 2
F21A P2 F21 134.6(4) . .
F21A P2 F21 134.6(4) 2 .
F21A P2 F23 122.9(9) . 2
F21A P2 F23 51.6(6) 2 2
F21 P2 F23 93.2(6) . 2
F21A P2 F23 51.6(6) . .
F21A P2 F23 122.9(9) 2 .
F21 P2 F23 93.2(6) . .
F23 P2 F23 173.7(12) 2 .
F21A P2 F23A 101.6(9) . 2
F21A P2 F23A 88.1(8) 2 2
F21 P2 F23A 83.1(6) . 2
F23 P2 F23A 46.3(6) 2 2
F23 P2 F23A 134.7(6) . 2
F21A P2 F23A 88.1(7) . .
F21A P2 F23A 101.6(9) 2 .
F21 P2 F23A 83.1(6) . .
F23 P2 F23A 134.7(6) 2 .
F23 P2 F23A 46.3(6) . .
F23A P2 F23A 166.3(12) 2 .
F21A P2 F24 45.4(4) . .
F21A P2 F24 45.4(4) 2 .
F21 P2 F24 180.000(4) . .
F23 P2 F24 86.8(6) 2 .
F23 P2 F24 86.8(6) . .
F23A P2 F24 96.9(6) 2 .
F23A P2 F24 96.9(6) . .
F21A P2 F22 65.2(7) . 2
F21A P2 F22 108.8(7) 2 2
F21 P2 F22 94.0(4) . 2
F23 P2 F22 86.2(6) 2 2
F23 P2 F22 93.4(6) . 2
F23A P2 F22 42.4(6) 2 2
F23A P2 F22 139.1(5) . 2
F24 P2 F22 86.0(4) . 2
F21A P2 F22 108.8(7) . .
F21A P2 F22 65.2(7) 2 .
F21 P2 F22 94.0(4) . .
F23 P2 F22 93.4(6) 2 .
F23 P2 F22 86.2(6) . .
F23A P2 F22 139.1(5) 2 .
F23A P2 F22 42.4(6) . .
F24 P2 F22 86.0(4) . .
F22 P2 F22 172.1(7) 2 .
F21A P2 F22A 84.2(8) . .
F21A P2 F22A 170.6(8) 2 .
F21 P2 F22A 50.9(6) . .
F23 P2 F22A 125.3(8) 2 .
F23 P2 F22A 59.4(6) . .
F23A P2 F22A 85.1(6) 2 .
F23A P2 F22A 86.3(8) . .
F24 P2 F22A 129.1(6) . .
F22 P2 F22A 61.8(6) 2 .
F22 P2 F22A 124.0(6) . .
F21A P2 F22A 170.6(8) . 2
F21A P2 F22A 84.2(8) 2 2
F21 P2 F22A 50.9(6) . 2
F23 P2 F22A 59.4(6) 2 2
F23 P2 F22A 125.3(8) . 2
F23A P2 F22A 86.3(8) 2 2
F23A P2 F22A 85.1(6) . 2
F24 P2 F22A 129.1(6) . 2
F22 P2 F22A 124.0(6) 2 2
F22 P2 F22A 61.8(6) . 2
F22A P2 F22A 101.8(12) . 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 N12 1.332(4) .
C11 N22 1.339(4) .
C13 C14 1.354(5) .
C13 N12 1.370(4) .
C14 N22 1.395(4) .
C14 C15 1.432(5) .
C15 C16 1.340(5) .
C16 C17 1.432(5) .
C17 C18 1.358(5) .
C17 N21 1.393(4) .
C18 N19 1.373(4) .
C20 N19 1.329(4) .
C20 N21 1.330(4) .
C121 N12 1.478(4) .
C121 C122 1.481(8) .
C121 C22A 1.62(2) .
C122 C123 1.513(13) .
C23A C22A 1.38(3) .
C191 N19 1.484(4) .
C191 C192 1.491(6) .
C192 C193 1.517(6) .
N21 N22 1.368(3) .
N100 C102 1.092(5) .
C102 C10A 1.483(9) .
C102 C103 1.548(11) .
P1 F12 1.575(2) .
P1 F16 1.576(3) .
P1 F11 1.577(2) .
P1 F13 1.587(3) .
P1 F15 1.588(3) .
P1 F14 1.604(3) .
P2 F21A 1.476(7) .
P2 F21A 1.476(7) 2
P2 F21 1.497(10) .
P2 F23 1.534(7) 2
P2 F23 1.534(7) .
P2 F23A 1.540(8) 2
P2 F23A 1.540(8) .
P2 F24 1.548(11) .
P2 F22 1.574(6) 2
P2 F22 1.574(6) .
P2 F22A 1.578(8) .
P2 F22A 1.578(8) 2
