#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:37:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180270 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/56/7115613.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_7115613
loop_
_publ_author_name
'Xiangqing Jia'
'Lei Zhang'
'Chuan Qin'
'Xuebing Leng'
'Zheng Huang'
_publ_section_title
;
 Iridium complexes of new NCP pincer ligands: catalytic alkane
 dehydrogenation and alkene isomerization
;
_journal_name_full               Chem.Commun.
_journal_page_first              11056
_journal_paper_doi               10.1039/C3cc46851H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C20 H28 Cl Ir N O P'
_chemical_formula_weight         557.05
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.782(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1303(10)
_cell_length_b                   13.7700(14)
_cell_length_c                   15.0040(15)
_cell_measurement_reflns_used    9615
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.56
_cell_volume                     2014.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19210
_diffrn_reflns_theta_full        30.60
_diffrn_reflns_theta_max         30.60
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    6.849
_exptl_absorpt_correction_T_max  0.4070
_exptl_absorpt_correction_T_min  0.2331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.315
_refine_diff_density_min         -1.768
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         6175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.9757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0544
_reflns_number_gt                5127
_reflns_number_total             6175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46851h2.cif
_cod_data_source_block           mo_dm12657_0m_1
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7115613
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
Ir1 Ir 0.257854(9) 0.667313(7) 0.080833(6) 0.01493(3) Uani 1 1 d .
H1M H 0.1835 0.6649 0.0092 0.022 Uiso 1 1 d R
Cl1 Cl 0.48364(6) 0.66707(5) 0.18486(5) 0.02488(13) Uani 1 1 d .
N1 N 0.2180(2) 0.51911(17) 0.11252(15) 0.0208(5) Uani 1 1 d .
O1 O 0.05616(19) 0.83905(14) 0.03017(14) 0.0204(4) Uani 1 1 d .
P1 P 0.22401(6) 0.82373(5) 0.04501(5) 0.01460(12) Uani 1 1 d .
C1 C 0.0659(3) 0.67566(19) 0.08266(18) 0.0166(5) Uani 1 1 d .
C2 C -0.0077(3) 0.7616(2) 0.06076(19) 0.0195(5) Uani 1 1 d .
C3 C -0.1390(3) 0.7704(2) 0.0712(2) 0.0256(6) Uani 1 1 d .
H3 H -0.1893 0.8291 0.0558 0.031 Uiso 1 1 calc R
C4 C -0.1955(3) 0.6903(3) 0.1052(2) 0.0310(7) Uani 1 1 d .
H4 H -0.2850 0.6954 0.1133 0.037 Uiso 1 1 calc R
C5 C -0.1245(3) 0.6042(2) 0.1273(2) 0.0275(6) Uani 1 1 d .
H5 H -0.1651 0.5508 0.1501 0.033 Uiso 1 1 calc R
C6 C 0.0083(3) 0.5957(2) 0.11576(18) 0.0205(5) Uani 1 1 d .
C7 C 0.0967(3) 0.5096(2) 0.13488(17) 0.0219(5) Uani 1 1 d .
C8 C 0.0635(4) 0.4236(2) 0.1726(2) 0.0310(7) Uani 1 1 d .
H8 H -0.0192 0.4186 0.1906 0.037 Uiso 1 1 calc R
C9 C 0.1522(4) 0.3459(2) 0.1836(2) 0.0390(9) Uani 1 1 d .
H9 H 0.1332 0.2878 0.2119 0.047 Uiso 1 1 calc R
C10 C 0.2685(4) 0.3531(2) 0.1534(3) 0.0368(8) Uani 1 1 d .
H10 H 0.3277 0.2987 0.1577 0.044 Uiso 1 1 calc R
C11 C 0.2989(3) 0.4404(2) 0.1165(2) 0.0256(6) Uani 1 1 d .
C12 C 0.4176(3) 0.4498(2) 0.0761(3) 0.0343(7) Uani 1 1 d .
H12A H 0.3856 0.4754 0.0129 0.052 Uiso 1 1 calc R
H12B H 0.4598 0.3860 0.0747 0.052 Uiso 1 1 calc R
H12C H 0.4855 0.4944 0.1141 0.052 Uiso 1 1 calc R
C13 C 0.2495(3) 0.8625(2) -0.06827(17) 0.0182(5) Uani 1 1 d .
C14 C 0.1381(3) 0.8121(2) -0.1449(2) 0.0276(6) Uani 1 1 d .
H14A H 0.0481 0.8392 -0.1463 0.041 Uiso 1 1 calc R
H14B H 0.1387 0.7423 -0.1324 0.041 Uiso 1 1 calc R
H14C H 0.1566 0.8229 -0.2050 0.041 Uiso 1 1 calc R
C15 C 0.2387(3) 0.9717(2) -0.0867(2) 0.0245(6) Uani 1 1 d .
H15A H 0.3126 1.0051 -0.0412 0.037 Uiso 1 1 calc R
H15B H 0.1498 0.9952 -0.0816 0.037 Uiso 1 1 calc R
H15C H 0.2469 0.9847 -0.1492 0.037 Uiso 1 1 calc R
C16 C 0.3917(3) 0.8253(2) -0.0714(2) 0.0260(6) Uani 1 1 d .
H16A H 0.4072 0.8420 -0.1312 0.039 Uiso 1 1 calc R
H16B H 0.3955 0.7546 -0.0634 0.039 Uiso 1 1 calc R
H16C H 0.4628 0.8556 -0.0214 0.039 Uiso 1 1 calc R
C17 C 0.2909(3) 0.9155(2) 0.13793(18) 0.0188(5) Uani 1 1 d .
C18 C 0.2120(3) 1.0123(2) 0.1229(2) 0.0288(6) Uani 1 1 d .
H18A H 0.1143 0.9998 0.1153 0.043 Uiso 1 1 calc R
H18B H 0.2239 1.0441 0.0672 0.043 Uiso 1 1 calc R
H18C H 0.2476 1.0545 0.1766 0.043 Uiso 1 1 calc R
C19 C 0.4441(3) 0.9335(2) 0.1497(2) 0.0234(6) Uani 1 1 d .
H19A H 0.4567 0.9634 0.0934 0.035 Uiso 1 1 calc R
H19B H 0.4935 0.8716 0.1609 0.035 Uiso 1 1 calc R
H19C H 0.4800 0.9770 0.2025 0.035 Uiso 1 1 calc R
C20 C 0.2713(3) 0.8696(2) 0.2267(2) 0.0251(6) Uani 1 1 d .
H20A H 0.3044 0.9145 0.2787 0.038 Uiso 1 1 calc R
H20B H 0.3233 0.8088 0.2396 0.038 Uiso 1 1 calc R
H20C H 0.1737 0.8562 0.2186 0.038 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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
C1 Ir1 N1 78.82(10)
C1 Ir1 P1 81.83(8)
N1 Ir1 P1 160.61(7)
C1 Ir1 Cl1 140.23(8)
N1 Ir1 Cl1 93.32(6)
P1 Ir1 Cl1 102.49(2)
C1 Ir1 H1M 66.9
N1 Ir1 H1M 93.8
P1 Ir1 H1M 77.3
Cl1 Ir1 H1M 152.8
C11 N1 C7 119.2(3)
C11 N1 Ir1 128.4(2)
C7 N1 Ir1 112.33(19)
C2 O1 P1 114.10(17)
O1 P1 C13 103.35(11)
O1 P1 C17 99.43(11)
C13 P1 C17 111.98(12)
O1 P1 Ir1 103.85(7)
C13 P1 Ir1 116.57(9)
C17 P1 Ir1 118.32(9)
C2 C1 C6 120.4(2)
C2 C1 Ir1 121.22(19)
C6 C1 Ir1 118.1(2)
C3 C2 O1 121.2(3)
C3 C2 C1 121.2(3)
O1 C2 C1 117.7(2)
C2 C3 C4 118.1(3)
C2 C3 H3 120.9
C4 C3 H3 120.9
C5 C4 C3 121.7(3)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 119.7(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 118.9(3)
C1 C6 C7 114.5(2)
C5 C6 C7 126.6(3)
N1 C7 C8 121.0(3)
N1 C7 C6 114.6(2)
C8 C7 C6 124.4(3)
C9 C8 C7 119.2(3)
C9 C8 H8 120.4
C7 C8 H8 120.4
C10 C9 C8 119.6(3)
C10 C9 H9 120.2
C8 C9 H9 120.2
C9 C10 C11 119.6(3)
C9 C10 H10 120.2
C11 C10 H10 120.2
N1 C11 C10 120.9(3)
N1 C11 C12 117.3(3)
C10 C11 C12 121.8(3)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C15 C13 C14 107.8(2)
C15 C13 C16 110.1(2)
C14 C13 C16 109.2(2)
C15 C13 P1 115.25(19)
C14 C13 P1 107.25(19)
C16 C13 P1 107.10(18)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C19 C17 C20 109.4(2)
C19 C17 C18 110.2(2)
C20 C17 C18 107.4(2)
C19 C17 P1 110.23(18)
C20 C17 P1 105.23(19)
C18 C17 P1 114.10(19)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 C1 1.955(2)
Ir1 N1 2.158(2)
Ir1 P1 2.2239(7)
Ir1 Cl1 2.3929(7)
Ir1 H1M 1.1328
N1 C11 1.351(4)
N1 C7 1.366(4)
O1 C2 1.388(3)
O1 P1 1.6672(19)
P1 C13 1.866(3)
P1 C17 1.867(3)
C1 C2 1.389(4)
C1 C6 1.399(4)
C2 C3 1.387(4)
C3 C4 1.401(5)
C3 H3 0.9500
C4 C5 1.380(5)
C4 H4 0.9500
C5 C6 1.407(4)
C5 H5 0.9500
C6 C7 1.466(4)
C7 C8 1.392(4)
C8 C9 1.377(5)
C8 H8 0.9500
C9 C10 1.376(6)
C9 H9 0.9500
C10 C11 1.393(4)
C10 H10 0.9500
C11 C12 1.493(5)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C15 1.526(4)
C13 C14 1.540(4)
C13 C16 1.542(4)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 C19 1.534(4)
C17 C20 1.536(4)
C17 C18 1.538(4)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 Ir1 N1 C11 171.7(2)
P1 Ir1 N1 C11 167.54(17)
Cl1 Ir1 N1 C11 -47.7(2)
C1 Ir1 N1 C7 -11.58(18)
P1 Ir1 N1 C7 -15.7(3)
Cl1 Ir1 N1 C7 129.08(17)
C2 O1 P1 C13 134.21(19)
C2 O1 P1 C17 -110.36(19)
C2 O1 P1 Ir1 12.07(19)
C1 Ir1 P1 O1 -7.20(11)
N1 Ir1 P1 O1 -3.1(2)
Cl1 Ir1 P1 O1 -146.98(8)
C1 Ir1 P1 C13 -120.11(12)
N1 Ir1 P1 C13 -116.0(2)
Cl1 Ir1 P1 C13 100.12(10)
C1 Ir1 P1 C17 101.74(12)
N1 Ir1 P1 C17 105.8(2)
Cl1 Ir1 P1 C17 -38.03(10)
N1 Ir1 C1 C2 -176.4(2)
P1 Ir1 C1 C2 2.2(2)
Cl1 Ir1 C1 C2 101.9(2)
N1 Ir1 C1 C6 10.02(19)
P1 Ir1 C1 C6 -171.4(2)
Cl1 Ir1 C1 C6 -71.6(2)
P1 O1 C2 C3 166.6(2)
P1 O1 C2 C1 -11.9(3)
C6 C1 C2 C3 0.1(4)
Ir1 C1 C2 C3 -173.3(2)
C6 C1 C2 O1 178.6(2)
Ir1 C1 C2 O1 5.2(3)
O1 C2 C3 C4 -178.0(3)
C1 C2 C3 C4 0.4(4)
C2 C3 C4 C5 -0.6(5)
C3 C4 C5 C6 0.1(5)
C2 C1 C6 C5 -0.6(4)
Ir1 C1 C6 C5 173.0(2)
C2 C1 C6 C7 179.2(2)
Ir1 C1 C6 C7 -7.1(3)
C4 C5 C6 C1 0.5(4)
C4 C5 C6 C7 -179.3(3)
C11 N1 C7 C8 8.2(4)
Ir1 N1 C7 C8 -168.9(2)
C11 N1 C7 C6 -171.8(2)
Ir1 N1 C7 C6 11.1(3)
C1 C6 C7 N1 -3.5(3)
C5 C6 C7 N1 176.3(3)
C1 C6 C7 C8 176.6(3)
C5 C6 C7 C8 -3.6(4)
N1 C7 C8 C9 -2.8(4)
C6 C7 C8 C9 177.1(3)
C7 C8 C9 C10 -2.9(5)
C8 C9 C10 C11 3.3(5)
C7 N1 C11 C10 -7.7(4)
Ir1 N1 C11 C10 168.8(2)
C7 N1 C11 C12 169.6(2)
Ir1 N1 C11 C12 -13.8(4)
C9 C10 C11 N1 2.0(5)
C9 C10 C11 C12 -175.2(3)
O1 P1 C13 C15 72.3(2)
C17 P1 C13 C15 -33.8(2)
Ir1 P1 C13 C15 -174.49(17)
O1 P1 C13 C14 -47.7(2)
C17 P1 C13 C14 -153.85(19)
Ir1 P1 C13 C14 65.4(2)
O1 P1 C13 C16 -164.83(18)
C17 P1 C13 C16 89.1(2)
Ir1 P1 C13 C16 -51.6(2)
O1 P1 C17 C19 -166.95(19)
C13 P1 C17 C19 -58.3(2)
Ir1 P1 C17 C19 81.6(2)
O1 P1 C17 C20 75.22(19)
C13 P1 C17 C20 -176.14(18)
Ir1 P1 C17 C20 -36.2(2)
O1 P1 C17 C18 -42.3(2)
C13 P1 C17 C18 66.3(2)
Ir1 P1 C17 C18 -153.71(17)
