#------------------------------------------------------------------------------
#$Date: 2020-10-06 08:49:05 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257213 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558697.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_1558697
loop_
_publ_author_name
'Zhang, Dejin'
'Yang, Guoqiang'
'Zhao, Yue'
'Shao, Shouyan'
'Zhu, Guisheng'
'Liu, Peijun'
'Liu, Jia'
'Hu, Xingbang'
'Zhang, Zhibing'
_publ_section_title
;
 Efficient methanol carbonylation to methyl acetate catalyzed by a
 cyclic(alkyl)(amino)carbene iridium complex
;
_journal_issue                   17
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              6045
_journal_page_last               6049
_journal_paper_doi               10.1039/D0CY00054J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C24 H35 Cl I0 Ir N O2'
_chemical_formula_weight         597.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.9040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4294(3)
_cell_length_b                   15.2306(4)
_cell_length_c                   16.4958(5)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.55
_cell_volume                     2360.38(12)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23267
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         2.547
_exptl_absorpt_coefficient_mu    5.789
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         5835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0239P)²+1.7835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5173
_reflns_number_total             5835
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cy00054j2.cif
_cod_data_source_block           20191119LI_HXB_ZDJ_0m_a
_cod_depositor_comments
'Adding full bibliography for 1558696--1558697.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1558697
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.543
_shelx_estimated_absorpt_t_max   0.624
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0210(3) 0.62621(19) 0.4758(2) 0.0450(7) Uani 1 1 d . . . . .
H1A H -0.040993 0.663190 0.441593 0.068 Uiso 1 1 calc R U . . .
H1B H -0.010791 0.624796 0.529551 0.068 Uiso 1 1 calc R U . . .
H1C H 0.019694 0.567834 0.453812 0.068 Uiso 1 1 calc R U . . .
C2 C 0.2234(4) 0.6591(2) 0.39374(19) 0.0485(8) Uani 1 1 d . . . . .
H2A H 0.321817 0.675561 0.395312 0.073 Uiso 1 1 calc R U . . .
H2B H 0.167265 0.698796 0.359064 0.073 Uiso 1 1 calc R U . . .
H2C H 0.211791 0.600407 0.372909 0.073 Uiso 1 1 calc R U . . .
C3 C 0.1742(3) 0.66291(17) 0.47984(17) 0.0326(6) Uani 1 1 d . . . . .
H3 H 0.172930 0.724354 0.497403 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2762(2) 0.61174(15) 0.53885(16) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.2882(3) 0.52191(16) 0.52441(17) 0.0320(5) Uani 1 1 d . . . . .
H5 H 0.232909 0.497048 0.480948 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3787(3) 0.46890(16) 0.57218(19) 0.0355(6) Uani 1 1 d . . . . .
H6 H 0.382321 0.408851 0.562320 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4641(3) 0.50606(16) 0.63490(18) 0.0330(6) Uani 1 1 d . . . . .
H7 H 0.526580 0.470244 0.666582 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4602(2) 0.59566(15) 0.65260(16) 0.0259(5) Uani 1 1 d . . . . .
C9 C 0.3624(2) 0.64793(14) 0.60444(15) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.5677(3) 0.62941(17) 0.71909(17) 0.0320(5) Uani 1 1 d . . . . .
H10 H 0.553126 0.692656 0.725437 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5530(4) 0.5845(2) 0.80148(19) 0.0512(8) Uani 1 1 d . . . . .
H11A H 0.455665 0.587508 0.814283 0.077 Uiso 1 1 calc R U . . .
H11B H 0.612663 0.613793 0.843112 0.077 Uiso 1 1 calc R U . . .
H11C H 0.581356 0.524124 0.798462 0.077 Uiso 1 1 calc R U . . .
C12 C 0.7190(3) 0.6142(2) 0.6947(2) 0.0475(8) Uani 1 1 d . . . . .
H12A H 0.737381 0.552328 0.692470 0.071 Uiso 1 1 calc R U . . .
H12B H 0.786216 0.641066 0.734165 0.071 Uiso 1 1 calc R U . . .
H12C H 0.728197 0.639818 0.642233 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2268(2) 0.76367(15) 0.68323(15) 0.0243(5) Uani 1 1 d . . . . .
C14 C 0.0845(2) 0.72056(17) 0.65888(18) 0.0326(6) Uani 1 1 d . . . . .
H14A H 0.018041 0.735587 0.697615 0.049 Uiso 1 1 calc R U . . .
H14B H 0.096318 0.657976 0.657745 0.049 Uiso 1 1 calc R U . . .
H14C H 0.049028 0.740814 0.605872 0.049 Uiso 1 1 calc R U . . .
C15 C 0.2768(3) 0.73569(19) 0.76939(17) 0.0362(6) Uani 1 1 d . . . . .
H15A H 0.367246 0.762311 0.785204 0.054 Uiso 1 1 calc R U . . .
H15B H 0.286210 0.672955 0.771498 0.054 Uiso 1 1 calc R U . . .
H15C H 0.208578 0.754141 0.805887 0.054 Uiso 1 1 calc R U . . .
C16 C 0.2201(2) 0.86324(15) 0.67281(18) 0.0299(5) Uani 1 1 d . . . . .
H16A H 0.140733 0.879379 0.634399 0.036 Uiso 1 1 calc R U . . .
H16B H 0.207822 0.891413 0.724476 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3605(2) 0.89171(14) 0.64110(15) 0.0228(4) Uani 1 1 d . . . . .
C18 C 0.4698(2) 0.92552(16) 0.70938(16) 0.0280(5) Uani 1 1 d . . . . .
H18A H 0.497356 0.876833 0.745242 0.034 Uiso 1 1 calc R U . . .
H18B H 0.554340 0.944813 0.684788 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4186(3) 1.0003(2) 0.7604(2) 0.0462(8) Uani 1 1 d . . . . .
H19A H 0.394647 1.049891 0.726045 0.069 Uiso 1 1 calc R U . . .
H19B H 0.492697 1.016350 0.801223 0.069 Uiso 1 1 calc R U . . .
H19C H 0.336087 0.981751 0.786121 0.069 Uiso 1 1 calc R U . . .
C20 C 0.3411(3) 0.96277(16) 0.57467(17) 0.0337(6) Uani 1 1 d . . . . .
H20A H 0.313630 1.016953 0.599987 0.040 Uiso 1 1 calc R U . . .
H20B H 0.432578 0.972874 0.553556 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2330(4) 0.9435(2) 0.5034(2) 0.0495(8) Uani 1 1 d . . . . .
H21A H 0.249049 0.885674 0.483038 0.074 Uiso 1 1 calc R U . . .
H21B H 0.242919 0.985833 0.461120 0.074 Uiso 1 1 calc R U . . .
H21C H 0.138744 0.946975 0.521024 0.074 Uiso 1 1 calc R U . . .
C22 C 0.7182(3) 0.81967(17) 0.6474(2) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.7763(3) 0.82053(17) 0.49442(19) 0.0357(6) Uani 1 1 d . . . . .
Cl1 Cl 0.48499(10) 0.80787(6) 0.41781(5) 0.0551(2) Uani 1 1 d . . . . .
Ir1 Ir 0.60630(2) 0.80939(2) 0.54747(2) 0.02671(4) Uani 1 1 d . . . . .
N1 N 0.34141(18) 0.74040(12) 0.62596(12) 0.0205(4) Uani 1 1 d . . . . .
C24 C 0.4191(2) 0.80696(14) 0.60644(14) 0.0212(4) Uani 1 1 d . . . . .
O1 O 0.7854(2) 0.82960(17) 0.70206(17) 0.0571(6) Uani 1 1 d . . . . .
O2 O 0.8776(2) 0.83014(16) 0.46419(15) 0.0519(6) 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 0.0000 0.0000 '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'
I I -0.4742 1.8119 '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'
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'
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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C2 110.4(2) . . ?
C4 C3 C1 112.3(2) . . ?
C2 C3 C1 107.6(2) . . ?
C4 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C1 C3 H3 108.8 . . ?
C5 C4 C9 117.7(2) . . ?
C5 C4 C3 116.7(2) . . ?
C9 C4 C3 125.6(2) . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C8 122.3(2) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C9 117.5(2) . . ?
C7 C8 C10 117.0(2) . . ?
C9 C8 C10 125.4(2) . . ?
C8 C9 C4 121.2(2) . . ?
C8 C9 N1 120.0(2) . . ?
C4 C9 N1 118.67(19) . . ?
C8 C10 C12 109.8(2) . . ?
C8 C10 C11 112.5(2) . . ?
C12 C10 C11 108.7(2) . . ?
C8 C10 H10 108.6 . . ?
C12 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 108.9(2) . . ?
C14 C13 C16 111.91(19) . . ?
C15 C13 C16 113.0(2) . . ?
C14 C13 N1 113.0(2) . . ?
C15 C13 N1 109.38(18) . . ?
C16 C13 N1 100.62(17) . . ?
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 . . ?
C17 C16 C13 106.98(18) . . ?
C17 C16 H16A 110.3 . . ?
C13 C16 H16A 110.3 . . ?
C17 C16 H16B 110.3 . . ?
C13 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 C24 103.82(18) . . ?
C16 C17 C20 112.90(19) . . ?
C24 C17 C20 110.6(2) . . ?
C16 C17 C18 112.8(2) . . ?
C24 C17 C18 108.21(18) . . ?
C20 C17 C18 108.38(19) . . ?
C19 C18 C17 115.4(2) . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
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 . . ?
C21 C20 C17 116.6(2) . . ?
C21 C20 H20A 108.2 . . ?
C17 C20 H20A 108.2 . . ?
C21 C20 H20B 108.2 . . ?
C17 C20 H20B 108.2 . . ?
H20A C20 H20B 107.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 Ir1 175.7(3) . . ?
O2 C23 Ir1 177.4(3) . . ?
C22 Ir1 C23 87.94(12) . . ?
C22 Ir1 C24 91.52(10) . . ?
C23 Ir1 C24 175.88(10) . . ?
C22 Ir1 Cl1 173.60(8) . . ?
C23 Ir1 Cl1 86.87(10) . . ?
C24 Ir1 Cl1 93.38(7) . . ?
C24 N1 C9 126.44(19) . . ?
C24 N1 C13 114.26(18) . . ?
C9 N1 C13 119.06(17) . . ?
N1 C24 C17 109.5(2) . . ?
N1 C24 Ir1 129.98(16) . . ?
C17 C24 Ir1 120.30(15) . . ?
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 C3 1.545(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.532(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.523(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.395(3) . ?
C4 C9 1.409(3) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(3) . ?
C8 C10 1.518(3) . ?
C9 N1 1.470(3) . ?
C10 C12 1.532(4) . ?
C10 C11 1.538(4) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.517(3) . ?
C13 C15 1.520(4) . ?
C13 C16 1.527(3) . ?
C13 N1 1.537(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.528(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C24 1.533(3) . ?
C17 C20 1.540(3) . ?
C17 C18 1.548(3) . ?
C18 C19 1.519(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.517(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O1 1.068(4) . ?
C22 Ir1 1.886(3) . ?
C23 O2 1.124(3) . ?
C23 Ir1 1.898(3) . ?
Cl1 Ir1 2.3378(9) . ?
Ir1 C24 2.088(2) . ?
N1 C24 1.307(3) . ?
