#------------------------------------------------------------------------------
#$Date: 2016-04-05 17:20:53 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181524 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/88/7118801.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_7118801
loop_
_publ_author_name
'Tian, Cheng'
'Gong, Lei'
'Meggers, Eric'
_publ_section_title
;
 Chiral-at-metal iridium complex for efficient enantioselective transfer
 hydrogenation of ketones.
;
_journal_issue                   22
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4207
_journal_page_last               4210
_journal_paper_doi               10.1039/c6cc00972g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C45 H44 Cl Ir N4 O S2'
_chemical_formula_sum            'C45 H44 Cl Ir N4 O S2'
_chemical_formula_weight         948.61
_chemical_name_systematic        'Compound S2'
_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
_audit_update_record
;
2016-01-27 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.999(4)
_cell_length_b                   13.938(3)
_cell_length_c                   18.330(4)
_cell_measurement_reflns_used    4356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.30
_cell_volume                     4772.3(18)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28219
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.975
_exptl_absorpt_correction_T_max  0.6808
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethene, n-hexane'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.322
_refine_diff_density_min         -2.400
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0597
_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)+(0.1330P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1909
_reflns_number_gt                6783
_reflns_number_total             8827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00972g2.cif
_cod_data_source_block           tc1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7118801.cif.
;
_cod_original_cell_volume        4772.4(17)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7118801
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
O1 O 1.0051(5) -0.0780(6) 1.1349(4) 0.096(3) Uani 1 1 d .
Cl1 Cl 0.80444(9) 0.26576(14) 0.80060(10) 0.0387(4) Uani 1 1 d .
Ir1 Ir 0.701136(13) 0.378000(18) 0.829017(14) 0.03102(15) Uani 1 1 d .
S1 S 0.48404(9) 0.23274(14) 0.86309(12) 0.0483(5) Uani 1 1 d .
S2 S 0.81133(13) 0.61508(14) 0.70352(14) 0.0516(5) Uani 1 1 d .
N1 N 0.6189(3) 0.2730(4) 0.8434(3) 0.0343(13) Uani 1 1 d .
N2 N 0.7685(3) 0.4947(4) 0.8025(3) 0.0370(13) Uani 1 1 d .
N3 N 0.7463(3) 0.3566(4) 0.9542(3) 0.0369(13) Uani 1 1 d .
N4 N 0.7950(3) 0.2767(4) 0.9690(3) 0.0465(15) Uani 1 1 d .
H4A H 0.8128 0.2470 0.9340 0.056 Uiso 1 1 calc R
C1 C 0.7312(4) 0.3778(5) 1.0246(4) 0.0430(19) Uani 1 1 d .
C2 C 0.7721(4) 0.3171(6) 1.0823(4) 0.0501(19) Uani 1 1 d .
H2A H 0.7726 0.3205 1.1342 0.060 Uiso 1 1 calc R
C3 C 0.8117(4) 0.2507(5) 1.0441(4) 0.0426(17) Uani 1 1 d .
C4 C 0.6787(5) 0.4613(7) 1.0353(5) 0.064(2) Uani 1 1 d .
H4B H 0.6585 0.4892 0.9869 0.096 Uiso 1 1 calc R
H4C H 0.7049 0.5109 1.0672 0.096 Uiso 1 1 calc R
H4D H 0.6400 0.4361 1.0585 0.096 Uiso 1 1 calc R
C5 C 0.8636(4) 0.1673(6) 1.0713(4) 0.0487(18) Uani 1 1 d .
C6 C 0.8754(7) 0.0938(9) 1.0171(6) 0.087(4) Uani 1 1 d .
H6A H 0.8525 0.0991 0.9667 0.105 Uiso 1 1 calc R
C7 C 0.9226(7) 0.0125(8) 1.0414(6) 0.097(4) Uani 1 1 d .
H7A H 0.9299 -0.0357 1.0070 0.117 Uiso 1 1 calc R
C8 C 0.9584(5) 0.0057(6) 1.1187(5) 0.062(2) Uani 1 1 d .
C9 C 0.9466(4) 0.0755(6) 1.1715(4) 0.0515(19) Uani 1 1 d .
H9A H 0.9692 0.0694 1.2220 0.062 Uiso 1 1 calc R
C10 C 0.8987(4) 0.1581(6) 1.1471(4) 0.0496(19) Uani 1 1 d .
H10A H 0.8913 0.2054 1.1822 0.059 Uiso 1 1 calc R
C11 C 1.0419(5) -0.0928(7) 1.2136(6) 0.072(3) Uani 1 1 d .
H11A H 1.0711 -0.1512 1.2169 0.108 Uiso 1 1 calc R
H11B H 1.0060 -0.0994 1.2455 0.108 Uiso 1 1 calc R
H11C H 1.0727 -0.0376 1.2299 0.108 Uiso 1 1 calc R
C12 C 0.6177(4) 0.4725(5) 0.8462(4) 0.0380(16) Uani 1 1 d .
C13 C 0.6182(4) 0.5771(5) 0.8471(5) 0.0483(19) Uani 1 1 d .
H13A H 0.6595 0.6106 0.8385 0.058 Uiso 1 1 calc R
C14 C 0.5567(6) 0.6305(6) 0.8610(7) 0.061(3) Uani 1 1 d .
H14A H 0.5576 0.6986 0.8606 0.073 Uiso 1 1 calc R
C15 C 0.4933(5) 0.5800(7) 0.8756(6) 0.061(2) Uani 1 1 d .
H15A H 0.4538 0.6159 0.8860 0.074 Uiso 1 1 calc R
C16 C 0.4896(4) 0.4800(6) 0.8744(5) 0.052(2) Uani 1 1 d .
H16A H 0.4477 0.4478 0.8828 0.062 Uiso 1 1 calc R
C17 C 0.5528(3) 0.4246(5) 0.8596(4) 0.0380(16) Uani 1 1 d .
C18 C 0.5559(3) 0.3150(5) 0.8555(4) 0.0384(16) Uani 1 1 d .
C19 C 0.6125(3) 0.1683(5) 0.8391(4) 0.0347(15) Uani 1 1 d .
C20 C 0.6697(4) 0.0998(5) 0.8293(4) 0.0376(15) Uani 1 1 d .
H20A H 0.7155 0.1222 0.8231 0.045 Uiso 1 1 calc R
C21 C 0.6540(4) -0.0038(5) 0.8294(4) 0.0449(18) Uani 1 1 d .
C22 C 0.5819(4) -0.0362(6) 0.8377(5) 0.0495(19) Uani 1 1 d .
H22A H 0.5720 -0.1031 0.8370 0.059 Uiso 1 1 calc R
C23 C 0.5251(4) 0.0310(6) 0.8470(4) 0.0493(19) Uani 1 1 d .
H23A H 0.4789 0.0090 0.8521 0.059 Uiso 1 1 calc R
C024 C 0.8523(5) 0.6288(5) 0.8027(6) 0.047(2) Uani 1 1 d .
C24 C 0.5418(4) 0.1324(5) 0.8482(4) 0.0384(17) Uani 1 1 d .
C25 C 0.7148(4) -0.0857(6) 0.8218(5) 0.050(2) Uani 1 1 d .
C26 C 0.7319(7) -0.1418(7) 0.8966(8) 0.082(4) Uani 1 1 d .
H26A H 0.6881 -0.1719 0.9068 0.123 Uiso 1 1 calc R
H26B H 0.7507 -0.0973 0.9369 0.123 Uiso 1 1 calc R
H26C H 0.7677 -0.1914 0.8931 0.123 Uiso 1 1 calc R
C27 C 0.7856(5) -0.0362(7) 0.8034(7) 0.076(3) Uani 1 1 d .
H27A H 0.8213 -0.0856 0.7993 0.114 Uiso 1 1 calc R
H27B H 0.8050 0.0086 0.8432 0.114 Uiso 1 1 calc R
H27C H 0.7738 -0.0012 0.7563 0.114 Uiso 1 1 calc R
C28 C 0.6847(5) -0.1573(7) 0.7594(7) 0.075(3) Uani 1 1 d .
H28A H 0.6415 -0.1880 0.7709 0.112 Uiso 1 1 calc R
H28B H 0.7207 -0.2065 0.7557 0.112 Uiso 1 1 calc R
H28C H 0.6726 -0.1230 0.7121 0.112 Uiso 1 1 calc R
C29 C 0.6641(4) 0.3863(4) 0.7125(4) 0.0300(15) Uani 1 1 d .
C30 C 0.6106(4) 0.3285(6) 0.6656(4) 0.0467(18) Uani 1 1 d .
H30A H 0.5843 0.2825 0.6878 0.056 Uiso 1 1 calc R
C31 C 0.5962(5) 0.3396(7) 0.5840(5) 0.057(2) Uani 1 1 d .
H31A H 0.5632 0.2980 0.5541 0.069 Uiso 1 1 calc R
C32 C 0.6325(5) 0.4143(7) 0.5496(5) 0.061(2) Uani 1 1 d .
H32A H 0.6212 0.4235 0.4974 0.073 Uiso 1 1 calc R
C33 C 0.6862(5) 0.4752(6) 0.5943(4) 0.056(2) Uani 1 1 d .
H33A H 0.7103 0.5234 0.5717 0.068 Uiso 1 1 calc R
C34 C 0.7022(4) 0.4604(5) 0.6755(4) 0.0394(16) Uani 1 1 d .
C35 C 0.7575(4) 0.5173(5) 0.7275(4) 0.0391(16) Uani 1 1 d .
C36 C 0.8222(3) 0.5581(5) 0.8470(4) 0.0382(16) Uani 1 1 d .
C37 C 0.8467(4) 0.5575(6) 0.9275(4) 0.0440(17) Uani 1 1 d .
H37A H 0.8284 0.5110 0.9571 0.053 Uiso 1 1 calc R
C38 C 0.8991(5) 0.6278(5) 0.9628(5) 0.047(2) Uani 1 1 d .
C39 C 0.9272(4) 0.6962(6) 0.9157(5) 0.059(2) Uani 1 1 d .
H39A H 0.9620 0.7412 0.9383 0.071 Uiso 1 1 calc R
C40 C 0.9047(4) 0.6989(6) 0.8360(5) 0.056(2) Uani 1 1 d .
H40A H 0.9235 0.7451 0.8066 0.067 Uiso 1 1 calc R
C41 C 0.9229(6) 0.6298(6) 1.0527(6) 0.063(3) Uani 1 1 d .
C42 C 0.8770(8) 0.7050(13) 1.0838(7) 0.130(6) Uani 1 1 d .
H42A H 0.8264 0.6873 1.0705 0.195 Uiso 1 1 calc R
H42B H 0.8844 0.7681 1.0628 0.195 Uiso 1 1 calc R
H42C H 0.8909 0.7076 1.1379 0.195 Uiso 1 1 calc R
C43 C 0.9206(8) 0.5256(10) 1.0867(6) 0.117(5) Uani 1 1 d .
H43A H 0.8717 0.5003 1.0746 0.176 Uiso 1 1 calc R
H43B H 0.9356 0.5286 1.1407 0.176 Uiso 1 1 calc R
H43C H 0.9530 0.4833 1.0658 0.176 Uiso 1 1 calc R
C44 C 1.0055(6) 0.6640(10) 1.0751(7) 0.107(4) Uani 1 1 d .
H44A H 1.0105 0.7289 1.0561 0.160 Uiso 1 1 calc R
H44B H 1.0362 0.6198 1.0536 0.160 Uiso 1 1 calc R
H44C H 1.0198 0.6640 1.1293 0.160 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'
S S 0.1246 0.1234 '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
C8 O1 C11 117.7(7)
C29 Ir1 C12 89.8(3)
C29 Ir1 N2 80.5(2)
C12 Ir1 N2 93.2(3)
C29 Ir1 N1 92.5(2)
C12 Ir1 N1 80.1(3)
N2 Ir1 N1 170.4(2)
C29 Ir1 N3 175.0(2)
C12 Ir1 N3 94.8(2)
N2 Ir1 N3 101.0(2)
N1 Ir1 N3 86.4(2)
C29 Ir1 Cl1 87.46(18)
C12 Ir1 Cl1 176.8(2)
N2 Ir1 Cl1 84.81(15)
N1 Ir1 Cl1 101.56(16)
N3 Ir1 Cl1 88.00(15)
C18 S1 C24 89.5(3)
C35 S2 C024 89.6(3)
C18 N1 C19 111.3(5)
C18 N1 Ir1 113.1(4)
C19 N1 Ir1 135.4(4)
C35 N2 C36 112.1(5)
C35 N2 Ir1 113.7(4)
C36 N2 Ir1 134.2(4)
C1 N3 N4 102.8(5)
C1 N3 Ir1 141.5(5)
N4 N3 Ir1 113.2(4)
C3 N4 N3 114.0(6)
N3 C1 C2 111.9(6)
N3 C1 C4 120.9(6)
C2 C1 C4 127.2(7)
C3 C2 C1 105.9(6)
N4 C3 C2 105.3(6)
N4 C3 C5 121.8(6)
C2 C3 C5 132.9(7)
C10 C5 C6 119.4(8)
C10 C5 C3 122.4(7)
C6 C5 C3 118.2(8)
C7 C6 C5 119.6(9)
C8 C7 C6 119.8(9)
C9 C8 C7 121.0(8)
C9 C8 O1 125.0(8)
C7 C8 O1 114.0(7)
C8 C9 C10 119.4(7)
C5 C10 C9 120.8(8)
C13 C12 C17 117.4(6)
C13 C12 Ir1 128.1(5)
C17 C12 Ir1 114.6(5)
C14 C13 C12 120.8(7)
C13 C14 C15 120.3(7)
C16 C15 C14 121.3(7)
C15 C16 C17 118.6(7)
C12 C17 C16 121.7(6)
C12 C17 C18 114.0(5)
C16 C17 C18 124.3(6)
N1 C18 C17 118.1(5)
N1 C18 S1 115.5(5)
C17 C18 S1 126.3(5)
N1 C19 C24 113.6(6)
N1 C19 C20 126.3(6)
C24 C19 C20 120.0(6)
C21 C20 C19 118.5(6)
C20 C21 C22 119.5(7)
C20 C21 C25 122.2(7)
C22 C21 C25 118.4(7)
C23 C22 C21 122.3(7)
C24 C23 C22 117.6(7)
C40 C024 C36 122.0(9)
C40 C024 S2 128.1(7)
C36 C024 S2 109.9(6)
C23 C24 C19 122.2(7)
C23 C24 S1 127.8(6)
C19 C24 S1 110.0(5)
C28 C25 C26 108.4(10)
C28 C25 C27 109.5(8)
C26 C25 C27 110.7(8)
C28 C25 C21 109.8(7)
C26 C25 C21 108.1(7)
C27 C25 C21 110.4(7)
C30 C29 C34 117.5(7)
C30 C29 Ir1 129.3(5)
C34 C29 Ir1 113.2(5)
C29 C30 C31 121.5(7)
C32 C31 C30 119.8(8)
C31 C32 C33 120.8(7)
C32 C33 C34 118.6(7)
C33 C34 C29 121.7(7)
C33 C34 C35 123.7(7)
C29 C34 C35 114.6(6)
N2 C35 C34 118.0(6)
N2 C35 S2 115.0(5)
C34 C35 S2 127.1(5)
C024 C36 C37 118.7(7)
C024 C36 N2 113.4(7)
C37 C36 N2 127.9(6)
C38 C37 C36 120.5(7)
C39 C38 C37 118.2(8)
C39 C38 C41 121.8(7)
C37 C38 C41 120.0(7)
C40 C39 C38 123.0(7)
C39 C40 C024 117.5(8)
C42 C41 C43 114.9(12)
C42 C41 C44 107.1(10)
C43 C41 C44 105.4(9)
C42 C41 C38 108.4(9)
C43 C41 C38 111.1(7)
C44 C41 C38 109.8(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.464(10)
O1 C11 1.497(12)
Cl1 Ir1 2.6353(18)
Ir1 C29 2.127(7)
Ir1 C12 2.129(6)
Ir1 N2 2.179(6)
Ir1 N1 2.192(6)
Ir1 N3 2.318(6)
S1 C18 1.808(7)
S1 C24 1.829(8)
S2 C35 1.807(7)
S2 C024 1.852(11)
N1 C18 1.385(9)
N1 C19 1.465(9)
N2 C35 1.388(9)
N2 C36 1.477(9)
N3 C1 1.403(10)
N3 N4 1.442(8)
N4 C3 1.403(9)
C1 C2 1.462(11)
C1 C4 1.569(10)
C2 C3 1.452(11)
C3 C5 1.546(11)
C5 C10 1.434(11)
C5 C6 1.472(13)
C6 C7 1.464(14)
C7 C8 1.457(13)
C8 C9 1.418(11)
C9 C10 1.484(11)
C12 C13 1.458(10)
C12 C17 1.461(10)
C13 C14 1.446(12)
C14 C15 1.462(13)
C15 C16 1.396(12)
C16 C17 1.494(9)
C17 C18 1.531(11)
C19 C24 1.470(10)
C19 C20 1.482(10)
C20 C21 1.476(10)
C21 C22 1.476(10)
C21 C25 1.647(10)
C22 C23 1.462(11)
C23 C24 1.448(10)
C024 C40 1.448(11)
C024 C36 1.459(11)
C25 C28 1.548(14)
C25 C26 1.560(16)
C25 C27 1.603(13)
C29 C30 1.448(10)
C29 C34 1.494(10)
C30 C31 1.479(11)
C31 C32 1.455(14)
C32 C33 1.459(12)
C33 C34 1.478(10)
C34 C35 1.508(9)
C36 C37 1.464(10)
C37 C38 1.461(10)
C38 C39 1.452(12)
C38 C41 1.628(14)
C39 C40 1.446(12)
C41 C42 1.537(15)
C41 C43 1.585(16)
C41 C44 1.621(15)
