#------------------------------------------------------------------------------
#$Date: 2019-09-20 03:06:39 +0300 (Fri, 20 Sep 2019) $
#$Revision: 218559 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/42/7124215.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_7124215
loop_
_publ_author_name
'Ito, Jun-ichi'
'Ishihara, Takahiro'
'Fukuoka, Takaki'
'Binti Mat Napi, Siti Rokiah'
'Kameo, Hajime'
'Nishiyama, Hisao'
_publ_section_title
;
 Modulation of Coordination Geometry of NCN and NCNC Rh Complexes for
 Ambidextrous Chiral Catalysts
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06520B
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C26 H31 Cl2 N2 Rh'
_chemical_formula_weight         545.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2016-09-30 deposited with the CCDC.    2019-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.0881(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4067(10)
_cell_length_b                   17.1103(11)
_cell_length_c                   10.8096(7)
_cell_measurement_reflns_used    8128
_cell_measurement_temperature    93.0(2)
_cell_measurement_theta_max      25.0283
_cell_measurement_theta_min      2.5298
_cell_volume                     2420.7(3)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v3.0.29'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruke AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      93.0(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8335
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear pale red'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.856
_refine_ls_abs_structure_details
;
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_coef       0.0085(6)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.290
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0447P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                4052
_reflns_number_total             4104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06520b2.cif
_cod_data_source_block           Nishiyama_ito34
_cod_database_code               7124215
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0 0.4745(5) 0 0.0106(16) Uani d T P S 1
C C2 0.0637(4) 0.4360(3) 0.1417(6) 0.0122(12) Uani d . . . 1
C C3 0.0625(4) 0.3568(4) 0.1428(6) 0.0117(11) Uani d . . . 1
C C4 0 0.3167(5) 0 0.0161(18) Uani d T P S 1
H H4 0 0.2612 0 0.019 Uiso calc U P R 1
C C5 0.1256(4) 0.3101(3) 0.2924(6) 0.0176(12) Uani d . . . 1
H H5A 0.1979 0.3243 0.35 0.026 Uiso calc U . R 1
H H5B 0.1172 0.2542 0.2681 0.026 Uiso calc U . R 1
H H5C 0.1026 0.3218 0.3556 0.026 Uiso calc U . R 1
C C6 0.1315(4) 0.4897(3) 0.2803(6) 0.0141(12) Uani d . . . 1
H H6A 0.1357 0.4702 0.3703 0.017 Uiso calc U . R 1
H H6B 0.2013 0.4907 0.3092 0.017 Uiso calc U . R 1
C C7 0.1649(4) 0.6334(3) 0.3383(6) 0.0146(10) Uani d . . . 1
H H7 0.2191 0.6305 0.3227 0.017 Uiso calc U . R 1
C C8 0.1139(5) 0.7130(3) 0.2818(7) 0.0257(15) Uani d . . . 1
H H8A 0.0894 0.721 0.1747 0.039 Uiso calc U . R 1
H H8B 0.1634 0.7539 0.3481 0.039 Uiso calc U . R 1
H H8C 0.0561 0.7155 0.2864 0.039 Uiso calc U . R 1
C C9 0.2151(4) 0.6186(3) 0.5077(5) 0.0140(10) Uani d . . . 1
C C10 0.1601(4) 0.6230(3) 0.5678(6) 0.0219(12) Uani d . . . 1
H H10 0.0894 0.6357 0.5008 0.026 Uiso calc U . R 1
C C11 0.2065(5) 0.6093(3) 0.7225(7) 0.0295(13) Uani d . . . 1
H H11 0.168 0.6119 0.7617 0.035 Uiso calc U . R 1
C C12 0.3093(5) 0.5917(4) 0.8202(6) 0.0311(13) Uani d . . . 1
H H12 0.3419 0.583 0.9273 0.037 Uiso calc U . R 1
C C13 0.3653(4) 0.5865(4) 0.7638(6) 0.0288(12) Uani d . . . 1
H H13 0.436 0.5741 0.8319 0.035 Uiso calc U . R 1
C C14 0.3183(4) 0.5995(3) 0.6069(6) 0.0194(12) Uani d . . . 1
H H14 0.3567 0.5953 0.5679 0.023 Uiso calc U . R 1
C C15 0.5 0.5259(4) 0.5 0.0103(15) Uani d T P S 1
C C16 0.5542(4) 0.5615(3) 0.6426(6) 0.0103(12) Uani d . . . 1
C C17 0.5537(4) 0.6458(3) 0.6427(7) 0.0154(12) Uani d . . . 1
C C18 0.5 0.6824(4) 0.5 0.0128(17) Uani d T P S 1
H H18 0.5 0.7379 0.5 0.015 Uiso calc U P R 1
C C19 0.6078(4) 0.6912(3) 0.7916(6) 0.0198(12) Uani d . . . 1
H H19A 0.615 0.7458 0.7723 0.03 Uiso calc U . R 1
H H19B 0.6756 0.6686 0.8677 0.03 Uiso calc U . R 1
H H19C 0.5681 0.6888 0.8321 0.03 Uiso calc U . R 1
C C20 0.6026(4) 0.5081(3) 0.7810(6) 0.0121(11) Uani d . . . 1
H H20A 0.6697 0.5293 0.8682 0.014 Uiso calc U . R 1
H H20B 0.5585 0.5041 0.8147 0.014 Uiso calc U . R 1
C C21 0.6279(3) 0.3656(3) 0.8420(5) 0.0134(10) Uani d . . . 1
H H21 0.561 0.3599 0.8247 0.016 Uiso calc U . R 1
C C22 0.6490(4) 0.2900(3) 0.7937(6) 0.0214(13) Uani d . . . 1
H H22A 0.5925 0.2787 0.6852 0.032 Uiso calc U . R 1
H H22B 0.6554 0.2473 0.8596 0.032 Uiso calc U . R 1
H H22C 0.7127 0.2949 0.805 0.032 Uiso calc U . R 1
C C23 0.7093(3) 0.3831(3) 1.0132(5) 0.0132(10) Uani d . . . 1
C C24 0.6836(4) 0.3789(3) 1.1146(6) 0.0174(10) Uani d . . . 1
H H24 0.6153 0.3673 1.0753 0.021 Uiso calc U . R 1
C C25 0.7568(4) 0.3914(3) 1.2724(6) 0.0222(13) Uani d . . . 1
H H25 0.7387 0.3879 1.3407 0.027 Uiso calc U . R 1
C C26 0.8555(3) 0.4088(4) 1.3295(5) 0.0188(10) Uani d . . . 1
H H26 0.9058 0.4177 1.4373 0.023 Uiso calc U . R 1
C C27 0.8814(4) 0.4133(4) 1.2286(5) 0.0178(11) Uani d . . . 1
H H27 0.9496 0.4254 1.2682 0.021 Uiso calc U . R 1
C C28 0.8096(3) 0.4005(3) 1.0725(5) 0.0145(12) Uani d . . . 1
H H28 0.8284 0.4035 1.005 0.017 Uiso calc U . R 1
Cl Cl1 0.14219(8) 0.59501(8) 0.00407(13) 0.0161(3) Uani d . . . 1
Cl Cl2 0.37808(8) 0.40558(8) 0.54227(13) 0.0147(3) Uani d . . . 1
N N1 0.0867(3) 0.5714(2) 0.2385(4) 0.0131(8) Uani d . . . 1
N N2 0.6162(3) 0.4292(2) 0.7361(4) 0.0122(8) Uani d . . . 1
Rh Rh1 0 0.58602(2) 0 0.00917(16) Uani d T P S 1
Rh Rh2 0.5 0.41376(2) 0.5 0.00883(16) Uani d T P S 1
H H30 0.036(4) 0.575(3) 0.255(6) 0.027(14) Uiso d . . . 1
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C2 2 . 123.6(7)
C2 C1 Rh1 2 . 118.2(4)
C2 C1 Rh1 . . 118.2(4)
C3 C2 C1 . . 118.5(6)
C3 C2 C6 . . 126.9(6)
C1 C2 C6 . . 114.5(5)
C2 C3 C4 . . 118.7(6)
C2 C3 C5 . . 122.1(6)
C4 C3 C5 . . 119.2(6)
C3 C4 C3 2 . 121.9(8)
N1 C6 C2 . . 109.2(4)
N1 C7 C9 . . 111.0(4)
N1 C7 C8 . . 108.6(4)
C9 C7 C8 . . 113.7(4)
C14 C9 C10 . . 118.8(5)
C14 C9 C7 . . 119.7(4)
C10 C9 C7 . . 121.5(5)
C11 C10 C9 . . 121.1(5)
C10 C11 C12 . . 119.4(5)
C13 C12 C11 . . 120.6(5)
C12 C13 C14 . . 120.1(5)
C9 C14 C13 . . 119.9(5)
C16 C15 C16 . 2_656 127.3(7)
C16 C15 Rh2 . . 116.4(4)
C16 C15 Rh2 2_656 . 116.4(4)
C15 C16 C17 . . 116.4(6)
C15 C16 C20 . . 116.2(5)
C17 C16 C20 . . 127.3(5)
C18 C17 C16 . . 116.9(6)
C18 C17 C19 . . 122.0(6)
C16 C17 C19 . . 121.1(5)
C17 C18 C17 2_656 . 126.1(8)
N2 C20 C16 . . 108.5(4)
N2 C21 C22 . . 107.8(4)
N2 C21 C23 . . 113.5(4)
C22 C21 C23 . . 111.9(4)
C28 C23 C24 . . 118.9(4)
C28 C23 C21 . . 122.0(4)
C24 C23 C21 . . 119.1(4)
C25 C24 C23 . . 120.7(4)
C26 C25 C24 . . 119.8(4)
C25 C26 C27 . . 119.6(4)
C28 C27 C26 . . 120.9(5)
C27 C28 C23 . . 120.0(4)
C7 N1 C6 . . 112.7(4)
C7 N1 Rh1 . . 117.1(3)
C6 N1 Rh1 . . 109.1(3)
C20 N2 C21 . . 112.4(3)
C20 N2 Rh2 . . 107.8(3)
C21 N2 Rh2 . . 116.3(3)
C1 Rh1 N1 . 2 83.09(11)
C1 Rh1 N1 . . 83.09(11)
N1 Rh1 N1 2 . 166.2(2)
C1 Rh1 Cl1 . . 93.82(4)
N1 Rh1 Cl1 2 . 87.70(11)
N1 Rh1 Cl1 . . 93.22(11)
C1 Rh1 Cl1 . 2 93.82(4)
N1 Rh1 Cl1 2 2 93.22(11)
N1 Rh1 Cl1 . 2 87.70(11)
Cl1 Rh1 Cl1 . 2 172.37(7)
C15 Rh2 N2 . 2_656 82.74(10)
C15 Rh2 N2 . . 82.74(10)
N2 Rh2 N2 2_656 . 165.5(2)
C15 Rh2 Cl2 . . 93.47(4)
N2 Rh2 Cl2 2_656 . 89.33(10)
N2 Rh2 Cl2 . . 91.55(10)
C15 Rh2 Cl2 . 2_656 93.48(4)
N2 Rh2 Cl2 2_656 2_656 91.55(10)
N2 Rh2 Cl2 . 2_656 89.33(10)
Cl2 Rh2 Cl2 . 2_656 173.05(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 2 1.393(7)
C1 C2 . 1.393(7)
C1 Rh1 . 1.909(8)
C2 C3 . 1.355(9)
C2 C6 . 1.523(8)
C3 C4 . 1.413(7)
C3 C5 . 1.518(8)
C4 C3 2 1.413(7)
C6 N1 . 1.515(6)
C7 N1 . 1.504(6)
C7 C9 . 1.509(7)
C7 C8 . 1.521(7)
C9 C14 . 1.390(7)
C9 C10 . 1.397(7)
C10 C11 . 1.377(8)
C11 C12 . 1.380(9)
C12 C13 . 1.377(8)
C13 C14 . 1.394(7)
C15 C16 . 1.373(6)
C15 C16 2_656 1.373(6)
C15 Rh2 . 1.919(8)
C16 C17 . 1.443(9)
C16 C20 . 1.507(7)
C17 C18 . 1.381(7)
C17 C19 . 1.503(8)
C18 C17 2_656 1.381(7)
C20 N2 . 1.496(6)
C21 N2 . 1.505(6)
C21 C22 . 1.512(7)
C21 C23 . 1.522(6)
C23 C28 . 1.391(6)
C23 C24 . 1.393(6)
C24 C25 . 1.388(7)
C25 C26 . 1.374(7)
C26 C27 . 1.391(6)
C27 C28 . 1.373(7)
Cl1 Rh1 . 2.3117(10)
Cl2 Rh2 . 2.3091(10)
N1 Rh1 . 2.076(4)
N2 Rh2 . 2.086(4)
Rh1 N1 2 2.076(4)
Rh1 Cl1 2 2.3117(10)
Rh2 N2 2_656 2.086(4)
Rh2 Cl2 2_656 2.3092(10)
