#------------------------------------------------------------------------------
#$Date: 2020-12-04 04:21:09 +0200 (Fri, 04 Dec 2020) $
#$Revision: 259520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/53/4135360.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_4135360
loop_
_publ_author_name
'Das, Anuvab'
'Wang, Chen-Hao'
'Van Trieste, 3rd, Gerard P'
'Sun, Cheng-Jun'
'Chen, Yu-Sheng'
'Reibenspies, Joseph H.'
'Powers, David C.'
_publ_section_title
;
 In Crystallo Snapshots of Rh₂-Catalyzed C-H Amination.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19862
_journal_page_last               19867
_journal_paper_doi               10.1021/jacs.0c09842
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C56 H58 N6 O8 Rh2, 2(C H Cl3)'
_chemical_formula_sum            'C58 H60 Cl6 N6 O8 Rh2'
_chemical_formula_weight         1387.64
_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_date             2020-07-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.871(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8813(18)
_cell_length_b                   12.9498(18)
_cell_length_c                   18.331(3)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      14.83
_cell_measurement_theta_min      2.20
_cell_volume                     2981.0(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 2 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'Charge-integrating Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            65756
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         14.989
_diffrn_reflns_theta_min         1.129
_diffrn_source                   synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0887 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.8996.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.699
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+8.4919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4709
_reflns_number_total             5868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c09842_si_002.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 4135359--4135363.cif.'
_cod_original_cell_volume        2981.0(7)
_cod_database_code               4135360
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1S(H1S)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C11(H11), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8),
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Rh1 Rh 0.54608(2) 0.53901(2) 0.55705(2) 0.02175(10) Uani 1 1 d . . . . .
O1 O 0.4035(2) 0.5798(2) 0.57849(16) 0.0261(6) Uani 1 1 d . . . . .
O2 O 0.3155(2) 0.5053(2) 0.47101(16) 0.0259(6) Uani 1 1 d . . . . .
O3 O 0.5503(2) 0.6719(2) 0.50011(15) 0.0262(6) Uani 1 1 d . . . . .
O4 O 0.4657(2) 0.5993(2) 0.39109(15) 0.0258(6) Uani 1 1 d . . . . .
N1 N 0.6342(3) 0.6276(3) 0.65976(19) 0.0293(8) Uani 1 1 d . . . . .
N2 N 0.6023(3) 0.6197(3) 0.7198(2) 0.0333(9) Uani 1 1 d . . . . .
N3 N 0.5682(4) 0.6025(4) 0.7712(3) 0.0487(11) Uani 1 1 d . . . . .
C1 C 0.3195(3) 0.5541(3) 0.5321(2) 0.0249(8) Uani 1 1 d . . . . .
C2 C 0.2123(3) 0.5808(4) 0.5498(2) 0.0303(9) Uani 1 1 d . . . . .
C3 C 0.2282(4) 0.6388(4) 0.6246(3) 0.0359(11) Uani 1 1 d . . . . .
H3A H 0.2671 0.5946 0.6649 0.054 Uiso 1 1 calc GR . . . .
H3B H 0.1586 0.6566 0.6344 0.054 Uiso 1 1 calc GR . . . .
H3C H 0.2689 0.7021 0.6221 0.054 Uiso 1 1 calc GR . . . .
C4 C 0.1521(4) 0.4794(4) 0.5552(3) 0.0369(11) Uani 1 1 d . . . . .
H4A H 0.1439 0.4410 0.5081 0.055 Uiso 1 1 calc GR . . . .
H4B H 0.0817 0.4950 0.5644 0.055 Uiso 1 1 calc GR . . . .
H4C H 0.1925 0.4375 0.5964 0.055 Uiso 1 1 calc GR . . . .
C5 C 0.1473(3) 0.6468(4) 0.4840(3) 0.0329(10) Uani 1 1 d . . . . .
H5A H 0.1291 0.6027 0.4388 0.039 Uiso 1 1 calc R . . . .
H5B H 0.0797 0.6679 0.4968 0.039 Uiso 1 1 calc R . . . .
C6 C 0.2032(3) 0.7422(4) 0.4653(2) 0.0308(10) Uani 1 1 d . . . . .
C7 C 0.1901(4) 0.8383(4) 0.4972(3) 0.0349(10) Uani 1 1 d . . . . .
H7 H 0.1434 0.8444 0.5304 0.042 Uiso 1 1 calc R . . . .
C8 C 0.2447(4) 0.9248(4) 0.4808(3) 0.0372(11) Uani 1 1 d . . . . .
H8 H 0.2349 0.9897 0.5026 0.045 Uiso 1 1 calc R . . . .
C9 C 0.3139(4) 0.9164(4) 0.4324(3) 0.0348(10) Uani 1 1 d . . . . .
H9 H 0.3512 0.9757 0.4216 0.042 Uiso 1 1 calc R . . . .
C10 C 0.3289(3) 0.8214(4) 0.3995(2) 0.0302(9) Uani 1 1 d . . . . .
C11 C 0.2711(3) 0.7370(4) 0.4159(2) 0.0292(9) Uani 1 1 d . . . . .
H11 H 0.2784 0.6729 0.3923 0.035 Uiso 1 1 calc R . . . .
C12 C 0.4053(3) 0.8098(4) 0.3489(2) 0.0303(9) Uani 1 1 d . . . . .
H12A H 0.4100 0.8764 0.3234 0.036 Uiso 1 1 calc R . . . .
H12B H 0.3764 0.7580 0.3099 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5192(3) 0.7761(4) 0.3895(2) 0.0283(9) Uani 1 1 d . . . . .
C14 C 0.5728(4) 0.8594(4) 0.4444(3) 0.0340(10) Uani 1 1 d . . . . .
H14A H 0.5752 0.9244 0.4175 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.6455 0.8377 0.4679 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.5321 0.8694 0.4831 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.5859(4) 0.7555(4) 0.3309(3) 0.0382(11) Uani 1 1 d . . . . .
H15A H 0.5516 0.7014 0.2964 0.057 Uiso 1 1 calc GR . . . .
H15B H 0.6574 0.7328 0.3563 0.057 Uiso 1 1 calc GR . . . .
H15C H 0.5910 0.8189 0.3029 0.057 Uiso 1 1 calc GR . . . .
C16 C 0.5109(3) 0.6750(3) 0.4304(2) 0.0257(9) Uani 1 1 d . . . . .
Cl1 Cl 0.36132(11) 0.52151(12) 0.84840(8) 0.0501(3) Uani 1 1 d . . . . .
Cl2 Cl 0.39225(14) 0.73939(13) 0.82527(10) 0.0630(4) Uani 1 1 d . . . . .
Cl3 Cl 0.39745(11) 0.66300(13) 0.97410(8) 0.0543(4) Uani 1 1 d . . . . .
C1S C 0.4273(4) 0.6349(4) 0.8870(3) 0.0422(12) Uani 1 1 d . . . . .
H1S H 0.5058 0.6233 0.8950 0.051 Uiso 1 1 calc R . . . .
C1_2 C 0.7140(3) 0.7050(4) 0.6597(2) 0.0275(9) Uani 1 1 d . . . . .
C2_2 C 0.8035(3) 0.6718(4) 0.6363(2) 0.0302(9) Uani 1 1 d . . . . .
H2_2 H 0.8079 0.6025 0.6203 0.036 Uiso 1 1 calc R . . . .
C3_2 C 0.8867(4) 0.7398(4) 0.6363(3) 0.0360(11) Uani 1 1 d . . . . .
H3_2 H 0.9483 0.7170 0.6205 0.043 Uiso 1 1 calc R . . . .
C4_2 C 0.8800(4) 0.8407(4) 0.6593(3) 0.0368(11) Uani 1 1 d . . . . .
H4_2 H 0.9375 0.8870 0.6604 0.044 Uiso 1 1 calc R . . . .
C5_2 C 0.7886(4) 0.8743(4) 0.6808(2) 0.0325(10) Uani 1 1 d . . . . .
H5_2 H 0.7845 0.9441 0.6959 0.039 Uiso 1 1 calc R . . . .
C6_2 C 0.7028(3) 0.8083(4) 0.6807(2) 0.0283(9) Uani 1 1 d . . . . .
C7_2 C 0.6046(3) 0.8513(3) 0.6992(2) 0.0277(9) Uani 1 1 d . . . . .
C8_2 C 0.5036(4) 0.8332(4) 0.6530(3) 0.0320(10) Uani 1 1 d . . . . .
H8_2 H 0.4963 0.7875 0.6116 0.038 Uiso 1 1 calc R . . . .
C9_2 C 0.4144(4) 0.8817(4) 0.6677(3) 0.0340(10) Uani 1 1 d . . . . .
H9_2 H 0.3467 0.8708 0.6352 0.041 Uiso 1 1 calc R . . . .
C10_2 C 0.4230(4) 0.9456(4) 0.7289(3) 0.0342(10) Uani 1 1 d . . . . .
H10_2 H 0.3611 0.9773 0.7389 0.041 Uiso 1 1 calc R . . . .
C11_2 C 0.5220(4) 0.9641(4) 0.7760(3) 0.0325(9) Uani 1 1 d . . . . .
H11_2 H 0.5278 1.0080 0.8182 0.039 Uiso 1 1 calc R . . . .
C12_2 C 0.6122(4) 0.9176(4) 0.7609(2) 0.0325(10) Uani 1 1 d . . . . .
H12_2 H 0.6799 0.9308 0.7926 0.039 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 -0.0001 0.0005 '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 0.0554 0.0529 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0005 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0017 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -0.3400 2.3829 '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
O1 Rh1 Rh1 89.14(8) . 3_666 ?
O1 Rh1 O2 176.37(11) . 3_666 ?
O1 Rh1 O4 88.50(12) . 3_666 ?
O1 Rh1 N1 90.84(12) . . ?
O2 Rh1 Rh1 87.25(8) 3_666 3_666 ?
O2 Rh1 O4 91.74(12) 3_666 3_666 ?
O2 Rh1 N1 92.72(12) 3_666 . ?
O3 Rh1 Rh1 88.46(8) . 3_666 ?
O3 Rh1 O1 90.46(12) . . ?
O3 Rh1 O2 89.06(12) . 3_666 ?
O3 Rh1 O4 176.19(11) . 3_666 ?
O3 Rh1 N1 86.12(13) . . ?
O4 Rh1 Rh1 87.86(8) 3_666 3_666 ?
O4 Rh1 N1 97.56(12) 3_666 . ?
N1 Rh1 Rh1 174.58(10) . 3_666 ?
C1 O1 Rh1 118.5(3) . . ?
C1 O2 Rh1 119.5(3) . 3_666 ?
C16 O3 Rh1 119.8(3) . . ?
C16 O4 Rh1 118.7(3) . 3_666 ?
N2 N1 Rh1 118.7(3) . . ?
N2 N1 C1_2 115.4(4) . . ?
C1_2 N1 Rh1 125.1(3) . . ?
N3 N2 N1 172.4(5) . . ?
O1 C1 O2 125.5(4) . . ?
O1 C1 C2 118.6(4) . . ?
O2 C1 C2 115.9(4) . . ?
C1 C2 C3 110.6(4) . . ?
C1 C2 C4 108.2(4) . . ?
C1 C2 C5 108.4(3) . . ?
C3 C2 C4 109.2(4) . . ?
C3 C2 C5 111.4(4) . . ?
C4 C2 C5 109.0(4) . . ?
C6 C5 C2 115.1(4) . . ?
C7 C6 C5 121.7(4) . . ?
C11 C6 C5 120.6(4) . . ?
C11 C6 C7 117.7(4) . . ?
C8 C7 C6 120.8(4) . . ?
C7 C8 C9 120.0(4) . . ?
C8 C9 C10 120.7(4) . . ?
C9 C10 C12 121.7(4) . . ?
C11 C10 C9 117.7(4) . . ?
C11 C10 C12 120.6(4) . . ?
C10 C11 C6 123.1(4) . . ?
C10 C12 C13 114.3(4) . . ?
C14 C13 C12 111.0(4) . . ?
C14 C13 C15 110.0(4) . . ?
C15 C13 C12 109.2(4) . . ?
C16 C13 C12 108.3(3) . . ?
C16 C13 C14 110.6(4) . . ?
C16 C13 C15 107.7(4) . . ?
O3 C16 O4 125.1(4) . . ?
O3 C16 C13 117.8(4) . . ?
O4 C16 C13 117.0(4) . . ?
Cl2 C1S Cl1 110.6(3) . . ?
Cl2 C1S Cl3 110.3(3) . . ?
Cl3 C1S Cl1 110.6(3) . . ?
C2_2 C1_2 N1 115.5(4) . . ?
C2_2 C1_2 C6_2 121.5(4) . . ?
C6_2 C1_2 N1 123.0(4) . . ?
C1_2 C2_2 C3_2 120.0(5) . . ?
C4_2 C3_2 C2_2 119.9(4) . . ?
C3_2 C4_2 C5_2 119.8(4) . . ?
C4_2 C5_2 C6_2 121.8(5) . . ?
C1_2 C6_2 C7_2 124.2(4) . . ?
C5_2 C6_2 C1_2 116.8(4) . . ?
C5_2 C6_2 C7_2 118.9(4) . . ?
C8_2 C7_2 C6_2 121.3(4) . . ?
C12_2 C7_2 C6_2 120.1(4) . . ?
C12_2 C7_2 C8_2 118.4(4) . . ?
C9_2 C8_2 C7_2 120.2(4) . . ?
C10_2 C9_2 C8_2 120.7(4) . . ?
C9_2 C10_2 C11_2 120.3(4) . . ?
C12_2 C11_2 C10_2 119.5(4) . . ?
C11_2 C12_2 C7_2 120.9(4) . . ?
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
Rh1 Rh1 2.3872(6) 3_666 ?
Rh1 O1 2.031(3) . ?
Rh1 O2 2.044(3) 3_666 ?
Rh1 O3 2.019(3) . ?
Rh1 O4 2.049(3) 3_666 ?
Rh1 N1 2.280(4) . ?
O1 C1 1.263(5) . ?
O2 Rh1 2.044(3) 3_666 ?
O2 C1 1.278(5) . ?
O3 C16 1.266(5) . ?
O4 Rh1 2.049(3) 3_666 ?
O4 C16 1.277(5) . ?
N1 N2 1.262(5) . ?
N1 C1_2 1.436(6) . ?
N2 N3 1.146(6) . ?
C1 C2 1.527(6) . ?
C2 C3 1.536(6) . ?
C2 C4 1.539(7) . ?
C2 C5 1.560(7) . ?
C5 C6 1.508(7) . ?
C6 C7 1.402(7) . ?
C6 C11 1.394(6) . ?
C7 C8 1.391(7) . ?
C8 C9 1.394(7) . ?
C9 C10 1.402(7) . ?
C10 C11 1.392(6) . ?
C10 C12 1.503(6) . ?
C12 C13 1.552(6) . ?
C13 C14 1.531(6) . ?
C13 C15 1.540(6) . ?
C13 C16 1.525(6) . ?
Cl1 C1S 1.763(6) . ?
Cl2 C1S 1.757(6) . ?
Cl3 C1S 1.762(5) . ?
C1_2 C2_2 1.385(6) . ?
C1_2 C6_2 1.409(7) . ?
C2_2 C3_2 1.386(7) . ?
C3_2 C4_2 1.382(7) . ?
C4_2 C5_2 1.392(7) . ?
C5_2 C6_2 1.398(6) . ?
C6_2 C7_2 1.488(6) . ?
C7_2 C8_2 1.406(6) . ?
C7_2 C12_2 1.406(6) . ?
C8_2 C9_2 1.387(7) . ?
C9_2 C10_2 1.379(7) . ?
C10_2 C11_2 1.392(7) . ?
C11_2 C12_2 1.391(7) . ?
