#------------------------------------------------------------------------------
#$Date: 2017-12-07 02:14:00 +0200 (Thu, 07 Dec 2017) $
#$Revision: 204025 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/32/4033255.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_4033255
loop_
_publ_author_name
'O'Brien, Jessica G K'
'Chintala, Srinivasa R.'
'Fox, Joseph M.'
_publ_section_title
;
 Stereoselective Synthesis of Bicyclo[6.1.0]nonene Precursors of the
 Bioorthogonal Reagents s-TCO and BCN.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02329
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C60 H80 N4 O17 Rh2'
_chemical_formula_weight         1335.10
_space_group_crystal_system      tetragonal
_space_group_IT_number           97
_space_group_name_Hall           'I 4 2'
_space_group_name_H-M_alt        'I 4 2 2'
_symmetry_space_group_name_Hall  'I 4 2'
_symmetry_space_group_name_H-M   'I 4 2 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0141(8)
_cell_length_b                   13.0141(8)
_cell_length_c                   40.507(3)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.17
_cell_volume                     6860.5(8)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            52422
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.586
_diffrn_reflns_theta_min         1.644
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             2776
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.218
_refine_diff_density_max         1.570
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
; 
 Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.030(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0701P)²+7.2052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3852
_reflns_number_total             3974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02329_si_002.cif
_cod_data_source_block           joef123_sq
_cod_original_cell_volume        6860.5(9)
_cod_database_code               4033255
_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. 
;
_shelx_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.890
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+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
O5 O 0.5000 0.5000 0.26802(19) 0.0406(14) Uani 0.560(9) 4 d S T P A 1
O6 O 0.5000 0.5000 0.4434(2) 0.0406(14) Uani 0.440(9) 4 d S T P A 2
Rh1 Rh 0.5000 0.5000 0.38225(2) 0.02686(14) Uani 1 4 d S T P . .
Rh2 Rh 0.5000 0.5000 0.32325(2) 0.03143(15) Uani 1 4 d S T P A .
O1 O 0.4128(2) 0.3709(2) 0.38057(6) 0.0316(5) Uani 1 1 d . . . . .
O2 O 0.4147(2) 0.3686(2) 0.32462(6) 0.0368(6) Uani 1 1 d . . . . .
O3 O 0.1933(2) 0.4223(2) 0.35678(8) 0.0474(7) Uani 1 1 d . . . . .
O4 O 0.2590(3) 0.1264(3) 0.41264(11) 0.0627(10) Uani 1 1 d . . . . .
N1 N 0.2349(2) 0.2634(2) 0.37736(8) 0.0383(8) Uani 1 1 d . . . . .
C1 C 0.3881(3) 0.3347(3) 0.35262(9) 0.0343(7) Uani 1 1 d . . . . .
C2 C 0.3195(3) 0.2380(3) 0.35469(10) 0.0382(7) Uani 1 1 d . . . . .
H2 H 0.3617 0.1851 0.3664 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2832(4) 0.1862(4) 0.32215(11) 0.0528(11) Uani 1 1 d . . . . .
C4 C 0.2176(5) 0.0919(5) 0.33197(15) 0.0697(15) Uani 1 1 d . . . . .
H4A H 0.1546 0.1151 0.3429 0.105 Uiso 1 1 calc R U . . .
H4B H 0.2569 0.0481 0.3471 0.105 Uiso 1 1 calc R U . . .
H4C H 0.1998 0.0526 0.3121 0.105 Uiso 1 1 calc R U . . .
C5 C 0.3788(5) 0.1492(5) 0.30336(15) 0.0724(16) Uani 1 1 d . . . . .
H5A H 0.3576 0.1135 0.2832 0.109 Uiso 1 1 calc R U . . .
H5B H 0.4183 0.1021 0.3174 0.109 Uiso 1 1 calc R U . . .
H5C H 0.4216 0.2085 0.2976 0.109 Uiso 1 1 calc R U . . .
C6 C 0.2194(4) 0.2571(5) 0.30056(12) 0.0641(16) Uani 1 1 d . . . . .
H6A H 0.2565 0.3217 0.2971 0.096 Uiso 1 1 calc R U . . .
H6B H 0.1536 0.2712 0.3114 0.096 Uiso 1 1 calc R U . . .
H6C H 0.2069 0.2241 0.2792 0.096 Uiso 1 1 calc R U . . .
C7 C 0.1806(3) 0.3555(3) 0.37675(10) 0.0398(8) Uani 1 1 d . . . . .
C8 C 0.1066(3) 0.3562(4) 0.40580(12) 0.0477(10) Uani 1 1 d . . . . .
H8 H 0.0338 0.3597 0.3980 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1280(5) 0.4396(4) 0.43250(13) 0.0601(13) Uani 1 1 d . . . . .
H9 H 0.0982 0.5089 0.4278 0.072 Uiso 1 1 calc R U . . .
C10 C 0.2411(5) 0.4383(5) 0.44007(13) 0.0645(14) Uani 1 1 d . . . . .
H10A H 0.2818 0.4402 0.4194 0.077 Uiso 1 1 calc R U . . .
H10B H 0.2602 0.4982 0.4538 0.077 Uiso 1 1 calc R U . . .
C11 C 0.2590(4) 0.3464(5) 0.45723(13) 0.0660(14) Uani 1 1 d . . . . .
H11A H 0.2863 0.3610 0.4796 0.079 Uiso 1 1 calc R U . . .
H11B H 0.3093 0.3033 0.4452 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1566(4) 0.2920(4) 0.45957(13) 0.0606(13) Uani 1 1 d . . . . .
H12 H 0.1509 0.2393 0.4774 0.073 Uiso 1 1 calc R U . . .
C13 C 0.1274(4) 0.2542(4) 0.42402(13) 0.0506(11) Uani 1 1 d . . . . .
H13 H 0.0648 0.2097 0.4244 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2130(4) 0.2044(4) 0.40530(10) 0.0467(8) Uani 1 1 d . . . . .
C15 C 0.0826(5) 0.3841(5) 0.46249(13) 0.0718(16) Uani 1 1 d . . . . .
H15A H 0.0096 0.3646 0.4594 0.086 Uiso 1 1 calc R U . . .
H15B H 0.0913 0.4229 0.4833 0.086 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Rh1 O1 176.14(14) . 2_665
O1 Rh1 O1 89.935(5) . 4_565
O1 Rh1 O1 89.935(5) 2_665 4_565
O1 Rh1 O1 89.935(5) . 3_655
O1 Rh1 O1 89.935(5) 2_665 3_655
O1 Rh1 O1 176.14(14) 4_565 3_655
O1 Rh1 Rh2 88.07(7) . .
O1 Rh1 Rh2 88.07(7) 2_665 .
O1 Rh1 Rh2 88.07(7) 4_565 .
O1 Rh1 Rh2 88.07(7) 3_655 .
O1 Rh1 O6 91.93(7) . .
O1 Rh1 O6 91.93(7) 2_665 .
O1 Rh1 O6 91.93(7) 4_565 .
O1 Rh1 O6 91.93(7) 3_655 .
Rh2 Rh1 O6 180.0 . .
O2 Rh2 O2 176.89(14) . 2_665
O2 Rh2 O2 89.958(4) . 4_565
O2 Rh2 O2 89.958(4) 2_665 4_565
O2 Rh2 O2 89.958(4) . 3_655
O2 Rh2 O2 89.958(4) 2_665 3_655
O2 Rh2 O2 176.89(14) 4_565 3_655
O2 Rh2 O5 91.55(7) . .
O2 Rh2 O5 91.55(7) 2_665 .
O2 Rh2 O5 91.55(7) 4_565 .
O2 Rh2 O5 91.55(7) 3_655 .
O2 Rh2 Rh1 88.45(7) . .
O2 Rh2 Rh1 88.45(7) 2_665 .
O2 Rh2 Rh1 88.45(7) 4_565 .
O2 Rh2 Rh1 88.45(7) 3_655 .
O5 Rh2 Rh1 180.0 . .
C1 O1 Rh1 118.7(2) . .
C1 O2 Rh2 117.7(2) . .
C7 N1 C14 112.6(4) . .
C7 N1 C2 124.2(3) . .
C14 N1 C2 122.4(4) . .
O2 C1 O1 127.0(3) . .
O2 C1 C2 119.3(3) . .
O1 C1 C2 113.6(3) . .
N1 C2 C1 106.5(3) . .
N1 C2 C3 113.5(3) . .
C1 C2 C3 118.9(3) . .
N1 C2 H2 105.6 . .
C1 C2 H2 105.6 . .
C3 C2 H2 105.6 . .
C6 C3 C5 110.4(5) . .
C6 C3 C4 109.2(5) . .
C5 C3 C4 109.0(5) . .
C6 C3 C2 113.0(4) . .
C5 C3 C2 108.0(4) . .
C4 C3 C2 107.1(4) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O3 C7 N1 124.5(4) . .
O3 C7 C8 127.3(4) . .
N1 C7 C8 108.2(3) . .
C7 C8 C13 104.8(4) . .
C7 C8 C9 115.4(4) . .
C13 C8 C9 103.7(4) . .
C7 C8 H8 110.9 . .
C13 C8 H8 110.9 . .
C9 C8 H8 110.9 . .
C10 C9 C15 102.2(5) . .
C10 C9 C8 107.9(4) . .
C15 C9 C8 98.8(4) . .
C10 C9 H9 115.3 . .
C15 C9 H9 115.3 . .
C8 C9 H9 115.3 . .
C11 C10 C9 105.9(5) . .
C11 C10 H10A 110.6 . .
C9 C10 H10A 110.6 . .
C11 C10 H10B 110.6 . .
C9 C10 H10B 110.6 . .
H10A C10 H10B 108.7 . .
C10 C11 C12 106.5(5) . .
C10 C11 H11A 110.4 . .
C12 C11 H11A 110.4 . .
C10 C11 H11B 110.4 . .
C12 C11 H11B 110.4 . .
H11A C11 H11B 108.6 . .
C11 C12 C15 101.1(5) . .
C11 C12 C13 107.6(4) . .
C15 C12 C13 99.4(4) . .
C11 C12 H12 115.6 . .
C15 C12 H12 115.6 . .
C13 C12 H12 115.6 . .
C14 C13 C8 105.2(4) . .
C14 C13 C12 114.9(4) . .
C8 C13 C12 102.3(4) . .
C14 C13 H13 111.3 . .
C8 C13 H13 111.3 . .
C12 C13 H13 111.3 . .
O4 C14 N1 123.8(5) . .
O4 C14 C13 127.3(4) . .
N1 C14 C13 108.9(4) . .
C9 C15 C12 93.7(4) . .
C9 C15 H15A 113.0 . .
C12 C15 H15A 113.0 . .
C9 C15 H15B 113.0 . .
C12 C15 H15B 113.0 . .
H15A C15 H15B 110.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O5 Rh2 2.237(8) .
O6 Rh1 2.477(10) .
Rh1 O1 2.028(3) .
Rh1 O1 2.028(3) 2_665
Rh1 O1 2.028(3) 4_565
Rh1 O1 2.028(3) 3_655
Rh1 Rh2 2.3898(6) .
Rh2 O2 2.039(3) .
Rh2 O2 2.040(3) 2_665
Rh2 O2 2.040(3) 4_565
Rh2 O2 2.040(3) 3_655
O1 C1 1.268(4) .
O2 C1 1.265(5) .
O3 C7 1.198(5) .
O4 C14 1.215(7) .
N1 C7 1.392(5) .
N1 C14 1.397(5) .
N1 C2 1.471(5) .
C1 C2 1.546(5) .
C2 C3 1.554(6) .
C2 H2 1.0000 .
C3 C6 1.519(8) .
C3 C5 1.536(8) .
C3 C4 1.546(7) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.520(6) .
C8 C13 1.542(7) .
C8 C9 1.558(7) .
C8 H8 1.0000 .
C9 C10 1.504(9) .
C9 C15 1.532(7) .
C9 H9 1.0000 .
C10 C11 1.403(9) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.512(8) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C15 1.542(8) .
C12 C13 1.568(8) .
C12 H12 1.0000 .
C13 C14 1.495(7) .
C13 H13 1.0000 .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
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
Rh2 O2 C1 O1 -3.6(5)
Rh2 O2 C1 C2 177.4(2)
Rh1 O1 C1 O2 2.4(5)
Rh1 O1 C1 C2 -178.6(2)
C7 N1 C2 C1 44.2(5)
C14 N1 C2 C1 -124.4(4)
C7 N1 C2 C3 -88.5(4)
C14 N1 C2 C3 102.9(4)
O2 C1 C2 N1 -130.9(4)
O1 C1 C2 N1 50.0(4)
O2 C1 C2 C3 -1.2(6)
O1 C1 C2 C3 179.7(4)
N1 C2 C3 C6 66.1(5)
C1 C2 C3 C6 -60.3(5)
N1 C2 C3 C5 -171.5(4)
C1 C2 C3 C5 62.1(5)
N1 C2 C3 C4 -54.2(5)
C1 C2 C3 C4 179.4(4)
C14 N1 C7 O3 173.3(4)
C2 N1 C7 O3 3.7(6)
C14 N1 C7 C8 -5.3(5)
C2 N1 C7 C8 -174.9(3)
O3 C7 C8 C13 -176.8(4)
N1 C7 C8 C13 1.8(5)
O3 C7 C8 C9 -63.5(6)
N1 C7 C8 C9 115.1(4)
C7 C8 C9 C10 -46.3(6)
C13 C8 C9 C10 67.6(5)
C7 C8 C9 C15 -152.2(4)
C13 C8 C9 C15 -38.3(5)
C15 C9 C10 C11 33.0(6)
C8 C9 C10 C11 -70.6(5)
C9 C10 C11 C12 0.7(6)
C10 C11 C12 C15 -33.7(5)
C10 C11 C12 C13 69.9(5)
C7 C8 C13 C14 1.9(5)
C9 C8 C13 C14 -119.4(4)
C7 C8 C13 C12 122.3(4)
C9 C8 C13 C12 1.0(4)
C11 C12 C13 C14 44.9(6)
C15 C12 C13 C14 149.7(4)
C11 C12 C13 C8 -68.4(5)
C15 C12 C13 C8 36.4(5)
C7 N1 C14 O4 -172.2(4)
C2 N1 C14 O4 -2.4(6)
C7 N1 C14 C13 6.7(4)
C2 N1 C14 C13 176.5(3)
C8 C13 C14 O4 173.7(5)
C12 C13 C14 O4 62.1(6)
C8 C13 C14 N1 -5.1(5)
C12 C13 C14 N1 -116.7(4)
C10 C9 C15 C12 -50.7(5)
C8 C9 C15 C12 60.0(5)
C11 C12 C15 C9 50.5(5)
C13 C12 C15 C9 -59.7(5)
