Stereoselective Synthesis of Bicyclo[6.1.0]nonene Precursors of the Bioorthogonal Reagents s-TCO and BCN.
O'Brien, Jessica G K; Chintala, Srinivasa R.; Fox, Joseph M.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02329

data_4033255
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0701P)^2^+7.2052P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.890
_shelx_res_checksum              38198
_shelx_hkl_checksum              10208
_shelx_fab_checksum              26145