Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.
Shaw, Megan H.; Croft, Rosemary A.; Whittingham, William G.; Bower, John F.; Journal of the American Chemical Society 137 (2015) 8054–8057; doi:10.1021/jacs.5b05215

data_4123849
_publ_section_title
;
 Modular Access to Substituted Azocanes via a Rhodium-Catalyzed
 Cycloaddition-Fragmentation Strategy.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8054
_journal_page_last               8057
_journal_paper_doi               10.1021/jacs.5b05215
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C20 H30 Cl2 N2 O8 Rh2'
_chemical_formula_sum            'C20 H30 Cl2 N2 O8 Rh2'
_chemical_formula_weight         703.18
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.336(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2575(17)
_cell_length_b                   19.844(5)
_cell_length_c                   9.142(2)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.88
_cell_measurement_theta_min      4.46
_cell_volume                     1299.2(5)
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Proteum CCD'
_diffrn_detector_type            'Bruker Proteum CCD'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_laue_measured_fraction_full 0.972
_diffrn_reflns_laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2291
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.258
_diffrn_reflns_theta_min         4.456
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.573
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1353 before and 0.0737 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1678 before and 0.0782 after correction.
 The Ratio of minimum to maximum transmission is 0.23.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 23905 reflections, Rint = 0.0725
 (22594 with I > 3sig(I), Rint = 0.0725)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.397
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.351
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.9613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2289
_reflns_number_total             2291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05215_si_005.cif
_cod_data_source_block           hklf5
_cod_depositor_comments
'Adding full bibliography for 4123848--4123850.cif.'
_cod_database_code               4123849
_shelxl_version_number           2013-3
_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. Uiso/Uaniso restraints and constraints
C3 \\sim C2 \\sim O2: within 1.7A with sigma of 0.003 and sigma for terminal
atoms of 0.006
Uanis(Rh1) \\sim Ueq: with sigma of 0.0003 and sigma for terminal atoms of
0.0006
3.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              51351
_shelx_hkl_checksum              71698