Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.
See, Yi Yang; Herrmann, Aaron T.; Aihara, Yoshinori; Baran, Phil S.; Journal of the American Chemical Society 137 (2015) 13776–13779; doi:10.1021/jacs.5b09463

data_4124716
_publ_section_title
;
 Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13776
_journal_page_last               13779
_journal_paper_doi               10.1021/jacs.5b09463
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H42 N O, C F3 O3 S'
_chemical_formula_sum            'C26 H42 F3 N O4 S'
_chemical_formula_weight         521.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.599(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.155(3)
_cell_length_b                   8.548(2)
_cell_length_c                   23.428(6)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.222
_cell_measurement_theta_min      2.542
_cell_volume                     2589.5(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36454
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.391
_diffrn_reflns_theta_min         1.575
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1308 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.7303.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         9449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0422
_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/[\s^2^(Fo^2^)+(0.0379P)^2^+1.7084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                8628
_reflns_number_total             9449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09463_si_007.cif
_cod_data_source_block           baran528_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4124715--4124721.cif.
;
_cod_database_code               4124716
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.948
_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:
 C9(H9), C16(H16), C17(H17), C23(H23), C34(H34), C42(H42), C43(H43), C48(H48)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B),
 C14(H14A,H14B), C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B), C26(H26A,H26B),
  C27(H27A,H27B), C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C35(H35A,
 H35B), C36(H36A,H36B), C39(H39A,H39B), C41(H41A,H41B), C45(H45A,H45B),
 C46(H46A,H46B), C49(H49A,H49B), C50(H50A,H50B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C40(H40)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C),
 C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C33(H33A,H33B,
 H33C), C44(H44A,H44B,H44C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              16993
_shelx_hkl_checksum              82549
_olex2_submission_original_sample_id ath-2-069
_olex2_submission_special_instructions 'No special instructions were received'