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_4124718
_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         'C21 H36 O5, H2 O'
_chemical_formula_sum            'C21 H38 O6'
_chemical_formula_weight         386.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.304(7)
_cell_angle_beta                 91.320(7)
_cell_angle_gamma                115.381(4)
_cell_formula_units_Z            1
_cell_length_a                   6.2827(6)
_cell_length_b                   7.1127(6)
_cell_length_c                   12.6469(13)
_cell_measurement_temperature    100(2)
_cell_volume                     510.13(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.10-0 (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, 2015)'
_computing_structure_solution    'XT (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 0.963
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6603
_diffrn_reflns_point_group_measured_fraction_full 0.816
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         68.034
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.5209
_exptl_absorpt_correction_T_min  0.4278
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8213.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       irregular
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0562P)^2^+0.0111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.669
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                2754
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09463_si_008.cif
_cod_data_source_block           small_cell_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_original_cell_volume        510.13(8)
_cod_database_code               4124718
_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, All O(H,H,H,H,H,H,H) groups
2. Restrained distances
 O3-H3 = O2-H2A = O4-H4
 0.84 with sigma of 0.02
 O5-H5
 0.84 with sigma of 0.02
 O1-H1
 0.84 with sigma of 0.02
 O6-H6A = O6-H6B
 0.84 with sigma of 0.02
3.a Free rotating group:
 O6(H4,H2A,H3,H5,H1)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C9(H9), C11(H11), C12(H12), C15(H15), C20(H20)
3.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B),
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              60247
_shelx_hkl_checksum              60123
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'