Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity.
Lopchuk, Justin M.; Fjelbye, Kasper; Kawamata, Yu; Malins, Lara R.; Pan, Chung-Mao; Gianatassio, Ryan; Wang, Jie; Prieto, Liher; Bradow, James; Brandt, Thomas A.; Collins, Michael R.; Elleraas, Jeff; Ewanicki, Jason; Farrell, William; Fadeyi, Olugbeminiyi O.; Gallego, Gary M.; Mousseau, James J.; Oliver, Robert; Sach, Neal W.; Smith, Jason K.; Spangler, Jillian E.; Zhu, Huichin; Zhu, Jinjiang; Baran, Phil S.; Journal of the American Chemical Society 139 (2017) 3209–3226; doi:10.1021/jacs.6b13229

data_4125433
_publ_section_title
;
 Strain-Release Heteroatom Functionalization: Development, Scope, and
 Stereospecificity.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3209
_journal_page_last               3226
_journal_paper_doi               10.1021/jacs.6b13229
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H33 F3 O4 S'
_chemical_formula_sum            'C30 H33 F3 O4 S'
_chemical_formula_weight         546.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6458(2)
_cell_length_b                   8.1522(3)
_cell_length_c                   48.2280(15)
_cell_measurement_reflns_used    9519
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.109
_cell_measurement_theta_min      5.503
_cell_volume                     2612.89(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_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    'ShelXT (Sheldrick, 2015)'
_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 0.997
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            15810
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.217
_diffrn_reflns_theta_min         1.832
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.592
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0852 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.6732.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       Block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0362P)^2^+0.9874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4450
_reflns_number_total             4723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13229_si_012.cif
_cod_data_source_block           Baran599
_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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125430--4125440.cif.
;
_cod_database_code               4125433
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4B) = Uanis(O4)
Uanis(S1) = Uanis(S1B)
Uanis(O3) = Uanis(O3B)
Uanis(C5B) = Uanis(C5)
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(S1B)=Sof(O3B)=Sof(O4B)=Sof(H1B)=Sof(H4BC)=Sof(H4BD)=Sof(C5B)=Sof(H5BA)=
 Sof(H5BB)=1-FVAR(2)
 Sof(S1)=Sof(O3)=Sof(O4)=Sof(H1A)=Sof(H4AA)=Sof(H4AB)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C3(H3), C12(H12), C13(H13), C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4AA,H4AB), C4(H4BC,H4BD), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B), C5(H5A,H5B),
 C5B(H5BA,H5BB)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C25(H25), C26(H26), C28(H28), C29(H29)
4.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              82708
_shelx_hkl_checksum              46964
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'