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_4125431
_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 unk
_chemical_formula_moiety         'C11 H10 F2 O2 S'
_chemical_formula_sum            'C11 H10 F2 O2 S'
_chemical_formula_weight         244.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_audit_creation_date             2016-03-02
_audit_creation_method
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7725(7)
_cell_length_b                   13.8233(13)
_cell_length_c                   11.1737(18)
_cell_measurement_reflns_used    1879
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.366
_cell_measurement_theta_min      2.344
_cell_volume                     1046.1(2)
_computing_cell_refinement       'SAINT v8.34A (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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.8386
_diffrn_measured_fraction_theta_max 0.8386
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5198
_diffrn_reflns_theta_full        26.5000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0469 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.7167.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5509
_exptl_crystal_description       block
_exptl_crystal_F_000             504.8378
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.3468
_refine_diff_density_min         -0.3026
_refine_diff_density_rms         0.0490
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             8.6898
_refine_ls_goodness_of_fit_ref   1.0374
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0374
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.9727
_refine_ls_shift/su_mean         0.1832
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.1936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.659
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              13
_reflns_limit_l_min              -10
_reflns_number_gt                1549
_reflns_number_total             1792
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja6b13229_si_021.cif
_cod_data_source_block           baran566_b
_cod_depositor_comments
'Adding full bibliography for 4125430--4125440.cif.'
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               4125431
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(2) 0.3(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7')
Uanis(C9') = Uanis(C9)
Uanis(C11) = Uanis(C8')
4. Rigid body (RIGU) restrains
 C8, C9, C11, C10, C8', C9', C10', C11', C7, C7'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C8')=Sof(H8'A)=Sof(H8'B)=Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(C10')=Sof(H10')=
 Sof(C11')=Sof(H11C)=Sof(H11D)=Sof(C7')=1-FVAR(1)
 Sof(C7)=Sof(C8)=Sof(H8a)=Sof(H8b)=Sof(C9)=Sof(H9a)=Sof(H9b)=Sof(C11)=
 Sof(H11a)=Sof(H11b)=Sof(C10)=Sof(H10)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C10'(H10')
6.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C11(H11a,H11b), C8'(H8'A,H8'B), C9'(H9'A,H9'B),
 C11'(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'