#------------------------------------------------------------------------------
#$Date: 2016-03-04 10:39:01 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177353 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/27/1542703.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1542703
loop_
_publ_author_name
'Friese, Florian W.'
'Dreier, Anna-Lena'
'Matsnev, Andrej V.'
'Daniliuc, Constantin G.'
'Thrasher, Joseph S.'
'Haufe, Günter'
_publ_section_title
;
 Anti-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters
 with Aldehydes Mediated by Dicyclohexylchloroborane.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1012
_journal_paper_doi               10.1021/acs.orglett.6b00136
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C16 H15 F5 O3 S'
_chemical_formula_weight         382.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
_cell_angle_alpha                85.184(5)
_cell_angle_beta                 83.294(5)
_cell_angle_gamma                87.881(5)
_cell_formula_units_Z            2
_cell_length_a                   5.5840(4)
_cell_length_b                   11.7071(9)
_cell_length_c                   12.0947(9)
_cell_measurement_reflns_used    5304
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6522
_cell_measurement_theta_min      3.6917
_cell_volume                     782.18(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15047
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         3.69
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0769
_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/[σ²(Fo²)+(0.0613P)²+2.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                1833
_reflns_number_total             2631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b00136_si_002.cif
_cod_data_source_block           haf8005
_cod_database_code               1542703
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
S S1 0.8464(2) 0.38249(11) 0.19227(12) 0.0241(4) Uani d . . 1
F F1 0.7034(6) 0.4308(3) 0.0917(3) 0.0333(8) Uani d . . 1
F F2 0.6022(6) 0.3351(3) 0.2564(3) 0.0371(9) Uani d . . 1
F F3 0.9872(6) 0.3234(3) 0.2889(3) 0.0387(9) Uani d . . 1
F F4 1.0908(5) 0.4195(3) 0.1235(3) 0.0353(8) Uani d . . 1
F F5 0.8777(5) 0.2648(2) 0.1349(3) 0.0311(8) Uani d . . 1
O O1 0.9979(6) 0.6623(3) 0.1261(3) 0.0250(9) Uani d . . 1
O O2 0.5908(6) 0.6580(3) 0.1504(3) 0.0223(8) Uani d . . 1
O O3 1.2173(6) 0.5346(4) 0.3033(4) 0.0302(10) Uani d . . 1
H H1 1.257(16) 0.571(8) 0.246(8) 0.09(3) Uiso d . . 1
C C1 0.8133(8) 0.6217(4) 0.1677(4) 0.0184(11) Uani d . . 1
C C2 0.8010(9) 0.5204(4) 0.2579(4) 0.0218(11) Uani d . . 1
H H2 0.6332 0.521 0.2972 0.026 Uiso calc U R 1
C C3 0.9709(8) 0.5400(4) 0.3456(5) 0.0239(12) Uani d . . 1
H H3 0.944 0.4772 0.4067 0.029 Uiso calc U R 1
C C4 0.5701(10) 0.7549(4) 0.0649(5) 0.0257(12) Uani d . . 1
H H4A 0.4531 0.7365 0.0139 0.031 Uiso calc U R 1
H H4B 0.7285 0.7669 0.0201 0.031 Uiso calc U R 1
C C11 0.8947(9) 0.6540(4) 0.3967(5) 0.0230(12) Uani d . . 1
C C12 1.0520(10) 0.7450(5) 0.3804(5) 0.0291(13) Uani d . . 1
H H12 1.206 0.7369 0.3388 0.035 Uiso calc U R 1
C C13 0.9801(11) 0.8487(5) 0.4261(5) 0.0377(15) Uani d . . 1
H H13 1.0855 0.9115 0.4151 0.045 Uiso calc U R 1
C C14 0.7589(11) 0.8597(5) 0.4865(5) 0.0350(14) Uani d . . 1
H H14 0.7117 0.9301 0.5175 0.042 Uiso calc U R 1
C C15 0.6039(10) 0.7694(5) 0.5027(5) 0.0310(13) Uani d . . 1
H H15 0.4508 0.7772 0.5451 0.037 Uiso calc U R 1
C C16 0.6728(10) 0.6670(5) 0.4566(5) 0.0291(13) Uani d . . 1
H H16 0.5649 0.6052 0.4667 0.035 Uiso calc U R 1
C C21 0.4882(8) 0.8625(4) 0.1192(5) 0.0222(11) Uani d . . 1
C C22 0.2768(9) 0.9192(4) 0.0935(5) 0.0262(12) Uani d . . 1
H H22 0.1797 0.8875 0.0449 0.031 Uiso calc U R 1
C C23 0.2066(10) 1.0221(5) 0.1386(5) 0.0308(13) Uani d . . 1
H H23 0.0622 1.0607 0.1201 0.037 Uiso calc U R 1
C C24 0.3443(9) 1.0688(5) 0.2100(5) 0.0301(13) Uani d . . 1
H H24 0.2964 1.1397 0.2399 0.036 Uiso calc U R 1
C C25 0.5541(10) 1.0112(5) 0.2379(5) 0.0303(13) Uani d . . 1
H H25 0.6487 1.0423 0.2879 0.036 Uiso calc U R 1
C C26 0.6252(9) 0.9087(5) 0.1931(5) 0.0263(12) Uani d . . 1
H H26 0.7681 0.8695 0.2127 0.032 Uiso calc U R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F4 S1 F3 90.5(2)
F4 S1 F2 175.03(19)
F3 S1 F2 89.5(2)
F4 S1 F1 90.4(2)
F3 S1 F1 174.93(18)
F2 S1 F1 89.23(19)
F4 S1 F5 87.82(17)
F3 S1 F5 87.71(17)
F2 S1 F5 87.22(17)
F1 S1 F5 87.34(17)
F4 S1 C2 93.2(2)
F3 S1 C2 93.6(2)
F2 S1 C2 91.8(2)
F1 S1 C2 91.3(2)
F5 S1 C2 178.3(2)
C1 O2 C4 116.6(4)
C3 O3 H1 117.(7)
O1 C1 O2 127.2(5)
O1 C1 C2 123.1(4)
O2 C1 C2 109.7(4)
C3 C2 C1 109.8(4)
C3 C2 S1 115.8(3)
C1 C2 S1 110.4(3)
C3 C2 H2 106.8
C1 C2 H2 106.8
S1 C2 H2 106.8
O3 C3 C2 113.2(4)
O3 C3 C11 113.0(4)
C2 C3 C11 108.4(4)
O3 C3 H3 107.3
C2 C3 H3 107.3
C11 C3 H3 107.3
O2 C4 C21 110.5(4)
O2 C4 H4A 109.6
C21 C4 H4A 109.6
O2 C4 H4B 109.6
C21 C4 H4B 109.6
H4A C4 H4B 108.1
C16 C11 C12 119.8(5)
C16 C11 C3 120.6(4)
C12 C11 C3 119.5(5)
C11 C12 C13 119.1(5)
C11 C12 H12 120.4
C13 C12 H12 120.4
C14 C13 C12 120.2(5)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 120.5(6)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C16 119.6(5)
C14 C15 H15 120.2
C16 C15 H15 120.2
C11 C16 C15 120.8(5)
C11 C16 H16 119.6
C15 C16 H16 119.6
C22 C21 C26 119.1(5)
C22 C21 C4 119.8(5)
C26 C21 C4 121.0(5)
C21 C22 C23 120.2(5)
C21 C22 H22 119.9
C23 C22 H22 119.9
C24 C23 C22 120.7(5)
C24 C23 H23 119.7
C22 C23 H23 119.7
C23 C24 C25 119.4(5)
C23 C24 H24 120.3
C25 C24 H24 120.3
C26 C25 C24 120.2(5)
C26 C25 H25 119.9
C24 C25 H25 119.9
C25 C26 C21 120.4(5)
C25 C26 H26 119.8
C21 C26 H26 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 F4 1.568(3)
S1 F3 1.582(3)
S1 F2 1.583(3)
S1 F1 1.586(3)
S1 F5 1.589(3)
S1 C2 1.854(5)
O1 C1 1.190(6)
O2 C1 1.332(6)
O2 C4 1.480(6)
O3 C3 1.411(6)
O3 H1 0.80(9)
C1 C2 1.541(7)
C2 C3 1.539(7)
C2 H2 1.0
C3 C11 1.543(7)
C3 H3 1.0
C4 C21 1.501(7)
C4 H4A 0.99
C4 H4B 0.99
C11 C16 1.371(7)
C11 C12 1.392(7)
C12 C13 1.402(8)
C12 H12 0.95
C13 C14 1.367(9)
C13 H13 0.95
C14 C15 1.378(8)
C14 H14 0.95
C15 C16 1.386(8)
C15 H15 0.95
C16 H16 0.95
C21 C22 1.387(7)
C21 C26 1.396(7)
C22 C23 1.389(7)
C22 H22 0.95
C23 C24 1.379(8)
C23 H23 0.95
C24 C25 1.392(8)
C24 H24 0.95
C25 C26 1.384(7)
C25 H25 0.95
C26 H26 0.95
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H1 O2 1_655 0.80(9) 2.30(9) 2.955(6) 140.(8)
C2 H2 O3 1_455 1.0 2.32 3.242(6) 153.7
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O2 C1 O1 4.3(7)
C4 O2 C1 C2 -179.4(4)
O1 C1 C2 C3 44.9(7)
O2 C1 C2 C3 -131.6(4)
O1 C1 C2 S1 -84.0(5)
O2 C1 C2 S1 99.5(4)
F4 S1 C2 C3 -71.3(4)
F3 S1 C2 C3 19.4(4)
F2 S1 C2 C3 109.0(4)
F1 S1 C2 C3 -161.7(4)
F4 S1 C2 C1 54.3(3)
F3 S1 C2 C1 145.0(3)
F2 S1 C2 C1 -125.4(3)
F1 S1 C2 C1 -36.2(3)
C1 C2 C3 O3 -68.0(5)
S1 C2 C3 O3 57.9(5)
C1 C2 C3 C11 58.2(5)
S1 C2 C3 C11 -175.9(4)
C1 O2 C4 C21 -107.6(5)
O3 C3 C11 C16 -169.9(5)
C2 C3 C11 C16 63.7(7)
O3 C3 C11 C12 11.0(7)
C2 C3 C11 C12 -115.3(5)
C16 C11 C12 C13 0.2(8)
C3 C11 C12 C13 179.3(5)
C11 C12 C13 C14 0.4(9)
C12 C13 C14 C15 -0.3(10)
C13 C14 C15 C16 -0.5(9)
C12 C11 C16 C15 -0.9(9)
C3 C11 C16 C15 180.0(5)
C14 C15 C16 C11 1.0(9)
O2 C4 C21 C22 -121.0(5)
O2 C4 C21 C26 60.8(6)
C26 C21 C22 C23 1.7(8)
C4 C21 C22 C23 -176.5(5)
C21 C22 C23 C24 -0.5(9)
C22 C23 C24 C25 -0.8(9)
C23 C24 C25 C26 0.9(9)
C24 C25 C26 C21 0.3(9)
C22 C21 C26 C25 -1.6(8)
C4 C21 C26 C25 176.6(5)
