# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_paqun2
_database_code_depnum_ccdc_archive 'CCDC 1497178'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(R)-(4-Chlorophenyl)(4-(pentafluorosulfanyl)phenyl)methanol '
_chemical_formula_moiety         'C13 H10 Cl F5 O S'
_chemical_formula_sum            'C13 H10 Cl F5 O S'
_chemical_formula_weight         344.72
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1495(2)
_cell_length_b                   9.3429(3)
_cell_length_c                   27.7278(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1334.02(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.113
_cell_measurement_theta_min      4.733
_exptl_absorpt_coefficient_mu    4.551
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0322 after correction.
The Ratio of minimum to maximum transmission is 0.7529.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             696
_exptl_crystal_preparation       'synthesized by the autors'
_exptl_crystal_recrystallization_method 'crystallized from CHCl3'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27044
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.106
_diffrn_reflns_theta_min         4.995
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2576
_reflns_number_total             2576
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.35A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.35A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+0.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0522
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.10734(10) 0.18526(5) 0.41023(2) 0.01939(12) Uani 1 1 d . . . . .
S1 S 0.64747(9) 1.07832(5) 0.27049(2) 0.01409(12) Uani 1 1 d . . . . .
F1 F 0.6312(2) 1.18543(12) 0.22583(4) 0.0216(2) Uani 1 1 d . . . . .
F2 F 0.7937(2) 0.97119(13) 0.23529(4) 0.0224(3) Uani 1 1 d . . . . .
F3 F 0.9169(2) 1.15044(13) 0.28375(4) 0.0221(3) Uani 1 1 d . . . . .
F4 F 0.5009(3) 1.19622(13) 0.30097(4) 0.0240(3) Uani 1 1 d . . . . .
F5 F 0.3774(2) 1.01412(13) 0.25323(4) 0.0247(3) Uani 1 1 d . . . . .
O1 O 0.6611(3) 0.71382(15) 0.48348(5) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.6979(4) 0.6503(2) 0.43685(6) 0.0138(4) Uani 1 1 d . . . . .
H1A H 0.8686 0.6039 0.4363 0.017 Uiso 1 1 calc R . . . .
C2 C 0.4907(4) 0.5356(2) 0.43022(6) 0.0131(4) Uani 1 1 d . . . . .
C3 C 0.3817(4) 0.4667(2) 0.47006(6) 0.0157(4) Uani 1 1 d . . . . .
H3 H 0.4334 0.4932 0.5009 0.019 Uiso 1 1 calc R . . . .
C4 C 0.1976(4) 0.3594(2) 0.46447(7) 0.0165(4) Uani 1 1 d . . . . .
H4 H 0.1251 0.3149 0.4913 0.020 Uiso 1 1 calc R . . . .
C5 C 0.1235(4) 0.31969(19) 0.41830(6) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.2291(4) 0.3852(2) 0.37799(7) 0.0165(4) Uani 1 1 d . . . . .
H6 H 0.1772 0.3577 0.3472 0.020 Uiso 1 1 calc R . . . .
C7 C 0.4132(4) 0.4923(2) 0.38403(6) 0.0147(4) Uani 1 1 d . . . . .
H7 H 0.4860 0.5359 0.3571 0.018 Uiso 1 1 calc R . . . .
C8 C 0.6901(4) 0.7623(2) 0.39704(7) 0.0134(4) Uani 1 1 d . . . . .
C9 C 0.8755(4) 0.7597(2) 0.36053(7) 0.0155(4) Uani 1 1 d . . . . .
H9 H 1.0085 0.6925 0.3617 0.019 Uiso 1 1 calc R . . . .
C10 C 0.8649(4) 0.8562(2) 0.32240(6) 0.0160(4) Uani 1 1 d . . . . .
H10 H 0.9902 0.8541 0.2982 0.019 Uiso 1 1 calc R . . . .
C11 C 0.6658(4) 0.95543(19) 0.32084(6) 0.0128(4) Uani 1 1 d . . . . .
C12 C 0.4789(4) 0.9612(2) 0.35727(7) 0.0150(4) Uani 1 1 d . . . . .
H12 H 0.3464 1.0288 0.3561 0.018 Uiso 1 1 calc R . . . .
C13 C 0.4934(4) 0.8646(2) 0.39525(7) 0.0153(4) Uani 1 1 d . . . . .
H13 H 0.3705 0.8683 0.4198 0.018 Uiso 1 1 calc R . . . .
H1 H 0.790(5) 0.744(3) 0.4910(10) 0.023(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.7438(19) . ?
S1 F1 1.5942(11) . ?
S1 F2 1.5878(12) . ?
S1 F3 1.5854(12) . ?
S1 F4 1.5803(12) . ?
S1 F5 1.5883(13) . ?
S1 C11 1.8100(18) . ?
O1 C1 1.435(2) . ?
O1 H1 0.75(3) . ?
C1 H1A 0.9800 . ?
C1 C2 1.523(3) . ?
C1 C8 1.522(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.401(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(2) . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(3) . ?
C11 C12 1.396(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 S1 C11 179.51(8) . . ?
F2 S1 F1 86.75(6) . . ?
F2 S1 F5 89.54(7) . . ?
F2 S1 C11 92.83(7) . . ?
F3 S1 F1 87.67(6) . . ?
F3 S1 F2 89.74(7) . . ?
F3 S1 F5 175.19(7) . . ?
F3 S1 C11 92.58(7) . . ?
F4 S1 F1 87.30(6) . . ?
F4 S1 F2 174.04(7) . . ?
F4 S1 F3 89.86(7) . . ?
F4 S1 F5 90.36(7) . . ?
F4 S1 C11 93.12(7) . . ?
F5 S1 F1 87.54(6) . . ?
F5 S1 C11 92.20(7) . . ?
C1 O1 H1 107(2) . . ?
O1 C1 H1A 108.4 . . ?
O1 C1 C2 107.91(14) . . ?
O1 C1 C8 111.43(15) . . ?
C2 C1 H1A 108.4 . . ?
C8 C1 H1A 108.4 . . ?
C8 C1 C2 112.21(15) . . ?
C3 C2 C1 120.68(16) . . ?
C3 C2 C7 118.41(17) . . ?
C7 C2 C1 120.86(16) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.26(17) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.97(17) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 Cl1 119.93(15) . . ?
C6 C5 Cl1 118.82(14) . . ?
C6 C5 C4 121.25(18) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.26(17) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.85(17) . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C1 119.86(16) . . ?
C9 C8 C13 118.97(17) . . ?
C13 C8 C1 121.12(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.00(18) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.17(18) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 S1 119.21(14) . . ?
C10 C11 C12 120.94(17) . . ?
C12 C11 S1 119.85(14) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.11(17) . . ?
C13 C12 H12 120.4 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.79(18) . . ?
C12 C13 H13 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.75(3) 2.07(3) 2.8152(11) 168(3) 4_566

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C5 C6 C7 -179.97(15) . . . . ?
S1 C11 C12 C13 178.99(14) . . . . ?
F2 S1 C11 C10 26.67(16) . . . . ?
F2 S1 C11 C12 -152.90(15) . . . . ?
F3 S1 C11 C10 -63.20(16) . . . . ?
F3 S1 C11 C12 117.23(15) . . . . ?
F4 S1 C11 C10 -153.19(15) . . . . ?
F4 S1 C11 C12 27.23(16) . . . . ?
F5 S1 C11 C10 116.32(15) . . . . ?
F5 S1 C11 C12 -63.25(15) . . . . ?
O1 C1 C2 C3 -26.6(2) . . . . ?
O1 C1 C2 C7 156.22(17) . . . . ?
O1 C1 C8 C9 135.01(17) . . . . ?
O1 C1 C8 C13 -47.7(2) . . . . ?
C1 C2 C3 C4 -178.33(17) . . . . ?
C1 C2 C7 C6 178.36(18) . . . . ?
C1 C8 C9 C10 176.63(17) . . . . ?
C1 C8 C13 C12 -176.16(16) . . . . ?
C2 C1 C8 C9 -103.9(2) . . . . ?
C2 C1 C8 C13 73.4(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C3 C4 C5 Cl1 180.00(15) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C2 -0.7(3) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C8 C1 C2 C3 -149.70(18) . . . . ?
C8 C1 C2 C7 33.1(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C9 C10 C11 S1 -178.57(14) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-30
_olex2_date_sample_submission    2015-12-04
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id JD-7-092-F3
_olex2_submission_special_instructions 'No special instructions were received'
