# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 1820347'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 Cl2 F8 O4 S2'
_chemical_formula_weight         399.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.4994(11)
_cell_length_b                   19.724(4)
_cell_length_c                   6.2190(12)
_cell_angle_alpha                90
_cell_angle_beta                 114.278(5)
_cell_angle_gamma                90
_cell_volume                     614.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    1720
_cell_measurement_theta_min      4.0651
_cell_measurement_theta_max      26.7042

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.978
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'REQAB, CrystalClear'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Mercury CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4905
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.740
_diffrn_reflns_theta_max         25.239
_diffrn_reflns_theta_full        25.239
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1119
_reflns_number_gt                782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Rigaku CrystalClear'
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+2.3138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.009(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1119
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.1987
_refine_ls_wR_factor_gt          0.1808
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S1 S 0.4584(4) 0.34499(10) 0.6942(4) 0.0806(8) Uani 1 1 d . . . . .
Cl1 Cl 0.1133(5) 0.29838(12) 0.5114(4) 0.1005(9) Uani 1 1 d . . . . .
C1 C 0.3301(15) 0.4175(4) 0.8103(13) 0.0723(19) Uani 1 1 d . . . . .
C2 C 0.5493(14) 0.4708(3) 0.9466(13) 0.0669(17) Uani 1 1 d . . . . .
F1 F 0.1412(11) 0.4467(3) 0.6275(9) 0.123(2) Uani 1 1 d . . . . .
F2 F 0.2249(11) 0.3926(3) 0.9495(10) 0.1125(19) Uani 1 1 d . . . . .
F3 F 0.7426(9) 0.4373(2) 1.1220(9) 0.1040(18) Uani 1 1 d . . . . .
F4 F 0.6480(12) 0.4948(3) 0.8006(10) 0.1105(19) Uani 1 1 d . . . . .
O1 O 0.5639(16) 0.3708(4) 0.5401(14) 0.133(3) Uani 1 1 d . . . . .
O2 O 0.6126(14) 0.3029(3) 0.8861(13) 0.125(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0713(13) 0.0730(13) 0.0947(15) -0.0077(10) 0.0313(11) 0.0020(9)
Cl1 0.0825(15) 0.1002(17) 0.1067(18) -0.0289(13) 0.0266(12) -0.0104(11)
C1 0.073(5) 0.073(5) 0.064(4) 0.000(3) 0.022(4) -0.002(4)
C2 0.063(4) 0.065(4) 0.068(4) 0.006(3) 0.022(3) 0.004(3)
F1 0.102(4) 0.097(4) 0.104(4) -0.017(3) -0.024(3) 0.032(3)
F2 0.110(4) 0.131(4) 0.122(4) -0.036(3) 0.073(4) -0.040(3)
F3 0.078(3) 0.086(3) 0.104(4) -0.017(3) -0.007(3) 0.020(2)
F4 0.145(5) 0.100(4) 0.128(4) -0.023(3) 0.097(4) -0.030(3)
O1 0.170(7) 0.118(5) 0.173(7) -0.036(5) 0.133(6) -0.038(5)
O2 0.113(5) 0.084(4) 0.121(5) -0.002(4) -0.007(4) 0.030(4)

_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
S1 O1 1.404(7) . ?
S1 O2 1.415(6) . ?
S1 C1 1.866(8) . ?
S1 Cl1 1.991(3) . ?
S1 F1 2.578(5) . ?
Cl1 O2 2.778(7) . ?
Cl1 O1 2.801(7) . ?
Cl1 C1 2.928(8) . ?
Cl1 F1 3.002(6) . ?
Cl1 F2 3.143(6) . ?
Cl1 O2 3.227(7) 4_465 ?
Cl1 Cl1 3.649(3) 4_565 ?
C1 F1 1.317(8) . ?
C1 F2 1.319(9) . ?
C1 C2 1.561(10) . ?
C2 F4 1.322(8) . ?
C2 F3 1.343(8) . ?
C2 C2 1.535(14) 3_667 ?
C2 F1 2.354(8) . ?
C2 F1 2.975(9) 3_667 ?
F1 F2 2.146(9) . ?
F1 F3 2.692(7) 3_667 ?
F1 F1 2.705(10) 3_566 ?
F3 F1 2.692(7) 3_667 ?
F3 F1 3.009(7) 1_656 ?
O1 F1 3.347(10) 1_655 ?
O2 Cl1 3.227(7) 4_666 ?

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
O1 S1 O2 121.0(5) . . ?
O1 S1 C1 108.3(4) . . ?
O2 S1 C1 108.3(4) . . ?
O1 S1 Cl1 110.0(4) . . ?
O2 S1 Cl1 108.1(3) . . ?
C1 S1 Cl1 98.7(3) . . ?
O1 S1 F1 92.9(4) . . ?
O2 S1 F1 136.4(4) . . ?
C1 S1 F1 29.2(2) . . ?
Cl1 S1 F1 81.05(15) . . ?
S1 Cl1 O2 28.96(17) . . ?
S1 Cl1 O1 28.10(18) . . ?
O2 Cl1 O1 52.2(3) . . ?
S1 Cl1 C1 39.04(17) . . ?
O2 Cl1 C1 55.8(2) . . ?
O1 Cl1 C1 55.4(2) . . ?
S1 Cl1 F1 58.02(13) . . ?
O2 Cl1 F1 80.34(16) . . ?
O1 Cl1 F1 62.1(2) . . ?
C1 Cl1 F1 25.61(16) . . ?
S1 Cl1 F2 55.35(12) . . ?
O2 Cl1 F2 58.70(19) . . ?
O1 Cl1 F2 77.95(17) . . ?
C1 Cl1 F2 24.77(17) . . ?
F1 Cl1 F2 40.80(16) . . ?
S1 Cl1 O2 160.37(19) . 4_465 ?
O2 Cl1 O2 132.3(2) . 4_465 ?
O1 Cl1 O2 167.3(2) . 4_465 ?
C1 Cl1 O2 137.2(2) . 4_465 ?
F1 Cl1 O2 128.0(2) . 4_465 ?
F2 Cl1 O2 114.72(19) . 4_465 ?
S1 Cl1 Cl1 113.22(9) . 4_565 ?
O2 Cl1 Cl1 112.66(17) . 4_565 ?
O1 Cl1 Cl1 90.63(14) . 4_565 ?
C1 Cl1 Cl1 144.89(18) . 4_565 ?
F1 Cl1 Cl1 134.17(16) . 4_565 ?
F2 Cl1 Cl1 168.43(11) . 4_565 ?
O2 Cl1 Cl1 76.67(17) 4_465 4_565 ?
F1 C1 F2 109.1(7) . . ?
F1 C1 C2 109.5(6) . . ?
F2 C1 C2 110.1(6) . . ?
F1 C1 S1 106.9(5) . . ?
F2 C1 S1 107.8(5) . . ?
C2 C1 S1 113.3(5) . . ?
F1 C1 Cl1 80.3(4) . . ?
F2 C1 Cl1 86.8(4) . . ?
C2 C1 Cl1 155.1(5) . . ?
S1 C1 Cl1 42.23(17) . . ?
F4 C2 F3 108.8(6) . . ?
F4 C2 C2 110.3(7) . 3_667 ?
F3 C2 C2 108.6(7) . 3_667 ?
F4 C2 C1 108.1(6) . . ?
F3 C2 C1 106.7(6) . . ?
C2 C2 C1 114.1(7) 3_667 . ?
F4 C2 F1 90.7(5) . . ?
F3 C2 F1 138.4(5) . . ?
C2 C2 F1 97.6(6) 3_667 . ?
C1 C2 F1 31.8(3) . . ?
F4 C2 F1 99.8(5) . 3_667 ?
F3 C2 F1 64.7(3) . 3_667 ?
C2 C2 F1 51.6(5) 3_667 3_667 ?
C1 C2 F1 152.0(5) . 3_667 ?
F1 C2 F1 149.2(3) . 3_667 ?
C1 F1 F2 35.5(4) . . ?
C1 F1 C2 38.7(4) . . ?
F2 F1 C2 63.2(3) . . ?
C1 F1 S1 43.8(4) . . ?
F2 F1 S1 65.9(2) . . ?
C2 F1 S1 71.0(2) . . ?
C1 F1 F3 87.5(4) . 3_667 ?
F2 F1 F3 88.5(3) . 3_667 ?
C2 F1 F3 54.8(2) . 3_667 ?
S1 F1 F3 125.7(2) . 3_667 ?
C1 F1 F1 154.9(5) . 3_566 ?
F2 F1 F1 141.7(4) . 3_566 ?
C2 F1 F1 117.1(4) . 3_566 ?
S1 F1 F1 152.4(4) . 3_566 ?
F3 F1 F1 67.8(2) 3_667 3_566 ?
C1 F2 F1 35.4(4) . . ?
C1 F2 Cl1 68.5(4) . . ?
F1 F2 Cl1 66.08(19) . . ?
C2 F3 F1 88.4(4) . 3_667 ?
C2 F3 F1 144.3(4) . 1_656 ?
F1 F3 F1 56.32(19) 3_667 1_656 ?
C2 F4 F1 60.2(4) . . ?
S1 O1 Cl1 41.9(2) . . ?
S1 O1 F1 59.2(3) . . ?
Cl1 O1 F1 62.26(19) . . ?
S1 O1 F1 133.0(5) . 1_655 ?
Cl1 O1 F1 173.6(4) . 1_655 ?
F1 O1 F1 120.1(3) . 1_655 ?
S1 O2 Cl1 42.9(2) . . ?
S1 O2 Cl1 136.3(5) . 4_666 ?
Cl1 O2 Cl1 129.3(2) . 4_666 ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.108

_shelx_res_file                  
;

    C4.res created by SHELXL-2014/7


TITL p21c in P2(1)/c
CELL 0.71073   5.4994  19.7239   6.2190  90.000 114.278  90.000
ZERR    2.00   0.0011   0.0039   0.0012   0.000   0.005   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C O F S CL
UNIT 8 8 16 4 4
TEMP 26
L.S. 12
BOND
FMAP 2
PLAN 20
CONN 8 2.2 CL1
CONN 6 2.2 F1
OMIT -3 50.5
ACTA
SIZE 0.38 0.30 0.07
WGHT    0.039230    2.313800
EXTI    0.009443
FVAR       1.03524
S1    4    0.458382    0.344993    0.694237    11.00000    0.07134    0.07302 =
         0.09466   -0.00769    0.03133    0.00201
CL1   5    0.113304    0.298384    0.511411    11.00000    0.08253    0.10023 =
         0.10666   -0.02893    0.02661   -0.01045
C1    1    0.330149    0.417514    0.810298    11.00000    0.07278    0.07338 =
         0.06432   -0.00012    0.02175   -0.00249
C2    1    0.549278    0.470816    0.946578    11.00000    0.06271    0.06497 =
         0.06824    0.00650    0.02207    0.00403
F1    3    0.141168    0.446722    0.627451    11.00000    0.10175    0.09651 =
         0.10425   -0.01695   -0.02409    0.03249
F2    3    0.224907    0.392577    0.949548    11.00000    0.10963    0.13125 =
         0.12216   -0.03554    0.07344   -0.04014
F3    3    0.742600    0.437339    1.121973    11.00000    0.07814    0.08617 =
         0.10362   -0.01669   -0.00705    0.02048
F4    3    0.647989    0.494765    0.800621    11.00000    0.14472    0.10034 =
         0.12754   -0.02338    0.09741   -0.02980
O1    2    0.563932    0.370751    0.540141    11.00000    0.16978    0.11776 =
         0.17322   -0.03605    0.13317   -0.03844
O2    2    0.612627    0.302866    0.886143    11.00000    0.11350    0.08443 =
         0.12125   -0.00196   -0.00670    0.02990
HKLF 4

REM  p21c in P2(1)/c
REM R1 =  0.0892 for     782 Fo > 4sig(Fo)  and  0.1148 for all    1119 data
REM     92 parameters refined using      0 restraints

END

WGHT      0.1427      1.3305

REM Highest difference peak  0.442,  deepest hole -0.474,  1-sigma level  0.108
Q1    1   0.4555  0.5108  0.7275  11.00000  0.05    0.44
Q2    1   0.2832  0.3755  0.4298  11.00000  0.05    0.42
Q3    1   0.1543  0.4228  0.7994  11.00000  0.05    0.37
Q4    1   0.3399  0.2514  0.7488  11.00000  0.05    0.35
Q5    1   0.1615  0.2383  0.7528  11.00000  0.05    0.32
Q6    1   0.8933  0.5212  1.0045  11.00000  0.05    0.32
Q7    1   0.0336  0.3235  0.7521  11.00000  0.05    0.31
Q8    1   0.9636  0.2937  1.0908  11.00000  0.05    0.30
Q9    1   0.5056  0.2189  0.9019  11.00000  0.05    0.29
Q10   1   0.1146  0.3912  0.4984  11.00000  0.05    0.29
Q11   1   0.7446  0.3196  0.6741  11.00000  0.05    0.28
Q12   1   0.7431  0.3416  0.7966  11.00000  0.05    0.27
Q13   1   0.6653  0.3748  0.9847  11.00000  0.05    0.26
Q14   1  -0.0267  0.3672  0.5569  11.00000  0.05    0.26
Q15   1   0.4842  0.3363  0.8021  11.00000  0.05    0.26
Q16   1   0.4659  0.3190  1.0831  11.00000  0.05    0.26
Q17   1   0.7613  0.4296  0.8316  11.00000  0.05    0.25
Q18   1   0.3527  0.2881  0.4290  11.00000  0.05    0.24
Q19   1   0.8536  0.3600  0.9080  11.00000  0.05    0.24
Q20   1   0.8399  0.2921  0.8977  11.00000  0.05    0.24
;
_shelx_res_checksum              35622

# start Validation Reply Form
_vrf_PLAT031_C4                  
;
PROBLEM: Refined Extinction Parameter Within Range ......      1.800 Sigma 
RESPONSE: While the value for the extinction parameter is within 3x the 
uncertainty, it does appear to help the refinement to keep it
included in the model.  This is probably due to some additional 
contributions to certain reflection intensities due to twinning,
which could not be definitively be accounted for during data processing.
;
_vrf_PLAT340_C4                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0105 Ang.  
RESPONSE: The data quality is somewhat lower because of twinning that
could not be definitively accounted for during data processing.  
However, the data is certainly suitable to build a model that 
successfully resolves the structure and can be used to identify the 
important intermolecular interactions in the present study.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_C6
_database_code_depnum_ccdc_archive 'CCDC 1820348'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 Cl2 F12 O4 S2'
_chemical_formula_weight         499.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3148(7)
_cell_length_b                   24.007(3)
_cell_length_c                   5.8975(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.669(3)
_cell_angle_gamma                90
_cell_volume                     699.29(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5467
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      28.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.370
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.926
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8387
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Ius
_diffrn_measurement_device_type  'Bruker Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7587
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.395
_diffrn_reflns_theta_max         25.231
_diffrn_reflns_theta_full        25.231
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1264
_reflns_number_gt                1159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0080P)²+12.7120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1264
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1578
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S1 S 0.5624(3) 0.67417(7) 0.4368(3) 0.0143(4) Uani 1 1 d . . . . .
Cl1 Cl 0.9116(3) 0.71018(7) 0.6423(3) 0.0189(4) Uani 1 1 d . . . . .
F1 F 0.8919(8) 0.58999(17) 0.5164(7) 0.0191(9) Uani 1 1 d . . . . .
F2 F 0.8328(8) 0.63542(17) 0.1800(8) 0.0197(9) Uani 1 1 d . . . . .
F3 F 0.2939(8) 0.59807(17) 0.0025(8) 0.0216(10) Uani 1 1 d . . . . .
F4 F 0.3881(8) 0.54885(17) 0.3342(8) 0.0206(10) Uani 1 1 d . . . . .
F5 F 0.8168(8) 0.50028(18) 0.2381(8) 0.0276(11) Uani 1 1 d . . . . .
F6 F 0.6881(10) 0.54628(18) -0.1033(9) 0.0284(11) Uani 1 1 d . . . . .
O1 O 0.4380(10) 0.6520(2) 0.5922(10) 0.0220(12) Uani 1 1 d . . . . .
O2 O 0.4234(10) 0.7093(2) 0.2360(10) 0.0230(12) Uani 1 1 d . . . . .
C2 C 0.4888(12) 0.5710(3) 0.1777(12) 0.0116(14) Uani 1 1 d . . . . .
C1 C 0.7117(13) 0.6144(3) 0.3198(12) 0.0122(14) Uani 1 1 d . . . . .
C3 C 0.6018(13) 0.5237(3) 0.0613(13) 0.0144(14) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0093(8) 0.0140(8) 0.0169(9) -0.0006(7) 0.0018(7) 0.0013(6)
Cl1 0.0119(8) 0.0192(9) 0.0214(9) -0.0065(7) 0.0013(7) -0.0014(7)
F1 0.013(2) 0.019(2) 0.014(2) -0.0019(17) -0.0070(16) 0.0056(16)
F2 0.019(2) 0.022(2) 0.021(2) -0.0037(18) 0.0115(18) -0.0069(17)
F3 0.013(2) 0.018(2) 0.022(2) -0.0014(18) -0.0066(17) 0.0041(16)
F4 0.022(2) 0.023(2) 0.022(2) -0.0056(18) 0.0137(19) -0.0083(17)
F5 0.015(2) 0.023(2) 0.030(3) -0.0088(19) -0.0105(18) 0.0098(18)
F6 0.041(3) 0.024(2) 0.036(3) -0.011(2) 0.032(2) -0.013(2)
O1 0.021(3) 0.025(3) 0.025(3) -0.003(2) 0.014(2) -0.001(2)
O2 0.017(3) 0.018(3) 0.026(3) 0.004(2) -0.001(2) 0.005(2)
C2 0.005(3) 0.017(3) 0.012(3) 0.002(3) 0.003(3) 0.002(3)
C1 0.013(3) 0.014(3) 0.010(3) 0.001(3) 0.005(3) 0.002(3)
C3 0.010(3) 0.014(3) 0.015(4) -0.001(3) 0.000(3) 0.002(3)

_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
S1 O1 1.417(5) . ?
S1 O2 1.418(5) . ?
S1 C1 1.889(7) . ?
S1 Cl1 2.000(2) . ?
F1 C1 1.336(8) . ?
F2 C1 1.319(8) . ?
F3 C2 1.331(8) . ?
F4 C2 1.337(8) . ?
F5 C3 1.353(8) . ?
F6 C3 1.332(8) . ?
C2 C3 1.558(9) . ?
C2 C1 1.568(9) . ?
C3 C3 1.552(13) 3_665 ?

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
O1 S1 O2 122.6(3) . . ?
O1 S1 C1 108.1(3) . . ?
O2 S1 C1 107.8(3) . . ?
O1 S1 Cl1 108.7(2) . . ?
O2 S1 Cl1 109.3(2) . . ?
C1 S1 Cl1 97.4(2) . . ?
F3 C2 F4 109.6(5) . . ?
F3 C2 C3 109.3(5) . . ?
F4 C2 C3 109.3(5) . . ?
F3 C2 C1 108.0(5) . . ?
F4 C2 C1 108.2(5) . . ?
C3 C2 C1 112.5(5) . . ?
F2 C1 F1 110.6(5) . . ?
F2 C1 C2 111.5(5) . . ?
F1 C1 C2 109.3(5) . . ?
F2 C1 S1 107.8(4) . . ?
F1 C1 S1 106.2(4) . . ?
C2 C1 S1 111.3(4) . . ?
F6 C3 F5 108.1(6) . . ?
F6 C3 C3 109.1(7) . 3_665 ?
F5 C3 C3 107.4(7) . 3_665 ?
F6 C3 C2 108.4(5) . . ?
F5 C3 C2 108.5(5) . . ?
C3 C3 C2 115.1(7) 3_665 . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.143

_shelx_res_file                  
;

    d8-0074_a.res created by SHELXL-2014/7


TITL d8-0074_a.res in P2(1)/c
REM Old TITL d8-0074 in P2(1)/m

REM SHELXT solution in P2(1)/c
REM R1 0.362,  Rweak 0.043,  Alpha 0.057,  Orientation as input
REM Formula found by SHELXT:  C4 O2 F6 Cl

CELL  0.71073   5.3148  24.0065   5.8975   90.000  111.669   90.000
ZERR    2.000   0.0007   0.0033   0.0008    0.000    0.003    0.000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C O F S CL
UNIT 12 8 24 4 4
TEMP -173.110
SIZE 0.021 0.242 0.268
L.S. 10
BOND $H
LIST 4
ACTA
OMIT -3 50.5
FMAP 2
PLAN 20
WGHT    0.008000   12.712000
FVAR       0.62705
S1    4    0.562402    0.674169    0.436813    11.00000    0.00930    0.01399 =
         0.01689   -0.00065    0.00177    0.00126
CL1   5    0.911646    0.710181    0.642272    11.00000    0.01193    0.01921 =
         0.02140   -0.00649    0.00130   -0.00145
F1    3    0.891880    0.589987    0.516368    11.00000    0.01342    0.01913 =
         0.01444   -0.00186   -0.00698    0.00559
F2    3    0.832766    0.635420    0.180014    11.00000    0.01912    0.02246 =
         0.02112   -0.00374    0.01151   -0.00691
F3    3    0.293881    0.598072    0.002457    11.00000    0.01274    0.01844 =
         0.02240   -0.00138   -0.00655    0.00414
F4    3    0.388084    0.548848    0.334180    11.00000    0.02232    0.02260 =
         0.02175   -0.00555    0.01369   -0.00829
F5    3    0.816807    0.500276    0.238127    11.00000    0.01457    0.02288 =
         0.02953   -0.00879   -0.01048    0.00980
F6    3    0.688142    0.546284   -0.103259    11.00000    0.04102    0.02399 =
         0.03595   -0.01139    0.03248   -0.01336
O1    2    0.438030    0.652024    0.592209    11.00000    0.02147    0.02473 =
         0.02497   -0.00311    0.01448   -0.00088
O2    2    0.423353    0.709257    0.236011    11.00000    0.01732    0.01769 =
         0.02619    0.00405   -0.00121    0.00458
C2    1    0.488825    0.571035    0.177686    11.00000    0.00535    0.01716 =
         0.01194    0.00211    0.00265    0.00242
C1    1    0.711691    0.614429    0.319830    11.00000    0.01252    0.01448 =
         0.01021    0.00150    0.00499    0.00210
C3    1    0.601816    0.523689    0.061270    11.00000    0.00978    0.01435 =
         0.01521   -0.00104    0.00017    0.00151
HKLF 4

REM  d8-0074_a.res in P2(1)/c
REM R1 =  0.0616 for    1159 Fo > 4sig(Fo)  and  0.0667 for all    1264 data
REM    118 parameters refined using      0 restraints

END

WGHT      0.0000      7.2176

REM Highest difference peak  0.498,  deepest hole -0.637,  1-sigma level  0.143
Q1    1   0.9403  0.7475  0.6933  11.00000  0.05    0.50
Q2    1   0.6874  0.7790  0.5622  11.00000  0.05    0.48
Q3    1   0.1146  0.7186  0.0974  11.00000  0.05    0.47
Q4    1   0.9394  0.6893  0.8153  11.00000  0.05    0.46
Q5    1   0.9635  0.5698  0.6830  11.00000  0.05    0.44
Q6    1   0.7643  0.5739 -0.2941  11.00000  0.05    0.44
Q7    1   0.7718  0.7319  0.8718  11.00000  0.05    0.43
Q8    1   1.1044  0.5047  0.3857  11.00000  0.05    0.41
Q9    1   0.8385  0.4584  0.2615  11.00000  0.05    0.41
Q10   1   0.1863  0.5849 -0.2802  11.00000  0.05    0.41
Q11   1   0.6939  0.5908 -0.1270  11.00000  0.05    0.40
Q12   1   0.5109  0.5522 -0.1064  11.00000  0.05    0.40
Q13   1   0.8938  0.6697  0.6552  11.00000  0.05    0.40
Q14   1   0.6238  0.6787 -0.0247  11.00000  0.05    0.40
Q15   1   0.5257  0.7110  0.4444  11.00000  0.05    0.40
Q16   1   0.5349  0.5394  0.5557  11.00000  0.05    0.39
Q17   1   0.4420  0.5846  0.4912  11.00000  0.05    0.39
Q18   1   0.9375  0.6531  0.7958  11.00000  0.05    0.38
Q19   1   0.8130  0.5358 -0.1899  11.00000  0.05    0.38
Q20   1   1.0781  0.7059  0.4372  11.00000  0.05    0.38
;
_shelx_res_checksum              56714
