# 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_haf8587
_database_code_depnum_ccdc_archive 'CCDC 1511242'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H17 Cl F6 N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         410.71
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.0208(8)
_cell_length_b                   5.0952(4)
_cell_length_c                   14.7276(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.403(6)
_cell_angle_gamma                90
_cell_volume                     804.48(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2344
_cell_measurement_theta_min      4.1237
_cell_measurement_theta_max      68.1708
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.055
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420

_exptl_absorpt_coefficient_mu    3.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           ' Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            7433
_diffrn_reflns_av_R_equivalents  0.1473
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         63.65
_diffrn_reflns_theta_full        63.65
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_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_number_total             2417
_reflns_number_gt                1807
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0918
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1690
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.188
_refine_ls_number_reflns         2417
_refine_ls_number_parameters     248
_refine_ls_number_restraints     34
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.2516P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.548
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 494 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)

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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v.2014.1.1 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.1215(3) 0.1791(6) 0.4042(2) 0.0168(7) Uani d . . . 1 . .
N N1A 0.6781(11) 0.171(3) 0.5643(7) 0.020(2) Uani d . . D 1 . .
H H4 0.720(12) 0.014(16) 0.563(10) 0.03 Uiso d U . D 1 . .
H H5 0.729(12) 0.31(2) 0.557(11) 0.03 Uiso d U . D 1 . .
H H6 0.605(8) 0.25(3) 0.532(9) 0.03 Uiso d U . D 1 . .
O O1A 0.6391(8) -0.0238(18) 0.8338(6) 0.021(2) Uani d . . . 1 . .
H H1C 0.412(12) 0.69(3) 0.696(8) 0.03(4) Uiso d . . . 1 . .
O O2A 0.5449(8) 0.6002(15) 0.5689(6) 0.016(2) Uani d . . . 1 . .
O O3A 0.4780(9) 0.4762(19) 0.6937(7) 0.025(2) Uani d . . . 1 . .
F F1A 0.5269(8) -0.2748(16) 0.9001(6) 0.036(2) Uani d . . . 1 . .
F F2A 0.6599(8) -0.016(2) 0.9877(5) 0.039(2) Uani d . . . 1 . .
F F3A 0.4932(7) 0.1384(16) 0.9017(5) 0.027(2) Uani d . . . 1 . .
C C1A 0.6276(12) 0.204(3) 0.6484(8) 0.019(3) Uani d . . . 1 . .
H H1A 0.5772 0.046 0.6562 0.022 Uiso calc U . R 1 . .
C C2A 0.7358(12) 0.231(3) 0.7338(8) 0.018(3) Uani d . . . 1 . .
H H201 0.7957 0.0872 0.7328 0.021 Uiso calc U . R 1 . .
H H202 0.7794 0.3987 0.7288 0.021 Uiso calc U . R 1 . .
C C3A 0.6997(12) 0.226(3) 0.8266(9) 0.021(3) Uani d . . . 1 . .
H H301 0.7748 0.2447 0.8782 0.026 Uiso calc U . R 1 . .
H H302 0.642 0.3724 0.8304 0.026 Uiso calc U . R 1 . .
C C4A 0.5825(14) -0.034(3) 0.9045(9) 0.026(3) Uani d . . . 1 . .
C C5A 0.5426(12) 0.447(3) 0.6340(9) 0.018(3) Uani d . . . 1 . .
N N1B 0.0647(11) 1.178(3) 0.6068(8) 0.024(3) Uani d . . . 1 . .
H H1 0.047(14) 1.17(4) 0.549(10) 0.036 Uiso d U . . 1 . .
H H2 0.008(16) 1.30(3) 0.617(11) 0.036 Uiso d U . . 1 . .
H H3 0.022(16) 1.02(4) 0.616(11) 0.036 Uiso d U . . 1 . .
O O1B 0.0715(9) 0.9861(19) 0.8081(6) 0.024(2) Uani d U . . 1 . .
O O2B 0.1974(9) 0.7463(15) 0.5914(7) 0.021(2) Uani d U . . 1 . .
O O3B 0.3664(9) 0.8837(17) 0.6970(7) 0.023(2) Uani d U . . 1 . .
F F1B 0.1067(8) 0.647(2) 0.9056(6) 0.045(2) Uani d . . . 1 . .
F F2B 0.0375(10) 0.9989(19) 0.9499(6) 0.053(3) Uani d . . . 1 . .
F F3B -0.0792(9) 0.7652(19) 0.8457(7) 0.052(3) Uani d . . . 1 . .
C C1B 0.1975(12) 1.177(3) 0.6585(8) 0.021(3) Uani d . . . 1 . .
H H1B 0.2408 1.3073 0.6263 0.025 Uiso calc U . R 1 . .
C C2B 0.2160(14) 1.273(2) 0.7589(9) 0.018(3) Uani d . . . 1 . .
H H211 0.3015 1.3447 0.7789 0.022 Uiso calc U . R 1 . .
H H212 0.1573 1.4193 0.7597 0.022 Uiso calc U . R 1 . .
C C3B 0.1986(12) 1.076(3) 0.8294(9) 0.019(3) Uani d . . . 1 . .
H H311 0.2553 0.9251 0.8291 0.023 Uiso calc U . R 1 . .
H H312 0.2193 1.1555 0.8924 0.023 Uiso calc U . R 1 . .
C C4B 0.0342(15) 0.852(3) 0.8751(11) 0.026(4) Uani d U . . 1 . .
C C5B 0.2553(13) 0.913(3) 0.6470(9) 0.018(3) Uani d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1A C1A . 1.482(16) ?
N1A H4 . 0.92(3) ?
N1A H5 . 0.92(3) ?
N1A H6 . 0.92(3) ?
O1A C4A . 1.334(16) ?
O1A C3A . 1.452(16) ?
O2A C5A . 1.240(15) ?
O3A C5A . 1.262(16) ?
O3A H1C . 1.30(17) ?
F1A C4A . 1.366(18) ?
F2A C4A . 1.324(14) ?
F3A C4A . 1.312(16) ?
C1A C2A . 1.525(16) ?
C1A C5A . 1.54(2) ?
C1A H1A . 1.0 ?
C2A C3A . 1.510(17) ?
C2A H201 . 0.99 ?
C2A H202 . 0.99 ?
C3A H301 . 0.99 ?
C3A H302 . 0.99 ?
N1B C1B . 1.485(16) ?
N1B H1 . 0.82(14) ?
N1B H2 . 0.93(18) ?
N1B H3 . 0.93(18) ?
O1B C4B . 1.342(18) ?
O1B C3B . 1.437(15) ?
O2B C5B . 1.246(16) ?
O3B C5B . 1.283(16) ?
O3B H1C . 1.12(17) ?
F1B C4B . 1.329(16) ?
F2B C4B . 1.326(17) ?
F3B C4B . 1.301(17) ?
C1B C5B . 1.52(2) ?
C1B C2B . 1.525(18) ?
C1B H1B . 1.0 ?
C2B C3B . 1.488(17) ?
C2B H211 . 0.99 ?
C2B H212 . 0.99 ?
C3B H311 . 0.99 ?
C3B H312 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1A N1A H4 . . 114.(10) ?
C1A N1A H5 . . 112.(10) ?
H4 N1A H5 . . 110.(10) ?
C1A N1A H6 . . 87.(9) ?
H4 N1A H6 . . 136.(10) ?
H5 N1A H6 . . 96.(10) ?
C4A O1A C3A . . 113.4(11) ?
C5A O3A H1C . . 121.(6) ?
N1A C1A C2A . . 109.1(10) ?
N1A C1A C5A . . 108.2(11) ?
C2A C1A C5A . . 112.0(11) ?
N1A C1A H1A . . 109.2 ?
C2A C1A H1A . . 109.2 ?
C5A C1A H1A . . 109.2 ?
C3A C2A C1A . . 115.1(11) ?
C3A C2A H201 . . 108.5 ?
C1A C2A H201 . . 108.5 ?
C3A C2A H202 . . 108.5 ?
C1A C2A H202 . . 108.5 ?
H201 C2A H202 . . 107.5 ?
O1A C3A C2A . . 107.7(11) ?
O1A C3A H301 . . 110.2 ?
C2A C3A H301 . . 110.2 ?
O1A C3A H302 . . 110.2 ?
C2A C3A H302 . . 110.2 ?
H301 C3A H302 . . 108.5 ?
F3A C4A F2A . . 107.5(11) ?
F3A C4A O1A . . 115.7(12) ?
F2A C4A O1A . . 113.7(13) ?
F3A C4A F1A . . 106.0(12) ?
F2A C4A F1A . . 107.0(12) ?
O1A C4A F1A . . 106.5(11) ?
O2A C5A O3A . . 125.6(13) ?
O2A C5A C1A . . 119.5(12) ?
O3A C5A C1A . . 114.9(12) ?
C1B N1B H1 . . 120.(10) ?
C1B N1B H2 . . 122.(10) ?
H1 N1B H2 . . 100.(10) ?
C1B N1B H3 . . 113.(10) ?
H1 N1B H3 . . 97.(10) ?
H2 N1B H3 . . 100.(10) ?
C4B O1B C3B . . 116.8(11) ?
C5B O3B H1C . . 117.(7) ?
N1B C1B C5B . . 109.5(12) ?
N1B C1B C2B . . 113.1(11) ?
C5B C1B C2B . . 115.3(11) ?
N1B C1B H1B . . 106.1 ?
C5B C1B H1B . . 106.1 ?
C2B C1B H1B . . 106.1 ?
C3B C2B C1B . . 116.8(11) ?
C3B C2B H211 . . 108.1 ?
C1B C2B H211 . . 108.1 ?
C3B C2B H212 . . 108.1 ?
C1B C2B H212 . . 108.1 ?
H211 C2B H212 . . 107.3 ?
O1B C3B C2B . . 109.9(11) ?
O1B C3B H311 . . 109.7 ?
C2B C3B H311 . . 109.7 ?
O1B C3B H312 . . 109.7 ?
C2B C3B H312 . . 109.7 ?
H311 C3B H312 . . 108.2 ?
F3B C4B F2B . . 107.9(14) ?
F3B C4B F1B . . 107.6(12) ?
F2B C4B F1B . . 105.4(12) ?
F3B C4B O1B . . 111.2(12) ?
F2B C4B O1B . . 111.6(12) ?
F1B C4B O1B . . 112.7(13) ?
O2B C5B O3B . . 125.1(13) ?
O2B C5B C1B . . 120.9(12) ?
O3B C5B C1B . . 114.0(12) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1A C1A C2A C3A . . . . -171.2(12) ?
C5A C1A C2A C3A . . . . 69.1(15) ?
C4A O1A C3A C2A . . . . -168.3(11) ?
C1A C2A C3A O1A . . . . 59.8(15) ?
C3A O1A C4A F3A . . . . 60.6(16) ?
C3A O1A C4A F2A . . . . -64.5(16) ?
C3A O1A C4A F1A . . . . 178.0(10) ?
N1A C1A C5A O2A . . . . -12.7(17) ?
C2A C1A C5A O2A . . . . 107.6(13) ?
N1A C1A C5A O3A . . . . 169.4(11) ?
C2A C1A C5A O3A . . . . -70.3(16) ?
N1B C1B C2B C3B . . . . 83.8(17) ?
C5B C1B C2B C3B . . . . -43.2(17) ?
C4B O1B C3B C2B . . . . -166.2(12) ?
C1B C2B C3B O1B . . . . -63.8(16) ?
C3B O1B C4B F3B . . . . -175.5(11) ?
C3B O1B C4B F2B . . . . 63.9(16) ?
C3B O1B C4B F1B . . . . -54.5(16) ?
N1B C1B C5B O2B . . . . 8.2(18) ?
C2B C1B C5B O2B . . . . 137.0(13) ?
N1B C1B C5B O3B . . . . -173.2(11) ?
C2B C1B C5B O3B . . . . -44.4(17) ?

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
_geom_hbond_publ_flag
N1A H4 Cl1 2_646 0.92(3) 2.41(5) 3.300(13) 162.(12) ?
N1A H5 Cl1 2_656 0.92(3) 2.48(6) 3.366(13) 160.(13) ?
N1A H6 O2A 2_646 0.92(3) 2.08(10) 2.789(14) 133.(12) ?
O3B H1C O3A . 1.12(17) 1.30(17) 2.419(12) 172.(14) ?
N1B H1 Cl1 1_565 0.82(14) 2.46(15) 3.188(12) 148.(13) ?
N1B H2 Cl1 2_566 0.93(18) 2.36(18) 3.258(14) 161.(14) ?
N1B H3 Cl1 2_556 0.93(18) 2.34(19) 3.245(14) 163.(14) ?

