# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1835508'
_audit_update_record             
;
2018-04-08 deposited with the CCDC.
2018-06-22 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         'C12 H24 O6, C6 H6 F2 N, Cl O4'
_chemical_formula_sum            'C18 H30 Cl F2 N O10 '
_chemical_formula_weight         493.88

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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.558(5)
_cell_length_b                   11.247(4)
_cell_length_c                   14.392(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2356.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    203
_cell_measurement_reflns_used    5200
_cell_measurement_theta_min      3.136
_cell_measurement_theta_max      27.457

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16630
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.136
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5200
_reflns_number_gt                4132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.958

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0862P)²+19.4170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1193 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5200
_refine_ls_number_parameters     319
_refine_ls_number_restraints     169
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.1402
_refine_ls_wR_factor_ref         0.3392
_refine_ls_wR_factor_gt          0.3273
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.2163(2) 0.2517(3) 0.8873(3) 0.0444(8) Uani 1 1 d D . . . .
O7 O 0.3108(7) 0.2360(10) 0.9098(9) 0.064(3) Uani 1 1 d . . . . .
O8 O 0.1969(17) 0.2036(19) 0.7942(14) 0.067(5) Uani 0.491(12) 1 d D U P A 1
O9 O 0.1632(16) 0.187(2) 0.9570(14) 0.068(5) Uani 0.491(12) 1 d D U P A 1
O10 O 0.1852(16) 0.3686(15) 0.8779(18) 0.068(5) Uani 0.491(12) 1 d D U P A 1
O8' O 0.2046(18) 0.3371(17) 0.8158(16) 0.069(5) Uani 0.509(12) 1 d D U P A 2
O9' O 0.1819(14) 0.1365(14) 0.8654(15) 0.062(5) Uani 0.509(12) 1 d D U P A 2
O10' O 0.1704(17) 0.298(2) 0.9676(15) 0.073(5) Uani 0.509(12) 1 d D U P A 2
C6 C 0.0663(12) 0.6531(14) 0.5170(13) 0.062(5) Uani 1 1 d . . . . .
H6A H 0.0111 0.6054 0.5108 0.074 Uiso 1 1 calc R U . . .
H6B H 0.0963 0.6574 0.4569 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0980(11) 0.9731(11) 0.5783(13) 0.055(4) Uani 1 1 d . . . . .
H4A H 0.0648 0.9758 0.6367 0.066 Uiso 1 1 calc R U . . .
H4B H 0.0585 1.0048 0.5301 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1855(12) 1.0488(13) 0.5855(13) 0.061(5) Uani 1 1 d . . . . .
H3A H 0.2177 1.0481 0.5265 0.074 Uiso 1 1 calc R U . . .
H3B H 0.1693 1.1304 0.5999 0.074 Uiso 1 1 calc R U . . .
C1 C 0.3793(12) 1.0224(15) 0.7451(11) 0.062(4) Uani 1 1 d . U . . .
H1A H 0.4335 1.0712 0.7544 0.074 Uiso 1 1 calc R U . . .
H1B H 0.3432 1.0235 0.8018 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0423(10) 0.7785(10) 0.5520(9) 0.038(3) Uani 1 1 d . . . . .
H5A H -0.0021 0.8147 0.5104 0.046 Uiso 1 1 calc R U . . .
H5B H 0.0147 0.7731 0.6132 0.046 Uiso 1 1 calc R U . . .
C2 C 0.3233(11) 1.0693(12) 0.6647(13) 0.060(4) Uani 1 1 d . U . . .
H2A H 0.3087 1.1523 0.6754 0.072 Uiso 1 1 calc R U . . .
H2B H 0.3592 1.0642 0.6080 0.072 Uiso 1 1 calc R U . . .
O6 O 0.2415(7) 1.0043(7) 0.6538(7) 0.045(2) Uani 1 1 d . . . . .
O5 O 0.1222(6) 0.8503(9) 0.5564(7) 0.049(3) Uani 1 1 d . . . . .
O4 O 0.1271(8) 0.6014(9) 0.5850(8) 0.057(3) Uani 1 1 d . . . . .
C8 C 0.1657(12) 0.4904(15) 0.5449(13) 0.066(5) Uani 1 1 d . . . . .
H8A H 0.2017 0.5083 0.4899 0.079 Uiso 1 1 calc R U . . .
H8B H 0.1167 0.4364 0.5276 0.079 Uiso 1 1 calc R U . . .
C9 C 0.2254(14) 0.4352(16) 0.6184(19) 0.105(10) Uani 1 1 d . . . . .
H9A H 0.1898 0.4201 0.6741 0.126 Uiso 1 1 calc R U . . .
H9B H 0.2504 0.3603 0.5964 0.126 Uiso 1 1 calc R U . . .
O3 O 0.2984(8) 0.5179(8) 0.6378(8) 0.055(3) Uani 1 1 d . . . . .
N1 N 0.7569(7) 0.2486(9) 0.1976(7) 0.036(2) Uani 1 1 d . . . . .
H1E H 0.7542 0.1729 0.1776 0.043 Uiso 1 1 d R U . . .
H1D H 0.6990 0.2741 0.2067 0.043 Uiso 1 1 d R U . . .
H1C H 0.7844 0.2922 0.1532 0.043 Uiso 1 1 d R U . . .
F1 F 0.9528(10) 0.2689(15) 0.5278(9) 0.119(5) Uani 1 1 d . U . . .
C15 C 0.9038(10) 0.2702(19) 0.4452(11) 0.072(4) Uani 1 1 d . U . . .
C17 C 0.8846(13) 0.1623(18) 0.4090(12) 0.069(4) Uani 1 1 d . U . . .
C11 C 0.8743(11) 0.3701(18) 0.4069(11) 0.071(4) Uani 1 1 d . U . . .
H11 H 0.8860 0.4439 0.4335 0.086 Uiso 1 1 calc R U . . .
C13 C 0.8085(8) 0.2485(12) 0.2853(9) 0.038(3) Uani 1 1 d . U . . .
C12 C 0.4450(12) 0.5436(15) 0.7202(16) 0.078(6) Uani 1 1 d . . . . .
H12A H 0.4826 0.5040 0.7665 0.093 Uiso 1 1 calc R U . . .
H12B H 0.4824 0.5567 0.6654 0.093 Uiso 1 1 calc R U . . .
C18 C 0.8263(12) 0.3590(15) 0.3274(11) 0.061(4) Uani 1 1 d . U . . .
H18A H 0.8040 0.4274 0.2991 0.073 Uiso 1 1 calc R U . . .
C19 C 0.8383(11) 0.1459(15) 0.3246(11) 0.055(3) Uani 1 1 d . U . . .
H19A H 0.8288 0.0715 0.2980 0.066 Uiso 1 1 calc R U . . .
O2 O 0.4148(6) 0.6524(9) 0.7550(7) 0.045(2) Uani 1 1 d . . . . .
C20 C 0.4899(10) 0.7307(11) 0.7664(11) 0.046(3) Uani 1 1 d . . . . .
H20A H 0.5213 0.7415 0.7076 0.055 Uiso 1 1 calc R U . . .
H20B H 0.5332 0.6979 0.8107 0.055 Uiso 1 1 calc R U . . .
O1 O 0.4049(6) 0.9045(9) 0.7226(7) 0.047(2) Uani 1 1 d . . . . .
F2 F 0.9230(11) 0.0673(14) 0.4498(10) 0.125(5) Uani 1 1 d . U . . .
C21 C 0.4549(10) 0.8463(14) 0.8003(12) 0.056(4) Uani 1 1 d . . . . .
H21A H 0.5055 0.8961 0.8206 0.067 Uiso 1 1 calc R U . . .
H21B H 0.4138 0.8342 0.8526 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3658(14) 0.4679(15) 0.6963(18) 0.088(7) Uani 1 1 d . . . . .
H22A H 0.3890 0.3965 0.6666 0.105 Uiso 1 1 calc R U . . .
H22B H 0.3362 0.4438 0.7536 0.105 Uiso 1 1 calc R U . . .


_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 O10 1.397(16) . ?
Cl1 O8' 1.417(17) . ?
Cl1 O9' 1.424(14) . ?
Cl1 O7 1.425(10) . ?
Cl1 O10' 1.434(17) . ?
Cl1 O9 1.459(17) . ?
Cl1 O8 1.472(17) . ?
C6 O4 1.44(2) . ?
C6 C5 1.538(18) . ?
C4 O5 1.459(16) . ?
C4 C3 1.54(2) . ?
C3 O6 1.372(17) . ?
C1 O1 1.42(2) . ?
C1 C2 1.51(2) . ?
C5 O5 1.418(17) . ?
C2 O6 1.406(18) . ?
O4 C8 1.486(18) . ?
C8 C9 1.50(3) . ?
C9 O3 1.44(2) . ?
O3 C22 1.41(2) . ?
N1 C13 1.468(15) . ?
F1 C15 1.39(2) . ?
C15 C11 1.32(3) . ?
C15 C17 1.35(3) . ?
C17 F2 1.34(2) . ?
C17 C19 1.40(2) . ?
C11 C18 1.35(2) . ?
C13 C19 1.36(2) . ?
C13 C18 1.407(19) . ?
C12 O2 1.393(18) . ?
C12 C22 1.47(2) . ?
O2 C20 1.413(16) . ?
C20 C21 1.48(2) . ?
O1 C21 1.486(17) . ?

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
O8' Cl1 O9' 114.4(13) . . ?
O10 Cl1 O7 116.8(11) . . ?
O8' Cl1 O7 111.4(12) . . ?
O9' Cl1 O7 106.1(11) . . ?
O8' Cl1 O10' 106.4(13) . . ?
O9' Cl1 O10' 110.3(13) . . ?
O7 Cl1 O10' 108.2(12) . . ?
O10 Cl1 O9 111.2(14) . . ?
O7 Cl1 O9 107.1(11) . . ?
O10 Cl1 O8 101.3(13) . . ?
O7 Cl1 O8 110.2(11) . . ?
O9 Cl1 O8 110.0(13) . . ?
O4 C6 C5 106.6(12) . . ?
O5 C4 C3 109.8(13) . . ?
O6 C3 C4 109.8(12) . . ?
O1 C1 C2 107.0(14) . . ?
O5 C5 C6 110.6(11) . . ?
O6 C2 C1 111.1(12) . . ?
C3 O6 C2 113.1(10) . . ?
C5 O5 C4 110.5(10) . . ?
C6 O4 C8 107.9(11) . . ?
O4 C8 C9 107.0(13) . . ?
O3 C9 C8 107.3(18) . . ?
C22 O3 C9 111.9(13) . . ?
C11 C15 C17 122.3(16) . . ?
C11 C15 F1 122.3(17) . . ?
C17 C15 F1 115.4(19) . . ?
F2 C17 C15 117.4(16) . . ?
F2 C17 C19 118.4(16) . . ?
C15 C17 C19 123.6(18) . . ?
C15 C11 C18 116.4(17) . . ?
C19 C13 C18 120.9(13) . . ?
C19 C13 N1 121.5(12) . . ?
C18 C13 N1 117.6(12) . . ?
O2 C12 C22 110.2(14) . . ?
C11 C18 C13 122.9(18) . . ?
C13 C19 C17 113.7(15) . . ?
C12 O2 C20 110.2(12) . . ?
O2 C20 C21 108.7(12) . . ?
C1 O1 C21 111.6(12) . . ?
C20 C21 O1 107.8(13) . . ?
O3 C22 C12 117.0(15) . . ?

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
N1 H1E O6 0.90 2.03 2.923(9) 170.0 2_664
N1 H1C O4 0.90 2.01 2.880(11) 162.8 2_664
N1 H1D O2 0.90 1.97 2.856(10) 166.0 2_664


_refine_diff_density_max         0.818
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.116


_vrf_PLAT340_1                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02333 Ang.  
RESPONSE: The alert is due to the weaker diffraction points at this temperature.
;

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1835670'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-22 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            'C18 H30 Cl F2 N O10'
_chemical_formula_weight         493.88


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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.5486(9)
_cell_length_b                   11.2914(7)
_cell_length_c                   14.5674(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2393.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4419
_cell_measurement_theta_min      2.6630
_cell_measurement_theta_max      28.6350

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku oxford synergy Xtalab'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11819
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         31.620
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.792
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.792
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             5598
_reflns_number_gt                3473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.591
_reflns_Friedel_fraction_full    0.841

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0487P)²+0.2375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1244 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5598
_refine_ls_number_parameters     328
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.018
_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
Cl1 Cl 0.78526(5) 0.74897(8) 0.11167(8) 0.0671(2) Uani 1 1 d D . . . .
O7 O 0.6915(2) 0.7540(3) 0.0906(3) 0.1158(12) Uani 1 1 d . . . . .
O8 O 0.8111(5) 0.8225(9) 0.1858(8) 0.139(7) Uani 0.59(2) 1 d D . P A 1
O9 O 0.8332(5) 0.7807(12) 0.0352(6) 0.161(9) Uani 0.59(2) 1 d D . P A 1
O10 O 0.8095(5) 0.6350(5) 0.1358(7) 0.109(4) Uani 0.59(2) 1 d D . P A 1
O8' O 0.8239(7) 0.8576(7) 0.1051(12) 0.118(6) Uani 0.41(2) 1 d D . P A 2
O9' O 0.8373(7) 0.6755(13) 0.0566(13) 0.158(12) Uani 0.41(2) 1 d D . P A 2
O10' O 0.7954(9) 0.709(2) 0.1976(8) 0.208(17) Uani 0.41(2) 1 d D . P A 2
C6 C 0.9329(3) 0.3397(4) 0.4811(3) 0.0922(12) Uani 1 1 d . . . . .
H6A H 0.9009 0.3305 0.5385 0.111 Uiso 1 1 d R U . . .
H6B H 0.9868 0.3867 0.4922 0.111 Uiso 1 1 d R U . . .
C4 C 0.9011(3) 0.0307(4) 0.4216(3) 0.1005(14) Uani 1 1 d . . . . .
H4A H 0.9415 -0.0009 0.4677 0.121 Uiso 1 1 d R U . . .
H4B H 0.9319 0.0259 0.3633 0.121 Uiso 1 1 d R U . . .
C3 C 0.8167(3) -0.0401(4) 0.4180(3) 0.1010(14) Uani 1 1 d . . . . .
H3A H 0.8318 -0.1219 0.4078 0.121 Uiso 1 1 d R U . . .
H3B H 0.7848 -0.0341 0.4756 0.121 Uiso 1 1 d R U . . .
C1 C 0.6254(3) -0.0179(4) 0.2567(3) 0.0949(12) Uani 1 1 d . . . . .
H1A H 0.6629 -0.0183 0.2023 0.114 Uiso 1 1 d R U . . .
H1B H 0.5725 -0.0666 0.2455 0.114 Uiso 1 1 d R U . . .
C5 C 0.9600(3) 0.2235(4) 0.4453(3) 0.0887(12) Uani 1 1 d . . . . .
H5A H 0.9866 0.2314 0.3851 0.106 Uiso 1 1 d R U . . .
H5B H 1.0049 0.1884 0.4853 0.106 Uiso 1 1 d R U . . .
C2 C 0.6780(3) -0.0652(4) 0.3351(3) 0.0956(13) Uani 1 1 d . . . . .
H2A H 0.6417 -0.0607 0.3902 0.115 Uiso 1 1 d R U . . .
H2B H 0.6930 -0.1470 0.3243 0.115 Uiso 1 1 d R U . . .
O6 O 0.76048(18) 0.0027(2) 0.34649(18) 0.0778(7) Uani 1 1 d . . . . .
O5 O 0.88149(17) 0.1513(2) 0.44160(18) 0.0816(7) Uani 1 1 d . . . . .
O4 O 0.87453(17) 0.3992(2) 0.41692(16) 0.0771(6) Uani 1 1 d . . . . .
C8 C 0.8352(3) 0.5043(4) 0.4530(3) 0.0917(12) Uani 1 1 d . . . . .
H8A H 0.8830 0.5578 0.4720 0.110 Uiso 1 1 d R U . . .
H8B H 0.7986 0.4853 0.5060 0.110 Uiso 1 1 d R U . . .
C9 C 0.7786(3) 0.5620(3) 0.3824(3) 0.0932(13) Uani 1 1 d . . . . .
H9A H 0.7556 0.6361 0.4055 0.112 Uiso 1 1 d R U . . .
H9B H 0.8146 0.5780 0.3284 0.112 Uiso 1 1 d R U . . .
O3 O 0.70303(18) 0.4855(2) 0.35965(19) 0.0837(7) Uani 1 1 d . . . . .
N1 N 0.23851(16) 0.75071(18) 0.80033(17) 0.0524(5) Uani 1 1 d . . . . .
H1C H 0.2041 0.7211 0.8446 0.079 Uiso 1 1 d R U . . .
H1D H 0.2533 0.8244 0.8138 0.079 Uiso 1 1 d R U . . .
H1E H 0.2889 0.7080 0.7947 0.079 Uiso 1 1 d R U . . .
F1 F 0.0421(3) 0.7387(3) 0.4748(2) 0.1552(15) Uani 1 1 d . . . . .
C15 C 0.0914(3) 0.7404(5) 0.5541(3) 0.1014(15) Uani 1 1 d . . . . .
C17 C 0.1112(4) 0.8451(5) 0.5929(3) 0.1038(15) Uani 1 1 d . . . . .
C11 C 0.1187(4) 0.6374(5) 0.5939(3) 0.1132(18) Uani 1 1 d . . . . .
C13 C 0.18704(19) 0.7486(3) 0.71458(19) 0.0523(6) Uani 1 1 d . . . . .
C12 C 0.5609(3) 0.4591(4) 0.2871(4) 0.1017(13) Uani 1 1 d . . . . .
H12A H 0.5319 0.4450 0.3454 0.122 Uiso 1 1 d R U . . .
H12B H 0.5168 0.4966 0.2474 0.122 Uiso 1 1 d R U . . .
C18 C 0.1668(3) 0.6413(3) 0.6750(3) 0.0885(12) Uani 1 1 d . . . . .
H18A H 0.1850 0.5725 0.7038 0.106 Uiso 1 1 d R U . . .
C19 C 0.1600(3) 0.8509(3) 0.6741(2) 0.0809(11) Uani 1 1 d . . . . .
H19A H 0.1734 0.9233 0.7001 0.097 Uiso 1 1 d R U . . .
O2 O 0.58969(17) 0.3476(3) 0.24831(18) 0.0809(7) Uani 1 1 d . . . . .
C20 C 0.5145(3) 0.2704(4) 0.2359(4) 0.0959(13) Uani 1 1 d . . . . .
H20A H 0.4727 0.3028 0.1915 0.115 Uiso 1 1 d R U . . .
H20B H 0.4823 0.2617 0.2932 0.115 Uiso 1 1 d R U . . .
O1 O 0.59836(18) 0.0988(3) 0.27666(17) 0.0839(7) Uani 1 1 d . . . . .
F2 F 0.0741(4) 0.9352(4) 0.5561(3) 0.152(2) Uani 0.680(6) 1 d . . P . .
C21 C 0.5471(3) 0.1534(4) 0.2041(3) 0.1038(15) Uani 1 1 d . . . . .
H21A H 0.4958 0.1045 0.1872 0.125 Uiso 1 1 d R U . . .
H21B H 0.5858 0.1629 0.1511 0.125 Uiso 1 1 d R U . . .
C22 C 0.6398(3) 0.5368(4) 0.2984(4) 0.1056(15) Uani 1 1 d . . . . .
H22A H 0.6688 0.5510 0.2401 0.127 Uiso 1 1 d R U . . .
H22B H 0.6198 0.6117 0.3227 0.127 Uiso 1 1 d R U . . .
F2' F 0.0619(8) 0.5614(7) 0.5656(7) 0.147(5) Uani 0.320(6) 1 d . . P . .


_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 O10' 1.340(8) . ?
Cl1 O8' 1.353(7) . ?
Cl1 O9 1.362(6) . ?
Cl1 O10 1.380(5) . ?
Cl1 O9' 1.380(10) . ?
Cl1 O7 1.399(3) . ?
Cl1 O8 1.413(6) . ?
C6 O4 1.431(5) . ?
C6 C5 1.466(6) . ?
C4 O5 1.422(5) . ?
C4 C3 1.466(6) . ?
C3 O6 1.410(5) . ?
C1 O1 1.405(5) . ?
C1 C2 1.476(6) . ?
C5 O5 1.404(5) . ?
C2 O6 1.433(5) . ?
O4 C8 1.418(5) . ?
C8 C9 1.471(6) . ?
C9 O3 1.437(5) . ?
O3 C22 1.406(5) . ?
N1 C13 1.457(4) . ?
F1 C15 1.360(5) . ?
C15 C17 1.342(6) . ?
C15 C11 1.359(7) . ?
C17 F2 1.270(5) . ?
C17 C19 1.381(5) . ?
C11 F2' 1.260(9) . ?
C11 C18 1.374(6) . ?
C13 C19 1.355(4) . ?
C13 C18 1.374(4) . ?
C12 O2 1.443(5) . ?
C12 C22 1.455(6) . ?
O2 C20 1.410(5) . ?
C20 C21 1.478(6) . ?
O1 C21 1.432(5) . ?

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
O10' Cl1 O8' 109.1(9) . . ?
O9 Cl1 O10 108.8(6) . . ?
O10' Cl1 O9' 106.3(9) . . ?
O8' Cl1 O9' 106.0(8) . . ?
O10' Cl1 O7 109.0(6) . . ?
O8' Cl1 O7 110.7(5) . . ?
O9 Cl1 O7 108.0(4) . . ?
O10 Cl1 O7 110.1(3) . . ?
O9' Cl1 O7 115.6(5) . . ?
O9 Cl1 O8 109.5(6) . . ?
O10 Cl1 O8 106.6(6) . . ?
O7 Cl1 O8 113.8(3) . . ?
O4 C6 C5 110.3(3) . . ?
O5 C4 C3 111.2(4) . . ?
O6 C3 C4 109.0(3) . . ?
O1 C1 C2 108.9(3) . . ?
O5 C5 C6 108.3(3) . . ?
O6 C2 C1 109.2(3) . . ?
C3 O6 C2 112.8(3) . . ?
C5 O5 C4 113.6(3) . . ?
C8 O4 C6 112.9(3) . . ?
O4 C8 C9 109.7(3) . . ?
O3 C9 C8 108.8(3) . . ?
C22 O3 C9 113.5(3) . . ?
C17 C15 C11 120.8(4) . . ?
C17 C15 F1 119.0(5) . . ?
C11 C15 F1 120.3(4) . . ?
F2 C17 C15 115.9(4) . . ?
F2 C17 C19 122.9(5) . . ?
C15 C17 C19 120.8(4) . . ?
F2' C11 C15 104.6(6) . . ?
F2' C11 C18 129.6(7) . . ?
C15 C11 C18 119.2(4) . . ?
C19 C13 C18 120.4(3) . . ?
C19 C13 N1 120.6(3) . . ?
C18 C13 N1 119.0(3) . . ?
O2 C12 C22 110.0(3) . . ?
C13 C18 C11 119.9(4) . . ?
C13 C19 C17 118.8(4) . . ?
C20 O2 C12 111.4(3) . . ?
O2 C20 C21 110.1(4) . . ?
C1 O1 C21 113.3(3) . . ?
O1 C21 C20 108.7(3) . . ?
O3 C22 C12 109.8(4) . . ?

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
N1 H1D O6 0.88 2.02 2.865(3) 160.2 2_665
N1 H1C O5 0.88 2.37 2.916(4) 120.2 2_665
N1 H1C O4 0.88 2.06 2.907(3) 159.5 2_665
N1 H1E O3 0.88 2.38 2.930(3) 120.4 2_665
N1 H1E O2 0.88 1.99 2.838(3) 160.3 2_665
N1 H1D O1 0.88 2.39 2.939(3) 120.8 2_665

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.028


_vrf_PLAT112_1                   
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         C         92 %Fit.  
RESPONSE: The structure had been gleaned from an actual PLATON run. The disordered leaded to misinformation. 
;

