# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_vm600
_database_code_depnum_ccdc_archive 'CCDC 1849099'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Cl F N O6'
_chemical_formula_sum            'C21 H19 Cl F N O6'
_chemical_formula_weight         435.82

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.5372(7)
_cell_length_b                   10.0615(8)
_cell_length_c                   11.5029(9)
_cell_angle_alpha                74.116(2)
_cell_angle_beta                 83.655(2)
_cell_angle_gamma                71.870(2)
_cell_volume                     1008.56(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3087
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12672
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5374
_reflns_number_gt                4315
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0477P)²+0.2906P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
N1 N 0.35223(13) 0.47228(12) 0.74246(11) 0.0179(2) Uani 1 1 d . . . . .
O1 O 0.37717(11) 0.37799(10) 0.85706(9) 0.0195(2) Uani 1 1 d . . . . .
O2 O 0.40947(10) 0.59344(10) 0.74649(9) 0.0187(2) Uani 1 1 d . . . . .
O3 O 0.31577(12) 0.93124(11) 0.52186(9) 0.0229(2) Uani 1 1 d . . . . .
O4 O 0.50719(11) 0.72774(11) 0.53669(9) 0.0200(2) Uani 1 1 d . . . . .
O5 O 0.15982(12) 0.85597(13) 0.82907(10) 0.0275(3) Uani 1 1 d . . . . .
O6 O 0.39504(12) 0.85841(13) 0.78685(10) 0.0270(3) Uani 1 1 d . . . . .
F1 F 0.13180(10) 0.46097(9) 0.69079(8) 0.0239(2) Uani 1 1 d . . . . .
Cl1 Cl 0.12702(5) 0.73674(4) 0.12495(3) 0.02726(10) Uani 1 1 d . . . . .
C1 C 0.27291(16) 0.44417(15) 0.94477(12) 0.0180(3) Uani 1 1 d . . . . .
H1A H 0.3139 0.5098 0.9730 0.022 Uiso 1 1 calc R U . . .
C2 C 0.13503(16) 0.53276(16) 0.87042(13) 0.0206(3) Uani 1 1 d . . . . .
H2A H 0.0574 0.4831 0.8902 0.025 Uiso 1 1 calc R U . . .
H2B H 0.0948 0.6299 0.8859 0.025 Uiso 1 1 calc R U . . .
C3 C 0.18952(15) 0.54379(15) 0.73900(12) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.17098(15) 0.69472(14) 0.65438(12) 0.0152(3) Uani 1 1 d . . . . .
H4A H 0.0804 0.7639 0.6800 0.018 Uiso 1 1 calc R U . . .
C5 C 0.30998(15) 0.72768(14) 0.68490(12) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.25294(15) 0.32365(14) 1.04971(12) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.15990(15) 0.70064(14) 0.52245(12) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.27019(15) 0.61220(15) 0.46293(13) 0.0182(3) Uani 1 1 d . . . . .
H8A H 0.3527 0.5444 0.5066 0.022 Uiso 1 1 calc R U . . .
C9 C 0.26092(16) 0.62199(16) 0.34114(13) 0.0192(3) Uani 1 1 d . . . . .
H9A H 0.3370 0.5628 0.3009 0.023 Uiso 1 1 calc R U . . .
C10 C 0.13820(17) 0.72004(16) 0.27918(13) 0.0193(3) Uani 1 1 d . . . . .
C11 C 0.02634(17) 0.80667(16) 0.33617(13) 0.0215(3) Uani 1 1 d . . . . .
H11A H -0.0574 0.8722 0.2927 0.026 Uiso 1 1 calc R U . . .
C12 C 0.03769(16) 0.79691(15) 0.45814(13) 0.0190(3) Uani 1 1 d . . . . .
H12A H -0.0387 0.8565 0.4978 0.023 Uiso 1 1 calc R U . . .
C13 C 0.37879(15) 0.80745(15) 0.57110(12) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.5711(2) 0.79708(18) 0.42396(14) 0.0289(4) Uani 1 1 d . . . . .
H14A H 0.6708 0.7359 0.4110 0.043 Uiso 1 1 calc R U . . .
H14B H 0.5758 0.8913 0.4288 0.043 Uiso 1 1 calc R U . . .
H14C H 0.5095 0.8105 0.3565 0.043 Uiso 1 1 calc R U . . .
C15 C 0.27493(16) 0.82305(15) 0.77524(12) 0.0178(3) Uani 1 1 d . . . . .
C16 C 0.3847(2) 0.9393(2) 0.87602(17) 0.0346(4) Uani 1 1 d . . . . .
H16A H 0.4790 0.9581 0.8783 0.052 Uiso 1 1 calc R U . . .
H16B H 0.3615 0.8830 0.9558 0.052 Uiso 1 1 calc R U . . .
H16C H 0.3065 1.0313 0.8542 0.052 Uiso 1 1 calc R U . . .
C17 C 0.20559(16) 0.21356(15) 1.02971(13) 0.0188(3) Uani 1 1 d . . . . .
H17A H 0.1875 0.2150 0.9497 0.023 Uiso 1 1 calc R U . . .
C18 C 0.18492(16) 0.10263(16) 1.12551(14) 0.0218(3) Uani 1 1 d . . . . .
H18A H 0.1530 0.0282 1.1111 0.026 Uiso 1 1 calc R U . . .
C19 C 0.21076(17) 0.09989(17) 1.24287(14) 0.0243(3) Uani 1 1 d . . . . .
H19A H 0.1973 0.0233 1.3086 0.029 Uiso 1 1 calc R U . . .
C20 C 0.25615(17) 0.20928(18) 1.26358(13) 0.0244(3) Uani 1 1 d . . . . .
H20A H 0.2725 0.2083 1.3438 0.029 Uiso 1 1 calc R U . . .
C21 C 0.27789(16) 0.32080(16) 1.16731(13) 0.0206(3) Uani 1 1 d . . . . .
H21A H 0.3098 0.3951 1.1821 0.025 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
N1 O1 1.3924(14) . ?
N1 C3 1.4935(18) . ?
N1 O2 1.4956(15) . ?
O1 C1 1.4778(16) . ?
O2 C5 1.4331(16) . ?
O3 C13 1.2069(17) . ?
O4 C13 1.3247(17) . ?
O4 C14 1.4608(17) . ?
O5 C15 1.1975(17) . ?
O6 C15 1.3305(18) . ?
O6 C16 1.4518(19) . ?
F1 C3 1.3823(16) . ?
Cl1 C10 1.7478(14) . ?
C1 C6 1.5018(19) . ?
C1 C2 1.535(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.5291(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5319(19) . ?
C4 C7 1.5165(18) . ?
C4 C5 1.5591(19) . ?
C4 H4A 1.0000 . ?
C5 C13 1.5333(19) . ?
C5 C15 1.5433(19) . ?
C6 C21 1.390(2) . ?
C6 C17 1.3992(19) . ?
C7 C12 1.3928(19) . ?
C7 C8 1.3996(19) . ?
C8 C9 1.3880(19) . ?
C8 H8A 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.381(2) . ?
C11 C12 1.393(2) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.384(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.390(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?

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 N1 C3 105.34(10) . . ?
O1 N1 O2 104.68(10) . . ?
C3 N1 O2 101.70(9) . . ?
N1 O1 C1 108.84(9) . . ?
C5 O2 N1 109.02(9) . . ?
C13 O4 C14 115.09(12) . . ?
C15 O6 C16 116.12(12) . . ?
O1 C1 C6 107.49(10) . . ?
O1 C1 C2 103.44(11) . . ?
C6 C1 C2 115.66(12) . . ?
O1 C1 H1A 110.0 . . ?
C6 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
C3 C2 C1 104.38(11) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
F1 C3 N1 105.55(11) . . ?
F1 C3 C2 109.17(11) . . ?
N1 C3 C2 106.42(11) . . ?
F1 C3 C4 111.65(11) . . ?
N1 C3 C4 105.00(11) . . ?
C2 C3 C4 118.10(12) . . ?
C7 C4 C3 113.53(11) . . ?
C7 C4 C5 114.97(11) . . ?
C3 C4 C5 100.71(10) . . ?
C7 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
O2 C5 C13 113.44(11) . . ?
O2 C5 C15 104.89(10) . . ?
C13 C5 C15 106.92(11) . . ?
O2 C5 C4 107.57(10) . . ?
C13 C5 C4 111.27(11) . . ?
C15 C5 C4 112.66(11) . . ?
C21 C6 C17 119.12(13) . . ?
C21 C6 C1 121.12(12) . . ?
C17 C6 C1 119.74(12) . . ?
C12 C7 C8 118.86(13) . . ?
C12 C7 C4 119.50(12) . . ?
C8 C7 C4 121.65(12) . . ?
C9 C8 C7 121.05(13) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 118.71(13) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C11 C10 C9 121.49(13) . . ?
C11 C10 Cl1 119.24(11) . . ?
C9 C10 Cl1 119.25(11) . . ?
C10 C11 C12 119.25(13) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C7 C12 C11 120.63(13) . . ?
C7 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
O3 C13 O4 126.32(13) . . ?
O3 C13 C5 120.03(13) . . ?
O4 C13 C5 113.65(11) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O6 125.53(13) . . ?
O5 C15 C5 125.53(13) . . ?
O6 C15 C5 108.90(12) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C6 120.51(13) . . ?
C18 C17 H17A 119.7 . . ?
C6 C17 H17A 119.7 . . ?
C17 C18 C19 120.14(14) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C20 C19 C18 119.72(13) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C19 C20 C21 120.35(14) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C6 C21 C20 120.17(14) . . ?
C6 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?

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
C3 N1 O1 C1 -35.06(13) . . . . ?
O2 N1 O1 C1 71.76(12) . . . . ?
O1 N1 O2 C5 -139.22(10) . . . . ?
C3 N1 O2 C5 -29.74(12) . . . . ?
N1 O1 C1 C6 155.16(11) . . . . ?
N1 O1 C1 C2 32.33(14) . . . . ?
O1 C1 C2 C3 -16.04(14) . . . . ?
C6 C1 C2 C3 -133.27(12) . . . . ?
O1 N1 C3 F1 -92.74(12) . . . . ?
O2 N1 C3 F1 158.28(9) . . . . ?
O1 N1 C3 C2 23.20(14) . . . . ?
O2 N1 C3 C2 -85.78(11) . . . . ?
O1 N1 C3 C4 149.16(10) . . . . ?
O2 N1 C3 C4 40.18(12) . . . . ?
C1 C2 C3 F1 109.97(12) . . . . ?
C1 C2 C3 N1 -3.51(14) . . . . ?
C1 C2 C3 C4 -121.11(13) . . . . ?
F1 C3 C4 C7 -25.54(16) . . . . ?
N1 C3 C4 C7 88.35(13) . . . . ?
C2 C3 C4 C7 -153.30(12) . . . . ?
F1 C3 C4 C5 -148.97(11) . . . . ?
N1 C3 C4 C5 -35.08(13) . . . . ?
C2 C3 C4 C5 83.27(14) . . . . ?
N1 O2 C5 C13 -115.67(11) . . . . ?
N1 O2 C5 C15 127.99(11) . . . . ?
N1 O2 C5 C4 7.84(13) . . . . ?
C7 C4 C5 O2 -105.82(12) . . . . ?
C3 C4 C5 O2 16.61(13) . . . . ?
C7 C4 C5 C13 19.01(15) . . . . ?
C3 C4 C5 C13 141.43(11) . . . . ?
C7 C4 C5 C15 139.08(12) . . . . ?
C3 C4 C5 C15 -98.50(12) . . . . ?
O1 C1 C6 C21 125.10(14) . . . . ?
C2 C1 C6 C21 -119.95(15) . . . . ?
O1 C1 C6 C17 -56.19(16) . . . . ?
C2 C1 C6 C17 58.75(17) . . . . ?
C3 C4 C7 C12 123.83(14) . . . . ?
C5 C4 C7 C12 -120.93(14) . . . . ?
C3 C4 C7 C8 -56.60(17) . . . . ?
C5 C4 C7 C8 58.63(17) . . . . ?
C12 C7 C8 C9 1.7(2) . . . . ?
C4 C7 C8 C9 -177.91(13) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C8 C9 C10 Cl1 178.48(11) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
Cl1 C10 C11 C12 -177.80(11) . . . . ?
C8 C7 C12 C11 -1.0(2) . . . . ?
C4 C7 C12 C11 178.62(13) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C14 O4 C13 O3 -3.9(2) . . . . ?
C14 O4 C13 C5 176.03(12) . . . . ?
O2 C5 C13 O3 -168.19(12) . . . . ?
C15 C5 C13 O3 -53.06(16) . . . . ?
C4 C5 C13 O3 70.35(16) . . . . ?
O2 C5 C13 O4 11.91(16) . . . . ?
C15 C5 C13 O4 127.04(12) . . . . ?
C4 C5 C13 O4 -109.56(13) . . . . ?
C16 O6 C15 O5 2.4(2) . . . . ?
C16 O6 C15 C5 -175.43(13) . . . . ?
O2 C5 C15 O5 -108.15(15) . . . . ?
C13 C5 C15 O5 131.11(15) . . . . ?
C4 C5 C15 O5 8.57(19) . . . . ?
O2 C5 C15 O6 69.64(13) . . . . ?
C13 C5 C15 O6 -51.11(14) . . . . ?
C4 C5 C15 O6 -173.65(11) . . . . ?
C21 C6 C17 C18 -0.5(2) . . . . ?
C1 C6 C17 C18 -179.23(13) . . . . ?
C6 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C18 C19 C20 C21 -0.9(2) . . . . ?
C17 C6 C21 C20 0.1(2) . . . . ?
C1 C6 C21 C20 178.86(13) . . . . ?
C19 C20 C21 C6 0.5(2) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_vm591
_database_code_depnum_ccdc_archive 'CCDC 1849100'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl F N2 O6'
_chemical_formula_sum            'C16 H14 Cl F N2 O6'
_chemical_formula_weight         384.74

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      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                   16.4649(14)
_cell_length_b                   6.9417(6)
_cell_length_c                   15.0372(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.483(2)
_cell_angle_gamma                90
_cell_volume                     1715.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3854
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20566
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.479
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4568
_reflns_number_gt                3368
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0654P)²+0.0212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4568
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
N1 N 0.18431(8) 0.16839(19) 0.59933(9) 0.0166(3) Uani 1 1 d . . . . .
N2 N 0.11847(9) -0.1887(2) 0.42875(10) 0.0240(3) Uani 1 1 d . . . . .
O1 O 0.09466(7) 0.16824(16) 0.57882(7) 0.0188(2) Uani 1 1 d . . . . .
O2 O 0.19418(7) 0.25419(15) 0.68332(7) 0.0174(2) Uani 1 1 d . . . . .
O3 O 0.26127(7) 0.47029(17) 0.81522(7) 0.0225(3) Uani 1 1 d . . . . .
O4 O 0.22332(7) 0.74642(16) 0.74371(8) 0.0205(3) Uani 1 1 d . . . . .
O5 O 0.06046(7) 0.60668(17) 0.60800(7) 0.0214(3) Uani 1 1 d . . . . .
O6 O 0.06030(6) 0.45018(15) 0.73909(7) 0.0159(2) Uani 1 1 d . . . . .
F1 F 0.28572(6) 0.23874(14) 0.50707(7) 0.0253(2) Uani 1 1 d . . . . .
Cl1 Cl 0.57272(3) 0.78631(10) 0.62785(4) 0.05059(19) Uani 1 1 d . . . . .
C1 C 0.08802(10) 0.1627(2) 0.48396(11) 0.0186(3) Uani 1 1 d . . . . .
H1A H 0.0319 0.2017 0.4618 0.022 Uiso 1 1 calc R U . . .
C2 C 0.14949(11) 0.3107(2) 0.45531(11) 0.0202(3) Uani 1 1 d . . . . .
H2A H 0.1240 0.4391 0.4467 0.024 Uiso 1 1 calc R U . . .
H2B H 0.1736 0.2712 0.3994 0.024 Uiso 1 1 calc R U . . .
C3 C 0.21338(10) 0.3122(2) 0.53316(10) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.22612(9) 0.5055(2) 0.58396(10) 0.0150(3) Uani 1 1 d . . . . .
H4A H 0.1938 0.6077 0.5510 0.018 Uiso 1 1 calc R U . . .
C5 C 0.18525(9) 0.4612(2) 0.67181(10) 0.0148(3) Uani 1 1 d . . . . .
C6 C 0.10577(9) -0.0354(2) 0.45259(10) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.31368(9) 0.5710(2) 0.59544(10) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.33473(11) 0.7495(3) 0.56149(12) 0.0245(4) Uani 1 1 d . . . . .
H8A H 0.2941 0.8265 0.5314 0.029 Uiso 1 1 calc R U . . .
C9 C 0.41425(12) 0.8166(3) 0.57096(13) 0.0321(4) Uani 1 1 d . . . . .
H9A H 0.4282 0.9382 0.5472 0.038 Uiso 1 1 calc R U . . .
C10 C 0.47254(11) 0.7041(3) 0.61542(13) 0.0332(5) Uani 1 1 d . . . . .
C11 C 0.45351(11) 0.5269(3) 0.65033(13) 0.0348(5) Uani 1 1 d . . . . .
H11A H 0.4944 0.4514 0.6809 0.042 Uiso 1 1 calc R U . . .
C12 C 0.37382(10) 0.4601(3) 0.64034(12) 0.0281(4) Uani 1 1 d . . . . .
H12A H 0.3603 0.3383 0.6642 0.034 Uiso 1 1 calc R U . . .
C13 C 0.22823(9) 0.5560(2) 0.75382(10) 0.0168(3) Uani 1 1 d . . . . .
C14 C 0.27271(11) 0.8603(3) 0.80791(12) 0.0279(4) Uani 1 1 d . . . . .
H14A H 0.2670 0.9972 0.7931 0.042 Uiso 1 1 calc R U . . .
H14B H 0.3299 0.8224 0.8060 0.042 Uiso 1 1 calc R U . . .
H14C H 0.2545 0.8377 0.8679 0.042 Uiso 1 1 calc R U . . .
C15 C 0.09446(9) 0.5155(2) 0.66715(10) 0.0148(3) Uani 1 1 d . . . . .
C16 C -0.02770(9) 0.4744(2) 0.73993(11) 0.0191(3) Uani 1 1 d . . . . .
H16A H -0.0459 0.4354 0.7981 0.029 Uiso 1 1 calc R U . . .
H16B H -0.0545 0.3940 0.6933 0.029 Uiso 1 1 calc R U . . .
H16C H -0.0418 0.6098 0.7289 0.029 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
N1 O2 1.3970(17) . ?
N1 O1 1.4894(17) . ?
N1 C3 1.508(2) . ?
N2 C6 1.146(2) . ?
O1 C1 1.4245(19) . ?
O2 C5 1.4536(18) . ?
O3 C13 1.2005(19) . ?
O4 C13 1.3325(19) . ?
O4 C14 1.457(2) . ?
O5 C15 1.2019(18) . ?
O6 C15 1.3291(18) . ?
O6 C16 1.4594(18) . ?
F1 C3 1.3746(18) . ?
Cl1 C10 1.7448(19) . ?
C1 C6 1.489(2) . ?
C1 C2 1.523(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.526(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.552(2) . ?
C4 C7 1.512(2) . ?
C4 C5 1.549(2) . ?
C4 H4A 1.0000 . ?
C5 C13 1.533(2) . ?
C5 C15 1.539(2) . ?
C7 C8 1.392(2) . ?
C7 C12 1.396(2) . ?
C8 C9 1.389(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.381(3) . ?
C11 C12 1.391(2) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
O2 N1 O1 104.29(10) . . ?
O2 N1 C3 106.86(11) . . ?
O1 N1 C3 102.37(11) . . ?
C1 O1 N1 102.83(10) . . ?
N1 O2 C5 107.96(11) . . ?
C13 O4 C14 115.78(13) . . ?
C15 O6 C16 115.93(12) . . ?
O1 C1 C6 109.73(13) . . ?
O1 C1 C2 104.67(13) . . ?
C6 C1 C2 112.77(14) . . ?
O1 C1 H1A 109.8 . . ?
C6 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
C1 C2 C3 103.11(13) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
F1 C3 N1 104.94(12) . . ?
F1 C3 C2 110.33(13) . . ?
N1 C3 C2 105.66(12) . . ?
F1 C3 C4 111.58(13) . . ?
N1 C3 C4 106.65(12) . . ?
C2 C3 C4 116.75(13) . . ?
C7 C4 C5 115.03(12) . . ?
C7 C4 C3 114.57(13) . . ?
C5 C4 C3 101.27(12) . . ?
C7 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4A 108.5 . . ?
O2 C5 C13 106.87(12) . . ?
O2 C5 C15 109.80(12) . . ?
C13 C5 C15 109.33(12) . . ?
O2 C5 C4 104.58(12) . . ?
C13 C5 C4 113.42(13) . . ?
C15 C5 C4 112.55(12) . . ?
N2 C6 C1 179.12(18) . . ?
C8 C7 C12 118.91(16) . . ?
C8 C7 C4 118.88(14) . . ?
C12 C7 C4 122.20(15) . . ?
C9 C8 C7 121.02(17) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C10 C9 C8 118.91(18) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 121.46(17) . . ?
C9 C10 Cl1 119.49(16) . . ?
C11 C10 Cl1 119.05(16) . . ?
C10 C11 C12 119.37(18) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C7 120.32(18) . . ?
C11 C12 H12A 119.8 . . ?
C7 C12 H12A 119.8 . . ?
O3 C13 O4 126.94(15) . . ?
O3 C13 C5 124.85(15) . . ?
O4 C13 C5 108.20(13) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O6 125.51(14) . . ?
O5 C15 C5 124.77(14) . . ?
O6 C15 C5 109.71(12) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O2 N1 O1 C1 155.48(11) . . . . ?
C3 N1 O1 C1 44.24(13) . . . . ?
O1 N1 O2 C5 -77.98(12) . . . . ?
C3 N1 O2 C5 29.97(14) . . . . ?
N1 O1 C1 C6 76.14(14) . . . . ?
N1 O1 C1 C2 -45.12(14) . . . . ?
O1 C1 C2 C3 27.80(16) . . . . ?
C6 C1 C2 C3 -91.43(15) . . . . ?
O2 N1 C3 F1 108.04(13) . . . . ?
O1 N1 C3 F1 -142.66(11) . . . . ?
O2 N1 C3 C2 -135.33(12) . . . . ?
O1 N1 C3 C2 -26.03(14) . . . . ?
O2 N1 C3 C4 -10.46(15) . . . . ?
O1 N1 C3 C4 98.84(12) . . . . ?
C1 C2 C3 F1 112.80(14) . . . . ?
C1 C2 C3 N1 -0.11(16) . . . . ?
C1 C2 C3 C4 -118.44(14) . . . . ?
F1 C3 C4 C7 -0.83(18) . . . . ?
N1 C3 C4 C7 113.22(14) . . . . ?
C2 C3 C4 C7 -128.99(15) . . . . ?
F1 C3 C4 C5 -125.27(13) . . . . ?
N1 C3 C4 C5 -11.21(15) . . . . ?
C2 C3 C4 C5 106.57(14) . . . . ?
N1 O2 C5 C13 -157.96(11) . . . . ?
N1 O2 C5 C15 83.56(14) . . . . ?
N1 O2 C5 C4 -37.43(14) . . . . ?
C7 C4 C5 O2 -95.79(15) . . . . ?
C3 C4 C5 O2 28.34(14) . . . . ?
C7 C4 C5 C13 20.28(18) . . . . ?
C3 C4 C5 C13 144.41(13) . . . . ?
C7 C4 C5 C15 145.06(14) . . . . ?
C3 C4 C5 C15 -90.81(14) . . . . ?
C5 C4 C7 C8 -121.62(16) . . . . ?
C3 C4 C7 C8 121.60(16) . . . . ?
C5 C4 C7 C12 57.2(2) . . . . ?
C3 C4 C7 C12 -59.6(2) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C4 C7 C8 C9 179.51(16) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 Cl1 179.98(15) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
Cl1 C10 C11 C12 -179.74(15) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C4 C7 C12 C11 -179.22(16) . . . . ?
C14 O4 C13 O3 9.1(2) . . . . ?
C14 O4 C13 C5 -169.92(13) . . . . ?
O2 C5 C13 O3 -1.0(2) . . . . ?
C15 C5 C13 O3 117.77(16) . . . . ?
C4 C5 C13 O3 -115.73(17) . . . . ?
O2 C5 C13 O4 177.99(11) . . . . ?
C15 C5 C13 O4 -63.22(15) . . . . ?
C4 C5 C13 O4 63.28(16) . . . . ?
C16 O6 C15 O5 7.2(2) . . . . ?
C16 O6 C15 C5 -174.19(12) . . . . ?
O2 C5 C15 O5 -126.02(16) . . . . ?
C13 C5 C15 O5 117.03(17) . . . . ?
C4 C5 C15 O5 -10.0(2) . . . . ?
O2 C5 C15 O6 55.34(16) . . . . ?
C13 C5 C15 O6 -61.62(16) . . . . ?
C4 C5 C15 O6 171.39(12) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055

_shelxl_version_number           2014/6



