# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_jakir11
_database_code_depnum_ccdc_archive 'CCDC 1564320'
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 F17 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         586.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   34.79(7)
_cell_length_b                   5.967(12)
_cell_length_c                   23.94(5)
_cell_angle_alpha                90
_cell_angle_beta                 126.10(5)
_cell_angle_gamma                90
_cell_volume                     4016.(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    704
_cell_measurement_theta_min      2.3667
_cell_measurement_theta_max      20.4326
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320

_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine focus sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9482
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             3688
_reflns_number_gt                2002
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1664
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_number_reflns         3688
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+9.7390P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.438
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 '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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.56463(19) 0.5410(10) 0.6461(3) 0.0206(13) Uani d . . . 1 . .
C C2 0.52819(18) 0.4176(9) 0.5936(3) 0.0162(12) Uani d . . . 1 . .
H H2 0.5342 0.2962 0.574 0.019 Uiso calc U . R 1 . .
C C3 0.48205(18) 0.4732(9) 0.5692(3) 0.0166(12) Uani d . . . 1 . .
C C4 0.47239(18) 0.6552(9) 0.5960(3) 0.0156(12) Uani d . . . 1 . .
C C5 0.5115(2) 0.7766(9) 0.6503(3) 0.0176(13) Uani d . . . 1 . .
C C6 0.5575(2) 0.7215(9) 0.6749(3) 0.0180(13) Uani d . . . 1 . .
H H6 0.5837 0.8061 0.711 0.022 Uiso calc U . R 1 . .
C C7 0.6220(2) 0.3140(10) 0.6483(3) 0.0265(14) Uani d . . . 1 . .
H H7A 0.6084 0.1776 0.6529 0.04 Uiso calc U . R 1 . .
H H7B 0.6566 0.2971 0.6746 0.04 Uiso calc U . R 1 . .
H H7C 0.6083 0.3389 0.5994 0.04 Uiso calc U . R 1 . .
C C8 0.4518(2) 0.1557(9) 0.4932(3) 0.0204(13) Uani d . . . 1 . .
H H8A 0.4676 0.1926 0.4714 0.031 Uiso calc U . R 1 . .
H H8B 0.4214 0.082 0.4594 0.031 Uiso calc U . R 1 . .
H H8C 0.4721 0.0547 0.5323 0.031 Uiso calc U . R 1 . .
C C9 0.5399(2) 1.0918(10) 0.7274(3) 0.0271(14) Uani d . . . 1 . .
H H9A 0.5577 1.014 0.772 0.041 Uiso calc U . R 1 . .
H H9B 0.5272 1.2327 0.7312 0.041 Uiso calc U . R 1 . .
H H9C 0.5612 1.1238 0.7141 0.041 Uiso calc U . R 1 . .
C C10 0.4223(2) 0.7057(9) 0.5711(3) 0.0190(13) Uani d . . . 1 . .
C C11 0.40737(19) 0.5767(8) 0.6119(3) 0.0170(12) Uani d . . . 1 . .
C C12 0.35811(19) 0.6343(9) 0.5946(3) 0.0173(13) Uani d . . . 1 . .
C C13 0.33940(19) 0.4633(9) 0.6207(3) 0.0181(13) Uani d . . . 1 . .
C C14 0.29811(18) 0.5487(9) 0.6225(3) 0.0184(13) Uani d . . . 1 . .
C C15 0.26874(19) 0.3638(9) 0.6253(3) 0.0201(13) Uani d . . . 1 . .
C C16 0.2366(2) 0.4446(10) 0.6450(3) 0.0229(14) Uani d . . . 1 . .
C C17 0.1956(2) 0.2861(11) 0.6251(4) 0.0356(17) Uani d . . . 1 . .
F F1 0.39026(10) 0.6604(5) 0.50320(15) 0.0218(7) Uani d . . . 1 . .
F F2 0.41570(11) 0.9276(5) 0.57787(17) 0.0241(8) Uani d . . . 1 . .
F F3 0.40749(11) 0.3562(5) 0.59948(16) 0.0223(8) Uani d . . . 1 . .
F F4 0.44086(10) 0.6108(5) 0.67992(15) 0.0209(7) Uani d . . . 1 . .
F F5 0.32662(11) 0.6576(6) 0.52652(16) 0.0294(8) Uani d . . . 1 . .
F F6 0.36238(11) 0.8326(5) 0.62498(18) 0.0269(8) Uani d . . . 1 . .
F F7 0.32393(11) 0.2821(5) 0.57930(17) 0.0268(8) Uani d . . . 1 . .
F F8 0.37493(11) 0.3972(5) 0.68494(16) 0.0238(8) Uani d . . . 1 . .
F F9 0.26914(11) 0.6724(6) 0.56560(17) 0.0318(9) Uani d . . . 1 . .
F F10 0.31621(11) 0.6819(5) 0.67770(17) 0.0265(8) Uani d . . . 1 . .
F F11 0.24159(12) 0.2642(6) 0.56341(18) 0.0375(10) Uani d . . . 1 . .
F F12 0.29883(12) 0.2102(5) 0.67200(19) 0.0331(9) Uani d . . . 1 . .
F F13 0.21681(12) 0.6421(6) 0.6141(2) 0.0366(9) Uani d . . . 1 . .
F F14 0.26254(12) 0.4760(6) 0.71333(18) 0.0388(10) Uani d . . . 1 . .
F F15 0.16305(13) 0.2838(7) 0.5578(2) 0.0508(11) Uani d . . . 1 . .
F F16 0.17552(13) 0.3544(6) 0.6551(2) 0.0454(11) Uani d . . . 1 . .
F F17 0.21230(14) 0.0812(6) 0.6469(2) 0.0532(12) Uani d . . . 1 . .
O O1 0.61149(13) 0.5000(7) 0.67420(19) 0.0242(10) Uani d . . . 1 . .
O O2 0.44365(12) 0.3565(6) 0.51719(19) 0.0204(9) Uani d . . . 1 . .
O O3 0.50147(13) 0.9527(6) 0.6758(2) 0.0249(10) Uani d . . . 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
C1 C2 . 1.361(8) ?
C1 O1 . 1.370(7) ?
C1 C6 . 1.378(8) ?
C2 C3 . 1.387(8) ?
C2 H2 . 0.95 ?
C3 O2 . 1.364(6) ?
C3 C4 . 1.399(7) ?
C4 C5 . 1.406(8) ?
C4 C10 . 1.503(8) ?
C5 O3 . 1.359(6) ?
C5 C6 . 1.382(8) ?
C6 H6 . 0.95 ?
C7 O1 . 1.421(7) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 O2 . 1.429(6) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 O3 . 1.435(7) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 F1 . 1.350(7) ?
C10 F2 . 1.369(6) ?
C10 C11 . 1.552(8) ?
C11 F4 . 1.348(7) ?
C11 F3 . 1.350(6) ?
C11 C12 . 1.546(8) ?
C12 F5 . 1.331(7) ?
C12 F6 . 1.350(6) ?
C12 C13 . 1.528(8) ?
C13 F8 . 1.345(6) ?
C13 F7 . 1.346(6) ?
C13 C14 . 1.549(8) ?
C14 F10 . 1.340(6) ?
C14 F9 . 1.341(6) ?
C14 C15 . 1.532(8) ?
C15 F11 . 1.338(7) ?
C15 F12 . 1.344(6) ?
C15 C16 . 1.526(8) ?
C16 F14 . 1.337(7) ?
C16 F13 . 1.345(7) ?
C16 C17 . 1.535(9) ?
C17 F15 . 1.315(8) ?
C17 F17 . 1.323(7) ?
C17 F16 . 1.325(7) ?

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
C2 C1 O1 . . 123.3(5) ?
C2 C1 C6 . . 122.7(5) ?
O1 C1 C6 . . 114.0(5) ?
C1 C2 C3 . . 118.5(5) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
O2 C3 C2 . . 122.0(5) ?
O2 C3 C4 . . 116.4(5) ?
C2 C3 C4 . . 121.6(5) ?
C3 C4 C5 . . 117.4(5) ?
C3 C4 C10 . . 120.6(5) ?
C5 C4 C10 . . 121.8(5) ?
O3 C5 C6 . . 122.1(5) ?
O3 C5 C4 . . 116.7(5) ?
C6 C5 C4 . . 121.2(5) ?
C1 C6 C5 . . 118.5(5) ?
C1 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
F1 C10 F2 . . 105.0(4) ?
F1 C10 C4 . . 112.3(4) ?
F2 C10 C4 . . 112.5(5) ?
F1 C10 C11 . . 108.3(5) ?
F2 C10 C11 . . 105.3(4) ?
C4 C10 C11 . . 113.0(5) ?
F4 C11 F3 . . 107.5(4) ?
F4 C11 C12 . . 108.8(4) ?
F3 C11 C12 . . 107.7(4) ?
F4 C11 C10 . . 108.3(5) ?
F3 C11 C10 . . 107.4(4) ?
C12 C11 C10 . . 116.7(5) ?
F5 C12 F6 . . 108.5(4) ?
F5 C12 C13 . . 109.2(4) ?
F6 C12 C13 . . 107.7(4) ?
F5 C12 C11 . . 109.5(4) ?
F6 C12 C11 . . 107.3(4) ?
C13 C12 C11 . . 114.5(5) ?
F8 C13 F7 . . 107.8(4) ?
F8 C13 C12 . . 109.7(5) ?
F7 C13 C12 . . 108.5(4) ?
F8 C13 C14 . . 107.9(4) ?
F7 C13 C14 . . 108.0(4) ?
C12 C13 C14 . . 114.7(5) ?
F10 C14 F9 . . 108.1(5) ?
F10 C14 C15 . . 108.8(4) ?
F9 C14 C15 . . 108.6(4) ?
F10 C14 C13 . . 108.6(4) ?
F9 C14 C13 . . 107.9(4) ?
C15 C14 C13 . . 114.7(5) ?
F11 C15 F12 . . 108.3(5) ?
F11 C15 C16 . . 108.3(5) ?
F12 C15 C16 . . 108.2(5) ?
F11 C15 C14 . . 109.0(5) ?
F12 C15 C14 . . 108.3(4) ?
C16 C15 C14 . . 114.6(5) ?
F14 C16 F13 . . 107.9(5) ?
F14 C16 C15 . . 109.4(5) ?
F13 C16 C15 . . 109.7(5) ?
F14 C16 C17 . . 107.5(5) ?
F13 C16 C17 . . 106.8(5) ?
C15 C16 C17 . . 115.3(5) ?
F15 C17 F17 . . 109.5(6) ?
F15 C17 F16 . . 108.7(5) ?
F17 C17 F16 . . 108.7(5) ?
F15 C17 C16 . . 110.9(5) ?
F17 C17 C16 . . 109.5(5) ?
F16 C17 C16 . . 109.4(5) ?
C1 O1 C7 . . 117.5(5) ?
C3 O2 C8 . . 118.4(4) ?
C5 O3 C9 . . 118.5(5) ?

####################################################################### 
# 
# 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_jakir13
_database_code_depnum_ccdc_archive 'CCDC 1564319'
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 F9 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         386.22
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.7087(17)
_cell_length_b                   26.381(6)
_cell_length_c                   7.3447(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1493.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2319
_cell_measurement_theta_min      2.7528
_cell_measurement_theta_max      28.9363
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776

_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine focus sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9739
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             3327
_reflns_number_gt                2724
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1090
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_number_reflns         3327
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)

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'
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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
F F1 0.1961(3) 0.37010(7) 0.8046(3) 0.0215(5) Uani d . . . 1 . .
F F2 0.1154(2) 0.43288(7) 0.6366(3) 0.0210(5) Uani d . . . 1 . .
F F3 0.4899(2) 0.35878(7) 0.5974(3) 0.0215(5) Uani d . . . 1 . .
F F4 0.4063(3) 0.42035(8) 0.4210(3) 0.0222(5) Uani d . . . 1 . .
F F8 0.7438(3) 0.48176(9) 0.7996(4) 0.0372(6) Uani d . . . 1 . .
O O1 0.2326(3) 0.28286(9) 0.6751(3) 0.0203(6) Uani d . . . 1 . .
F F6 0.4202(3) 0.48723(8) 0.6847(4) 0.0368(6) Uani d . . . 1 . .
O O2 -0.0580(3) 0.25102(9) 0.1062(4) 0.0217(6) Uani d . . . 1 . .
F F5 0.4528(3) 0.42930(10) 0.8934(3) 0.0395(7) Uani d . . . 1 . .
O O3 0.0440(3) 0.41842(8) 0.3062(4) 0.0212(6) Uani d . . . 1 . .
F F7 0.7584(3) 0.40201(9) 0.7572(4) 0.0454(8) Uani d . . . 1 . .
F F9 0.7280(3) 0.45159(12) 0.5279(4) 0.0436(7) Uani d . . . 1 . .
C C1 0.1488(4) 0.29816(12) 0.5228(5) 0.0157(7) Uani d . . . 1 . .
C C2 0.0838(4) 0.26367(13) 0.3970(5) 0.0176(7) Uani d . . . 1 . .
H H2 0.0932 0.229 0.4181 0.021 Uiso calc U . R 1 . .
C C3 0.0051(4) 0.28136(13) 0.2406(5) 0.0173(7) Uani d . . . 1 . .
C C4 -0.0110(5) 0.33309(13) 0.2068(5) 0.0179(7) Uani d . . . 1 . .
H H4 -0.0636 0.3444 0.1003 0.021 Uiso calc U . R 1 . .
C C6 0.1304(4) 0.35093(13) 0.4958(5) 0.0156(7) Uani d . . . 1 . .
C C10 0.2037(4) 0.38820(12) 0.6308(5) 0.0163(7) Uani d . . . 1 . .
C C5 0.0514(5) 0.36738(13) 0.3319(5) 0.0174(7) Uani d . . . 1 . .
C C11 0.3959(4) 0.40191(12) 0.5918(5) 0.0151(7) Uani d . . . 1 . .
C C7 0.2249(5) 0.23017(13) 0.7216(5) 0.0212(8) Uani d . . . 1 . .
H H7A 0.106 0.22 0.7344 0.032 Uiso calc U . R 1 . .
H H7B 0.2849 0.2246 0.8344 0.032 Uiso calc U . R 1 . .
H H7C 0.2788 0.2105 0.6271 0.032 Uiso calc U . R 1 . .
C C12 0.4839(5) 0.44083(13) 0.7194(5) 0.0195(8) Uani d . . . 1 . .
C C13 0.6834(5) 0.44421(15) 0.6983(6) 0.0264(9) Uani d . . . 1 . .
C C8 -0.0391(5) 0.19734(12) 0.1271(5) 0.0222(8) Uani d . . . 1 . .
H H8A 0.0818 0.1889 0.1342 0.033 Uiso calc U . R 1 . .
H H8B -0.0902 0.1804 0.0244 0.033 Uiso calc U . R 1 . .
H H8C -0.0965 0.1867 0.2366 0.033 Uiso calc U . R 1 . .
C C9 -0.0460(5) 0.43671(13) 0.1489(6) 0.0240(8) Uani d . . . 1 . .
H H9A 0.0092 0.424 0.041 0.036 Uiso calc U . R 1 . .
H H9B -0.0434 0.4731 0.1478 0.036 Uiso calc U . R 1 . .
H H9C -0.1643 0.4253 0.1523 0.036 Uiso calc U . R 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
F1 C10 . 1.364(4) ?
F2 C10 . 1.362(4) ?
F3 C11 . 1.349(4) ?
F4 C11 . 1.348(4) ?
F8 C13 . 1.324(4) ?
O1 C1 . 1.353(4) ?
O1 C7 . 1.433(4) ?
F6 C12 . 1.343(4) ?
O2 C3 . 1.361(4) ?
O2 C8 . 1.432(4) ?
F5 C12 . 1.335(4) ?
O3 C5 . 1.361(4) ?
O3 C9 . 1.432(5) ?
F7 C13 . 1.327(5) ?
F9 C13 . 1.313(5) ?
C1 C2 . 1.390(5) ?
C1 C6 . 1.413(5) ?
C2 C3 . 1.381(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.392(5) ?
C4 C5 . 1.376(5) ?
C4 H4 . 0.93 ?
C6 C5 . 1.417(5) ?
C6 C10 . 1.507(5) ?
C10 C11 . 1.552(5) ?
C11 C12 . 1.547(5) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C12 C13 . 1.548(5) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?

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
C1 O1 C7 . . 117.8(3) ?
C3 O2 C8 . . 117.9(3) ?
C5 O3 C9 . . 117.7(3) ?
O1 C1 C2 . . 121.7(3) ?
O1 C1 C6 . . 117.2(3) ?
C2 C1 C6 . . 121.0(3) ?
C3 C2 C1 . . 119.4(3) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
O2 C3 C2 . . 124.2(3) ?
O2 C3 C4 . . 114.5(3) ?
C2 C3 C4 . . 121.2(3) ?
C5 C4 C3 . . 119.6(3) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C1 C6 C5 . . 117.7(3) ?
C1 C6 C10 . . 120.8(3) ?
C5 C6 C10 . . 121.4(3) ?
F2 C10 F1 . . 104.6(3) ?
F2 C10 C6 . . 113.4(3) ?
F1 C10 C6 . . 111.8(3) ?
F2 C10 C11 . . 106.3(2) ?
F1 C10 C11 . . 107.2(3) ?
C6 C10 C11 . . 112.9(3) ?
O3 C5 C4 . . 122.9(3) ?
O3 C5 C6 . . 116.0(3) ?
C4 C5 C6 . . 121.1(3) ?
F4 C11 F3 . . 107.5(3) ?
F4 C11 C12 . . 107.4(3) ?
F3 C11 C12 . . 107.8(3) ?
F4 C11 C10 . . 108.2(3) ?
F3 C11 C10 . . 108.1(3) ?
C12 C11 C10 . . 117.5(3) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
F5 C12 F6 . . 108.9(3) ?
F5 C12 C11 . . 110.5(3) ?
F6 C12 C11 . . 109.3(3) ?
F5 C12 C13 . . 106.7(3) ?
F6 C12 C13 . . 106.9(3) ?
C11 C12 C13 . . 114.4(3) ?
F9 C13 F8 . . 109.5(4) ?
F9 C13 F7 . . 108.7(4) ?
F8 C13 F7 . . 106.9(3) ?
F9 C13 C12 . . 111.4(3) ?
F8 C13 C12 . . 109.7(3) ?
F7 C13 C12 . . 110.6(3) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?

####################################################################### 
# 
# 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_Jakir33
_database_code_depnum_ccdc_archive 'CCDC 1564328'
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 F7 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         336.21

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.585(11)
_cell_length_b                   4.968(4)
_cell_length_c                   17.834(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.188(13)
_cell_angle_gamma                90
_cell_volume                     1319.2(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1040
_cell_measurement_theta_min      3.0861
_cell_measurement_theta_max      27.5073
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680

_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7188
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             2910
_reflns_number_gt                1812
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_gt          0.1895
_refine_ls_wR_factor_ref         0.2324
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_number_reflns         2910
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1062P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.605
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.5979(3) 0.4353(9) 0.3886(3) 0.0139(9) Uani d . . . 1 . .
C C2 0.6420(3) 0.2621(9) 0.4502(2) 0.0113(9) Uani d . . . 1 . .
C C3 0.7349(3) 0.2690(9) 0.4801(2) 0.0133(9) Uani d . . . 1 . .
H H3 0.7647 0.154 0.5223 0.016 Uiso calc U . R 1 . .
C C4 0.7845(3) 0.4448(9) 0.4481(2) 0.0128(9) Uani d . . . 1 . .
C C5 0.7408(3) 0.6115(9) 0.3859(2) 0.0119(9) Uani d . . . 1 . .
C C6 0.6463(3) 0.6042(9) 0.3572(2) 0.0127(9) Uani d . . . 1 . .
H H6 0.6161 0.7195 0.3152 0.015 Uiso calc U . R 1 . .
C C7 0.4592(3) 0.6420(10) 0.3205(3) 0.0199(11) Uani d . . . 1 . .
H H7A 0.4843 0.8101 0.3467 0.03 Uiso calc U . R 1 . .
H H7B 0.3953 0.6314 0.3166 0.03 Uiso calc U . R 1 . .
H H7C 0.4665 0.6376 0.2677 0.03 Uiso calc U . R 1 . .
C C8 0.6312(3) -0.0777(10) 0.5409(3) 0.0174(10) Uani d . . . 1 . .
H H8A 0.6713 -0.2011 0.5244 0.026 Uiso calc U . R 1 . .
H H8B 0.5854 -0.1816 0.5559 0.026 Uiso calc U . R 1 . .
H H8C 0.6661 0.0284 0.5859 0.026 Uiso calc U . R 1 . .
C C9 0.9214(3) 0.2932(11) 0.5407(2) 0.0181(10) Uani d . . . 1 . .
H H9A 0.9011 0.3398 0.586 0.027 Uiso calc U . R 1 . .
H H9B 0.9864 0.3219 0.5537 0.027 Uiso calc U . R 1 . .
H H9C 0.9077 0.1038 0.5269 0.027 Uiso calc U . R 1 . .
C C10 0.7890(3) 0.7860(9) 0.3425(2) 0.0109(9) Uani d . . . 1 . .
C C11 0.8175(3) 0.6311(9) 0.2784(2) 0.0136(9) Uani d . . . 1 . .
C C12 0.8604(3) 0.7934(10) 0.2245(3) 0.0199(10) Uani d . . . 1 . .
F F1 0.73492(17) 0.9906(5) 0.30535(15) 0.0156(6) Uani d . . . 1 . .
F F2 0.86432(17) 0.9029(5) 0.38956(14) 0.0151(6) Uani d . . . 1 . .
F F3 0.74200(19) 0.5176(6) 0.22940(15) 0.0208(6) Uani d . . . 1 . .
F F4 0.87454(19) 0.4346(5) 0.31084(16) 0.0197(6) Uani d . . . 1 . .
F F5 0.8063(2) 0.9828(6) 0.18559(18) 0.0332(8) Uani d . . . 1 . .
F F6 0.9370(2) 0.9041(7) 0.26633(18) 0.0322(8) Uani d . . . 1 . .
F F7 0.8774(2) 0.6264(6) 0.17204(17) 0.0287(8) Uani d . . . 1 . .
O O1 0.5053(2) 0.4193(7) 0.36476(18) 0.0183(8) Uani d . . . 1 . .
O O2 0.5886(2) 0.0991(7) 0.47736(18) 0.0169(7) Uani d . . . 1 . .
O O3 0.8761(2) 0.4610(7) 0.47505(18) 0.0158(7) Uani d . . . 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
C1 C6 . 1.355(6) ?
C1 O1 . 1.382(5) ?
C1 C2 . 1.405(6) ?
C2 O2 . 1.350(5) ?
C2 C3 . 1.387(6) ?
C3 C4 . 1.395(6) ?
C3 H3 . 0.95 ?
C4 O3 . 1.368(5) ?
C4 C5 . 1.390(6) ?
C5 C6 . 1.409(6) ?
C5 C10 . 1.503(6) ?
C6 H6 . 0.95 ?
C7 O1 . 1.423(6) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 O2 . 1.432(5) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 O3 . 1.440(5) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 F2 . 1.355(5) ?
C10 F1 . 1.361(5) ?
C10 C11 . 1.548(6) ?
C11 F4 . 1.331(5) ?
C11 F3 . 1.364(5) ?
C11 C12 . 1.549(6) ?
C12 F5 . 1.316(6) ?
C12 F6 . 1.326(6) ?
C12 F7 . 1.335(5) ?

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
C6 C1 O1 . . 124.6(4) ?
C6 C1 C2 . . 119.9(4) ?
O1 C1 C2 . . 115.5(4) ?
O2 C2 C3 . . 124.2(4) ?
O2 C2 C1 . . 115.9(4) ?
C3 C2 C1 . . 119.9(4) ?
C2 C3 C4 . . 120.0(4) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
O3 C4 C5 . . 117.3(4) ?
O3 C4 C3 . . 122.7(4) ?
C5 C4 C3 . . 120.0(4) ?
C4 C5 C6 . . 119.1(4) ?
C4 C5 C10 . . 123.6(4) ?
C6 C5 C10 . . 117.1(4) ?
C1 C6 C5 . . 121.0(4) ?
C1 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
F2 C10 F1 . . 106.3(3) ?
F2 C10 C5 . . 113.7(3) ?
F1 C10 C5 . . 110.4(3) ?
F2 C10 C11 . . 106.6(3) ?
F1 C10 C11 . . 106.5(3) ?
C5 C10 C11 . . 112.9(4) ?
F4 C11 F3 . . 108.3(4) ?
F4 C11 C10 . . 110.1(3) ?
F3 C11 C10 . . 107.3(3) ?
F4 C11 C12 . . 107.3(4) ?
F3 C11 C12 . . 105.5(3) ?
C10 C11 C12 . . 118.0(4) ?
F5 C12 F6 . . 109.3(4) ?
F5 C12 F7 . . 107.7(4) ?
F6 C12 F7 . . 108.6(4) ?
F5 C12 C11 . . 111.9(4) ?
F6 C12 C11 . . 110.4(4) ?
F7 C12 C11 . . 108.8(4) ?
C1 O1 C7 . . 115.8(3) ?
C2 O2 C8 . . 117.4(3) ?
C4 O3 C9 . . 117.6(3) ?

####################################################################### 
# 
# 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_jakir7
_database_code_depnum_ccdc_archive 'CCDC 1564317'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 F3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         236.19

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.7627(19)
_cell_length_b                   10.491(2)
_cell_length_c                   20.351(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.785(3)
_cell_angle_gamma                90
_cell_volume                     2084.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1844
_cell_measurement_theta_min      2.8502
_cell_measurement_theta_max      30.2996
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine focus sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6150
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             2504
_reflns_number_gt                1800
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1181
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         2504
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.56858(14) 0.55746(14) 0.58923(6) 0.0149(3) Uani d . . . 1 . .
C C2 0.57426(15) 0.42446(14) 0.58900(7) 0.0168(3) Uani d . . . 1 . .
H H2 0.6321 0.3802 0.5596 0.02 Uiso calc U . R 1 . .
C C3 0.49279(16) 0.35871(14) 0.63313(7) 0.0176(3) Uani d . . . 1 . .
C C4 0.40710(15) 0.42139(14) 0.67617(7) 0.0177(3) Uani d . . . 1 . .
H H4 0.3521 0.374 0.7056 0.021 Uiso calc U . R 1 . .
C C5 0.40183(14) 0.55393(14) 0.67619(7) 0.0159(3) Uani d . . . 1 . .
C C6 0.48437(15) 0.62410(13) 0.63279(7) 0.0152(3) Uani d . . . 1 . .
C C7 0.73912(16) 0.56844(14) 0.50540(7) 0.0213(3) Uani d . . . 1 . .
H H7A 0.8051 0.5201 0.5322 0.032 Uiso calc U . R 1 . .
H H7B 0.7878 0.6325 0.4796 0.032 Uiso calc U . R 1 . .
H H7C 0.69 0.5103 0.4757 0.032 Uiso calc U . R 1 . .
C C8 0.57702(18) 0.15744(15) 0.59541(8) 0.0248(4) Uani d . . . 1 . .
H H8A 0.551 0.1744 0.5496 0.037 Uiso calc U . R 1 . .
H H8B 0.5669 0.0663 0.6046 0.037 Uiso calc U . R 1 . .
H H8C 0.6725 0.1828 0.603 0.037 Uiso calc U . R 1 . .
C C9 0.22940(16) 0.54972(15) 0.75862(7) 0.0224(4) Uani d . . . 1 . .
H H9A 0.168 0.4969 0.7316 0.034 Uiso calc U . R 1 . .
H H9B 0.1751 0.6089 0.7849 0.034 Uiso calc U . R 1 . .
H H9C 0.284 0.495 0.7879 0.034 Uiso calc U . R 1 . .
C C10 0.48809(16) 0.76705(14) 0.63079(7) 0.0189(3) Uani d . . . 1 . .
F F1 0.61579(10) 0.81415(8) 0.63811(5) 0.0293(3) Uani d . . . 1 . .
F F2 0.44249(11) 0.81357(9) 0.57199(5) 0.0324(3) Uani d . . . 1 . .
F F3 0.41312(11) 0.82554(9) 0.67575(5) 0.0369(3) Uani d . . . 1 . .
O O1 0.64321(11) 0.63062(10) 0.54746(5) 0.0196(3) Uani d . . . 1 . .
O O2 0.49027(12) 0.22871(10) 0.63791(5) 0.0243(3) Uani d . . . 1 . .
O O3 0.31901(11) 0.62072(10) 0.71677(5) 0.0204(3) Uani d . . . 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
C1 O1 . 1.3637(17) ?
C1 C2 . 1.397(2) ?
C1 C6 . 1.404(2) ?
C2 C3 . 1.391(2) ?
C2 H2 . 0.95 ?
C3 O2 . 1.3676(17) ?
C3 C4 . 1.385(2) ?
C4 C5 . 1.391(2) ?
C4 H4 . 0.95 ?
C5 O3 . 1.3583(17) ?
C5 C6 . 1.411(2) ?
C6 C10 . 1.501(2) ?
C7 O1 . 1.4342(17) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 O2 . 1.4298(19) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 O3 . 1.4374(17) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 F3 . 1.3297(17) ?
C10 F1 . 1.3474(18) ?
C10 F2 . 1.3616(17) ?

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
O1 C1 C2 . . 122.60(13) ?
O1 C1 C6 . . 115.84(12) ?
C2 C1 C6 . . 121.56(13) ?
C3 C2 C1 . . 118.05(14) ?
C3 C2 H2 . . 121.0 ?
C1 C2 H2 . . 121.0 ?
O2 C3 C4 . . 114.64(13) ?
O2 C3 C2 . . 123.47(13) ?
C4 C3 C2 . . 121.90(13) ?
C3 C4 C5 . . 119.82(13) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
O3 C5 C4 . . 122.56(13) ?
O3 C5 C6 . . 117.46(13) ?
C4 C5 C6 . . 119.98(13) ?
C1 C6 C5 . . 118.68(13) ?
C1 C6 C10 . . 117.78(13) ?
C5 C6 C10 . . 123.54(13) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
F3 C10 F1 . . 105.78(12) ?
F3 C10 F2 . . 105.25(12) ?
F1 C10 F2 . . 104.87(12) ?
F3 C10 C6 . . 115.39(12) ?
F1 C10 C6 . . 112.71(13) ?
F2 C10 C6 . . 111.98(12) ?
C1 O1 C7 . . 118.35(11) ?
C3 O2 C8 . . 117.85(12) ?
C5 O3 C9 . . 117.71(12) ?

####################################################################### 
# 
# 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_jakir1
_database_code_depnum_ccdc_archive 'CCDC 1564327'
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 F21 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         686.28

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   39.651(3)
_cell_length_b                   5.9379(5)
_cell_length_c                   24.590(2)
_cell_angle_alpha                90
_cell_angle_beta                 126.9300(10)
_cell_angle_gamma                90
_cell_volume                     4628.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3694
_cell_measurement_theta_min      2.5704
_cell_measurement_theta_max      30.3024
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2704

_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'time focus sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15703
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       33

_refine_special_details          
;
;

_reflns_number_total             5942
_reflns_number_gt                4289
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1266
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         5942
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+1.2579P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.426
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.48954(7) 0.7823(3) 0.12865(10) 0.0207(4) Uani d . . . 1 . .
C C2 0.44895(7) 0.7326(4) 0.07296(11) 0.0230(4) Uani d . . . 1 . .
H H2 0.426 0.8213 0.0634 0.028 Uiso calc U . R 1 . .
C C3 0.44156(6) 0.5530(4) 0.03093(10) 0.0210(4) Uani d . . . 1 . .
C C4 0.47449(6) 0.4209(3) 0.04379(10) 0.0198(4) Uani d . . . 1 . .
H H4 0.4692 0.2987 0.0147 0.024 Uiso calc U . R 1 . .
C C5 0.51562(6) 0.4708(3) 0.10037(10) 0.0179(4) Uani d . . . 1 . .
C C6 0.52441(6) 0.6533(3) 0.14350(10) 0.0187(4) Uani d . . . 1 . .
C C7 0.39079(7) 0.3334(4) -0.06660(11) 0.0314(5) Uani d . . . 1 . .
H H7A 0.4055 0.3524 -0.0872 0.047 Uiso calc U . R 1 . .
H H7B 0.3603 0.3282 -0.1025 0.047 Uiso calc U . R 1 . .
H H7C 0.3999 0.1926 -0.0406 0.047 Uiso calc U . R 1 . .
C C8 0.54132(7) 0.1517(3) 0.07598(10) 0.0220(4) Uani d . . . 1 . .
H H8A 0.522 0.0511 0.0766 0.033 Uiso calc U . R 1 . .
H H8B 0.568 0.0731 0.0949 0.033 Uiso calc U . R 1 . .
H H8C 0.5286 0.1967 0.029 0.033 Uiso calc U . R 1 . .
C C9 0.46484(8) 1.0976(4) 0.15675(13) 0.0305(5) Uani d . . . 1 . .
H H9A 0.4487 1.1495 0.1095 0.046 Uiso calc U . R 1 . .
H H9B 0.4764 1.2278 0.1874 0.046 Uiso calc U . R 1 . .
H H9C 0.4463 1.0125 0.1632 0.046 Uiso calc U . R 1 . .
C C10 0.56888(6) 0.7046(3) 0.20494(10) 0.0192(4) Uani d . . . 1 . .
C C11 0.58153(6) 0.5814(3) 0.27046(10) 0.0178(4) Uani d . . . 1 . .
C C12 0.62491(6) 0.6466(3) 0.33700(10) 0.0200(4) Uani d . . . 1 . .
C C13 0.64039(6) 0.4889(3) 0.39852(10) 0.0194(4) Uani d . . . 1 . .
C C14 0.67703(6) 0.5897(4) 0.46842(11) 0.0226(4) Uani d . . . 1 . .
C C15 0.70069(6) 0.4134(4) 0.52670(11) 0.0223(4) Uani d . . . 1 . .
C C16 0.73010(6) 0.5192(4) 0.59888(11) 0.0223(4) Uani d . . . 1 . .
C C17 0.76415(7) 0.3544(4) 0.65393(11) 0.0244(4) Uani d . . . 1 . .
C C18 0.78654(7) 0.4347(4) 0.72823(11) 0.0251(4) Uani d . . . 1 . .
C C19 0.82782(7) 0.3088(4) 0.78154(12) 0.0303(5) Uani d . . . 1 . .
F F1 0.59784(4) 0.6487(2) 0.19443(6) 0.0238(3) Uani d . . . 1 . .
F F2 0.57502(4) 0.92808(19) 0.21987(6) 0.0247(3) Uani d . . . 1 . .
F F3 0.58127(4) 0.35795(18) 0.26115(6) 0.0230(3) Uani d . . . 1 . .
F F4 0.55158(4) 0.6263(2) 0.27932(6) 0.0236(3) Uani d . . . 1 . .
F F5 0.65427(4) 0.6450(2) 0.32620(6) 0.0322(3) Uani d . . . 1 . .
F F6 0.62236(4) 0.8565(2) 0.35504(6) 0.0316(3) Uani d . . . 1 . .
F F7 0.65353(4) 0.2938(2) 0.38935(6) 0.0280(3) Uani d . . . 1 . .
F F8 0.60800(4) 0.4441(2) 0.40068(6) 0.0255(3) Uani d . . . 1 . .
F F9 0.70495(4) 0.6844(2) 0.46147(7) 0.0349(3) Uani d . . . 1 . .
F F10 0.66141(4) 0.7483(2) 0.48653(6) 0.0296(3) Uani d . . . 1 . .
F F11 0.72413(4) 0.2821(3) 0.51680(7) 0.0352(3) Uani d . . . 1 . .
F F12 0.67211(4) 0.2821(2) 0.52424(6) 0.0276(3) Uani d . . . 1 . .
F F13 0.74974(4) 0.6976(2) 0.59626(7) 0.0335(3) Uani d . . . 1 . .
F F14 0.70639(4) 0.5894(2) 0.61797(6) 0.0290(3) Uani d . . . 1 . .
F F15 0.79349(4) 0.3250(3) 0.64390(7) 0.0431(4) Uani d . . . 1 . .
F F16 0.74560(5) 0.1556(2) 0.64644(7) 0.0368(3) Uani d . . . 1 . .
F F17 0.79583(4) 0.6549(2) 0.73254(7) 0.0342(3) Uani d . . . 1 . .
F F18 0.76012(4) 0.4075(2) 0.74483(6) 0.0322(3) Uani d . . . 1 . .
F F19 0.85760(4) 0.3555(3) 0.77474(8) 0.0445(4) Uani d . . . 1 . .
F F20 0.82125(4) 0.0889(2) 0.77588(7) 0.0408(4) Uani d . . . 1 . .
F F21 0.84112(5) 0.3721(3) 0.84349(7) 0.0430(4) Uani d . . . 1 . .
O O1 0.40055(5) 0.5185(3) -0.02222(7) 0.0291(4) Uani d . . . 1 . .
O O2 0.54910(4) 0.3465(2) 0.11570(7) 0.0216(3) Uani d . . . 1 . .
O O3 0.49875(5) 0.9554(3) 0.17165(8) 0.0283(4) Uani d . . . 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
C1 O3 . 1.358(2) ?
C1 C2 . 1.380(3) ?
C1 C6 . 1.423(3) ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.95 ?
C3 O1 . 1.357(2) ?
C3 C4 . 1.387(3) ?
C4 C5 . 1.399(3) ?
C4 H4 . 0.95 ?
C5 O2 . 1.359(2) ?
C5 C6 . 1.406(3) ?
C6 C10 . 1.511(3) ?
C7 O1 . 1.429(3) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 O2 . 1.423(2) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 O3 . 1.436(3) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 F2 . 1.359(2) ?
C10 F1 . 1.361(2) ?
C10 C11 . 1.553(3) ?
C11 F3 . 1.345(2) ?
C11 F4 . 1.357(2) ?
C11 C12 . 1.550(3) ?
C12 F5 . 1.341(2) ?
C12 F6 . 1.347(2) ?
C12 C13 . 1.558(3) ?
C13 F7 . 1.343(2) ?
C13 F8 . 1.344(2) ?
C13 C14 . 1.556(3) ?
C14 F9 . 1.341(2) ?
C14 F10 . 1.342(2) ?
C14 C15 . 1.554(3) ?
C15 F11 . 1.343(2) ?
C15 F12 . 1.347(2) ?
C15 C16 . 1.555(3) ?
C16 F13 . 1.339(2) ?
C16 F14 . 1.345(2) ?
C16 C17 . 1.554(3) ?
C17 F15 . 1.338(2) ?
C17 F16 . 1.344(2) ?
C17 C18 . 1.550(3) ?
C18 F18 . 1.343(2) ?
C18 F17 . 1.346(2) ?
C18 C19 . 1.542(3) ?
C19 F19 . 1.318(3) ?
C19 F20 . 1.323(3) ?
C19 F21 . 1.332(3) ?

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
O3 C1 C2 . . 122.86(18) ?
O3 C1 C6 . . 116.26(18) ?
C2 C1 C6 . . 120.88(18) ?
C1 C2 C3 . . 120.13(19) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
O1 C3 C4 . . 123.61(19) ?
O1 C3 C2 . . 115.33(18) ?
C4 C3 C2 . . 121.06(19) ?
C3 C4 C5 . . 118.83(19) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
O2 C5 C4 . . 121.44(17) ?
O2 C5 C6 . . 116.82(17) ?
C4 C5 C6 . . 121.73(18) ?
C5 C6 C1 . . 117.34(18) ?
C5 C6 C10 . . 121.39(17) ?
C1 C6 C10 . . 121.21(17) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
F2 C10 F1 . . 104.78(15) ?
F2 C10 C6 . . 112.25(16) ?
F1 C10 C6 . . 111.83(15) ?
F2 C10 C11 . . 106.61(15) ?
F1 C10 C11 . . 107.39(16) ?
C6 C10 C11 . . 113.43(16) ?
F3 C11 F4 . . 107.66(15) ?
F3 C11 C12 . . 108.42(16) ?
F4 C11 C12 . . 107.73(15) ?
F3 C11 C10 . . 108.86(15) ?
F4 C11 C10 . . 107.82(16) ?
C12 C11 C10 . . 116.06(16) ?
F5 C12 F6 . . 108.52(16) ?
F5 C12 C11 . . 109.50(15) ?
F6 C12 C11 . . 108.88(16) ?
F5 C12 C13 . . 107.80(16) ?
F6 C12 C13 . . 107.47(15) ?
C11 C12 C13 . . 114.52(16) ?
F7 C13 F8 . . 108.20(16) ?
F7 C13 C14 . . 108.55(16) ?
F8 C13 C14 . . 108.21(15) ?
F7 C13 C12 . . 108.76(15) ?
F8 C13 C12 . . 109.21(16) ?
C14 C13 C12 . . 113.77(16) ?
F9 C14 F10 . . 109.22(17) ?
F9 C14 C15 . . 108.24(17) ?
F10 C14 C15 . . 108.05(16) ?
F9 C14 C13 . . 108.35(16) ?
F10 C14 C13 . . 109.00(16) ?
C15 C14 C13 . . 113.90(17) ?
F11 C15 F12 . . 108.11(17) ?
F11 C15 C14 . . 108.91(16) ?
F12 C15 C14 . . 108.88(16) ?
F11 C15 C16 . . 108.37(16) ?
F12 C15 C16 . . 108.60(16) ?
C14 C15 C16 . . 113.82(17) ?
F13 C16 F14 . . 108.67(17) ?
F13 C16 C17 . . 108.30(16) ?
F14 C16 C17 . . 108.34(16) ?
F13 C16 C15 . . 108.89(16) ?
F14 C16 C15 . . 108.75(16) ?
C17 C16 C15 . . 113.79(17) ?
F15 C17 F16 . . 108.97(18) ?
F15 C17 C18 . . 108.16(18) ?
F16 C17 C18 . . 108.07(17) ?
F15 C17 C16 . . 108.54(17) ?
F16 C17 C16 . . 108.43(17) ?
C18 C17 C16 . . 114.56(17) ?
F18 C18 F17 . . 108.63(17) ?
F18 C18 C19 . . 107.86(17) ?
F17 C18 C19 . . 107.67(18) ?
F18 C18 C17 . . 108.81(17) ?
F17 C18 C17 . . 109.11(17) ?
C19 C18 C17 . . 114.62(18) ?
F19 C19 F20 . . 109.2(2) ?
F19 C19 F21 . . 108.46(19) ?
F20 C19 F21 . . 108.44(19) ?
F19 C19 C18 . . 111.38(19) ?
F20 C19 C18 . . 110.35(18) ?
F21 C19 C18 . . 108.9(2) ?
C3 O1 C7 . . 118.02(17) ?
C5 O2 C8 . . 118.55(16) ?
C1 O3 C9 . . 118.27(18) ?

####################################################################### 
# 
# 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_jakir27_1
_database_code_depnum_ccdc_archive 'CCDC 1564329'
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 F9 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         363.23

_chemical_melting_point          ?

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

_cell_length_a                   7.024(3)
_cell_length_b                   8.522(3)
_cell_length_c                   23.918(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.184(6)
_cell_angle_gamma                90
_cell_volume                     1423.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2740
_cell_measurement_theta_min      2.9410
_cell_measurement_theta_max      24.9928
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14129
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             2510
_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          0.0950
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.2111
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_number_reflns         2510
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²+1.8130P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.502
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.7271(5) 0.4788(4) 0.42216(16) 0.0210(8) Uani d . . . 1 . .
C C2 0.7574(5) 0.6379(4) 0.41832(15) 0.0178(8) Uani d . . . 1 . .
C C3 0.7770(5) 0.6999(4) 0.47446(15) 0.0171(8) Uani d . . . 1 . .
C C4 0.8031(5) 0.8507(4) 0.49768(16) 0.0198(8) Uani d . . . 1 . .
H H4 0.813 0.9396 0.4742 0.024 Uiso calc U . R 1 . .
C C5 0.8141(6) 0.8668(5) 0.55498(16) 0.0241(9) Uani d . . . 1 . .
H H5 0.8293 0.9686 0.5711 0.029 Uiso calc U . R 1 . .
C C6 0.8032(6) 0.7368(5) 0.59030(16) 0.0268(9) Uani d . . . 1 . .
H H6 0.8142 0.7516 0.6299 0.032 Uiso calc U . R 1 . .
C C7 0.7768(5) 0.5877(5) 0.56858(16) 0.0227(9) Uani d . . . 1 . .
H H7 0.7683 0.4994 0.5924 0.027 Uiso calc U . R 1 . .
C C8 0.7631(5) 0.5714(4) 0.51049(15) 0.0165(8) Uani d . . . 1 . .
C C9 0.6933(6) 0.3563(5) 0.37745(19) 0.0334(11) Uani d . . . 1 . .
H H9A 0.7987 0.2803 0.3813 0.05 Uiso calc U . R 1 . .
H H9B 0.6868 0.4061 0.3404 0.05 Uiso calc U . R 1 . .
H H9C 0.5724 0.3021 0.3813 0.05 Uiso calc U . R 1 . .
C C10 0.7087(6) 0.2818(4) 0.4996(2) 0.0324(10) Uani d . . . 1 . .
H H10A 0.6008 0.2297 0.4777 0.049 Uiso calc U . R 1 . .
H H10B 0.684 0.2883 0.5391 0.049 Uiso calc U . R 1 . .
H H10C 0.826 0.2213 0.4968 0.049 Uiso calc U . R 1 . .
C C11 0.7612(6) 0.7308(5) 0.36643(16) 0.0260(9) Uani d . . . 1 . .
C C12 0.5655(6) 0.8006(5) 0.34355(17) 0.0288(10) Uani d . . . 1 . .
C C13 0.5458(7) 0.8672(5) 0.28368(17) 0.0326(10) Uani d . . . 1 . .
C C14 0.3699(7) 0.9714(5) 0.26811(18) 0.0371(11) Uani d . . . 1 . .
F F1 0.8240(4) 0.6482(3) 0.32386(10) 0.0409(7) Uani d . . . 1 . .
F F2 0.8827(4) 0.8586(3) 0.37565(10) 0.0396(7) Uani d . . . 1 . .
F F3 0.4334(4) 0.6855(3) 0.34429(11) 0.0416(7) Uani d . . . 1 . .
F F4 0.5200(4) 0.9142(3) 0.37939(9) 0.0367(7) Uani d . . . 1 . .
F F5 0.5339(5) 0.7463(4) 0.24671(11) 0.0524(9) Uani d . . . 1 . .
F F6 0.7017(5) 0.9494(4) 0.27582(12) 0.0556(9) Uani d . . . 1 . .
F F7 0.2154(5) 0.9085(4) 0.28448(14) 0.0598(9) Uani d . . . 1 . .
F F8 0.3979(6) 1.1112(3) 0.29159(12) 0.0624(10) Uani d . . . 1 . .
F F9 0.3446(5) 0.9914(4) 0.21362(11) 0.0512(8) Uani d . . . 1 . .
N N008 0.7316(4) 0.4391(3) 0.47763(14) 0.0197(7) Uani d . . . 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
C1 N008 . 1.366(5) ?
C1 C2 . 1.377(6) ?
C1 C9 . 1.495(5) ?
C2 C3 . 1.436(5) ?
C2 C11 . 1.475(5) ?
C3 C4 . 1.403(5) ?
C3 C8 . 1.404(5) ?
C4 C5 . 1.371(5) ?
C4 H4 . 0.95 ?
C5 C6 . 1.401(6) ?
C5 H5 . 0.95 ?
C6 C7 . 1.377(6) ?
C6 H6 . 0.95 ?
C7 C8 . 1.389(5) ?
C7 H7 . 0.95 ?
C8 N008 . 1.379(5) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 N008 . 1.455(5) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 F1 . 1.351(4) ?
C11 F2 . 1.387(5) ?
C11 C12 . 1.543(6) ?
C12 F3 . 1.352(5) ?
C12 F4 . 1.354(5) ?
C12 C13 . 1.533(6) ?
C13 F6 . 1.330(5) ?
C13 F5 . 1.354(5) ?
C13 C14 . 1.535(7) ?
C14 F9 . 1.307(5) ?
C14 F7 . 1.308(6) ?
C14 F8 . 1.323(5) ?

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
N008 C1 C2 . . 108.7(3) ?
N008 C1 C9 . . 120.5(4) ?
C2 C1 C9 . . 130.8(4) ?
C1 C2 C3 . . 107.5(3) ?
C1 C2 C11 . . 127.0(3) ?
C3 C2 C11 . . 125.5(3) ?
C4 C3 C8 . . 119.1(3) ?
C4 C3 C2 . . 134.6(3) ?
C8 C3 C2 . . 106.3(3) ?
C5 C4 C3 . . 118.6(4) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C4 C5 C6 . . 121.5(4) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C7 C6 C5 . . 121.1(4) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 117.5(3) ?
C6 C7 H7 . . 121.3 ?
C8 C7 H7 . . 121.3 ?
N008 C8 C7 . . 129.9(3) ?
N008 C8 C3 . . 107.8(3) ?
C7 C8 C3 . . 122.3(3) ?
C1 C9 H9A . . 109.5 ?
C1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N008 C10 H10A . . 109.5 ?
N008 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N008 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
F1 C11 F2 . . 106.5(3) ?
F1 C11 C2 . . 113.0(3) ?
F2 C11 C2 . . 110.8(3) ?
F1 C11 C12 . . 106.5(3) ?
F2 C11 C12 . . 105.3(3) ?
C2 C11 C12 . . 114.2(3) ?
F3 C12 F4 . . 107.5(3) ?
F3 C12 C13 . . 106.7(3) ?
F4 C12 C13 . . 108.9(3) ?
F3 C12 C11 . . 107.6(3) ?
F4 C12 C11 . . 108.3(3) ?
C13 C12 C11 . . 117.5(4) ?
F6 C13 F5 . . 107.6(4) ?
F6 C13 C12 . . 109.5(4) ?
F5 C13 C12 . . 108.8(3) ?
F6 C13 C14 . . 108.3(4) ?
F5 C13 C14 . . 106.8(4) ?
C12 C13 C14 . . 115.5(4) ?
F9 C14 F7 . . 108.9(4) ?
F9 C14 F8 . . 107.7(4) ?
F7 C14 F8 . . 109.4(4) ?
F9 C14 C13 . . 109.7(4) ?
F7 C14 C13 . . 111.3(4) ?
F8 C14 C13 . . 109.8(4) ?
C1 N008 C8 . . 109.7(3) ?
C1 N008 C10 . . 125.9(3) ?
C8 N008 C10 . . 124.4(3) ?

####################################################################### 
# 
# 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_jakir32
_database_code_depnum_ccdc_archive 'CCDC 1564330'
_audit_update_record             
;
2017-07-25 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 F17 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         563.27

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.192(3)
_cell_length_b                   9.755(4)
_cell_length_c                   14.736(7)
_cell_angle_alpha                83.238(7)
_cell_angle_beta                 76.919(7)
_cell_angle_gamma                81.099(7)
_cell_volume                     991.2(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1979
_cell_measurement_theta_min      2.8488
_cell_measurement_theta_max      24.5343
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556

_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14524
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             5309
_reflns_number_gt                3068
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.2371
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_number_reflns         5309
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1131P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         1.003
_refine_diff_density_min         -0.455
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.2336(5) 0.6050(4) 0.9360(3) 0.0235(8) Uani d . . . 1 . .
C C2 0.2519(5) 0.5336(4) 0.8577(3) 0.0215(7) Uani d . . . 1 . .
C C3 0.2697(5) 0.3870(3) 0.8879(2) 0.0184(7) Uani d . . . 1 . .
C C4 0.2618(5) 0.3764(4) 0.9852(2) 0.0191(7) Uani d . . . 1 . .
C C5 0.2739(5) 0.2492(4) 1.0386(3) 0.0240(8) Uani d . . . 1 . .
H H5 0.2664 0.2443 1.1041 0.029 Uiso calc U . R 1 . .
C C6 0.2974(5) 0.1303(4) 0.9924(3) 0.0261(8) Uani d . . . 1 . .
H H6 0.3068 0.0418 1.027 0.031 Uiso calc U . R 1 . .
C C7 0.3076(5) 0.1369(4) 0.8960(3) 0.0269(8) Uani d . . . 1 . .
H H7 0.3241 0.0531 0.8664 0.032 Uiso calc U . R 1 . .
C C8 0.2940(5) 0.2639(4) 0.8432(3) 0.0240(8) Uani d . . . 1 . .
H H8 0.3011 0.2676 0.7778 0.029 Uiso calc U . R 1 . .
C C9 0.2163(6) 0.7569(4) 0.9462(3) 0.0317(9) Uani d . . . 1 . .
H H9A 0.1035 0.7836 0.9951 0.048 Uiso calc U . R 1 . .
H H9B 0.2017 0.8096 0.8868 0.048 Uiso calc U . R 1 . .
H H9C 0.3325 0.7774 0.9633 0.048 Uiso calc U . R 1 . .
C C10 0.2291(6) 0.5444(5) 1.1066(3) 0.0303(9) Uani d . . . 1 . .
H H10A 0.3527 0.5709 1.1107 0.045 Uiso calc U . R 1 . .
H H10B 0.201 0.4631 1.1507 0.045 Uiso calc U . R 1 . .
H H10C 0.1269 0.6222 1.1221 0.045 Uiso calc U . R 1 . .
C C11 0.2639(5) 0.5936(4) 0.7589(3) 0.0269(8) Uani d . . . 1 . .
C C12 0.4692(6) 0.6204(4) 0.7081(3) 0.0267(8) Uani d . . . 1 . .
C C13 0.4989(5) 0.6926(4) 0.6086(3) 0.0259(8) Uani d . . . 1 . .
C C14 0.7127(6) 0.6920(4) 0.5578(3) 0.0249(8) Uani d . . . 1 . .
C C15 0.7452(5) 0.8037(4) 0.4733(3) 0.0225(8) Uani d . . . 1 . .
C C16 0.9533(5) 0.7897(4) 0.4117(2) 0.0210(7) Uani d . . . 1 . .
C C17 0.9976(5) 0.9205(4) 0.3435(2) 0.0224(7) Uani d . . . 1 . .
C C18 1.1926(6) 0.9027(4) 0.2721(3) 0.0285(9) Uani d . . . 1 . .
F F1 0.1462(3) 0.7171(2) 0.75316(17) 0.0353(6) Uani d . . . 1 . .
F F2 0.2082(4) 0.5053(3) 0.70768(17) 0.0373(6) Uani d . . . 1 . .
F F3 0.5284(3) 0.7039(2) 0.76149(16) 0.0329(6) Uani d . . . 1 . .
F F4 0.5849(3) 0.4974(2) 0.70681(15) 0.0282(5) Uani d . . . 1 . .
F F5 0.4107(4) 0.8222(2) 0.60997(17) 0.0421(7) Uani d . . . 1 . .
F F6 0.4162(4) 0.6261(3) 0.55597(16) 0.0416(7) Uani d . . . 1 . .
F F7 0.8153(3) 0.7172(3) 0.61859(15) 0.0339(6) Uani d . . . 1 . .
F F8 0.7855(4) 0.5668(2) 0.52666(17) 0.0374(6) Uani d . . . 1 . .
F F9 0.7073(3) 0.9306(2) 0.50600(16) 0.0308(5) Uani d . . . 1 . .
F F10 0.6221(3) 0.7954(3) 0.41881(16) 0.0346(6) Uani d . . . 1 . .
F F11 1.0808(3) 0.7655(2) 0.46704(15) 0.0275(5) Uani d . . . 1 . .
F F12 0.9771(3) 0.6804(2) 0.36020(16) 0.0324(6) Uani d . . . 1 . .
F F13 0.9997(3) 1.0269(2) 0.39274(15) 0.0310(6) Uani d . . . 1 . .
F F14 0.8579(3) 0.9553(2) 0.29451(15) 0.0317(6) Uani d . . . 1 . .
F F15 1.3341(4) 0.8583(3) 0.31553(19) 0.0524(8) Uani d . . . 1 . .
F F16 1.2240(4) 1.0247(3) 0.22688(17) 0.0442(7) Uani d . . . 1 . .
F F17 1.1917(4) 0.8164(3) 0.21059(18) 0.0535(8) Uani d . . . 1 . .
N N1 0.2388(4) 0.5103(3) 1.0124(2) 0.0223(7) Uani d . . . 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
C1 N1 . 1.373(5) ?
C1 C2 . 1.388(5) ?
C1 C9 . 1.490(5) ?
C2 C3 . 1.441(5) ?
C2 C11 . 1.493(5) ?
C3 C8 . 1.406(5) ?
C3 C4 . 1.414(5) ?
C4 N1 . 1.386(5) ?
C4 C5 . 1.391(5) ?
C5 C6 . 1.382(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.400(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.385(5) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 N1 . 1.449(5) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 F1 . 1.367(4) ?
C11 F2 . 1.368(4) ?
C11 C12 . 1.543(5) ?
C12 F4 . 1.350(4) ?
C12 F3 . 1.369(4) ?
C12 C13 . 1.533(5) ?
C13 F5 . 1.324(4) ?
C13 F6 . 1.350(5) ?
C13 C14 . 1.550(5) ?
C14 F8 . 1.342(4) ?
C14 F7 . 1.347(4) ?
C14 C15 . 1.556(5) ?
C15 F10 . 1.339(4) ?
C15 F9 . 1.348(4) ?
C15 C16 . 1.560(5) ?
C16 F11 . 1.337(4) ?
C16 F12 . 1.349(4) ?
C16 C17 . 1.555(5) ?
C17 F13 . 1.338(4) ?
C17 F14 . 1.346(4) ?
C17 C18 . 1.550(5) ?
C18 F17 . 1.310(5) ?
C18 F15 . 1.313(5) ?
C18 F16 . 1.320(5) ?

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
N1 C1 C2 . . 108.9(3) ?
N1 C1 C9 . . 120.2(3) ?
C2 C1 C9 . . 130.9(4) ?
C1 C2 C3 . . 107.3(3) ?
C1 C2 C11 . . 127.5(3) ?
C3 C2 C11 . . 125.2(3) ?
C8 C3 C4 . . 118.6(3) ?
C8 C3 C2 . . 134.9(3) ?
C4 C3 C2 . . 106.5(3) ?
N1 C4 C5 . . 129.6(3) ?
N1 C4 C3 . . 107.7(3) ?
C5 C4 C3 . . 122.6(3) ?
C6 C5 C4 . . 117.2(3) ?
C6 C5 H5 . . 121.4 ?
C4 C5 H5 . . 121.4 ?
C5 C6 C7 . . 121.7(3) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 120.9(3) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 C3 . . 119.0(3) ?
C7 C8 H8 . . 120.5 ?
C3 C8 H8 . . 120.5 ?
C1 C9 H9A . . 109.5 ?
C1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N1 C10 H10A . . 109.5 ?
N1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
F1 C11 F2 . . 106.9(3) ?
F1 C11 C2 . . 111.9(3) ?
F2 C11 C2 . . 110.8(3) ?
F1 C11 C12 . . 107.2(3) ?
F2 C11 C12 . . 106.4(3) ?
C2 C11 C12 . . 113.3(3) ?
F4 C12 F3 . . 108.3(3) ?
F4 C12 C13 . . 108.6(3) ?
F3 C12 C13 . . 106.4(3) ?
F4 C12 C11 . . 108.1(3) ?
F3 C12 C11 . . 106.5(3) ?
C13 C12 C11 . . 118.6(3) ?
F5 C13 F6 . . 106.9(3) ?
F5 C13 C12 . . 110.0(3) ?
F6 C13 C12 . . 109.0(3) ?
F5 C13 C14 . . 109.7(3) ?
F6 C13 C14 . . 106.5(3) ?
C12 C13 C14 . . 114.4(3) ?
F8 C14 F7 . . 107.9(3) ?
F8 C14 C13 . . 110.4(3) ?
F7 C14 C13 . . 109.1(3) ?
F8 C14 C15 . . 108.0(3) ?
F7 C14 C15 . . 107.3(3) ?
C13 C14 C15 . . 113.9(3) ?
F10 C15 F9 . . 108.8(3) ?
F10 C15 C14 . . 108.7(3) ?
F9 C15 C14 . . 108.5(3) ?
F10 C15 C16 . . 108.3(3) ?
F9 C15 C16 . . 107.8(3) ?
C14 C15 C16 . . 114.6(3) ?
F11 C16 F12 . . 108.6(3) ?
F11 C16 C17 . . 108.5(3) ?
F12 C16 C17 . . 107.9(3) ?
F11 C16 C15 . . 109.4(3) ?
F12 C16 C15 . . 108.7(3) ?
C17 C16 C15 . . 113.8(3) ?
F13 C17 F14 . . 108.6(3) ?
F13 C17 C18 . . 107.2(3) ?
F14 C17 C18 . . 107.4(3) ?
F13 C17 C16 . . 109.3(3) ?
F14 C17 C16 . . 109.1(3) ?
C18 C17 C16 . . 115.0(3) ?
F17 C18 F15 . . 109.7(4) ?
F17 C18 F16 . . 108.1(3) ?
F15 C18 F16 . . 108.1(3) ?
F17 C18 C17 . . 111.5(3) ?
F15 C18 C17 . . 110.4(3) ?
F16 C18 C17 . . 109.0(3) ?
C1 N1 C4 . . 109.6(3) ?
C1 N1 C10 . . 125.4(3) ?
C4 N1 C10 . . 125.0(3) ?

####################################################################### 
# 
# 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_jakir9
_database_code_depnum_ccdc_archive 'CCDC 1564318'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 F7 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         336.21

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3629(7)
_cell_length_b                   8.6815(7)
_cell_length_c                   9.7649(8)
_cell_angle_alpha                84.6860(10)
_cell_angle_beta                 69.8510(10)
_cell_angle_gamma                79.6210(10)
_cell_volume                     654.32(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2397
_cell_measurement_theta_min      2.2228
_cell_measurement_theta_max      30.4528
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340

_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            3741
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2462
_reflns_number_gt                2182
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1008
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_restrained_S_all      1.348
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.394
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.68994(18) 0.65979(16) 0.29444(15) 0.0132(3) Uani d . . . 1 . .
C C2 0.73524(18) 0.71501(16) 0.40436(15) 0.0139(3) Uani d . . . 1 . .
C C3 0.76549(17) 0.61636(16) 0.51701(15) 0.0138(3) Uani d . . . 1 . .
H H3 0.7924 0.6564 0.5923 0.017 Uiso calc U . R 1 . .
C C4 0.75540(17) 0.45839(16) 0.51680(16) 0.0141(3) Uani d . . . 1 . .
C C5 0.71736(18) 0.39854(16) 0.40716(16) 0.0154(3) Uani d . . . 1 . .
H H5 0.7135 0.2898 0.4077 0.019 Uiso calc U . R 1 . .
C C6 0.68494(17) 0.49730(16) 0.29646(15) 0.0136(3) Uani d . . . 1 . .
C C7 0.65477(18) 0.76797(16) 0.17464(15) 0.0136(3) Uani d . . . 1 . .
C C8 0.81878(18) 0.78504(16) 0.04110(16) 0.0149(3) Uani d . . . 1 . .
C C9 0.79065(18) 0.87843(16) -0.09283(16) 0.0148(3) Uani d . . . 1 . .
C C10 0.8069(2) 0.92734(17) 0.49904(17) 0.0213(3) Uani d . . . 1 . .
H H10A 0.718 0.9237 0.5954 0.032 Uiso calc U . R 1 . .
H H10B 0.8259 1.0358 0.4722 0.032 Uiso calc U . R 1 . .
H H10C 0.9147 0.8626 0.5018 0.032 Uiso calc U . R 1 . .
C C11 0.8059(2) 0.40731(18) 0.74510(16) 0.0200(3) Uani d . . . 1 . .
H H11A 0.9061 0.4619 0.7138 0.03 Uiso calc U . R 1 . .
H H11B 0.8237 0.3185 0.8108 0.03 Uiso calc U . R 1 . .
H H11C 0.7023 0.4798 0.7964 0.03 Uiso calc U . R 1 . .
C C12 0.6462(2) 0.28112(17) 0.18264(17) 0.0203(3) Uani d . . . 1 . .
H H12A 0.7607 0.2228 0.1745 0.03 Uiso calc U . R 1 . .
H H12B 0.6158 0.2606 0.0984 0.03 Uiso calc U . R 1 . .
H H12C 0.5609 0.2476 0.2726 0.03 Uiso calc U . R 1 . .
F F1 0.58229(11) 0.91568(9) 0.22134(9) 0.0186(2) Uani d . . . 1 . .
F F2 0.54151(10) 0.72096(10) 0.12225(9) 0.0183(2) Uani d . . . 1 . .
F F3 0.92551(11) 0.85493(12) 0.08139(10) 0.0264(3) Uani d . . . 1 . .
F F4 0.90130(12) 0.64147(10) -0.00539(10) 0.0292(3) Uani d . . . 1 . .
F F5 0.70592(14) 1.02027(11) -0.05965(10) 0.0351(3) Uani d . . . 1 . .
F F6 0.70386(14) 0.80677(13) -0.15092(10) 0.0361(3) Uani d . . . 1 . .
F F7 0.94188(11) 0.89156(11) -0.19528(10) 0.0279(3) Uani d . . . 1 . .
O O1 0.75191(14) 0.86912(11) 0.39401(11) 0.0193(3) Uani d . . . 1 . .
O O2 0.78464(13) 0.35138(11) 0.61992(11) 0.0186(3) Uani d . . . 1 . .
O O3 0.64779(14) 0.44495(12) 0.18620(11) 0.0194(3) Uani d . . . 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
C1 C2 . 1.402(2) ?
C1 C6 . 1.4170(19) ?
C1 C7 . 1.5070(18) ?
C2 O1 . 1.3609(16) ?
C2 C3 . 1.3952(19) ?
C3 C4 . 1.3894(19) ?
C3 H3 . 0.95 ?
C4 O2 . 1.3607(16) ?
C4 C5 . 1.384(2) ?
C5 C6 . 1.3870(19) ?
C5 H5 . 0.95 ?
C6 O3 . 1.3543(16) ?
C7 F2 . 1.3555(15) ?
C7 F1 . 1.3629(16) ?
C7 C8 . 1.5521(19) ?
C8 F3 . 1.3420(16) ?
C8 F4 . 1.3472(17) ?
C8 C9 . 1.5394(19) ?
C9 F5 . 1.3133(17) ?
C9 F6 . 1.3219(16) ?
C9 F7 . 1.3314(16) ?
C10 O1 . 1.4225(17) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 O2 . 1.4325(18) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 O3 . 1.4285(17) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?

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
C2 C1 C6 . . 117.69(12) ?
C2 C1 C7 . . 121.31(12) ?
C6 C1 C7 . . 120.96(13) ?
O1 C2 C3 . . 121.57(13) ?
O1 C2 C1 . . 116.65(12) ?
C3 C2 C1 . . 121.77(13) ?
C4 C3 C2 . . 118.66(13) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
O2 C4 C5 . . 115.14(12) ?
O2 C4 C3 . . 123.66(13) ?
C5 C4 C3 . . 121.19(13) ?
C4 C5 C6 . . 120.01(13) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
O3 C6 C5 . . 122.49(12) ?
O3 C6 C1 . . 116.91(12) ?
C5 C6 C1 . . 120.60(13) ?
F2 C7 F1 . . 104.96(10) ?
F2 C7 C1 . . 112.70(11) ?
F1 C7 C1 . . 112.24(12) ?
F2 C7 C8 . . 106.36(11) ?
F1 C7 C8 . . 106.37(11) ?
C1 C7 C8 . . 113.57(11) ?
F3 C8 F4 . . 108.07(11) ?
F3 C8 C9 . . 107.05(11) ?
F4 C8 C9 . . 106.32(12) ?
F3 C8 C7 . . 109.41(12) ?
F4 C8 C7 . . 109.09(11) ?
C9 C8 C7 . . 116.57(12) ?
F5 C9 F6 . . 108.23(12) ?
F5 C9 F7 . . 107.96(11) ?
F6 C9 F7 . . 107.30(12) ?
F5 C9 C8 . . 111.89(12) ?
F6 C9 C8 . . 111.15(11) ?
F7 C9 C8 . . 110.13(12) ?
O1 C10 H10A . . 109.5 ?
O1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O3 C12 H12A . . 109.5 ?
O3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 O1 C10 . . 118.23(11) ?
C4 O2 C11 . . 118.15(11) ?
C6 O3 C12 . . 118.42(11) ?

