# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1445533'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-03-05 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C23 H13 Br F4 O3'

_chemical_formula_weight         493.24



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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/n



loop_

_symmetry_equiv_pos_as_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                   9.7650(12)

_cell_length_b                   18.091(2)

_cell_length_c                   11.2978(15)

_cell_angle_alpha                90.00

_cell_angle_beta                 91.058(2)

_cell_angle_gamma                90.00

_cell_volume                     1995.5(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3068

_cell_measurement_theta_min      2.25

_cell_measurement_theta_max      22.11



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.33

_exptl_crystal_size_min          0.28

_exptl_crystal_density_meas      none

_exptl_crystal_density_diffrn    1.642

_exptl_crystal_density_method    none

_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    2.120

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.5241

_exptl_absorpt_correction_T_max  0.5882

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            12304

_diffrn_reflns_av_R_equivalents  0.0346

_diffrn_reflns_av_sigmaI/netI    0.0398

_diffrn_reflns_limit_h_min       -12

_diffrn_reflns_limit_h_max       12

_diffrn_reflns_limit_k_min       -22

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -14

_diffrn_reflns_limit_l_max       14

_diffrn_reflns_theta_min         2.13

_diffrn_reflns_theta_max         26.37

_reflns_number_total             4083

_reflns_number_gt                2707

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0844P)²+0.5172P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         4083

_refine_ls_number_parameters     282

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0830

_refine_ls_R_factor_gt           0.0495

_refine_ls_wR_factor_ref         0.1482

_refine_ls_wR_factor_gt          0.1270

_refine_ls_goodness_of_fit_ref   1.020

_refine_ls_restrained_S_all      1.020

_refine_ls_shift/su_max          0.016

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group












































Br1 Br 0.47028(5) 0.16660(3) 0.82304(4) 0.0786(2) Uani 1 1 d . . .
C1 C 0.2484(3) 0.37278(17) 0.9813(3) 0.0424(7) Uani 1 1 d . . .
C2 C 0.3726(3) 0.37847(18) 0.9239(3) 0.0477(8) Uani 1 1 d . . .
C3 C 0.4381(4) 0.3175(2) 0.8800(3) 0.0533(9) Uani 1 1 d . . .
C4 C 0.3811(3) 0.24790(19) 0.8878(3) 0.0469(8) Uani 1 1 d . . .
C5 C 0.2577(3) 0.24160(18) 0.9427(3) 0.0447(7) Uani 1 1 d . . .
C6 C 0.1935(3) 0.30225(19) 0.9888(3) 0.0446(7) Uani 1 1 d . . .
C7 C 0.1784(3) 0.44084(19) 1.0379(3) 0.0415(7) Uani 1 1 d . . .
C8 C 0.1481(5) 0.8578(3) 0.9230(4) 0.0847(14) Uani 1 1 d . . .
H8 H 0.0801 0.8287 0.9560 0.102 Uiso 1 1 calc R . .
C9 C 0.1302(6) 0.9311(3) 0.9161(5) 0.0973(16) Uani 1 1 d . . .
H9 H 0.0506 0.9522 0.9449 0.117 Uiso 1 1 calc R . .
C10 C 0.2300(5) 0.9763(3) 0.8662(4) 0.0864(14) Uani 1 1 d . . .
H10 H 0.2159 1.0271 0.8622 0.104 Uiso 1 1 calc R . .
C11 C 0.3473(4) 0.9471(2) 0.8235(4) 0.0683(11) Uani 1 1 d . . .
H11 H 0.4122 0.9781 0.7903 0.082 Uiso 1 1 calc R . .
C12 C 0.3719(4) 0.8694(2) 0.8290(3) 0.0508(8) Uani 1 1 d . . .
C13 C 0.2697(4) 0.8234(2) 0.8808(3) 0.0586(9) Uani 1 1 d . . .
C14 C 0.4191(4) 0.6348(2) 0.8324(4) 0.0642(11) Uani 1 1 d . . .
H14 H 0.3535 0.6047 0.8666 0.077 Uiso 1 1 calc R . .
C15 C 0.4023(4) 0.7137(2) 0.8355(3) 0.0521(9) Uani 1 1 d . . .
C16 C 0.5050(3) 0.75857(18) 0.7821(3) 0.0469(8) Uani 1 1 d . . .
C17 C 0.6190(4) 0.7232(2) 0.7307(3) 0.0576(9) Uani 1 1 d . . .
H17 H 0.6877 0.7516 0.6974 0.069 Uiso 1 1 calc R . .
C18 C 0.6292(4) 0.6475(2) 0.7296(4) 0.0686(11) Uani 1 1 d . . .
H18 H 0.7038 0.6251 0.6944 0.082 Uiso 1 1 calc R . .
C19 C 0.5275(5) 0.6038(2) 0.7813(4) 0.0726(12) Uani 1 1 d . . .
H19 H 0.5356 0.5526 0.7799 0.087 Uiso 1 1 calc R . .
C20 C 0.2889(4) 0.7471(2) 0.8845(3) 0.0594(10) Uani 1 1 d . . .
H20 H 0.2238 0.7178 0.9209 0.071 Uiso 1 1 calc R . .
C21 C 0.4878(4) 0.83612(17) 0.7817(3) 0.0472(8) Uani 1 1 d . . .
C22 C 0.5942(4) 0.88391(19) 0.7256(4) 0.0541(9) Uani 1 1 d . . .
C23 C 0.6954(5) 0.9218(3) 0.8047(4) 0.0799(13) Uani 1 1 d . . .
H23A H 0.7505 0.8856 0.8454 0.120 Uiso 1 1 calc R . .
H23B H 0.6478 0.9513 0.8614 0.120 Uiso 1 1 calc R . .
H23C H 0.7530 0.9531 0.7583 0.120 Uiso 1 1 calc R . .
F1 F 0.5604(2) 0.32654(13) 0.8295(2) 0.0815(8) Uani 1 1 d . . .
F2 F 0.4360(2) 0.44357(12) 0.9149(2) 0.0710(6) Uani 1 1 d . . .
F3 F 0.0744(2) 0.29078(12) 1.04273(19) 0.0661(6) Uani 1 1 d . . .
F4 F 0.1977(2) 0.17515(11) 0.9519(2) 0.0645(6) Uani 1 1 d . . .
O1 O 0.2000(3) 0.49849(15) 0.9881(3) 0.0785(9) Uani 1 1 d . . .
O2 O 0.1115(3) 0.43035(15) 1.1253(2) 0.0694(8) Uani 1 1 d . . .
H2 H 0.1353 0.4595 1.1773 0.104 Uiso 1 1 calc R . .
O3 O 0.5962(3) 0.88998(15) 0.6195(3) 0.0742(8) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag














































Br1 C4 1.865(3) . ?
C1 C6 1.387(5) . ?
C1 C2 1.389(4) . ?
C1 C7 1.552(4) . ?
C2 F2 1.336(4) . ?
C2 C3 1.373(5) . ?
C3 F1 1.343(4) . ?
C3 C4 1.380(5) . ?
C4 C5 1.371(4) . ?
C5 F4 1.342(4) . ?
C5 C6 1.371(4) . ?
C6 F3 1.339(4) . ?
C7 O1 1.206(4) . ?
C7 O2 1.209(4) . ?
C8 C9 1.341(7) . ?
C8 C13 1.430(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.357(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.428(5) . ?
C11 H11 0.9300 . ?
C12 C21 1.397(5) . ?
C12 C13 1.433(5) . ?
C13 C20 1.392(5) . ?
C14 C19 1.338(6) . ?
C14 C15 1.437(6) . ?
C14 H14 0.9300 . ?
C15 C20 1.386(5) . ?
C15 C16 1.432(5) . ?
C16 C21 1.413(4) . ?
C16 C17 1.418(5) . ?
C17 C18 1.372(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.405(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.501(5) . ?
C22 O3 1.204(4) . ?
C22 C23 1.487(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O2 H2 0.8200 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag









































































C6 C1 C2 116.0(3) . . ?
C6 C1 C7 122.1(3) . . ?
C2 C1 C7 121.9(3) . . ?
F2 C2 C3 117.4(3) . . ?
F2 C2 C1 120.8(3) . . ?
C3 C2 C1 121.7(3) . . ?
F1 C3 C2 118.7(3) . . ?
F1 C3 C4 120.0(3) . . ?
C2 C3 C4 121.3(3) . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 Br1 122.2(3) . . ?
C3 C4 Br1 120.2(3) . . ?
F4 C5 C4 119.9(3) . . ?
F4 C5 C6 119.0(3) . . ?
C4 C5 C6 121.2(3) . . ?
F3 C6 C5 117.1(3) . . ?
F3 C6 C1 120.7(3) . . ?
C5 C6 C1 122.2(3) . . ?
O1 C7 O2 128.2(3) . . ?
O1 C7 C1 114.3(3) . . ?
O2 C7 C1 117.4(3) . . ?
C9 C8 C13 121.3(5) . . ?
C9 C8 H8 119.4 . . ?
C13 C8 H8 119.4 . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.9(5) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C21 C12 C11 123.0(3) . . ?
C21 C12 C13 118.8(3) . . ?
C11 C12 C13 118.2(4) . . ?
C20 C13 C8 122.3(4) . . ?
C20 C13 C12 119.5(4) . . ?
C8 C13 C12 118.2(4) . . ?
C19 C14 C15 121.2(4) . . ?
C19 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C20 C15 C16 119.4(3) . . ?
C20 C15 C14 122.4(3) . . ?
C16 C15 C14 118.1(4) . . ?
C21 C16 C17 122.7(3) . . ?
C21 C16 C15 118.7(3) . . ?
C17 C16 C15 118.5(3) . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.9(4) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C15 C20 C13 121.9(3) . . ?
C15 C20 H20 119.0 . . ?
C13 C20 H20 119.0 . . ?
C12 C21 C16 121.6(3) . . ?
C12 C21 C22 119.0(3) . . ?
C16 C21 C22 119.4(3) . . ?
O3 C22 C23 122.2(3) . . ?
O3 C22 C21 119.8(3) . . ?
C23 C22 C21 118.0(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 O2 H2 109.5 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


































































C6 C1 C2 F2 -178.1(3) . . . . ?
C7 C1 C2 F2 -0.4(5) . . . . ?
C6 C1 C2 C3 -1.5(5) . . . . ?
C7 C1 C2 C3 176.1(3) . . . . ?
F2 C2 C3 F1 -0.8(5) . . . . ?
C1 C2 C3 F1 -177.5(3) . . . . ?
F2 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
F1 C3 C4 C5 178.5(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
F1 C3 C4 Br1 -2.4(5) . . . . ?
C2 C3 C4 Br1 178.1(3) . . . . ?
C3 C4 C5 F4 179.7(3) . . . . ?
Br1 C4 C5 F4 0.5(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
Br1 C4 C5 C6 -179.5(2) . . . . ?
F4 C5 C6 F3 1.1(5) . . . . ?
C4 C5 C6 F3 -178.9(3) . . . . ?
F4 C5 C6 C1 -179.2(3) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C2 C1 C6 F3 179.8(3) . . . . ?
C7 C1 C6 F3 2.1(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C7 C1 C6 C5 -177.6(3) . . . . ?
C6 C1 C7 O1 -151.2(3) . . . . ?
C2 C1 C7 O1 31.3(5) . . . . ?
C6 C1 C7 O2 29.6(5) . . . . ?
C2 C1 C7 O2 -147.9(3) . . . . ?
C13 C8 C9 C10 0.6(8) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C21 177.1(4) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C9 C8 C13 C20 -178.4(5) . . . . ?
C9 C8 C13 C12 -0.9(7) . . . . ?
C21 C12 C13 C20 1.0(5) . . . . ?
C11 C12 C13 C20 178.2(3) . . . . ?
C21 C12 C13 C8 -176.6(4) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C19 C14 C15 C20 177.9(4) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C20 C15 C16 C21 0.4(5) . . . . ?
C14 C15 C16 C21 178.3(3) . . . . ?
C20 C15 C16 C17 -179.0(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C21 C16 C17 C18 -177.8(3) . . . . ?
C15 C16 C17 C18 1.6(5) . . . . ?
C16 C17 C18 C19 -1.1(6) . . . . ?
C15 C14 C19 C18 0.5(6) . . . . ?
C17 C18 C19 C14 0.0(6) . . . . ?
C16 C15 C20 C13 1.7(5) . . . . ?
C14 C15 C20 C13 -176.1(3) . . . . ?
C8 C13 C20 C15 175.1(4) . . . . ?
C12 C13 C20 C15 -2.4(6) . . . . ?
C11 C12 C21 C16 -176.0(3) . . . . ?
C13 C12 C21 C16 1.1(5) . . . . ?
C11 C12 C21 C22 2.0(5) . . . . ?
C13 C12 C21 C22 179.0(3) . . . . ?
C17 C16 C21 C12 177.5(3) . . . . ?
C15 C16 C21 C12 -1.8(5) . . . . ?
C17 C16 C21 C22 -0.4(5) . . . . ?
C15 C16 C21 C22 -179.7(3) . . . . ?
C12 C21 C22 O3 -99.7(4) . . . . ?
C16 C21 C22 O3 78.3(4) . . . . ?
C12 C21 C22 C23 80.9(4) . . . . ?
C16 C21 C22 C23 -101.1(4) . . . . ?



_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        26.37

_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.398

_refine_diff_density_min         -0.694

_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_exp_3352
_database_code_depnum_ccdc_archive 'CCDC 1445534'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-03-05 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H12 O, C10 H2 N4'
_chemical_formula_sum            'C26 H14 N4 O'
_chemical_formula_weight         398.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.4098(14)
_cell_length_b                   8.1627(6)
_cell_length_c                   17.1171(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.710(7)
_cell_angle_gamma                90.00
_cell_volume                     2003.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    100.6
_cell_measurement_theta_max      29.5649
_cell_measurement_theta_min      2.9655
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9790
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.06
_diffrn_ambient_temperature      100.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2918  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043 -131.0000  -93.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043  -37.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043   77.0000  -60.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0419394000
_diffrn_orient_matrix_UB_12      -0.0459670000
_diffrn_orient_matrix_UB_13      0.0047471000
_diffrn_orient_matrix_UB_21      0.0261929000
_diffrn_orient_matrix_UB_22      0.0737173000
_diffrn_orient_matrix_UB_23      0.0015869000
_diffrn_orient_matrix_UB_31      -0.0008752000
_diffrn_orient_matrix_UB_32      0.0024883000
_diffrn_orient_matrix_UB_33      0.0413401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2488
_reflns_number_total             3922
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0226P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24319(11) 0.67719(19) 0.34525(9) 0.0369(4) Uani 1 1 d . . .
N4 N 0.40823(13) 0.6197(2) -0.04913(10) 0.0258(5) Uani 1 1 d . . .
C22 C 0.26585(14) 0.3258(3) 0.02785(11) 0.0198(5) Uani 1 1 d . . .
H22 H 0.2377 0.4232 0.0447 0.024 Uiso 1 1 calc R . .
N3 N 0.52735(13) 0.2026(2) -0.12070(10) 0.0278(5) Uani 1 1 d . . .
N1 N 0.08520(14) 0.1609(2) 0.12403(11) 0.0346(5) Uani 1 1 d . . .
C2 C 0.16174(15) 0.3021(3) 0.33358(11) 0.0214(5) Uani 1 1 d . . .
C17 C 0.23044(14) 0.1740(3) 0.04619(11) 0.0195(5) Uani 1 1 d . . .
C1 C 0.21872(14) 0.4094(3) 0.29507(11) 0.0189(5) Uani 1 1 d . . .
C19 C 0.34779(14) 0.0389(3) -0.02313(11) 0.0205(5) Uani 1 1 d . . .
H19 H 0.3754 -0.0585 -0.0406 0.025 Uiso 1 1 calc R . .
C10 C 0.38787(15) 0.1193(3) 0.21646(11) 0.0238(5) Uani 1 1 d . . .
H10 H 0.4001 0.0050 0.2155 0.029 Uiso 1 1 calc R . .
C9 C 0.31155(15) 0.1782(3) 0.25569(11) 0.0209(5) Uani 1 1 d . . .
C12 C 0.42567(15) 0.3950(3) 0.18118(12) 0.0260(6) Uani 1 1 d . . .
H12 H 0.4648 0.4675 0.1560 0.031 Uiso 1 1 calc R . .
C25 C 0.46333(15) 0.1989(2) -0.08632(12) 0.0196(5) Uani 1 1 d . . .
N2 N 0.20714(14) -0.2567(2) 0.05189(11) 0.0336(5) Uani 1 1 d . . .
C20 C 0.38348(15) 0.1910(3) -0.04121(11) 0.0194(5) Uani 1 1 d . . .
C11 C 0.44350(15) 0.2243(3) 0.18035(11) 0.0270(6) Uani 1 1 d . . .
H11 H 0.4941 0.1832 0.1547 0.032 Uiso 1 1 calc R . .
C21 C 0.34256(14) 0.3353(3) -0.01531(11) 0.0180(5) Uani 1 1 d . . .
C14 C 0.29380(15) 0.3510(3) 0.25627(11) 0.0192(5) Uani 1 1 d . . .
C8 C 0.25526(14) 0.0723(3) 0.29451(11) 0.0221(5) Uani 1 1 d . . .
H8 H 0.2678 -0.0420 0.2944 0.027 Uiso 1 1 calc R . .
C13 C 0.35371(15) 0.4567(3) 0.21734(11) 0.0243(5) Uani 1 1 d . . .
H13 H 0.3429 0.5715 0.2168 0.029 Uiso 1 1 calc R . .
C23 C 0.14974(16) 0.1659(3) 0.09003(12) 0.0236(5) Uani 1 1 d . . .
C7 C 0.18120(15) 0.1302(3) 0.33334(11) 0.0210(5) Uani 1 1 d . . .
C24 C 0.23548(16) -0.1288(3) 0.03838(12) 0.0256(6) Uani 1 1 d . . .
C6 C 0.12406(15) 0.0228(3) 0.37420(11) 0.0275(6) Uani 1 1 d . . .
H6 H 0.1366 -0.0914 0.3753 0.033 Uiso 1 1 calc R . .
C15 C 0.19950(16) 0.5903(3) 0.29660(12) 0.0241(5) Uani 1 1 d . . .
C3 C 0.08607(14) 0.3596(3) 0.37459(11) 0.0252(5) Uani 1 1 d . . .
H3 H 0.0727 0.4735 0.3757 0.030 Uiso 1 1 calc R . .
C26 C 0.37901(15) 0.4935(3) -0.03441(11) 0.0194(5) Uani 1 1 d . . .
C4 C 0.03319(16) 0.2525(3) 0.41194(12) 0.0298(6) Uani 1 1 d . . .
H4 H -0.0169 0.2923 0.4387 0.036 Uiso 1 1 calc R . .
C16 C 0.12684(17) 0.6554(3) 0.23609(12) 0.0348(6) Uani 1 1 d . . .
H16A H 0.1206 0.7739 0.2430 0.052 Uiso 1 1 calc R . .
H16B H 0.0670 0.6022 0.2421 0.052 Uiso 1 1 calc R . .
H16C H 0.1453 0.6326 0.1836 0.052 Uiso 1 1 calc R . .
C5 C 0.05208(16) 0.0821(3) 0.41140(12) 0.0307(6) Uani 1 1 d . . .
H5 H 0.0141 0.0087 0.4373 0.037 Uiso 1 1 calc R . .
C18 C 0.27173(15) 0.0295(3) 0.02055(11) 0.0220(5) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.220(2) . ?
N4 C26 1.150(3) . ?
C22 H22 0.9500 . ?
C22 C17 1.388(3) . ?
C22 C21 1.392(3) . ?
N3 C25 1.143(3) . ?
N1 C23 1.146(3) . ?
C2 C1 1.409(3) . ?
C2 C7 1.431(3) . ?
C2 C3 1.433(3) . ?
C17 C23 1.447(3) . ?
C17 C18 1.411(3) . ?
C1 C14 1.408(3) . ?
C1 C15 1.503(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(3) . ?
C19 C18 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.428(3) . ?
C10 C11 1.363(3) . ?
C9 C14 1.434(3) . ?
C9 C8 1.398(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.417(3) . ?
C12 C13 1.356(3) . ?
C25 C20 1.450(3) . ?
N2 C24 1.153(3) . ?
C20 C21 1.408(3) . ?
C11 H11 0.9500 . ?
C21 C26 1.444(3) . ?
C14 C13 1.431(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.395(3) . ?
C13 H13 0.9500 . ?
C7 C6 1.432(3) . ?
C24 C18 1.438(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.359(3) . ?
C15 C16 1.495(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.361(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 C22 H22 120.0 . . ?
C17 C22 C21 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C1 C2 C7 119.01(19) . . ?
C1 C2 C3 122.2(2) . . ?
C7 C2 C3 118.8(2) . . ?
C22 C17 C23 119.36(19) . . ?
C22 C17 C18 120.03(19) . . ?
C18 C17 C23 120.59(19) . . ?
C2 C1 C15 119.07(19) . . ?
C14 C1 C2 121.4(2) . . ?
C14 C1 C15 119.50(19) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C10 C9 C14 118.76(19) . . ?
C8 C9 C10 121.7(2) . . ?
C8 C9 C14 119.53(19) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C13 C12 C11 121.1(2) . . ?
N3 C25 C20 178.4(2) . . ?
C19 C20 C25 119.25(19) . . ?
C19 C20 C21 120.07(19) . . ?
C21 C20 C25 120.68(19) . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C22 C21 C20 120.05(19) . . ?
C22 C21 C26 119.72(19) . . ?
C20 C21 C26 120.23(18) . . ?
C1 C14 C9 118.85(19) . . ?
C1 C14 C13 122.9(2) . . ?
C13 C14 C9 118.25(19) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 H8 119.2 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
N1 C23 C17 179.1(3) . . ?
C2 C7 C6 118.45(19) . . ?
C8 C7 C2 119.56(19) . . ?
C8 C7 C6 122.0(2) . . ?
N2 C24 C18 179.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
O1 C15 C1 119.96(19) . . ?
O1 C15 C16 123.0(2) . . ?
C16 C15 C1 117.01(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
N4 C26 C21 179.6(2) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C17 C18 C24 120.79(19) . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 C24 119.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 C17 C23 N1 51(17) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C22 C17 C18 C24 -179.44(19) . . . . ?
C22 C21 C26 N4 68(36) . . . . ?
N3 C25 C20 C19 -52(9) . . . . ?
N3 C25 C20 C21 128(9) . . . . ?
C2 C1 C14 C9 0.6(3) . . . . ?
C2 C1 C14 C13 -179.27(18) . . . . ?
C2 C1 C15 O1 96.4(3) . . . . ?
C2 C1 C15 C16 -84.4(2) . . . . ?
C2 C7 C6 C5 1.0(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C17 C22 C21 C20 0.8(3) . . . . ?
C17 C22 C21 C26 179.86(18) . . . . ?
C1 C2 C7 C8 -0.6(3) . . . . ?
C1 C2 C7 C6 178.61(18) . . . . ?
C1 C2 C3 C4 -179.20(19) . . . . ?
C1 C14 C13 C12 179.51(19) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C19 C20 C21 C26 -179.59(18) . . . . ?
C10 C9 C14 C1 -179.85(18) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
C10 C9 C8 C7 179.48(19) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C9 C14 C13 C12 -0.3(3) . . . . ?
C9 C8 C7 C2 0.1(3) . . . . ?
C9 C8 C7 C6 -179.08(19) . . . . ?
C25 C20 C21 C22 179.91(18) . . . . ?
C25 C20 C21 C26 0.9(3) . . . . ?
N2 C24 C18 C17 165(100) . . . . ?
N2 C24 C18 C19 -14(18) . . . . ?
C20 C19 C18 C17 0.3(3) . . . . ?
C20 C19 C18 C24 179.71(19) . . . . ?
C20 C21 C26 N4 -113(36) . . . . ?
C11 C10 C9 C14 0.3(3) . . . . ?
C11 C10 C9 C8 -178.50(19) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C21 C22 C17 C23 -179.02(18) . . . . ?
C21 C22 C17 C18 -0.5(3) . . . . ?
C14 C1 C15 O1 -82.7(3) . . . . ?
C14 C1 C15 C16 96.5(2) . . . . ?
C14 C9 C8 C7 0.7(3) . . . . ?
C8 C9 C14 C1 -1.0(3) . . . . ?
C8 C9 C14 C13 178.79(18) . . . . ?
C8 C7 C6 C5 -179.8(2) . . . . ?
C13 C12 C11 C10 -0.1(3) . . . . ?
C23 C17 C18 C19 178.44(18) . . . . ?
C23 C17 C18 C24 -1.0(3) . . . . ?
C7 C2 C1 C14 0.3(3) . . . . ?
C7 C2 C1 C15 -178.83(18) . . . . ?
C7 C2 C3 C4 -0.6(3) . . . . ?
C7 C6 C5 C4 -1.3(3) . . . . ?
C15 C1 C14 C9 179.66(18) . . . . ?
C15 C1 C14 C13 -0.2(3) . . . . ?
C3 C2 C1 C14 178.84(18) . . . . ?
C3 C2 C1 C15 -0.3(3) . . . . ?
C3 C2 C7 C8 -179.24(18) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C18 C17 C23 N1 -128(17) . . . . ?
C18 C19 C20 C25 179.53(18) . . . . ?
C18 C19 C20 C21 0.0(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_150517c_0m
_database_code_depnum_ccdc_archive 'CCDC 1445535'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F4 O3'
_chemical_formula_weight         402.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   7.912(5)
_cell_length_b                   14.265(9)
_cell_length_c                   16.133(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.637(12)
_cell_angle_gamma                90.00
_cell_volume                     1815(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2020
_cell_measurement_theta_min      2.534
_cell_measurement_theta_max      21.048

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    none
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12266
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.59
_reflns_number_total             4206
_reflns_number_gt                2380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.0383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4206
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4093(2) 0.23773(14) 0.80539(12) 0.0487(5) Uani 1 1 d . . .
C2 C 0.3833(2) 0.27809(14) 0.88101(12) 0.0486(5) Uani 1 1 d . . .
C3 C 0.4434(2) 0.23748(14) 0.95514(11) 0.0470(5) Uani 1 1 d . . .
C4 C 0.5341(2) 0.15519(13) 0.95738(11) 0.0450(4) Uani 1 1 d . . .
C5 C 0.5629(2) 0.11615(13) 0.88112(11) 0.0467(4) Uani 1 1 d . . .
C6 C 0.5018(2) 0.15620(14) 0.80771(11) 0.0481(5) Uani 1 1 d . . .
C7 C 0.8045(3) 0.42535(16) 0.86762(14) 0.0676(6) Uani 1 1 d . . .
H7 H 0.7914 0.4537 0.8156 0.081 Uiso 1 1 calc R . .
C8 C 0.7613(4) 0.47281(19) 0.93525(18) 0.0945(8) Uani 1 1 d . . .
H8 H 0.7166 0.5329 0.9290 0.113 Uiso 1 1 calc R . .
C9 C 0.7833(4) 0.4323(2) 1.01522(17) 0.1024(10) Uani 1 1 d . . .
H9 H 0.7533 0.4661 1.0611 0.123 Uiso 1 1 calc R . .
C10 C 0.8470(3) 0.3454(2) 1.02585(15) 0.0807(7) Uani 1 1 d . . .
H10 H 0.8604 0.3198 1.0790 0.097 Uiso 1 1 calc R . .
C11 C 0.8941(2) 0.29225(16) 0.95717(11) 0.0554(5) Uani 1 1 d . . .
C12 C 0.8696(2) 0.33265(14) 0.87496(11) 0.0478(5) Uani 1 1 d . . .
C13 C 0.9152(2) 0.27941(13) 0.80704(10) 0.0410(4) Uani 1 1 d . . .
C14 C 0.9834(2) 0.18842(13) 0.81734(11) 0.0422(4) Uani 1 1 d . . .
C15 C 1.0127(2) 0.15140(14) 0.89978(12) 0.0478(5) Uani 1 1 d . . .
C16 C 0.9659(2) 0.20414(16) 0.96658(12) 0.0557(5) Uani 1 1 d . . .
H16 H 0.9836 0.1792 1.0198 0.067 Uiso 1 1 calc R . .
C17 C 1.0904(2) 0.06136(16) 0.90988(14) 0.0623(6) Uani 1 1 d . . .
H17 H 1.1149 0.0375 0.9632 0.075 Uiso 1 1 calc R . .
C18 C 1.1287(3) 0.01044(17) 0.84404(16) 0.0709(6) Uani 1 1 d . . .
H18 H 1.1802 -0.0478 0.8523 0.085 Uiso 1 1 calc R . .
C19 C 1.0917(3) 0.04417(16) 0.76242(14) 0.0652(6) Uani 1 1 d . . .
H19 H 1.1146 0.0070 0.7173 0.078 Uiso 1 1 calc R . .
C20 C 1.0231(2) 0.13032(14) 0.74935(12) 0.0533(5) Uani 1 1 d . . .
H20 H 1.0015 0.1521 0.6952 0.064 Uiso 1 1 calc R . .
C21 C 0.9004(2) 0.31972(13) 0.72119(11) 0.0437(4) Uani 1 1 d . . .
C22 C 0.7300(2) 0.33210(16) 0.67666(12) 0.0622(6) Uani 1 1 d . . .
H22A H 0.7397 0.3694 0.6278 0.093 Uiso 1 1 calc R . .
H22B H 0.6565 0.3630 0.7125 0.093 Uiso 1 1 calc R . .
H22C H 0.6837 0.2719 0.6609 0.093 Uiso 1 1 calc R . .
F1 F 0.29378(14) 0.35821(9) 0.88253(8) 0.0738(4) Uani 1 1 d . . .
F2 F 0.41201(15) 0.27904(9) 1.02781(7) 0.0706(4) Uani 1 1 d . . .
F3 F 0.65202(15) 0.03581(8) 0.87945(7) 0.0689(4) Uani 1 1 d . . .
F4 F 0.53252(15) 0.11428(10) 0.73545(7) 0.0743(4) Uani 1 1 d . . .
O1 O 0.35385(16) 0.27615(12) 0.73076(8) 0.0686(4) Uani 1 1 d . . .
H1 H 0.2564 0.2951 0.7328 0.103 Uiso 1 1 calc R . .
O2 O 0.59865(18) 0.11206(11) 1.02767(8) 0.0640(4) Uani 1 1 d . . .
H2 H 0.5606 0.1368 1.0681 0.096 Uiso 1 1 calc R . .
O3 O 1.02900(15) 0.33777(10) 0.68695(7) 0.0543(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.363(2) . ?
C1 C6 1.373(3) . ?
C1 C2 1.379(3) . ?
C2 F1 1.346(2) . ?
C2 C3 1.379(3) . ?
C3 F2 1.354(2) . ?
C3 C4 1.375(3) . ?
C4 O2 1.353(2) . ?
C4 C5 1.386(3) . ?
C5 F3 1.347(2) . ?
C5 C6 1.367(3) . ?
C6 F4 1.349(2) . ?
C7 C8 1.351(3) . ?
C7 C12 1.421(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.344(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.417(3) . ?
C10 H10 0.9300 . ?
C11 C16 1.383(3) . ?
C11 C12 1.445(3) . ?
C12 C13 1.404(3) . ?
C13 C14 1.410(3) . ?
C13 C21 1.495(3) . ?
C14 C20 1.430(3) . ?
C14 C15 1.432(3) . ?
C15 C16 1.389(3) . ?
C15 C17 1.428(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.341(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.410(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.353(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O3 1.224(2) . ?
C21 C22 1.486(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 119.83(18) . . ?
O1 C1 C2 123.58(19) . . ?
C6 C1 C2 116.54(17) . . ?
F1 C2 C3 119.10(17) . . ?
F1 C2 C1 119.14(17) . . ?
C3 C2 C1 121.75(18) . . ?
F2 C3 C4 118.87(17) . . ?
F2 C3 C2 119.50(17) . . ?
C4 C3 C2 121.63(17) . . ?
O2 C4 C3 124.82(17) . . ?
O2 C4 C5 118.89(17) . . ?
C3 C4 C5 116.27(17) . . ?
F3 C5 C6 119.14(16) . . ?
F3 C5 C4 118.90(16) . . ?
C6 C5 C4 121.95(18) . . ?
F4 C6 C5 119.17(18) . . ?
F4 C6 C1 118.98(17) . . ?
C5 C6 C1 121.84(17) . . ?
C8 C7 C12 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C12 C7 H7 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C16 C11 C10 122.1(2) . . ?
C16 C11 C12 119.15(18) . . ?
C10 C11 C12 118.7(2) . . ?
C13 C12 C7 123.57(18) . . ?
C13 C12 C11 118.46(18) . . ?
C7 C12 C11 117.95(18) . . ?
C12 C13 C14 121.73(16) . . ?
C12 C13 C21 120.58(17) . . ?
C14 C13 C21 117.62(16) . . ?
C13 C14 C20 123.28(16) . . ?
C13 C14 C15 118.71(17) . . ?
C20 C14 C15 118.00(18) . . ?
C16 C15 C17 122.56(18) . . ?
C16 C15 C14 119.18(18) . . ?
C17 C15 C14 118.27(19) . . ?
C11 C16 C15 122.69(18) . . ?
C11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C18 C17 C15 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C15 C17 H17 119.4 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C14 121.14(19) . . ?
C19 C20 H20 119.4 . . ?
C14 C20 H20 119.4 . . ?
O3 C21 C22 120.78(17) . . ?
O3 C21 C13 119.55(15) . . ?
C22 C21 C13 119.58(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 F1 2.3(3) . . . . ?
C6 C1 C2 F1 179.84(16) . . . . ?
O1 C1 C2 C3 -179.14(16) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
F1 C2 C3 F2 -0.3(3) . . . . ?
C1 C2 C3 F2 -178.87(16) . . . . ?
F1 C2 C3 C4 179.35(16) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
F2 C3 C4 O2 -1.2(3) . . . . ?
C2 C3 C4 O2 179.14(17) . . . . ?
F2 C3 C4 C5 -179.74(15) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
O2 C4 C5 F3 1.0(3) . . . . ?
C3 C4 C5 F3 179.56(15) . . . . ?
O2 C4 C5 C6 -179.78(17) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
F3 C5 C6 F4 0.0(3) . . . . ?
C4 C5 C6 F4 -179.28(16) . . . . ?
F3 C5 C6 C1 179.61(16) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
O1 C1 C6 F4 -1.7(3) . . . . ?
C2 C1 C6 F4 -179.34(15) . . . . ?
O1 C1 C6 C5 178.70(16) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C16 177.5(2) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C8 C7 C12 C13 179.4(2) . . . . ?
C8 C7 C12 C11 -2.3(3) . . . . ?
C16 C11 C12 C13 1.9(3) . . . . ?
C10 C11 C12 C13 -179.51(17) . . . . ?
C16 C11 C12 C7 -176.51(17) . . . . ?
C10 C11 C12 C7 2.1(3) . . . . ?
C7 C12 C13 C14 178.38(17) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C7 C12 C13 C21 1.3(3) . . . . ?
C11 C12 C13 C21 -176.97(15) . . . . ?
C12 C13 C14 C20 176.67(16) . . . . ?
C21 C13 C14 C20 -6.2(2) . . . . ?
C12 C13 C14 C15 -2.5(2) . . . . ?
C21 C13 C14 C15 174.63(14) . . . . ?
C13 C14 C15 C16 3.0(2) . . . . ?
C20 C14 C15 C16 -176.23(16) . . . . ?
C13 C14 C15 C17 -176.60(15) . . . . ?
C20 C14 C15 C17 4.2(2) . . . . ?
C10 C11 C16 C15 -179.95(18) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
C17 C15 C16 C11 178.51(17) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C16 C15 C17 C18 177.54(18) . . . . ?
C14 C15 C17 C18 -2.9(3) . . . . ?
C15 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C20 2.7(3) . . . . ?
C18 C19 C20 C14 -1.3(3) . . . . ?
C13 C14 C20 C19 178.61(17) . . . . ?
C15 C14 C20 C19 -2.2(3) . . . . ?
C12 C13 C21 O3 110.6(2) . . . . ?
C14 C13 C21 O3 -66.6(2) . . . . ?
C12 C13 C21 C22 -73.0(2) . . . . ?
C14 C13 C21 C22 109.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_exp_3230
_database_code_depnum_ccdc_archive 'CCDC 1445536'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-03-05 downloaded from the CCDC.
;
_audit_creation_date             2015-05-26
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 F8, C16 H12 O'
_chemical_formula_sum            'C26 H12 F8 O'
_chemical_formula_weight         492.36
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5602(7)
_cell_length_b                   13.8550(5)
_cell_length_c                   13.7535(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.907(6)
_cell_angle_gamma                90.00
_cell_volume                     2013.85(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2494
_cell_measurement_temperature    103.4
_cell_measurement_theta_max      29.5724
_cell_measurement_theta_min      2.9348
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10894
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.94
_diffrn_ambient_temperature      103.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -63.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  121.0000   11.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00  -46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  152.0000 -128.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00   12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -77.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega  -32.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000   60.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0272424000
_diffrn_orient_matrix_UB_12      -0.0439078000
_diffrn_orient_matrix_UB_13      -0.0069743000
_diffrn_orient_matrix_UB_21      -0.0532367000
_diffrn_orient_matrix_UB_22      -0.0256882000
_diffrn_orient_matrix_UB_23      -0.0003708000
_diffrn_orient_matrix_UB_31      -0.0304402000
_diffrn_orient_matrix_UB_32      0.0056468000
_diffrn_orient_matrix_UB_33      -0.0559666000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2794
_reflns_number_total             3947
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.0893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1190
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F7 F 0.78340(12) 0.10820(9) 0.35007(9) 0.0340(3) Uani 1 1 d . . .
F3 F 1.15133(13) 0.40440(10) 0.09895(9) 0.0398(4) Uani 1 1 d . . .
F5 F 0.82540(12) 0.42646(8) 0.25830(9) 0.0299(3) Uani 1 1 d . . .
F8 F 0.96038(13) 0.04743(8) 0.28441(9) 0.0323(3) Uani 1 1 d . . .
F6 F 0.71970(12) 0.29478(9) 0.33962(9) 0.0319(3) Uani 1 1 d . . .
F4 F 0.97406(13) 0.46487(8) 0.16430(9) 0.0332(3) Uani 1 1 d . . .
C6 C 0.95067(19) 0.30638(14) 0.22212(14) 0.0197(5) Uani 1 1 d . . .
C10 C 0.9272(2) 0.14171(14) 0.27337(14) 0.0221(5) Uani 1 1 d . . .
C8 C 0.80535(19) 0.26815(15) 0.30279(14) 0.0223(5) Uani 1 1 d . . .
F1 F 1.10828(12) 0.08589(9) 0.19004(9) 0.0370(4) Uani 1 1 d . . .
C7 C 0.86010(19) 0.33414(14) 0.26149(14) 0.0199(5) Uani 1 1 d . . .
C12 C 0.63809(18) 0.21118(14) 0.00876(14) 0.0193(4) Uani 1 1 d . . .
C5 C 1.0088(2) 0.37167(15) 0.17683(15) 0.0242(5) Uani 1 1 d . . .
F2 F 1.21326(12) 0.21747(10) 0.10758(9) 0.0404(4) Uani 1 1 d . . .
C24 C 0.79122(18) 0.20065(14) -0.07237(14) 0.0191(5) Uani 1 1 d . . .
C17 C 0.64955(19) 0.31462(14) 0.01142(14) 0.0199(5) Uani 1 1 d . . .
C19 C 0.80213(19) 0.30387(14) -0.06893(14) 0.0203(5) Uani 1 1 d . . .
C3 C 1.1289(2) 0.24492(17) 0.14600(15) 0.0281(5) Uani 1 1 d . . .
C4 C 1.0965(2) 0.34199(16) 0.14148(15) 0.0260(5) Uani 1 1 d . . .
C1 C 0.98493(19) 0.20656(14) 0.22806(14) 0.0202(5) Uani 1 1 d . . .
C9 C 0.8387(2) 0.17075(15) 0.30829(14) 0.0228(5) Uani 1 1 d . . .
C11 C 0.70881(18) 0.15663(14) -0.03378(13) 0.0187(4) Uani 1 1 d . . .
C2 C 1.0750(2) 0.17912(15) 0.18814(15) 0.0246(5) Uani 1 1 d . . .
C13 C 0.5549(2) 0.16840(16) 0.05025(14) 0.0250(5) Uani 1 1 d . . .
H13 H 0.5472 0.1016 0.0501 0.030 Uiso 1 1 calc R . .
C25 C 0.6930(2) 0.04860(15) -0.04134(15) 0.0249(5) Uani 1 1 d . . .
C23 C 0.8631(2) 0.14766(16) -0.11758(14) 0.0241(5) Uani 1 1 d . . .
H23 H 0.8550 0.0809 -0.1229 0.029 Uiso 1 1 calc R . .
C15 C 0.4971(2) 0.32549(17) 0.09092(15) 0.0309(6) Uani 1 1 d . . .
H15 H 0.4492 0.3625 0.1174 0.037 Uiso 1 1 calc R . .
C18 C 0.73063(19) 0.35777(15) -0.02763(14) 0.0219(5) Uani 1 1 d . . .
H18 H 0.7374 0.4247 -0.0262 0.026 Uiso 1 1 calc R . .
C16 C 0.5758(2) 0.36947(16) 0.05375(14) 0.0266(5) Uani 1 1 d . . .
H16 H 0.5820 0.4364 0.0558 0.032 Uiso 1 1 calc R . .
C26 C 0.7942(2) -0.01122(16) 0.03858(16) 0.0385(6) Uani 1 1 d . . .
H26A H 0.8755 0.0155 0.0506 0.058 Uiso 1 1 calc R . .
H26B H 0.7891 -0.0760 0.0125 0.058 Uiso 1 1 calc R . .
H26C H 0.7833 -0.0117 0.1041 0.058 Uiso 1 1 calc R . .
C21 C 0.9549(2) 0.29455(17) -0.14779(16) 0.0312(5) Uani 1 1 d . . .
H21 H 1.0101 0.3249 -0.1718 0.037 Uiso 1 1 calc R . .
C20 C 0.8861(2) 0.34777(16) -0.10805(15) 0.0276(5) Uani 1 1 d . . .
H20 H 0.8939 0.4146 -0.1062 0.033 Uiso 1 1 calc R . .
C14 C 0.4870(2) 0.22339(17) 0.08977(15) 0.0307(5) Uani 1 1 d . . .
H14 H 0.4335 0.1940 0.1163 0.037 Uiso 1 1 calc R . .
C22 C 0.9431(2) 0.19255(16) -0.15304(15) 0.0291(5) Uani 1 1 d . . .
H22 H 0.9903 0.1563 -0.1808 0.035 Uiso 1 1 calc R . .
O1 O 0.59866(16) 0.01316(11) -0.10869(12) 0.0397(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F7 C9 1.337(2) . ?
F3 C4 1.339(2) . ?
F5 C7 1.336(2) . ?
F8 C10 1.353(2) . ?
F6 C8 1.334(2) . ?
F4 C5 1.343(2) . ?
C6 C7 1.413(3) . ?
C6 C5 1.413(3) . ?
C6 C1 1.432(3) . ?
C10 C1 1.407(3) . ?
C10 C9 1.355(3) . ?
C8 C7 1.360(3) . ?
C8 C9 1.397(3) . ?
F1 C2 1.345(2) . ?
C12 C17 1.438(3) . ?
C12 C11 1.403(3) . ?
C12 C13 1.431(3) . ?
C5 C4 1.353(3) . ?
F2 C3 1.339(2) . ?
C24 C19 1.435(3) . ?
C24 C11 1.404(3) . ?
C24 C23 1.427(3) . ?
C17 C18 1.390(3) . ?
C17 C16 1.430(3) . ?
C19 C18 1.394(3) . ?
C19 C20 1.424(3) . ?
C3 C4 1.391(3) . ?
C3 C2 1.359(3) . ?
C1 C2 1.412(3) . ?
C11 C25 1.506(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.355(3) . ?
C25 C26 1.490(3) . ?
C25 O1 1.213(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.358(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.356(3) . ?
C15 C14 1.419(3) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C20 1.351(3) . ?
C21 C22 1.419(3) . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C6 C5 123.59(18) . . ?
C7 C6 C1 118.15(18) . . ?
C5 C6 C1 118.25(18) . . ?
F8 C10 C1 120.17(19) . . ?
F8 C10 C9 117.88(18) . . ?
C9 C10 C1 121.95(18) . . ?
F6 C8 C7 121.01(18) . . ?
F6 C8 C9 118.54(18) . . ?
C7 C8 C9 120.44(19) . . ?
F5 C7 C6 120.49(18) . . ?
F5 C7 C8 118.22(18) . . ?
C8 C7 C6 121.29(18) . . ?
C11 C12 C17 118.95(18) . . ?
C11 C12 C13 122.85(18) . . ?
C13 C12 C17 118.20(18) . . ?
F4 C5 C6 120.06(18) . . ?
F4 C5 C4 118.36(18) . . ?
C4 C5 C6 121.53(19) . . ?
C11 C24 C19 118.99(18) . . ?
C11 C24 C23 123.07(18) . . ?
C23 C24 C19 117.93(18) . . ?
C18 C17 C12 119.22(18) . . ?
C18 C17 C16 122.36(18) . . ?
C16 C17 C12 118.42(18) . . ?
C18 C19 C24 119.25(18) . . ?
C18 C19 C20 122.21(18) . . ?
C20 C19 C24 118.54(18) . . ?
F2 C3 C4 118.9(2) . . ?
F2 C3 C2 120.7(2) . . ?
C2 C3 C4 120.4(2) . . ?
F3 C4 C5 121.1(2) . . ?
F3 C4 C3 118.52(19) . . ?
C5 C4 C3 120.3(2) . . ?
C10 C1 C6 118.19(18) . . ?
C10 C1 C2 123.88(19) . . ?
C2 C1 C6 117.93(19) . . ?
F7 C9 C10 121.40(18) . . ?
F7 C9 C8 118.64(18) . . ?
C10 C9 C8 119.95(19) . . ?
C12 C11 C24 121.51(18) . . ?
C12 C11 C25 119.30(18) . . ?
C24 C11 C25 119.16(18) . . ?
F1 C2 C3 118.42(19) . . ?
F1 C2 C1 120.07(19) . . ?
C3 C2 C1 121.50(19) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
C26 C25 C11 117.70(18) . . ?
O1 C25 C11 120.09(19) . . ?
O1 C25 C26 122.2(2) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 C24 121.5(2) . . ?
C22 C23 H23 119.3 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C17 C18 C19 122.06(18) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C17 C16 H16 119.4 . . ?
C15 C16 C17 121.1(2) . . ?
C15 C16 H16 119.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(2) . . ?
C21 C20 H20 119.2 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F8 C10 C1 C6 -177.39(16) . . . . ?
F8 C10 C1 C2 2.5(3) . . . . ?
F8 C10 C9 F7 -1.6(3) . . . . ?
F8 C10 C9 C8 177.24(17) . . . . ?
F6 C8 C7 F5 -0.3(3) . . . . ?
F6 C8 C7 C6 -179.86(16) . . . . ?
F6 C8 C9 F7 0.1(3) . . . . ?
F6 C8 C9 C10 -178.76(17) . . . . ?
F4 C5 C4 F3 2.7(3) . . . . ?
F4 C5 C4 C3 -175.49(18) . . . . ?
C6 C5 C4 F3 -179.82(17) . . . . ?
C6 C5 C4 C3 2.0(3) . . . . ?
C6 C1 C2 F1 -178.66(17) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C10 C1 C2 F1 1.5(3) . . . . ?
C10 C1 C2 C3 -179.38(18) . . . . ?
C7 C6 C5 F4 -3.5(3) . . . . ?
C7 C6 C5 C4 179.07(18) . . . . ?
C7 C6 C1 C10 -0.4(3) . . . . ?
C7 C6 C1 C2 179.70(17) . . . . ?
C7 C8 C9 F7 179.57(17) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C12 C17 C18 C19 -0.4(3) . . . . ?
C12 C17 C16 C15 0.2(3) . . . . ?
C12 C11 C25 C26 -103.5(2) . . . . ?
C12 C11 C25 O1 74.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C5 C6 C7 F5 -0.6(3) . . . . ?
C5 C6 C7 C8 178.91(18) . . . . ?
C5 C6 C1 C10 179.86(17) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
F2 C3 C4 F3 -0.1(3) . . . . ?
F2 C3 C4 C5 178.10(17) . . . . ?
F2 C3 C2 F1 -0.2(3) . . . . ?
F2 C3 C2 C1 -179.35(16) . . . . ?
C24 C19 C18 C17 0.6(3) . . . . ?
C24 C19 C20 C21 0.0(3) . . . . ?
C24 C11 C25 C26 78.3(2) . . . . ?
C24 C11 C25 O1 -103.9(2) . . . . ?
C24 C23 C22 C21 -1.3(3) . . . . ?
C17 C12 C11 C24 0.8(3) . . . . ?
C17 C12 C11 C25 -177.31(17) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C19 C24 C11 C12 -0.6(3) . . . . ?
C19 C24 C11 C25 177.52(17) . . . . ?
C19 C24 C23 C22 2.3(3) . . . . ?
C4 C3 C2 F1 179.41(17) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C1 C6 C7 F5 179.64(17) . . . . ?
C1 C6 C7 C8 -0.8(3) . . . . ?
C1 C6 C5 F4 176.23(17) . . . . ?
C1 C6 C5 C4 -1.2(3) . . . . ?
C1 C10 C9 F7 179.19(16) . . . . ?
C1 C10 C9 C8 -2.0(3) . . . . ?
C9 C10 C1 C6 1.8(3) . . . . ?
C9 C10 C1 C2 -178.30(18) . . . . ?
C9 C8 C7 F5 -179.75(17) . . . . ?
C9 C8 C7 C6 0.7(3) . . . . ?
C11 C12 C17 C18 -0.3(3) . . . . ?
C11 C12 C17 C16 179.24(16) . . . . ?
C11 C12 C13 C14 -179.32(18) . . . . ?
C11 C24 C19 C18 -0.1(3) . . . . ?
C11 C24 C19 C20 179.87(17) . . . . ?
C11 C24 C23 C22 -179.23(18) . . . . ?
C2 C3 C4 F3 -179.73(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C13 C12 C17 C18 179.46(17) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C13 C12 C11 C24 -178.97(17) . . . . ?
C13 C12 C11 C25 2.9(3) . . . . ?
C23 C24 C19 C18 178.42(16) . . . . ?
C23 C24 C19 C20 -1.6(3) . . . . ?
C23 C24 C11 C12 -179.03(17) . . . . ?
C23 C24 C11 C25 -0.9(3) . . . . ?
C18 C17 C16 C15 179.73(18) . . . . ?
C18 C19 C20 C21 179.96(18) . . . . ?
C16 C17 C18 C19 -179.90(17) . . . . ?
C16 C15 C14 C13 -0.8(3) . . . . ?
C20 C19 C18 C17 -179.39(17) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C22 C21 C20 C19 1.0(3) . . . . ?

