# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_2q_18srv269
_database_code_depnum_ccdc_archive 'CCDC 1856218'
_audit_update_record             
;
2018-07-16 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-06-26
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H12 F8 N2 O2'
_chemical_formula_sum            'C30 H12 F8 N2 O2'
_chemical_formula_weight         584.42
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_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                   13.2804(5)
_cell_length_b                   8.7572(4)
_cell_length_c                   21.1478(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.2235(15)
_cell_angle_gamma                90
_cell_volume                     2361.53(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.60
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;    
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0912 before and 0.0401 after correction. 
The Ratio of minimum to maximum transmission is 0.9582. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.498
_diffrn_reflns_theta_min         2.187
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5390
_reflns_number_total             6565
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+1.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.27353(6) -0.22978(10) 0.34379(4) 0.02599(18) Uani 1 1 d . . . . .
F2 F 0.27754(7) -0.23889(11) 0.47211(4) 0.0323(2) Uani 1 1 d . . . . .
F3 F 0.00493(7) 0.08715(12) 0.44008(4) 0.0334(2) Uani 1 1 d . . . . .
F4 F -0.01184(6) 0.11185(9) 0.31018(4) 0.02242(17) Uani 1 1 d . . . . .
F5 F 0.01409(6) 0.09929(10) 0.11270(4) 0.02770(19) Uani 1 1 d . . . . .
F6 F 0.08858(9) 0.09812(13) 0.00519(4) 0.0444(3) Uani 1 1 d . . . . .
F7 F 0.32280(7) 0.46747(11) 0.08941(5) 0.0360(2) Uani 1 1 d . . . . .
F8 F 0.26148(7) 0.48657(9) 0.20043(4) 0.02611(18) Uani 1 1 d . . . . .
O1 O 0.11502(6) -0.05146(10) 0.25627(4) 0.01604(17) Uani 1 1 d . . . . .
O2 O 0.10040(6) 0.28739(10) 0.21481(4) 0.01598(17) Uani 1 1 d . . . . .
N1 N 0.14170(9) -0.07500(15) 0.45592(5) 0.0243(2) Uani 1 1 d . . . . .
N2 N 0.20557(10) 0.28190(15) 0.04795(6) 0.0275(3) Uani 1 1 d . . . . .
C1 C 0.27245(9) 0.07633(13) 0.24796(5) 0.0122(2) Uani 1 1 d . . . . .
C2 C 0.20167(9) -0.04124(14) 0.23045(6) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.20339(10) -0.14958(14) 0.18165(6) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.28092(10) -0.14150(14) 0.15090(6) 0.0184(2) Uani 1 1 d . . . . .
C5 C 0.44260(10) -0.02174(14) 0.13826(6) 0.0170(2) Uani 1 1 d . . . . .
C6 C 0.51865(10) 0.08771(15) 0.15561(6) 0.0184(2) Uani 1 1 d . . . . .
C7 C 0.51364(10) 0.19961(15) 0.20266(6) 0.0180(2) Uani 1 1 d . . . . .
C8 C 0.43371(9) 0.19840(14) 0.23220(6) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.35570(9) 0.08332(13) 0.21696(5) 0.0121(2) Uani 1 1 d . . . . .
C10 C 0.35953(9) -0.02747(13) 0.16826(6) 0.0141(2) Uani 1 1 d . . . . .
C11 C 0.13102(9) -0.05650(14) 0.32237(6) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.20552(9) -0.14634(14) 0.36542(6) 0.0177(2) Uani 1 1 d . . . . .
C13 C 0.20653(10) -0.15011(16) 0.43079(6) 0.0217(3) Uani 1 1 d . . . . .
C14 C 0.07173(10) 0.01059(16) 0.41519(6) 0.0220(3) Uani 1 1 d . . . . .
C15 C 0.06273(9) 0.02448(14) 0.34899(6) 0.0169(2) Uani 1 1 d . . . . .
C21 C 0.25786(9) 0.19659(13) 0.29471(5) 0.0124(2) Uani 1 1 d . . . . .
C22 C 0.17383(9) 0.29447(13) 0.27727(6) 0.0137(2) Uani 1 1 d . . . . .
C23 C 0.14961(10) 0.40032(14) 0.32084(6) 0.0167(2) Uani 1 1 d . . . . .
C24 C 0.21473(10) 0.41138(14) 0.38332(6) 0.0175(2) Uani 1 1 d . . . . .
C25 C 0.37644(10) 0.33495(16) 0.46787(6) 0.0194(2) Uani 1 1 d . . . . .
C26 C 0.46308(10) 0.24501(16) 0.48745(6) 0.0210(3) Uani 1 1 d . . . . .
C27 C 0.48385(10) 0.13388(15) 0.44427(6) 0.0187(2) Uani 1 1 d . . . . .
C28 C 0.41743(9) 0.11581(14) 0.38225(6) 0.0154(2) Uani 1 1 d . . . . .
C29 C 0.32756(9) 0.20989(13) 0.35983(5) 0.0125(2) Uani 1 1 d . . . . .
C30 C 0.30603(9) 0.32016(14) 0.40390(6) 0.0149(2) Uani 1 1 d . . . . .
C31 C 0.13772(9) 0.28906(14) 0.16103(6) 0.0147(2) Uani 1 1 d . . . . .
C32 C 0.09162(10) 0.19285(15) 0.10889(6) 0.0189(2) Uani 1 1 d . . . . .
C33 C 0.12967(12) 0.19381(17) 0.05454(6) 0.0255(3) Uani 1 1 d . . . . .
C34 C 0.24633(11) 0.37583(16) 0.09624(7) 0.0232(3) Uani 1 1 d . . . . .
C35 C 0.21588(10) 0.38674(14) 0.15333(6) 0.0182(2) Uani 1 1 d . . . . .
H3 H 0.1520(13) -0.225(2) 0.1705(8) 0.023(4) Uiso 1 1 d . . . . .
H4 H 0.2831(13) -0.216(2) 0.1175(8) 0.025(4) Uiso 1 1 d . . . . .
H5 H 0.4463(13) -0.100(2) 0.1071(8) 0.028(4) Uiso 1 1 d . . . . .
H6 H 0.5772(13) 0.088(2) 0.1369(8) 0.024(4) Uiso 1 1 d . . . . .
H7 H 0.5678(13) 0.2771(19) 0.2157(8) 0.021(4) Uiso 1 1 d . . . . .
H8 H 0.4330(13) 0.274(2) 0.2641(8) 0.025(4) Uiso 1 1 d . . . . .
H23 H 0.0900(12) 0.4617(18) 0.3075(7) 0.016(4) Uiso 1 1 d . . . . .
H24 H 0.2005(12) 0.4835(19) 0.4147(8) 0.019(4) Uiso 1 1 d . . . . .
H25 H 0.3611(13) 0.410(2) 0.4969(8) 0.026(4) Uiso 1 1 d . . . . .
H26 H 0.5117(13) 0.255(2) 0.5298(8) 0.026(4) Uiso 1 1 d . . . . .
H27 H 0.5451(12) 0.0687(19) 0.4579(8) 0.019(4) Uiso 1 1 d . . . . .
H28 H 0.4332(12) 0.0392(18) 0.3534(7) 0.016(4) Uiso 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
F1 C12 1.3379(14) . ?
F2 C13 1.3404(15) . ?
F3 C14 1.3322(15) . ?
F4 C15 1.3362(14) . ?
F5 C32 1.3358(15) . ?
F6 C33 1.3307(16) . ?
F7 C34 1.3334(15) . ?
F8 C35 1.3363(15) . ?
O1 C2 1.4076(13) . ?
O1 C11 1.3549(14) . ?
O2 C22 1.4071(13) . ?
O2 C31 1.3617(14) . ?
N1 C13 1.3085(18) . ?
N1 C14 1.3115(18) . ?
N2 C33 1.3073(19) . ?
N2 C34 1.3052(19) . ?
C1 C2 1.3733(16) . ?
C1 C9 1.4355(15) . ?
C1 C21 1.4939(15) . ?
C2 C3 1.4067(16) . ?
C3 C4 1.3646(17) . ?
C3 H3 0.931(17) . ?
C4 C10 1.4170(17) . ?
C4 H4 0.965(18) . ?
C5 C6 1.3661(18) . ?
C5 C10 1.4188(16) . ?
C5 H5 0.963(18) . ?
C6 C7 1.4113(18) . ?
C6 H6 0.965(17) . ?
C7 C8 1.3739(16) . ?
C7 H7 0.971(17) . ?
C8 C9 1.4164(16) . ?
C8 H8 0.944(17) . ?
C9 C10 1.4263(15) . ?
C11 C12 1.3869(17) . ?
C11 C15 1.3883(16) . ?
C12 C13 1.3790(18) . ?
C14 C15 1.3768(18) . ?
C21 C22 1.3733(16) . ?
C21 C29 1.4333(15) . ?
C22 C23 1.4061(16) . ?
C23 C24 1.3655(17) . ?
C23 H23 0.933(16) . ?
C24 C30 1.4153(17) . ?
C24 H24 0.972(16) . ?
C25 C26 1.3599(19) . ?
C25 C30 1.4193(16) . ?
C25 H25 0.962(18) . ?
C26 C27 1.4136(19) . ?
C26 H26 0.950(17) . ?
C27 C28 1.3699(17) . ?
C27 H27 0.969(16) . ?
C28 C29 1.4183(16) . ?
C28 H28 0.968(16) . ?
C29 C30 1.4255(16) . ?
C31 C32 1.3868(17) . ?
C31 C35 1.3893(17) . ?
C32 C33 1.3788(18) . ?
C34 C35 1.3795(18) . ?

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
C11 O1 C2 119.53(9) . . ?
C31 O2 C22 117.72(9) . . ?
C13 N1 C14 116.51(11) . . ?
C34 N2 C33 116.88(12) . . ?
C2 C1 C9 117.73(10) . . ?
C2 C1 C21 120.09(10) . . ?
C9 C1 C21 122.07(10) . . ?
C1 C2 O1 121.01(10) . . ?
C1 C2 C3 123.59(11) . . ?
C3 C2 O1 115.10(10) . . ?
C2 C3 H3 120.2(10) . . ?
C4 C3 C2 118.93(11) . . ?
C4 C3 H3 120.9(10) . . ?
C3 C4 C10 120.83(11) . . ?
C3 C4 H4 119.6(10) . . ?
C10 C4 H4 119.5(10) . . ?
C6 C5 C10 120.90(11) . . ?
C6 C5 H5 120.7(10) . . ?
C10 C5 H5 118.4(11) . . ?
C5 C6 C7 119.97(11) . . ?
C5 C6 H6 120.9(10) . . ?
C7 C6 H6 119.1(10) . . ?
C6 C7 H7 120.5(10) . . ?
C8 C7 C6 120.65(12) . . ?
C8 C7 H7 118.8(10) . . ?
C7 C8 C9 120.73(11) . . ?
C7 C8 H8 118.8(10) . . ?
C9 C8 H8 120.4(10) . . ?
C8 C9 C1 122.29(10) . . ?
C8 C9 C10 118.48(10) . . ?
C10 C9 C1 119.22(10) . . ?
C4 C10 C5 121.18(11) . . ?
C4 C10 C9 119.61(10) . . ?
C5 C10 C9 119.20(11) . . ?
O1 C11 C12 124.97(11) . . ?
O1 C11 C15 118.02(11) . . ?
C12 C11 C15 116.79(11) . . ?
F1 C12 C11 120.76(11) . . ?
F1 C12 C13 120.75(11) . . ?
C13 C12 C11 118.48(11) . . ?
F2 C13 C12 118.38(12) . . ?
N1 C13 F2 116.72(12) . . ?
N1 C13 C12 124.88(12) . . ?
F3 C14 C15 118.63(12) . . ?
N1 C14 F3 117.13(12) . . ?
N1 C14 C15 124.24(12) . . ?
F4 C15 C11 119.96(11) . . ?
F4 C15 C14 120.94(11) . . ?
C14 C15 C11 119.08(12) . . ?
C22 C21 C1 120.54(10) . . ?
C22 C21 C29 117.75(10) . . ?
C29 C21 C1 121.65(10) . . ?
C21 C22 O2 121.51(10) . . ?
C21 C22 C23 123.57(11) . . ?
C23 C22 O2 114.75(10) . . ?
C22 C23 H23 120.8(9) . . ?
C24 C23 C22 118.80(11) . . ?
C24 C23 H23 120.4(9) . . ?
C23 C24 C30 120.94(11) . . ?
C23 C24 H24 121.0(9) . . ?
C30 C24 H24 118.0(9) . . ?
C26 C25 C30 120.90(12) . . ?
C26 C25 H25 121.0(10) . . ?
C30 C25 H25 118.1(10) . . ?
C25 C26 C27 120.21(12) . . ?
C25 C26 H26 121.8(10) . . ?
C27 C26 H26 118.0(10) . . ?
C26 C27 H27 120.8(9) . . ?
C28 C27 C26 120.55(12) . . ?
C28 C27 H27 118.6(9) . . ?
C27 C28 C29 120.64(11) . . ?
C27 C28 H28 119.2(9) . . ?
C29 C28 H28 120.1(9) . . ?
C28 C29 C21 122.09(10) . . ?
C28 C29 C30 118.59(10) . . ?
C30 C29 C21 119.31(10) . . ?
C24 C30 C25 121.42(11) . . ?
C24 C30 C29 119.50(10) . . ?
C25 C30 C29 119.08(11) . . ?
O2 C31 C32 118.34(11) . . ?
O2 C31 C35 124.24(11) . . ?
C32 C31 C35 117.34(11) . . ?
F5 C32 C31 120.08(11) . . ?
F5 C32 C33 121.48(12) . . ?
C33 C32 C31 118.42(12) . . ?
F6 C33 C32 118.98(13) . . ?
N2 C33 F6 116.58(12) . . ?
N2 C33 C32 124.43(13) . . ?
F7 C34 C35 118.13(13) . . ?
N2 C34 F7 117.16(12) . . ?
N2 C34 C35 124.71(12) . . ?
F8 C35 C31 120.88(11) . . ?
F8 C35 C34 121.00(12) . . ?
C34 C35 C31 118.11(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 O1 C11 -57.03(15) . . . . ?
C2 C1 C21 C22 -66.01(15) . . . . ?
C2 C1 C21 C29 111.21(13) . . . . ?
C3 C2 O1 C11 129.01(12) . . . . ?
C9 C1 C21 C22 110.25(13) . . . . ?
C9 C1 C21 C29 -72.53(15) . . . . ?
C12 C11 O1 C2 -45.19(16) . . . . ?
C15 C11 O1 C2 140.26(11) . . . . ?
C21 C22 O2 C31 -51.47(15) . . . . ?
C23 C22 O2 C31 133.04(11) . . . . ?
C32 C31 O2 C22 139.06(11) . . . . ?
C35 C31 O2 C22 -44.35(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2i_18srv271
_database_code_depnum_ccdc_archive 'CCDC 1856219'
_audit_update_record             
;
2018-07-16 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-06-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H4 F4 N2 O3'
_chemical_formula_sum            'C11 H4 F4 N2 O3'
_chemical_formula_weight         288.16
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_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                   7.4591(17)
_cell_length_b                   10.786(3)
_cell_length_c                   26.797(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.012(6)
_cell_angle_gamma                90
_cell_volume                     2155.6(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2845
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      20.72
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;    
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1383 before and 0.0677 after correction. 
The Ratio of minimum to maximum transmission is 0.6618. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1252
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            26864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2619
_reflns_number_total             5207
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+1.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1393
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.0513(2) -0.12517(17) 0.37830(7) 0.0364(5) Uani 1 1 d . . . . .
F2 F -0.0082(2) 0.12331(16) 0.38718(7) 0.0298(5) Uani 1 1 d . . . . .
F3 F 0.6131(2) 0.05393(17) 0.39473(7) 0.0346(5) Uani 1 1 d . . . . .
F4 F 0.5423(2) -0.19049(16) 0.38538(7) 0.0375(5) Uani 1 1 d . . . . .
O1 O 0.3405(3) 0.21895(18) 0.39816(8) 0.0235(5) Uani 1 1 d . . . . .
O2 O 0.0615(3) 0.5602(2) 0.22558(10) 0.0505(7) Uani 1 1 d . . . . .
O3 O 0.0897(3) 0.6925(2) 0.28525(9) 0.0393(6) Uani 1 1 d . . . . .
N1 N 0.2456(4) -0.1566(2) 0.38224(9) 0.0271(7) Uani 1 1 d . . . . .
N2 N 0.1038(3) 0.5875(3) 0.26830(11) 0.0314(7) Uani 1 1 d . . . . .
C1 C 0.1135(4) -0.0765(3) 0.38197(11) 0.0240(8) Uani 1 1 d . . . . .
C2 C 0.1335(4) 0.0477(3) 0.38654(11) 0.0209(7) Uani 1 1 d . . . . .
C3 C 0.3043(4) 0.0964(3) 0.39050(11) 0.0195(7) Uani 1 1 d . . . . .
C4 C 0.4444(4) 0.0132(3) 0.39098(11) 0.0234(8) Uani 1 1 d . . . . .
C5 C 0.4067(4) -0.1098(3) 0.38635(11) 0.0234(7) Uani 1 1 d . . . . .
C6 C 0.2782(4) 0.3061(3) 0.36355(11) 0.0208(7) Uani 1 1 d . . . . .
C7 C 0.2173(4) 0.2753(3) 0.31660(11) 0.0233(7) Uani 1 1 d . . . . .
H7 H 0.213208 0.191223 0.306106 0.028 Uiso 1 1 calc R . . . .
C8 C 0.1620(4) 0.3694(3) 0.28486(12) 0.0245(8) Uani 1 1 d . . . . .
H8 H 0.119017 0.351125 0.252099 0.029 Uiso 1 1 calc R . . . .
C9 C 0.1702(4) 0.4898(3) 0.30150(12) 0.0236(7) Uani 1 1 d . . . . .
C10 C 0.2340(4) 0.5208(3) 0.34829(12) 0.0227(8) Uani 1 1 d . . . . .
H10 H 0.240272 0.604981 0.358562 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2886(4) 0.4271(3) 0.37989(11) 0.0217(7) Uani 1 1 d . . . . .
H11 H 0.332805 0.445590 0.412520 0.026 Uiso 1 1 calc R . . . .
F1A F 1.1681(2) 0.84187(18) 0.50818(7) 0.0407(5) Uani 1 1 d . . . . .
F2A F 1.1872(2) 0.61751(16) 0.46382(6) 0.0313(5) Uani 1 1 d . . . . .
F3A F 0.5569(2) 0.61546(17) 0.45675(7) 0.0347(5) Uani 1 1 d . . . . .
F4A F 0.5669(2) 0.84559(18) 0.49764(7) 0.0407(5) Uani 1 1 d . . . . .
O1A O 0.8790(3) 0.49635(19) 0.43690(8) 0.0271(5) Uani 1 1 d . . . . .
O2A O 0.5581(4) 0.4860(3) 0.22015(10) 0.0559(8) Uani 1 1 d . . . . .
O3A O 0.5522(3) 0.2908(3) 0.23810(9) 0.0444(7) Uani 1 1 d . . . . .
N1A N 0.8676(4) 0.8427(3) 0.50248(9) 0.0306(7) Uani 1 1 d . . . . .
N2A N 0.5862(4) 0.3989(3) 0.24832(11) 0.0351(7) Uani 1 1 d . . . . .
C1A C 1.0177(4) 0.7842(3) 0.49413(12) 0.0282(8) Uani 1 1 d . . . . .
C2A C 1.0284(4) 0.6709(3) 0.47173(11) 0.0225(7) Uani 1 1 d . . . . .
C3A C 0.8724(4) 0.6118(3) 0.45747(11) 0.0232(7) Uani 1 1 d . . . . .
C4A C 0.7125(4) 0.6708(3) 0.46792(12) 0.0251(8) Uani 1 1 d . . . . .
C5A C 0.7198(4) 0.7854(3) 0.48934(12) 0.0288(8) Uani 1 1 d . . . . .
C6A C 0.8010(4) 0.4782(3) 0.38967(11) 0.0217(7) Uani 1 1 d . . . . .
C7A C 0.7669(4) 0.5743(3) 0.35692(12) 0.0226(7) Uani 1 1 d . . . . .
H7A H 0.792855 0.657427 0.366218 0.027 Uiso 1 1 calc R . . . .
C8A C 0.6945(4) 0.5477(3) 0.31053(11) 0.0238(8) Uani 1 1 d . . . . .
H8A H 0.665581 0.612389 0.287735 0.029 Uiso 1 1 calc R . . . .
C9A C 0.6647(4) 0.4257(3) 0.29774(12) 0.0258(8) Uani 1 1 d . . . . .
C10A C 0.7006(4) 0.3295(3) 0.33043(13) 0.0281(8) Uani 1 1 d . . . . .
H10A H 0.678472 0.246009 0.320805 0.034 Uiso 1 1 calc R . . . .
C11A C 0.7687(4) 0.3566(3) 0.37707(12) 0.0257(8) Uani 1 1 d . . . . .
H11A H 0.793216 0.292172 0.400370 0.031 Uiso 1 1 calc R . . . .


_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
F1 C1 1.339(3) . ?
F2 C2 1.335(3) . ?
F3 C4 1.335(3) . ?
F4 C5 1.336(3) . ?
O1 C3 1.364(3) . ?
O1 C6 1.395(3) . ?
O2 N2 1.218(3) . ?
O3 N2 1.225(3) . ?
N1 C1 1.310(4) . ?
N1 C5 1.306(4) . ?
N2 C9 1.460(4) . ?
C1 C2 1.354(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.361(4) . ?
C6 C7 1.371(4) . ?
C6 C11 1.379(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(4) . ?
C9 C10 1.375(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9500 . ?
F1A C1A 1.331(3) . ?
F2A C2A 1.337(3) . ?
F3A C4A 1.334(3) . ?
F4A C5A 1.335(3) . ?
O1A C3A 1.363(3) . ?
O1A C6A 1.398(3) . ?
O2A N2A 1.222(4) . ?
O3A N2A 1.223(4) . ?
N1A C1A 1.308(4) . ?
N1A C5A 1.307(4) . ?
N2A C9A 1.467(4) . ?
C1A C2A 1.364(4) . ?
C2A C3A 1.375(4) . ?
C3A C4A 1.385(4) . ?
C4A C5A 1.364(4) . ?
C6A C7A 1.379(4) . ?
C6A C11A 1.374(4) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.377(4) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.377(4) . ?
C9A C10A 1.381(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.373(4) . ?
C11A H11A 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
C3 O1 C6 119.4(2) . . ?
C5 N1 C1 115.9(3) . . ?
O2 N2 O3 123.3(3) . . ?
O2 N2 C9 118.5(3) . . ?
O3 N2 C9 118.1(3) . . ?
F1 C1 C2 119.6(3) . . ?
N1 C1 F1 115.6(3) . . ?
N1 C1 C2 124.8(3) . . ?
F2 C2 C1 121.3(3) . . ?
F2 C2 C3 119.8(3) . . ?
C1 C2 C3 118.9(3) . . ?
O1 C3 C2 124.1(3) . . ?
O1 C3 C4 118.8(3) . . ?
C4 C3 C2 116.9(3) . . ?
F3 C4 C3 120.0(3) . . ?
F3 C4 C5 121.4(3) . . ?
C5 C4 C3 118.6(3) . . ?
F4 C5 C4 118.8(3) . . ?
N1 C5 F4 116.3(3) . . ?
N1 C5 C4 124.9(3) . . ?
C7 C6 O1 123.2(3) . . ?
C7 C6 C11 122.5(3) . . ?
C11 C6 O1 114.3(3) . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.5(3) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 N2 118.2(3) . . ?
C8 C9 C10 122.6(3) . . ?
C10 C9 N2 119.2(3) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.5(3) . . ?
C11 C10 H10 120.8 . . ?
C6 C11 H11 120.5 . . ?
C10 C11 C6 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C3A O1A C6A 118.5(2) . . ?
C5A N1A C1A 116.5(3) . . ?
O2A N2A O3A 124.2(3) . . ?
O2A N2A C9A 117.9(3) . . ?
O3A N2A C9A 117.9(3) . . ?
F1A C1A C2A 119.2(3) . . ?
N1A C1A F1A 116.5(3) . . ?
N1A C1A C2A 124.4(3) . . ?
F2A C2A C1A 121.0(3) . . ?
F2A C2A C3A 120.2(3) . . ?
C1A C2A C3A 118.8(3) . . ?
O1A C3A C2A 120.0(3) . . ?
O1A C3A C4A 122.6(3) . . ?
C2A C3A C4A 117.3(3) . . ?
F3A C4A C3A 119.9(3) . . ?
F3A C4A C5A 121.9(3) . . ?
C5A C4A C3A 118.3(3) . . ?
F4A C5A C4A 118.9(3) . . ?
N1A C5A F4A 116.4(3) . . ?
N1A C5A C4A 124.7(3) . . ?
C7A C6A O1A 122.7(3) . . ?
C11A C6A O1A 115.1(3) . . ?
C11A C6A C7A 122.1(3) . . ?
C6A C7A H7A 120.6 . . ?
C8A C7A C6A 118.9(3) . . ?
C8A C7A H7A 120.6 . . ?
C7A C8A H8A 120.6 . . ?
C7A C8A C9A 118.9(3) . . ?
C9A C8A H8A 120.6 . . ?
C8A C9A N2A 118.2(3) . . ?
C8A C9A C10A 122.1(3) . . ?
C10A C9A N2A 119.6(3) . . ?
C9A C10A H10A 120.6 . . ?
C11A C10A C9A 118.8(3) . . ?
C11A C10A H10A 120.6 . . ?
C6A C11A H11A 120.4 . . ?
C10A C11A C6A 119.2(3) . . ?
C10A C11A H11A 120.4 . . ?

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
C2 C3 O1 C6 -59.6(4) . . . . ?
C4 C3 O1 C6 126.4(3) . . . . ?
C7 C6 O1 C3 -15.2(4) . . . . ?
C8 C9 N2 O2 -7.6(4) . . . . ?
C8 C9 N2 O3 170.9(3) . . . . ?
C10 C9 N2 O2 174.0(3) . . . . ?
C10 C9 N2 O3 -7.6(4) . . . . ?
C11 C6 O1 C3 166.9(3) . . . . ?
C2A C3A O1A C6A -123.0(3) . . . . ?
C4A C3A O1A C6A 61.3(4) . . . . ?
C7A C6A O1A C3A 20.1(4) . . . . ?
C8A C9A N2A O2A 3.0(4) . . . . ?
C8A C9A N2A O3A -176.6(3) . . . . ?
C10A C9A N2A O2A -179.2(3) . . . . ?
C10A C9A N2A O3A 1.2(4) . . . . ?
C11A C6A O1A C3A -163.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
