# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1818026'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;
_audit_creation_date             2018-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, C25 H20 F3 N O2'
_chemical_formula_sum            'C26 H22 Cl2 F3 N O2'
_chemical_formula_weight         508.34
_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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3021(9)
_cell_length_b                   11.1033(11)
_cell_length_c                   11.8279(11)
_cell_angle_alpha                81.577(2)
_cell_angle_beta                 80.9200(10)
_cell_angle_gamma                72.3840(10)
_cell_volume                     1143.41(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4883
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0730 before and 0.0335 after correction. The Ratio of minimum to maximum transmission is 0.8665. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6309
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.753
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3934
_reflns_number_total             4441
_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_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.028
_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)+(0.0703P)²+1.0156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: Cl1(0.75) C26(0.5) H26A(0.5) H26B(0.5) Cl1'(0.25) C26'(0.5)
 H26C(0.5) H26D(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C2(H2A,H2B), C19(H19A,H19B), C26'(H26C,H26D)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl -0.17331(17) 0.24367(14) 0.98731(10) 0.0665(3) Uani 0.75 1 d . . P A 1
Cl2 Cl -0.15486(12) 0.09176(11) 0.79554(12) 0.0919(4) Uani 1 1 d . . . . .
C26 C -0.0699(9) 0.1832(8) 0.8652(7) 0.0643(19) Uani 0.5 1 d . . P A 1
H26A H 0.0286 0.1295 0.8844 0.077 Uiso 0.5 1 calc R . P A 1
H26B H -0.0527 0.2531 0.8106 0.077 Uiso 0.5 1 calc R . P A 1
F1 F 0.17431(14) 0.77591(12) 0.53947(12) 0.0363(3) Uani 1 1 d . . . . .
F2 F -0.06555(14) 0.86496(12) 0.57057(12) 0.0347(3) Uani 1 1 d . . . . .
F3 F 0.06894(14) 0.81472(12) 0.71129(11) 0.0316(3) Uani 1 1 d . . . . .
O1 O -0.12313(14) 0.66409(13) 0.70058(11) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.03388(15) 0.37952(13) 0.63242(12) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.29036(18) 0.35644(15) 0.60673(13) 0.0199(3) Uani 1 1 d . . . . .
C1 C -0.1122(2) 0.57876(18) 0.80626(15) 0.0195(4) Uani 1 1 d . . . . .
H1 H -0.1452 0.5054 0.7967 0.023 Uiso 1 1 calc R . . . .
C2 C 0.0566(2) 0.53466(18) 0.82020(16) 0.0199(4) Uani 1 1 d . . . . .
H2A H 0.0845 0.4499 0.8606 0.024 Uiso 1 1 calc R . . . .
H2B H 0.0829 0.5923 0.8621 0.024 Uiso 1 1 calc R . . . .
C3 C 0.1358(2) 0.53581(17) 0.69553(15) 0.0184(4) Uani 1 1 d . . . . .
C4 C 0.0194(2) 0.64751(18) 0.63236(15) 0.0192(4) Uani 1 1 d . . . . .
H4 H 0.0119 0.6233 0.5576 0.023 Uiso 1 1 calc R . . . .
C5 C 0.0506(2) 0.77570(19) 0.61393(18) 0.0252(4) Uani 1 1 d . . . . .
C6 C 0.3015(2) 0.53101(18) 0.68407(15) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.3753(2) 0.60700(19) 0.71960(17) 0.0227(4) Uani 1 1 d . . . . .
H7 H 0.3201 0.6794 0.7549 0.027 Uiso 1 1 calc R . . . .
C8 C 0.5336(2) 0.5738(2) 0.70183(17) 0.0251(4) Uani 1 1 d . . . . .
H8 H 0.5841 0.6256 0.7239 0.030 Uiso 1 1 calc R . . . .
C9 C 0.6163(2) 0.4647(2) 0.65178(17) 0.0261(4) Uani 1 1 d . . . . .
H9 H 0.7218 0.4440 0.6404 0.031 Uiso 1 1 calc R . . . .
C10 C 0.5435(2) 0.38524(19) 0.61809(17) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.5984 0.3107 0.5861 0.028 Uiso 1 1 calc R . . . .
C11 C 0.3871(2) 0.42146(18) 0.63412(15) 0.0193(4) Uani 1 1 d . . . . .
C12 C 0.1431(2) 0.41520(18) 0.64264(15) 0.0190(4) Uani 1 1 d . . . . .
C13 C -0.2144(2) 0.64758(19) 0.90298(16) 0.0221(4) Uani 1 1 d . . . . .
C14 C -0.2026(2) 0.7627(2) 0.92657(19) 0.0303(5) Uani 1 1 d . . . . .
H14 H -0.1310 0.7982 0.8819 0.036 Uiso 1 1 calc R . . . .
C15 C -0.2961(3) 0.8252(2) 1.0156(2) 0.0393(5) Uani 1 1 d . . . . .
H15 H -0.2880 0.9030 1.0297 0.047 Uiso 1 1 calc R . . . .
C16 C -0.4018(3) 0.7726(3) 1.08389(19) 0.0392(6) Uani 1 1 d . . . . .
H16 H -0.4639 0.8144 1.1444 0.047 Uiso 1 1 calc R . . . .
C17 C -0.4143(2) 0.6583(2) 1.06170(19) 0.0349(5) Uani 1 1 d . . . . .
H17 H -0.4847 0.6224 1.1075 0.042 Uiso 1 1 calc R . . . .
C18 C -0.3219(2) 0.5961(2) 0.97087(17) 0.0265(4) Uani 1 1 d . . . . .
H18 H -0.3321 0.5195 0.9555 0.032 Uiso 1 1 calc R . . . .
C19 C 0.3406(2) 0.24288(18) 0.54450(17) 0.0234(4) Uani 1 1 d . . . . .
H19A H 0.4285 0.2473 0.4895 0.028 Uiso 1 1 calc R . . . .
H19B H 0.2602 0.2418 0.5018 0.028 Uiso 1 1 calc R . . . .
C20 C 0.3812(2) 0.12143(18) 0.62360(17) 0.0229(4) Uani 1 1 d . . . . .
C21 C 0.5315(2) 0.0528(2) 0.63270(19) 0.0282(4) Uani 1 1 d . . . . .
H21 H 0.6091 0.0802 0.5872 0.034 Uiso 1 1 calc R . . . .
C22 C 0.5669(3) -0.0561(2) 0.7091(2) 0.0340(5) Uani 1 1 d . . . . .
H22 H 0.6680 -0.1015 0.7145 0.041 Uiso 1 1 calc R . . . .
C23 C 0.4526(3) -0.0974(2) 0.7773(2) 0.0334(5) Uani 1 1 d . . . . .
H23 H 0.4764 -0.1690 0.8303 0.040 Uiso 1 1 calc R . . . .
C24 C 0.3029(3) -0.0319(2) 0.7662(2) 0.0364(5) Uani 1 1 d . . . . .
H24 H 0.2255 -0.0607 0.8103 0.044 Uiso 1 1 calc R . . . .
C25 C 0.2673(2) 0.0769(2) 0.6893(2) 0.0316(5) Uani 1 1 d . . . . .
H25 H 0.1661 0.1202 0.6819 0.038 Uiso 1 1 calc R . . . .
Cl1' Cl -0.0865(6) 0.2027(6) 0.9600(4) 0.108(2) Uani 0.25 1 d . . P A 2
C26' C -0.1567(9) 0.2234(6) 0.8372(6) 0.0549(15) Uani 0.5 1 d . . P A 2
H26C H -0.2604 0.2779 0.8457 0.066 Uiso 0.5 1 calc R . P A 2
H26D H -0.0980 0.2660 0.7788 0.066 Uiso 0.5 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C26 1.708(7) . ?
Cl2 C26 1.809(7) . ?
Cl2 C26' 1.604(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
F1 C5 1.335(2) . ?
F2 C5 1.338(2) . ?
F3 C5 1.340(2) . ?
O1 C1 1.451(2) . ?
O1 C4 1.414(2) . ?
O2 C12 1.225(2) . ?
N1 C11 1.410(2) . ?
N1 C12 1.356(2) . ?
N1 C19 1.469(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.525(2) . ?
C1 C13 1.507(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.541(3) . ?
C3 C4 1.562(2) . ?
C3 C6 1.511(2) . ?
C3 C12 1.538(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.516(3) . ?
C6 C7 1.380(3) . ?
C6 C11 1.392(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(3) . ?
C13 C14 1.387(3) . ?
C13 C18 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.507(3) . ?
C20 C21 1.388(3) . ?
C20 C25 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(3) . ?
C25 H25 0.9300 . ?
Cl1' C26' 1.642(9) . ?
C26' H26C 0.9700 . ?
C26' H26D 0.9700 . ?

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
Cl1 C26 Cl2 115.4(4) . . ?
Cl1 C26 H26A 108.4 . . ?
Cl1 C26 H26B 108.4 . . ?
Cl2 C26 H26A 108.4 . . ?
Cl2 C26 H26B 108.4 . . ?
H26A C26 H26B 107.5 . . ?
C4 O1 C1 111.69(13) . . ?
C11 N1 C19 124.99(16) . . ?
C12 N1 C11 110.80(15) . . ?
C12 N1 C19 124.18(16) . . ?
O1 C1 H1 109.2 . . ?
O1 C1 C2 104.78(14) . . ?
O1 C1 C13 109.16(15) . . ?
C2 C1 H1 109.2 . . ?
C13 C1 H1 109.2 . . ?
C13 C1 C2 115.23(15) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C1 C2 C3 103.89(14) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 C4 101.70(14) . . ?
C6 C3 C2 114.50(15) . . ?
C6 C3 C4 120.98(15) . . ?
C6 C3 C12 102.08(14) . . ?
C12 C3 C2 111.19(15) . . ?
C12 C3 C4 106.22(14) . . ?
O1 C4 C3 107.05(14) . . ?
O1 C4 H4 108.8 . . ?
O1 C4 C5 106.49(15) . . ?
C3 C4 H4 108.8 . . ?
C5 C4 C3 116.71(15) . . ?
C5 C4 H4 108.8 . . ?
F1 C5 F2 106.79(16) . . ?
F1 C5 F3 107.43(17) . . ?
F1 C5 C4 112.12(16) . . ?
F2 C5 F3 106.58(16) . . ?
F2 C5 C4 110.37(17) . . ?
F3 C5 C4 113.20(16) . . ?
C7 C6 C3 132.39(17) . . ?
C7 C6 C11 119.15(17) . . ?
C11 C6 C3 108.30(16) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.16(18) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.65(19) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.85(18) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 121.3 . . ?
C11 C10 C9 117.42(18) . . ?
C11 C10 H10 121.3 . . ?
C6 C11 N1 110.05(16) . . ?
C10 C11 N1 127.20(18) . . ?
C10 C11 C6 122.74(18) . . ?
O2 C12 N1 125.62(17) . . ?
O2 C12 C3 125.70(17) . . ?
N1 C12 C3 108.67(15) . . ?
C14 C13 C1 120.89(17) . . ?
C14 C13 C18 118.71(19) . . ?
C18 C13 C1 120.39(18) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.5(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
N1 C19 H19A 109.1 . . ?
N1 C19 H19B 109.1 . . ?
N1 C19 C20 112.62(16) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C21 C20 C19 121.26(19) . . ?
C25 C20 C19 119.87(18) . . ?
C25 C20 C21 118.87(19) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.5(2) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
Cl2 C26' Cl1' 112.3(5) . . ?
Cl2 C26' H26C 109.1 . . ?
Cl2 C26' H26D 109.1 . . ?
Cl1' C26' H26C 109.1 . . ?
Cl1' C26' H26D 109.1 . . ?
H26C C26' H26D 107.9 . . ?

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
O1 C1 C2 C3 -30.98(18) . . . . ?
O1 C1 C13 C14 -53.9(2) . . . . ?
O1 C1 C13 C18 126.56(18) . . . . ?
O1 C4 C5 F1 -172.79(15) . . . . ?
O1 C4 C5 F2 -53.9(2) . . . . ?
O1 C4 C5 F3 65.48(19) . . . . ?
N1 C19 C20 C21 -104.2(2) . . . . ?
N1 C19 C20 C25 75.5(2) . . . . ?
C1 O1 C4 C3 2.92(19) . . . . ?
C1 O1 C4 C5 -122.60(16) . . . . ?
C1 C2 C3 C4 31.69(18) . . . . ?
C1 C2 C3 C6 163.92(15) . . . . ?
C1 C2 C3 C12 -81.03(18) . . . . ?
C1 C13 C14 C15 -179.7(2) . . . . ?
C1 C13 C18 C17 178.71(18) . . . . ?
C2 C1 C13 C14 63.6(2) . . . . ?
C2 C1 C13 C18 -115.91(19) . . . . ?
C2 C3 C4 O1 -21.86(18) . . . . ?
C2 C3 C4 C5 97.26(18) . . . . ?
C2 C3 C6 C7 -56.0(3) . . . . ?
C2 C3 C6 C11 119.14(17) . . . . ?
C2 C3 C12 O2 58.0(2) . . . . ?
C2 C3 C12 N1 -123.44(16) . . . . ?
C3 C4 C5 F1 67.8(2) . . . . ?
C3 C4 C5 F2 -173.30(15) . . . . ?
C3 C4 C5 F3 -53.9(2) . . . . ?
C3 C6 C7 C8 176.36(18) . . . . ?
C3 C6 C11 N1 2.7(2) . . . . ?
C3 C6 C11 C10 -176.06(17) . . . . ?
C4 O1 C1 C2 17.72(19) . . . . ?
C4 O1 C1 C13 141.67(15) . . . . ?
C4 C3 C6 C7 66.3(3) . . . . ?
C4 C3 C6 C11 -118.61(18) . . . . ?
C4 C3 C12 O2 -51.9(2) . . . . ?
C4 C3 C12 N1 126.73(15) . . . . ?
C6 C3 C4 O1 -150.05(16) . . . . ?
C6 C3 C4 C5 -30.9(2) . . . . ?
C6 C3 C12 O2 -179.48(18) . . . . ?
C6 C3 C12 N1 -0.90(19) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C7 C6 C11 N1 178.61(16) . . . . ?
C7 C6 C11 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 N1 -179.98(17) . . . . ?
C9 C10 C11 C6 -1.4(3) . . . . ?
C11 N1 C12 O2 -178.81(18) . . . . ?
C11 N1 C12 C3 2.6(2) . . . . ?
C11 N1 C19 C20 88.6(2) . . . . ?
C11 C6 C7 C8 1.7(3) . . . . ?
C12 N1 C11 C6 -3.4(2) . . . . ?
C12 N1 C11 C10 175.29(18) . . . . ?
C12 N1 C19 C20 -93.5(2) . . . . ?
C12 C3 C4 O1 94.55(16) . . . . ?
C12 C3 C4 C5 -146.33(16) . . . . ?
C12 C3 C6 C7 -176.2(2) . . . . ?
C12 C3 C6 C11 -1.12(19) . . . . ?
C13 C1 C2 C3 -150.95(16) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 1.1(3) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C19 N1 C11 C6 174.72(16) . . . . ?
C19 N1 C11 C10 -6.6(3) . . . . ?
C19 N1 C12 O2 3.0(3) . . . . ?
C19 N1 C12 C3 -175.56(16) . . . . ?
C19 C20 C21 C22 177.54(19) . . . . ?
C19 C20 C25 C24 -177.3(2) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C20 C25 C24 2.4(3) . . . . ?
C21 C22 C23 C24 2.1(3) . . . . ?
C22 C23 C24 C25 -1.8(4) . . . . ?
C23 C24 C25 C20 -0.5(4) . . . . ?
C25 C20 C21 C22 -2.1(3) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1822716'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;
_audit_creation_date             2018-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 F3 N O2'
_chemical_formula_sum            'C25 H20 F3 N O2'
_chemical_formula_weight         423.42
_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                   9.330(4)
_cell_length_b                   11.138(5)
_cell_length_c                   19.656(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.194(8)
_cell_angle_gamma                90
_cell_volume                     2034.2(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.80
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1399 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.5564.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9966
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.212
_diffrn_reflns_theta_max         25.212
_diffrn_reflns_theta_min         2.081
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2157
_reflns_number_total             3623
_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_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.024
_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)+(0.0919P)²+0.0742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1835
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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 0.3387(3) 0.44143(18) 0.52396(10) 0.0821(7) Uani 1 1 d . . . . .
F2 F 0.1403(2) 0.45738(17) 0.46120(11) 0.0770(7) Uani 1 1 d . . . . .
F3 F 0.3365(2) 0.51203(17) 0.42232(10) 0.0812(7) Uani 1 1 d . . . . .
O1 O 0.5087(2) 0.1515(2) 0.52208(11) 0.0622(7) Uani 1 1 d . . . . .
O2 O 0.2334(3) 0.29202(18) 0.36786(10) 0.0627(7) Uani 1 1 d . . . . .
N1 N 0.3256(3) 0.1465(2) 0.59216(11) 0.0457(6) Uani 1 1 d . . . . .
C1 C 0.1784(3) 0.1715(2) 0.58646(14) 0.0433(7) Uani 1 1 d . . . . .
C2 C 0.0860(4) 0.1629(3) 0.63661(16) 0.0529(8) Uani 1 1 d . . . . .
H2 H 0.1180 0.1396 0.6808 0.064 Uiso 1 1 calc R . . . .
C3 C -0.0565(4) 0.1905(3) 0.61858(18) 0.0619(10) Uani 1 1 d . . . . .
H3 H -0.1222 0.1842 0.6513 0.074 Uiso 1 1 calc R . . . .
C4 C -0.1044(4) 0.2271(3) 0.55327(19) 0.0628(10) Uani 1 1 d . . . . .
H4 H -0.2011 0.2454 0.5426 0.075 Uiso 1 1 calc R . . . .
C5 C -0.0092(4) 0.2364(3) 0.50396(17) 0.0556(9) Uani 1 1 d . . . . .
H5 H -0.0410 0.2614 0.4600 0.067 Uiso 1 1 calc R . . . .
C6 C 0.1331(3) 0.2086(2) 0.52015(15) 0.0452(7) Uani 1 1 d . . . . .
C7 C 0.2606(3) 0.1990(2) 0.47818(14) 0.0438(7) Uani 1 1 d . . . . .
C8 C 0.3824(3) 0.1631(3) 0.53149(15) 0.0450(7) Uani 1 1 d . . . . .
C9 C 0.2365(3) 0.1045(3) 0.42073(14) 0.0488(8) Uani 1 1 d . . . . .
H9A H 0.3271 0.0729 0.4079 0.059 Uiso 1 1 calc R . . . .
H9B H 0.1770 0.0388 0.4341 0.059 Uiso 1 1 calc R . . . .
C10 C 0.1597(3) 0.1779(3) 0.36315(15) 0.0509(8) Uani 1 1 d . . . . .
H10 H 0.0596 0.1901 0.3729 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3054(3) 0.3052(3) 0.43447(14) 0.0493(8) Uani 1 1 d . . . . .
H11 H 0.4089 0.2979 0.4303 0.059 Uiso 1 1 calc R . . . .
C12 C 0.2786(4) 0.4286(3) 0.46045(16) 0.0567(9) Uani 1 1 d . . . . .
C13 C 0.0351(4) 0.0767(3) 0.26212(16) 0.0564(9) Uani 1 1 d . . . . .
H13 H -0.0477 0.0783 0.2852 0.068 Uiso 1 1 calc R . . . .
C14 C 0.0311(4) 0.0250(3) 0.19817(18) 0.0637(9) Uani 1 1 d . . . . .
H14 H -0.0534 -0.0103 0.1789 0.076 Uiso 1 1 calc R . . . .
C15 C 0.1521(4) 0.0258(3) 0.16281(17) 0.0587(9) Uani 1 1 d . . . . .
H15 H 0.1487 -0.0071 0.1192 0.070 Uiso 1 1 calc R . . . .
C16 C 0.2775(4) 0.0750(3) 0.19216(16) 0.0550(9) Uani 1 1 d . . . . .
H16 H 0.3592 0.0754 0.1684 0.066 Uiso 1 1 calc R . . . .
C17 C 0.2830(3) 0.1241(3) 0.25682(15) 0.0503(8) Uani 1 1 d . . . . .
H17 H 0.3688 0.1560 0.2768 0.060 Uiso 1 1 calc R . . . .
C18 C 0.1609(3) 0.1261(3) 0.29204(14) 0.0462(8) Uani 1 1 d . . . . .
C19 C 0.4082(4) 0.1087(3) 0.65448(15) 0.0500(8) Uani 1 1 d . . . . .
H19A H 0.3932 0.1660 0.6903 0.060 Uiso 1 1 calc R . . . .
H19B H 0.5096 0.1101 0.6472 0.060 Uiso 1 1 calc R . . . .
C20 C 0.3697(3) -0.0150(3) 0.67817(14) 0.0426(7) Uani 1 1 d . . . . .
C21 C 0.3585(3) -0.0363(3) 0.74652(15) 0.0485(8) Uani 1 1 d . . . . .
H21 H 0.3684 0.0270 0.7774 0.058 Uiso 1 1 calc R . . . .
C22 C 0.3327(3) -0.1511(3) 0.76962(16) 0.0567(9) Uani 1 1 d . . . . .
H22 H 0.3268 -0.1648 0.8159 0.068 Uiso 1 1 calc R . . . .
C23 C 0.3160(4) -0.2440(3) 0.72431(18) 0.0592(9) Uani 1 1 d . . . . .
H23 H 0.2981 -0.3210 0.7397 0.071 Uiso 1 1 calc R . . . .
C24 C 0.3256(4) -0.2236(3) 0.65626(17) 0.0596(9) Uani 1 1 d . . . . .
H24 H 0.3144 -0.2872 0.6256 0.071 Uiso 1 1 calc R . . . .
C25 C 0.3517(4) -0.1099(3) 0.63263(15) 0.0523(8) Uani 1 1 d . . . . .
H25 H 0.3572 -0.0969 0.5862 0.063 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 C12 1.329(4) . ?
F2 C12 1.332(4) . ?
F3 C12 1.338(3) . ?
O1 C8 1.216(3) . ?
O2 C10 1.444(4) . ?
O2 C11 1.424(4) . ?
N1 C1 1.396(4) . ?
N1 C8 1.361(4) . ?
N1 C19 1.449(4) . ?
C1 C2 1.370(4) . ?
C1 C6 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C6 C7 1.512(4) . ?
C7 C8 1.528(4) . ?
C7 C9 1.545(4) . ?
C7 C11 1.542(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.521(4) . ?
C10 H10 0.9800 . ?
C10 C18 1.513(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.495(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(5) . ?
C13 C18 1.379(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.509(4) . ?
C20 C21 1.378(4) . ?
C20 C25 1.385(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.365(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.368(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C25 H25 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
C11 O2 C10 109.4(2) . . ?
C1 N1 C19 124.7(2) . . ?
C8 N1 C1 111.1(2) . . ?
C8 N1 C19 124.1(3) . . ?
N1 C1 C6 110.3(2) . . ?
C2 C1 N1 127.3(3) . . ?
C2 C1 C6 122.3(3) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 107.5(3) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 133.0(3) . . ?
C6 C7 C8 102.6(2) . . ?
C6 C7 C9 112.2(2) . . ?
C6 C7 C11 121.1(2) . . ?
C8 C7 C9 111.9(2) . . ?
C8 C7 C11 111.1(2) . . ?
C11 C7 C9 98.3(2) . . ?
O1 C8 N1 125.3(3) . . ?
O1 C8 C7 126.5(3) . . ?
N1 C8 C7 108.2(3) . . ?
C7 C9 H9A 111.4 . . ?
C7 C9 H9B 111.4 . . ?
H9A C9 H9B 109.3 . . ?
C10 C9 C7 101.9(2) . . ?
C10 C9 H9A 111.4 . . ?
C10 C9 H9B 111.4 . . ?
O2 C10 C9 103.6(2) . . ?
O2 C10 H10 108.7 . . ?
O2 C10 C18 110.6(2) . . ?
C9 C10 H10 108.7 . . ?
C18 C10 C9 116.1(3) . . ?
C18 C10 H10 108.7 . . ?
O2 C11 C7 107.7(2) . . ?
O2 C11 H11 107.5 . . ?
O2 C11 C12 109.2(2) . . ?
C7 C11 H11 107.5 . . ?
C12 C11 C7 116.9(2) . . ?
C12 C11 H11 107.5 . . ?
F1 C12 F2 106.9(3) . . ?
F1 C12 F3 107.1(3) . . ?
F1 C12 C11 110.5(3) . . ?
F2 C12 F3 106.2(3) . . ?
F2 C12 C11 114.7(3) . . ?
F3 C12 C11 111.0(3) . . ?
C14 C13 H13 119.8 . . ?
C18 C13 H13 119.8 . . ?
C18 C13 C14 120.4(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C10 118.0(3) . . ?
C13 C18 C17 119.2(3) . . ?
C17 C18 C10 122.8(3) . . ?
N1 C19 H19A 108.8 . . ?
N1 C19 H19B 108.8 . . ?
N1 C19 C20 113.7(3) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 C25 118.9(3) . . ?
C25 C20 C19 121.1(3) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.7(3) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.9(3) . . ?
C24 C25 H25 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C10 C18 C13 -136.0(3) . . . . ?
O2 C10 C18 C17 45.3(4) . . . . ?
O2 C11 C12 F1 176.9(3) . . . . ?
O2 C11 C12 F2 56.0(3) . . . . ?
O2 C11 C12 F3 -64.4(4) . . . . ?
N1 C1 C2 C3 -178.8(3) . . . . ?
N1 C1 C6 C5 179.4(3) . . . . ?
N1 C1 C6 C7 3.9(3) . . . . ?
N1 C19 C20 C21 -138.3(3) . . . . ?
N1 C19 C20 C25 44.8(4) . . . . ?
C1 N1 C8 O1 177.6(3) . . . . ?
C1 N1 C8 C7 -2.2(3) . . . . ?
C1 N1 C19 C20 68.0(4) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C6 C7 C8 -4.8(3) . . . . ?
C1 C6 C7 C9 115.4(3) . . . . ?
C1 C6 C7 C11 -129.3(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 -176.1(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 174.0(3) . . . . ?
C5 C6 C7 C8 -179.4(3) . . . . ?
C5 C6 C7 C9 -59.2(4) . . . . ?
C5 C6 C7 C11 56.1(5) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C6 C7 C8 O1 -175.5(3) . . . . ?
C6 C7 C8 N1 4.3(3) . . . . ?
C6 C7 C9 C10 86.8(3) . . . . ?
C6 C7 C11 O2 -91.6(3) . . . . ?
C6 C7 C11 C12 31.7(4) . . . . ?
C7 C9 C10 O2 39.7(3) . . . . ?
C7 C9 C10 C18 161.2(3) . . . . ?
C7 C11 C12 F1 54.3(4) . . . . ?
C7 C11 C12 F2 -66.5(4) . . . . ?
C7 C11 C12 F3 173.0(3) . . . . ?
C8 N1 C1 C2 178.9(3) . . . . ?
C8 N1 C1 C6 -1.1(3) . . . . ?
C8 N1 C19 C20 -112.6(3) . . . . ?
C8 C7 C9 C10 -158.5(2) . . . . ?
C8 C7 C11 O2 148.1(2) . . . . ?
C8 C7 C11 C12 -88.6(3) . . . . ?
C9 C7 C8 O1 64.1(4) . . . . ?
C9 C7 C8 N1 -116.2(3) . . . . ?
C9 C7 C11 O2 30.6(3) . . . . ?
C9 C7 C11 C12 154.0(3) . . . . ?
C9 C10 C18 C13 106.3(3) . . . . ?
C9 C10 C18 C17 -72.4(4) . . . . ?
C10 O2 C11 C7 -7.0(3) . . . . ?
C10 O2 C11 C12 -134.9(3) . . . . ?
C11 O2 C10 C9 -20.6(3) . . . . ?
C11 O2 C10 C18 -145.7(2) . . . . ?
C11 C7 C8 O1 -44.7(4) . . . . ?
C11 C7 C8 N1 135.0(2) . . . . ?
C11 C7 C9 C10 -41.7(3) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?
C14 C13 C18 C10 -178.1(3) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C17 C18 C10 179.7(3) . . . . ?
C16 C17 C18 C13 1.0(5) . . . . ?
C18 C13 C14 C15 -2.0(5) . . . . ?
C19 N1 C1 C2 -1.6(5) . . . . ?
C19 N1 C1 C6 178.4(3) . . . . ?
C19 N1 C8 O1 -1.9(5) . . . . ?
C19 N1 C8 C7 178.4(2) . . . . ?
C19 C20 C21 C22 -175.7(3) . . . . ?
C19 C20 C25 C24 175.9(3) . . . . ?
C20 C21 C22 C23 -1.0(5) . . . . ?
C21 C20 C25 C24 -1.1(5) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C20 0.5(5) . . . . ?
C25 C20 C21 C22 1.3(5) . . . . ?

_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_20180103_zubing_c14ho2nf3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1822730'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;
_audit_creation_date             2018-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 F3 N O2'
_chemical_formula_sum            'C14 H14 F3 N O2'
_chemical_formula_weight         285.26
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.7429(4)
_cell_length_b                   13.5554(6)
_cell_length_c                   21.9361(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2599.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7520
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.558
_cell_measurement_theta_min      3.260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1214 before and 0.0709 after correction. The Ratio of minimum to maximum transmission is 0.7731. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10551
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.628
_diffrn_reflns_theta_max         66.628
_diffrn_reflns_theta_min         4.030
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2113
_reflns_number_total             2237
_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_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+1.1650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C13(H13), C4(H4)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.39105(12) 0.10630(8) 0.61652(5) 0.0469(3) Uani 1 1 d . . . . .
C1 C 0.70559(16) 0.34110(11) 0.58389(7) 0.0264(3) Uani 1 1 d . . . . .
H1 H 0.7852 0.3298 0.6125 0.032 Uiso 1 1 calc R . . . .
N1 N 0.29538(13) 0.32896(9) 0.58475(5) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.68882(12) 0.20414(8) 0.70663(5) 0.0298(3) Uani 1 1 d . . . . .
H1A H 0.6921 0.2228 0.7431 0.045 Uiso 1 1 calc GR . . . .
F2 F 0.55108(13) 0.02637(7) 0.67165(4) 0.0407(3) Uani 1 1 d . . . . .
C2 C 0.73860(17) 0.37248(11) 0.52472(7) 0.0286(4) Uani 1 1 d . . . . .
H2 H 0.8420 0.3823 0.5129 0.034 Uiso 1 1 calc R . . . .
O2 O 0.20395(11) 0.27543(8) 0.67693(5) 0.0291(3) Uani 1 1 d . . . . .
F3 F 0.63151(13) 0.11646(7) 0.59883(4) 0.0421(3) Uani 1 1 d . . . . .
C3 C 0.62246(17) 0.38943(11) 0.48307(7) 0.0267(3) Uani 1 1 d . . . . .
H3 H 0.6476 0.4105 0.4430 0.032 Uiso 1 1 calc R . . . .
C5 C 0.43937(15) 0.34565(10) 0.55756(6) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.48127(16) 0.29785(11) 0.65950(6) 0.0225(3) Uani 1 1 d . . . . .
C6 C 0.55440(16) 0.32691(11) 0.59980(6) 0.0215(3) Uani 1 1 d . . . . .
C13 C 0.43293(19) 0.47716(12) 0.69033(7) 0.0317(4) Uani 1 1 d . . . . .
H13 H 0.3246 0.4828 0.6910 0.038 Uiso 1 1 calc R . . . .
C12 C 0.50209(17) 0.37994(12) 0.70859(7) 0.0276(4) Uani 1 1 d . . . . .
H12A H 0.4544 0.3578 0.7472 0.033 Uiso 1 1 calc R . . . .
H12B H 0.6127 0.3894 0.7163 0.033 Uiso 1 1 calc R . . . .
C8 C 0.31061(16) 0.29691(10) 0.64291(6) 0.0224(3) Uani 1 1 d . . . . .
C14 C 0.5121(2) 0.55437(14) 0.67359(8) 0.0396(4) Uani 1 1 d . . . . .
H14A H 0.6206 0.5512 0.6724 0.047 Uiso 1 1 calc R . . . .
H14B H 0.4612 0.6137 0.6626 0.047 Uiso 1 1 calc R . . . .
C9 C 0.14954(16) 0.35308(12) 0.55664(7) 0.0272(3) Uani 1 1 d . . . . .
H9A H 0.0661 0.3341 0.5841 0.041 Uiso 1 1 calc GR . . . .
H9B H 0.1395 0.3172 0.5180 0.041 Uiso 1 1 calc GR . . . .
H9C H 0.1447 0.4242 0.5489 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.53543(16) 0.19912(11) 0.68735(6) 0.0242(3) Uani 1 1 d . . . . .
H10 H 0.4699 0.1839 0.7235 0.029 Uiso 1 1 calc R . . . .
C11 C 0.52778(18) 0.11229(12) 0.64344(7) 0.0284(4) Uani 1 1 d . . . . .
C4 C 0.46939(17) 0.37623(11) 0.49883(7) 0.0236(3) Uani 1 1 d . . . . .
H4 H 0.3894 0.3878 0.4704 0.028 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 C11 1.3358(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(2) . ?
C1 C6 1.381(2) . ?
N1 C5 1.4113(18) . ?
N1 C8 1.3544(18) . ?
N1 C9 1.4535(18) . ?
O1 H1A 0.8400 . ?
O1 C10 1.4079(17) . ?
F2 C11 1.3345(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
O2 C8 1.2294(18) . ?
F3 C11 1.3355(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C5 C6 1.391(2) . ?
C5 C4 1.379(2) . ?
C7 C6 1.510(2) . ?
C7 C12 1.559(2) . ?
C7 C8 1.5359(19) . ?
C7 C10 1.546(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.504(2) . ?
C13 C14 1.307(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.522(2) . ?
C4 H4 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
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.38(14) . . ?
C5 N1 C9 124.55(12) . . ?
C8 N1 C5 111.21(11) . . ?
C8 N1 C9 123.91(12) . . ?
C10 O1 H1A 109.5 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.82(14) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.27(14) . . ?
C4 C3 H3 119.4 . . ?
C6 C5 N1 109.53(12) . . ?
C4 C5 N1 127.80(13) . . ?
C4 C5 C6 122.67(13) . . ?
C6 C7 C12 111.31(12) . . ?
C6 C7 C8 102.01(11) . . ?
C6 C7 C10 116.05(12) . . ?
C8 C7 C12 106.44(11) . . ?
C8 C7 C10 112.59(12) . . ?
C10 C7 C12 108.01(11) . . ?
C1 C6 C5 119.91(13) . . ?
C1 C6 C7 131.38(13) . . ?
C5 C6 C7 108.62(12) . . ?
C12 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C14 C13 C12 124.27(16) . . ?
C7 C12 H12A 108.9 . . ?
C7 C12 H12B 108.9 . . ?
C13 C12 C7 113.23(12) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
N1 C8 C7 108.42(11) . . ?
O2 C8 N1 124.98(13) . . ?
O2 C8 C7 126.51(12) . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 111.64(12) . . ?
O1 C10 H10 108.5 . . ?
O1 C10 C11 105.62(12) . . ?
C7 C10 H10 108.5 . . ?
C11 C10 C7 113.95(12) . . ?
C11 C10 H10 108.5 . . ?
F1 C11 C10 111.48(12) . . ?
F2 C11 F1 106.77(13) . . ?
F2 C11 F3 105.84(12) . . ?
F2 C11 C10 112.00(12) . . ?
F3 C11 F1 106.64(13) . . ?
F3 C11 C10 113.65(13) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 C3 116.95(13) . . ?
C5 C4 H4 121.5 . . ?

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
C1 C2 C3 C4 0.3(2) . . . . ?
N1 C5 C6 C1 -178.14(13) . . . . ?
N1 C5 C6 C7 -1.26(16) . . . . ?
N1 C5 C4 C3 178.71(13) . . . . ?
O1 C10 C11 F1 -173.05(12) . . . . ?
O1 C10 C11 F2 67.38(16) . . . . ?
O1 C10 C11 F3 -52.51(16) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C2 C1 C6 C7 -177.25(15) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C5 N1 C8 O2 -178.96(14) . . . . ?
C5 N1 C8 C7 4.14(16) . . . . ?
C7 C10 C11 F1 -50.16(17) . . . . ?
C7 C10 C11 F2 -169.73(12) . . . . ?
C7 C10 C11 F3 70.38(16) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C5 C4 C3 -0.9(2) . . . . ?
C6 C7 C12 C13 59.64(16) . . . . ?
C6 C7 C8 N1 -4.56(15) . . . . ?
C6 C7 C8 O2 178.59(14) . . . . ?
C6 C7 C10 O1 67.66(15) . . . . ?
C6 C7 C10 C11 -51.88(17) . . . . ?
C12 C7 C6 C1 66.7(2) . . . . ?
C12 C7 C6 C5 -109.73(13) . . . . ?
C12 C7 C8 N1 112.19(13) . . . . ?
C12 C7 C8 O2 -64.65(18) . . . . ?
C12 C7 C10 O1 -58.09(15) . . . . ?
C12 C7 C10 C11 -177.64(12) . . . . ?
C8 N1 C5 C6 -1.88(16) . . . . ?
C8 N1 C5 C4 178.45(14) . . . . ?
C8 C7 C6 C1 179.83(15) . . . . ?
C8 C7 C6 C5 3.44(15) . . . . ?
C8 C7 C12 C13 -50.72(16) . . . . ?
C8 C7 C10 O1 -175.33(11) . . . . ?
C8 C7 C10 C11 65.12(16) . . . . ?
C14 C13 C12 C7 -106.61(18) . . . . ?
C9 N1 C5 C6 171.85(13) . . . . ?
C9 N1 C5 C4 -7.8(2) . . . . ?
C9 N1 C8 O2 7.3(2) . . . . ?
C9 N1 C8 C7 -169.64(13) . . . . ?
C10 C7 C6 C1 -57.4(2) . . . . ?
C10 C7 C6 C5 126.20(13) . . . . ?
C10 C7 C12 C13 -171.86(13) . . . . ?
C10 C7 C8 N1 -129.64(13) . . . . ?
C10 C7 C8 O2 53.51(19) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C4 C5 C6 C7 178.43(13) . . . . ?

_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_cb5_82a
_database_code_depnum_ccdc_archive 'CCDC 1822707'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;
_audit_creation_date             2018-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 F3 N O2'
_chemical_formula_sum            'C11 H8 F3 N O2'
_chemical_formula_weight         243.18
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4267(18)
_cell_length_b                   8.6492(19)
_cell_length_c                   9.7530(17)
_cell_angle_alpha                87.306(16)
_cell_angle_beta                 68.08(2)
_cell_angle_gamma                67.56(2)
_cell_volume                     533.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    951
_cell_measurement_temperature    294.47(10)
_cell_measurement_theta_max      23.6490
_cell_measurement_theta_min      4.4420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3584
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.355
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.47(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    4.00   55.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega   29.00   54.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000   60.0000 17

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   23.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -150.0000 18

#__ type_ start__ end____ width___ exp.time_
  4 omega   47.00  105.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega  -53.00   82.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  6 omega    9.00   94.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega -102.00  -72.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -120.0000 20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0640707000
_diffrn_orient_matrix_UB_12      -0.0267860000
_diffrn_orient_matrix_UB_13      0.0422485000
_diffrn_orient_matrix_UB_21      0.0861557000
_diffrn_orient_matrix_UB_22      -0.0508492000
_diffrn_orient_matrix_UB_23      -0.0637334000
_diffrn_orient_matrix_UB_31      0.0317324000
_diffrn_orient_matrix_UB_32      0.0683269000
_diffrn_orient_matrix_UB_33      -0.0193854000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1339
_reflns_number_total             2083
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.044
_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)+(0.0597P)²+0.1418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1660
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 -0.4454(3) 0.3453(3) 0.3130(3) 0.1335(9) Uani 1 1 d . . . . .
F2 F -0.4260(3) 0.1317(3) 0.4319(2) 0.1396(10) Uani 1 1 d . . . . .
F3 F -0.3278(3) 0.3106(3) 0.4832(2) 0.1228(8) Uani 1 1 d . . . . .
O1 O 0.0569(3) 0.0782(2) 0.3049(2) 0.0783(6) Uani 1 1 d . . . . .
O2 O 0.2611(3) -0.0211(2) -0.0177(2) 0.0822(6) Uani 1 1 d . . . . .
N1 N 0.2757(3) 0.2405(3) -0.0266(2) 0.0656(6) Uani 1 1 d . . . . .
C1 C 0.1917(4) 0.3832(3) 0.0754(3) 0.0639(7) Uani 1 1 d . . . . .
C2 C 0.2287(5) 0.5289(4) 0.0511(4) 0.0870(10) Uani 1 1 d . . . . .
H2 H 0.3150 0.5437 -0.0417 0.104 Uiso 1 1 calc R . . . .
C3 C 0.1314(6) 0.6523(4) 0.1710(6) 0.1001(13) Uani 1 1 d . . . . .
H3 H 0.1535 0.7517 0.1579 0.120 Uiso 1 1 calc R . . . .
C4 C 0.0053(6) 0.6322(4) 0.3066(5) 0.0979(12) Uani 1 1 d . . . . .
H4 H -0.0560 0.7169 0.3848 0.117 Uiso 1 1 calc R . . . .
C5 C -0.0333(5) 0.4868(3) 0.3297(4) 0.0779(8) Uani 1 1 d . . . . .
H5 H -0.1204 0.4734 0.4228 0.094 Uiso 1 1 calc R . . . .
C6 C 0.0595(4) 0.3618(3) 0.2126(3) 0.0600(7) Uani 1 1 d . . . . .
C7 C 0.0541(4) 0.1947(3) 0.1951(3) 0.0583(6) Uani 1 1 d . . . . .
C8 C 0.2097(4) 0.1190(3) 0.0388(3) 0.0628(7) Uani 1 1 d . . . . .
C9 C 0.4233(4) 0.2179(5) -0.1793(3) 0.0921(10) Uani 1 1 d . . . . .
H9A H 0.5522 0.2202 -0.1808 0.138 Uiso 1 1 calc GR . . . .
H9B H 0.3632 0.3070 -0.2315 0.138 Uiso 1 1 calc GR . . . .
H9C H 0.4522 0.1116 -0.2268 0.138 Uiso 1 1 calc GR . . . .
C10 C -0.1151(4) 0.1324(3) 0.2580(3) 0.0685(7) Uani 1 1 d . . . . .
H10 H -0.1105 0.0484 0.1912 0.082 Uiso 1 1 calc R . . . .
C11 C -0.3285(6) 0.2308(4) 0.3713(4) 0.0875(10) 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
F1 C11 1.310(4) . ?
F2 C11 1.310(3) . ?
F3 C11 1.321(4) . ?
O1 C7 1.436(3) . ?
O1 C10 1.422(3) . ?
O2 C8 1.213(3) . ?
N1 C1 1.402(3) . ?
N1 C8 1.359(3) . ?
N1 C9 1.450(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 C7 1.480(3) . ?
C7 C8 1.513(3) . ?
C7 C10 1.468(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.486(4) . ?

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
C10 O1 C7 61.84(16) . . ?
C1 N1 C9 125.7(2) . . ?
C8 N1 C1 110.9(2) . . ?
C8 N1 C9 123.3(3) . . ?
C2 C1 N1 127.5(3) . . ?
C2 C1 C6 121.7(3) . . ?
C6 C1 N1 110.8(2) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.1(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.3(2) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 134.2(3) . . ?
O1 C7 C6 124.2(2) . . ?
O1 C7 C8 114.7(2) . . ?
O1 C7 C10 58.60(16) . . ?
C6 C7 C8 105.3(2) . . ?
C10 C7 C6 132.2(2) . . ?
C10 C7 C8 115.5(2) . . ?
O2 C8 N1 127.0(3) . . ?
O2 C8 C7 126.6(2) . . ?
N1 C8 C7 106.4(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 59.57(16) . . ?
O1 C10 H10 114.6 . . ?
O1 C10 C11 117.3(3) . . ?
C7 C10 H10 114.6 . . ?
C7 C10 C11 124.7(2) . . ?
C11 C10 H10 114.6 . . ?
F1 C11 F3 106.5(3) . . ?
F1 C11 C10 111.6(3) . . ?
F2 C11 F1 108.1(3) . . ?
F2 C11 F3 105.5(3) . . ?
F2 C11 C10 110.6(3) . . ?
F3 C11 C10 114.2(3) . . ?

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 C7 C8 O2 35.8(4) . . . . ?
O1 C7 C8 N1 -145.8(2) . . . . ?
O1 C7 C10 C11 103.9(3) . . . . ?
O1 C10 C11 F1 145.4(3) . . . . ?
O1 C10 C11 F2 -94.3(3) . . . . ?
O1 C10 C11 F3 24.6(4) . . . . ?
N1 C1 C2 C3 -178.3(3) . . . . ?
N1 C1 C6 C5 177.8(2) . . . . ?
N1 C1 C6 C7 -1.7(3) . . . . ?
C1 N1 C8 O2 -176.8(3) . . . . ?
C1 N1 C8 C7 4.8(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 O1 139.7(2) . . . . ?
C1 C6 C7 C8 4.4(3) . . . . ?
C1 C6 C7 C10 -143.8(3) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
C5 C6 C7 O1 -39.8(4) . . . . ?
C5 C6 C7 C8 -175.0(3) . . . . ?
C5 C6 C7 C10 36.7(5) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C6 C7 C8 O2 175.9(3) . . . . ?
C6 C7 C8 N1 -5.7(3) . . . . ?
C6 C7 C10 O1 -109.6(3) . . . . ?
C6 C7 C10 C11 -5.8(5) . . . . ?
C7 O1 C10 C11 -116.1(3) . . . . ?
C7 C10 C11 F1 75.0(4) . . . . ?
C7 C10 C11 F2 -164.6(3) . . . . ?
C7 C10 C11 F3 -45.8(4) . . . . ?
C8 N1 C1 C2 177.7(2) . . . . ?
C8 N1 C1 C6 -2.1(3) . . . . ?
C8 C7 C10 O1 104.6(2) . . . . ?
C8 C7 C10 C11 -151.6(3) . . . . ?
C9 N1 C1 C2 1.2(4) . . . . ?
C9 N1 C1 C6 -178.6(2) . . . . ?
C9 N1 C8 O2 -0.2(4) . . . . ?
C9 N1 C8 C7 -178.6(2) . . . . ?
C10 O1 C7 C6 122.4(3) . . . . ?
C10 O1 C7 C8 -106.0(2) . . . . ?
C10 C7 C8 O2 -29.6(4) . . . . ?
C10 C7 C8 N1 148.7(2) . . . . ?

_olex2_date_sample_data_collection 2017-09-20
_olex2_submission_special_instructions 'No special instructions were received'
