# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_shengyi_0508
_database_code_depnum_ccdc_archive 'CCDC 1813400'
_audit_update_record             
;
2017-12-26 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;
_audit_creation_date             2017-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 F5 O2'
_chemical_formula_sum            'C15 H9 F5 O2'
_chemical_formula_weight         316.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.7847(11)
_cell_length_b                   8.7041(9)
_cell_length_c                   28.524(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.114(10)
_cell_angle_gamma                90
_cell_volume                     2643.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1151
_cell_measurement_temperature    296.61(19)
_cell_measurement_theta_max      20.9260
_cell_measurement_theta_min      3.8250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_preparation       ?
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.1210
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.480
_diffrn_ambient_temperature      296.61(19)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    8.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   65.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -90.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0096560000
_diffrn_orient_matrix_UB_12      0.0355445000
_diffrn_orient_matrix_UB_13      0.0215089000
_diffrn_orient_matrix_UB_21      0.0658979000
_diffrn_orient_matrix_UB_22      0.0048074000
_diffrn_orient_matrix_UB_23      0.0072337000
_diffrn_orient_matrix_UB_31      0.0003630000
_diffrn_orient_matrix_UB_32      0.0731505000
_diffrn_orient_matrix_UB_33      -0.0109394000
_diffrn_radiation_monochromator  mirror
_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                2172
_reflns_number_total             5195
_reflns_odcompleteness_completeness 99.60
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1804
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+0.9360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.2310
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_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
F1 F 0.1044(3) -0.1046(4) 0.43578(11) 0.0789(10) Uani 1 1 d . . . . .
F2 F -0.0766(4) -0.1664(4) 0.48694(13) 0.0954(12) Uani 1 1 d . . . . .
F3 F -0.3084(3) -0.0452(5) 0.46225(14) 0.1030(14) Uani 1 1 d . . . . .
F4 F -0.3608(3) 0.1331(4) 0.38282(14) 0.0940(12) Uani 1 1 d . . . . .
F5 F -0.1779(3) 0.2012(4) 0.33257(12) 0.0717(9) Uani 1 1 d . . . . .
O1 O 0.1745(4) 0.2246(5) 0.41641(14) 0.0783(13) Uani 1 1 d . . . . .
O2 O 0.1276(3) 0.0047(4) 0.23486(13) 0.0659(11) Uani 1 1 d . . . . .
C1 C -0.1504(5) 0.1064(6) 0.3704(2) 0.0541(14) Uani 1 1 d . . . . .
C2 C -0.2455(5) 0.0738(7) 0.3963(2) 0.0625(15) Uani 1 1 d . . . . .
C3 C -0.2198(6) -0.0163(7) 0.4354(2) 0.0648(16) Uani 1 1 d . . . . .
C4 C -0.1016(6) -0.0755(7) 0.4489(2) 0.0625(15) Uani 1 1 d . . . . .
C5 C -0.0100(5) -0.0437(6) 0.42165(19) 0.0550(14) Uani 1 1 d . . . . .
C6 C -0.0316(4) 0.0488(6) 0.38204(18) 0.0470(12) Uani 1 1 d . . . . .
C7 C 0.0688(4) 0.0835(5) 0.35295(18) 0.0456(12) Uani 1 1 d . . . . .
C8 C 0.1709(5) 0.1747(6) 0.3706(2) 0.0561(14) Uani 1 1 d . . . . .
C9 C 0.2593(5) 0.2164(6) 0.3421(2) 0.0605(15) Uani 1 1 d . . . . .
H9 H 0.3258 0.2803 0.3541 0.073 Uiso 1 1 calc R . . . .
C10 C 0.2481(5) 0.1628(6) 0.2959(2) 0.0619(15) Uani 1 1 d . . . . .
H10 H 0.3064 0.1899 0.2766 0.074 Uiso 1 1 calc R . . . .
C11 C 0.1489(5) 0.0688(6) 0.27946(19) 0.0495(13) Uani 1 1 d . . . . .
C12 C 0.0593(4) 0.0274(5) 0.30740(18) 0.0439(12) Uani 1 1 d . . . . .
C13 C -0.0340(5) -0.0772(6) 0.27850(17) 0.0511(13) Uani 1 1 d . . . . .
H13A H -0.1192 -0.0401 0.2775 0.061 Uiso 1 1 calc R . . . .
H13B H -0.0280 -0.1811 0.2909 0.061 Uiso 1 1 calc R . . . .
C14 C 0.0065(5) -0.0691(7) 0.2296(2) 0.0646(15) Uani 1 1 d . . . . .
H14A H 0.0117 -0.1717 0.2168 0.077 Uiso 1 1 calc R . . . .
H14B H -0.0543 -0.0107 0.2079 0.077 Uiso 1 1 calc R . . . .
C15 C 0.2750(6) 0.3222(9) 0.4371(2) 0.099(2) Uani 1 1 d . . . . .
H15A H 0.2692 0.4188 0.4206 0.148 Uiso 1 1 calc GR . . . .
H15B H 0.3538 0.2743 0.4345 0.148 Uiso 1 1 calc GR . . . .
H15C H 0.2694 0.3390 0.4699 0.148 Uiso 1 1 calc GR . . . .
F6 F 0.5725(3) 0.4116(4) 0.44013(12) 0.0881(11) Uani 1 1 d . . . . .
F7 F 0.8002(4) 0.3401(5) 0.48537(13) 0.0976(12) Uani 1 1 d . . . . .
F8 F 1.0081(3) 0.4457(5) 0.45312(12) 0.0953(12) Uani 1 1 d . . . . .
F9 F 0.9847(3) 0.6276(4) 0.37560(12) 0.0794(10) Uani 1 1 d . . . . .
F10 F 0.7548(3) 0.7070(4) 0.33103(11) 0.0686(9) Uani 1 1 d . . . . .
O3 O 0.4885(4) 0.7450(5) 0.41943(16) 0.0884(14) Uani 1 1 d . . . . .
O4 O 0.3557(4) 0.5114(5) 0.24041(15) 0.0722(11) Uani 1 1 d . . . . .
C16 C 0.6716(5) 0.4676(6) 0.4231(2) 0.0577(14) Uani 1 1 d . . . . .
C17 C 0.7895(6) 0.4304(6) 0.4469(2) 0.0610(15) Uani 1 1 d . . . . .
C18 C 0.8929(5) 0.4830(7) 0.4305(2) 0.0593(15) Uani 1 1 d . . . . .
C19 C 0.8805(5) 0.5741(6) 0.3906(2) 0.0570(14) Uani 1 1 d . . . . .
C20 C 0.7632(5) 0.6126(6) 0.36846(19) 0.0506(13) Uani 1 1 d . . . . .
C21 C 0.6549(5) 0.5587(5) 0.38330(18) 0.0487(13) Uani 1 1 d . . . . .
C22 C 0.5298(4) 0.5959(6) 0.3560(2) 0.0495(13) Uani 1 1 d . . . . .
C23 C 0.4459(5) 0.6924(7) 0.3748(2) 0.0656(16) Uani 1 1 d . . . . .
C24 C 0.3324(5) 0.7310(7) 0.3478(2) 0.0756(18) Uani 1 1 d . . . . .
H24 H 0.2777 0.7953 0.3607 0.091 Uiso 1 1 calc R . . . .
C25 C 0.2980(5) 0.6767(7) 0.3023(2) 0.0730(18) Uani 1 1 d . . . . .
H25 H 0.2226 0.7062 0.2841 0.088 Uiso 1 1 calc R . . . .
C26 C 0.3785(5) 0.5774(6) 0.2846(2) 0.0591(15) Uani 1 1 d . . . . .
C27 C 0.4708(5) 0.4369(7) 0.2326(2) 0.0682(16) Uani 1 1 d . . . . .
H27A H 0.5113 0.4963 0.2105 0.082 Uiso 1 1 calc R . . . .
H27B H 0.4531 0.3350 0.2195 0.082 Uiso 1 1 calc R . . . .
C28 C 0.5565(5) 0.4267(6) 0.28127(18) 0.0563(14) Uani 1 1 d . . . . .
H28A H 0.5586 0.3233 0.2940 0.068 Uiso 1 1 calc R . . . .
H28B H 0.6415 0.4595 0.2792 0.068 Uiso 1 1 calc R . . . .
C29 C 0.4927(5) 0.5366(5) 0.3106(2) 0.0500(13) Uani 1 1 d . . . . .
C30 C 0.4085(7) 0.8362(9) 0.4432(3) 0.111(3) Uani 1 1 d . . . . .
H30A H 0.3871 0.9289 0.4256 0.166 Uiso 1 1 calc GR . . . .
H30B H 0.4511 0.8615 0.4744 0.166 Uiso 1 1 calc GR . . . .
H30C H 0.3334 0.7797 0.4457 0.166 Uiso 1 1 calc GR . . . .


_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 C5 1.345(6) . ?
F2 C4 1.336(6) . ?
F3 C3 1.340(5) . ?
F4 C2 1.344(6) . ?
F5 C1 1.353(6) . ?
O1 C8 1.372(6) . ?
O1 C15 1.428(7) . ?
O2 C11 1.375(6) . ?
O2 C14 1.442(6) . ?
C1 C2 1.385(7) . ?
C1 C6 1.367(7) . ?
C2 C3 1.357(8) . ?
C3 C4 1.372(8) . ?
C4 C5 1.378(7) . ?
C5 C6 1.377(7) . ?
C6 C7 1.495(6) . ?
C7 C8 1.386(7) . ?
C7 C12 1.377(6) . ?
C8 C9 1.395(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(7) . ?
C11 C12 1.394(6) . ?
C12 C13 1.502(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.528(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
F6 C16 1.334(6) . ?
F7 C17 1.339(6) . ?
F8 C18 1.347(6) . ?
F9 C19 1.348(6) . ?
F10 C20 1.339(6) . ?
O3 C23 1.363(7) . ?
O3 C30 1.421(6) . ?
O4 C26 1.372(6) . ?
O4 C27 1.449(6) . ?
C16 C17 1.382(7) . ?
C16 C21 1.373(7) . ?
C17 C18 1.357(8) . ?
C18 C19 1.375(7) . ?
C19 C20 1.363(7) . ?
C20 C21 1.385(6) . ?
C21 C22 1.484(7) . ?
C22 C23 1.402(7) . ?
C22 C29 1.391(7) . ?
C23 C24 1.381(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(7) . ?
C26 C29 1.380(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.544(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.508(7) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C8 O1 C15 119.1(4) . . ?
C11 O2 C14 107.0(4) . . ?
F5 C1 C2 117.5(5) . . ?
F5 C1 C6 119.8(4) . . ?
C6 C1 C2 122.7(5) . . ?
F4 C2 C1 119.9(6) . . ?
F4 C2 C3 121.1(5) . . ?
C3 C2 C1 119.0(5) . . ?
F3 C3 C2 120.5(6) . . ?
F3 C3 C4 119.0(6) . . ?
C2 C3 C4 120.5(5) . . ?
F2 C4 C3 120.6(5) . . ?
F2 C4 C5 120.4(6) . . ?
C3 C4 C5 118.9(5) . . ?
F1 C5 C4 117.2(5) . . ?
F1 C5 C6 120.3(5) . . ?
C6 C5 C4 122.4(5) . . ?
C1 C6 C5 116.4(5) . . ?
C1 C6 C7 121.6(5) . . ?
C5 C6 C7 122.0(5) . . ?
C8 C7 C6 121.2(5) . . ?
C12 C7 C6 120.0(4) . . ?
C12 C7 C8 118.8(4) . . ?
O1 C8 C7 115.3(4) . . ?
O1 C8 C9 123.7(5) . . ?
C7 C8 C9 121.0(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.3(5) . . ?
C11 C10 H10 120.9 . . ?
O2 C11 C12 113.2(4) . . ?
C10 C11 O2 124.5(5) . . ?
C10 C11 C12 122.2(5) . . ?
C7 C12 C11 119.5(5) . . ?
C7 C12 C13 132.5(4) . . ?
C11 C12 C13 107.9(4) . . ?
C12 C13 H13A 111.3 . . ?
C12 C13 H13B 111.3 . . ?
C12 C13 C14 102.1(4) . . ?
H13A C13 H13B 109.2 . . ?
C14 C13 H13A 111.4 . . ?
C14 C13 H13B 111.3 . . ?
O2 C14 C13 108.1(4) . . ?
O2 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 O3 C30 119.6(5) . . ?
C26 O4 C27 107.2(4) . . ?
F6 C16 C17 117.6(5) . . ?
F6 C16 C21 120.3(5) . . ?
C21 C16 C17 122.1(5) . . ?
F7 C17 C16 119.6(5) . . ?
F7 C17 C18 120.8(5) . . ?
C18 C17 C16 119.6(5) . . ?
F8 C18 C17 120.0(5) . . ?
F8 C18 C19 119.8(5) . . ?
C17 C18 C19 120.2(5) . . ?
F9 C19 C18 119.0(5) . . ?
F9 C19 C20 121.8(5) . . ?
C20 C19 C18 119.2(5) . . ?
F10 C20 C19 117.5(4) . . ?
F10 C20 C21 119.9(5) . . ?
C19 C20 C21 122.6(5) . . ?
C16 C21 C20 116.3(5) . . ?
C16 C21 C22 123.3(5) . . ?
C20 C21 C22 120.4(5) . . ?
C23 C22 C21 121.2(5) . . ?
C29 C22 C21 120.7(4) . . ?
C29 C22 C23 118.0(5) . . ?
O3 C23 C22 114.6(5) . . ?
O3 C23 C24 125.3(5) . . ?
C24 C23 C22 120.1(6) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.7(5) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 118.1(6) . . ?
C26 C25 H25 121.0 . . ?
O4 C26 C25 124.7(5) . . ?
O4 C26 C29 113.7(5) . . ?
C25 C26 C29 121.7(6) . . ?
O4 C27 H27A 110.3 . . ?
O4 C27 H27B 110.3 . . ?
O4 C27 C28 107.0(4) . . ?
H27A C27 H27B 108.6 . . ?
C28 C27 H27A 110.3 . . ?
C28 C27 H27B 110.3 . . ?
C27 C28 H28A 111.4 . . ?
C27 C28 H28B 111.4 . . ?
H28A C28 H28B 109.3 . . ?
C29 C28 C27 101.7(4) . . ?
C29 C28 H28A 111.4 . . ?
C29 C28 H28B 111.4 . . ?
C22 C29 C28 131.5(5) . . ?
C26 C29 C22 120.3(5) . . ?
C26 C29 C28 108.2(5) . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C6 C1 -179.7(5) . . . . ?
F1 C5 C6 C7 0.9(8) . . . . ?
F2 C4 C5 F1 -1.7(8) . . . . ?
F2 C4 C5 C6 179.7(5) . . . . ?
F3 C3 C4 F2 3.1(8) . . . . ?
F3 C3 C4 C5 -179.1(5) . . . . ?
F4 C2 C3 F3 -1.6(9) . . . . ?
F4 C2 C3 C4 -179.7(5) . . . . ?
F5 C1 C2 F4 1.5(8) . . . . ?
F5 C1 C2 C3 -177.6(5) . . . . ?
F5 C1 C6 C5 178.4(4) . . . . ?
F5 C1 C6 C7 -2.2(8) . . . . ?
O1 C8 C9 C10 -179.1(5) . . . . ?
O2 C11 C12 C7 -179.9(4) . . . . ?
O2 C11 C12 C13 0.0(6) . . . . ?
C1 C2 C3 F3 177.5(5) . . . . ?
C1 C2 C3 C4 -0.6(9) . . . . ?
C1 C6 C7 C8 111.5(6) . . . . ?
C1 C6 C7 C12 -67.0(7) . . . . ?
C2 C1 C6 C5 -0.5(8) . . . . ?
C2 C1 C6 C7 178.9(5) . . . . ?
C2 C3 C4 F2 -178.8(5) . . . . ?
C2 C3 C4 C5 -0.9(9) . . . . ?
C3 C4 C5 F1 -179.5(5) . . . . ?
C3 C4 C5 C6 1.8(9) . . . . ?
C4 C5 C6 C1 -1.1(8) . . . . ?
C4 C5 C6 C7 179.5(5) . . . . ?
C5 C6 C7 C8 -69.1(7) . . . . ?
C5 C6 C7 C12 112.4(6) . . . . ?
C6 C1 C2 F4 -179.5(5) . . . . ?
C6 C1 C2 C3 1.4(9) . . . . ?
C6 C7 C8 O1 2.2(7) . . . . ?
C6 C7 C8 C9 -175.0(5) . . . . ?
C6 C7 C12 C11 175.7(4) . . . . ?
C6 C7 C12 C13 -4.1(8) . . . . ?
C7 C8 C9 C10 -2.0(8) . . . . ?
C7 C12 C13 C14 172.5(5) . . . . ?
C8 C7 C12 C11 -2.9(7) . . . . ?
C8 C7 C12 C13 177.3(5) . . . . ?
C8 C9 C10 C11 -0.1(8) . . . . ?
C9 C10 C11 O2 -178.5(5) . . . . ?
C9 C10 C11 C12 0.7(8) . . . . ?
C10 C11 C12 C7 0.8(8) . . . . ?
C10 C11 C12 C13 -179.3(5) . . . . ?
C11 O2 C14 C13 -12.6(6) . . . . ?
C11 C12 C13 C14 -7.4(5) . . . . ?
C12 C7 C8 O1 -179.2(4) . . . . ?
C12 C7 C8 C9 3.5(8) . . . . ?
C12 C13 C14 O2 12.1(5) . . . . ?
C14 O2 C11 C10 -172.7(5) . . . . ?
C14 O2 C11 C12 8.0(6) . . . . ?
C15 O1 C8 C7 -178.5(5) . . . . ?
C15 O1 C8 C9 -1.3(9) . . . . ?
F6 C16 C17 F7 0.5(8) . . . . ?
F6 C16 C17 C18 179.0(5) . . . . ?
F6 C16 C21 C20 179.5(5) . . . . ?
F6 C16 C21 C22 -2.3(8) . . . . ?
F7 C17 C18 F8 -0.7(8) . . . . ?
F7 C17 C18 C19 179.2(5) . . . . ?
F8 C18 C19 F9 -1.5(7) . . . . ?
F8 C18 C19 C20 -179.1(5) . . . . ?
F9 C19 C20 F10 -0.3(7) . . . . ?
F9 C19 C20 C21 179.9(4) . . . . ?
F10 C20 C21 C16 -177.4(4) . . . . ?
F10 C20 C21 C22 4.3(7) . . . . ?
O3 C23 C24 C25 177.9(6) . . . . ?
O4 C26 C29 C22 179.2(4) . . . . ?
O4 C26 C29 C28 -1.0(6) . . . . ?
O4 C27 C28 C29 -14.6(5) . . . . ?
C16 C17 C18 F8 -179.2(5) . . . . ?
C16 C17 C18 C19 0.7(9) . . . . ?
C16 C21 C22 C23 69.7(7) . . . . ?
C16 C21 C22 C29 -110.7(6) . . . . ?
C17 C16 C21 C20 -0.6(8) . . . . ?
C17 C16 C21 C22 177.7(5) . . . . ?
C17 C18 C19 F9 178.6(5) . . . . ?
C17 C18 C19 C20 1.0(8) . . . . ?
C18 C19 C20 F10 177.1(5) . . . . ?
C18 C19 C20 C21 -2.6(8) . . . . ?
C19 C20 C21 C16 2.4(8) . . . . ?
C19 C20 C21 C22 -175.9(5) . . . . ?
C20 C21 C22 C23 -112.1(6) . . . . ?
C20 C21 C22 C29 67.4(6) . . . . ?
C21 C16 C17 F7 -179.4(5) . . . . ?
C21 C16 C17 C18 -1.0(9) . . . . ?
C21 C22 C23 O3 -0.9(8) . . . . ?
C21 C22 C23 C24 177.0(5) . . . . ?
C21 C22 C29 C26 -177.1(5) . . . . ?
C21 C22 C29 C28 3.2(8) . . . . ?
C22 C23 C24 C25 0.2(9) . . . . ?
C23 C22 C29 C26 2.5(7) . . . . ?
C23 C22 C29 C28 -177.3(5) . . . . ?
C23 C24 C25 C26 2.2(9) . . . . ?
C24 C25 C26 O4 178.5(5) . . . . ?
C24 C25 C26 C29 -2.3(8) . . . . ?
C25 C26 C29 C22 -0.1(8) . . . . ?
C25 C26 C29 C28 179.7(5) . . . . ?
C26 O4 C27 C28 14.7(6) . . . . ?
C27 O4 C26 C25 170.4(5) . . . . ?
C27 O4 C26 C29 -8.9(6) . . . . ?
C27 C28 C29 C22 -170.6(5) . . . . ?
C27 C28 C29 C26 9.5(5) . . . . ?
C29 C22 C23 O3 179.5(5) . . . . ?
C29 C22 C23 C24 -2.5(8) . . . . ?
C30 O3 C23 C22 -176.2(6) . . . . ?
C30 O3 C23 C24 6.0(9) . . . . ?

_olex2_date_sample_data_collection 2017-05-09
_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_shenyi_0914
_database_code_depnum_ccdc_archive 'CCDC 1813402'
_audit_update_record             
;
2017-12-26 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;
_audit_creation_date             2017-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H19 Cl4 N O2'
_chemical_formula_sum            'C21 H19 Cl4 N O2'
_chemical_formula_weight         459.17
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   12.8660(3)
_cell_length_b                   13.4392(4)
_cell_length_c                   11.7656(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2034.38(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2106
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4930
_cell_measurement_theta_min      3.8290
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4894
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.42
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   17.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -47.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  -30.0000 113
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0045829000
_diffrn_orient_matrix_UB_12      0.0524739000
_diffrn_orient_matrix_UB_13      0.0043043000
_diffrn_orient_matrix_UB_21      -0.0302312000
_diffrn_orient_matrix_UB_22      0.0007073000
_diffrn_orient_matrix_UB_23      -0.0504126000
_diffrn_orient_matrix_UB_31      -0.0458581000
_diffrn_orient_matrix_UB_32      -0.0057341000
_diffrn_orient_matrix_UB_33      0.0327777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2416
_reflns_number_total             2818
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.156
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.1211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0782
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl -0.75263(7) 0.18183(6) -0.47350(9) 0.0584(3) Uani 1 d . . .
Cl2 Cl -0.98145(7) 0.15341(7) -0.40861(12) 0.0750(3) Uani 1 d . . .
Cl3 Cl -0.91818(7) -0.18564(8) -0.22111(10) 0.0719(3) Uani 1 d . . .
Cl4 Cl -0.68302(7) -0.18184(6) -0.27676(9) 0.0545(2) Uani 1 d . . .
O1 O -0.73226(17) -0.00433(19) -0.6348(2) 0.0560(6) Uani 1 d . . .
O2 O -0.67591(19) -0.40753(19) -0.6160(3) 0.0637(7) Uani 1 d . . .
N1 N -0.9307(2) -0.0165(2) -0.3240(3) 0.0486(7) Uani 1 d . . .
C1 C -0.7251(2) -0.1062(3) -0.6281(3) 0.0420(8) Uani 1 d . . .
C2 C -0.7948(2) -0.1686(3) -0.6830(3) 0.0526(9) Uani 1 d . . .
H2 H -0.8502 -0.1411 -0.7230 0.063 Uiso 1 calc . . R
C3 C -0.7835(3) -0.2705(3) -0.6796(4) 0.0562(10) Uani 1 d . . .
H3 H -0.8309 -0.3125 -0.7150 0.067 Uiso 1 calc . . R
C4 C -0.6996(3) -0.3073(3) -0.6219(3) 0.0492(9) Uani 1 d . . .
C5 C -0.5844(3) -0.4159(3) -0.5464(4) 0.0749(13) Uani 1 d . . .
H5A H -0.5292 -0.4480 -0.5890 0.090 Uiso 1 calc . . R
H5B H -0.5993 -0.4563 -0.4800 0.090 Uiso 1 calc . . R
C6 C -0.5503(3) -0.3130(2) -0.5100(4) 0.0550(10) Uani 1 d . . .
H6A H -0.5512 -0.3064 -0.4279 0.066 Uiso 1 calc . . R
H6B H -0.4812 -0.2977 -0.5379 0.066 Uiso 1 calc . . R
C7 C -0.6310(2) -0.2473(3) -0.5645(3) 0.0426(8) Uani 1 d . . .
C8 C -0.6420(2) -0.1439(2) -0.5637(3) 0.0382(7) Uani 1 d . . .
C9 C -0.5629(2) -0.0835(2) -0.4967(3) 0.0409(7) Uani 1 d . . .
H9 H -0.5210 -0.1327 -0.4558 0.049 Uiso 1 calc . . R
C10 C -0.60077(19) -0.0071(2) -0.4021(3) 0.0395(7) Uani 1 d . . .
H10 H -0.5712 -0.0324 -0.3310 0.047 Uiso 1 calc . . R
C11 C -0.5366(2) 0.0867(3) -0.4294(4) 0.0508(9) Uani 1 d . . .
H11 H -0.5643 0.1486 -0.3973 0.061 Uiso 1 calc . . R
C12 C -0.4233(2) 0.0633(3) -0.3962(4) 0.0593(10) Uani 1 d . . .
H12A H -0.3815 0.1233 -0.3942 0.071 Uiso 1 calc . . R
H12B H -0.4200 0.0310 -0.3225 0.071 Uiso 1 calc . . R
C13 C -0.3866(3) -0.0073(3) -0.4911(4) 0.0620(11) Uani 1 d . . .
H13A H -0.3303 0.0220 -0.5345 0.074 Uiso 1 calc . . R
H13B H -0.3637 -0.0705 -0.4602 0.074 Uiso 1 calc . . R
C14 C -0.4837(2) -0.0202(3) -0.5645(3) 0.0519(9) Uani 1 d . . .
H14 H -0.4701 -0.0443 -0.6416 0.062 Uiso 1 calc . . R
C15 C -0.5279(3) 0.0855(3) -0.5587(4) 0.0567(10) Uani 1 d . . .
H15A H -0.4801 0.1352 -0.5876 0.068 Uiso 1 calc . . R
H15B H -0.5948 0.0915 -0.5962 0.068 Uiso 1 calc . . R
C16 C -0.7177(2) -0.0033(2) -0.3807(3) 0.0363(7) Uani 1 d . . .
C17 C -0.7879(2) 0.0730(2) -0.4069(3) 0.0412(7) Uani 1 d . . .
C18 C -0.8917(2) 0.0614(2) -0.3770(3) 0.0472(9) Uani 1 d . . .
C19 C -0.8649(2) -0.0876(2) -0.2960(3) 0.0443(8) Uani 1 d . . .
C20 C -0.7600(2) -0.0842(2) -0.3220(3) 0.0390(8) Uani 1 d . . .
C21 C -0.8035(3) 0.0388(3) -0.7117(4) 0.0810(14) Uani 1 d . . .
H21A H -0.7934 0.0107 -0.7859 0.122 Uiso 1 calc . . GR
H21B H -0.7924 0.1094 -0.7148 0.122 Uiso 1 calc . . GR
H21C H -0.8732 0.0256 -0.6866 0.122 Uiso 1 calc . . GR


_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 C17 1.720(3) . ?
Cl2 C18 1.732(3) . ?
Cl3 C19 1.728(3) . ?
Cl4 C20 1.727(3) . ?
O1 C1 1.374(4) . ?
O1 C21 1.412(4) . ?
O2 C4 1.383(4) . ?
O2 C5 1.439(5) . ?
N1 C18 1.318(4) . ?
N1 C19 1.318(4) . ?
C1 C2 1.388(5) . ?
C1 C8 1.405(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(5) . ?
C4 C7 1.373(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.513(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.505(5) . ?
C7 C8 1.397(5) . ?
C8 C9 1.523(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.591(4) . ?
C9 C14 1.548(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.540(4) . ?
C10 C16 1.526(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.542(4) . ?
C11 C15 1.526(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.540(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.529(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.531(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.401(4) . ?
C16 C20 1.399(4) . ?
C17 C18 1.390(4) . ?
C19 C20 1.385(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C1 O1 C21 119.2(3) . . ?
C4 O2 C5 106.6(3) . . ?
C19 N1 C18 116.7(3) . . ?
O1 C1 C2 122.2(3) . . ?
O1 C1 C8 116.2(3) . . ?
C2 C1 C8 121.6(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 O2 123.4(3) . . ?
C3 C4 C7 122.6(3) . . ?
C7 C4 O2 113.9(3) . . ?
O2 C5 H5A 109.9 . . ?
O2 C5 H5B 109.9 . . ?
O2 C5 C6 109.0(3) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
C5 C6 H6A 111.3 . . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C7 C6 C5 102.5(3) . . ?
C7 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
C4 C7 C6 108.0(3) . . ?
C4 C7 C8 121.4(3) . . ?
C8 C7 C6 130.6(3) . . ?
C1 C8 C9 126.5(3) . . ?
C7 C8 C1 115.7(3) . . ?
C7 C8 C9 117.8(3) . . ?
C8 C9 H9 105.2 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 C14 117.8(3) . . ?
C10 C9 H9 105.2 . . ?
C14 C9 H9 105.2 . . ?
C14 C9 C10 102.0(3) . . ?
C9 C10 H10 104.7 . . ?
C11 C10 C9 102.6(3) . . ?
C11 C10 H10 104.7 . . ?
C16 C10 C9 116.0(2) . . ?
C16 C10 H10 104.7 . . ?
C16 C10 C11 122.4(3) . . ?
C10 C11 H11 114.8 . . ?
C10 C11 C12 106.7(3) . . ?
C12 C11 H11 114.8 . . ?
C15 C11 C10 103.8(3) . . ?
C15 C11 H11 114.8 . . ?
C15 C11 C12 100.4(3) . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 C11 103.4(3) . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 C12 103.2(3) . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C9 C14 H14 114.5 . . ?
C13 C14 C9 108.0(3) . . ?
C13 C14 H14 114.5 . . ?
C13 C14 C15 100.0(3) . . ?
C15 C14 C9 104.0(3) . . ?
C15 C14 H14 114.5 . . ?
C11 C15 C14 94.7(3) . . ?
C11 C15 H15A 112.8 . . ?
C11 C15 H15B 112.8 . . ?
C14 C15 H15A 112.8 . . ?
C14 C15 H15B 112.8 . . ?
H15A C15 H15B 110.3 . . ?
C17 C16 C10 128.6(3) . . ?
C20 C16 C10 116.1(3) . . ?
C20 C16 C17 115.3(3) . . ?
C16 C17 Cl1 123.5(2) . . ?
C18 C17 Cl1 117.7(2) . . ?
C18 C17 C16 118.8(3) . . ?
N1 C18 Cl2 114.5(2) . . ?
N1 C18 C17 125.1(3) . . ?
C17 C18 Cl2 120.4(3) . . ?
N1 C19 Cl3 115.1(2) . . ?
N1 C19 C20 123.3(3) . . ?
C20 C19 Cl3 121.6(3) . . ?
C16 C20 Cl4 121.3(2) . . ?
C19 C20 Cl4 117.8(2) . . ?
C19 C20 C16 120.9(3) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C17 C18 Cl2 1.1(4) . . . . ?
Cl1 C17 C18 N1 -178.8(3) . . . . ?
Cl3 C19 C20 Cl4 0.0(4) . . . . ?
Cl3 C19 C20 C16 -178.7(3) . . . . ?
O1 C1 C2 C3 177.0(3) . . . . ?
O1 C1 C8 C7 -175.4(3) . . . . ?
O1 C1 C8 C9 3.0(5) . . . . ?
O2 C4 C7 C6 -1.1(4) . . . . ?
O2 C4 C7 C8 178.6(3) . . . . ?
O2 C5 C6 C7 0.4(5) . . . . ?
N1 C19 C20 Cl4 178.6(3) . . . . ?
N1 C19 C20 C16 0.0(5) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
C1 C8 C9 C10 56.1(5) . . . . ?
C1 C8 C9 C14 -69.1(4) . . . . ?
C2 C1 C8 C7 3.7(5) . . . . ?
C2 C1 C8 C9 -177.9(3) . . . . ?
C2 C3 C4 O2 -176.8(4) . . . . ?
C2 C3 C4 C7 3.0(6) . . . . ?
C3 C4 C7 C6 179.0(3) . . . . ?
C3 C4 C7 C8 -1.3(5) . . . . ?
C4 O2 C5 C6 -1.0(5) . . . . ?
C4 C7 C8 C1 -2.1(5) . . . . ?
C4 C7 C8 C9 179.4(3) . . . . ?
C5 O2 C4 C3 -178.8(4) . . . . ?
C5 O2 C4 C7 1.3(4) . . . . ?
C5 C6 C7 C4 0.4(4) . . . . ?
C5 C6 C7 C8 -179.3(4) . . . . ?
C6 C7 C8 C1 177.5(3) . . . . ?
C6 C7 C8 C9 -1.1(6) . . . . ?
C7 C8 C9 C10 -125.5(3) . . . . ?
C7 C8 C9 C14 109.3(3) . . . . ?
C8 C1 C2 C3 -2.1(5) . . . . ?
C8 C9 C10 C11 -133.2(3) . . . . ?
C8 C9 C10 C16 2.9(4) . . . . ?
C8 C9 C14 C13 -153.9(3) . . . . ?
C8 C9 C14 C15 100.5(3) . . . . ?
C9 C10 C11 C12 -70.8(3) . . . . ?
C9 C10 C11 C15 34.7(3) . . . . ?
C9 C10 C16 C17 -110.1(4) . . . . ?
C9 C10 C16 C20 73.4(4) . . . . ?
C9 C14 C15 C11 53.5(3) . . . . ?
C10 C9 C14 C13 72.3(3) . . . . ?
C10 C9 C14 C15 -33.3(3) . . . . ?
C10 C11 C12 C13 74.1(4) . . . . ?
C10 C11 C15 C14 -53.9(3) . . . . ?
C10 C16 C17 Cl1 0.8(5) . . . . ?
C10 C16 C17 C18 -178.5(3) . . . . ?
C10 C16 C20 Cl4 0.2(4) . . . . ?
C10 C16 C20 C19 178.8(3) . . . . ?
C11 C10 C16 C17 16.6(6) . . . . ?
C11 C10 C16 C20 -159.9(3) . . . . ?
C11 C12 C13 C14 -2.6(4) . . . . ?
C12 C11 C15 C14 56.3(3) . . . . ?
C12 C13 C14 C9 -70.5(4) . . . . ?
C12 C13 C14 C15 37.9(4) . . . . ?
C13 C14 C15 C11 -58.1(3) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C14 C9 C10 C16 135.3(3) . . . . ?
C15 C11 C12 C13 -33.8(4) . . . . ?
C16 C10 C11 C12 156.7(3) . . . . ?
C16 C10 C11 C15 -97.7(4) . . . . ?
C16 C17 C18 Cl2 -179.6(3) . . . . ?
C16 C17 C18 N1 0.6(5) . . . . ?
C17 C16 C20 Cl4 -176.8(2) . . . . ?
C17 C16 C20 C19 1.8(5) . . . . ?
C18 N1 C19 Cl3 177.2(3) . . . . ?
C18 N1 C19 C20 -1.5(5) . . . . ?
C19 N1 C18 Cl2 -178.6(3) . . . . ?
C19 N1 C18 C17 1.3(5) . . . . ?
C20 C16 C17 Cl1 177.3(3) . . . . ?
C20 C16 C17 C18 -2.0(5) . . . . ?
C21 O1 C1 C2 -8.8(5) . . . . ?
C21 O1 C1 C8 170.3(3) . . . . ?

_olex2_date_sample_data_collection 2017-09-14
_olex2_submission_special_instructions 'No special instructions were received'
