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

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

data_zxg-3fs-2
_database_code_depnum_ccdc_archive 'CCDC 1551150'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 F N O'
_chemical_formula_sum            'C14 H11 F N O'
_chemical_formula_weight         228.24
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.4508(8)
_cell_length_b                   24.9276(18)
_cell_length_c                   9.8093(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.630(9)
_cell_angle_gamma                90
_cell_volume                     2435.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2256
_cell_measurement_temperature    294.94(10)
_cell_measurement_theta_max      71.2030
_cell_measurement_theta_min      4.7690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            c
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6817
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.534
_diffrn_reflns_theta_min         4.781
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.94(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  150.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   90.00  175.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  116.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  177.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -30.0000 138

#__ type_ start__ end____ width___ exp.time_
 13 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
 14 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 15 omega  -33.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1501619000
_diffrn_orient_matrix_UB_12      -0.0057085000
_diffrn_orient_matrix_UB_13      -0.0830621000
_diffrn_orient_matrix_UB_21      0.0302030000
_diffrn_orient_matrix_UB_22      0.0140504000
_diffrn_orient_matrix_UB_23      -0.1400111000
_diffrn_orient_matrix_UB_31      0.0215098000
_diffrn_orient_matrix_UB_32      -0.0599420000
_diffrn_orient_matrix_UB_33      -0.0249600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1790
_reflns_number_total             2373
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.045
_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)+(0.1300P)²+0.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_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
N001 N 0.38587(15) 0.30595(6) 0.28939(17) 0.0649(5) Uani 1 1 d . . . . .
F002 F 0.1136(2) 0.13456(8) 0.16477(18) 0.1335(8) Uani 1 1 d . . . . .
O003 O 0.2188(2) 0.23192(8) 0.15429(18) 0.1058(7) Uani 1 1 d . . . . .
H003 H 0.2518 0.2620 0.1671 0.159 Uiso 1 1 calc GR . . . .
C004 C 0.35989(18) 0.22245(8) 0.39676(19) 0.0618(5) Uani 1 1 d . . . . .
C005 C 0.45664(18) 0.35708(7) 0.3017(2) 0.0626(5) Uani 1 1 d . . . . .
H005 H 0.5158 0.3611 0.4000 0.075 Uiso 1 1 calc R . . . .
C006 C 0.41927(18) 0.27500(8) 0.39724(19) 0.0637(5) Uani 1 1 d . . . . .
H006 H 0.4843 0.2865 0.4797 0.076 Uiso 1 1 calc R . . . .
C007 C 0.35794(19) 0.40339(8) 0.2676(2) 0.0684(5) Uani 1 1 d . . . . .
C008 C 0.3997(2) 0.19015(9) 0.5182(2) 0.0751(6) Uani 1 1 d . . . . .
H008 H 0.4648 0.2026 0.5994 0.090 Uiso 1 1 calc R . . . .
C009 C 0.2625(2) 0.20354(9) 0.2753(2) 0.0722(6) Uani 1 1 d . . . . .
C00A C 0.2478(3) 0.12138(9) 0.4004(3) 0.0840(7) Uani 1 1 d . . . . .
H00A H 0.2100 0.0876 0.4009 0.101 Uiso 1 1 calc R . . . .
C00B C 0.3447(3) 0.14021(10) 0.5202(3) 0.0830(7) Uani 1 1 d . . . . .
H00B H 0.3726 0.1191 0.6022 0.100 Uiso 1 1 calc R . . . .
C00C C 0.2452(2) 0.40157(11) 0.1476(3) 0.0862(7) Uani 1 1 d . . . . .
H00C H 0.2306 0.3723 0.0861 0.103 Uiso 1 1 calc R . . . .
C00D C 0.2086(3) 0.15267(10) 0.2822(3) 0.0844(7) Uani 1 1 d . . . . .
C00E C 0.3784(3) 0.44801(10) 0.3551(3) 0.0876(7) Uani 1 1 d . . . . .
H00E H 0.4542 0.4496 0.4347 0.105 Uiso 1 1 calc R . . . .
C00F C 0.1543(3) 0.44418(15) 0.1205(4) 0.1115(11) Uani 1 1 d . . . . .
H00F H 0.0777 0.4428 0.0417 0.134 Uiso 1 1 calc R . . . .
C00G C 0.2889(3) 0.49014(12) 0.3267(4) 0.1139(11) Uani 1 1 d . . . . .
H00G H 0.3043 0.5198 0.3869 0.137 Uiso 1 1 calc R . . . .
C00H C 0.1771(3) 0.48815(14) 0.2094(5) 0.1234(13) Uani 1 1 d . . . . .
H00H H 0.1165 0.5165 0.1899 0.148 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
N001 C005 1.460(2) . ?
N001 C006 1.270(2) . ?
F002 C00D 1.350(3) . ?
O003 H003 0.8200 . ?
O003 C009 1.338(2) . ?
C004 C006 1.449(3) . ?
C004 C008 1.393(3) . ?
C004 C009 1.394(3) . ?
C005 C005 1.552(4) 2_655 ?
C005 H005 0.9800 . ?
C005 C007 1.516(3) . ?
C006 H006 0.9300 . ?
C007 C00C 1.391(3) . ?
C007 C00E 1.381(3) . ?
C008 H008 0.9300 . ?
C008 C00B 1.374(3) . ?
C009 C00D 1.397(3) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.381(4) . ?
C00A C00D 1.354(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00F 1.396(4) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.378(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.375(6) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.370(5) . ?
C00H H00H 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
C006 N001 C005 117.18(16) . . ?
C009 O003 H003 109.5 . . ?
C008 C004 C006 120.19(18) . . ?
C008 C004 C009 119.2(2) . . ?
C009 C004 C006 120.64(17) . . ?
N001 C005 C005 109.10(12) . 2_655 ?
N001 C005 H005 108.9 . . ?
N001 C005 C007 110.65(14) . . ?
C005 C005 H005 108.9 2_655 . ?
C007 C005 C005 110.40(14) . 2_655 ?
C007 C005 H005 108.9 . . ?
N001 C006 C004 122.49(17) . . ?
N001 C006 H006 118.8 . . ?
C004 C006 H006 118.8 . . ?
C00C C007 C005 120.5(2) . . ?
C00E C007 C005 120.57(19) . . ?
C00E C007 C00C 119.0(2) . . ?
C004 C008 H008 119.4 . . ?
C00B C008 C004 121.2(2) . . ?
C00B C008 H008 119.4 . . ?
O003 C009 C004 122.97(19) . . ?
O003 C009 C00D 119.3(2) . . ?
C004 C009 C00D 117.78(19) . . ?
C00B C00A H00A 120.4 . . ?
C00D C00A H00A 120.4 . . ?
C00D C00A C00B 119.2(2) . . ?
C008 C00B C00A 119.9(2) . . ?
C008 C00B H00B 120.1 . . ?
C00A C00B H00B 120.1 . . ?
C007 C00C H00C 120.3 . . ?
C007 C00C C00F 119.3(3) . . ?
C00F C00C H00C 120.3 . . ?
F002 C00D C009 117.7(2) . . ?
F002 C00D C00A 119.5(2) . . ?
C00A C00D C009 122.8(2) . . ?
C007 C00E H00E 119.3 . . ?
C00G C00E C007 121.3(3) . . ?
C00G C00E H00E 119.3 . . ?
C00C C00F H00F 119.7 . . ?
C00H C00F C00C 120.6(3) . . ?
C00H C00F H00F 119.7 . . ?
C00E C00G H00G 120.1 . . ?
C00H C00G C00E 119.8(3) . . ?
C00H C00G H00G 120.1 . . ?
C00F C00H H00H 120.0 . . ?
C00G C00H C00F 120.0(3) . . ?
C00G C00H H00H 120.0 . . ?

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
N001 C005 C007 C00C -46.5(3) . . . . ?
N001 C005 C007 C00E 133.5(2) . . . . ?
O003 C009 C00D F002 -0.2(4) . . . . ?
O003 C009 C00D C00A 179.7(3) . . . . ?
C004 C008 C00B C00A -0.2(4) . . . . ?
C004 C009 C00D F002 179.6(2) . . . . ?
C004 C009 C00D C00A -0.6(4) . . . . ?
C005 N001 C006 C004 -177.84(17) . . . . ?
C005 C005 C007 C00C 74.4(2) 2_655 . . . ?
C005 C005 C007 C00E -105.6(2) 2_655 . . . ?
C005 C007 C00C C00F 178.5(2) . . . . ?
C005 C007 C00E C00G -179.2(2) . . . . ?
C006 N001 C005 C005 112.9(2) . . . 2_655 ?
C006 N001 C005 C007 -125.40(19) . . . . ?
C006 C004 C008 C00B 179.9(2) . . . . ?
C006 C004 C009 O003 0.2(4) . . . . ?
C006 C004 C009 C00D -179.6(2) . . . . ?
C007 C00C C00F C00H 1.5(4) . . . . ?
C007 C00E C00G C00H -0.1(5) . . . . ?
C008 C004 C006 N001 -179.73(19) . . . . ?
C008 C004 C009 O003 -179.9(2) . . . . ?
C008 C004 C009 C00D 0.4(4) . . . . ?
C009 C004 C006 N001 0.3(3) . . . . ?
C009 C004 C008 C00B -0.1(3) . . . . ?
C00B C00A C00D F002 -179.8(2) . . . . ?
C00B C00A C00D C009 0.3(4) . . . . ?
C00C C007 C00E C00G 0.8(4) . . . . ?
C00C C00F C00H C00G -0.8(5) . . . . ?
C00D C00A C00B C008 0.0(4) . . . . ?
C00E C007 C00C C00F -1.5(3) . . . . ?
C00E C00G C00H C00F 0.1(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2017-05-05
_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_zxg-3cls-136k
_database_code_depnum_ccdc_archive 'CCDC 1551147'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H11 Cl N O)'
_chemical_formula_sum            'C28 H22 Cl2 N2 O2'
_chemical_formula_weight         489.37
_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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   10.4917(2)
_cell_length_b                   25.8936(5)
_cell_length_c                   18.0444(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.0418(17)
_cell_angle_gamma                90
_cell_volume                     4898.98(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9056
_cell_measurement_temperature    136.12(18)
_cell_measurement_theta_max      72.3990
_cell_measurement_theta_min      4.5410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27245
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.653
_diffrn_reflns_theta_min         4.905
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      136.12(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  9 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00  126.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00  146.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  109.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega   84.00  176.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  140.0000   71.0000 92

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  109.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   90.00  175.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  109.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00  116.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 20 omega   90.00  175.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 21 omega  100.00  178.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 22 omega   38.00   91.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 23 omega   37.00  146.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  150.0000 109

#__ type_ start__ end____ width___ exp.time_
 24 omega   40.00   98.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 25 omega   38.00   91.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 26 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
 27 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
 29 omega  -33.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
 30 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0020940000
_diffrn_orient_matrix_UB_12      -0.0444409000
_diffrn_orient_matrix_UB_13      0.0567827000
_diffrn_orient_matrix_UB_21      -0.0102150000
_diffrn_orient_matrix_UB_22      -0.0395054000
_diffrn_orient_matrix_UB_23      -0.0637674000
_diffrn_orient_matrix_UB_31      0.1465909000
_diffrn_orient_matrix_UB_32      -0.0020372000
_diffrn_orient_matrix_UB_33      -0.0021744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4213
_reflns_number_total             4842
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.033
_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)+(0.1120P)²+2.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00G(H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_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
Cl01 Cl 0.81933(5) 0.49222(2) 0.28427(3) 0.04140(18) Uani 1 1 d . . . . .
Cl02 Cl 0.48562(6) 0.36345(2) 0.32464(4) 0.0492(2) Uani 1 1 d . . . . .
O003 O 0.41911(14) 0.26543(6) 0.39279(9) 0.0382(4) Uani 1 1 d . . . . .
H003 H 0.3967 0.2378 0.4101 0.057 Uiso 1 1 calc GR . . . .
O004 O 0.77734(15) 0.39237(6) 0.35357(9) 0.0393(4) Uani 1 1 d . . . . .
H004 H 0.7715 0.3638 0.3727 0.059 Uiso 1 1 calc GR . . . .
N005 N 0.26466(15) 0.19118(6) 0.42481(9) 0.0268(3) Uani 1 1 d . . . . .
N006 N 0.83501(16) 0.31672(6) 0.44361(9) 0.0288(3) Uani 1 1 d . . . . .
C007 C 0.19971(19) 0.26350(7) 0.34945(10) 0.0284(4) Uani 1 1 d . . . . .
C008 C 0.29654(18) 0.09759(7) 0.41970(10) 0.0262(4) Uani 1 1 d . . . . .
C009 C 0.23035(18) 0.14178(7) 0.45785(10) 0.0258(4) Uani 1 1 d . . . . .
H009 H 0.1378 0.1370 0.4523 0.031 Uiso 1 1 calc R . . . .
C00A C 0.17818(18) 0.21390(7) 0.38525(10) 0.0279(4) Uani 1 1 d . . . . .
H00A H 0.0987 0.1983 0.3791 0.033 Uiso 1 1 calc R . . . .
C00B C 0.81527(18) 0.22270(7) 0.42637(11) 0.0284(4) Uani 1 1 d . . . . .
C00C C 0.88231(19) 0.41612(8) 0.38078(10) 0.0303(4) Uani 1 1 d . . . . .
C00D C 0.32020(19) 0.28723(7) 0.35495(11) 0.0291(4) Uani 1 1 d . . . . .
C00E C 0.4191(2) 0.10349(8) 0.39390(11) 0.0313(4) Uani 1 1 d . . . . .
H00E H 0.4603 0.1352 0.3989 0.038 Uiso 1 1 calc R . . . .
C00F C 0.93074(19) 0.34333(8) 0.46689(11) 0.0328(4) Uani 1 1 d . . . . .
H00F H 0.9832 0.3300 0.5049 0.039 Uiso 1 1 calc R . . . .
C00G C 0.81552(18) 0.26736(7) 0.48074(10) 0.0283(4) Uani 1 1 d . . . . .
H00G H 0.8840 0.2621 0.5184 0.034 Uiso 1 1 calc R . . . .
C00H C 0.2371(2) 0.04980(8) 0.41251(11) 0.0320(4) Uani 1 1 d . . . . .
H00H H 0.1546 0.0455 0.4288 0.038 Uiso 1 1 calc R . . . .
C00I C 0.7504(2) 0.22597(8) 0.35769(12) 0.0361(5) Uani 1 1 d . . . . .
H00I H 0.7106 0.2567 0.3435 0.043 Uiso 1 1 calc R . . . .
C00J C 0.3358(2) 0.33463(8) 0.31947(12) 0.0343(4) Uani 1 1 d . . . . .
C00K C 0.87228(19) 0.17622(8) 0.44697(12) 0.0327(4) Uani 1 1 d . . . . .
H00K H 0.9151 0.1735 0.4928 0.039 Uiso 1 1 calc R . . . .
C00L C 0.9611(2) 0.39381(8) 0.43619(12) 0.0352(4) Uani 1 1 d . . . . .
C00M C 0.4802(2) 0.06236(9) 0.36075(12) 0.0372(5) Uani 1 1 d . . . . .
H00M H 0.5613 0.0669 0.3426 0.045 Uiso 1 1 calc R . . . .
C00N C 0.9161(2) 0.46448(8) 0.35311(11) 0.0346(4) Uani 1 1 d . . . . .
C00O C 0.2996(2) 0.00853(8) 0.38136(13) 0.0390(5) Uani 1 1 d . . . . .
H00O H 0.2600 -0.0236 0.3784 0.047 Uiso 1 1 calc R . . . .
C00P C 0.0994(2) 0.28760(9) 0.30988(12) 0.0378(5) Uani 1 1 d . . . . .
H00P H 0.0201 0.2716 0.3059 0.045 Uiso 1 1 calc R . . . .
C00Q C 0.4209(2) 0.01469(9) 0.35458(13) 0.0395(5) Uani 1 1 d . . . . .
H00Q H 0.4620 -0.0129 0.3327 0.047 Uiso 1 1 calc R . . . .
C00R C 0.2360(2) 0.35840(8) 0.28141(12) 0.0380(5) Uani 1 1 d . . . . .
H00R H 0.2482 0.3902 0.2589 0.046 Uiso 1 1 calc R . . . .
C00S C 0.8660(2) 0.13363(8) 0.39975(14) 0.0388(5) Uani 1 1 d . . . . .
H00S H 0.9040 0.1026 0.4143 0.047 Uiso 1 1 calc R . . . .
C00T C 0.7449(2) 0.18368(9) 0.31050(12) 0.0414(5) Uani 1 1 d . . . . .
H00T H 0.7019 0.1863 0.2647 0.050 Uiso 1 1 calc R . . . .
C00U C 0.1168(2) 0.33483(9) 0.27667(13) 0.0420(5) Uani 1 1 d . . . . .
H00U H 0.0492 0.3509 0.2512 0.050 Uiso 1 1 calc R . . . .
C00V C 0.8031(2) 0.13748(9) 0.33108(13) 0.0402(5) Uani 1 1 d . . . . .
H00V H 0.8000 0.1093 0.2991 0.048 Uiso 1 1 calc R . . . .
C00W C 1.0247(3) 0.48964(10) 0.37823(16) 0.0516(6) Uani 1 1 d . . . . .
H00W H 1.0456 0.5216 0.3587 0.062 Uiso 1 1 calc R . . . .
C00X C 1.0697(3) 0.42004(12) 0.46187(16) 0.0581(8) Uani 1 1 d . . . . .
H00X H 1.1211 0.4055 0.4994 0.070 Uiso 1 1 calc R . . . .
C00Y C 1.1026(3) 0.46734(13) 0.43246(19) 0.0703(10) Uani 1 1 d . . . . .
H00Y H 1.1767 0.4840 0.4492 0.084 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
Cl01 C00N 1.732(2) . ?
Cl02 C00J 1.740(2) . ?
O003 H003 0.8200 . ?
O003 C00D 1.346(2) . ?
O004 H004 0.8200 . ?
O004 C00C 1.339(3) . ?
N005 C009 1.462(2) . ?
N005 C00A 1.278(3) . ?
N006 C00F 1.277(3) . ?
N006 C00G 1.461(2) . ?
C007 C00A 1.459(3) . ?
C007 C00D 1.406(3) . ?
C007 C00P 1.398(3) . ?
C008 C009 1.516(3) . ?
C008 C00E 1.391(3) . ?
C008 C00H 1.390(3) . ?
C009 C009 1.562(4) 2_556 ?
C009 H009 0.9800 . ?
C00A H00A 0.9300 . ?
C00B C00G 1.517(3) . ?
C00B C00I 1.395(3) . ?
C00B C00K 1.389(3) . ?
C00C C00L 1.399(3) . ?
C00C C00N 1.398(3) . ?
C00D C00J 1.397(3) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.389(3) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.459(3) . ?
C00G C00G 1.562(4) 2_656 ?
C00G H00G 0.9800 . ?
C00H H00H 0.9300 . ?
C00H C00O 1.383(3) . ?
C00I H00I 0.9300 . ?
C00I C00T 1.387(3) . ?
C00J C00R 1.377(3) . ?
C00K H00K 0.9300 . ?
C00K C00S 1.394(3) . ?
C00L C00X 1.392(3) . ?
C00M H00M 0.9300 . ?
C00M C00Q 1.385(3) . ?
C00N C00W 1.375(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.386(3) . ?
C00P H00P 0.9300 . ?
C00P C00U 1.377(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00U 1.391(4) . ?
C00S H00S 0.9300 . ?
C00S C00V 1.386(4) . ?
C00T H00T 0.9300 . ?
C00T C00V 1.388(4) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00W C00Y 1.379(4) . ?
C00X H00X 0.9300 . ?
C00X C00Y 1.383(4) . ?
C00Y H00Y 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
C00D O003 H003 109.5 . . ?
C00C O004 H004 109.5 . . ?
C00A N005 C009 116.78(16) . . ?
C00F N006 C00G 116.27(17) . . ?
C00D C007 C00A 120.43(17) . . ?
C00P C007 C00A 119.58(18) . . ?
C00P C007 C00D 120.00(18) . . ?
C00E C008 C009 120.85(17) . . ?
C00H C008 C009 120.19(17) . . ?
C00H C008 C00E 118.91(18) . . ?
N005 C009 C008 110.59(15) . . ?
N005 C009 C009 109.69(11) . 2_556 ?
N005 C009 H009 109.0 . . ?
C008 C009 C009 109.44(13) . 2_556 ?
C008 C009 H009 109.0 . . ?
C009 C009 H009 109.0 2_556 . ?
N005 C00A C007 122.32(18) . . ?
N005 C00A H00A 118.8 . . ?
C007 C00A H00A 118.8 . . ?
C00I C00B C00G 121.19(18) . . ?
C00K C00B C00G 119.79(18) . . ?
C00K C00B C00I 118.83(19) . . ?
O004 C00C C00L 121.97(18) . . ?
O004 C00C C00N 119.74(19) . . ?
C00N C00C C00L 118.30(19) . . ?
O003 C00D C007 121.85(17) . . ?
O003 C00D C00J 120.03(18) . . ?
C00J C00D C007 118.12(18) . . ?
C008 C00E H00E 119.8 . . ?
C00M C00E C008 120.41(19) . . ?
C00M C00E H00E 119.8 . . ?
N006 C00F H00F 118.7 . . ?
N006 C00F C00L 122.57(19) . . ?
C00L C00F H00F 118.7 . . ?
N006 C00G C00B 111.56(15) . . ?
N006 C00G C00G 110.11(11) . 2_656 ?
N006 C00G H00G 109.1 . . ?
C00B C00G C00G 107.84(14) . 2_656 ?
C00B C00G H00G 109.1 . . ?
C00G C00G H00G 109.1 2_656 . ?
C008 C00H H00H 119.7 . . ?
C00O C00H C008 120.52(19) . . ?
C00O C00H H00H 119.7 . . ?
C00B C00I H00I 119.8 . . ?
C00T C00I C00B 120.4(2) . . ?
C00T C00I H00I 119.8 . . ?
C00D C00J Cl02 118.20(17) . . ?
C00R C00J Cl02 120.33(16) . . ?
C00R C00J C00D 121.5(2) . . ?
C00B C00K H00K 119.6 . . ?
C00B C00K C00S 120.8(2) . . ?
C00S C00K H00K 119.6 . . ?
C00C C00L C00F 120.65(19) . . ?
C00X C00L C00C 119.5(2) . . ?
C00X C00L C00F 119.9(2) . . ?
C00E C00M H00M 119.8 . . ?
C00Q C00M C00E 120.3(2) . . ?
C00Q C00M H00M 119.8 . . ?
C00C C00N Cl01 118.54(17) . . ?
C00W C00N Cl01 119.84(17) . . ?
C00W C00N C00C 121.6(2) . . ?
C00H C00O H00O 119.8 . . ?
C00H C00O C00Q 120.5(2) . . ?
C00Q C00O H00O 119.8 . . ?
C007 C00P H00P 119.7 . . ?
C00U C00P C007 120.6(2) . . ?
C00U C00P H00P 119.7 . . ?
C00M C00Q C00O 119.3(2) . . ?
C00M C00Q H00Q 120.3 . . ?
C00O C00Q H00Q 120.3 . . ?
C00J C00R H00R 120.0 . . ?
C00J C00R C00U 120.04(19) . . ?
C00U C00R H00R 120.0 . . ?
C00K C00S H00S 120.0 . . ?
C00V C00S C00K 120.0(2) . . ?
C00V C00S H00S 120.0 . . ?
C00I C00T H00T 119.7 . . ?
C00I C00T C00V 120.5(2) . . ?
C00V C00T H00T 119.7 . . ?
C00P C00U C00R 119.7(2) . . ?
C00P C00U H00U 120.1 . . ?
C00R C00U H00U 120.1 . . ?
C00S C00V C00T 119.5(2) . . ?
C00S C00V H00V 120.3 . . ?
C00T C00V H00V 120.3 . . ?
C00N C00W H00W 120.0 . . ?
C00N C00W C00Y 119.9(2) . . ?
C00Y C00W H00W 120.0 . . ?
C00L C00X H00X 119.4 . . ?
C00Y C00X C00L 121.1(2) . . ?
C00Y C00X H00X 119.4 . . ?
C00W C00Y C00X 119.6(2) . . ?
C00W C00Y H00Y 120.2 . . ?
C00X C00Y H00Y 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl01 C00N C00W C00Y -179.3(3) . . . . ?
Cl02 C00J C00R C00U 179.16(18) . . . . ?
O003 C00D C00J Cl02 1.0(3) . . . . ?
O003 C00D C00J C00R -178.8(2) . . . . ?
O004 C00C C00L C00F -0.3(3) . . . . ?
O004 C00C C00L C00X 179.4(2) . . . . ?
O004 C00C C00N Cl01 0.3(3) . . . . ?
O004 C00C C00N C00W -178.4(2) . . . . ?
N006 C00F C00L C00C 2.3(3) . . . . ?
N006 C00F C00L C00X -177.4(2) . . . . ?
C007 C00D C00J Cl02 -178.74(15) . . . . ?
C007 C00D C00J C00R 1.4(3) . . . . ?
C007 C00P C00U C00R 1.1(4) . . . . ?
C008 C00E C00M C00Q -1.5(3) . . . . ?
C008 C00H C00O C00Q -2.2(3) . . . . ?
C009 N005 C00A C007 179.69(16) . . . . ?
C009 C008 C00E C00M 178.31(18) . . . . ?
C009 C008 C00H C00O -176.51(18) . . . . ?
C00A N005 C009 C008 108.34(19) . . . . ?
C00A N005 C009 C009 -130.86(19) . . . 2_556 ?
C00A C007 C00D O003 0.1(3) . . . . ?
C00A C007 C00D C00J 179.84(17) . . . . ?
C00A C007 C00P C00U 178.9(2) . . . . ?
C00B C00I C00T C00V 0.4(3) . . . . ?
C00B C00K C00S C00V 0.5(3) . . . . ?
C00C C00L C00X C00Y -1.4(5) . . . . ?
C00C C00N C00W C00Y -0.6(4) . . . . ?
C00D C007 C00A N005 2.7(3) . . . . ?
C00D C007 C00P C00U -0.7(3) . . . . ?
C00D C00J C00R C00U -1.0(3) . . . . ?
C00E C008 C009 N005 35.2(2) . . . . ?
C00E C008 C009 C009 -85.8(2) . . . 2_556 ?
C00E C008 C00H C00O 1.1(3) . . . . ?
C00E C00M C00Q C00O 0.4(3) . . . . ?
C00F N006 C00G C00B -122.25(19) . . . . ?
C00F N006 C00G C00G 118.0(2) . . . 2_656 ?
C00F C00L C00X C00Y 178.4(3) . . . . ?
C00G N006 C00F C00L -178.87(18) . . . . ?
C00G C00B C00I C00T -176.19(19) . . . . ?
C00G C00B C00K C00S 175.81(18) . . . . ?
C00H C008 C009 N005 -147.25(17) . . . . ?
C00H C008 C009 C009 91.8(2) . . . 2_556 ?
C00H C008 C00E C00M 0.7(3) . . . . ?
C00H C00O C00Q C00M 1.4(3) . . . . ?
C00I C00B C00G N006 -43.3(2) . . . . ?
C00I C00B C00G C00G 77.8(2) . . . 2_656 ?
C00I C00B C00K C00S 0.6(3) . . . . ?
C00I C00T C00V C00S 0.7(3) . . . . ?
C00J C00R C00U C00P -0.3(4) . . . . ?
C00K C00B C00G N006 141.59(18) . . . . ?
C00K C00B C00G C00G -97.4(2) . . . 2_656 ?
C00K C00B C00I C00T -1.0(3) . . . . ?
C00K C00S C00V C00T -1.1(3) . . . . ?
C00L C00C C00N Cl01 179.76(16) . . . . ?
C00L C00C C00N C00W 1.0(3) . . . . ?
C00L C00X C00Y C00W 1.8(6) . . . . ?
C00N C00C C00L C00F -179.77(19) . . . . ?
C00N C00C C00L C00X -0.1(3) . . . . ?
C00N C00W C00Y C00X -0.9(5) . . . . ?
C00P C007 C00A N005 -176.88(19) . . . . ?
C00P C007 C00D O003 179.69(19) . . . . ?
C00P C007 C00D C00J -0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2017-04-06
_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_zxg-ljy-f
_database_code_depnum_ccdc_archive 'CCDC 1551151'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2015-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H20 F2 N2 O2)'
_chemical_formula_sum            'C40 H40 F4 N4 O4'
_chemical_formula_weight         716.76
_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      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                   10.4661(4)
_cell_length_b                   11.0082(5)
_cell_length_c                   17.6201(5)
_cell_angle_alpha                95.216(3)
_cell_angle_beta                 96.508(3)
_cell_angle_gamma                110.291(4)
_cell_volume                     1873.27(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7859
_cell_measurement_temperature    293.28(10)
_cell_measurement_theta_max      72.3470
_cell_measurement_theta_min      4.5290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.559
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.28(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  8 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   98.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00  126.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  177.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 138

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00   98.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00  109.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   91.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   91.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 22 omega   91.00  176.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 23 omega   37.00   99.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -22.0000 -152.0000 62

#__ type_ start__ end____ width___ exp.time_
 24 omega   40.00   98.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 25 omega   41.00  126.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00  116.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 27 omega  -35.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -22.0000 -152.0000 99

#__ type_ start__ end____ width___ exp.time_
 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
 29 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 31 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1519572000
_diffrn_orient_matrix_UB_12      0.0825816000
_diffrn_orient_matrix_UB_13      -0.0020485000
_diffrn_orient_matrix_UB_21      -0.0253796000
_diffrn_orient_matrix_UB_22      0.1245456000
_diffrn_orient_matrix_UB_23      0.0294041000
_diffrn_orient_matrix_UB_31      0.0387295000
_diffrn_orient_matrix_UB_32      -0.0193431000
_diffrn_orient_matrix_UB_33      0.0838407000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5515
_reflns_number_total             6681
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.040
_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)+(0.0979P)²+0.1978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1621
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00O(H00O), C00S(H00S), C00Y(H00Y)
2.b Secondary CH2 refined with riding coordinates:
 C00X(H00C,H00D), C00Z(H00A,H00B), C010(H01A,H01B), C015(H01C,H01D), C017(H01E,
 H01F), C018(H01J,H01K), C01B(H01M,H01N), C01E(H01P,H01Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00N(H00N), C00P(H00P), C00Q(H00Q), C00T(H00T),
 C00U(H00U), C00V(H00V), C011(H011), C013(H013), C014(H014), C01A(H01L),
 C01C(H01O), C01D(H01G), C01F(H01H), C01G(H01I)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003), O005(H005), O006(H006)
;
_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
O001 O 0.15346(17) 0.77275(15) 0.87438(9) 0.0794(4) Uani 1 1 d . . . . .
H001 H 0.1442 0.6953 0.8681 0.119 Uiso 1 1 calc GR . . . .
F002 F 0.87555(18) 0.17643(12) 0.59060(9) 0.1051(5) Uani 1 1 d . . . . .
O003 O 1.01908(17) 0.43408(13) 0.60887(10) 0.0825(4) Uani 1 1 d . . . . .
H003 H 1.0501 0.5143 0.6164 0.124 Uiso 1 1 calc GR . . . .
F004 F 0.87128(14) 0.71111(18) 0.94655(9) 0.1113(5) Uani 1 1 d . . . . .
O005 O 0.71456(18) 0.85690(18) 0.59753(9) 0.0871(5) Uani 1 1 d . . . . .
H005 H 0.7974 0.8705 0.6061 0.131 Uiso 1 1 calc GR . . . .
O006 O 0.60791(15) 0.54979(17) 0.91608(10) 0.0878(5) Uani 1 1 d . . . . .
H006 H 0.5270 0.5050 0.8998 0.132 Uiso 1 1 calc GR . . . .
N007 N 0.37219(15) 0.48384(14) 0.83174(9) 0.0589(3) Uani 1 1 d . . . . .
N008 N 1.04828(15) 0.66340(14) 0.67044(8) 0.0567(3) Uani 1 1 d . . . . .
N009 N 0.94304(16) 0.82268(14) 0.57923(8) 0.0601(4) Uani 1 1 d . . . . .
N00A N 0.18262(15) 0.55964(14) 0.90843(8) 0.0583(3) Uani 1 1 d . . . . .
F00B F 0.2166(2) 1.02945(16) 0.91641(13) 0.1327(7) Uani 1 1 d . . . . .
F00C F 0.44193(17) 0.7798(2) 0.55091(10) 0.1299(7) Uani 1 1 d . . . . .
C00D C 0.56719(17) 0.66073(15) 0.81005(9) 0.0529(4) Uani 1 1 d . . . . .
C00E C 0.42245(18) 0.57619(16) 0.79288(10) 0.0551(4) Uani 1 1 d . . . . .
H00E H 0.3656 0.5900 0.7527 0.066 Uiso 1 1 calc R . . . .
C00F C 0.94692(17) 0.61296(17) 0.70571(9) 0.0555(4) Uani 1 1 d . . . . .
H00F H 0.9195 0.6674 0.7383 0.067 Uiso 1 1 calc R . . . .
C00G C 0.87302(17) 0.47250(16) 0.69632(9) 0.0542(4) Uani 1 1 d . . . . .
C00H C 0.65274(19) 0.64379(18) 0.87168(10) 0.0601(4) Uani 1 1 d . . . . .
C00I C 0.73147(19) 0.70615(17) 0.49551(10) 0.0596(4) Uani 1 1 d . . . . .
C00J C 0.16515(18) 0.42229(17) 0.89038(10) 0.0579(4) Uani 1 1 d . . . . .
H00J H 0.2150 0.3977 0.9332 0.069 Uiso 1 1 calc R . . . .
C00K C 0.91302(19) 0.38960(17) 0.64692(10) 0.0596(4) Uani 1 1 d . . . . .
C00L C 0.23070(19) 0.83006(19) 0.94303(11) 0.0634(4) Uani 1 1 d . . . . .
C00M C 0.7892(2) 0.7286(2) 0.88704(11) 0.0682(5) Uani 1 1 d . . . . .
C00N C 0.87770(19) 0.74015(17) 0.52027(10) 0.0595(4) Uani 1 1 d . . . . .
H00N H 0.9255 0.7000 0.4919 0.071 Uiso 1 1 calc R . . . .
C00O C 0.22594(18) 0.40389(17) 0.81726(10) 0.0584(4) Uani 1 1 d . . . . .
H00O H 0.1796 0.4319 0.7745 0.070 Uiso 1 1 calc R . . . .
C00P C 0.8418(2) 0.8265(2) 0.84460(11) 0.0683(5) Uani 1 1 d . . . . .
H00P H 0.9338 0.8817 0.8567 0.082 Uiso 1 1 calc R . . . .
C00Q C 0.25384(19) 0.62297(18) 0.97217(10) 0.0617(4) Uani 1 1 d . . . . .
H00Q H 0.2894 0.5791 1.0066 0.074 Uiso 1 1 calc R . . . .
C00R C 0.28176(19) 0.76096(18) 0.99332(10) 0.0609(4) Uani 1 1 d . . . . .
C00S C 1.09036(19) 0.85031(17) 0.60020(10) 0.0586(4) Uani 1 1 d . . . . .
H00S H 1.1205 0.8024 0.5607 0.070 Uiso 1 1 calc R . . . .
C00T C 0.76143(19) 0.4183(2) 0.73512(11) 0.0673(5) Uani 1 1 d . . . . .
H00T H 0.7356 0.4730 0.7684 0.081 Uiso 1 1 calc R . . . .
C00U C 0.7579(2) 0.84300(18) 0.78366(11) 0.0687(5) Uani 1 1 d . . . . .
H00U H 0.7930 0.9096 0.7543 0.082 Uiso 1 1 calc R . . . .
C00V C 0.6222(2) 0.76091(18) 0.76621(11) 0.0630(4) Uani 1 1 d . . . . .
H00V H 0.5660 0.7721 0.7247 0.076 Uiso 1 1 calc R . . . .
C00W C 0.6559(2) 0.7650(2) 0.53625(11) 0.0655(5) Uani 1 1 d . . . . .
C00X C 1.2715(2) 0.84042(19) 0.70301(11) 0.0660(5) Uani 1 1 d . . . . .
H00C H 1.3062 0.7924 0.6669 0.079 Uiso 1 1 calc R . . . .
H00D H 1.2872 0.8148 0.7534 0.079 Uiso 1 1 calc R . . . .
C00Y C 1.11753(18) 0.80472(16) 0.67820(10) 0.0563(4) Uani 1 1 d . . . . .
H00Y H 1.0807 0.8468 0.7171 0.068 Uiso 1 1 calc R . . . .
C00Z C 0.2081(2) 0.26085(19) 0.79695(13) 0.0710(5) Uani 1 1 d . . . . .
H00A H 0.2426 0.2498 0.7489 0.085 Uiso 1 1 calc R . . . .
H00B H 0.2623 0.2364 0.8370 0.085 Uiso 1 1 calc R . . . .
C010 C 0.0137(2) 0.3356(2) 0.87964(13) 0.0721(5) Uani 1 1 d . . . . .
H01A H -0.0372 0.3615 0.8387 0.087 Uiso 1 1 calc R . . . .
H01B H -0.0232 0.3470 0.9268 0.087 Uiso 1 1 calc R . . . .
C011 C 0.6895(2) 0.2862(2) 0.72498(12) 0.0765(5) Uani 1 1 d . . . . .
H011 H 0.6153 0.2519 0.7510 0.092 Uiso 1 1 calc R . . . .
C012 C 0.8369(2) 0.25596(18) 0.63829(12) 0.0706(5) Uani 1 1 d . . . . .
C013 C 0.6638(2) 0.6137(2) 0.43071(13) 0.0771(5) Uani 1 1 d . . . . .
H013 H 0.7143 0.5762 0.4027 0.093 Uiso 1 1 calc R . . . .
C014 C 0.7280(2) 0.2040(2) 0.67567(13) 0.0763(5) Uani 1 1 d . . . . .
H014 H 0.6797 0.1141 0.6683 0.092 Uiso 1 1 calc R . . . .
C015 C 0.0579(2) 0.1710(2) 0.78857(14) 0.0801(6) Uani 1 1 d . . . . .
H01C H 0.0060 0.1870 0.7439 0.096 Uiso 1 1 calc R . . . .
H01D H 0.0518 0.0807 0.7801 0.096 Uiso 1 1 calc R . . . .
C016 C 0.5157(2) 0.7246(3) 0.51040(13) 0.0798(6) Uani 1 1 d . . . . .
C017 C -0.0054(2) 0.1921(2) 0.85946(14) 0.0796(6) Uani 1 1 d . . . . .
H01E H 0.0373 0.1638 0.9027 0.096 Uiso 1 1 calc R . . . .
H01F H -0.1031 0.1395 0.8501 0.096 Uiso 1 1 calc R . . . .
C018 C 1.3503(2) 0.9866(2) 0.70649(13) 0.0775(5) Uani 1 1 d . . . . .
H01J H 1.3223 1.0343 0.7463 0.093 Uiso 1 1 calc R . . . .
H01K H 1.4483 1.0050 0.7200 0.093 Uiso 1 1 calc R . . . .
C019 C 0.2646(3) 0.9626(2) 0.96599(16) 0.0848(6) Uani 1 1 d . . . . .
C01A C 0.5249(3) 0.5767(3) 0.40737(15) 0.0876(6) Uani 1 1 d . . . . .
H01L H 0.4815 0.5142 0.3644 0.105 Uiso 1 1 calc R . . . .
C01B C 1.1696(2) 0.99640(19) 0.60361(13) 0.0726(5) Uani 1 1 d . . . . .
H01M H 1.1550 1.0217 0.5530 0.087 Uiso 1 1 calc R . . . .
H01N H 1.1341 1.0446 0.6391 0.087 Uiso 1 1 calc R . . . .
C01C C 0.4500(2) 0.6327(3) 0.44795(14) 0.0858(6) Uani 1 1 d . . . . .
H01O H 0.3555 0.6081 0.4329 0.103 Uiso 1 1 calc R . . . .
C01D C 0.3629(3) 0.8273(2) 1.06370(13) 0.0855(6) Uani 1 1 d . . . . .
H01G H 0.3968 0.7812 1.0973 0.103 Uiso 1 1 calc R . . . .
C01E C 1.3235(2) 1.0328(2) 0.62957(14) 0.0818(6) Uani 1 1 d . . . . .
H01P H 1.3617 0.9931 0.5910 0.098 Uiso 1 1 calc R . . . .
H01Q H 1.3692 1.1269 0.6345 0.098 Uiso 1 1 calc R . . . .
C01F C 0.3432(3) 1.0255(2) 1.03456(18) 0.0964(8) Uani 1 1 d . . . . .
H01H H 0.3630 1.1145 1.0479 0.116 Uiso 1 1 calc R . . . .
C01G C 0.3934(3) 0.9577(3) 1.08417(16) 0.0988(8) Uani 1 1 d . . . . .
H01I H 0.4475 1.0003 1.1312 0.119 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
O001 H001 0.8200 . ?
O001 C00L 1.342(2) . ?
F002 C012 1.351(2) . ?
O003 H003 0.8200 . ?
O003 C00K 1.332(2) . ?
F004 C00M 1.350(2) . ?
O005 H005 0.8200 . ?
O005 C00W 1.337(3) . ?
O006 H006 0.8200 . ?
O006 C00H 1.340(2) . ?
N007 C00E 1.271(2) . ?
N007 C00O 1.456(2) . ?
N008 C00F 1.274(2) . ?
N008 C00Y 1.456(2) . ?
N009 C00N 1.268(2) . ?
N009 C00S 1.460(2) . ?
N00A C00J 1.459(2) . ?
N00A C00Q 1.269(2) . ?
F00B C019 1.353(3) . ?
F00C C016 1.358(3) . ?
C00D C00E 1.456(2) . ?
C00D C00H 1.396(2) . ?
C00D C00V 1.400(2) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00G 1.453(2) . ?
C00G C00K 1.403(2) . ?
C00G C00T 1.400(2) . ?
C00H C00M 1.388(3) . ?
C00I C00N 1.447(3) . ?
C00I C00W 1.400(3) . ?
C00I C013 1.395(3) . ?
C00J H00J 0.9800 . ?
C00J C00O 1.528(3) . ?
C00J C010 1.520(3) . ?
C00K C012 1.393(3) . ?
C00L C00R 1.395(3) . ?
C00L C019 1.385(3) . ?
C00M C00P 1.361(3) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9800 . ?
C00O C00Z 1.524(3) . ?
C00P H00P 0.9300 . ?
C00P C00U 1.375(3) . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.448(3) . ?
C00R C01D 1.400(3) . ?
C00S H00S 0.9800 . ?
C00S C00Y 1.535(2) . ?
C00S C01B 1.525(3) . ?
C00T H00T 0.9300 . ?
C00T C011 1.370(3) . ?
C00U H00U 0.9300 . ?
C00U C00V 1.375(3) . ?
C00V H00V 0.9300 . ?
C00W C016 1.385(3) . ?
C00X H00C 0.9700 . ?
C00X H00D 0.9700 . ?
C00X C00Y 1.521(3) . ?
C00X C018 1.524(3) . ?
C00Y H00Y 0.9800 . ?
C00Z H00A 0.9700 . ?
C00Z H00B 0.9700 . ?
C00Z C015 1.522(3) . ?
C010 H01A 0.9700 . ?
C010 H01B 0.9700 . ?
C010 C017 1.524(3) . ?
C011 H011 0.9300 . ?
C011 C014 1.388(3) . ?
C012 C014 1.359(3) . ?
C013 H013 0.9300 . ?
C013 C01A 1.368(3) . ?
C014 H014 0.9300 . ?
C015 H01C 0.9700 . ?
C015 H01D 0.9700 . ?
C015 C017 1.515(3) . ?
C016 C01C 1.360(3) . ?
C017 H01E 0.9700 . ?
C017 H01F 0.9700 . ?
C018 H01J 0.9700 . ?
C018 H01K 0.9700 . ?
C018 C01E 1.521(3) . ?
C019 C01F 1.358(4) . ?
C01A H01L 0.9300 . ?
C01A C01C 1.374(4) . ?
C01B H01M 0.9700 . ?
C01B H01N 0.9700 . ?
C01B C01E 1.522(3) . ?
C01C H01O 0.9300 . ?
C01D H01G 0.9300 . ?
C01D C01G 1.362(4) . ?
C01E H01P 0.9700 . ?
C01E H01Q 0.9700 . ?
C01F H01H 0.9300 . ?
C01F C01G 1.372(4) . ?
C01G H01I 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
C00L O001 H001 109.5 . . ?
C00K O003 H003 109.5 . . ?
C00W O005 H005 109.5 . . ?
C00H O006 H006 109.5 . . ?
C00E N007 C00O 121.24(15) . . ?
C00F N008 C00Y 120.85(14) . . ?
C00N N009 C00S 118.63(15) . . ?
C00Q N00A C00J 118.66(14) . . ?
C00H C00D C00E 120.02(15) . . ?
C00H C00D C00V 119.06(16) . . ?
C00V C00D C00E 120.91(16) . . ?
N007 C00E C00D 121.29(15) . . ?
N007 C00E H00E 119.4 . . ?
C00D C00E H00E 119.4 . . ?
N008 C00F H00F 119.2 . . ?
N008 C00F C00G 121.67(15) . . ?
C00G C00F H00F 119.2 . . ?
C00K C00G C00F 119.58(15) . . ?
C00T C00G C00F 121.13(16) . . ?
C00T C00G C00K 119.29(16) . . ?
O006 C00H C00D 122.57(17) . . ?
O006 C00H C00M 119.40(17) . . ?
C00M C00H C00D 118.03(17) . . ?
C00W C00I C00N 120.60(17) . . ?
C013 C00I C00N 120.29(17) . . ?
C013 C00I C00W 119.11(18) . . ?
N00A C00J H00J 108.8 . . ?
N00A C00J C00O 109.22(14) . . ?
N00A C00J C010 110.77(14) . . ?
C00O C00J H00J 108.8 . . ?
C010 C00J H00J 108.8 . . ?
C010 C00J C00O 110.31(16) . . ?
O003 C00K C00G 122.59(16) . . ?
O003 C00K C012 119.93(17) . . ?
C012 C00K C00G 117.48(17) . . ?
O001 C00L C00R 122.24(17) . . ?
O001 C00L C019 120.39(19) . . ?
C019 C00L C00R 117.4(2) . . ?
F004 C00M C00H 117.60(18) . . ?
F004 C00M C00P 119.73(18) . . ?
C00P C00M C00H 122.67(18) . . ?
N009 C00N C00I 122.40(16) . . ?
N009 C00N H00N 118.8 . . ?
C00I C00N H00N 118.8 . . ?
N007 C00O C00J 108.17(14) . . ?
N007 C00O H00O 109.7 . . ?
N007 C00O C00Z 109.41(14) . . ?
C00J C00O H00O 109.7 . . ?
C00Z C00O C00J 110.19(15) . . ?
C00Z C00O H00O 109.7 . . ?
C00M C00P H00P 120.3 . . ?
C00M C00P C00U 119.41(18) . . ?
C00U C00P H00P 120.3 . . ?
N00A C00Q H00Q 118.8 . . ?
N00A C00Q C00R 122.40(16) . . ?
C00R C00Q H00Q 118.8 . . ?
C00L C00R C00Q 120.40(17) . . ?
C00L C00R C01D 119.20(19) . . ?
C01D C00R C00Q 120.39(18) . . ?
N009 C00S H00S 108.9 . . ?
N009 C00S C00Y 109.79(14) . . ?
N009 C00S C01B 109.48(14) . . ?
C00Y C00S H00S 108.9 . . ?
C01B C00S H00S 108.9 . . ?
C01B C00S C00Y 110.82(15) . . ?
C00G C00T H00T 119.4 . . ?
C011 C00T C00G 121.27(18) . . ?
C011 C00T H00T 119.4 . . ?
C00P C00U H00U 120.1 . . ?
C00P C00U C00V 119.88(18) . . ?
C00V C00U H00U 120.1 . . ?
C00D C00V H00V 119.5 . . ?
C00U C00V C00D 120.95(17) . . ?
C00U C00V H00V 119.5 . . ?
O005 C00W C00I 122.37(18) . . ?
O005 C00W C016 120.36(18) . . ?
C016 C00W C00I 117.27(19) . . ?
H00C C00X H00D 107.9 . . ?
C00Y C00X H00C 109.3 . . ?
C00Y C00X H00D 109.3 . . ?
C00Y C00X C018 111.73(15) . . ?
C018 C00X H00C 109.3 . . ?
C018 C00X H00D 109.3 . . ?
N008 C00Y C00S 108.76(14) . . ?
N008 C00Y C00X 109.61(14) . . ?
N008 C00Y H00Y 109.4 . . ?
C00S C00Y H00Y 109.4 . . ?
C00X C00Y C00S 110.28(15) . . ?
C00X C00Y H00Y 109.4 . . ?
C00O C00Z H00A 109.3 . . ?
C00O C00Z H00B 109.3 . . ?
H00A C00Z H00B 107.9 . . ?
C015 C00Z C00O 111.80(17) . . ?
C015 C00Z H00A 109.3 . . ?
C015 C00Z H00B 109.3 . . ?
C00J C010 H01A 109.4 . . ?
C00J C010 H01B 109.4 . . ?
C00J C010 C017 111.00(16) . . ?
H01A C010 H01B 108.0 . . ?
C017 C010 H01A 109.4 . . ?
C017 C010 H01B 109.4 . . ?
C00T C011 H011 120.2 . . ?
C00T C011 C014 119.64(19) . . ?
C014 C011 H011 120.2 . . ?
F002 C012 C00K 117.32(18) . . ?
F002 C012 C014 119.69(18) . . ?
C014 C012 C00K 122.98(19) . . ?
C00I C013 H013 119.2 . . ?
C01A C013 C00I 121.5(2) . . ?
C01A C013 H013 119.2 . . ?
C011 C014 H014 120.3 . . ?
C012 C014 C011 119.33(19) . . ?
C012 C014 H014 120.3 . . ?
C00Z C015 H01C 109.3 . . ?
C00Z C015 H01D 109.3 . . ?
H01C C015 H01D 107.9 . . ?
C017 C015 C00Z 111.74(18) . . ?
C017 C015 H01C 109.3 . . ?
C017 C015 H01D 109.3 . . ?
F00C C016 C00W 117.2(2) . . ?
F00C C016 C01C 119.5(2) . . ?
C01C C016 C00W 123.2(2) . . ?
C010 C017 H01E 109.4 . . ?
C010 C017 H01F 109.4 . . ?
C015 C017 C010 111.27(18) . . ?
C015 C017 H01E 109.4 . . ?
C015 C017 H01F 109.4 . . ?
H01E C017 H01F 108.0 . . ?
C00X C018 H01J 109.4 . . ?
C00X C018 H01K 109.4 . . ?
H01J C018 H01K 108.0 . . ?
C01E C018 C00X 111.22(17) . . ?
C01E C018 H01J 109.4 . . ?
C01E C018 H01K 109.4 . . ?
F00B C019 C00L 117.1(2) . . ?
F00B C019 C01F 120.2(2) . . ?
C01F C019 C00L 122.7(2) . . ?
C013 C01A H01L 120.3 . . ?
C013 C01A C01C 119.5(2) . . ?
C01C C01A H01L 120.3 . . ?
C00S C01B H01M 109.2 . . ?
C00S C01B H01N 109.2 . . ?
H01M C01B H01N 107.9 . . ?
C01E C01B C00S 112.06(16) . . ?
C01E C01B H01M 109.2 . . ?
C01E C01B H01N 109.2 . . ?
C016 C01C C01A 119.3(2) . . ?
C016 C01C H01O 120.3 . . ?
C01A C01C H01O 120.3 . . ?
C00R C01D H01G 119.2 . . ?
C01G C01D C00R 121.6(2) . . ?
C01G C01D H01G 119.2 . . ?
C018 C01E C01B 110.83(18) . . ?
C018 C01E H01P 109.5 . . ?
C018 C01E H01Q 109.5 . . ?
C01B C01E H01P 109.5 . . ?
C01B C01E H01Q 109.5 . . ?
H01P C01E H01Q 108.1 . . ?
C019 C01F H01H 120.0 . . ?
C019 C01F C01G 120.0(2) . . ?
C01G C01F H01H 120.0 . . ?
C01D C01G C01F 119.1(2) . . ?
C01D C01G H01I 120.4 . . ?
C01F C01G H01I 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00L C00R C00Q 0.8(3) . . . . ?
O001 C00L C00R C01D 179.32(19) . . . . ?
O001 C00L C019 F00B 0.0(3) . . . . ?
O001 C00L C019 C01F -179.5(2) . . . . ?
F002 C012 C014 C011 179.5(2) . . . . ?
O003 C00K C012 F002 0.0(3) . . . . ?
O003 C00K C012 C014 179.6(2) . . . . ?
F004 C00M C00P C00U 179.44(19) . . . . ?
O005 C00W C016 F00C -1.6(3) . . . . ?
O005 C00W C016 C01C 179.2(2) . . . . ?
O006 C00H C00M F004 0.5(3) . . . . ?
O006 C00H C00M C00P -179.82(19) . . . . ?
N007 C00O C00Z C015 174.64(16) . . . . ?
N008 C00F C00G C00K -0.4(3) . . . . ?
N008 C00F C00G C00T -179.71(16) . . . . ?
N009 C00S C00Y N008 63.20(17) . . . . ?
N009 C00S C00Y C00X -176.57(14) . . . . ?
N009 C00S C01B C01E 176.84(17) . . . . ?
N00A C00J C00O N007 60.77(17) . . . . ?
N00A C00J C00O C00Z -179.67(14) . . . . ?
N00A C00J C010 C017 179.07(17) . . . . ?
N00A C00Q C00R C00L -0.3(3) . . . . ?
N00A C00Q C00R C01D -178.87(19) . . . . ?
F00B C019 C01F C01G -179.0(2) . . . . ?
F00C C016 C01C C01A -179.7(2) . . . . ?
C00D C00H C00M F004 -179.73(17) . . . . ?
C00D C00H C00M C00P 0.0(3) . . . . ?
C00E N007 C00O C00J -118.05(17) . . . . ?
C00E N007 C00O C00Z 121.90(18) . . . . ?
C00E C00D C00H O006 1.3(3) . . . . ?
C00E C00D C00H C00M -178.50(16) . . . . ?
C00E C00D C00V C00U 178.25(16) . . . . ?
C00F N008 C00Y C00S -113.01(17) . . . . ?
C00F N008 C00Y C00X 126.35(17) . . . . ?
C00F C00G C00K O003 1.5(3) . . . . ?
C00F C00G C00K C012 -178.41(16) . . . . ?
C00F C00G C00T C011 178.44(17) . . . . ?
C00G C00K C012 F002 179.92(17) . . . . ?
C00G C00K C012 C014 -0.5(3) . . . . ?
C00G C00T C011 C014 0.3(3) . . . . ?
C00H C00D C00E N007 -2.0(2) . . . . ?
C00H C00D C00V C00U -0.8(3) . . . . ?
C00H C00M C00P C00U -0.3(3) . . . . ?
C00I C00W C016 F00C 178.66(18) . . . . ?
C00I C00W C016 C01C -0.5(3) . . . . ?
C00I C013 C01A C01C 0.7(4) . . . . ?
C00J N00A C00Q C00R 177.15(16) . . . . ?
C00J C00O C00Z C015 55.8(2) . . . . ?
C00J C010 C017 C015 -55.9(2) . . . . ?
C00K C00G C00T C011 -0.9(3) . . . . ?
C00K C012 C014 C011 -0.1(3) . . . . ?
C00L C00R C01D C01G -0.1(3) . . . . ?
C00L C019 C01F C01G 0.4(4) . . . . ?
C00M C00P C00U C00V 0.0(3) . . . . ?
C00N N009 C00S C00Y -114.77(17) . . . . ?
C00N N009 C00S C01B 123.36(18) . . . . ?
C00N C00I C00W O005 2.1(3) . . . . ?
C00N C00I C00W C016 -178.14(17) . . . . ?
C00N C00I C013 C01A 178.0(2) . . . . ?
C00O N007 C00E C00D 176.63(14) . . . . ?
C00O C00J C010 C017 58.0(2) . . . . ?
C00O C00Z C015 C017 -54.1(2) . . . . ?
C00P C00U C00V C00D 0.5(3) . . . . ?
C00Q N00A C00J C00O -119.01(17) . . . . ?
C00Q N00A C00J C010 119.30(18) . . . . ?
C00Q C00R C01D C01G 178.4(2) . . . . ?
C00R C00L C019 F00B 178.97(19) . . . . ?
C00R C00L C019 C01F -0.5(3) . . . . ?
C00R C01D C01G C01F 0.0(4) . . . . ?
C00S N009 C00N C00I 179.60(15) . . . . ?
C00S C01B C01E C018 -55.1(3) . . . . ?
C00T C00G C00K O003 -179.19(18) . . . . ?
C00T C00G C00K C012 0.9(3) . . . . ?
C00T C011 C014 C012 0.1(3) . . . . ?
C00V C00D C00E N007 179.00(16) . . . . ?
C00V C00D C00H O006 -179.68(18) . . . . ?
C00V C00D C00H C00M 0.5(3) . . . . ?
C00W C00I C00N N009 0.5(3) . . . . ?
C00W C00I C013 C01A -1.8(3) . . . . ?
C00W C016 C01C C01A -0.5(4) . . . . ?
C00X C018 C01E C01B 54.9(3) . . . . ?
C00Y N008 C00F C00G 177.53(14) . . . . ?
C00Y C00S C01B C01E 55.6(2) . . . . ?
C00Y C00X C018 C01E -56.3(2) . . . . ?
C00Z C015 C017 C010 53.6(3) . . . . ?
C010 C00J C00O N007 -177.26(14) . . . . ?
C010 C00J C00O C00Z -57.70(19) . . . . ?
C013 C00I C00N N009 -179.29(18) . . . . ?
C013 C00I C00W O005 -178.13(19) . . . . ?
C013 C00I C00W C016 1.6(3) . . . . ?
C013 C01A C01C C016 0.4(4) . . . . ?
C018 C00X C00Y N008 175.97(16) . . . . ?
C018 C00X C00Y C00S 56.2(2) . . . . ?
C019 C00L C00R C00Q -178.21(18) . . . . ?
C019 C00L C00R C01D 0.3(3) . . . . ?
C019 C01F C01G C01D -0.2(4) . . . . ?
C01B C00S C00Y N008 -175.73(15) . . . . ?
C01B C00S C00Y C00X -55.50(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-24
_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_zxg-ss-f-130k
_database_code_depnum_ccdc_archive 'CCDC 1496280'
_audit_update_record             
;
2016-07-23 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2016-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C10 H10 F N O)'
_chemical_formula_sum            'C30 H30 F3 N3 O3'
_chemical_formula_weight         537.57
_chemical_absolute_configuration syn
_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   11.1476(2)
_cell_length_b                   11.1476(2)
_cell_length_c                   38.1525(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4106.0(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    294.33(10)
_cell_measurement_theta_max      72.6170
_cell_measurement_theta_min      4.5760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15282
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.555
_diffrn_reflns_theta_min         4.580
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.33(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  150.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   92.0000   55.9865 27

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega  100.00  178.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   87.00  178.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
 12 omega    9.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
 13 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -90.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1200743000
_diffrn_orient_matrix_UB_12      0.0106675000
_diffrn_orient_matrix_UB_13      -0.0223353000
_diffrn_orient_matrix_UB_21      0.0876191000
_diffrn_orient_matrix_UB_22      0.1549339000
_diffrn_orient_matrix_UB_23      0.0091947000
_diffrn_orient_matrix_UB_31      0.0579400000
_diffrn_orient_matrix_UB_32      -0.0366778000
_diffrn_orient_matrix_UB_33      0.0323739000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                5035
_reflns_number_total             5245
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_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     355
_refine_ls_number_reflns         5245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.094
_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)+(0.0860P)²+0.0740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1256
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00H(H00J), C00K(H00K), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00T(H00C,H00E), C00Z(H00G,H00H), C010(H01A,H01B), C012(H01C,
 H01D), C013(H01E,H01F)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00G(H00I), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C011(H011)
2.d Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005), O006(H006)
;
_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
F001 F 0.47260(17) 0.6098(2) 0.15579(4) 0.0442(4) Uani 1 1 d . . . . .
F002 F 0.93716(19) 1.0867(2) 0.27159(5) 0.0453(4) Uani 1 1 d . . . . .
F003 F -0.0907(2) 0.5944(2) 0.32182(5) 0.0488(5) Uani 1 1 d . . . . .
O004 O 0.6403(2) 0.5031(2) 0.15871(5) 0.0326(4) Uani 1 1 d . . . . .
H004 H 0.6989 0.4783 0.1625 0.049 Uiso 1 1 calc GR . . . .
O005 O 0.7131(2) 1.1128(2) 0.26067(4) 0.0337(4) Uani 1 1 d . . . . .
H005 H 0.6546 1.1392 0.2594 0.051 Uiso 1 1 calc GR . . . .
O006 O 0.0654(2) 0.8553(2) 0.29950(6) 0.0411(5) Uani 1 1 d . . . . .
H006 H 0.1262 0.9339 0.2925 0.062 Uiso 1 1 calc GR . . . .
N007 N 0.2729(2) 1.0292(2) 0.26324(5) 0.0288(5) Uani 1 1 d . . . . .
N008 N 0.8627(2) 0.5217(2) 0.18232(5) 0.0274(5) Uani 1 1 d . . . . .
N009 N 0.5605(2) 1.2097(2) 0.28367(5) 0.0276(4) Uani 1 1 d . . . . .
C00A C 0.7763(3) 1.1477(3) 0.29225(6) 0.0285(5) Uani 1 1 d . . . . .
C00B C 0.2119(3) 0.7921(3) 0.26728(6) 0.0269(5) Uani 1 1 d . . . . .
C00C C 0.7308(3) 1.2000(3) 0.31956(6) 0.0280(5) Uani 1 1 d . . . . .
C00D C 0.6190(3) 1.2293(3) 0.31359(6) 0.0279(5) Uani 1 1 d . . . . .
H00D H 0.5889 1.2638 0.3324 0.034 Uiso 1 1 calc R . . . .
C00E C 0.6742(3) 0.6184(3) 0.17694(6) 0.0280(5) Uani 1 1 d . . . . .
C00F C 0.2974(3) 0.9334(3) 0.25427(6) 0.0272(5) Uani 1 1 d . . . . .
H00F H 0.3724 0.9542 0.2389 0.033 Uiso 1 1 calc R . . . .
C00G C 0.8857(3) 0.6278(3) 0.20021(6) 0.0282(5) Uani 1 1 d . . . . .
H00I H 0.9641 0.6701 0.2152 0.034 Uiso 1 1 calc R . . . .
C00H C 0.9556(3) 0.4653(3) 0.18337(6) 0.0287(5) Uani 1 1 d . . . . .
H00J H 1.0168 0.5017 0.2044 0.034 Uiso 1 1 calc R . . . .
C00I C 0.7937(3) 0.6852(3) 0.19798(6) 0.0278(5) Uani 1 1 d . . . . .
C00J C 0.8926(3) 1.1362(3) 0.29806(7) 0.0327(6) Uani 1 1 d . . . . .
C00K C 0.3595(3) 1.1694(3) 0.24957(6) 0.0278(5) Uani 1 1 d . . . . .
H00K H 0.4110 1.1654 0.2286 0.033 Uiso 1 1 calc R . . . .
C00L C 0.4640(3) 1.2598(3) 0.27759(6) 0.0271(5) Uani 1 1 d . . . . .
H00L H 0.4143 1.2548 0.2998 0.033 Uiso 1 1 calc R . . . .
C00M C 0.0984(3) 0.7611(3) 0.28938(7) 0.0298(5) Uani 1 1 d . . . . .
C00N C 0.4530(3) 1.4673(3) 0.25425(7) 0.0355(6) Uani 1 1 d . . . . .
H00A H 0.4002 1.4696 0.2749 0.043 Uiso 1 1 calc R . . . .
H00B H 0.5099 1.5631 0.2454 0.043 Uiso 1 1 calc R . . . .
C00O C 0.0181(3) 0.6246(3) 0.30091(7) 0.0339(6) Uani 1 1 d . . . . .
C00P C 0.8022(3) 1.2348(3) 0.35151(7) 0.0353(6) Uani 1 1 d . . . . .
H00P H 0.7705 1.2682 0.3702 0.042 Uiso 1 1 calc R . . . .
C00Q C 0.2408(3) 0.6883(3) 0.25819(6) 0.0317(6) Uani 1 1 d . . . . .
H00Q H 0.3168 0.7096 0.2431 0.038 Uiso 1 1 calc R . . . .
C00R C 0.5889(3) 0.6754(3) 0.17553(7) 0.0334(6) Uani 1 1 d . . . . .
C00S C 0.6164(3) 0.7937(3) 0.19354(7) 0.0387(6) Uani 1 1 d . . . . .
H00S H 0.5557 0.8301 0.1918 0.046 Uiso 1 1 calc R . . . .
C00T C 0.3527(3) 1.3771(3) 0.22584(7) 0.0363(6) Uani 1 1 d . . . . .
H00C H 0.4052 1.3800 0.2046 0.044 Uiso 1 1 calc R . . . .
H00E H 0.2907 1.4134 0.2196 0.044 Uiso 1 1 calc R . . . .
C00U C 0.9173(3) 1.2217(3) 0.35627(7) 0.0387(7) Uani 1 1 d . . . . .
H00U H 0.9649 1.2463 0.3781 0.046 Uiso 1 1 calc R . . . .
C00V C 0.0478(3) 0.5230(3) 0.29224(7) 0.0371(6) Uani 1 1 d . . . . .
H00V H -0.0084 0.4315 0.3008 0.045 Uiso 1 1 calc R . . . .
C00W C 0.1610(3) 0.5546(3) 0.27070(7) 0.0374(6) Uani 1 1 d . . . . .
H00W H 0.1830 0.4851 0.2647 0.045 Uiso 1 1 calc R . . . .
C00X C 0.9637(3) 1.1723(3) 0.32913(8) 0.0383(6) Uani 1 1 d . . . . .
H00X H 1.0437 1.1636 0.3321 0.046 Uiso 1 1 calc R . . . .
C00Y C 0.8218(3) 0.8048(3) 0.21650(7) 0.0358(6) Uani 1 1 d . . . . .
H00Y H 0.9022 0.8495 0.2308 0.043 Uiso 1 1 calc R . . . .
C00Z C 0.2663(3) 1.2274(3) 0.23851(7) 0.0355(6) Uani 1 1 d . . . . .
H00G H 0.2037 1.1696 0.2195 0.043 Uiso 1 1 calc R . . . .
H00H H 0.2085 1.2237 0.2586 0.043 Uiso 1 1 calc R . . . .
C010 C 0.5474(3) 1.4110(3) 0.26514(7) 0.0324(6) Uani 1 1 d . . . . .
H01A H 0.6092 1.4690 0.2843 0.039 Uiso 1 1 calc R . . . .
H01B H 0.6060 1.4168 0.2450 0.039 Uiso 1 1 calc R . . . .
C011 C 0.7348(4) 0.8590(3) 0.21438(7) 0.0400(7) Uani 1 1 d . . . . .
H011 H 0.7554 0.9404 0.2271 0.048 Uiso 1 1 calc R . . . .
C012 C 0.8691(3) 0.3083(3) 0.18546(9) 0.0403(6) Uani 1 1 d . . . . .
H01C H 0.8165 0.2818 0.2077 0.048 Uiso 1 1 calc R . . . .
H01D H 0.8015 0.2739 0.1660 0.048 Uiso 1 1 calc R . . . .
C013 C 0.9574(4) 0.2400(4) 0.18353(11) 0.0569(9) Uani 1 1 d . . . . .
H01E H 0.8971 0.1380 0.1841 0.068 Uiso 1 1 calc R . . . .
H01F H 1.0202 0.2680 0.2040 0.068 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
F001 C00R 1.354(3) . ?
F002 C00J 1.358(3) . ?
F003 C00O 1.346(3) . ?
O004 H004 0.8400 . ?
O004 C00E 1.340(3) . ?
O005 H005 0.8400 . ?
O005 C00A 1.351(3) . ?
O006 H006 0.8400 . ?
O006 C00M 1.332(4) . ?
N007 C00F 1.275(4) . ?
N007 C00K 1.462(3) . ?
N008 C00G 1.276(3) . ?
N008 C00H 1.456(3) . ?
N009 C00D 1.278(3) . ?
N009 C00L 1.458(3) . ?
C00A C00C 1.407(4) . ?
C00A C00J 1.383(4) . ?
C00B C00F 1.461(4) . ?
C00B C00M 1.412(4) . ?
C00B C00Q 1.392(4) . ?
C00C C00D 1.455(4) . ?
C00C C00P 1.400(4) . ?
C00D H00D 0.9500 . ?
C00E C00I 1.408(4) . ?
C00E C00R 1.384(4) . ?
C00F H00F 0.9500 . ?
C00G H00I 0.9500 . ?
C00G C00I 1.457(4) . ?
C00H C00H 1.537(5) 6_765 ?
C00H H00J 1.0000 . ?
C00H C012 1.520(4) . ?
C00I C00Y 1.399(4) . ?
C00J C00X 1.370(4) . ?
C00K H00K 1.0000 . ?
C00K C00L 1.530(3) . ?
C00K C00Z 1.532(4) . ?
C00L H00L 1.0000 . ?
C00L C010 1.537(4) . ?
C00M C00O 1.395(4) . ?
C00N H00A 0.9900 . ?
C00N H00B 0.9900 . ?
C00N C00T 1.520(4) . ?
C00N C010 1.528(4) . ?
C00O C00V 1.370(4) . ?
C00P H00P 0.9500 . ?
C00P C00U 1.375(4) . ?
C00Q H00Q 0.9500 . ?
C00Q C00W 1.383(4) . ?
C00R C00S 1.379(4) . ?
C00S H00S 0.9500 . ?
C00S C011 1.394(5) . ?
C00T H00C 0.9900 . ?
C00T H00E 0.9900 . ?
C00T C00Z 1.529(4) . ?
C00U H00U 0.9500 . ?
C00U C00X 1.389(4) . ?
C00V H00V 0.9500 . ?
C00V C00W 1.396(4) . ?
C00W H00W 0.9500 . ?
C00X H00X 0.9500 . ?
C00Y H00Y 0.9500 . ?
C00Y C011 1.377(4) . ?
C00Z H00G 0.9900 . ?
C00Z H00H 0.9900 . ?
C010 H01A 0.9900 . ?
C010 H01B 0.9900 . ?
C011 H011 0.9500 . ?
C012 H01C 0.9900 . ?
C012 H01D 0.9900 . ?
C012 C013 1.518(5) . ?
C013 C013 1.527(7) 6_765 ?
C013 H01E 0.9900 . ?
C013 H01F 0.9900 . ?

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
C00E O004 H004 109.5 . . ?
C00A O005 H005 109.5 . . ?
C00M O006 H006 109.5 . . ?
C00F N007 C00K 119.8(2) . . ?
C00G N008 C00H 122.0(2) . . ?
C00D N009 C00L 119.2(2) . . ?
O005 C00A C00C 122.4(2) . . ?
O005 C00A C00J 119.6(2) . . ?
C00J C00A C00C 118.0(2) . . ?
C00M C00B C00F 119.3(2) . . ?
C00Q C00B C00F 121.0(2) . . ?
C00Q C00B C00M 119.8(2) . . ?
C00A C00C C00D 120.3(2) . . ?
C00P C00C C00A 119.1(3) . . ?
C00P C00C C00D 120.4(3) . . ?
N009 C00D C00C 121.5(2) . . ?
N009 C00D H00D 119.3 . . ?
C00C C00D H00D 119.3 . . ?
O004 C00E C00I 122.8(2) . . ?
O004 C00E C00R 119.5(2) . . ?
C00R C00E C00I 117.7(2) . . ?
N007 C00F C00B 121.0(2) . . ?
N007 C00F H00F 119.5 . . ?
C00B C00F H00F 119.5 . . ?
N008 C00G H00I 119.4 . . ?
N008 C00G C00I 121.1(2) . . ?
C00I C00G H00I 119.4 . . ?
N008 C00H C00H 108.73(17) . 6_765 ?
N008 C00H H00J 109.6 . . ?
N008 C00H C012 108.7(2) . . ?
C00H C00H H00J 109.6 6_765 . ?
C012 C00H C00H 110.49(18) . 6_765 ?
C012 C00H H00J 109.6 . . ?
C00E C00I C00G 119.3(2) . . ?
C00Y C00I C00E 119.5(3) . . ?
C00Y C00I C00G 121.2(2) . . ?
F002 C00J C00A 117.9(2) . . ?
F002 C00J C00X 119.2(3) . . ?
C00X C00J C00A 122.9(3) . . ?
N007 C00K H00K 108.9 . . ?
N007 C00K C00L 109.5(2) . . ?
N007 C00K C00Z 108.9(2) . . ?
C00L C00K H00K 108.9 . . ?
C00L C00K C00Z 111.6(2) . . ?
C00Z C00K H00K 108.9 . . ?
N009 C00L C00K 108.9(2) . . ?
N009 C00L H00L 109.8 . . ?
N009 C00L C010 108.2(2) . . ?
C00K C00L H00L 109.8 . . ?
C00K C00L C010 110.5(2) . . ?
C010 C00L H00L 109.8 . . ?
O006 C00M C00B 123.2(2) . . ?
O006 C00M C00O 119.2(2) . . ?
C00O C00M C00B 117.6(3) . . ?
H00A C00N H00B 108.1 . . ?
C00T C00N H00A 109.5 . . ?
C00T C00N H00B 109.5 . . ?
C00T C00N C010 110.6(2) . . ?
C010 C00N H00A 109.5 . . ?
C010 C00N H00B 109.5 . . ?
F003 C00O C00M 117.8(3) . . ?
F003 C00O C00V 119.7(3) . . ?
C00V C00O C00M 122.4(3) . . ?
C00C C00P H00P 119.4 . . ?
C00U C00P C00C 121.1(3) . . ?
C00U C00P H00P 119.4 . . ?
C00B C00Q H00Q 119.4 . . ?
C00W C00Q C00B 121.2(3) . . ?
C00W C00Q H00Q 119.4 . . ?
F001 C00R C00E 117.8(3) . . ?
F001 C00R C00S 119.3(3) . . ?
C00S C00R C00E 123.0(3) . . ?
C00R C00S H00S 120.5 . . ?
C00R C00S C011 118.9(3) . . ?
C011 C00S H00S 120.5 . . ?
C00N C00T H00C 109.6 . . ?
C00N C00T H00E 109.6 . . ?
C00N C00T C00Z 110.5(2) . . ?
H00C C00T H00E 108.1 . . ?
C00Z C00T H00C 109.6 . . ?
C00Z C00T H00E 109.6 . . ?
C00P C00U H00U 120.1 . . ?
C00P C00U C00X 119.8(3) . . ?
C00X C00U H00U 120.1 . . ?
C00O C00V H00V 120.2 . . ?
C00O C00V C00W 119.7(3) . . ?
C00W C00V H00V 120.2 . . ?
C00Q C00W C00V 119.2(3) . . ?
C00Q C00W H00W 120.4 . . ?
C00V C00W H00W 120.4 . . ?
C00J C00X C00U 119.1(3) . . ?
C00J C00X H00X 120.5 . . ?
C00U C00X H00X 120.5 . . ?
C00I C00Y H00Y 119.4 . . ?
C011 C00Y C00I 121.2(3) . . ?
C011 C00Y H00Y 119.4 . . ?
C00K C00Z H00G 109.5 . . ?
C00K C00Z H00H 109.5 . . ?
C00T C00Z C00K 110.9(2) . . ?
C00T C00Z H00G 109.5 . . ?
C00T C00Z H00H 109.5 . . ?
H00G C00Z H00H 108.0 . . ?
C00L C010 H01A 109.3 . . ?
C00L C010 H01B 109.3 . . ?
C00N C010 C00L 111.8(2) . . ?
C00N C010 H01A 109.3 . . ?
C00N C010 H01B 109.3 . . ?
H01A C010 H01B 107.9 . . ?
C00S C011 H011 120.2 . . ?
C00Y C011 C00S 119.7(3) . . ?
C00Y C011 H011 120.2 . . ?
C00H C012 H01C 109.2 . . ?
C00H C012 H01D 109.2 . . ?
H01C C012 H01D 107.9 . . ?
C013 C012 C00H 112.2(2) . . ?
C013 C012 H01C 109.2 . . ?
C013 C012 H01D 109.2 . . ?
C012 C013 C013 110.1(3) . 6_765 ?
C012 C013 H01E 109.6 . . ?
C012 C013 H01F 109.6 . . ?
C013 C013 H01E 109.6 6_765 . ?
C013 C013 H01F 109.6 6_765 . ?
H01E C013 H01F 108.2 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-14
_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_zxg-rr-f-133
_database_code_depnum_ccdc_archive 'CCDC 1496279'
_audit_update_record             
;
2016-07-23 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2016-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C10 H10 F N O)'
_chemical_formula_sum            'C30 H30 F3 N3 O3'
_chemical_formula_weight         537.57
_chemical_absolute_configuration syn
_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      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   11.14762(19)
_cell_length_b                   11.14762(19)
_cell_length_c                   38.1285(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4103.41(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5801
_cell_measurement_temperature    294.33(10)
_cell_measurement_theta_max      72.4630
_cell_measurement_theta_min      4.6870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            12993
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.616
_diffrn_reflns_theta_min         4.725
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.33(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   91.00   1.0000    2.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00  116.00   1.0000    2.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  109.00   1.0000    2.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   98.00   1.0000    2.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    2.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   90.00   1.0000    2.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -51.0000   26.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0159582000
_diffrn_orient_matrix_UB_12      -0.0385922000
_diffrn_orient_matrix_UB_13      0.0378427000
_diffrn_orient_matrix_UB_21      -0.0982323000
_diffrn_orient_matrix_UB_22      -0.1541618000
_diffrn_orient_matrix_UB_23      -0.0083788000
_diffrn_orient_matrix_UB_31      0.1246658000
_diffrn_orient_matrix_UB_32      -0.0144942000
_diffrn_orient_matrix_UB_33      -0.0114301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                4887
_reflns_number_total             5156
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1804 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.107
_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)+(0.0849P)²+1.7289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1516
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00K), C00J(H00J), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00S(H00D,H00E), C00Y(H00G,H00H), C011(H01A,H01B), C012(H01C,
 H01D), C013(H01E,H01F)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00I), C00P(H00P), C00Q(H00Q), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010)
2.d Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005), O006(H006)
;
_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
F001 F 0.5274(2) 0.3903(3) 0.84423(6) 0.0398(6) Uani 1 1 d . . . . .
F002 F 0.0627(3) -0.0869(3) 0.72844(6) 0.0410(6) Uani 1 1 d . . . . .
F003 F 1.0910(3) 0.4058(3) 0.67814(7) 0.0452(6) Uani 1 1 d . . . . .
O004 O 0.2868(3) -0.1127(3) 0.73923(6) 0.0294(6) Uani 1 1 d . . . . .
H004 H 0.3457 -0.1361 0.7401 0.044 Uiso 1 1 calc GR . . . .
O005 O 0.3596(3) 0.4972(3) 0.84132(6) 0.0282(5) Uani 1 1 d . . . . .
H005 H 0.3039 0.5230 0.8370 0.042 Uiso 1 1 calc GR . . . .
O006 O 0.9347(3) 0.1449(3) 0.70042(8) 0.0368(7) Uani 1 1 d . . . . .
H006 H 0.8828 0.0705 0.7099 0.055 Uiso 1 1 calc GR . . . .
N007 N 0.7270(3) -0.0290(3) 0.73670(7) 0.0246(6) Uani 1 1 d . . . . .
N008 N 0.1372(3) 0.4782(3) 0.81777(7) 0.0233(6) Uani 1 1 d . . . . .
N009 N 0.4395(3) -0.2096(3) 0.71625(7) 0.0234(6) Uani 1 1 d . . . . .
C00A C 0.7885(4) 0.2079(4) 0.73270(8) 0.0225(7) Uani 1 1 d . . . . .
C00B C 0.2233(4) -0.1478(4) 0.70782(9) 0.0243(7) Uani 1 1 d . . . . .
C00C C 0.3813(4) -0.2296(4) 0.68642(9) 0.0247(7) Uani 1 1 d . . . . .
H00C H 0.4107 -0.2636 0.6681 0.030 Uiso 1 1 calc R . . . .
C00D C 0.2691(4) -0.2001(4) 0.68046(8) 0.0237(7) Uani 1 1 d . . . . .
C00E C 0.3256(4) 0.3818(4) 0.82306(8) 0.0228(7) Uani 1 1 d . . . . .
C00F C 0.7029(3) 0.0667(4) 0.74578(8) 0.0224(7) Uani 1 1 d . . . . .
H00F H 0.6298 0.0466 0.7609 0.027 Uiso 1 1 calc R . . . .
C00G C 0.1140(4) 0.3721(4) 0.79977(8) 0.0243(7) Uani 1 1 d . . . . .
H00I H 0.0372 0.3306 0.7851 0.029 Uiso 1 1 calc R . . . .
C00H C 0.2066(4) 0.3153(4) 0.80202(8) 0.0230(7) Uani 1 1 d . . . . .
C00I C 0.0445(3) 0.5349(4) 0.81659(9) 0.0243(7) Uani 1 1 d . . . . .
H00K H -0.0156 0.4992 0.7959 0.029 Uiso 1 1 calc R . . . .
C00J C 0.6408(3) -0.1694(4) 0.75038(8) 0.0227(7) Uani 1 1 d . . . . .
H00J H 0.5903 -0.1653 0.7710 0.027 Uiso 1 1 calc R . . . .
C00K C 0.9011(4) 0.2384(4) 0.71057(9) 0.0252(7) Uani 1 1 d . . . . .
C00L C 0.5361(4) -0.2599(4) 0.72246(8) 0.0237(7) Uani 1 1 d . . . . .
H00L H 0.5847 -0.2554 0.7006 0.028 Uiso 1 1 calc R . . . .
C00M C 0.1080(4) -0.1363(4) 0.70199(9) 0.0284(8) Uani 1 1 d . . . . .
C00N C 0.4112(4) 0.3246(4) 0.82439(9) 0.0281(8) Uani 1 1 d . . . . .
C00O C 0.5472(4) -0.4670(4) 0.74570(9) 0.0306(8) Uani 1 1 d . . . . .
H00A H 0.4915 -0.5610 0.7543 0.037 Uiso 1 1 calc R . . . .
H00B H 0.5987 -0.4692 0.7254 0.037 Uiso 1 1 calc R . . . .
C00P C 0.1980(4) -0.2346(4) 0.64850(9) 0.0305(8) Uani 1 1 d . . . . .
H00P H 0.2294 -0.2666 0.6301 0.037 Uiso 1 1 calc R . . . .
C00Q C 0.3835(4) 0.2064(4) 0.80655(10) 0.0335(9) Uani 1 1 d . . . . .
H00Q H 0.4426 0.1704 0.8084 0.040 Uiso 1 1 calc R . . . .
C00R C 0.9822(4) 0.3759(4) 0.69903(9) 0.0302(8) Uani 1 1 d . . . . .
C00S C 0.6478(4) -0.3768(4) 0.77416(9) 0.0327(8) Uani 1 1 d . . . . .
H00D H 0.7090 -0.4121 0.7802 0.039 Uiso 1 1 calc R . . . .
H00E H 0.5966 -0.3800 0.7950 0.039 Uiso 1 1 calc R . . . .
C00T C 0.0827(4) -0.2220(4) 0.64373(10) 0.0336(9) Uani 1 1 d . . . . .
H00T H 0.0359 -0.2466 0.6224 0.040 Uiso 1 1 calc R . . . .
C00U C 0.8391(4) 0.4450(4) 0.72929(9) 0.0331(8) Uani 1 1 d . . . . .
H00U H 0.8174 0.5129 0.7352 0.040 Uiso 1 1 calc R . . . .
C00V C 0.9524(4) 0.4771(4) 0.70768(10) 0.0332(9) Uani 1 1 d . . . . .
H00V H 1.0072 0.5668 0.6992 0.040 Uiso 1 1 calc R . . . .
C00W C 0.7597(4) 0.3119(4) 0.74179(9) 0.0279(8) Uani 1 1 d . . . . .
H00W H 0.6855 0.2911 0.7566 0.033 Uiso 1 1 calc R . . . .
C00X C 0.1783(4) 0.1953(4) 0.78351(9) 0.0315(8) Uani 1 1 d . . . . .
H00X H 0.0995 0.1514 0.7695 0.038 Uiso 1 1 calc R . . . .
C00Y C 0.7334(4) -0.2274(4) 0.76153(10) 0.0317(8) Uani 1 1 d . . . . .
H00G H 0.7903 -0.2236 0.7418 0.038 Uiso 1 1 calc R . . . .
H00H H 0.7945 -0.1707 0.7802 0.038 Uiso 1 1 calc R . . . .
C00Z C 0.2654(5) 0.1417(4) 0.78573(10) 0.0352(9) Uani 1 1 d . . . . .
H00Z H 0.2454 0.0621 0.7733 0.042 Uiso 1 1 calc R . . . .
C010 C 0.0360(4) -0.1723(4) 0.67095(11) 0.0345(9) Uani 1 1 d . . . . .
H010 H -0.0422 -0.1637 0.6681 0.041 Uiso 1 1 calc R . . . .
C011 C 0.4527(4) -0.4105(4) 0.73494(9) 0.0279(8) Uani 1 1 d . . . . .
H01A H 0.3957 -0.4159 0.7548 0.033 Uiso 1 1 calc R . . . .
H01B H 0.3917 -0.4673 0.7163 0.033 Uiso 1 1 calc R . . . .
C012 C 0.1308(4) 0.6920(4) 0.81453(12) 0.0359(9) Uani 1 1 d . . . . .
H01C H 0.1972 0.7257 0.8336 0.043 Uiso 1 1 calc R . . . .
H01D H 0.1822 0.7181 0.7927 0.043 Uiso 1 1 calc R . . . .
C013 C 0.0427(6) 0.7602(5) 0.81656(15) 0.0535(13) Uani 1 1 d . . . . .
H01E H -0.0185 0.7332 0.7964 0.064 Uiso 1 1 calc R . . . .
H01F H 0.1019 0.8601 0.8161 0.064 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
F001 C00N 1.356(4) . ?
F002 C00M 1.362(4) . ?
F003 C00R 1.346(5) . ?
O004 H004 0.8200 . ?
O004 C00B 1.346(4) . ?
O005 H005 0.8200 . ?
O005 C00E 1.341(4) . ?
O006 H006 0.8200 . ?
O006 C00K 1.329(5) . ?
N007 C00F 1.273(5) . ?
N007 C00J 1.463(5) . ?
N008 C00G 1.277(5) . ?
N008 C00I 1.457(5) . ?
N009 C00C 1.273(5) . ?
N009 C00L 1.461(5) . ?
C00A C00F 1.461(5) . ?
C00A C00K 1.406(5) . ?
C00A C00W 1.392(5) . ?
C00B C00D 1.409(5) . ?
C00B C00M 1.372(5) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.461(5) . ?
C00D C00P 1.398(5) . ?
C00E C00H 1.404(5) . ?
C00E C00N 1.388(5) . ?
C00F H00F 0.9300 . ?
C00G H00I 0.9300 . ?
C00G C00H 1.459(5) . ?
C00H C00X 1.401(5) . ?
C00I C00I 1.539(6) 6_556 ?
C00I H00K 0.9800 . ?
C00I C012 1.521(5) . ?
C00J H00J 0.9800 . ?
C00J C00L 1.528(5) . ?
C00J C00Y 1.528(5) . ?
C00K C00R 1.405(5) . ?
C00L H00L 0.9800 . ?
C00L C011 1.532(5) . ?
C00M C010 1.372(5) . ?
C00N C00Q 1.373(6) . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00O C00S 1.523(6) . ?
C00O C011 1.530(5) . ?
C00P H00P 0.9300 . ?
C00P C00T 1.373(6) . ?
C00Q H00Q 0.9300 . ?
C00Q C00Z 1.390(6) . ?
C00R C00V 1.367(6) . ?
C00S H00D 0.9700 . ?
C00S H00E 0.9700 . ?
C00S C00Y 1.525(6) . ?
C00T H00T 0.9300 . ?
C00T C010 1.394(6) . ?
C00U H00U 0.9300 . ?
C00U C00V 1.396(6) . ?
C00U C00W 1.378(6) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00X C00Z 1.374(6) . ?
C00Y H00G 0.9700 . ?
C00Y H00H 0.9700 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C012 H01C 0.9700 . ?
C012 H01D 0.9700 . ?
C012 C013 1.515(7) . ?
C013 C013 1.521(10) 6_556 ?
C013 H01E 0.9700 . ?
C013 H01F 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
C00B O004 H004 109.5 . . ?
C00E O005 H005 109.5 . . ?
C00K O006 H006 109.5 . . ?
C00F N007 C00J 119.9(3) . . ?
C00G N008 C00I 121.7(3) . . ?
C00C N009 C00L 119.1(3) . . ?
C00K C00A C00F 119.3(3) . . ?
C00W C00A C00F 120.9(3) . . ?
C00W C00A C00K 119.8(3) . . ?
O004 C00B C00D 122.2(3) . . ?
O004 C00B C00M 119.9(3) . . ?
C00M C00B C00D 117.9(3) . . ?
N009 C00C H00C 119.4 . . ?
N009 C00C C00D 121.2(3) . . ?
C00D C00C H00C 119.4 . . ?
C00B C00D C00C 120.4(3) . . ?
C00P C00D C00B 119.1(3) . . ?
C00P C00D C00C 120.3(3) . . ?
O005 C00E C00H 122.8(3) . . ?
O005 C00E C00N 119.6(3) . . ?
C00N C00E C00H 117.6(3) . . ?
N007 C00F C00A 120.8(3) . . ?
N007 C00F H00F 119.6 . . ?
C00A C00F H00F 119.6 . . ?
N008 C00G H00I 119.6 . . ?
N008 C00G C00H 120.7(3) . . ?
C00H C00G H00I 119.6 . . ?
C00E C00H C00G 119.5(3) . . ?
C00X C00H C00E 119.6(3) . . ?
C00X C00H C00G 121.0(3) . . ?
N008 C00I C00I 108.5(2) . 6_556 ?
N008 C00I H00K 109.7 . . ?
N008 C00I C012 108.9(3) . . ?
C00I C00I H00K 109.7 6_556 . ?
C012 C00I C00I 110.4(2) . 6_556 ?
C012 C00I H00K 109.7 . . ?
N007 C00J H00J 108.8 . . ?
N007 C00J C00L 109.5(3) . . ?
N007 C00J C00Y 109.3(3) . . ?
C00L C00J H00J 108.8 . . ?
C00Y C00J H00J 108.8 . . ?
C00Y C00J C00L 111.6(3) . . ?
O006 C00K C00A 123.5(3) . . ?
O006 C00K C00R 119.0(3) . . ?
C00R C00K C00A 117.5(3) . . ?
N009 C00L C00J 109.0(3) . . ?
N009 C00L H00L 109.7 . . ?
N009 C00L C011 108.1(3) . . ?
C00J C00L H00L 109.7 . . ?
C00J C00L C011 110.6(3) . . ?
C011 C00L H00L 109.7 . . ?
F002 C00M C00B 118.1(3) . . ?
F002 C00M C010 118.4(4) . . ?
C00B C00M C010 123.4(4) . . ?
F001 C00N C00E 117.5(4) . . ?
F001 C00N C00Q 119.4(4) . . ?
C00Q C00N C00E 123.1(4) . . ?
H00A C00O H00B 108.1 . . ?
C00S C00O H00A 109.5 . . ?
C00S C00O H00B 109.5 . . ?
C00S C00O C011 110.5(3) . . ?
C011 C00O H00A 109.5 . . ?
C011 C00O H00B 109.5 . . ?
C00D C00P H00P 119.4 . . ?
C00T C00P C00D 121.2(4) . . ?
C00T C00P H00P 119.4 . . ?
C00N C00Q H00Q 120.6 . . ?
C00N C00Q C00Z 118.7(4) . . ?
C00Z C00Q H00Q 120.6 . . ?
F003 C00R C00K 117.7(4) . . ?
F003 C00R C00V 119.9(4) . . ?
C00V C00R C00K 122.4(4) . . ?
C00O C00S H00D 109.6 . . ?
C00O C00S H00E 109.6 . . ?
C00O C00S C00Y 110.4(3) . . ?
H00D C00S H00E 108.1 . . ?
C00Y C00S H00D 109.6 . . ?
C00Y C00S H00E 109.6 . . ?
C00P C00T H00T 120.1 . . ?
C00P C00T C010 119.8(3) . . ?
C010 C00T H00T 120.1 . . ?
C00V C00U H00U 120.3 . . ?
C00W C00U H00U 120.3 . . ?
C00W C00U C00V 119.4(4) . . ?
C00R C00V C00U 119.5(4) . . ?
C00R C00V H00V 120.2 . . ?
C00U C00V H00V 120.2 . . ?
C00A C00W H00W 119.4 . . ?
C00U C00W C00A 121.3(4) . . ?
C00U C00W H00W 119.4 . . ?
C00H C00X H00X 119.6 . . ?
C00Z C00X C00H 120.9(4) . . ?
C00Z C00X H00X 119.6 . . ?
C00J C00Y H00G 109.4 . . ?
C00J C00Y H00H 109.4 . . ?
C00S C00Y C00J 111.3(3) . . ?
C00S C00Y H00G 109.4 . . ?
C00S C00Y H00H 109.4 . . ?
H00G C00Y H00H 108.0 . . ?
C00Q C00Z H00Z 120.0 . . ?
C00X C00Z C00Q 120.1(4) . . ?
C00X C00Z H00Z 120.0 . . ?
C00M C010 C00T 118.6(4) . . ?
C00M C010 H010 120.7 . . ?
C00T C010 H010 120.7 . . ?
C00L C011 H01A 109.3 . . ?
C00L C011 H01B 109.3 . . ?
C00O C011 C00L 111.6(3) . . ?
C00O C011 H01A 109.3 . . ?
C00O C011 H01B 109.3 . . ?
H01A C011 H01B 108.0 . . ?
C00I C012 H01C 109.1 . . ?
C00I C012 H01D 109.1 . . ?
H01C C012 H01D 107.9 . . ?
C013 C012 C00I 112.3(3) . . ?
C013 C012 H01C 109.1 . . ?
C013 C012 H01D 109.1 . . ?
C012 C013 C013 110.3(4) . 6_556 ?
C012 C013 H01E 109.6 . . ?
C012 C013 H01F 109.6 . . ?
C013 C013 H01E 109.6 6_556 . ?
C013 C013 H01F 109.6 6_556 . ?
H01E C013 H01F 108.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-14
_olex2_submission_special_instructions 'No special instructions were received'
