# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cyj-2-2f-2a
_database_code_depnum_ccdc_archive 'CCDC 1910663'
loop_
_audit_author_name
_audit_author_address
'Li menghua'
;Fuzhou University
China
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.04.16 svn.r3589 for OlexSys, GUI svn.r5734)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 F2 N3 O'
_chemical_formula_sum            'C10 H9 F2 N3 O'
_chemical_formula_weight         225.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   15.8495(17)
_cell_length_b                   10.2381(11)
_cell_length_c                   13.1866(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.544(12)
_cell_angle_gamma                90
_cell_volume                     2071.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    295.54(10)
_cell_measurement_theta_max      28.1300
_cell_measurement_theta_min      2.6970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7396
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.471
_diffrn_reflns_theta_min         2.550
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.54(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  77.00   0.50   13.00    --   -9.70  43.00 -30.00  250
  2  ω    -92.00 -65.00   0.50   13.00    --   -9.70  43.00 -60.00   54
  3  ω    -34.00  66.00   0.50   13.00    --   -9.70  43.00 -60.00  200
  4  ω    -98.00 -58.00   0.50   13.00    --   -9.70  43.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0164707000
_diffrn_orient_matrix_UB_12      0.0637387000
_diffrn_orient_matrix_UB_13      -0.0038361000
_diffrn_orient_matrix_UB_21      -0.0420053000
_diffrn_orient_matrix_UB_22      0.0209169000
_diffrn_orient_matrix_UB_23      -0.0282544000
_diffrn_orient_matrix_UB_31      -0.0099985000
_diffrn_orient_matrix_UB_32      0.0174710000
_diffrn_orient_matrix_UB_33      0.0476997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1751
_reflns_number_total             2380
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.228
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0112(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.5681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F)
2.c Idealised Me refined as rotating group:
 C00G(H00C,H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.44892(6) 0.92447(9) 0.39586(7) 0.0620(3) Uani 1 1 d . . . . .
F002 F 0.45876(7) 0.72061(10) 0.35941(8) 0.0643(3) Uani 1 1 d . . . . .
O003 O 0.64352(6) 0.72111(11) 0.74737(8) 0.0501(3) Uani 1 1 d . . . . .
N004 N 0.55328(7) 0.76045(11) 0.58038(8) 0.0356(3) Uani 1 1 d . . . . .
N005 N 0.65182(7) 0.83686(13) 0.50289(9) 0.0444(3) Uani 1 1 d . . . . .
N006 N 0.68904(7) 0.80623(13) 0.60580(9) 0.0458(3) Uani 1 1 d . . . . .
H006 H 0.743580 0.816479 0.635067 0.055 Uiso 1 1 calc R . . . .
C007 C 0.47266(8) 0.71182(13) 0.59709(10) 0.0354(3) Uani 1 1 d . . . . .
C008 C 0.57053(9) 0.80911(13) 0.49060(11) 0.0373(3) Uani 1 1 d . . . . .
C009 C 0.63170(9) 0.75857(14) 0.65632(11) 0.0389(3) Uani 1 1 d . . . . .
C00A C 0.46627(9) 0.58051(14) 0.61702(12) 0.0437(4) Uani 1 1 d . . . . .
H00A H 0.512669 0.524673 0.617567 0.052 Uiso 1 1 calc R . . . .
C00B C 0.40431(9) 0.79486(15) 0.59624(12) 0.0432(4) Uani 1 1 d . . . . .
H00B H 0.408872 0.883547 0.583336 0.052 Uiso 1 1 calc R . . . .
C00C C 0.32034(9) 0.61391(17) 0.63521(11) 0.0493(4) Uani 1 1 d . . . . .
C00D C 0.32871(10) 0.74441(17) 0.61488(13) 0.0498(4) Uani 1 1 d . . . . .
H00D H 0.282191 0.800277 0.613652 0.060 Uiso 1 1 calc R . . . .
C00E C 0.50654(9) 0.82940(14) 0.38843(11) 0.0417(3) Uani 1 1 d . . . . .
H00E H 0.537011 0.852709 0.334867 0.050 Uiso 1 1 calc R . . . .
C00F C 0.39028(10) 0.53272(16) 0.63618(12) 0.0515(4) Uani 1 1 d . . . . .
H00F H 0.386047 0.444219 0.649997 0.062 Uiso 1 1 calc R . . . .
C00G C 0.23759(12) 0.5601(2) 0.65523(17) 0.0768(6) Uani 1 1 d . . . . .
H00C H 0.199084 0.630768 0.660333 0.115 Uiso 1 1 calc GR . . . .
H00G H 0.251131 0.511520 0.719572 0.115 Uiso 1 1 calc GR . . . .
H00H H 0.209812 0.503596 0.598544 0.115 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00E 1.3550(16) . ?
F002 C00E 1.3471(17) . ?
O003 C009 1.2291(17) . ?
N004 C007 1.4391(16) . ?
N004 C008 1.3737(17) . ?
N004 C009 1.3866(17) . ?
N005 N006 1.3733(17) . ?
N005 C008 1.2893(17) . ?
N006 H006 0.8600 . ?
N006 C009 1.3461(18) . ?
C007 C00A 1.378(2) . ?
C007 C00B 1.3748(19) . ?
C008 C00E 1.484(2) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.381(2) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.382(2) . ?
C00C C00D 1.376(2) . ?
C00C C00F 1.383(2) . ?
C00C C00G 1.506(2) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9800 . ?
C00F H00F 0.9300 . ?
C00G H00C 0.9600 . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 N004 C007 129.34(11) . . ?
C008 N004 C009 106.93(11) . . ?
C009 N004 C007 123.64(11) . . ?
C008 N005 N006 103.98(11) . . ?
N005 N006 H006 123.3 . . ?
C009 N006 N005 113.32(11) . . ?
C009 N006 H006 123.3 . . ?
C00A C007 N004 118.50(12) . . ?
C00B C007 N004 120.86(12) . . ?
C00B C007 C00A 120.61(12) . . ?
N004 C008 C00E 126.51(12) . . ?
N005 C008 N004 112.36(12) . . ?
N005 C008 C00E 121.13(12) . . ?
O003 C009 N004 126.79(13) . . ?
O003 C009 N006 129.81(13) . . ?
N006 C009 N004 103.40(11) . . ?
C007 C00A H00A 120.3 . . ?
C007 C00A C00F 119.31(13) . . ?
C00F C00A H00A 120.3 . . ?
C007 C00B H00B 120.5 . . ?
C007 C00B C00D 118.94(14) . . ?
C00D C00B H00B 120.5 . . ?
C00D C00C C00F 117.98(13) . . ?
C00D C00C C00G 121.37(16) . . ?
C00F C00C C00G 120.64(16) . . ?
C00B C00D H00D 119.1 . . ?
C00C C00D C00B 121.86(14) . . ?
C00C C00D H00D 119.1 . . ?
F001 C00E C008 110.75(11) . . ?
F001 C00E H00E 109.9 . . ?
F002 C00E F001 105.87(11) . . ?
F002 C00E C008 110.46(12) . . ?
F002 C00E H00E 109.9 . . ?
C008 C00E H00E 109.9 . . ?
C00A C00F C00C 121.29(14) . . ?
C00A C00F H00F 119.4 . . ?
C00C C00F H00F 119.4 . . ?
C00C C00G H00C 109.5 . . ?
C00C C00G H00G 109.5 . . ?
C00C C00G H00H 109.5 . . ?
H00C C00G H00G 109.5 . . ?
H00C C00G H00H 109.5 . . ?
H00G C00G H00H 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_cyj-2-2a
_database_code_depnum_ccdc_archive 'CCDC 1914002'
loop_
_audit_author_name
_audit_author_address
cyj
;Fuzhou University
China
;
_audit_update_record             
;
2019-05-05 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '3(C10 H8 F3 N3 O)'
_chemical_formula_sum            'C30 H24 F9 N9 O3'
_chemical_formula_weight         729.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.042(4)
_cell_length_b                   10.654(5)
_cell_length_c                   20.098(9)
_cell_angle_alpha                84.402(6)
_cell_angle_beta                 81.612(7)
_cell_angle_gamma                85.682(7)
_cell_volume                     1692.3(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1814
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.722
_cell_measurement_theta_min      2.565
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.7122.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.065
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13751
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.745
_diffrn_reflns_theta_min         1.028
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3141
_reflns_number_total             7329
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.281
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1827
_refine_ls_R_factor_gt           0.0816
_refine_ls_restrained_S_all      0.964
_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)+(0.1092P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N008(H008), N00A(H00A), N00B(H00B), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012), C013(H013),
 C017(H017), C019(H019), C01A(H01G)
2.b Idealised Me refined as rotating group:
 C01D(H01A,H01B,H01C), C01E(H01D,H01E,H01F), C01F(H01H,H01I,H01J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.4254(3) 0.3525(3) 0.32044(14) 0.0634(7) Uani 1 1 d . . . . .
O002 O 0.8048(3) 0.2907(3) 0.19361(14) 0.0656(8) Uani 1 1 d . . . . .
O003 O 1.1416(3) 0.1250(3) 0.28417(13) 0.0662(8) Uani 1 1 d . . . . .
F004 F 0.1353(4) 0.7539(3) 0.21487(14) 0.0996(9) Uani 1 1 d . . . . .
N005 N 0.2708(3) 0.5078(3) 0.26057(14) 0.0470(7) Uani 1 1 d . . . . .
N006 N 0.7310(4) 0.1385(3) 0.12874(15) 0.0530(8) Uani 1 1 d . . . . .
N007 N 0.9320(4) 0.1100(3) 0.37887(14) 0.0490(8) Uani 1 1 d . . . . .
N008 N 0.5201(4) 0.4543(3) 0.21500(16) 0.0601(9) Uani 1 1 d . . . . .
H008 H 0.619588 0.418150 0.208299 0.072 Uiso 1 1 calc R . . . .
F009 F 0.6369(4) 0.1993(3) 0.48155(16) 0.1206(11) Uani 1 1 d . . . . .
N00A N 0.9401(4) 0.0928(3) 0.18358(15) 0.0603(9) Uani 1 1 d . . . . .
H00A H 1.016042 0.097879 0.209047 0.072 Uiso 1 1 calc R . . . .
N00B N 1.1457(4) 0.2169(3) 0.38448(16) 0.0596(9) Uani 1 1 d . . . . .
H00B H 1.240336 0.251625 0.374386 0.072 Uiso 1 1 calc R . . . .
N00C N 0.4603(4) 0.5436(3) 0.17031(16) 0.0651(9) Uani 1 1 d . . . . .
F00D F 0.7437(4) 0.0241(3) 0.50795(16) 0.1287(13) Uani 1 1 d . . . . .
F00E F 0.2728(4) 0.7395(3) 0.11800(15) 0.1348(14) Uani 1 1 d . . . . .
F00F F 0.0652(5) 0.6281(4) 0.15260(18) 0.1325(13) Uani 1 1 d . . . . .
N00G N 1.0451(5) 0.2252(3) 0.44479(16) 0.0642(9) Uani 1 1 d . . . . .
C00H C 0.1179(4) 0.5146(3) 0.30795(17) 0.0441(9) Uani 1 1 d . . . . .
C00I C 0.8238(4) 0.1859(4) 0.17235(17) 0.0478(9) Uani 1 1 d . . . . .
F00J F 0.8075(4) 0.1841(4) 0.55050(15) 0.1479(16) Uani 1 1 d . . . . .
C00K C 0.8184(4) 0.0351(3) 0.35322(17) 0.0476(9) Uani 1 1 d . . . . .
C00L C 0.4096(4) 0.4270(4) 0.2711(2) 0.0500(9) Uani 1 1 d . . . . .
N00M N 0.9260(5) -0.0106(4) 0.15065(19) 0.0795(11) Uani 1 1 d . . . . .
C00N C 1.0819(5) 0.1486(4) 0.3423(2) 0.0528(9) Uani 1 1 d . . . . .
C00O C 0.5871(5) 0.2046(4) 0.10341(19) 0.0530(9) Uani 1 1 d . . . . .
C00P C 0.3102(5) 0.5744(4) 0.19919(18) 0.0561(10) Uani 1 1 d . . . . .
C00Q C -0.0237(5) 0.4626(4) 0.2948(2) 0.0584(10) Uani 1 1 d . . . . .
H00Q H -0.022668 0.422953 0.255463 0.070 Uiso 1 1 calc R . . . .
C00R C 0.6660(5) 0.0861(4) 0.33940(19) 0.0564(10) Uani 1 1 d . . . . .
H00R H 0.633691 0.169758 0.346905 0.068 Uiso 1 1 calc R . . . .
C00S C 0.1197(5) 0.5709(4) 0.36606(18) 0.0540(10) Uani 1 1 d . . . . .
H00S H 0.217415 0.604352 0.374379 0.065 Uiso 1 1 calc R . . . .
C00T C 0.9184(5) 0.1603(4) 0.43942(19) 0.0563(10) Uani 1 1 d . . . . .
C00U C -0.0245(6) 0.5779(4) 0.4122(2) 0.0706(12) Uani 1 1 d . . . . .
H00U H -0.024132 0.615352 0.452073 0.085 Uiso 1 1 calc R . . . .
C00V C -0.1710(5) 0.5286(4) 0.3991(2) 0.0709(12) Uani 1 1 d . . . . .
C00W C 0.8681(6) -0.0886(4) 0.3418(2) 0.0667(11) Uani 1 1 d . . . . .
H00W H 0.972009 -0.123562 0.351812 0.080 Uiso 1 1 calc R . . . .
C00X C 0.1978(6) 0.6743(5) 0.1711(2) 0.0730(12) Uani 1 1 d . . . . .
C00Y C 0.5598(5) 0.0131(5) 0.3142(2) 0.0724(12) Uani 1 1 d . . . . .
H00Y H 0.455139 0.047916 0.305066 0.087 Uiso 1 1 calc R . . . .
C00Z C 0.6045(6) 0.2666(4) 0.0408(2) 0.0710(12) Uani 1 1 d . . . . .
H00Z H 0.709147 0.267809 0.014090 0.085 Uiso 1 1 calc R . . . .
C010 C 0.8006(6) 0.0193(4) 0.1183(2) 0.0726(12) Uani 1 1 d . . . . .
F011 F 0.7610(7) -0.0212(4) 0.0110(2) 0.1731(19) Uani 1 1 d . . . . .
C012 C -0.1666(5) 0.4705(4) 0.3410(3) 0.0740(13) Uani 1 1 d . . . . .
H012 H -0.263165 0.435440 0.332599 0.089 Uiso 1 1 calc R . . . .
C013 C 0.4330(5) 0.2072(4) 0.1437(2) 0.0733(12) Uani 1 1 d . . . . .
H013 H 0.421443 0.165097 0.186743 0.088 Uiso 1 1 calc R . . . .
C014 C 0.3114(6) 0.3329(4) 0.0557(3) 0.0727(12) Uani 1 1 d . . . . .
C015 C 0.7779(7) 0.1408(5) 0.4950(2) 0.0744(13) Uani 1 1 d . . . . .
C016 C 0.6063(6) -0.1105(5) 0.3024(2) 0.0768(13) Uani 1 1 d . . . . .
C017 C 0.2969(5) 0.2721(5) 0.1199(3) 0.0781(13) Uani 1 1 d . . . . .
H017 H 0.193369 0.275193 0.147459 0.094 Uiso 1 1 calc R . . . .
F018 F 0.5793(7) -0.0792(4) 0.0882(3) 0.180(2) Uani 1 1 d . . . . .
C019 C 0.4638(7) 0.3278(5) 0.0172(2) 0.0819(14) Uani 1 1 d . . . . .
H019 H 0.474563 0.366716 -0.026506 0.098 Uiso 1 1 calc R . . . .
C01A C 0.7627(7) -0.1590(4) 0.3155(2) 0.0826(14) Uani 1 1 d . . . . .
H01G H 0.797350 -0.241555 0.306301 0.099 Uiso 1 1 calc R . . . .
F01B F 0.8158(8) -0.1753(4) 0.0790(3) 0.236(3) Uani 1 1 d . . . . .
C01C C 0.7418(12) -0.0662(6) 0.0742(4) 0.117(2) Uani 1 1 d . . . . .
C01D C -0.3300(6) 0.5387(6) 0.4491(3) 0.126(2) Uani 1 1 d . . . . .
H01A H -0.301620 0.551758 0.492604 0.189 Uiso 1 1 calc GR . . . .
H01B H -0.387420 0.462024 0.452355 0.189 Uiso 1 1 calc GR . . . .
H01C H -0.402046 0.608560 0.434264 0.189 Uiso 1 1 calc GR . . . .
C01E C 0.1586(7) 0.4028(6) 0.0299(3) 0.118(2) Uani 1 1 d . . . . .
H01D H 0.081656 0.342861 0.022103 0.176 Uiso 1 1 calc GR . . . .
H01E H 0.193810 0.452251 -0.011650 0.176 Uiso 1 1 calc GR . . . .
H01F H 0.103778 0.457384 0.062756 0.176 Uiso 1 1 calc GR . . . .
C01F C 0.4886(8) -0.1905(6) 0.2750(3) 0.131(2) Uani 1 1 d . . . . .
H01H H 0.462513 -0.262155 0.306652 0.196 Uiso 1 1 calc GR . . . .
H01I H 0.542026 -0.219127 0.232782 0.196 Uiso 1 1 calc GR . . . .
H01J H 0.386735 -0.141072 0.268193 0.196 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00L 1.224(4) . ?
O002 C00I 1.226(4) . ?
O003 C00N 1.238(4) . ?
F004 C00X 1.303(5) . ?
N005 C00H 1.443(4) . ?
N005 C00L 1.386(5) . ?
N005 C00P 1.370(5) . ?
N006 C00I 1.383(4) . ?
N006 C00O 1.440(5) . ?
N006 C010 1.372(5) . ?
N007 C00K 1.437(4) . ?
N007 C00N 1.386(5) . ?
N007 C00T 1.363(5) . ?
N008 N00C 1.354(4) . ?
N008 C00L 1.352(4) . ?
F009 C015 1.304(5) . ?
N00A C00I 1.337(5) . ?
N00A N00M 1.359(4) . ?
N00B N00G 1.363(4) . ?
N00B C00N 1.348(5) . ?
N00C C00P 1.294(4) . ?
F00D C015 1.287(5) . ?
F00E C00X 1.310(5) . ?
F00F C00X 1.322(5) . ?
N00G C00T 1.297(5) . ?
C00H C00Q 1.373(5) . ?
C00H C00S 1.366(5) . ?
F00J C015 1.306(5) . ?
C00K C00R 1.357(5) . ?
C00K C00W 1.380(5) . ?
N00M C010 1.282(5) . ?
C00O C00Z 1.357(5) . ?
C00O C013 1.378(5) . ?
C00P C00X 1.468(6) . ?
C00Q C012 1.371(5) . ?
C00R C00Y 1.376(5) . ?
C00S C00U 1.377(5) . ?
C00T C015 1.480(6) . ?
C00U C00V 1.394(6) . ?
C00V C012 1.369(6) . ?
C00V C01D 1.512(6) . ?
C00W C01A 1.366(6) . ?
C00Y C016 1.376(7) . ?
C00Z C019 1.383(6) . ?
C010 C01C 1.478(7) . ?
F011 C01C 1.304(8) . ?
C013 C017 1.371(6) . ?
C014 C017 1.379(6) . ?
C014 C019 1.351(6) . ?
C014 C01E 1.519(6) . ?
C016 C01A 1.375(7) . ?
C016 C01F 1.513(6) . ?
F018 C01C 1.311(8) . ?
F01B C01C 1.267(7) . ?

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 N005 C00H 123.7(3) . . ?
C00P N005 C00H 129.4(3) . . ?
C00P N005 C00L 106.9(3) . . ?
C00I N006 C00O 124.5(3) . . ?
C010 N006 C00I 106.1(3) . . ?
C010 N006 C00O 129.4(3) . . ?
C00N N007 C00K 123.8(3) . . ?
C00T N007 C00K 130.0(3) . . ?
C00T N007 C00N 106.2(3) . . ?
C00L N008 N00C 114.1(3) . . ?
C00I N00A N00M 113.1(3) . . ?
C00N N00B N00G 113.1(3) . . ?
C00P N00C N008 103.7(3) . . ?
C00T N00G N00B 103.7(3) . . ?
C00Q C00H N005 119.9(3) . . ?
C00S C00H N005 118.5(3) . . ?
C00S C00H C00Q 121.6(3) . . ?
O002 C00I N006 127.2(4) . . ?
O002 C00I N00A 128.8(4) . . ?
N00A C00I N006 104.0(3) . . ?
C00R C00K N007 120.5(3) . . ?
C00R C00K C00W 120.7(4) . . ?
C00W C00K N007 118.8(3) . . ?
O001 C00L N005 127.2(3) . . ?
O001 C00L N008 130.0(4) . . ?
N008 C00L N005 102.8(3) . . ?
C010 N00M N00A 104.3(4) . . ?
O003 C00N N007 127.3(4) . . ?
O003 C00N N00B 128.7(3) . . ?
N00B C00N N007 104.0(3) . . ?
C00Z C00O N006 120.0(3) . . ?
C00Z C00O C013 120.3(4) . . ?
C013 C00O N006 119.7(4) . . ?
N005 C00P C00X 123.6(3) . . ?
N00C C00P N005 112.5(4) . . ?
N00C C00P C00X 123.9(4) . . ?
C012 C00Q C00H 118.4(4) . . ?
C00K C00R C00Y 119.6(4) . . ?
C00H C00S C00U 119.5(4) . . ?
N007 C00T C015 124.5(4) . . ?
N00G C00T N007 113.1(3) . . ?
N00G C00T C015 122.4(4) . . ?
C00S C00U C00V 119.9(4) . . ?
C00U C00V C01D 119.8(5) . . ?
C012 C00V C00U 118.8(4) . . ?
C012 C00V C01D 121.4(5) . . ?
C01A C00W C00K 119.1(4) . . ?
F004 C00X F00E 107.5(4) . . ?
F004 C00X F00F 104.8(4) . . ?
F004 C00X C00P 112.5(4) . . ?
F00E C00X F00F 107.0(4) . . ?
F00E C00X C00P 112.6(4) . . ?
F00F C00X C00P 111.9(4) . . ?
C00R C00Y C016 121.0(4) . . ?
C00O C00Z C019 118.9(4) . . ?
N006 C010 C01C 124.7(5) . . ?
N00M C010 N006 112.4(4) . . ?
N00M C010 C01C 122.8(5) . . ?
C00V C012 C00Q 121.8(4) . . ?
C017 C013 C00O 119.6(4) . . ?
C017 C014 C01E 120.1(5) . . ?
C019 C014 C017 118.1(4) . . ?
C019 C014 C01E 121.7(5) . . ?
F009 C015 F00J 105.4(4) . . ?
F009 C015 C00T 112.8(4) . . ?
F00D C015 F009 104.6(4) . . ?
F00D C015 F00J 108.8(4) . . ?
F00D C015 C00T 112.9(4) . . ?
F00J C015 C00T 111.9(4) . . ?
C00Y C016 C01F 120.7(5) . . ?
C01A C016 C00Y 118.3(4) . . ?
C01A C016 C01F 120.9(5) . . ?
C013 C017 C014 120.9(4) . . ?
C014 C019 C00Z 122.2(4) . . ?
C00W C01A C016 121.4(4) . . ?
F011 C01C C010 112.2(6) . . ?
F011 C01C F018 103.3(6) . . ?
F018 C01C C010 112.0(6) . . ?
F01B C01C C010 112.0(5) . . ?
F01B C01C F011 109.0(7) . . ?
F01B C01C F018 107.8(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
