# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_FVE671
_database_code_depnum_ccdc_archive 'CCDC 1963617'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 Cl N2 O3,C4 H10 O'
_chemical_formula_sum            'C26 H25 Cl N2 O4'
_chemical_formula_weight         464.93

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8999(3)
_cell_length_b                   15.9931(4)
_cell_length_c                   15.6852(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.928(3)
_cell_angle_gamma                90
_cell_volume                     2399.62(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10568
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      67.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .13
_exptl_absorpt_coefficient_mu    1.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.617


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            16528
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.019
_diffrn_reflns_theta_max         68.107
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4172
_reflns_number_gt                2606
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4172
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.97758(8) 0.63664(4) 0.69296(4) 0.0896(3) Uani 1 1 d . . . . .
O1 O 0.20756(16) 0.61005(11) -0.09133(11) 0.0702(5) Uani 1 1 d . . . . .
O2 O 0.69275(17) 0.73709(8) 0.31860(10) 0.0636(4) Uani 1 1 d . . . . .
O3 O 0.65515(17) 0.45614(8) 0.27511(11) 0.0687(4) Uani 1 1 d . . . . .
N1 N 0.8291(2) 0.77883(12) 0.22778(14) 0.0660(5) Uani 1 1 d . . . . .
N2 N 0.66408(17) 0.58239(9) 0.20085(11) 0.0522(4) Uani 1 1 d . . . . .
C2 C 0.7611(2) 0.72280(12) 0.26602(15) 0.0542(5) Uani 1 1 d . . . . .
C3 C 0.7891(2) 0.63586(11) 0.23213(14) 0.0515(5) Uani 1 1 d . . . . .
C4 C 0.9337(3) 0.60421(15) 0.11755(16) 0.0682(6) Uani 1 1 d . . . . .
H4 H 0.920894 0.546597 0.117412 0.082 Uiso 1 1 calc R U . . .
C5 C 1.0120(3) 0.6401(2) 0.0663(2) 0.0884(8) Uani 1 1 d . . . . .
H5 H 1.051556 0.606572 0.030749 0.106 Uiso 1 1 calc R U . . .
C6 C 1.0320(3) 0.7251(2) 0.0674(2) 0.1009(10) Uani 1 1 d . . . . .
H6 H 1.085484 0.748189 0.032522 0.121 Uiso 1 1 calc R U . . .
C7 C 0.9746(3) 0.77717(18) 0.1189(2) 0.0896(8) Uani 1 1 d . . . . .
H7 H 0.988219 0.834719 0.119249 0.107 Uiso 1 1 calc R U . . .
C8 C 0.8968(2) 0.74088(14) 0.16963(16) 0.0645(6) Uani 1 1 d . . . . .
C9 C 0.8749(2) 0.65481(13) 0.16877(15) 0.0565(5) Uani 1 1 d . . . . .
C10 C 0.8444(2) 0.56646(12) 0.30469(15) 0.0557(5) Uani 1 1 d . . . . .
C11 C 0.7085(2) 0.52154(12) 0.26154(15) 0.0564(5) Uani 1 1 d . . . . .
C12 C 0.5475(2) 0.59091(11) 0.12681(13) 0.0500(5) Uani 1 1 d . . . . .
C13 C 0.4525(2) 0.52621(12) 0.10308(15) 0.0579(6) Uani 1 1 d . . . . .
H13 H 0.464796 0.477137 0.135997 0.069 Uiso 1 1 calc R U . . .
C14 C 0.3402(2) 0.53431(13) 0.03111(15) 0.0618(6) Uani 1 1 d . . . . .
H14 H 0.276200 0.490801 0.016024 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3210(2) 0.60639(12) -0.01936(14) 0.0540(5) Uani 1 1 d . . . . .
C16 C 0.4156(2) 0.67068(12) 0.00419(15) 0.0608(6) Uani 1 1 d . . . . .
H16 H 0.403664 0.719658 -0.028879 0.073 Uiso 1 1 calc R U . . .
C17 C 0.5281(2) 0.66249(12) 0.07690(15) 0.0603(6) Uani 1 1 d . . . . .
H17 H 0.591709 0.706176 0.092320 0.072 Uiso 1 1 calc R U . . .
C18 C 0.8763(2) 0.58624(11) 0.40084(14) 0.0543(5) Uani 1 1 d . . . . .
C19 C 0.7717(3) 0.58819(14) 0.44473(17) 0.0653(6) Uani 1 1 d . . . . .
H19 H 0.679555 0.578662 0.413529 0.078 Uiso 1 1 calc R U . . .
C20 C 0.8023(3) 0.60410(14) 0.53436(17) 0.0685(6) Uani 1 1 d . . . . .
H20 H 0.731252 0.605591 0.563296 0.082 Uiso 1 1 calc R U . . .
C21 C 0.9392(3) 0.61773(13) 0.58032(16) 0.0639(6) Uani 1 1 d . . . . .
C22 C 1.0446(3) 0.61689(13) 0.53841(17) 0.0644(6) Uani 1 1 d . . . . .
H22 H 1.136520 0.626746 0.569941 0.077 Uiso 1 1 calc R U . . .
C23 C 1.0132(2) 0.60125(12) 0.44886(16) 0.0594(6) Uani 1 1 d . . . . .
H23 H 1.084570 0.600751 0.420219 0.071 Uiso 1 1 calc R U . . .
O4 O 1.2612(3) 0.67023(18) 0.3420(2) 0.1451(10) Uani 1 1 d . . . . .
C24 C 1.2820(5) 0.7536(3) 0.3321(3) 0.1379(14) Uani 1 1 d . . . . .
H24A H 1.256956 0.767655 0.269866 0.165 Uiso 1 1 calc R U . . .
H24B H 1.380147 0.766756 0.356039 0.165 Uiso 1 1 calc R U . . .
C25 C 1.1994(5) 0.8024(3) 0.3766(4) 0.1594(18) Uani 1 1 d . . . . .
H25A H 1.102452 0.788765 0.353579 0.239 Uiso 1 1 calc R U . . .
H25B H 1.213386 0.860793 0.367316 0.239 Uiso 1 1 calc R U . . .
H25C H 1.227252 0.790420 0.438628 0.239 Uiso 1 1 calc R U . . .
C26 C 1.3369(6) 0.6186(4) 0.2956(4) 0.168(2) Uani 1 1 d . . . . .
H26A H 1.301886 0.627899 0.232612 0.202 Uiso 1 1 calc R U . . .
H26B H 1.434957 0.634034 0.312442 0.202 Uiso 1 1 calc R U . . .
C27 C 1.3240(8) 0.5362(4) 0.3135(6) 0.231(4) Uani 1 1 d . . . . .
H27A H 1.352167 0.527586 0.376134 0.347 Uiso 1 1 calc R U . . .
H27B H 1.382317 0.503628 0.285881 0.347 Uiso 1 1 calc R U . . .
H27C H 1.228336 0.519356 0.291072 0.347 Uiso 1 1 calc R U . . .
H10 H 0.922(2) 0.5404(14) 0.2915(13) 0.055(6) Uiso 1 1 d . . . . .
H1 H 0.209(3) 0.6599(19) -0.1216(18) 0.088(8) Uiso 1 1 d . . . . .
H11 H 0.821(3) 0.8334(19) 0.2339(17) 0.082(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.735(2) . ?
O1 C15 1.373(3) . ?
O1 H1 0.93(3) . ?
O2 C2 1.215(3) . ?
O3 C11 1.215(2) . ?
N1 C2 1.351(3) . ?
N1 C8 1.402(3) . ?
N1 H11 0.88(3) . ?
N2 C11 1.353(3) . ?
N2 C12 1.417(3) . ?
N2 C3 1.480(2) . ?
C2 C3 1.539(3) . ?
C3 C9 1.496(3) . ?
C3 C10 1.583(3) . ?
C4 C9 1.371(3) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(3) . ?
C10 C18 1.493(3) . ?
C10 C11 1.521(3) . ?
C10 H10 0.94(2) . ?
C12 C17 1.372(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 C23 1.391(3) . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(4) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
O4 C24 1.364(5) . ?
O4 C26 1.434(5) . ?
C24 C25 1.434(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.359(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C15 O1 H1 109.9(17) . . ?
C2 N1 C8 112.23(19) . . ?
C2 N1 H11 122.5(17) . . ?
C8 N1 H11 124.8(17) . . ?
C11 N2 C12 133.96(17) . . ?
C11 N2 C3 95.14(15) . . ?
C12 N2 C3 130.61(16) . . ?
O2 C2 N1 127.21(19) . . ?
O2 C2 C3 125.84(19) . . ?
N1 C2 C3 106.9(2) . . ?
N2 C3 C9 117.80(17) . . ?
N2 C3 C2 115.27(17) . . ?
C9 C3 C2 103.31(16) . . ?
N2 C3 C10 86.46(14) . . ?
C9 C3 C10 117.98(18) . . ?
C2 C3 C10 116.42(17) . . ?
C9 C4 C5 118.9(2) . . ?
C9 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.5(3) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C8 C9 121.5(2) . . ?
C7 C8 N1 128.9(2) . . ?
C9 C8 N1 109.6(2) . . ?
C4 C9 C8 120.0(2) . . ?
C4 C9 C3 132.0(2) . . ?
C8 C9 C3 107.91(19) . . ?
C18 C10 C11 118.8(2) . . ?
C18 C10 C3 121.44(17) . . ?
C11 C10 C3 84.76(15) . . ?
C18 C10 H10 110.1(13) . . ?
C11 C10 H10 111.7(13) . . ?
C3 C10 H10 107.7(13) . . ?
O3 C11 N2 131.7(2) . . ?
O3 C11 C10 134.68(19) . . ?
N2 C11 C10 93.63(16) . . ?
C17 C12 C13 119.0(2) . . ?
C17 C12 N2 120.85(17) . . ?
C13 C12 N2 120.15(18) . . ?
C14 C13 C12 120.11(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.85(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
O1 C15 C16 123.01(19) . . ?
O1 C15 C14 117.95(18) . . ?
C16 C15 C14 119.0(2) . . ?
C15 C16 C17 119.97(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.03(19) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C23 118.4(2) . . ?
C19 C18 C10 121.1(2) . . ?
C23 C18 C10 120.4(2) . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 Cl1 119.76(19) . . ?
C20 C21 Cl1 119.2(2) . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C24 O4 C26 113.0(4) . . ?
O4 C24 C25 110.8(4) . . ?
O4 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 O4 111.3(4) . . ?
C27 C26 H26A 109.4 . . ?
O4 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
O4 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_fve762
_database_code_depnum_ccdc_archive 'CCDC 1963623'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl F N2 O2'
_chemical_formula_sum            'C22 H14 Cl F N2 O2'
_chemical_formula_weight         392.80

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'
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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   11.7246(2)
_cell_length_b                   11.7246(2)
_cell_length_c                   27.1515(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3732.41(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    15801
_cell_measurement_theta_min      23.1
_cell_measurement_theta_max      72.2

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .21
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.617


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            17893
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         28.260
_diffrn_reflns_theta_max         72.854
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6307
_reflns_number_gt                5501
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.822
_reflns_Friedel_fraction_full    0.831

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+0.1042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6307
_refine_ls_number_parameters     506
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1A Cl -0.48448(11) 0.19075(14) 0.50230(6) 0.0668(5) Uani 1 1 d . . . . .
O1A O 0.0487(4) -0.0880(4) 0.5239(2) 0.0732(13) Uani 1 1 d . . . . .
O2A O 0.2579(3) 0.2436(3) 0.52194(14) 0.0529(8) Uani 1 1 d . . . . .
N1A N 0.1740(4) 0.3423(3) 0.45835(16) 0.0480(9) Uani 1 1 d . . . . .
H1A H 0.207638 0.406864 0.462256 0.058 Uiso 1 1 calc R U . . .
N2A N 0.1433(4) 0.0403(3) 0.47093(16) 0.0483(9) Uani 1 1 d . . . . .
F1A F 0.4443(7) -0.1878(7) 0.3517(3) 0.124(2) Uani 1 1 d . . . . .
C2A C 0.1914(4) 0.2506(4) 0.48784(17) 0.0425(9) Uani 1 1 d . . . . .
C3A C 0.1060(4) 0.1589(4) 0.47080(17) 0.0427(9) Uani 1 1 d . . . . .
C4A C -0.0166(5) 0.1637(5) 0.3904(2) 0.0536(11) Uani 1 1 d . . . . .
H4A H -0.040662 0.088230 0.392419 0.064 Uiso 1 1 calc R U . . .
C5A C -0.0532(6) 0.2334(6) 0.3523(2) 0.0614(13) Uani 1 1 d . . . . .
H5A H -0.102874 0.204529 0.328692 0.074 Uiso 1 1 calc R U . . .
C6A C -0.0169(6) 0.3452(5) 0.3491(2) 0.0606(13) Uani 1 1 d . . . . .
H6A H -0.043711 0.391121 0.323719 0.073 Uiso 1 1 calc R U . . .
C7A C 0.0593(5) 0.3900(4) 0.3833(2) 0.0547(11) Uani 1 1 d . . . . .
H7A H 0.085117 0.464813 0.380840 0.066 Uiso 1 1 calc R U . . .
C8A C 0.0948(4) 0.3202(4) 0.42073(18) 0.0446(10) Uani 1 1 d . . . . .
C9A C 0.0561(4) 0.2084(4) 0.42514(17) 0.0432(9) Uani 1 1 d . . . . .
C10A C 0.0221(4) 0.1241(4) 0.51524(18) 0.0489(10) Uani 1 1 d . . . . .
H10A H 0.049106 0.155356 0.546629 0.059 Uiso 1 1 calc R U . . .
C11A C 0.0685(4) 0.0040(4) 0.5068(2) 0.0512(11) Uani 1 1 d . . . . .
C12A C 0.2203(5) -0.0175(4) 0.4400(2) 0.0532(11) Uani 1 1 d . . . . .
C13A C 0.2176(6) -0.1357(5) 0.4382(3) 0.0702(17) Uani 1 1 d . . . . .
H13A H 0.165744 -0.176440 0.457278 0.084 Uiso 1 1 calc R U . . .
C14A C 0.2934(8) -0.1919(7) 0.4078(4) 0.085(2) Uani 1 1 d . . . . .
H14A H 0.292997 -0.271118 0.406217 0.102 Uiso 1 1 calc R U . . .
C15A C 0.3682(8) -0.1314(8) 0.3802(3) 0.083(2) Uani 1 1 d . . . . .
C16A C 0.3742(7) -0.0131(7) 0.3812(3) 0.0757(18) Uani 1 1 d . . . . .
H16A H 0.427177 0.026658 0.362373 0.091 Uiso 1 1 calc R U . . .
C17A C 0.2977(6) 0.0431(5) 0.4117(2) 0.0625(14) Uani 1 1 d . . . . .
H17A H 0.298278 0.122350 0.413106 0.075 Uiso 1 1 calc R U . . .
C18A C -0.1032(4) 0.1421(4) 0.50921(17) 0.0471(10) Uani 1 1 d . . . . .
C19A C -0.1717(4) 0.0659(5) 0.48389(19) 0.0509(11) Uani 1 1 d . . . . .
H19A H -0.138644 0.002531 0.469058 0.061 Uiso 1 1 calc R U . . .
C20A C -0.2888(4) 0.0821(5) 0.4801(2) 0.0535(11) Uani 1 1 d . . . . .
H20A H -0.333689 0.030654 0.462707 0.064 Uiso 1 1 calc R U . . .
C21A C -0.3370(4) 0.1753(5) 0.50266(19) 0.0510(10) Uani 1 1 d . . . . .
C22A C -0.2713(6) 0.2531(6) 0.5274(3) 0.0660(15) Uani 1 1 d . . . . .
H22A H -0.304751 0.316520 0.542034 0.079 Uiso 1 1 calc R U . . .
C23A C -0.1545(5) 0.2364(5) 0.5303(2) 0.0607(13) Uani 1 1 d . . . . .
H23A H -0.109722 0.289634 0.546806 0.073 Uiso 1 1 calc R U . . .
Cl1B Cl 1.05351(14) 0.59034(19) 0.48935(12) 0.1073(9) Uani 1 1 d . . . . .
O1B O 0.5227(3) 0.8792(4) 0.47206(17) 0.0623(10) Uani 1 1 d . . . . .
O2B O 0.3123(3) 0.5439(3) 0.47642(13) 0.0489(8) Uani 1 1 d . . . . .
F1B F 0.1341(4) 0.9538(5) 0.6520(2) 0.0930(14) Uani 1 1 d . . . . .
N1B N 0.4003(3) 0.4479(3) 0.53971(16) 0.0470(9) Uani 1 1 d . . . . .
H1B H 0.363063 0.384813 0.538093 0.056 Uiso 1 1 calc R U . . .
N2B N 0.4342(4) 0.7463(3) 0.52417(14) 0.0448(8) Uani 1 1 d . . . . .
C2B C 0.3831(4) 0.5375(4) 0.50930(16) 0.0400(9) Uani 1 1 d . . . . .
C3B C 0.4723(4) 0.6284(4) 0.52201(16) 0.0408(9) Uani 1 1 d . . . . .
C4B C 0.6156(5) 0.6206(5) 0.59621(18) 0.0509(11) Uani 1 1 d . . . . .
H4B H 0.644626 0.693472 0.591158 0.061 Uiso 1 1 calc R U . . .
C5B C 0.6570(5) 0.5531(6) 0.63381(19) 0.0586(13) Uani 1 1 d . . . . .
H5B H 0.714823 0.580262 0.654094 0.070 Uiso 1 1 calc R U . . .
C6B C 0.6126(6) 0.4446(6) 0.6415(2) 0.0621(14) Uani 1 1 d . . . . .
H6B H 0.641392 0.399828 0.666886 0.075 Uiso 1 1 calc R U . . .
C7B C 0.5262(5) 0.4021(5) 0.6119(2) 0.0571(12) Uani 1 1 d . . . . .
H7B H 0.495988 0.329793 0.617323 0.069 Uiso 1 1 calc R U . . .
C8B C 0.4862(4) 0.4702(4) 0.57415(17) 0.0430(9) Uani 1 1 d . . . . .
C9B C 0.5309(4) 0.5785(4) 0.56635(15) 0.0421(9) Uani 1 1 d . . . . .
C10B C 0.5486(4) 0.6651(4) 0.47602(17) 0.0448(9) Uani 1 1 d . . . . .
H10B H 0.516918 0.635640 0.445127 0.054 Uiso 1 1 calc R U . . .
C11B C 0.5037(4) 0.7856(4) 0.48716(17) 0.0466(10) Uani 1 1 d . . . . .
C12B C 0.3577(4) 0.7994(4) 0.55686(17) 0.0457(10) Uani 1 1 d . . . . .
C13B C 0.3505(5) 0.9182(4) 0.5586(2) 0.0533(11) Uani 1 1 d . . . . .
H13B H 0.395573 0.962294 0.537868 0.064 Uiso 1 1 calc R U . . .
C14B C 0.2765(6) 0.9704(6) 0.5912(3) 0.0658(15) Uani 1 1 d . . . . .
H14B H 0.272345 1.049517 0.593120 0.079 Uiso 1 1 calc R U . . .
C15B C 0.2091(5) 0.9032(6) 0.6207(2) 0.0661(15) Uani 1 1 d . . . . .
C16B C 0.2139(6) 0.7868(6) 0.6194(2) 0.0651(14) Uani 1 1 d . . . . .
H16B H 0.167221 0.743393 0.639804 0.078 Uiso 1 1 calc R U . . .
C17B C 0.2892(5) 0.7345(5) 0.5875(2) 0.0546(11) Uani 1 1 d . . . . .
H17B H 0.293779 0.655385 0.586489 0.066 Uiso 1 1 calc R U . . .
C18B C 0.6748(4) 0.6471(4) 0.47845(15) 0.0435(9) Uani 1 1 d . . . . .
C19B C 0.7466(4) 0.7306(4) 0.49675(19) 0.0496(10) Uani 1 1 d . . . . .
H19B H 0.716128 0.800229 0.506635 0.060 Uiso 1 1 calc R U . . .
C20B C 0.8631(4) 0.7124(5) 0.5006(2) 0.0562(12) Uani 1 1 d . . . . .
H20B H 0.910853 0.768515 0.513273 0.067 Uiso 1 1 calc R U . . .
C21B C 0.9063(5) 0.6102(5) 0.4854(3) 0.0629(14) Uani 1 1 d . . . . .
C22B C 0.8380(6) 0.5258(5) 0.4667(3) 0.0739(18) Uani 1 1 d . . . . .
H22B H 0.869340 0.456849 0.456529 0.089 Uiso 1 1 calc R U . . .
C23B C 0.7223(5) 0.5445(5) 0.4633(3) 0.0622(14) Uani 1 1 d . . . . .
H23B H 0.675416 0.487640 0.450747 0.075 Uiso 1 1 calc R U . . .


_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
Cl1A C21A 1.739(5) . ?
O1A C11A 1.197(7) . ?
O2A C2A 1.214(6) . ?
N1A C2A 1.356(7) . ?
N1A C8A 1.404(7) . ?
N1A H1A 0.8600 . ?
N2A C11A 1.377(7) . ?
N2A C12A 1.408(8) . ?
N2A C3A 1.457(6) . ?
F1A C15A 1.354(10) . ?
C2A C3A 1.540(6) . ?
C3A C9A 1.489(7) . ?
C3A C10A 1.609(7) . ?
C4A C9A 1.375(7) . ?
C4A C5A 1.386(8) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.381(10) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.391(9) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.370(7) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.392(7) . ?
C10A C18A 1.494(7) . ?
C10A C11A 1.527(8) . ?
C10A H10A 0.9800 . ?
C12A C17A 1.385(10) . ?
C12A C13A 1.387(8) . ?
C13A C14A 1.381(13) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.354(16) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.389(13) . ?
C16A C17A 1.386(10) . ?
C16A H16A 0.9300 . ?
C17A H17A 0.9300 . ?
C18A C23A 1.383(8) . ?
C18A C19A 1.384(7) . ?
C19A C20A 1.389(8) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.374(8) . ?
C20A H20A 0.9300 . ?
C21A C22A 1.370(9) . ?
C22A C23A 1.386(10) . ?
C22A H22A 0.9300 . ?
C23A H23A 0.9300 . ?
Cl1B C21B 1.745(6) . ?
O1B C11B 1.193(6) . ?
O2B C2B 1.221(6) . ?
F1B C15B 1.359(8) . ?
N1B C2B 1.352(6) . ?
N1B C8B 1.399(7) . ?
N1B H1B 0.8600 . ?
N2B C11B 1.374(6) . ?
N2B C12B 1.407(7) . ?
N2B C3B 1.455(6) . ?
C2B C3B 1.533(6) . ?
C3B C9B 1.504(7) . ?
C3B C10B 1.595(6) . ?
C4B C9B 1.374(7) . ?
C4B C5B 1.380(8) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.390(10) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.386(10) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.382(7) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.389(7) . ?
C10B C18B 1.497(7) . ?
C10B C11B 1.537(7) . ?
C10B H10B 0.9800 . ?
C12B C17B 1.384(8) . ?
C12B C13B 1.396(7) . ?
C13B C14B 1.382(9) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.373(12) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.367(11) . ?
C16B C17B 1.381(9) . ?
C16B H16B 0.9300 . ?
C17B H17B 0.9300 . ?
C18B C19B 1.384(7) . ?
C18B C23B 1.387(8) . ?
C19B C20B 1.388(7) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.365(9) . ?
C20B H20B 0.9300 . ?
C21B C22B 1.369(9) . ?
C22B C23B 1.377(10) . ?
C22B H22B 0.9300 . ?
C23B H23B 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
C2A N1A C8A 112.5(4) . . ?
C2A N1A H1A 123.8 . . ?
C8A N1A H1A 123.8 . . ?
C11A N2A C12A 132.9(4) . . ?
C11A N2A C3A 96.1(4) . . ?
C12A N2A C3A 130.6(4) . . ?
O2A C2A N1A 126.9(4) . . ?
O2A C2A C3A 126.8(4) . . ?
N1A C2A C3A 106.2(4) . . ?
N2A C3A C9A 119.5(4) . . ?
N2A C3A C2A 118.1(4) . . ?
C9A C3A C2A 103.5(4) . . ?
N2A C3A C10A 86.6(3) . . ?
C9A C3A C10A 118.9(4) . . ?
C2A C3A C10A 110.4(4) . . ?
C9A C4A C5A 118.6(5) . . ?
C9A C4A H4A 120.7 . . ?
C5A C4A H4A 120.7 . . ?
C6A C5A C4A 120.7(5) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C5A C6A C7A 121.0(5) . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A H6A 119.5 . . ?
C8A C7A C6A 117.6(5) . . ?
C8A C7A H7A 121.2 . . ?
C6A C7A H7A 121.2 . . ?
C7A C8A C9A 121.8(5) . . ?
C7A C8A N1A 129.1(4) . . ?
C9A C8A N1A 109.1(4) . . ?
C4A C9A C8A 120.1(5) . . ?
C4A C9A C3A 131.7(4) . . ?
C8A C9A C3A 108.1(4) . . ?
C18A C10A C11A 117.6(4) . . ?
C18A C10A C3A 118.9(4) . . ?
C11A C10A C3A 84.4(4) . . ?
C18A C10A H10A 111.1 . . ?
C11A C10A H10A 111.1 . . ?
C3A C10A H10A 111.1 . . ?
O1A C11A N2A 132.6(6) . . ?
O1A C11A C10A 134.7(6) . . ?
N2A C11A C10A 92.7(4) . . ?
C17A C12A C13A 120.6(6) . . ?
C17A C12A N2A 120.3(5) . . ?
C13A C12A N2A 119.1(6) . . ?
C14A C13A C12A 118.8(8) . . ?
C14A C13A H13A 120.6 . . ?
C12A C13A H13A 120.6 . . ?
C15A C14A C13A 119.9(7) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
F1A C15A C14A 119.1(8) . . ?
F1A C15A C16A 117.8(10) . . ?
C14A C15A C16A 123.0(7) . . ?
C17A C16A C15A 117.0(8) . . ?
C17A C16A H16A 121.5 . . ?
C15A C16A H16A 121.5 . . ?
C12A C17A C16A 120.7(6) . . ?
C12A C17A H17A 119.6 . . ?
C16A C17A H17A 119.6 . . ?
C23A C18A C19A 118.0(5) . . ?
C23A C18A C10A 119.6(4) . . ?
C19A C18A C10A 122.3(5) . . ?
C18A C19A C20A 121.5(5) . . ?
C18A C19A H19A 119.3 . . ?
C20A C19A H19A 119.3 . . ?
C21A C20A C19A 118.8(5) . . ?
C21A C20A H20A 120.6 . . ?
C19A C20A H20A 120.6 . . ?
C22A C21A C20A 121.1(5) . . ?
C22A C21A Cl1A 119.5(4) . . ?
C20A C21A Cl1A 119.3(4) . . ?
C21A C22A C23A 119.3(5) . . ?
C21A C22A H22A 120.3 . . ?
C23A C22A H22A 120.3 . . ?
C18A C23A C22A 121.2(5) . . ?
C18A C23A H23A 119.4 . . ?
C22A C23A H23A 119.4 . . ?
C2B N1B C8B 111.8(4) . . ?
C2B N1B H1B 124.1 . . ?
C8B N1B H1B 124.1 . . ?
C11B N2B C12B 133.7(4) . . ?
C11B N2B C3B 96.1(4) . . ?
C12B N2B C3B 130.0(4) . . ?
O2B C2B N1B 126.6(4) . . ?
O2B C2B C3B 125.8(4) . . ?
N1B C2B C3B 107.5(4) . . ?
N2B C3B C9B 118.5(4) . . ?
N2B C3B C2B 117.4(4) . . ?
C9B C3B C2B 102.8(3) . . ?
N2B C3B C10B 87.0(3) . . ?
C9B C3B C10B 118.4(4) . . ?
C2B C3B C10B 113.2(3) . . ?
C9B C4B C5B 119.0(5) . . ?
C9B C4B H4B 120.5 . . ?
C5B C4B H4B 120.5 . . ?
C4B C5B C6B 120.3(5) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C7B C6B C5B 121.1(5) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C8B C7B C6B 118.0(5) . . ?
C8B C7B H7B 121.0 . . ?
C6B C7B H7B 121.0 . . ?
C7B C8B C9B 120.9(5) . . ?
C7B C8B N1B 129.2(4) . . ?
C9B C8B N1B 109.9(4) . . ?
C4B C9B C8B 120.7(4) . . ?
C4B C9B C3B 131.5(4) . . ?
C8B C9B C3B 107.8(4) . . ?
C18B C10B C11B 117.3(4) . . ?
C18B C10B C3B 118.8(4) . . ?
C11B C10B C3B 84.4(3) . . ?
C18B C10B H10B 111.3 . . ?
C11B C10B H10B 111.3 . . ?
C3B C10B H10B 111.3 . . ?
O1B C11B N2B 132.1(5) . . ?
O1B C11B C10B 135.6(5) . . ?
N2B C11B C10B 92.2(3) . . ?
C17B C12B C13B 119.5(5) . . ?
C17B C12B N2B 120.4(4) . . ?
C13B C12B N2B 120.2(5) . . ?
C14B C13B C12B 120.2(6) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C15B C14B C13B 118.7(6) . . ?
C15B C14B H14B 120.7 . . ?
C13B C14B H14B 120.7 . . ?
F1B C15B C16B 118.5(7) . . ?
F1B C15B C14B 119.1(6) . . ?
C16B C15B C14B 122.4(6) . . ?
C15B C16B C17B 119.0(6) . . ?
C15B C16B H16B 120.5 . . ?
C17B C16B H16B 120.5 . . ?
C16B C17B C12B 120.3(5) . . ?
C16B C17B H17B 119.8 . . ?
C12B C17B H17B 119.8 . . ?
C19B C18B C23B 118.4(5) . . ?
C19B C18B C10B 121.1(4) . . ?
C23B C18B C10B 120.4(4) . . ?
C18B C19B C20B 121.1(5) . . ?
C18B C19B H19B 119.5 . . ?
C20B C19B H19B 119.5 . . ?
C21B C20B C19B 118.6(5) . . ?
C21B C20B H20B 120.7 . . ?
C19B C20B H20B 120.7 . . ?
C20B C21B C22B 122.0(5) . . ?
C20B C21B Cl1B 117.7(4) . . ?
C22B C21B Cl1B 120.3(5) . . ?
C21B C22B C23B 119.0(6) . . ?
C21B C22B H22B 120.5 . . ?
C23B C22B H22B 120.5 . . ?
C22B C23B C18B 121.0(5) . . ?
C22B C23B H23B 119.5 . . ?
C18B C23B H23B 119.5 . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_FVE2
_database_code_depnum_ccdc_archive 'CCDC 1963624'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl F N2 O2'
_chemical_formula_sum            'C22 H14 Cl F N2 O2'
_chemical_formula_weight         392.80

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'
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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   11.6632(2)
_cell_length_b                   11.6632(2)
_cell_length_c                   27.4472(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3733.65(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10361
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      70.1

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    2.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.617


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            27161
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.790
_diffrn_reflns_theta_max         70.908
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6706
_reflns_number_gt                3637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.881

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(11)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         6706
_refine_ls_number_parameters     506
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1A Cl -0.47471(12) 0.19577(13) 0.50784(7) 0.0701(5) Uani 1 1 d . . . . .
O1A O 0.0654(3) -0.1028(3) 0.51003(19) 0.0858(15) Uani 1 1 d . . . . .
O2A O 0.2616(3) 0.2470(3) 0.52203(15) 0.0539(10) Uani 1 1 d . . . . .
N1A N 0.1755(3) 0.3473(3) 0.45977(17) 0.0478(12) Uani 1 1 d . . . . .
H1A H 0.207397 0.412880 0.464469 0.057 Uiso 1 1 calc R U . . .
N2A N 0.1596(4) 0.0425(3) 0.46586(18) 0.0493(12) Uani 1 1 d . . . . .
F1A F 0.3293(6) -0.2723(4) 0.3842(2) 0.177(3) Uani 1 1 d . . . . .
C2A C 0.1945(4) 0.2540(4) 0.4877(2) 0.0421(13) Uani 1 1 d . . . . .
C3A C 0.1137(4) 0.1600(4) 0.4700(2) 0.0423(13) Uani 1 1 d . . . . .
C4A C -0.0126(4) 0.1668(5) 0.3910(2) 0.0520(14) Uani 1 1 d . . . . .
H4A H -0.036184 0.090742 0.392601 0.062 Uiso 1 1 calc R U . . .
C5A C -0.0507(5) 0.2377(5) 0.3545(2) 0.0622(17) Uani 1 1 d . . . . .
H5A H -0.100124 0.208871 0.330923 0.075 Uiso 1 1 calc R U . . .
C6A C -0.0172(5) 0.3500(6) 0.3522(2) 0.0672(18) Uani 1 1 d . . . . .
H6A H -0.045298 0.396366 0.327340 0.081 Uiso 1 1 calc R U . . .
C7A C 0.0575(5) 0.3959(5) 0.3860(2) 0.0575(16) Uani 1 1 d . . . . .
H7A H 0.080132 0.472287 0.384421 0.069 Uiso 1 1 calc R U . . .
C8A C 0.0972(4) 0.3242(4) 0.4220(2) 0.0434(13) Uani 1 1 d . . . . .
C9A C 0.0609(4) 0.2111(4) 0.4252(2) 0.0397(12) Uani 1 1 d . . . . .
C10A C 0.0341(4) 0.1113(4) 0.5117(2) 0.0475(14) Uani 1 1 d . . . . .
H10A H 0.063191 0.135262 0.543629 0.057 Uiso 1 1 calc R U . . .
C11A C 0.0832(4) -0.0041(5) 0.4983(2) 0.0564(16) Uani 1 1 d . . . . .
C12A C -0.0923(4) 0.1315(4) 0.5090(2) 0.0459(13) Uani 1 1 d . . . . .
C13A C -0.1664(4) 0.0604(4) 0.4838(2) 0.0498(14) Uani 1 1 d . . . . .
H13A H -0.137152 -0.003234 0.467638 0.060 Uiso 1 1 calc R U . . .
C14A C -0.2825(4) 0.0818(4) 0.4822(2) 0.0509(15) Uani 1 1 d . . . . .
H14A H -0.330755 0.034280 0.464325 0.061 Uiso 1 1 calc R U . . .
C15A C -0.3263(4) 0.1732(4) 0.5071(2) 0.0512(15) Uani 1 1 d . . . . .
C16A C -0.2556(5) 0.2453(5) 0.5321(2) 0.0685(19) Uani 1 1 d . . . . .
H16A H -0.285477 0.308260 0.548528 0.082 Uiso 1 1 calc R U . . .
C17A C -0.1394(5) 0.2240(5) 0.5328(2) 0.0645(18) Uani 1 1 d . . . . .
H17A H -0.091443 0.273619 0.549757 0.077 Uiso 1 1 calc R U . . .
C18A C 0.2412(5) -0.0037(5) 0.4331(2) 0.0565(15) Uani 1 1 d . . . . .
C19A C 0.2427(6) -0.1217(5) 0.4256(3) 0.078(2) Uani 1 1 d . . . . .
H19A H 0.192738 -0.171792 0.441180 0.094 Uiso 1 1 calc R U . . .
C20A C 0.3267(9) -0.1584(7) 0.3921(4) 0.103(3) Uani 1 1 d . . . . .
C21A C 0.4010(8) -0.0861(10) 0.3687(3) 0.107(3) Uani 1 1 d . . . . .
H21A H 0.451962 -0.117168 0.346191 0.129 Uiso 1 1 calc R U . . .
C22A C 0.4039(7) 0.0279(8) 0.3766(3) 0.109(3) Uani 1 1 d . . . . .
H22A H 0.456709 0.076356 0.361755 0.130 Uiso 1 1 calc R U . . .
C23A C 0.3184(5) 0.0677(6) 0.4101(2) 0.0665(18) Uani 1 1 d . . . . .
H23A H 0.314800 0.145850 0.416629 0.080 Uiso 1 1 calc R U . . .
Cl1B Cl 1.04759(12) 0.59022(15) 0.49507(9) 0.0978(7) Uani 1 1 d . . . . .
O1B O 0.5139(3) 0.8857(3) 0.47666(16) 0.0640(11) Uani 1 1 d . . . . .
O2B O 0.3047(3) 0.5467(3) 0.48369(15) 0.0526(10) Uani 1 1 d . . . . .
F1B F 0.1293(5) 0.7494(4) 0.6477(2) 0.1332(18) Uani 1 1 d . . . . .
N1B N 0.3951(3) 0.4526(3) 0.54697(17) 0.0500(12) Uani 1 1 d . . . . .
H1B H 0.358661 0.388514 0.545741 0.060 Uiso 1 1 calc R U . . .
N2B N 0.4246(3) 0.7541(3) 0.52929(16) 0.0444(11) Uani 1 1 d . . . . .
C2B C 0.3753(4) 0.5418(4) 0.5165(2) 0.0452(14) Uani 1 1 d . . . . .
C3B C 0.4651(4) 0.6352(4) 0.52836(19) 0.0414(13) Uani 1 1 d . . . . .
C4B C 0.6104(4) 0.6310(5) 0.6021(2) 0.0504(15) Uani 1 1 d . . . . .
H4B H 0.638368 0.704756 0.597246 0.060 Uiso 1 1 calc R U . . .
C5B C 0.6534(5) 0.5637(5) 0.6387(2) 0.0632(17) Uani 1 1 d . . . . .
H5B H 0.711067 0.592356 0.658704 0.076 Uiso 1 1 calc R U . . .
C6B C 0.6129(5) 0.4545(5) 0.6464(2) 0.0622(17) Uani 1 1 d . . . . .
H6B H 0.644489 0.410062 0.671055 0.075 Uiso 1 1 calc R U . . .
C7B C 0.5259(5) 0.4097(5) 0.6180(2) 0.0568(16) Uani 1 1 d . . . . .
H7B H 0.497491 0.336436 0.623649 0.068 Uiso 1 1 calc R U . . .
C8B C 0.4825(4) 0.4771(4) 0.5810(2) 0.0448(13) Uani 1 1 d . . . . .
C9B C 0.5246(4) 0.5878(4) 0.57243(19) 0.0411(13) Uani 1 1 d . . . . .
C10B C 0.5406(4) 0.6708(4) 0.4825(2) 0.0448(13) Uani 1 1 d . . . . .
H10B H 0.508197 0.640077 0.452232 0.054 Uiso 1 1 calc R U . . .
C11B C 0.4956(4) 0.7923(5) 0.4927(2) 0.0479(15) Uani 1 1 d . . . . .
C12B C 0.6673(4) 0.6517(4) 0.4847(2) 0.0439(13) Uani 1 1 d . . . . .
C13B C 0.7415(4) 0.7347(4) 0.5009(2) 0.0549(16) Uani 1 1 d . . . . .
H13B H 0.712342 0.805887 0.509811 0.066 Uiso 1 1 calc R U . . .
C14B C 0.8588(4) 0.7158(4) 0.5043(2) 0.0586(17) Uani 1 1 d . . . . .
H14B H 0.907578 0.773458 0.515212 0.070 Uiso 1 1 calc R U . . .
C15B C 0.9005(4) 0.6124(5) 0.4916(2) 0.0595(17) Uani 1 1 d . . . . .
C16B C 0.8304(5) 0.5265(5) 0.4755(3) 0.083(2) Uani 1 1 d . . . . .
H16B H 0.860446 0.455093 0.467407 0.100 Uiso 1 1 calc R U . . .
C17B C 0.7133(5) 0.5475(5) 0.4712(3) 0.076(2) Uani 1 1 d . . . . .
H17B H 0.665444 0.490407 0.459168 0.092 Uiso 1 1 calc R U . . .
C18B C 0.3485(4) 0.8119(5) 0.5614(2) 0.0486(14) Uani 1 1 d . . . . .
C19B C 0.3453(5) 0.9309(5) 0.5623(2) 0.0605(17) Uani 1 1 d . . . . .
H19B H 0.391548 0.972985 0.541303 0.073 Uiso 1 1 calc R U . . .
C20B C 0.2723(6) 0.9873(7) 0.5949(3) 0.078(2) Uani 1 1 d . . . . .
H20B H 0.272758 1.066993 0.596487 0.093 Uiso 1 1 calc R U . . .
C21B C 0.2015(7) 0.9273(6) 0.6239(3) 0.086(2) Uani 1 1 d . . . . .
H21B H 0.151146 0.964256 0.644977 0.103 Uiso 1 1 calc R U . . .
C22B C 0.2056(5) 0.8106(7) 0.6215(3) 0.076(2) Uani 1 1 d . . . . .
C23B C 0.2771(5) 0.7497(5) 0.5909(2) 0.0590(16) Uani 1 1 d . . . . .
H23B H 0.276775 0.669930 0.590312 0.071 Uiso 1 1 calc R U . . .


_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
Cl1A C15A 1.752(5) . ?
O1A C11A 1.213(6) . ?
O2A C2A 1.228(6) . ?
N1A C2A 1.349(6) . ?
N1A C8A 1.407(7) . ?
N1A H1A 0.8600 . ?
N2A C11A 1.371(7) . ?
N2A C18A 1.415(7) . ?
N2A C3A 1.475(6) . ?
F1A C20A 1.347(9) . ?
C2A C3A 1.524(7) . ?
C3A C9A 1.501(7) . ?
C3A C10A 1.579(7) . ?
C4A C9A 1.371(7) . ?
C4A C5A 1.373(8) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.368(8) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.380(8) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.376(7) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.387(6) . ?
C10A C12A 1.495(7) . ?
C10A C11A 1.509(7) . ?
C10A H10A 0.9800 . ?
C12A C17A 1.375(8) . ?
C12A C13A 1.382(7) . ?
C13A C14A 1.378(7) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.365(7) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.363(8) . ?
C16A C17A 1.378(8) . ?
C16A H16A 0.9300 . ?
C17A H17A 0.9300 . ?
C18A C23A 1.380(8) . ?
C18A C19A 1.392(8) . ?
C19A C20A 1.410(12) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.369(12) . ?
C21A C22A 1.348(12) . ?
C21A H21A 0.9300 . ?
C22A C23A 1.433(10) . ?
C22A H22A 0.9300 . ?
C23A H23A 0.9300 . ?
Cl1B C15B 1.738(5) . ?
O1B C11B 1.195(6) . ?
O2B C2B 1.221(6) . ?
F1B C22B 1.348(7) . ?
N1B C2B 1.356(7) . ?
N1B C8B 1.411(6) . ?
N1B H1B 0.8600 . ?
N2B C11B 1.376(6) . ?
N2B C18B 1.421(7) . ?
N2B C3B 1.466(6) . ?
C2B C3B 1.546(6) . ?
C3B C9B 1.500(7) . ?
C3B C10B 1.592(7) . ?
C4B C5B 1.370(8) . ?
C4B C9B 1.385(7) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.374(8) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.381(8) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.381(8) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.401(7) . ?
C10B C12B 1.496(6) . ?
C10B C11B 1.536(7) . ?
C10B H10B 0.9800 . ?
C12B C13B 1.372(7) . ?
C12B C17B 1.379(7) . ?
C13B C14B 1.389(7) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.347(7) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.367(7) . ?
C16B C17B 1.392(8) . ?
C16B H16B 0.9300 . ?
C17B H17B 0.9300 . ?
C18B C23B 1.369(8) . ?
C18B C19B 1.389(7) . ?
C19B C20B 1.399(9) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.344(10) . ?
C20B H20B 0.9300 . ?
C21B C22B 1.364(10) . ?
C21B H21B 0.9300 . ?
C22B C23B 1.381(9) . ?
C23B H23B 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
C2A N1A C8A 111.7(4) . . ?
C2A N1A H1A 124.1 . . ?
C8A N1A H1A 124.1 . . ?
C11A N2A C18A 134.2(5) . . ?
C11A N2A C3A 94.7(4) . . ?
C18A N2A C3A 130.3(5) . . ?
O2A C2A N1A 126.5(5) . . ?
O2A C2A C3A 126.1(5) . . ?
N1A C2A C3A 107.3(4) . . ?
N2A C3A C9A 117.0(4) . . ?
N2A C3A C2A 117.9(4) . . ?
C9A C3A C2A 103.2(4) . . ?
N2A C3A C10A 86.3(4) . . ?
C9A C3A C10A 119.7(4) . . ?
C2A C3A C10A 113.1(4) . . ?
C9A C4A C5A 118.3(5) . . ?
C9A C4A H4A 120.9 . . ?
C5A C4A H4A 120.9 . . ?
C6A C5A C4A 121.2(6) . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A H5A 119.4 . . ?
C5A C6A C7A 121.3(6) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C8A C7A C6A 117.4(6) . . ?
C8A C7A H7A 121.3 . . ?
C6A C7A H7A 121.3 . . ?
C7A C8A C9A 121.3(5) . . ?
C7A C8A N1A 129.1(5) . . ?
C9A C8A N1A 109.5(5) . . ?
C4A C9A C8A 120.4(5) . . ?
C4A C9A C3A 131.9(5) . . ?
C8A C9A C3A 107.6(4) . . ?
C12A C10A C11A 120.2(4) . . ?
C12A C10A C3A 119.1(4) . . ?
C11A C10A C3A 85.4(4) . . ?
C12A C10A H10A 110.0 . . ?
C11A C10A H10A 110.0 . . ?
C3A C10A H10A 110.0 . . ?
O1A C11A N2A 131.3(6) . . ?
O1A C11A C10A 135.8(6) . . ?
N2A C11A C10A 92.9(4) . . ?
C17A C12A C13A 117.3(5) . . ?
C17A C12A C10A 119.6(5) . . ?
C13A C12A C10A 123.2(5) . . ?
C14A C13A C12A 121.5(5) . . ?
C14A C13A H13A 119.3 . . ?
C12A C13A H13A 119.3 . . ?
C15A C14A C13A 119.5(5) . . ?
C15A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
C16A C15A C14A 120.5(5) . . ?
C16A C15A Cl1A 120.0(4) . . ?
C14A C15A Cl1A 119.5(4) . . ?
C15A C16A C17A 119.4(5) . . ?
C15A C16A H16A 120.3 . . ?
C17A C16A H16A 120.3 . . ?
C12A C17A C16A 121.8(5) . . ?
C12A C17A H17A 119.1 . . ?
C16A C17A H17A 119.1 . . ?
C23A C18A C19A 121.3(6) . . ?
C23A C18A N2A 120.0(5) . . ?
C19A C18A N2A 118.7(6) . . ?
C18A C19A C20A 114.0(7) . . ?
C18A C19A H19A 123.0 . . ?
C20A C19A H19A 123.0 . . ?
F1A C20A C21A 121.2(10) . . ?
F1A C20A C19A 114.8(10) . . ?
C21A C20A C19A 124.0(7) . . ?
C22A C21A C20A 123.2(8) . . ?
C22A C21A H21A 118.4 . . ?
C20A C21A H21A 118.4 . . ?
C21A C22A C23A 113.9(9) . . ?
C21A C22A H22A 123.0 . . ?
C23A C22A H22A 123.0 . . ?
C18A C23A C22A 123.6(7) . . ?
C18A C23A H23A 118.2 . . ?
C22A C23A H23A 118.2 . . ?
C2B N1B C8B 112.1(4) . . ?
C2B N1B H1B 124.0 . . ?
C8B N1B H1B 124.0 . . ?
C11B N2B C18B 132.5(4) . . ?
C11B N2B C3B 95.7(4) . . ?
C18B N2B C3B 131.4(4) . . ?
O2B C2B N1B 127.3(5) . . ?
O2B C2B C3B 125.4(5) . . ?
N1B C2B C3B 107.2(5) . . ?
N2B C3B C9B 118.9(4) . . ?
N2B C3B C2B 116.9(4) . . ?
C9B C3B C2B 103.0(4) . . ?
N2B C3B C10B 86.8(4) . . ?
C9B C3B C10B 118.6(4) . . ?
C2B C3B C10B 113.1(4) . . ?
C5B C4B C9B 119.2(5) . . ?
C5B C4B H4B 120.4 . . ?
C9B C4B H4B 120.4 . . ?
C4B C5B C6B 121.1(6) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B H5B 119.5 . . ?
C5B C6B C7B 121.1(6) . . ?
C5B C6B H6B 119.4 . . ?
C7B C6B H6B 119.4 . . ?
C8B C7B C6B 118.0(5) . . ?
C8B C7B H7B 121.0 . . ?
C6B C7B H7B 121.0 . . ?
C7B C8B C9B 121.2(5) . . ?
C7B C8B N1B 129.5(5) . . ?
C9B C8B N1B 109.2(5) . . ?
C4B C9B C8B 119.4(5) . . ?
C4B C9B C3B 132.4(5) . . ?
C8B C9B C3B 108.2(4) . . ?
C12B C10B C11B 117.8(4) . . ?
C12B C10B C3B 118.3(5) . . ?
C11B C10B C3B 84.7(4) . . ?
C12B C10B H10B 111.2 . . ?
C11B C10B H10B 111.2 . . ?
C3B C10B H10B 111.2 . . ?
O1B C11B N2B 132.2(5) . . ?
O1B C11B C10B 135.5(5) . . ?
N2B C11B C10B 92.3(4) . . ?
C13B C12B C17B 117.6(5) . . ?
C13B C12B C10B 122.1(5) . . ?
C17B C12B C10B 120.3(5) . . ?
C12B C13B C14B 122.1(5) . . ?
C12B C13B H13B 119.0 . . ?
C14B C13B H13B 119.0 . . ?
C15B C14B C13B 118.7(5) . . ?
C15B C14B H14B 120.7 . . ?
C13B C14B H14B 120.7 . . ?
C14B C15B C16B 121.7(5) . . ?
C14B C15B Cl1B 118.4(4) . . ?
C16B C15B Cl1B 120.0(4) . . ?
C15B C16B C17B 119.0(5) . . ?
C15B C16B H16B 120.5 . . ?
C17B C16B H16B 120.5 . . ?
C12B C17B C16B 121.0(5) . . ?
C12B C17B H17B 119.5 . . ?
C16B C17B H17B 119.5 . . ?
C23B C18B C19B 120.2(5) . . ?
C23B C18B N2B 119.7(5) . . ?
C19B C18B N2B 120.1(5) . . ?
C18B C19B C20B 119.9(6) . . ?
C18B C19B H19B 120.1 . . ?
C20B C19B H19B 120.1 . . ?
C21B C20B C19B 120.5(7) . . ?
C21B C20B H20B 119.8 . . ?
C19B C20B H20B 119.8 . . ?
C20B C21B C22B 118.0(7) . . ?
C20B C21B H21B 121.0 . . ?
C22B C21B H21B 121.0 . . ?
F1B C22B C21B 118.7(7) . . ?
F1B C22B C23B 116.8(7) . . ?
C21B C22B C23B 124.3(7) . . ?
C18B C23B C22B 117.0(6) . . ?
C18B C23B H23B 121.5 . . ?
C22B C23B H23B 121.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A N1A C2A O2A 177.1(5) . . . . ?
C8A N1A C2A C3A -5.1(5) . . . . ?
C11A N2A C3A C9A -115.7(5) . . . . ?
C18A N2A C3A C9A 55.3(7) . . . . ?
C11A N2A C3A C2A 120.1(5) . . . . ?
C18A N2A C3A C2A -68.9(7) . . . . ?
C11A N2A C3A C10A 5.9(4) . . . . ?
C18A N2A C3A C10A 176.9(5) . . . . ?
O2A C2A C3A N2A -44.4(7) . . . . ?
N1A C2A C3A N2A 137.8(5) . . . . ?
O2A C2A C3A C9A -175.1(5) . . . . ?
N1A C2A C3A C9A 7.1(5) . . . . ?
O2A C2A C3A C10A 54.0(6) . . . . ?
N1A C2A C3A C10A -123.8(4) . . . . ?
C9A C4A C5A C6A -0.5(9) . . . . ?
C4A C5A C6A C7A 1.0(10) . . . . ?
C5A C6A C7A C8A 0.1(9) . . . . ?
C6A C7A C8A C9A -1.8(8) . . . . ?
C6A C7A C8A N1A 178.0(5) . . . . ?
C2A N1A C8A C7A -179.0(5) . . . . ?
C2A N1A C8A C9A 0.8(6) . . . . ?
C5A C4A C9A C8A -1.1(8) . . . . ?
C5A C4A C9A C3A 177.1(5) . . . . ?
C7A C8A C9A C4A 2.4(8) . . . . ?
N1A C8A C9A C4A -177.5(5) . . . . ?
C7A C8A C9A C3A -176.2(5) . . . . ?
N1A C8A C9A C3A 3.9(6) . . . . ?
N2A C3A C9A C4A 43.7(8) . . . . ?
C2A C3A C9A C4A 175.0(5) . . . . ?
C10A C3A C9A C4A -58.2(8) . . . . ?
N2A C3A C9A C8A -137.9(4) . . . . ?
C2A C3A C9A C8A -6.6(5) . . . . ?
C10A C3A C9A C8A 120.1(5) . . . . ?
N2A C3A C10A C12A -127.5(5) . . . . ?
C9A C3A C10A C12A -8.4(7) . . . . ?
C2A C3A C10A C12A 113.6(5) . . . . ?
N2A C3A C10A C11A -5.4(4) . . . . ?
C9A C3A C10A C11A 113.8(5) . . . . ?
C2A C3A C10A C11A -124.2(4) . . . . ?
C18A N2A C11A O1A 3.1(10) . . . . ?
C3A N2A C11A O1A 173.5(6) . . . . ?
C18A N2A C11A C10A -176.6(5) . . . . ?
C3A N2A C11A C10A -6.2(4) . . . . ?
C12A C10A C11A O1A -52.6(10) . . . . ?
C3A C10A C11A O1A -173.9(7) . . . . ?
C12A C10A C11A N2A 127.0(5) . . . . ?
C3A C10A C11A N2A 5.8(4) . . . . ?
C11A C10A C12A C17A 163.1(6) . . . . ?
C3A C10A C12A C17A -94.2(7) . . . . ?
C11A C10A C12A C13A -16.1(8) . . . . ?
C3A C10A C12A C13A 86.5(6) . . . . ?
C17A C12A C13A C14A 0.6(8) . . . . ?
C10A C12A C13A C14A 179.9(5) . . . . ?
C12A C13A C14A C15A -1.9(9) . . . . ?
C13A C14A C15A C16A 2.2(9) . . . . ?
C13A C14A C15A Cl1A -176.5(4) . . . . ?
C14A C15A C16A C17A -1.2(10) . . . . ?
Cl1A C15A C16A C17A 177.5(5) . . . . ?
C13A C12A C17A C16A 0.5(9) . . . . ?
C10A C12A C17A C16A -178.8(6) . . . . ?
C15A C16A C17A C12A -0.2(10) . . . . ?
C11A N2A C18A C23A -170.3(6) . . . . ?
C3A N2A C18A C23A 22.2(8) . . . . ?
C11A N2A C18A C19A 8.6(9) . . . . ?
C3A N2A C18A C19A -158.9(5) . . . . ?
C23A C18A C19A C20A -1.5(9) . . . . ?
N2A C18A C19A C20A 179.6(5) . . . . ?
C18A C19A C20A F1A -179.9(6) . . . . ?
C18A C19A C20A C21A 0.0(11) . . . . ?
F1A C20A C21A C22A -177.7(7) . . . . ?
C19A C20A C21A C22A 2.4(14) . . . . ?
C20A C21A C22A C23A -2.9(12) . . . . ?
C19A C18A C23A C22A 0.9(9) . . . . ?
N2A C18A C23A C22A 179.7(5) . . . . ?
C21A C22A C23A C18A 1.3(10) . . . . ?
C8B N1B C2B O2B -179.4(5) . . . . ?
C8B N1B C2B C3B 4.5(5) . . . . ?
C11B N2B C3B C9B 115.9(4) . . . . ?
C18B N2B C3B C9B -57.1(6) . . . . ?
C11B N2B C3B C2B -119.5(5) . . . . ?
C18B N2B C3B C2B 67.4(7) . . . . ?
C11B N2B C3B C10B -5.2(4) . . . . ?
C18B N2B C3B C10B -178.3(5) . . . . ?
O2B C2B C3B N2B 45.4(7) . . . . ?
N1B C2B C3B N2B -138.4(5) . . . . ?
O2B C2B C3B C9B 177.7(5) . . . . ?
N1B C2B C3B C9B -6.1(5) . . . . ?
O2B C2B C3B C10B -53.2(6) . . . . ?
N1B C2B C3B C10B 123.1(5) . . . . ?
C9B C4B C5B C6B 0.0(9) . . . . ?
C4B C5B C6B C7B -1.2(9) . . . . ?
C5B C6B C7B C8B 1.3(9) . . . . ?
C6B C7B C8B C9B -0.3(9) . . . . ?
C6B C7B C8B N1B 179.8(5) . . . . ?
C2B N1B C8B C7B 179.1(6) . . . . ?
C2B N1B C8B C9B -0.9(6) . . . . ?
C5B C4B C9B C8B 1.0(8) . . . . ?
C5B C4B C9B C3B -175.9(5) . . . . ?
C7B C8B C9B C4B -0.9(8) . . . . ?
N1B C8B C9B C4B 179.1(5) . . . . ?
C7B C8B C9B C3B 176.7(5) . . . . ?
N1B C8B C9B C3B -3.3(6) . . . . ?
N2B C3B C9B C4B -46.1(8) . . . . ?
C2B C3B C9B C4B -177.2(5) . . . . ?
C10B C3B C9B C4B 57.1(8) . . . . ?
N2B C3B C9B C8B 136.7(4) . . . . ?
C2B C3B C9B C8B 5.6(5) . . . . ?
C10B C3B C9B C8B -120.0(5) . . . . ?
N2B C3B C10B C12B 123.5(5) . . . . ?
C9B C3B C10B C12B 2.1(7) . . . . ?
C2B C3B C10B C12B -118.6(5) . . . . ?
N2B C3B C10B C11B 4.6(3) . . . . ?
C9B C3B C10B C11B -116.8(4) . . . . ?
C2B C3B C10B C11B 122.6(4) . . . . ?
C18B N2B C11B O1B -0.8(9) . . . . ?
C3B N2B C11B O1B -173.8(6) . . . . ?
C18B N2B C11B C10B 178.3(5) . . . . ?
C3B N2B C11B C10B 5.4(4) . . . . ?
C12B C10B C11B O1B 54.8(9) . . . . ?
C3B C10B C11B O1B 174.2(6) . . . . ?
C12B C10B C11B N2B -124.3(5) . . . . ?
C3B C10B C11B N2B -5.0(4) . . . . ?
C11B C10B C12B C13B 7.6(8) . . . . ?
C3B C10B C12B C13B -91.9(6) . . . . ?
C11B C10B C12B C17B -173.7(6) . . . . ?
C3B C10B C12B C17B 86.8(7) . . . . ?
C17B C12B C13B C14B -0.7(9) . . . . ?
C10B C12B C13B C14B 178.1(6) . . . . ?
C12B C13B C14B C15B -0.4(10) . . . . ?
C13B C14B C15B C16B 0.1(11) . . . . ?
C13B C14B C15B Cl1B 179.0(5) . . . . ?
C14B C15B C16B C17B 1.2(11) . . . . ?
Cl1B C15B C16B C17B -177.6(6) . . . . ?
C13B C12B C17B C16B 2.0(10) . . . . ?
C10B C12B C17B C16B -176.7(6) . . . . ?
C15B C16B C17B C12B -2.3(11) . . . . ?
C11B N2B C18B C23B 172.1(5) . . . . ?
C3B N2B C18B C23B -17.2(8) . . . . ?
C11B N2B C18B C19B -6.9(8) . . . . ?
C3B N2B C18B C19B 163.8(5) . . . . ?
C23B C18B C19B C20B 2.6(8) . . . . ?
N2B C18B C19B C20B -178.4(5) . . . . ?
C18B C19B C20B C21B -2.9(9) . . . . ?
C19B C20B C21B C22B 1.9(11) . . . . ?
C20B C21B C22B F1B -175.2(6) . . . . ?
C20B C21B C22B C23B -0.6(11) . . . . ?
C19B C18B C23B C22B -1.4(9) . . . . ?
N2B C18B C23B C22B 179.6(5) . . . . ?
F1B C22B C23B C18B 175.0(6) . . . . ?
C21B C22B C23B C18B 0.4(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A Cl1B 0.86 2.91 3.345(4) 113.5 1_455
N1A H1A O2B 0.86 2.00 2.848(5) 168.1 .
C14A H14A O1B 0.93 2.53 3.300(6) 140.4 1_445
C19A H19A O1A 0.93 2.53 3.115(9) 120.7 .
N1B H1B O2A 0.86 2.11 2.940(5) 163.5 .
C14B H14B O1A 0.93 2.34 3.211(6) 155.0 1_665
C19B H19B O1B 0.93 2.49 3.110(8) 123.9 .

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_FVE761
_database_code_depnum_ccdc_archive 'CCDC 1963622'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Cl F N2 O3'
_chemical_formula_weight         466.92

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3504(5)
_cell_length_b                   9.0371(2)
_cell_length_c                   20.1515(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.169(2)
_cell_angle_gamma                90
_cell_volume                     2496.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    12796
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      72.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    1.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.617


_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            16986
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.593
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4839
_reflns_number_gt                3419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4839
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.12222(5) 1.13960(8) 0.03728(3) 0.0984(3) Uani 1 1 d . . . . .
F1 F 0.30012(19) 0.9151(3) 0.67706(9) 0.1671(9) Uani 1 1 d . . . . .
O1 O 0.00840(11) 0.97355(18) 0.35039(9) 0.0897(5) Uani 1 1 d . . . . .
O2 O 0.31044(9) 0.93938(14) 0.34373(8) 0.0697(4) Uani 1 1 d . . . . .
N1 N 0.34172(11) 0.69106(17) 0.33680(8) 0.0596(4) Uani 1 1 d . . . . .
N2 N 0.14987(11) 0.83229(16) 0.39590(8) 0.0575(4) Uani 1 1 d . . . . .
C2 C 0.28744(12) 0.81069(19) 0.34210(9) 0.0522(4) Uani 1 1 d . . . . .
C3 C 0.18911(11) 0.75091(17) 0.34703(8) 0.0485(4) Uani 1 1 d . . . . .
C4 C 0.14926(13) 0.47530(19) 0.36784(9) 0.0587(4) Uani 1 1 d . . . . .
H4 H 0.0889 0.4952 0.3742 0.070 Uiso 1 1 calc R U . . .
C5 C 0.18350(17) 0.3317(2) 0.37069(11) 0.0716(5) Uani 1 1 d . . . . .
H5 H 0.1463 0.2542 0.3795 0.086 Uiso 1 1 calc R U . . .
C6 C 0.27234(18) 0.3031(2) 0.36051(12) 0.0803(6) Uani 1 1 d . . . . .
H6 H 0.2940 0.2058 0.3621 0.096 Uiso 1 1 calc R U . . .
C7 C 0.33043(15) 0.4159(2) 0.34788(12) 0.0749(6) Uani 1 1 d . . . . .
H7 H 0.3903 0.3957 0.3408 0.090 Uiso 1 1 calc R U . . .
C8 C 0.29641(12) 0.55860(18) 0.34624(9) 0.0540(4) Uani 1 1 d . . . . .
C9 C 0.20619(11) 0.58794(17) 0.35546(8) 0.0479(4) Uani 1 1 d . . . . .
C10 C 0.09596(12) 0.8053(2) 0.28804(9) 0.0547(4) Uani 1 1 d . . . . .
C11 C 0.07152(13) 0.8891(2) 0.34647(11) 0.0628(5) Uani 1 1 d . . . . .
C12 C 0.18846(15) 0.85376(19) 0.46783(10) 0.0623(5) Uani 1 1 d . . . . .
C13 C 0.14173(19) 0.9458(2) 0.50291(12) 0.0799(6) Uani 1 1 d . . . . .
H13 H 0.0842 0.9933 0.4788 0.096 Uiso 1 1 calc R U . . .
C14 C 0.1798(3) 0.9669(3) 0.57283(16) 0.0996(9) Uani 1 1 d . . . . .
H14 H 0.1490 1.0296 0.5964 0.120 Uiso 1 1 calc R U . . .
C15 C 0.2621(3) 0.8963(4) 0.60709(14) 0.1073(9) Uani 1 1 d . . . . .
C16 C 0.3112(2) 0.8039(4) 0.57480(13) 0.1085(9) Uani 1 1 d . . . . .
H16 H 0.3685 0.7572 0.5998 0.130 Uiso 1 1 calc R U . . .
C17 C 0.27291(17) 0.7824(3) 0.50406(11) 0.0846(6) Uani 1 1 d . . . . .
H17 H 0.3042 0.7196 0.4809 0.102 Uiso 1 1 calc R U . . .
C18 C 0.10516(11) 0.88991(18) 0.22667(9) 0.0509(4) Uani 1 1 d . . . . .
C19 C 0.12236(12) 1.04105(19) 0.22963(9) 0.0565(4) Uani 1 1 d . . . . .
H19 H 0.1304 1.0911 0.2713 0.068 Uiso 1 1 calc R U . . .
C20 C 0.12781(13) 1.1188(2) 0.17182(10) 0.0623(4) Uani 1 1 d . . . . .
H20 H 0.1388 1.2203 0.1742 0.075 Uiso 1 1 calc R U . . .
C21 C 0.11679(13) 1.0436(2) 0.11085(10) 0.0627(5) Uani 1 1 d . . . . .
C22 C 0.10131(14) 0.8937(2) 0.10670(10) 0.0671(5) Uani 1 1 d . . . . .
H22 H 0.0952 0.8439 0.0652 0.081 Uiso 1 1 calc R U . . .
C23 C 0.09489(13) 0.8174(2) 0.16448(10) 0.0603(4) Uani 1 1 d . . . . .
H23 H 0.0835 0.7159 0.1616 0.072 Uiso 1 1 calc R U . . .
O3 O 0.54930(15) 0.6786(3) 0.36628(17) 0.1521(10) Uani 1 1 d . . . . .
C24 C 0.6016(4) 0.7366(11) 0.4355(5) 0.262(4) Uani 1 1 d . . . . .
H24A H 0.6369 0.6558 0.4636 0.314 Uiso 1 1 calc R U . . .
H24B H 0.6494 0.8084 0.4305 0.314 Uiso 1 1 calc R U . . .
C25 C 0.5440(6) 0.8020(11) 0.4701(4) 0.287(5) Uani 1 1 d . . . . .
H25A H 0.5026 0.8739 0.4405 0.430 Uiso 1 1 calc R U . . .
H25B H 0.5842 0.8500 0.5111 0.430 Uiso 1 1 calc R U . . .
H25C H 0.5046 0.7281 0.4831 0.430 Uiso 1 1 calc R U . . .
C26 C 0.6064(4) 0.6445(8) 0.3262(5) 0.227(3) Uani 1 1 d . . . . .
H26A H 0.6384 0.7341 0.3177 0.273 Uiso 1 1 calc R U . . .
H26B H 0.6569 0.5769 0.3517 0.273 Uiso 1 1 calc R U . . .
C27 C 0.5607(6) 0.5842(10) 0.2663(4) 0.257(4) Uani 1 1 d . . . . .
H27A H 0.5155 0.5114 0.2729 0.385 Uiso 1 1 calc R U . . .
H27B H 0.6072 0.5377 0.2472 0.385 Uiso 1 1 calc R U . . .
H27C H 0.5259 0.6593 0.2350 0.385 Uiso 1 1 calc R U . . .
H10 H 0.0534(15) 0.725(2) 0.2760(10) 0.066(5) Uiso 1 1 d . . . . .
H1 H 0.3990(18) 0.700(2) 0.3347(11) 0.080(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.7392(19) . ?
F1 C15 1.364(3) . ?
O1 C11 1.205(2) . ?
O2 C2 1.207(2) . ?
N1 C2 1.355(2) . ?
N1 C8 1.402(2) . ?
N1 H1 0.84(2) . ?
N2 C11 1.363(2) . ?
N2 C12 1.404(2) . ?
N2 C3 1.4681(19) . ?
C2 C3 1.541(2) . ?
C3 C9 1.494(2) . ?
C3 C10 1.582(2) . ?
C4 C9 1.373(2) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(2) . ?
C10 C18 1.492(2) . ?
C10 C11 1.525(3) . ?
C10 H10 0.94(2) . ?
C12 C17 1.377(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.341(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.383(2) . ?
C18 C19 1.386(2) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
O3 C26 1.345(6) . ?
O3 C24 1.472(8) . ?
C24 C25 1.364(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.310(9) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C2 N1 C8 111.72(14) . . ?
C2 N1 H1 121.6(16) . . ?
C8 N1 H1 125.9(16) . . ?
C11 N2 C12 133.73(15) . . ?
C11 N2 C3 95.47(13) . . ?
C12 N2 C3 130.49(14) . . ?
O2 C2 N1 127.74(15) . . ?
O2 C2 C3 125.75(15) . . ?
N1 C2 C3 106.50(14) . . ?
N2 C3 C9 119.99(13) . . ?
N2 C3 C2 114.04(13) . . ?
C9 C3 C2 103.31(12) . . ?
N2 C3 C10 86.67(12) . . ?
C9 C3 C10 117.75(13) . . ?
C2 C3 C10 115.41(13) . . ?
C9 C4 C5 118.68(17) . . ?
C9 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 120.28(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.56(18) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.71(19) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 120.98(17) . . ?
C7 C8 N1 128.92(16) . . ?
C9 C8 N1 110.10(14) . . ?
C4 C9 C8 120.77(15) . . ?
C4 C9 C3 131.66(14) . . ?
C8 C9 C3 107.55(13) . . ?
C18 C10 C11 118.85(15) . . ?
C18 C10 C3 121.33(13) . . ?
C11 C10 C3 84.84(13) . . ?
C18 C10 H10 113.2(12) . . ?
C11 C10 H10 107.8(12) . . ?
C3 C10 H10 107.1(12) . . ?
O1 C11 N2 131.64(19) . . ?
O1 C11 C10 135.53(19) . . ?
N2 C11 C10 92.83(13) . . ?
C17 C12 C13 119.6(2) . . ?
C17 C12 N2 120.00(16) . . ?
C13 C12 N2 120.4(2) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 F1 119.7(3) . . ?
C14 C15 C16 122.9(3) . . ?
F1 C15 C16 117.4(4) . . ?
C15 C16 C17 118.1(3) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C12 C17 C16 120.0(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C23 C18 C19 118.41(16) . . ?
C23 C18 C10 119.76(16) . . ?
C19 C18 C10 121.82(15) . . ?
C20 C19 C18 121.21(16) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 118.88(17) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C20 121.18(17) . . ?
C22 C21 Cl1 119.21(15) . . ?
C20 C21 Cl1 119.61(15) . . ?
C21 C22 C23 119.50(17) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C18 120.80(17) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C26 O3 C24 114.8(5) . . ?
C25 C24 O3 115.0(4) . . ?
C25 C24 H24A 108.5 . . ?
O3 C24 H24A 108.5 . . ?
C25 C24 H24B 108.5 . . ?
O3 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 O3 114.8(5) . . ?
C27 C26 H26A 108.6 . . ?
O3 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
O3 C26 H26B 108.6 . . ?
H26A C26 H26B 107.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_FVE2C
_database_code_depnum_ccdc_archive 'CCDC 1963625'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl F N2 O2'
_chemical_formula_sum            'C22 H14 Cl F N2 O2'
_chemical_formula_weight         392.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   11.6433(4)
_cell_length_b                   11.6433(4)
_cell_length_c                   27.2378(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3692.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    22785
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.0

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .23
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_T_max  0.620

_exptl_special_details           
;
 ?
;

_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            54705
_diffrn_reflns_av_unetI/netI     0.105
_diffrn_reflns_av_R_equivalents  0.118
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         28.844
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9279
_reflns_number_gt                3584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1335P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.92(10)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         9279
_refine_ls_number_parameters     506
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2100
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2662
_refine_ls_wR_factor_gt          0.1717
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1A Cl 1.0454(3) 0.4184(3) 0.49981(16) 0.0932(13) Uani 1 1 d . . . . .
O1A O 0.5152(6) 0.1151(6) 0.5224(3) 0.0592(19) Uani 1 1 d . . . . .
O2A O 0.3056(5) 0.4576(5) 0.5182(3) 0.0487(17) Uani 1 1 d . . . . .
F1A F 0.2767(6) 0.3605(5) 0.4058(3) 0.0742(19) Uani 1 1 d . . . . .
N1A N 0.4017(7) 0.5545(7) 0.4573(3) 0.046(2) Uani 1 1 d . . . . .
H1A H 0.369377 0.620588 0.460297 0.055 Uiso 1 1 calc R U . . .
N2A N 0.4222(6) 0.2483(6) 0.4710(3) 0.0424(19) Uani 1 1 d . . . . .
C2A C 0.3771(8) 0.4621(7) 0.4861(4) 0.040(2) Uani 1 1 d . . . . .
C3A C 0.4637(7) 0.3681(7) 0.4724(4) 0.040(2) Uani 1 1 d . . . . .
C4A C 0.6057(8) 0.3712(9) 0.3976(4) 0.049(2) Uani 1 1 d . . . . .
H4A H 0.630790 0.295791 0.401121 0.059 Uiso 1 1 calc R U . . .
C5A C 0.6508(9) 0.4415(10) 0.3613(4) 0.057(3) Uani 1 1 d . . . . .
H5A H 0.706838 0.413147 0.340219 0.068 Uiso 1 1 calc R U . . .
C6A C 0.6135(10) 0.5523(10) 0.3562(4) 0.060(3) Uani 1 1 d . . . . .
H6A H 0.645882 0.597924 0.331859 0.072 Uiso 1 1 calc R U . . .
C7A C 0.5304(9) 0.5983(9) 0.3857(4) 0.055(3) Uani 1 1 d . . . . .
H7A H 0.504909 0.673334 0.381451 0.066 Uiso 1 1 calc R U . . .
C8A C 0.4860(8) 0.5291(8) 0.4220(4) 0.044(2) Uani 1 1 d . . . . .
C9A C 0.5230(8) 0.4158(8) 0.4283(3) 0.041(2) Uani 1 1 d . . . . .
C10A C 0.5409(8) 0.3296(8) 0.5177(3) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.509666 0.359325 0.548549 0.051 Uiso 1 1 calc R U . . .
C11A C 0.4958(8) 0.2096(8) 0.5073(3) 0.044(2) Uani 1 1 d . . . . .
C12A C 0.6663(8) 0.3500(8) 0.5147(3) 0.043(2) Uani 1 1 d . . . . .
C13A C 0.7408(8) 0.2678(8) 0.4963(4) 0.048(2) Uani 1 1 d . . . . .
H13A H 0.711903 0.196512 0.487099 0.057 Uiso 1 1 calc R U . . .
C14A C 0.8572(9) 0.2892(8) 0.4913(4) 0.051(3) Uani 1 1 d . . . . .
H14A H 0.905750 0.233290 0.478425 0.061 Uiso 1 1 calc R U . . .
C15A C 0.8998(9) 0.3930(10) 0.5053(4) 0.059(3) Uani 1 1 d . . . . .
C16A C 0.8284(10) 0.4773(10) 0.5243(5) 0.072(4) Uani 1 1 d . . . . .
H16A H 0.858132 0.548401 0.533271 0.087 Uiso 1 1 calc R U . . .
C17A C 0.7134(10) 0.4548(10) 0.5296(5) 0.067(3) Uani 1 1 d . . . . .
H17A H 0.665943 0.510249 0.543422 0.080 Uiso 1 1 calc R U . . .
C18A C 0.3527(8) 0.1880(8) 0.4371(3) 0.041(2) Uani 1 1 d . . . . .
C19A C 0.3524(9) 0.0683(9) 0.4365(4) 0.051(3) Uani 1 1 d . . . . .
H19A H 0.397022 0.027250 0.458679 0.061 Uiso 1 1 calc R U . . .
C20A C 0.2845(10) 0.0107(10) 0.4021(5) 0.067(3) Uani 1 1 d . . . . .
H20A H 0.286448 -0.069083 0.401058 0.080 Uiso 1 1 calc R U . . .
C21A C 0.2150(12) 0.0689(11) 0.3699(5) 0.071(4) Uani 1 1 d . . . . .
H21A H 0.169530 0.028923 0.347662 0.086 Uiso 1 1 calc R U . . .
C22A C 0.2131(10) 0.1863(11) 0.3710(4) 0.067(3) Uani 1 1 d . . . . .
H22A H 0.166655 0.226940 0.349307 0.080 Uiso 1 1 calc R U . . .
C23A C 0.2806(9) 0.2438(9) 0.4043(4) 0.049(2) Uani 1 1 d . . . . .
Cl1B Cl -0.4699(2) 0.8128(3) 0.49360(13) 0.0666(8) Uani 1 1 d . . . . .
F1B F 0.3205(5) 0.8563(5) 0.5871(2) 0.0688(18) Uani 1 1 d . . . . .
O1B O 0.0660(6) 1.1058(6) 0.4801(3) 0.074(2) Uani 1 1 d . . . . .
O2B O 0.2714(5) 0.7626(5) 0.4781(2) 0.0473(17) Uani 1 1 d . . . . .
N1B N 0.1760(6) 0.6616(6) 0.5382(3) 0.0428(19) Uani 1 1 d . . . . .
H1B H 0.204541 0.594617 0.533007 0.051 Uiso 1 1 calc R U . . .
N2B N 0.1617(6) 0.9710(6) 0.5298(3) 0.0446(19) Uani 1 1 d . . . . .
C2B C 0.2016(8) 0.7564(8) 0.5115(4) 0.039(2) Uani 1 1 d . . . . .
C3B C 0.1197(7) 0.8506(7) 0.5281(3) 0.039(2) Uani 1 1 d . . . . .
C4B C -0.0084(9) 0.8477(9) 0.6074(4) 0.048(2) Uani 1 1 d . . . . .
H4B H -0.028939 0.924861 0.606499 0.057 Uiso 1 1 calc R U . . .
C5B C -0.0500(10) 0.7756(10) 0.6435(4) 0.057(3) Uani 1 1 d . . . . .
H5B H -0.099108 0.804671 0.667427 0.068 Uiso 1 1 calc R U . . .
C6B C -0.0197(9) 0.6612(10) 0.6447(4) 0.058(3) Uani 1 1 d . . . . .
H6B H -0.050597 0.614273 0.668979 0.070 Uiso 1 1 calc R U . . .
C7B C 0.0542(9) 0.6151(9) 0.6115(4) 0.052(3) Uani 1 1 d . . . . .
H7B H 0.075315 0.538122 0.612839 0.063 Uiso 1 1 calc R U . . .
C8B C 0.0964(8) 0.6873(8) 0.5756(4) 0.041(2) Uani 1 1 d . . . . .
C9B C 0.0642(8) 0.8019(8) 0.5727(3) 0.038(2) Uani 1 1 d . . . . .
C10B C 0.0387(8) 0.8912(8) 0.4851(4) 0.044(2) Uani 1 1 d . . . . .
H10B H 0.067534 0.862377 0.453621 0.053 Uiso 1 1 calc R U . . .
C11B C 0.0862(8) 1.0107(8) 0.4949(4) 0.050(2) Uani 1 1 d . . . . .
C12B C -0.0889(8) 0.8721(8) 0.4885(3) 0.042(2) Uani 1 1 d . . . . .
C13B C -0.1600(9) 0.9464(9) 0.5147(4) 0.048(2) Uani 1 1 d . . . . .
H13B H -0.128954 1.009795 0.530659 0.058 Uiso 1 1 calc R U . . .
C14B C -0.2748(9) 0.9259(9) 0.5169(4) 0.050(3) Uani 1 1 d . . . . .
H14B H -0.322341 0.974838 0.534602 0.061 Uiso 1 1 calc R U . . .
C15B C -0.3210(8) 0.8320(9) 0.4926(4) 0.049(2) Uani 1 1 d . . . . .
C16B C -0.2524(10) 0.7587(10) 0.4673(4) 0.060(3) Uani 1 1 d . . . . .
H16B H -0.283628 0.695449 0.451335 0.072 Uiso 1 1 calc R U . . .
C17B C -0.1372(9) 0.7788(9) 0.4656(4) 0.055(3) Uani 1 1 d . . . . .
H17B H -0.090150 0.728151 0.448555 0.066 Uiso 1 1 calc R U . . .
C18B C 0.2355(9) 1.0289(8) 0.5627(4) 0.045(2) Uani 1 1 d . . . . .
C19B C 0.2307(11) 1.1483(9) 0.5670(5) 0.066(3) Uani 1 1 d . . . . .
H19B H 0.179777 1.190887 0.548032 0.079 Uiso 1 1 calc R U . . .
C20B C 0.3033(15) 1.2022(13) 0.6002(6) 0.092(5) Uani 1 1 d . . . . .
H20B H 0.299544 1.281596 0.603702 0.111 Uiso 1 1 calc R U . . .
C21B C 0.3804(14) 1.1415(16) 0.6281(5) 0.091(5) Uani 1 1 d . . . . .
H21B H 0.428405 1.179500 0.649989 0.110 Uiso 1 1 calc R U . . .
C22B C 0.3862(11) 1.0265(12) 0.6234(4) 0.067(3) Uani 1 1 d . . . . .
H22B H 0.438236 0.984654 0.642159 0.081 Uiso 1 1 calc R U . . .
C23B C 0.3150(9) 0.9712(9) 0.5909(4) 0.053(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1A C15A 1.727(11) . ?
O1A C11A 1.196(10) . ?
O2A C2A 1.209(11) . ?
F1A C23A 1.361(11) . ?
N1A C2A 1.362(12) . ?
N1A C8A 1.406(12) . ?
N1A H1A 0.8600 . ?
N2A C11A 1.385(12) . ?
N2A C18A 1.415(12) . ?
N2A C3A 1.476(12) . ?
C2A C3A 1.533(12) . ?
C3A C9A 1.494(13) . ?
C3A C10A 1.590(13) . ?
C4A C9A 1.377(13) . ?
C4A C5A 1.387(14) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.367(15) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.367(16) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.375(14) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.398(13) . ?
C10A C12A 1.482(13) . ?
C10A C11A 1.519(13) . ?
C10A H10A 0.9800 . ?
C12A C13A 1.386(12) . ?
C12A C17A 1.397(15) . ?
C13A C14A 1.385(13) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.362(14) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.385(15) . ?
C16A C17A 1.372(16) . ?
C16A H16A 0.9300 . ?
C17A H17A 0.9300 . ?
C18A C23A 1.386(13) . ?
C18A C19A 1.393(13) . ?
C19A C20A 1.396(17) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.373(18) . ?
C20A H20A 0.9300 . ?
C21A C22A 1.367(17) . ?
C21A H21A 0.9300 . ?
C22A C23A 1.375(15) . ?
C22A H22A 0.9300 . ?
Cl1B C15B 1.748(10) . ?
F1B C23B 1.344(12) . ?
O1B C11B 1.201(11) . ?
O2B C2B 1.221(11) . ?
N1B C2B 1.354(12) . ?
N1B C8B 1.408(11) . ?
N1B H1B 0.8600 . ?
N2B C11B 1.374(13) . ?
N2B C18B 1.413(13) . ?
N2B C3B 1.485(12) . ?
C2B C3B 1.523(12) . ?
C3B C9B 1.488(12) . ?
C3B C10B 1.578(13) . ?
C4B C9B 1.374(13) . ?
C4B C5B 1.382(14) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.378(15) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.360(15) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.380(14) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.389(12) . ?
C10B C12B 1.504(12) . ?
C10B C11B 1.521(14) . ?
C10B H10B 0.9800 . ?
C12B C17B 1.372(13) . ?
C12B C13B 1.394(13) . ?
C13B C14B 1.359(14) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.385(13) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.357(14) . ?
C16B C17B 1.362(14) . ?
C16B H16B 0.9300 . ?
C17B H17B 0.9300 . ?
C18B C23B 1.377(15) . ?
C18B C19B 1.396(14) . ?
C19B C20B 1.39(2) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.37(2) . ?
C20B H20B 0.9300 . ?
C21B C22B 1.35(2) . ?
C21B H21B 0.9300 . ?
C22B C23B 1.374(16) . ?
C22B H22B 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
C2A N1A C8A 111.9(8) . . ?
C2A N1A H1A 124.0 . . ?
C8A N1A H1A 124.0 . . ?
C11A N2A C18A 131.2(8) . . ?
C11A N2A C3A 95.0(7) . . ?
C18A N2A C3A 132.3(8) . . ?
O2A C2A N1A 126.5(9) . . ?
O2A C2A C3A 126.7(8) . . ?
N1A C2A C3A 106.7(8) . . ?
N2A C3A C9A 118.8(8) . . ?
N2A C3A C2A 117.8(7) . . ?
C9A C3A C2A 103.5(7) . . ?
N2A C3A C10A 86.5(7) . . ?
C9A C3A C10A 117.8(7) . . ?
C2A C3A C10A 112.6(7) . . ?
C9A C4A C5A 118.3(10) . . ?
C9A C4A H4A 120.8 . . ?
C5A C4A H4A 120.8 . . ?
C6A C5A C4A 120.6(10) . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
C7A C6A C5A 122.3(10) . . ?
C7A C6A H6A 118.8 . . ?
C5A C6A H6A 118.8 . . ?
C6A C7A C8A 117.3(10) . . ?
C6A C7A H7A 121.4 . . ?
C8A C7A H7A 121.4 . . ?
C7A C8A C9A 121.7(9) . . ?
C7A C8A N1A 129.0(9) . . ?
C9A C8A N1A 109.3(8) . . ?
C4A C9A C8A 119.8(9) . . ?
C4A C9A C3A 132.2(9) . . ?
C8A C9A C3A 107.9(8) . . ?
C12A C10A C11A 118.6(8) . . ?
C12A C10A C3A 118.0(8) . . ?
C11A C10A C3A 85.4(7) . . ?
C12A C10A H10A 110.8 . . ?
C11A C10A H10A 110.8 . . ?
C3A C10A H10A 110.8 . . ?
O1A C11A N2A 131.5(9) . . ?
O1A C11A C10A 135.8(9) . . ?
N2A C11A C10A 92.7(7) . . ?
C13A C12A C17A 117.5(9) . . ?
C13A C12A C10A 121.7(9) . . ?
C17A C12A C10A 120.8(9) . . ?
C14A C13A C12A 121.6(9) . . ?
C14A C13A H13A 119.2 . . ?
C12A C13A H13A 119.2 . . ?
C15A C14A C13A 119.2(9) . . ?
C15A C14A H14A 120.4 . . ?
C13A C14A H14A 120.4 . . ?
C14A C15A C16A 121.0(10) . . ?
C14A C15A Cl1A 119.0(8) . . ?
C16A C15A Cl1A 120.0(9) . . ?
C17A C16A C15A 119.3(11) . . ?
C17A C16A H16A 120.4 . . ?
C15A C16A H16A 120.4 . . ?
C16A C17A C12A 121.3(10) . . ?
C16A C17A H17A 119.4 . . ?
C12A C17A H17A 119.4 . . ?
C23A C18A C19A 117.4(10) . . ?
C23A C18A N2A 122.2(8) . . ?
C19A C18A N2A 120.3(9) . . ?
C18A C19A C20A 119.3(11) . . ?
C18A C19A H19A 120.4 . . ?
C20A C19A H19A 120.4 . . ?
C21A C20A C19A 121.7(11) . . ?
C21A C20A H20A 119.2 . . ?
C19A C20A H20A 119.2 . . ?
C22A C21A C20A 119.3(11) . . ?
C22A C21A H21A 120.3 . . ?
C20A C21A H21A 120.3 . . ?
C21A C22A C23A 119.4(12) . . ?
C21A C22A H22A 120.3 . . ?
C23A C22A H22A 120.3 . . ?
F1A C23A C22A 119.1(10) . . ?
F1A C23A C18A 118.0(9) . . ?
C22A C23A C18A 122.8(10) . . ?
C2B N1B C8B 111.1(7) . . ?
C2B N1B H1B 124.4 . . ?
C8B N1B H1B 124.4 . . ?
C11B N2B C18B 131.8(8) . . ?
C11B N2B C3B 95.0(7) . . ?
C18B N2B C3B 132.0(8) . . ?
O2B C2B N1B 126.5(8) . . ?
O2B C2B C3B 126.5(8) . . ?
N1B C2B C3B 106.8(8) . . ?
N2B C3B C9B 118.6(7) . . ?
N2B C3B C2B 118.9(7) . . ?
C9B C3B C2B 103.9(7) . . ?
N2B C3B C10B 86.3(7) . . ?
C9B C3B C10B 117.4(7) . . ?
C2B C3B C10B 111.7(7) . . ?
C9B C4B C5B 118.0(9) . . ?
C9B C4B H4B 121.0 . . ?
C5B C4B H4B 121.0 . . ?
C6B C5B C4B 120.9(10) . . ?
C6B C5B H5B 119.5 . . ?
C4B C5B H5B 119.5 . . ?
C7B C6B C5B 121.9(10) . . ?
C7B C6B H6B 119.1 . . ?
C5B C6B H6B 119.1 . . ?
C6B C7B C8B 117.2(10) . . ?
C6B C7B H7B 121.4 . . ?
C8B C7B H7B 121.4 . . ?
C7B C8B C9B 121.9(9) . . ?
C7B C8B N1B 128.1(8) . . ?
C9B C8B N1B 110.0(8) . . ?
C4B C9B C8B 120.1(9) . . ?
C4B C9B C3B 132.8(8) . . ?
C8B C9B C3B 107.1(8) . . ?
C12B C10B C11B 118.9(8) . . ?
C12B C10B C3B 120.0(8) . . ?
C11B C10B C3B 85.7(7) . . ?
C12B C10B H10B 110.0 . . ?
C11B C10B H10B 110.0 . . ?
C3B C10B H10B 110.0 . . ?
O1B C11B N2B 131.8(10) . . ?
O1B C11B C10B 135.5(10) . . ?
N2B C11B C10B 92.7(7) . . ?
C17B C12B C13B 118.7(9) . . ?
C17B C12B C10B 119.6(9) . . ?
C13B C12B C10B 121.8(9) . . ?
C14B C13B C12B 119.8(9) . . ?
C14B C13B H13B 120.1 . . ?
C12B C13B H13B 120.1 . . ?
C13B C14B C15B 120.0(9) . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.6(9) . . ?
C16B C15B Cl1B 120.7(8) . . ?
C14B C15B Cl1B 118.6(8) . . ?
C15B C16B C17B 119.2(10) . . ?
C15B C16B H16B 120.4 . . ?
C17B C16B H16B 120.4 . . ?
C16B C17B C12B 121.6(10) . . ?
C16B C17B H17B 119.2 . . ?
C12B C17B H17B 119.2 . . ?
C23B C18B C19B 117.7(11) . . ?
C23B C18B N2B 122.0(8) . . ?
C19B C18B N2B 120.3(10) . . ?
C20B C19B C18B 118.8(13) . . ?
C20B C19B H19B 120.6 . . ?
C18B C19B H19B 120.6 . . ?
C21B C20B C19B 121.7(13) . . ?
C21B C20B H20B 119.1 . . ?
C19B C20B H20B 119.1 . . ?
C22B C21B C20B 119.6(13) . . ?
C22B C21B H21B 120.2 . . ?
C20B C21B H21B 120.2 . . ?
C21B C22B C23B 119.7(13) . . ?
C21B C22B H22B 120.1 . . ?
C23B C22B H22B 120.1 . . ?
F1B C23B C22B 119.1(11) . . ?
F1B C23B C18B 118.4(9) . . ?
C22B C23B C18B 122.5(11) . . ?

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
C8A N1A C2A O2A -177.3(9) . . . . ?
C8A N1A C2A C3A 6.8(10) . . . . ?
C11A N2A C3A C9A 115.0(8) . . . . ?
C18A N2A C3A C9A -51.9(12) . . . . ?
C11A N2A C3A C2A -118.8(8) . . . . ?
C18A N2A C3A C2A 74.3(12) . . . . ?
C11A N2A C3A C10A -5.0(7) . . . . ?
C18A N2A C3A C10A -171.9(9) . . . . ?
O2A C2A C3A N2A 42.3(13) . . . . ?
N1A C2A C3A N2A -141.8(8) . . . . ?
O2A C2A C3A C9A 175.6(9) . . . . ?
N1A C2A C3A C9A -8.5(9) . . . . ?
O2A C2A C3A C10A -56.0(12) . . . . ?
N1A C2A C3A C10A 119.8(8) . . . . ?
C9A C4A C5A C6A -0.1(15) . . . . ?
C4A C5A C6A C7A -0.8(17) . . . . ?
C5A C6A C7A C8A 1.2(16) . . . . ?
C6A C7A C8A C9A -0.7(15) . . . . ?
C6A C7A C8A N1A 179.4(10) . . . . ?
C2A N1A C8A C7A 177.8(10) . . . . ?
C2A N1A C8A C9A -2.1(10) . . . . ?
C5A C4A C9A C8A 0.5(14) . . . . ?
C5A C4A C9A C3A -175.0(10) . . . . ?
C7A C8A C9A C4A -0.1(14) . . . . ?
N1A C8A C9A C4A 179.8(8) . . . . ?
C7A C8A C9A C3A 176.4(9) . . . . ?
N1A C8A C9A C3A -3.7(10) . . . . ?
N2A C3A C9A C4A -44.0(14) . . . . ?
C2A C3A C9A C4A -176.8(10) . . . . ?
C10A C3A C9A C4A 58.2(14) . . . . ?
N2A C3A C9A C8A 140.1(8) . . . . ?
C2A C3A C9A C8A 7.3(9) . . . . ?
C10A C3A C9A C8A -117.7(9) . . . . ?
N2A C3A C10A C12A 124.7(8) . . . . ?
C9A C3A C10A C12A 3.8(12) . . . . ?
C2A C3A C10A C12A -116.6(9) . . . . ?
N2A C3A C10A C11A 4.6(6) . . . . ?
C9A C3A C10A C11A -116.3(8) . . . . ?
C2A C3A C10A C11A 123.3(8) . . . . ?
C18A N2A C11A O1A -5.9(16) . . . . ?
C3A N2A C11A O1A -173.0(10) . . . . ?
C18A N2A C11A C10A 172.4(9) . . . . ?
C3A N2A C11A C10A 5.3(7) . . . . ?
C12A C10A C11A O1A 53.7(15) . . . . ?
C3A C10A C11A O1A 173.3(11) . . . . ?
C12A C10A C11A N2A -124.5(8) . . . . ?
C3A C10A C11A N2A -4.9(7) . . . . ?
C11A C10A C12A C13A 9.1(14) . . . . ?
C3A C10A C12A C13A -91.6(11) . . . . ?
C11A C10A C12A C17A -172.2(10) . . . . ?
C3A C10A C12A C17A 87.1(12) . . . . ?
C17A C12A C13A C14A -2.0(15) . . . . ?
C10A C12A C13A C14A 176.7(10) . . . . ?
C12A C13A C14A C15A 0.9(16) . . . . ?
C13A C14A C15A C16A -0.4(17) . . . . ?
C13A C14A C15A Cl1A 179.1(8) . . . . ?
C14A C15A C16A C17A 1.1(19) . . . . ?
Cl1A C15A C16A C17A -178.3(10) . . . . ?
C15A C16A C17A C12A -2.3(19) . . . . ?
C13A C12A C17A C16A 2.8(17) . . . . ?
C10A C12A C17A C16A -176.0(11) . . . . ?
C11A N2A C18A C23A 177.5(9) . . . . ?
C3A N2A C18A C23A -20.1(14) . . . . ?
C11A N2A C18A C19A -0.9(14) . . . . ?
C3A N2A C18A C19A 161.6(9) . . . . ?
C23A C18A C19A C20A 2.6(13) . . . . ?
N2A C18A C19A C20A -179.0(9) . . . . ?
C18A C19A C20A C21A -2.2(16) . . . . ?
C19A C20A C21A C22A 0.9(18) . . . . ?
C20A C21A C22A C23A -0.2(18) . . . . ?
C21A C22A C23A F1A -178.7(10) . . . . ?
C21A C22A C23A C18A 0.8(17) . . . . ?
C19A C18A C23A F1A 177.5(9) . . . . ?
N2A C18A C23A F1A -0.8(14) . . . . ?
C19A C18A C23A C22A -2.0(14) . . . . ?
N2A C18A C23A C22A 179.6(10) . . . . ?
C8B N1B C2B O2B 176.5(9) . . . . ?
C8B N1B C2B C3B -8.2(10) . . . . ?
C11B N2B C3B C9B -115.2(9) . . . . ?
C18B N2B C3B C9B 53.1(13) . . . . ?
C11B N2B C3B C2B 117.0(9) . . . . ?
C18B N2B C3B C2B -74.7(12) . . . . ?
C11B N2B C3B C10B 4.2(7) . . . . ?
C18B N2B C3B C10B 172.5(9) . . . . ?
O2B C2B C3B N2B -39.8(13) . . . . ?
N1B C2B C3B N2B 144.9(8) . . . . ?
O2B C2B C3B C9B -174.2(9) . . . . ?
N1B C2B C3B C9B 10.5(9) . . . . ?
O2B C2B C3B C10B 58.3(12) . . . . ?
N1B C2B C3B C10B -117.0(8) . . . . ?
C9B C4B C5B C6B -0.1(16) . . . . ?
C4B C5B C6B C7B 1.7(17) . . . . ?
C5B C6B C7B C8B -1.2(16) . . . . ?
C6B C7B C8B C9B -0.9(15) . . . . ?
C6B C7B C8B N1B 177.8(10) . . . . ?
C2B N1B C8B C7B -176.5(10) . . . . ?
C2B N1B C8B C9B 2.4(11) . . . . ?
C5B C4B C9B C8B -1.9(14) . . . . ?
C5B C4B C9B C3B 176.6(10) . . . . ?
C7B C8B C9B C4B 2.5(14) . . . . ?
N1B C8B C9B C4B -176.4(8) . . . . ?
C7B C8B C9B C3B -176.3(9) . . . . ?
N1B C8B C9B C3B 4.7(10) . . . . ?
N2B C3B C9B C4B 37.7(15) . . . . ?
C2B C3B C9B C4B 172.3(10) . . . . ?
C10B C3B C9B C4B -63.8(13) . . . . ?
N2B C3B C9B C8B -143.6(8) . . . . ?
C2B C3B C9B C8B -9.1(9) . . . . ?
C10B C3B C9B C8B 114.8(9) . . . . ?
N2B C3B C10B C12B -124.9(9) . . . . ?
C9B C3B C10B C12B -4.5(12) . . . . ?
C2B C3B C10B C12B 115.4(9) . . . . ?
N2B C3B C10B C11B -3.8(6) . . . . ?
C9B C3B C10B C11B 116.7(8) . . . . ?
C2B C3B C10B C11B -123.5(8) . . . . ?
C18B N2B C11B O1B 5.4(18) . . . . ?
C3B N2B C11B O1B 173.7(11) . . . . ?
C18B N2B C11B C10B -172.6(9) . . . . ?
C3B N2B C11B C10B -4.4(7) . . . . ?
C12B C10B C11B O1B -51.7(16) . . . . ?
C3B C10B C11B O1B -173.8(12) . . . . ?
C12B C10B C11B N2B 126.2(8) . . . . ?
C3B C10B C11B N2B 4.1(7) . . . . ?
C11B C10B C12B C17B 159.7(9) . . . . ?
C3B C10B C12B C17B -97.6(11) . . . . ?
C11B C10B C12B C13B -20.7(14) . . . . ?
C3B C10B C12B C13B 82.0(12) . . . . ?
C17B C12B C13B C14B -0.4(15) . . . . ?
C10B C12B C13B C14B 180.0(9) . . . . ?
C12B C13B C14B C15B -0.7(15) . . . . ?
C13B C14B C15B C16B 1.2(15) . . . . ?
C13B C14B C15B Cl1B -176.7(8) . . . . ?
C14B C15B C16B C17B -0.5(16) . . . . ?
Cl1B C15B C16B C17B 177.3(8) . . . . ?
C15B C16B C17B C12B -0.6(17) . . . . ?
C13B C12B C17B C16B 1.1(15) . . . . ?
C10B C12B C17B C16B -179.3(10) . . . . ?
C11B N2B C18B C23B -172.0(10) . . . . ?
C3B N2B C18B C23B 23.8(15) . . . . ?
C11B N2B C18B C19B 7.0(15) . . . . ?
C3B N2B C18B C19B -157.2(9) . . . . ?
C23B C18B C19B C20B -1.8(15) . . . . ?
N2B C18B C19B C20B 179.1(9) . . . . ?
C18B C19B C20B C21B 1.1(18) . . . . ?
C19B C20B C21B C22B 0(2) . . . . ?
C20B C21B C22B C23B 0.1(19) . . . . ?
C21B C22B C23B F1B -179.0(10) . . . . ?
C21B C22B C23B C18B -0.8(17) . . . . ?
C19B C18B C23B F1B 179.9(9) . . . . ?
N2B C18B C23B F1B -1.0(14) . . . . ?
C19B C18B C23B C22B 1.7(15) . . . . ?
N2B C18B C23B C22B -179.2(9) . . . . ?

_refine_diff_density_max         0.931
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.238

