# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

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

data_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc214bbw
_database_code_depnum_ccdc_archive 'CCDC 1880997'
loop_
_audit_author_name
_audit_author_address
'chao li'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2018-11-24 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Cl N O2'
_chemical_formula_weight         465.95

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.3331(3)
_cell_length_b                   14.0402(2)
_cell_length_c                   20.1069(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.894(2)
_cell_angle_gamma                90
_cell_volume                     4925.17(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5999
_cell_measurement_theta_min      4.0250
_cell_measurement_theta_max      71.1720

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.581
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.722
_exptl_absorpt_correction_T_min  0.32706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            9721
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_max         71.352
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4666
_reflns_number_gt                4009
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0876P)²+2.9235P] 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
_refine_ls_extinction_coef       0.00074(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4666
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.006
_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 0.85385(4) 0.15205(7) 0.42066(5) 0.1067(3) Uani 1 1 d . . . . .
O2 O 0.33265(8) 0.30459(10) 0.22039(7) 0.0557(4) Uani 1 1 d . . . . .
N1 N 0.40054(8) 0.37825(11) 0.32073(8) 0.0450(4) Uani 1 1 d . . . . .
O1 O 0.49080(10) 0.00515(12) 0.30862(11) 0.0816(5) Uani 1 1 d . . . . .
C25 C 0.47153(10) 0.38960(13) 0.37643(9) 0.0453(4) Uani 1 1 d . . . . .
C16 C 0.38893(10) 0.30697(13) 0.27244(9) 0.0447(4) Uani 1 1 d . . . . .
C9 C 0.42378(11) 0.15547(12) 0.38606(9) 0.0446(4) Uani 1 1 d . . . . .
C8 C 0.46161(10) 0.16317(13) 0.33069(9) 0.0452(4) Uani 1 1 d . . . . .
C19 C 0.34283(11) 0.45074(13) 0.31348(9) 0.0475(4) Uani 1 1 d . . . . .
C15 C 0.44938(11) 0.23150(14) 0.28194(9) 0.0490(4) Uani 1 1 d . . . . .
C4 C 0.60045(12) 0.09912(14) 0.35738(9) 0.0502(4) Uani 1 1 d . . . . .
C10 C 0.34744(11) 0.18017(14) 0.37442(11) 0.0521(5) Uani 1 1 d . . . . .
H10 H 0.3176 0.1989 0.3300 0.062 Uiso 1 1 calc R U . . .
C7 C 0.51659(12) 0.08247(14) 0.33079(10) 0.0533(5) Uani 1 1 d . . . . .
C30 C 0.53636(12) 0.42203(15) 0.36251(11) 0.0551(5) Uani 1 1 d . . . . .
H30 H 0.5352 0.4346 0.3168 0.066 Uiso 1 1 calc R U . . .
C20 C 0.36391(13) 0.54528(15) 0.31827(11) 0.0567(5) Uani 1 1 d . . . . .
H20 H 0.4152 0.5618 0.3276 0.068 Uiso 1 1 calc R U . . .
C26 C 0.47355(13) 0.37138(15) 0.44456(10) 0.0549(5) Uani 1 1 d . . . . .
H26 H 0.4298 0.3502 0.4541 0.066 Uiso 1 1 calc R U . . .
C14 C 0.46591(12) 0.12248(15) 0.45236(10) 0.0548(5) Uani 1 1 d . . . . .
H14 H 0.5164 0.1029 0.4605 0.066 Uiso 1 1 calc R U . . .
C3 C 0.63051(12) 0.18615(16) 0.38589(12) 0.0590(5) Uani 1 1 d . . . . .
H3 H 0.5977 0.2340 0.3914 0.071 Uiso 1 1 calc R U . . .
C24 C 0.26658(12) 0.42655(17) 0.30058(12) 0.0613(5) Uani 1 1 d . . . . .
H24 H 0.2522 0.3628 0.2990 0.074 Uiso 1 1 calc R U . . .
C5 C 0.65029(13) 0.02739(16) 0.35190(11) 0.0599(5) Uani 1 1 d . . . . .
H5 H 0.6310 -0.0320 0.3346 0.072 Uiso 1 1 calc R U . . .
C29 C 0.60336(12) 0.43578(17) 0.41743(13) 0.0656(6) Uani 1 1 d . . . . .
H29 H 0.6472 0.4580 0.4084 0.079 Uiso 1 1 calc R U . . .
C27 C 0.54073(15) 0.38480(18) 0.49821(11) 0.0671(6) Uani 1 1 d . . . . .
H27 H 0.5422 0.3719 0.5440 0.081 Uiso 1 1 calc R U . . .
C11 C 0.31554(13) 0.17708(18) 0.42837(13) 0.0660(6) Uani 1 1 d . . . . .
H11 H 0.2649 0.1955 0.4205 0.079 Uiso 1 1 calc R U . . .
C6 C 0.72823(14) 0.04353(19) 0.37192(13) 0.0713(7) Uani 1 1 d . . . . .
H6 H 0.7615 -0.0044 0.3677 0.086 Uiso 1 1 calc R U . . .
C2 C 0.70873(14) 0.20232(18) 0.40618(13) 0.0688(6) Uani 1 1 d . . . . .
H2 H 0.7288 0.2607 0.4250 0.083 Uiso 1 1 calc R U . . .
C13 C 0.43357(15) 0.11855(18) 0.50599(12) 0.0675(6) Uani 1 1 d . . . . .
H13 H 0.4623 0.0970 0.5500 0.081 Uiso 1 1 calc R U . . .
C28 C 0.60538(14) 0.41691(17) 0.48491(12) 0.0682(6) Uani 1 1 d . . . . .
H28 H 0.6504 0.4259 0.5214 0.082 Uiso 1 1 calc R U . . .
C1 C 0.75609(13) 0.1309(2) 0.39805(13) 0.0682(6) Uani 1 1 d . . . . .
C21 C 0.30879(17) 0.61573(17) 0.30924(13) 0.0730(7) Uani 1 1 d . . . . .
H21 H 0.3232 0.6795 0.3135 0.088 Uiso 1 1 calc R U . . .
C12 C 0.35875(16) 0.1466(2) 0.49411(14) 0.0742(7) Uani 1 1 d . . . . .
H12 H 0.3372 0.1452 0.5303 0.089 Uiso 1 1 calc R U . . .
C22 C 0.23286(16) 0.5916(2) 0.29404(15) 0.0809(8) Uani 1 1 d . . . . .
H22 H 0.1957 0.6389 0.2865 0.097 Uiso 1 1 calc R U . . .
C17 C 0.48843(17) 0.2363(2) 0.22492(13) 0.0809(8) Uani 1 1 d . . . . .
H17A H 0.5003 0.3023 0.2187 0.097 Uiso 1 1 calc R U . . .
H17B H 0.5366 0.2020 0.2411 0.097 Uiso 1 1 calc R U . . .
C23 C 0.21182(14) 0.4973(2) 0.29002(15) 0.0784(7) Uani 1 1 d . . . . .
H23 H 0.1604 0.4810 0.2801 0.094 Uiso 1 1 calc R U . . .
C18 C 0.4445(2) 0.1979(3) 0.15733(16) 0.1218(15) Uani 1 1 d . . . . .
H18A H 0.4736 0.2043 0.1251 0.183 Uiso 1 1 calc R U . . .
H18B H 0.3972 0.2322 0.1399 0.183 Uiso 1 1 calc R U . . .
H18C H 0.4338 0.1318 0.1623 0.183 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
Cl1 C1 1.734(3) . ?
O2 C16 1.224(2) . ?
N1 C16 1.365(2) . ?
N1 C25 1.442(2) . ?
N1 C19 1.443(2) . ?
O1 C7 1.213(3) . ?
C25 C30 1.379(3) . ?
C25 C26 1.383(3) . ?
C16 C15 1.502(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.398(3) . ?
C9 C8 1.485(3) . ?
C8 C15 1.340(3) . ?
C8 C7 1.516(3) . ?
C19 C20 1.377(3) . ?
C19 C24 1.383(3) . ?
C15 C17 1.528(3) . ?
C4 C5 1.387(3) . ?
C4 C3 1.390(3) . ?
C4 C7 1.483(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C30 C29 1.390(3) . ?
C30 H30 0.9300 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9300 . ?
C26 C27 1.378(3) . ?
C26 H26 0.9300 . ?
C14 C13 1.382(3) . ?
C14 H14 0.9300 . ?
C3 C2 1.384(3) . ?
C3 H3 0.9300 . ?
C24 C23 1.381(3) . ?
C24 H24 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C29 C28 1.372(4) . ?
C29 H29 0.9300 . ?
C27 C28 1.369(4) . ?
C27 H27 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C6 C1 1.371(4) . ?
C6 H6 0.9300 . ?
C2 C1 1.368(3) . ?
C2 H2 0.9300 . ?
C13 C12 1.376(4) . ?
C13 H13 0.9300 . ?
C28 H28 0.9300 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C22 C23 1.374(4) . ?
C22 H22 0.9300 . ?
C17 C18 1.454(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C23 H23 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C16 N1 C25 122.68(15) . . ?
C16 N1 C19 119.76(15) . . ?
C25 N1 C19 117.35(14) . . ?
C30 C25 C26 119.98(18) . . ?
C30 C25 N1 120.49(17) . . ?
C26 C25 N1 119.48(17) . . ?
O2 C16 N1 122.31(17) . . ?
O2 C16 C15 119.00(16) . . ?
N1 C16 C15 118.62(15) . . ?
C10 C9 C14 118.41(18) . . ?
C10 C9 C8 122.24(17) . . ?
C14 C9 C8 119.35(17) . . ?
C15 C8 C9 126.05(17) . . ?
C15 C8 C7 119.85(17) . . ?
C9 C8 C7 114.08(16) . . ?
C20 C19 C24 119.69(19) . . ?
C20 C19 N1 119.44(18) . . ?
C24 C19 N1 120.86(18) . . ?
C8 C15 C16 123.29(16) . . ?
C8 C15 C17 124.63(18) . . ?
C16 C15 C17 111.78(17) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 119.49(19) . . ?
C3 C4 C7 121.53(17) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
O1 C7 C4 121.15(18) . . ?
O1 C7 C8 118.98(19) . . ?
C4 C7 C8 119.86(17) . . ?
C25 C30 C29 119.4(2) . . ?
C25 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C27 C26 C25 119.7(2) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C23 C24 C19 119.8(2) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C28 C29 C30 120.5(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C27 C28 C29 119.7(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C2 C1 C6 121.8(2) . . ?
C2 C1 Cl1 119.1(2) . . ?
C6 C1 Cl1 119.15(19) . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C17 C15 115.6(3) . . ?
C18 C17 H17A 108.4 . . ?
C15 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C15 C17 H17B 108.4 . . ?
H17A C17 H17B 107.4 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C25 C30 72.3(2) . . . . ?
C19 N1 C25 C30 -102.4(2) . . . . ?
C16 N1 C25 C26 -110.3(2) . . . . ?
C19 N1 C25 C26 75.0(2) . . . . ?
C25 N1 C16 O2 -170.52(17) . . . . ?
C19 N1 C16 O2 4.1(3) . . . . ?
C25 N1 C16 C15 6.5(3) . . . . ?
C19 N1 C16 C15 -178.97(16) . . . . ?
C10 C9 C8 C15 36.6(3) . . . . ?
C14 C9 C8 C15 -143.3(2) . . . . ?
C10 C9 C8 C7 -141.41(18) . . . . ?
C14 C9 C8 C7 38.7(2) . . . . ?
C16 N1 C19 C20 -130.55(19) . . . . ?
C25 N1 C19 C20 44.3(2) . . . . ?
C16 N1 C19 C24 48.3(3) . . . . ?
C25 N1 C19 C24 -136.85(19) . . . . ?
C9 C8 C15 C16 -5.8(3) . . . . ?
C7 C8 C15 C16 172.13(17) . . . . ?
C9 C8 C15 C17 -178.9(2) . . . . ?
C7 C8 C15 C17 -1.0(3) . . . . ?
O2 C16 C15 C8 -109.8(2) . . . . ?
N1 C16 C15 C8 73.1(2) . . . . ?
O2 C16 C15 C17 64.2(3) . . . . ?
N1 C16 C15 C17 -112.9(2) . . . . ?
C14 C9 C10 C11 3.5(3) . . . . ?
C8 C9 C10 C11 -176.35(19) . . . . ?
C5 C4 C7 O1 5.0(3) . . . . ?
C3 C4 C7 O1 -176.9(2) . . . . ?
C5 C4 C7 C8 -174.61(17) . . . . ?
C3 C4 C7 C8 3.4(3) . . . . ?
C15 C8 C7 O1 -103.1(3) . . . . ?
C9 C8 C7 O1 75.0(2) . . . . ?
C15 C8 C7 C4 76.5(2) . . . . ?
C9 C8 C7 C4 -105.3(2) . . . . ?
C26 C25 C30 C29 0.2(3) . . . . ?
N1 C25 C30 C29 177.60(19) . . . . ?
C24 C19 C20 C21 -0.9(3) . . . . ?
N1 C19 C20 C21 177.97(19) . . . . ?
C30 C25 C26 C27 -0.7(3) . . . . ?
N1 C25 C26 C27 -178.12(19) . . . . ?
C10 C9 C14 C13 -2.9(3) . . . . ?
C8 C9 C14 C13 177.01(19) . . . . ?
C5 C4 C3 C2 2.3(3) . . . . ?
C7 C4 C3 C2 -175.7(2) . . . . ?
C20 C19 C24 C23 2.4(3) . . . . ?
N1 C19 C24 C23 -176.4(2) . . . . ?
C3 C4 C5 C6 -2.5(3) . . . . ?
C7 C4 C5 C6 175.59(19) . . . . ?
C25 C30 C29 C28 0.3(4) . . . . ?
C25 C26 C27 C28 0.7(4) . . . . ?
C9 C10 C11 C12 -1.9(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C9 C14 C13 C12 0.5(4) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
C30 C29 C28 C27 -0.4(4) . . . . ?
C3 C2 C1 C6 -1.5(4) . . . . ?
C3 C2 C1 Cl1 177.88(19) . . . . ?
C5 C6 C1 C2 1.3(4) . . . . ?
C5 C6 C1 Cl1 -178.05(17) . . . . ?
C19 C20 C21 C22 -1.4(4) . . . . ?
C14 C13 C12 C11 1.2(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C20 C21 C22 C23 2.1(4) . . . . ?
C8 C15 C17 C18 97.2(3) . . . . ?
C16 C15 C17 C18 -76.7(3) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C19 C24 C23 C22 -1.7(4) . . . . ?

_refine_diff_density_max         0.810
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.043

_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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1565189'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 F N O2'
_chemical_formula_weight         421.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9409(2)
_cell_length_b                   10.8429(2)
_cell_length_c                   32.9352(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2121.57(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    6944
_cell_measurement_theta_min      4.2800
_cell_measurement_theta_max      71.2520

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.718
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_T_min  0.65218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            10995
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         4.293
_diffrn_reflns_theta_max         71.267
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3964
_reflns_number_gt                3831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.989

_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0294P)²+1.2011P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3964
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
F1 F 0.4936(4) 0.38698(17) 0.58191(6) 0.0549(5) Uani 1 1 d . . . . .
O2 O 0.6256(4) 0.2638(2) 0.67365(6) 0.0512(6) Uani 1 1 d . . . . .
N1 N 0.5595(4) 0.1516(2) 0.61678(7) 0.0380(6) Uani 1 1 d . . . . .
O1 O 1.1070(5) 0.3305(2) 0.64148(8) 0.0654(7) Uani 1 1 d . . . . .
C7 C 0.8063(6) 0.4540(3) 0.61919(9) 0.0392(7) Uani 1 1 d . . . . .
C15 C 0.6475(6) 0.3718(3) 0.61201(8) 0.0391(7) Uani 1 1 d . . . . .
C17 C 0.5903(5) 0.1322(3) 0.57399(9) 0.0382(6) Uani 1 1 d . . . . .
C16 C 0.6107(6) 0.2576(3) 0.63683(9) 0.0399(7) Uani 1 1 d . . . . .
C23 C 0.5064(6) 0.0433(3) 0.64028(8) 0.0399(7) Uani 1 1 d . . . . .
C1 C 0.8456(6) 0.5721(3) 0.59723(9) 0.0428(7) Uani 1 1 d . . . . .
C8 C 0.9846(5) 0.4150(3) 0.65016(10) 0.0421(7) Uani 1 1 d . . . . .
C9 C 1.0082(6) 0.4864(3) 0.68849(9) 0.0426(7) Uani 1 1 d . . . . .
C22 C 0.7880(6) 0.1634(3) 0.55500(10) 0.0470(8) Uani 1 1 d . . . . .
H22 H 0.9028 0.2014 0.5696 0.056 Uiso 1 1 calc R U . . .
C6 C 1.0505(6) 0.6328(3) 0.60101(11) 0.0544(9) Uani 1 1 d . . . . .
H6 H 1.1620 0.5989 0.6174 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8415(6) 0.5653(3) 0.70157(10) 0.0486(8) Uani 1 1 d . . . . .
H14 H 0.7071 0.5709 0.6872 0.058 Uiso 1 1 calc R U . . .
C19 C 0.4531(7) 0.0461(3) 0.51199(10) 0.0560(9) Uani 1 1 d . . . . .
H19 H 0.3401 0.0058 0.4976 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4233(6) 0.0724(3) 0.55250(10) 0.0477(8) Uani 1 1 d . . . . .
H18 H 0.2903 0.0499 0.5654 0.057 Uiso 1 1 calc R U . . .
C24 C 0.6567(7) -0.0520(3) 0.64039(11) 0.0541(9) Uani 1 1 d . . . . .
H24 H 0.7929 -0.0443 0.6267 0.065 Uiso 1 1 calc R U . . .
C2 C 0.6824(7) 0.6265(3) 0.57252(10) 0.0510(8) Uani 1 1 d . . . . .
H2 H 0.5422 0.5893 0.5698 0.061 Uiso 1 1 calc R U . . .
C28 C 0.3069(6) 0.0342(3) 0.66113(11) 0.0533(9) Uani 1 1 d . . . . .
H28 H 0.2056 0.0996 0.6614 0.064 Uiso 1 1 calc R U . . .
C10 C 1.2053(6) 0.4736(3) 0.71099(10) 0.0533(9) Uani 1 1 d . . . . .
H10 H 1.3160 0.4181 0.7030 0.064 Uiso 1 1 calc R U . . .
C20 C 0.6493(7) 0.0791(4) 0.49262(10) 0.0597(10) Uani 1 1 d . . . . .
H20 H 0.6688 0.0615 0.4652 0.072 Uiso 1 1 calc R U . . .
C12 C 1.0701(8) 0.6268(4) 0.75763(11) 0.0669(12) Uani 1 1 d . . . . .
H12 H 1.0927 0.6758 0.7804 0.080 Uiso 1 1 calc R U . . .
C21 C 0.8160(7) 0.1380(3) 0.51389(10) 0.0556(9) Uani 1 1 d . . . . .
H21 H 0.9481 0.1611 0.5008 0.067 Uiso 1 1 calc R U . . .
C11 C 1.2336(7) 0.5454(4) 0.74561(11) 0.0653(11) Uani 1 1 d . . . . .
H11 H 1.3650 0.5380 0.7608 0.078 Uiso 1 1 calc R U . . .
C13 C 0.8737(8) 0.6362(4) 0.73613(10) 0.0615(10) Uani 1 1 d . . . . .
H13 H 0.7617 0.6903 0.7447 0.074 Uiso 1 1 calc R U . . .
C27 C 0.2589(8) -0.0740(4) 0.68175(12) 0.0656(11) Uani 1 1 d . . . . .
H27 H 0.1245 -0.0811 0.6960 0.079 Uiso 1 1 calc R U . . .
C5 C 1.0924(8) 0.7422(4) 0.58101(13) 0.0659(10) Uani 1 1 d . . . . .
H5 H 1.2302 0.7817 0.5843 0.079 Uiso 1 1 calc R U . . .
C26 C 0.4068(9) -0.1705(4) 0.68134(12) 0.0695(12) Uani 1 1 d . . . . .
H26 H 0.3723 -0.2432 0.6949 0.083 Uiso 1 1 calc R U . . .
C3 C 0.7274(8) 0.7352(3) 0.55213(11) 0.0624(10) Uani 1 1 d . . . . .
H3 H 0.6177 0.7693 0.5354 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9296(8) 0.7932(3) 0.55614(12) 0.0667(11) Uani 1 1 d . . . . .
H4 H 0.9578 0.8663 0.5423 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6071(9) -0.1593(4) 0.66072(12) 0.0725(12) Uani 1 1 d . . . . .
H25 H 0.7090 -0.2245 0.6605 0.087 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
F1 C15 1.359(3) . ?
O2 C16 1.218(3) . ?
N1 C16 1.360(4) . ?
N1 C17 1.437(4) . ?
N1 C23 1.441(4) . ?
O1 C8 1.204(4) . ?
C7 C15 1.320(4) . ?
C7 C1 1.489(4) . ?
C7 C8 1.530(4) . ?
C15 C16 1.500(4) . ?
C17 C22 1.373(5) . ?
C17 C18 1.380(4) . ?
C23 C24 1.366(5) . ?
C23 C28 1.373(5) . ?
C1 C6 1.390(5) . ?
C1 C2 1.397(5) . ?
C8 C9 1.487(4) . ?
C9 C14 1.378(5) . ?
C9 C10 1.392(5) . ?
C22 C21 1.392(5) . ?
C22 H22 0.9300 . ?
C6 C5 1.380(5) . ?
C6 H6 0.9300 . ?
C14 C13 1.387(5) . ?
C14 H14 0.9300 . ?
C19 C18 1.376(5) . ?
C19 C20 1.376(5) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C24 C25 1.374(5) . ?
C24 H24 0.9300 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C28 C27 1.385(5) . ?
C28 H28 0.9300 . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C20 C21 1.371(5) . ?
C20 H20 0.9300 . ?
C12 C13 1.369(6) . ?
C12 C11 1.371(6) . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C27 C26 1.366(6) . ?
C27 H27 0.9300 . ?
C5 C4 1.383(6) . ?
C5 H5 0.9300 . ?
C26 C25 1.375(6) . ?
C26 H26 0.9300 . ?
C3 C4 1.362(6) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C17 124.8(2) . . ?
C16 N1 C23 118.5(2) . . ?
C17 N1 C23 115.8(2) . . ?
C15 C7 C1 127.3(3) . . ?
C15 C7 C8 115.3(3) . . ?
C1 C7 C8 117.0(3) . . ?
C7 C15 F1 122.0(3) . . ?
C7 C15 C16 124.4(3) . . ?
F1 C15 C16 113.6(3) . . ?
C22 C17 C18 119.8(3) . . ?
C22 C17 N1 121.3(3) . . ?
C18 C17 N1 118.7(3) . . ?
O2 C16 N1 123.1(3) . . ?
O2 C16 C15 119.1(3) . . ?
N1 C16 C15 117.8(2) . . ?
C24 C23 C28 120.6(3) . . ?
C24 C23 N1 118.3(3) . . ?
C28 C23 N1 121.1(3) . . ?
C6 C1 C2 117.4(3) . . ?
C6 C1 C7 120.1(3) . . ?
C2 C1 C7 122.5(3) . . ?
O1 C8 C9 122.7(3) . . ?
O1 C8 C7 118.0(3) . . ?
C9 C8 C7 119.1(3) . . ?
C14 C9 C10 120.0(3) . . ?
C14 C9 C8 121.4(3) . . ?
C10 C9 C8 118.6(3) . . ?
C17 C22 C21 119.8(3) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C9 C14 C13 120.1(3) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C23 C24 C25 120.1(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C23 C28 C27 118.9(3) . . ?
C23 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C11 C10 C9 118.9(4) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C26 C27 C28 120.7(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C27 C26 C25 119.6(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C24 C25 C26 120.0(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C7 C15 F1 0.1(5) . . . . ?
C8 C7 C15 F1 -172.0(3) . . . . ?
C1 C7 C15 C16 -176.7(3) . . . . ?
C8 C7 C15 C16 11.2(4) . . . . ?
C16 N1 C17 C22 47.2(4) . . . . ?
C23 N1 C17 C22 -121.9(3) . . . . ?
C16 N1 C17 C18 -137.7(3) . . . . ?
C23 N1 C17 C18 53.2(4) . . . . ?
C17 N1 C16 O2 -164.9(3) . . . . ?
C23 N1 C16 O2 4.0(5) . . . . ?
C17 N1 C16 C15 15.9(5) . . . . ?
C23 N1 C16 C15 -175.2(3) . . . . ?
C7 C15 C16 O2 41.2(5) . . . . ?
F1 C15 C16 O2 -135.8(3) . . . . ?
C7 C15 C16 N1 -139.5(3) . . . . ?
F1 C15 C16 N1 43.5(4) . . . . ?
C16 N1 C23 C24 -110.1(3) . . . . ?
C17 N1 C23 C24 59.8(4) . . . . ?
C16 N1 C23 C28 71.8(4) . . . . ?
C17 N1 C23 C28 -118.3(3) . . . . ?
C15 C7 C1 C6 -163.2(3) . . . . ?
C8 C7 C1 C6 8.8(4) . . . . ?
C15 C7 C1 C2 17.1(5) . . . . ?
C8 C7 C1 C2 -170.9(3) . . . . ?
C15 C7 C8 O1 65.9(4) . . . . ?
C1 C7 C8 O1 -107.1(3) . . . . ?
C15 C7 C8 C9 -117.4(3) . . . . ?
C1 C7 C8 C9 69.6(4) . . . . ?
O1 C8 C9 C14 -166.8(3) . . . . ?
C7 C8 C9 C14 16.6(5) . . . . ?
O1 C8 C9 C10 14.1(5) . . . . ?
C7 C8 C9 C10 -162.4(3) . . . . ?
C18 C17 C22 C21 2.0(5) . . . . ?
N1 C17 C22 C21 177.0(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C10 C9 C14 C13 2.9(5) . . . . ?
C8 C9 C14 C13 -176.1(3) . . . . ?
C20 C19 C18 C17 0.0(6) . . . . ?
C22 C17 C18 C19 -1.1(5) . . . . ?
N1 C17 C18 C19 -176.3(3) . . . . ?
C28 C23 C24 C25 1.4(5) . . . . ?
N1 C23 C24 C25 -176.6(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C7 C1 C2 C3 -178.9(3) . . . . ?
C24 C23 C28 C27 -1.0(5) . . . . ?
N1 C23 C28 C27 177.0(3) . . . . ?
C14 C9 C10 C11 -2.7(5) . . . . ?
C8 C9 C10 C11 176.4(3) . . . . ?
C18 C19 C20 C21 0.3(6) . . . . ?
C19 C20 C21 C22 0.6(6) . . . . ?
C17 C22 C21 C20 -1.7(5) . . . . ?
C13 C12 C11 C10 1.7(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C11 C12 C13 C14 -1.4(6) . . . . ?
C9 C14 C13 C12 -0.9(6) . . . . ?
C23 C28 C27 C26 -0.2(6) . . . . ?
C1 C6 C5 C4 -0.8(6) . . . . ?
C28 C27 C26 C25 1.0(6) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C6 C5 C4 C3 0.9(6) . . . . ?
C23 C24 C25 C26 -0.7(6) . . . . ?
C27 C26 C25 C24 -0.5(7) . . . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

