# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_i17822
_database_code_depnum_ccdc_archive 'CCDC 1988309'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2020-03-05 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36

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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   14.6384(3)
_cell_length_b                   6.90900(10)
_cell_length_c                   30.7229(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3107.21(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      65.07

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.656
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8284
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60225
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.877
_diffrn_reflns_theta_max         65.073
_diffrn_reflns_theta_full        65.073
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2641
_reflns_number_gt                2367
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0472P)²+1.3833P] 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_number_reflns         2641
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
O1 O 0.20890(6) 0.35914(15) 0.47376(3) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.55618(7) 0.33473(16) 0.34701(4) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.62377(7) 0.38901(16) 0.41684(4) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.55309(9) 0.35943(18) 0.39115(4) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.63727(9) 0.33371(19) 0.32804(4) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.71980(9) 0.35162(19) 0.35262(4) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.80966(9) 0.33565(19) 0.33582(4) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.818680 0.310689 0.305721 0.020 Uiso 1 1 calc R U . . .
C5 C 0.88358(9) 0.35604(19) 0.36279(5) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.943572 0.345143 0.351259 0.023 Uiso 1 1 calc R U . . .
C6 C 0.87127(9) 0.3930(2) 0.40749(5) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.923144 0.408790 0.425733 0.023 Uiso 1 1 calc R U . . .
C7 C 0.78575(9) 0.4066(2) 0.42493(4) 0.0182(3) Uani 1 1 d . . . . .
H7 H 0.778309 0.431651 0.455129 0.022 Uiso 1 1 calc R U . . .
C8 C 0.70819(9) 0.38319(19) 0.39796(4) 0.0153(3) Uani 1 1 d . . . . .
C9 C 0.46137(9) 0.35464(19) 0.41141(4) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.45272(9) 0.36193(19) 0.45681(4) 0.0158(3) Uani 1 1 d . . . . .
H10 H 0.506226 0.366221 0.474286 0.019 Uiso 1 1 calc R U . . .
C11 C 0.36836(9) 0.3630(2) 0.47665(4) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.363975 0.368777 0.507477 0.021 Uiso 1 1 calc R U . . .
C12 C 0.28924(9) 0.35556(19) 0.45127(4) 0.0162(3) Uani 1 1 d . . . . .
C13 C 0.29619(9) 0.3455(2) 0.40612(4) 0.0171(3) Uani 1 1 d . . . . .
H13 H 0.242606 0.339181 0.388732 0.021 Uiso 1 1 calc R U . . .
C14 C 0.38187(9) 0.34474(19) 0.38660(4) 0.0164(3) Uani 1 1 d . . . . .
H14 H 0.386268 0.337346 0.355791 0.020 Uiso 1 1 calc R U . . .
C15 C 0.12582(9) 0.3576(2) 0.44921(5) 0.0200(3) Uani 1 1 d . . . . .
H15A H 0.124750 0.469047 0.429492 0.030 Uiso 1 1 calc R U . . .
H15B H 0.073621 0.364804 0.469119 0.030 Uiso 1 1 calc R U . . .
H15C H 0.122182 0.237796 0.432212 0.030 Uiso 1 1 calc R U . . .
C16 C 0.63470(9) 0.3108(2) 0.27977(4) 0.0157(3) Uani 1 1 d . . . . .
C17 C 0.57412(9) 0.1763(2) 0.26169(4) 0.0180(3) Uani 1 1 d . . . . .
H17 H 0.536549 0.100248 0.280217 0.022 Uiso 1 1 calc R U . . .
C18 C 0.56850(9) 0.1532(2) 0.21700(4) 0.0207(3) Uani 1 1 d . . . . .
H18 H 0.528230 0.059481 0.205005 0.025 Uiso 1 1 calc R U . . .
C19 C 0.62174(9) 0.2670(2) 0.18972(4) 0.0220(3) Uani 1 1 d . . . . .
H19 H 0.617544 0.251717 0.159055 0.026 Uiso 1 1 calc R U . . .
C20 C 0.68087(10) 0.4025(2) 0.20716(5) 0.0214(3) Uani 1 1 d . . . . .
H20 H 0.716593 0.481503 0.188428 0.026 Uiso 1 1 calc R U . . .
C21 C 0.68813(9) 0.4234(2) 0.25194(4) 0.0184(3) Uani 1 1 d . . . . .
H21 H 0.729741 0.514909 0.263743 0.022 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
O1 C12 1.3642(16) . ?
O1 C15 1.4311(16) . ?
N1 C2 1.3224(17) . ?
N1 C1 1.3676(17) . ?
N2 C1 1.3174(17) . ?
N2 C8 1.3658(17) . ?
C1 C9 1.4803(18) . ?
C2 C3 1.4301(18) . ?
C2 C16 1.4919(18) . ?
C3 C4 1.4173(18) . ?
C3 C8 1.4199(19) . ?
C4 C5 1.3701(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3650(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4148(18) . ?
C7 H7 0.9500 . ?
C9 C14 1.3929(18) . ?
C9 C10 1.4017(19) . ?
C10 C11 1.3772(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3972(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3926(19) . ?
C13 C14 1.3902(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.3956(19) . ?
C16 C17 1.3994(19) . ?
C17 C18 1.3846(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C12 O1 C15 117.76(10) . . ?
C2 N1 C1 117.86(11) . . ?
C1 N2 C8 116.84(11) . . ?
N2 C1 N1 125.98(12) . . ?
N2 C1 C9 117.64(12) . . ?
N1 C1 C9 116.37(11) . . ?
N1 C2 C3 121.68(12) . . ?
N1 C2 C16 114.57(11) . . ?
C3 C2 C16 123.75(12) . . ?
C4 C3 C8 118.70(12) . . ?
C4 C3 C2 125.80(12) . . ?
C8 C3 C2 115.48(12) . . ?
C5 C4 C3 120.31(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.48(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.83(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.88(12) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N2 C8 C7 118.28(12) . . ?
N2 C8 C3 121.97(12) . . ?
C7 C8 C3 119.74(12) . . ?
C14 C9 C10 118.10(12) . . ?
C14 C9 C1 121.93(12) . . ?
C10 C9 C1 119.97(12) . . ?
C11 C10 C9 121.45(12) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.74(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O1 C12 C13 124.63(12) . . ?
O1 C12 C11 115.55(12) . . ?
C13 C12 C11 119.82(12) . . ?
C14 C13 C12 119.72(12) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.16(12) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.82(12) . . ?
C21 C16 C2 122.38(12) . . ?
C17 C16 C2 118.76(12) . . ?
C18 C17 C16 120.52(13) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.00(13) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.05(13) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.15(13) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.44(13) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.202
_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_i17855
_database_code_depnum_ccdc_archive 'CCDC 1996087'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2020-04-10 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 F N2'
_chemical_formula_sum            'C20 H12 F N2'
_chemical_formula_weight         299.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.3439(4)
_cell_length_b                   6.8286(2)
_cell_length_c                   20.1913(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.8600(10)
_cell_angle_gamma                90
_cell_volume                     1412.80(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      27.07

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44058
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.152
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3120
_reflns_number_gt                2704
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0524P)²+0.7391P] 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_number_reflns         3120
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.58228(11) 0.82153(19) 0.32227(5) 0.0261(3) Uani 0.6615(15) 1 d . . P A 1
F1' F 0.9157(2) 0.8819(4) 0.48706(11) 0.0261(3) Uani 0.3385(15) 1 d . . P A 2
N1 N 0.55348(10) 0.73621(16) 0.61485(5) 0.0173(2) Uani 1 1 d . . . . .
N2 N 0.37320(10) 0.70081(15) 0.52792(5) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.49681(12) 0.73406(17) 0.54954(6) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.47782(12) 0.70644(18) 0.66145(6) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.34035(12) 0.67511(18) 0.64478(6) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.25007(12) 0.6532(2) 0.69119(6) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.279452 0.661831 0.737774 0.024 Uiso 1 1 calc R U . . .
C5 C 0.12078(13) 0.6195(2) 0.66922(6) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.061516 0.601221 0.700721 0.026 Uiso 1 1 calc R U . . .
C6 C 0.07499(12) 0.6118(2) 0.60022(7) 0.0214(3) Uani 1 1 d . . . . .
H6 H -0.014823 0.587578 0.585613 0.026 Uiso 1 1 calc R U . . .
C7 C 0.15870(12) 0.63894(19) 0.55413(6) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.126487 0.636421 0.507764 0.024 Uiso 1 1 calc R U . . .
C8 C 0.29329(12) 0.67078(18) 0.57535(6) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.58623(12) 0.77303(18) 0.49948(6) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.53802(13) 0.77793(19) 0.43141(6) 0.0197(3) Uani 1 1 d . . . . .
H10 H 0.448070 0.755489 0.416591 0.024 Uiso 1 1 calc R U . . .
C11 C 0.62316(14) 0.8159(2) 0.38609(7) 0.0240(3) Uani 1 1 d . . . . .
C12 C 0.75434(14) 0.8500(2) 0.40493(7) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.810909 0.875905 0.372659 0.029 Uiso 1 1 calc R U . . .
C13 C 0.80080(14) 0.8451(2) 0.47262(7) 0.0249(3) Uani 1 1 d . . . . .
C14 C 0.71863(13) 0.80681(19) 0.51986(6) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.752469 0.803609 0.566020 0.025 Uiso 1 1 calc R U . . .
C15 C 0.54440(12) 0.71282(19) 0.73168(6) 0.0178(3) Uani 1 1 d . . . . .
C16 C 0.63701(12) 0.8585(2) 0.75005(6) 0.0210(3) Uani 1 1 d . . . . .
H16 H 0.656985 0.951239 0.717877 0.025 Uiso 1 1 calc R U . . .
C17 C 0.70016(13) 0.8682(2) 0.81540(7) 0.0245(3) Uani 1 1 d . . . . .
H17 H 0.762067 0.968913 0.827942 0.029 Uiso 1 1 calc R U . . .
C18 C 0.67281(13) 0.7308(2) 0.86237(6) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.715577 0.737922 0.907039 0.030 Uiso 1 1 calc R U . . .
C19 C 0.58296(12) 0.5834(2) 0.84383(6) 0.0238(3) Uani 1 1 d . . . . .
H19 H 0.565139 0.488370 0.875731 0.029 Uiso 1 1 calc R U . . .
C20 C 0.51892(12) 0.5742(2) 0.77881(6) 0.0208(3) Uani 1 1 d . . . . .
H20 H 0.457435 0.472826 0.766424 0.025 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 C11 1.3006(17) . ?
F1' C13 1.211(3) . ?
N1 C2 1.3193(16) . ?
N1 C1 1.3681(15) . ?
N2 C1 1.3131(16) . ?
N2 C8 1.3633(16) . ?
C1 C9 1.4844(17) . ?
C2 C3 1.4319(17) . ?
C2 C15 1.4899(16) . ?
C3 C4 1.4184(17) . ?
C3 C8 1.4201(16) . ?
C4 C5 1.3695(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4099(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3678(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4163(17) . ?
C7 H7 0.9500 . ?
C9 C14 1.3943(18) . ?
C9 C10 1.3970(17) . ?
C10 C11 1.3786(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3864(18) . ?
C14 H14 0.9500 . ?
C15 C20 1.3929(18) . ?
C15 C16 1.3957(18) . ?
C16 C17 1.3915(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3887(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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 C1 117.91(10) . . ?
C1 N2 C8 116.67(10) . . ?
N2 C1 N1 126.27(11) . . ?
N2 C1 C9 118.28(11) . . ?
N1 C1 C9 115.45(11) . . ?
N1 C2 C3 121.48(11) . . ?
N1 C2 C15 115.61(11) . . ?
C3 C2 C15 122.89(11) . . ?
C4 C3 C8 118.83(11) . . ?
C4 C3 C2 125.66(11) . . ?
C8 C3 C2 115.50(11) . . ?
C5 C4 C3 120.38(11) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.50(12) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.59(12) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.17(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N2 C8 C7 118.42(11) . . ?
N2 C8 C3 122.10(11) . . ?
C7 C8 C3 119.46(11) . . ?
C14 C9 C10 119.37(12) . . ?
C14 C9 C1 120.47(11) . . ?
C10 C9 C1 120.16(11) . . ?
C11 C10 C9 118.89(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
F1 C11 C12 116.29(12) . . ?
F1 C11 C10 120.83(13) . . ?
C12 C11 C10 122.88(13) . . ?
C11 C12 C13 117.63(12) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
F1' C13 C12 115.41(15) . . ?
F1' C13 C14 123.19(16) . . ?
C12 C13 C14 121.36(13) . . ?
C13 C14 C9 119.87(12) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C20 C15 C16 119.34(11) . . ?
C20 C15 C2 121.63(11) . . ?
C16 C15 C2 119.01(11) . . ?
C17 C16 C15 120.15(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.11(13) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.82(12) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.25(12) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.31(12) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_i17869
_database_code_depnum_ccdc_archive 'CCDC 2002377'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2020-05-07 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 F N2'
_chemical_formula_sum            'C20 H13 F N2'
_chemical_formula_weight         300.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.0455(5)
_cell_length_b                   11.0023(10)
_cell_length_c                   11.7294(10)
_cell_angle_alpha                112.103(4)
_cell_angle_beta                 96.044(4)
_cell_angle_gamma                93.256(4)
_cell_volume                     714.87(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    6556
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      27.17

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8496
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29678
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.009
_diffrn_reflns_theta_max         27.096
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3149
_reflns_number_gt                2244
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0583P)²+0.4044P] 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_number_reflns         3149
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.24202(19) -0.00849(12) 0.03561(10) 0.0338(3) Uani 1 1 d . . . . .
N1 N 0.6515(2) 0.33303(14) 0.58471(14) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.6131(2) 0.39279(15) 0.79974(14) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.7186(3) 0.39978(17) 0.70932(16) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.4604(3) 0.25589(17) 0.55022(16) 0.0192(4) Uani 1 1 d . . . . .
C3 C 0.3298(3) 0.24084(17) 0.63929(16) 0.0200(4) Uani 1 1 d . . . . .
C4 C 0.1265(3) 0.15848(18) 0.60935(18) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.066413 0.110357 0.524827 0.027 Uiso 1 1 calc R U . . .
C5 C 0.0163(3) 0.14787(18) 0.70148(18) 0.0237(4) Uani 1 1 d . . . . .
H5 H -0.120363 0.092392 0.680571 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1032(3) 0.21837(18) 0.82719(18) 0.0247(4) Uani 1 1 d . . . . .
H6 H 0.025475 0.209306 0.890327 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2988(3) 0.29995(18) 0.85932(17) 0.0228(4) Uani 1 1 d . . . . .
H7 H 0.354994 0.348225 0.944395 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4167(3) 0.31220(17) 0.76603(17) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.9300(3) 0.48854(17) 0.74369(16) 0.0192(4) Uani 1 1 d . . . . .
C10 C 1.0507(3) 0.49797(18) 0.65184(17) 0.0220(4) Uani 1 1 d . . . . .
H10 H 0.996047 0.448080 0.566853 0.026 Uiso 1 1 calc R U . . .
C11 C 1.2498(3) 0.57941(18) 0.68332(18) 0.0246(4) Uani 1 1 d . . . . .
H11 H 1.330215 0.585984 0.620159 0.030 Uiso 1 1 calc R U . . .
C12 C 1.3309(3) 0.65114(18) 0.80720(18) 0.0244(4) Uani 1 1 d . . . . .
H12 H 1.468279 0.706092 0.829140 0.029 Uiso 1 1 calc R U . . .
C13 C 1.2118(3) 0.64287(18) 0.89925(18) 0.0253(4) Uani 1 1 d . . . . .
H13 H 1.267216 0.693006 0.984099 0.030 Uiso 1 1 calc R U . . .
C14 C 1.0125(3) 0.56186(18) 0.86818(17) 0.0222(4) Uani 1 1 d . . . . .
H14 H 0.932038 0.556258 0.931668 0.027 Uiso 1 1 calc R U . . .
C15 C 0.3955(3) 0.18432(17) 0.41396(16) 0.0199(4) Uani 1 1 d . . . . .
C16 C 0.1955(3) 0.19952(18) 0.35278(17) 0.0233(4) Uani 1 1 d . . . . .
H16 H 0.093844 0.254273 0.399134 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1426(3) 0.13568(18) 0.22479(17) 0.0245(4) Uani 1 1 d . . . . .
H17 H 0.007799 0.147582 0.182584 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2913(3) 0.05472(18) 0.16096(16) 0.0241(4) Uani 1 1 d . . . . .
C19 C 0.4893(3) 0.03618(18) 0.21761(17) 0.0249(4) Uani 1 1 d . . . . .
H19 H 0.587822 -0.020891 0.170825 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5418(3) 0.10286(18) 0.34485(17) 0.0230(4) Uani 1 1 d . . . . .
H20 H 0.679751 0.092858 0.385606 0.028 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 C18 1.360(2) . ?
N1 C2 1.323(2) . ?
N1 C1 1.369(2) . ?
N2 C1 1.317(2) . ?
N2 C8 1.367(2) . ?
C1 C9 1.484(2) . ?
C2 C3 1.425(2) . ?
C2 C15 1.488(2) . ?
C3 C4 1.414(2) . ?
C3 C8 1.419(2) . ?
C4 C5 1.365(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.395(2) . ?
C9 C14 1.395(2) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 C20 1.392(2) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.370(3) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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 C1 117.71(15) . . ?
C1 N2 C8 116.98(15) . . ?
N2 C1 N1 126.20(16) . . ?
N2 C1 C9 117.91(15) . . ?
N1 C1 C9 115.89(15) . . ?
N1 C2 C3 121.42(16) . . ?
N1 C2 C15 115.78(15) . . ?
C3 C2 C15 122.78(15) . . ?
C4 C3 C8 119.09(16) . . ?
C4 C3 C2 124.52(16) . . ?
C8 C3 C2 116.38(15) . . ?
C5 C4 C3 120.22(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.62(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.60(17) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.96(17) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N2 C8 C7 119.19(16) . . ?
N2 C8 C3 121.29(16) . . ?
C7 C8 C3 119.51(16) . . ?
C10 C9 C14 119.13(16) . . ?
C10 C9 C1 120.35(16) . . ?
C14 C9 C1 120.52(16) . . ?
C11 C10 C9 120.67(17) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.72(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.09(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.36(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.02(17) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C16 C15 C20 118.86(17) . . ?
C16 C15 C2 121.91(16) . . ?
C20 C15 C2 119.20(16) . . ?
C17 C16 C15 120.86(17) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 118.02(17) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
F1 C18 C19 118.20(16) . . ?
F1 C18 C17 118.76(16) . . ?
C19 C18 C17 123.03(17) . . ?
C18 C19 C20 118.21(17) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C15 121.00(17) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_i17847
_database_code_depnum_ccdc_archive 'CCDC 1994079'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 F2 N2'
_chemical_formula_sum            'C20 H12 F2 N2'
_chemical_formula_weight         318.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.8602(2)
_cell_length_b                   8.9830(2)
_cell_length_c                   11.3189(3)
_cell_angle_alpha                94.7750(10)
_cell_angle_beta                 108.4430(10)
_cell_angle_gamma                100.7540(10)
_cell_volume                     736.11(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.207
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31661
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3247
_reflns_number_gt                2902
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0333P)²+0.3862P] 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_number_reflns         3247
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 -0.09564(10) -0.02482(8) 0.22867(7) 0.02437(18) Uani 1 1 d . . . . .
N1 N 0.37186(13) 0.14468(11) 0.29829(9) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.23270(15) 0.20263(13) 0.30320(10) 0.0148(2) Uani 1 1 d . . . . .
F2 F 0.24045(10) 0.40097(9) 0.12479(7) 0.02688(19) Uani 1 1 d . . . . .
N2 N 0.20992(13) 0.27345(11) 0.40618(9) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.51657(15) 0.16757(12) 0.40867(11) 0.0148(2) Uani 1 1 d . . . . .
C3 C 0.67390(16) 0.11297(13) 0.40793(11) 0.0178(2) Uani 1 1 d . . . . .
H3 H 0.673486 0.055007 0.333668 0.021 Uiso 1 1 calc R U . . .
C4 C 0.82635(16) 0.14365(13) 0.51404(12) 0.0190(2) Uani 1 1 d . . . . .
H4 H 0.931237 0.105894 0.513404 0.023 Uiso 1 1 calc R U . . .
C5 C 0.82949(16) 0.23090(13) 0.62459(11) 0.0180(2) Uani 1 1 d . . . . .
H5 H 0.937603 0.253546 0.697019 0.022 Uiso 1 1 calc R U . . .
C6 C 0.67817(16) 0.28331(13) 0.62854(11) 0.0163(2) Uani 1 1 d . . . . .
H6 H 0.682259 0.342776 0.703245 0.020 Uiso 1 1 calc R U . . .
C7 C 0.51505(15) 0.24889(12) 0.52111(10) 0.0141(2) Uani 1 1 d . . . . .
C8 C 0.34805(15) 0.29448(12) 0.51451(10) 0.0138(2) Uani 1 1 d . . . . .
C9 C 0.31811(15) 0.36841(13) 0.62640(10) 0.0145(2) Uani 1 1 d . . . . .
C10 C 0.37307(15) 0.31751(13) 0.74320(11) 0.0167(2) Uani 1 1 d . . . . .
H10 H 0.430540 0.233001 0.752140 0.020 Uiso 1 1 calc R U . . .
C11 C 0.34416(16) 0.38973(14) 0.84606(11) 0.0198(2) Uani 1 1 d . . . . .
H11 H 0.381537 0.354458 0.925088 0.024 Uiso 1 1 calc R U . . .
C12 C 0.26068(17) 0.51344(14) 0.83356(11) 0.0215(3) Uani 1 1 d . . . . .
H12 H 0.244345 0.564840 0.904638 0.026 Uiso 1 1 calc R U . . .
C13 C 0.20100(17) 0.56213(14) 0.71717(12) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.141013 0.645164 0.708220 0.025 Uiso 1 1 calc R U . . .
C14 C 0.22883(16) 0.48971(13) 0.61392(11) 0.0171(2) Uani 1 1 d . . . . .
H14 H 0.186899 0.522855 0.534323 0.021 Uiso 1 1 calc R U . . .
C15 C 0.07892(15) 0.18750(13) 0.18109(10) 0.0154(2) Uani 1 1 d . . . . .
C16 C -0.07894(16) 0.07200(13) 0.14541(11) 0.0174(2) Uani 1 1 d . . . . .
C17 C -0.21674(16) 0.04853(14) 0.02960(12) 0.0214(3) Uani 1 1 d . . . . .
H17 H -0.322100 -0.033397 0.008404 0.026 Uiso 1 1 calc R U . . .
C18 C -0.19681(17) 0.14812(15) -0.05487(11) 0.0218(3) Uani 1 1 d . . . . .
H18 H -0.289019 0.133365 -0.135577 0.026 Uiso 1 1 calc R U . . .
C19 C -0.04454(18) 0.26860(14) -0.02322(11) 0.0207(3) Uani 1 1 d . . . . .
H19 H -0.032478 0.338370 -0.080257 0.025 Uiso 1 1 calc R U . . .
C20 C 0.08946(16) 0.28474(13) 0.09347(11) 0.0184(2) 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
F1 C16 1.3542(14) . ?
N1 C1 1.3102(15) . ?
N1 C2 1.3667(15) . ?
C1 N2 1.3589(14) . ?
C1 C15 1.4968(15) . ?
F2 C20 1.3543(14) . ?
N2 C8 1.3269(14) . ?
C2 C3 1.4149(16) . ?
C2 C7 1.4184(15) . ?
C3 C4 1.3658(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4110(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3702(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4217(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.4283(15) . ?
C8 C9 1.4857(15) . ?
C9 C14 1.3957(16) . ?
C9 C10 1.3986(16) . ?
C10 C11 1.3873(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3875(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3887(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3875(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3827(16) . ?
C15 C20 1.3866(16) . ?
C16 C17 1.3807(17) . ?
C17 C18 1.3870(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3831(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.3805(16) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 115.78(10) . . ?
N1 C1 N2 127.84(10) . . ?
N1 C1 C15 116.26(10) . . ?
N2 C1 C15 115.90(9) . . ?
C8 N2 C1 116.99(10) . . ?
N1 C2 C3 118.32(10) . . ?
N1 C2 C7 121.79(10) . . ?
C3 C2 C7 119.85(10) . . ?
C4 C3 C2 119.97(11) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.61(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.66(11) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.15(11) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 118.62(10) . . ?
C2 C7 C8 116.03(10) . . ?
C6 C7 C8 125.31(10) . . ?
N2 C8 C7 121.21(10) . . ?
N2 C8 C9 116.03(10) . . ?
C7 C8 C9 122.76(10) . . ?
C14 C9 C10 119.06(10) . . ?
C14 C9 C8 119.09(10) . . ?
C10 C9 C8 121.82(10) . . ?
C11 C10 C9 120.39(11) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.03(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.01(11) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.11(11) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.35(11) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C16 C15 C20 115.50(10) . . ?
C16 C15 C1 122.52(10) . . ?
C20 C15 C1 121.92(10) . . ?
F1 C16 C17 118.80(11) . . ?
F1 C16 C15 117.45(10) . . ?
C17 C16 C15 123.74(11) . . ?
C16 C17 C18 118.04(11) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 120.91(11) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 118.22(11) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
F2 C20 C19 118.74(11) . . ?
F2 C20 C15 117.70(10) . . ?
C19 C20 C15 123.56(11) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_i17854
_database_code_depnum_ccdc_archive 'CCDC 1996086'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2020-04-10 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.38

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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.9542(2)
_cell_length_b                   10.6468(4)
_cell_length_c                   13.6281(5)
_cell_angle_alpha                83.162(2)
_cell_angle_beta                 86.529(2)
_cell_angle_gamma                76.8570(10)
_cell_volume                     834.81(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.11

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8094
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36007
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.976
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3684
_reflns_number_gt                3226
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0616P)²+0.3299P] 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_number_reflns         3684
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
O1 O 1.08170(15) 1.03130(8) 0.64369(6) 0.0165(2) Uani 1 1 d . . . . .
O2 O 1.20896(16) 0.62256(9) 0.50073(7) 0.0217(2) Uani 1 1 d . . . . .
N1 N 0.58775(17) 0.60113(10) 0.75313(7) 0.0142(2) Uani 1 1 d . . . . .
N2 N 0.45497(17) 0.82117(10) 0.78947(7) 0.0138(2) Uani 1 1 d . . . . .
C1 C 0.5984(2) 0.72908(11) 0.74599(8) 0.0134(2) Uani 1 1 d . . . . .
C2 C 0.4129(2) 0.56665(11) 0.80474(8) 0.0136(2) Uani 1 1 d . . . . .
C3 C 0.2415(2) 0.65750(11) 0.85313(8) 0.0134(2) Uani 1 1 d . . . . .
C4 C 0.0500(2) 0.62692(12) 0.90963(9) 0.0155(3) Uani 1 1 d . . . . .
H4 H 0.027945 0.540652 0.916489 0.019 Uiso 1 1 calc R U . . .
C5 C -0.1037(2) 0.72093(12) 0.95446(9) 0.0164(3) Uani 1 1 d . . . . .
H5 H -0.232231 0.699832 0.992135 0.020 Uiso 1 1 calc R U . . .
C6 C -0.0714(2) 0.84929(12) 0.94474(9) 0.0165(3) Uani 1 1 d . . . . .
H6 H -0.179417 0.914099 0.975724 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1131(2) 0.88157(11) 0.89134(9) 0.0158(3) Uani 1 1 d . . . . .
H7 H 0.133105 0.968182 0.885967 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2749(2) 0.78614(11) 0.84395(8) 0.0135(2) Uani 1 1 d . . . . .
C9 C 0.7926(2) 0.76421(11) 0.68325(8) 0.0135(2) Uani 1 1 d . . . . .
C10 C 0.8498(2) 0.88339(11) 0.68811(8) 0.0137(2) Uani 1 1 d . . . . .
H10 H 0.760926 0.943546 0.729399 0.016 Uiso 1 1 calc R U . . .
C11 C 1.0370(2) 0.91355(11) 0.63239(8) 0.0142(2) Uani 1 1 d . . . . .
C12 C 1.1668(2) 0.82756(12) 0.56966(9) 0.0151(3) Uani 1 1 d . . . . .
H12 H 1.296312 0.847949 0.532397 0.018 Uiso 1 1 calc R U . . .
C13 C 1.1019(2) 0.71123(12) 0.56299(9) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.9178(2) 0.67799(11) 0.61982(9) 0.0148(2) Uani 1 1 d . . . . .
H14 H 0.877813 0.597437 0.615486 0.018 Uiso 1 1 calc R U . . .
C15 C 0.4095(2) 0.42645(11) 0.81213(8) 0.0145(2) Uani 1 1 d . . . . .
C16 C 0.6040(2) 0.33535(12) 0.84638(9) 0.0179(3) Uani 1 1 d . . . . .
H16 H 0.732012 0.363459 0.867319 0.021 Uiso 1 1 calc R U . . .
C17 C 0.6107(2) 0.20372(12) 0.84992(10) 0.0213(3) Uani 1 1 d . . . . .
H17 H 0.742886 0.142076 0.873977 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4263(2) 0.16170(12) 0.81865(10) 0.0212(3) Uani 1 1 d . . . . .
H18 H 0.432730 0.071527 0.820092 0.025 Uiso 1 1 calc R U . . .
C19 C 0.2313(2) 0.25216(12) 0.78506(9) 0.0196(3) Uani 1 1 d . . . . .
H19 H 0.103901 0.223565 0.764010 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2221(2) 0.38425(12) 0.78216(9) 0.0165(3) Uani 1 1 d . . . . .
H20 H 0.088014 0.445669 0.759750 0.020 Uiso 1 1 calc R U . . .
C21 C 1.2777(2) 1.06467(12) 0.59031(9) 0.0171(3) Uani 1 1 d . . . . .
H21A H 1.261588 1.062587 0.519418 0.026 Uiso 1 1 calc R U . . .
H21B H 1.418025 1.002270 0.612348 0.026 Uiso 1 1 calc R U . . .
H21C H 1.287791 1.152031 0.602564 0.026 Uiso 1 1 calc R U . . .
C22 C 1.3904(2) 0.65411(13) 0.43600(10) 0.0245(3) Uani 1 1 d . . . . .
H22A H 1.443812 0.585750 0.392310 0.037 Uiso 1 1 calc R U . . .
H22B H 1.518836 0.661329 0.475110 0.037 Uiso 1 1 calc R U . . .
H22C H 1.333204 0.736933 0.396137 0.037 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
O1 C11 1.3672(15) . ?
O1 C21 1.4286(14) . ?
O2 C13 1.3673(15) . ?
O2 C22 1.4274(15) . ?
N1 C2 1.3179(15) . ?
N1 C1 1.3698(15) . ?
N2 C1 1.3183(16) . ?
N2 C8 1.3636(15) . ?
C1 C9 1.4865(16) . ?
C2 C3 1.4260(16) . ?
C2 C15 1.4888(16) . ?
C3 C4 1.4149(16) . ?
C3 C8 1.4181(16) . ?
C4 C5 1.3690(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4126(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3678(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4188(16) . ?
C7 H7 0.9500 . ?
C9 C14 1.3947(17) . ?
C9 C10 1.3963(17) . ?
C10 C11 1.3870(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3967(17) . ?
C12 C13 1.3928(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3909(17) . ?
C14 H14 0.9500 . ?
C15 C20 1.3932(17) . ?
C15 C16 1.3952(17) . ?
C16 C17 1.3880(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3914(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3907(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C11 O1 C21 117.28(9) . . ?
C13 O2 C22 117.88(10) . . ?
C2 N1 C1 117.55(10) . . ?
C1 N2 C8 116.66(10) . . ?
N2 C1 N1 126.17(11) . . ?
N2 C1 C9 118.34(10) . . ?
N1 C1 C9 115.50(10) . . ?
N1 C2 C3 121.95(11) . . ?
N1 C2 C15 115.94(10) . . ?
C3 C2 C15 122.08(10) . . ?
C4 C3 C8 119.58(11) . . ?
C4 C3 C2 124.79(11) . . ?
C8 C3 C2 115.61(11) . . ?
C5 C4 C3 120.39(11) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.04(11) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.92(11) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.22(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N2 C8 C3 121.97(11) . . ?
N2 C8 C7 119.17(11) . . ?
C3 C8 C7 118.84(11) . . ?
C14 C9 C10 120.11(11) . . ?
C14 C9 C1 119.97(11) . . ?
C10 C9 C1 119.92(11) . . ?
C11 C10 C9 119.70(11) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
O1 C11 C10 115.29(10) . . ?
O1 C11 C12 123.71(11) . . ?
C10 C11 C12 121.00(11) . . ?
C13 C12 C11 118.47(11) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
O2 C13 C14 114.97(11) . . ?
O2 C13 C12 123.65(11) . . ?
C14 C13 C12 121.37(11) . . ?
C13 C14 C9 119.28(11) . . ?
C13 C14 H14 120.4 . . ?
C9 C14 H14 120.4 . . ?
C20 C15 C16 119.51(11) . . ?
C20 C15 C2 121.83(11) . . ?
C16 C15 C2 118.61(11) . . ?
C17 C16 C15 120.11(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.43(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.68(12) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.29(12) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 119.97(11) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.736
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.136



####################################################################### 
# 
# 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_i17856
_database_code_depnum_ccdc_archive 'CCDC 1996497'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2020-04-14 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O3'
_chemical_formula_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   14.2321(7)
_cell_length_b                   13.7476(6)
_cell_length_c                   19.4973(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3814.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7376
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            103031
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4210
_reflns_number_gt                3215
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0324P)²+2.2681P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0078(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4210
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O1 O 0.76296(8) 0.58490(8) 0.27222(5) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.90501(7) 0.58598(7) 0.36036(5) 0.0191(2) Uani 1 1 d . . . . .
O3 O 0.88830(7) 0.51320(8) 0.48691(5) 0.0196(2) Uani 1 1 d . . . . .
N1 N 0.55976(8) 0.37758(8) 0.50442(6) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.49284(8) 0.41208(9) 0.39461(6) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.56159(10) 0.41614(10) 0.43996(7) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.48279(10) 0.33226(10) 0.52490(7) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.40152(10) 0.32716(10) 0.48196(7) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.31421(10) 0.28564(10) 0.50065(8) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.305554 0.260682 0.545647 0.024 Uiso 1 1 calc R U . . .
C5 C 0.24213(10) 0.28125(11) 0.45422(8) 0.0216(3) Uani 1 1 d . . . . .
H5 H 0.184154 0.252117 0.466917 0.026 Uiso 1 1 calc R U . . .
C6 C 0.25341(11) 0.31971(11) 0.38766(8) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.203261 0.315247 0.355656 0.028 Uiso 1 1 calc R U . . .
C7 C 0.33584(10) 0.36340(11) 0.36866(8) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.342179 0.390294 0.324021 0.025 Uiso 1 1 calc R U . . .
C8 C 0.41155(10) 0.36849(10) 0.41551(7) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.65139(10) 0.46234(10) 0.41946(7) 0.0157(3) Uani 1 1 d . . . . .
C10 C 0.66082(10) 0.50158(10) 0.35393(7) 0.0180(3) Uani 1 1 d . . . . .
H10 H 0.609811 0.499219 0.322548 0.022 Uiso 1 1 calc R U . . .
C11 C 0.74518(10) 0.54409(10) 0.33487(7) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.82027(10) 0.54712(10) 0.38092(7) 0.0163(3) Uani 1 1 d . . . . .
C13 C 0.81032(10) 0.50722(10) 0.44640(7) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.72585(9) 0.46499(10) 0.46578(7) 0.0161(3) Uani 1 1 d . . . . .
H14 H 0.718844 0.438061 0.510361 0.019 Uiso 1 1 calc R U . . .
C15 C 0.48985(10) 0.28637(10) 0.59371(7) 0.0167(3) Uani 1 1 d . . . . .
C16 C 0.53518(10) 0.33756(11) 0.64614(8) 0.0190(3) Uani 1 1 d . . . . .
H16 H 0.557185 0.401731 0.637849 0.023 Uiso 1 1 calc R U . . .
C17 C 0.54831(11) 0.29570(11) 0.70995(8) 0.0212(3) Uani 1 1 d . . . . .
H17 H 0.578462 0.331421 0.745377 0.025 Uiso 1 1 calc R U . . .
C18 C 0.51730(11) 0.20112(11) 0.72227(8) 0.0219(3) Uani 1 1 d . . . . .
H18 H 0.525937 0.172397 0.766132 0.026 Uiso 1 1 calc R U . . .
C19 C 0.47380(11) 0.14914(11) 0.67024(8) 0.0231(3) Uani 1 1 d . . . . .
H19 H 0.453412 0.084347 0.678345 0.028 Uiso 1 1 calc R U . . .
C20 C 0.45991(11) 0.19144(11) 0.60629(8) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.429851 0.155476 0.570945 0.025 Uiso 1 1 calc R U . . .
C21 C 0.68693(13) 0.58943(15) 0.22510(9) 0.0356(4) Uani 1 1 d . . . . .
H21A H 0.708108 0.620143 0.182451 0.053 Uiso 1 1 calc R U . . .
H21B H 0.635728 0.627806 0.245033 0.053 Uiso 1 1 calc R U . . .
H21C H 0.664518 0.523478 0.215299 0.053 Uiso 1 1 calc R U . . .
C22 C 0.92109(12) 0.68140(11) 0.38714(8) 0.0262(4) Uani 1 1 d . . . . .
H22A H 0.982365 0.705106 0.371446 0.039 Uiso 1 1 calc R U . . .
H22B H 0.920262 0.679109 0.437370 0.039 Uiso 1 1 calc R U . . .
H22C H 0.871641 0.725379 0.370939 0.039 Uiso 1 1 calc R U . . .
C23 C 0.88220(11) 0.47265(11) 0.55422(7) 0.0208(3) Uani 1 1 d . . . . .
H23A H 0.867450 0.403179 0.550940 0.031 Uiso 1 1 calc R U . . .
H23B H 0.832572 0.505878 0.580012 0.031 Uiso 1 1 calc R U . . .
H23C H 0.942399 0.481089 0.577889 0.031 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
O1 C11 1.3677(17) . ?
O1 C21 1.4209(19) . ?
O2 C12 1.3786(16) . ?
O2 C22 1.4303(18) . ?
O3 C13 1.3647(16) . ?
O3 C23 1.4284(17) . ?
N1 C2 1.3219(18) . ?
N1 C1 1.3644(18) . ?
N2 C1 1.3200(18) . ?
N2 C8 1.3652(18) . ?
C1 C9 1.4820(19) . ?
C2 C3 1.4296(19) . ?
C2 C15 1.486(2) . ?
C3 C4 1.4152(19) . ?
C3 C8 1.422(2) . ?
C4 C5 1.370(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.369(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(2) . ?
C7 H7 0.9500 . ?
C9 C14 1.3929(19) . ?
C9 C10 1.393(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C12 C13 1.397(2) . ?
C13 C14 1.3876(19) . ?
C14 H14 0.9500 . ?
C15 C20 1.395(2) . ?
C15 C16 1.399(2) . ?
C16 C17 1.383(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C11 O1 C21 117.04(12) . . ?
C12 O2 C22 112.90(11) . . ?
C13 O3 C23 117.32(11) . . ?
C2 N1 C1 118.49(12) . . ?
C1 N2 C8 116.54(12) . . ?
N2 C1 N1 125.91(13) . . ?
N2 C1 C9 118.47(12) . . ?
N1 C1 C9 115.56(12) . . ?
N1 C2 C3 121.12(13) . . ?
N1 C2 C15 114.62(13) . . ?
C3 C2 C15 124.24(13) . . ?
C4 C3 C8 118.95(13) . . ?
C4 C3 C2 125.40(13) . . ?
C8 C3 C2 115.65(12) . . ?
C5 C4 C3 120.34(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.43(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.73(14) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.99(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N2 C8 C7 118.34(13) . . ?
N2 C8 C3 122.17(13) . . ?
C7 C8 C3 119.48(13) . . ?
C14 C9 C10 120.74(13) . . ?
C14 C9 C1 119.50(12) . . ?
C10 C9 C1 119.76(13) . . ?
C11 C10 C9 119.51(13) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
O1 C11 C10 124.93(13) . . ?
O1 C11 C12 114.86(12) . . ?
C10 C11 C12 120.20(13) . . ?
O2 C12 C11 119.61(12) . . ?
O2 C12 C13 120.44(13) . . ?
C11 C12 C13 119.90(13) . . ?
O3 C13 C14 124.89(13) . . ?
O3 C13 C12 115.03(12) . . ?
C14 C13 C12 120.08(13) . . ?
C13 C14 C9 119.57(13) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C20 C15 C16 118.89(13) . . ?
C20 C15 C2 122.38(13) . . ?
C16 C15 C2 118.52(13) . . ?
C17 C16 C15 120.68(14) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.02(14) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.74(14) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.26(14) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.39(14) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.050



