# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ga_201125a_a
_database_code_depnum_ccdc_archive 'CCDC 2090475'
loop_
_audit_author_name
_audit_author_address
'Yi Xing'
;Fudan University
China
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F N O2'
_chemical_formula_weight         207.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.2434(6)
_cell_length_b                   3.8259(2)
_cell_length_c                   19.1220(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.630(2)
_cell_angle_gamma                90
_cell_volume                     967.85(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6835
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      58.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.599
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            11220
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.027
_diffrn_reflns_theta_max         57.995
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2043
_reflns_number_gt                1855
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0634P)²+0.2110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2043
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.52455(6) 0.0066(2) 0.36035(4) 0.0402(2) Uani 1 1 d . . . . .
O1 O 0.14632(6) 0.5815(3) 0.36821(4) 0.0305(2) Uani 1 1 d . . . . .
H1 H 0.1290(15) 0.670(5) 0.3289(12) 0.057(5) Uiso 1 1 d . . . . .
O2 O 0.07296(6) 0.8698(2) 0.24961(4) 0.0286(2) Uani 1 1 d . . . . .
H2A H 0.0280(15) 1.042(5) 0.2561(10) 0.053(5) Uiso 1 1 d . . . . .
H2B H 0.1075(15) 0.920(5) 0.2126(11) 0.053(5) Uiso 1 1 d . . . . .
N1 N 0.16396(8) 0.4735(3) 0.62849(5) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.23915(8) 0.4349(3) 0.36492(6) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.28589(9) 0.3901(3) 0.30153(6) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.251214 0.458434 0.259131 0.033 Uiso 1 1 calc R U . . .
C3 C 0.38167(9) 0.2481(3) 0.29936(6) 0.0293(3) Uani 1 1 d . . . . .
H3 H 0.413172 0.218583 0.256106 0.035 Uiso 1 1 calc R U . . .
C4 C 0.43017(8) 0.1508(3) 0.36144(6) 0.0278(3) Uani 1 1 d . . . . .
C5 C 0.38685(8) 0.1900(3) 0.42494(6) 0.0257(3) Uani 1 1 d . . . . .
H5 H 0.422748 0.120608 0.466802 0.031 Uiso 1 1 calc R U . . .
C6 C 0.29002(8) 0.3319(3) 0.42780(5) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.10762(9) 0.3504(3) 0.57391(6) 0.0308(3) Uani 1 1 d . . . . .
H7 H 0.038918 0.294375 0.580863 0.037 Uiso 1 1 calc R U . . .
C8 C 0.14410(8) 0.3005(3) 0.50799(6) 0.0268(3) Uani 1 1 d . . . . .
H8 H 0.101020 0.213404 0.470892 0.032 Uiso 1 1 calc R U . . .
C9 C 0.24473(8) 0.3793(3) 0.49667(6) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.30375(9) 0.5028(3) 0.55366(6) 0.0265(3) Uani 1 1 d . . . . .
H10 H 0.373050 0.556893 0.548644 0.032 Uiso 1 1 calc R U . . .
C11 C 0.26047(10) 0.5457(3) 0.61758(6) 0.0300(3) Uani 1 1 d . . . . .
H11 H 0.301745 0.631305 0.655764 0.036 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 C4 1.3674(14) . ?
O1 C1 1.3553(14) . ?
O1 H1 0.85(2) . ?
O2 H2A 0.90(2) . ?
O2 H2B 0.88(2) . ?
N1 C11 1.3334(17) . ?
N1 C7 1.3403(17) . ?
C1 C2 1.3966(15) . ?
C1 C6 1.4074(15) . ?
C2 C3 1.3823(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3750(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3746(16) . ?
C5 C6 1.3959(15) . ?
C5 H5 0.9500 . ?
C6 C9 1.4830(14) . ?
C7 C8 1.3838(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3930(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3941(16) . ?
C10 C11 1.3834(16) . ?
C10 H10 0.9500 . ?
C11 H11 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 O1 H1 109.4(13) . . ?
H2A O2 H2B 108.8(18) . . ?
C11 N1 C7 117.02(10) . . ?
O1 C1 C2 122.02(10) . . ?
O1 C1 C6 118.41(10) . . ?
C2 C1 C6 119.55(10) . . ?
C3 C2 C1 121.22(11) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 118.25(10) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
F1 C4 C5 118.45(11) . . ?
F1 C4 C3 119.16(10) . . ?
C5 C4 C3 122.39(11) . . ?
C4 C5 C6 119.90(10) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 118.68(10) . . ?
C5 C6 C9 119.48(10) . . ?
C1 C6 C9 121.81(10) . . ?
N1 C7 C8 123.55(11) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 119.22(11) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.26(10) . . ?
C8 C9 C6 122.71(10) . . ?
C10 C9 C6 120.03(10) . . ?
C11 C10 C9 119.39(11) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.55(11) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.34(11) . . . . ?
C6 C1 C2 C3 -0.40(17) . . . . ?
C1 C2 C3 C4 0.11(18) . . . . ?
C2 C3 C4 F1 179.34(10) . . . . ?
C2 C3 C4 C5 -0.03(19) . . . . ?
F1 C4 C5 C6 -179.13(10) . . . . ?
C3 C4 C5 C6 0.25(18) . . . . ?
C4 C5 C6 C1 -0.53(17) . . . . ?
C4 C5 C6 C9 -178.85(10) . . . . ?
O1 C1 C6 C5 -178.19(10) . . . . ?
C2 C1 C6 C5 0.60(16) . . . . ?
O1 C1 C6 C9 0.10(16) . . . . ?
C2 C1 C6 C9 178.89(10) . . . . ?
C11 N1 C7 C8 -0.9(2) . . . . ?
N1 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 0.61(17) . . . . ?
C7 C8 C9 C6 179.69(11) . . . . ?
C5 C6 C9 C8 -137.84(12) . . . . ?
C1 C6 C9 C8 43.89(16) . . . . ?
C5 C6 C9 C10 41.22(15) . . . . ?
C1 C6 C9 C10 -137.05(12) . . . . ?
C8 C9 C10 C11 -0.90(17) . . . . ?
C6 C9 C10 C11 179.99(10) . . . . ?
C7 N1 C11 C10 0.54(19) . . . . ?
C9 C10 C11 N1 0.34(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.85(2) 1.83(2) 2.6649(12) 171.3(19) .
O2 H2A O2 0.90(2) 1.83(2) 2.7197(12) 168.0(19) 2
O2 H2B N1 0.88(2) 1.85(2) 2.7261(13) 172.6(18) 4_575

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_ga_201106b_a
_database_code_depnum_ccdc_archive 'CCDC 2090477'
loop_
_audit_author_name
_audit_author_address
'Yi Xing'
;Fudan University
China
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.9480(6)
_cell_length_b                   5.7541(3)
_cell_length_c                   23.8405(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.984(3)
_cell_angle_gamma                90
_cell_volume                     1339.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1001
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      31.60

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.456
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            18175
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.286
_diffrn_reflns_theta_max         56.494
_diffrn_reflns_theta_full        53.594
_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             2695
_reflns_number_gt                2359
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0313P)²+0.4768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2695
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85277(11) 1.1176(2) 0.48669(4) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.81350(11) -0.02618(19) 0.80889(4) 0.0304(3) Uani 1 1 d . . . . .
O1 O 0.85375(8) 0.54804(16) 0.65403(4) 0.0275(2) Uani 1 1 d . . . . .
H1 H 0.9031(19) 0.617(3) 0.6292(8) 0.056(5) Uiso 1 1 d . . . . .
O2 O 0.05562(9) 0.66706(16) 0.60552(4) 0.0271(2) Uani 1 1 d . . . . .
H2A H 0.0978(18) 0.765(3) 0.6327(8) 0.052(5) Uiso 1 1 d . . . . .
H2B H 0.0740(19) 0.730(3) 0.5731(9) 0.059(5) Uiso 1 1 d . . . . .
C1 C 0.71592(11) 0.5675(2) 0.64016(5) 0.0205(2) Uani 1 1 d . . . . .
C2 C 0.64877(12) 0.7053(2) 0.59498(5) 0.0219(2) Uani 1 1 d . . . . .
C3 C 0.50599(12) 0.7127(2) 0.58344(5) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.460312 0.805247 0.552619 0.032 Uiso 1 1 calc R U . . .
C4 C 0.42946(12) 0.5885(2) 0.61586(5) 0.0283(3) Uani 1 1 d . . . . .
H4 H 0.332388 0.599122 0.608250 0.034 Uiso 1 1 calc R U . . .
C5 C 0.49654(12) 0.4483(2) 0.65957(5) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.444362 0.359712 0.681380 0.029 Uiso 1 1 calc R U . . .
C6 C 0.63931(11) 0.4344(2) 0.67230(5) 0.0206(2) Uani 1 1 d . . . . .
C7 C 0.85915(14) 1.1727(2) 0.54156(6) 0.0307(3) Uani 1 1 d . . . . .
H7 H 0.908094 1.308597 0.555924 0.037 Uiso 1 1 calc R U . . .
C8 C 0.79837(13) 1.0424(2) 0.57849(5) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.806879 1.087813 0.617317 0.034 Uiso 1 1 calc R U . . .
C9 C 0.72469(11) 0.8446(2) 0.55845(5) 0.0221(2) Uani 1 1 d . . . . .
C10 C 0.71883(14) 0.7859(2) 0.50171(5) 0.0313(3) Uani 1 1 d . . . . .
H10 H 0.670586 0.651066 0.486108 0.038 Uiso 1 1 calc R U . . .
C11 C 0.78399(14) 0.9257(3) 0.46807(5) 0.0343(3) Uani 1 1 d . . . . .
H11 H 0.779407 0.882100 0.429314 0.041 Uiso 1 1 calc R U . . .
C12 C 0.70546(13) -0.0849(2) 0.76905(5) 0.0274(3) Uani 1 1 d . . . . .
H12 H 0.664823 -0.232700 0.771972 0.033 Uiso 1 1 calc R U . . .
C13 C 0.64935(12) 0.0565(2) 0.72388(5) 0.0235(3) Uani 1 1 d . . . . .
H13 H 0.573002 0.004713 0.696507 0.028 Uiso 1 1 calc R U . . .
C14 C 0.70535(11) 0.2758(2) 0.71863(5) 0.0205(2) Uani 1 1 d . . . . .
C15 C 0.81966(12) 0.3366(2) 0.75967(5) 0.0249(3) Uani 1 1 d . . . . .
H15 H 0.863278 0.482405 0.757617 0.030 Uiso 1 1 calc R U . . .
C16 C 0.86874(13) 0.1831(2) 0.80325(5) 0.0304(3) Uani 1 1 d . . . . .
H16 H 0.946229 0.228352 0.830885 0.036 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
N1 C11 1.3303(18) . ?
N1 C7 1.3356(17) . ?
N2 C12 1.3350(17) . ?
N2 C16 1.3410(17) . ?
O1 C1 1.3525(13) . ?
O1 H1 0.93(2) . ?
O2 H2A 0.90(2) . ?
O2 H2B 0.90(2) . ?
C1 C2 1.4004(16) . ?
C1 C6 1.4058(16) . ?
C2 C3 1.3950(16) . ?
C2 C9 1.4906(16) . ?
C3 C4 1.3829(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3845(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3969(16) . ?
C5 H5 0.9500 . ?
C6 C14 1.4861(16) . ?
C7 C8 1.3803(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3885(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3846(17) . ?
C10 C11 1.3816(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.3798(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3947(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3960(16) . ?
C15 C16 1.3802(17) . ?
C15 H15 0.9500 . ?
C16 H16 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
C11 N1 C7 116.69(11) . . ?
C12 N2 C16 116.46(11) . . ?
C1 O1 H1 116.3(11) . . ?
H2A O2 H2B 103.0(16) . . ?
O1 C1 C2 123.20(10) . . ?
O1 C1 C6 116.84(10) . . ?
C2 C1 C6 119.92(10) . . ?
C3 C2 C1 119.18(11) . . ?
C3 C2 C9 118.58(10) . . ?
C1 C2 C9 122.23(10) . . ?
C4 C3 C2 121.48(11) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.96(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 121.40(11) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.00(11) . . ?
C5 C6 C14 118.93(10) . . ?
C1 C6 C14 122.05(10) . . ?
N1 C7 C8 123.44(12) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.50(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 117.22(11) . . ?
C10 C9 C2 120.52(11) . . ?
C8 C9 C2 122.20(11) . . ?
C11 C10 C9 119.21(12) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.92(12) . . ?
N1 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
N2 C12 C13 123.87(12) . . ?
N2 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C12 C13 C14 119.62(11) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 116.74(11) . . ?
C13 C14 C6 119.66(10) . . ?
C15 C14 C6 123.55(11) . . ?
C16 C15 C14 119.42(12) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N2 C16 C15 123.86(12) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?

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
O1 C1 C2 C3 179.32(11) . . . . ?
C6 C1 C2 C3 1.58(17) . . . . ?
O1 C1 C2 C9 -0.50(18) . . . . ?
C6 C1 C2 C9 -178.24(11) . . . . ?
C1 C2 C3 C4 0.48(18) . . . . ?
C9 C2 C3 C4 -179.70(12) . . . . ?
C2 C3 C4 C5 -2.00(19) . . . . ?
C3 C4 C5 C6 1.50(19) . . . . ?
C4 C5 C6 C1 0.51(18) . . . . ?
C4 C5 C6 C14 -178.27(11) . . . . ?
O1 C1 C6 C5 -179.94(10) . . . . ?
C2 C1 C6 C5 -2.05(17) . . . . ?
O1 C1 C6 C14 -1.19(16) . . . . ?
C2 C1 C6 C14 176.69(10) . . . . ?
C11 N1 C7 C8 -0.31(19) . . . . ?
N1 C7 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C10 1.32(18) . . . . ?
C7 C8 C9 C2 -175.79(11) . . . . ?
C3 C2 C9 C10 -68.29(16) . . . . ?
C1 C2 C9 C10 111.53(14) . . . . ?
C3 C2 C9 C8 108.73(14) . . . . ?
C1 C2 C9 C8 -71.45(16) . . . . ?
C8 C9 C10 C11 -0.74(19) . . . . ?
C2 C9 C10 C11 176.42(12) . . . . ?
C7 N1 C11 C10 0.9(2) . . . . ?
C9 C10 C11 N1 -0.4(2) . . . . ?
C16 N2 C12 C13 -0.37(18) . . . . ?
N2 C12 C13 C14 -0.77(19) . . . . ?
C12 C13 C14 C15 1.69(16) . . . . ?
C12 C13 C14 C6 -175.87(11) . . . . ?
C5 C6 C14 C13 40.87(16) . . . . ?
C1 C6 C14 C13 -137.88(11) . . . . ?
C5 C6 C14 C15 -136.51(12) . . . . ?
C1 C6 C14 C15 44.74(17) . . . . ?
C13 C14 C15 C16 -1.53(17) . . . . ?
C6 C14 C15 C16 175.92(11) . . . . ?
C12 N2 C16 C15 0.54(19) . . . . ?
C14 C15 C16 N2 0.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.93(2) 1.740(19) 2.5931(12) 151.4(17) 1_655
O2 H2A N2 0.90(2) 1.92(2) 2.8218(14) 179.5(17) 2_666
O2 H2B N1 0.90(2) 1.93(2) 2.8215(14) 168.6(17) 3_676

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_ga_201027a_a
_database_code_depnum_ccdc_archive 'CCDC 2090476'
loop_
_audit_author_name
_audit_author_address
'Yi Xing'
;Fudan University
China
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 F N2 O2'
_chemical_formula_weight         284.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 '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                   10.5395(10)
_cell_length_b                   10.6712(10)
_cell_length_c                   13.2594(12)
_cell_angle_alpha                76.844(4)
_cell_angle_beta                 85.075(4)
_cell_angle_gamma                72.914(4)
_cell_volume                     1387.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6898
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      55.71

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.532
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            21600
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.818
_diffrn_reflns_theta_max         55.499
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5368
_reflns_number_gt                3902
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0711P)²+0.2802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5368
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.31484(17) 0.36701(17) -0.15622(12) 0.0480(4) Uani 1 1 d . . . . .
N2 N 0.35892(16) -0.27738(16) 0.54274(12) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.34772(14) 0.03640(13) 0.18455(10) 0.0413(3) Uani 1 1 d . . . . .
H1 H 0.412(3) 0.009(3) 0.234(2) 0.085(9) Uiso 1 1 d . . . . .
F1 F -0.12988(13) 0.34879(13) 0.30122(10) 0.0679(4) Uani 1 1 d . . . . .
C1 C 0.23000(18) 0.11053(18) 0.21642(13) 0.0349(4) Uani 1 1 d . . . . .
C2 C 0.16207(19) 0.22599(18) 0.14649(13) 0.0375(4) Uani 1 1 d . . . . .
C3 C 0.0392(2) 0.3041(2) 0.17479(15) 0.0450(5) Uani 1 1 d . . . . .
H3 H -0.008772 0.381209 0.127366 0.054 Uiso 1 1 calc R U . . .
C4 C -0.0117(2) 0.2678(2) 0.27239(16) 0.0475(5) Uani 1 1 d . . . . .
C5 C 0.0519(2) 0.1556(2) 0.34204(15) 0.0444(5) Uani 1 1 d . . . . .
H5 H 0.013307 0.133932 0.408789 0.053 Uiso 1 1 calc R U . . .
C6 C 0.17351(19) 0.07280(18) 0.31520(13) 0.0368(4) Uani 1 1 d . . . . .
C7 C 0.1918(2) 0.3558(2) -0.14086(14) 0.0444(5) Uani 1 1 d . . . . .
H7 H 0.136264 0.381374 -0.199179 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1400(2) 0.30911(19) -0.04519(14) 0.0411(4) Uani 1 1 d . . . . .
H8 H 0.050997 0.304312 -0.038960 0.049 Uiso 1 1 calc R U . . .
C9 C 0.21832(18) 0.26923(18) 0.04188(13) 0.0361(4) Uani 1 1 d . . . . .
C10 C 0.3477(2) 0.2784(2) 0.02641(15) 0.0479(5) Uani 1 1 d . . . . .
H10 H 0.406163 0.251149 0.083039 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3904(2) 0.3273(2) -0.07163(16) 0.0537(5) Uani 1 1 d . . . . .
H11 H 0.478975 0.333470 -0.080152 0.064 Uiso 1 1 calc R U . . .
C12 C 0.3665(2) -0.27992(19) 0.44201(14) 0.0412(4) Uani 1 1 d . . . . .
H12 H 0.413703 -0.361404 0.421964 0.049 Uiso 1 1 calc R U . . .
C13 C 0.30921(19) -0.16998(18) 0.36525(14) 0.0387(4) Uani 1 1 d . . . . .
H13 H 0.317324 -0.177205 0.294745 0.046 Uiso 1 1 calc R U . . .
C14 C 0.23998(18) -0.04941(18) 0.39190(13) 0.0356(4) Uani 1 1 d . . . . .
C15 C 0.2329(2) -0.04710(19) 0.49717(14) 0.0401(4) Uani 1 1 d . . . . .
H15 H 0.187126 0.033037 0.519720 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2923(2) -0.1612(2) 0.56802(14) 0.0429(5) Uani 1 1 d . . . . .
H16 H 0.285481 -0.157050 0.639172 0.051 Uiso 1 1 calc R U . . .
N3 N 0.67608(17) 0.13868(17) 1.15452(12) 0.0463(4) Uani 1 1 d . . . . .
N4 N 0.66050(18) 0.76964(19) 0.45852(12) 0.0497(4) Uani 1 1 d . . . . .
O2 O 0.66884(15) 0.46090(14) 0.81724(10) 0.0429(3) Uani 1 1 d . . . . .
H2 H 0.604(3) 0.493(3) 0.775(2) 0.084(9) Uiso 1 1 d . . . . .
F2 F 1.11193(13) 0.10885(15) 0.68920(10) 0.0707(4) Uani 1 1 d . . . . .
C17 C 0.78011(18) 0.37770(19) 0.78312(13) 0.0370(4) Uani 1 1 d . . . . .
C18 C 0.83883(18) 0.25577(19) 0.85041(13) 0.0373(4) Uani 1 1 d . . . . .
C19 C 0.9501(2) 0.1652(2) 0.81762(15) 0.0450(5) Uani 1 1 d . . . . .
H19 H 0.989814 0.081613 0.862200 0.054 Uiso 1 1 calc R U . . .
C20 C 1.0017(2) 0.1984(2) 0.71973(16) 0.0487(5) Uani 1 1 d . . . . .
C21 C 0.9476(2) 0.3168(2) 0.65298(15) 0.0471(5) Uani 1 1 d . . . . .
H21 H 0.986466 0.336026 0.586002 0.057 Uiso 1 1 calc R U . . .
C22 C 0.8351(2) 0.4099(2) 0.68270(14) 0.0403(4) Uani 1 1 d . . . . .
C23 C 0.6930(2) 0.2612(2) 1.12093(14) 0.0435(5) Uani 1 1 d . . . . .
H23 H 0.668785 0.321842 1.166483 0.052 Uiso 1 1 calc R U . . .
C24 C 0.74357(19) 0.30436(19) 1.02420(14) 0.0406(4) Uani 1 1 d . . . . .
H24 H 0.752970 0.392562 1.004368 0.049 Uiso 1 1 calc R U . . .
C25 C 0.78078(18) 0.21786(18) 0.95571(13) 0.0364(4) Uani 1 1 d . . . . .
C26 C 0.7635(2) 0.0909(2) 0.99042(15) 0.0463(5) Uani 1 1 d . . . . .
H26 H 0.787412 0.027750 0.946920 0.056 Uiso 1 1 calc R U . . .
C27 C 0.7116(2) 0.0572(2) 1.08824(15) 0.0500(5) Uani 1 1 d . . . . .
H27 H 0.700358 -0.030173 1.109892 0.060 Uiso 1 1 calc R U . . .
C28 C 0.6595(2) 0.7703(2) 0.55930(16) 0.0483(5) Uani 1 1 d . . . . .
H28 H 0.618538 0.852407 0.580554 0.058 Uiso 1 1 calc R U . . .
C29 C 0.7150(2) 0.6576(2) 0.63447(15) 0.0454(5) Uani 1 1 d . . . . .
H29 H 0.712434 0.664150 0.704929 0.054 Uiso 1 1 calc R U . . .
C30 C 0.7743(2) 0.5354(2) 0.60695(14) 0.0413(5) Uani 1 1 d . . . . .
C31 C 0.7744(2) 0.5350(2) 0.50147(14) 0.0467(5) Uani 1 1 d . . . . .
H31 H 0.813315 0.454232 0.477893 0.056 Uiso 1 1 calc R U . . .
C32 C 0.7178(2) 0.6522(2) 0.43181(15) 0.0503(5) Uani 1 1 d . . . . .
H32 H 0.719773 0.649102 0.360635 0.060 Uiso 1 1 calc R U . . .
O3 O 0.46935(15) 0.50948(16) 0.70020(12) 0.0473(4) Uani 1 1 d . . . . .
H3A H 0.411(3) 0.475(3) 0.727(2) 0.079(9) Uiso 1 1 d . . . . .
H3B H 0.429(3) 0.578(3) 0.651(2) 0.066(7) Uiso 1 1 d . . . . .
O4 O 0.53445(16) 0.99585(18) 0.31148(12) 0.0515(4) Uani 1 1 d . . . . .
H4A H 0.581(4) 0.919(4) 0.358(3) 0.119(13) Uiso 1 1 d . . . . .
H4B H 0.588(3) 1.034(3) 0.281(2) 0.069(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.332(3) . ?
N1 C11 1.346(3) . ?
N2 C16 1.334(3) . ?
N2 C12 1.337(2) . ?
O1 C1 1.352(2) . ?
O1 H1 0.91(3) . ?
F1 C4 1.371(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.414(2) . ?
C2 C3 1.392(3) . ?
C2 C9 1.489(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C14 1.486(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N3 C27 1.330(3) . ?
N3 C23 1.341(3) . ?
N4 C32 1.335(3) . ?
N4 C28 1.337(3) . ?
O2 C17 1.359(2) . ?
O2 H2 0.86(3) . ?
F2 C20 1.367(2) . ?
C17 C18 1.402(3) . ?
C17 C22 1.415(3) . ?
C18 C19 1.392(3) . ?
C18 C25 1.493(2) . ?
C19 C20 1.374(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.363(3) . ?
C21 C22 1.398(3) . ?
C21 H21 0.9500 . ?
C22 C30 1.486(3) . ?
C23 C24 1.378(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(3) . ?
C26 C27 1.376(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.400(3) . ?
C31 C32 1.379(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
O3 H3A 0.82(3) . ?
O3 H3B 0.88(3) . ?
O4 H4A 0.93(4) . ?
O4 H4B 0.82(3) . ?

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
C7 N1 C11 115.87(16) . . ?
C16 N2 C12 116.61(16) . . ?
C1 O1 H1 113.2(18) . . ?
O1 C1 C2 117.65(15) . . ?
O1 C1 C6 122.17(16) . . ?
C2 C1 C6 120.15(17) . . ?
C3 C2 C1 119.85(16) . . ?
C3 C2 C9 118.37(16) . . ?
C1 C2 C9 121.78(17) . . ?
C4 C3 C2 118.92(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 F1 118.95(17) . . ?
C5 C4 C3 122.55(19) . . ?
F1 C4 C3 118.49(17) . . ?
C4 C5 C6 120.06(17) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 118.40(17) . . ?
C5 C6 C14 119.04(16) . . ?
C1 C6 C14 122.54(17) . . ?
N1 C7 C8 123.91(17) . . ?
N1 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
C7 C8 C9 119.88(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 116.67(16) . . ?
C8 C9 C2 120.67(17) . . ?
C10 C9 C2 122.59(16) . . ?
C11 C10 C9 119.44(18) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 124.2(2) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
N2 C12 C13 123.51(18) . . ?
N2 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C12 C13 C14 119.69(17) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 116.58(17) . . ?
C13 C14 C6 123.42(16) . . ?
C15 C14 C6 119.99(17) . . ?
C16 C15 C14 119.77(18) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N2 C16 C15 123.84(17) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
C27 N3 C23 116.00(16) . . ?
C32 N4 C28 116.48(18) . . ?
C17 O2 H2 115(2) . . ?
O2 C17 C18 117.74(15) . . ?
O2 C17 C22 122.05(17) . . ?
C18 C17 C22 120.20(17) . . ?
C19 C18 C17 119.84(17) . . ?
C19 C18 C25 118.86(17) . . ?
C17 C18 C25 121.24(16) . . ?
C20 C19 C18 118.95(19) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 F2 119.31(18) . . ?
C21 C20 C19 122.52(19) . . ?
F2 C20 C19 118.17(19) . . ?
C20 C21 C22 120.25(18) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 118.22(18) . . ?
C21 C22 C30 119.25(17) . . ?
C17 C22 C30 122.47(18) . . ?
N3 C23 C24 123.81(17) . . ?
N3 C23 H23 118.1 . . ?
C24 C23 H23 118.1 . . ?
C23 C24 C25 119.59(18) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 116.68(17) . . ?
C26 C25 C18 120.38(16) . . ?
C24 C25 C18 122.94(16) . . ?
C27 C26 C25 119.54(18) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
N3 C27 C26 124.38(19) . . ?
N3 C27 H27 117.8 . . ?
C26 C27 H27 117.8 . . ?
N4 C28 C29 123.5(2) . . ?
N4 C28 H28 118.2 . . ?
C29 C28 H28 118.2 . . ?
C30 C29 C28 120.10(18) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 116.16(19) . . ?
C29 C30 C22 123.46(17) . . ?
C31 C30 C22 120.38(18) . . ?
C32 C31 C30 119.9(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
N4 C32 C31 123.85(18) . . ?
N4 C32 H32 118.1 . . ?
C31 C32 H32 118.1 . . ?
H3A O3 H3B 105(3) . . ?
H4A O4 H4B 108(3) . . ?

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
O1 C1 C2 C3 178.62(16) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
O1 C1 C2 C9 -2.0(2) . . . . ?
C6 C1 C2 C9 179.87(16) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C9 C2 C3 C4 -177.77(17) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 F1 177.03(18) . . . . ?
F1 C4 C5 C6 -178.89(18) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
C4 C5 C6 C14 -179.36(17) . . . . ?
O1 C1 C6 C5 179.65(16) . . . . ?
C2 C1 C6 C5 -2.3(2) . . . . ?
O1 C1 C6 C14 1.1(3) . . . . ?
C2 C1 C6 C14 179.14(15) . . . . ?
C11 N1 C7 C8 1.1(3) . . . . ?
N1 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C2 176.51(17) . . . . ?
C3 C2 C9 C8 -46.1(2) . . . . ?
C1 C2 C9 C8 134.47(19) . . . . ?
C3 C2 C9 C10 130.6(2) . . . . ?
C1 C2 C9 C10 -48.8(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C2 C9 C10 C11 -175.84(19) . . . . ?
C7 N1 C11 C10 -0.5(3) . . . . ?
C9 C10 C11 N1 -0.6(4) . . . . ?
C16 N2 C12 C13 -0.2(3) . . . . ?
N2 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C6 -178.94(16) . . . . ?
C5 C6 C14 C13 142.44(18) . . . . ?
C1 C6 C14 C13 -39.0(2) . . . . ?
C5 C6 C14 C15 -36.6(2) . . . . ?
C1 C6 C14 C15 141.99(18) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C6 C14 C15 C16 178.70(16) . . . . ?
C12 N2 C16 C15 -0.1(3) . . . . ?
C14 C15 C16 N2 0.4(3) . . . . ?
O2 C17 C18 C19 177.71(16) . . . . ?
C22 C17 C18 C19 -1.2(3) . . . . ?
O2 C17 C18 C25 0.4(2) . . . . ?
C22 C17 C18 C25 -178.44(16) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C25 C18 C19 C20 178.38(17) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C18 C19 C20 F2 179.31(17) . . . . ?
F2 C20 C21 C22 -179.85(18) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C20 C21 C22 C30 -177.24(17) . . . . ?
O2 C17 C22 C21 -178.21(16) . . . . ?
C18 C17 C22 C21 0.6(3) . . . . ?
O2 C17 C22 C30 -1.0(3) . . . . ?
C18 C17 C22 C30 177.80(16) . . . . ?
C27 N3 C23 C24 0.1(3) . . . . ?
N3 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C23 C24 C25 C18 -178.75(17) . . . . ?
C19 C18 C25 C26 -44.6(3) . . . . ?
C17 C18 C25 C26 132.66(19) . . . . ?
C19 C18 C25 C24 134.28(19) . . . . ?
C17 C18 C25 C24 -48.4(2) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C18 C25 C26 C27 179.10(18) . . . . ?
C23 N3 C27 C26 0.2(3) . . . . ?
C25 C26 C27 N3 -0.4(3) . . . . ?
C32 N4 C28 C29 0.6(3) . . . . ?
N4 C28 C29 C30 -0.8(3) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C28 C29 C30 C22 -179.54(17) . . . . ?
C21 C22 C30 C29 -145.52(19) . . . . ?
C17 C22 C30 C29 37.3(3) . . . . ?
C21 C22 C30 C31 34.6(3) . . . . ?
C17 C22 C30 C31 -142.57(19) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C22 C30 C31 C32 -179.91(17) . . . . ?
C28 N4 C32 C31 0.0(3) . . . . ?
C30 C31 C32 N4 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.91(3) 1.68(3) 2.575(2) 166(3) 1_545
O2 H2 O3 0.86(3) 1.75(3) 2.579(2) 163(3) .
C28 H28 O4 0.95 2.53 3.419(3) 156.0 2_676
O3 H3A N1 0.82(3) 2.09(3) 2.862(2) 157(3) 1_556
O3 H3B N2 0.88(3) 1.87(3) 2.754(2) 175(2) 1_565
O4 H4A N4 0.93(4) 1.86(4) 2.795(2) 175(3) .
O4 H4B N3 0.82(3) 2.10(3) 2.871(2) 158(3) 1_564

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042



