# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_BSK061
_audit_block_doi                 10.5517/ccdc.csd.cc2dy1s6
_database_code_depnum_ccdc_archive 'CCDC 2232458'
loop_
_audit_author_name
_audit_author_address
Dao-Wen-Luo
;Tunghai University
Taiwan
;
_audit_update_record             
;
2022-12-23 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H13 Br O2'
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         317.17

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   10.1139(5)
_cell_length_b                   11.6747(7)
_cell_length_c                   11.8454(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.9428(18)
_cell_angle_gamma                90
_cell_volume                     1322.92(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.753
_cell_measurement_theta_max      27.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    3.101
_shelx_estimated_absorpt_T_min   0.370
_shelx_estimated_absorpt_T_max   0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5911
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            35462
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.893
_diffrn_reflns_theta_max         27.889
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3156
_reflns_number_gt                2873
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0321P)²+0.6515P] 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         3156
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_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
Br Br 0.86138(2) 0.08898(2) 0.13078(2) 0.02319(6) Uani 1 1 d . . . . .
O1 O 0.45329(11) 0.30080(9) 0.32920(9) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.63148(10) 0.13523(8) 0.28884(8) 0.01995(19) Uani 1 1 d . . . . .
C1 C 0.18320(15) 0.34986(12) 0.17834(12) 0.0214(3) Uani 1 1 d . . . . .
H1A H 0.213300 0.383844 0.255379 0.026 Uiso 1 1 calc R U . . .
C2 C 0.05286(15) 0.37621(13) 0.09940(14) 0.0257(3) Uani 1 1 d . . . . .
H2A H -0.006308 0.428190 0.122034 0.031 Uiso 1 1 calc R U . . .
C3 C 0.00853(15) 0.32645(12) -0.01322(13) 0.0250(3) Uani 1 1 d . . . . .
H3A H -0.081065 0.344541 -0.067684 0.030 Uiso 1 1 calc R U . . .
C4 C 0.09455(15) 0.25057(12) -0.04631(12) 0.0246(3) Uani 1 1 d . . . . .
H4A H 0.063505 0.216215 -0.123153 0.029 Uiso 1 1 calc R U . . .
C5 C 0.22608(15) 0.22455(12) 0.03254(12) 0.0217(3) Uani 1 1 d . . . . .
H5A H 0.285365 0.173227 0.009221 0.026 Uiso 1 1 calc R U . . .
C6 C 0.27122(13) 0.27374(11) 0.14599(11) 0.0170(2) Uani 1 1 d . . . . .
C7 C 0.40951(14) 0.24869(11) 0.23560(11) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.49467(13) 0.15439(11) 0.20602(12) 0.0186(2) Uani 1 1 d . . . . .
H8A H 0.441959 0.084796 0.166712 0.022 Uiso 1 1 calc R U . . .
C9 C 0.62255(13) 0.18334(11) 0.17512(11) 0.0164(2) Uani 1 1 d . . . . .
C10 C 0.67089(13) 0.30489(11) 0.17779(11) 0.0160(2) Uani 1 1 d . . . . .
C11 C 0.64697(15) 0.36497(12) 0.07125(12) 0.0220(3) Uani 1 1 d . . . . .
H11A H 0.599374 0.329223 -0.002875 0.026 Uiso 1 1 calc R U . . .
C12 C 0.69319(16) 0.47768(13) 0.07406(14) 0.0264(3) Uani 1 1 d . . . . .
H12A H 0.676506 0.518971 0.001654 0.032 Uiso 1 1 calc R U . . .
C13 C 0.76340(15) 0.52979(12) 0.18200(14) 0.0256(3) Uani 1 1 d . . . . .
H13A H 0.794662 0.606685 0.183473 0.031 Uiso 1 1 calc R U . . .
C14 C 0.78805(15) 0.46978(12) 0.28787(13) 0.0231(3) Uani 1 1 d . . . . .
H14A H 0.836823 0.505353 0.361817 0.028 Uiso 1 1 calc R U . . .
C15 C 0.74131(13) 0.35735(11) 0.28578(12) 0.0187(2) Uani 1 1 d . . . . .
H15A H 0.757640 0.316475 0.358391 0.022 Uiso 1 1 calc R U . . .
C16 C 0.65903(14) 0.10125(11) 0.09199(12) 0.0194(3) Uani 1 1 d . . . . .
H16A H 0.617250 0.128217 0.008720 0.023 Uiso 1 1 calc R U . . .
H16B H 0.619574 0.024850 0.098361 0.023 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
Br C16 1.9518(13) . ?
O1 C7 1.2152(16) . ?
O2 C8 1.4303(15) . ?
O2 C9 1.4351(15) . ?
C1 C2 1.381(2) . ?
C1 C6 1.3966(18) . ?
C1 H1A 0.9500 . ?
C2 C3 1.389(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3949(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4848(18) . ?
C7 C8 1.5075(18) . ?
C8 C9 1.4928(18) . ?
C8 H8A 1.0000 . ?
C9 C10 1.4979(17) . ?
C9 C16 1.5033(18) . ?
C10 C11 1.3947(18) . ?
C10 C15 1.3882(18) . ?
C11 C12 1.393(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3927(19) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C8 O2 C9 62.80(8) . . ?
C2 C1 C6 120.63(13) . . ?
C2 C1 H1A 119.7 . . ?
C6 C1 H1A 119.7 . . ?
C1 C2 C3 119.78(13) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 C4 120.19(13) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 120.16(13) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.04(13) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 119.20(12) . . ?
C5 C6 C7 123.05(12) . . ?
C1 C6 C7 117.75(12) . . ?
O1 C7 C6 122.23(12) . . ?
O1 C7 C8 120.75(12) . . ?
C6 C7 C8 117.03(11) . . ?
O2 C8 C9 58.76(8) . . ?
O2 C8 C7 116.96(11) . . ?
C9 C8 C7 119.84(11) . . ?
O2 C8 H8A 116.3 . . ?
C9 C8 H8A 116.3 . . ?
C7 C8 H8A 116.3 . . ?
O2 C9 C8 58.45(8) . . ?
O2 C9 C10 115.49(10) . . ?
C8 C9 C10 120.81(11) . . ?
O2 C9 C16 114.29(10) . . ?
C8 C9 C16 115.64(11) . . ?
C10 C9 C16 118.03(11) . . ?
C11 C10 C15 119.89(12) . . ?
C11 C10 C9 119.85(12) . . ?
C15 C10 C9 120.25(11) . . ?
C10 C11 C12 119.68(13) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 120.28(13) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.03(13) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.99(13) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C10 C15 C14 120.12(13) . . ?
C10 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C9 C16 Br 110.74(9) . . ?
C9 C16 H16A 109.5 . . ?
Br C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
Br C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?

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
C6 C1 C2 C3 0.1(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 179.09(12) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 -179.57(13) . . . . ?
C5 C6 C7 O1 172.26(13) . . . . ?
C1 C6 C7 O1 -8.03(19) . . . . ?
C5 C6 C7 C8 -8.02(18) . . . . ?
C1 C6 C7 C8 171.68(12) . . . . ?
C9 O2 C8 C7 -110.14(13) . . . . ?
O1 C7 C8 O2 -4.15(18) . . . . ?
C6 C7 C8 O2 176.14(10) . . . . ?
O1 C7 C8 C9 -71.87(17) . . . . ?
C6 C7 C8 C9 108.41(13) . . . . ?
C8 O2 C9 C10 111.90(12) . . . . ?
C8 O2 C9 C16 -106.26(12) . . . . ?
C7 C8 C9 O2 105.27(13) . . . . ?
O2 C8 C9 C10 -102.81(12) . . . . ?
C7 C8 C9 C10 2.46(18) . . . . ?
O2 C8 C9 C16 103.92(12) . . . . ?
C7 C8 C9 C16 -150.81(11) . . . . ?
O2 C9 C10 C11 -170.29(11) . . . . ?
C8 C9 C10 C11 -103.29(15) . . . . ?
C16 C9 C10 C11 49.36(17) . . . . ?
O2 C9 C10 C15 10.71(17) . . . . ?
C8 C9 C10 C15 77.71(16) . . . . ?
C16 C9 C10 C15 -129.64(13) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C12 -179.43(12) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C9 C10 C15 C14 179.00(12) . . . . ?
C13 C14 C15 C10 0.5(2) . . . . ?
O2 C9 C16 Br -80.75(12) . . . . ?
C8 C9 C16 Br -145.90(9) . . . . ?
C10 C9 C16 Br 60.06(13) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.053

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_BSK020_1
_audit_block_doi                 10.5517/ccdc.csd.cc2dy1q4
_database_code_depnum_ccdc_archive 'CCDC 2232456'
loop_
_audit_author_name
_audit_author_address
Dao-Wen-Luo
;Tunghai University
Taiwan
;
_audit_update_record             
;
2022-12-23 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H11 N O5'
_chemical_formula_sum            'C17 H11 N O5'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         309.27

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

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

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

_cell_length_a                   14.3346(9)
_cell_length_b                   12.1876(8)
_cell_length_c                   7.9189(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.995(3)
_cell_angle_gamma                90
_cell_volume                     1381.58(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9470
_cell_measurement_theta_min      2.846
_cell_measurement_theta_max      27.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6299
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            21696
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.071
_diffrn_reflns_theta_max         27.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3314
_reflns_number_gt                2653
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0591P)²+0.9166P] 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         3314
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.44021(8) 0.36482(9) 1.11013(14) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.32027(9) 0.36424(11) 1.27491(15) 0.0313(3) Uani 1 1 d . . . . .
O3 O 0.29712(9) 0.60485(11) 0.69877(17) 0.0337(3) Uani 1 1 d . . . . .
O4 O 0.14850(9) 0.48197(12) 0.95805(18) 0.0375(3) Uani 1 1 d . . . . .
O5 O 0.14997(10) 0.32025(12) 1.0720(2) 0.0407(4) Uani 1 1 d . . . . .
N N 0.18846(10) 0.39782(12) 1.00641(18) 0.0268(3) Uani 1 1 d . . . . .
C1 C 0.47646(11) 0.37150(12) 0.9525(2) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.57234(12) 0.36124(13) 0.9483(2) 0.0261(4) Uani 1 1 d . . . . .
H2A H 0.609866 0.350869 1.049540 0.031 Uiso 1 1 calc R U . . .
C3 C 0.61246(12) 0.36645(14) 0.7930(2) 0.0285(4) Uani 1 1 d . . . . .
H3A H 0.678215 0.359092 0.787646 0.034 Uiso 1 1 calc R U . . .
C4 C 0.55750(13) 0.38236(14) 0.6446(2) 0.0280(4) Uani 1 1 d . . . . .
H4A H 0.585877 0.385627 0.538997 0.034 Uiso 1 1 calc R U . . .
C5 C 0.46210(12) 0.39337(13) 0.6509(2) 0.0247(3) Uani 1 1 d . . . . .
H5A H 0.425125 0.404874 0.549347 0.030 Uiso 1 1 calc R U . . .
C6 C 0.41890(11) 0.38774(12) 0.8060(2) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.31955(11) 0.39756(12) 0.8227(2) 0.0207(3) Uani 1 1 d . . . . .
C8 C 0.28837(11) 0.38950(13) 0.9802(2) 0.0224(3) Uani 1 1 d . . . . .
C9 C 0.34715(12) 0.37174(13) 1.1334(2) 0.0230(3) Uani 1 1 d . . . . .
C10 C 0.25428(12) 0.41642(14) 0.6698(2) 0.0236(3) Uani 1 1 d . . . . .
H10A H 0.191810 0.386640 0.691764 0.028 Uiso 1 1 calc R U . . .
H10B H 0.277946 0.376738 0.571691 0.028 Uiso 1 1 calc R U . . .
C11 C 0.24569(11) 0.53816(14) 0.6279(2) 0.0230(3) Uani 1 1 d . . . . .
C12 C 0.17275(11) 0.57235(14) 0.4973(2) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.16002(14) 0.68457(16) 0.4687(2) 0.0335(4) Uani 1 1 d . . . . .
H13A H 0.198427 0.736086 0.529656 0.040 Uiso 1 1 calc R U . . .
C14 C 0.09183(16) 0.72107(18) 0.3521(3) 0.0425(5) Uani 1 1 d . . . . .
H14A H 0.082679 0.797493 0.334361 0.051 Uiso 1 1 calc R U . . .
C15 C 0.03698(14) 0.64599(19) 0.2614(3) 0.0387(5) Uani 1 1 d . . . . .
H15A H -0.009719 0.671080 0.180968 0.046 Uiso 1 1 calc R U . . .
C16 C 0.04968(13) 0.53451(18) 0.2869(2) 0.0343(4) Uani 1 1 d . . . . .
H16A H 0.012143 0.483417 0.223355 0.041 Uiso 1 1 calc R U . . .
C17 C 0.11726(12) 0.49723(16) 0.4055(2) 0.0287(4) Uani 1 1 d . . . . .
H17A H 0.125587 0.420741 0.423801 0.034 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 C9 1.359(2) . ?
O1 C1 1.3793(19) . ?
O2 C9 1.208(2) . ?
O3 C11 1.215(2) . ?
O4 N 1.2262(19) . ?
O5 N 1.224(2) . ?
N C8 1.461(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.386(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.406(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.442(2) . ?
C7 C8 1.350(2) . ?
C7 C10 1.509(2) . ?
C8 C9 1.456(2) . ?
C10 C11 1.524(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.491(2) . ?
C12 C17 1.393(2) . ?
C12 C13 1.397(3) . ?
C13 C14 1.383(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 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
C9 O1 C1 122.53(13) . . ?
O5 N O4 124.41(15) . . ?
O5 N C8 118.26(14) . . ?
O4 N C8 117.32(14) . . ?
O1 C1 C2 115.99(14) . . ?
O1 C1 C6 121.60(14) . . ?
C2 C1 C6 122.40(15) . . ?
C1 C2 C3 118.43(16) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 C4 120.80(16) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 120.12(16) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.67(16) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 117.57(15) . . ?
C1 C6 C7 118.49(14) . . ?
C5 C6 C7 123.94(15) . . ?
C8 C7 C6 117.05(14) . . ?
C8 C7 C10 122.08(15) . . ?
C6 C7 C10 120.86(14) . . ?
C7 C8 C9 125.10(15) . . ?
C7 C8 N 120.02(14) . . ?
C9 C8 N 114.88(14) . . ?
O2 C9 O1 118.95(15) . . ?
O2 C9 C8 125.83(16) . . ?
O1 C9 C8 115.21(14) . . ?
C7 C10 C11 111.27(13) . . ?
C7 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C7 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 C12 121.34(16) . . ?
O3 C11 C10 120.70(15) . . ?
C12 C11 C10 117.96(14) . . ?
C17 C12 C13 119.52(16) . . ?
C17 C12 C11 122.63(16) . . ?
C13 C12 C11 117.85(15) . . ?
C14 C13 C12 120.35(18) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.44(18) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 120.09(18) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C12 119.79(18) . . ?
C16 C17 H17A 120.1 . . ?
C12 C17 H17A 120.1 . . ?

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
C9 O1 C1 C2 -178.95(14) . . . . ?
C9 O1 C1 C6 1.1(2) . . . . ?
O1 C1 C2 C3 179.50(14) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
O1 C1 C6 C5 -179.94(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
O1 C1 C6 C7 0.0(2) . . . . ?
C2 C1 C6 C7 -179.98(15) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 -179.46(15) . . . . ?
C1 C6 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C8 179.45(15) . . . . ?
C1 C6 C7 C10 179.29(14) . . . . ?
C5 C6 C7 C10 -0.8(2) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C10 C7 C8 C9 -179.79(15) . . . . ?
C6 C7 C8 N -179.53(14) . . . . ?
C10 C7 C8 N 0.7(2) . . . . ?
O5 N C8 C7 120.71(18) . . . . ?
O4 N C8 C7 -58.0(2) . . . . ?
O5 N C8 C9 -58.9(2) . . . . ?
O4 N C8 C9 122.39(17) . . . . ?
C1 O1 C9 O2 179.35(14) . . . . ?
C1 O1 C9 C8 -1.5(2) . . . . ?
C7 C8 C9 O2 -179.92(16) . . . . ?
N C8 C9 O2 -0.4(2) . . . . ?
C7 C8 C9 O1 1.0(2) . . . . ?
N C8 C9 O1 -179.48(13) . . . . ?
C8 C7 C10 C11 93.81(18) . . . . ?
C6 C7 C10 C11 -85.95(18) . . . . ?
C7 C10 C11 O3 9.6(2) . . . . ?
C7 C10 C11 C12 -170.62(14) . . . . ?
O3 C11 C12 C17 175.35(17) . . . . ?
C10 C11 C12 C17 -4.4(2) . . . . ?
O3 C11 C12 C13 -5.2(2) . . . . ?
C10 C11 C12 C13 175.03(15) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
C11 C12 C13 C14 -178.41(18) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C12 -0.6(3) . . . . ?
C13 C12 C17 C16 -0.2(3) . . . . ?
C11 C12 C17 C16 179.22(16) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_wc367
_database_code_depnum_ccdc_archive 'CCDC 2233123'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;Tunghai University, Taichung
Taiwan
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H12 N2 O4'
_chemical_formula_sum            'C17 H12 N2 O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            red

_diffrn_ambient_temperature      299(2)
_chemical_formula_weight         308.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9701(6)
_cell_length_b                   13.2908(8)
_cell_length_c                   15.0201(8)
_cell_angle_alpha                95.001(2)
_cell_angle_beta                 105.659(2)
_cell_angle_gamma                110.163(2)
_cell_volume                     1762.88(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      26.44
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29560
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         26.44
_reflns_number_total             7212
_reflns_number_gt                5010
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1806P)²+0.4219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7212
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2894
_refine_ls_wR_factor_gt          0.2620
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0383(2) 0.78143(15) 0.68543(14) 0.0479(5) Uani 1 1 d . . .
O2 O 0.3857(3) 0.7091(2) 0.6834(2) 0.0852(8) Uani 1 1 d . . .
O3 O 0.5798(3) 0.85503(19) 0.69830(19) 0.0688(6) Uani 1 1 d . . .
O4 O 0.9024(3) 1.02069(16) 0.7887(2) 0.0689(7) Uani 1 1 d . . .
N1 N 0.5237(3) 0.7560(2) 0.69754(17) 0.0519(6) Uani 1 1 d . . .
N2 N 1.1041(3) 0.9579(2) 0.7321(2) 0.0570(6) Uani 1 1 d . . .
H2B H 1.0755 1.0005 0.7450 0.077(13) Uiso 1 1 calc R . .
H2C H 1.2055 0.9652 0.7222 0.104(14) Uiso 1 1 d R . .
C1 C 0.9545(3) 0.6730(2) 0.68154(18) 0.0418(6) Uani 1 1 d . . .
C2 C 1.0154(3) 0.5996(2) 0.6567(2) 0.0535(7) Uani 1 1 d . . .
H2A H 1.1069 0.6234 0.6447 0.064 Uiso 1 1 calc R . .
C3 C 0.9347(4) 0.4894(3) 0.6505(3) 0.0629(8) Uani 1 1 d . . .
H3A H 0.9719 0.4381 0.6333 0.075 Uiso 1 1 calc R . .
C4 C 0.8002(3) 0.4551(2) 0.6697(2) 0.0588(8) Uani 1 1 d . . .
H4A H 0.7483 0.3811 0.6662 0.071 Uiso 1 1 calc R . .
C5 C 0.7418(3) 0.5296(2) 0.6937(2) 0.0468(6) Uani 1 1 d . . .
H5A H 0.6511 0.5052 0.7067 0.056 Uiso 1 1 calc R . .
C6 C 0.8174(3) 0.64151(19) 0.69894(16) 0.0382(5) Uani 1 1 d . . .
C7 C 0.7603(3) 0.72640(19) 0.71983(16) 0.0362(5) Uani 1 1 d . . .
C8 C 0.8679(3) 0.83610(19) 0.74538(18) 0.0393(5) Uani 1 1 d . . .
C9 C 1.0020(3) 0.8607(2) 0.72256(18) 0.0420(6) Uani 1 1 d . . .
C10 C 0.6093(3) 0.6915(2) 0.70892(18) 0.0434(6) Uani 1 1 d . . .
H10A H 0.5594 0.6181 0.7091 0.052 Uiso 1 1 calc R . .
C11 C 0.8537(3) 0.9268(2) 0.8015(2) 0.0467(6) Uani 1 1 d . . .
C12 C 0.7935(3) 0.9057(2) 0.8822(2) 0.0473(6) Uani 1 1 d . . .
C13 C 0.8009(3) 0.8208(2) 0.92847(19) 0.0511(7) Uani 1 1 d . . .
H13A H 0.8408 0.7732 0.9075 0.061 Uiso 1 1 calc R . .
C14 C 0.7495(4) 0.8060(3) 1.0057(2) 0.0656(8) Uani 1 1 d . . .
H14A H 0.7558 0.7493 1.0366 0.079 Uiso 1 1 calc R . .
C15 C 0.6888(4) 0.8764(3) 1.0359(3) 0.0770(11) Uani 1 1 d . . .
H15A H 0.6527 0.8665 1.0868 0.092 Uiso 1 1 calc R . .
C16 C 0.6820(5) 0.9603(3) 0.9912(3) 0.0858(13) Uani 1 1 d . . .
H16A H 0.6411 1.0072 1.0121 0.103 Uiso 1 1 calc R . .
C17 C 0.7350(4) 0.9771(3) 0.9151(3) 0.0691(9) Uani 1 1 d . . .
H17A H 0.7314 1.0357 0.8863 0.083 Uiso 1 1 calc R . .
O5 O 0.9685(2) 0.56513(15) 0.11241(14) 0.0459(5) Uani 1 1 d . . .
O6 O 0.3133(2) 0.5026(2) 0.0943(2) 0.0773(7) Uani 1 1 d . . .
O7 O 0.5170(2) 0.64842(17) 0.12921(16) 0.0586(5) Uani 1 1 d . . .
O8 O 0.8505(3) 0.80348(15) 0.23721(17) 0.0604(6) Uani 1 1 d . . .
N3 N 0.4525(2) 0.5474(2) 0.11678(16) 0.0470(5) Uani 1 1 d . . .
N4 N 1.0387(3) 0.7413(2) 0.1645(2) 0.0603(7) Uani 1 1 d . . .
H7A H 1.1171 0.7483 0.1480 0.082(12) Uiso 1 1 calc R . .
H7B H 1.0290 0.7982 0.1893 0.073(11) Uiso 1 1 calc R . .
C18 C 0.8830(3) 0.4569(2) 0.10668(16) 0.0391(5) Uani 1 1 d . . .
C19 C 0.9433(3) 0.3824(2) 0.08458(19) 0.0490(6) Uani 1 1 d . . .
H19A H 1.0360 0.4055 0.0740 0.059 Uiso 1 1 calc R . .
C20 C 0.8627(3) 0.2734(3) 0.0787(2) 0.0606(8) Uani 1 1 d . . .
H20A H 0.9004 0.2218 0.0630 0.073 Uiso 1 1 calc R . .
C21 C 0.7249(4) 0.2394(3) 0.0959(3) 0.0679(9) Uani 1 1 d . . .
H21A H 0.6738 0.1660 0.0952 0.081 Uiso 1 1 calc R . .
C22 C 0.6646(3) 0.3149(2) 0.1140(2) 0.0535(7) Uani 1 1 d . . .
H22A H 0.5707 0.2913 0.1229 0.064 Uiso 1 1 calc R . .
C23 C 0.7416(3) 0.4258(2) 0.11924(16) 0.0385(5) Uani 1 1 d . . .
C24 C 0.6867(3) 0.51163(19) 0.13940(16) 0.0360(5) Uani 1 1 d . . .
C25 C 0.7993(3) 0.61999(19) 0.17387(17) 0.0373(5) Uani 1 1 d . . .
C26 C 0.9339(3) 0.6439(2) 0.15191(18) 0.0424(6) Uani 1 1 d . . .
C27 C 0.5339(3) 0.4800(2) 0.12143(18) 0.0425(6) Uani 1 1 d . . .
H27A H 0.4784 0.4052 0.1112 0.051 Uiso 1 1 calc R . .
C28 C 0.7893(3) 0.7059(2) 0.23733(19) 0.0412(5) Uani 1 1 d . . .
C29 C 0.7222(3) 0.6748(2) 0.31443(17) 0.0406(5) Uani 1 1 d . . .
C30 C 0.7282(3) 0.5861(2) 0.35397(18) 0.0438(6) Uani 1 1 d . . .
H30A H 0.7650 0.5389 0.3287 0.053 Uiso 1 1 calc R . .
C31 C 0.6791(3) 0.5668(3) 0.4317(2) 0.0584(8) Uani 1 1 d . . .
H31A H 0.6850 0.5077 0.4591 0.070 Uiso 1 1 calc R . .
C32 C 0.6215(4) 0.6360(3) 0.4678(2) 0.0670(9) Uani 1 1 d . . .
H32A H 0.5877 0.6229 0.5192 0.080 Uiso 1 1 calc R . .
C33 C 0.6141(4) 0.7240(3) 0.4281(2) 0.0682(9) Uani 1 1 d . . .
H33A H 0.5740 0.7696 0.4522 0.082 Uiso 1 1 calc R . .
C34 C 0.6658(3) 0.7450(2) 0.3526(2) 0.0539(7) Uani 1 1 d . . .
H34A H 0.6632 0.8058 0.3271 0.065 Uiso 1 1 calc R . .


_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 C9 1.350(3) . ?
O1 C1 1.381(3) . ?
O2 N1 1.247(3) . ?
O3 N1 1.238(3) . ?
O4 C11 1.226(3) . ?
N1 C10 1.394(3) . ?
N2 C9 1.307(3) . ?
N2 H2B 0.7500 . ?
N2 H2C 1.0341 . ?
C1 C2 1.387(4) . ?
C1 C6 1.389(3) . ?
C2 C3 1.388(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.474(3) . ?
C7 C10 1.372(3) . ?
C7 C8 1.423(3) . ?
C8 C9 1.406(3) . ?
C8 C11 1.480(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.499(4) . ?
C12 C13 1.388(4) . ?
C12 C17 1.393(4) . ?
C13 C14 1.392(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.382(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.363(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
O5 C26 1.349(3) . ?
O5 C18 1.378(3) . ?
O6 N3 1.240(3) . ?
O7 N3 1.244(3) . ?
O8 C28 1.229(3) . ?
N3 C27 1.395(3) . ?
N4 C26 1.312(3) . ?
N4 H7A 0.8600 . ?
N4 H7B 0.8600 . ?
C18 C19 1.383(3) . ?
C18 C23 1.396(3) . ?
C19 C20 1.375(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.394(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.378(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.390(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.467(3) . ?
C24 C27 1.374(3) . ?
C24 C25 1.430(3) . ?
C25 C26 1.404(3) . ?
C25 C28 1.471(3) . ?
C27 H27A 0.9300 . ?
C28 C29 1.507(3) . ?
C29 C30 1.378(4) . ?
C29 C34 1.398(4) . ?
C30 C31 1.394(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.384(5) . ?
C31 H31A 0.9300 . ?
C32 C33 1.373(5) . ?
C32 H32A 0.9300 . ?
C33 C34 1.378(5) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 119.92(19) . . ?
O3 N1 O2 120.7(3) . . ?
O3 N1 C10 122.1(2) . . ?
O2 N1 C10 117.1(3) . . ?
C9 N2 H2B 109.5 . . ?
C9 N2 H2C 119.6 . . ?
H2B N2 H2C 130.9 . . ?
O1 C1 C2 115.2(2) . . ?
O1 C1 C6 121.3(2) . . ?
C2 C1 C6 123.5(2) . . ?
C1 C2 C3 117.5(3) . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 H2A 121.2 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 116.8(2) . . ?
C1 C6 C7 118.6(2) . . ?
C5 C6 C7 124.6(2) . . ?
C10 C7 C8 127.5(2) . . ?
C10 C7 C6 116.7(2) . . ?
C8 C7 C6 115.8(2) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 C11 116.5(2) . . ?
C7 C8 C11 124.0(2) . . ?
N2 C9 O1 111.6(2) . . ?
N2 C9 C8 126.8(2) . . ?
O1 C9 C8 121.6(2) . . ?
C7 C10 N1 125.9(2) . . ?
C7 C10 H10A 117.1 . . ?
N1 C10 H10A 117.1 . . ?
O4 C11 C8 121.4(2) . . ?
O4 C11 C12 119.2(2) . . ?
C8 C11 C12 119.2(2) . . ?
C13 C12 C17 118.8(3) . . ?
C13 C12 C11 122.4(2) . . ?
C17 C12 C11 118.8(3) . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16A 119.3 . . ?
C17 C16 H16A 119.3 . . ?
C16 C17 C12 119.6(3) . . ?
C16 C17 H17A 120.2 . . ?
C12 C17 H17A 120.2 . . ?
C26 O5 C18 119.54(18) . . ?
O6 N3 O7 121.3(2) . . ?
O6 N3 C27 117.6(2) . . ?
O7 N3 C27 120.9(2) . . ?
C26 N4 H7A 120.0 . . ?
C26 N4 H7B 120.0 . . ?
H7A N4 H7B 120.0 . . ?
O5 C18 C19 116.0(2) . . ?
O5 C18 C23 121.0(2) . . ?
C19 C18 C23 122.9(2) . . ?
C20 C19 C18 118.2(2) . . ?
C20 C19 H19A 120.9 . . ?
C18 C19 H19A 120.9 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C21 C22 C23 121.3(3) . . ?
C21 C22 H22A 119.4 . . ?
C23 C22 H22A 119.4 . . ?
C22 C23 C18 117.0(2) . . ?
C22 C23 C24 124.8(2) . . ?
C18 C23 C24 118.2(2) . . ?
C27 C24 C25 127.3(2) . . ?
C27 C24 C23 117.0(2) . . ?
C25 C24 C23 115.7(2) . . ?
C26 C25 C24 118.1(2) . . ?
C26 C25 C28 117.4(2) . . ?
C24 C25 C28 124.4(2) . . ?
N4 C26 O5 111.5(2) . . ?
N4 C26 C25 126.5(2) . . ?
O5 C26 C25 122.0(2) . . ?
C24 C27 N3 127.3(2) . . ?
C24 C27 H27A 116.4 . . ?
N3 C27 H27A 116.4 . . ?
O8 C28 C25 122.0(2) . . ?
O8 C28 C29 118.5(2) . . ?
C25 C28 C29 118.9(2) . . ?
C30 C29 C34 119.5(2) . . ?
C30 C29 C28 122.0(2) . . ?
C34 C29 C28 118.2(2) . . ?
C29 C30 C31 120.2(3) . . ?
C29 C30 H30A 119.9 . . ?
C31 C30 H30A 119.9 . . ?
C32 C31 C30 119.6(3) . . ?
C32 C31 H31A 120.2 . . ?
C30 C31 H31A 120.2 . . ?
C33 C32 C31 120.4(3) . . ?
C33 C32 H32A 119.8 . . ?
C31 C32 H32A 119.8 . . ?
C32 C33 C34 120.2(3) . . ?
C32 C33 H33A 119.9 . . ?
C34 C33 H33A 119.9 . . ?
C33 C34 C29 120.1(3) . . ?
C33 C34 H34A 120.0 . . ?
C29 C34 H34A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.088

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.006 0.000 0.500 392 70 ' '
_platon_squeeze_details          
; 
;
####################################################################### 
# 
# 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_BSK054
_audit_block_doi                 10.5517/ccdc.csd.cc2dy1r5
_database_code_depnum_ccdc_archive 'CCDC 2232457'
loop_
_audit_author_name
_audit_author_address
Dao-Wen-Luo
;Tunghai University
Taiwan
;
_audit_update_record             
;
2022-12-23 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H11 N O2'
_chemical_formula_sum            'C17 H11 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         261.27

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      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                   13.1240(5)
_cell_length_b                   7.1357(3)
_cell_length_c                   13.3340(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.3102(15)
_cell_angle_gamma                90
_cell_volume                     1238.56(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      3.080
_cell_measurement_theta_max      27.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            43722
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         27.906
_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             2969
_reflns_number_gt                2162
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0744P)²+0.7917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2969
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.72358(10) 0.09609(19) 0.52895(9) 0.0341(3) Uani 1 1 d . . . . .
O2 O 0.86722(11) 0.0476(2) 0.45985(10) 0.0385(4) Uani 1 1 d . . . . .
N N 0.98290(12) 0.0727(2) 0.66811(11) 0.0295(4) Uani 1 1 d . . . . .
H0A H 1.029952 0.054788 0.627599 0.085(10) Uiso 1 1 calc R . . . .
C1 C 0.67160(15) 0.1306(3) 0.61039(13) 0.0307(4) Uani 1 1 d . . . . .
C2 C 0.56742(15) 0.1628(3) 0.58809(15) 0.0376(5) Uani 1 1 d . . . . .
H2A H 0.535392 0.157260 0.520132 0.045 Uiso 1 1 calc R U . . .
C3 C 0.51015(16) 0.2032(3) 0.66548(16) 0.0423(5) Uani 1 1 d . . . . .
H3A H 0.438385 0.224996 0.650852 0.051 Uiso 1 1 calc R U . . .
C4 C 0.55768(15) 0.2120(3) 0.76500(15) 0.0408(5) Uani 1 1 d . . . . .
H4A H 0.518144 0.239630 0.818085 0.049 Uiso 1 1 calc R U . . .
C5 C 0.66166(15) 0.1808(3) 0.78669(14) 0.0351(4) Uani 1 1 d . . . . .
H5A H 0.693280 0.187820 0.854748 0.042 Uiso 1 1 calc R U . . .
C6 C 0.72159(14) 0.1387(3) 0.70969(13) 0.0293(4) Uani 1 1 d . . . . .
C7 C 0.83126(14) 0.1129(2) 0.72319(13) 0.0269(4) Uani 1 1 d . . . . .
C8 C 0.90808(13) 0.1200(3) 0.80714(13) 0.0274(4) Uani 1 1 d . . . . .
H8A H 0.897529 0.138477 0.875618 0.033 Uiso 1 1 calc R U . . .
C9 C 1.00177(14) 0.0952(2) 0.77156(13) 0.0277(4) Uani 1 1 d . . . . .
C10 C 0.88025(14) 0.0828(2) 0.63884(13) 0.0283(4) Uani 1 1 d . . . . .
C11 C 0.82850(15) 0.0730(3) 0.53841(14) 0.0303(4) Uani 1 1 d . . . . .
C12 C 1.10479(14) 0.0995(2) 0.82773(14) 0.0290(4) Uani 1 1 d . . . . .
C13 C 1.11734(15) 0.1115(3) 0.93298(15) 0.0353(4) Uani 1 1 d . . . . .
H13A H 1.058440 0.115418 0.967620 0.042 Uiso 1 1 calc R U . . .
C14 C 1.21402(16) 0.1179(3) 0.98770(16) 0.0395(5) Uani 1 1 d . . . . .
H14A H 1.221094 0.125745 1.059369 0.047 Uiso 1 1 calc R U . . .
C15 C 1.30056(16) 0.1128(3) 0.93838(18) 0.0418(5) Uani 1 1 d . . . . .
H15A H 1.367104 0.117189 0.975873 0.050 Uiso 1 1 calc R U . . .
C16 C 1.28944(16) 0.1014(3) 0.83466(17) 0.0450(5) Uani 1 1 d . . . . .
H16A H 1.348742 0.097936 0.800603 0.054 Uiso 1 1 calc R U . . .
C17 C 1.19276(15) 0.0949(3) 0.77915(16) 0.0377(5) Uani 1 1 d . . . . .
H17A H 1.186387 0.087230 0.707497 0.045 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 1.377(2) . ?
O1 C1 1.376(2) . ?
O2 C11 1.234(2) . ?
N C10 1.356(2) . ?
N C9 1.379(2) . ?
N H0A 0.8800 . ?
C1 C2 1.381(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.382(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.403(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.439(3) . ?
C7 C10 1.382(2) . ?
C7 C8 1.409(3) . ?
C8 C9 1.384(2) . ?
C8 H8A 0.9500 . ?
C9 C12 1.460(3) . ?
C10 C11 1.424(3) . ?
C12 C13 1.395(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.375(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 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 O1 C1 122.66(14) . . ?
C10 N C9 109.09(14) . . ?
C10 N H0A 125.5 . . ?
C9 N H0A 125.5 . . ?
O1 C1 C2 115.88(16) . . ?
O1 C1 C6 122.22(17) . . ?
C2 C1 C6 121.86(17) . . ?
C1 C2 C3 119.44(18) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 120.01(19) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.28(19) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.93(17) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C1 117.48(17) . . ?
C5 C6 C7 125.49(16) . . ?
C1 C6 C7 116.94(16) . . ?
C10 C7 C8 107.00(16) . . ?
C10 C7 C6 118.66(16) . . ?
C8 C7 C6 134.26(16) . . ?
C9 C8 C7 107.47(15) . . ?
C9 C8 H8A 126.3 . . ?
C7 C8 H8A 126.3 . . ?
N C9 C8 107.65(16) . . ?
N C9 C12 123.51(16) . . ?
C8 C9 C12 128.78(16) . . ?
N C10 C7 108.79(16) . . ?
N C10 C11 127.28(16) . . ?
C7 C10 C11 123.88(18) . . ?
O2 C11 O1 117.06(16) . . ?
O2 C11 C10 127.34(18) . . ?
O1 C11 C10 115.61(15) . . ?
C13 C12 C17 118.05(18) . . ?
C13 C12 C9 120.03(16) . . ?
C17 C12 C9 121.91(18) . . ?
C14 C13 C12 121.08(18) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C17 120.80(19) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?

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
C11 O1 C1 C2 175.86(17) . . . . ?
C11 O1 C1 C6 -2.1(3) . . . . ?
O1 C1 C2 C3 -178.38(19) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 176.70(19) . . . . ?
O1 C1 C6 C5 177.98(17) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
O1 C1 C6 C7 1.2(3) . . . . ?
C2 C1 C6 C7 -176.63(18) . . . . ?
C5 C6 C7 C10 -176.25(18) . . . . ?
C1 C6 C7 C10 0.2(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C1 C6 C7 C8 176.31(19) . . . . ?
C10 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C9 -176.06(19) . . . . ?
C10 N C9 C8 -0.1(2) . . . . ?
C10 N C9 C12 -177.42(16) . . . . ?
C7 C8 C9 N -0.2(2) . . . . ?
C7 C8 C9 C12 176.98(17) . . . . ?
C9 N C10 C7 0.3(2) . . . . ?
C9 N C10 C11 177.75(17) . . . . ?
C8 C7 C10 N -0.4(2) . . . . ?
C6 C7 C10 N 176.66(16) . . . . ?
C8 C7 C10 C11 -177.96(17) . . . . ?
C6 C7 C10 C11 -0.9(3) . . . . ?
C1 O1 C11 O2 -178.14(17) . . . . ?
C1 O1 C11 C10 1.4(2) . . . . ?
N C10 C11 O2 2.5(3) . . . . ?
C7 C10 C11 O2 179.57(19) . . . . ?
N C10 C11 O1 -176.97(16) . . . . ?
C7 C10 C11 O1 0.1(3) . . . . ?
N C9 C12 C13 -176.20(16) . . . . ?
C8 C9 C12 C13 7.1(3) . . . . ?
N C9 C12 C17 4.9(3) . . . . ?
C8 C9 C12 C17 -171.89(18) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C9 C12 C13 C14 -179.28(17) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C9 C12 C17 C16 179.23(19) . . . . ?

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

