# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1515610'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   19.090(6)
_cell_length_b                   7.095(2)
_cell_length_c                   10.995(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.304(11)
_cell_angle_gamma                90.00
_cell_volume                     1489.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2428
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      21.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16726
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2626
_reflns_number_gt                1652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0454P)²+0.1902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23461(7) 1.21063(19) 0.03178(13) 0.0832(5) Uani 1 1 d . . .
O2 O 0.24707(6) 0.92851(17) 0.16400(11) 0.0665(4) Uani 1 1 d . . .
O3 O 0.53356(8) 0.7685(2) 0.43004(13) 0.0830(4) Uani 1 1 d . . .
N1 N 0.17385(8) 1.0981(2) 0.03932(14) 0.0673(4) Uani 1 1 d . . .
C1 C 0.08556(11) 0.5434(3) 0.23133(19) 0.0787(6) Uani 1 1 d . . .
H1A H 0.0924 0.4456 0.2865 0.094 Uiso 1 1 calc R . .
C2 C 0.02267(12) 0.5594(3) 0.1711(2) 0.0817(6) Uani 1 1 d . . .
H2A H -0.0128 0.4730 0.1862 0.098 Uiso 1 1 calc R . .
C3 C 0.01170(11) 0.7024(3) 0.08836(19) 0.0760(6) Uani 1 1 d . . .
H3A H -0.0310 0.7120 0.0477 0.091 Uiso 1 1 calc R . .
C4 C 0.06392(11) 0.8308(3) 0.06609(18) 0.0697(5) Uani 1 1 d . . .
H4A H 0.0566 0.9264 0.0095 0.084 Uiso 1 1 calc R . .
C5 C 0.12780(10) 0.8187(2) 0.12774(16) 0.0581(5) Uani 1 1 d . . .
C6 C 0.18364(10) 0.9550(3) 0.10823(15) 0.0567(5) Uani 1 1 d . . .
C7 C 0.25823(10) 0.7816(2) 0.24523(14) 0.0581(5) Uani 1 1 d . . .
C8 C 0.32966(9) 0.7837(2) 0.29409(15) 0.0572(5) Uani 1 1 d . . .
C9 C 0.37872(11) 0.9115(3) 0.25288(18) 0.0686(5) Uani 1 1 d . . .
H9A H 0.3655 0.9997 0.1945 0.082 Uiso 1 1 calc R . .
C10 C 0.44714(11) 0.9121(3) 0.29607(18) 0.0712(5) Uani 1 1 d . . .
H10A H 0.4791 0.9998 0.2669 0.085 Uiso 1 1 calc R . .
C11 C 0.46738(10) 0.7830(3) 0.38193(17) 0.0652(5) Uani 1 1 d . . .
C12 C 0.41879(11) 0.6553(3) 0.42602(17) 0.0717(6) Uani 1 1 d . . .
H12A H 0.4321 0.5686 0.4853 0.086 Uiso 1 1 calc R . .
C13 C 0.35116(10) 0.6558(3) 0.38279(17) 0.0690(5) Uani 1 1 d . . .
H13A H 0.3192 0.5692 0.4133 0.083 Uiso 1 1 calc R . .
C14 C 0.20696(10) 0.6605(3) 0.26917(17) 0.0677(5) Uani 1 1 d . . .
H14A H 0.2149 0.5650 0.3255 0.081 Uiso 1 1 calc R . .
C15 C 0.13930(10) 0.6727(3) 0.21053(16) 0.0631(5) Uani 1 1 d . . .
C16 C 0.21856(13) 1.3698(3) -0.0419(2) 0.0971(8) Uani 1 1 d . . .
H16A H 0.2592 1.4486 -0.0484 0.146 Uiso 1 1 calc R . .
H16B H 0.1811 1.4400 -0.0056 0.146 Uiso 1 1 calc R . .
H16C H 0.2045 1.3282 -0.1215 0.146 Uiso 1 1 calc R . .
C17 C 0.58673(11) 0.8879(3) 0.3820(2) 0.0941(7) Uani 1 1 d . . .
H17A H 0.6303 0.8629 0.4229 0.141 Uiso 1 1 calc R . .
H17B H 0.5738 1.0173 0.3941 0.141 Uiso 1 1 calc R . .
H17C H 0.5919 0.8638 0.2966 0.141 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 N1 1.4109(19) . ?
O1 C16 1.422(2) . ?
O2 C6 1.367(2) . ?
O2 C7 1.3886(19) . ?
O3 C11 1.371(2) . ?
O3 C17 1.426(2) . ?
N1 C6 1.280(2) . ?
C1 C2 1.373(3) . ?
C1 C15 1.396(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(3) . ?
C4 H4A 0.9300 . ?
C5 C15 1.396(3) . ?
C5 C6 1.456(2) . ?
C7 C14 1.330(2) . ?
C7 C8 1.463(3) . ?
C8 C9 1.382(2) . ?
C8 C13 1.393(2) . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.386(3) . ?
C12 C13 1.373(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.443(3) . ?
C14 H14A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C16 107.95(14) . . ?
C6 O2 C7 121.60(14) . . ?
C11 O3 C17 117.97(16) . . ?
C6 N1 O1 111.48(15) . . ?
C2 C1 C15 120.5(2) . . ?
C2 C1 H1A 119.7 . . ?
C15 C1 H1A 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.43(19) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C15 119.77(18) . . ?
C4 C5 C6 121.79(17) . . ?
C15 C5 C6 118.44(17) . . ?
N1 C6 O2 120.03(17) . . ?
N1 C6 C5 120.61(17) . . ?
O2 C6 C5 119.36(15) . . ?
C14 C7 O2 120.12(17) . . ?
C14 C7 C8 128.30(17) . . ?
O2 C7 C8 111.58(15) . . ?
C9 C8 C13 117.35(17) . . ?
C9 C8 C7 121.24(16) . . ?
C13 C8 C7 121.40(16) . . ?
C8 C9 C10 121.90(17) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C11 C10 C9 119.69(19) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 O3 124.89(18) . . ?
C10 C11 C12 119.44(18) . . ?
O3 C11 C12 115.67(17) . . ?
C13 C12 C11 120.45(18) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C8 121.15(18) . . ?
C12 C13 H13A 119.4 . . ?
C8 C13 H13A 119.4 . . ?
C7 C14 C15 122.07(17) . . ?
C7 C14 H14A 119.0 . . ?
C15 C14 H14A 119.0 . . ?
C1 C15 C5 118.78(18) . . ?
C1 C15 C14 122.98(18) . . ?
C5 C15 C14 118.24(17) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 O1 N1 C6 -177.62(17) . . . . ?
C15 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C15 1.5(3) . . . . ?
C3 C4 C5 C6 -178.61(17) . . . . ?
O1 N1 C6 O2 0.4(2) . . . . ?
O1 N1 C6 C5 -179.33(14) . . . . ?
C7 O2 C6 N1 175.92(15) . . . . ?
C7 O2 C6 C5 -4.3(2) . . . . ?
C4 C5 C6 N1 4.7(3) . . . . ?
C15 C5 C6 N1 -175.39(16) . . . . ?
C4 C5 C6 O2 -175.06(16) . . . . ?
C15 C5 C6 O2 4.8(2) . . . . ?
C6 O2 C7 C14 1.0(2) . . . . ?
C6 O2 C7 C8 -179.27(14) . . . . ?
C14 C7 C8 C9 174.99(19) . . . . ?
O2 C7 C8 C9 -4.7(2) . . . . ?
C14 C7 C8 C13 -4.2(3) . . . . ?
O2 C7 C8 C13 176.10(15) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
C7 C8 C9 C10 -178.31(18) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 O3 179.12(18) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C17 O3 C11 C10 -4.4(3) . . . . ?
C17 O3 C11 C12 175.83(17) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
O3 C11 C12 C13 -179.14(18) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C7 C8 C13 C12 178.27(18) . . . . ?
O2 C7 C14 C15 1.7(3) . . . . ?
C8 C7 C14 C15 -177.91(17) . . . . ?
C2 C1 C15 C5 0.2(3) . . . . ?
C2 C1 C15 C14 -178.61(19) . . . . ?
C4 C5 C15 C1 -1.2(3) . . . . ?
C6 C5 C15 C1 178.89(16) . . . . ?
C4 C5 C15 C14 177.68(16) . . . . ?
C6 C5 C15 C14 -2.2(2) . . . . ?
C7 C14 C15 C1 177.81(18) . . . . ?
C7 C14 C15 C5 -1.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1515607'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.0672(6)
_cell_length_b                   14.8765(9)
_cell_length_c                   9.2489(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.386(2)
_cell_angle_gamma                90.00
_cell_volume                     1289.78(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4128
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      24.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14771
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2264
_reflns_number_gt                1738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0400P)²+0.2305P] 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         2264
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
N1 N 0.28243(12) 0.05706(8) 0.21912(13) 0.0478(3) Uani 1 1 d . . .
O1 O 0.15493(10) 0.08718(7) 0.22904(12) 0.0557(3) Uani 1 1 d . . .
O2 O 0.32833(12) 0.20021(7) 0.16468(14) 0.0694(3) Uani 1 1 d . . .
C1 C 0.36618(16) 0.12160(10) 0.18611(16) 0.0504(4) Uani 1 1 d . . .
C2 C 0.50056(15) 0.08630(10) 0.18227(15) 0.0479(4) Uani 1 1 d . . .
C3 C 0.59321(17) 0.14463(11) 0.14729(18) 0.0600(4) Uani 1 1 d . . .
H3A H 0.5680 0.2045 0.1242 0.072 Uiso 1 1 calc R . .
C4 C 0.72099(18) 0.11387(13) 0.1469(2) 0.0674(5) Uani 1 1 d . . .
H4A H 0.7826 0.1531 0.1240 0.081 Uiso 1 1 calc R . .
C5 C 0.75939(18) 0.02460(13) 0.1803(2) 0.0669(5) Uani 1 1 d . . .
H5A H 0.8469 0.0044 0.1805 0.080 Uiso 1 1 calc R . .
C6 C 0.66961(16) -0.03394(11) 0.21293(18) 0.0577(4) Uani 1 1 d . . .
H6A H 0.6959 -0.0939 0.2336 0.069 Uiso 1 1 calc R . .
C7 C 0.53800(15) -0.00455(10) 0.21552(16) 0.0476(3) Uani 1 1 d . . .
C8 C 0.44114(15) -0.06338(10) 0.24936(17) 0.0494(4) Uani 1 1 d . . .
H8A H 0.4657 -0.1235 0.2715 0.059 Uiso 1 1 calc R . .
C9 C 0.31547(15) -0.03378(9) 0.24984(15) 0.0448(3) Uani 1 1 d . . .
C10 C 0.20601(15) -0.09146(9) 0.27597(16) 0.0453(3) Uani 1 1 d . . .
C11 C 0.07807(16) -0.10976(10) 0.15590(17) 0.0527(4) Uani 1 1 d . . .
H11A H 0.0605 -0.0857 0.0578 0.063 Uiso 1 1 calc R . .
C12 C -0.02328(17) -0.16337(10) 0.1808(2) 0.0581(4) Uani 1 1 d . . .
H12A H -0.1079 -0.1761 0.0990 0.070 Uiso 1 1 calc R . .
C13 C -0.00013(18) -0.19808(10) 0.3258(2) 0.0609(4) Uani 1 1 d . . .
H13A H -0.0698 -0.2329 0.3428 0.073 Uiso 1 1 calc R . .
C14 C 0.1266(2) -0.18094(11) 0.4451(2) 0.0651(5) Uani 1 1 d . . .
H14A H 0.1432 -0.2048 0.5431 0.078 Uiso 1 1 calc R . .
C15 C 0.22961(18) -0.12836(10) 0.42038(18) 0.0582(4) Uani 1 1 d . . .
H15A H 0.3156 -0.1177 0.5017 0.070 Uiso 1 1 calc R . .
C16 C 0.1791(2) 0.11549(13) 0.3854(2) 0.0756(5) Uani 1 1 d . . .
H16A H 0.0912 0.1366 0.3915 0.113 Uiso 1 1 calc R . .
H16B H 0.2482 0.1631 0.4140 0.113 Uiso 1 1 calc R . .
H16C H 0.2141 0.0657 0.4549 0.113 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
N1 C1 1.3832(18) . ?
N1 O1 1.3938(14) . ?
N1 C9 1.3959(18) . ?
O1 C16 1.4389(19) . ?
O2 C1 1.2236(17) . ?
C1 C2 1.464(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.367(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.366(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.404(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.427(2) . ?
C8 C9 1.3412(19) . ?
C8 H8A 0.9300 . ?
C9 C10 1.4843(19) . ?
C10 C15 1.382(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.379(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.383(2) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O1 116.20(11) . . ?
C1 N1 C9 126.71(12) . . ?
O1 N1 C9 117.04(11) . . ?
N1 O1 C16 109.74(11) . . ?
O2 C1 N1 121.35(14) . . ?
O2 C1 C2 125.09(14) . . ?
N1 C1 C2 113.55(12) . . ?
C3 C2 C7 119.97(14) . . ?
C3 C2 C1 118.97(13) . . ?
C7 C2 C1 121.05(13) . . ?
C4 C3 C2 120.12(16) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.42(16) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 120.47(16) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 120.66(16) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C2 118.35(14) . . ?
C6 C7 C8 122.50(14) . . ?
C2 C7 C8 119.14(13) . . ?
C9 C8 C7 121.34(13) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 N1 118.18(13) . . ?
C8 C9 C10 124.60(13) . . ?
N1 C9 C10 117.19(12) . . ?
C15 C10 C11 118.55(13) . . ?
C15 C10 C9 120.72(13) . . ?
C11 C10 C9 120.73(13) . . ?
C12 C11 C10 120.48(14) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C13 C12 C11 120.50(15) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 119.45(15) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C13 C14 C15 120.36(15) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C10 C15 C14 120.62(15) . . ?
C10 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 O1 C16 -88.38(15) . . . . ?
C9 N1 O1 C16 88.96(15) . . . . ?
O1 N1 C1 O2 -1.1(2) . . . . ?
C9 N1 C1 O2 -178.14(14) . . . . ?
O1 N1 C1 C2 178.12(11) . . . . ?
C9 N1 C1 C2 1.1(2) . . . . ?
O2 C1 C2 C3 -2.0(2) . . . . ?
N1 C1 C2 C3 178.83(13) . . . . ?
O2 C1 C2 C7 177.00(14) . . . . ?
N1 C1 C2 C7 -2.17(19) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 178.32(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C2 0.6(2) . . . . ?
C5 C6 C7 C8 -179.87(14) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
C1 C2 C7 C6 -178.76(13) . . . . ?
C3 C2 C7 C8 -179.32(13) . . . . ?
C1 C2 C7 C8 1.7(2) . . . . ?
C6 C7 C8 C9 -179.44(13) . . . . ?
C2 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 N1 -1.2(2) . . . . ?
C7 C8 C9 C10 176.77(13) . . . . ?
C1 N1 C9 C8 0.6(2) . . . . ?
O1 N1 C9 C8 -176.43(12) . . . . ?
C1 N1 C9 C10 -177.54(13) . . . . ?
O1 N1 C9 C10 5.44(17) . . . . ?
C8 C9 C10 C15 69.5(2) . . . . ?
N1 C9 C10 C15 -112.46(15) . . . . ?
C8 C9 C10 C11 -110.22(17) . . . . ?
N1 C9 C10 C11 67.78(17) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C9 C10 C11 C12 -179.98(13) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -1.7(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C11 C10 C15 C14 -1.2(2) . . . . ?
C9 C10 C15 C14 178.98(14) . . . . ?
C13 C14 C15 C10 0.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1515606'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   30.495(3)
_cell_length_b                   4.1711(4)
_cell_length_c                   20.4558(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.745(3)
_cell_angle_gamma                90.00
_cell_volume                     2537.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      23.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13654
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2212
_reflns_number_gt                1616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0444P)²+0.4118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2212
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15858(3) 0.8179(3) 0.05782(5) 0.0532(3) Uani 1 1 d . . .
O2 O 0.23967(3) 0.9759(3) 0.06337(5) 0.0711(4) Uani 1 1 d . . .
N1 N 0.23315(4) 0.7939(3) 0.11820(6) 0.0598(4) Uani 1 1 d . . .
C1 C 0.12574(5) 0.5372(3) 0.13091(7) 0.0477(4) Uani 1 1 d . . .
C2 C 0.09672(5) 0.3858(4) 0.16490(8) 0.0585(4) Uani 1 1 d . . .
H2A H 0.0659 0.3807 0.1472 0.070 Uiso 1 1 calc R . .
C3 C 0.11505(6) 0.2439(4) 0.22543(8) 0.0653(5) Uani 1 1 d . . .
H3A H 0.0963 0.1413 0.2490 0.078 Uiso 1 1 calc R . .
C4 C 0.16094(6) 0.2506(4) 0.25208(8) 0.0661(5) Uani 1 1 d . . .
H4A H 0.1724 0.1509 0.2929 0.079 Uiso 1 1 calc R . .
C5 C 0.18982(6) 0.4021(4) 0.21919(8) 0.0617(4) Uani 1 1 d . . .
H5A H 0.2206 0.4086 0.2373 0.074 Uiso 1 1 calc R . .
C6 C 0.17145(5) 0.5445(3) 0.15816(7) 0.0494(4) Uani 1 1 d . . .
C7 C 0.19182(5) 0.7246(4) 0.11167(7) 0.0499(4) Uani 1 1 d . . .
C8 C 0.11713(5) 0.7087(3) 0.06753(7) 0.0471(4) Uani 1 1 d . . .
C9 C 0.07874(5) 0.7636(3) 0.02330(7) 0.0500(4) Uani 1 1 d . . .
H9A H 0.0533 0.6798 0.0352 0.060 Uiso 1 1 calc R . .
C10 C 0.06985(5) 0.9330(3) -0.04060(7) 0.0472(4) Uani 1 1 d . . .
C11 C 0.10279(5) 1.0862(4) -0.06705(7) 0.0555(4) Uani 1 1 d . . .
H11A H 0.1325 1.0854 -0.0430 0.067 Uiso 1 1 calc R . .
C12 C 0.09191(5) 1.2384(4) -0.12820(7) 0.0599(4) Uani 1 1 d . . .
H12A H 0.1143 1.3387 -0.1451 0.072 Uiso 1 1 calc R . .
C13 C 0.04824(5) 1.2436(4) -0.16462(8) 0.0610(4) Uani 1 1 d . . .
H13A H 0.0411 1.3466 -0.2059 0.073 Uiso 1 1 calc R . .
C14 C 0.01536(5) 1.0954(4) -0.13936(8) 0.0638(5) Uani 1 1 d . . .
H14A H -0.0142 1.0974 -0.1637 0.077 Uiso 1 1 calc R . .
C15 C 0.02595(5) 0.9438(4) -0.07820(7) 0.0559(4) Uani 1 1 d . . .
H15A H 0.0032 0.8463 -0.0616 0.067 Uiso 1 1 calc R . .
C16 C 0.28603(5) 1.0534(5) 0.07300(9) 0.0792(6) Uani 1 1 d . . .
H16A H 0.2908 1.1772 0.0356 0.119 Uiso 1 1 calc R . .
H16B H 0.3034 0.8596 0.0764 0.119 Uiso 1 1 calc R . .
H16C H 0.2952 1.1758 0.1135 0.119 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 C7 1.3784(16) . ?
O1 C8 1.3981(16) . ?
O2 N1 1.4042(16) . ?
O2 C16 1.4209(18) . ?
N1 C7 1.2712(18) . ?
C1 C6 1.383(2) . ?
C1 C2 1.392(2) . ?
C1 C8 1.4530(19) . ?
C2 C3 1.375(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.454(2) . ?
C8 C9 1.3321(19) . ?
C9 C10 1.4576(19) . ?
C9 H9A 0.9300 . ?
C10 C15 1.3897(19) . ?
C10 C11 1.397(2) . ?
C11 C12 1.376(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(2) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 108.84(11) . . ?
N1 O2 C16 108.91(11) . . ?
C7 N1 O2 110.54(11) . . ?
C6 C1 C2 120.27(14) . . ?
C6 C1 C8 108.45(12) . . ?
C2 C1 C8 131.28(14) . . ?
C3 C2 C1 117.93(15) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 121.34(15) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 121.17(15) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 117.59(15) . . ?
C4 C5 H5A 121.2 . . ?
C6 C5 H5A 121.2 . . ?
C1 C6 C5 121.71(14) . . ?
C1 C6 C7 106.60(12) . . ?
C5 C6 C7 131.68(14) . . ?
N1 C7 O1 123.86(13) . . ?
N1 C7 C6 127.26(13) . . ?
O1 C7 C6 108.87(12) . . ?
C9 C8 O1 122.29(13) . . ?
C9 C8 C1 130.48(13) . . ?
O1 C8 C1 107.23(11) . . ?
C8 C9 C10 130.84(13) . . ?
C8 C9 H9A 114.6 . . ?
C10 C9 H9A 114.6 . . ?
C15 C10 C11 117.27(14) . . ?
C15 C10 C9 118.55(13) . . ?
C11 C10 C9 124.18(13) . . ?
C12 C11 C10 120.88(14) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 120.67(15) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 119.32(15) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C13 C14 C15 120.34(14) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C14 C15 C10 121.51(15) . . ?
C14 C15 H15A 119.2 . . ?
C10 C15 H15A 119.2 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 O2 N1 C7 178.96(14) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C8 C1 C2 C3 -179.33(15) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C8 C1 C6 C5 179.45(13) . . . . ?
C2 C1 C6 C7 -178.67(12) . . . . ?
C8 C1 C6 C7 0.42(15) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 178.97(15) . . . . ?
O2 N1 C7 O1 0.0(2) . . . . ?
O2 N1 C7 C6 -178.92(13) . . . . ?
C8 O1 C7 N1 -178.48(14) . . . . ?
C8 O1 C7 C6 0.61(15) . . . . ?
C1 C6 C7 N1 178.40(15) . . . . ?
C5 C6 C7 N1 -0.5(3) . . . . ?
C1 C6 C7 O1 -0.64(15) . . . . ?
C5 C6 C7 O1 -179.53(15) . . . . ?
C7 O1 C8 C9 -179.99(13) . . . . ?
C7 O1 C8 C1 -0.34(15) . . . . ?
C6 C1 C8 C9 179.54(15) . . . . ?
C2 C1 C8 C9 -1.5(3) . . . . ?
C6 C1 C8 O1 -0.07(15) . . . . ?
C2 C1 C8 O1 178.89(14) . . . . ?
O1 C8 C9 C10 0.1(2) . . . . ?
C1 C8 C9 C10 -179.43(13) . . . . ?
C8 C9 C10 C15 177.65(15) . . . . ?
C8 C9 C10 C11 -2.2(2) . . . . ?
C15 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C11 C12 179.24(13) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C9 C10 C15 C14 -179.01(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
