# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

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

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1590160'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.4127(1)
_cell_length_b                   8.0298(1)
_cell_length_c                   10.9583(2)
_cell_angle_alpha                73.3544(8)
_cell_angle_beta                 83.3366(8)
_cell_angle_gamma                73.6078(8)
_cell_volume                     599.091(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2711
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   'Scalepack (Otwinowsky & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(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  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ=55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5421
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2737
_reflns_number_gt                2367
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Nonius, 2002)'
_computing_cell_refinement       'Denzo-SMN (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'XP in SHELXTL (Sheldrick, 1995)'

_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)+(0.0562P)²+0.2835P] 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         2737
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.89376(17) 0.50765(16) 0.19707(11) 0.0141(3) Uani 1 1 d . . .
C2 C 0.89827(16) 0.66923(16) 0.10211(11) 0.0140(3) Uani 1 1 d . . .
C3 C 1.07183(18) 0.69758(17) 0.04779(12) 0.0166(3) Uani 1 1 d . . .
H3 H 1.0736 0.8065 -0.0154 0.020 Uiso 1 1 calc R . .
C4 C 1.23983(17) 0.57162(18) 0.08359(12) 0.0188(3) Uani 1 1 d . . .
H4 H 1.3561 0.5934 0.0464 0.023 Uiso 1 1 calc R . .
C5 C 1.23506(18) 0.41145(18) 0.17579(12) 0.0189(3) Uani 1 1 d . . .
H5 H 1.3495 0.3228 0.2007 0.023 Uiso 1 1 calc R . .
C6 C 1.06682(18) 0.37982(16) 0.23142(12) 0.0171(3) Uani 1 1 d . . .
H6 H 1.0676 0.2698 0.2941 0.021 Uiso 1 1 calc R . .
N7 N 0.72925(14) 0.47052(14) 0.25545(10) 0.0157(2) Uani 1 1 d . . .
H7 H 0.6222 0.5234 0.2168 0.019 Uiso 1 1 calc R . .
C8 C 0.73234(16) 0.34527(16) 0.37969(11) 0.0145(3) Uani 1 1 d . . .
C9 C 0.74339(17) 0.40487(16) 0.48644(12) 0.0161(3) Uani 1 1 d . . .
C10 C 0.74712(17) 0.28478(17) 0.60703(12) 0.0181(3) Uani 1 1 d . . .
H10 H 0.7552 0.3229 0.6802 0.022 Uiso 1 1 calc R . .
C11 C 0.73911(18) 0.10896(17) 0.62088(12) 0.0186(3) Uani 1 1 d . . .
H11 H 0.7404 0.0281 0.7035 0.022 Uiso 1 1 calc R . .
C12 C 0.72932(17) 0.05196(16) 0.51471(12) 0.0180(3) Uani 1 1 d . . .
H12 H 0.7236 -0.0681 0.5254 0.022 Uiso 1 1 calc R . .
C13 C 0.72763(16) 0.16801(16) 0.39177(12) 0.0153(3) Uani 1 1 d . . .
C14 C 0.72515(17) 0.81033(16) 0.05941(11) 0.0148(3) Uani 1 1 d . . .
O15 O 0.56576(12) 0.79984(12) 0.10276(9) 0.0195(2) Uani 1 1 d . . .
O16 O 0.75187(12) 0.95254(12) -0.03021(9) 0.0202(2) Uani 1 1 d . . .
H16 H 0.6474 1.0262 -0.0508 0.030 Uiso 1 1 calc R . .
C17 C 0.75090(18) 0.59544(17) 0.47099(13) 0.0195(3) Uani 1 1 d . . .
H17A H 0.7620 0.6122 0.5547 0.029 Uiso 1 1 calc R . .
H17B H 0.6355 0.6794 0.4323 0.029 Uiso 1 1 calc R . .
H17C H 0.8600 0.6187 0.4160 0.029 Uiso 1 1 calc R . .
C18 C 0.72769(19) 0.09830(17) 0.27785(12) 0.0198(3) Uani 1 1 d . . .
H18A H 0.6921 0.2001 0.2026 0.030 Uiso 1 1 calc R . .
H18B H 0.6372 0.0252 0.2940 0.030 Uiso 1 1 calc R . .
H18C H 0.8538 0.0243 0.2630 0.030 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
C1 N7 1.3784(15) . ?
C1 C6 1.4101(17) . ?
C1 C2 1.4178(16) . ?
C2 C3 1.4041(17) . ?
C2 C14 1.4712(16) . ?
C3 C4 1.3795(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3962(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3803(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.4407(14) . ?
N7 H7 0.8800 . ?
C8 C13 1.4013(17) . ?
C8 C9 1.4032(18) . ?
C9 C10 1.3929(17) . ?
C9 C17 1.5070(17) . ?
C10 C11 1.3937(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3826(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.4006(17) . ?
C12 H12 0.9500 . ?
C13 C18 1.5072(17) . ?
C14 O15 1.2377(15) . ?
C14 O16 1.3220(14) . ?
O16 H16 0.8400 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 C1 C6 119.28(11) . . ?
N7 C1 C2 123.06(11) . . ?
C6 C1 C2 117.66(11) . . ?
C3 C2 C1 119.63(11) . . ?
C3 C2 C14 118.65(11) . . ?
C1 C2 C14 121.71(11) . . ?
C4 C3 C2 121.84(11) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 118.48(11) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 121.09(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 121.29(11) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C1 N7 C8 120.09(10) . . ?
C1 N7 H7 120.0 . . ?
C8 N7 H7 120.0 . . ?
C13 C8 C9 121.56(11) . . ?
C13 C8 N7 120.12(11) . . ?
C9 C8 N7 118.31(10) . . ?
C10 C9 C8 118.82(11) . . ?
C10 C9 C17 120.55(11) . . ?
C8 C9 C17 120.62(11) . . ?
C9 C10 C11 120.34(12) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.15(11) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.21(11) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 117.90(11) . . ?
C12 C13 C18 119.73(11) . . ?
C8 C13 C18 122.34(11) . . ?
O15 C14 O16 121.61(11) . . ?
O15 C14 C2 123.69(11) . . ?
O16 C14 C2 114.70(10) . . ?
C14 O16 H16 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 C1 C2 C3 179.56(11) . . . . ?
C6 C1 C2 C3 -1.01(17) . . . . ?
N7 C1 C2 C14 0.28(19) . . . . ?
C6 C1 C2 C14 179.71(11) . . . . ?
C1 C2 C3 C4 0.39(19) . . . . ?
C14 C2 C3 C4 179.70(11) . . . . ?
C2 C3 C4 C5 0.51(19) . . . . ?
C3 C4 C5 C6 -0.78(19) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
N7 C1 C6 C5 -179.79(11) . . . . ?
C2 C1 C6 C5 0.75(18) . . . . ?
C6 C1 N7 C8 24.40(17) . . . . ?
C2 C1 N7 C8 -156.18(11) . . . . ?
C1 N7 C8 C13 -100.56(13) . . . . ?
C1 N7 C8 C9 78.36(14) . . . . ?
C13 C8 C9 C10 -0.88(18) . . . . ?
N7 C8 C9 C10 -179.78(10) . . . . ?
C13 C8 C9 C17 179.18(11) . . . . ?
N7 C8 C9 C17 0.27(17) . . . . ?
C8 C9 C10 C11 -0.29(18) . . . . ?
C17 C9 C10 C11 179.65(11) . . . . ?
C9 C10 C11 C12 0.66(19) . . . . ?
C10 C11 C12 C13 0.14(19) . . . . ?
C11 C12 C13 C8 -1.26(18) . . . . ?
C11 C12 C13 C18 176.63(11) . . . . ?
C9 C8 C13 C12 1.64(18) . . . . ?
N7 C8 C13 C12 -179.48(10) . . . . ?
C9 C8 C13 C18 -176.19(11) . . . . ?
N7 C8 C13 C18 2.69(17) . . . . ?
C3 C2 C14 O15 -178.73(11) . . . . ?
C1 C2 C14 O15 0.56(19) . . . . ?
C3 C2 C14 O16 1.12(16) . . . . ?
C1 C2 C14 O16 -179.60(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yf_170724
_database_code_depnum_ccdc_archive 'CCDC 1590161'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.524(2)
_cell_length_b                   8.103(2)
_cell_length_c                   11.191(3)
_cell_angle_alpha                72.582(4)
_cell_angle_beta                 83.740(4)
_cell_angle_gamma                73.854(4)
_cell_volume                     625.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2386
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9749
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3780
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.908
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2769
_reflns_number_gt                2321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0682P)²+0.1340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.52(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2769
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.39469(18) 1.17222(17) 0.10256(12) 0.0374(3) Uani 1 1 d . . . . .
C2 C 0.5642(2) 1.2003(2) 0.04776(14) 0.0458(4) Uani 1 1 d . . . . .
H2 H 0.565185 1.305626 -0.014918 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7294(2) 1.0759(2) 0.08429(15) 0.0530(4) Uani 1 1 d . . . . .
H3 H 0.840876 1.096812 0.047370 0.064 Uiso 1 1 calc R U . . .
C4 C 0.7262(2) 0.9187(2) 0.17720(16) 0.0533(4) Uani 1 1 d . . . . .
H4 H 0.836984 0.833285 0.201887 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5631(2) 0.88673(19) 0.23345(14) 0.0462(4) Uani 1 1 d . . . . .
H5 H 0.565402 0.780213 0.295694 0.055 Uiso 1 1 calc R U . . .
C6 C 0.39228(18) 1.01199(16) 0.19877(12) 0.0366(3) Uani 1 1 d . . . . .
N7 N 0.23161(17) 0.97457(15) 0.25687(11) 0.0437(3) Uani 1 1 d . . . . .
H7 H 0.132(3) 1.066(2) 0.2383(16) 0.052 Uiso 1 1 d . U . . .
C8 C 0.23438(18) 0.84981(17) 0.37980(12) 0.0385(3) Uani 1 1 d . . . . .
C9 C 0.24285(19) 0.90747(18) 0.48458(14) 0.0430(3) Uani 1 1 d . . . . .
C10 C 0.2459(2) 0.7859(2) 0.60330(15) 0.0507(4) Uani 1 1 d . . . . .
H10 H 0.251796 0.821951 0.673895 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2402(2) 0.6118(2) 0.61679(14) 0.0530(4) Uani 1 1 d . . . . .
H11 H 0.241493 0.531934 0.696331 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2327(2) 0.55680(18) 0.51314(14) 0.0496(4) Uani 1 1 d . . . . .
H12 H 0.228527 0.439644 0.523647 0.060 Uiso 1 1 calc R U . . .
C13 C 0.23112(19) 0.67304(17) 0.39217(13) 0.0419(3) Uani 1 1 d . . . . .
C14 C 0.22345(19) 1.31128(17) 0.05973(12) 0.0404(3) Uani 1 1 d . . . . .
O15 O 0.06841(14) 1.30138(14) 0.10310(11) 0.0562(3) Uani 1 1 d . . . . .
O16 O 0.24769(16) 1.45199(15) -0.03085(11) 0.0603(4) Uani 1 1 d . . . . .
H16 H 0.127(3) 1.539(3) -0.0530(16) 0.090 Uiso 1 1 calc R U . . .
C17 C 0.2477(2) 1.0971(2) 0.47042(17) 0.0556(4) Uani 1 1 d . . . . .
H17A H 0.355273 1.120908 0.421235 0.083 Uiso 1 1 calc R U . . .
H17B H 0.252411 1.112644 0.551649 0.083 Uiso 1 1 calc R U . . .
H17C H 0.138428 1.178568 0.429351 0.083 Uiso 1 1 calc R U . . .
C18 C 0.2304(3) 0.6066(2) 0.27996(15) 0.0572(4) Uani 1 1 d . . . . .
H18A H 0.192056 0.706856 0.207929 0.086 Uiso 1 1 calc R U . . .
H18B H 0.146002 0.532221 0.296020 0.086 Uiso 1 1 calc R U . . .
H18C H 0.352673 0.538340 0.264522 0.086 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
C1 C2 1.4005(19) . ?
C1 C6 1.4204(17) . ?
C1 C14 1.4709(18) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.4071(19) . ?
C5 H5 0.9300 . ?
C6 N7 1.3750(18) . ?
N7 C8 1.4412(16) . ?
N7 H7 0.889(19) . ?
C8 C9 1.399(2) . ?
C8 C13 1.4042(19) . ?
C9 C10 1.395(2) . ?
C9 C17 1.507(2) . ?
C10 C11 1.385(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3979(19) . ?
C12 H12 0.9300 . ?
C13 C18 1.508(2) . ?
C14 O15 1.2281(17) . ?
C14 O16 1.3207(16) . ?
O16 H16 0.99(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.44(12) . . ?
C2 C1 C14 118.88(12) . . ?
C6 C1 C14 121.68(12) . . ?
C3 C2 C1 121.69(13) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 118.68(14) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.33(14) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.26(14) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N7 C6 C5 119.53(12) . . ?
N7 C6 C1 122.88(12) . . ?
C5 C6 C1 117.59(13) . . ?
C6 N7 C8 120.73(11) . . ?
C6 N7 H7 114.1(11) . . ?
C8 N7 H7 117.0(11) . . ?
C9 C8 C13 121.37(12) . . ?
C9 C8 N7 118.97(12) . . ?
C13 C8 N7 119.66(13) . . ?
C10 C9 C8 118.66(13) . . ?
C10 C9 C17 120.31(14) . . ?
C8 C9 C17 121.03(13) . . ?
C11 C10 C9 120.50(15) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.23(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.44(13) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 117.79(13) . . ?
C12 C13 C18 120.17(13) . . ?
C8 C13 C18 122.02(13) . . ?
O15 C14 O16 121.26(12) . . ?
O15 C14 C1 124.04(11) . . ?
O16 C14 C1 114.70(12) . . ?
C14 O16 H16 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(2) . . . . ?
C14 C1 C2 C3 179.55(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 N7 179.64(14) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C2 C1 C6 N7 -179.85(13) . . . . ?
C14 C1 C6 N7 0.9(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C14 C1 C6 C5 179.99(12) . . . . ?
C5 C6 N7 C8 23.7(2) . . . . ?
C1 C6 N7 C8 -157.22(13) . . . . ?
C6 N7 C8 C9 79.63(17) . . . . ?
C6 N7 C8 C13 -99.50(16) . . . . ?
C13 C8 C9 C10 -0.7(2) . . . . ?
N7 C8 C9 C10 -179.86(12) . . . . ?
C13 C8 C9 C17 179.56(13) . . . . ?
N7 C8 C9 C17 0.4(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C17 C9 C10 C11 179.56(15) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 -1.0(2) . . . . ?
C11 C12 C13 C18 177.58(15) . . . . ?
C9 C8 C13 C12 1.3(2) . . . . ?
N7 C8 C13 C12 -179.57(12) . . . . ?
C9 C8 C13 C18 -177.28(14) . . . . ?
N7 C8 C13 C18 1.8(2) . . . . ?
C2 C1 C14 O15 -178.63(14) . . . . ?
C6 C1 C14 O15 0.6(2) . . . . ?
C2 C1 C14 O16 1.20(19) . . . . ?
C6 C1 C14 O16 -179.58(13) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.058

