# 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_xhj
_database_code_depnum_ccdc_archive 'CCDC 1848721'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-14 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 H19 N0 O2'
_chemical_formula_weight         255.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   9.5307(4)
_cell_length_b                   9.5307(4)
_cell_length_c                   12.9688(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1020.19(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             411
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10947
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.97
_reflns_number_total             3153
_reflns_number_gt                2596
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0507P)²+1.1314P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(2)
_refine_ls_number_reflns         3153
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O2 O 0.7163(2) 0.5459(3) 0.17880(17) 0.0249(5) Uani 1 1 d . . .
O1 O 0.7517(3) 0.6028(3) 0.36623(18) 0.0257(5) Uani 1 1 d . . .
C10 C 0.8778(3) 0.6222(4) 0.1697(2) 0.0184(6) Uani 1 1 d . . .
C6 C 1.0110(4) 0.7131(4) 0.4462(2) 0.0204(6) Uani 1 1 d . . .
H6A H 0.9581 0.6942 0.5154 0.025 Uiso 1 1 calc R . .
C14 C 1.0259(4) 0.6235(4) -0.1431(2) 0.0195(6) Uani 1 1 d . . .
C8 C 0.9764(4) 0.6843(4) 0.2542(2) 0.0181(6) Uani 1 1 d . . .
C12 C 0.8427(4) 0.4903(4) -0.0006(2) 0.0208(6) Uani 1 1 d . . .
H12A H 0.7488 0.3985 0.0260 0.025 Uiso 1 1 calc R . .
C15 C 1.1114(4) 0.7586(4) -0.0813(2) 0.0218(6) Uani 1 1 d . . .
H15A H 1.2025 0.8519 -0.1090 0.026 Uiso 1 1 calc R . .
C11 C 0.9312(3) 0.6246(4) 0.0623(2) 0.0181(6) Uani 1 1 d . . .
C16 C 1.0667(4) 0.7608(4) 0.0207(2) 0.0203(6) Uani 1 1 d . . .
H16A H 1.1280 0.8544 0.0620 0.024 Uiso 1 1 calc R . .
C3 C 1.2627(4) 0.9520(4) 0.5267(3) 0.0284(7) Uani 1 1 d . . .
H3A H 1.3575 1.0581 0.5123 0.043 Uiso 1 1 calc R . .
H3B H 1.2985 0.8780 0.5519 0.043 Uiso 1 1 calc R . .
H3C H 1.1954 0.9637 0.5793 0.043 Uiso 1 1 calc R . .
C5 C 1.1224(4) 0.6396(4) 0.4288(3) 0.0213(6) Uani 1 1 d . . .
H5A H 1.1766 0.6321 0.4919 0.026 Uiso 1 1 calc R . .
H5B H 1.0708 0.5362 0.3901 0.026 Uiso 1 1 calc R . .
C9 C 1.1608(3) 0.7638(4) 0.2521(2) 0.0201(6) Uani 1 1 d . . .
H9A H 1.2075 0.8691 0.2157 0.024 Uiso 1 1 calc R . .
H9B H 1.1922 0.6938 0.2139 0.024 Uiso 1 1 calc R . .
C17 C 1.0799(4) 0.6235(4) -0.2554(3) 0.0217(6) Uani 1 1 d . . .
H17A H 1.1764 0.7280 -0.2706 0.033 Uiso 1 1 calc R . .
H17B H 0.9923 0.6062 -0.3026 0.033 Uiso 1 1 calc R . .
H17C H 1.1052 0.5364 -0.2642 0.033 Uiso 1 1 calc R . .
C7 C 0.9014(4) 0.6643(4) 0.3547(2) 0.0192(6) Uani 1 1 d . . .
C13 C 0.8897(4) 0.4884(4) -0.1016(2) 0.0210(6) Uani 1 1 d . . .
H13A H 0.8289 0.3948 -0.1430 0.025 Uiso 1 1 calc R . .
C4 C 1.2282(4) 0.7908(4) 0.3618(2) 0.0201(6) Uani 1 1 d . . .
H4A H 1.3475 0.8336 0.3667 0.024 Uiso 1 1 calc R . .
C2 C 1.1639(4) 0.8835(4) 0.4279(2) 0.0219(6) Uani 1 1 d . . .
C1 C 1.1408(5) 1.0144(4) 0.3772(3) 0.0300(7) Uani 1 1 d . . .
H1A H 1.2461 1.1137 0.3703 0.045 Uiso 1 1 calc R . .
H1B H 1.0689 1.0361 0.4198 0.045 Uiso 1 1 calc R . .
H1C H 1.0926 0.9777 0.3087 0.045 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
O2 C10 1.339(4) . ?
O1 C7 1.251(4) . ?
C10 C8 1.370(4) . ?
C10 C11 1.479(4) . ?
C6 C7 1.494(4) . ?
C6 C5 1.554(4) . ?
C6 C2 1.566(4) . ?
C6 H6A 1.0000 . ?
C14 C15 1.384(4) . ?
C14 C13 1.400(4) . ?
C14 C17 1.544(4) . ?
C8 C7 1.452(4) . ?
C8 C9 1.527(4) . ?
C12 C13 1.387(4) . ?
C12 C11 1.391(4) . ?
C12 H12A 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15A 0.9500 . ?
C11 C16 1.403(4) . ?
C16 H16A 0.9500 . ?
C3 C2 1.530(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 C4 1.547(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C9 C4 1.530(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 H13A 0.9500 . ?
C4 C2 1.559(4) . ?
C4 H4A 1.0000 . ?
C2 C1 1.521(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
O2 C10 C8 121.2(3) . . ?
O2 C10 C11 112.6(3) . . ?
C8 C10 C11 126.2(3) . . ?
C7 C6 C5 105.9(2) . . ?
C7 C6 C2 110.2(2) . . ?
C5 C6 C2 87.3(2) . . ?
C7 C6 H6A 116.5 . . ?
C5 C6 H6A 116.5 . . ?
C2 C6 H6A 116.5 . . ?
C15 C14 C13 118.4(3) . . ?
C15 C14 C17 120.3(3) . . ?
C13 C14 C17 121.2(3) . . ?
C10 C8 C7 118.3(3) . . ?
C10 C8 C9 124.8(3) . . ?
C7 C8 C9 116.7(2) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C12 C11 C16 118.7(3) . . ?
C12 C11 C10 119.5(3) . . ?
C16 C11 C10 121.8(3) . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C5 C6 86.3(2) . . ?
C4 C5 H5A 114.3 . . ?
C6 C5 H5A 114.3 . . ?
C4 C5 H5B 114.3 . . ?
C6 C5 H5B 114.3 . . ?
H5A C5 H5B 111.4 . . ?
C8 C9 C4 110.4(2) . . ?
C8 C9 H9A 109.6 . . ?
C4 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C4 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C7 C8 122.7(3) . . ?
O1 C7 C6 120.4(3) . . ?
C8 C7 C6 116.8(3) . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C9 C4 C5 110.0(2) . . ?
C9 C4 C2 110.8(3) . . ?
C5 C4 C2 87.8(2) . . ?
C9 C4 H4A 115.0 . . ?
C5 C4 H4A 115.0 . . ?
C2 C4 H4A 115.0 . . ?
C1 C2 C3 108.8(3) . . ?
C1 C2 C4 119.1(3) . . ?
C3 C2 C4 111.7(3) . . ?
C1 C2 C6 118.4(3) . . ?
C3 C2 C6 111.8(3) . . ?
C4 C2 C6 85.5(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.97
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.060
