# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_xhj
_database_code_depnum_ccdc_archive 'CCDC 1535362'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 N4 O0'
_chemical_formula_weight         348.48

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'
'-x, -y, -z'

_cell_length_a                   7.6253(3)
_cell_length_b                   10.0149(4)
_cell_length_c                   12.9039(5)
_cell_angle_alpha                95.695(2)
_cell_angle_beta                 93.482(2)
_cell_angle_gamma                97.522(2)
_cell_volume                     969.41(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(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    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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            24230
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3808
_reflns_number_gt                2242
_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)+(0.0851P)²+0.1791P] 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         3808
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
N3 N 0.3799(3) 0.18555(19) 0.15438(15) 0.0215(5) Uani 1 1 d . . .
N2 N 0.2081(3) -0.02354(19) 0.08118(15) 0.0210(5) Uani 1 1 d . . .
N4 N 0.1277(3) 0.1816(2) 0.04617(17) 0.0298(6) Uani 1 1 d . . .
H4A H 0.0366 0.1374 0.0063 0.036 Uiso 1 1 calc R . .
H4B H 0.1446 0.2707 0.0536 0.036 Uiso 1 1 calc R . .
C6 C 0.3069(3) -0.0880(2) 0.14293(18) 0.0191(6) Uani 1 1 d . . .
C8 C 0.4752(3) 0.1170(2) 0.21425(17) 0.0182(6) Uani 1 1 d . . .
C7 C 0.4389(3) -0.0231(2) 0.21701(18) 0.0198(6) Uani 1 1 d . . .
C18 C 0.7511(3) 0.1201(3) 0.34341(19) 0.0222(6) Uani 1 1 d . . .
C13 C 0.6361(3) 0.2001(2) 0.27435(18) 0.0203(6) Uani 1 1 d . . .
H13A H 0.7139 0.2380 0.2217 0.024 Uiso 1 1 calc R . .
C9 C 0.2402(3) 0.1134(2) 0.09532(18) 0.0205(6) Uani 1 1 d . . .
C10 C 0.5481(3) -0.0960(3) 0.2874(2) 0.0243(6) Uani 1 1 d . . .
H10A H 0.5426 -0.1913 0.2570 0.029 Uiso 1 1 calc R . .
H10B H 0.4967 -0.0963 0.3560 0.029 Uiso 1 1 calc R . .
C11 C 0.7429(3) -0.0311(3) 0.30369(19) 0.0240(6) Uani 1 1 d . . .
C3 C 0.2671(3) -0.2392(2) 0.1244(2) 0.0229(6) Uani 1 1 d . . .
C23 C 0.8376(4) -0.1089(3) 0.3820(2) 0.0392(8) Uani 1 1 d . . .
H23A H 0.7844 -0.0995 0.4492 0.059 Uiso 1 1 calc R . .
H23B H 0.9637 -0.0720 0.3916 0.059 Uiso 1 1 calc R . .
H23C H 0.8251 -0.2050 0.3552 0.059 Uiso 1 1 calc R . .
C21 C 0.4051(4) 0.3162(3) 0.3789(2) 0.0365(7) Uani 1 1 d . . .
H21A H 0.3909 0.3956 0.4269 0.055 Uiso 1 1 calc R . .
H21B H 0.3724 0.2337 0.4123 0.055 Uiso 1 1 calc R . .
H21C H 0.3281 0.3142 0.3149 0.055 Uiso 1 1 calc R . .
N1 N 0.1900(3) -0.5206(2) 0.0831(2) 0.0456(7) Uani 1 1 d . . .
C17 C 0.9381(3) 0.2030(3) 0.3565(2) 0.0335(7) Uani 1 1 d . . .
H17A H 0.9769 0.2289 0.2885 0.040 Uiso 1 1 calc R . .
H17B H 1.0259 0.1510 0.3876 0.040 Uiso 1 1 calc R . .
C19 C 0.6866(4) 0.1545(3) 0.45293(19) 0.0303(7) Uani 1 1 d . . .
H19A H 0.5603 0.1190 0.4578 0.036 Uiso 1 1 calc R . .
H19B H 0.7612 0.1246 0.5094 0.036 Uiso 1 1 calc R . .
C14 C 0.5983(3) 0.3244(3) 0.3517(2) 0.0269(6) Uani 1 1 d . . .
C16 C 0.9148(4) 0.3293(3) 0.4309(2) 0.0435(8) Uani 1 1 d . . .
H16A H 0.9889 0.3339 0.4972 0.052 Uiso 1 1 calc R . .
H16B H 0.9462 0.4135 0.3980 0.052 Uiso 1 1 calc R . .
C4 C 0.1924(4) -0.3157(3) 0.1972(3) 0.0416(8) Uani 1 1 d . . .
H4C H 0.1667 -0.2740 0.2628 0.050 Uiso 1 1 calc R . .
C15 C 0.7174(4) 0.3075(3) 0.4493(2) 0.0342(7) Uani 1 1 d . . .
H15A H 0.6877 0.3601 0.5144 0.041 Uiso 1 1 calc R . .
C22 C 0.8288(4) -0.0470(3) 0.2006(2) 0.0389(8) Uani 1 1 d . . .
H22A H 0.7701 0.0021 0.1496 0.058 Uiso 1 1 calc R . .
H22B H 0.8169 -0.1432 0.1744 0.058 Uiso 1 1 calc R . .
H22C H 0.9548 -0.0099 0.2114 0.058 Uiso 1 1 calc R . .
C20 C 0.6450(4) 0.4592(3) 0.3062(2) 0.0423(8) Uani 1 1 d . . .
H20A H 0.6203 0.5337 0.3559 0.063 Uiso 1 1 calc R . .
H20B H 0.5734 0.4582 0.2404 0.063 Uiso 1 1 calc R . .
H20C H 0.7711 0.4716 0.2933 0.063 Uiso 1 1 calc R . .
C2 C 0.3041(5) -0.3060(3) 0.0311(2) 0.0458(9) Uani 1 1 d . . .
H2B H 0.3563 -0.2570 -0.0212 0.055 Uiso 1 1 calc R . .
C5 C 0.1553(4) -0.4551(3) 0.1730(3) 0.0501(9) Uani 1 1 d . . .
H5A H 0.1020 -0.5069 0.2234 0.060 Uiso 1 1 calc R . .
C1 C 0.2636(5) -0.4454(3) 0.0154(3) 0.0551(10) Uani 1 1 d . . .
H1B H 0.2910 -0.4900 -0.0488 0.066 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
N3 C8 1.328(3) . ?
N3 C9 1.352(3) . ?
N2 C6 1.332(3) . ?
N2 C9 1.353(3) . ?
N4 C9 1.333(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C6 C7 1.392(3) . ?
C6 C3 1.497(3) . ?
C8 C7 1.399(3) . ?
C8 C13 1.513(3) . ?
C7 C10 1.500(3) . ?
C18 C11 1.541(3) . ?
C18 C19 1.546(4) . ?
C18 C17 1.545(4) . ?
C18 C13 1.561(3) . ?
C13 C14 1.584(3) . ?
C13 H13A 1.0000 . ?
C10 C11 1.534(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C22 1.522(4) . ?
C11 C23 1.538(3) . ?
C3 C2 1.380(4) . ?
C3 C4 1.373(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21 C14 1.529(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 C1 1.313(4) . ?
N1 C5 1.333(4) . ?
C17 C16 1.547(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C15 1.525(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C14 C20 1.533(4) . ?
C14 C15 1.544(4) . ?
C16 C15 1.528(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C4 C5 1.387(4) . ?
C4 H4C 0.9500 . ?
C15 H15A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C2 C1 1.382(4) . ?
C2 H2B 0.9500 . ?
C5 H5A 0.9500 . ?
C1 H1B 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
C8 N3 C9 116.7(2) . . ?
C6 N2 C9 115.9(2) . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C6 C7 124.1(2) . . ?
N2 C6 C3 114.0(2) . . ?
C7 C6 C3 121.9(2) . . ?
N3 C8 C7 123.3(2) . . ?
N3 C8 C13 114.9(2) . . ?
C7 C8 C13 121.6(2) . . ?
C6 C7 C8 114.4(2) . . ?
C6 C7 C10 123.9(2) . . ?
C8 C7 C10 121.4(2) . . ?
C11 C18 C19 117.2(2) . . ?
C11 C18 C17 115.6(2) . . ?
C19 C18 C17 100.3(2) . . ?
C11 C18 C13 114.39(19) . . ?
C19 C18 C13 101.83(19) . . ?
C17 C18 C13 105.5(2) . . ?
C8 C13 C18 115.4(2) . . ?
C8 C13 C14 116.0(2) . . ?
C18 C13 C14 104.08(19) . . ?
C8 C13 H13A 106.9 . . ?
C18 C13 H13A 106.9 . . ?
C14 C13 H13A 106.9 . . ?
N4 C9 N2 117.6(2) . . ?
N4 C9 N3 117.9(2) . . ?
N2 C9 N3 124.5(2) . . ?
C7 C10 C11 112.7(2) . . ?
C7 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C7 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C18 109.1(2) . . ?
C10 C11 C22 109.2(2) . . ?
C18 C11 C22 110.4(2) . . ?
C10 C11 C23 107.8(2) . . ?
C18 C11 C23 112.1(2) . . ?
C22 C11 C23 108.3(2) . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 C6 119.9(2) . . ?
C4 C3 C6 122.3(2) . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C5 116.2(3) . . ?
C18 C17 C16 103.5(2) . . ?
C18 C17 H17A 111.1 . . ?
C16 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.0 . . ?
C15 C19 C18 94.9(2) . . ?
C15 C19 H19A 112.8 . . ?
C18 C19 H19A 112.8 . . ?
C15 C19 H19B 112.8 . . ?
C18 C19 H19B 112.8 . . ?
H19A C19 H19B 110.2 . . ?
C21 C14 C20 107.1(2) . . ?
C21 C14 C15 109.7(2) . . ?
C20 C14 C15 114.2(2) . . ?
C21 C14 C13 113.6(2) . . ?
C20 C14 C13 111.5(2) . . ?
C15 C14 C13 100.8(2) . . ?
C15 C16 C17 103.3(2) . . ?
C15 C16 H16A 111.1 . . ?
C17 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
C17 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4C 120.6 . . ?
C5 C4 H4C 120.6 . . ?
C19 C15 C16 100.8(2) . . ?
C19 C15 C14 102.0(2) . . ?
C16 C15 C14 112.5(2) . . ?
C19 C15 H15A 113.4 . . ?
C16 C15 H15A 113.4 . . ?
C14 C15 H15A 113.4 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2B 120.7 . . ?
C1 C2 H2B 120.7 . . ?
N1 C5 C4 123.9(3) . . ?
N1 C5 H5A 118.1 . . ?
C4 C5 H5A 118.1 . . ?
N1 C1 C2 124.6(3) . . ?
N1 C1 H1B 117.7 . . ?
C2 C1 H1B 117.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
