# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20180620GT
_database_code_depnum_ccdc_archive 'CCDC 1890798'
loop_
_audit_author_name
_audit_author_address
'Tao Guo'
;Henan University of Technology
China
;
_audit_update_record             
;
2019-01-14 deposited with the CCDC.	2019-02-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         401.45

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8542(2)
_cell_length_b                   10.4047(2)
_cell_length_c                   11.6372(2)
_cell_angle_alpha                112.5430(10)
_cell_angle_beta                 94.2880(10)
_cell_angle_gamma                106.4650(10)
_cell_volume                     1033.89(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      4.7832
_cell_measurement_theta_max      68.5313
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420

_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_T_max  0.7531

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'D8 Venture PhotonII'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            27772
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_theta_min         4.78
_diffrn_reflns_theta_max         69.00
_diffrn_reflns_theta_full        69.00
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3786
_reflns_number_gt                3317
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1053
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3786
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.2113P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.92525(10) 0.28149(10) 0.40550(9) 0.0373(2) Uani d . . . 1 . .
N N1 0.70740(11) 0.48364(11) 0.47787(9) 0.0281(2) Uani d . . . 1 . .
N N2 0.88539(11) 0.40787(11) 0.81640(9) 0.0295(2) Uani d . . . 1 . .
N N3 0.83252(10) 0.55790(10) 0.73665(9) 0.0255(2) Uani d . . . 1 . .
C C1 0.4633(2) -0.09183(19) 0.11033(17) 0.0661(5) Uani d . . . 1 . .
H H1 0.389202 -0.175703 0.047087 0.079 Uiso calc U . R 1 . .
C C2 0.6066(2) -0.0714(2) 0.10217(18) 0.0705(6) Uani d . . . 1 . .
H H15 0.630356 -0.140649 0.032887 0.085 Uiso calc U . R 1 . .
C C3 0.71525(18) 0.04928(18) 0.19435(14) 0.0503(4) Uani d . . . 1 . .
H H18 0.8136 0.062778 0.188754 0.06 Uiso calc U . R 1 . .
C C4 0.68018(14) 0.15137(14) 0.29576(12) 0.0324(3) Uani d . . . 1 . .
C C5 0.79910(13) 0.27319(13) 0.39923(11) 0.0284(3) Uani d . . . 1 . .
C C6 0.76264(12) 0.39632(12) 0.50228(11) 0.0254(3) Uani d . . . 1 . .
C C7 0.80425(12) 0.42044(12) 0.63338(11) 0.0255(3) Uani d . . . 1 . .
C C8 0.83718(12) 0.33185(13) 0.68844(11) 0.0263(3) Uani d . . . 1 . .
C C9 0.82522(13) 0.17486(13) 0.62882(11) 0.0289(3) Uani d . . . 1 . .
C C10 0.70541(15) 0.06736(14) 0.53687(13) 0.0362(3) Uani d . . . 1 . .
H H10 0.628943 0.094799 0.509969 0.043 Uiso calc U . R 1 . .
C C11 0.69695(18) -0.07983(15) 0.48417(14) 0.0456(4) Uani d . . . 1 . .
H H9 0.616072 -0.152286 0.419715 0.055 Uiso calc U . R 1 . .
C C12 0.80585(19) -0.12107(15) 0.52526(15) 0.0477(4) Uani d . . . 1 . .
H H2 0.799608 -0.221902 0.489381 0.057 Uiso calc U . R 1 . .
C C13 0.62385(16) 0.4868(2) 0.12090(15) 0.0503(4) Uani d . . . 1 . .
H H3 0.603216 0.48798 0.040305 0.06 Uiso calc U . R 1 . .
C C14 0.52295(16) 0.4944(2) 0.19791(15) 0.0517(4) Uani d . . . 1 . .
H H4 0.433323 0.50146 0.170051 0.062 Uiso calc U . R 1 . .
C C15 0.55172(14) 0.49183(16) 0.31474(13) 0.0377(3) Uani d . . . 1 . .
H H19 0.482968 0.499315 0.367837 0.045 Uiso calc U . R 1 . .
C C16 0.68158(13) 0.47823(13) 0.35472(11) 0.0277(3) Uani d . . . 1 . .
C C17 0.78392(13) 0.47414(14) 0.27830(12) 0.0329(3) Uani d . . . 1 . .
H H6 0.874458 0.46893 0.306302 0.039 Uiso calc U . R 1 . .
C C18 0.75403(15) 0.47763(16) 0.16167(14) 0.0396(3) Uani d . . . 1 . .
H H5 0.823771 0.473658 0.109456 0.048 Uiso calc U . R 1 . .
C C19 0.93430(15) 0.13176(14) 0.67016(12) 0.0346(3) Uani d . . . 1 . .
H H7 1.01594 0.20387 0.73392 0.042 Uiso calc U . R 1 . .
C C20 0.92412(18) -0.01556(16) 0.61872(14) 0.0437(3) Uani d . . . 1 . .
H H8 0.998431 -0.044242 0.647622 0.052 Uiso calc U . R 1 . .
C C21 0.88335(13) 0.54421(13) 0.84450(11) 0.0277(3) Uani d . . . 1 . .
C C22 0.92533(14) 0.66715(14) 0.96340(12) 0.0345(3) Uani d . . . 1 . .
H H14 0.963028 0.660253 1.037553 0.041 Uiso calc U . R 1 . .
C C23 0.91104(15) 0.79606(15) 0.97042(13) 0.0386(3) Uani d . . . 1 . .
H H11 0.936984 0.879414 1.050322 0.046 Uiso calc U . R 1 . .
C C24 0.85779(15) 0.80649(14) 0.85937(13) 0.0368(3) Uani d . . . 1 . .
H H13 0.847813 0.896978 0.865613 0.044 Uiso calc U . R 1 . .
C C25 0.82068(13) 0.68957(13) 0.74406(12) 0.0303(3) Uani d . . . 1 . .
H H12 0.787082 0.698238 0.669602 0.036 Uiso calc U . R 1 . .
C C26 0.42731(17) 0.00882(17) 0.20974(15) 0.0484(4) Uani d . . . 1 . .
H H16 0.328783 -0.005724 0.215113 0.058 Uiso calc U . R 1 . .
C C27 0.53545(14) 0.13103(14) 0.30152(13) 0.0356(3) Uani d . . . 1 . .
H H17 0.510751 0.20159 0.368987 0.043 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.2161(15) ?
N1 C6 . 1.2874(15) ?
N1 C16 . 1.4133(15) ?
N2 C21 . 1.3346(15) ?
N2 C8 . 1.3590(15) ?
N3 C25 . 1.3782(15) ?
N3 C21 . 1.3893(15) ?
N3 C7 . 1.4048(15) ?
C1 C26 . 1.380(2) ?
C1 C2 . 1.383(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.381(2) ?
C2 H15 . 0.95 ?
C3 C4 . 1.3958(19) ?
C3 H18 . 0.95 ?
C4 C27 . 1.3920(19) ?
C4 C5 . 1.4854(18) ?
C5 C6 . 1.5349(16) ?
C6 C7 . 1.4537(16) ?
C7 C8 . 1.3988(16) ?
C8 C9 . 1.4741(16) ?
C9 C10 . 1.3909(18) ?
C9 C19 . 1.3961(18) ?
C10 C11 . 1.3887(19) ?
C10 H10 . 0.95 ?
C11 C12 . 1.381(2) ?
C11 H9 . 0.95 ?
C12 C20 . 1.384(2) ?
C12 H2 . 0.95 ?
C13 C18 . 1.376(2) ?
C13 C14 . 1.386(2) ?
C13 H3 . 0.95 ?
C14 C15 . 1.3800(19) ?
C14 H4 . 0.95 ?
C15 C16 . 1.3922(17) ?
C15 H19 . 0.95 ?
C16 C17 . 1.3926(18) ?
C17 C18 . 1.3836(18) ?
C17 H6 . 0.95 ?
C18 H5 . 0.95 ?
C19 C20 . 1.3850(19) ?
C19 H7 . 0.95 ?
C20 H8 . 0.95 ?
C21 C22 . 1.4068(17) ?
C22 C23 . 1.3602(19) ?
C22 H14 . 0.95 ?
C23 C24 . 1.4127(19) ?
C23 H11 . 0.95 ?
C24 C25 . 1.3553(18) ?
C24 H13 . 0.95 ?
C25 H12 . 0.95 ?
C26 C27 . 1.383(2) ?
C26 H16 . 0.95 ?
C27 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C16 . . 122.61(10) ?
C21 N2 C8 . . 105.83(10) ?
C25 N3 C21 . . 121.18(10) ?
C25 N3 C7 . . 132.18(10) ?
C21 N3 C7 . . 106.63(9) ?
C26 C1 C2 . . 120.43(15) ?
C26 C1 H1 . . 119.8 ?
C2 C1 H1 . . 119.8 ?
C3 C2 C1 . . 120.26(16) ?
C3 C2 H15 . . 119.9 ?
C1 C2 H15 . . 119.9 ?
C2 C3 C4 . . 119.82(16) ?
C2 C3 H18 . . 120.1 ?
C4 C3 H18 . . 120.1 ?
C27 C4 C3 . . 119.34(13) ?
C27 C4 C5 . . 121.77(12) ?
C3 C4 C5 . . 118.76(12) ?
O1 C5 C4 . . 123.05(11) ?
O1 C5 C6 . . 117.99(11) ?
C4 C5 C6 . . 118.95(10) ?
N1 C6 C7 . . 119.75(11) ?
N1 C6 C5 . . 122.86(10) ?
C7 C6 C5 . . 117.20(10) ?
C8 C7 N3 . . 104.32(10) ?
C8 C7 C6 . . 132.89(11) ?
N3 C7 C6 . . 122.58(10) ?
N2 C8 C7 . . 111.72(10) ?
N2 C8 C9 . . 118.44(10) ?
C7 C8 C9 . . 129.83(11) ?
C10 C9 C19 . . 118.98(12) ?
C10 C9 C8 . . 121.99(11) ?
C19 C9 C8 . . 118.96(11) ?
C11 C10 C9 . . 120.38(13) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C12 C11 C10 . . 120.12(14) ?
C12 C11 H9 . . 119.9 ?
C10 C11 H9 . . 119.9 ?
C11 C12 C20 . . 120.03(13) ?
C11 C12 H2 . . 120.0 ?
C20 C12 H2 . . 120.0 ?
C18 C13 C14 . . 119.72(13) ?
C18 C13 H3 . . 120.1 ?
C14 C13 H3 . . 120.1 ?
C15 C14 C13 . . 120.49(13) ?
C15 C14 H4 . . 119.8 ?
C13 C14 H4 . . 119.8 ?
C14 C15 C16 . . 119.94(13) ?
C14 C15 H19 . . 120.0 ?
C16 C15 H19 . . 120.0 ?
C15 C16 C17 . . 119.28(11) ?
C15 C16 N1 . . 117.09(11) ?
C17 C16 N1 . . 123.35(11) ?
C18 C17 C16 . . 120.14(12) ?
C18 C17 H6 . . 119.9 ?
C16 C17 H6 . . 119.9 ?
C13 C18 C17 . . 120.37(13) ?
C13 C18 H5 . . 119.8 ?
C17 C18 H5 . . 119.8 ?
C20 C19 C9 . . 120.36(13) ?
C20 C19 H7 . . 119.8 ?
C9 C19 H7 . . 119.8 ?
C12 C20 C19 . . 120.11(14) ?
C12 C20 H8 . . 119.9 ?
C19 C20 H8 . . 119.9 ?
N2 C21 N3 . . 111.48(10) ?
N2 C21 C22 . . 128.89(11) ?
N3 C21 C22 . . 119.62(11) ?
C23 C22 C21 . . 118.90(12) ?
C23 C22 H14 . . 120.5 ?
C21 C22 H14 . . 120.5 ?
C22 C23 C24 . . 120.26(12) ?
C22 C23 H11 . . 119.9 ?
C24 C23 H11 . . 119.9 ?
C25 C24 C23 . . 121.12(12) ?
C25 C24 H13 . . 119.4 ?
C23 C24 H13 . . 119.4 ?
C24 C25 N3 . . 118.88(11) ?
C24 C25 H12 . . 120.6 ?
N3 C25 H12 . . 120.6 ?
C1 C26 C27 . . 119.65(16) ?
C1 C26 H16 . . 120.2 ?
C27 C26 H16 . . 120.2 ?
C26 C27 C4 . . 120.49(14) ?
C26 C27 H17 . . 119.8 ?
C4 C27 H17 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C26 C1 C2 C3 . . . . 0.7(3) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C2 C3 C4 C27 . . . . -0.9(2) ?
C2 C3 C4 C5 . . . . 174.94(16) ?
C27 C4 C5 O1 . . . . 169.38(12) ?
C3 C4 C5 O1 . . . . -6.36(19) ?
C27 C4 C5 C6 . . . . -11.70(17) ?
C3 C4 C5 C6 . . . . 172.56(12) ?
C16 N1 C6 C7 . . . . 171.79(10) ?
C16 N1 C6 C5 . . . . -3.00(17) ?
O1 C5 C6 N1 . . . . 116.25(13) ?
C4 C5 C6 N1 . . . . -62.72(15) ?
O1 C5 C6 C7 . . . . -58.67(15) ?
C4 C5 C6 C7 . . . . 122.36(11) ?
C25 N3 C7 C8 . . . . -179.78(12) ?
C21 N3 C7 C8 . . . . 1.55(12) ?
C25 N3 C7 C6 . . . . 4.83(19) ?
C21 N3 C7 C6 . . . . -173.83(10) ?
N1 C6 C7 C8 . . . . 164.56(12) ?
C5 C6 C7 C8 . . . . -20.35(18) ?
N1 C6 C7 N3 . . . . -21.55(17) ?
C5 C6 C7 N3 . . . . 153.54(11) ?
C21 N2 C8 C7 . . . . 0.24(13) ?
C21 N2 C8 C9 . . . . -179.07(10) ?
N3 C7 C8 N2 . . . . -1.14(13) ?
C6 C7 C8 N2 . . . . 173.54(12) ?
N3 C7 C8 C9 . . . . 178.07(11) ?
C6 C7 C8 C9 . . . . -7.2(2) ?
N2 C8 C9 C10 . . . . 136.01(12) ?
C7 C8 C9 C10 . . . . -43.16(19) ?
N2 C8 C9 C19 . . . . -40.94(17) ?
C7 C8 C9 C19 . . . . 139.90(13) ?
C19 C9 C10 C11 . . . . -2.1(2) ?
C8 C9 C10 C11 . . . . -179.03(12) ?
C9 C10 C11 C12 . . . . 1.7(2) ?
C10 C11 C12 C20 . . . . -0.3(2) ?
C18 C13 C14 C15 . . . . -0.4(3) ?
C13 C14 C15 C16 . . . . -1.4(3) ?
C14 C15 C16 C17 . . . . 2.9(2) ?
C14 C15 C16 N1 . . . . 176.96(13) ?
C6 N1 C16 C15 . . . . 138.08(13) ?
C6 N1 C16 C17 . . . . -48.12(17) ?
C15 C16 C17 C18 . . . . -2.55(19) ?
N1 C16 C17 C18 . . . . -176.23(12) ?
C14 C13 C18 C17 . . . . 0.8(3) ?
C16 C17 C18 C13 . . . . 0.7(2) ?
C10 C9 C19 C20 . . . . 1.03(19) ?
C8 C9 C19 C20 . . . . 178.07(12) ?
C11 C12 C20 C19 . . . . -0.7(2) ?
C9 C19 C20 C12 . . . . 0.4(2) ?
C8 N2 C21 N3 . . . . 0.80(13) ?
C8 N2 C21 C22 . . . . -178.72(13) ?
C25 N3 C21 N2 . . . . 179.63(10) ?
C7 N3 C21 N2 . . . . -1.53(13) ?
C25 N3 C21 C22 . . . . -0.80(17) ?
C7 N3 C21 C22 . . . . 178.04(11) ?
N2 C21 C22 C23 . . . . -178.61(13) ?
N3 C21 C22 C23 . . . . 1.91(19) ?
C21 C22 C23 C24 . . . . -1.3(2) ?
C22 C23 C24 C25 . . . . -0.3(2) ?
C23 C24 C25 N3 . . . . 1.5(2) ?
C21 N3 C25 C24 . . . . -0.89(18) ?
C7 N3 C25 C24 . . . . -179.39(12) ?
C2 C1 C26 C27 . . . . 0.1(3) ?
C1 C26 C27 C4 . . . . -1.4(2) ?
C3 C4 C27 C26 . . . . 1.8(2) ?
C5 C4 C27 C26 . . . . -173.94(12) ?

