# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1954666'
loop_
_audit_author_name
_audit_author_address
'Chunshuang Liang'
;Jilin Institute of Chemical Technology
China
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H27 N O'
_chemical_formula_sum            'C37 H27 N O'
_chemical_formula_weight         501.59

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                   9.3440(5)
_cell_length_b                   12.1505(5)
_cell_length_c                   12.6030(5)
_cell_angle_alpha                82.8769(14)
_cell_angle_beta                 69.9436(10)
_cell_angle_gamma                86.0352(14)
_cell_volume                     1333.18(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8254
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15184
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5367
_reflns_number_gt                4489
_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 D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0574P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5367
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.002
_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 1.07704(16) 0.86089(11) 0.56172(13) 0.0580(3) Uani 1 1 d . . . . .
H1 H 1.0121 0.8960 0.6226 0.070 Uiso 1 1 calc R U . . .
C2 C 1.19283(19) 0.91925(13) 0.47938(16) 0.0735(5) Uani 1 1 d . . . . .
H2 H 1.2068 0.9928 0.4859 0.088 Uiso 1 1 calc R U . . .
C3 C 1.28774(18) 0.86894(15) 0.38749(16) 0.0756(5) Uani 1 1 d . . . . .
H3 H 1.3669 0.9078 0.3327 0.091 Uiso 1 1 calc R U . . .
C4 C 1.26457(17) 0.76099(14) 0.37748(13) 0.0696(4) Uani 1 1 d . . . . .
H4 H 1.3264 0.7274 0.3144 0.084 Uiso 1 1 calc R U . . .
C5 C 1.14983(15) 0.70165(11) 0.46066(11) 0.0547(3) Uani 1 1 d . . . . .
H5 H 1.1355 0.6284 0.4533 0.066 Uiso 1 1 calc R U . . .
C6 C 1.05647(13) 0.75049(10) 0.55456(10) 0.0447(3) Uani 1 1 d . . . . .
C7 C 0.93381(13) 0.68909(10) 0.64815(10) 0.0441(3) Uani 1 1 d . . . . .
C8 C 0.96390(14) 0.59417(10) 0.70587(10) 0.0458(3) Uani 1 1 d . . . . .
C9 C 1.12231(14) 0.54755(10) 0.68507(10) 0.0455(3) Uani 1 1 d . . . . .
C10 C 1.23870(16) 0.61045(12) 0.68805(13) 0.0586(3) Uani 1 1 d . . . . .
H10 H 1.2184 0.6838 0.7040 0.070 Uiso 1 1 calc R U . . .
C11 C 1.38394(18) 0.56608(14) 0.66782(16) 0.0721(4) Uani 1 1 d . . . . .
H11 H 1.4605 0.6092 0.6710 0.087 Uiso 1 1 calc R U . . .
C12 C 1.41607(17) 0.45875(15) 0.64310(14) 0.0701(4) Uani 1 1 d . . . . .
H12 H 1.5152 0.4299 0.6267 0.084 Uiso 1 1 calc R U . . .
C13 C 1.30224(18) 0.39373(13) 0.64248(14) 0.0671(4) Uani 1 1 d . . . . .
H13 H 1.3235 0.3201 0.6277 0.080 Uiso 1 1 calc R U . . .
C14 C 1.15596(16) 0.43762(11) 0.66382(13) 0.0584(3) Uani 1 1 d . . . . .
H14 H 1.0790 0.3930 0.6639 0.070 Uiso 1 1 calc R U . . .
C15 C 0.84356(14) 0.52712(10) 0.79468(11) 0.0500(3) Uani 1 1 d . . . . .
C16 C 0.85796(19) 0.49590(15) 0.90048(13) 0.0723(5) Uani 1 1 d . . . . .
H16 H 0.9418 0.5178 0.9156 0.087 Uiso 1 1 calc R U . . .
C17 C 0.7482(2) 0.43234(18) 0.98361(16) 0.0953(7) Uani 1 1 d . . . . .
H17 H 0.7573 0.4129 1.0548 0.114 Uiso 1 1 calc R U . . .
C18 C 0.6252(2) 0.39790(15) 0.96062(19) 0.0942(7) Uani 1 1 d . . . . .
H18 H 0.5521 0.3545 1.0161 0.113 Uiso 1 1 calc R U . . .
C19 C 0.6107(2) 0.42718(14) 0.85716(17) 0.0820(5) Uani 1 1 d . . . . .
H19 H 0.5276 0.4038 0.8421 0.098 Uiso 1 1 calc R U . . .
C20 C 0.71895(16) 0.49158(12) 0.77415(13) 0.0609(4) Uani 1 1 d . . . . .
H20 H 0.7079 0.5113 0.7036 0.073 Uiso 1 1 calc R U . . .
C21 C 0.77921(13) 0.74329(9) 0.67361(10) 0.0431(3) Uani 1 1 d . . . . .
C22 C 0.69051(15) 0.76662(11) 0.78248(11) 0.0501(3) Uani 1 1 d . . . . .
H22 H 0.7256 0.7449 0.8428 0.060 Uiso 1 1 calc R U . . .
C23 C 0.55027(15) 0.82191(11) 0.80228(11) 0.0506(3) Uani 1 1 d . . . . .
H23 H 0.4924 0.8368 0.8756 0.061 Uiso 1 1 calc R U . . .
C24 C 0.49574(13) 0.85510(10) 0.71352(11) 0.0457(3) Uani 1 1 d . . . . .
C25 C 0.58495(14) 0.83446(11) 0.60412(11) 0.0492(3) Uani 1 1 d . . . . .
H25 H 0.5507 0.8577 0.5436 0.059 Uiso 1 1 calc R U . . .
C26 C 0.72427(14) 0.77951(10) 0.58501(11) 0.0482(3) Uani 1 1 d . . . . .
H26 H 0.7829 0.7663 0.5113 0.058 Uiso 1 1 calc R U . . .
C27 C 0.23544(14) 0.88256(11) 0.81139(11) 0.0486(3) Uani 1 1 d . . . . .
H27 H 0.2418 0.8184 0.8583 0.058 Uiso 1 1 calc R U . . .
C28 C 0.09061(14) 0.94262(11) 0.83416(11) 0.0485(3) Uani 1 1 d . . . . .
C29 C -0.04549(14) 0.89904(11) 0.91981(11) 0.0509(3) Uani 1 1 d . . . . .
C30 C -0.05155(17) 0.79359(13) 0.98192(13) 0.0650(4) Uani 1 1 d . . . . .
H30 H 0.0361 0.7484 0.9667 0.078 Uiso 1 1 calc R U . . .
C31 C -0.18270(19) 0.75574(17) 1.06399(15) 0.0785(5) Uani 1 1 d . . . . .
H31 H -0.1826 0.6860 1.1038 0.094 Uiso 1 1 calc R U . . .
C32 C -0.31689(19) 0.82105(18) 1.08840(16) 0.0787(5) Uani 1 1 d . . . . .
H32 H -0.4058 0.7953 1.1444 0.094 Uiso 1 1 calc R U . . .
C33 C -0.31596(17) 0.92135(17) 1.03011(16) 0.0741(5) Uani 1 1 d . . . . .
H33 H -0.4054 0.9646 1.0468 0.089 Uiso 1 1 calc R U . . .
C34 C -0.18289(15) 0.96357(13) 0.94380(13) 0.0596(4) Uani 1 1 d . . . . .
C35 C -0.18306(19) 1.06833(15) 0.88160(17) 0.0740(5) Uani 1 1 d . . . . .
H35 H -0.2729 1.1111 0.8974 0.089 Uiso 1 1 calc R U . . .
C36 C -0.0558(2) 1.10830(14) 0.79952(17) 0.0759(5) Uani 1 1 d . . . . .
H36 H -0.0598 1.1775 0.7597 0.091 Uiso 1 1 calc R U . . .
C37 C 0.08281(16) 1.04600(12) 0.77374(12) 0.0563(3) Uani 1 1 d . . . . .
N1 N 0.35533(12) 0.91441(9) 0.72893(9) 0.0520(3) Uani 1 1 d . . . . .
O1 O 0.20329(13) 1.08999(9) 0.69108(10) 0.0724(3) Uani 1 1 d . . . . .
H1A H 0.2772 1.0472 0.6831 0.109 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 1.380(2) . ?
C1 C6 1.3864(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.3846(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3813(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4947(16) . ?
C7 C8 1.3512(17) . ?
C7 C21 1.4921(16) . ?
C8 C15 1.4893(17) . ?
C8 C9 1.4951(17) . ?
C9 C10 1.3851(18) . ?
C9 C14 1.3883(19) . ?
C10 C11 1.376(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.383(2) . ?
C15 C16 1.389(2) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.3907(17) . ?
C21 C26 1.3943(18) . ?
C22 C23 1.3879(17) . ?
C22 H22 0.9300 . ?
C23 C24 1.3872(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.3883(18) . ?
C24 N1 1.4169(16) . ?
C25 C26 1.3795(17) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N1 1.2831(16) . ?
C27 C28 1.4475(17) . ?
C27 H27 0.9300 . ?
C28 C37 1.3967(19) . ?
C28 C29 1.4397(18) . ?
C29 C30 1.410(2) . ?
C29 C34 1.4170(18) . ?
C30 C31 1.369(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.398(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.342(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.419(2) . ?
C33 H33 0.9300 . ?
C34 C35 1.410(2) . ?
C35 C36 1.353(2) . ?
C35 H35 0.9300 . ?
C36 C37 1.412(2) . ?
C36 H36 0.9300 . ?
C37 O1 1.3338(17) . ?
O1 H1A 0.8200 . ?

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 120.67(14) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.24(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.48(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.46(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.47(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.60(12) . . ?
C5 C6 C7 122.52(11) . . ?
C1 C6 C7 118.88(11) . . ?
C8 C7 C21 123.75(11) . . ?
C8 C7 C6 121.83(11) . . ?
C21 C7 C6 114.40(10) . . ?
C7 C8 C15 123.32(11) . . ?
C7 C8 C9 122.32(11) . . ?
C15 C8 C9 114.36(10) . . ?
C10 C9 C14 117.91(12) . . ?
C10 C9 C8 121.97(11) . . ?
C14 C9 C8 120.11(11) . . ?
C11 C10 C9 120.99(14) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.22(15) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.01(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.92(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.88(13) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C20 C15 C16 118.43(13) . . ?
C20 C15 C8 121.94(12) . . ?
C16 C15 C8 119.60(13) . . ?
C17 C16 C15 120.41(18) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.87(18) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.20(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.27(19) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.81(16) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 C26 117.84(11) . . ?
C22 C21 C7 122.36(11) . . ?
C26 C21 C7 119.64(11) . . ?
C23 C22 C21 120.87(12) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.52(12) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.06(11) . . ?
C23 C24 N1 122.60(11) . . ?
C25 C24 N1 118.26(11) . . ?
C26 C25 C24 120.11(12) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 121.56(11) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
N1 C27 C28 122.55(12) . . ?
N1 C27 H27 118.7 . . ?
C28 C27 H27 118.7 . . ?
C37 C28 C29 119.13(12) . . ?
C37 C28 C27 119.56(12) . . ?
C29 C28 C27 121.29(11) . . ?
C30 C29 C34 117.00(13) . . ?
C30 C29 C28 123.65(12) . . ?
C34 C29 C28 119.35(13) . . ?
C31 C30 C29 121.92(15) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
C30 C31 C32 120.54(17) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C32 C31 119.23(15) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 122.12(15) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
C35 C34 C29 118.93(14) . . ?
C35 C34 C33 121.91(14) . . ?
C29 C34 C33 119.15(15) . . ?
C36 C35 C34 121.69(14) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C35 C36 C37 120.70(15) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
O1 C37 C28 122.36(12) . . ?
O1 C37 C36 117.48(13) . . ?
C28 C37 C36 120.16(14) . . ?
C27 N1 C24 120.16(11) . . ?
C37 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.024


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_lzh_190904_02_0m
_database_code_depnum_ccdc_archive 'CCDC 1954667'
loop_
_audit_author_name
_audit_author_address
'Chunshuang Liang'
;Jilin Institute of Chemical Technology
China
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H27 N O'
_chemical_formula_sum            'C37 H27 N O'
_chemical_formula_weight         501.59

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                   7.1407(6)
_cell_length_b                   10.6510(8)
_cell_length_c                   19.6362(17)
_cell_angle_alpha                74.506(3)
_cell_angle_beta                 87.202(3)
_cell_angle_gamma                72.731(3)
_cell_volume                     1373.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    2205
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      22.03

_exptl_crystal_description       sheet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13742
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_full        25.001
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4807
_reflns_number_gt                2586
_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 D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0691P)²+0.0867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4807
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 -0.0007(4) 0.5069(3) 0.26287(14) 0.0705(8) Uani 1 1 d . . . . .
H1 H -0.0664 0.5755 0.2840 0.085 Uiso 1 1 calc R U . . .
C2 C -0.0598(6) 0.3909(4) 0.27511(18) 0.0950(11) Uani 1 1 d . . . . .
H2 H -0.1654 0.3819 0.3036 0.114 Uiso 1 1 calc R U . . .
C3 C 0.0391(7) 0.2887(4) 0.2447(2) 0.1031(12) Uani 1 1 d . . . . .
H3 H -0.0005 0.2105 0.2525 0.124 Uiso 1 1 calc R U . . .
C4 C 0.1948(6) 0.3015(3) 0.20329(19) 0.0964(11) Uani 1 1 d . . . . .
H4 H 0.2623 0.2317 0.1832 0.116 Uiso 1 1 calc R U . . .
C5 C 0.2520(5) 0.4182(3) 0.19119(15) 0.0753(8) Uani 1 1 d . . . . .
H5 H 0.3588 0.4259 0.1631 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1545(4) 0.5234(3) 0.21981(13) 0.0575(7) Uani 1 1 d . . . . .
C7 C 0.2212(4) 0.6483(2) 0.20945(13) 0.0556(7) Uani 1 1 d . . . . .
C8 C 0.2703(4) 0.7155(2) 0.14646(13) 0.0590(7) Uani 1 1 d . . . . .
C9 C 0.2306(4) 0.6908(3) 0.07759(14) 0.0638(7) Uani 1 1 d . . . . .
C10 C 0.0492(5) 0.6837(3) 0.05982(17) 0.0878(10) Uani 1 1 d . . . . .
H10 H -0.0517 0.6921 0.0916 0.105 Uiso 1 1 calc R U . . .
C11 C 0.0177(7) 0.6641(4) -0.0049(2) 0.1161(14) Uani 1 1 d . . . . .
H11 H -0.1041 0.6587 -0.0163 0.139 Uiso 1 1 calc R U . . .
C12 C 0.1652(9) 0.6525(4) -0.0525(2) 0.1217(16) Uani 1 1 d . . . . .
H12 H 0.1435 0.6396 -0.0961 0.146 Uiso 1 1 calc R U . . .
C13 C 0.3419(8) 0.6598(4) -0.0355(2) 0.1117(14) Uani 1 1 d . . . . .
H13 H 0.4423 0.6512 -0.0675 0.134 Uiso 1 1 calc R U . . .
C14 C 0.3750(5) 0.6799(3) 0.02856(16) 0.0861(10) Uani 1 1 d . . . . .
H14 H 0.4970 0.6862 0.0390 0.103 Uiso 1 1 calc R U . . .
C15 C 0.3810(4) 0.8169(3) 0.14008(13) 0.0593(7) Uani 1 1 d . . . . .
C16 C 0.3200(5) 0.9453(3) 0.09313(15) 0.0811(9) Uani 1 1 d . . . . .
H16 H 0.2036 0.9720 0.0666 0.097 Uiso 1 1 calc R U . . .
C17 C 0.4326(6) 1.0337(3) 0.08574(19) 0.0967(11) Uani 1 1 d . . . . .
H17 H 0.3903 1.1200 0.0545 0.116 Uiso 1 1 calc R U . . .
C18 C 0.6040(6) 0.9959(4) 0.1236(2) 0.0966(11) Uani 1 1 d . . . . .
H18 H 0.6779 1.0564 0.1183 0.116 Uiso 1 1 calc R U . . .
C19 C 0.6678(5) 0.8687(4) 0.16940(18) 0.0883(10) Uani 1 1 d . . . . .
H19 H 0.7856 0.8420 0.1950 0.106 Uiso 1 1 calc R U . . .
C20 C 0.5563(4) 0.7809(3) 0.17721(16) 0.0719(8) Uani 1 1 d . . . . .
H20 H 0.6002 0.6947 0.2085 0.086 Uiso 1 1 calc R U . . .
C21 C 0.2332(3) 0.6922(2) 0.27481(12) 0.0514(6) Uani 1 1 d . . . . .
C22 C 0.1583(3) 0.8274(2) 0.27685(13) 0.0546(6) Uani 1 1 d . . . . .
H22 H 0.1017 0.8933 0.2359 0.065 Uiso 1 1 calc R U . . .
C23 C 0.1657(3) 0.8665(2) 0.33799(13) 0.0546(6) Uani 1 1 d . . . . .
H23 H 0.1144 0.9576 0.3380 0.066 Uiso 1 1 calc R U . . .
C24 C 0.2499(3) 0.7693(2) 0.39940(12) 0.0488(6) Uani 1 1 d . . . . .
C25 C 0.3215(4) 0.6347(2) 0.39810(13) 0.0566(7) Uani 1 1 d . . . . .
H25 H 0.3768 0.5687 0.4392 0.068 Uiso 1 1 calc R U . . .
C26 C 0.3125(4) 0.5964(2) 0.33719(13) 0.0575(7) Uani 1 1 d . . . . .
H26 H 0.3603 0.5048 0.3378 0.069 Uiso 1 1 calc R U . . .
C27 C 0.2493(3) 0.9212(3) 0.47072(13) 0.0528(6) Uani 1 1 d . . . . .
H27 H 0.2156 0.9948 0.4308 0.063 Uiso 1 1 calc R U . . .
C28 C 0.2784(3) 0.9459(2) 0.53606(12) 0.0493(6) Uani 1 1 d . . . . .
C29 C 0.2578(3) 1.0813(2) 0.54228(14) 0.0521(6) Uani 1 1 d . . . . .
C30 C 0.1916(4) 1.1996(3) 0.48642(15) 0.0642(7) Uani 1 1 d . . . . .
H30 H 0.1584 1.1921 0.4428 0.077 Uiso 1 1 calc R U . . .
C31 C 0.1751(4) 1.3255(3) 0.49504(19) 0.0783(9) Uani 1 1 d . . . . .
H31 H 0.1319 1.4021 0.4571 0.094 Uiso 1 1 calc R U . . .
C32 C 0.2217(4) 1.3411(3) 0.5594(2) 0.0829(9) Uani 1 1 d . . . . .
H32 H 0.2085 1.4274 0.5647 0.100 Uiso 1 1 calc R U . . .
C33 C 0.2867(4) 1.2291(3) 0.61450(18) 0.0745(8) Uani 1 1 d . . . . .
H33 H 0.3190 1.2393 0.6576 0.089 Uiso 1 1 calc R U . . .
C34 C 0.3059(4) 1.0986(3) 0.60754(14) 0.0595(7) Uani 1 1 d . . . . .
C35 C 0.3749(4) 0.9804(3) 0.66498(15) 0.0735(8) Uani 1 1 d . . . . .
H35 H 0.4096 0.9910 0.7077 0.088 Uiso 1 1 calc R U . . .
C36 C 0.3918(4) 0.8541(3) 0.65995(15) 0.0752(8) Uani 1 1 d . . . . .
H36 H 0.4366 0.7798 0.6989 0.090 Uiso 1 1 calc R U . . .
C37 C 0.3419(4) 0.8333(3) 0.59573(14) 0.0586(7) Uani 1 1 d . . . . .
N1 N 0.2677(3) 0.7999(2) 0.46411(10) 0.0532(5) Uani 1 1 d . . . . .
O1 O 0.3613(3) 0.70848(19) 0.59429(9) 0.0758(6) Uani 1 1 d . . . . .
H1A H 0.3383 0.7073 0.5540 0.114 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 1.380(4) . ?
C1 C6 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 C8 1.341(3) . ?
C7 C21 1.493(3) . ?
C8 C15 1.495(3) . ?
C8 C9 1.500(3) . ?
C9 C14 1.377(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.350(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.378(4) . ?
C15 C16 1.386(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.385(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(3) . ?
C24 N1 1.414(3) . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N1 1.300(3) . ?
C27 C28 1.413(3) . ?
C27 H27 0.9300 . ?
C28 C37 1.412(3) . ?
C28 C29 1.444(3) . ?
C29 C30 1.404(3) . ?
C29 C34 1.415(3) . ?
C30 C31 1.366(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.385(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.357(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.398(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.424(4) . ?
C35 C36 1.344(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.417(4) . ?
C36 H36 0.9300 . ?
C37 O1 1.303(3) . ?
O1 H1A 0.8200 . ?

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 121.4(3) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C7 121.7(3) . . ?
C1 C6 C7 120.4(2) . . ?
C8 C7 C21 121.6(2) . . ?
C8 C7 C6 123.1(2) . . ?
C21 C7 C6 115.4(2) . . ?
C7 C8 C15 121.8(2) . . ?
C7 C8 C9 123.9(2) . . ?
C15 C8 C9 114.3(2) . . ?
C14 C9 C10 118.0(3) . . ?
C14 C9 C8 119.8(3) . . ?
C10 C9 C8 122.2(3) . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C20 C15 C16 118.0(3) . . ?
C20 C15 C8 120.3(2) . . ?
C16 C15 C8 121.6(3) . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C15 121.9(3) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
C26 C21 C22 117.5(2) . . ?
C26 C21 C7 120.2(2) . . ?
C22 C21 C7 122.2(2) . . ?
C23 C22 C21 121.8(2) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 119.7(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 118.9(2) . . ?
C25 C24 N1 117.4(2) . . ?
C23 C24 N1 123.7(2) . . ?
C26 C25 C24 121.1(2) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
N1 C27 C28 122.7(2) . . ?
N1 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
C37 C28 C27 118.6(2) . . ?
C37 C28 C29 119.4(2) . . ?
C27 C28 C29 121.9(2) . . ?
C30 C29 C34 117.1(2) . . ?
C30 C29 C28 123.5(2) . . ?
C34 C29 C28 119.4(2) . . ?
C31 C30 C29 121.2(3) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 121.2(3) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C33 C32 C31 119.3(3) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 121.1(3) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C33 C34 C29 120.2(3) . . ?
C33 C34 C35 121.5(3) . . ?
C29 C34 C35 118.3(2) . . ?
C36 C35 C34 122.6(3) . . ?
C36 C35 H35 118.7 . . ?
C34 C35 H35 118.7 . . ?
C35 C36 C37 120.5(3) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
O1 C37 C28 122.8(2) . . ?
O1 C37 C36 117.6(3) . . ?
C28 C37 C36 119.7(2) . . ?
C27 N1 C24 124.8(2) . . ?
C37 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
