# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_i18213
_database_code_depnum_ccdc_archive 'CCDC 2085356'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 N O2'
_chemical_formula_sum            'C24 H17 N O2'
_chemical_formula_weight         351.38

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.4058(2)
_cell_length_b                   12.1092(3)
_cell_length_c                   21.6453(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.2490(10)
_cell_angle_gamma                90
_cell_volume                     1677.71(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50975
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.927
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3704
_reflns_number_gt                3271
_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0446P)²+0.7291P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3704
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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
O1 O 0.91233(13) 0.66636(8) 0.51659(4) 0.0225(2) Uani 1 1 d . . . . .
O2 O 1.25667(13) 0.60515(7) 0.52173(4) 0.0217(2) Uani 1 1 d . . . . .
N1 N 0.61256(14) 0.62219(8) 0.17468(4) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.78876(17) 0.56265(9) 0.18174(5) 0.0152(2) Uani 1 1 d . . . . .
C2 C 0.90334(17) 0.55679(9) 0.23786(5) 0.0158(2) Uani 1 1 d . . . . .
H2 H 1.024257 0.511480 0.241522 0.019 Uiso 1 1 calc R U . . .
C3 C 0.83983(17) 0.61769(9) 0.28862(5) 0.0150(2) Uani 1 1 d . . . . .
C4 C 0.65835(17) 0.68103(9) 0.28027(5) 0.0161(2) Uani 1 1 d . . . . .
H4 H 0.610463 0.724818 0.313261 0.019 Uiso 1 1 calc R U . . .
C5 C 0.54733(17) 0.67988(9) 0.22329(5) 0.0148(2) Uani 1 1 d . . . . .
C6 C 0.85011(18) 0.49772(9) 0.12684(5) 0.0162(2) Uani 1 1 d . . . . .
C7 C 0.69764(18) 0.46862(9) 0.08174(5) 0.0186(2) Uani 1 1 d . . . . .
H7 H 0.558244 0.493892 0.085324 0.022 Uiso 1 1 calc R U . . .
C8 C 0.7479(2) 0.40320(10) 0.03182(5) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.643108 0.384663 0.001288 0.026 Uiso 1 1 calc R U . . .
C9 C 0.9504(2) 0.36474(10) 0.02627(5) 0.0226(3) Uani 1 1 d . . . . .
H9 H 0.983572 0.318186 -0.007281 0.027 Uiso 1 1 calc R U . . .
C10 C 1.10416(19) 0.39478(10) 0.07010(5) 0.0211(3) Uani 1 1 d . . . . .
H10 H 1.243316 0.369309 0.066254 0.025 Uiso 1 1 calc R U . . .
C11 C 1.05519(18) 0.46207(9) 0.11966(5) 0.0180(2) Uani 1 1 d . . . . .
H11 H 1.162031 0.483899 0.148814 0.022 Uiso 1 1 calc R U . . .
C12 C 0.95796(17) 0.61387(9) 0.34924(5) 0.0155(2) Uani 1 1 d . . . . .
C13 C 1.16467(18) 0.57602(9) 0.35327(5) 0.0176(2) Uani 1 1 d . . . . .
H13 H 1.229219 0.553644 0.316528 0.021 Uiso 1 1 calc R U . . .
C14 C 1.27967(18) 0.56999(10) 0.40966(5) 0.0185(2) Uani 1 1 d . . . . .
H14 H 1.419315 0.543442 0.411955 0.022 Uiso 1 1 calc R U . . .
C15 C 1.18061(18) 0.60433(9) 0.46137(5) 0.0171(2) Uani 1 1 d . . . . .
C16 C 0.97636(18) 0.64144(9) 0.45831(5) 0.0166(2) Uani 1 1 d . . . . .
C17 C 0.86056(18) 0.64749(9) 0.40363(5) 0.0165(2) Uani 1 1 d . . . . .
H17 H 0.720398 0.673280 0.402412 0.020 Uiso 1 1 calc R U . . .
C18 C 1.09230(18) 0.65118(10) 0.55714(5) 0.0204(3) Uani 1 1 d . . . . .
H18A H 1.058679 0.600607 0.591281 0.024 Uiso 1 1 calc R U . . .
H18B H 1.137109 0.722872 0.575198 0.024 Uiso 1 1 calc R U . . .
C19 C 0.34921(17) 0.74308(9) 0.21253(5) 0.0151(2) Uani 1 1 d . . . . .
C20 C 0.25287(18) 0.79916(9) 0.26008(5) 0.0176(2) Uani 1 1 d . . . . .
H20 H 0.314444 0.797461 0.300713 0.021 Uiso 1 1 calc R U . . .
C21 C 0.06825(18) 0.85742(9) 0.24884(5) 0.0198(2) Uani 1 1 d . . . . .
H21 H 0.004827 0.895077 0.281728 0.024 Uiso 1 1 calc R U . . .
C22 C -0.02387(18) 0.86074(9) 0.18962(6) 0.0203(2) Uani 1 1 d . . . . .
H22 H -0.149740 0.900734 0.181821 0.024 Uiso 1 1 calc R U . . .
C23 C 0.07007(18) 0.80497(10) 0.14196(5) 0.0208(3) Uani 1 1 d . . . . .
H23 H 0.008299 0.807114 0.101350 0.025 Uiso 1 1 calc R U . . .
C24 C 0.25341(18) 0.74621(9) 0.15330(5) 0.0173(2) Uani 1 1 d . . . . .
H24 H 0.314848 0.707552 0.120418 0.021 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
O1 C16 1.3751(13) . ?
O1 C18 1.4331(14) . ?
O2 C15 1.3764(13) . ?
O2 C18 1.4387(14) . ?
N1 C1 1.3430(14) . ?
N1 C5 1.3431(14) . ?
C1 C2 1.3962(15) . ?
C1 C6 1.4905(15) . ?
C2 C3 1.3969(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3985(16) . ?
C3 C12 1.4894(15) . ?
C4 C5 1.3993(15) . ?
C4 H4 0.9500 . ?
C5 C19 1.4925(15) . ?
C6 C11 1.3973(16) . ?
C6 C7 1.3986(16) . ?
C7 C8 1.3878(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3879(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3891(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3928(16) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.4007(16) . ?
C12 C17 1.4137(15) . ?
C13 C14 1.4027(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3727(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3826(16) . ?
C16 C17 1.3740(15) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3968(16) . ?
C19 C24 1.4000(15) . ?
C20 C21 1.3903(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.3906(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.3896(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3868(16) . ?
C23 H23 0.9500 . ?
C24 H24 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
C16 O1 C18 105.78(9) . . ?
C15 O2 C18 105.62(9) . . ?
C1 N1 C5 118.42(9) . . ?
N1 C1 C2 122.48(10) . . ?
N1 C1 C6 116.05(10) . . ?
C2 C1 C6 121.39(10) . . ?
C1 C2 C3 119.87(10) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.00(10) . . ?
C2 C3 C12 121.53(10) . . ?
C4 C3 C12 121.46(10) . . ?
C3 C4 C5 119.97(10) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 122.18(10) . . ?
N1 C5 C19 115.67(9) . . ?
C4 C5 C19 122.15(10) . . ?
C11 C6 C7 118.58(10) . . ?
C11 C6 C1 122.01(10) . . ?
C7 C6 C1 119.38(10) . . ?
C8 C7 C6 120.69(11) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.32(11) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.55(11) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.28(11) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.50(11) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C13 C12 C17 119.30(10) . . ?
C13 C12 C3 120.75(10) . . ?
C17 C12 C3 119.94(10) . . ?
C12 C13 C14 122.28(10) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 116.75(10) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
C14 C15 O2 128.21(10) . . ?
C14 C15 C16 121.75(10) . . ?
O2 C15 C16 110.01(10) . . ?
C17 C16 O1 127.46(10) . . ?
C17 C16 C15 122.45(10) . . ?
O1 C16 C15 110.07(10) . . ?
C16 C17 C12 117.46(10) . . ?
C16 C17 H17 121.3 . . ?
C12 C17 H17 121.3 . . ?
O1 C18 O2 108.15(9) . . ?
O1 C18 H18A 110.1 . . ?
O2 C18 H18A 110.1 . . ?
O1 C18 H18B 110.1 . . ?
O2 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C20 C19 C24 118.11(10) . . ?
C20 C19 C5 122.13(10) . . ?
C24 C19 C5 119.76(10) . . ?
C21 C20 C19 121.01(10) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 120.21(11) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.33(11) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 120.42(11) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.91(11) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_i18212
_database_code_depnum_ccdc_archive 'CCDC 2085361'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N2'
_chemical_formula_sum            'C30 H26 N2'
_chemical_formula_weight         414.53

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'

_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                   9.8179(3)
_cell_length_b                   10.4973(3)
_cell_length_c                   11.9206(3)
_cell_angle_alpha                76.3210(10)
_cell_angle_beta                 87.7270(10)
_cell_angle_gamma                66.7560(10)
_cell_volume                     1094.83(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      30.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.214
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54798
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6393
_reflns_number_gt                5364
_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0539P)²+0.3917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6393
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.70705(9) 0.44975(9) 0.47178(7) 0.01501(16) Uani 1 1 d . . . . .
H1 H 0.6434(16) 0.4235(15) 0.5205(12) 0.024(3) Uiso 1 1 d . . . . .
N2 N 0.52102(9) 0.67358(9) 0.35981(7) 0.01470(16) Uani 1 1 d . . . . .
C1 C 0.65583(11) 0.60651(10) 0.44030(8) 0.01419(18) Uani 1 1 d . . . . .
C2 C 0.69909(10) 0.51498(10) 0.26011(8) 0.01350(17) Uani 1 1 d . . . . .
H2 H 0.706660 0.481443 0.187365 0.016 Uiso 1 1 calc R U . . .
C3 C 0.72142(10) 0.39111(10) 0.36900(8) 0.01368(17) Uani 1 1 d . . . . .
H3 H 0.638923 0.358460 0.366553 0.016 Uiso 1 1 calc R U . . .
C4 C 0.54595(10) 0.62552(10) 0.26757(8) 0.01363(17) Uani 1 1 d . . . . .
C5 C 0.81121(11) 0.58452(10) 0.26631(8) 0.01410(18) Uani 1 1 d . . . . .
H5 H 0.913911 0.508361 0.274519 0.017 Uiso 1 1 calc R U . . .
C6 C 0.78276(11) 0.64032(11) 0.37764(8) 0.01622(18) Uani 1 1 d . . . . .
H6A H 0.874268 0.594221 0.429275 0.019 Uiso 1 1 calc R U . . .
H6AB H 0.755435 0.744756 0.357640 0.019 Uiso 1 1 calc R U . . .
C7 C 0.86703(11) 0.26422(10) 0.37154(8) 0.01450(18) Uani 1 1 d . . . . .
C8 C 0.99689(12) 0.24778(11) 0.42732(9) 0.0198(2) Uani 1 1 d . . . . .
H8 H 0.995269 0.316749 0.467137 0.024 Uiso 1 1 calc R U . . .
C9 C 1.12921(12) 0.13129(12) 0.42542(10) 0.0223(2) Uani 1 1 d . . . . .
H9 H 1.217433 0.122104 0.462802 0.027 Uiso 1 1 calc R U . . .
C10 C 1.13259(12) 0.02868(12) 0.36912(9) 0.0220(2) Uani 1 1 d . . . . .
H10 H 1.222675 -0.051111 0.368259 0.026 Uiso 1 1 calc R U . . .
C11 C 1.00339(13) 0.04339(12) 0.31402(10) 0.0231(2) Uani 1 1 d . . . . .
H11 H 1.004823 -0.026848 0.275735 0.028 Uiso 1 1 calc R U . . .
C12 C 0.87193(12) 0.16074(11) 0.31478(9) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.784284 0.170550 0.276115 0.022 Uiso 1 1 calc R U . . .
C13 C 0.42685(11) 0.67372(10) 0.17532(8) 0.01451(18) Uani 1 1 d . . . . .
C14 C 0.46172(11) 0.65558(11) 0.06374(9) 0.01725(19) Uani 1 1 d . . . . .
H14 H 0.562702 0.613619 0.046281 0.021 Uiso 1 1 calc R U . . .
C15 C 0.34962(12) 0.69853(11) -0.02200(9) 0.0201(2) Uani 1 1 d . . . . .
H15 H 0.374490 0.685936 -0.097589 0.024 Uiso 1 1 calc R U . . .
C16 C 0.20178(12) 0.75963(12) 0.00253(9) 0.0220(2) Uani 1 1 d . . . . .
H16 H 0.125455 0.788455 -0.055991 0.026 Uiso 1 1 calc R U . . .
C17 C 0.16560(12) 0.77859(12) 0.11348(10) 0.0217(2) Uani 1 1 d . . . . .
H17 H 0.064428 0.820279 0.130539 0.026 Uiso 1 1 calc R U . . .
C18 C 0.27709(11) 0.73668(11) 0.19904(9) 0.01755(19) Uani 1 1 d . . . . .
H18 H 0.251738 0.750755 0.274203 0.021 Uiso 1 1 calc R U . . .
C19 C 0.79635(11) 0.69585(10) 0.15452(8) 0.01520(18) Uani 1 1 d . . . . .
C20 C 0.70232(12) 0.83966(11) 0.13775(9) 0.0214(2) Uani 1 1 d . . . . .
H20 H 0.647155 0.872979 0.199735 0.026 Uiso 1 1 calc R U . . .
C21 C 0.68834(14) 0.93509(12) 0.03112(10) 0.0263(2) Uani 1 1 d . . . . .
H21 H 0.624979 1.033060 0.021446 0.032 Uiso 1 1 calc R U . . .
C22 C 0.76590(13) 0.88842(12) -0.06076(10) 0.0248(2) Uani 1 1 d . . . . .
H22 H 0.755463 0.953735 -0.133476 0.030 Uiso 1 1 calc R U . . .
C23 C 0.85902(13) 0.74550(12) -0.04586(9) 0.0232(2) Uani 1 1 d . . . . .
H23 H 0.912208 0.712415 -0.108656 0.028 Uiso 1 1 calc R U . . .
C24 C 0.87458(12) 0.65051(11) 0.06110(9) 0.0196(2) Uani 1 1 d . . . . .
H24 H 0.939624 0.553030 0.070746 0.023 Uiso 1 1 calc R U . . .
C25 C 0.62522(11) 0.66473(11) 0.54795(8) 0.01539(18) Uani 1 1 d . . . . .
C26 C 0.70918(12) 0.58479(11) 0.65147(9) 0.0199(2) Uani 1 1 d . . . . .
H26 H 0.783573 0.492168 0.655167 0.024 Uiso 1 1 calc R U . . .
C27 C 0.68460(13) 0.63984(13) 0.74919(9) 0.0238(2) Uani 1 1 d . . . . .
H27 H 0.740618 0.583762 0.819700 0.029 Uiso 1 1 calc R U . . .
C28 C 0.57846(13) 0.77656(13) 0.74416(9) 0.0232(2) Uani 1 1 d . . . . .
H28 H 0.562363 0.814352 0.810777 0.028 Uiso 1 1 calc R U . . .
C29 C 0.49611(12) 0.85750(12) 0.64105(9) 0.0208(2) Uani 1 1 d . . . . .
H29 H 0.423999 0.951251 0.637030 0.025 Uiso 1 1 calc R U . . .
C30 C 0.51877(11) 0.80183(11) 0.54336(9) 0.01795(19) Uani 1 1 d . . . . .
H30 H 0.461409 0.857563 0.473335 0.022 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
N1 C1 1.4735(12) . ?
N1 C3 1.4746(12) . ?
N1 H1 0.913(15) . ?
N2 C4 1.2912(12) . ?
N2 C1 1.4879(12) . ?
C1 C25 1.5185(13) . ?
C1 C6 1.5449(13) . ?
C2 C4 1.5087(13) . ?
C2 C5 1.5545(13) . ?
C2 C3 1.5567(13) . ?
C2 H2 1.0000 . ?
C3 C7 1.5167(13) . ?
C3 H3 1.0000 . ?
C4 C13 1.4847(13) . ?
C5 C19 1.5189(13) . ?
C5 C6 1.5463(13) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.3916(14) . ?
C7 C12 1.3942(14) . ?
C8 C9 1.3930(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.3870(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3884(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3903(14) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3982(13) . ?
C13 C18 1.4024(14) . ?
C14 C15 1.3924(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.3870(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3951(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3886(14) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3939(14) . ?
C19 C24 1.3968(13) . ?
C20 C21 1.3932(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.3831(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.3865(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.3918(15) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.3952(14) . ?
C25 C26 1.3970(14) . ?
C26 C27 1.3912(14) . ?
C26 H26 0.9500 . ?
C27 C28 1.3904(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.3889(16) . ?
C28 H28 0.9500 . ?
C29 C30 1.3949(14) . ?
C29 H29 0.9500 . ?
C30 H30 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
C1 N1 C3 111.90(7) . . ?
C1 N1 H1 110.0(9) . . ?
C3 N1 H1 110.2(9) . . ?
C4 N2 C1 110.96(8) . . ?
N1 C1 N2 111.06(8) . . ?
N1 C1 C25 110.48(8) . . ?
N2 C1 C25 110.38(8) . . ?
N1 C1 C6 106.61(8) . . ?
N2 C1 C6 108.65(8) . . ?
C25 C1 C6 109.57(8) . . ?
C4 C2 C5 107.25(8) . . ?
C4 C2 C3 104.77(7) . . ?
C5 C2 C3 110.69(8) . . ?
C4 C2 H2 111.3 . . ?
C5 C2 H2 111.3 . . ?
C3 C2 H2 111.3 . . ?
N1 C3 C7 113.04(8) . . ?
N1 C3 C2 107.76(7) . . ?
C7 C3 C2 112.19(8) . . ?
N1 C3 H3 107.9 . . ?
C7 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
N2 C4 C13 121.07(8) . . ?
N2 C4 C2 117.04(8) . . ?
C13 C4 C2 121.85(8) . . ?
C19 C5 C6 115.65(8) . . ?
C19 C5 C2 109.58(8) . . ?
C6 C5 C2 106.65(7) . . ?
C19 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C2 C5 H5 108.2 . . ?
C1 C6 C5 109.59(8) . . ?
C1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C1 C6 H6AB 109.8 . . ?
C5 C6 H6AB 109.8 . . ?
H6A C6 H6AB 108.2 . . ?
C8 C7 C12 118.55(9) . . ?
C8 C7 C3 122.48(9) . . ?
C12 C7 C3 118.96(9) . . ?
C7 C8 C9 120.72(10) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.22(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.54(10) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.11(10) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.86(10) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 118.80(9) . . ?
C14 C13 C4 120.68(9) . . ?
C18 C13 C4 120.51(9) . . ?
C15 C14 C13 120.52(9) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.26(10) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.75(10) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.17(10) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.49(9) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C20 C19 C24 118.01(9) . . ?
C20 C19 C5 123.60(9) . . ?
C24 C19 C5 118.29(9) . . ?
C21 C20 C19 120.74(10) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.56(10) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.45(10) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 120.00(10) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 121.22(10) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C30 C25 C26 118.98(9) . . ?
C30 C25 C1 120.55(9) . . ?
C26 C25 C1 120.36(9) . . ?
C27 C26 C25 120.47(10) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 120.31(10) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 119.53(10) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.33(10) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.35(10) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045

