# 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_b191223a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1974555'
loop_
_audit_author_name
_audit_author_address
'Stepan Kashtanov'
;Xian Jiaotong Liverpool  University
China
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-02-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_b191223a_0m_a       
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.367 Check
RESPONSE: Indeed but low intensity peaks will not be governing the refinement.
;
_vrf_PLAT910_b191223a_0m_a       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
RESPONSE: This has little or no effect at all since the data completeness is very good.
;
_vrf_PLAT911_b191223a_0m_a       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
RESPONSE: This has little or no effect at all since the data completeness is very good.
;
# Added during the CSD deposition process: Saturday 22 February 2020 03:50 PM
# end Validation Reply Form

_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
vsevolod@suda.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        none
_chemical_formula_moiety         '0.07(C32 H27 N O), 0.07(C3 H7 N O)'
_chemical_formula_sum            'C2.59 H2.52 N0.15 O0.15'
_chemical_formula_weight         38.12
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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                   10.9118(6)
_cell_length_b                   11.6167(6)
_cell_length_c                   13.1533(7)
_cell_angle_alpha                114.900(2)
_cell_angle_beta                 109.637(2)
_cell_angle_gamma                96.010(2)
_cell_volume                     1363.93(13)
_cell_formula_units_Z            27
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.7217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1731 before and 0.0625 after correction. The Ratio of minimum to maximum transmission is 0.9698. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_preparation       'as described in the publication'
_exptl_crystal_recrystallization_method 'as described in the publication'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64042
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.439
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4275
_reflns_number_total             6259
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0266(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.4145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.40517(10) 0.81427(10) 0.57252(10) 0.0325(3) Uani 1 1 d . . . . .
N002 N 0.13727(11) 0.39279(11) 0.40847(10) 0.0224(3) Uani 1 1 d . . . . .
O003 O 0.93505(12) 1.20462(13) 0.97561(12) 0.0549(4) Uani 1 1 d . . . . .
N004 N 0.71467(13) 1.07930(13) 0.88125(13) 0.0386(3) Uani 1 1 d . . . . .
C005 C 0.46948(14) 0.62329(13) 0.79460(13) 0.0227(3) Uani 1 1 d . . . . .
C006 C 0.26922(13) 0.59462(13) 0.48374(12) 0.0212(3) Uani 1 1 d . . . . .
C007 C 0.30260(14) 0.72376(14) 0.49246(13) 0.0228(3) Uani 1 1 d . . . . .
C008 C 0.33185(13) 0.54364(13) 0.56481(12) 0.0209(3) Uani 1 1 d . . . . .
C009 C 0.02412(14) 0.27449(13) 0.33204(12) 0.0226(3) Uani 1 1 d . . . . .
C00A C 0.15063(13) 0.49911(13) 0.38976(12) 0.0219(3) Uani 1 1 d . . . . .
C00B C 0.24859(13) 0.41846(13) 0.51554(12) 0.0218(3) Uani 1 1 d . . . . .
C00C C 0.36416(15) 0.59428(14) 0.82414(14) 0.0280(3) Uani 1 1 d . . . . .
C00D C 0.11379(14) 0.62109(14) 0.26983(13) 0.0257(3) Uani 1 1 d . . . . .
C00E C -0.10051(14) 0.28149(15) 0.33385(13) 0.0256(3) Uani 1 1 d . . . . .
C00F C 0.26779(14) 0.31427(13) 0.55100(12) 0.0237(3) Uani 1 1 d . . . . .
C00G C 0.19545(15) 0.74437(15) 0.39734(14) 0.0263(3) Uani 1 1 d . . . . .
C00H C 0.61694(14) 0.68191(13) 0.87975(13) 0.0260(3) Uani 1 1 d . . . . .
C00I C 0.05084(15) 0.50846(15) 0.28579(14) 0.0276(3) Uani 1 1 d . . . . .
C00J C 0.58846(15) 0.65942(14) 0.69329(14) 0.0284(3) Uani 1 1 d . . . . .
C00K C 0.45768(13) 0.60857(13) 0.67971(13) 0.0227(3) Uani 1 1 d . . . . .
C00L C 0.68372(15) 0.70251(15) 0.81239(14) 0.0302(3) Uani 1 1 d . . . . .
C00M C 0.39000(16) 0.28241(16) 0.57082(14) 0.0315(4) Uani 1 1 d . . . . .
C00N C 0.16577(16) 0.24199(15) 0.56013(14) 0.0315(4) Uani 1 1 d . . . . .
C00O C 0.04199(16) 0.15565(15) 0.26106(15) 0.0321(4) Uani 1 1 d . . . . .
C00P C -0.20907(16) 0.16775(16) 0.26549(15) 0.0330(4) Uani 1 1 d . . . . .
C00Q C -0.00134(17) 0.65264(18) 0.19041(17) 0.0355(4) Uani 1 1 d . . . . .
C00R C 0.67834(17) 0.70525(15) 0.99998(14) 0.0331(4) Uani 1 1 d . . . . .
C00S C 0.20707(18) 0.57875(18) 0.20502(16) 0.0354(4) Uani 1 1 d . . . . .
C00T C 0.36883(18) 0.60845(16) 0.93569(15) 0.0360(4) Uani 1 1 d . . . . .
C00U C 0.30607(19) 0.10806(16) 0.60320(15) 0.0401(4) Uani 1 1 d . . . . .
C00V C 0.61850(19) 0.69020(16) 1.07329(15) 0.0399(4) Uani 1 1 d . . . . .
C00W C -0.19104(17) 0.04803(17) 0.19682(17) 0.0414(4) Uani 1 1 d . . . . .
C00X C 0.40808(19) 0.17978(18) 0.59601(16) 0.0406(4) Uani 1 1 d . . . . .
C00Y C -0.06604(17) 0.04171(16) 0.19379(17) 0.0416(4) Uani 1 1 d . . . . .
C00Z C 0.18481(19) 0.13970(16) 0.58617(15) 0.0389(4) Uani 1 1 d . . . . .
C010 C 0.4824(2) 0.65026(17) 1.04551(15) 0.0412(4) Uani 1 1 d . . . . .
C011 C 0.83039(19) 1.16173(18) 0.97889(18) 0.0448(4) Uani 1 1 d . . . . .
C012 C 0.7027(2) 1.0340(2) 0.75698(18) 0.0483(5) Uani 1 1 d . . . . .
C013 C 0.5953(2) 1.0331(2) 0.8945(2) 0.0549(5) Uani 1 1 d . . . . .
H00E H -0.1107(14) 0.3636(16) 0.3837(14) 0.026(4) Uiso 1 1 d . . . . .
H00A H 0.2405(15) 0.8161(15) 0.3887(13) 0.029(4) Uiso 1 1 d . . . . .
H00B H 0.1302(15) 0.7770(15) 0.4327(14) 0.029(4) Uiso 1 1 d . . . . .
H00C H 0.2725(16) 0.5617(15) 0.7561(15) 0.030(4) Uiso 1 1 d . . . . .
H00N H 0.0815(18) 0.2645(17) 0.5482(15) 0.042(5) Uiso 1 1 d . . . . .
H00D H -0.0329(16) 0.5248(15) 0.3027(14) 0.030(4) Uiso 1 1 d . . . . .
H00J H 0.6070(16) 0.6617(16) 0.6270(15) 0.037(4) Uiso 1 1 d . . . . .
H00F H 0.0175(15) 0.4245(16) 0.2094(15) 0.028(4) Uiso 1 1 d . . . . .
H00M H 0.4623(17) 0.3340(17) 0.5649(15) 0.043(5) Uiso 1 1 d . . . . .
H00K H 0.2856(18) 0.5566(16) 0.2521(16) 0.041(5) Uiso 1 1 d . . . . .
H00Q H 0.1557(17) 0.4981(18) 0.1239(17) 0.045(5) Uiso 1 1 d . . . . .
H00G H -0.0650(18) 0.6785(17) 0.2293(16) 0.043(5) Uiso 1 1 d . . . . .
H00W H -0.2671(18) -0.0311(18) 0.1492(16) 0.049(5) Uiso 1 1 d . . . . .
H00L H 0.7815(17) 0.7405(16) 0.8458(15) 0.038(4) Uiso 1 1 d . . . . .
H00P H -0.2990(17) 0.1726(16) 0.2653(15) 0.040(5) Uiso 1 1 d . . . . .
H00H H 0.0353(18) 0.7225(19) 0.1749(17) 0.053(5) Uiso 1 1 d . . . . .
H010 H 0.4597(18) 0.6487(17) 1.1111(17) 0.050(5) Uiso 1 1 d . . . . .
H00O H 0.1304(17) 0.1539(15) 0.2610(15) 0.036(4) Uiso 1 1 d . . . . .
H00R H 0.7773(18) 0.7392(16) 1.0361(15) 0.038(4) Uiso 1 1 d . . . . .
H00T H 0.2789(18) 0.5834(17) 0.9368(16) 0.046(5) Uiso 1 1 d . . . . .
H00Z H 0.1123(18) 0.0917(18) 0.5914(16) 0.045(5) Uiso 1 1 d . . . . .
H00Y H -0.0525(17) -0.0415(18) 0.1432(17) 0.049(5) Uiso 1 1 d . . . . .
H00U H 0.3171(17) 0.0358(18) 0.6188(16) 0.046(5) Uiso 1 1 d . . . . .
H00I H -0.0566(18) 0.5703(18) 0.1079(17) 0.046(5) Uiso 1 1 d . . . . .
H00V H 0.6828(18) 0.7126(17) 1.1568(17) 0.048(5) Uiso 1 1 d . . . . .
H00S H 0.2429(17) 0.6499(18) 0.1898(16) 0.045(5) Uiso 1 1 d . . . . .
H00X H 0.4947(19) 0.1580(18) 0.6075(16) 0.053(5) Uiso 1 1 d . . . . .
H01A H 0.796(2) 1.066(2) 0.760(2) 0.072(7) Uiso 1 1 d . . . . .
H011 H 0.8200(19) 1.1851(19) 1.0581(19) 0.063(6) Uiso 1 1 d . . . . .
H01D H 0.611(2) 1.075(2) 0.981(2) 0.075(7) Uiso 1 1 d . . . . .
H01E H 0.565(2) 0.935(2) 0.856(2) 0.072(7) Uiso 1 1 d . . . . .
H01B H 0.665(2) 0.936(3) 0.707(2) 0.085(7) Uiso 1 1 d . . . . .
H01F H 0.516(2) 1.056(2) 0.849(2) 0.076(7) Uiso 1 1 d . . . . .
H01C H 0.641(2) 1.072(2) 0.720(2) 0.084(8) Uiso 1 1 d . . . . .


_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
O001 C007 1.2232(16) . ?
N002 C009 1.4390(17) . ?
N002 C00A 1.3599(17) . ?
N002 C00B 1.4031(17) . ?
O003 C011 1.219(2) . ?
N004 C011 1.335(2) . ?
N004 C012 1.443(2) . ?
N004 C013 1.450(2) . ?
C005 C00C 1.384(2) . ?
C005 C00H 1.4914(19) . ?
C005 C00K 1.4059(19) . ?
C006 C007 1.4522(19) . ?
C006 C008 1.4428(18) . ?
C006 C00A 1.3795(19) . ?
C007 C00G 1.5223(19) . ?
C008 C00B 1.3763(19) . ?
C008 C00K 1.4720(19) . ?
C009 C00E 1.378(2) . ?
C009 C00O 1.382(2) . ?
C00A C00I 1.4888(19) . ?
C00B C00F 1.4795(19) . ?
C00C C00T 1.388(2) . ?
C00D C00G 1.537(2) . ?
C00D C00I 1.539(2) . ?
C00D C00Q 1.530(2) . ?
C00D C00S 1.530(2) . ?
C00E C00P 1.383(2) . ?
C00F C00M 1.391(2) . ?
C00F C00N 1.392(2) . ?
C00H C00L 1.396(2) . ?
C00H C00R 1.383(2) . ?
C00J C00K 1.407(2) . ?
C00J C00L 1.386(2) . ?
C00M C00X 1.381(2) . ?
C00N C00Z 1.385(2) . ?
C00O C00Y 1.382(2) . ?
C00P C00W 1.381(2) . ?
C00R C00V 1.388(2) . ?
C00T C010 1.392(2) . ?
C00U C00X 1.373(3) . ?
C00U C00Z 1.381(3) . ?
C00V C010 1.379(3) . ?
C00W C00Y 1.386(2) . ?

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
C00A N002 C009 124.98(11) . . ?
C00A N002 C00B 109.37(11) . . ?
C00B N002 C009 125.63(11) . . ?
C011 N004 C012 120.99(16) . . ?
C011 N004 C013 121.99(17) . . ?
C012 N004 C013 117.01(16) . . ?
C00C C005 C00H 126.75(13) . . ?
C00C C005 C00K 126.60(13) . . ?
C00K C005 C00H 106.59(12) . . ?
C008 C006 C007 132.07(12) . . ?
C00A C006 C007 119.83(12) . . ?
C00A C006 C008 107.81(12) . . ?
O001 C007 C006 124.33(13) . . ?
O001 C007 C00G 120.38(12) . . ?
C006 C007 C00G 115.20(12) . . ?
C006 C008 C00K 128.89(12) . . ?
C00B C008 C006 106.46(11) . . ?
C00B C008 C00K 124.63(12) . . ?
C00E C009 N002 118.84(12) . . ?
C00E C009 C00O 120.98(13) . . ?
C00O C009 N002 120.15(13) . . ?
N002 C00A C006 108.30(12) . . ?
N002 C00A C00I 124.62(12) . . ?
C006 C00A C00I 127.06(12) . . ?
N002 C00B C00F 120.94(12) . . ?
C008 C00B N002 108.05(11) . . ?
C008 C00B C00F 130.69(12) . . ?
C005 C00C C00T 129.39(15) . . ?
C00G C00D C00I 109.43(12) . . ?
C00Q C00D C00G 109.89(13) . . ?
C00Q C00D C00I 108.37(12) . . ?
C00S C00D C00G 109.65(12) . . ?
C00S C00D C00I 110.53(13) . . ?
C00S C00D C00Q 108.94(13) . . ?
C009 C00E C00P 119.77(14) . . ?
C00M C00F C00B 119.21(13) . . ?
C00M C00F C00N 118.16(14) . . ?
C00N C00F C00B 122.56(13) . . ?
C007 C00G C00D 115.98(12) . . ?
C00L C00H C005 106.66(12) . . ?
C00R C00H C005 127.38(14) . . ?
C00R C00H C00L 125.88(14) . . ?
C00A C00I C00D 111.09(12) . . ?
C00L C00J C00K 110.36(14) . . ?
C005 C00K C008 125.56(12) . . ?
C005 C00K C00J 107.66(12) . . ?
C00J C00K C008 126.67(13) . . ?
C00J C00L C00H 108.69(13) . . ?
C00X C00M C00F 120.73(16) . . ?
C00Z C00N C00F 120.83(15) . . ?
C009 C00O C00Y 119.27(15) . . ?
C00W C00P C00E 119.55(15) . . ?
C00H C00R C00V 128.96(16) . . ?
C00C C00T C010 128.48(16) . . ?
C00X C00U C00Z 119.64(15) . . ?
C010 C00V C00R 128.87(16) . . ?
C00P C00W C00Y 120.50(15) . . ?
C00U C00X C00M 120.58(16) . . ?
C00O C00Y C00W 119.90(16) . . ?
C00U C00Z C00N 120.05(16) . . ?
C00V C010 C00T 129.75(16) . . ?
O003 C011 N004 126.01(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
