# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 2178135'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.09(C30 H25 N O2)'
_chemical_formula_sum            'C2.61 H2.17 N0.09 O0.17'
_chemical_formula_weight         37.52
_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                   9.206(3)
_cell_length_b                   10.087(3)
_cell_length_c                   13.161(4)
_cell_angle_alpha                99.033(4)
_cell_angle_beta                 97.884(4)
_cell_angle_gamma                107.657(4)
_cell_volume                     1127.8(5)
_cell_formula_units_Z            23
_cell_measurement_reflns_used    5487
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14151
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.783
_diffrn_reflns_theta_min         1.598
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3807
_reflns_number_total             4768
_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       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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         0.213
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.034
_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)+(0.0659P)²+0.2182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1257
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N003(H003)
2.b Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
2.c Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00C), C00K(H00I,H00K)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
;
_atom_sites_solution_hydrogens   mixed
_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 0.22852(14) 0.30014(12) 0.39797(8) 0.0488(3) Uani 1 1 d . . . . .
O002 O 0.38412(12) 0.67079(11) 0.28162(9) 0.0496(3) Uani 1 1 d . . . . .
N003 N 0.14113(13) 0.40908(12) 0.11561(9) 0.0335(3) Uani 1 1 d . . . . .
H003 H 0.1480 0.3546 0.0605 0.040 Uiso 1 1 d R . . . .
C004 C 0.27789(14) 0.28148(14) 0.22000(10) 0.0306(3) Uani 1 1 d . . . . .
C005 C 0.25526(14) 0.42215(14) 0.21091(10) 0.0302(3) Uani 1 1 d . . . . .
C006 C 0.00584(15) 0.40251(14) 0.25056(11) 0.0331(3) Uani 1 1 d . . . . .
C007 C 0.17590(15) 0.47317(14) 0.29814(10) 0.0319(3) Uani 1 1 d . . . . .
C008 C -0.00655(15) 0.37113(14) 0.14149(11) 0.0333(3) Uani 1 1 d . . . . .
C009 C 0.21629(16) 0.73256(14) 0.39380(11) 0.0352(3) Uani 1 1 d . . . . .
C00A C 0.30542(15) 0.19581(15) 0.13607(11) 0.0364(3) Uani 1 1 d . . . . .
H00A H 0.3133 0.2273 0.0737 0.044 Uiso 1 1 calc R . . . .
C00B C 0.60839(16) 0.69674(14) 0.13571(10) 0.0330(3) Uani 1 1 d . . . . .
C00C C 0.26327(16) 0.22991(15) 0.31185(11) 0.0358(3) Uani 1 1 d . . . . .
C00D C 0.22791(16) 0.63536(14) 0.29808(11) 0.0357(3) Uani 1 1 d . . . . .
H00D H 0.1640 0.6485 0.2370 0.043 Uiso 1 1 calc R . . . .
C00E C 0.40828(15) 0.54777(14) 0.22533(11) 0.0335(3) Uani 1 1 d . . . . .
H00E H 0.4905 0.5276 0.2693 0.040 Uiso 1 1 calc R . . . .
C00F C -0.12637(17) 0.37550(15) 0.29366(13) 0.0400(3) Uani 1 1 d . . . . .
H00F H -0.1185 0.3951 0.3660 0.048 Uiso 1 1 calc R . . . .
C00G C 0.75067(17) 0.67500(16) 0.13938(12) 0.0417(3) Uani 1 1 d . . . . .
H00G H 0.7554 0.5838 0.1367 0.050 Uiso 1 1 calc R . . . .
C00H C 0.07238(18) 0.74748(16) 0.40088(12) 0.0423(3) Uani 1 1 d . . . . .
H00H H -0.0130 0.6976 0.3473 0.051 Uiso 1 1 calc R . . . .
C00I C 0.23784(18) 0.44499(16) 0.40241(11) 0.0396(3) Uani 1 1 d . . . . .
H00B H 0.3456 0.5053 0.4263 0.048 Uiso 1 1 calc R . . . .
H00C H 0.1796 0.4711 0.4537 0.048 Uiso 1 1 calc R . . . .
C00J C 0.27832(18) 0.09832(16) 0.31922(13) 0.0439(4) Uani 1 1 d . . . . .
H00J H 0.2685 0.0653 0.3809 0.053 Uiso 1 1 calc R . . . .
C00K C 0.45985(17) 0.57350(16) 0.12349(11) 0.0405(3) Uani 1 1 d . . . . .
H00I H 0.4739 0.4877 0.0880 0.049 Uiso 1 1 calc R . . . .
H00K H 0.3774 0.5905 0.0787 0.049 Uiso 1 1 calc R . . . .
C00L C 0.60648(19) 0.83434(16) 0.14124(12) 0.0446(4) Uani 1 1 d . . . . .
H00L H 0.5127 0.8518 0.1396 0.053 Uiso 1 1 calc R . . . .
C00M C 0.32126(17) 0.06562(16) 0.14275(13) 0.0431(3) Uani 1 1 d . . . . .
H00M H 0.3409 0.0108 0.0859 0.052 Uiso 1 1 calc R . . . .
C00N C -0.27101(17) 0.31859(16) 0.22707(14) 0.0457(4) Uani 1 1 d . . . . .
H00N H -0.3608 0.2993 0.2550 0.055 Uiso 1 1 calc R . . . .
C00O C 0.30760(17) 0.01721(16) 0.23549(13) 0.0458(4) Uani 1 1 d . . . . .
H00O H 0.3183 -0.0703 0.2408 0.055 Uiso 1 1 calc R . . . .
C00P C -0.15077(16) 0.31631(15) 0.07457(12) 0.0408(3) Uani 1 1 d . . . . .
H00P H -0.1593 0.2974 0.0021 0.049 Uiso 1 1 calc R . . . .
C00Q C -0.28237(17) 0.29050(16) 0.11952(14) 0.0454(4) Uani 1 1 d . . . . .
H00Q H -0.3802 0.2535 0.0761 0.054 Uiso 1 1 calc R . . . .
C00R C 0.3414(2) 0.80815(18) 0.47406(13) 0.0497(4) Uani 1 1 d . . . . .
H00R H 0.4384 0.7992 0.4711 0.060 Uiso 1 1 calc R . . . .
C00S C 0.7420(2) 0.94647(16) 0.14921(14) 0.0554(4) Uani 1 1 d . . . . .
H00S H 0.7383 1.0382 0.1531 0.066 Uiso 1 1 calc R . . . .
C00T C 0.88600(18) 0.7879(2) 0.14696(14) 0.0525(4) Uani 1 1 d . . . . .
H00T H 0.9804 0.7717 0.1491 0.063 Uiso 1 1 calc R . . . .
C00U C 0.0550(2) 0.83559(18) 0.48652(14) 0.0520(4) Uani 1 1 d . . . . .
H00U H -0.0420 0.8438 0.4908 0.062 Uiso 1 1 calc R . . . .
C00V C 0.1808(3) 0.91105(19) 0.56531(13) 0.0591(5) Uani 1 1 d . . . . .
H00V H 0.1694 0.9712 0.6226 0.071 Uiso 1 1 calc R . . . .
C00W C 0.8813(2) 0.92322(19) 0.15133(14) 0.0559(4) Uani 1 1 d . . . . .
H00W H 0.9719 0.9985 0.1557 0.067 Uiso 1 1 calc R . . . .
C00X C 0.3230(2) 0.8975(2) 0.55921(14) 0.0610(5) Uani 1 1 d . . . . .
H00X H 0.4081 0.9486 0.6127 0.073 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.3687(17) . ?
O001 C00I 1.4288(18) . ?
O002 C00D 1.4286(17) . ?
O002 C00E 1.4361(17) . ?
N003 H003 0.8601 . ?
N003 C005 1.4822(17) . ?
N003 C008 1.4011(17) . ?
C004 C005 1.5156(18) . ?
C004 C00A 1.3933(19) . ?
C004 C00C 1.3963(19) . ?
C005 C007 1.5456(17) . ?
C005 C00E 1.5474(18) . ?
C006 C007 1.5050(19) . ?
C006 C008 1.401(2) . ?
C006 C00F 1.3836(19) . ?
C007 C00D 1.5592(19) . ?
C007 C00I 1.515(2) . ?
C008 C00P 1.388(2) . ?
C009 C00D 1.5075(19) . ?
C009 C00H 1.392(2) . ?
C009 C00R 1.380(2) . ?
C00A H00A 0.9300 . ?
C00A C00M 1.379(2) . ?
C00B C00G 1.388(2) . ?
C00B C00K 1.5123(19) . ?
C00B C00L 1.384(2) . ?
C00C C00J 1.392(2) . ?
C00D H00D 0.9800 . ?
C00E H00E 0.9800 . ?
C00E C00K 1.5160(19) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.389(2) . ?
C00G H00G 0.9300 . ?
C00G C00T 1.389(2) . ?
C00H H00H 0.9300 . ?
C00H C00U 1.381(2) . ?
C00I H00B 0.9700 . ?
C00I H00C 0.9700 . ?
C00J H00J 0.9300 . ?
C00J C00O 1.374(2) . ?
C00K H00I 0.9700 . ?
C00K H00K 0.9700 . ?
C00L H00L 0.9300 . ?
C00L C00S 1.385(2) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.391(2) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.382(2) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.393(2) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00X 1.387(2) . ?
C00S H00S 0.9300 . ?
C00S C00W 1.369(3) . ?
C00T H00T 0.9300 . ?
C00T C00W 1.371(3) . ?
C00U H00U 0.9300 . ?
C00U C00V 1.372(3) . ?
C00V H00V 0.9300 . ?
C00V C00X 1.369(3) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?

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
C00C O001 C00I 118.06(11) . . ?
C00D O002 C00E 110.13(10) . . ?
C005 N003 H003 114.4 . . ?
C008 N003 H003 114.2 . . ?
C008 N003 C005 107.43(10) . . ?
C00A C004 C005 121.66(12) . . ?
C00A C004 C00C 117.68(12) . . ?
C00C C004 C005 120.58(12) . . ?
N003 C005 C004 112.22(10) . . ?
N003 C005 C007 101.08(10) . . ?
N003 C005 C00E 113.16(10) . . ?
C004 C005 C007 111.72(10) . . ?
C004 C005 C00E 114.32(11) . . ?
C007 C005 C00E 103.17(10) . . ?
C008 C006 C007 107.04(11) . . ?
C00F C006 C007 132.47(13) . . ?
C00F C006 C008 120.34(13) . . ?
C005 C007 C00D 99.77(10) . . ?
C006 C007 C005 102.60(10) . . ?
C006 C007 C00D 110.79(11) . . ?
C006 C007 C00I 118.61(11) . . ?
C00I C007 C005 111.24(11) . . ?
C00I C007 C00D 111.80(11) . . ?
N003 C008 C006 110.52(12) . . ?
C00P C008 N003 128.45(13) . . ?
C00P C008 C006 120.97(13) . . ?
C00H C009 C00D 118.21(13) . . ?
C00R C009 C00D 123.26(13) . . ?
C00R C009 C00H 118.53(14) . . ?
C004 C00A H00A 119.0 . . ?
C00M C00A C004 121.96(13) . . ?
C00M C00A H00A 119.0 . . ?
C00G C00B C00K 121.02(13) . . ?
C00L C00B C00G 117.85(13) . . ?
C00L C00B C00K 121.11(13) . . ?
O001 C00C C004 123.50(13) . . ?
O001 C00C C00J 115.66(12) . . ?
C00J C00C C004 120.80(13) . . ?
O002 C00D C007 105.04(11) . . ?
O002 C00D C009 111.28(11) . . ?
O002 C00D H00D 107.8 . . ?
C007 C00D H00D 107.8 . . ?
C009 C00D C007 116.71(11) . . ?
C009 C00D H00D 107.8 . . ?
O002 C00E C005 106.56(10) . . ?
O002 C00E H00E 108.2 . . ?
O002 C00E C00K 111.44(12) . . ?
C005 C00E H00E 108.2 . . ?
C00K C00E C005 114.04(11) . . ?
C00K C00E H00E 108.2 . . ?
C006 C00F H00F 120.5 . . ?
C006 C00F C00N 118.91(15) . . ?
C00N C00F H00F 120.5 . . ?
C00B C00G H00G 119.6 . . ?
C00B C00G C00T 120.75(14) . . ?
C00T C00G H00G 119.6 . . ?
C009 C00H H00H 119.6 . . ?
C00U C00H C009 120.75(15) . . ?
C00U C00H H00H 119.6 . . ?
O001 C00I C007 113.54(11) . . ?
O001 C00I H00B 108.9 . . ?
O001 C00I H00C 108.9 . . ?
C007 C00I H00B 108.9 . . ?
C007 C00I H00C 108.9 . . ?
H00B C00I H00C 107.7 . . ?
C00C C00J H00J 119.9 . . ?
C00O C00J C00C 120.11(14) . . ?
C00O C00J H00J 119.9 . . ?
C00B C00K C00E 114.91(12) . . ?
C00B C00K H00I 108.5 . . ?
C00B C00K H00K 108.5 . . ?
C00E C00K H00I 108.5 . . ?
C00E C00K H00K 108.5 . . ?
H00I C00K H00K 107.5 . . ?
C00B C00L H00L 119.5 . . ?
C00B C00L C00S 121.07(15) . . ?
C00S C00L H00L 119.5 . . ?
C00A C00M H00M 120.4 . . ?
C00A C00M C00O 119.23(14) . . ?
C00O C00M H00M 120.4 . . ?
C00F C00N H00N 119.8 . . ?
C00Q C00N C00F 120.43(14) . . ?
C00Q C00N H00N 119.8 . . ?
C00J C00O C00M 120.22(14) . . ?
C00J C00O H00O 119.9 . . ?
C00M C00O H00O 119.9 . . ?
C008 C00P H00P 121.1 . . ?
C008 C00P C00Q 117.76(14) . . ?
C00Q C00P H00P 121.1 . . ?
C00N C00Q C00P 121.57(14) . . ?
C00N C00Q H00Q 119.2 . . ?
C00P C00Q H00Q 119.2 . . ?
C009 C00R H00R 119.9 . . ?
C009 C00R C00X 120.26(16) . . ?
C00X C00R H00R 119.9 . . ?
C00L C00S H00S 119.8 . . ?
C00W C00S C00L 120.47(15) . . ?
C00W C00S H00S 119.8 . . ?
C00G C00T H00T 119.8 . . ?
C00W C00T C00G 120.44(15) . . ?
C00W C00T H00T 119.8 . . ?
C00H C00U H00U 120.0 . . ?
C00V C00U C00H 120.04(16) . . ?
C00V C00U H00U 120.0 . . ?
C00U C00V H00V 120.1 . . ?
C00X C00V C00U 119.77(16) . . ?
C00X C00V H00V 120.1 . . ?
C00S C00W C00T 119.42(15) . . ?
C00S C00W H00W 120.3 . . ?
C00T C00W H00W 120.3 . . ?
C00R C00X H00X 119.7 . . ?
C00V C00X C00R 120.64(17) . . ?
C00V C00X H00X 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
