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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1953756'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_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         'C23 H19 N O'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.012(3)
_cell_length_b                   9.465(3)
_cell_length_c                   15.801(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.447(5)
_cell_angle_gamma                90
_cell_volume                     1795.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_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    1.204
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21384
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         2.104
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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                2477
_reflns_number_total             3680
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.032
_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)+(0.0628P)²+0.2965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1352
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00M), C00M(H00N),
 C00N(H00O), C00O(H00P), C00P(H00Q)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00K,H00L)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   geom
_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 1.03963(11) 0.23288(15) 0.80669(9) 0.0677(4) Uani 1 1 d . . . . .
H001 H 1.0345 0.2286 0.7549 0.102 Uiso 1 1 calc GR . . . .
N002 N 0.94887(11) 0.25985(15) 0.65831(9) 0.0511(4) Uani 1 1 d . . . . .
C003 C 0.86487(12) 0.32441(16) 0.69112(11) 0.0464(4) Uani 1 1 d . . . . .
C004 C 0.86102(13) 0.34639(17) 0.78245(10) 0.0467(4) Uani 1 1 d . . . . .
C005 C 0.45858(13) 0.29680(18) 0.65804(11) 0.0483(4) Uani 1 1 d . . . . .
C006 C 0.92781(14) 0.25099(18) 0.56877(11) 0.0515(4) Uani 1 1 d . . . . .
C007 C 0.82634(14) 0.30872(18) 0.54669(11) 0.0514(4) Uani 1 1 d . . . . .
C008 C 0.77572(13) 0.37207(17) 0.62564(11) 0.0501(4) Uani 1 1 d . . . . .
C009 C 0.66391(13) 0.30607(17) 0.64238(11) 0.0501(4) Uani 1 1 d . . . . .
H009 H 0.6644 0.2092 0.6522 0.060 Uiso 1 1 calc R . . . .
C00A C 0.95033(14) 0.30027(18) 0.83651(11) 0.0522(4) Uani 1 1 d . . . . .
C00B C 0.77102(14) 0.41287(18) 0.82104(12) 0.0548(5) Uani 1 1 d . . . . .
H00B H 0.7108 0.4426 0.7874 0.066 Uiso 1 1 calc R . . . .
C00C C 0.56544(13) 0.36795(19) 0.64493(12) 0.0549(4) Uani 1 1 d . . . . .
H00C H 0.5636 0.4655 0.6378 0.066 Uiso 1 1 calc R . . . .
C00D C 0.45105(14) 0.15625(19) 0.68164(11) 0.0566(5) Uani 1 1 d . . . . .
H00D H 0.5159 0.1049 0.6923 0.068 Uiso 1 1 calc R . . . .
C00E C 0.35918(14) 0.3696(2) 0.64582(13) 0.0621(5) Uani 1 1 d . . . . .
H00E H 0.3612 0.4651 0.6322 0.075 Uiso 1 1 calc R . . . .
C00F C 0.34925(15) 0.0912(2) 0.68958(12) 0.0631(5) Uani 1 1 d . . . . .
H00F H 0.3462 -0.0035 0.7050 0.076 Uiso 1 1 calc R . . . .
C00G C 0.25255(15) 0.1646(2) 0.67493(12) 0.0648(5) Uani 1 1 d . . . . .
H00G H 0.1841 0.1198 0.6797 0.078 Uiso 1 1 calc R . . . .
C00H C 0.94672(17) 0.3245(2) 0.92278(12) 0.0645(5) Uani 1 1 d . . . . .
H00H H 1.0055 0.2951 0.9580 0.077 Uiso 1 1 calc R . . . .
C00I C 0.76890(17) 0.4353(2) 0.90636(13) 0.0656(5) Uani 1 1 d . . . . .
H00I H 0.7082 0.4799 0.9302 0.079 Uiso 1 1 calc R . . . .
C00J C 0.25723(15) 0.3037(2) 0.65336(13) 0.0696(6) Uani 1 1 d . . . . .
H00J H 0.1918 0.3544 0.6437 0.084 Uiso 1 1 calc R . . . .
C00K C 0.77443(16) 0.53435(19) 0.61888(15) 0.0696(6) Uani 1 1 d . . . . .
H00A H 0.7480 0.5739 0.6706 0.104 Uiso 1 1 calc GR . . . .
H00K H 0.7260 0.5624 0.5726 0.104 Uiso 1 1 calc GR . . . .
H00L H 0.8485 0.5679 0.6093 0.104 Uiso 1 1 calc GR . . . .
C00L C 0.78666(17) 0.3022(2) 0.46417(13) 0.0704(6) Uani 1 1 d . . . . .
H00M H 0.7170 0.3387 0.4491 0.085 Uiso 1 1 calc R . . . .
C00M C 0.99516(17) 0.1907(2) 0.50977(12) 0.0677(5) Uani 1 1 d . . . . .
H00N H 1.0644 0.1537 0.5253 0.081 Uiso 1 1 calc R . . . .
C00N C 0.85739(19) 0.3914(2) 0.95655(13) 0.0717(6) Uani 1 1 d . . . . .
H00O H 0.8564 0.4075 1.0146 0.086 Uiso 1 1 calc R . . . .
C00O C 0.95690(19) 0.1868(3) 0.42659(13) 0.0786(6) Uani 1 1 d . . . . .
H00P H 1.0017 0.1479 0.3855 0.094 Uiso 1 1 calc R . . . .
C00P C 0.8537(2) 0.2393(3) 0.40352(14) 0.0819(7) Uani 1 1 d . . . . .
H00Q H 0.8285 0.2330 0.3475 0.098 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 H001 0.8200 . ?
O001 C00A 1.343(2) . ?
N002 C003 1.299(2) . ?
N002 C006 1.433(2) . ?
C003 C004 1.460(2) . ?
C003 C008 1.538(2) . ?
C004 C00A 1.423(2) . ?
C004 C00B 1.403(2) . ?
C005 C00C 1.469(2) . ?
C005 C00D 1.385(3) . ?
C005 C00E 1.388(2) . ?
C006 C007 1.373(2) . ?
C006 C00M 1.374(2) . ?
C007 C008 1.524(2) . ?
C007 C00L 1.378(3) . ?
C008 C009 1.511(2) . ?
C008 C00K 1.540(2) . ?
C009 H009 0.9300 . ?
C009 C00C 1.321(2) . ?
C00A C00H 1.384(3) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.366(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00F 1.378(2) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.382(3) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.368(3) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.362(3) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.366(3) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.374(3) . ?
C00J H00J 0.9300 . ?
C00K H00A 0.9600 . ?
C00K H00K 0.9600 . ?
C00K H00L 0.9600 . ?
C00L H00M 0.9300 . ?
C00L C00P 1.400(3) . ?
C00M H00N 0.9300 . ?
C00M C00O 1.382(3) . ?
C00N H00O 0.9300 . ?
C00O H00P 0.9300 . ?
C00O C00P 1.376(3) . ?
C00P H00Q 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
C00A O001 H001 109.5 . . ?
C003 N002 C006 107.57(14) . . ?
N002 C003 C004 120.39(15) . . ?
N002 C003 C008 113.85(15) . . ?
C004 C003 C008 125.76(14) . . ?
C00A C004 C003 120.49(14) . . ?
C00B C004 C003 122.50(16) . . ?
C00B C004 C00A 117.01(16) . . ?
C00D C005 C00C 122.79(14) . . ?
C00D C005 C00E 116.90(16) . . ?
C00E C005 C00C 120.30(16) . . ?
C007 C006 N002 111.16(15) . . ?
C007 C006 C00M 121.81(18) . . ?
C00M C006 N002 127.01(17) . . ?
C006 C007 C008 108.58(15) . . ?
C006 C007 C00L 120.41(17) . . ?
C00L C007 C008 131.01(17) . . ?
C003 C008 C00K 110.18(15) . . ?
C007 C008 C003 98.62(13) . . ?
C007 C008 C00K 109.83(15) . . ?
C009 C008 C003 111.59(13) . . ?
C009 C008 C007 110.82(14) . . ?
C009 C008 C00K 114.66(14) . . ?
C008 C009 H009 115.7 . . ?
C00C C009 C008 128.50(15) . . ?
C00C C009 H009 115.7 . . ?
O001 C00A C004 122.12(16) . . ?
O001 C00A C00H 117.98(17) . . ?
C00H C00A C004 119.89(17) . . ?
C004 C00B H00B 118.9 . . ?
C00I C00B C004 122.17(18) . . ?
C00I C00B H00B 118.9 . . ?
C005 C00C H00C 117.0 . . ?
C009 C00C C005 125.96(16) . . ?
C009 C00C H00C 117.0 . . ?
C005 C00D H00D 119.4 . . ?
C00F C00D C005 121.20(16) . . ?
C00F C00D H00D 119.4 . . ?
C005 C00E H00E 119.2 . . ?
C00J C00E C005 121.67(18) . . ?
C00J C00E H00E 119.2 . . ?
C00D C00F H00F 119.7 . . ?
C00G C00F C00D 120.61(19) . . ?
C00G C00F H00F 119.7 . . ?
C00F C00G H00G 120.2 . . ?
C00J C00G C00F 119.55(18) . . ?
C00J C00G H00G 120.2 . . ?
C00A C00H H00H 119.8 . . ?
C00N C00H C00A 120.40(19) . . ?
C00N C00H H00H 119.8 . . ?
C00B C00I H00I 120.4 . . ?
C00B C00I C00N 119.28(19) . . ?
C00N C00I H00I 120.4 . . ?
C00E C00J H00J 120.0 . . ?
C00G C00J C00E 120.02(17) . . ?
C00G C00J H00J 120.0 . . ?
C008 C00K H00A 109.5 . . ?
C008 C00K H00K 109.5 . . ?
C008 C00K H00L 109.5 . . ?
H00A C00K H00K 109.5 . . ?
H00A C00K H00L 109.5 . . ?
H00K C00K H00L 109.5 . . ?
C007 C00L H00M 120.8 . . ?
C007 C00L C00P 118.37(19) . . ?
C00P C00L H00M 120.8 . . ?
C006 C00M H00N 121.0 . . ?
C006 C00M C00O 118.00(19) . . ?
C00O C00M H00N 121.0 . . ?
C00H C00N C00I 121.24(19) . . ?
C00H C00N H00O 119.4 . . ?
C00I C00N H00O 119.4 . . ?
C00M C00O H00P 119.4 . . ?
C00P C00O C00M 121.2(2) . . ?
C00P C00O H00P 119.4 . . ?
C00L C00P H00Q 119.9 . . ?
C00O C00P C00L 120.2(2) . . ?
C00O C00P H00Q 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
