# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_dwt-20230313-2m-b_auto
_database_code_depnum_ccdc_archive 'CCDC 2248219'
loop_
_audit_author_name
_audit_author_address
'Fukuan Zhang.'
;Gannan normal university
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-08-21 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         ?
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.5009(11)
_cell_length_b                   9.4353(11)
_cell_length_c                   16.3857(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.365(11)
_cell_angle_gamma                90
_cell_volume                     1468.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.574
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8504
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.654
_diffrn_reflns_theta_max         65.951
_diffrn_reflns_theta_full        65.951
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             2407
_reflns_number_gt                1970
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1176P)²+0.8592P] 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         2407
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2049
_refine_ls_wR_factor_gt          0.1927
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O001 O 0.8763(2) 0.5887(2) 0.81831(11) 0.0566(6) Uani 1 1 d . . . . .
N002 N 0.7717(2) 0.5294(2) 0.69833(12) 0.0432(6) Uani 1 1 d . . . . .
C003 C 0.5442(3) 0.4607(3) 0.76244(14) 0.0407(6) Uani 1 1 d . . . . .
C004 C 0.7470(3) 0.5544(3) 0.61267(15) 0.0429(7) Uani 1 1 d . . . . .
C005 C 0.6904(3) 0.4170(3) 0.73805(15) 0.0419(6) Uani 1 1 d . . . . .
H00A H 0.7421 0.3851 0.7874 0.050 Uiso 1 1 calc R U . . .
H00B H 0.6834 0.3351 0.7004 0.050 Uiso 1 1 calc R U . . .
C006 C 0.7804(3) 0.4317(3) 0.55939(14) 0.0430(7) Uani 1 1 d . . . . .
C007 C 0.5193(3) 0.5278(3) 0.83682(15) 0.0444(6) Uani 1 1 d . . . . .
H007 H 0.5962 0.5492 0.8721 0.053 Uiso 1 1 calc R U . . .
C008 C 0.4300(3) 0.4324(3) 0.71128(15) 0.0456(7) Uani 1 1 d . . . . .
H008 H 0.4449 0.3869 0.6604 0.055 Uiso 1 1 calc R U . . .
C009 C 0.6952(3) 0.3981(3) 0.49259(15) 0.0453(7) Uani 1 1 d . . . . .
H009 H 0.6179 0.4578 0.4793 0.054 Uiso 1 1 calc R U . . .
C00A C 0.7208(3) 0.2794(3) 0.44505(15) 0.0504(7) Uani 1 1 d . . . . .
H00C H 0.6608 0.2585 0.4001 0.060 Uiso 1 1 calc R U . . .
C00B C 0.6968(3) 0.6803(3) 0.58960(16) 0.0460(7) Uani 1 1 d . . . . .
H00D H 0.6655 0.7410 0.6321 0.055 Uiso 1 1 calc R U . . .
C00C C 0.8676(3) 0.6049(3) 0.74375(16) 0.0461(7) Uani 1 1 d . . . . .
C00D C 0.8952(3) 0.3405(3) 0.57571(15) 0.0486(7) Uani 1 1 d . . . . .
H00E H 0.9563 0.3603 0.6204 0.058 Uiso 1 1 calc R U . . .
C00E C 0.9197(3) 0.2230(3) 0.52755(16) 0.0511(7) Uani 1 1 d . . . . .
H00F H 0.9976 0.1633 0.5395 0.061 Uiso 1 1 calc R U . . .
C00F C 0.2948(3) 0.4702(3) 0.73402(17) 0.0508(7) Uani 1 1 d . . . . .
H00G H 0.2180 0.4516 0.6982 0.061 Uiso 1 1 calc R U . . .
C00G C 0.3843(3) 0.5635(3) 0.85989(17) 0.0494(7) Uani 1 1 d . . . . .
H00H H 0.3688 0.6080 0.9111 0.059 Uiso 1 1 calc R U . . .
C00H C 0.2710(3) 0.5346(3) 0.80846(17) 0.0498(7) Uani 1 1 d . . . . .
H00I H 0.1780 0.5589 0.8243 0.060 Uiso 1 1 calc R U . . .
C00I C 0.8334(3) 0.1912(3) 0.46272(16) 0.0525(7) Uani 1 1 d . . . . .
H00J H 0.8506 0.1096 0.4303 0.063 Uiso 1 1 calc R U . . .
C00J C 0.9642(3) 0.7027(3) 0.69906(16) 0.0510(7) Uani 1 1 d . . . . .
H00K H 0.9162 0.7930 0.6889 0.077 Uiso 1 1 calc R U . . .
H00L H 0.9907 0.6598 0.6469 0.077 Uiso 1 1 calc R U . . .
H00M H 1.0489 0.7194 0.7321 0.077 Uiso 1 1 calc R U . . .
C00K C 0.6838(3) 0.7374(3) 0.50441(16) 0.0519(7) Uani 1 1 d . . . . .
H00N H 0.7346 0.6753 0.4668 0.078 Uiso 1 1 calc R U . . .
H00O H 0.7240 0.8329 0.5023 0.078 Uiso 1 1 calc R U . . .
H00P H 0.5842 0.7412 0.4886 0.078 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
O001 C00C 1.234(3) . ?
N002 C00C 1.372(3) . ?
N002 C004 1.441(3) . ?
N002 C005 1.468(3) . ?
C003 C008 1.393(4) . ?
C003 C007 1.395(4) . ?
C003 C005 1.505(4) . ?
C004 C00B 1.334(4) . ?
C004 C006 1.486(4) . ?
C005 H00A 0.9900 . ?
C005 H00B 0.9900 . ?
C006 C009 1.393(4) . ?
C006 C00D 1.413(4) . ?
C007 C00G 1.382(4) . ?
C007 H007 0.9500 . ?
C008 C00F 1.386(4) . ?
C008 H008 0.9500 . ?
C009 C00A 1.386(4) . ?
C009 H009 0.9500 . ?
C00A C00I 1.385(4) . ?
C00A H00C 0.9500 . ?
C00B C00K 1.500(4) . ?
C00B H00D 0.9500 . ?
C00C C00J 1.496(4) . ?
C00D C00E 1.382(4) . ?
C00D H00E 0.9500 . ?
C00E C00I 1.371(4) . ?
C00E H00F 0.9500 . ?
C00F C00H 1.383(4) . ?
C00F H00G 0.9500 . ?
C00G C00H 1.390(4) . ?
C00G H00H 0.9500 . ?
C00H H00I 0.9500 . ?
C00I H00J 0.9500 . ?
C00J H00K 0.9800 . ?
C00J H00L 0.9800 . ?
C00J H00M 0.9800 . ?
C00K H00N 0.9800 . ?
C00K H00O 0.9800 . ?
C00K H00P 0.9800 . ?

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 N002 C004 123.1(2) . . ?
C00C N002 C005 119.0(2) . . ?
C004 N002 C005 117.9(2) . . ?
C008 C003 C007 118.5(3) . . ?
C008 C003 C005 120.3(2) . . ?
C007 C003 C005 121.2(2) . . ?
C00B C004 N002 118.5(2) . . ?
C00B C004 C006 127.2(2) . . ?
N002 C004 C006 114.2(2) . . ?
N002 C005 C003 114.1(2) . . ?
N002 C005 H00A 108.7 . . ?
C003 C005 H00A 108.7 . . ?
N002 C005 H00B 108.7 . . ?
C003 C005 H00B 108.7 . . ?
H00A C005 H00B 107.6 . . ?
C009 C006 C00D 117.0(3) . . ?
C009 C006 C004 121.0(2) . . ?
C00D C006 C004 122.0(2) . . ?
C00G C007 C003 120.8(2) . . ?
C00G C007 H007 119.6 . . ?
C003 C007 H007 119.6 . . ?
C00F C008 C003 120.6(3) . . ?
C00F C008 H008 119.7 . . ?
C003 C008 H008 119.7 . . ?
C00A C009 C006 121.5(3) . . ?
C00A C009 H009 119.3 . . ?
C006 C009 H009 119.3 . . ?
C00I C00A C009 120.4(3) . . ?
C00I C00A H00C 119.8 . . ?
C009 C00A H00C 119.8 . . ?
C004 C00B C00K 127.6(3) . . ?
C004 C00B H00D 116.2 . . ?
C00K C00B H00D 116.2 . . ?
O001 C00C N002 120.8(3) . . ?
O001 C00C C00J 121.6(2) . . ?
N002 C00C C00J 117.5(2) . . ?
C00E C00D C006 120.9(2) . . ?
C00E C00D H00E 119.6 . . ?
C006 C00D H00E 119.6 . . ?
C00I C00E C00D 121.1(3) . . ?
C00I C00E H00F 119.5 . . ?
C00D C00E H00F 119.5 . . ?
C00H C00F C008 120.5(3) . . ?
C00H C00F H00G 119.7 . . ?
C008 C00F H00G 119.7 . . ?
C007 C00G C00H 120.2(3) . . ?
C007 C00G H00H 119.9 . . ?
C00H C00G H00H 119.9 . . ?
C00F C00H C00G 119.3(3) . . ?
C00F C00H H00I 120.3 . . ?
C00G C00H H00I 120.3 . . ?
C00E C00I C00A 119.2(3) . . ?
C00E C00I H00J 120.4 . . ?
C00A C00I H00J 120.4 . . ?
C00C C00J H00K 109.5 . . ?
C00C C00J H00L 109.5 . . ?
H00K C00J H00L 109.5 . . ?
C00C C00J H00M 109.5 . . ?
H00K C00J H00M 109.5 . . ?
H00L C00J H00M 109.5 . . ?
C00B C00K H00N 109.5 . . ?
C00B C00K H00O 109.5 . . ?
H00N C00K H00O 109.5 . . ?
C00B C00K H00P 109.5 . . ?
H00N C00K H00P 109.5 . . ?
H00O C00K H00P 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C00C N002 C004 C00B -62.9(4) . . . . ?
C005 N002 C004 C00B 117.4(3) . . . . ?
C00C N002 C004 C006 117.8(3) . . . . ?
C005 N002 C004 C006 -61.8(3) . . . . ?
C00C N002 C005 C003 99.1(3) . . . . ?
C004 N002 C005 C003 -81.3(3) . . . . ?
C008 C003 C005 N002 95.5(3) . . . . ?
C007 C003 C005 N002 -85.6(3) . . . . ?
C00B C004 C006 C009 -38.3(4) . . . . ?
N002 C004 C006 C009 140.9(2) . . . . ?
C00B C004 C006 C00D 144.4(3) . . . . ?
N002 C004 C006 C00D -36.4(3) . . . . ?
C008 C003 C007 C00G 1.0(4) . . . . ?
C005 C003 C007 C00G -177.9(2) . . . . ?
C007 C003 C008 C00F 0.0(4) . . . . ?
C005 C003 C008 C00F 178.8(3) . . . . ?
C00D C006 C009 C00A 0.9(4) . . . . ?
C004 C006 C009 C00A -176.5(2) . . . . ?
C006 C009 C00A C00I -0.5(4) . . . . ?
N002 C004 C00B C00K 170.0(2) . . . . ?
C006 C004 C00B C00K -10.9(5) . . . . ?
C004 N002 C00C O001 173.4(3) . . . . ?
C005 N002 C00C O001 -6.9(4) . . . . ?
C004 N002 C00C C00J -8.9(4) . . . . ?
C005 N002 C00C C00J 170.7(2) . . . . ?
C009 C006 C00D C00E -0.6(4) . . . . ?
C004 C006 C00D C00E 176.7(2) . . . . ?
C006 C00D C00E C00I -0.2(4) . . . . ?
C003 C008 C00F C00H -1.0(5) . . . . ?
C003 C007 C00G C00H -0.9(4) . . . . ?
C008 C00F C00H C00G 1.1(5) . . . . ?
C007 C00G C00H C00F -0.1(4) . . . . ?
C00D C00E C00I C00A 0.7(4) . . . . ?
C009 C00A C00I C00E -0.4(4) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054

