# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2057127'
loop_
_audit_author_name
_audit_author_address
'Jiangfei Chen'
;hunnan university
China
;
_audit_update_record             
;
2021-01-19 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.059(8)
_cell_length_b                   19.92(2)
_cell_length_c                   9.454(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.125(12)
_cell_angle_gamma                90
_cell_volume                     1329(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3236
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      23.04

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9430
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4784
_reflns_number_gt                2781
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_chemical_absolute_configuration S
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1398P)²+4.1104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(6)
_refine_ls_number_reflns         4784
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1885
_refine_ls_R_factor_gt           0.1241
_refine_ls_wR_factor_ref         0.3636
_refine_ls_wR_factor_gt          0.3191
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9412(8) 0.1812(4) 0.1899(6) 0.043(2) Uani 1 1 d . . .
O1 O 1.1161(7) 0.1788(4) 0.2247(6) 0.0549(19) Uani 1 1 d . . .
C7 C 0.8662(11) 0.1996(5) 0.0701(8) 0.041(2) Uani 1 1 d . . .
C6 C 0.9789(11) 0.2248(6) -0.0441(8) 0.047(3) Uani 1 1 d . . .
C10 C 0.7994(11) 0.1508(5) 0.2892(8) 0.041(2) Uani 1 1 d . . .
H10 H 0.8037 0.1018 0.2828 0.049 Uiso 1 1 calc R . .
C1 C 1.0656(12) 0.1794(7) -0.1332(11) 0.064(3) Uani 1 1 d . . .
H1 H 1.0628 0.1334 -0.1157 0.077 Uiso 1 1 calc R . .
C5 C 1.0013(17) 0.2903(7) -0.0599(12) 0.069(3) Uani 1 1 d . . .
H5 H 0.9527 0.3194 0.0069 0.082 Uiso 1 1 calc R . .
C9 C 0.6085(11) 0.1777(6) 0.2280(10) 0.055(3) Uani 1 1 d . . .
H9 H 0.5095 0.1441 0.2407 0.066 Uiso 1 1 calc R . .
C2 C 1.1537(17) 0.2049(9) -0.2457(11) 0.079(4) Uani 1 1 d . . .
H2 H 1.2014 0.1752 -0.3116 0.095 Uiso 1 1 calc R . .
C8 C 0.6553(11) 0.1852(5) 0.0650(11) 0.057(3) Uani 1 1 d . . .
C4 C 1.0963(19) 0.3158(8) -0.1749(14) 0.088(5) Uani 1 1 d . . .
H4 H 1.1063 0.3619 -0.1894 0.106 Uiso 1 1 calc R . .
C12 C 0.6213(15) 0.1194(7) -0.0158(12) 0.073(3) Uani 1 1 d . . .
H12A H 0.6887 0.1205 -0.1030 0.109 Uiso 1 1 calc R . .
H12B H 0.4882 0.1146 -0.0357 0.109 Uiso 1 1 calc R . .
H12C H 0.6657 0.0821 0.0410 0.109 Uiso 1 1 calc R . .
C3 C 1.177(2) 0.2702(10) -0.2687(14) 0.098(5) Uani 1 1 d . . .
H3 H 1.2457 0.2853 -0.3455 0.117 Uiso 1 1 calc R . .
C13 C 0.8485(19) 0.1714(9) 0.4334(11) 0.093(5) Uani 1 1 d . . .
H13 H 0.9708 0.1626 0.4673 0.111 Uiso 1 1 calc R . .
C16 C 0.5514(14) 0.2405(7) 0.2907(16) 0.091(5) Uani 1 1 d . . .
H16A H 0.4252 0.2533 0.2575 0.109 Uiso 1 1 calc R . .
H16B H 0.6385 0.2758 0.2655 0.109 Uiso 1 1 calc R . .
C15 C 0.5541(19) 0.2282(8) 0.4689(16) 0.100(5) Uani 1 1 d . . .
H15A H 0.5309 0.2706 0.5155 0.120 Uiso 1 1 calc R . .
H15B H 0.4535 0.1977 0.4939 0.120 Uiso 1 1 calc R . .
C11 C 0.5500(16) 0.2453(8) -0.0045(18) 0.099(5) Uani 1 1 d . . .
H11A H 0.6195 0.2857 0.0134 0.148 Uiso 1 1 calc R . .
H11B H 0.4259 0.2493 0.0346 0.148 Uiso 1 1 calc R . .
H11C H 0.5387 0.2384 -0.1046 0.148 Uiso 1 1 calc R . .
C14 C 0.731(2) 0.2012(10) 0.5169(17) 0.128(7) Uani 1 1 d . . .
H14 H 0.7638 0.2050 0.6122 0.154 Uiso 1 1 calc R . .
O2 O 1.1496(9) 0.4862(4) 0.7515(7) 0.0631(19) Uani 1 1 d . . .
N2 N 0.9713(8) 0.4856(4) 0.7147(7) 0.0390(16) Uani 1 1 d . . .
C23 C 0.8821(12) 0.4673(5) 0.6038(8) 0.045(2) Uani 1 1 d . . .
C26 C 0.8254(14) 0.5137(5) 0.8215(10) 0.051(2) Uani 1 1 d . . .
H26 H 0.8208 0.5627 0.8115 0.061 Uiso 1 1 calc R . .
C22 C 0.9961(14) 0.4393(5) 0.4814(9) 0.046(2) Uani 1 1 d . . .
C25 C 0.6485(12) 0.4864(6) 0.7622(11) 0.059(3) Uani 1 1 d . . .
H25 H 0.5492 0.5205 0.7728 0.071 Uiso 1 1 calc R . .
C31 C 0.760(2) 0.4644(8) 1.0517(12) 0.087(4) Uani 1 1 d . . .
H31 H 0.7925 0.4585 1.1469 0.105 Uiso 1 1 calc R . .
C21 C 1.0966(13) 0.4825(6) 0.3987(10) 0.059(3) Uani 1 1 d . . .
H21 H 1.0962 0.5282 0.4181 0.071 Uiso 1 1 calc R . .
C17 C 0.9945(15) 0.3725(7) 0.4446(11) 0.064(3) Uani 1 1 d . . .
H17 H 0.9257 0.3420 0.4977 0.076 Uiso 1 1 calc R . .
C20 C 1.1999(13) 0.4581(7) 0.2852(11) 0.067(3) Uani 1 1 d . . .
H20 H 1.2761 0.4871 0.2344 0.080 Uiso 1 1 calc R . .
C18 C 1.0979(18) 0.3495(7) 0.3252(12) 0.073(3) Uani 1 1 d . . .
H18 H 1.0999 0.3042 0.3019 0.088 Uiso 1 1 calc R . .
C32 C 0.8708(18) 0.4971(6) 0.9683(11) 0.068(3) Uani 1 1 d . . .
H32 H 0.9872 0.5108 1.0049 0.081 Uiso 1 1 calc R . .
C19 C 1.1905(15) 0.3938(7) 0.2488(12) 0.065(3) Uani 1 1 d . . .
H19 H 1.2507 0.3796 0.1675 0.078 Uiso 1 1 calc R . .
C29 C 0.5897(16) 0.4255(6) 0.8404(12) 0.065(3) Uani 1 1 d . . .
H29A H 0.4664 0.4116 0.8048 0.079 Uiso 1 1 calc R . .
H29B H 0.6791 0.3894 0.8228 0.079 Uiso 1 1 calc R . .
C24 C 0.6785(12) 0.4768(6) 0.6036(10) 0.056(3) Uani 1 1 d . . .
C28 C 0.6295(19) 0.5381(8) 0.5285(13) 0.089(4) Uani 1 1 d . . .
H28A H 0.7039 0.5743 0.5656 0.134 Uiso 1 1 calc R . .
H28B H 0.4974 0.5479 0.5402 0.134 Uiso 1 1 calc R . .
H28C H 0.6546 0.5328 0.4298 0.134 Uiso 1 1 calc R . .
C30 C 0.580(3) 0.4362(9) 0.9934(18) 0.126(7) Uani 1 1 d . . .
H30A H 0.5541 0.3938 1.0403 0.152 Uiso 1 1 calc R . .
H30B H 0.4759 0.4668 1.0125 0.152 Uiso 1 1 calc R . .
C27 C 0.5669(13) 0.4191(9) 0.5439(16) 0.113(7) Uani 1 1 d . . .
H27A H 0.4353 0.4252 0.5645 0.170 Uiso 1 1 calc R . .
H27B H 0.6122 0.3778 0.5859 0.170 Uiso 1 1 calc R . .
H27C H 0.5822 0.4176 0.4433 0.170 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
N1 O1 1.272(8) . ?
N1 C7 1.290(10) . ?
N1 C10 1.512(10) . ?
C7 C6 1.443(12) . ?
C7 C8 1.519(11) . ?
C6 C5 1.324(16) . ?
C6 C1 1.388(15) . ?
C10 C13 1.463(13) . ?
C10 C9 1.546(12) . ?
C10 H10 0.9800 . ?
C1 C2 1.341(16) . ?
C1 H1 0.9300 . ?
C5 C4 1.384(15) . ?
C5 H5 0.9300 . ?
C9 C16 1.446(17) . ?
C9 C8 1.589(14) . ?
C9 H9 0.9800 . ?
C2 C3 1.33(2) . ?
C2 H2 0.9300 . ?
C8 C11 1.539(15) . ?
C8 C12 1.541(16) . ?
C4 C3 1.40(2) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C3 H3 0.9300 . ?
C13 C14 1.301(19) . ?
C13 H13 0.9300 . ?
C16 C15 1.70(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 C14 1.42(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 H14 0.9300 . ?
O2 N2 1.299(9) . ?
N2 C23 1.270(10) . ?
N2 C26 1.560(12) . ?
C23 C24 1.448(12) . ?
C23 C22 1.529(12) . ?
C26 C32 1.452(14) . ?
C26 C25 1.469(14) . ?
C26 H26 0.9800 . ?
C22 C21 1.369(14) . ?
C22 C17 1.379(16) . ?
C25 C29 1.482(16) . ?
C25 C24 1.532(13) . ?
C25 H25 0.9800 . ?
C31 C32 1.297(17) . ?
C31 C30 1.49(2) . ?
C31 H31 0.9300 . ?
C21 C20 1.397(14) . ?
C21 H21 0.9300 . ?
C17 C18 1.432(15) . ?
C17 H17 0.9300 . ?
C20 C19 1.331(17) . ?
C20 H20 0.9300 . ?
C18 C19 1.320(17) . ?
C18 H18 0.9300 . ?
C32 H32 0.9300 . ?
C19 H19 0.9300 . ?
C29 C30 1.467(19) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C24 C28 1.442(18) . ?
C24 C27 1.506(17) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
O1 N1 C7 127.9(7) . . ?
O1 N1 C10 118.6(6) . . ?
C7 N1 C10 112.9(6) . . ?
N1 C7 C6 122.0(7) . . ?
N1 C7 C8 111.0(7) . . ?
C6 C7 C8 126.8(7) . . ?
C5 C6 C1 121.4(10) . . ?
C5 C6 C7 119.6(10) . . ?
C1 C6 C7 119.0(10) . . ?
C13 C10 N1 108.4(8) . . ?
C13 C10 C9 116.1(9) . . ?
N1 C10 C9 102.5(6) . . ?
C13 C10 H10 109.9 . . ?
N1 C10 H10 109.9 . . ?
C9 C10 H10 109.9 . . ?
C2 C1 C6 116.8(13) . . ?
C2 C1 H1 121.6 . . ?
C6 C1 H1 121.6 . . ?
C6 C5 C4 120.6(13) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C16 C9 C10 112.7(9) . . ?
C16 C9 C8 112.7(10) . . ?
C10 C9 C8 101.3(6) . . ?
C16 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C3 C2 C1 124.0(14) . . ?
C3 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?
C7 C8 C11 109.1(8) . . ?
C7 C8 C12 109.2(9) . . ?
C11 C8 C12 112.3(9) . . ?
C7 C8 C9 102.1(7) . . ?
C11 C8 C9 111.9(11) . . ?
C12 C8 C9 111.8(9) . . ?
C5 C4 C3 118.0(14) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C3 C4 118.7(13) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C14 C13 C10 123.7(14) . . ?
C14 C13 H13 118.1 . . ?
C10 C13 H13 118.1 . . ?
C9 C16 C15 106.9(10) . . ?
C9 C16 H16A 110.3 . . ?
C15 C16 H16A 110.3 . . ?
C9 C16 H16B 110.3 . . ?
C15 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C14 C15 C16 111.1(9) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C14 C15 122.8(15) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C23 N2 O2 133.6(7) . . ?
C23 N2 C26 108.6(7) . . ?
O2 N2 C26 117.9(7) . . ?
N2 C23 C24 116.1(8) . . ?
N2 C23 C22 118.3(7) . . ?
C24 C23 C22 125.5(7) . . ?
C32 C26 C25 116.8(10) . . ?
C32 C26 N2 113.8(8) . . ?
C25 C26 N2 100.6(7) . . ?
C32 C26 H26 108.4 . . ?
C25 C26 H26 108.4 . . ?
N2 C26 H26 108.4 . . ?
C21 C22 C17 117.7(9) . . ?
C21 C22 C23 119.2(9) . . ?
C17 C22 C23 122.9(9) . . ?
C26 C25 C29 111.4(9) . . ?
C26 C25 C24 106.9(8) . . ?
C29 C25 C24 115.2(10) . . ?
C26 C25 H25 107.7 . . ?
C29 C25 H25 107.7 . . ?
C24 C25 H25 107.7 . . ?
C32 C31 C30 119.3(11) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C22 C21 C20 120.2(11) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C17 C18 120.6(11) . . ?
C22 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C20 C21 120.8(10) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C19 C18 C17 118.8(13) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C31 C32 C26 124.5(12) . . ?
C31 C32 H32 117.8 . . ?
C26 C32 H32 117.8 . . ?
C18 C19 C20 121.7(10) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C30 C29 C25 112.7(11) . . ?
C30 C29 H29A 109.0 . . ?
C25 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
C25 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C28 C24 C23 109.4(10) . . ?
C28 C24 C27 110.1(10) . . ?
C23 C24 C27 114.7(9) . . ?
C28 C24 C25 109.6(10) . . ?
C23 C24 C25 99.8(7) . . ?
C27 C24 C25 112.8(10) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C29 C30 C31 111.4(12) . . ?
C29 C30 H30A 109.3 . . ?
C31 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
C31 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
O1 N1 C7 C6 -3.5(16) . . . . ?
C10 N1 C7 C6 -174.8(9) . . . . ?
O1 N1 C7 C8 171.4(9) . . . . ?
C10 N1 C7 C8 0.1(12) . . . . ?
N1 C7 C6 C5 -94.6(12) . . . . ?
C8 C7 C6 C5 91.2(13) . . . . ?
N1 C7 C6 C1 83.7(11) . . . . ?
C8 C7 C6 C1 -90.4(12) . . . . ?
O1 N1 C10 C13 44.4(13) . . . . ?
C7 N1 C10 C13 -143.4(10) . . . . ?
O1 N1 C10 C9 167.6(8) . . . . ?
C7 N1 C10 C9 -20.2(11) . . . . ?
C5 C6 C1 C2 -7.8(13) . . . . ?
C7 C6 C1 C2 173.8(8) . . . . ?
C1 C6 C5 C4 6.7(17) . . . . ?
C7 C6 C5 C4 -175.0(11) . . . . ?
C13 C10 C9 C16 26.8(13) . . . . ?
N1 C10 C9 C16 -91.1(9) . . . . ?
C13 C10 C9 C8 147.5(10) . . . . ?
N1 C10 C9 C8 29.6(10) . . . . ?
C6 C1 C2 C3 6.4(16) . . . . ?
N1 C7 C8 C11 137.9(11) . . . . ?
C6 C7 C8 C11 -47.5(15) . . . . ?
N1 C7 C8 C12 -99.1(10) . . . . ?
C6 C7 C8 C12 75.5(12) . . . . ?
N1 C7 C8 C9 19.4(11) . . . . ?
C6 C7 C8 C9 -166.0(10) . . . . ?
C16 C9 C8 C7 91.0(9) . . . . ?
C10 C9 C8 C7 -29.7(10) . . . . ?
C16 C9 C8 C11 -25.5(12) . . . . ?
C10 C9 C8 C11 -146.1(9) . . . . ?
C16 C9 C8 C12 -152.4(8) . . . . ?
C10 C9 C8 C12 86.9(9) . . . . ?
C6 C5 C4 C3 -4(2) . . . . ?
C1 C2 C3 C4 -4(2) . . . . ?
C5 C4 C3 C2 2(2) . . . . ?
N1 C10 C13 C14 125.4(15) . . . . ?
C9 C10 C13 C14 11(2) . . . . ?
C10 C9 C16 C15 -53.8(10) . . . . ?
C8 C9 C16 C15 -167.7(8) . . . . ?
C9 C16 C15 C14 52.5(14) . . . . ?
C10 C13 C14 C15 -12(3) . . . . ?
C16 C15 C14 C13 -19(2) . . . . ?
O2 N2 C23 C24 -178.3(10) . . . . ?
C26 N2 C23 C24 0.3(12) . . . . ?
O2 N2 C23 C22 0.0(16) . . . . ?
C26 N2 C23 C22 178.6(8) . . . . ?
C23 N2 C26 C32 142.9(9) . . . . ?
O2 N2 C26 C32 -38.3(12) . . . . ?
C23 N2 C26 C25 17.1(10) . . . . ?
O2 N2 C26 C25 -164.1(8) . . . . ?
N2 C23 C22 C21 -74.8(12) . . . . ?
C24 C23 C22 C21 103.3(12) . . . . ?
N2 C23 C22 C17 108.9(12) . . . . ?
C24 C23 C22 C17 -72.9(14) . . . . ?
C32 C26 C25 C29 -23.8(13) . . . . ?
N2 C26 C25 C29 99.9(9) . . . . ?
C32 C26 C25 C24 -150.5(10) . . . . ?
N2 C26 C25 C24 -26.8(11) . . . . ?
C17 C22 C21 C20 -2.8(14) . . . . ?
C23 C22 C21 C20 -179.2(8) . . . . ?
C21 C22 C17 C18 1.1(15) . . . . ?
C23 C22 C17 C18 177.4(9) . . . . ?
C22 C21 C20 C19 5.3(16) . . . . ?
C22 C17 C18 C19 -1.8(17) . . . . ?
C30 C31 C32 C26 5(2) . . . . ?
C25 C26 C32 C31 -5.2(17) . . . . ?
N2 C26 C32 C31 -121.9(12) . . . . ?
C17 C18 C19 C20 4.4(18) . . . . ?
C21 C20 C19 C18 -6.1(18) . . . . ?
C26 C25 C29 C30 52.9(15) . . . . ?
C24 C25 C29 C30 174.9(11) . . . . ?
N2 C23 C24 C28 98.2(11) . . . . ?
C22 C23 C24 C28 -80.0(13) . . . . ?
N2 C23 C24 C27 -137.6(12) . . . . ?
C22 C23 C24 C27 44.3(15) . . . . ?
N2 C23 C24 C25 -16.8(13) . . . . ?
C22 C23 C24 C25 165.0(10) . . . . ?
C26 C25 C24 C28 -87.8(11) . . . . ?
C29 C25 C24 C28 147.8(10) . . . . ?
C26 C25 C24 C23 27.1(12) . . . . ?
C29 C25 C24 C23 -97.4(11) . . . . ?
C26 C25 C24 C27 149.2(9) . . . . ?
C29 C25 C24 C27 24.8(13) . . . . ?
C25 C29 C30 C31 -52.9(17) . . . . ?
C32 C31 C30 C29 24(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2057134'
loop_
_audit_author_name
_audit_author_address
'Jiangfei Chen'
;hunnan university
China
;
_audit_update_record             
;
2021-01-19 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_audit_creation_method           'Created with Diamond (www.crystalimpact.com)'
_audit_creation_date             18-03-15
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.350
_refine_ls_R_factor_all          0.044
_cell_length_a                   6.5441(19)
_cell_length_b                   8.977(3)
_cell_length_c                   28.197(8)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     1656.5(8)
_cell_formula_units_Z            4
_symmetry_int_tables_number      19
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  P_2ac_2ab

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '0.500-x, -y, 0.500+z'
3 '0.500+x, 0.500-y, -z'
4 '-x, 0.500+y, 0.500-z'

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C5 C 0.5119(3) 0.2725(2) 0.1978(1) 1.000 4 a ? d Uani 0.0591(4)
H5 H 0.6475 0.2962 0.1915 1.000 4 a ? calc Uiso 0.07100
C4 C 0.4650(3) 0.1398(2) 0.2197(1) 1.000 4 a ? d Uani 0.0695(5)
H4 H 0.5701 0.0751 0.2280 1.000 4 a ? calc Uiso 0.08300
C1 C 0.1577(3) 0.3312(2) 0.1954(1) 1.000 4 a ? d Uani 0.0757(6)
H1 H 0.0515 0.3956 0.1877 1.000 4 a ? calc Uiso 0.09100
C3 C 0.2681(4) 0.1008(2) 0.2293(1) 1.000 4 a ? d Uani 0.0801(6)
H3 H 0.2387 0.0106 0.2441 1.000 4 a ? calc Uiso 0.09600
C2 C 0.1146(4) 0.1964(3) 0.2170(1) 1.000 4 a ? d Uani 0.0919(7)
H2 H -0.0204 0.1706 0.2233 1.000 4 a ? calc Uiso 0.11000
C6 C 0.3574(3) 0.3714(2) 0.1852(0) 1.000 4 a ? d Uani 0.0508(4)
N1 N 0.5715(2) 0.5653(1) 0.1491(0) 1.000 4 a ? d Uani 0.0487(3)
C7 C 0.3939(2) 0.5149(2) 0.1624(0) 1.000 4 a ? d Uani 0.0498(4)
O1 O 0.7468(2) 0.5016(1) 0.1528(0) 1.000 4 a ? d Uani 0.0662(3)
C9 C 0.3377(3) 0.7566(2) 0.1294(1) 1.000 4 a ? d Uani 0.0649(5)
H9A H 0.3173 0.8440 0.1491 1.000 4 a ? calc Uiso 0.07800
H9B H 0.2842 0.7770 0.0980 1.000 4 a ? calc Uiso 0.07800
C10 C 0.5647(3) 0.7175(2) 0.1267(1) 1.000 4 a ? d Uani 0.0540(4)
C11 C 0.7010(3) 0.8212(2) 0.1553(1) 1.000 4 a ? d Uani 0.0751(6)
H11A H 0.6594 0.8197 0.1880 1.000 4 a ? calc Uiso 0.11300
H11B H 0.6893 0.9207 0.1431 1.000 4 a ? calc Uiso 0.11300
H11C H 0.8404 0.7887 0.1529 1.000 4 a ? calc Uiso 0.11300
C8 C 0.2316(3) 0.6240(2) 0.1508(1) 1.000 4 a ? d Uani 0.0790(6)
H8A H 0.1579 0.6527 0.1792 1.000 4 a ? calc Uiso 0.09500
H8B H 0.1354 0.5815 0.1284 1.000 4 a ? calc Uiso 0.09500
C12 C 0.6471(3) 0.7048(2) 0.0771(1) 1.000 4 a ? d Uani 0.0616(5)
H12A H 0.6481 0.8019 0.0620 1.000 4 a ? calc Uiso 0.07400
H12B H 0.7861 0.6673 0.0779 1.000 4 a ? calc Uiso 0.07400
O2 O 0.5188(2) 0.6044(1) 0.0509(0) 1.000 4 a ? d Uani 0.0588(3)
O3 O 0.7225(2) 0.6352(2) -0.0115(0) 1.000 4 a ? d Uani 0.0962(5)
C15 C 0.2333(3) 0.4538(2) -0.0022(1) 1.000 4 a ? d Uani 0.0675(5)
H15 H 0.1896 0.4989 0.0257 1.000 4 a ? calc Uiso 0.08100
C13 C 0.5718(3) 0.5807(2) 0.0058(1) 1.000 4 a ? d Uani 0.0638(5)
C14 C 0.4277(3) 0.4815(2) -0.0192(1) 1.000 4 a ? d Uani 0.0616(4)
C19 C 0.4909(4) 0.4135(2) -0.0610(1) 1.000 4 a ? d Uani 0.0822(6)
H19 H 0.6203 0.4325 -0.0733 1.000 4 a ? calc Uiso 0.09900
C17 C 0.1681(5) 0.2903(2) -0.0671(1) 1.000 4 a ? d Uani 0.0983(8)
H17 H 0.0819 0.2247 -0.0829 1.000 4 a ? calc Uiso 0.11800
C16 C 0.1036(4) 0.3595(2) -0.0265(1) 1.000 4 a ? d Uani 0.0832(6)
H16 H -0.0280 0.3429 -0.0153 1.000 4 a ? calc Uiso 0.10000
C18 C 0.3603(5) 0.3179(3) -0.0842(1) 1.000 4 a ? d Uani 0.1011(8)
H18 H 0.4033 0.2713 -0.1119 1.000 4 a ? calc Uiso 0.12100



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C5 C4 . . 1.375(2) no
C5 C6 . . 1.393(2) no
C5 H5 . . 0.9300 no
C4 C3 . . 1.363(3) no
C4 H4 . . 0.9300 no
C1 C2 . . 1.384(3) no
C1 C6 . . 1.386(2) no
C1 H1 . . 0.9300 no
C3 C2 . . 1.366(3) no
C3 H3 . . 0.9300 no
C2 H2 . . 0.9300 no
C6 C7 . . 1.459(2) no
N1 O1 . . 1.2861(16) no
N1 C7 . . 1.3020(19) no
N1 C10 . . 1.505(2) no
C7 C8 . . 1.481(2) no
C9 C8 . . 1.504(3) no
C9 C10 . . 1.529(2) no
C9 H9A . . 0.9700 no
C9 H9B . . 0.9700 no
C10 C12 . . 1.502(2) no
C10 C11 . . 1.521(2) no
C11 H11A . . 0.9600 no
C11 H11B . . 0.9600 no
C11 H11C . . 0.9600 no
C8 H8A . . 0.9700 no
C8 H8B . . 0.9700 no
C12 O2 . . 1.4364(19) no
C12 H12A . . 0.9700 no
C12 H12B . . 0.9700 no
O2 C13 . . 1.337(2) no
O3 C13 . . 1.204(2) no
C15 C14 . . 1.382(3) no
C15 C16 . . 1.380(3) no
C15 H15 . . 0.9300 no
C13 C14 . . 1.477(3) no
C14 C19 . . 1.390(3) no
C19 C18 . . 1.376(3) no
C19 H19 . . 0.9300 no
C17 C18 . . 1.370(4) no
C17 C16 . . 1.368(3) no
C17 H17 . . 0.9300 no
C16 H16 . . 0.9300 no
C18 H18 . . 0.9300 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 C5 C6 . . . 120.35(18) no
C4 C5 H5 . . . 119.80 no
C6 C5 H5 . . . 119.80 no
C3 C4 C5 . . . 121.54(19) no
C3 C4 H4 . . . 119.20 no
C5 C4 H4 . . . 119.20 no
C2 C1 C6 . . . 120.8(2) no
C2 C1 H1 . . . 119.60 no
C6 C1 H1 . . . 119.60 no
C4 C3 C2 . . . 118.87(19) no
C4 C3 H3 . . . 120.60 no
C2 C3 H3 . . . 120.60 no
C3 C2 C1 . . . 120.8(2) no
C3 C2 H2 . . . 119.60 no
C1 C2 H2 . . . 119.60 no
C1 C6 C5 . . . 117.70(16) no
C1 C6 C7 . . . 118.44(15) no
C5 C6 C7 . . . 123.86(15) no
O1 N1 C7 . . . 128.19(12) no
O1 N1 C10 . . . 117.63(13) no
C7 N1 C10 . . . 114.18(13) no
N1 C7 C6 . . . 125.42(14) no
N1 C7 C8 . . . 110.31(14) no
C6 C7 C8 . . . 124.27(14) no
C8 C9 C10 . . . 106.69(14) no
C8 C9 H9A . . . 110.40 no
C10 C9 H9A . . . 110.40 no
C8 C9 H9B . . . 110.40 no
C10 C9 H9B . . . 110.40 no
H9A C9 H9B . . . 108.60 no
C12 C10 N1 . . . 108.11(13) no
C12 C10 C11 . . . 109.24(15) no
N1 C10 C11 . . . 108.42(13) no
C12 C10 C9 . . . 114.38(15) no
N1 C10 C9 . . . 102.47(13) no
C11 C10 C9 . . . 113.74(15) no
C10 C11 H11A . . . 109.50 no
C10 C11 H11B . . . 109.50 no
H11A C11 H11B . . . 109.50 no
C10 C11 H11C . . . 109.50 no
H11A C11 H11C . . . 109.50 no
H11B C11 H11C . . . 109.50 no
C7 C8 C9 . . . 106.27(14) no
C7 C8 H8A . . . 110.50 no
C9 C8 H8A . . . 110.50 no
C7 C8 H8B . . . 110.50 no
C9 C8 H8B . . . 110.50 no
H8A C8 H8B . . . 108.70 no
O2 C12 C10 . . . 108.45(13) no
O2 C12 H12A . . . 110.00 no
C10 C12 H12A . . . 110.00 no
O2 C12 H12B . . . 110.00 no
C10 C12 H12B . . . 110.00 no
H12A C12 H12B . . . 108.40 no
C13 O2 C12 . . . 115.96(14) no
C14 C15 C16 . . . 120.3(2) no
C14 C15 H15 . . . 119.90 no
C16 C15 H15 . . . 119.90 no
O3 C13 O2 . . . 122.28(18) no
O3 C13 C14 . . . 125.08(17) no
O2 C13 C14 . . . 112.63(16) no
C15 C14 C19 . . . 119.25(19) no
C15 C14 C13 . . . 122.07(16) no
C19 C14 C13 . . . 118.67(18) no
C18 C19 C14 . . . 119.4(2) no
C18 C19 H19 . . . 120.30 no
C14 C19 H19 . . . 120.30 no
C18 C17 C16 . . . 119.7(2) no
C18 C17 H17 . . . 120.10 no
C16 C17 H17 . . . 120.10 no
C17 C16 C15 . . . 120.2(2) no
C17 C16 H16 . . . 119.90 no
C15 C16 H16 . . . 119.90 no
C17 C18 C19 . . . 121.1(2) no
C17 C18 H18 . . . 119.50 no
C19 C18 H18 . . . 119.50 no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C5 C4 C3 . . . . 0.3(3) no
C5 C4 C3 C2 . . . . -0.1(3) no
C4 C3 C2 C1 . . . . -0.5(3) no
C6 C1 C2 C3 . . . . 0.9(3) no
C2 C1 C6 C5 . . . . -0.7(3) no
C2 C1 C6 C7 . . . . -179.96(18) no
C4 C5 C6 C1 . . . . 0.1(2) no
C4 C5 C6 C7 . . . . 179.36(15) no
O1 N1 C7 C6 . . . . 0.4(2) no
C10 N1 C7 C6 . . . . -179.68(14) no
O1 N1 C7 C8 . . . . -179.16(16) no
C10 N1 C7 C8 . . . . 0.75(19) no
C1 C6 C7 N1 . . . . -177.36(16) no
C5 C6 C7 N1 . . . . 3.4(2) no
C1 C6 C7 C8 . . . . 2.1(3) no
C5 C6 C7 C8 . . . . -177.05(17) no
O1 N1 C10 C12 . . . . 59.85(17) no
C7 N1 C10 C12 . . . . -120.06(15) no
O1 N1 C10 C11 . . . . -58.46(18) no
C7 N1 C10 C11 . . . . 121.63(16) no
O1 N1 C10 C9 . . . . -179.00(14) no
C7 N1 C10 C9 . . . . 1.08(17) no
C8 C9 C10 C12 . . . . 114.34(17) no
C8 C9 C10 N1 . . . . -2.39(19) no
C8 C9 C10 C11 . . . . -119.18(17) no
N1 C7 C8 C9 . . . . -2.3(2) no
C6 C7 C8 C9 . . . . 178.12(15) no
C10 C9 C8 C7 . . . . 2.9(2) no
N1 C10 C12 O2 . . . . 61.18(17) no
C11 C10 C12 O2 . . . . 178.96(13) no
C9 C10 C12 O2 . . . . -52.25(18) no
C10 C12 O2 C13 . . . . -179.98(14) no
C12 O2 C13 O3 . . . . 3.0(2) no
C12 O2 C13 C14 . . . . -177.57(14) no
C16 C15 C14 C19 . . . . 0.1(3) no
C16 C15 C14 C13 . . . . -179.55(15) no
O3 C13 C14 C15 . . . . -162.81(18) no
O2 C13 C14 C15 . . . . 17.7(2) no
O3 C13 C14 C19 . . . . 17.5(3) no
O2 C13 C14 C19 . . . . -161.94(15) no
C15 C14 C19 C18 . . . . -1.3(3) no
C13 C14 C19 C18 . . . . 178.43(17) no
C18 C17 C16 C15 . . . . -1.7(3) no
C14 C15 C16 C17 . . . . 1.3(3) no
C16 C17 C18 C19 . . . . 0.5(4) no
C14 C19 C18 C17 . . . . 0.9(3) no
