# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_mo_20191230c_0m
_database_code_depnum_ccdc_archive 'CCDC 1976897'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;
_audit_creation_date             2019-12-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40
_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                   13.583(3)
_cell_length_b                   8.561(2)
_cell_length_c                   15.116(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.03(3)
_cell_angle_gamma                90
_cell_volume                     1744.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.532
_cell_measurement_theta_min      3.022
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0770 before and 0.0484 after correction. The Ratio of minimum to maximum transmission is 0.9182. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_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            32906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.819
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                3069
_reflns_number_total             4008
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.198
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.036
_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)+(0.0591P)²+0.6672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1402
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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
O1 O 0.69501(10) 0.4269(2) 0.11789(8) 0.0694(4) Uani 1 1 d . . . . .
O2 O 0.52894(8) 0.32346(14) 0.19585(7) 0.0483(3) Uani 1 1 d . . . . .
N1 N 0.54927(9) 0.26476(17) 0.36787(8) 0.0416(3) Uani 1 1 d . . . . .
H1 H 0.498517 0.245491 0.329600 0.050 Uiso 1 1 calc R . . . .
C1 C 0.70208(12) 0.4068(2) 0.19918(10) 0.0466(4) Uani 1 1 d . . . . .
C2 C 0.61973(11) 0.35844(18) 0.24455(10) 0.0397(3) Uani 1 1 d . . . . .
C3 C 0.62947(10) 0.32424(17) 0.33336(9) 0.0348(3) Uani 1 1 d . . . . .
C4 C 0.72577(10) 0.34975(19) 0.39157(10) 0.0393(3) Uani 1 1 d . . . . .
H4A H 0.759919 0.250514 0.400950 0.047 Uiso 1 1 calc R . . . .
H4B H 0.711957 0.387899 0.449210 0.047 Uiso 1 1 calc R . . . .
C5 C 0.79349(11) 0.4652(2) 0.35224(11) 0.0466(4) Uani 1 1 d . . . . .
H5 H 0.763885 0.569377 0.354113 0.056 Uiso 1 1 calc R . . . .
C6 C 0.80035(12) 0.4247(2) 0.25568(11) 0.0507(4) Uani 1 1 d . . . . .
H6A H 0.837863 0.505794 0.229995 0.061 Uiso 1 1 calc R . . . .
H6B H 0.837050 0.327828 0.253632 0.061 Uiso 1 1 calc R . . . .
C7 C 0.47916(15) 0.4522(3) 0.14834(14) 0.0673(5) Uani 1 1 d . . . . .
H7A H 0.523035 0.501760 0.110747 0.081 Uiso 1 1 calc R . . . .
H7B H 0.460155 0.529310 0.190119 0.081 Uiso 1 1 calc R . . . .
C8 C 0.3911(2) 0.3920(4) 0.0938(2) 0.1073(10) Uani 1 1 d . . . . .
H8A H 0.357915 0.476022 0.060239 0.161 Uiso 1 1 calc GR . . . .
H8B H 0.347114 0.346400 0.131670 0.161 Uiso 1 1 calc GR . . . .
H8C H 0.410477 0.314151 0.053618 0.161 Uiso 1 1 calc GR . . . .
C9 C 0.89565(13) 0.4700(3) 0.40637(14) 0.0668(6) Uani 1 1 d . . . . .
H9A H 0.888834 0.493678 0.467399 0.100 Uiso 1 1 calc GR . . . .
H9B H 0.935209 0.548992 0.382702 0.100 Uiso 1 1 calc GR . . . .
H9C H 0.927302 0.370216 0.403151 0.100 Uiso 1 1 calc GR . . . .
C10 C 0.53731(10) 0.23014(18) 0.45721(9) 0.0367(3) Uani 1 1 d . . . . .
C11 C 0.61014(11) 0.14809(19) 0.51101(10) 0.0429(4) Uani 1 1 d . . . . .
H11 H 0.667250 0.116207 0.487876 0.051 Uiso 1 1 calc R . . . .
C12 C 0.59858(12) 0.1135(2) 0.59827(11) 0.0484(4) Uani 1 1 d . . . . .
H12 H 0.648624 0.061485 0.634168 0.058 Uiso 1 1 calc R . . . .
C13 C 0.51284(13) 0.1562(2) 0.63226(11) 0.0511(4) Uani 1 1 d . . . . .
H13 H 0.505573 0.135446 0.691509 0.061 Uiso 1 1 calc R . . . .
C14 C 0.43800(12) 0.2296(2) 0.57804(11) 0.0462(4) Uani 1 1 d . . . . .
H14 H 0.379376 0.253999 0.600918 0.055 Uiso 1 1 calc R . . . .
C15 C 0.44744(10) 0.26845(18) 0.48968(10) 0.0383(3) Uani 1 1 d . . . . .
C16 C 0.36121(10) 0.33944(18) 0.43327(10) 0.0393(3) Uani 1 1 d . . . . .
C17 C 0.36895(12) 0.4691(2) 0.37937(11) 0.0467(4) Uani 1 1 d . . . . .
H17 H 0.430913 0.513202 0.375861 0.056 Uiso 1 1 calc R . . . .
C18 C 0.28563(14) 0.5339(2) 0.33062(12) 0.0574(5) Uani 1 1 d . . . . .
H18 H 0.292109 0.620483 0.294655 0.069 Uiso 1 1 calc R . . . .
C19 C 0.19325(14) 0.4699(3) 0.33546(13) 0.0616(5) Uani 1 1 d . . . . .
H19 H 0.137336 0.513300 0.302987 0.074 Uiso 1 1 calc R . . . .
C20 C 0.18428(13) 0.3419(3) 0.38840(14) 0.0642(5) Uani 1 1 d . . . . .
H20 H 0.122024 0.298566 0.391607 0.077 Uiso 1 1 calc R . . . .
C21 C 0.26700(12) 0.2765(2) 0.43712(12) 0.0525(4) Uani 1 1 d . . . . .
H21 H 0.259767 0.189727 0.472784 0.063 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
O1 C1 1.2328(19) . ?
O2 C2 1.3893(18) . ?
O2 C7 1.438(2) . ?
N1 H1 0.8600 . ?
N1 C3 1.3629(18) . ?
N1 C10 1.4112(18) . ?
C1 C2 1.443(2) . ?
C1 C6 1.502(2) . ?
C2 C3 1.364(2) . ?
C3 C4 1.500(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.520(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.514(2) . ?
C5 C9 1.523(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.461(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.392(2) . ?
C10 C15 1.409(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.398(2) . ?
C15 C16 1.491(2) . ?
C16 C17 1.388(2) . ?
C16 C21 1.396(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 H21 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
C2 O2 C7 115.58(14) . . ?
C3 N1 H1 115.3 . . ?
C3 N1 C10 129.49(12) . . ?
C10 N1 H1 115.3 . . ?
O1 C1 C2 122.92(16) . . ?
O1 C1 C6 120.53(15) . . ?
C2 C1 C6 116.48(13) . . ?
O2 C2 C1 119.98(13) . . ?
C3 C2 O2 116.61(13) . . ?
C3 C2 C1 122.81(14) . . ?
N1 C3 C2 118.10(13) . . ?
N1 C3 C4 120.67(12) . . ?
C2 C3 C4 121.23(13) . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 113.02(13) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5 108.1 . . ?
C4 C5 C9 111.25(14) . . ?
C6 C5 C4 109.86(14) . . ?
C6 C5 H5 108.1 . . ?
C6 C5 C9 111.38(14) . . ?
C9 C5 H5 108.1 . . ?
C1 C6 C5 114.60(13) . . ?
C1 C6 H6A 108.6 . . ?
C1 C6 H6B 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
O2 C7 H7A 110.0 . . ?
O2 C7 H7B 110.0 . . ?
O2 C7 C8 108.3(2) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 120.55(13) . . ?
C11 C10 C15 119.88(13) . . ?
C15 C10 N1 119.39(13) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.73(15) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.00(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.66(15) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.02(15) . . ?
C15 C14 H14 119.0 . . ?
C10 C15 C16 123.30(13) . . ?
C14 C15 C10 117.53(14) . . ?
C14 C15 C16 119.08(13) . . ?
C17 C16 C15 123.42(14) . . ?
C17 C16 C21 117.94(15) . . ?
C21 C16 C15 118.59(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.03(16) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.06(19) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.66(17) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.62(18) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.68(18) . . ?
C20 C21 H21 119.7 . . ?

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 C1 C2 O2 3.8(3) . . . . ?
O1 C1 C2 C3 174.60(17) . . . . ?
O1 C1 C6 C5 155.21(17) . . . . ?
O2 C2 C3 N1 -2.5(2) . . . . ?
O2 C2 C3 C4 176.99(13) . . . . ?
N1 C3 C4 C5 -159.94(14) . . . . ?
N1 C10 C11 C12 -179.77(15) . . . . ?
N1 C10 C15 C14 178.85(14) . . . . ?
N1 C10 C15 C16 2.4(2) . . . . ?
C1 C2 C3 N1 -173.56(15) . . . . ?
C1 C2 C3 C4 5.9(2) . . . . ?
C2 O2 C7 C8 174.1(2) . . . . ?
C2 C1 C6 C5 -27.7(2) . . . . ?
C2 C3 C4 C5 20.6(2) . . . . ?
C3 N1 C10 C11 -46.8(2) . . . . ?
C3 N1 C10 C15 138.23(16) . . . . ?
C3 C4 C5 C6 -47.98(18) . . . . ?
C3 C4 C5 C9 -171.78(14) . . . . ?
C4 C5 C6 C1 52.3(2) . . . . ?
C6 C1 C2 O2 -173.27(14) . . . . ?
C6 C1 C2 C3 -2.5(2) . . . . ?
C7 O2 C2 C1 -65.1(2) . . . . ?
C7 O2 C2 C3 123.52(17) . . . . ?
C9 C5 C6 C1 175.98(16) . . . . ?
C10 N1 C3 C2 -175.09(15) . . . . ?
C10 N1 C3 C4 5.5(2) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C10 C15 C16 C17 -49.6(2) . . . . ?
C10 C15 C16 C21 132.88(16) . . . . ?
C11 C10 C15 C14 3.8(2) . . . . ?
C11 C10 C15 C16 -172.68(14) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C12 C13 C14 C15 -2.6(3) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C13 C14 C15 C16 176.48(16) . . . . ?
C14 C15 C16 C17 133.93(17) . . . . ?
C14 C15 C16 C21 -43.6(2) . . . . ?
C15 C10 C11 C12 -4.8(2) . . . . ?
C15 C16 C17 C18 -177.66(15) . . . . ?
C15 C16 C21 C20 177.70(16) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
C21 C16 C17 C18 -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mp_a
_database_code_depnum_ccdc_archive 'CCDC 1976950'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36

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'

_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                   7.2409(13)
_cell_length_b                   19.433(4)
_cell_length_c                   10.923(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.667(2)
_cell_angle_gamma                90
_cell_volume                     1529.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5559
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.984
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14727
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2800
_reflns_number_gt                2181
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0630P)²+0.4168P] 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         2800
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.4168(2) 0.58338(9) 0.78751(16) 0.0315(4) Uani 1 1 d . . . . .
C2 C 0.3547(3) 0.55030(10) 0.88887(18) 0.0410(5) Uani 1 1 d . . . . .
H2 H 0.414322 0.557973 0.967060 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2058(3) 0.50640(11) 0.8735(2) 0.0513(6) Uani 1 1 d . . . . .
H3 H 0.161176 0.485740 0.941537 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1226(3) 0.49303(12) 0.7570(2) 0.0527(6) Uani 1 1 d . . . . .
H4 H 0.027713 0.460708 0.745501 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1803(2) 0.52765(10) 0.65758(19) 0.0434(5) Uani 1 1 d . . . . .
H5 H 0.121456 0.518848 0.579583 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3249(2) 0.57572(9) 0.67046(16) 0.0316(4) Uani 1 1 d . . . . .
C7 C 0.3674(2) 0.61573(9) 0.56021(16) 0.0306(4) Uani 1 1 d . . . . .
C8 C 0.2127(2) 0.64440(10) 0.48086(16) 0.0353(4) Uani 1 1 d . . . . .
C9 C 0.2543(2) 0.68458(10) 0.36917(17) 0.0407(5) Uani 1 1 d . . . . .
H9A H 0.279561 0.732011 0.392911 0.049 Uiso 1 1 calc R U . . .
H9B H 0.145482 0.684224 0.309791 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4188(2) 0.65636(10) 0.30824(16) 0.0351(4) Uani 1 1 d . . . . .
C11 C 0.5835(2) 0.65569(10) 0.40689(16) 0.0376(4) Uani 1 1 d . . . . .
H11A H 0.683013 0.629206 0.376626 0.045 Uiso 1 1 calc R U . . .
H11B H 0.627680 0.702497 0.419890 0.045 Uiso 1 1 calc R U . . .
C12 C 0.5423(2) 0.62640(9) 0.52796(16) 0.0312(4) Uani 1 1 d . . . . .
C13 C 0.7204(2) 0.62811(9) 0.72998(16) 0.0328(4) Uani 1 1 d . . . . .
C14 C 0.8737(2) 0.65274(11) 0.79804(18) 0.0417(5) Uani 1 1 d . . . . .
H14 H 0.988954 0.662182 0.771147 0.050 Uiso 1 1 calc R U . . .
C15 C 0.8211(3) 0.66086(10) 0.91730(18) 0.0418(5) Uani 1 1 d . . . . .
C16 C 0.3774(3) 0.58414(11) 0.25831(19) 0.0477(5) Uani 1 1 d . . . . .
H16A H 0.482192 0.567345 0.219879 0.072 Uiso 1 1 calc R U . . .
H16B H 0.270486 0.585509 0.198917 0.072 Uiso 1 1 calc R U . . .
H16C H 0.353403 0.554107 0.324701 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4614(3) 0.70320(13) 0.20240(19) 0.0551(6) Uani 1 1 d . . . . .
H17A H 0.488126 0.748768 0.233197 0.083 Uiso 1 1 calc R U . . .
H17B H 0.356053 0.704655 0.141795 0.083 Uiso 1 1 calc R U . . .
H17C H 0.566942 0.685645 0.165665 0.083 Uiso 1 1 calc R U . . .
C18 C 0.9372(3) 0.68534(14) 1.0294(2) 0.0637(7) Uani 1 1 d . . . . .
H18A H 0.957272 0.733996 1.023240 0.096 Uiso 1 1 calc R U . . .
H18B H 1.054522 0.661921 1.036025 0.096 Uiso 1 1 calc R U . . .
H18C H 0.874527 0.675837 1.100969 0.096 Uiso 1 1 calc R U . . .
N1 N 0.58234(19) 0.62302(8) 0.80569(13) 0.0344(4) Uani 1 1 d . . . . .
N2 N 0.6459(2) 0.64305(9) 0.92369(14) 0.0423(4) Uani 1 1 d . . . . .
N3 N 0.69942(19) 0.61192(8) 0.60559(14) 0.0393(4) Uani 1 1 d . . . . .
H3A H 0.789955 0.591626 0.575068 0.047 Uiso 1 1 calc R U . . .
O1 O 0.05050(17) 0.63938(9) 0.50405(13) 0.0554(4) Uani 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
C1 C6 1.390(2) . ?
C1 C2 1.392(2) . ?
C1 N1 1.422(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(2) . ?
C7 C12 1.364(2) . ?
C7 C8 1.457(2) . ?
C8 O1 1.230(2) . ?
C8 C9 1.504(3) . ?
C9 C10 1.523(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C16 1.525(3) . ?
C10 C11 1.526(2) . ?
C10 C17 1.527(3) . ?
C11 C12 1.497(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.379(2) . ?
C13 C14 1.361(3) . ?
C13 N1 1.362(2) . ?
C13 N3 1.388(2) . ?
C14 C15 1.402(3) . ?
C14 H14 0.9300 . ?
C15 N2 1.323(2) . ?
C15 C18 1.493(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 N2 1.381(2) . ?
N3 H3A 0.8600 . ?

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
C6 C1 C2 121.28(16) . . ?
C6 C1 N1 120.46(15) . . ?
C2 C1 N1 118.20(16) . . ?
C3 C2 C1 120.07(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.78(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.81(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.95(19) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.70(16) . . ?
C1 C6 C7 124.68(15) . . ?
C5 C6 C7 118.61(16) . . ?
C12 C7 C8 117.83(16) . . ?
C12 C7 C6 123.99(15) . . ?
C8 C7 C6 118.17(14) . . ?
O1 C8 C7 122.73(16) . . ?
O1 C8 C9 118.71(16) . . ?
C7 C8 C9 118.50(14) . . ?
C8 C9 C10 113.31(15) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C16 110.67(15) . . ?
C9 C10 C11 106.54(14) . . ?
C16 C10 C11 110.92(16) . . ?
C9 C10 C17 109.98(16) . . ?
C16 C10 C17 108.98(16) . . ?
C11 C10 C17 109.72(15) . . ?
C12 C11 C10 114.66(14) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C7 C12 N3 122.76(16) . . ?
C7 C12 C11 123.88(16) . . ?
N3 C12 C11 113.36(14) . . ?
C14 C13 N1 107.57(16) . . ?
C14 C13 N3 128.25(16) . . ?
N1 C13 N3 124.17(15) . . ?
C13 C14 C15 105.40(16) . . ?
C13 C14 H14 127.3 . . ?
C15 C14 H14 127.3 . . ?
N2 C15 C14 111.68(16) . . ?
N2 C15 C18 120.35(18) . . ?
C14 C15 C18 127.97(18) . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 N1 N2 110.43(14) . . ?
C13 N1 C1 127.84(15) . . ?
N2 N1 C1 118.79(14) . . ?
C15 N2 N1 104.91(15) . . ?
C12 N3 C13 124.01(14) . . ?
C12 N3 H3A 118.0 . . ?
C13 N3 H3A 118.0 . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.038

