# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_202007121
_database_code_depnum_ccdc_archive 'CCDC 2189779'
loop_
_audit_author_name
_audit_author_address
'wenbo cai'
;zhegnzhou university
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2023-11-12 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         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O1
_chemical_oxdiff_usercomment     r
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'

_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                   10.8216(3)
_cell_length_b                   6.14060(16)
_cell_length_c                   24.5560(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.460(2)
_cell_angle_gamma                90
_cell_volume                     1614.02(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2076
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4040
_cell_measurement_theta_min      4.2450
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.640
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   0.50    2.50    --  -33.50 -37.00  90.00  186
  2  ω   -108.00 -32.00   0.50    2.50    --  -33.50 178.00 -30.00  152
  3  ω    -88.00 -24.00   0.50    2.50    --  -33.50 -57.00-150.00  128
  4  ω    -15.00  25.00   0.50    2.50    --   36.47   0.00-180.00   80
  5  ω     58.00  83.00   0.50    2.50    --   36.47 178.00 -90.00   50
  6  ω     -2.00  64.00   0.50    2.50    --   36.47 -99.00  60.00  132
  7  ω     64.00  92.00   0.50    2.50    --   36.47 178.00  60.00   56
  8  ω     51.00 108.00   0.50    2.50    --   36.47   0.00-180.00  114
  9  ω     85.00 127.00   0.50    7.50    --  108.00 -61.00 150.00   84
 10  ω     54.00  81.00   0.50    7.50    --  108.00 -61.00 150.00   54
 11  ω     40.00 108.00   0.50    7.50    --  108.00 -94.00-150.00  136
 12  ω     38.00 128.00   0.50    7.50    --  108.00 -45.00  60.00  180
 13  ω     53.00  99.00   0.50    7.50    --  108.00 -94.00 -60.00   92
 14  ω    117.00 170.00   0.50    7.50    --  108.00  77.00-150.00  106
 15  ω     79.00 106.00   0.50    7.50    --  108.00  77.00-150.00   54
 16  ω     85.00 157.00   0.50    7.50    --  108.00  77.00 -90.00  144
 17  ω     98.00 162.00   0.50    7.50    --  108.00  45.00-120.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0851300000
_diffrn_orient_matrix_UB_12      0.1158723000
_diffrn_orient_matrix_UB_13      0.0469758000
_diffrn_orient_matrix_UB_21      0.1124961000
_diffrn_orient_matrix_UB_22      -0.1328135000
_diffrn_orient_matrix_UB_23      -0.0133893000
_diffrn_orient_matrix_UB_31      0.0284392000
_diffrn_orient_matrix_UB_32      0.1785648000
_diffrn_orient_matrix_UB_33      -0.0404586000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2224
_reflns_number_total             2882
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.031
_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)+(0.0630P)²+0.0774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.52029(19) 1.2541(3) 0.43534(7) 0.0633(5) Uani 1 1 d . . . . .
H1A H 0.5400 1.2431 0.4751 0.076 Uiso 1 1 calc R . . . .
H1B H 0.4764 1.3899 0.4261 0.076 Uiso 1 1 calc R . . . .
N1 N 0.44549(14) 1.0699(2) 0.41295(6) 0.0596(4) Uani 1 1 d . . . . .
O1 O 0.75787(12) 0.7360(2) 0.35455(5) 0.0658(4) Uani 1 1 d . . . . .
C2 C 0.63812(16) 1.2420(3) 0.40874(7) 0.0551(4) Uani 1 1 d . . . . .
H2 H 0.6230 1.3180 0.3733 0.066 Uiso 1 1 calc R . . . .
O2 O 0.76713(15) 1.0768(2) 0.32412(6) 0.0806(4) Uani 1 1 d . . . . .
C3 C 0.65015(15) 0.9998(3) 0.39785(6) 0.0515(4) Uani 1 1 d . . . . .
H3 H 0.6864 0.9295 0.4324 0.062 Uiso 1 1 calc R . . . .
C4 C 0.51338(15) 0.9185(3) 0.38264(6) 0.0506(4) Uani 1 1 d . . . . .
H4 H 0.5069 0.7721 0.3979 0.061 Uiso 1 1 calc R . . . .
C5 C 0.46590(14) 0.9118(3) 0.32121(6) 0.0475(4) Uani 1 1 d . . . . .
C6 C 0.40629(16) 1.0874(3) 0.29364(7) 0.0552(4) Uani 1 1 d . . . . .
H6 H 0.3934 1.2133 0.3131 0.066 Uiso 1 1 calc R . . . .
C7 C 0.36550(17) 1.0790(3) 0.23770(7) 0.0650(5) Uani 1 1 d . . . . .
H7 H 0.3249 1.1984 0.2199 0.078 Uiso 1 1 calc R . . . .
C8 C 0.38455(18) 0.8952(4) 0.20810(7) 0.0684(5) Uani 1 1 d . . . . .
H8 H 0.3573 0.8901 0.1704 0.082 Uiso 1 1 calc R . . . .
C9 C 0.44430(19) 0.7188(4) 0.23474(8) 0.0693(5) Uani 1 1 d . . . . .
H9 H 0.4580 0.5942 0.2149 0.083 Uiso 1 1 calc R . . . .
C10 C 0.48405(17) 0.7264(3) 0.29093(7) 0.0587(4) Uani 1 1 d . . . . .
H10 H 0.5234 0.6057 0.3086 0.070 Uiso 1 1 calc R . . . .
C11 C 0.7526(2) 1.3420(3) 0.44324(8) 0.0718(5) Uani 1 1 d . . . . .
H11A H 0.7691 1.2679 0.4780 0.108 Uiso 1 1 calc GR . . . .
H11B H 0.7373 1.4934 0.4494 0.108 Uiso 1 1 calc GR . . . .
H11C H 0.8234 1.3276 0.4241 0.108 Uiso 1 1 calc GR . . . .
C12 C 0.73130(16) 0.9475(3) 0.35476(6) 0.0549(4) Uani 1 1 d . . . . .
C13 C 0.8248(2) 0.6594(4) 0.31132(10) 0.0866(7) Uani 1 1 d . . . . .
H13A H 0.8451 0.5082 0.3171 0.130 Uiso 1 1 calc GR . . . .
H13B H 0.9002 0.7420 0.3119 0.130 Uiso 1 1 calc GR . . . .
H13C H 0.7733 0.6771 0.2763 0.130 Uiso 1 1 calc GR . . . .
C14 C 0.32277(17) 1.0396(3) 0.42007(6) 0.0563(4) Uani 1 1 d . . . . .
C15 C 0.25990(19) 1.1972(4) 0.44714(7) 0.0674(5) Uani 1 1 d . . . . .
H15 H 0.3021 1.3217 0.4611 0.081 Uiso 1 1 calc R . . . .
C16 C 0.1365(2) 1.1690(4) 0.45315(9) 0.0794(6) Uani 1 1 d . . . . .
H16 H 0.0964 1.2753 0.4711 0.095 Uiso 1 1 calc R . . . .
C17 C 0.0714(2) 0.9867(5) 0.43319(8) 0.0813(6) Uani 1 1 d . . . . .
H17 H -0.0123 0.9702 0.4371 0.098 Uiso 1 1 calc R . . . .
C18 C 0.13238(19) 0.8285(4) 0.40726(8) 0.0743(6) Uani 1 1 d . . . . .
H18 H 0.0897 0.7031 0.3943 0.089 Uiso 1 1 calc R . . . .
C19 C 0.25557(17) 0.8541(3) 0.40038(7) 0.0620(5) Uani 1 1 d . . . . .
H19 H 0.2946 0.7465 0.3824 0.074 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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 N1 1.451(2) . ?
C1 C2 1.518(2) . ?
N1 C4 1.456(2) . ?
N1 C14 1.377(2) . ?
O1 C12 1.330(2) . ?
O1 C13 1.449(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.520(2) . ?
C2 C11 1.523(3) . ?
O2 C12 1.197(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.555(2) . ?
C3 C12 1.506(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.521(2) . ?
C5 C6 1.381(2) . ?
C5 C10 1.390(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.405(3) . ?
C14 C19 1.399(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(3) . ?
C19 H19 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
H1A C1 H1B 108.9 . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
N1 C1 C2 104.82(14) . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C1 N1 C4 113.34(14) . . ?
C14 N1 C1 123.49(14) . . ?
C14 N1 C4 123.16(15) . . ?
C12 O1 C13 116.85(16) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 102.88(14) . . ?
C1 C2 C11 113.99(15) . . ?
C3 C2 H2 108.5 . . ?
C3 C2 C11 114.12(15) . . ?
C11 C2 H2 108.5 . . ?
C2 C3 H3 108.2 . . ?
C2 C3 C4 104.67(13) . . ?
C4 C3 H3 108.2 . . ?
C12 C3 C2 113.95(14) . . ?
C12 C3 H3 108.2 . . ?
C12 C3 C4 113.32(13) . . ?
N1 C4 C3 101.91(13) . . ?
N1 C4 H4 108.7 . . ?
N1 C4 C5 113.70(14) . . ?
C3 C4 H4 108.7 . . ?
C5 C4 C3 114.69(12) . . ?
C5 C4 H4 108.7 . . ?
C6 C5 C4 122.04(15) . . ?
C6 C5 C10 118.02(15) . . ?
C10 C5 C4 119.93(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.10(17) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.39(18) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.44(17) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.17(18) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.87(18) . . ?
C9 C10 H10 119.6 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C3 111.07(14) . . ?
O2 C12 O1 123.71(16) . . ?
O2 C12 C3 125.22(17) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 120.66(18) . . ?
N1 C14 C19 121.88(16) . . ?
C19 C14 C15 117.45(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.92(18) . . ?
C18 C19 H19 119.5 . . ?

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
C1 N1 C4 C3 11.19(18) . . . . ?
C1 N1 C4 C5 -112.78(17) . . . . ?
C1 N1 C14 C15 4.2(3) . . . . ?
C1 N1 C14 C19 -176.53(16) . . . . ?
C1 C2 C3 C4 35.50(15) . . . . ?
C1 C2 C3 C12 159.83(14) . . . . ?
N1 C1 C2 C3 -28.42(17) . . . . ?
N1 C1 C2 C11 -152.52(16) . . . . ?
N1 C4 C5 C6 26.3(2) . . . . ?
N1 C4 C5 C10 -154.82(15) . . . . ?
N1 C14 C15 C16 178.54(18) . . . . ?
N1 C14 C19 C18 -179.06(17) . . . . ?
C2 C1 N1 C4 10.77(19) . . . . ?
C2 C1 N1 C14 -169.87(15) . . . . ?
C2 C3 C4 N1 -28.75(15) . . . . ?
C2 C3 C4 C5 94.55(15) . . . . ?
C2 C3 C12 O1 167.97(14) . . . . ?
C2 C3 C12 O2 -12.6(2) . . . . ?
C3 C4 C5 C6 -90.38(18) . . . . ?
C3 C4 C5 C10 88.45(19) . . . . ?
C4 N1 C14 C15 -176.50(15) . . . . ?
C4 N1 C14 C19 2.8(3) . . . . ?
C4 C3 C12 O1 -72.48(17) . . . . ?
C4 C3 C12 O2 106.9(2) . . . . ?
C4 C5 C6 C7 179.06(16) . . . . ?
C4 C5 C10 C9 -178.42(16) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C5 C10 C9 0.5(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C5 -0.8(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C11 C2 C3 C4 159.51(14) . . . . ?
C11 C2 C3 C12 -76.16(18) . . . . ?
C12 C3 C4 N1 -153.49(14) . . . . ?
C12 C3 C4 C5 -30.2(2) . . . . ?
C13 O1 C12 O2 -5.6(3) . . . . ?
C13 O1 C12 C3 173.89(16) . . . . ?
C14 N1 C4 C3 -168.18(15) . . . . ?
C14 N1 C4 C5 67.9(2) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C14 0.8(3) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.920
####################################################################### 
# 
# 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_202007127
_database_code_depnum_ccdc_archive 'CCDC 2190240'
loop_
_audit_author_name
_audit_author_address
'wenbo cai'
;zhengzhou university
China
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2023-11-12 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            'C16 H14 N2 O S'
_chemical_formula_weight         282.35

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.4233(6)
_cell_length_b                   5.92585(16)
_cell_length_c                   24.5767(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.764(3)
_cell_angle_gamma                90
_cell_volume                     2822.67(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(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    1.329
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.003
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.840
_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     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5251
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.605
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_full        67.076
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2510
_reflns_number_gt                2138
_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)+(0.0613P)²+0.3909P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2510
_refine_ls_number_parameters     248
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
S1 S 0.73471(17) 1.0414(6) 0.56670(15) 0.0471(3) Uani 0.301(2) 1 d . . P A 1
S1A S 0.69295(5) 0.59906(16) 0.60035(4) 0.0471(3) Uani 0.699(2) 1 d . . P A 2
O1 O 0.50037(7) 1.2624(2) 0.64132(5) 0.0572(3) Uani 1 1 d . . . . .
N1 N 0.60634(10) 1.2289(3) 0.47468(7) 0.0675(5) Uani 1 1 d . . . . .
N2 N 0.57277(6) 0.8559(2) 0.64415(5) 0.0399(3) Uani 1 1 d . . . . .
C1 C 0.59298(9) 1.1746(3) 0.51754(7) 0.0477(4) Uani 1 1 d . . . . .
C2 C 0.50670(11) 1.2499(3) 0.58455(8) 0.0536(4) Uani 1 1 d . . . . .
H2A H 0.5151(11) 1.404(4) 0.5714(9) 0.064 Uiso 1 1 d . U . . .
H2B H 0.4618(12) 1.189(4) 0.5662(9) 0.064 Uiso 1 1 d . U . . .
C3 C 0.56991(8) 1.1181(3) 0.56970(6) 0.0413(4) Uani 1 1 d . . . . .
C4 C 0.60374(8) 0.9598(2) 0.60154(6) 0.0371(3) Uani 1 1 d D . . . .
C5 C 0.49714(9) 0.8524(3) 0.64220(8) 0.0487(4) Uani 1 1 d . . . . .
H5A H 0.4816(11) 0.723(3) 0.6660(8) 0.058 Uiso 1 1 d . U . . .
H5B H 0.4806(11) 0.820(3) 0.6041(8) 0.058 Uiso 1 1 d . U . . .
C6 C 0.46745(10) 1.0698(4) 0.66257(9) 0.0564(5) Uani 1 1 d . . . . .
H6A H 0.4179(12) 1.070(4) 0.6533(9) 0.068 Uiso 1 1 d . U . . .
H6B H 0.4733(11) 1.084(4) 0.7012(10) 0.068 Uiso 1 1 d . U . . .
C7 C 0.6700(9) 0.841(2) 0.5934(9) 0.0306(8) Uani 0.301(2) 1 d D . P A 1
C7A C 0.6733(3) 0.8895(7) 0.5895(3) 0.0306(8) Uani 0.699(2) 1 d . . P A 2
C8 C 0.6993(7) 0.650(2) 0.6057(6) 0.0596(16) Uani 0.301(2) 1 d D . P A 1
H8 H 0.659(4) 0.495(13) 0.619(3) 0.071 Uiso 0.301(2) 1 d . U P A 1
C8A C 0.7287(3) 0.9870(8) 0.5708(2) 0.0596(16) Uani 0.699(2) 1 d . . P A 2
H8A H 0.7226(18) 1.160(6) 0.5627(13) 0.071 Uiso 0.699(2) 1 d . U P A 2
C9 C 0.7609(7) 0.630(3) 0.5835(6) 0.0494(11) Uani 0.301(2) 1 d D . P A 1
H9 H 0.798(4) 0.453(11) 0.588(3) 0.059 Uiso 0.301(2) 1 d . U P A 1
C9A C 0.7841(3) 0.8581(7) 0.5660(2) 0.0494(11) Uani 0.699(2) 1 d . . P A 2
H9A H 0.830(2) 0.906(5) 0.5532(16) 0.059 Uiso 0.699(2) 1 d . U P A 2
C10 C 0.7965(9) 0.819(2) 0.5651(7) 0.0466(9) Uani 0.301(2) 1 d D . P A 1
H10 H 0.836(5) 0.836(12) 0.547(4) 0.056 Uiso 0.301(2) 1 d . U P A 1
C10A C 0.7759(2) 0.6397(10) 0.5795(2) 0.0466(9) Uani 0.699(2) 1 d . . P A 2
H10A H 0.8053(19) 0.533(5) 0.5759(13) 0.056 Uiso 0.699(2) 1 d . U P A 2
C11 C 0.60936(8) 0.8207(3) 0.69585(6) 0.0370(3) Uani 1 1 d . . . . .
C12 C 0.59823(9) 0.6251(3) 0.72490(7) 0.0466(4) Uani 1 1 d . . . . .
H12 H 0.5665(10) 0.509(3) 0.7102(8) 0.056 Uiso 1 1 d . U . . .
C13 C 0.63306(10) 0.5914(3) 0.77526(7) 0.0524(4) Uani 1 1 d . . . . .
H13 H 0.6272(11) 0.452(4) 0.7953(9) 0.063 Uiso 1 1 d . U . . .
C14 C 0.67904(10) 0.7504(3) 0.79652(7) 0.0532(5) Uani 1 1 d . . . . .
H14 H 0.7025(11) 0.725(3) 0.8321(9) 0.064 Uiso 1 1 d . U . . .
C15 C 0.69022(9) 0.9444(3) 0.76752(7) 0.0513(4) Uani 1 1 d . . . . .
H15 H 0.7224(11) 1.055(3) 0.7817(9) 0.062 Uiso 1 1 d . U . . .
C16 C 0.65530(8) 0.9810(3) 0.71745(7) 0.0434(4) Uani 1 1 d . . . . .
H16 H 0.6627(10) 1.119(3) 0.6977(8) 0.052 Uiso 1 1 d . 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
S1 C10 1.783(13) . ?
S1 C7 1.877(16) . ?
S1A C10A 1.740(3) . ?
S1A C7A 1.779(4) . ?
O1 C2 1.411(2) . ?
O1 C6 1.424(2) . ?
N1 C1 1.147(2) . ?
N2 C4 1.3857(19) . ?
N2 C11 1.4297(19) . ?
N2 C5 1.467(2) . ?
C1 C3 1.425(2) . ?
C2 C3 1.520(2) . ?
C2 H2A 0.99(2) . ?
C2 H2B 1.02(2) . ?
C3 C4 1.363(2) . ?
C4 C7A 1.462(7) . ?
C4 C7 1.492(15) . ?
C5 C6 1.510(3) . ?
C5 H5A 1.02(2) . ?
C5 H5B 0.99(2) . ?
C6 H6A 0.98(2) . ?
C6 H6B 0.95(2) . ?
C7 C8 1.297(15) . ?
C7A C8A 1.331(9) . ?
C8 C9 1.354(14) . ?
C8 H8 1.26(8) . ?
C8A C9A 1.331(7) . ?
C8A H8A 1.05(4) . ?
C9 C10 1.408(15) . ?
C9 H9 1.27(8) . ?
C9A C10A 1.348(6) . ?
C9A H9A 1.00(4) . ?
C10 H10 0.92(9) . ?
C10A H10A 0.86(4) . ?
C11 C16 1.385(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.98(2) . ?
C13 C14 1.377(3) . ?
C13 H13 0.97(2) . ?
C14 C15 1.377(3) . ?
C14 H14 0.97(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.96(2) . ?
C16 H16 0.96(2) . ?

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
C10 S1 C7 90.5(7) . . ?
C10A S1A C7A 90.9(3) . . ?
C2 O1 C6 113.01(15) . . ?
C4 N2 C11 121.42(12) . . ?
C4 N2 C5 117.71(13) . . ?
C11 N2 C5 117.74(13) . . ?
N1 C1 C3 174.3(2) . . ?
O1 C2 C3 112.88(15) . . ?
O1 C2 H2A 107.5(13) . . ?
C3 C2 H2A 104.2(13) . . ?
O1 C2 H2B 109.2(12) . . ?
C3 C2 H2B 113.1(12) . . ?
H2A C2 H2B 109.8(18) . . ?
C4 C3 C1 120.67(15) . . ?
C4 C3 C2 125.63(15) . . ?
C1 C3 C2 113.69(15) . . ?
C3 C4 N2 121.54(14) . . ?
C3 C4 C7A 119.8(3) . . ?
N2 C4 C7A 118.6(2) . . ?
C3 C4 C7 129.4(7) . . ?
N2 C4 C7 108.3(6) . . ?
N2 C5 C6 112.37(15) . . ?
N2 C5 H5A 108.9(12) . . ?
C6 C5 H5A 108.4(11) . . ?
N2 C5 H5B 107.3(12) . . ?
C6 C5 H5B 111.9(12) . . ?
H5A C5 H5B 107.8(17) . . ?
O1 C6 C5 111.82(14) . . ?
O1 C6 H6A 112.0(13) . . ?
C5 C6 H6A 108.3(13) . . ?
O1 C6 H6B 105.6(13) . . ?
C5 C6 H6B 112.4(13) . . ?
H6A C6 H6B 106.6(18) . . ?
C8 C7 C4 138.6(14) . . ?
C8 C7 S1 110.0(12) . . ?
C4 C7 S1 110.7(7) . . ?
C8A C7A C4 136.5(4) . . ?
C8A C7A S1A 107.5(4) . . ?
C4 C7A S1A 116.0(3) . . ?
C7 C8 C9 111.5(15) . . ?
C7 C8 H8 116(4) . . ?
C9 C8 H8 128(4) . . ?
C7A C8A C9A 117.3(5) . . ?
C7A C8A H8A 114(2) . . ?
C9A C8A H8A 129(2) . . ?
C8 C9 C10 121.7(18) . . ?
C8 C9 H9 123(3) . . ?
C10 C9 H9 114(4) . . ?
C8A C9A C10A 114.9(6) . . ?
C8A C9A H9A 127(2) . . ?
C10A C9A H9A 118.0(19) . . ?
C9 C10 S1 103.7(15) . . ?
C9 C10 H10 133(5) . . ?
S1 C10 H10 121(5) . . ?
C9A C10A S1A 109.3(5) . . ?
C9A C10A H10A 126(2) . . ?
S1A C10A H10A 124(2) . . ?
C16 C11 C12 119.64(15) . . ?
C16 C11 N2 120.72(14) . . ?
C12 C11 N2 119.64(14) . . ?
C13 C12 C11 119.83(17) . . ?
C13 C12 H12 119.1(12) . . ?
C11 C12 H12 121.0(11) . . ?
C14 C13 C12 120.44(17) . . ?
C14 C13 H13 119.0(13) . . ?
C12 C13 H13 120.5(13) . . ?
C15 C14 C13 119.66(17) . . ?
C15 C14 H14 121.0(13) . . ?
C13 C14 H14 119.3(13) . . ?
C14 C15 C16 120.45(18) . . ?
C14 C15 H15 120.3(13) . . ?
C16 C15 H15 119.3(13) . . ?
C15 C16 C11 119.97(17) . . ?
C15 C16 H16 120.0(12) . . ?
C11 C16 H16 120.0(12) . . ?

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
C6 O1 C2 C3 -84.14(19) . . . . ?
O1 C2 C3 C4 23.2(3) . . . . ?
O1 C2 C3 C1 -156.55(15) . . . . ?
C1 C3 C4 N2 -161.43(15) . . . . ?
C2 C3 C4 N2 18.9(2) . . . . ?
C1 C3 C4 C7A 15.9(4) . . . . ?
C2 C3 C4 C7A -163.8(4) . . . . ?
C1 C3 C4 C7 7.3(10) . . . . ?
C2 C3 C4 C7 -172.4(10) . . . . ?
C11 N2 C4 C3 -136.88(16) . . . . ?
C5 N2 C4 C3 22.6(2) . . . . ?
C11 N2 C4 C7A 45.7(4) . . . . ?
C5 N2 C4 C7A -154.8(4) . . . . ?
C11 N2 C4 C7 52.3(9) . . . . ?
C5 N2 C4 C7 -148.2(9) . . . . ?
C4 N2 C5 C6 -82.19(19) . . . . ?
C11 N2 C5 C6 78.09(19) . . . . ?
C2 O1 C6 C5 47.4(2) . . . . ?
N2 C5 C6 O1 44.4(2) . . . . ?
C3 C4 C7 C8 -151(2) . . . . ?
N2 C4 C7 C8 19(3) . . . . ?
C3 C4 C7 S1 40.3(17) . . . . ?
N2 C4 C7 S1 -149.8(8) . . . . ?
C10 S1 C7 C8 8.6(16) . . . . ?
C10 S1 C7 C4 -179.5(13) . . . . ?
C3 C4 C7A C8A 35.3(11) . . . . ?
N2 C4 C7A C8A -147.3(8) . . . . ?
C3 C4 C7A S1A -143.3(3) . . . . ?
N2 C4 C7A S1A 34.2(6) . . . . ?
C10A S1A C7A C8A 1.1(6) . . . . ?
C10A S1A C7A C4 -179.9(5) . . . . ?
C4 C7 C8 C9 176(2) . . . . ?
S1 C7 C8 C9 -16(2) . . . . ?
C4 C7A C8A C9A 179.4(8) . . . . ?
S1A C7A C8A C9A -1.9(8) . . . . ?
C7 C8 C9 C10 19(3) . . . . ?
C7A C8A C9A C10A 2.0(10) . . . . ?
C8 C9 C10 S1 -11(2) . . . . ?
C7 S1 C10 C9 0.8(15) . . . . ?
C8A C9A C10A S1A -0.9(8) . . . . ?
C7A S1A C10A C9A -0.2(6) . . . . ?
C4 N2 C11 C16 37.5(2) . . . . ?
C5 N2 C11 C16 -122.00(17) . . . . ?
C4 N2 C11 C12 -143.13(15) . . . . ?
C5 N2 C11 C12 57.4(2) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
N2 C11 C12 C13 -179.36(15) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
N2 C11 C16 C15 179.95(15) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_202104116
_database_code_depnum_ccdc_archive 'CCDC 2190017'
loop_
_audit_author_name
_audit_author_address
'wenbo cai'
;zhengzhou university
China
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2023-11-12 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            'C26 H25 N3 O'
_chemical_formula_weight         395.49

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.7602(3)
_cell_length_b                   10.5608(4)
_cell_length_c                   21.6908(8)
_cell_angle_alpha                84.366(3)
_cell_angle_beta                 81.071(3)
_cell_angle_gamma                89.652(3)
_cell_volume                     2197.93(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(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    1.195
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.578
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.966
_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     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16357
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.146
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_full        67.080
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7859
_reflns_number_gt                4660
_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)+(0.0744P)²] 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         7859
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
O1 O 0.9887(3) 0.6551(3) 0.05954(11) 0.1284(9) Uani 1 1 d . . . . .
N1 N 0.1912(3) 0.6039(3) 0.38826(12) 0.1048(8) Uani 1 1 d . . . . .
N2 N 0.4734(2) 0.4086(2) 0.23110(12) 0.0869(6) Uani 1 1 d . . . . .
N3 N 0.6450(2) 0.43555(19) 0.32578(11) 0.0775(6) Uani 1 1 d . . . . .
C1 C 0.3671(3) 0.4188(3) 0.28466(14) 0.0888(8) Uani 1 1 d . . . . .
H1A H 0.3424 0.3339 0.3043 0.107 Uiso 1 1 calc R U . . .
H1B H 0.2853 0.4555 0.2699 0.107 Uiso 1 1 calc R U . . .
C2 C 0.4071(3) 0.4987(2) 0.33417(12) 0.0727(6) Uani 1 1 d . . . . .
C3 C 0.5380(3) 0.5112(2) 0.34853(12) 0.0714(6) Uani 1 1 d . . . . .
C4 C 0.6155(3) 0.3122(2) 0.30584(16) 0.0931(9) Uani 1 1 d . . . . .
H4A H 0.5382 0.2730 0.3348 0.112 Uiso 1 1 calc R U . . .
H4B H 0.6955 0.2581 0.3085 0.112 Uiso 1 1 calc R U . . .
C5 C 0.5808(3) 0.3168(3) 0.23996(17) 0.0956(9) Uani 1 1 d . . . . .
H5A H 0.6634 0.3395 0.2099 0.115 Uiso 1 1 calc R U . . .
H5B H 0.5499 0.2333 0.2325 0.115 Uiso 1 1 calc R U . . .
C6 C 0.2920(3) 0.5593(3) 0.36648(12) 0.0791(7) Uani 1 1 d . . . . .
C7 C 0.5661(3) 0.6012(2) 0.39368(11) 0.0760(7) Uani 1 1 d . . . . .
C8 C 0.5192(3) 0.7252(3) 0.39001(13) 0.0831(7) Uani 1 1 d . . . . .
H8 H 0.4731 0.7553 0.3572 0.100 Uiso 1 1 calc R U . . .
C9 C 0.5403(4) 0.8047(3) 0.43473(16) 0.1054(10) Uani 1 1 d . . . . .
H9 H 0.5068 0.8874 0.4322 0.127 Uiso 1 1 calc R U . . .
C10 C 0.6103(5) 0.7623(5) 0.48267(17) 0.1234(14) Uani 1 1 d . . . . .
H10 H 0.6245 0.8160 0.5127 0.148 Uiso 1 1 calc R U . . .
C11 C 0.6596(5) 0.6401(5) 0.48625(16) 0.1256(14) Uani 1 1 d . . . . .
H11 H 0.7085 0.6117 0.5184 0.151 Uiso 1 1 calc R U . . .
C12 C 0.6372(4) 0.5587(3) 0.44239(14) 0.1011(9) Uani 1 1 d . . . . .
H12 H 0.6696 0.4757 0.4456 0.121 Uiso 1 1 calc R U . . .
C13 C 0.4805(2) 0.4918(3) 0.17759(14) 0.0765(7) Uani 1 1 d . . . . .
C14 C 0.5565(3) 0.4629(3) 0.12066(15) 0.0904(8) Uani 1 1 d . . . . .
H14 H 0.6021 0.3854 0.1187 0.108 Uiso 1 1 calc R U . . .
C15 C 0.5651(3) 0.5464(4) 0.06787(17) 0.1141(12) Uani 1 1 d . . . . .
H15 H 0.6176 0.5253 0.0308 0.137 Uiso 1 1 calc R U . . .
C16 C 0.4975(4) 0.6607(4) 0.06868(19) 0.1232(12) Uani 1 1 d . . . . .
H16 H 0.5038 0.7170 0.0326 0.148 Uiso 1 1 calc R U . . .
C17 C 0.4207(3) 0.6903(4) 0.12368(19) 0.1086(10) Uani 1 1 d . . . . .
H17 H 0.3738 0.7671 0.1246 0.130 Uiso 1 1 calc R U . . .
C18 C 0.4118(3) 0.6079(3) 0.17776(15) 0.0867(8) Uani 1 1 d . . . . .
H18 H 0.3594 0.6302 0.2146 0.104 Uiso 1 1 calc R U . . .
C19 C 0.7903(3) 0.4787(3) 0.31288(14) 0.0834(7) Uani 1 1 d . . . . .
H19A H 0.8480 0.4102 0.3271 0.100 Uiso 1 1 calc R U . . .
H19B H 0.8005 0.5496 0.3371 0.100 Uiso 1 1 calc R U . . .
C20 C 0.8423(2) 0.5194(2) 0.24467(13) 0.0714(6) Uani 1 1 d . . . . .
C21 C 0.9602(3) 0.4668(3) 0.21317(16) 0.0896(8) Uani 1 1 d . . . . .
H21 H 1.0054 0.4017 0.2338 0.108 Uiso 1 1 calc R U . . .
C22 C 1.0122(3) 0.5098(3) 0.15106(16) 0.0964(9) Uani 1 1 d . . . . .
H22 H 1.0918 0.4739 0.1307 0.116 Uiso 1 1 calc R U . . .
C23 C 0.9455(3) 0.6054(3) 0.12006(14) 0.0880(8) Uani 1 1 d . . . . .
C24 C 0.8279(3) 0.6566(3) 0.15074(14) 0.0831(7) Uani 1 1 d . . . . .
H24 H 0.7817 0.7206 0.1298 0.100 Uiso 1 1 calc R U . . .
C25 C 0.7776(2) 0.6148(2) 0.21183(13) 0.0740(6) Uani 1 1 d . . . . .
H25 H 0.6980 0.6514 0.2317 0.089 Uiso 1 1 calc R U . . .
C26 C 1.1153(4) 0.6135(5) 0.02788(19) 0.159(2) Uani 1 1 d . . . . .
H26A H 1.1296 0.6520 -0.0146 0.239 Uiso 1 1 calc R U . . .
H26B H 1.1128 0.5226 0.0280 0.239 Uiso 1 1 calc R U . . .
H26C H 1.1898 0.6374 0.0486 0.239 Uiso 1 1 calc R U . . .
O1' O 0.2902(3) 0.8803(3) 0.92756(11) 0.1185(8) Uani 1 1 d . . . . .
N1' N -0.3726(2) 0.9145(2) 0.62210(12) 0.0932(7) Uani 1 1 d . . . . .
N2' N -0.1781(2) 1.0902(2) 0.78044(12) 0.0845(6) Uani 1 1 d . . . . .
N3' N 0.04718(19) 1.06836(19) 0.67834(11) 0.0747(5) Uani 1 1 d . . . . .
C1' C -0.2561(2) 1.0862(3) 0.72926(14) 0.0834(7) Uani 1 1 d . . . . .
H1'A H -0.2706 1.1728 0.7122 0.100 Uiso 1 1 calc R U . . .
H1'B H -0.3465 1.0488 0.7457 0.100 Uiso 1 1 calc R U . . .
C2' C -0.1882(2) 1.0117(2) 0.67624(11) 0.0660(6) Uani 1 1 d . . . . .
C3' C -0.0491(2) 0.9967(2) 0.65785(11) 0.0644(5) Uani 1 1 d . . . . .
C4' C 0.0074(3) 1.1898(2) 0.70218(16) 0.0895(8) Uani 1 1 d . . . . .
H4'A H -0.0546 1.2322 0.6761 0.107 Uiso 1 1 calc R U . . .
H4'B H 0.0899 1.2426 0.6981 0.107 Uiso 1 1 calc R U . . .
C5' C -0.0631(3) 1.1806(3) 0.76992(16) 0.0908(9) Uani 1 1 d . . . . .
H5'A H 0.0036 1.1539 0.7973 0.109 Uiso 1 1 calc R U . . .
H5'B H -0.0971 1.2637 0.7801 0.109 Uiso 1 1 calc R U . . .
C6' C -0.2853(2) 0.9551(2) 0.64415(12) 0.0705(6) Uani 1 1 d . . . . .
C7' C 0.0015(2) 0.9054(2) 0.61216(11) 0.0710(6) Uani 1 1 d . . . . .
C8' C 0.0936(3) 0.9443(4) 0.55830(14) 0.1036(10) Uani 1 1 d . . . . .
H8' H 0.1261 1.0279 0.5512 0.124 Uiso 1 1 calc R U . . .
C9' C 0.1372(5) 0.8583(6) 0.51512(17) 0.1393(17) Uani 1 1 d . . . . .
H9' H 0.1987 0.8848 0.4790 0.167 Uiso 1 1 calc R U . . .
C10' C 0.0908(6) 0.7353(6) 0.5251(2) 0.150(2) Uani 1 1 d . . . . .
H10' H 0.1201 0.6785 0.4957 0.180 Uiso 1 1 calc R U . . .
C11' C 0.0019(4) 0.6958(4) 0.5780(2) 0.1179(12) Uani 1 1 d . . . . .
H11' H -0.0289 0.6117 0.5849 0.141 Uiso 1 1 calc R U . . .
C12' C -0.0431(3) 0.7798(3) 0.62179(14) 0.0832(7) Uani 1 1 d . . . . .
H12' H -0.1036 0.7518 0.6579 0.100 Uiso 1 1 calc R U . . .
C13' C -0.1919(2) 0.9959(3) 0.83014(14) 0.0810(7) Uani 1 1 d . . . . .
C14' C -0.1433(3) 1.0143(4) 0.88611(16) 0.0983(9) Uani 1 1 d . . . . .
H14' H -0.1031 1.0919 0.8904 0.118 Uiso 1 1 calc R U . . .
C15' C -0.1544(4) 0.9185(5) 0.93508(18) 0.1203(12) Uani 1 1 d . . . . .
H15' H -0.1203 0.9326 0.9716 0.144 Uiso 1 1 calc R U . . .
C16' C -0.2151(4) 0.8025(5) 0.9309(2) 0.1335(14) Uani 1 1 d . . . . .
H16' H -0.2209 0.7379 0.9635 0.160 Uiso 1 1 calc R U . . .
C17' C -0.2663(4) 0.7861(4) 0.8770(2) 0.1196(12) Uani 1 1 d . . . . .
H17' H -0.3104 0.7096 0.8739 0.144 Uiso 1 1 calc R U . . .
C18' C -0.2550(3) 0.8789(3) 0.82693(17) 0.0947(9) Uani 1 1 d . . . . .
H18' H -0.2897 0.8634 0.7908 0.114 Uiso 1 1 calc R U . . .
C19' C 0.1896(2) 1.0267(3) 0.68108(13) 0.0795(7) Uani 1 1 d . . . . .
H19C H 0.2529 1.0948 0.6617 0.095 Uiso 1 1 calc R U . . .
H19D H 0.2084 0.9543 0.6569 0.095 Uiso 1 1 calc R U . . .
C20' C 0.2172(2) 0.9901(2) 0.74694(12) 0.0660(6) Uani 1 1 d . . . . .
C21' C 0.3225(2) 1.0481(2) 0.76987(13) 0.0747(7) Uani 1 1 d . . . . .
H21' H 0.3757 1.1115 0.7444 0.090 Uiso 1 1 calc R U . . .
C22' C 0.3509(3) 1.0142(3) 0.82959(14) 0.0832(7) Uani 1 1 d . . . . .
H22' H 0.4226 1.0543 0.8440 0.100 Uiso 1 1 calc R U . . .
C23' C 0.2728(3) 0.9212(3) 0.86763(13) 0.0832(7) Uani 1 1 d . . . . .
C24' C 0.1667(3) 0.8619(3) 0.84528(14) 0.0851(8) Uani 1 1 d . . . . .
H24' H 0.1133 0.7988 0.8708 0.102 Uiso 1 1 calc R U . . .
C25' C 0.1404(2) 0.8961(2) 0.78588(13) 0.0764(7) Uani 1 1 d . . . . .
H25' H 0.0693 0.8553 0.7714 0.092 Uiso 1 1 calc R U . . .
C26' C 0.3938(4) 0.9421(5) 0.95291(17) 0.1425(17) Uani 1 1 d . . . . .
H26D H 0.3922 0.9091 0.9959 0.214 Uiso 1 1 calc R U . . .
H26E H 0.3765 1.0319 0.9507 0.214 Uiso 1 1 calc R U . . .
H26F H 0.4831 0.9272 0.9293 0.214 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
O1 C23 1.368(4) . ?
O1 C26 1.407(5) . ?
N1 C6 1.144(3) . ?
N2 C13 1.378(4) . ?
N2 C1 1.445(3) . ?
N2 C5 1.446(4) . ?
N3 C3 1.371(3) . ?
N3 C4 1.456(3) . ?
N3 C19 1.468(3) . ?
C1 C2 1.526(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.371(3) . ?
C2 C6 1.413(4) . ?
C3 C7 1.486(4) . ?
C4 C5 1.515(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C8 1.383(4) . ?
C7 C12 1.389(4) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.394(4) . ?
C13 C14 1.399(4) . ?
C14 C15 1.367(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.509(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.382(4) . ?
C20 C21 1.386(4) . ?
C21 C22 1.396(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(4) . ?
C24 C25 1.370(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O1' C23' 1.365(3) . ?
O1' C26' 1.415(5) . ?
N1' C6' 1.145(3) . ?
N2' C13' 1.385(4) . ?
N2' C1' 1.445(3) . ?
N2' C5' 1.454(3) . ?
N3' C3' 1.363(3) . ?
N3' C4' 1.457(3) . ?
N3' C19' 1.463(3) . ?
C1' C2' 1.522(3) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C2' C3' 1.366(3) . ?
C2' C6' 1.426(3) . ?
C3' C7' 1.478(3) . ?
C4' C5' 1.517(4) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C7' C12' 1.384(4) . ?
C7' C8' 1.388(4) . ?
C8' C9' 1.386(5) . ?
C8' H8' 0.9300 . ?
C9' C10' 1.365(7) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.359(6) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.383(4) . ?
C11' H11' 0.9300 . ?
C12' H12' 0.9300 . ?
C13' C18' 1.396(4) . ?
C13' C14' 1.401(4) . ?
C14' C15' 1.385(5) . ?
C14' H14' 0.9300 . ?
C15' C16' 1.381(6) . ?
C15' H15' 0.9300 . ?
C16' C17' 1.366(6) . ?
C16' H16' 0.9300 . ?
C17' C18' 1.382(5) . ?
C17' H17' 0.9300 . ?
C18' H18' 0.9300 . ?
C19' C20' 1.508(3) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C20' C21' 1.380(3) . ?
C20' C25' 1.382(3) . ?
C21' C22' 1.379(4) . ?
C21' H21' 0.9300 . ?
C22' C23' 1.371(4) . ?
C22' H22' 0.9300 . ?
C23' C24' 1.387(4) . ?
C24' C25' 1.366(4) . ?
C24' H24' 0.9300 . ?
C25' H25' 0.9300 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 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
C23 O1 C26 118.5(4) . . ?
C13 N2 C1 121.6(2) . . ?
C13 N2 C5 122.1(2) . . ?
C1 N2 C5 115.9(3) . . ?
C3 N3 C4 119.9(2) . . ?
C3 N3 C19 123.0(2) . . ?
C4 N3 C19 116.6(2) . . ?
N2 C1 C2 115.1(2) . . ?
N2 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N2 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C6 121.6(3) . . ?
C3 C2 C1 125.8(2) . . ?
C6 C2 C1 112.6(2) . . ?
C2 C3 N3 121.8(2) . . ?
C2 C3 C7 120.6(2) . . ?
N3 C3 C7 117.4(2) . . ?
N3 C4 C5 114.7(2) . . ?
N3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
N3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
N2 C5 C4 110.9(2) . . ?
N2 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C2 172.9(3) . . ?
C8 C7 C12 118.9(3) . . ?
C8 C7 C3 121.9(2) . . ?
C12 C7 C3 119.2(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.7(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
N2 C13 C18 121.6(3) . . ?
N2 C13 C14 121.3(3) . . ?
C18 C13 C14 117.2(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 121.1(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
N3 C19 C20 114.3(2) . . ?
N3 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
N3 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C25 C20 C21 117.3(3) . . ?
C25 C20 C19 121.2(2) . . ?
C21 C20 C19 121.4(3) . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O1 C23 C24 116.4(3) . . ?
O1 C23 C22 124.4(3) . . ?
C24 C23 C22 119.2(3) . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C20 121.7(3) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23' O1' C26' 117.1(3) . . ?
C13' N2' C1' 121.6(2) . . ?
C13' N2' C5' 121.1(2) . . ?
C1' N2' C5' 115.9(3) . . ?
C3' N3' C4' 119.7(2) . . ?
C3' N3' C19' 123.2(2) . . ?
C4' N3' C19' 117.0(2) . . ?
N2' C1' C2' 114.7(2) . . ?
N2' C1' H1'A 108.6 . . ?
C2' C1' H1'A 108.6 . . ?
N2' C1' H1'B 108.6 . . ?
C2' C1' H1'B 108.6 . . ?
H1'A C1' H1'B 107.6 . . ?
C3' C2' C6' 119.9(2) . . ?
C3' C2' C1' 126.7(2) . . ?
C6' C2' C1' 113.4(2) . . ?
N3' C3' C2' 121.8(2) . . ?
N3' C3' C7' 117.7(2) . . ?
C2' C3' C7' 120.4(2) . . ?
N3' C4' C5' 115.0(2) . . ?
N3' C4' H4'A 108.5 . . ?
C5' C4' H4'A 108.5 . . ?
N3' C4' H4'B 108.5 . . ?
C5' C4' H4'B 108.5 . . ?
H4'A C4' H4'B 107.5 . . ?
N2' C5' C4' 110.8(2) . . ?
N2' C5' H5'A 109.5 . . ?
C4' C5' H5'A 109.5 . . ?
N2' C5' H5'B 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
H5'A C5' H5'B 108.1 . . ?
N1' C6' C2' 173.7(3) . . ?
C12' C7' C8' 118.6(3) . . ?
C12' C7' C3' 120.8(2) . . ?
C8' C7' C3' 120.6(3) . . ?
C9' C8' C7' 119.9(4) . . ?
C9' C8' H8' 120.1 . . ?
C7' C8' H8' 120.1 . . ?
C10' C9' C8' 120.7(4) . . ?
C10' C9' H9' 119.7 . . ?
C8' C9' H9' 119.7 . . ?
C11' C10' C9' 119.9(4) . . ?
C11' C10' H10' 120.0 . . ?
C9' C10' H10' 120.0 . . ?
C10' C11' C12' 120.4(4) . . ?
C10' C11' H11' 119.8 . . ?
C12' C11' H11' 119.8 . . ?
C11' C12' C7' 120.5(3) . . ?
C11' C12' H12' 119.8 . . ?
C7' C12' H12' 119.8 . . ?
N2' C13' C18' 121.8(3) . . ?
N2' C13' C14' 121.2(3) . . ?
C18' C13' C14' 117.1(3) . . ?
C15' C14' C13' 120.9(4) . . ?
C15' C14' H14' 119.6 . . ?
C13' C14' H14' 119.6 . . ?
C16' C15' C14' 121.4(4) . . ?
C16' C15' H15' 119.3 . . ?
C14' C15' H15' 119.3 . . ?
C17' C16' C15' 117.7(4) . . ?
C17' C16' H16' 121.1 . . ?
C15' C16' H16' 121.1 . . ?
C16' C17' C18' 122.3(4) . . ?
C16' C17' H17' 118.8 . . ?
C18' C17' H17' 118.8 . . ?
C17' C18' C13' 120.6(3) . . ?
C17' C18' H18' 119.7 . . ?
C13' C18' H18' 119.7 . . ?
N3' C19' C20' 113.3(2) . . ?
N3' C19' H19C 108.9 . . ?
C20' C19' H19C 108.9 . . ?
N3' C19' H19D 108.9 . . ?
C20' C19' H19D 108.9 . . ?
H19C C19' H19D 107.7 . . ?
C21' C20' C25' 117.8(2) . . ?
C21' C20' C19' 120.8(2) . . ?
C25' C20' C19' 121.4(2) . . ?
C22' C21' C20' 121.6(2) . . ?
C22' C21' H21' 119.2 . . ?
C20' C21' H21' 119.2 . . ?
C23' C22' C21' 119.7(3) . . ?
C23' C22' H22' 120.1 . . ?
C21' C22' H22' 120.1 . . ?
O1' C23' C22' 125.1(3) . . ?
O1' C23' C24' 115.5(3) . . ?
C22' C23' C24' 119.4(3) . . ?
C25' C24' C23' 120.1(3) . . ?
C25' C24' H24' 119.9 . . ?
C23' C24' H24' 119.9 . . ?
C24' C25' C20' 121.4(2) . . ?
C24' C25' H25' 119.3 . . ?
C20' C25' H25' 119.3 . . ?
O1' C26' H26D 109.5 . . ?
O1' C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
O1' C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 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
C13 N2 C1 C2 -92.5(3) . . . . ?
C5 N2 C1 C2 80.1(3) . . . . ?
N2 C1 C2 C3 -31.5(4) . . . . ?
N2 C1 C2 C6 149.9(3) . . . . ?
C6 C2 C3 N3 168.0(2) . . . . ?
C1 C2 C3 N3 -10.5(4) . . . . ?
C6 C2 C3 C7 -7.1(4) . . . . ?
C1 C2 C3 C7 174.4(2) . . . . ?
C4 N3 C3 C2 -22.9(4) . . . . ?
C19 N3 C3 C2 149.4(2) . . . . ?
C4 N3 C3 C7 152.4(2) . . . . ?
C19 N3 C3 C7 -35.4(3) . . . . ?
C3 N3 C4 C5 82.5(3) . . . . ?
C19 N3 C4 C5 -90.2(3) . . . . ?
C13 N2 C5 C4 136.5(3) . . . . ?
C1 N2 C5 C4 -36.2(3) . . . . ?
N3 C4 C5 N2 -51.1(3) . . . . ?
C2 C3 C7 C8 -47.5(3) . . . . ?
N3 C3 C7 C8 137.2(3) . . . . ?
C2 C3 C7 C12 130.1(3) . . . . ?
N3 C3 C7 C12 -45.2(3) . . . . ?
C12 C7 C8 C9 -1.2(4) . . . . ?
C3 C7 C8 C9 176.4(2) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 -1.1(6) . . . . ?
C10 C11 C12 C7 1.0(6) . . . . ?
C8 C7 C12 C11 0.1(5) . . . . ?
C3 C7 C12 C11 -177.6(3) . . . . ?
C1 N2 C13 C18 17.4(4) . . . . ?
C5 N2 C13 C18 -154.8(3) . . . . ?
C1 N2 C13 C14 -162.3(2) . . . . ?
C5 N2 C13 C14 25.6(4) . . . . ?
N2 C13 C14 C15 -179.0(3) . . . . ?
C18 C13 C14 C15 1.3(4) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
N2 C13 C18 C17 179.7(3) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C3 N3 C19 C20 -99.9(3) . . . . ?
C4 N3 C19 C20 72.6(3) . . . . ?
N3 C19 C20 C25 57.5(3) . . . . ?
N3 C19 C20 C21 -125.3(3) . . . . ?
C25 C20 C21 C22 0.9(4) . . . . ?
C19 C20 C21 C22 -176.5(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C26 O1 C23 C24 174.6(3) . . . . ?
C26 O1 C23 C22 -5.1(5) . . . . ?
C21 C22 C23 O1 179.3(3) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
O1 C23 C24 C25 -178.9(2) . . . . ?
C22 C23 C24 C25 0.8(4) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C21 C20 C25 C24 -0.4(4) . . . . ?
C19 C20 C25 C24 176.9(2) . . . . ?
C13' N2' C1' C2' -87.3(3) . . . . ?
C5' N2' C1' C2' 79.1(3) . . . . ?
N2' C1' C2' C3' -30.1(4) . . . . ?
N2' C1' C2' C6' 150.5(2) . . . . ?
C4' N3' C3' C2' -21.2(4) . . . . ?
C19' N3' C3' C2' 155.3(2) . . . . ?
C4' N3' C3' C7' 155.9(2) . . . . ?
C19' N3' C3' C7' -27.6(3) . . . . ?
C6' C2' C3' N3' 166.8(2) . . . . ?
C1' C2' C3' N3' -12.6(4) . . . . ?
C6' C2' C3' C7' -10.2(4) . . . . ?
C1' C2' C3' C7' 170.4(2) . . . . ?
C3' N3' C4' C5' 81.8(3) . . . . ?
C19' N3' C4' C5' -94.9(3) . . . . ?
C13' N2' C5' C4' 130.5(3) . . . . ?
C1' N2' C5' C4' -35.9(3) . . . . ?
N3' C4' C5' N2' -51.4(3) . . . . ?
N3' C3' C7' C12' 130.0(3) . . . . ?
C2' C3' C7' C12' -52.9(3) . . . . ?
N3' C3' C7' C8' -50.7(3) . . . . ?
C2' C3' C7' C8' 126.4(3) . . . . ?
C12' C7' C8' C9' 1.0(5) . . . . ?
C3' C7' C8' C9' -178.3(3) . . . . ?
C7' C8' C9' C10' -0.2(6) . . . . ?
C8' C9' C10' C11' -0.6(7) . . . . ?
C9' C10' C11' C12' 0.6(7) . . . . ?
C10' C11' C12' C7' 0.2(5) . . . . ?
C8' C7' C12' C11' -1.0(4) . . . . ?
C3' C7' C12' C11' 178.3(3) . . . . ?
C1' N2' C13' C18' 15.3(4) . . . . ?
C5' N2' C13' C18' -150.3(2) . . . . ?
C1' N2' C13' C14' -164.4(2) . . . . ?
C5' N2' C13' C14' 29.9(4) . . . . ?
N2' C13' C14' C15' -178.4(3) . . . . ?
C18' C13' C14' C15' 1.8(4) . . . . ?
C13' C14' C15' C16' -0.9(5) . . . . ?
C14' C15' C16' C17' -1.1(6) . . . . ?
C15' C16' C17' C18' 2.2(6) . . . . ?
C16' C17' C18' C13' -1.2(5) . . . . ?
N2' C13' C18' C17' 179.4(3) . . . . ?
C14' C13' C18' C17' -0.8(4) . . . . ?
C3' N3' C19' C20' -107.2(3) . . . . ?
C4' N3' C19' C20' 69.4(3) . . . . ?
N3' C19' C20' C21' -123.6(2) . . . . ?
N3' C19' C20' C25' 57.8(3) . . . . ?
C25' C20' C21' C22' -0.1(4) . . . . ?
C19' C20' C21' C22' -178.8(2) . . . . ?
C20' C21' C22' C23' -0.3(4) . . . . ?
C26' O1' C23' C22' 2.3(4) . . . . ?
C26' O1' C23' C24' -177.5(3) . . . . ?
C21' C22' C23' O1' -179.5(3) . . . . ?
C21' C22' C23' C24' 0.4(4) . . . . ?
O1' C23' C24' C25' 179.9(2) . . . . ?
C22' C23' C24' C25' 0.0(4) . . . . ?
C23' C24' C25' C20' -0.4(4) . . . . ?
C21' C20' C25' C24' 0.5(4) . . . . ?
C19' C20' C25' C24' 179.2(2) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030



