# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2118284'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25

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/a
_symmetry_space_group_name_Hall  '-P 2yab'

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

_cell_length_a                   11.8013(2)
_cell_length_b                   6.8401(2)
_cell_length_c                   14.1778(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9732(11)
_cell_angle_gamma                90.00
_cell_volume                     1143.78(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2830
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   'Scalepack (Otwinowsky & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(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  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ=55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5005
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2613
_reflns_number_gt                2058
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Nonius, 2002)'
_computing_cell_refinement       'Denzo-SMN (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'XP in SHELXTL (Sheldrick, 1995)'

_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
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0810P)²+0.1988P] 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_number_reflns         2613
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
C1 C 0.53558(11) 0.5060(2) 0.18949(9) 0.0192(3) Uani 1 1 d . . .
C2 C 0.45880(11) 0.5738(2) 0.11787(9) 0.0195(3) Uani 1 1 d . . .
C3 C 0.36169(12) 0.4655(2) 0.09346(9) 0.0227(3) Uani 1 1 d . . .
H3 H 0.3107 0.5119 0.0452 0.027 Uiso 1 1 calc R . .
C4 C 0.33909(12) 0.2919(2) 0.13880(10) 0.0255(3) Uani 1 1 d . . .
H4 H 0.2726 0.2194 0.1225 0.031 Uiso 1 1 calc R . .
C5 C 0.41501(12) 0.2247(2) 0.20865(10) 0.0252(3) Uani 1 1 d . . .
H5 H 0.3991 0.1055 0.2399 0.030 Uiso 1 1 calc R . .
C6 C 0.51335(12) 0.3261(2) 0.23432(9) 0.0223(3) Uani 1 1 d . . .
N7 N 0.63568(10) 0.60806(18) 0.21481(8) 0.0204(3) Uani 1 1 d . . .
H7 H 0.6583(14) 0.688(2) 0.1722(12) 0.024 Uiso 1 1 d . . .
C8 C 0.65137(11) 0.69398(19) 0.30553(9) 0.0209(3) Uani 1 1 d . . .
C9 C 0.56756(13) 0.6907(2) 0.37258(10) 0.0247(3) Uani 1 1 d . . .
H9 H 0.4980 0.6250 0.3589 0.030 Uiso 1 1 calc R . .
C10 C 0.58518(13) 0.7827(2) 0.45922(10) 0.0283(4) Uani 1 1 d . . .
H10 H 0.5279 0.7782 0.5046 0.034 Uiso 1 1 calc R . .
C11 C 0.68513(13) 0.8805(2) 0.47987(10) 0.0294(4) Uani 1 1 d . . .
H11 H 0.6968 0.9438 0.5390 0.035 Uiso 1 1 calc R . .
C12 C 0.76838(13) 0.8854(2) 0.41328(10) 0.0295(4) Uani 1 1 d . . .
H12 H 0.8372 0.9535 0.4270 0.035 Uiso 1 1 calc R . .
C13 C 0.75255(12) 0.7921(2) 0.32675(10) 0.0250(3) Uani 1 1 d . . .
H13 H 0.8107 0.7953 0.2821 0.030 Uiso 1 1 calc R . .
C14 C 0.47787(11) 0.7610(2) 0.06798(9) 0.0200(3) Uani 1 1 d . . .
O15 O 0.56604(8) 0.85661(15) 0.07584(7) 0.0245(3) Uani 1 1 d . . .
O16 O 0.39157(9) 0.81718(15) 0.01323(7) 0.0290(3) Uani 1 1 d . . .
H16 H 0.4092 0.9190 -0.0160 0.044 Uiso 1 1 calc R . .
C17 C 0.59626(13) 0.2413(2) 0.30602(10) 0.0281(4) Uani 1 1 d . . .
H17A H 0.5912 0.3127 0.3656 0.042 Uiso 1 1 calc R . .
H17B H 0.6733 0.2527 0.2829 0.042 Uiso 1 1 calc R . .
H17C H 0.5784 0.1032 0.3162 0.042 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 N7 1.4080(17) . ?
C1 C6 1.4139(19) . ?
C1 C2 1.4155(18) . ?
C2 C3 1.3979(19) . ?
C2 C14 1.4842(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3906(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C17 1.5028(19) . ?
N7 C8 1.4204(17) . ?
N7 H7 0.864(17) . ?
C8 C13 1.3937(19) . ?
C8 C9 1.395(2) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O15 1.2306(16) . ?
C14 O16 1.3164(16) . ?
O16 H16 0.8400 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 C1 C6 118.95(12) . . ?
N7 C1 C2 122.09(12) . . ?
C6 C1 C2 118.91(12) . . ?
C3 C2 C1 120.22(12) . . ?
C3 C2 C14 118.40(12) . . ?
C1 C2 C14 121.38(12) . . ?
C4 C3 C2 120.67(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.07(13) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 122.24(13) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C1 118.86(13) . . ?
C5 C6 C17 120.21(13) . . ?
C1 C6 C17 120.89(13) . . ?
C1 N7 C8 121.20(11) . . ?
C1 N7 H7 114.3(11) . . ?
C8 N7 H7 109.8(11) . . ?
C13 C8 C9 118.87(13) . . ?
C13 C8 N7 118.61(12) . . ?
C9 C8 N7 122.47(13) . . ?
C10 C9 C8 120.46(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.56(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.23(14) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.88(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 120.00(13) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O15 C14 O16 122.21(12) . . ?
O15 C14 C2 123.85(12) . . ?
O16 C14 C2 113.95(11) . . ?
C14 O16 H16 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N7 C1 C2 C3 178.52(11) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
N7 C1 C2 C14 -2.4(2) . . . . ?
C6 C1 C2 C14 -179.72(11) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C14 C2 C3 C4 -178.95(12) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C4 C5 C6 C17 -176.25(13) . . . . ?
N7 C1 C6 C5 -179.45(12) . . . . ?
C2 C1 C6 C5 -2.01(19) . . . . ?
N7 C1 C6 C17 -1.6(2) . . . . ?
C2 C1 C6 C17 175.80(12) . . . . ?
C6 C1 N7 C8 -68.26(17) . . . . ?
C2 C1 N7 C8 114.38(14) . . . . ?
C1 N7 C8 C13 179.59(12) . . . . ?
C1 N7 C8 C9 -3.1(2) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
N7 C8 C9 C10 -177.70(13) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
N7 C8 C13 C12 177.05(13) . . . . ?
C3 C2 C14 O15 -171.36(12) . . . . ?
C1 C2 C14 O15 9.5(2) . . . . ?
C3 C2 C14 O16 8.27(18) . . . . ?
C1 C2 C14 O16 -170.87(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2118307'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.0335(12)
_cell_length_b                   6.9116(5)
_cell_length_c                   13.0522(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.715(9)
_cell_angle_gamma                90
_cell_volume                     1268.52(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4910
_cell_measurement_theta_min      6.1760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4306
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.245
_diffrn_reflns_theta_min         6.295
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 117.00   0.50    0.05    --   47.45  37.00   0.00  162
  2  ω     72.00  97.00   0.50    0.05    --   47.45 131.00-103.00   50
  3  ω     73.00  99.00   0.50    0.19    --  107.75 131.00-103.00   52
  4  ω     70.00 117.00   0.50    0.05    --   47.45 138.00  72.00   94
  5  ω    -16.00  10.00   0.50    0.05    --   47.45 -19.00-150.00   52
  6  ω    -26.00  23.00   0.50    0.05    --   47.45 -19.00-180.00   98
  7  ω     63.00 106.00   0.50    0.19    --  107.75 -99.00-180.00   86
  8  ω     62.00 100.00   0.50    0.19    --  107.75 -77.00-180.00   76
  9  ω     51.00  76.00   0.50    0.19    --  107.75-131.00-174.00   50
 10  ω     36.00  62.00   0.50    0.19    --  107.75 -57.00-180.00   52
 11  ω     78.00 116.00   0.50    0.19    --  107.75-138.00  10.00   76
 12  ω     80.00 105.00   0.50    0.19    --  107.75 -99.00  30.00   50
 13  ω     35.00  61.00   0.50    0.19    --  107.75 -57.00  30.00   52
 14  ω     38.00  74.00   0.50    0.19    --  107.75 -99.00  30.00   72
 15  ω    -19.00  20.00   0.50    0.05    --   47.45 -19.00  60.00   78
 16  ω    -81.00 -55.00   0.50    0.05    --  -47.45 131.00-103.00   52
 17  ω    -73.00 -27.00   0.50    0.19    -- -100.00 131.00-103.00   92
 18  ω   -108.00 -58.00   0.50    0.19    -- -100.00 110.00 -87.06  100
 19  ω    -86.00 -33.00   0.50    0.05    --  -47.45 138.00  72.00  106
 20  ω    -53.00 -27.00   0.50    0.19    -- -100.00  57.00  60.00   52
 21  ω    -56.00 -27.00   0.50    0.19    -- -100.00  57.00 120.00   58
 22  ω   -120.00 -32.00   0.50    0.19    -- -100.00 138.00  72.00  176
 23  ω   -136.00-100.00   0.50    0.19    -- -100.00 -19.00   0.00   72
 24  ω   -121.00 -88.00   0.50    0.19    -- -100.00 -57.00  90.00   66
 25  ω   -158.00 -86.00   0.50    0.19    -- -100.00-125.00 150.00  144
 26  ω   -172.00-141.00   0.50    0.19    -- -100.00 -19.00   0.00   62
 27  ω   -170.00-127.00   0.50    0.19    -- -100.00 -57.00  90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0519504000
_diffrn_orient_matrix_UB_12      -0.1693309000
_diffrn_orient_matrix_UB_13      0.0738587000
_diffrn_orient_matrix_UB_21      -0.0624366000
_diffrn_orient_matrix_UB_22      -0.1448072000
_diffrn_orient_matrix_UB_23      -0.0846885000
_diffrn_orient_matrix_UB_31      0.0735674000
_diffrn_orient_matrix_UB_32      -0.0036841000
_diffrn_orient_matrix_UB_33      -0.0574587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3727
_reflns_number_total             4306
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.237
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.073
_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)+(0.1408P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2154
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.496(3)
 0.504(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 N3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C15(H15), C1(H1A), C2(H2)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.01934(13) 0.6621(3) 0.61734(15) 0.0770(5) Uani 1 1 d . . . . .
H1 H -0.005557 0.560821 0.588392 0.115 Uiso 1 1 calc GR . . . .
O2 O 0.06490(11) 0.6649(2) 0.47366(14) 0.0681(5) Uani 1 1 d . . . . .
N3 N 0.18630(14) 0.9460(3) 0.46347(16) 0.0692(5) Uani 1 1 d . . . . .
H3 H 0.142371 0.863836 0.431068 0.083 Uiso 1 1 d R . . . .
C4 C 0.06340(13) 0.7432(3) 0.55738(18) 0.0574(5) Uani 1 1 d . . . . .
C5 C 0.10883(13) 0.9303(3) 0.59991(18) 0.0582(5) Uani 1 1 d . . . . .
C6 C 0.16992(14) 1.0237(3) 0.55447(18) 0.0608(5) Uani 1 1 d . . . . .
C7 C 0.27557(17) 0.8734(3) 0.46838(18) 0.0639(6) Uani 1 1 d . . . . .
C8 C 0.09038(16) 1.0156(4) 0.6877(2) 0.0673(6) Uani 1 1 d . . . . .
H8 H 0.049340 0.955311 0.716785 0.081 Uiso 1 1 calc R . . . .
C9 C 0.35680(16) 0.8830(3) 0.5617(2) 0.0661(6) Uani 1 1 d . . . . .
H9 H 0.353704 0.939899 0.624887 0.079 Uiso 1 1 calc R . . . .
C10 C 0.21078(16) 1.2033(3) 0.5977(2) 0.0711(7) Uani 1 1 d . . . . .
C11 C 0.19210(18) 1.2787(4) 0.6862(2) 0.0803(8) Uani 1 1 d . . . . .
H11 H 0.220642 1.394717 0.716692 0.096 Uiso 1 1 calc R . . . .
C12 C 0.2699(2) 1.3162(4) 0.5461(3) 0.0910(9) Uani 1 1 d . . . . .
H12A H 0.334687 1.272815 0.575701 0.136 Uiso 1 1 calc GR . . . .
H12B H 0.267083 1.451400 0.561520 0.136 Uiso 1 1 calc GR . . . .
H12C H 0.245539 1.296128 0.468321 0.136 Uiso 1 1 calc GR . . . .
C13 C 0.13254(17) 1.1876(4) 0.7308(2) 0.0783(7) Uani 1 1 d . . . . .
H13 H 0.121054 1.242724 0.789925 0.094 Uiso 1 1 calc R . . . .
C14 C 0.4430(2) 0.8083(4) 0.5618(3) 0.0798(7) Uani 1 1 d . . . . .
C15 C 0.2804(2) 0.7863(4) 0.3751(2) 0.0839(8) Uani 1 1 d . . . . .
H15 H 0.226476 0.778181 0.312119 0.101 Uiso 1 1 calc R . . . .
C16 C 0.5300(2) 0.8199(5) 0.6650(3) 0.1078(11) Uani 1 1 d . . . . .
H16A H 0.535084 0.947702 0.695331 0.162 Uiso 1 1 calc GR . . . .
H16B H 0.585781 0.791801 0.647959 0.162 Uiso 1 1 calc GR . . . .
H16C H 0.524485 0.727455 0.717348 0.162 Uiso 1 1 calc GR . . . .
C1 C 0.3653(3) 0.7121(5) 0.3760(3) 0.1105(12) Uani 1 1 d . . . . .
H1A H 0.368057 0.651268 0.313649 0.133 Uiso 1 1 calc R . . . .
C2 C 0.4465(3) 0.7259(5) 0.4676(3) 0.1035(11) Uani 1 1 d . . . . .
H2 H 0.503872 0.679205 0.465625 0.124 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 C4 1.316(3) . ?
O2 C4 1.227(3) . ?
N3 C6 1.403(3) . ?
N3 C7 1.413(3) . ?
C4 C5 1.476(3) . ?
C5 C6 1.413(3) . ?
C5 C8 1.400(3) . ?
C6 C10 1.411(3) . ?
C7 C9 1.388(3) . ?
C7 C15 1.383(4) . ?
C8 C13 1.371(4) . ?
C9 C14 1.395(4) . ?
C10 C11 1.383(4) . ?
C10 C12 1.508(4) . ?
C11 C13 1.380(4) . ?
C14 C16 1.512(4) . ?
C14 C2 1.372(5) . ?
C15 C1 1.371(5) . ?
C1 C2 1.377(5) . ?

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 N3 C7 123.10(18) . . ?
O1 C4 C5 114.39(19) . . ?
O2 C4 O1 120.9(2) . . ?
O2 C4 C5 124.7(2) . . ?
C6 C5 C4 121.7(2) . . ?
C8 C5 C4 118.5(2) . . ?
C8 C5 C6 119.8(2) . . ?
N3 C6 C5 121.0(2) . . ?
N3 C6 C10 119.6(2) . . ?
C10 C6 C5 119.3(2) . . ?
C9 C7 N3 123.3(2) . . ?
C15 C7 N3 117.4(2) . . ?
C15 C7 C9 119.3(3) . . ?
C13 C8 C5 120.3(2) . . ?
C7 C9 C14 120.8(2) . . ?
C6 C10 C12 121.2(2) . . ?
C11 C10 C6 118.5(2) . . ?
C11 C10 C12 120.3(2) . . ?
C13 C11 C10 122.3(2) . . ?
C8 C13 C11 119.8(2) . . ?
C9 C14 C16 119.5(3) . . ?
C2 C14 C9 118.8(3) . . ?
C2 C14 C16 121.7(3) . . ?
C1 C15 C7 119.6(3) . . ?
C15 C1 C2 121.2(3) . . ?
C14 C2 C1 120.2(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 1.829
_oxdiff_exptl_absorpt_empirical_full_min 0.452
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.496(3) 5597 3317 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.504(3) 5580 3317 nmt -1.0006 -0.0031 -0.8145 0.0010 -1.0002 0.0004 0.0012
-0.0018 1.0004

_twin_special_details            
;
Component 2 rotated by 179.8883° 
around [-0.38 0.00 0.93] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
####################################################################### 
# 
# 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_5-I
_database_code_depnum_ccdc_archive 'CCDC 2118309'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_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 0.0181 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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.0796(3)
_cell_length_b                   10.1603(10)
_cell_length_c                   26.6290(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.589(6)
_cell_angle_gamma                90
_cell_volume                     1373.79(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3376
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.1740
_cell_measurement_theta_min      3.3360
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8751
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.676
_diffrn_reflns_theta_min         3.321
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  27.00   1.00    0.22    --  -47.57  19.00  60.00   55
  2  ω     71.00 114.00   1.00    0.22    --   47.57 139.00-115.00   43
  3  ω     96.00 128.00   1.00    0.89    --  107.75  37.00  60.00   32
  4  ω     36.00  63.00   1.00    0.89    --  107.75 -57.00  60.00   27
  5  ω     51.00  76.00   1.00    0.89    --  107.75-130.00  -2.00   25
  6  ω     45.00  91.00   1.00    0.89    --  107.75-125.00  30.00   46
  7  ω     58.00  85.00   1.00    0.22    --   47.57-139.00-176.00   27
  8  ω     68.00  93.00   1.00    0.89    --  107.75-139.00-176.00   25
  9  ω    -24.00  23.00   1.00    0.22    --   47.57 -19.00-120.00   47
 10  ω    -86.00 -61.00   1.00    0.22    --  -47.57 130.00  69.00   25
 11  ω    -26.00  15.00   1.00    0.22    --   47.57 -19.00 150.00   41
 12  ω    -85.00 -59.00   1.00    0.22    --  -47.57 139.00-115.00   26
 13  ω    -76.00 -51.00   1.00    0.89    -- -100.00 139.00-115.00   25
 14  ω   -120.00 -86.00   1.00    0.89    -- -100.00 136.00-104.61   34
 15  ω    -60.00 -27.00   1.00    0.89    -- -100.00  57.00 -60.00   33
 16  ω    -69.00 -37.00   1.00    0.89    -- -100.00  57.00 -90.00   32
 17  ω    -73.00 -31.00   1.00    0.89    -- -100.00 141.00  49.35   42
 18  ω   -112.00 -48.00   1.00    0.89    -- -100.00 125.00  30.00   64
 19  ω   -112.00 -62.00   1.00    0.89    -- -100.00 125.00   0.00   50
 20  ω   -123.00 -91.00   1.00    0.89    -- -100.00 141.00  49.35   32
 21  ω   -175.00-100.00   1.00    0.89    -- -100.00 -19.00   0.00   75
 22  ω   -150.00-125.00   1.00    0.89    -- -100.00-130.00  -2.00   25
 23  ω   -137.00 -89.00   1.00    0.89    -- -100.00-125.00  60.00   48
 24  ω   -118.00 -74.00   1.00    0.22    --  -47.57-139.00-176.00   44
 25  ω   -146.00 -76.00   1.00    0.89    -- -100.00-139.00-176.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0117664000
_diffrn_orient_matrix_UB_12      -0.1247204000
_diffrn_orient_matrix_UB_13      -0.0328835000
_diffrn_orient_matrix_UB_21      0.0006946000
_diffrn_orient_matrix_UB_22      -0.0860876000
_diffrn_orient_matrix_UB_23      0.0476653000
_diffrn_orient_matrix_UB_31      -0.3030209000
_diffrn_orient_matrix_UB_32      0.0046518000
_diffrn_orient_matrix_UB_33      -0.0002583000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1883
_reflns_number_total             2699
_reflns_odcompleteness_completeness 98.84
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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         0.190
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0717
_refine_ls_restrained_S_all      1.088
_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)+(0.0892P)²+0.4680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2009
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.3492(4) 0.0566(2) 0.44040(7) 0.0727(6) Uani 1 1 d . . . . .
H1 H 0.328958 0.051267 0.470779 0.109 Uiso 1 1 calc GR . . . .
O2 O 0.7292(4) -0.0384(2) 0.46166(6) 0.0679(6) Uani 1 1 d . . . . .
N1 N 0.9550(4) -0.1707(2) 0.38453(8) 0.0586(6) Uani 1 1 d . . . . .
H1A H 0.947341 -0.146985 0.415496 0.070 Uiso 1 1 d R . . . .
C1 C 0.9254(5) -0.3082(3) 0.38152(8) 0.0518(6) Uani 1 1 d . . . . .
C2 C 1.0849(5) -0.3856(3) 0.41361(9) 0.0556(6) Uani 1 1 d . . . . .
C3 C 1.0570(6) -0.5224(3) 0.41222(11) 0.0653(7) Uani 1 1 d . . . . .
C4 C 0.8771(7) -0.5795(3) 0.37865(12) 0.0749(8) Uani 1 1 d . . . . .
H4 H 0.861516 -0.670622 0.377212 0.090 Uiso 1 1 calc R . . . .
C5 C 0.7217(6) -0.5022(4) 0.34751(12) 0.0740(8) Uani 1 1 d . . . . .
H5 H 0.601223 -0.541641 0.325298 0.089 Uiso 1 1 calc R . . . .
C6 C 0.7423(5) -0.3670(3) 0.34881(10) 0.0618(7) Uani 1 1 d . . . . .
H6 H 0.634529 -0.315392 0.327984 0.074 Uiso 1 1 calc R . . . .
C7 C 1.2807(6) -0.3201(4) 0.44891(12) 0.0768(9) Uani 1 1 d . . . . .
H7A H 1.384044 -0.258343 0.430601 0.115 Uiso 1 1 calc GR . . . .
H7B H 1.394220 -0.385527 0.463927 0.115 Uiso 1 1 calc GR . . . .
H7C H 1.188650 -0.274698 0.474719 0.115 Uiso 1 1 calc GR . . . .
C8 C 1.2203(7) -0.6095(4) 0.44684(14) 0.0876(10) Uani 1 1 d . . . . .
H8A H 1.403794 -0.595882 0.440855 0.131 Uiso 1 1 calc GR . . . .
H8B H 1.175985 -0.699994 0.440583 0.131 Uiso 1 1 calc GR . . . .
H8C H 1.184932 -0.588063 0.481114 0.131 Uiso 1 1 calc GR . . . .
C9 C 0.8125(5) -0.0809(3) 0.35428(9) 0.0522(6) Uani 1 1 d . . . . .
C10 C 0.6323(5) 0.0071(3) 0.37509(9) 0.0541(6) Uani 1 1 d . . . . .
C11 C 0.5011(6) 0.0985(3) 0.34416(11) 0.0659(7) Uani 1 1 d . . . . .
H11 H 0.381056 0.156369 0.357928 0.079 Uiso 1 1 calc R . . . .
C12 C 0.5476(6) 0.1035(4) 0.29373(11) 0.0741(9) Uani 1 1 d . . . . .
H12 H 0.459321 0.164323 0.273300 0.089 Uiso 1 1 calc R . . . .
C13 C 0.7270(6) 0.0175(3) 0.27352(10) 0.0703(8) Uani 1 1 d . . . . .
H13 H 0.759278 0.022097 0.239359 0.084 Uiso 1 1 calc R . . . .
C14 C 0.8592(5) -0.0746(3) 0.30242(9) 0.0596(7) Uani 1 1 d . . . . .
C15 C 1.0629(6) -0.1620(4) 0.27923(11) 0.0756(9) Uani 1 1 d . . . . .
H15A H 1.222108 -0.159890 0.299480 0.113 Uiso 1 1 calc GR . . . .
H15B H 1.098334 -0.131179 0.246017 0.113 Uiso 1 1 calc GR . . . .
H15C H 0.997711 -0.250650 0.277418 0.113 Uiso 1 1 calc GR . . . .
C16 C 0.5780(5) 0.0060(3) 0.42923(9) 0.0561(6) 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
O1 C16 1.313(3) . ?
O2 C16 1.225(3) . ?
N1 C1 1.407(4) . ?
N1 C9 1.404(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.504(4) . ?
C3 C4 1.388(4) . ?
C3 C8 1.510(4) . ?
C4 C5 1.375(5) . ?
C5 C6 1.378(4) . ?
C9 C10 1.404(4) . ?
C9 C14 1.409(3) . ?
C10 C11 1.398(4) . ?
C10 C16 1.475(3) . ?
C11 C12 1.371(4) . ?
C12 C13 1.382(5) . ?
C13 C14 1.375(4) . ?
C14 C15 1.509(4) . ?

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
C9 N1 C1 124.0(2) . . ?
C2 C1 N1 117.6(2) . . ?
C6 C1 N1 122.0(2) . . ?
C6 C1 C2 120.4(3) . . ?
C1 C2 C7 119.6(3) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 C7 121.4(3) . . ?
C2 C3 C8 120.9(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 C8 119.3(3) . . ?
C5 C4 C3 120.4(3) . . ?
C4 C5 C6 120.8(3) . . ?
C5 C6 C1 119.5(3) . . ?
N1 C9 C10 121.2(2) . . ?
N1 C9 C14 119.6(2) . . ?
C10 C9 C14 119.1(2) . . ?
C9 C10 C16 121.5(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 C16 118.8(3) . . ?
C12 C11 C10 120.7(3) . . ?
C11 C12 C13 119.4(3) . . ?
C14 C13 C12 122.0(3) . . ?
C9 C14 C15 120.7(3) . . ?
C13 C14 C9 119.1(3) . . ?
C13 C14 C15 120.1(3) . . ?
O1 C16 C10 114.1(2) . . ?
O2 C16 O1 121.7(2) . . ?
O2 C16 C10 124.1(2) . . ?

_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 6.994
_oxdiff_exptl_absorpt_empirical_full_min 0.538
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2118285'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-10-24
_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         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.128(3)
_cell_length_b                   5.9193(19)
_cell_length_c                   23.562(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.810(4)
_cell_angle_gamma                90
_cell_volume                     1271.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8524
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         1.731
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1795
_reflns_number_total             2339
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.060
_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)+(0.0793P)²+0.4595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.7633(2) 0.2595(4) 0.34992(8) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.8704(2) 0.0958(4) 0.36393(8) 0.0368(5) Uani 1 1 d . . . . .
C3 C 0.9278(2) -0.0374(4) 0.32101(9) 0.0462(6) Uani 1 1 d . . . . .
H3 H 0.9986 -0.1460 0.3304 0.055 Uiso 1 1 calc R . . . .
C4 C 0.8805(3) -0.0088(5) 0.26513(10) 0.0518(6) Uani 1 1 d . . . . .
H4 H 0.9165 -0.1005 0.2370 0.062 Uiso 1 1 calc R . . . .
C5 C 0.7793(2) 0.1567(5) 0.25135(9) 0.0485(6) Uani 1 1 d . . . . .
H5 H 0.7490 0.1764 0.2134 0.058 Uiso 1 1 calc R . . . .
C6 C 0.7206(2) 0.2956(4) 0.29182(9) 0.0414(5) Uani 1 1 d . . . . .
C7 C 0.9253(2) 0.0569(4) 0.42311(9) 0.0391(5) Uani 1 1 d . . . . .
C8 C 0.6216(3) 0.4872(5) 0.27368(10) 0.0573(7) Uani 1 1 d . . . . .
H8A H 0.5214 0.4451 0.2787 0.086 Uiso 1 1 calc GR . . . .
H8B H 0.6343 0.5211 0.2344 0.086 Uiso 1 1 calc GR . . . .
H8C H 0.6455 0.6179 0.2964 0.086 Uiso 1 1 calc GR . . . .
C9 C 0.5478(2) 0.4149(4) 0.39643(8) 0.0355(5) Uani 1 1 d . . . . .
C10 C 0.4966(2) 0.6040(4) 0.42520(9) 0.0419(5) Uani 1 1 d . . . . .
C11 C 0.3458(3) 0.6265(4) 0.42938(11) 0.0553(7) Uani 1 1 d . . . . .
H11 H 0.3095 0.7509 0.4483 0.066 Uiso 1 1 calc R . . . .
C12 C 0.2484(3) 0.4692(5) 0.40617(11) 0.0583(7) Uani 1 1 d . . . . .
H12 H 0.1480 0.4895 0.4089 0.070 Uiso 1 1 calc R . . . .
C13 C 0.3002(3) 0.2838(5) 0.37919(10) 0.0517(6) Uani 1 1 d . . . . .
H13 H 0.2350 0.1759 0.3643 0.062 Uiso 1 1 calc R . . . .
C14 C 0.4500(2) 0.2560(4) 0.37400(9) 0.0446(6) Uani 1 1 d . . . . .
H14 H 0.4847 0.1299 0.3553 0.054 Uiso 1 1 calc R . . . .
C15 C 0.6016(3) 0.7753(4) 0.44997(11) 0.0573(7) Uani 1 1 d . . . . .
H15A H 0.6515 0.7142 0.4834 0.086 Uiso 1 1 calc GR . . . .
H15B H 0.5488 0.9087 0.4599 0.086 Uiso 1 1 calc GR . . . .
H15C H 0.6720 0.8131 0.4225 0.086 Uiso 1 1 calc GR . . . .
N1 N 0.70149(18) 0.3931(3) 0.39105(7) 0.0416(5) Uani 1 1 d D . . . .
O1 O 0.90489(17) 0.1890(3) 0.46212(6) 0.0516(5) Uani 1 1 d . . . . .
O2 O 0.9988(2) -0.1302(3) 0.43106(7) 0.0618(6) Uani 1 1 d . . . . .
H2 H 1.0252 -0.1416 0.4647 0.093 Uiso 1 1 calc GR . . . .
H1 H 0.754(3) 0.393(6) 0.4231(10) 0.093 Uiso 1 1 d DR . . . .


_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 C2 1.405(3) . ?
C1 C6 1.421(3) . ?
C1 N1 1.391(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.476(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C8 1.500(3) . ?
C7 O1 1.228(3) . ?
C7 O2 1.304(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.401(3) . ?
C9 C14 1.384(3) . ?
C9 N1 1.420(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.494(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1 0.873(18) . ?
O2 H2 0.8200 . ?

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 C1 C6 118.99(19) . . ?
N1 C1 C2 121.99(17) . . ?
N1 C1 C6 118.98(19) . . ?
C1 C2 C7 121.97(18) . . ?
C3 C2 C1 119.89(19) . . ?
C3 C2 C7 118.15(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.5(2) . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C8 121.4(2) . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C8 120.0(2) . . ?
O1 C7 C2 123.44(19) . . ?
O1 C7 O2 121.96(18) . . ?
O2 C7 C2 114.60(19) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 118.04(19) . . ?
C14 C9 C10 120.23(19) . . ?
C14 C9 N1 121.73(19) . . ?
C9 C10 C15 120.6(2) . . ?
C11 C10 C9 117.7(2) . . ?
C11 C10 C15 121.7(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.4(2) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C9 123.33(17) . . ?
C1 N1 H1 112(2) . . ?
C9 N1 H1 115(2) . . ?
C7 O2 H2 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 1.83 2.648(2) 174.6 3_756
N1 H1 O1 0.873(18) 2.02(3) 2.721(2) 137(3) .

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 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C7 O1 -14.8(3) . . . . ?
C1 C2 C7 O2 165.5(2) . . . . ?
C2 C1 C6 C5 4.4(3) . . . . ?
C2 C1 C6 C8 -172.1(2) . . . . ?
C2 C1 N1 C9 -127.3(2) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C2 C7 O1 165.6(2) . . . . ?
C3 C2 C7 O2 -14.1(3) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C4 C5 C6 C8 174.2(2) . . . . ?
C6 C1 C2 C3 -3.4(3) . . . . ?
C6 C1 C2 C7 176.96(19) . . . . ?
C6 C1 N1 C9 55.1(3) . . . . ?
C7 C2 C3 C4 179.9(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C9 C14 C13 0.8(3) . . . . ?
C10 C9 N1 C1 -159.2(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 -1.4(4) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C14 C9 C10 C11 -1.0(3) . . . . ?
C14 C9 C10 C15 179.5(2) . . . . ?
C14 C9 N1 C1 20.6(3) . . . . ?
C15 C10 C11 C12 179.5(2) . . . . ?
N1 C1 C2 C3 179.0(2) . . . . ?
N1 C1 C2 C7 -0.6(3) . . . . ?
N1 C1 C6 C5 -178.0(2) . . . . ?
N1 C1 C6 C8 5.6(3) . . . . ?
N1 C9 C10 C11 178.79(19) . . . . ?
N1 C9 C10 C15 -0.7(3) . . . . ?
N1 C9 C14 C13 -179.0(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_5-II
_database_code_depnum_ccdc_archive 'CCDC 2118313'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.2982(2)
_cell_length_b                   15.8116(3)
_cell_length_c                   7.97734(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.196(2)
_cell_angle_gamma                90
_cell_volume                     1368.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9240
_cell_measurement_theta_min      2.8220
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.186
_diffrn_reflns_theta_min         4.075
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  13.00   0.50    0.05    --  -47.57  37.00 -90.00  114
  2  ω    -59.00 -30.00   0.50    0.05    -- -100.00 134.00 -72.00   58
  3  ω    -87.00 -61.00   0.50    0.05    --  -47.57 134.00 -72.00   52
  4  ω   -116.00 -66.00   0.50    0.05    -- -100.00 134.00 -72.00  100
  5  ω   -106.00 -28.00   0.50    0.05    -- -100.00  77.00 -60.00  156
  6  ω    -69.00 -44.00   0.50    0.05    -- -100.00  57.00 -60.00   50
  7  ω   -113.00 -87.00   0.50    0.05    -- -100.00 -19.00 -90.00   52
  8  ω   -172.00-144.00   0.50    0.05    -- -100.00 -57.00-120.00   56
  9  ω   -174.00-120.00   0.50    0.05    -- -100.00 -19.00 -90.00  108
 10  ω    -80.00 -55.00   0.50    0.05    --  -47.57 135.00 107.00   50
 11  ω     78.00 119.00   0.50    0.05    --   47.57 134.00 -72.00   82
 12  ω     89.00 123.00   0.50    0.05    --  107.75 134.00 -72.00   68
 13  ω     96.00 172.00   0.50    0.05    --  107.75  37.00-180.00  152
 14  ω     38.00  63.00   0.50    0.05    --   47.57-135.00  41.00   50
 15  ω     53.00  78.00   0.50    0.05    --  107.75-135.00  41.00   50
 16  ω     61.00 111.00   0.50    0.05    --  107.75-125.00  60.00  100
 17  ω     36.00  62.00   0.50    0.05    --  107.75 -57.00  60.00   52
 18  ω     37.00  62.00   0.50    0.05    --  107.75 -57.00  90.00   50
 19  ω    115.00 141.00   0.50    0.05    --  107.75  19.00 120.00   52
 20  ω     70.00 105.00   0.50    0.05    --   47.57 135.00 107.00   70
 21  ω    -27.00  -1.00   0.50    0.05    --   47.57 -19.00-150.00   52
 22  ω    -21.00   4.00   0.50    0.05    --   47.57 -19.00-180.00   50
 23  ω    -27.00  21.00   0.50    0.05    --   47.57 -19.00 -60.00   96
 24  ω     37.00 106.00   0.50    0.05    --  107.75 -99.00-150.00  138
 25  ω     53.00  78.00   0.50    0.05    --  107.75-134.00-139.00   50
 26  ω   -119.00 -77.00   0.50    0.05    -- -100.00 135.00 107.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0980249000
_diffrn_orient_matrix_UB_12      -0.0266898000
_diffrn_orient_matrix_UB_13      0.1679714000
_diffrn_orient_matrix_UB_21      -0.0281178000
_diffrn_orient_matrix_UB_22      -0.0937448000
_diffrn_orient_matrix_UB_23      -0.0474861000
_diffrn_orient_matrix_UB_31      0.0987117000
_diffrn_orient_matrix_UB_32      -0.0003003000
_diffrn_orient_matrix_UB_33      -0.0998193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2478
_reflns_number_total             2719
_reflns_odcompleteness_completeness 99.30
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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         0.367
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.097
_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)+(0.0825P)²+0.2168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C13(H13), C6(H6), C12(H12), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.92819(10) 0.03813(6) 0.80443(13) 0.0602(3) Uani 1 1 d . . . . .
N1 N 0.79581(10) 0.06987(7) 0.46819(15) 0.0518(3) Uani 1 1 d . . . . .
H1 H 0.856485 0.100771 0.524724 0.062 Uiso 1 1 calc R . . . .
O2 O 0.96698(13) -0.09652(7) 0.87850(14) 0.0708(4) Uani 1 1 d . . . . .
H2 H 0.994490 -0.075032 0.975111 0.106 Uiso 1 1 calc GR . . . .
C10 C 0.88093(11) -0.06777(8) 0.58146(17) 0.0453(3) Uani 1 1 d . . . . .
C9 C 0.81843(11) -0.01497(8) 0.44212(17) 0.0451(3) Uani 1 1 d . . . . .
C1 C 0.67773(12) 0.10820(9) 0.40637(16) 0.0470(3) Uani 1 1 d . . . . .
C11 C 0.90276(14) -0.15263(9) 0.5499(2) 0.0537(4) Uani 1 1 d . . . . .
H11 H 0.944219 -0.186929 0.642335 0.064 Uiso 1 1 calc R . . . .
C14 C 0.78422(13) -0.04892(10) 0.27106(18) 0.0527(3) Uani 1 1 d . . . . .
C16 C 0.92608(12) -0.03669(8) 0.76169(18) 0.0482(3) Uani 1 1 d . . . . .
C13 C 0.80681(15) -0.13363(11) 0.2485(2) 0.0611(4) Uani 1 1 d . . . . .
H13 H 0.782314 -0.156200 0.136445 0.073 Uiso 1 1 calc R . . . .
C6 C 0.57229(14) 0.05874(10) 0.3666(2) 0.0580(4) Uani 1 1 d . . . . .
H6 H 0.578415 0.000291 0.379064 0.070 Uiso 1 1 calc R . . . .
C2 C 0.67002(13) 0.19644(9) 0.39045(17) 0.0510(3) Uani 1 1 d . . . . .
C12 C 0.86421(16) -0.18593(10) 0.3856(2) 0.0625(4) Uani 1 1 d . . . . .
H12 H 0.876444 -0.242871 0.366440 0.075 Uiso 1 1 calc R . . . .
C7 C 0.78520(16) 0.24948(10) 0.4367(3) 0.0697(5) Uani 1 1 d . . . . .
H7A H 0.798482 0.271833 0.552331 0.105 Uiso 1 1 calc GR . . . .
H7B H 0.776213 0.295250 0.354995 0.105 Uiso 1 1 calc GR . . . .
H7C H 0.854361 0.215191 0.432144 0.105 Uiso 1 1 calc GR . . . .
C3 C 0.55332(15) 0.23400(11) 0.3312(2) 0.0615(4) Uani 1 1 d . . . . .
C4 C 0.44902(15) 0.18284(13) 0.2900(2) 0.0723(5) Uani 1 1 d . . . . .
H4 H 0.371604 0.207561 0.249203 0.087 Uiso 1 1 calc R . . . .
C15 C 0.73109(18) 0.00581(13) 0.1137(2) 0.0714(5) Uani 1 1 d . . . . .
H15A H 0.643169 0.008626 0.091324 0.107 Uiso 1 1 calc GR . . . .
H15B H 0.751027 -0.017957 0.014255 0.107 Uiso 1 1 calc GR . . . .
H15C H 0.765179 0.061694 0.135273 0.107 Uiso 1 1 calc GR . . . .
C5 C 0.45814(15) 0.09668(12) 0.3082(2) 0.0696(5) Uani 1 1 d . . . . .
H5 H 0.387175 0.063691 0.281231 0.083 Uiso 1 1 calc R . . . .
C8 C 0.5388(2) 0.32866(12) 0.3102(3) 0.0887(6) Uani 1 1 d . . . . .
H8A H 0.565611 0.355207 0.422654 0.133 Uiso 1 1 calc GR . . . .
H8B H 0.453814 0.342136 0.256722 0.133 Uiso 1 1 calc GR . . . .
H8C H 0.587908 0.348822 0.237714 0.133 Uiso 1 1 calc GR . . . .


_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 C16 1.2295(16) . ?
N1 C9 1.3920(17) . ?
N1 C1 1.4225(17) . ?
O2 C16 1.3178(16) . ?
C10 C9 1.4119(18) . ?
C10 C11 1.3996(19) . ?
C10 C16 1.4696(19) . ?
C9 C14 1.4161(19) . ?
C1 C6 1.386(2) . ?
C1 C2 1.401(2) . ?
C11 C12 1.366(2) . ?
C14 C13 1.385(2) . ?
C14 C15 1.505(2) . ?
C13 C12 1.380(2) . ?
C6 C5 1.380(2) . ?
C2 C7 1.505(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.391(3) . ?
C3 C8 1.510(2) . ?
C4 C5 1.371(3) . ?

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
C9 N1 C1 123.53(11) . . ?
C9 C10 C16 122.23(12) . . ?
C11 C10 C9 119.98(12) . . ?
C11 C10 C16 117.79(12) . . ?
N1 C9 C10 121.64(12) . . ?
N1 C9 C14 119.81(12) . . ?
C10 C9 C14 118.46(12) . . ?
C6 C1 N1 120.14(13) . . ?
C6 C1 C2 120.89(13) . . ?
C2 C1 N1 118.96(12) . . ?
C12 C11 C10 121.14(14) . . ?
C9 C14 C15 121.59(14) . . ?
C13 C14 C9 118.77(13) . . ?
C13 C14 C15 119.54(14) . . ?
O1 C16 O2 121.25(13) . . ?
O1 C16 C10 124.59(12) . . ?
O2 C16 C10 114.16(12) . . ?
C12 C13 C14 122.65(14) . . ?
C5 C6 C1 119.64(15) . . ?
C1 C2 C7 120.33(13) . . ?
C1 C2 C3 118.74(13) . . ?
C3 C2 C7 120.93(14) . . ?
C11 C12 C13 118.88(14) . . ?
C2 C3 C8 121.31(16) . . ?
C4 C3 C2 119.22(15) . . ?
C4 C3 C8 119.46(15) . . ?
C5 C4 C3 121.28(15) . . ?
C4 C5 C6 120.21(16) . . ?

_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 2.971
_oxdiff_exptl_absorpt_empirical_full_min 0.794
####################################################################### 
# 
# 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_5-III
_database_code_depnum_ccdc_archive 'CCDC 2118317'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H17 N O2)'
_chemical_formula_sum            'C32 H34 N2 O4'
_chemical_formula_weight         510.61
_chemical_absolute_configuration ?
_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 0.0181 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      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   26.6725(2)
_cell_length_b                   19.70800(10)
_cell_length_c                   10.37290(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5452.64(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14525
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.2710
_cell_measurement_theta_min      4.4910
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16750
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.481
_diffrn_reflns_theta_min         4.487
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -164.00 -89.00   0.50    0.12    -- -100.00 -60.00 117.00  150
  2  ω     -5.00  50.00   0.50    0.05    --   47.57 -60.00 117.00  110
  3  ω    -24.00  11.00   0.50    0.05    --   47.57 -19.00   0.00   70
  4  ω     35.00  60.00   0.50    0.12    --  107.75-100.00  25.00   50
  5  ω     45.00  96.00   0.50    0.12    --  107.75 -77.00  60.00  102
  6  ω     81.00 106.00   0.50    0.12    --  107.75-100.00  25.00   50
  7  ω     40.00 105.00   0.50    0.12    --  107.75 -99.00  60.00  130
  8  ω     35.00  61.00   0.50    0.12    --  107.75 -57.00  60.00   52
  9  ω     38.00  63.00   0.50    0.12    --  107.75 -57.00   0.00   50
 10  ω     35.00  71.00   0.50    0.12    --  107.75 -68.00 -94.00   72
 11  ω     36.00  63.00   0.50    0.12    --  107.75 -57.00 -90.00   54
 12  ω     35.00 103.00   0.50    0.05    --   47.57  37.00-120.00  136
 13  ω     38.00  64.00   0.50    0.12    --  107.75 -60.00 117.00   52
 14  ω    -22.00   3.00   0.50    0.05    --   47.57 -19.00 150.00   50
 15  ω    -69.00 -29.00   0.50    0.12    -- -100.00  57.00-180.00   80
 16  ω     92.00 130.00   0.50    0.12    --  107.75  68.00  38.00   76
 17  ω    -27.00   4.00   0.50    0.05    --  -47.57  19.00 -90.00   62
 18  ω    -26.00  15.00   0.50    0.05    --   47.57 -19.00-120.00   82
 19  ω   -156.00 -98.00   0.50    0.12    -- -100.00 -19.00 -60.00  116
 20  ω    -53.00 -27.00   0.50    0.12    -- -100.00  57.00  30.00   52
 21  ω    108.00 134.00   0.50    0.12    --  107.75  77.00 120.00   52
 22  ω     73.00 100.00   0.50    0.12    --  107.75 -77.00-150.00   54
 23  ω     35.00  60.00   0.50    0.12    --  107.75 -57.00-150.00   50
 24  ω    150.00 175.00   0.50    0.12    --  107.75  77.00 120.00   50
 25  ω     35.00  63.00   0.50    0.12    --  107.75 -57.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1041265000
_diffrn_orient_matrix_UB_12      0.0534733000
_diffrn_orient_matrix_UB_13      0.0116210000
_diffrn_orient_matrix_UB_21      0.0126122000
_diffrn_orient_matrix_UB_22      -0.0281673000
_diffrn_orient_matrix_UB_23      0.0536697000
_diffrn_orient_matrix_UB_31      0.1051183000
_diffrn_orient_matrix_UB_32      -0.0495748000
_diffrn_orient_matrix_UB_33      -0.0179307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_full    0.755
_reflns_Friedel_fraction_max     0.695
_reflns_number_gt                4757
_reflns_number_total             4881
_reflns_odcompleteness_completeness 99.16
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C19(H19), C20(H20),
 C21(H21), C27(H27), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C23(H23A,H23B,
 H23C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_atom_sites_solution_hydrogens   mixed
_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 0.77149(5) 0.63782(7) 0.58794(17) 0.0626(4) Uani 1 1 d . . . . .
H1 H 0.741143 0.644366 0.589843 0.094 Uiso 1 1 calc GR . . . .
O2 O 0.75338(5) 0.60492(7) 0.38825(16) 0.0617(3) Uani 1 1 d . . . . .
O3 O 0.65564(5) 0.62993(9) 0.39000(17) 0.0680(4) Uani 1 1 d . . . . .
H3A H 0.685167 0.618431 0.392371 0.102 Uiso 1 1 calc GR . . . .
O4 O 0.67078(4) 0.65932(7) 0.59410(16) 0.0594(3) Uani 1 1 d . . . . .
N1 N 0.82006(5) 0.51614(7) 0.28432(16) 0.0490(3) Uani 1 1 d . . . . .
H1A H 0.7918(9) 0.5379(11) 0.277(2) 0.053(6) Uiso 1 1 d . . . . .
N2 N 0.59163(6) 0.72772(7) 0.70768(16) 0.0510(3) Uani 1 1 d . . . . .
H2 H 0.6194(11) 0.7116(16) 0.726(3) 0.082(8) Uiso 1 1 d . . . . .
C1 C 0.85421(5) 0.55030(7) 0.36336(17) 0.0451(3) Uani 1 1 d . . . . .
C2 C 0.83763(6) 0.59487(7) 0.46154(18) 0.0459(3) Uani 1 1 d . . . . .
C3 C 0.87243(7) 0.62532(9) 0.5443(2) 0.0557(4) Uani 1 1 d . . . . .
H3 H 0.861318 0.652858 0.611224 0.067 Uiso 1 1 calc R . . . .
C4 C 0.92309(8) 0.61474(10) 0.5271(2) 0.0643(5) Uani 1 1 d . . . . .
H4 H 0.946173 0.634200 0.583224 0.077 Uiso 1 1 calc R . . . .
C5 C 0.93912(6) 0.57508(10) 0.4260(2) 0.0605(4) Uani 1 1 d . . . . .
H5 H 0.973393 0.569834 0.412890 0.073 Uiso 1 1 calc R . . . .
C6 C 0.90608(6) 0.54253(8) 0.34272(19) 0.0508(4) Uani 1 1 d . . . . .
C7 C 0.92621(7) 0.50353(12) 0.2293(2) 0.0634(5) Uani 1 1 d . . . . .
H7A H 0.932275 0.457355 0.254289 0.095 Uiso 1 1 calc GR . . . .
H7B H 0.957008 0.523804 0.200836 0.095 Uiso 1 1 calc GR . . . .
H7C H 0.902191 0.504555 0.160403 0.095 Uiso 1 1 calc GR . . . .
C8 C 0.81639(5) 0.44460(7) 0.27732(15) 0.0420(3) Uani 1 1 d . . . . .
C9 C 0.77907(5) 0.41731(8) 0.19677(16) 0.0447(3) Uani 1 1 d . . . . .
C10 C 0.77433(6) 0.34675(8) 0.18710(19) 0.0499(4) Uani 1 1 d . . . . .
C11 C 0.80706(7) 0.30482(9) 0.2554(2) 0.0555(4) Uani 1 1 d . . . . .
H11 H 0.804639 0.257967 0.246788 0.067 Uiso 1 1 calc R . . . .
C12 C 0.84309(7) 0.33238(9) 0.3357(2) 0.0553(4) Uani 1 1 d . . . . .
H12 H 0.864486 0.303944 0.381427 0.066 Uiso 1 1 calc R . . . .
C13 C 0.84750(6) 0.40218(8) 0.34842(18) 0.0499(4) Uani 1 1 d . . . . .
H13 H 0.871166 0.420510 0.404283 0.060 Uiso 1 1 calc R . . . .
C14 C 0.74536(8) 0.46420(9) 0.1221(2) 0.0587(4) Uani 1 1 d . . . . .
H14A H 0.724568 0.489172 0.180869 0.088 Uiso 1 1 calc GR . . . .
H14B H 0.724607 0.438101 0.065001 0.088 Uiso 1 1 calc GR . . . .
H14C H 0.765390 0.495235 0.072750 0.088 Uiso 1 1 calc GR . . . .
C15 C 0.73511(7) 0.31530(11) 0.1016(3) 0.0713(6) Uani 1 1 d . . . . .
H15A H 0.702834 0.333858 0.122444 0.107 Uiso 1 1 calc GR . . . .
H15B H 0.734628 0.267081 0.114681 0.107 Uiso 1 1 calc GR . . . .
H15C H 0.742840 0.324893 0.013044 0.107 Uiso 1 1 calc GR . . . .
C16 C 0.78405(6) 0.61226(8) 0.47550(19) 0.0483(3) Uani 1 1 d . . . . .
C17 C 0.56296(6) 0.68933(8) 0.62049(17) 0.0471(3) Uani 1 1 d . . . . .
C18 C 0.58568(6) 0.65184(8) 0.52077(18) 0.0479(4) Uani 1 1 d . . . . .
C19 C 0.55583(8) 0.61464(10) 0.4345(2) 0.0608(5) Uani 1 1 d . . . . .
H19 H 0.570800 0.590483 0.367799 0.073 Uiso 1 1 calc R . . . .
C20 C 0.50464(8) 0.61380(12) 0.4482(3) 0.0713(6) Uani 1 1 d . . . . .
H20 H 0.484924 0.589067 0.391122 0.086 Uiso 1 1 calc R . . . .
C21 C 0.48253(7) 0.64997(11) 0.5475(3) 0.0651(5) Uani 1 1 d . . . . .
H21 H 0.447817 0.649150 0.555752 0.078 Uiso 1 1 calc R . . . .
C22 C 0.51051(6) 0.68745(9) 0.6353(2) 0.0558(4) Uani 1 1 d . . . . .
C23 C 0.48549(8) 0.72272(14) 0.7464(3) 0.0733(6) Uani 1 1 d . . . . .
H23A H 0.503168 0.712518 0.824618 0.110 Uiso 1 1 calc GR . . . .
H23B H 0.451446 0.707350 0.753512 0.110 Uiso 1 1 calc GR . . . .
H23C H 0.485853 0.770837 0.731984 0.110 Uiso 1 1 calc GR . . . .
C24 C 0.59072(5) 0.79904(8) 0.70814(15) 0.0426(3) Uani 1 1 d . . . . .
C25 C 0.61995(6) 0.83276(8) 0.80102(16) 0.0455(3) Uani 1 1 d . . . . .
C26 C 0.62178(6) 0.90374(9) 0.80026(19) 0.0507(4) Uani 1 1 d . . . . .
C27 C 0.59403(7) 0.93997(9) 0.7099(2) 0.0558(4) Uani 1 1 d . . . . .
H27 H 0.595283 0.987131 0.709428 0.067 Uiso 1 1 calc R . . . .
C28 C 0.56459(7) 0.90623(10) 0.6208(2) 0.0574(4) Uani 1 1 d . . . . .
H28 H 0.545705 0.930960 0.561874 0.069 Uiso 1 1 calc R . . . .
C29 C 0.56295(6) 0.83623(9) 0.61844(17) 0.0492(4) Uani 1 1 d . . . . .
H29 H 0.543445 0.813930 0.557398 0.059 Uiso 1 1 calc R . . . .
C30 C 0.64894(9) 0.79208(11) 0.8978(2) 0.0662(5) Uani 1 1 d . . . . .
H30A H 0.627162 0.759367 0.937390 0.099 Uiso 1 1 calc GR . . . .
H30B H 0.662227 0.821801 0.962687 0.099 Uiso 1 1 calc GR . . . .
H30C H 0.675997 0.769014 0.855315 0.099 Uiso 1 1 calc GR . . . .
C31 C 0.65386(9) 0.94168(12) 0.8958(3) 0.0731(6) Uani 1 1 d . . . . .
H31A H 0.641873 0.933170 0.981531 0.110 Uiso 1 1 calc GR . . . .
H31B H 0.652173 0.989426 0.878016 0.110 Uiso 1 1 calc GR . . . .
H31C H 0.687970 0.926584 0.888610 0.110 Uiso 1 1 calc GR . . . .
C32 C 0.64094(6) 0.64796(8) 0.50614(19) 0.0490(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
O1 C16 1.314(2) . ?
O2 C16 1.229(2) . ?
O3 C32 1.316(3) . ?
O4 C32 1.231(2) . ?
N1 C1 1.398(2) . ?
N1 C8 1.415(2) . ?
N2 C17 1.405(2) . ?
N2 C24 1.406(2) . ?
C1 C2 1.416(2) . ?
C1 C6 1.408(2) . ?
C2 C3 1.399(2) . ?
C2 C16 1.477(2) . ?
C3 C4 1.379(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.504(3) . ?
C8 C9 1.406(2) . ?
C8 C13 1.390(2) . ?
C9 C10 1.400(2) . ?
C9 C14 1.504(2) . ?
C10 C11 1.395(3) . ?
C10 C15 1.505(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.387(2) . ?
C17 C18 1.408(2) . ?
C17 C22 1.408(2) . ?
C18 C19 1.404(2) . ?
C18 C32 1.484(2) . ?
C19 C20 1.373(3) . ?
C20 C21 1.384(4) . ?
C21 C22 1.390(3) . ?
C22 C23 1.502(3) . ?
C24 C25 1.406(2) . ?
C24 C29 1.397(2) . ?
C25 C26 1.400(2) . ?
C25 C30 1.500(3) . ?
C26 C27 1.391(3) . ?
C26 C31 1.508(3) . ?
C27 C28 1.383(3) . ?
C28 C29 1.380(3) . ?

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
C1 N1 C8 123.70(13) . . ?
C17 N2 C24 122.08(13) . . ?
N1 C1 C2 121.13(13) . . ?
N1 C1 C6 119.90(15) . . ?
C6 C1 C2 118.93(15) . . ?
C1 C2 C16 121.13(15) . . ?
C3 C2 C1 119.99(15) . . ?
C3 C2 C16 118.83(16) . . ?
C4 C3 C2 120.41(19) . . ?
C5 C4 C3 119.26(18) . . ?
C4 C5 C6 122.59(17) . . ?
C1 C6 C7 121.67(16) . . ?
C5 C6 C1 118.54(17) . . ?
C5 C6 C7 119.70(17) . . ?
C9 C8 N1 117.42(13) . . ?
C13 C8 N1 122.06(14) . . ?
C13 C8 C9 120.51(14) . . ?
C8 C9 C14 119.61(14) . . ?
C10 C9 C8 119.11(14) . . ?
C10 C9 C14 121.28(15) . . ?
C9 C10 C15 120.94(16) . . ?
C11 C10 C9 119.69(15) . . ?
C11 C10 C15 119.36(15) . . ?
C12 C11 C10 120.54(16) . . ?
C11 C12 C13 120.38(16) . . ?
C12 C13 C8 119.71(15) . . ?
O1 C16 C2 115.01(16) . . ?
O2 C16 O1 121.96(16) . . ?
O2 C16 C2 123.01(17) . . ?
N2 C17 C18 121.40(14) . . ?
N2 C17 C22 118.99(16) . . ?
C22 C17 C18 119.60(16) . . ?
C17 C18 C32 121.98(15) . . ?
C19 C18 C17 119.86(16) . . ?
C19 C18 C32 118.12(16) . . ?
C20 C19 C18 120.3(2) . . ?
C19 C20 C21 119.64(19) . . ?
C20 C21 C22 122.17(17) . . ?
C17 C22 C23 120.86(18) . . ?
C21 C22 C17 118.43(19) . . ?
C21 C22 C23 120.67(17) . . ?
N2 C24 C25 117.72(14) . . ?
C29 C24 N2 122.11(14) . . ?
C29 C24 C25 120.15(15) . . ?
C24 C25 C30 119.46(15) . . ?
C26 C25 C24 119.19(15) . . ?
C26 C25 C30 121.34(15) . . ?
C25 C26 C31 120.77(17) . . ?
C27 C26 C25 119.87(16) . . ?
C27 C26 C31 119.35(17) . . ?
C28 C27 C26 120.36(16) . . ?
C29 C28 C27 120.68(16) . . ?
C28 C29 C24 119.72(15) . . ?
O3 C32 C18 113.80(16) . . ?
O4 C32 O3 122.35(16) . . ?
O4 C32 C18 123.85(17) . . ?

_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 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.744
####################################################################### 
# 
# 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_5-S
_database_code_depnum_ccdc_archive 'CCDC 2118318'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2021-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C16 H17 N O2'
_chemical_formula_sum            'C18 H23 N O3 S'
_chemical_formula_weight         333.43
_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 0.0181 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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.8712(11)
_cell_length_b                   15.0167(14)
_cell_length_c                   10.3420(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.057(11)
_cell_angle_gamma                90
_cell_volume                     1852.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4717
_cell_measurement_temperature    300.16(10)
_cell_measurement_theta_max      73.8210
_cell_measurement_theta_min      3.6670
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12806
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.820
_diffrn_reflns_theta_min         3.705
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.16(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  30.00   1.00    1.80    --  -43.05  80.00-137.00  100
  2  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00-120.00   30
  3  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00-180.00   30
  4  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00-150.00   30
  5  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00 -60.00   30
  6  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00   0.00   30
  7  ω    -70.00 -30.00   1.00    6.00    -- -100.00  61.00 -30.00   40
  8  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00  90.00   30
  9  ω    -54.00 -24.00   1.00    6.00    -- -100.00  45.00 150.00   30
 10  ω   -100.00 -20.00   1.00    1.80    --  -43.05 -80.00  98.00   80
 11  ω    -37.00  23.00   1.00    1.80    --   43.05 -19.00 -60.00   60
 12  ω     38.00  68.00   1.00    6.00    --  109.26 -61.00   0.00   30
 13  ω     35.00  65.00   1.00    6.00    --  109.26 -61.00  30.00   30
 14  ω     44.00 104.00   1.00    6.00    --  109.26 -94.00 -30.00   60
 15  ω     79.00 109.00   1.00    6.00    --  109.26-125.00 -30.00   30
 16  ω    108.00 138.00   1.00    6.00    --  109.26 -80.00  98.00   30
 17  ω     52.00 112.00   1.00    6.00    --  109.26 -80.00  98.00   60
 18  ω     41.00  81.00   1.00    6.00    --  109.26-125.00 -30.00   40
 19  ω     -3.00  27.00   1.00    1.80    --   43.05 -80.00  98.00   30
 20  ω    -22.00   8.00   1.00    1.80    --   43.05 -19.00  90.00   30
 21  ω     40.00  70.00   1.00    6.00    --  109.26 -61.00 150.00   30
 22  ω     81.00 171.00   1.00    6.00    --  109.26  80.00-137.00   90
 23  ω    -61.00 -31.00   1.00    6.00    -- -100.00  61.00-180.00   30
 24  ω   -102.00 -72.00   1.00    6.00    -- -100.00  80.00-137.00   30
 25  ω   -166.00-136.00   1.00    6.00    -- -100.00-125.00-180.00   30
 26  ω   -135.00 -85.00   1.00    6.00    -- -100.00-125.00-180.00   50
 27  ω    -41.00 -15.00   1.00    1.80    --  -42.93 -80.00 101.00   26
 28  ω    -31.00  32.00   1.00    1.80    --  -42.93  37.00  90.00   63
 29  ω    -22.00  28.00   1.00    1.80    --  -42.93  19.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462070000
_diffrn_orient_matrix_UB_12      0.0844795000
_diffrn_orient_matrix_UB_13      0.0440130000
_diffrn_orient_matrix_UB_21      0.0712088000
_diffrn_orient_matrix_UB_22      -0.0199093000
_diffrn_orient_matrix_UB_23      0.1540736000
_diffrn_orient_matrix_UB_31      0.0972628000
_diffrn_orient_matrix_UB_32      0.0547847000
_diffrn_orient_matrix_UB_33      -0.0118927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2322
_reflns_number_total             3622
_reflns_odcompleteness_completeness 98.56
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0028(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.045
_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)+(0.1446P)²+0.0949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2009
_refine_ls_wR_factor_ref         0.2317
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: S1(0.75) S1B(0.25) H17A(0.75) H17B(0.75) H17C(0.75) H17D(0.25)
 H17E(0.25) H17F(0.25) C18(0.7) H18A(0.7) H18B(0.7) H18C(0.7) C18B(0.3)
 H18D(0.3) H18E(0.3) H18F(0.3)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17(H17D,H17E,H17F), C18(H18A,H18B,H18C), C18B(H18D,H18E,
 H18F), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
S1 S 0.52091(8) 0.83692(8) 0.17641(12) 0.0989(4) Uani 0.75 1 d . . P A 1
S1B S 0.4110(3) 0.8180(3) 0.0827(5) 0.1050(9) Uani 0.25 1 d . . P A 2
O3 O 0.5434(3) 0.74227(19) 0.1741(4) 0.1556(12) Uani 1 1 d . . . . .
C17 C 0.4231(4) 0.8517(3) 0.2569(5) 0.1358(14) Uani 1 1 d . . . . .
H17A H 0.360239 0.812801 0.214129 0.204 Uiso 0.75 1 calc R U P A 1
H17B H 0.397754 0.912377 0.245795 0.204 Uiso 0.75 1 calc R U P A 1
H17C H 0.457928 0.837931 0.354384 0.204 Uiso 0.75 1 calc R U P A 1
H17D H 0.358132 0.831980 0.273311 0.204 Uiso 0.25 1 calc R U P A 2
H17E H 0.428367 0.915387 0.264339 0.204 Uiso 0.25 1 calc R U P A 2
H17F H 0.489019 0.825448 0.324754 0.204 Uiso 0.25 1 calc R U P A 2
C18 C 0.4222(8) 0.8530(7) 0.0021(8) 0.162(3) Uani 0.7 1 d . . P A 1
H18A H 0.461644 0.860485 -0.059674 0.243 Uiso 0.7 1 calc R U P A 1
H18B H 0.378128 0.905187 -0.001317 0.243 Uiso 0.7 1 calc R U P A 1
H18C H 0.373899 0.802054 -0.026281 0.243 Uiso 0.7 1 calc R U P A 1
C18B C 0.4691(18) 0.9155(14) 0.037(3) 0.198(11) Uani 0.3 1 d . . P A 2
H18D H 0.416066 0.963401 0.017825 0.297 Uiso 0.3 1 calc R U P A 2
H18E H 0.485965 0.903625 -0.044077 0.297 Uiso 0.3 1 calc R U P A 2
H18F H 0.536642 0.931833 0.113333 0.297 Uiso 0.3 1 calc R U P A 2
O1 O 0.29527(19) 0.65145(14) 0.1395(3) 0.1075(7) Uani 1 1 d . . . . .
O2 O 0.44152(19) 0.59155(17) 0.1094(3) 0.1153(8) Uani 1 1 d . . . . .
H2 H 0.463654 0.643216 0.122463 0.173 Uiso 1 1 calc R U . . .
N1 N 0.16479(19) 0.52842(15) 0.2023(2) 0.0835(6) Uani 1 1 d . . . . .
H1 H 0.134804 0.578644 0.168236 0.100 Uiso 1 1 calc R U . . .
C1 C 0.1755(2) 0.50637(17) 0.3394(3) 0.0772(6) Uani 1 1 d . . . . .
C2 C 0.1307(2) 0.56633(19) 0.4092(3) 0.0857(7) Uani 1 1 d . . . . .
C3 C 0.1439(3) 0.5478(2) 0.5467(3) 0.0980(9) Uani 1 1 d . . . . .
C4 C 0.1977(3) 0.4717(3) 0.6093(3) 0.1109(11) Uani 1 1 d . . . . .
H4 H 0.205622 0.459590 0.700667 0.133 Uiso 1 1 calc R U . . .
C5 C 0.2405(3) 0.4125(2) 0.5408(3) 0.1064(10) Uani 1 1 d . . . . .
H5 H 0.276101 0.360943 0.585520 0.128 Uiso 1 1 calc R U . . .
C6 C 0.2306(2) 0.42981(19) 0.4051(3) 0.0876(7) Uani 1 1 d . . . . .
H6 H 0.260433 0.390570 0.358646 0.105 Uiso 1 1 calc R U . . .
C7 C 0.2008(2) 0.47221(17) 0.1189(3) 0.0799(7) Uani 1 1 d . . . . .
C8 C 0.2866(2) 0.49823(17) 0.0742(3) 0.0796(7) Uani 1 1 d . . . . .
C9 C 0.3223(3) 0.4405(2) -0.0050(3) 0.0919(8) Uani 1 1 d . . . . .
H9 H 0.380091 0.457534 -0.033073 0.110 Uiso 1 1 calc R U . . .
C10 C 0.2734(3) 0.3586(2) -0.0426(3) 0.1037(9) Uani 1 1 d . . . . .
H10 H 0.298902 0.319565 -0.094070 0.124 Uiso 1 1 calc R U . . .
C11 C 0.1856(3) 0.3343(2) -0.0033(3) 0.1044(9) Uani 1 1 d . . . . .
H11 H 0.151572 0.279189 -0.030747 0.125 Uiso 1 1 calc R U . . .
C12 C 0.1472(2) 0.3899(2) 0.0757(3) 0.0902(7) Uani 1 1 d . . . . .
C13 C 0.0714(3) 0.6479(3) 0.3361(4) 0.1158(11) Uani 1 1 d . . . . .
H13A H 0.124912 0.694781 0.347513 0.174 Uiso 1 1 calc R U . . .
H13B H 0.017889 0.666236 0.375085 0.174 Uiso 1 1 calc R U . . .
H13C H 0.033316 0.635361 0.238591 0.174 Uiso 1 1 calc R U . . .
C14 C 0.0995(4) 0.6118(3) 0.6282(4) 0.1348(14) Uani 1 1 d . . . . .
H14A H 0.019038 0.611158 0.589544 0.202 Uiso 1 1 calc R U . . .
H14B H 0.125800 0.670880 0.622328 0.202 Uiso 1 1 calc R U . . .
H14C H 0.125714 0.593579 0.724166 0.202 Uiso 1 1 calc R U . . .
C15 C 0.3399(2) 0.5869(2) 0.1112(3) 0.0845(7) Uani 1 1 d . . . . .
C16 C 0.0456(3) 0.3642(2) 0.1082(4) 0.1143(10) Uani 1 1 d . . . . .
H16A H 0.069613 0.332974 0.195488 0.171 Uiso 1 1 calc R U . . .
H16B H -0.002485 0.326420 0.035417 0.171 Uiso 1 1 calc R U . . .
H16C H 0.005523 0.416945 0.114092 0.171 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
S1 O3 1.452(3) . ?
S1 C17 1.765(4) . ?
S1 C18 1.790(7) . ?
S1B O3 1.970(5) . ?
S1B C17 1.821(6) . ?
S1B C18B 1.785(18) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
O1 C15 1.217(3) . ?
O2 H2 0.8200 . ?
O2 C15 1.317(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.412(3) . ?
N1 C7 1.404(3) . ?
C1 C2 1.406(4) . ?
C1 C6 1.387(4) . ?
C2 C3 1.395(4) . ?
C2 C13 1.491(4) . ?
C3 C4 1.368(5) . ?
C3 C14 1.523(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(4) . ?
C7 C12 1.404(4) . ?
C8 C9 1.385(4) . ?
C8 C15 1.480(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(4) . ?
C12 C16 1.517(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O3 S1 C17 108.2(2) . . ?
O3 S1 C18 100.7(3) . . ?
C17 S1 C18 95.5(4) . . ?
C17 S1B O3 87.0(3) . . ?
C18B S1B O3 103.1(8) . . ?
C18B S1B C17 98.3(11) . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
S1B C17 H17D 109.5 . . ?
S1B C17 H17E 109.5 . . ?
S1B C17 H17F 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S1B C18B H18D 109.5 . . ?
S1B C18B H18E 109.5 . . ?
S1B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C15 O2 H2 109.5 . . ?
C1 N1 H1 118.5 . . ?
C7 N1 H1 118.5 . . ?
C7 N1 C1 123.1(2) . . ?
C2 C1 N1 117.5(2) . . ?
C6 C1 N1 121.7(2) . . ?
C6 C1 C2 120.8(2) . . ?
C1 C2 C13 119.8(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C13 121.6(3) . . ?
C2 C3 C14 120.7(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C14 119.6(3) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C8 C7 N1 121.1(2) . . ?
C8 C7 C12 119.6(2) . . ?
C12 C7 N1 119.2(2) . . ?
C7 C8 C15 120.7(2) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 C15 119.4(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C16 121.0(3) . . ?
C11 C12 C7 118.5(3) . . ?
C11 C12 C16 120.4(3) . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O2 121.4(3) . . ?
O1 C15 C8 124.3(2) . . ?
O2 C15 C8 114.2(2) . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
N1 C1 C2 C3 -177.6(2) . . . . ?
N1 C1 C2 C13 1.9(4) . . . . ?
N1 C1 C6 C5 178.7(3) . . . . ?
N1 C7 C8 C9 178.4(2) . . . . ?
N1 C7 C8 C15 -1.5(4) . . . . ?
N1 C7 C12 C11 -178.3(3) . . . . ?
N1 C7 C12 C16 4.9(4) . . . . ?
C1 N1 C7 C8 -116.6(3) . . . . ?
C1 N1 C7 C12 65.5(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C2 C3 C14 178.4(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C1 C2 C13 -179.7(3) . . . . ?
C7 N1 C1 C2 -176.7(2) . . . . ?
C7 N1 C1 C6 5.0(4) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C7 C8 C15 O1 -24.5(4) . . . . ?
C7 C8 C15 O2 156.5(3) . . . . ?
C8 C7 C12 C11 3.8(4) . . . . ?
C8 C7 C12 C16 -173.0(3) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C9 C8 C15 O1 155.7(3) . . . . ?
C9 C8 C15 O2 -23.4(4) . . . . ?
C9 C10 C11 C12 -1.4(5) . . . . ?
C10 C11 C12 C7 -1.3(5) . . . . ?
C10 C11 C12 C16 175.6(3) . . . . ?
C12 C7 C8 C9 -3.8(4) . . . . ?
C12 C7 C8 C15 176.4(2) . . . . ?
C13 C2 C3 C4 179.3(3) . . . . ?
C13 C2 C3 C14 -1.1(5) . . . . ?
C14 C3 C4 C5 -179.1(3) . . . . ?
C15 C8 C9 C10 -179.0(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 2.907
_oxdiff_exptl_absorpt_empirical_full_min 0.433
####################################################################### 
# 
# 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_cmpd-4
_database_code_depnum_ccdc_archive 'CCDC 2118308'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.00116(17)
_cell_length_b                   7.02328(8)
_cell_length_c                   12.03785(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.2525(10)
_cell_angle_gamma                90
_cell_volume                     1267.30(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6864
_cell_measurement_theta_max      76.6180
_cell_measurement_theta_min      3.7160

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8400
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.904
_diffrn_reflns_theta_max         76.793
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2526
_reflns_number_gt                2353
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0917P)²+0.2004P] 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         2526
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
O2 O 0.42761(7) 0.14008(16) 0.55649(9) 0.0623(3) Uani 1 1 d . . . . .
N1 N 0.29907(8) 0.3883(2) 0.61414(10) 0.0585(4) Uani 1 1 d . . . . .
H1 H 0.337936 0.365402 0.666868 0.070 Uiso 1 1 calc R U . . .
C9 C 0.21096(9) 0.3221(2) 0.62416(10) 0.0494(3) Uani 1 1 d . . . . .
O1 O 0.48502(8) 0.17578(18) 0.39094(10) 0.0741(4) Uani 1 1 d . . . . .
H1A H 0.509826 0.075984 0.409356 0.111 Uiso 1 1 calc R U . . .
C1 C 0.32521(8) 0.4907(2) 0.52036(11) 0.0514(4) Uani 1 1 d . . . . .
C2 C 0.38983(8) 0.4182(2) 0.44941(11) 0.0501(3) Uani 1 1 d . . . . .
C12 C 0.03625(10) 0.1828(2) 0.65169(12) 0.0564(4) Uani 1 1 d . . . . .
C14 C 0.18937(11) 0.2189(2) 0.71860(11) 0.0576(4) Uani 1 1 d . . . . .
H14 H 0.233033 0.195654 0.773925 0.069 Uiso 1 1 calc R U . . .
C6 C 0.28854(9) 0.6727(2) 0.49868(13) 0.0581(4) Uani 1 1 d . . . . .
C3 C 0.41398(9) 0.5230(2) 0.35642(13) 0.0594(4) Uani 1 1 d . . . . .
H3 H 0.456547 0.474755 0.309869 0.071 Uiso 1 1 calc R U . . .
C11 C 0.05886(10) 0.2816(2) 0.55678(12) 0.0600(4) Uani 1 1 d . . . . .
H11 H 0.015180 0.303156 0.501235 0.072 Uiso 1 1 calc R U . . .
C10 C 0.14422(10) 0.3487(2) 0.54239(11) 0.0586(4) Uani 1 1 d . . . . .
H10 H 0.157128 0.412341 0.477217 0.070 Uiso 1 1 calc R U . . .
C8 C 0.43463(8) 0.2334(2) 0.47104(11) 0.0511(3) Uani 1 1 d . . . . .
C13 C 0.10403(11) 0.1511(2) 0.73069(12) 0.0596(4) Uani 1 1 d . . . . .
H13 H 0.091653 0.081841 0.794087 0.072 Uiso 1 1 calc R U . . .
C5 C 0.31374(10) 0.7690(2) 0.40412(15) 0.0647(4) Uani 1 1 d . . . . .
H5 H 0.288048 0.886853 0.388050 0.078 Uiso 1 1 calc R U . . .
C15 C -0.05797(12) 0.1174(3) 0.66837(17) 0.0780(5) Uani 1 1 d . . . . .
H15A H -0.098079 0.222991 0.657956 0.117 Uiso 1 1 calc R U . . .
H15B H -0.062432 0.068153 0.742335 0.117 Uiso 1 1 calc R U . . .
H15C H -0.073419 0.019426 0.615448 0.117 Uiso 1 1 calc R U . . .
C4 C 0.37521(10) 0.6971(3) 0.33325(15) 0.0669(4) Uani 1 1 d . . . . .
H4 H 0.390386 0.765189 0.270490 0.080 Uiso 1 1 calc R U . . .
C7 C 0.22689(13) 0.7662(3) 0.57789(16) 0.0765(5) Uani 1 1 d . . . . .
H7A H 0.166796 0.724969 0.561459 0.115 Uiso 1 1 calc R U . . .
H7B H 0.230369 0.901965 0.569970 0.115 Uiso 1 1 calc R U . . .
H7C H 0.244183 0.731261 0.652772 0.115 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
O2 C8 1.2278(17) . ?
N1 C1 1.4073(19) . ?
N1 C9 1.4108(19) . ?
N1 H1 0.8600 . ?
C9 C10 1.3889(19) . ?
C9 C14 1.3968(19) . ?
O1 C8 1.3125(16) . ?
O1 H1A 0.8200 . ?
C1 C6 1.412(2) . ?
C1 C2 1.4119(19) . ?
C2 C3 1.399(2) . ?
C2 C8 1.480(2) . ?
C12 C13 1.383(2) . ?
C12 C11 1.390(2) . ?
C12 C15 1.507(2) . ?
C14 C13 1.379(2) . ?
C14 H14 0.9300 . ?
C6 C5 1.389(2) . ?
C6 C7 1.505(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C11 C10 1.382(2) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C5 C4 1.377(2) . ?
C5 H5 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 H4 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C1 N1 C9 121.92(11) . . ?
C1 N1 H1 119.0 . . ?
C9 N1 H1 119.0 . . ?
C10 C9 C14 117.57(14) . . ?
C10 C9 N1 123.14(12) . . ?
C14 C9 N1 119.25(12) . . ?
C8 O1 H1A 109.5 . . ?
N1 C1 C6 119.49(13) . . ?
N1 C1 C2 121.37(13) . . ?
C6 C1 C2 119.11(14) . . ?
C3 C2 C1 119.99(13) . . ?
C3 C2 C8 118.17(12) . . ?
C1 C2 C8 121.84(13) . . ?
C13 C12 C11 116.69(14) . . ?
C13 C12 C15 121.83(14) . . ?
C11 C12 C15 121.47(15) . . ?
C13 C14 C9 120.72(13) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C5 C6 C1 118.41(14) . . ?
C5 C6 C7 120.03(15) . . ?
C1 C6 C7 121.51(15) . . ?
C4 C3 C2 120.55(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C10 C11 C12 122.04(14) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C10 C9 120.73(13) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
O2 C8 O1 121.44(13) . . ?
O2 C8 C2 124.23(12) . . ?
O1 C8 C2 114.33(12) . . ?
C14 C13 C12 122.18(13) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C4 C5 C6 122.65(15) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C4 C3 119.20(15) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C1 N1 C9 C10 1.4(2) . . . . ?
C1 N1 C9 C14 179.13(13) . . . . ?
C9 N1 C1 C6 65.58(18) . . . . ?
C9 N1 C1 C2 -116.69(14) . . . . ?
N1 C1 C2 C3 179.60(12) . . . . ?
C6 C1 C2 C3 -2.7(2) . . . . ?
N1 C1 C2 C8 -1.3(2) . . . . ?
C6 C1 C2 C8 176.48(12) . . . . ?
C10 C9 C14 C13 -1.7(2) . . . . ?
N1 C9 C14 C13 -179.61(13) . . . . ?
N1 C1 C6 C5 -178.45(13) . . . . ?
C2 C1 C6 C5 3.8(2) . . . . ?
N1 C1 C6 C7 4.4(2) . . . . ?
C2 C1 C6 C7 -173.41(14) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C8 C2 C3 C4 -179.14(13) . . . . ?
C13 C12 C11 C10 -1.3(2) . . . . ?
C15 C12 C11 C10 177.48(16) . . . . ?
C12 C11 C10 C9 -1.1(3) . . . . ?
C14 C9 C10 C11 2.5(2) . . . . ?
N1 C9 C10 C11 -179.68(14) . . . . ?
C3 C2 C8 O2 170.55(13) . . . . ?
C1 C2 C8 O2 -8.6(2) . . . . ?
C3 C2 C8 O1 -8.41(19) . . . . ?
C1 C2 C8 O1 172.44(13) . . . . ?
C9 C14 C13 C12 -0.6(2) . . . . ?
C11 C12 C13 C14 2.1(2) . . . . ?
C15 C12 C13 C14 -176.65(15) . . . . ?
C1 C6 C5 C4 -2.4(2) . . . . ?
C7 C6 C5 C4 174.84(16) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O2 0.82 1.82 2.6409(15) 175.4 3_656 yes

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.031



