# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_7641
_database_code_depnum_ccdc_archive 'CCDC 2125971'
loop_
_audit_author_name
_audit_author_address
'Zhenyao Lei'
;State Key Laboratory of NBC Protection for Civilian
China
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-03-02 downloaded from the CCDC.
;
_audit_creation_date             2010-04-12
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3322(12)
_cell_length_b                   11.6410(19)
_cell_length_c                   12.031(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.751(14)
_cell_angle_gamma                90.00
_cell_volume                     1019.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    941
_cell_measurement_temperature    119(2)
_cell_measurement_theta_max      27.3840
_cell_measurement_theta_min      4.8910
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4091
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.10
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8242
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00    4.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070   37.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   77.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   77.0000   60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0140767000
_diffrn_orient_matrix_UB_12      0.0518745000
_diffrn_orient_matrix_UB_13      -0.0308094000
_diffrn_orient_matrix_UB_21      0.0638173000
_diffrn_orient_matrix_UB_22      0.0283448000
_diffrn_orient_matrix_UB_23      0.0396355000
_diffrn_orient_matrix_UB_31      0.0722195000
_diffrn_orient_matrix_UB_32      -0.0149192000
_diffrn_orient_matrix_UB_33      -0.0316373000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1495
_reflns_number_total             1958
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0368P)²+0.1357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1048
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O1 O 0.44808(15) 0.52680(9) 0.22704(9) 0.0247(3) Uani 1 1 d . . .
O2 O 0.24445(15) 0.36803(9) 0.34172(10) 0.0278(3) Uani 1 1 d . . .
N1 N 0.52052(17) 0.44480(11) 0.30350(11) 0.0222(3) Uani 1 1 d . . .
C1 C 0.4133(2) 0.36722(13) 0.34905(14) 0.0204(4) Uani 1 1 d . . .
C9 C 0.8234(2) 0.52702(15) 0.37230(15) 0.0295(4) Uani 1 1 d . . .
H9A H 0.8040 0.5921 0.3233 0.044 Uiso 1 1 calc R . .
H9B H 0.9523 0.5099 0.3849 0.044 Uiso 1 1 calc R . .
H9C H 0.7790 0.5442 0.4424 0.044 Uiso 1 1 calc R . .
C4 C 0.5454(2) 0.28678(13) 0.41021(13) 0.0202(4) Uani 1 1 d . . .
C3 C 0.7228(2) 0.31977(14) 0.39477(13) 0.0196(4) Uani 1 1 d . . .
C2 C 0.7200(2) 0.42354(14) 0.31864(13) 0.0211(4) Uani 1 1 d . . .
C5 C 0.5111(2) 0.19216(14) 0.47471(14) 0.0249(4) Uani 1 1 d . . .
H5 H 0.3917 0.1705 0.4838 0.030 Uiso 1 1 calc R . .
C7 C 0.8383(2) 0.16343(15) 0.51009(14) 0.0268(4) Uani 1 1 d . . .
H7 H 0.9368 0.1211 0.5445 0.032 Uiso 1 1 calc R . .
C6 C 0.6605(2) 0.13097(14) 0.52506(15) 0.0270(4) Uani 1 1 d . . .
H6 H 0.6416 0.0675 0.5693 0.032 Uiso 1 1 calc R . .
C11 C 0.3744(3) 0.62199(14) 0.28444(17) 0.0336(5) Uani 1 1 d . . .
H11A H 0.3335 0.6807 0.2313 0.050 Uiso 1 1 calc R . .
H11B H 0.4681 0.6525 0.3389 0.050 Uiso 1 1 calc R . .
H11C H 0.2727 0.5960 0.3213 0.050 Uiso 1 1 calc R . .
C8 C 0.8725(2) 0.25811(14) 0.44451(14) 0.0247(4) Uani 1 1 d . . .
H8 H 0.9918 0.2792 0.4345 0.030 Uiso 1 1 calc R . .
C10 C 0.7892(2) 0.39366(16) 0.20709(15) 0.0269(4) Uani 1 1 d . . .
H10A H 0.7239 0.3279 0.1750 0.040 Uiso 1 1 calc R . .
H10B H 0.9182 0.3767 0.2194 0.040 Uiso 1 1 calc R . .
H10C H 0.7690 0.4577 0.1568 0.040 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 N1 1.3873(16) . ?
O1 C11 1.4436(19) . ?
O2 C1 1.2305(18) . ?
N1 C1 1.355(2) . ?
N1 C2 1.4738(19) . ?
C1 C4 1.480(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C2 1.526(2) . ?
C4 C3 1.389(2) . ?
C4 C5 1.387(2) . ?
C3 C2 1.515(2) . ?
C3 C8 1.387(2) . ?
C2 C10 1.530(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.390(2) . ?
C7 C8 1.395(2) . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
N1 O1 C11 110.27(12) . . ?
O1 N1 C2 119.64(12) . . ?
C1 N1 O1 122.12(12) . . ?
C1 N1 C2 116.94(13) . . ?
O2 C1 N1 126.35(15) . . ?
O2 C1 C4 129.40(15) . . ?
N1 C1 C4 104.22(13) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
C3 C4 C1 109.10(14) . . ?
C5 C4 C1 129.01(15) . . ?
C5 C4 C3 121.90(15) . . ?
C4 C3 C2 110.81(13) . . ?
C8 C3 C4 120.34(15) . . ?
C8 C3 C2 128.84(14) . . ?
N1 C2 C9 110.87(13) . . ?
N1 C2 C3 98.68(12) . . ?
N1 C2 C10 110.89(13) . . ?
C9 C2 C10 110.57(13) . . ?
C3 C2 C9 113.78(13) . . ?
C3 C2 C10 111.53(13) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.83(15) . . ?
C6 C5 H5 121.1 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.45(16) . . ?
C8 C7 H7 119.3 . . ?
C5 C6 C7 120.63(16) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C8 C7 117.85(15) . . ?
C3 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 O2 -10.2(2) . . . . ?
O1 N1 C1 C4 171.43(13) . . . . ?
O1 N1 C2 C9 67.83(17) . . . . ?
O1 N1 C2 C3 -172.51(12) . . . . ?
O1 N1 C2 C10 -55.40(18) . . . . ?
O2 C1 C4 C3 -179.85(16) . . . . ?
O2 C1 C4 C5 -0.1(3) . . . . ?
N1 C1 C4 C3 -1.56(17) . . . . ?
N1 C1 C4 C5 178.20(16) . . . . ?
C1 N1 C2 C9 -124.92(15) . . . . ?
C1 N1 C2 C3 -5.27(17) . . . . ?
C1 N1 C2 C10 111.84(16) . . . . ?
C1 C4 C3 C2 -1.67(18) . . . . ?
C1 C4 C3 C8 179.60(15) . . . . ?
C1 C4 C5 C6 -179.13(16) . . . . ?
C4 C3 C2 N1 3.87(17) . . . . ?
C4 C3 C2 C9 121.33(15) . . . . ?
C4 C3 C2 C10 -112.75(16) . . . . ?
C4 C3 C8 C7 -0.3(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C2 N1 C1 O2 -177.12(15) . . . . ?
C2 N1 C1 C4 4.52(18) . . . . ?
C2 C3 C8 C7 -178.77(15) . . . . ?
C5 C4 C3 C2 178.55(14) . . . . ?
C5 C4 C3 C8 -0.2(2) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C11 O1 N1 C1 80.32(17) . . . . ?
C11 O1 N1 C2 -113.12(15) . . . . ?
C8 C3 C2 N1 -177.54(16) . . . . ?
C8 C3 C2 C9 -60.1(2) . . . . ?
C8 C3 C2 C10 65.8(2) . . . . ?
C8 C7 C6 C5 0.1(3) . . . . ?

####################################################################### 
# 
# 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_cu_20211228_yang1_0m
_database_code_depnum_ccdc_archive 'CCDC 2131719'
loop_
_audit_author_name
_audit_author_address
'Zhenyao Lei'
;State Key Laboratory of NBC Protection for Civilian
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-03-02 downloaded from the CCDC.
;
_audit_creation_date             2021-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H15 N O2'
_chemical_formula_sum            'C12 H15 N O2'
_chemical_formula_weight         205.25
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9132(5)
_cell_length_b                   11.7925(6)
_cell_length_c                   12.0168(6)
_cell_angle_alpha                71.738(3)
_cell_angle_beta                 69.902(3)
_cell_angle_gamma                72.397(3)
_cell_volume                     1099.23(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9474
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.419
_cell_measurement_theta_min      4.045
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0996 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8404.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19166
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.557
_diffrn_reflns_theta_min         4.029
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3438
_reflns_number_total             4022
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.068
_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)+(0.0539P)²+0.1757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1093
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C20(H20), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50878(11) 0.26596(9) 0.96874(9) 0.0494(3) Uani 1 1 d . . . . .
O2 O 0.66947(15) 0.09717(10) 0.82190(10) 0.0624(3) Uani 1 1 d . . . . .
N1 N 0.67361(13) 0.20888(10) 0.94641(10) 0.0426(3) Uani 1 1 d . . . . .
C1 C 0.74249(18) 0.13519(12) 0.86708(12) 0.0436(3) Uani 1 1 d . . . . .
C2 C 0.91998(17) 0.11165(11) 0.85289(11) 0.0417(3) Uani 1 1 d . . . . .
C3 C 1.0478(2) 0.03444(12) 0.78885(13) 0.0540(4) Uani 1 1 d . . . . .
H3 H 1.027965 -0.010048 0.743644 0.065 Uiso 1 1 calc R U . . .
C4 C 1.2044(2) 0.02413(13) 0.79270(14) 0.0589(4) Uani 1 1 d . . . . .
H4 H 1.293916 -0.028034 0.749523 0.071 Uiso 1 1 calc R U . . .
C5 C 1.23232(18) 0.08926(14) 0.85905(15) 0.0580(4) Uani 1 1 d . . . . .
H5 H 1.340846 0.080696 0.861143 0.070 Uiso 1 1 calc R U . . .
C6 C 1.10448(17) 0.16663(13) 0.92236(13) 0.0489(3) Uani 1 1 d . . . . .
H6 H 1.124451 0.210717 0.967887 0.059 Uiso 1 1 calc R U . . .
C7 C 0.94682(16) 0.17852(11) 0.91802(11) 0.0386(3) Uani 1 1 d . . . . .
C8 C 0.78621(15) 0.25480(12) 0.97671(11) 0.0393(3) Uani 1 1 d . . . . .
H8 H 0.767793 0.232922 1.067063 0.047 Uiso 1 1 calc R U . . .
C9 C 0.76481(17) 0.39439(12) 0.92850(13) 0.0462(3) Uani 1 1 d . . . . .
H9 H 0.647170 0.432059 0.962202 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8661(2) 0.44237(16) 0.97510(18) 0.0664(5) Uani 1 1 d . . . . .
H10A H 0.846693 0.409353 1.063273 0.100 Uiso 1 1 calc R U . . .
H10B H 0.834558 0.531920 0.957687 0.100 Uiso 1 1 calc R U . . .
H10C H 0.982479 0.416811 0.934425 0.100 Uiso 1 1 calc R U . . .
C11 C 0.80362(19) 0.43428(14) 0.79024(14) 0.0547(4) Uani 1 1 d . . . . .
H11A H 0.922083 0.411547 0.754516 0.082 Uiso 1 1 calc R U . . .
H11B H 0.766022 0.523196 0.765651 0.082 Uiso 1 1 calc R U . . .
H11C H 0.747766 0.393793 0.761499 0.082 Uiso 1 1 calc R U . . .
C12 C 0.41739(18) 0.20196(16) 1.08188(14) 0.0564(4) Uani 1 1 d . . . . .
H12A H 0.433479 0.116794 1.079186 0.085 Uiso 1 1 calc R U . . .
H12B H 0.300843 0.241268 1.095319 0.085 Uiso 1 1 calc R U . . .
H12C H 0.455278 0.204017 1.148587 0.085 Uiso 1 1 calc R U . . .
O3 O 0.71543(13) 0.08551(8) 0.47597(9) 0.0511(3) Uani 1 1 d . . . . .
O4 O 0.56643(15) 0.25019(11) 0.29859(11) 0.0634(3) Uani 1 1 d . . . . .
N2 N 0.68694(15) 0.21228(10) 0.45218(10) 0.0454(3) Uani 1 1 d . . . . .
C13 C 0.62624(17) 0.28348(13) 0.35738(12) 0.0450(3) Uani 1 1 d . . . . .
C14 C 0.64619(16) 0.40746(12) 0.34611(11) 0.0408(3) Uani 1 1 d . . . . .
C15 C 0.59392(17) 0.51722(13) 0.27019(12) 0.0469(3) Uani 1 1 d . . . . .
H15 H 0.541862 0.520083 0.212086 0.056 Uiso 1 1 calc R U . . .
C16 C 0.61954(17) 0.62277(13) 0.28119(13) 0.0490(3) Uani 1 1 d . . . . .
H16 H 0.585359 0.699355 0.229866 0.059 Uiso 1 1 calc R U . . .
C17 C 0.69507(17) 0.61709(13) 0.36703(13) 0.0483(3) Uani 1 1 d . . . . .
H17 H 0.710374 0.690452 0.374376 0.058 Uiso 1 1 calc R U . . .
C18 C 0.74862(17) 0.50675(12) 0.44223(12) 0.0445(3) Uani 1 1 d . . . . .
H18 H 0.799618 0.503982 0.500945 0.053 Uiso 1 1 calc R U . . .
C19 C 0.72607(15) 0.40052(11) 0.42980(11) 0.0383(3) Uani 1 1 d . . . . .
C20 C 0.77561(16) 0.26874(12) 0.49496(11) 0.0407(3) Uani 1 1 d . . . . .
H20 H 0.731624 0.259479 0.585148 0.049 Uiso 1 1 calc R U . . .
C21 C 0.96094(17) 0.21308(12) 0.46137(13) 0.0461(3) Uani 1 1 d . . . . .
H21 H 0.976490 0.123669 0.501026 0.055 Uiso 1 1 calc R U . . .
C22 C 1.0517(2) 0.26766(15) 0.51066(15) 0.0575(4) Uani 1 1 d . . . . .
H22A H 0.999112 0.262925 0.597755 0.086 Uiso 1 1 calc R U . . .
H22B H 1.049050 0.353447 0.467037 0.086 Uiso 1 1 calc R U . . .
H22C H 1.165653 0.221856 0.499000 0.086 Uiso 1 1 calc R U . . .
C23 C 1.0339(2) 0.22552(16) 0.32434(14) 0.0585(4) Uani 1 1 d . . . . .
H23A H 0.968779 0.195167 0.293438 0.088 Uiso 1 1 calc R U . . .
H23B H 1.146829 0.177610 0.307974 0.088 Uiso 1 1 calc R U . . .
H23C H 1.033050 0.311785 0.283571 0.088 Uiso 1 1 calc R U . . .
C24 C 0.5947(2) 0.04321(14) 0.58389(13) 0.0538(4) Uani 1 1 d . . . . .
H24A H 0.485132 0.085172 0.574318 0.081 Uiso 1 1 calc R U . . .
H24B H 0.608280 0.060703 0.653952 0.081 Uiso 1 1 calc R U . . .
H24C H 0.607878 -0.045203 0.597275 0.081 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3885(14) . ?
O1 C12 1.4315(17) . ?
O2 C1 1.2212(17) . ?
N1 C1 1.3546(18) . ?
N1 C8 1.4616(16) . ?
C1 C2 1.479(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.3860(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3870(19) . ?
C7 C8 1.5102(18) . ?
C8 H8 1.0000 . ?
C8 C9 1.5395(18) . ?
C9 H9 1.0000 . ?
C9 C10 1.518(2) . ?
C9 C11 1.521(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O3 N2 1.3905(14) . ?
O3 C24 1.4316(17) . ?
O4 C13 1.2234(17) . ?
N2 C13 1.3582(18) . ?
N2 C20 1.4642(16) . ?
C13 C14 1.4846(19) . ?
C14 C15 1.3827(19) . ?
C14 C19 1.3893(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3865(18) . ?
C19 C20 1.5109(18) . ?
C20 H20 1.0000 . ?
C20 C21 1.5409(19) . ?
C21 H21 1.0000 . ?
C21 C22 1.518(2) . ?
C21 C23 1.525(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
N1 O1 C12 110.16(10) . . ?
O1 N1 C8 120.10(10) . . ?
C1 N1 O1 120.97(11) . . ?
C1 N1 C8 116.31(11) . . ?
O2 C1 N1 126.15(14) . . ?
O2 C1 C2 129.88(13) . . ?
N1 C1 C2 103.95(11) . . ?
C3 C2 C1 128.76(13) . . ?
C7 C2 C1 109.50(11) . . ?
C7 C2 C3 121.73(14) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.17(15) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.55(14) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.08(15) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.77(15) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 119.69(13) . . ?
C2 C7 C8 109.84(11) . . ?
C6 C7 C8 130.47(12) . . ?
N1 C8 C7 99.59(10) . . ?
N1 C8 H8 109.8 . . ?
N1 C8 C9 111.46(11) . . ?
C7 C8 H8 109.8 . . ?
C7 C8 C9 116.02(10) . . ?
C9 C8 H8 109.8 . . ?
C8 C9 H9 107.4 . . ?
C10 C9 C8 110.58(12) . . ?
C10 C9 H9 107.4 . . ?
C10 C9 C11 110.93(13) . . ?
C11 C9 C8 112.96(11) . . ?
C11 C9 H9 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 O3 C24 108.96(10) . . ?
O3 N2 C20 119.82(11) . . ?
C13 N2 O3 120.30(11) . . ?
C13 N2 C20 115.93(11) . . ?
O4 C13 N2 126.43(13) . . ?
O4 C13 C14 129.50(13) . . ?
N2 C13 C14 104.05(11) . . ?
C15 C14 C13 128.92(12) . . ?
C15 C14 C19 121.99(12) . . ?
C19 C14 C13 109.06(11) . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.17(13) . . ?
C16 C15 H15 120.9 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.20(13) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.47(13) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.48(13) . . ?
C19 C18 H18 120.8 . . ?
C14 C19 C20 110.00(11) . . ?
C18 C19 C14 119.63(12) . . ?
C18 C19 C20 130.37(12) . . ?
N2 C20 C19 99.42(10) . . ?
N2 C20 H20 110.1 . . ?
N2 C20 C21 111.56(11) . . ?
C19 C20 H20 110.1 . . ?
C19 C20 C21 115.11(10) . . ?
C21 C20 H20 110.1 . . ?
C20 C21 H21 107.4 . . ?
C22 C21 C20 111.50(12) . . ?
C22 C21 H21 107.4 . . ?
C22 C21 C23 110.80(12) . . ?
C23 C21 C20 112.05(12) . . ?
C23 C21 H21 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 O2 -11.1(2) . . . . ?
O1 N1 C1 C2 170.25(10) . . . . ?
O1 N1 C8 C7 -171.25(10) . . . . ?
O1 N1 C8 C9 -48.26(15) . . . . ?
O2 C1 C2 C3 -3.8(2) . . . . ?
O2 C1 C2 C7 177.63(13) . . . . ?
N1 C1 C2 C3 174.82(13) . . . . ?
N1 C1 C2 C7 -3.77(14) . . . . ?
N1 C8 C9 C10 172.47(12) . . . . ?
N1 C8 C9 C11 -62.54(15) . . . . ?
C1 N1 C8 C7 -9.44(14) . . . . ?
C1 N1 C8 C9 113.55(13) . . . . ?
C1 C2 C3 C4 -177.57(12) . . . . ?
C1 C2 C7 C6 177.18(11) . . . . ?
C1 C2 C7 C8 -1.91(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C7 C8 N1 6.29(13) . . . . ?
C2 C7 C8 C9 -113.41(12) . . . . ?
C3 C2 C7 C6 -1.52(19) . . . . ?
C3 C2 C7 C8 179.38(11) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C2 1.18(19) . . . . ?
C5 C6 C7 C8 -179.93(13) . . . . ?
C6 C7 C8 N1 -172.68(13) . . . . ?
C6 C7 C8 C9 67.62(18) . . . . ?
C7 C2 C3 C4 0.87(19) . . . . ?
C7 C8 C9 C10 -74.51(15) . . . . ?
C7 C8 C9 C11 50.49(16) . . . . ?
C8 N1 C1 O2 -172.72(12) . . . . ?
C8 N1 C1 C2 8.61(14) . . . . ?
C12 O1 N1 C1 101.60(14) . . . . ?
C12 O1 N1 C8 -97.45(14) . . . . ?
O3 N2 C13 O4 12.9(2) . . . . ?
O3 N2 C13 C14 -168.51(10) . . . . ?
O3 N2 C20 C19 170.76(10) . . . . ?
O3 N2 C20 C21 48.88(15) . . . . ?
O4 C13 C14 C15 3.8(2) . . . . ?
O4 C13 C14 C19 -177.94(14) . . . . ?
N2 C13 C14 C15 -174.73(13) . . . . ?
N2 C13 C14 C19 3.53(14) . . . . ?
N2 C20 C21 C22 -177.46(11) . . . . ?
N2 C20 C21 C23 57.70(15) . . . . ?
C13 N2 C20 C19 13.03(14) . . . . ?
C13 N2 C20 C21 -108.85(13) . . . . ?
C13 C14 C15 C16 176.51(13) . . . . ?
C13 C14 C19 C18 -175.56(11) . . . . ?
C13 C14 C19 C20 4.42(14) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C14 C19 C20 N2 -9.82(13) . . . . ?
C14 C19 C20 C21 109.46(13) . . . . ?
C15 C14 C19 C18 2.85(19) . . . . ?
C15 C14 C19 C20 -177.17(12) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C17 C18 C19 C14 -2.18(19) . . . . ?
C17 C18 C19 C20 177.84(13) . . . . ?
C18 C19 C20 N2 170.16(13) . . . . ?
C18 C19 C20 C21 -70.56(18) . . . . ?
C19 C14 C15 C16 -1.6(2) . . . . ?
C19 C20 C21 C22 70.24(15) . . . . ?
C19 C20 C21 C23 -54.60(16) . . . . ?
C20 N2 C13 O4 170.52(14) . . . . ?
C20 N2 C13 C14 -10.89(15) . . . . ?
C24 O3 N2 C13 -107.87(14) . . . . ?
C24 O3 N2 C20 95.38(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
