# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_14529_auto
_database_code_depnum_ccdc_archive 'CCDC 2420134'
loop_
_audit_author_name
_audit_author_address
'Cao Xiying'
;south china normal university
China
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2024-07-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_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                   12.8541(7)
_cell_length_b                   8.4683(5)
_cell_length_c                   15.3887(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.066(6)
_cell_angle_gamma                90
_cell_volume                     1573.41(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    200
_cell_measurement_theta_max      28.3170
_cell_measurement_theta_min      3.0010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13077
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.274
_diffrn_reflns_theta_min         2.743
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  86.00   1.00    1.50    --   17.28  57.00-180.00   82
  2  ω      2.00  62.00   1.00    1.50    --   17.28  57.00   0.00   60
  3  ω    -51.00  20.00   1.00    1.50    --   17.28 -57.00  30.00   71
  4  ω      3.00  86.00   1.00    1.50    --   17.28  57.00 -90.00   83
  5  ω    -39.00  26.00   1.00    1.50    --   17.28 -77.00 120.00   65
  6  ω    -26.00  17.00   1.00    1.50    --  -17.59 -92.00  61.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0111226000
_diffrn_orient_matrix_UB_12      -0.0755015000
_diffrn_orient_matrix_UB_13      0.0211566000
_diffrn_orient_matrix_UB_21      0.0093533000
_diffrn_orient_matrix_UB_22      -0.0304226000
_diffrn_orient_matrix_UB_23      -0.0396111000
_diffrn_orient_matrix_UB_31      0.0569276000
_diffrn_orient_matrix_UB_32      0.0198079000
_diffrn_orient_matrix_UB_33      0.0197398000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2847
_reflns_number_total             3816
_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 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.017
_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)+(0.0786P)²+0.7730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.09682(12) 0.3138(2) 0.26376(9) 0.0561(5) Uani 1 1 d . . . . .
H1 H 0.035942 0.285707 0.224873 0.084 Uiso 1 1 calc R U . . .
N1 N 0.39809(12) 0.38092(19) 0.56845(10) 0.0372(4) Uani 1 1 d . . . . .
N2 N 0.26038(13) 0.5339(2) 0.58665(10) 0.0395(4) Uani 1 1 d . . . . .
N3 N 0.10879(14) 0.6835(2) 0.34735(11) 0.0498(5) Uani 1 1 d . . . . .
C1 C 0.16378(15) 0.3697(2) 0.21881(12) 0.0384(4) Uani 1 1 d . . . . .
C2 C 0.13127(17) 0.3755(3) 0.12298(13) 0.0445(5) Uani 1 1 d . . . . .
H2 H 0.058775 0.341944 0.086873 0.053 Uiso 1 1 calc R U . . .
C3 C 0.20197(19) 0.4290(2) 0.07879(13) 0.0457(5) Uani 1 1 d . . . . .
C4 C 0.30709(19) 0.4782(3) 0.13301(15) 0.0513(5) Uani 1 1 d . . . . .
H4 H 0.356302 0.517881 0.104164 0.062 Uiso 1 1 calc R U . . .
C5 C 0.34123(16) 0.4705(3) 0.22817(14) 0.0441(5) Uani 1 1 d . . . . .
H5 H 0.414199 0.502822 0.263830 0.053 Uiso 1 1 calc R U . . .
C6 C 0.27061(14) 0.4162(2) 0.27293(12) 0.0348(4) Uani 1 1 d . . . . .
C7 C 0.31150(14) 0.4017(2) 0.37549(12) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.40386(15) 0.3106(2) 0.41959(13) 0.0396(4) Uani 1 1 d . . . . .
H8 H 0.438672 0.252089 0.384534 0.047 Uiso 1 1 calc R U . . .
C9 C 0.44515(14) 0.3055(2) 0.51540(13) 0.0380(4) Uani 1 1 d . . . . .
C10 C 0.30528(14) 0.4662(2) 0.52809(12) 0.0325(4) Uani 1 1 d . . . . .
C11 C 0.26108(13) 0.4831(2) 0.42994(12) 0.0315(4) Uani 1 1 d . . . . .
C12 C 0.14763(17) 0.5945(3) 0.56175(14) 0.0501(5) Uani 1 1 d . . . . .
H12A H 0.095118 0.528666 0.513101 0.060 Uiso 1 1 calc R U . . .
H12B H 0.143053 0.704836 0.539472 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1236(2) 0.5851(5) 0.65088(16) 0.0803(9) Uani 1 1 d . . . . .
H13A H 0.077660 0.675859 0.656304 0.096 Uiso 1 1 calc R U . . .
H13B H 0.083415 0.486289 0.653202 0.096 Uiso 1 1 calc R U . . .
C14 C 0.2300(2) 0.5880(4) 0.72485(16) 0.0721(8) Uani 1 1 d . . . . .
H14A H 0.226349 0.528579 0.779117 0.087 Uiso 1 1 calc R U . . .
H14B H 0.252191 0.698134 0.744062 0.087 Uiso 1 1 calc R U . . .
C15 C 0.31170(18) 0.5123(3) 0.68725(13) 0.0518(6) Uani 1 1 d . . . . .
H15A H 0.384619 0.565458 0.711147 0.062 Uiso 1 1 calc R U . . .
H15B H 0.321401 0.398830 0.703579 0.062 Uiso 1 1 calc R U . . .
C16 C 0.1661(2) 0.4309(3) -0.02555(15) 0.0662(7) Uani 1 1 d . . . . .
H16A H 0.090137 0.391038 -0.051906 0.099 Uiso 1 1 calc R U . . .
H16B H 0.215721 0.363542 -0.045532 0.099 Uiso 1 1 calc R U . . .
H16C H 0.169270 0.539201 -0.046901 0.099 Uiso 1 1 calc R U . . .
C17 C 0.54627(17) 0.2096(3) 0.56602(15) 0.0521(5) Uani 1 1 d . . . . .
H17A H 0.596214 0.272463 0.616726 0.078 Uiso 1 1 calc R U . . .
H17B H 0.584387 0.179853 0.523162 0.078 Uiso 1 1 calc R U . . .
H17C H 0.524118 0.114136 0.591159 0.078 Uiso 1 1 calc R U . . .
C18 C 0.17471(14) 0.5928(2) 0.38487(12) 0.0353(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 H1 0.8400 . ?
O1 C1 1.361(2) . ?
N1 C9 1.334(2) . ?
N1 C10 1.350(2) . ?
N2 C10 1.353(2) . ?
N2 C12 1.459(2) . ?
N2 C15 1.471(2) . ?
N3 C18 1.142(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 C4 1.386(3) . ?
C3 C16 1.511(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 C7 1.488(2) . ?
C7 C8 1.383(3) . ?
C7 C11 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 C17 1.503(3) . ?
C10 C11 1.427(2) . ?
C11 C18 1.432(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.449(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.505(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
C1 O1 H1 109.5 . . ?
C9 N1 C10 119.30(15) . . ?
C10 N2 C12 125.90(15) . . ?
C10 N2 C15 120.55(16) . . ?
C12 N2 C15 111.49(15) . . ?
O1 C1 C2 122.66(17) . . ?
O1 C1 C6 117.32(16) . . ?
C2 C1 C6 119.97(18) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.59(19) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 118.12(18) . . ?
C2 C3 C16 120.9(2) . . ?
C4 C3 C16 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.95(19) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.14(19) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 121.80(16) . . ?
C5 C6 C1 118.21(17) . . ?
C5 C6 C7 119.93(16) . . ?
C8 C7 C6 119.85(16) . . ?
C8 C7 C11 118.39(16) . . ?
C11 C7 C6 121.72(15) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.38(17) . . ?
C9 C8 H8 120.3 . . ?
N1 C9 C8 123.19(16) . . ?
N1 C9 C17 115.75(17) . . ?
C8 C9 C17 121.04(18) . . ?
N1 C10 N2 115.59(15) . . ?
N1 C10 C11 120.59(16) . . ?
N2 C10 C11 123.82(16) . . ?
C7 C11 C10 119.02(16) . . ?
C7 C11 C18 118.02(15) . . ?
C10 C11 C18 122.61(16) . . ?
N2 C12 H12A 111.0 . . ?
N2 C12 H12B 111.0 . . ?
N2 C12 C13 103.75(17) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C12 106.3(2) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C13 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
C13 C14 C15 106.61(19) . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
N2 C15 C14 103.38(18) . . ?
N2 C15 H15A 111.1 . . ?
N2 C15 H15B 111.1 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C11 177.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.2(2) . . . . ?
O1 C1 C6 C5 178.62(18) . . . . ?
O1 C1 C6 C7 1.5(3) . . . . ?
N1 C10 C11 C7 3.9(2) . . . . ?
N1 C10 C11 C18 -169.13(17) . . . . ?
N2 C10 C11 C7 -177.15(17) . . . . ?
N2 C10 C11 C18 9.8(3) . . . . ?
N2 C12 C13 C14 24.0(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C16 178.5(2) . . . . ?
C1 C6 C7 C8 120.7(2) . . . . ?
C1 C6 C7 C11 -61.6(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C1 C6 C7 -175.80(18) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 177.02(19) . . . . ?
C5 C6 C7 C8 -56.3(3) . . . . ?
C5 C6 C7 C11 121.4(2) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C6 C7 C8 C9 176.20(17) . . . . ?
C6 C7 C11 C10 -179.05(16) . . . . ?
C6 C7 C11 C18 -5.7(2) . . . . ?
C7 C8 C9 N1 2.1(3) . . . . ?
C7 C8 C9 C17 -179.16(18) . . . . ?
C8 C7 C11 C10 -1.3(2) . . . . ?
C8 C7 C11 C18 172.07(17) . . . . ?
C9 N1 C10 N2 177.51(16) . . . . ?
C9 N1 C10 C11 -3.5(3) . . . . ?
C10 N1 C9 C8 0.5(3) . . . . ?
C10 N1 C9 C17 -178.31(17) . . . . ?
C10 N2 C12 C13 154.7(2) . . . . ?
C10 N2 C15 C14 -173.4(2) . . . . ?
C11 C7 C8 C9 -1.6(3) . . . . ?
C12 N2 C10 N1 -162.58(19) . . . . ?
C12 N2 C10 C11 18.5(3) . . . . ?
C12 N2 C15 C14 -8.8(3) . . . . ?
C12 C13 C14 C15 -30.2(4) . . . . ?
C13 C14 C15 N2 23.9(3) . . . . ?
C15 N2 C10 N1 -0.3(3) . . . . ?
C15 N2 C10 C11 -179.29(18) . . . . ?
C15 N2 C12 C13 -8.9(3) . . . . ?
C16 C3 C4 C5 -177.4(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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.892
####################################################################### 
# 
# 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_14531_auto
_database_code_depnum_ccdc_archive 'CCDC 2420135'
loop_
_audit_author_name
_audit_author_address
'Cao Xiying'
;south china normal university
China
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2024-07-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 Cl N3 O'
_chemical_formula_sum            'C17 H16 Cl N3 O'
_chemical_formula_weight         313.78
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1028(13)
_cell_length_b                   8.8291(16)
_cell_length_c                   12.7916(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.609(13)
_cell_angle_gamma                90
_cell_volume                     798.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1704
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.1420
_cell_measurement_theta_min      3.1900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6298
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.314
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  82.00   1.00    1.50    --   17.12  72.00 176.00   91
  2  ω    -51.00  43.00   1.00    1.50    --   17.12 -72.00  46.00   94
  3  ω    -89.00  -4.00   1.00    1.50    --  -17.59 -19.00-120.00   85
  4  ω    -28.00  -1.00   1.00    1.50    --  -17.59  77.00 -90.00   27
  5  ω    -38.00   1.00   1.00    1.50    --  -17.59 -77.00 -60.00   39
  6  ω    -36.00  -2.00   1.00    1.50    --  -17.59 -77.00-150.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0892524000
_diffrn_orient_matrix_UB_12      0.0200790000
_diffrn_orient_matrix_UB_13      -0.0166280000
_diffrn_orient_matrix_UB_21      0.0461163000
_diffrn_orient_matrix_UB_22      -0.0446383000
_diffrn_orient_matrix_UB_23      0.0408670000
_diffrn_orient_matrix_UB_31      -0.0043813000
_diffrn_orient_matrix_UB_32      -0.0635992000
_diffrn_orient_matrix_UB_33      -0.0339295000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.771
_reflns_number_gt                2648
_reflns_number_total             3542
_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 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.030
_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)+(0.0459P)²+0.0745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
N3 \\sim C13 \\sim C13A \\sim C14 \\sim C14A \\sim C15 \\sim C15A \\sim C16:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=
 Sof(H15C)=Sof(H15D)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(H16A)=Sof(H16B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D), C14(H14A,H14B), C14A(H14C,H14D), C15(H15A,
 H15B), C15A(H15C,H15D), C16(H16A,H16B), C16(H16C,H16D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 0.71304(18) 0.61282(19) 0.82704(8) 0.0864(5) Uani 1 1 d . . . . .
O1 O 0.2128(4) 0.2942(3) 0.50832(18) 0.0517(7) Uani 1 1 d . . . . .
H1 H 0.121713 0.257453 0.533946 0.077 Uiso 1 1 calc R U . . .
N1 N 0.6002(4) 0.4479(4) 0.2327(2) 0.0488(8) Uani 1 1 d . . . . .
N2 N 0.0857(5) 0.6372(5) 0.4188(2) 0.0610(9) Uani 1 1 d . . . . .
N3 N 0.3310(5) 0.5754(4) 0.1728(2) 0.0625(10) Uani 1 1 d . U . . .
C1 C 0.3241(5) 0.3688(4) 0.5840(3) 0.0367(8) Uani 1 1 d . . . . .
C2 C 0.2970(6) 0.3584(5) 0.6899(3) 0.0504(10) Uani 1 1 d . . . . .
H2 H 0.197442 0.300735 0.710509 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4152(6) 0.4321(5) 0.7643(3) 0.0552(11) Uani 1 1 d . . . . .
H3 H 0.396544 0.424917 0.835039 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5625(5) 0.5171(5) 0.7325(3) 0.0525(10) Uani 1 1 d . . . . .
C5 C 0.5928(5) 0.5279(5) 0.6288(3) 0.0460(9) Uani 1 1 d . . . . .
H5 H 0.693560 0.584931 0.609105 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4738(5) 0.4541(4) 0.5532(2) 0.0369(8) Uani 1 1 d . . . . .
C7 C 0.5154(4) 0.4571(4) 0.4407(2) 0.0358(8) Uani 1 1 d . . . . .
C8 C 0.6810(5) 0.3937(4) 0.4139(3) 0.0418(9) Uani 1 1 d . . . . .
H8 H 0.768756 0.354823 0.465743 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7166(5) 0.3881(4) 0.3090(3) 0.0435(9) Uani 1 1 d . . . . .
C10 C 0.4389(5) 0.5156(4) 0.2560(2) 0.0443(9) Uani 1 1 d . . . . .
C11 C 0.3901(5) 0.5202(4) 0.3608(2) 0.0362(8) Uani 1 1 d . . . . .
C13 C 0.368(3) 0.545(2) 0.0662(19) 0.078(4) Uani 0.482(17) 1 d . U P A 1
H13A H 0.310406 0.449822 0.042050 0.093 Uiso 0.482(17) 1 calc R U P A 1
H13B H 0.502897 0.539509 0.060405 0.093 Uiso 0.482(17) 1 calc R U P A 1
C13A C 0.418(3) 0.584(2) 0.0679(17) 0.076(3) Uani 0.518(17) 1 d . U P A 2
H13C H 0.479074 0.490672 0.050104 0.091 Uiso 0.518(17) 1 calc R U P A 2
H13D H 0.502595 0.669291 0.063713 0.091 Uiso 0.518(17) 1 calc R U P A 2
C14 C 0.278(3) 0.680(2) 0.0010(12) 0.090(3) Uani 0.482(17) 1 d . U P A 1
H14A H 0.261969 0.660269 -0.074005 0.108 Uiso 0.482(17) 1 calc R U P A 1
H14B H 0.343541 0.774981 0.015569 0.108 Uiso 0.482(17) 1 calc R U P A 1
C14A C 0.206(3) 0.610(2) -0.0014(10) 0.090(3) Uani 0.518(17) 1 d . U P A 2
H14C H 0.217871 0.636751 -0.074136 0.108 Uiso 0.518(17) 1 calc R U P A 2
H14D H 0.122966 0.523769 0.002094 0.108 Uiso 0.518(17) 1 calc R U P A 2
C15 C 0.074(2) 0.666(2) 0.0584(11) 0.093(3) Uani 0.482(17) 1 d . U P A 1
H15A H -0.007335 0.752776 0.043341 0.111 Uiso 0.482(17) 1 calc R U P A 1
H15B H 0.005913 0.573542 0.038646 0.111 Uiso 0.482(17) 1 calc R U P A 1
C15A C 0.151(3) 0.737(2) 0.0593(10) 0.089(3) Uani 0.518(17) 1 d . U P A 2
H15C H 0.024199 0.770902 0.035524 0.106 Uiso 0.518(17) 1 calc R U P A 2
H15D H 0.238635 0.820469 0.057360 0.106 Uiso 0.518(17) 1 calc R U P A 2
C16 C 0.1598(7) 0.6629(6) 0.1734(3) 0.0735(13) Uani 1 1 d . U . . .
H16A H 0.187550 0.764746 0.198915 0.088 Uiso 0.482(17) 1 calc R U P A 1
H16B H 0.073415 0.615523 0.217779 0.088 Uiso 0.482(17) 1 calc R U P A 1
H16C H 0.170245 0.739274 0.228221 0.088 Uiso 0.518(17) 1 calc R U P A 2
H16D H 0.050853 0.599124 0.181301 0.088 Uiso 0.518(17) 1 calc R U P A 2
C17 C 0.8876(5) 0.3072(6) 0.2777(3) 0.0607(11) Uani 1 1 d . . . . .
H17A H 0.863167 0.200324 0.274346 0.091 Uiso 1 1 calc R U . . .
H17B H 0.993241 0.326880 0.328549 0.091 Uiso 1 1 calc R U . . .
H17C H 0.915918 0.342674 0.210007 0.091 Uiso 1 1 calc R U . . .
C18 C 0.2191(5) 0.5862(4) 0.3913(2) 0.0423(8) 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
Cl1 C4 1.752(4) . ?
O1 H1 0.8200 . ?
O1 C1 1.359(4) . ?
N1 C9 1.325(5) . ?
N1 C10 1.351(5) . ?
N2 C18 1.136(4) . ?
N3 C10 1.356(4) . ?
N3 C13 1.44(3) . ?
N3 C13A 1.53(2) . ?
N3 C16 1.442(5) . ?
C1 C2 1.389(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 C5 1.367(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 C7 1.497(4) . ?
C7 C8 1.376(5) . ?
C7 C11 1.404(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(5) . ?
C9 C17 1.496(5) . ?
C10 C11 1.418(4) . ?
C11 C18 1.436(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.56(3) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.68(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.69(3) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C14A C15A 1.44(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.536(13) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16 1.593(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 O1 H1 109.5 . . ?
C9 N1 C10 119.7(3) . . ?
C10 N3 C13 122.0(9) . . ?
C10 N3 C13A 117.5(8) . . ?
C10 N3 C16 128.1(3) . . ?
C13 N3 C16 109.8(9) . . ?
C16 N3 C13A 113.0(8) . . ?
O1 C1 C2 122.4(3) . . ?
O1 C1 C6 117.9(3) . . ?
C2 C1 C6 119.6(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Cl1 119.2(3) . . ?
C5 C4 Cl1 119.5(3) . . ?
C5 C4 C3 121.3(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 120.6(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 119.9(3) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 C11 118.4(3) . . ?
C11 C7 C6 122.5(3) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C8 122.5(3) . . ?
N1 C9 C17 117.2(3) . . ?
C8 C9 C17 120.3(3) . . ?
N1 C10 N3 115.2(3) . . ?
N1 C10 C11 120.8(3) . . ?
N3 C10 C11 124.0(3) . . ?
C7 C11 C10 118.8(3) . . ?
C7 C11 C18 117.1(3) . . ?
C10 C11 C18 124.1(3) . . ?
N3 C13 H13A 110.7 . . ?
N3 C13 H13B 110.7 . . ?
N3 C13 C14 105.1(17) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
N3 C13A H13C 113.1 . . ?
N3 C13A H13D 113.1 . . ?
N3 C13A C14A 93.2(13) . . ?
H13C C13A H13D 110.5 . . ?
C14A C13A H13C 113.1 . . ?
C14A C13A H13D 113.1 . . ?
C13 C14 H14A 113.3 . . ?
C13 C14 H14B 113.3 . . ?
C13 C14 C15 92.0(18) . . ?
H14A C14 H14B 110.6 . . ?
C15 C14 H14A 113.3 . . ?
C15 C14 H14B 113.3 . . ?
C13A C14A H14C 112.6 . . ?
C13A C14A H14D 112.6 . . ?
H14C C14A H14D 110.1 . . ?
C15A C14A C13A 95.7(16) . . ?
C15A C14A H14C 112.6 . . ?
C15A C14A H14D 112.6 . . ?
C14 C15 H15A 112.1 . . ?
C14 C15 H15B 112.1 . . ?
H15A C15 H15B 109.8 . . ?
C16 C15 C14 98.3(12) . . ?
C16 C15 H15A 112.1 . . ?
C16 C15 H15B 112.1 . . ?
C14A C15A H15C 111.6 . . ?
C14A C15A H15D 111.6 . . ?
C14A C15A C16 101.0(12) . . ?
H15C C15A H15D 109.4 . . ?
C16 C15A H15C 111.6 . . ?
C16 C15A H15D 111.6 . . ?
N3 C16 C15 104.9(7) . . ?
N3 C16 C15A 99.8(6) . . ?
N3 C16 H16A 110.8 . . ?
N3 C16 H16B 110.8 . . ?
N3 C16 H16C 111.8 . . ?
N3 C16 H16D 111.8 . . ?
C15 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C15A C16 H16C 111.8 . . ?
C15A C16 H16D 111.8 . . ?
H16A C16 H16B 108.8 . . ?
H16C C16 H16D 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C11 177.8(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
Cl1 C4 C5 C6 -179.3(3) . . . . ?
O1 C1 C2 C3 178.3(4) . . . . ?
O1 C1 C6 C5 -178.2(3) . . . . ?
O1 C1 C6 C7 -2.8(5) . . . . ?
N1 C10 C11 C7 1.9(5) . . . . ?
N1 C10 C11 C18 -178.2(4) . . . . ?
N3 C10 C11 C7 -178.7(3) . . . . ?
N3 C10 C11 C18 1.3(6) . . . . ?
N3 C13 C14 C15 -48(2) . . . . ?
N3 C13A C14A C15A 53(2) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C1 C6 C7 C8 -113.4(4) . . . . ?
C1 C6 C7 C11 65.6(5) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 C7 175.1(3) . . . . ?
C2 C3 C4 Cl1 179.5(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 -175.7(3) . . . . ?
C5 C6 C7 C8 62.0(5) . . . . ?
C5 C6 C7 C11 -119.0(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C6 C7 C8 C9 176.4(3) . . . . ?
C6 C7 C11 C10 -178.8(3) . . . . ?
C6 C7 C11 C18 1.3(5) . . . . ?
C7 C8 C9 N1 3.1(6) . . . . ?
C7 C8 C9 C17 -174.5(4) . . . . ?
C8 C7 C11 C10 0.3(5) . . . . ?
C8 C7 C11 C18 -179.7(3) . . . . ?
C9 N1 C10 N3 178.9(4) . . . . ?
C9 N1 C10 C11 -1.6(5) . . . . ?
C10 N1 C9 C8 -0.9(6) . . . . ?
C10 N1 C9 C17 176.7(3) . . . . ?
C10 N3 C13 C14 -156.7(13) . . . . ?
C10 N3 C13A C14A 163.3(9) . . . . ?
C10 N3 C16 C15 -166.3(10) . . . . ?
C10 N3 C16 C15A 162.8(8) . . . . ?
C11 C7 C8 C9 -2.6(5) . . . . ?
C13 N3 C10 N1 10.9(11) . . . . ?
C13 N3 C10 C11 -168.6(10) . . . . ?
C13 N3 C16 C15 8.1(10) . . . . ?
C13 C14 C15 C16 50(2) . . . . ?
C13A N3 C10 N1 -10.2(10) . . . . ?
C13A N3 C10 C11 170.4(9) . . . . ?
C13A N3 C16 C15A -3.0(10) . . . . ?
C13A C14A C15A C16 -58(2) . . . . ?
C14 C15 C16 N3 -37.5(16) . . . . ?
C14A C15A C16 N3 41.2(18) . . . . ?
C16 N3 C10 N1 -175.3(4) . . . . ?
C16 N3 C10 C11 5.2(6) . . . . ?
C16 N3 C13 C14 28.5(19) . . . . ?
C16 N3 C13A C14A -29.3(15) . . . . ?

_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.628
