# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_k10905-jjw-c
_database_code_depnum_ccdc_archive 'CCDC 2074760'
loop_
_audit_author_name
_audit_author_address
'Vishal Kudale'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2021-04-01 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-17
_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(C17 H12 Cl2 N2 O2)'
_chemical_formula_sum            'C34 H24 Cl4 N4 O4'
_chemical_formula_weight         694.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H22 N2 O2 Cl2'
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           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                   7.70700(10)
_cell_length_b                   17.6134(2)
_cell_length_c                   22.5179(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.0880(10)
_cell_angle_gamma                90
_cell_volume                     3052.29(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34871
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0120
_cell_measurement_theta_min      2.1410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.039
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  36.00   0.50    5.65    --   10.60 -77.00   0.00  230
  2  ω    -20.00 100.00   0.50    5.65    --   10.60  57.00-150.00  240
  3  ω    -17.00 100.00   0.50    5.65    --   10.60  82.00-150.00  234
  4  ω    -17.00 100.00   0.50    5.65    --   10.60  82.00-150.00  234
  5  ω    -79.00  41.00   0.50    5.65    --   10.60 -57.00   0.00  240
  6  ω   -100.00  17.00   0.50    5.65    --  -10.90 -82.00  30.00  234
  7  ω    -79.00  38.00   0.50    5.65    --   10.60 -82.00 150.00  234
  8  ω    -15.00 100.00   0.50    5.65    --   10.60  77.00 -30.00  230
  9  ω    -79.00 -54.00   0.50    5.65    --   10.60 -57.00 -90.00   50
 10  ω    -36.00  79.00   0.50    5.65    --  -10.90  77.00-120.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089302000
_diffrn_orient_matrix_UB_12      -0.0325750000
_diffrn_orient_matrix_UB_13      -0.0180949000
_diffrn_orient_matrix_UB_21      0.0195485000
_diffrn_orient_matrix_UB_22      0.0235939000
_diffrn_orient_matrix_UB_23      -0.0242821000
_diffrn_orient_matrix_UB_31      0.0896420000
_diffrn_orient_matrix_UB_32      -0.0018840000
_diffrn_orient_matrix_UB_33      0.0088250000
_diffrn_oxdiff_digest_frames     
;
01529f3da72ce609e168521cc37e37332e000254cd8
;
_diffrn_oxdiff_digest_hkl        
;
01ba08c94d5461a4b41e335418e23a0a18ff17
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5716
_reflns_number_total             6459
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.059
_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)+(0.0342P)²+1.4144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0777
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24B,H24A)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C19(H19),
 C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C29(H29)
2.c Idealised Me refined as rotating group:
 C17(H17C,H17A,H17B), C34(H34C,H34A,H34B)
;
_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 0.80664(5) 0.34067(2) 0.51929(2) 0.02756(9) Uani 1 1 d . . . . .
Cl2 Cl 0.16068(5) 0.44178(2) 0.46664(2) 0.02833(10) Uani 1 1 d . . . . .
O1 O 0.33556(14) 0.38903(6) 0.23775(5) 0.0273(2) Uani 1 1 d . . . . .
O2 O 0.57688(18) 0.38957(6) 0.14270(5) 0.0384(3) Uani 1 1 d . . . . .
N1 N 0.34736(15) 0.50046(6) 0.28894(5) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.50419(16) 0.56816(7) 0.19392(5) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.39367(18) 0.57676(7) 0.29284(6) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.46973(18) 0.60963(8) 0.24386(6) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.5147(2) 0.68680(8) 0.24565(7) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.564873 0.708728 0.213141 0.029 Uiso 1 1 calc R . . . .
C4 C 0.4860(2) 0.73030(8) 0.29448(7) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.516026 0.781443 0.295289 0.031 Uiso 1 1 calc R . . . .
C5 C 0.4110(2) 0.69679(8) 0.34308(7) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.391207 0.726217 0.376324 0.029 Uiso 1 1 calc R . . . .
C6 C 0.36570(19) 0.62105(8) 0.34293(6) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.316902 0.599622 0.375893 0.025 Uiso 1 1 calc R . . . .
C7 C 0.26997(18) 0.46356(8) 0.33943(6) 0.0195(3) Uani 1 1 d . . . . .
H7A H 0.201404 0.420363 0.325322 0.023 Uiso 1 1 calc R . . . .
H7B H 0.192845 0.498967 0.357853 0.023 Uiso 1 1 calc R . . . .
C8 C 0.40805(18) 0.43706(7) 0.38519(6) 0.0177(3) Uani 1 1 d . . . . .
C9 C 0.57660(19) 0.42062(8) 0.36968(6) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.606717 0.429073 0.330793 0.025 Uiso 1 1 calc R . . . .
C10 C 0.70042(19) 0.39207(8) 0.41054(6) 0.0214(3) Uani 1 1 d . . . . .
H10 H 0.812339 0.381613 0.399348 0.026 Uiso 1 1 calc R . . . .
C11 C 0.65497(19) 0.37934(8) 0.46834(6) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.49026(19) 0.39598(8) 0.48610(6) 0.0206(3) Uani 1 1 d . . . . .
H12 H 0.461451 0.388307 0.525229 0.025 Uiso 1 1 calc R . . . .
C13 C 0.36914(18) 0.42443(8) 0.44405(6) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.37912(19) 0.45592(8) 0.24017(6) 0.0208(3) Uani 1 1 d . . . . .
C15 C 0.4665(2) 0.49667(8) 0.19263(6) 0.0222(3) Uani 1 1 d . . . . .
C16 C 0.5259(2) 0.45396(9) 0.13907(7) 0.0284(3) Uani 1 1 d . . . . .
C17 C 0.5270(3) 0.49830(12) 0.08224(8) 0.0523(6) Uani 1 1 d . . . . .
H17C H 0.565743 0.466254 0.051108 0.078 Uiso 1 1 calc GR . . . .
H17A H 0.604274 0.540813 0.087487 0.078 Uiso 1 1 calc GR . . . .
H17B H 0.411782 0.516207 0.071752 0.078 Uiso 1 1 calc GR . . . .
Cl3 Cl 0.40203(5) 0.19777(2) 0.51466(2) 0.03039(10) Uani 1 1 d . . . . .
Cl4 Cl -0.24501(5) 0.17011(2) 0.41822(2) 0.03567(11) Uani 1 1 d . . . . .
O3 O -0.11815(15) 0.39050(6) 0.27022(5) 0.0303(3) Uani 1 1 d . . . . .
O4 O 0.0020(2) 0.49336(7) 0.18577(6) 0.0503(4) Uani 1 1 d . . . . .
N3 N -0.04846(16) 0.26754(7) 0.25241(5) 0.0202(2) Uani 1 1 d . . . . .
N4 N 0.04392(16) 0.30841(7) 0.13890(5) 0.0214(3) Uani 1 1 d . . . . .
C18 C 0.01898(18) 0.21231(8) 0.21560(6) 0.0196(3) Uani 1 1 d . . . . .
C19 C 0.04317(19) 0.13702(8) 0.23384(6) 0.0223(3) Uani 1 1 d . . . . .
H19 H 0.016449 0.122298 0.271947 0.027 Uiso 1 1 calc R . . . .
C20 C 0.10695(19) 0.08466(8) 0.19496(7) 0.0244(3) Uani 1 1 d . . . . .
H20 H 0.122821 0.034557 0.207109 0.029 Uiso 1 1 calc R . . . .
C21 C 0.1480(2) 0.10588(8) 0.13762(7) 0.0251(3) Uani 1 1 d . . . . .
H21 H 0.189601 0.069932 0.111680 0.030 Uiso 1 1 calc R . . . .
C22 C 0.12674(19) 0.18002(8) 0.11962(6) 0.0228(3) Uani 1 1 d . . . . .
H22 H 0.155434 0.194303 0.081619 0.027 Uiso 1 1 calc R . . . .
C23 C 0.06199(18) 0.23421(8) 0.15830(6) 0.0195(3) Uani 1 1 d . . . . .
C24 C -0.12007(19) 0.24512(8) 0.30865(6) 0.0229(3) Uani 1 1 d . . . . .
H24B H -0.181646 0.197454 0.302779 0.028 Uiso 1 1 calc R . . . .
H24A H -0.203963 0.283039 0.319514 0.028 Uiso 1 1 calc R . . . .
C25 C 0.01373(19) 0.23593(8) 0.35953(6) 0.0196(3) Uani 1 1 d . . . . .
C26 C 0.18443(19) 0.25997(8) 0.35695(6) 0.0197(3) Uani 1 1 d . . . . .
H26 H 0.218494 0.284405 0.322867 0.024 Uiso 1 1 calc R . . . .
C27 C 0.30587(19) 0.24854(8) 0.40388(6) 0.0205(3) Uani 1 1 d . . . . .
H27 H 0.420512 0.263986 0.401006 0.025 Uiso 1 1 calc R . . . .
C28 C 0.25332(19) 0.21375(8) 0.45503(6) 0.0221(3) Uani 1 1 d . . . . .
C29 C 0.0837(2) 0.19071(8) 0.46016(7) 0.0252(3) Uani 1 1 d . . . . .
H29 H 0.048745 0.168562 0.495045 0.030 Uiso 1 1 calc R . . . .
C30 C -0.03273(19) 0.20140(8) 0.41214(7) 0.0231(3) Uani 1 1 d . . . . .
C31 C -0.06191(19) 0.34338(8) 0.23631(6) 0.0225(3) Uani 1 1 d . . . . .
C32 C -0.00791(19) 0.35950(8) 0.17526(6) 0.0225(3) Uani 1 1 d . . . . .
C33 C -0.0061(2) 0.43991(9) 0.15272(7) 0.0288(3) Uani 1 1 d . . . . .
C34 C -0.0033(3) 0.45006(10) 0.08674(8) 0.0502(5) Uani 1 1 d . . . . .
H34C H 0.105133 0.431820 0.073249 0.075 Uiso 1 1 calc GR . . . .
H34A H -0.016095 0.502923 0.077101 0.075 Uiso 1 1 calc GR . . . .
H34B H -0.097232 0.421929 0.067588 0.075 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
Cl1 C11 1.7327(14) . ?
Cl2 C13 1.7382(14) . ?
O1 C14 1.2254(17) . ?
O2 C16 1.2016(19) . ?
N1 C1 1.3921(17) . ?
N1 C7 1.4641(17) . ?
N1 C14 1.3822(18) . ?
N2 C2 1.3788(18) . ?
N2 C15 1.2921(19) . ?
C1 C2 1.4018(19) . ?
C1 C6 1.3977(19) . ?
C2 C3 1.403(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5146(19) . ?
C8 C9 1.394(2) . ?
C8 C13 1.3925(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3841(19) . ?
C11 C12 1.383(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(2) . ?
C14 C15 1.481(2) . ?
C15 C16 1.513(2) . ?
C16 C17 1.499(2) . ?
C17 H17C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
Cl3 C28 1.7407(15) . ?
Cl4 C30 1.7388(15) . ?
O3 C31 1.2228(17) . ?
O4 C33 1.1997(19) . ?
N3 C18 1.3963(18) . ?
N3 C24 1.4628(18) . ?
N3 C31 1.3866(18) . ?
N4 C23 1.3826(18) . ?
N4 C32 1.2942(18) . ?
C18 C19 1.398(2) . ?
C18 C23 1.404(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.397(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.402(2) . ?
C24 H24B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 C25 1.508(2) . ?
C25 C26 1.386(2) . ?
C25 C30 1.395(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.388(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(2) . ?
C28 C29 1.379(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.380(2) . ?
C31 C32 1.485(2) . ?
C32 C33 1.505(2) . ?
C33 C34 1.498(2) . ?
C34 H34C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 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 C7 119.56(11) . . ?
C14 N1 C1 122.84(12) . . ?
C14 N1 C7 117.52(11) . . ?
C15 N2 C2 118.80(12) . . ?
N1 C1 C2 117.76(12) . . ?
N1 C1 C6 122.66(12) . . ?
C6 C1 C2 119.57(13) . . ?
N2 C2 C1 122.00(12) . . ?
N2 C2 C3 118.59(13) . . ?
C1 C2 C3 119.40(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.02(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.02(13) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.52(14) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.46(13) . . ?
C5 C6 H6 120.3 . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
N1 C7 C8 111.37(11) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C9 C8 C7 121.59(12) . . ?
C13 C8 C7 121.16(12) . . ?
C13 C8 C9 117.17(13) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.84(13) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 118.92(13) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 Cl1 119.37(11) . . ?
C12 C11 Cl1 119.26(11) . . ?
C12 C11 C10 121.36(13) . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.27(13) . . ?
C13 C12 H12 120.9 . . ?
C8 C13 Cl2 120.02(11) . . ?
C12 C13 Cl2 117.54(10) . . ?
C12 C13 C8 122.41(13) . . ?
O1 C14 N1 121.41(13) . . ?
O1 C14 C15 124.61(13) . . ?
N1 C14 C15 113.97(12) . . ?
N2 C15 C14 124.50(13) . . ?
N2 C15 C16 115.17(13) . . ?
C14 C15 C16 120.27(13) . . ?
O2 C16 C15 121.80(14) . . ?
O2 C16 C17 122.19(15) . . ?
C17 C16 C15 115.92(13) . . ?
C16 C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17C C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 N3 C24 119.72(12) . . ?
C31 N3 C18 122.74(12) . . ?
C31 N3 C24 117.39(12) . . ?
C32 N4 C23 119.12(12) . . ?
N3 C18 C19 122.31(13) . . ?
N3 C18 C23 117.91(12) . . ?
C19 C18 C23 119.78(13) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.60(13) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 120.91(14) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.83(14) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.30(14) . . ?
C23 C22 H22 119.8 . . ?
N4 C23 C18 121.70(12) . . ?
N4 C23 C22 118.72(13) . . ?
C22 C23 C18 119.57(13) . . ?
N3 C24 H24B 108.7 . . ?
N3 C24 H24A 108.7 . . ?
N3 C24 C25 114.34(12) . . ?
H24B C24 H24A 107.6 . . ?
C25 C24 H24B 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C26 C25 C24 123.16(13) . . ?
C26 C25 C30 117.14(13) . . ?
C30 C25 C24 119.70(13) . . ?
C25 C26 H26 119.1 . . ?
C25 C26 C27 121.76(13) . . ?
C27 C26 H26 119.1 . . ?
C26 C27 H27 120.6 . . ?
C28 C27 C26 118.82(13) . . ?
C28 C27 H27 120.6 . . ?
C27 C28 Cl3 120.22(12) . . ?
C29 C28 Cl3 118.38(11) . . ?
C29 C28 C27 121.39(14) . . ?
C28 C29 H29 120.9 . . ?
C28 C29 C30 118.25(13) . . ?
C30 C29 H29 120.9 . . ?
C25 C30 Cl4 119.38(12) . . ?
C29 C30 Cl4 118.03(11) . . ?
C29 C30 C25 122.59(13) . . ?
O3 C31 N3 120.97(13) . . ?
O3 C31 C32 125.07(13) . . ?
N3 C31 C32 113.93(12) . . ?
N4 C32 C31 124.34(13) . . ?
N4 C32 C33 115.61(13) . . ?
C31 C32 C33 120.03(13) . . ?
O4 C33 C32 122.04(14) . . ?
O4 C33 C34 121.24(15) . . ?
C34 C33 C32 116.60(13) . . ?
C33 C34 H34C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34C C34 H34A 109.5 . . ?
H34C C34 H34B 109.5 . . ?
H34A C34 H34B 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
Cl1 C11 C12 C13 -177.79(11) . . . . ?
O1 C14 C15 N2 176.21(14) . . . . ?
O1 C14 C15 C16 -6.6(2) . . . . ?
N1 C1 C2 N2 -2.2(2) . . . . ?
N1 C1 C2 C3 178.65(13) . . . . ?
N1 C1 C6 C5 -178.41(13) . . . . ?
N1 C7 C8 C9 -25.25(18) . . . . ?
N1 C7 C8 C13 158.04(12) . . . . ?
N1 C14 C15 N2 -3.1(2) . . . . ?
N1 C14 C15 C16 174.02(13) . . . . ?
N2 C2 C3 C4 -178.94(14) . . . . ?
N2 C15 C16 O2 143.95(17) . . . . ?
N2 C15 C16 C17 -32.6(2) . . . . ?
C1 N1 C7 C8 -83.37(15) . . . . ?
C1 N1 C14 O1 -179.38(13) . . . . ?
C1 N1 C14 C15 -0.02(19) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 N2 C15 C14 3.5(2) . . . . ?
C2 N2 C15 C16 -173.82(13) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C6 C1 C2 N2 178.37(13) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C7 N1 C1 C2 179.07(12) . . . . ?
C7 N1 C1 C6 -1.6(2) . . . . ?
C7 N1 C14 O1 3.9(2) . . . . ?
C7 N1 C14 C15 -176.70(12) . . . . ?
C7 C8 C9 C10 -176.07(13) . . . . ?
C7 C8 C13 Cl2 -1.92(18) . . . . ?
C7 C8 C13 C12 176.17(12) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C8 C13 Cl2 -178.77(10) . . . . ?
C9 C8 C13 C12 -0.7(2) . . . . ?
C9 C10 C11 Cl1 177.88(11) . . . . ?
C9 C10 C11 C12 -1.3(2) . . . . ?
C10 C11 C12 C13 1.4(2) . . . . ?
C11 C12 C13 Cl2 177.75(11) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
C13 C8 C9 C10 0.8(2) . . . . ?
C14 N1 C1 C2 2.46(19) . . . . ?
C14 N1 C1 C6 -178.17(13) . . . . ?
C14 N1 C7 C8 93.42(14) . . . . ?
C14 C15 C16 O2 -33.5(2) . . . . ?
C14 C15 C16 C17 150.01(17) . . . . ?
C15 N2 C2 C1 -0.7(2) . . . . ?
C15 N2 C2 C3 178.46(13) . . . . ?
Cl3 C28 C29 C30 -178.09(11) . . . . ?
O3 C31 C32 N4 -176.70(15) . . . . ?
O3 C31 C32 C33 5.2(2) . . . . ?
N3 C18 C19 C20 178.63(13) . . . . ?
N3 C18 C23 N4 2.0(2) . . . . ?
N3 C18 C23 C22 -178.72(13) . . . . ?
N3 C24 C25 C26 11.52(19) . . . . ?
N3 C24 C25 C30 -168.12(12) . . . . ?
N3 C31 C32 N4 1.5(2) . . . . ?
N3 C31 C32 C33 -176.68(13) . . . . ?
N4 C32 C33 O4 -156.55(17) . . . . ?
N4 C32 C33 C34 19.6(2) . . . . ?
C18 N3 C24 C25 83.51(16) . . . . ?
C18 N3 C31 O3 -178.39(13) . . . . ?
C18 N3 C31 C32 3.37(19) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C18 C23 N4 -178.49(13) . . . . ?
C19 C18 C23 C22 0.8(2) . . . . ?
C19 C20 C21 C22 0.7(2) . . . . ?
C20 C21 C22 C23 -0.8(2) . . . . ?
C21 C22 C23 N4 179.37(13) . . . . ?
C21 C22 C23 C18 0.0(2) . . . . ?
C23 N4 C32 C31 -4.4(2) . . . . ?
C23 N4 C32 C33 173.86(13) . . . . ?
C23 C18 C19 C20 -0.9(2) . . . . ?
C24 N3 C18 C19 -9.0(2) . . . . ?
C24 N3 C18 C23 170.51(12) . . . . ?
C24 N3 C31 O3 6.0(2) . . . . ?
C24 N3 C31 C32 -172.23(12) . . . . ?
C24 C25 C26 C27 -177.94(13) . . . . ?
C24 C25 C30 Cl4 -0.43(19) . . . . ?
C24 C25 C30 C29 179.47(13) . . . . ?
C25 C26 C27 C28 -1.5(2) . . . . ?
C26 C25 C30 Cl4 179.91(11) . . . . ?
C26 C25 C30 C29 -0.2(2) . . . . ?
C26 C27 C28 Cl3 179.53(10) . . . . ?
C26 C27 C28 C29 -0.2(2) . . . . ?
C27 C28 C29 C30 1.7(2) . . . . ?
C28 C29 C30 Cl4 178.44(11) . . . . ?
C28 C29 C30 C25 -1.5(2) . . . . ?
C30 C25 C26 C27 1.7(2) . . . . ?
C31 N3 C18 C19 175.47(13) . . . . ?
C31 N3 C18 C23 -5.0(2) . . . . ?
C31 N3 C24 C25 -100.75(15) . . . . ?
C31 C32 C33 O4 21.7(2) . . . . ?
C31 C32 C33 C34 -162.12(16) . . . . ?
C32 N4 C23 C18 2.6(2) . . . . ?
C32 N4 C23 C22 -176.74(13) . . . . ?

_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_k10908-jjw-b
_database_code_depnum_ccdc_archive 'CCDC 2074960'
loop_
_audit_author_name
_audit_author_address
'Vishal Kudale'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-30
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H14 N2 O1'
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                   4.69210(10)
_cell_length_b                   21.3139(7)
_cell_length_c                   14.5759(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.032(3)
_cell_angle_gamma                90
_cell_volume                     1446.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5265
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9660
_cell_measurement_theta_min      2.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9480
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.701
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  41.00   0.50   14.45    --   10.60 -57.00   0.00  240
  2  ω    -79.00 100.00   0.50   14.45    --   10.60 -19.00 150.00  358
  3  ω    -17.00  93.00   0.50   14.45    --   10.60  82.00-120.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1169968000
_diffrn_orient_matrix_UB_12      0.0187163000
_diffrn_orient_matrix_UB_13      0.0195041000
_diffrn_orient_matrix_UB_21      0.0463329000
_diffrn_orient_matrix_UB_22      0.0033249000
_diffrn_orient_matrix_UB_23      -0.0442677000
_diffrn_orient_matrix_UB_31      -0.0858357000
_diffrn_orient_matrix_UB_32      0.0273173000
_diffrn_orient_matrix_UB_33      -0.0079699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2068
_reflns_number_total             2512
_reflns_odcompleteness_completeness 96.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.094
_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)+(0.0400P)²+0.6344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C)
;
_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 -0.2515(2) 0.23336(5) 0.61515(8) 0.0264(3) Uani 1 1 d . . . . .
O2 O -0.0557(4) 0.14029(7) 0.47715(9) 0.0512(4) Uani 1 1 d . . . . .
N1 N 0.1159(3) 0.23938(6) 0.73389(8) 0.0174(3) Uani 1 1 d . . . . .
N2 N 0.2709(3) 0.11729(6) 0.68697(9) 0.0209(3) Uani 1 1 d . . . . .
C1 C 0.0345(3) 0.30427(7) 0.75530(11) 0.0192(4) Uani 1 1 d . . . . .
H1A H 0.035998 0.308621 0.821599 0.023 Uiso 1 1 calc R U . . .
H1B H -0.159330 0.312448 0.726404 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2360(3) 0.35200(7) 0.72179(11) 0.0179(4) Uani 1 1 d . . . . .
C3 C 0.3015(3) 0.35078(7) 0.63145(11) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.224003 0.319531 0.591374 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4803(3) 0.39543(8) 0.60040(11) 0.0215(4) Uani 1 1 d . . . . .
H4 H 0.520983 0.393697 0.539587 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6006(3) 0.44282(7) 0.65793(11) 0.0215(4) Uani 1 1 d . . . . .
C6 C 0.5349(3) 0.44393(8) 0.74838(12) 0.0237(4) Uani 1 1 d . . . . .
H6 H 0.612731 0.475165 0.788405 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3550(3) 0.39919(8) 0.77998(11) 0.0224(4) Uani 1 1 d . . . . .
H7 H 0.313788 0.400870 0.840738 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8003(4) 0.49035(8) 0.62396(13) 0.0286(4) Uani 1 1 d . . . . .
H8A H 0.986719 0.471926 0.623213 0.043 Uiso 1 1 calc R U . . .
H8B H 0.815194 0.526061 0.664393 0.043 Uiso 1 1 calc R U . . .
H8C H 0.726446 0.503385 0.562589 0.043 Uiso 1 1 calc R U . . .
C9 C 0.3445(3) 0.20945(7) 0.78651(10) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.5009(3) 0.23786(8) 0.86321(11) 0.0211(4) Uani 1 1 d . . . . .
H10 H 0.454219 0.278184 0.880645 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7242(3) 0.20609(8) 0.91290(11) 0.0229(4) Uani 1 1 d . . . . .
H11 H 0.827147 0.225381 0.963778 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7991(3) 0.14557(8) 0.88852(11) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.951517 0.124841 0.922472 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6456(3) 0.11694(8) 0.81393(11) 0.0205(4) Uani 1 1 d . . . . .
H13 H 0.693729 0.076494 0.797461 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4171(3) 0.14818(7) 0.76243(10) 0.0177(4) Uani 1 1 d . . . . .
C15 C -0.0398(3) 0.20997(8) 0.65999(11) 0.0196(4) Uani 1 1 d . . . . .
C16 C 0.0643(3) 0.14712(8) 0.63864(11) 0.0210(4) Uani 1 1 d . . . . .
C17 C -0.0718(4) 0.11550(9) 0.55115(12) 0.0275(4) Uani 1 1 d . . . . .
C18 C -0.2110(4) 0.05381(9) 0.56194(14) 0.0381(5) Uani 1 1 d . . . . .
H18A H -0.378942 0.059544 0.592568 0.057 Uiso 1 1 calc R U . . .
H18B H -0.078934 0.026456 0.598100 0.057 Uiso 1 1 calc R U . . .
H18C H -0.264993 0.035557 0.502128 0.057 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 C15 1.2264(19) . ?
O2 C17 1.212(2) . ?
N1 C1 1.478(2) . ?
N1 C9 1.395(2) . ?
N1 C15 1.376(2) . ?
N2 C14 1.389(2) . ?
N2 C16 1.294(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.510(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C5 C6 1.390(2) . ?
C5 C8 1.504(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.398(2) . ?
C9 C14 1.405(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(2) . ?
C15 C16 1.472(2) . ?
C16 C17 1.513(2) . ?
C17 C18 1.485(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C9 N1 C1 120.88(13) . . ?
C15 N1 C1 117.73(13) . . ?
C15 N1 C9 121.39(13) . . ?
C16 N2 C14 117.57(14) . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.95(12) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C3 C2 C1 120.94(14) . . ?
C7 C2 C1 120.76(14) . . ?
C7 C2 C3 118.28(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.78(15) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.47(15) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.66(15) . . ?
C4 C5 C8 120.99(15) . . ?
C6 C5 C8 121.34(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.14(16) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 120.67(15) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 122.33(15) . . ?
N1 C9 C14 118.80(14) . . ?
C10 C9 C14 118.86(14) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.92(15) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.36(16) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.29(15) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.45(16) . . ?
C14 C13 H13 119.8 . . ?
N2 C14 C9 121.80(14) . . ?
N2 C14 C13 118.08(14) . . ?
C13 C14 C9 120.10(15) . . ?
O1 C15 N1 123.35(15) . . ?
O1 C15 C16 121.69(15) . . ?
N1 C15 C16 114.96(14) . . ?
N2 C16 C15 125.31(15) . . ?
N2 C16 C17 116.81(15) . . ?
C15 C16 C17 117.83(14) . . ?
O2 C17 C16 119.36(16) . . ?
O2 C17 C18 123.81(17) . . ?
C18 C17 C16 116.80(15) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C15 C16 N2 -174.15(15) . . . . ?
O1 C15 C16 C17 8.5(2) . . . . ?
N1 C1 C2 C3 50.80(19) . . . . ?
N1 C1 C2 C7 -130.80(15) . . . . ?
N1 C9 C10 C11 179.80(13) . . . . ?
N1 C9 C14 N2 1.1(2) . . . . ?
N1 C9 C14 C13 179.98(13) . . . . ?
N1 C15 C16 N2 5.1(2) . . . . ?
N1 C15 C16 C17 -172.26(13) . . . . ?
N2 C16 C17 O2 -117.04(19) . . . . ?
N2 C16 C17 C18 61.0(2) . . . . ?
C1 N1 C9 C10 2.2(2) . . . . ?
C1 N1 C9 C14 -178.83(12) . . . . ?
C1 N1 C15 O1 -4.6(2) . . . . ?
C1 N1 C15 C16 176.11(12) . . . . ?
C1 C2 C3 C4 178.41(14) . . . . ?
C1 C2 C7 C6 -178.47(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C8 178.64(15) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
C8 C5 C6 C7 -178.69(15) . . . . ?
C9 N1 C1 C2 77.26(17) . . . . ?
C9 N1 C15 O1 175.94(14) . . . . ?
C9 N1 C15 C16 -3.31(19) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C9 C14 N2 -179.86(13) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 N2 179.31(13) . . . . ?
C12 C13 C14 C9 0.4(2) . . . . ?
C14 N2 C16 C15 -3.6(2) . . . . ?
C14 N2 C16 C17 173.78(13) . . . . ?
C14 C9 C10 C11 0.8(2) . . . . ?
C15 N1 C1 C2 -102.17(15) . . . . ?
C15 N1 C9 C10 -178.38(13) . . . . ?
C15 N1 C9 C14 0.6(2) . . . . ?
C15 C16 C17 O2 60.5(2) . . . . ?
C15 C16 C17 C18 -121.40(17) . . . . ?
C16 N2 C14 C9 0.4(2) . . . . ?
C16 N2 C14 C13 -178.49(14) . . . . ?

_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 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.511
