# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_202305130_auto
_database_code_depnum_ccdc_archive 'CCDC 2310414'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H26 N4 O3, C H Cl3'
_chemical_formula_sum            'C30 H27 Cl3 N4 O3'
_chemical_formula_weight         597.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.69500(14)
_cell_length_b                   18.7885(3)
_cell_length_c                   19.1891(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.4918(17)
_cell_angle_gamma                90
_cell_volume                     3060.64(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6110
_cell_measurement_theta_min      4.6990
_shelx_estimated_absorpt_T_max   0.753
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (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    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.331
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  34.00   1.00    3.50    --  -33.50  77.00   0.00   93
  2  ω    -87.00 -28.00   1.00    3.50    --  -33.50 -57.00-150.00   59
  3  ω   -100.00  -8.00   1.00    3.50    --  -33.50 -19.00-120.00   92
  4  ω     34.00  62.00   1.00    3.50    --   36.47 -99.00 -90.00   28
  5  ω    129.00 169.00   1.00   15.00    --  108.00 111.00 150.00   40
  6  ω    108.00 168.00   1.00   15.00    --  108.00 111.00 -60.00   60
  7  ω    153.00 178.00   1.00   15.00    --  108.00  45.00 -30.00   25
  8  ω     40.00 109.00   1.00   15.00    --  108.00-111.00-120.00   69
  9  ω     88.00 171.00   1.00   15.00    --  108.00  61.00   0.00   83
 10  ω     43.00 101.00   1.00   15.00    --  108.00-111.00   0.00   58
 11  ω     73.00 121.00   1.00   15.00    --  108.00 -45.00   0.00   48
 12  ω    111.00 166.00   1.00   15.00    --  108.00 111.00 -90.00   55
 13  ω    110.00 172.00   1.00   15.00    --  108.00 111.00-180.00   62
 14  ω     46.00  80.00   1.00   15.00    --  108.00 -94.00 -60.00   34
 15  ω     89.00 138.00   1.00   15.00    --  108.00  45.00 -30.00   49
;
_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      0.0894948000
_diffrn_orient_matrix_UB_12      -0.0499674000
_diffrn_orient_matrix_UB_13      -0.0410898000
_diffrn_orient_matrix_UB_21      0.0274360000
_diffrn_orient_matrix_UB_22      0.0625439000
_diffrn_orient_matrix_UB_23      -0.0477511000
_diffrn_orient_matrix_UB_31      0.1555122000
_diffrn_orient_matrix_UB_32      0.0177058000
_diffrn_orient_matrix_UB_33      0.0528395000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3733
_reflns_number_total             5472
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5472
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.027
_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)+(0.1131P)²+1.0852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2172
_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. Restrained distances
 C30-Cl2
 1.75 with sigma of 0.02
 C30-Cl3
 1.75 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq, Uanis(C30A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C30) = Uanis(C30A)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(Cl2) = Uanis(Cl2A)
Uanis(Cl3) = Uanis(Cl3A)
4. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C30A)=Sof(H30A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C30)=Sof(H30)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C30(H30), C30A(H30A)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C20(H20), C19(H19), C18(H18), C17(H17),
 C16(H16), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
5.c Fitted hexagon refined as free rotating group:
 C15(C20,C19,C18,C17,C16)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5036(3) 0.55547(11) 0.43407(10) 0.0469(5) Uani 1 1 d . . . . .
O2 O 0.3522(4) 0.78347(12) 0.45417(14) 0.0681(7) Uani 1 1 d . . . . .
O3 O 0.2524(4) 0.74507(13) 0.64060(15) 0.0703(7) Uani 1 1 d . . . . .
N1 N 0.4273(3) 0.58872(13) 0.53459(13) 0.0397(5) Uani 1 1 d . . . . .
H1 H 0.445(4) 0.5439(19) 0.5489(16) 0.039(8) Uiso 1 1 d . . . . .
N2 N 0.4108(3) 0.66781(13) 0.44083(13) 0.0453(6) Uani 1 1 d . . . . .
N3 N 0.3611(3) 0.70899(12) 0.54970(14) 0.0450(6) Uani 1 1 d . . . . .
N4 N 0.2575(3) 0.58356(15) 0.66940(14) 0.0521(6) Uani 1 1 d . . . . .
C1 C 0.4500(3) 0.59974(14) 0.46892(15) 0.0372(6) Uani 1 1 d . . . . .
C2 C 0.3732(4) 0.72497(16) 0.47983(17) 0.0466(7) Uani 1 1 d . . . . .
C3 C 0.3303(3) 0.63526(14) 0.56899(15) 0.0394(6) Uani 1 1 d . . . . .
C4 C 0.3712(4) 0.61547(16) 0.65026(16) 0.0456(7) Uani 1 1 d . . . . .
C5 C 0.1578(3) 0.61436(16) 0.55059(17) 0.0461(7) Uani 1 1 d . . . . .
C6 C 0.1254(4) 0.58325(18) 0.61117(17) 0.0506(7) Uani 1 1 d . . . . .
C7 C -0.0227(4) 0.5552(2) 0.6110(2) 0.0645(9) Uani 1 1 d . . . . .
H7 H -0.0447 0.5342 0.6517 0.077 Uiso 1 1 calc R . . . .
C8 C -0.1351(4) 0.5597(2) 0.5489(2) 0.0684(10) Uani 1 1 d . . . . .
H8 H -0.2349 0.5411 0.5476 0.082 Uiso 1 1 calc R . . . .
C9 C -0.1039(4) 0.5912(2) 0.4881(2) 0.0697(10) Uani 1 1 d . . . . .
H9 H -0.1829 0.5936 0.4468 0.084 Uiso 1 1 calc R . . . .
C10 C 0.0446(4) 0.6193(2) 0.4880(2) 0.0585(8) Uani 1 1 d . . . . .
H10 H 0.0664 0.6405 0.4474 0.070 Uiso 1 1 calc R . . . .
C11 C 0.5316(4) 0.6223(2) 0.70124(17) 0.0561(8) Uani 1 1 d . . . . .
C12 C 0.5996(6) 0.5474(3) 0.7158(3) 0.0874(14) Uani 1 1 d . . . . .
H12A H 0.5253 0.5177 0.7325 0.131 Uiso 1 1 calc GR . . . .
H12B H 0.6959 0.5496 0.7514 0.131 Uiso 1 1 calc GR . . . .
H12C H 0.6206 0.5278 0.6726 0.131 Uiso 1 1 calc GR . . . .
C13 C 0.5084(6) 0.6562(4) 0.7701(2) 0.103(2) Uani 1 1 d . . . . .
H13A H 0.4658 0.7032 0.7603 0.155 Uiso 1 1 calc GR . . . .
H13B H 0.6079 0.6591 0.8034 0.155 Uiso 1 1 calc GR . . . .
H13C H 0.4368 0.6278 0.7901 0.155 Uiso 1 1 calc GR . . . .
C14 C 0.6496(5) 0.6669(3) 0.6715(2) 0.0746(11) Uani 1 1 d . . . . .
H14A H 0.6657 0.6458 0.6281 0.112 Uiso 1 1 calc GR . . . .
H14B H 0.7479 0.6686 0.7058 0.112 Uiso 1 1 calc GR . . . .
H14C H 0.6093 0.7143 0.6620 0.112 Uiso 1 1 calc GR . . . .
C15 C 0.4313(3) 0.67972(12) 0.36942(9) 0.0495(7) Uani 1 1 d . . . . .
C20 C 0.5708(2) 0.70907(13) 0.35826(12) 0.0644(9) Uani 1 1 d G . . . .
H20 H 0.6484 0.7236 0.3970 0.077 Uiso 1 1 calc R . . . .
C19 C 0.5941(3) 0.71673(15) 0.28925(14) 0.0806(13) Uani 1 1 d G . . . .
H19 H 0.6874 0.7364 0.2818 0.097 Uiso 1 1 calc R . . . .
C18 C 0.4781(4) 0.69506(17) 0.23140(10) 0.0886(14) Uani 1 1 d G . . . .
H18 H 0.4937 0.7002 0.1852 0.106 Uiso 1 1 calc R . . . .
C17 C 0.3386(3) 0.66571(17) 0.24255(10) 0.0921(15) Uani 1 1 d G . . . .
H17 H 0.2610 0.6512 0.2038 0.110 Uiso 1 1 calc R . . . .
C16 C 0.3153(2) 0.65804(15) 0.31156(12) 0.0712(10) Uani 1 1 d G . . . .
H16 H 0.2220 0.6384 0.3190 0.085 Uiso 1 1 calc R . . . .
C21 C 0.3254(4) 0.76272(17) 0.59633(18) 0.0528(8) Uani 1 1 d . . . . .
C22 C 0.3906(4) 0.83421(17) 0.59249(19) 0.0546(8) Uani 1 1 d . . . . .
H22 H 0.4576 0.8431 0.5617 0.066 Uiso 1 1 calc R . . . .
C23 C 0.3544(4) 0.88603(18) 0.63264(19) 0.0557(8) Uani 1 1 d . . . . .
H23 H 0.2848 0.8745 0.6615 0.067 Uiso 1 1 calc R . . . .
C24 C 0.4114(4) 0.95925(17) 0.63667(17) 0.0507(7) Uani 1 1 d . . . . .
C25 C 0.3604(5) 1.00773(19) 0.6814(2) 0.0606(9) Uani 1 1 d . . . . .
H25 H 0.2902 0.9929 0.7088 0.073 Uiso 1 1 calc R . . . .
C26 C 0.4118(5) 1.07770(18) 0.6860(2) 0.0634(9) Uani 1 1 d . . . . .
H26 H 0.3766 1.1092 0.7166 0.076 Uiso 1 1 calc R . . . .
C27 C 0.5146(4) 1.10076(18) 0.64565(18) 0.0576(8) Uani 1 1 d . . . . .
H27 H 0.5489 1.1478 0.6486 0.069 Uiso 1 1 calc R . . . .
C28 C 0.5668(5) 1.0535(2) 0.6005(2) 0.0622(9) Uani 1 1 d . . . . .
H28 H 0.6359 1.0689 0.5728 0.075 Uiso 1 1 calc R . . . .
C29 C 0.5167(5) 0.98384(19) 0.59643(19) 0.0596(9) Uani 1 1 d . . . . .
H29 H 0.5536 0.9525 0.5663 0.072 Uiso 1 1 calc R . . . .
Cl1A Cl -0.0004(4) 0.1602(3) 0.54359(15) 0.1904(17) Uani 0.876(4) 1 d . . P A 2
Cl1 Cl 0.005(3) 0.106(2) 0.5572(12) 0.1904(17) Uani 0.124(4) 1 d . . P A 1
Cl2 Cl 0.079(5) 0.0359(17) 0.436(3) 0.1772(14) Uani 0.124(4) 1 d D . P A 1
Cl2A Cl 0.0867(6) 0.0680(2) 0.4383(3) 0.1772(14) Uani 0.876(4) 1 d . . P A 2
Cl3 Cl 0.160(2) 0.1854(17) 0.4906(10) 0.1723(13) Uani 0.124(4) 1 d D . P A 1
Cl3A Cl 0.2169(3) 0.2066(2) 0.46175(12) 0.1723(13) Uani 0.876(4) 1 d . . P A 2
C30 C 0.131(13) 0.094(2) 0.506(3) 0.154(3) Uani 0.124(4) 1 d D U P A 1
H30 H 0.2288 0.0757 0.5367 0.185 Uiso 0.124(4) 1 calc R . P A 1
C30A C 0.1418(17) 0.1286(7) 0.5026(6) 0.154(3) Uani 0.876(4) 1 d . U P A 2
H30A H 0.2277 0.1087 0.5390 0.185 Uiso 0.876(4) 1 calc R . P A 2


_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 C1 1.221(3) . ?
O2 C2 1.202(4) . ?
O3 C21 1.211(4) . ?
N1 H1 0.89(3) . ?
N1 C1 1.333(4) . ?
N1 C3 1.467(3) . ?
N2 C1 1.401(4) . ?
N2 C2 1.388(4) . ?
N2 C15 1.437(3) . ?
N3 C2 1.400(4) . ?
N3 C3 1.473(4) . ?
N3 C21 1.427(4) . ?
N4 C4 1.277(4) . ?
N4 C6 1.419(4) . ?
C3 C4 1.567(4) . ?
C3 C5 1.516(4) . ?
C4 C11 1.526(4) . ?
C5 C6 1.383(4) . ?
C5 C10 1.382(5) . ?
C6 C7 1.391(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.529(6) . ?
C11 C13 1.519(5) . ?
C11 C14 1.527(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.3900 . ?
C15 C16 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C21 C22 1.466(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.321(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.459(5) . ?
C24 C25 1.388(4) . ?
C24 C29 1.398(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.385(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.374(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.377(5) . ?
C29 H29 0.9300 . ?
Cl1A C30A 1.709(14) . ?
Cl1 C30 1.64(10) . ?
Cl2 C30 1.72(2) . ?
Cl2A C30A 1.670(13) . ?
Cl3 C30 1.78(2) . ?
Cl3A C30A 1.847(13) . ?
C30 H30 0.9800 . ?
C30A H30A 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 N1 H1 113(2) . . ?
C1 N1 C3 123.3(2) . . ?
C3 N1 H1 120(2) . . ?
C1 N2 C15 116.0(2) . . ?
C2 N2 C1 124.4(2) . . ?
C2 N2 C15 119.1(2) . . ?
C2 N3 C3 119.8(2) . . ?
C2 N3 C21 121.4(2) . . ?
C21 N3 C3 115.6(2) . . ?
C4 N4 C6 108.7(3) . . ?
O1 C1 N1 124.3(3) . . ?
O1 C1 N2 120.1(2) . . ?
N1 C1 N2 115.6(2) . . ?
O2 C2 N2 121.3(3) . . ?
O2 C2 N3 123.5(3) . . ?
N2 C2 N3 115.2(3) . . ?
N1 C3 N3 107.1(2) . . ?
N1 C3 C4 106.1(2) . . ?
N1 C3 C5 112.1(2) . . ?
N3 C3 C4 117.3(2) . . ?
N3 C3 C5 114.2(2) . . ?
C5 C3 C4 99.8(2) . . ?
N4 C4 C3 112.0(3) . . ?
N4 C4 C11 120.8(3) . . ?
C11 C4 C3 126.7(3) . . ?
C6 C5 C3 106.5(3) . . ?
C10 C5 C3 131.9(3) . . ?
C10 C5 C6 121.5(3) . . ?
C5 C6 N4 112.5(3) . . ?
C5 C6 C7 121.0(3) . . ?
C7 C6 N4 126.5(3) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.7(4) . . ?
C8 C7 H7 121.2 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.7(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 117.3(4) . . ?
C5 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C4 C11 C12 107.7(3) . . ?
C4 C11 C14 113.7(3) . . ?
C13 C11 C4 108.5(3) . . ?
C13 C11 C12 110.3(4) . . ?
C13 C11 C14 108.7(4) . . ?
C14 C11 C12 108.0(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 N2 120.06(18) . . ?
C20 C15 C16 120.0 . . ?
C16 C15 N2 119.84(18) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
O3 C21 N3 117.7(3) . . ?
O3 C21 C22 123.6(3) . . ?
N3 C21 C22 118.5(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 116.4 . . ?
C22 C23 C24 127.2(3) . . ?
C24 C23 H23 116.4 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 C29 117.4(3) . . ?
C29 C24 C23 122.6(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.5(3) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.2(3) . . ?
C29 C28 H28 119.9 . . ?
C24 C29 H29 119.3 . . ?
C28 C29 C24 121.3(3) . . ?
C28 C29 H29 119.3 . . ?
Cl1 C30 Cl2 118(6) . . ?
Cl1 C30 Cl3 96(4) . . ?
Cl1 C30 H30 107.5 . . ?
Cl2 C30 Cl3 120(3) . . ?
Cl2 C30 H30 107.5 . . ?
Cl3 C30 H30 107.5 . . ?
Cl1A C30A Cl3A 106.1(7) . . ?
Cl1A C30A H30A 108.7 . . ?
Cl2A C30A Cl1A 117.2(9) . . ?
Cl2A C30A Cl3A 107.4(6) . . ?
Cl2A C30A H30A 108.7 . . ?
Cl3A C30A H30A 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.89(3) 1.93(4) 2.812(3) 171(3) 3_666

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
O3 C21 C22 C23 -8.7(6) . . . . ?
N1 C3 C4 N4 -109.8(3) . . . . ?
N1 C3 C4 C11 62.0(4) . . . . ?
N1 C3 C5 C6 107.0(3) . . . . ?
N1 C3 C5 C10 -70.3(4) . . . . ?
N2 C15 C20 C19 176.3(2) . . . . ?
N2 C15 C16 C17 -176.3(2) . . . . ?
N3 C3 C4 N4 130.6(3) . . . . ?
N3 C3 C4 C11 -57.6(4) . . . . ?
N3 C3 C5 C6 -130.9(3) . . . . ?
N3 C3 C5 C10 51.7(4) . . . . ?
N3 C21 C22 C23 177.0(3) . . . . ?
N4 C4 C11 C12 64.9(4) . . . . ?
N4 C4 C11 C13 -54.5(5) . . . . ?
N4 C4 C11 C14 -175.6(3) . . . . ?
N4 C6 C7 C8 -179.5(3) . . . . ?
C1 N1 C3 N3 -39.4(4) . . . . ?
C1 N1 C3 C4 -165.4(2) . . . . ?
C1 N1 C3 C5 86.6(3) . . . . ?
C1 N2 C2 O2 174.3(3) . . . . ?
C1 N2 C2 N3 -6.1(4) . . . . ?
C1 N2 C15 C20 -94.0(3) . . . . ?
C1 N2 C15 C16 82.3(3) . . . . ?
C2 N2 C1 O1 -169.3(3) . . . . ?
C2 N2 C1 N1 9.5(4) . . . . ?
C2 N2 C15 C20 78.4(3) . . . . ?
C2 N2 C15 C16 -105.3(3) . . . . ?
C2 N3 C3 N1 41.7(3) . . . . ?
C2 N3 C3 C4 160.7(3) . . . . ?
C2 N3 C3 C5 -83.0(3) . . . . ?
C2 N3 C21 O3 148.9(3) . . . . ?
C2 N3 C21 C22 -36.5(5) . . . . ?
C3 N1 C1 O1 -165.2(3) . . . . ?
C3 N1 C1 N2 16.0(4) . . . . ?
C3 N3 C2 O2 157.5(3) . . . . ?
C3 N3 C2 N2 -22.1(4) . . . . ?
C3 N3 C21 O3 -10.7(5) . . . . ?
C3 N3 C21 C22 163.9(3) . . . . ?
C3 C4 C11 C12 -106.3(4) . . . . ?
C3 C4 C11 C13 134.3(4) . . . . ?
C3 C4 C11 C14 13.3(5) . . . . ?
C3 C5 C6 N4 2.2(4) . . . . ?
C3 C5 C6 C7 -177.2(3) . . . . ?
C3 C5 C10 C9 176.6(3) . . . . ?
C4 N4 C6 C5 2.3(4) . . . . ?
C4 N4 C6 C7 -178.3(3) . . . . ?
C4 C3 C5 C6 -4.9(3) . . . . ?
C4 C3 C5 C10 177.7(3) . . . . ?
C5 C3 C4 N4 6.8(3) . . . . ?
C5 C3 C4 C11 178.6(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C6 N4 C4 C3 -5.8(4) . . . . ?
C6 N4 C4 C11 -178.2(3) . . . . ?
C6 C5 C10 C9 -0.4(5) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C8 C9 C10 C5 0.0(6) . . . . ?
C10 C5 C6 N4 180.0(3) . . . . ?
C10 C5 C6 C7 0.5(5) . . . . ?
C15 N2 C1 O1 2.6(4) . . . . ?
C15 N2 C1 N1 -178.6(2) . . . . ?
C15 N2 C2 O2 2.6(5) . . . . ?
C15 N2 C2 N3 -177.8(2) . . . . ?
C15 C20 C19 C18 0.0 . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
C20 C19 C18 C17 0.0 . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
C21 N3 C2 O2 -1.3(5) . . . . ?
C21 N3 C2 N2 179.1(3) . . . . ?
C21 N3 C3 N1 -158.3(3) . . . . ?
C21 N3 C3 C4 -39.3(4) . . . . ?
C21 N3 C3 C5 76.9(3) . . . . ?
C21 C22 C23 C24 178.4(3) . . . . ?
C22 C23 C24 C25 179.4(4) . . . . ?
C22 C23 C24 C29 -0.2(6) . . . . ?
C23 C24 C25 C26 -179.6(4) . . . . ?
C23 C24 C29 C28 179.0(4) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C25 C24 C29 C28 -0.5(6) . . . . ?
C25 C26 C27 C28 -0.2(6) . . . . ?
C26 C27 C28 C29 -0.4(6) . . . . ?
C27 C28 C29 C24 0.8(6) . . . . ?
C29 C24 C25 C26 -0.1(6) . . . . ?

_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 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.803
