#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:58:19 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/26/1572609.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1572609
loop_
_publ_author_name
'Ran, Xiao-Yun'
'Xia, Wen-Li'
'Zhang, Li-Na'
'Yu, Xiao-Qi'
'Chen, Ping'
'Xie, Kun-Peng'
'Zhao, Yu'
'Yi, Cheng'
'Li, Kun'
_publ_section_title
;
 De novo design of type-l photosensitizer agents based on
 structure-inherent low triplet energy for hypoxia photodynamic therapy.
;
_journal_issue                   22
_journal_name_full               'Materials horizons'
_journal_page_first              5589
_journal_page_last               5599
_journal_paper_doi               10.1039/d4mh01167h
_journal_volume                  11
_journal_year                    2024
_chemical_formula_moiety         'C H2 Cl2, C32 H33 N5 O'
_chemical_formula_sum            'C33 H35 Cl2 N5 O'
_chemical_formula_weight         588.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-21 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.259(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.174(3)
_cell_length_b                   11.712(2)
_cell_length_c                   19.739(3)
_cell_measurement_reflns_used    6905
_cell_measurement_temperature    195(2)
_cell_measurement_theta_max      27.059
_cell_measurement_theta_min      2.311
_cell_volume                     3093.4(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      195.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18558
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.054
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1339 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.8105.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6919
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0631
_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)+(0.0783P)²+1.6043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4670
_reflns_number_total             6919
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4mh01167h2.cif
_cod_data_source_block           mo_yxq_lyz_fetcf_170k_2_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1572607--1572609.cif.'
_cod_original_cell_volume        3093.4(9)
_cod_database_code               1572609
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.898
_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. Uiso/Uaniso restraints and constraints
Uanis(C2A) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1A) = Uanis(C1)
Uanis(C2A) = Uanis(C2)
3. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=1-FVAR(1)
 Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C24(H24A,H24B), C28(H28A,H28B), C30(H30A,H30B), C34(H34A,H34B),
 C2A(H2AA,H2AB)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C23(H23), C26(H26), C32(H32), C33(H33)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,
 H25C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C1A(H1AA,H1AB,H1AC)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.99257(7) 0.46571(8) 0.39263(7) 0.0863(4) Uani 1 1 d . . . . .
Cl2 Cl 0.79729(9) 0.36426(9) 0.34420(8) 0.1034(4) Uani 1 1 d . . . . .
O1 O 1.02144(11) 0.89456(14) 0.62015(8) 0.0325(4) Uani 1 1 d . . . . .
N1 N 0.92555(18) 0.7572(2) 0.37804(12) 0.0475(6) Uani 1 1 d . . . . .
N2 N 1.17653(17) 0.9461(2) 0.52081(13) 0.0483(6) Uani 1 1 d . . . . .
N5 N 0.77552(17) 0.6398(2) 0.47562(13) 0.0509(6) Uani 1 1 d . . . . .
N4 N 0.37113(15) 0.72124(18) 0.41031(11) 0.0372(5) Uani 1 1 d . . . . .
C1 C 0.3655(3) 0.3724(3) 0.7237(2) 0.0529(10) Uani 0.834(6) 1 d . . P A 1
H1A H 0.3054 0.3358 0.6913 0.079 Uiso 0.834(6) 1 calc R U P A 1
H1B H 0.3678 0.4522 0.7093 0.079 Uiso 0.834(6) 1 calc R U P A 1
H1C H 0.3640 0.3696 0.7729 0.079 Uiso 0.834(6) 1 calc R U P A 1
C2 C 0.4577(3) 0.3099(3) 0.71984(19) 0.0414(8) Uani 0.841(6) 1 d . . P A 1
H2A H 0.4551 0.2296 0.7348 0.050 Uiso 0.841(6) 1 calc R U P A 1
H2B H 0.4568 0.3095 0.6695 0.050 Uiso 0.841(6) 1 calc R U P A 1
N3 N 0.55157(16) 0.36227(19) 0.76561(12) 0.0452(5) Uani 1 1 d . . . . .
C4 C 0.59592(18) 0.4507(2) 0.74101(13) 0.0349(5) Uani 1 1 d . . . . .
C5 C 0.69118(18) 0.4931(2) 0.78296(13) 0.0364(5) Uani 1 1 d . . . . .
H5 H 0.7225 0.4636 0.8299 0.044 Uiso 1 1 calc R U . . .
C6 C 0.73935(17) 0.5766(2) 0.75678(12) 0.0330(5) Uani 1 1 d . . . . .
H6 H 0.8041 0.6019 0.7850 0.040 Uiso 1 1 calc R U . . .
C7 C 0.69282(16) 0.62367(18) 0.68892(12) 0.0268(4) Uani 1 1 d . . . . .
C8 C 0.72808(16) 0.70547(18) 0.64638(11) 0.0253(4) Uani 1 1 d . . . . .
C9 C 0.82153(16) 0.75613(19) 0.67188(12) 0.0285(5) Uani 1 1 d . . . . .
H9 H 0.8498 0.7591 0.7227 0.034 Uiso 1 1 calc R U . . .
C10 C 0.88168(15) 0.80407(18) 0.63454(12) 0.0268(4) Uani 1 1 d . . . . .
C11 C 0.88391(16) 0.78584(19) 0.56561(12) 0.0283(5) Uani 1 1 d . . . . .
C12 C 0.97097(16) 0.84018(18) 0.55912(12) 0.0276(5) Uani 1 1 d . . . . .
C13 C 1.01015(16) 0.84257(19) 0.50386(12) 0.0301(5) Uani 1 1 d . . . . .
C14 C 0.96177(18) 0.7938(2) 0.43483(13) 0.0344(5) Uani 1 1 d . . . . .
C15 C 1.10298(18) 0.8999(2) 0.51408(13) 0.0347(5) Uani 1 1 d . . . . .
C16 C 0.97050(16) 0.87894(19) 0.67359(12) 0.0296(5) Uani 1 1 d . . . . .
C17 C 1.04467(18) 0.8226(2) 0.73862(14) 0.0405(6) Uani 1 1 d . . . . .
H17A H 1.0614 0.7464 0.7255 0.061 Uiso 1 1 calc R U . . .
H17B H 1.0151 0.8158 0.7768 0.061 Uiso 1 1 calc R U . . .
H17C H 1.1055 0.8691 0.7556 0.061 Uiso 1 1 calc R U . . .
C18 C 0.93983(19) 0.9978(2) 0.68981(15) 0.0402(6) Uani 1 1 d . . . . .
H18A H 0.9997 1.0437 0.7126 0.060 Uiso 1 1 calc R U . . .
H18B H 0.9005 0.9917 0.7223 0.060 Uiso 1 1 calc R U . . .
H18C H 0.8995 1.0345 0.6450 0.060 Uiso 1 1 calc R U . . .
C19 C 0.82358(17) 0.7063(2) 0.51464(13) 0.0344(5) Uani 1 1 d . . . . .
C20 C 0.64576(15) 0.72026(17) 0.57910(11) 0.0260(4) Uani 1 1 d . . . . .
C21 C 0.56623(16) 0.64690(17) 0.57947(12) 0.0265(4) Uani 1 1 d . . . . .
C22 C 0.59713(16) 0.58448(18) 0.64821(12) 0.0274(5) Uani 1 1 d . . . . .
C23 C 0.54851(17) 0.5003(2) 0.67239(13) 0.0332(5) Uani 1 1 d . . . . .
H23 H 0.4839 0.4756 0.6436 0.040 Uiso 1 1 calc R U . . .
C24 C 0.5913(2) 0.3258(2) 0.84071(15) 0.0436(6) Uani 1 1 d . . . . .
H24A H 0.6643 0.3143 0.8535 0.052 Uiso 1 1 calc R U . . .
H24B H 0.5612 0.2512 0.8454 0.052 Uiso 1 1 calc R U . . .
C25 C 0.5726(2) 0.4077(3) 0.89342(18) 0.0579(8) Uani 1 1 d . . . . .
H25A H 0.5985 0.4832 0.8874 0.087 Uiso 1 1 calc R U . . .
H25B H 0.6065 0.3803 0.9424 0.087 Uiso 1 1 calc R U . . .
H25C H 0.5006 0.4129 0.8849 0.087 Uiso 1 1 calc R U . . .
C26 C 0.47622(16) 0.64509(18) 0.52468(12) 0.0286(5) Uani 1 1 d . . . . .
H26 H 0.4253 0.5935 0.5262 0.034 Uiso 1 1 calc R U . . .
C27 C 0.45985(16) 0.72088(19) 0.46573(12) 0.0304(5) Uani 1 1 d . . . . .
C28 C 0.3457(2) 0.8138(3) 0.35695(15) 0.0486(7) Uani 1 1 d . . . . .
H28A H 0.2848 0.7920 0.3171 0.058 Uiso 1 1 calc R U . . .
H28B H 0.4007 0.8224 0.3369 0.058 Uiso 1 1 calc R U . . .
C29 C 0.3275(2) 0.9286(3) 0.38729(19) 0.0575(8) Uani 1 1 d . . . . .
H29A H 0.2781 0.9192 0.4117 0.086 Uiso 1 1 calc R U . . .
H29B H 0.3026 0.9837 0.3481 0.086 Uiso 1 1 calc R U . . .
H29C H 0.3904 0.9567 0.4215 0.086 Uiso 1 1 calc R U . . .
C30 C 0.29249(18) 0.6380(2) 0.40659(15) 0.0419(6) Uani 1 1 d . . . . .
H30A H 0.3239 0.5662 0.4297 0.050 Uiso 1 1 calc R U . . .
H30B H 0.2556 0.6210 0.3556 0.050 Uiso 1 1 calc R U . . .
C31 C 0.2187(2) 0.6782(3) 0.4424(2) 0.0624(9) Uani 1 1 d . . . . .
H31A H 0.2547 0.6974 0.4926 0.094 Uiso 1 1 calc R U . . .
H31B H 0.1705 0.6172 0.4403 0.094 Uiso 1 1 calc R U . . .
H31C H 0.1833 0.7458 0.4174 0.094 Uiso 1 1 calc R U . . .
C32 C 0.53801(16) 0.79726(19) 0.46697(12) 0.0310(5) Uani 1 1 d . . . . .
H32 H 0.5276 0.8504 0.4289 0.037 Uiso 1 1 calc R U . . .
C33 C 0.62852(16) 0.79688(19) 0.52162(12) 0.0301(5) Uani 1 1 d . . . . .
H33 H 0.6795 0.8487 0.5204 0.036 Uiso 1 1 calc R U . . .
C34 C 0.8701(3) 0.4804(4) 0.3852(3) 0.0958(15) Uani 1 1 d . . . . .
H34A H 0.8432 0.5501 0.3571 0.115 Uiso 1 1 calc R U . . .
H34B H 0.8651 0.4906 0.4337 0.115 Uiso 1 1 calc R U . . .
C2A C 0.4292(16) 0.3752(15) 0.7451(10) 0.0414(8) Uani 0.159(6) 1 d . U P A 2
H2AA H 0.4064 0.3605 0.7865 0.050 Uiso 0.159(6) 1 calc R U P A 2
H2AB H 0.4042 0.4502 0.7234 0.050 Uiso 0.159(6) 1 calc R U P A 2
C1A C 0.4029(16) 0.2803(17) 0.6913(12) 0.0529(10) Uani 0.166(6) 1 d . U P A 2
H1AA H 0.4318 0.2958 0.6535 0.079 Uiso 0.166(6) 1 calc R U P A 2
H1AB H 0.3301 0.2746 0.6702 0.079 Uiso 0.166(6) 1 calc R U P A 2
H1AC H 0.4297 0.2082 0.7152 0.079 Uiso 0.166(6) 1 calc R U P A 2
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'
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
C12 O1 C16 109.99(16) . . ?
C27 N4 C28 121.2(2) . . ?
C27 N4 C30 121.5(2) . . ?
C30 N4 C28 116.8(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N3 C2 C1 112.7(3) . . ?
N3 C2 H2A 109.1 . . ?
N3 C2 H2B 109.1 . . ?
C4 N3 C2 121.4(2) . . ?
C4 N3 C24 120.5(2) . . ?
C4 N3 C2A 114.1(6) . . ?
C24 N3 C2 117.8(2) . . ?
C24 N3 C2A 107.3(6) . . ?
N3 C4 C5 120.9(2) . . ?
N3 C4 C23 121.0(2) . . ?
C5 C4 C23 118.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 131.7(2) . . ?
C6 C7 C22 118.7(2) . . ?
C22 C7 C8 109.44(19) . . ?
C9 C8 C7 122.5(2) . . ?
C9 C8 C20 131.36(19) . . ?
C20 C8 C7 106.10(18) . . ?
C8 C9 H9 114.8 . . ?
C8 C9 C10 130.5(2) . . ?
C10 C9 H9 114.8 . . ?
C9 C10 C16 120.39(19) . . ?
C11 C10 C9 131.5(2) . . ?
C11 C10 C16 107.65(18) . . ?
C10 C11 C12 108.57(19) . . ?
C10 C11 C19 126.0(2) . . ?
C19 C11 C12 124.1(2) . . ?
O1 C12 C11 110.54(18) . . ?
O1 C12 C13 117.8(2) . . ?
C13 C12 C11 131.6(2) . . ?
C12 C13 C14 123.7(2) . . ?
C12 C13 C15 119.3(2) . . ?
C14 C13 C15 116.9(2) . . ?
N1 C14 C13 177.0(3) . . ?
N2 C15 C13 178.6(3) . . ?
O1 C16 C10 103.20(17) . . ?
O1 C16 C17 107.07(18) . . ?
O1 C16 C18 106.15(18) . . ?
C10 C16 C18 112.82(18) . . ?
C17 C16 C10 113.92(19) . . ?
C17 C16 C18 112.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 C11 177.6(3) . . ?
C21 C20 C8 108.74(18) . . ?
C33 C20 C8 133.2(2) . . ?
C33 C20 C21 117.7(2) . . ?
C20 C21 C22 108.02(18) . . ?
C26 C21 C20 122.6(2) . . ?
C26 C21 C22 129.30(19) . . ?
C7 C22 C21 107.56(18) . . ?
C23 C22 C7 122.3(2) . . ?
C23 C22 C21 130.1(2) . . ?
C4 C23 H23 120.3 . . ?
C22 C23 C4 119.3(2) . . ?
C22 C23 H23 120.3 . . ?
N3 C24 H24A 108.6 . . ?
N3 C24 H24B 108.6 . . ?
N3 C24 C25 114.7(2) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 C26 H26 120.2 . . ?
C21 C26 C27 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
N4 C27 C26 121.0(2) . . ?
N4 C27 C32 121.3(2) . . ?
C32 C27 C26 117.7(2) . . ?
N4 C28 H28A 108.8 . . ?
N4 C28 H28B 108.8 . . ?
N4 C28 C29 113.7(2) . . ?
H28A C28 H28B 107.7 . . ?
C29 C28 H28A 108.8 . . ?
C29 C28 H28B 108.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C30 H30A 108.8 . . ?
N4 C30 H30B 108.8 . . ?
N4 C30 C31 113.6(2) . . ?
H30A C30 H30B 107.7 . . ?
C31 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C27 C32 H32 118.9 . . ?
C33 C32 C27 122.2(2) . . ?
C33 C32 H32 118.9 . . ?
C20 C33 H33 119.9 . . ?
C32 C33 C20 120.3(2) . . ?
C32 C33 H33 119.9 . . ?
Cl1 C34 Cl2 113.2(2) . . ?
Cl1 C34 H34A 108.9 . . ?
Cl1 C34 H34B 108.9 . . ?
Cl2 C34 H34A 108.9 . . ?
Cl2 C34 H34B 108.9 . . ?
H34A C34 H34B 107.8 . . ?
N3 C2A H2AA 112.6 . . ?
N3 C2A H2AB 112.6 . . ?
H2AA C2A H2AB 110.1 . . ?
C1A C2A N3 95.8(14) . . ?
C1A C2A H2AA 112.6 . . ?
C1A C2A H2AB 112.6 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
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 C34 1.702(4) . ?
Cl2 C34 1.737(4) . ?
O1 C12 1.342(3) . ?
O1 C16 1.473(2) . ?
N1 C14 1.151(3) . ?
N2 C15 1.143(3) . ?
N5 C19 1.148(3) . ?
N4 C27 1.368(3) . ?
N4 C28 1.471(3) . ?
N4 C30 1.464(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.521(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N3 1.473(4) . ?
N3 C4 1.380(3) . ?
N3 C24 1.465(3) . ?
N3 C2A 1.65(2) . ?
C4 C5 1.421(3) . ?
C4 C23 1.422(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 C8 1.466(3) . ?
C7 C22 1.406(3) . ?
C8 C9 1.386(3) . ?
C8 C20 1.460(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.414(3) . ?
C10 C11 1.388(3) . ?
C10 C16 1.519(3) . ?
C11 C12 1.431(3) . ?
C11 C19 1.429(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.427(3) . ?
C13 C15 1.431(3) . ?
C16 C17 1.516(3) . ?
C16 C18 1.524(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.419(3) . ?
C20 C33 1.403(3) . ?
C21 C22 1.475(3) . ?
C21 C26 1.374(3) . ?
C22 C23 1.375(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.501(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26 0.9500 . ?
C26 C27 1.420(3) . ?
C27 C32 1.418(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.529(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.517(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C33 1.377(3) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C1A 1.50(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
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 C12 C13 C14 -176.5(2) . . . . ?
O1 C12 C13 C15 1.4(3) . . . . ?
N4 C27 C32 C33 -178.8(2) . . . . ?
C1 C2 N3 C4 -86.6(3) . . . . ?
C1 C2 N3 C24 87.1(3) . . . . ?
C2 N3 C4 C5 -173.9(2) . . . . ?
C2 N3 C4 C23 4.8(4) . . . . ?
C2 N3 C24 C25 -101.9(3) . . . . ?
N3 C4 C5 C6 175.6(2) . . . . ?
N3 C4 C23 C22 -176.8(2) . . . . ?
C4 N3 C24 C25 71.9(3) . . . . ?
C4 N3 C2A C1A 109.5(10) . . . . ?
C4 C5 C6 C7 2.2(4) . . . . ?
C5 C4 C23 C22 1.9(3) . . . . ?
C5 C6 C7 C8 -175.1(2) . . . . ?
C5 C6 C7 C22 -0.1(3) . . . . ?
C6 C7 C8 C9 -2.9(4) . . . . ?
C6 C7 C8 C20 179.1(2) . . . . ?
C6 C7 C22 C21 -179.54(19) . . . . ?
C6 C7 C22 C23 -1.1(3) . . . . ?
C7 C8 C9 C10 156.2(2) . . . . ?
C7 C8 C20 C21 -2.6(2) . . . . ?
C7 C8 C20 C33 170.1(2) . . . . ?
C7 C22 C23 C4 0.1(3) . . . . ?
C8 C7 C22 C21 -3.6(2) . . . . ?
C8 C7 C22 C23 174.9(2) . . . . ?
C8 C9 C10 C11 -23.2(4) . . . . ?
C8 C9 C10 C16 165.8(2) . . . . ?
C8 C20 C21 C22 0.5(2) . . . . ?
C8 C20 C21 C26 176.98(19) . . . . ?
C8 C20 C33 C32 -174.0(2) . . . . ?
C9 C8 C20 C21 179.6(2) . . . . ?
C9 C8 C20 C33 -7.7(4) . . . . ?
C9 C10 C11 C12 -169.4(2) . . . . ?
C9 C10 C11 C19 -2.2(4) . . . . ?
C9 C10 C16 O1 170.87(19) . . . . ?
C9 C10 C16 C17 55.2(3) . . . . ?
C9 C10 C16 C18 -75.0(3) . . . . ?
C10 C11 C12 O1 -2.0(2) . . . . ?
C10 C11 C12 C13 176.1(2) . . . . ?
C11 C10 C16 O1 -2.1(2) . . . . ?
C11 C10 C16 C17 -117.8(2) . . . . ?
C11 C10 C16 C18 112.0(2) . . . . ?
C11 C12 C13 C14 5.6(4) . . . . ?
C11 C12 C13 C15 -176.6(2) . . . . ?
C12 O1 C16 C10 0.9(2) . . . . ?
C12 O1 C16 C17 121.4(2) . . . . ?
C12 O1 C16 C18 -117.9(2) . . . . ?
C16 O1 C12 C11 0.5(2) . . . . ?
C16 O1 C12 C13 -177.82(19) . . . . ?
C16 C10 C11 C12 2.5(2) . . . . ?
C16 C10 C11 C19 169.7(2) . . . . ?
C19 C11 C12 O1 -169.5(2) . . . . ?
C19 C11 C12 C13 8.6(4) . . . . ?
C20 C8 C9 C10 -26.3(4) . . . . ?
C20 C21 C22 C7 1.9(2) . . . . ?
C20 C21 C22 C23 -176.4(2) . . . . ?
C20 C21 C26 C27 -1.6(3) . . . . ?
C21 C20 C33 C32 -1.8(3) . . . . ?
C21 C22 C23 C4 178.3(2) . . . . ?
C21 C26 C27 N4 180.0(2) . . . . ?
C21 C26 C27 C32 -1.0(3) . . . . ?
C22 C7 C8 C9 -178.15(19) . . . . ?
C22 C7 C8 C20 3.8(2) . . . . ?
C22 C21 C26 C27 174.1(2) . . . . ?
C23 C4 C5 C6 -3.1(4) . . . . ?
C24 N3 C4 C5 12.6(4) . . . . ?
C24 N3 C4 C23 -168.7(2) . . . . ?
C24 N3 C2A C1A -114.4(10) . . . . ?
C26 C21 C22 C7 -174.3(2) . . . . ?
C26 C21 C22 C23 7.4(4) . . . . ?
C26 C27 C32 C33 2.2(3) . . . . ?
C27 N4 C28 C29 -68.3(3) . . . . ?
C27 N4 C30 C31 90.9(3) . . . . ?
C27 C32 C33 C20 -0.7(3) . . . . ?
C28 N4 C27 C26 167.4(2) . . . . ?
C28 N4 C27 C32 -11.6(3) . . . . ?
C28 N4 C30 C31 -81.6(3) . . . . ?
C30 N4 C27 C26 -4.8(3) . . . . ?
C30 N4 C27 C32 176.3(2) . . . . ?
C30 N4 C28 C29 104.2(3) . . . . ?
C33 C20 C21 C22 -173.49(18) . . . . ?
C33 C20 C21 C26 3.0(3) . . . . ?
C2A N3 C4 C5 142.4(7) . . . . ?
C2A N3 C4 C23 -38.9(7) . . . . ?
C2A N3 C24 C25 -60.8(7) . . . . ?
