#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:13:18 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158102.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_7158102
loop_
_publ_author_name
'Kudale, Vishal Suresh'
'Mutra, Mohana Reddy'
'Chu, Ching-Piao'
'Wang, Jeh-Jeng'
_publ_section_title
;
Unusual C3-acetylation of quinoxalin-2(1H)-one
via oxidative C-C and C-O bond cleavages of PEG-400.
;
_journal_issue 25
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 5567
_journal_page_last 5571
_journal_paper_doi 10.1039/d1ob00769f
_journal_volume 19
_journal_year 2021
_chemical_formula_moiety '2(C17 H12 Cl2 N2 O2)'
_chemical_formula_sum 'C34 H24 Cl4 N4 O4'
_chemical_formula_weight 694.37
_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 2020-05-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC. 2021-05-28 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 93.0880(10)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.70700(10)
_cell_length_b 17.6134(2)
_cell_length_c 22.5179(2)
_cell_measurement_reflns_used 34871
_cell_measurement_temperature 113(2)
_cell_measurement_theta_max 27.0120
_cell_measurement_theta_min 2.1410
_cell_volume 3052.29(6)
_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)'
_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 t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -79.00 36.00 0.50 5.65 -- 10.60 -77.00 0.00 230
2 \w -20.00 100.00 0.50 5.65 -- 10.60 57.00-150.00 240
3 \w -17.00 100.00 0.50 5.65 -- 10.60 82.00-150.00 234
4 \w -17.00 100.00 0.50 5.65 -- 10.60 82.00-150.00 234
5 \w -79.00 41.00 0.50 5.65 -- 10.60 -57.00 0.00 240
6 \w -100.00 17.00 0.50 5.65 -- -10.90 -82.00 30.00 234
7 \w -79.00 38.00 0.50 5.65 -- 10.60 -82.00 150.00 234
8 \w -15.00 100.00 0.50 5.65 -- 10.60 77.00 -30.00 230
9 \w -79.00 -54.00 0.50 5.65 -- 10.60 -57.00 -90.00 50
10 \w -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 '\w 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_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_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_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'Rigaku (Mo) X-ray Source'
_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_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_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
_refine_diff_density_max 0.319
_refine_diff_density_min -0.292
_refine_diff_density_rms 0.045
_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_restrained_S_all 1.059
_refine_ls_R_factor_all 0.0355
_refine_ls_R_factor_gt 0.0305
_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/[\s^2^(Fo^2^)+(0.0342P)^2^+1.4144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0754
_refine_ls_wR_factor_ref 0.0777
_reflns_Friedel_coverage 0.000
_reflns_number_gt 5716
_reflns_number_total 6459
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d1ob00769f2.cif
_cod_data_source_block k10905-jjw-c
_cod_depositor_comments
'Adding full bibliography for 7158102--7158103.cif.'
_cod_database_code 7158102
_shelx_shelxl_version_number 2018/3
_chemical_oxdiff_formula 'C17 H22 N2 O2 Cl2'
_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.
;
_diffrn_oxdiff_digest_frames
;
01529f3da72ce609e168521cc37e37332e000254cd8
;
_diffrn_oxdiff_digest_hkl
;
01ba08c94d5461a4b41e335418e23a0a18ff17
;
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 26.32
_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)
;
_shelx_res_file
;
TITL k10905-jjw-c_a.res in P2(1)/c
k10905-jjw-c.res
created by SHELXL-2018/3 at 18:00:22 on 17-May-2020
REM Old TITL K10905-JJW-C in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.117, Rweak 0.004, Alpha 0.016
REM 0.897 for 216 systematic absences, Orientation as input
REM Formula found by SHELXT: C24 N4 O4 Cl4
CELL 0.71073 7.707 17.6134 22.5179 90 93.088 90
ZERR 4 0.0001 0.0002 0.0002 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 136 96 16 16 16
L.S. 4
PLAN 5
MORE -1
BOND $H
CONF
fmap 2
acta
OMIT 0 0 2
OMIT 0 1 1
OMIT -2 1 1
REM
REM
REM
WGHT 0.034200 1.414400
FVAR 0.77172
CL1 3 0.806642 0.340673 0.519294 11.00000 0.02223 0.04002 =
0.02011 0.00245 -0.00179 0.00339
CL2 3 0.160684 0.441780 0.466642 11.00000 0.01863 0.04233 =
0.02468 0.00265 0.00723 0.00225
O1 5 0.335564 0.389032 0.237746 11.00000 0.03152 0.01969 =
0.03074 -0.00371 0.00191 -0.00202
O2 5 0.576878 0.389565 0.142699 11.00000 0.05664 0.02919 =
0.03007 -0.00075 0.00937 0.01157
N1 4 0.347355 0.500456 0.288941 11.00000 0.01939 0.01766 =
0.01770 0.00145 0.00046 -0.00137
N2 4 0.504194 0.568160 0.193920 11.00000 0.02322 0.02458 =
0.01909 0.00351 0.00047 0.00320
C1 1 0.393667 0.576759 0.292841 11.00000 0.01539 0.01802 =
0.01935 0.00133 -0.00260 0.00032
C2 1 0.469731 0.609635 0.243863 11.00000 0.01804 0.02141 =
0.01938 0.00262 -0.00097 0.00156
C3 1 0.514739 0.686802 0.245654 11.00000 0.02241 0.02339 =
0.02653 0.00722 -0.00104 -0.00334
AFIX 43
H3 2 0.564873 0.708728 0.213141 11.00000 -1.20000
AFIX 0
C4 1 0.486025 0.730296 0.294484 11.00000 0.02627 0.01751 =
0.03390 0.00130 -0.00623 -0.00341
AFIX 43
H4 2 0.516026 0.781443 0.295289 11.00000 -1.20000
AFIX 0
C5 1 0.411046 0.696788 0.343076 11.00000 0.02407 0.02326 =
0.02565 -0.00446 -0.00494 0.00087
AFIX 43
H5 2 0.391207 0.726217 0.376324 11.00000 -1.20000
AFIX 0
C6 1 0.365698 0.621053 0.342931 11.00000 0.02079 0.02347 =
0.01920 0.00042 -0.00096 -0.00017
AFIX 43
H6 2 0.316902 0.599622 0.375893 11.00000 -1.20000
AFIX 0
C7 1 0.269966 0.463560 0.339428 11.00000 0.01910 0.01920 =
0.02044 0.00260 0.00232 -0.00197
AFIX 23
H7A 2 0.201404 0.420363 0.325322 11.00000 -1.20000
H7B 2 0.192845 0.498967 0.357853 11.00000 -1.20000
AFIX 0
C8 1 0.408049 0.437057 0.385188 11.00000 0.01897 0.01494 =
0.01919 0.00036 0.00182 -0.00333
C9 1 0.576596 0.420621 0.369684 11.00000 0.02148 0.02334 =
0.01754 0.00109 0.00421 -0.00199
AFIX 43
H9 2 0.606717 0.429073 0.330793 11.00000 -1.20000
AFIX 0
C10 1 0.700421 0.392072 0.410542 11.00000 0.01831 0.02444 =
0.02171 -0.00112 0.00398 -0.00100
AFIX 43
H10 2 0.812339 0.381613 0.399348 11.00000 -1.20000
AFIX 0
C11 1 0.654973 0.379340 0.468336 11.00000 0.01966 0.02202 =
0.01904 -0.00063 -0.00228 -0.00182
C12 1 0.490263 0.395985 0.486102 11.00000 0.02227 0.02286 =
0.01692 -0.00097 0.00244 -0.00431
AFIX 43
H12 2 0.461451 0.388307 0.525229 11.00000 -1.20000
AFIX 0
C13 1 0.369144 0.424429 0.444053 11.00000 0.01611 0.01955 =
0.02142 -0.00214 0.00457 -0.00290
C14 1 0.379116 0.455920 0.240169 11.00000 0.02207 0.01961 =
0.02032 -0.00025 -0.00240 0.00165
C15 1 0.466544 0.496675 0.192628 11.00000 0.02515 0.02390 =
0.01734 0.00119 -0.00128 0.00512
C16 1 0.525904 0.453958 0.139068 11.00000 0.03434 0.03031 =
0.02075 -0.00045 0.00207 0.00574
C17 1 0.527027 0.498296 0.082243 11.00000 0.09039 0.04546 =
0.02235 0.00545 0.01428 0.02514
AFIX 137
H17C 2 0.565743 0.466254 0.051108 11.00000 -1.50000
H17A 2 0.604274 0.540813 0.087487 11.00000 -1.50000
H17B 2 0.411782 0.516207 0.071752 11.00000 -1.50000
AFIX 0
CL3 3 0.402026 0.197769 0.514660 11.00000 0.02874 0.04042 =
0.02170 0.00319 -0.00159 0.00198
CL4 3 -0.245010 0.170108 0.418222 11.00000 0.02094 0.04408 =
0.04262 0.01120 0.00749 -0.00809
O3 5 -0.118154 0.390495 0.270215 11.00000 0.03657 0.02530 =
0.02971 -0.00706 0.00771 0.00194
O4 5 0.002013 0.493360 0.185771 11.00000 0.09380 0.02102 =
0.03631 -0.00382 0.00671 0.00301
N3 4 -0.048460 0.267537 0.252410 11.00000 0.01952 0.02191 =
0.01919 -0.00236 -0.00014 -0.00115
N4 4 0.043917 0.308413 0.138899 11.00000 0.02019 0.02176 =
0.02191 -0.00271 -0.00254 -0.00110
C18 1 0.018979 0.212311 0.215601 11.00000 0.01412 0.02176 =
0.02252 -0.00433 -0.00302 -0.00229
C19 1 0.043168 0.137021 0.233843 11.00000 0.02072 0.02308 =
0.02258 -0.00051 -0.00285 -0.00357
AFIX 43
H19 2 0.016449 0.122298 0.271947 11.00000 -1.20000
AFIX 0
C20 1 0.106954 0.084658 0.194959 11.00000 0.02141 0.01935 =
0.03177 -0.00155 -0.00597 -0.00110
AFIX 43
H20 2 0.122821 0.034557 0.207109 11.00000 -1.20000
AFIX 0
C21 1 0.147998 0.105876 0.137617 11.00000 0.02322 0.02332 =
0.02839 -0.00817 -0.00274 0.00198
AFIX 43
H21 2 0.189601 0.069932 0.111680 11.00000 -1.20000
AFIX 0
C22 1 0.126735 0.180023 0.119622 11.00000 0.02048 0.02557 =
0.02215 -0.00399 -0.00130 -0.00151
AFIX 43
H22 2 0.155434 0.194303 0.081619 11.00000 -1.20000
AFIX 0
C23 1 0.061986 0.234215 0.158297 11.00000 0.01684 0.02036 =
0.02083 -0.00260 -0.00407 -0.00141
C24 1 -0.120069 0.245123 0.308654 11.00000 0.01965 0.02612 =
0.02324 -0.00196 0.00332 -0.00258
AFIX 23
H24B 2 -0.181646 0.197454 0.302779 11.00000 -1.20000
H24A 2 -0.203963 0.283039 0.319514 11.00000 -1.20000
AFIX 0
C25 1 0.013726 0.235933 0.359529 11.00000 0.01991 0.01738 =
0.02174 -0.00300 0.00284 -0.00084
C26 1 0.184433 0.259970 0.356951 11.00000 0.02166 0.01902 =
0.01884 -0.00183 0.00541 -0.00210
AFIX 43
H26 2 0.218494 0.284405 0.322867 11.00000 -1.20000
AFIX 0
C27 1 0.305874 0.248544 0.403875 11.00000 0.01891 0.02126 =
0.02165 -0.00251 0.00332 -0.00240
AFIX 43
H27 2 0.420512 0.263986 0.401006 11.00000 -1.20000
AFIX 0
C28 1 0.253316 0.213751 0.455030 11.00000 0.02335 0.02307 =
0.01991 -0.00134 0.00041 0.00156
C29 1 0.083716 0.190712 0.460155 11.00000 0.02835 0.02488 =
0.02294 0.00491 0.00724 0.00067
AFIX 43
H29 2 0.048745 0.168562 0.495045 11.00000 -1.20000
AFIX 0
C30 1 -0.032730 0.201397 0.412139 11.00000 0.01902 0.02209 =
0.02885 0.00129 0.00708 -0.00246
C31 1 -0.061913 0.343377 0.236308 11.00000 0.01988 0.02284 =
0.02433 -0.00380 -0.00178 -0.00028
C32 1 -0.007907 0.359504 0.175262 11.00000 0.02159 0.02215 =
0.02325 -0.00260 -0.00268 0.00057
C33 1 -0.006121 0.439908 0.152720 11.00000 0.03433 0.02360 =
0.02851 -0.00122 0.00185 0.00329
C34 1 -0.003328 0.450056 0.086743 11.00000 0.08965 0.02788 =
0.03409 0.00380 0.01257 0.00268
AFIX 137
H34C 2 0.105133 0.431820 0.073249 11.00000 -1.50000
H34A 2 -0.016095 0.502923 0.077101 11.00000 -1.50000
H34B 2 -0.097232 0.421929 0.067588 11.00000 -1.50000
AFIX 0
HKLF 4
REM k10905-jjw-c_a.res in P2(1)/c
REM wR2 = 0.0777, GooF = S = 1.059, Restrained GooF = 1.059 for all data
REM R1 = 0.0305 for 5716 Fo > 4sig(Fo) and 0.0355 for all 6459 data
REM 417 parameters refined using 0 restraints
END
WGHT 0.0342 1.4144
REM Highest difference peak 0.319, deepest hole -0.292, 1-sigma level 0.045
Q1 1 -0.1066 0.4858 0.1751 11.00000 0.05 0.32
Q2 1 -0.0377 0.2359 0.3333 11.00000 0.05 0.27
Q3 1 0.4884 0.4770 0.1675 11.00000 0.05 0.26
Q4 1 0.5056 0.6418 0.2481 11.00000 0.05 0.26
Q5 1 0.0618 0.2220 0.1905 11.00000 0.05 0.25
;
_shelx_res_checksum 75159
_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
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 0.80664(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 . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.02223(19) 0.0400(2) 0.02011(17) 0.00245(14) -0.00179(14) 0.00339(15)
Cl2 0.01863(19) 0.0423(2) 0.02468(18) 0.00265(15) 0.00723(14) 0.00225(15)
O1 0.0315(6) 0.0197(5) 0.0307(6) -0.0037(4) 0.0019(5) -0.0020(4)
O2 0.0566(8) 0.0292(6) 0.0301(6) -0.0008(5) 0.0094(6) 0.0116(6)
N1 0.0194(6) 0.0177(5) 0.0177(6) 0.0015(4) 0.0005(5) -0.0014(5)
N2 0.0232(7) 0.0246(6) 0.0191(6) 0.0035(5) 0.0005(5) 0.0032(5)
C1 0.0154(7) 0.0180(6) 0.0194(6) 0.0013(5) -0.0026(5) 0.0003(5)
C2 0.0180(7) 0.0214(7) 0.0194(7) 0.0026(5) -0.0010(5) 0.0016(5)
C3 0.0224(8) 0.0234(7) 0.0265(7) 0.0072(6) -0.0010(6) -0.0033(6)
C4 0.0263(8) 0.0175(7) 0.0339(8) 0.0013(6) -0.0062(6) -0.0034(6)
C5 0.0241(8) 0.0233(7) 0.0257(7) -0.0045(6) -0.0049(6) 0.0009(6)
C6 0.0208(7) 0.0235(7) 0.0192(7) 0.0004(5) -0.0010(6) -0.0002(6)
C7 0.0191(7) 0.0192(7) 0.0204(7) 0.0026(5) 0.0023(5) -0.0020(5)
C8 0.0190(7) 0.0149(6) 0.0192(6) 0.0004(5) 0.0018(5) -0.0033(5)
C9 0.0215(8) 0.0233(7) 0.0175(6) 0.0011(5) 0.0042(5) -0.0020(6)
C10 0.0183(7) 0.0244(7) 0.0217(7) -0.0011(6) 0.0040(6) -0.0010(6)
C11 0.0197(7) 0.0220(7) 0.0190(7) -0.0006(5) -0.0023(5) -0.0018(6)
C12 0.0223(8) 0.0229(7) 0.0169(6) -0.0010(5) 0.0024(5) -0.0043(6)
C13 0.0161(7) 0.0195(7) 0.0214(7) -0.0021(5) 0.0046(5) -0.0029(5)
C14 0.0221(8) 0.0196(7) 0.0203(7) -0.0002(5) -0.0024(6) 0.0017(6)
C15 0.0251(8) 0.0239(7) 0.0173(7) 0.0012(5) -0.0013(6) 0.0051(6)
C16 0.0343(9) 0.0303(8) 0.0207(7) -0.0004(6) 0.0021(6) 0.0057(7)
C17 0.0904(17) 0.0455(11) 0.0223(8) 0.0054(8) 0.0143(9) 0.0251(11)
Cl3 0.0287(2) 0.0404(2) 0.02170(18) 0.00319(15) -0.00159(14) 0.00198(16)
Cl4 0.0209(2) 0.0441(2) 0.0426(2) 0.01120(18) 0.00749(16) -0.00809(16)
O3 0.0366(7) 0.0253(5) 0.0297(6) -0.0071(4) 0.0077(5) 0.0019(5)
O4 0.0938(12) 0.0210(6) 0.0363(7) -0.0038(5) 0.0067(7) 0.0030(6)
N3 0.0195(6) 0.0219(6) 0.0192(6) -0.0024(5) -0.0001(5) -0.0012(5)
N4 0.0202(6) 0.0218(6) 0.0219(6) -0.0027(5) -0.0025(5) -0.0011(5)
C18 0.0141(7) 0.0218(7) 0.0225(7) -0.0043(5) -0.0030(5) -0.0023(5)
C19 0.0207(7) 0.0231(7) 0.0226(7) -0.0005(6) -0.0028(6) -0.0036(6)
C20 0.0214(8) 0.0194(7) 0.0318(8) -0.0016(6) -0.0060(6) -0.0011(6)
C21 0.0232(8) 0.0233(7) 0.0284(8) -0.0082(6) -0.0027(6) 0.0020(6)
C22 0.0205(8) 0.0256(7) 0.0221(7) -0.0040(6) -0.0013(6) -0.0015(6)
C23 0.0168(7) 0.0204(7) 0.0208(7) -0.0026(5) -0.0041(5) -0.0014(5)
C24 0.0197(8) 0.0261(7) 0.0232(7) -0.0020(6) 0.0033(6) -0.0026(6)
C25 0.0199(7) 0.0174(6) 0.0217(7) -0.0030(5) 0.0028(5) -0.0008(5)
C26 0.0217(7) 0.0190(6) 0.0188(7) -0.0018(5) 0.0054(5) -0.0021(5)
C27 0.0189(7) 0.0213(7) 0.0216(7) -0.0025(5) 0.0033(5) -0.0024(6)
C28 0.0234(8) 0.0231(7) 0.0199(7) -0.0013(5) 0.0004(6) 0.0016(6)
C29 0.0284(8) 0.0249(7) 0.0229(7) 0.0049(6) 0.0072(6) 0.0007(6)
C30 0.0190(7) 0.0221(7) 0.0289(8) 0.0013(6) 0.0071(6) -0.0025(6)
C31 0.0199(7) 0.0228(7) 0.0243(7) -0.0038(6) -0.0018(6) -0.0003(6)
C32 0.0216(8) 0.0222(7) 0.0232(7) -0.0026(6) -0.0027(6) 0.0006(6)
C33 0.0343(9) 0.0236(8) 0.0285(8) -0.0012(6) 0.0019(7) 0.0033(6)
C34 0.0896(17) 0.0279(9) 0.0341(10) 0.0038(7) 0.0126(10) 0.0027(10)
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
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_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_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) . . . . ?