#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:59:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180283 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/69/7116997.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_7116997
loop_
_publ_author_name
'Chenhao Zhang'
'Ke Shi'
'Kang Cai'
'Jiajun Xie'
'Ting Lei'
'Qifan Yan'
'Jie-Yu Wang'
'Jian Pei'
'Dahui Zhao'
_publ_section_title
;
 Cyano- and chloro-substituted coronene diimides as solution-processable
 electron-transporting semiconductors
;
_journal_name_full               Chem.Commun.
_journal_page_first              7144
_journal_paper_doi               10.1039/C5cc01668A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C70 H66 Cl4 N6 O4'
_chemical_formula_weight         1197.08
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc144pwv
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-02-14 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                94.45(3)
_cell_angle_beta                 104.45(3)
_cell_angle_gamma                119.51(3)
_cell_formula_units_Z            1
_cell_length_a                   10.963(2)
_cell_length_b                   10.985(2)
_cell_length_c                   15.643(3)
_cell_measurement_reflns_used    4231
_cell_measurement_temperature    248(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.26
_cell_volume                     1542.0(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
OLEX2: A complete structure solution, refinement and analysis program.
(Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; 
Puschmann, H., J. Appl. Cryst., 2009, 42, 339-341.)
;
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      248(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23376
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.263
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.809
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7016
_refine_ls_number_restraints     272
_refine_ls_restrained_S_all      1.944
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0937
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2700
_refine_ls_wR_factor_ref         0.2784
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5971
_reflns_number_total             7016
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc01668a2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1542.0(7)
_cod_database_code               7116997
#BEGIN Tags that were not found in dictionaries:
_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_min   0.866
_shelx_estimated_absorpt_t_max   0.887
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.9900(2) 0.8938(2) 0.87469(12) 0.0822(6) Uani 1 1 d . . . . .
O2 O 1.4456(2) 1.0578(2) 0.84771(12) 0.0799(6) Uani 1 1 d . . . . .
N1 N 0.4888(3) 0.8062(3) 0.66489(18) 0.0872(7) Uani 1 1 d . . . . .
N2 N 0.3378(2) 0.8152(3) 0.40880(17) 0.0764(6) Uani 1 1 d . . . . .
N3 N 1.2184(2) 0.9748(2) 0.86316(12) 0.0607(5) Uani 1 1 d . . . . .
C2 C 1.0701(3) 0.9352(3) 0.82914(15) 0.0614(6) Uani 1 1 d . . . . .
C3 C 1.0134(2) 0.9441(2) 0.73380(14) 0.0502(5) Uani 1 1 d . . . . .
C4 C 0.8676(2) 0.9044(2) 0.69755(15) 0.0518(5) Uani 1 1 d . . . . .
H4 H 0.8052 0.8732 0.7331 0.062 Uiso 1 1 calc R U . . .
C5 C 0.8105(2) 0.9100(2) 0.60671(14) 0.0471(4) Uani 1 1 d . . . . .
C6 C 0.6601(2) 0.8722(2) 0.56724(15) 0.0510(5) Uani 1 1 d . . . . .
C7 C 0.6066(2) 0.8761(2) 0.47763(15) 0.0498(5) Uani 1 1 d . . . . .
C8 C 0.6995(2) 0.9189(2) 0.42203(14) 0.0477(5) Uani 1 1 d . . . . .
C9 C 0.8483(2) 0.95824(19) 0.46143(13) 0.0437(4) Uani 1 1 d . . . . .
C10 C 0.9038(2) 0.9546(2) 0.55293(13) 0.0437(4) Uani 1 1 d . . . . .
C11 C 1.0550(2) 0.99613(19) 0.59122(12) 0.0428(4) Uani 1 1 d . . . . .
C12 C 1.1092(2) 0.9907(2) 0.68176(14) 0.0470(4) Uani 1 1 d . . . . .
C13 C 1.2594(2) 1.0314(2) 0.71955(14) 0.0511(5) Uani 1 1 d . . . . .
C14 C 1.3173(3) 1.0236(3) 0.81467(16) 0.0611(6) Uani 1 1 d . . . . .
C15 C 1.3522(2) 1.0746(2) 0.66898(15) 0.0515(5) Uani 1 1 d . . . . .
H15 H 1.4512 1.1002 0.6948 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5643(3) 0.8340(3) 0.62160(17) 0.0617(6) Uani 1 1 d . . . . .
C17 C 0.4556(3) 0.8401(3) 0.43964(17) 0.0583(5) Uani 1 1 d . . . . .
C18 C 1.2758(3) 0.9586(3) 0.95716(15) 0.0710(7) Uani 1 1 d D . . . .
H18 H 1.3800 0.9880 0.9702 0.085 Uiso 0.723(4) 1 d R U P A 1
H18A H 1.1860 0.9257 0.9738 0.085 Uiso 0.277(4) 1 d R U P A 2
C19 C 1.2075(5) 0.8047(4) 0.9629(3) 0.0681(10) Uani 0.723(4) 1 d D U P A 1
H19A H 1.1085 0.7703 0.9670 0.082 Uiso 0.723(4) 1 calc R U P A 1
H19B H 1.2676 0.8005 1.0193 0.082 Uiso 0.723(4) 1 calc R U P A 1
C20 C 1.1925(7) 0.7019(5) 0.8840(3) 0.0752(12) Uani 0.723(4) 1 d D U P A 1
H20A H 1.1268 0.7000 0.8277 0.090 Uiso 0.723(4) 1 calc R U P A 1
H20B H 1.2903 0.7378 0.8774 0.090 Uiso 0.723(4) 1 calc R U P A 1
C21 C 1.1305(11) 0.5492(6) 0.8974(6) 0.095(2) Uani 0.723(4) 1 d D U P A 1
H21A H 1.0350 0.5142 0.9072 0.114 Uiso 0.723(4) 1 calc R U P A 1
H21B H 1.1991 0.5492 0.9514 0.114 Uiso 0.723(4) 1 calc R U P A 1
C22 C 1.1089(8) 0.4472(5) 0.8125(4) 0.1063(16) Uani 0.723(4) 1 d D U P A 1
H22A H 1.0281 0.4361 0.7616 0.128 Uiso 0.723(4) 1 calc R U P A 1
H22B H 1.1996 0.4939 0.7964 0.128 Uiso 0.723(4) 1 calc R U P A 1
C23 C 1.0740(8) 0.2987(5) 0.8231(5) 0.122(2) Uani 0.723(4) 1 d D U P A 1
H23A H 1.1478 0.3064 0.8773 0.146 Uiso 0.723(4) 1 calc R U P A 1
H23B H 1.0758 0.2471 0.7699 0.146 Uiso 0.723(4) 1 calc R U P A 1
C24 C 0.9202(12) 0.2189(9) 0.8319(10) 0.183(5) Uani 0.723(4) 1 d D U P A 1
H24A H 0.8525 0.1387 0.7794 0.274 Uiso 0.723(4) 1 calc R U P A 1
H24B H 0.8849 0.2839 0.8354 0.274 Uiso 0.723(4) 1 calc R U P A 1
H24C H 0.9251 0.1830 0.8866 0.274 Uiso 0.723(4) 1 calc R U P A 1
C19A C 1.2795(14) 0.8248(9) 0.9521(9) 0.086(3) Uani 0.277(4) 1 d D U P A 2
H19C H 1.3134 0.8170 1.0145 0.103 Uiso 0.277(4) 1 calc R U P A 2
H19D H 1.3550 0.8368 0.9249 0.103 Uiso 0.277(4) 1 calc R U P A 2
C20A C 1.1367(13) 0.6820(12) 0.8998(10) 0.093(4) Uani 0.277(4) 1 d D U P A 2
H20C H 1.0967 0.6875 0.8378 0.111 Uiso 0.277(4) 1 calc R U P A 2
H20D H 1.0622 0.6606 0.9297 0.111 Uiso 0.277(4) 1 calc R U P A 2
C21A C 1.172(2) 0.5629(13) 0.8974(18) 0.099(6) Uani 0.277(4) 1 d D U P A 2
H21C H 1.2153 0.5598 0.9594 0.118 Uiso 0.277(4) 1 calc R U P A 2
H21D H 1.2436 0.5823 0.8655 0.118 Uiso 0.277(4) 1 calc R U P A 2
C22A C 1.026(2) 0.4174(15) 0.8475(16) 0.180(7) Uani 0.277(4) 1 d D U P A 2
H22C H 0.9434 0.4241 0.8557 0.216 Uiso 0.277(4) 1 calc R U P A 2
H22D H 1.0120 0.4034 0.7824 0.216 Uiso 0.277(4) 1 calc R U P A 2
C23A C 1.014(2) 0.2829(18) 0.8768(17) 0.161(7) Uani 0.277(4) 1 d D U P A 2
H23C H 1.0923 0.2692 0.8679 0.193 Uiso 0.277(4) 1 calc R U P A 2
H23D H 1.0191 0.2879 0.9405 0.193 Uiso 0.277(4) 1 calc R U P A 2
C24A C 0.860(3) 0.163(2) 0.812(2) 0.181(12) Uani 0.277(4) 1 d D U P A 2
H24D H 0.8664 0.1409 0.7530 0.272 Uiso 0.277(4) 1 calc R U P A 2
H24E H 0.7911 0.1955 0.8069 0.272 Uiso 0.277(4) 1 calc R U P A 2
H24F H 0.8255 0.0780 0.8364 0.272 Uiso 0.277(4) 1 calc R U P A 2
C25 C 1.2873(5) 1.0611(4) 1.0320(2) 0.0664(9) Uani 0.723(4) 1 d D U P A 1
H25A H 1.3423 1.0553 1.0899 0.080 Uiso 0.723(4) 1 calc R U P A 1
H25B H 1.1868 1.0284 1.0328 0.080 Uiso 0.723(4) 1 calc R U P A 1
C26 C 1.3611(8) 1.2167(5) 1.0274(4) 0.0771(18) Uani 0.723(4) 1 d D U P A 1
H26A H 1.3062 1.2250 0.9706 0.092 Uiso 0.723(4) 1 calc R U P A 1
H26B H 1.4624 1.2518 1.0275 0.092 Uiso 0.723(4) 1 calc R U P A 1
C27 C 1.3665(6) 1.3101(5) 1.1081(3) 0.0871(13) Uani 0.723(4) 1 d D U P A 1
H27A H 1.2651 1.2726 1.1087 0.104 Uiso 0.723(4) 1 calc R U P A 1
H27B H 1.4227 1.3022 1.1646 0.104 Uiso 0.723(4) 1 calc R U P A 1
C28 C 1.4373(9) 1.4684(5) 1.1060(5) 0.114(2) Uani 0.723(4) 1 d D U P A 1
H28A H 1.5422 1.5086 1.1128 0.137 Uiso 0.723(4) 1 calc R U P A 1
H28B H 1.3889 1.4753 1.0464 0.137 Uiso 0.723(4) 1 calc R U P A 1
C29 C 1.4274(8) 1.5591(6) 1.1789(5) 0.125(2) Uani 0.723(4) 1 d D U P A 1
H29A H 1.4739 1.5487 1.2378 0.150 Uiso 0.723(4) 1 calc R U P A 1
H29B H 1.4885 1.6600 1.1772 0.150 Uiso 0.723(4) 1 calc R U P A 1
C30 C 1.2789(9) 1.5317(9) 1.1771(6) 0.146(3) Uani 0.723(4) 1 d D U P A 1
H30A H 1.2913 1.5972 1.2285 0.219 Uiso 0.723(4) 1 calc R U P A 1
H30B H 1.2166 1.4331 1.1807 0.219 Uiso 0.723(4) 1 calc R U P A 1
H30C H 1.2323 1.5469 1.1211 0.219 Uiso 0.723(4) 1 calc R U P A 1
C25A C 1.3749(12) 1.0973(8) 1.0270(6) 0.074(3) Uani 0.277(4) 1 d D U P A 2
H25C H 1.4699 1.1464 1.0157 0.089 Uiso 0.277(4) 1 calc R U P A 2
H25D H 1.3944 1.0737 1.0860 0.089 Uiso 0.277(4) 1 calc R U P A 2
C26A C 1.3299(18) 1.2051(14) 1.0370(14) 0.088(6) Uani 0.277(4) 1 d D U P A 2
H26C H 1.2428 1.1638 1.0570 0.106 Uiso 0.277(4) 1 calc R U P A 2
H26D H 1.3015 1.2250 0.9777 0.106 Uiso 0.277(4) 1 calc R U P A 2
C27A C 1.4561(14) 1.3488(12) 1.1062(8) 0.085(3) Uani 0.277(4) 1 d D U P A 2
H27C H 1.4874 1.3330 1.1665 0.102 Uiso 0.277(4) 1 calc R U P A 2
H27D H 1.5423 1.3973 1.0858 0.102 Uiso 0.277(4) 1 calc R U P A 2
C28A C 1.380(2) 1.4355(19) 1.1066(11) 0.125(6) Uani 0.277(4) 1 d D U P A 2
H28C H 1.4441 1.5311 1.0978 0.150 Uiso 0.277(4) 1 calc R U P A 2
H28D H 1.2865 1.3866 1.0553 0.150 Uiso 0.277(4) 1 calc R U P A 2
C29A C 1.347(2) 1.453(2) 1.1942(13) 0.152(6) Uani 0.277(4) 1 d D U P A 2
H29C H 1.2511 1.3679 1.1888 0.183 Uiso 0.277(4) 1 calc R U P A 2
H29D H 1.4230 1.4541 1.2440 0.183 Uiso 0.277(4) 1 calc R U P A 2
C30A C 1.343(4) 1.585(3) 1.220(2) 0.230(14) Uani 0.277(4) 1 d D U P A 2
H30D H 1.3094 1.5809 1.2717 0.346 Uiso 0.277(4) 1 calc R U P A 2
H30E H 1.2751 1.5904 1.1687 0.346 Uiso 0.277(4) 1 calc R U P A 2
H30F H 1.4417 1.6703 1.2346 0.346 Uiso 0.277(4) 1 calc R U P A 2
Cl1 Cl 0.33844(8) 0.47356(9) 0.43948(8) 0.1075(4) Uani 1 1 d . U . . .
Cl2 Cl 0.27495(13) 0.40101(10) 0.62107(7) 0.1257(5) Uani 1 1 d . U . . .
C31 C 0.1358(3) 0.3760(3) 0.5273(2) 0.0791(8) Uani 1 1 d . . . . .
C32 C -0.0078(4) 0.3222(3) 0.5303(2) 0.0800(8) Uani 1 1 d . . . . .
H32 H -0.0285 0.2994 0.5837 0.096 Uiso 1 1 calc R U . . .
C33 C -0.1173(3) 0.3028(3) 0.4567(2) 0.0751(7) Uani 1 1 d . . . . .
H33 H -0.2135 0.2660 0.4595 0.090 Uiso 1 1 calc R U . . .
C34 C -0.0904(3) 0.3357(3) 0.3788(2) 0.0760(7) Uani 1 1 d . . . . .
H34 H -0.1675 0.3228 0.3286 0.091 Uiso 1 1 calc R U . . .
C35 C 0.0522(3) 0.3889(3) 0.3730(2) 0.0713(6) Uani 1 1 d . . . . .
H35 H 0.0713 0.4112 0.3192 0.086 Uiso 1 1 calc R U . . .
C36 C 0.1634(3) 0.4079(3) 0.4475(2) 0.0703(7) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
C14 N3 C2 124.34(18) . .
C14 N3 C18 116.9(2) . .
C2 N3 C18 118.7(2) . .
O1 C2 N3 121.2(2) . .
O1 C2 C3 121.1(2) . .
N3 C2 C3 117.8(2) . .
C4 C3 C12 120.81(19) . .
C4 C3 C2 119.5(2) . .
C12 C3 C2 119.7(2) . .
C3 C4 C5 120.57(19) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C10 C5 C4 119.63(19) . .
C10 C5 C6 118.22(18) . .
C4 C5 C6 122.15(18) . .
C7 C6 C5 120.80(18) . .
C7 C6 C16 119.4(2) . .
C5 C6 C16 119.72(19) . .
C6 C7 C8 121.46(19) . .
C6 C7 C17 119.93(19) . .
C8 C7 C17 118.6(2) . .
C9 C8 C15 119.94(19) . 2_776
C9 C8 C7 117.68(18) . .
C15 C8 C7 122.36(19) 2_776 .
C8 C9 C10 121.21(18) . .
C8 C9 C11 119.39(18) . 2_776
C10 C9 C11 119.40(17) . 2_776
C5 C10 C9 120.60(18) . .
C5 C10 C11 119.40(18) . .
C9 C10 C11 120.00(17) . .
C12 C11 C10 119.82(18) . .
C12 C11 C9 119.59(18) . 2_776
C10 C11 C9 120.60(18) . 2_776
C3 C12 C11 119.77(19) . .
C3 C12 C13 120.52(19) . .
C11 C12 C13 119.71(19) . .
C15 C13 C12 120.74(19) . .
C15 C13 C14 119.1(2) . .
C12 C13 C14 120.2(2) . .
O2 C14 N3 121.7(2) . .
O2 C14 C13 120.8(2) . .
N3 C14 C13 117.5(2) . .
C13 C15 C8 120.6(2) . 2_776
C13 C15 H15 119.7 . .
C8 C15 H15 119.7 2_776 .
N1 C16 C6 178.8(3) . .
N2 C17 C7 178.0(3) . .
C19A C18 C25A 128.7(6) . .
C19 C18 C25 116.9(3) . .
C19A C18 N3 110.7(5) . .
C25A C18 N3 114.0(4) . .
C19 C18 N3 112.8(2) . .
C25 C18 N3 114.1(2) . .
C19 C18 H18 100.8 . .
C25 C18 H18 101.6 . .
N3 C18 H18 108.8 . .
C19A C18 H18A 99.1 . .
C25A C18 H18A 98.1 . .
N3 C18 H18A 98.5 . .
C18 C19 C20 115.7(3) . .
C18 C19 H19A 108.4 . .
C20 C19 H19A 108.4 . .
C18 C19 H19B 108.4 . .
C20 C19 H19B 108.4 . .
H19A C19 H19B 107.4 . .
C21 C20 C19 112.6(4) . .
C21 C20 H20A 109.1 . .
C19 C20 H20A 109.1 . .
C21 C20 H20B 109.1 . .
C19 C20 H20B 109.1 . .
H20A C20 H20B 107.8 . .
C20 C21 C22 110.3(6) . .
C20 C21 H21A 109.6 . .
C22 C21 H21A 109.6 . .
C20 C21 H21B 109.6 . .
C22 C21 H21B 109.6 . .
H21A C21 H21B 108.1 . .
C23 C22 C21 115.8(5) . .
C23 C22 H22A 108.3 . .
C21 C22 H22A 108.3 . .
C23 C22 H22B 108.3 . .
C21 C22 H22B 108.3 . .
H22A C22 H22B 107.4 . .
C22 C23 C24 107.5(6) . .
C22 C23 H23A 110.2 . .
C24 C23 H23A 110.2 . .
C22 C23 H23B 110.2 . .
C24 C23 H23B 110.2 . .
H23A C23 H23B 108.5 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C18 C19A C20A 118.5(9) . .
C18 C19A H19C 107.7 . .
C20A C19A H19C 107.7 . .
C18 C19A H19D 107.7 . .
C20A C19A H19D 107.7 . .
H19C C19A H19D 107.1 . .
C19A C20A C21A 108.6(9) . .
C19A C20A H20C 110.0 . .
C21A C20A H20C 110.0 . .
C19A C20A H20D 110.0 . .
C21A C20A H20D 110.0 . .
H20C C20A H20D 108.4 . .
C20A C21A C22A 108.5(11) . .
C20A C21A H21C 110.0 . .
C22A C21A H21C 110.0 . .
C20A C21A H21D 110.0 . .
C22A C21A H21D 110.0 . .
H21C C21A H21D 108.4 . .
C23A C22A C21A 116.8(12) . .
C23A C22A H22C 108.1 . .
C21A C22A H22C 108.1 . .
C23A C22A H22D 108.1 . .
C21A C22A H22D 108.1 . .
H22C C22A H22D 107.3 . .
C24A C23A C22A 101.7(11) . .
C24A C23A H23C 111.4 . .
C22A C23A H23C 111.4 . .
C24A C23A H23D 111.4 . .
C22A C23A H23D 111.4 . .
H23C C23A H23D 109.3 . .
C23A C24A H24D 109.5 . .
C23A C24A H24E 109.5 . .
H24D C24A H24E 109.5 . .
C23A C24A H24F 109.5 . .
H24D C24A H24F 109.5 . .
H24E C24A H24F 109.5 . .
C18 C25 C26 116.5(4) . .
C18 C25 H25A 108.2 . .
C26 C25 H25A 108.2 . .
C18 C25 H25B 108.2 . .
C26 C25 H25B 108.2 . .
H25A C25 H25B 107.3 . .
C25 C26 C27 111.3(5) . .
C25 C26 H26A 109.4 . .
C27 C26 H26A 109.4 . .
C25 C26 H26B 109.4 . .
C27 C26 H26B 109.4 . .
H26A C26 H26B 108.0 . .
C28 C27 C26 113.5(4) . .
C28 C27 H27A 108.9 . .
C26 C27 H27A 108.9 . .
C28 C27 H27B 108.9 . .
C26 C27 H27B 108.9 . .
H27A C27 H27B 107.7 . .
C29 C28 C27 114.2(5) . .
C29 C28 H28A 108.7 . .
C27 C28 H28A 108.7 . .
C29 C28 H28B 108.7 . .
C27 C28 H28B 108.7 . .
H28A C28 H28B 107.6 . .
C30 C29 C28 119.6(6) . .
C30 C29 H29A 107.4 . .
C28 C29 H29A 107.4 . .
C30 C29 H29B 107.4 . .
C28 C29 H29B 107.4 . .
H29A C29 H29B 107.0 . .
C29 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C29 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C18 C25A C26A 121.0(8) . .
C18 C25A H25C 107.1 . .
C26A C25A H25C 107.1 . .
C18 C25A H25D 107.1 . .
C26A C25A H25D 107.1 . .
H25C C25A H25D 106.8 . .
C25A C26A C27A 112.5(9) . .
C25A C26A H26C 109.1 . .
C27A C26A H26C 109.1 . .
C25A C26A H26D 109.1 . .
C27A C26A H26D 109.1 . .
H26C C26A H26D 107.8 . .
C28A C27A C26A 101.9(9) . .
C28A C27A H27C 111.4 . .
C26A C27A H27C 111.4 . .
C28A C27A H27D 111.4 . .
C26A C27A H27D 111.4 . .
H27C C27A H27D 109.2 . .
C29A C28A C27A 113.0(11) . .
C29A C28A H28C 109.0 . .
C27A C28A H28C 109.0 . .
C29A C28A H28D 109.0 . .
C27A C28A H28D 109.0 . .
H28C C28A H28D 107.8 . .
C30A C29A C28A 115.5(12) . .
C30A C29A H29C 108.4 . .
C28A C29A H29C 108.4 . .
C30A C29A H29D 108.4 . .
C28A C29A H29D 108.4 . .
H29C C29A H29D 107.5 . .
C29A C30A H30D 109.5 . .
C29A C30A H30E 109.5 . .
H30D C30A H30E 109.5 . .
C29A C30A H30F 109.5 . .
H30D C30A H30F 109.5 . .
H30E C30A H30F 109.5 . .
C36 C31 C32 118.8(3) . .
C36 C31 Cl2 121.0(2) . .
C32 C31 Cl2 120.2(3) . .
C33 C32 C31 120.3(3) . .
C33 C32 H32 119.8 . .
C31 C32 H32 119.8 . .
C32 C33 C34 121.1(3) . .
C32 C33 H33 119.5 . .
C34 C33 H33 119.5 . .
C33 C34 C35 120.1(3) . .
C33 C34 H34 119.9 . .
C35 C34 H34 119.9 . .
C36 C35 C34 118.9(3) . .
C36 C35 H35 120.5 . .
C34 C35 H35 120.5 . .
C35 C36 C31 120.7(3) . .
C35 C36 Cl1 118.4(2) . .
C31 C36 Cl1 120.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.207(3) .
O2 C14 1.213(3) .
N1 C16 1.140(3) .
N2 C17 1.138(3) .
N3 C14 1.392(3) .
N3 C2 1.397(3) .
N3 C18 1.510(3) .
C2 C3 1.497(3) .
C3 C4 1.374(3) .
C3 C12 1.411(3) .
C4 C5 1.422(3) .
C4 H4 0.9400 .
C5 C10 1.413(3) .
C5 C6 1.431(3) .
C6 C7 1.391(3) .
C6 C16 1.439(3) .
C7 C8 1.431(3) .
C7 C17 1.442(3) .
C8 C9 1.410(3) .
C8 C15 1.416(3) 2_776
C9 C10 1.421(3) .
C9 C11 1.425(3) 2_776
C10 C11 1.425(3) .
C11 C12 1.411(3) .
C11 C9 1.425(3) 2_776
C12 C13 1.418(3) .
C13 C15 1.367(3) .
C13 C14 1.492(3) .
C15 C8 1.416(3) 2_776
C15 H15 0.9400 .
C18 C19A 1.486(6) .
C18 C25A 1.488(6) .
C18 C19 1.495(4) .
C18 C25 1.496(4) .
C18 H18 0.9800 .
C18 H18A 0.9800 .
C19 C20 1.524(5) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C20 C21 1.524(6) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C21 C22 1.557(6) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C22 C23 1.514(5) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C23 C24 1.519(7) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C24 H24C 0.9700 .
C19A C20A 1.524(7) .
C19A H19C 0.9800 .
C19A H19D 0.9800 .
C20A C21A 1.535(7) .
C20A H20C 0.9800 .
C20A H20D 0.9800 .
C21A C22A 1.546(8) .
C21A H21C 0.9800 .
C21A H21D 0.9800 .
C22A C23A 1.535(8) .
C22A H22C 0.9800 .
C22A H22D 0.9800 .
C23A C24A 1.533(8) .
C23A H23C 0.9800 .
C23A H23D 0.9800 .
C24A H24D 0.9700 .
C24A H24E 0.9700 .
C24A H24F 0.9700 .
C25 C26 1.506(5) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C26 C27 1.533(6) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C27 C28 1.523(5) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C28 C29 1.516(6) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C29 C30 1.496(7) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C30 H30C 0.9700 .
C25A C26A 1.502(7) .
C25A H25C 0.9800 .
C25A H25D 0.9800 .
C26A C27A 1.553(7) .
C26A H26C 0.9800 .
C26A H26D 0.9800 .
C27A C28A 1.546(7) .
C27A H27C 0.9800 .
C27A H27D 0.9800 .
C28A C29A 1.522(8) .
C28A H28C 0.9800 .
C28A H28D 0.9800 .
C29A C30A 1.507(8) .
C29A H29C 0.9800 .
C29A H29D 0.9800 .
C30A H30D 0.9700 .
C30A H30E 0.9700 .
C30A H30F 0.9700 .
Cl1 C36 1.729(3) .
Cl2 C31 1.721(3) .
C31 C36 1.387(5) .
C31 C32 1.399(5) .
C32 C33 1.354(5) .
C32 H32 0.9400 .
C33 C34 1.358(4) .
C33 H33 0.9400 .
C34 C35 1.405(4) .
C34 H34 0.9400 .
C35 C36 1.374(4) .
C35 H35 0.9400 .
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
C14 N3 C2 O1 -179.9(2) . . . .
C18 N3 C2 O1 2.7(4) . . . .
C14 N3 C2 C3 0.9(4) . . . .
C18 N3 C2 C3 -176.5(2) . . . .
O1 C2 C3 C4 0.0(4) . . . .
N3 C2 C3 C4 179.19(19) . . . .
O1 C2 C3 C12 -179.0(2) . . . .
N3 C2 C3 C12 0.3(3) . . . .
C12 C3 C4 C5 -0.2(3) . . . .
C2 C3 C4 C5 -179.16(19) . . . .
C3 C4 C5 C10 1.0(3) . . . .
C3 C4 C5 C6 -178.75(19) . . . .
C10 C5 C6 C7 1.5(3) . . . .
C4 C5 C6 C7 -178.74(19) . . . .
C10 C5 C6 C16 -176.54(19) . . . .
C4 C5 C6 C16 3.3(3) . . . .
C5 C6 C7 C8 -0.5(3) . . . .
C16 C6 C7 C8 177.53(19) . . . .
C5 C6 C7 C17 -178.90(19) . . . .
C16 C6 C7 C17 -0.9(3) . . . .
C6 C7 C8 C9 -0.5(3) . . . .
C17 C7 C8 C9 177.96(18) . . . .
C6 C7 C8 C15 -179.16(19) . . . 2_776
C17 C7 C8 C15 -0.7(3) . . . 2_776
C15 C8 C9 C10 179.16(17) 2_776 . . .
C7 C8 C9 C10 0.5(3) . . . .
C15 C8 C9 C11 -0.2(3) 2_776 . . 2_776
C7 C8 C9 C11 -178.91(17) . . . 2_776
C4 C5 C10 C9 178.71(17) . . . .
C6 C5 C10 C9 -1.5(3) . . . .
C4 C5 C10 C11 -1.3(3) . . . .
C6 C5 C10 C11 178.53(17) . . . .
C8 C9 C10 C5 0.5(3) . . . .
C11 C9 C10 C5 179.92(16) 2_776 . . .
C8 C9 C10 C11 -179.47(17) . . . .
C11 C9 C10 C11 -0.1(3) 2_776 . . .
C5 C10 C11 C12 0.7(3) . . . .
C9 C10 C11 C12 -179.25(16) . . . .
C5 C10 C11 C9 -179.92(16) . . . 2_776
C9 C10 C11 C9 0.1(3) . . . 2_776
C4 C3 C12 C11 -0.3(3) . . . .
C2 C3 C12 C11 178.61(19) . . . .
C4 C3 C12 C13 -179.91(19) . . . .
C2 C3 C12 C13 -1.0(3) . . . .
C10 C11 C12 C3 0.1(3) . . . .
C9 C11 C12 C3 -179.30(16) 2_776 . . .
C10 C11 C12 C13 179.67(17) . . . .
C9 C11 C12 C13 0.3(3) 2_776 . . .
C3 C12 C13 C15 179.03(19) . . . .
C11 C12 C13 C15 -0.6(3) . . . .
C3 C12 C13 C14 0.7(3) . . . .
C11 C12 C13 C14 -178.92(18) . . . .
C2 N3 C14 O2 179.4(2) . . . .
C18 N3 C14 O2 -3.2(4) . . . .
C2 N3 C14 C13 -1.2(4) . . . .
C18 N3 C14 C13 176.26(19) . . . .
C15 C13 C14 O2 1.5(4) . . . .
C12 C13 C14 O2 179.8(2) . . . .
C15 C13 C14 N3 -178.00(19) . . . .
C12 C13 C14 N3 0.4(3) . . . .
C12 C13 C15 C8 0.7(3) . . . 2_776
C14 C13 C15 C8 179.02(18) . . . 2_776
C14 N3 C18 C19A -77.8(6) . . . .
C2 N3 C18 C19A 99.8(6) . . . .
C14 N3 C18 C25A 76.3(6) . . . .
C2 N3 C18 C25A -106.1(6) . . . .
C14 N3 C18 C19 -110.2(3) . . . .
C2 N3 C18 C19 67.4(3) . . . .
C14 N3 C18 C25 113.4(3) . . . .
C2 N3 C18 C25 -69.0(3) . . . .
C19A C18 C19 C20 -49.5(10) . . . .
C25A C18 C19 C20 -145.2(8) . . . .
C25 C18 C19 C20 178.0(4) . . . .
N3 C18 C19 C20 42.9(5) . . . .
C18 C19 C20 C21 176.6(5) . . . .
C19 C20 C21 C22 176.7(6) . . . .
C20 C21 C22 C23 169.6(6) . . . .
C21 C22 C23 C24 67.7(10) . . . .
C25A C18 C19A C20A 155.5(11) . . . .
C19 C18 C19A C20A 44.6(10) . . . .
C25 C18 C19A C20A 110.5(11) . . . .
N3 C18 C19A C20A -55.3(14) . . . .
C18 C19A C20A C21A 175.1(14) . . . .
C19A C20A C21A C22A 177.9(18) . . . .
C20A C21A C22A C23A -150(2) . . . .
C21A C22A C23A C24A -179(3) . . . .
C19A C18 C25 C26 147.0(8) . . . .
C25A C18 C25 C26 50.1(8) . . . .
C19 C18 C25 C26 177.9(4) . . . .
N3 C18 C25 C26 -47.5(5) . . . .
C18 C25 C26 C27 -179.7(4) . . . .
C25 C26 C27 C28 -178.8(5) . . . .
C26 C27 C28 C29 173.2(6) . . . .
C27 C28 C29 C30 -65.7(10) . . . .
C19A C18 C25A C26A -162.0(14) . . . .
C19 C18 C25A C26A -122.3(13) . . . .
C25 C18 C25A C26A -48.4(14) . . . .
N3 C18 C25A C26A 49.6(16) . . . .
C18 C25A C26A C27A -173.6(11) . . . .
C25A C26A C27A C28A -177.6(15) . . . .
C26A C27A C28A C29A 108.8(18) . . . .
C27A C28A C29A C30A 152(2) . . . .
C36 C31 C32 C33 -0.4(4) . . . .
Cl2 C31 C32 C33 179.8(2) . . . .
C31 C32 C33 C34 -0.4(4) . . . .
C32 C33 C34 C35 0.9(4) . . . .
C33 C34 C35 C36 -0.5(4) . . . .
C34 C35 C36 C31 -0.4(4) . . . .
C34 C35 C36 Cl1 -179.99(19) . . . .
C32 C31 C36 C35 0.8(4) . . . .
Cl2 C31 C36 C35 -179.4(2) . . . .
C32 C31 C36 Cl1 -179.57(18) . . . .
Cl2 C31 C36 Cl1 0.2(3) . . . .
