#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150893.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_7150893
loop_
_publ_author_name
'Wang, Ting'
'Bai, Yu'
'Ma, Liang'
'Yan, Xiu-Ping'
_publ_section_title
;
 Synthesis and characterization of indolocarbazole-quinoxalines with
 flat rigid structure for sensing fluoride and acetate anions
;
_journal_issue                   10
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1751
_journal_page_last               1755
_journal_paper_doi               10.1039/b801447g
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C43 H54 Cl3 N6 O4.5'
_chemical_formula_weight         833.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.73(3)
_cell_angle_beta                 107.18(3)
_cell_angle_gamma                95.52(3)
_cell_formula_units_Z            2
_cell_length_a                   12.077(2)
_cell_length_b                   13.878(3)
_cell_length_c                   14.279(3)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.3
_cell_volume                     2116.5(10)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13051
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             882
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         7406
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²+1.7395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                6095
_reflns_number_total             7406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801447g_b.txt
_cod_data_source_block           r70721a
_cod_original_cell_volume        2116.4(7)
_cod_original_sg_symbol_H-M      p-1
_cod_original_formula_sum        'C43 H54 Cl3 N6 O4.50'
_cod_database_code               7150893
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.29063(18) 0.73231(17) 1.00026(17) 0.0256(5) Uani 1 1 d . A .
N2 N 0.30503(17) 0.72923(16) 1.22180(16) 0.0242(4) Uani 1 1 d . A .
C1 C 0.2558(2) 0.6990(2) 0.8915(2) 0.0294(6) Uani 1 1 d . . .
C2 C 0.2804(3) 0.7518(2) 0.8299(2) 0.0391(7) Uani 1 1 d . . .
H2B H 0.3274 0.8204 0.8602 0.047 Uiso 1 1 calc R . .
C3 C 0.2326(3) 0.6987(3) 0.7213(2) 0.0485(8) Uani 1 1 d . . .
H3A H 0.2479 0.7320 0.6764 0.058 Uiso 1 1 calc R . .
C4 C 0.1627(3) 0.5979(3) 0.6760(2) 0.0451(8) Uani 1 1 d . . .
H4A H 0.1306 0.5652 0.6014 0.054 Uiso 1 1 calc R . .
C5 C 0.1397(2) 0.5456(2) 0.7369(2) 0.0358(7) Uani 1 1 d . . .
H5 H 0.0921 0.4771 0.7057 0.043 Uiso 1 1 calc R . .
C6 C 0.1882(2) 0.5957(2) 0.8469(2) 0.0285(6) Uani 1 1 d . . .
C7 C 0.1837(2) 0.56692(18) 0.93399(19) 0.0237(5) Uani 1 1 d . A .
C8 C 0.12868(19) 0.47345(18) 0.9396(2) 0.0259(6) Uani 1 1 d . . .
C9 C 0.13534(19) 0.47295(18) 1.0434(2) 0.0243(5) Uani 1 1 d . A .
C10 C 0.19616(19) 0.56445(18) 1.13410(19) 0.0231(5) Uani 1 1 d . . .
C11 C 0.2119(2) 0.59146(19) 1.2437(2) 0.0256(5) Uani 1 1 d . A .
C12 C 0.1739(2) 0.5414(2) 1.3032(2) 0.0340(6) Uani 1 1 d . . .
H12A H 0.1265 0.4729 1.2706 0.041 Uiso 1 1 calc R A .
C13 C 0.2069(3) 0.5942(3) 1.4102(2) 0.0448(7) Uani 1 1 d . A .
H13A H 0.1814 0.5611 1.4513 0.054 Uiso 1 1 calc R . .
C14 C 0.2762(3) 0.6942(3) 1.4599(2) 0.0458(7) Uani 1 1 d . . .
H14A H 0.2982 0.7274 1.5341 0.055 Uiso 1 1 calc R A .
C15 C 0.3139(2) 0.7465(2) 1.4037(2) 0.0358(6) Uani 1 1 d . A .
H15A H 0.3606 0.8153 1.4375 0.043 Uiso 1 1 calc R . .
C16 C 0.2806(2) 0.69413(19) 1.2955(2) 0.0263(5) Uani 1 1 d . . .
C17 C 0.25289(19) 0.65192(17) 1.12516(19) 0.0217(5) Uani 1 1 d . A .
C18 C 0.2463(2) 0.65312(18) 1.02477(19) 0.0229(5) Uani 1 1 d . . .
O1 O -0.1995(8) -0.0393(5) 0.7143(4) 0.0465(14) Uani 0.792(4) 1 d PD A 1
O2 O -0.1361(3) 0.0276(2) 0.6182(2) 0.0602(9) Uani 0.792(4) 1 d PD A 1
N5 N -0.1452(2) 0.0325(2) 0.7028(2) 0.0347(8) Uani 0.792(4) 1 d PD A 1
N3 N 0.0752(5) 0.3877(5) 0.8561(4) 0.0212(10) Uani 0.792(4) 1 d P A 1
N4 N 0.0869(6) 0.3919(5) 1.0600(4) 0.0218(11) Uani 0.792(4) 1 d P A 1
C19 C 0.0251(7) 0.3034(4) 0.8711(5) 0.0202(13) Uani 0.792(4) 1 d PD A 1
C20 C -0.0332(5) 0.2119(4) 0.7810(3) 0.0275(11) Uani 0.792(4) 1 d PD A 1
H20A H -0.0358 0.2089 0.7130 0.033 Uiso 0.792(4) 1 calc PR A 1
C21 C -0.0856(4) 0.1281(3) 0.7945(3) 0.0234(10) Uani 0.792(4) 1 d PD A 1
C22 C -0.0848(3) 0.1289(3) 0.8935(3) 0.0259(9) Uani 0.792(4) 1 d PD A 1
H22A H -0.1230 0.0693 0.8998 0.031 Uiso 0.792(4) 1 calc PR A 1
C23 C -0.0281(4) 0.2168(3) 0.9805(3) 0.0248(10) Uani 0.792(4) 1 d PD A 1
H23A H -0.0271 0.2184 1.0477 0.030 Uiso 0.792(4) 1 calc PR A 1
C24 C 0.0291(9) 0.3056(5) 0.9715(5) 0.0214(14) Uani 0.792(4) 1 d PD A 1
O1' O -0.185(2) -0.0418(17) 0.7554(15) 0.062(7) Uani 0.208(4) 1 d PD A 2
O2' O -0.1184(10) 0.0185(9) 0.9259(11) 0.071(4) Uani 0.208(4) 1 d PD A 2
N5' N -0.1323(10) 0.0266(8) 0.8410(10) 0.050(4) Uani 0.208(4) 1 d PDU A 2
N3' N 0.079(2) 0.398(2) 0.8321(17) 0.029(6) Uani 0.208(4) 1 d PU A 2
N4' N 0.082(3) 0.378(2) 1.0292(16) 0.023(5) Uani 0.208(4) 1 d PU A 2
C19' C 0.026(3) 0.3090(15) 0.8392(13) 0.016(5) Uani 0.208(4) 1 d PDU A 2
C20' C -0.030(2) 0.2246(12) 0.7439(12) 0.037(5) Uani 0.208(4) 1 d PD A 2
H20B H -0.0303 0.2301 0.6793 0.044 Uiso 0.208(4) 1 calc PR A 2
C21' C -0.0851(16) 0.1329(10) 0.7450(10) 0.044(5) Uani 0.208(4) 1 d PDU A 2
H21A H -0.1279 0.0765 0.6808 0.053 Uiso 0.208(4) 1 calc PR A 2
C22' C -0.0771(15) 0.1242(9) 0.8408(10) 0.019(4) Uani 0.208(4) 1 d PDU A 2
C23' C -0.0215(16) 0.2068(10) 0.9356(10) 0.034(5) Uani 0.208(4) 1 d PD A 2
H23B H -0.0189 0.2000 1.0003 0.041 Uiso 0.208(4) 1 calc PR A 2
C24' C 0.031(3) 0.3005(12) 0.9342(13) 0.016(6) Uani 0.208(4) 1 d PD A 2
N6 N 0.68536(16) 0.70861(15) 0.34447(15) 0.0238(4) Uani 1 1 d . . .
C25 C 0.5758(2) 0.65130(18) 0.3509(2) 0.0260(5) Uani 1 1 d . . .
H25A H 0.5063 0.6473 0.2908 0.031 Uiso 1 1 calc R . .
H25B H 0.5636 0.6929 0.4164 0.031 Uiso 1 1 calc R . .
C26 C 0.5796(2) 0.54182(19) 0.3499(2) 0.0277(6) Uani 1 1 d . . .
H26A H 0.6389 0.5454 0.4165 0.033 Uiso 1 1 calc R . .
H26B H 0.6042 0.5024 0.2909 0.033 Uiso 1 1 calc R . .
C27 C 0.4582(2) 0.4856(2) 0.3374(2) 0.0315(6) Uani 1 1 d . . .
H27A H 0.4000 0.4796 0.2693 0.038 Uiso 1 1 calc R . .
H27B H 0.4322 0.5272 0.3945 0.038 Uiso 1 1 calc R . .
C28 C 0.4604(3) 0.3772(2) 0.3412(2) 0.0415(7) Uani 1 1 d . . .
H28A H 0.4861 0.3357 0.2848 0.062 Uiso 1 1 calc R . .
H28B H 0.3808 0.3432 0.3317 0.062 Uiso 1 1 calc R . .
H28C H 0.5158 0.3830 0.4096 0.062 Uiso 1 1 calc R . .
C29 C 0.7970(2) 0.69760(19) 0.42099(19) 0.0263(5) Uani 1 1 d . . .
H29A H 0.8666 0.7340 0.4134 0.032 Uiso 1 1 calc R . .
H29B H 0.7999 0.6229 0.4003 0.032 Uiso 1 1 calc R . .
C30 C 0.8085(2) 0.73947(19) 0.5365(2) 0.0306(6) Uani 1 1 d . . .
H30A H 0.8235 0.8165 0.5631 0.037 Uiso 1 1 calc R . .
H30B H 0.7337 0.7135 0.5442 0.037 Uiso 1 1 calc R . .
C31 C 0.9099(2) 0.7046(2) 0.6002(2) 0.0310(6) Uani 1 1 d . . .
H31A H 0.8942 0.6276 0.5727 0.037 Uiso 1 1 calc R . .
H31B H 0.9840 0.7300 0.5911 0.037 Uiso 1 1 calc R . .
C32 C 0.9270(2) 0.7441(2) 0.7166(2) 0.0389(7) Uani 1 1 d . . .
H32A H 0.9439 0.8204 0.7447 0.058 Uiso 1 1 calc R . .
H32B H 0.9934 0.7198 0.7542 0.058 Uiso 1 1 calc R . .
H32C H 0.8546 0.7177 0.7264 0.058 Uiso 1 1 calc R . .
C33 C 0.6774(2) 0.82249(18) 0.3711(2) 0.0278(6) Uani 1 1 d . . .
H33A H 0.6740 0.8503 0.4431 0.033 Uiso 1 1 calc R . .
H33B H 0.6022 0.8265 0.3218 0.033 Uiso 1 1 calc R . .
C34 C 0.7793(2) 0.89208(19) 0.3660(2) 0.0327(6) Uani 1 1 d . . .
H34A H 0.8541 0.8947 0.4202 0.039 Uiso 1 1 calc R . .
H34B H 0.7875 0.8623 0.2960 0.039 Uiso 1 1 calc R . .
C35 C 0.7579(2) 1.0013(2) 0.3841(3) 0.0448(8) Uani 1 1 d . . .
H35A H 0.7343 1.0256 0.4472 0.054 Uiso 1 1 calc R . .
H35B H 0.6917 1.0001 0.3229 0.054 Uiso 1 1 calc R . .
C36 C 0.8670(3) 1.0772(2) 0.3998(3) 0.0561(9) Uani 1 1 d . . .
H36A H 0.9329 1.0785 0.4602 0.084 Uiso 1 1 calc R . .
H36B H 0.8499 1.1470 0.4129 0.084 Uiso 1 1 calc R . .
H36C H 0.8886 1.0551 0.3363 0.084 Uiso 1 1 calc R . .
C37 C 0.6924(2) 0.66167(19) 0.23464(18) 0.0251(5) Uani 1 1 d . . .
H37A H 0.7688 0.6958 0.2357 0.030 Uiso 1 1 calc R . .
H37B H 0.6937 0.5871 0.2195 0.030 Uiso 1 1 calc R . .
C38 C 0.5942(2) 0.66982(19) 0.14461(19) 0.0260(5) Uani 1 1 d . . .
H38A H 0.5865 0.7432 0.1604 0.031 Uiso 1 1 calc R . .
H38B H 0.5179 0.6280 0.1355 0.031 Uiso 1 1 calc R . .
C39 C 0.6232(2) 0.62989(19) 0.04382(19) 0.0267(5) Uani 1 1 d . . .
H39A H 0.6973 0.6748 0.0527 0.032 Uiso 1 1 calc R . .
H39B H 0.6374 0.5586 0.0323 0.032 Uiso 1 1 calc R . .
C40 C 0.5254(2) 0.6280(2) -0.0529(2) 0.0325(6) Uani 1 1 d . . .
H40A H 0.4513 0.5846 -0.0615 0.049 Uiso 1 1 calc R . .
H40B H 0.5474 0.5990 -0.1154 0.049 Uiso 1 1 calc R . .
H40C H 0.5143 0.6990 -0.0440 0.049 Uiso 1 1 calc R . .
Cl1 Cl 0.26393(7) 0.17879(6) 1.06753(6) 0.0469(2) Uani 1 1 d . B .
Cl2 Cl 0.38982(8) 0.07100(6) 0.93523(7) 0.0522(2) Uani 1 1 d . B .
Cl3 Cl 0.14619(16) -0.02436(13) 0.9062(4) 0.0445(9) Uani 0.73(2) 1 d P B 1
Cl3' Cl 0.1576(9) 0.0009(19) 0.8722(12) 0.079(6) Uani 0.27(2) 1 d P B 2
C41 C 0.2838(2) 0.0567(2) 0.9937(2) 0.0373(7) Uani 1 1 d . . .
H41A H 0.3155 0.0244 1.0431 0.045 Uiso 0.73(2) 1 d PR B 1
H41B H 0.2978 0.0112 1.0323 0.045 Uiso 0.27(2) 1 d PR B 2
H1A H 0.327(3) 0.796(2) 1.049(2) 0.045(9) Uiso 1 1 d . . .
H2A H 0.348(3) 0.792(2) 1.237(2) 0.045(9) Uiso 1 1 d . . .
O3 O 0.38572(17) -0.06664(14) 0.13254(15) 0.0378(5) Uani 1 1 d . . .
O4 O 0.43303(18) -0.07633(14) 0.29108(15) 0.0445(5) Uani 1 1 d . . .
C42 C 0.4266(2) -0.0262(2) 0.2313(2) 0.0329(6) Uani 1 1 d . . .
C43 C 0.4706(2) 0.0910(2) 0.2802(2) 0.0413(7) Uani 1 1 d . . .
H43C H 0.5140 0.1116 0.3558 0.062 Uiso 1 1 calc R . .
H43B H 0.4029 0.1249 0.2699 0.062 Uiso 1 1 calc R . .
H43A H 0.5234 0.1121 0.2465 0.062 Uiso 1 1 calc R . .
O5 O 0.4466(4) 0.0354(5) 0.4901(4) 0.0634(14) Uani 0.50 1 d PD . .
H5A H 0.502(6) 0.033(7) 0.542(3) 0.095 Uiso 0.50 1 d PD . .
H5B H 0.453(7) -0.001(6) 0.432(2) 0.095 Uiso 0.50 1 d PD . .
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
_geom_angle_publ_flag
C18 N1 C1 107.8(2) . . ?
C18 N1 H1A 123(2) . . ?
C1 N1 H1A 129(2) . . ?
C17 N2 C16 108.0(2) . . ?
C17 N2 H2A 128(2) . . ?
C16 N2 H2A 124(2) . . ?
N1 C1 C2 128.9(3) . . ?
N1 C1 C6 109.0(2) . . ?
C2 C1 C6 122.1(3) . . ?
C1 C2 C3 116.4(3) . . ?
C1 C2 H2B 121.8 . . ?
C3 C2 H2B 121.8 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 134.1(3) . . ?
C1 C6 C7 106.2(2) . . ?
C18 C7 C6 106.3(2) . . ?
C18 C7 C8 121.2(2) . . ?
C6 C7 C8 132.5(2) . . ?
N3 C8 C7 123.1(3) . . ?
N3 C8 N3' 16.6(10) . . ?
C7 C8 N3' 106.6(9) . . ?
N3 C8 C9 118.7(3) . . ?
C7 C8 C9 118.1(2) . . ?
N3' C8 C9 135.3(9) . . ?
N4' C9 N4 17.4(9) . . ?
N4' C9 C10 133.8(9) . . ?
N4 C9 C10 116.6(3) . . ?
N4' C9 C8 107.3(9) . . ?
N4 C9 C8 124.5(3) . . ?
C10 C9 C8 118.9(2) . . ?
C17 C10 C9 120.9(2) . . ?
C17 C10 C11 106.4(2) . . ?
C9 C10 C11 132.7(2) . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 C10 135.0(2) . . ?
C16 C11 C10 106.2(2) . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 H12A 120.9 . . ?
C11 C12 H12A 120.9 . . ?
C12 C13 C14 122.0(3) . . ?
C12 C13 H13A 119.0 . . ?
C14 C13 H13A 119.0 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 117.1(3) . . ?
C14 C15 H15A 121.4 . . ?
C16 C15 H15A 121.4 . . ?
N2 C16 C15 128.5(2) . . ?
N2 C16 C11 109.0(2) . . ?
C15 C16 C11 122.4(2) . . ?
N2 C17 C10 110.4(2) . . ?
N2 C17 C18 129.1(2) . . ?
C10 C17 C18 120.5(2) . . ?
N1 C18 C7 110.8(2) . . ?
N1 C18 C17 128.8(2) . . ?
C7 C18 C17 120.3(2) . . ?
O1 N5 O2 123.1(4) . . ?
O1 N5 C21 118.7(4) . . ?
O2 N5 C21 118.2(3) . . ?
C8 N3 C19 117.9(5) . . ?
C9 N4 C24 115.2(5) . . ?
N3 C19 C24 122.5(4) . . ?
N3 C19 C20 117.7(5) . . ?
C24 C19 C20 119.8(5) . . ?
C21 C20 C19 118.3(4) . . ?
C21 C20 H20A 120.8 . . ?
C19 C20 H20A 120.8 . . ?
C20 C21 C22 122.9(4) . . ?
C20 C21 N5 119.2(4) . . ?
C22 C21 N5 117.8(4) . . ?
C23 C22 C21 118.8(4) . . ?
C23 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
C22 C23 C24 120.7(4) . . ?
C22 C23 H23A 119.6 . . ?
C24 C23 H23A 119.6 . . ?
N4 C24 C19 121.2(5) . . ?
N4 C24 C23 119.5(5) . . ?
C19 C24 C23 119.3(5) . . ?
O2' N5' O1' 125.5(18) . . ?
O2' N5' C22' 117.8(11) . . ?
O1' N5' C22' 116.7(16) . . ?
C19' N3' C8 105.7(14) . . ?
C9 N4' C24' 124.2(18) . . ?
N3' C19' C24' 123.0(14) . . ?
N3' C19' C20' 116.1(14) . . ?
C24' C19' C20' 120.9(9) . . ?
C21' C20' C19' 119.2(9) . . ?
C21' C20' H20B 120.4 . . ?
C19' C20' H20B 120.4 . . ?
C20' C21' C22' 119.4(9) . . ?
C20' C21' H21A 120.3 . . ?
C22' C21' H21A 120.3 . . ?
C23' C22' C21' 121.9(8) . . ?
C23' C22' N5' 119.2(9) . . ?
C21' C22' N5' 118.9(9) . . ?
C22' C23' C24' 118.6(8) . . ?
C22' C23' H23B 120.7 . . ?
C24' C23' H23B 120.7 . . ?
N4' C24' C19' 124.5(16) . . ?
N4' C24' C23' 115.6(17) . . ?
C19' C24' C23' 119.9(9) . . ?
C25 N6 C29 110.38(18) . . ?
C25 N6 C33 107.62(17) . . ?
C29 N6 C33 110.71(18) . . ?
C25 N6 C37 110.49(18) . . ?
C29 N6 C37 106.68(17) . . ?
C33 N6 C37 111.00(19) . . ?
N6 C25 C26 115.40(19) . . ?
N6 C25 H25A 108.4 . . ?
C26 C25 H25A 108.4 . . ?
N6 C25 H25B 108.4 . . ?
C26 C25 H25B 108.4 . . ?
H25A C25 H25B 107.5 . . ?
C25 C26 C27 110.6(2) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 C28 111.9(2) . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N6 C29 C30 115.73(19) . . ?
N6 C29 H29A 108.3 . . ?
C30 C29 H29A 108.3 . . ?
N6 C29 H29B 108.3 . . ?
C30 C29 H29B 108.3 . . ?
H29A C29 H29B 107.4 . . ?
C31 C30 C29 109.8(2) . . ?
C31 C30 H30A 109.7 . . ?
C29 C30 H30A 109.7 . . ?
C31 C30 H30B 109.7 . . ?
C29 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
C32 C31 C30 112.7(2) . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N6 C33 C34 115.0(2) . . ?
N6 C33 H33A 108.5 . . ?
C34 C33 H33A 108.5 . . ?
N6 C33 H33B 108.5 . . ?
C34 C33 H33B 108.5 . . ?
H33A C33 H33B 107.5 . . ?
C35 C34 C33 111.0(2) . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C36 112.2(2) . . ?
C34 C35 H35A 109.2 . . ?
C36 C35 H35A 109.2 . . ?
C34 C35 H35B 109.2 . . ?
C36 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 N6 116.71(19) . . ?
C38 C37 H37A 108.1 . . ?
N6 C37 H37A 108.1 . . ?
C38 C37 H37B 108.1 . . ?
N6 C37 H37B 108.1 . . ?
H37A C37 H37B 107.3 . . ?
C37 C38 C39 109.13(19) . . ?
C37 C38 H38A 109.9 . . ?
C39 C38 H38A 109.9 . . ?
C37 C38 H38B 109.9 . . ?
C39 C38 H38B 109.9 . . ?
H38A C38 H38B 108.3 . . ?
C40 C39 C38 113.1(2) . . ?
C40 C39 H39A 109.0 . . ?
C38 C39 H39A 109.0 . . ?
C40 C39 H39B 109.0 . . ?
C38 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
Cl2 C41 Cl3 114.9(2) . . ?
Cl2 C41 Cl1 111.39(15) . . ?
Cl3 C41 Cl1 110.50(17) . . ?
Cl2 C41 Cl3' 96.3(8) . . ?
Cl3 C41 Cl3' 23.2(10) . . ?
Cl1 C41 Cl3' 108.0(4) . . ?
Cl2 C41 H41A 106.5 . . ?
Cl3 C41 H41A 106.5 . . ?
Cl1 C41 H41A 106.5 . . ?
Cl3' C41 H41A 127.4 . . ?
Cl2 C41 H41B 113.4 . . ?
Cl3 C41 H41B 92.1 . . ?
Cl1 C41 H41B 113.3 . . ?
Cl3' C41 H41B 113.2 . . ?
H41A C41 H41B 14.4 . . ?
O4 C42 O3 124.2(2) . . ?
O4 C42 C43 118.6(3) . . ?
O3 C42 C43 117.2(3) . . ?
C42 C43 H43C 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43C C43 H43B 109.5 . . ?
C42 C43 H43A 109.5 . . ?
H43C C43 H43A 109.5 . . ?
H43B C43 H43A 109.5 . . ?
O5 O5 H5A 43(5) 2_656 . ?
O5 O5 H5B 69(4) 2_656 . ?
H5A O5 H5B 110.6(19) . . ?
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
N1 C18 1.364(3) . ?
N1 C1 1.385(3) . ?
N1 H1A 0.90(3) . ?
N2 C17 1.363(3) . ?
N2 C16 1.385(3) . ?
N2 H2A 0.90(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.417(4) . ?
C2 C3 1.392(4) . ?
C2 H2B 0.9500 . ?
C3 C4 1.398(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.369(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.403(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.437(3) . ?
C7 C18 1.391(3) . ?
C7 C8 1.436(3) . ?
C8 N3 1.319(6) . ?
C8 N3' 1.45(2) . ?
C8 C9 1.463(4) . ?
C9 N4' 1.33(3) . ?
C9 N4 1.338(7) . ?
C9 C10 1.426(3) . ?
C10 C17 1.397(3) . ?
C10 C11 1.434(3) . ?
C11 C12 1.402(4) . ?
C11 C16 1.414(4) . ?
C12 C13 1.377(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H15A 0.9500 . ?
C17 C18 1.418(3) . ?
O1 N5 1.222(6) . ?
O2 N5 1.225(4) . ?
N5 C21 1.461(5) . ?
N3 C19 1.372(8) . ?
N4 C24 1.366(9) . ?
C19 C24 1.410(5) . ?
C19 C20 1.417(5) . ?
C20 C21 1.365(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.408(5) . ?
C22 C23 1.365(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.415(6) . ?
C23 H23A 0.9500 . ?
O1' N5' 1.217(10) . ?
O2' N5' 1.216(9) . ?
N5' C22' 1.452(12) . ?
N3' C19' 1.38(3) . ?
N4' C24' 1.35(3) . ?
C19' C24' 1.383(9) . ?
C19' C20' 1.401(10) . ?
C20' C21' 1.384(9) . ?
C20' H20B 0.9500 . ?
C21' C22' 1.388(9) . ?
C21' H21A 0.9500 . ?
C22' C23' 1.384(9) . ?
C23' C24' 1.400(9) . ?
C23' H23B 0.9500 . ?
N6 C25 1.519(3) . ?
N6 C29 1.520(3) . ?
N6 C33 1.522(3) . ?
N6 C37 1.525(3) . ?
C25 C26 1.520(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.525(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.526(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.520(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.516(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.516(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.523(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.515(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.517(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.514(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.525(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.520(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
Cl1 C41 1.766(3) . ?
Cl2 C41 1.750(3) . ?
Cl3 C41 1.761(3) . ?
Cl3' C41 1.811(7) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
O3 C42 1.255(3) . ?
O4 C42 1.254(3) . ?
C42 C43 1.516(4) . ?
C43 H43C 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43A 0.9800 . ?
O5 O5 1.707(8) 2_656 ?
O5 H5A 0.850(10) . ?
O5 H5B 0.851(10) . ?
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
C18 N1 C1 C2 -179.2(2) . . . . ?
C18 N1 C1 C6 -0.3(3) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 1.9(4) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
N1 C1 C6 C5 178.2(2) . . . . ?
C2 C1 C6 C5 -2.8(4) . . . . ?
N1 C1 C6 C7 -0.3(3) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
C5 C6 C7 C18 -177.4(3) . . . . ?
C1 C6 C7 C18 0.7(2) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C1 C6 C7 C8 179.7(2) . . . . ?
C18 C7 C8 N3 -175.4(4) . . . . ?
C6 C7 C8 N3 5.7(5) . . . . ?
C18 C7 C8 N3' -176.2(12) . . . . ?
C6 C7 C8 N3' 4.9(13) . . . . ?
C18 C7 C8 C9 2.9(3) . . . . ?
C6 C7 C8 C9 -175.9(2) . . . . ?
N3 C8 C9 N4' 0.3(13) . . . . ?
C7 C8 C9 N4' -178.1(13) . . . . ?
N3' C8 C9 N4' 1(2) . . . . ?
N3 C8 C9 N4 -2.4(5) . . . . ?
C7 C8 C9 N4 179.2(4) . . . . ?
N3' C8 C9 N4 -2.0(17) . . . . ?
N3 C8 C9 C10 178.2(4) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
N3' C8 C9 C10 178.6(17) . . . . ?
N4' C9 C10 C17 174.5(17) . . . . ?
N4 C9 C10 C17 177.9(4) . . . . ?
C8 C9 C10 C17 -2.6(3) . . . . ?
N4' C9 C10 C11 -7.5(17) . . . . ?
N4 C9 C10 C11 -4.1(5) . . . . ?
C8 C9 C10 C11 175.3(2) . . . . ?
C17 C10 C11 C12 177.0(3) . . . . ?
C9 C10 C11 C12 -1.2(5) . . . . ?
C17 C10 C11 C16 -1.4(2) . . . . ?
C9 C10 C11 C16 -179.6(2) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C10 C11 C12 C13 -179.3(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C17 N2 C16 C15 -179.0(2) . . . . ?
C17 N2 C16 C11 0.4(2) . . . . ?
C14 C15 C16 N2 178.9(2) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C12 C11 C16 N2 -178.1(2) . . . . ?
C10 C11 C16 N2 0.6(2) . . . . ?
C12 C11 C16 C15 1.4(4) . . . . ?
C10 C11 C16 C15 -179.9(2) . . . . ?
C16 N2 C17 C10 -1.4(3) . . . . ?
C16 N2 C17 C18 175.6(2) . . . . ?
C9 C10 C17 N2 -179.78(19) . . . . ?
C11 C10 C17 N2 1.8(3) . . . . ?
C9 C10 C17 C18 3.0(3) . . . . ?
C11 C10 C17 C18 -175.49(19) . . . . ?
C1 N1 C18 C7 0.8(3) . . . . ?
C1 N1 C18 C17 -176.3(2) . . . . ?
C6 C7 C18 N1 -0.9(3) . . . . ?
C8 C7 C18 N1 179.94(19) . . . . ?
C6 C7 C18 C17 176.43(19) . . . . ?
C8 C7 C18 C17 -2.7(3) . . . . ?
N2 C17 C18 N1 -0.1(4) . . . . ?
C10 C17 C18 N1 176.6(2) . . . . ?
N2 C17 C18 C7 -177.0(2) . . . . ?
C10 C17 C18 C7 -0.3(3) . . . . ?
C7 C8 N3 C19 -179.6(5) . . . . ?
N3' C8 N3 C19 -177(5) . . . . ?
C9 C8 N3 C19 2.1(7) . . . . ?
N4' C9 N4 C24 -8(5) . . . . ?
C10 C9 N4 C24 179.8(6) . . . . ?
C8 C9 N4 C24 0.4(9) . . . . ?
C8 N3 C19 C24 -0.1(11) . . . . ?
C8 N3 C19 C20 179.4(6) . . . . ?
N3 C19 C20 C21 -178.7(6) . . . . ?
C24 C19 C20 C21 0.8(10) . . . . ?
C19 C20 C21 C22 0.4(9) . . . . ?
C19 C20 C21 N5 -179.4(5) . . . . ?
O1 N5 C21 C20 -174.5(6) . . . . ?
O2 N5 C21 C20 7.0(6) . . . . ?
O1 N5 C21 C22 5.7(7) . . . . ?
O2 N5 C21 C22 -172.8(4) . . . . ?
C20 C21 C22 C23 -0.7(7) . . . . ?
N5 C21 C22 C23 179.1(4) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C9 N4 C24 C19 1.7(12) . . . . ?
C9 N4 C24 C23 -178.1(6) . . . . ?
N3 C19 C24 N4 -2.0(13) . . . . ?
C20 C19 C24 N4 178.5(9) . . . . ?
N3 C19 C24 C23 177.8(8) . . . . ?
C20 C19 C24 C23 -1.7(12) . . . . ?
C22 C23 C24 N4 -178.8(7) . . . . ?
C22 C23 C24 C19 1.4(11) . . . . ?
N3 C8 N3' C19' 3(4) . . . . ?
C7 C8 N3' C19' -180(2) . . . . ?
C9 C8 N3' C19' 1(3) . . . . ?
N4 C9 N4' C24' 171(7) . . . . ?
C10 C9 N4' C24' -179(2) . . . . ?
C8 C9 N4' C24' -1(3) . . . . ?
C8 N3' C19' C24' -3(4) . . . . ?
C8 N3' C19' C20' 179(3) . . . . ?
N3' C19' C20' C21' -180(3) . . . . ?
C24' C19' C20' C21' 3(5) . . . . ?
C19' C20' C21' C22' -4(4) . . . . ?
C20' C21' C22' C23' 4(3) . . . . ?
C20' C21' C22' N5' -178.3(17) . . . . ?
O2' N5' C22' C23' -6(2) . . . . ?
O1' N5' C22' C23' 176(2) . . . . ?
O2' N5' C22' C21' 175.8(18) . . . . ?
O1' N5' C22' C21' -2(3) . . . . ?
C21' C22' C23' C24' -2(3) . . . . ?
N5' C22' C23' C24' -180(2) . . . . ?
C9 N4' C24' C19' -1(5) . . . . ?
C9 N4' C24' C23' -179(2) . . . . ?
N3' C19' C24' N4' 3(5) . . . . ?
C20' C19' C24' N4' -179(3) . . . . ?
N3' C19' C24' C23' -178(3) . . . . ?
C20' C19' C24' C23' -1(5) . . . . ?
C22' C23' C24' N4' 179(2) . . . . ?
C22' C23' C24' C19' 0(4) . . . . ?
C29 N6 C25 C26 -46.6(3) . . . . ?
C33 N6 C25 C26 -167.5(2) . . . . ?
C37 N6 C25 C26 71.2(2) . . . . ?
N6 C25 C26 C27 -170.2(2) . . . . ?
C25 C26 C27 C28 -177.3(2) . . . . ?
C25 N6 C29 C30 -59.7(3) . . . . ?
C33 N6 C29 C30 59.3(3) . . . . ?
C37 N6 C29 C30 -179.8(2) . . . . ?
N6 C29 C30 C31 168.9(2) . . . . ?
C29 C30 C31 C32 179.7(2) . . . . ?
C25 N6 C33 C34 -178.6(2) . . . . ?
C29 N6 C33 C34 60.7(3) . . . . ?
C37 N6 C33 C34 -57.6(3) . . . . ?
N6 C33 C34 C35 175.0(2) . . . . ?
C33 C34 C35 C36 169.4(3) . . . . ?
C25 N6 C37 C38 63.9(3) . . . . ?
C29 N6 C37 C38 -176.1(2) . . . . ?
C33 N6 C37 C38 -55.4(3) . . . . ?
N6 C37 C38 C39 173.8(2) . . . . ?
C37 C38 C39 C40 176.0(2) . . . . ?
