#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:35:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180146 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/43/7104338.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_7104338
loop_
_publ_author_name
'Raatikainen, Kari'
'Huuskonen, Juhani'
'Lahtinen, Manu'
'Metrangolo, Pierangelo'
'Rissanen, Kari'
_publ_section_title
;
 Halogen bonding drives the self-assembly of piperazine cyclophanes
 into tubular structures.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2160
_journal_page_last               2162
_journal_paper_doi               10.1039/b901473j
_journal_volume                  34
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         '2(C37 H42 N6), 2(C6 F4 I2), C H Cl3'
_chemical_formula_sum            'C87 H85 Cl3 F8 I4 N12'
_chemical_formula_weight         2064.62
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-02-10T11:54:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.906(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9855(2)
_cell_length_b                   33.6650(10)
_cell_length_c                   22.8345(8)
_cell_measurement_reflns_used    10143
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      63.48
_cell_measurement_theta_min      2.35
_cell_measurement_wavelength     1.54184
_cell_volume                     4576.8(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.449388E-1
_diffrn_orient_matrix_UB_12      -0.247923E-1
_diffrn_orient_matrix_UB_13      0.198727E-1
_diffrn_orient_matrix_UB_21      0.146815
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      0.252323E-1
_diffrn_orient_matrix_UB_31      -0.680955E-1
_diffrn_orient_matrix_UB_32      0.163614E-1
_diffrn_orient_matrix_UB_33      0.301129E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13440
_diffrn_reflns_theta_full        63.48
_diffrn_reflns_theta_max         63.48
_diffrn_reflns_theta_min         2.35
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    12.037
_exptl_absorpt_correction_T_max  0.299
_exptl_absorpt_correction_T_min  0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing et al., 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2052
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.502
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         7310
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0951P)²+12.1523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.17
_reflns_number_gt                6224
_reflns_number_total             7310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901473j.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7104338
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.554(3) 0.7934(3) 0.7561(4) 0.084(4) Uani 1 1 d . . .
H1A H 0.7111 0.8029 0.7567 0.101 Uiso 1 1 calc R . .
H1B H 0.458 0.8169 0.7604 0.101 Uiso 1 1 calc R . .
C2 C 0.5388(17) 0.7662(2) 0.8088(4) 0.053(2) Uani 1 1 d . . .
C3 C 0.6907(16) 0.7363(3) 0.8208(4) 0.060(2) Uani 1 1 d . . .
H3 H 0.8012 0.7317 0.7945 0.072 Uiso 1 1 calc R . .
C4 C 0.6885(15) 0.7125(3) 0.8699(4) 0.054(2) Uani 1 1 d . . .
H4 H 0.7981 0.6922 0.877 0.065 Uiso 1 1 calc R . .
C5 C 0.5284(13) 0.7178(2) 0.9092(3) 0.0377(16) Uani 1 1 d . . .
C6 C 0.3720(15) 0.7474(2) 0.8969(4) 0.050(2) Uani 1 1 d . . .
H6 H 0.2582 0.7515 0.9223 0.06 Uiso 1 1 calc R . .
C7 C 0.3789(18) 0.7714(2) 0.8473(4) 0.060(3) Uani 1 1 d . . .
H7 H 0.2706 0.792 0.84 0.072 Uiso 1 1 calc R . .
C8 C 0.5409(14) 0.6932(2) 0.9640(3) 0.0434(18) Uani 1 1 d . . .
H8A H 0.6986 0.6924 0.982 0.052 Uiso 1 1 calc R . .
H8B H 0.45 0.7061 0.9925 0.052 Uiso 1 1 calc R . .
N9 N 0.4607(10) 0.65253(16) 0.9535(2) 0.0305(12) Uani 1 1 d . . .
C10 C 0.5445(12) 0.6265(2) 1.0016(3) 0.0334(15) Uani 1 1 d . . .
H10A H 0.4867 0.6354 1.0385 0.04 Uiso 1 1 calc R . .
H10B H 0.7106 0.6277 1.0072 0.04 Uiso 1 1 calc R . .
C11 C 0.4687(12) 0.5841(2) 0.9877(3) 0.0333(15) Uani 1 1 d . . .
H11A H 0.5254 0.5753 0.9506 0.04 Uiso 1 1 calc R . .
H11B H 0.5311 0.5662 1.0197 0.04 Uiso 1 1 calc R . .
N12 N 0.2235(9) 0.58200(16) 0.9819(2) 0.0273(11) Uani 1 1 d . . .
C13 C 0.1332(11) 0.6095(2) 0.9353(3) 0.0332(15) Uani 1 1 d . . .
H13A H -0.0329 0.6092 0.9326 0.04 Uiso 1 1 calc R . .
H13B H 0.1788 0.6005 0.897 0.04 Uiso 1 1 calc R . .
C14 C 0.2165(12) 0.6513(2) 0.9473(3) 0.0371(16) Uani 1 1 d . . .
H14A H 0.1575 0.6689 0.9145 0.044 Uiso 1 1 calc R . .
H14B H 0.1603 0.6613 0.9838 0.044 Uiso 1 1 calc R . .
C15 C 0.1324(12) 0.5413(2) 0.9738(3) 0.0341(15) Uani 1 1 d . . .
H15A H -0.0269 0.5416 0.9819 0.041 Uiso 1 1 calc R . .
H15B H 0.2151 0.5237 1.0032 0.041 Uiso 1 1 calc R . .
C16 C 0.1459(12) 0.5239(2) 0.9130(3) 0.0318(15) Uani 1 1 d . . .
C17 C 0.3426(12) 0.5075(2) 0.8965(3) 0.0317(14) Uani 1 1 d . . .
H17 H 0.463 0.5022 0.9259 0.038 Uiso 1 1 calc R . .
C18 C 0.3689(12) 0.49852(19) 0.8385(3) 0.0313(14) Uani 1 1 d . . .
H18 H 0.5048 0.4873 0.828 0.038 Uiso 1 1 calc R . .
C19 C 0.1903(12) 0.5064(2) 0.7959(3) 0.0312(14) Uani 1 1 d . . .
C20 C -0.0150(11) 0.5191(2) 0.8125(3) 0.0334(15) Uani 1 1 d . . .
H20 H -0.1416 0.5213 0.784 0.04 Uiso 1 1 calc R . .
C21 C -0.0343(12) 0.5285(2) 0.8709(3) 0.0341(15) Uani 1 1 d . . .
H21 H -0.173 0.5382 0.8819 0.041 Uiso 1 1 calc R . .
N22 N 0.2031(10) 0.50597(18) 0.7334(3) 0.0350(13) Uani 1 1 d . . .
N23 N 0.4004(10) 0.50716(17) 0.7207(2) 0.0323(12) Uani 1 1 d . . .
C24 C 0.4179(12) 0.5133(2) 0.6590(3) 0.0323(15) Uani 1 1 d . . .
C25 C 0.6281(12) 0.5253(2) 0.6461(3) 0.0355(16) Uani 1 1 d . . .
H25 H 0.7527 0.5241 0.6754 0.043 Uiso 1 1 calc R . .
C26 C 0.6553(12) 0.5390(2) 0.5901(3) 0.0376(16) Uani 1 1 d . . .
H26 H 0.8 0.5472 0.5813 0.045 Uiso 1 1 calc R . .
C27 C 0.4756(12) 0.5410(2) 0.5463(3) 0.0306(14) Uani 1 1 d . . .
C28 C 0.2691(12) 0.5265(2) 0.5599(3) 0.0326(15) Uani 1 1 d . . .
H28 H 0.1459 0.5261 0.5301 0.039 Uiso 1 1 calc R . .
C29 C 0.2387(12) 0.5129(2) 0.6153(3) 0.0329(15) Uani 1 1 d . . .
H29 H 0.0962 0.5032 0.6236 0.039 Uiso 1 1 calc R . .
C30 C 0.5104(13) 0.5605(2) 0.4882(3) 0.0358(16) Uani 1 1 d . . .
H30A H 0.6669 0.5556 0.4797 0.043 Uiso 1 1 calc R . .
H30B H 0.4097 0.5476 0.4567 0.043 Uiso 1 1 calc R . .
N31 N 0.4689(10) 0.60335(17) 0.4858(2) 0.0319(13) Uani 1 1 d . . .
C32 C 0.6025(11) 0.6251(2) 0.5327(3) 0.0332(15) Uani 1 1 d . . .
H32A H 0.7637 0.6191 0.5313 0.04 Uiso 1 1 calc R . .
H32B H 0.56 0.6163 0.5714 0.04 Uiso 1 1 calc R . .
C33 C 0.5659(12) 0.6696(2) 0.5265(3) 0.0383(16) Uani 1 1 d . . .
H33A H 0.6543 0.6835 0.5593 0.046 Uiso 1 1 calc R . .
H33B H 0.6179 0.6788 0.4891 0.046 Uiso 1 1 calc R . .
N34 N 0.3277(10) 0.67876(17) 0.5272(3) 0.0361(13) Uani 1 1 d . . .
C35 C 0.2018(12) 0.6586(2) 0.4779(3) 0.0371(16) Uani 1 1 d . . .
H35A H 0.2566 0.6673 0.4405 0.045 Uiso 1 1 calc R . .
H35B H 0.0407 0.6655 0.4766 0.045 Uiso 1 1 calc R . .
C36 C 0.2307(11) 0.6141(2) 0.4848(3) 0.0350(16) Uani 1 1 d . . .
H36A H 0.1733 0.6054 0.5219 0.042 Uiso 1 1 calc R . .
H36B H 0.1427 0.6004 0.4517 0.042 Uiso 1 1 calc R . .
C37 C 0.2877(15) 0.7217(2) 0.5265(4) 0.047(2) Uani 1 1 d . . .
H37A H 0.1255 0.7268 0.5162 0.056 Uiso 1 1 calc R . .
H37B H 0.3704 0.7341 0.4958 0.056 Uiso 1 1 calc R . .
C38 C 0.3614(14) 0.7407(2) 0.5852(3) 0.0420(18) Uani 1 1 d . . .
C39 C 0.5464(18) 0.7635(3) 0.5955(4) 0.061(2) Uani 1 1 d . . .
H39 H 0.636 0.7683 0.5643 0.073 Uiso 1 1 calc R . .
C40 C 0.6108(19) 0.7803(3) 0.6505(5) 0.070(3) Uani 1 1 d . . .
H40 H 0.7434 0.7959 0.6561 0.084 Uiso 1 1 calc R . .
C41 C 0.4850(18) 0.7743(2) 0.6964(4) 0.054(2) Uani 1 1 d . . .
C42 C 0.2969(18) 0.7518(4) 0.6862(4) 0.069(3) Uani 1 1 d . . .
H42 H 0.207 0.7474 0.7175 0.082 Uiso 1 1 calc R . .
C43 C 0.2327(16) 0.7354(3) 0.6325(4) 0.064(3) Uani 1 1 d . . .
H43 H 0.0989 0.7201 0.6271 0.077 Uiso 1 1 calc R . .
I44 I 0.63667(7) 0.611576(13) 0.372590(17) 0.03301(16) Uani 1 1 d . . .
C45 C 0.7778(11) 0.6061(2) 0.2927(3) 0.0310(15) Uani 1 1 d . . .
C46 C 0.6736(12) 0.6226(2) 0.2411(3) 0.0341(15) Uani 1 1 d . . .
F47 F 0.4809(7) 0.64340(15) 0.24219(18) 0.0496(12) Uani 1 1 d . . .
C48 C 0.7666(12) 0.6200(2) 0.1893(3) 0.0326(15) Uani 1 1 d . . .
F49 F 0.6609(7) 0.63785(15) 0.14085(17) 0.0500(12) Uani 1 1 d . . .
C50 C 0.9626(12) 0.5998(2) 0.1844(3) 0.0282(14) Uani 1 1 d . . .
I51 I 1.09360(7) 0.594653(13) 0.103109(18) 0.03365(17) Uani 1 1 d . . .
C52 C 1.0683(11) 0.5831(2) 0.2356(3) 0.0292(14) Uani 1 1 d . . .
F53 F 1.2623(7) 0.56302(13) 0.23472(18) 0.0407(10) Uani 1 1 d . . .
C54 C 0.9751(11) 0.5862(2) 0.2884(3) 0.0278(14) Uani 1 1 d . . .
F55 F 1.0822(7) 0.56904(13) 0.33618(16) 0.0388(9) Uani 1 1 d . . .
C56 C -0.103(4) 0.6309(7) 0.7269(8) 0.15(4) Uiso 0.2 1 d PD A 1
H56 H -0.1953 0.6109 0.746 0.186 Uiso 0.2 1 calc PR A 1
Cl57 Cl -0.285(4) 0.6667(8) 0.6904(11) 0.146(9) Uiso 0.2 1 d PD A 1
Cl58 Cl 0.083(5) 0.6542(9) 0.7821(9) 0.161(11) Uiso 0.2 1 d PD A 1
Cl59 Cl 0.053(4) 0.6061(6) 0.6757(8) 0.108(6) Uiso 0.2 1 d PD A 1
C64 C 0.112(3) 0.6588(5) 0.6997(6) 0.14(2) Uiso 0.3 1 d PD B 2
H64 H 0.199 0.679 0.6794 0.165 Uiso 0.3 1 calc PR B 2
Cl65 Cl -0.175(2) 0.6703(4) 0.6839(6) 0.111(4) Uiso 0.3 1 d PD B 2
Cl62 Cl 0.197(3) 0.6624(5) 0.7759(6) 0.141(6) Uiso 0.3 1 d PD B 2
Cl63 Cl 0.177(3) 0.6118(5) 0.6720(8) 0.165(7) Uiso 0.3 1 d PD B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C2 C1 C41 114.7(7) . . ?
C2 C1 H1A 108.6 . . ?
C41 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
C41 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C7 117.3(8) . . ?
C3 C2 C1 120.6(10) . . ?
C7 C2 C1 122.0(9) . . ?
C2 C3 C4 122.0(9) . . ?
C2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C3 C4 C5 121.0(8) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.4(7) . . ?
C6 C5 C8 123.1(8) . . ?
C4 C5 C8 119.4(7) . . ?
C5 C6 C7 120.7(8) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 121.6(8) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N9 C8 C5 113.1(6) . . ?
N9 C8 H8A 109 . . ?
C5 C8 H8A 109 . . ?
N9 C8 H8B 109 . . ?
C5 C8 H8B 109 . . ?
H8A C8 H8B 107.8 . . ?
C10 N9 C14 108.8(5) . . ?
C10 N9 C8 111.0(5) . . ?
C14 N9 C8 110.6(6) . . ?
N9 C10 C11 109.6(5) . . ?
N9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N12 C11 C10 109.8(6) . . ?
N12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 N12 C13 109.1(5) . . ?
C11 N12 C15 114.2(5) . . ?
C13 N12 C15 112.9(5) . . ?
N12 C13 C14 111.5(6) . . ?
N12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108 . . ?
N9 C14 C13 110.7(6) . . ?
N9 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N9 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N12 C15 C16 114.8(5) . . ?
N12 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
N12 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 118.7(6) . . ?
C21 C16 C15 118.9(6) . . ?
C17 C16 C15 122.0(6) . . ?
C18 C17 C16 122.0(7) . . ?
C18 C17 H17 119 . . ?
C16 C17 H17 119 . . ?
C17 C18 C19 118.2(6) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 120.2(6) . . ?
C20 C19 N22 114.4(6) . . ?
C18 C19 N22 125.1(6) . . ?
C21 C20 C19 119.8(7) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C16 C21 C20 120.6(7) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
N23 N22 C19 112.3(6) . . ?
N22 N23 C24 113.5(6) . . ?
C25 C24 C29 120.3(6) . . ?
C25 C24 N23 114.2(6) . . ?
C29 C24 N23 125.0(6) . . ?
C24 C25 C26 119.3(7) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 121.6(7) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C28 C27 C26 117.4(6) . . ?
C28 C27 C30 123.6(7) . . ?
C26 C27 C30 119.0(7) . . ?
C29 C28 C27 121.8(7) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C24 119.4(6) . . ?
C28 C29 H29 120.3 . . ?
C24 C29 H29 120.3 . . ?
N31 C30 C27 115.0(5) . . ?
N31 C30 H30A 108.5 . . ?
C27 C30 H30A 108.5 . . ?
N31 C30 H30B 108.5 . . ?
C27 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C30 N31 C32 112.8(6) . . ?
C30 N31 C36 113.9(6) . . ?
C32 N31 C36 110.0(5) . . ?
C30 N31 I44 93.2(4) . . ?
C32 N31 I44 113.2(4) . . ?
C36 N31 I44 113.0(4) . . ?
N31 C32 C33 111.2(6) . . ?
N31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
N31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108 . . ?
N34 C33 C32 109.9(6) . . ?
N34 C33 H33A 109.7 . . ?
C32 C33 H33A 109.7 . . ?
N34 C33 H33B 109.7 . . ?
C32 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C35 N34 C33 108.7(6) . . ?
C35 N34 C37 112.4(6) . . ?
C33 N34 C37 111.6(6) . . ?
N34 C35 C36 109.7(6) . . ?
N34 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
N34 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N31 C36 C35 110.3(6) . . ?
N31 C36 H36A 109.6 . . ?
C35 C36 H36A 109.6 . . ?
N31 C36 H36B 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
N34 C37 C38 112.1(6) . . ?
N34 C37 H37A 109.2 . . ?
C38 C37 H37A 109.2 . . ?
N34 C37 H37B 109.2 . . ?
C38 C37 H37B 109.2 . . ?
H37A C37 H37B 107.9 . . ?
C39 C38 C43 116.4(8) . . ?
C39 C38 C37 123.9(8) . . ?
C43 C38 C37 119.7(8) . . ?
C38 C39 C40 122.3(9) . . ?
C38 C39 H39 118.8 . . ?
C40 C39 H39 118.8 . . ?
C41 C40 C39 120.6(9) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C42 C41 C40 117.6(9) . . ?
C42 C41 C1 122.2(10) . . ?
C40 C41 C1 120.2(10) . . ?
C41 C42 C43 122.2(9) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
C42 C43 C38 121.0(10) . . ?
C42 C43 H43 119.5 . . ?
C38 C43 H43 119.5 . . ?
C45 I44 N31 168.9(2) . . ?
C54 C45 C46 116.7(6) . . ?
C54 C45 I44 122.3(5) . . ?
C46 C45 I44 121.0(5) . . ?
F47 C46 C48 118.4(6) . . ?
F47 C46 C45 120.0(6) . . ?
C48 C46 C45 121.5(7) . . ?
F49 C48 C46 118.8(6) . . ?
F49 C48 C50 118.9(6) . . ?
C46 C48 C50 122.2(6) . . ?
C48 C50 C52 116.8(6) . . ?
C48 C50 I51 121.0(5) . . ?
C52 C50 I51 122.2(5) . . ?
C50 I51 N12 172.5(2) . 1_654 ?
F53 C52 C54 118.5(6) . . ?
F53 C52 C50 120.6(6) . . ?
C54 C52 C50 120.9(6) . . ?
F55 C54 C45 119.7(6) . . ?
F55 C54 C52 118.4(6) . . ?
C45 C54 C52 121.9(6) . . ?
Cl57 C56 Cl58 110.1(6) . . ?
Cl57 C56 Cl59 110.4(6) . . ?
Cl58 C56 Cl59 109.9(7) . . ?
Cl57 C56 H56 108.8 . . ?
Cl58 C56 H56 108.8 . . ?
Cl59 C56 H56 108.8 . . ?
Cl63 C64 Cl65 111.8(7) . . ?
Cl63 C64 Cl62 111.3(6) . . ?
Cl65 C64 Cl62 111.3(6) . . ?
Cl63 C64 H64 107.4 . . ?
Cl65 C64 H64 107.4 . . ?
Cl62 C64 H64 107.4 . . ?
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
C1 C2 1.524(12) . ?
C1 C41 1.525(13) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C3 1.365(13) . ?
C2 C7 1.377(14) . ?
C3 C4 1.380(12) . ?
C3 H3 0.95 . ?
C4 C5 1.390(12) . ?
C4 H4 0.95 . ?
C5 C6 1.377(11) . ?
C5 C8 1.496(10) . ?
C6 C7 1.395(13) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N9 1.463(9) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
N9 C10 1.453(9) . ?
N9 C14 1.454(9) . ?
C10 C11 1.522(10) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 N12 1.462(9) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
N12 C13 1.470(9) . ?
N12 C15 1.478(8) . ?
C13 C14 1.509(9) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.517(9) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C21 1.379(10) . ?
C16 C17 1.387(10) . ?
C17 C18 1.382(10) . ?
C17 H17 0.95 . ?
C18 C19 1.396(10) . ?
C18 H18 0.95 . ?
C19 C20 1.390(10) . ?
C19 N22 1.437(9) . ?
C20 C21 1.386(10) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
N22 N23 1.245(8) . ?
N23 C24 1.439(9) . ?
C24 C25 1.380(10) . ?
C24 C29 1.387(10) . ?
C25 C26 1.387(10) . ?
C25 H25 0.95 . ?
C26 C27 1.393(10) . ?
C26 H26 0.95 . ?
C27 C28 1.393(10) . ?
C27 C30 1.514(9) . ?
C28 C29 1.377(10) . ?
C28 H28 0.95 . ?
C29 H29 0.95 . ?
C30 N31 1.462(9) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
N31 C32 1.467(9) . ?
N31 C36 1.470(9) . ?
N31 I44 2.880(5) . ?
C32 C33 1.516(10) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 N34 1.461(9) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
N34 C35 1.457(10) . ?
N34 C37 1.466(9) . ?
C35 C36 1.512(10) . ?
C35 H35A 0.99 . ?
C35 H35B 0.99 . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C37 C38 1.508(12) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 C39 1.348(13) . ?
C38 C43 1.401(12) . ?
C39 C40 1.393(14) . ?
C39 H39 0.95 . ?
C40 C41 1.367(14) . ?
C40 H40 0.95 . ?
C41 C42 1.357(14) . ?
C42 C43 1.365(13) . ?
C42 H42 0.95 . ?
C43 H43 0.95 . ?
I44 C45 2.095(7) . ?
C45 C54 1.369(10) . ?
C45 C46 1.393(10) . ?
C46 F47 1.351(8) . ?
C46 C48 1.361(10) . ?
C48 F49 1.357(8) . ?
C48 C50 1.371(10) . ?
C50 C52 1.390(10) . ?
C50 I51 2.095(6) . ?
I51 N12 2.982(5) 1_654 ?
C52 F53 1.346(8) . ?
C52 C54 1.383(9) . ?
C54 F55 1.339(8) . ?
C56 Cl57 1.775(5) . ?
C56 Cl58 1.776(7) . ?
C56 Cl59 1.776(7) . ?
C56 H56 1 . ?
C64 Cl63 1.762(7) . ?
C64 Cl65 1.764(7) . ?
C64 Cl62 1.766(5) . ?
C64 H64 1 . ?
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
C41 C1 C2 C3 72.9(14) . . . . ?
C41 C1 C2 C7 -109.8(11) . . . . ?
C7 C2 C3 C4 -1.1(15) . . . . ?
C1 C2 C3 C4 176.4(9) . . . . ?
C2 C3 C4 C5 0.7(16) . . . . ?
C3 C4 C5 C6 0.5(13) . . . . ?
C3 C4 C5 C8 -175.9(8) . . . . ?
C4 C5 C6 C7 -1.3(12) . . . . ?
C8 C5 C6 C7 175.0(8) . . . . ?
C3 C2 C7 C6 0.2(14) . . . . ?
C1 C2 C7 C6 -177.2(9) . . . . ?
C5 C6 C7 C2 1.0(14) . . . . ?
C6 C5 C8 N9 107.0(9) . . . . ?
C4 C5 C8 N9 -76.8(10) . . . . ?
C5 C8 N9 C10 160.4(6) . . . . ?
C5 C8 N9 C14 -78.8(8) . . . . ?
C14 N9 C10 C11 61.2(7) . . . . ?
C8 N9 C10 C11 -177.0(6) . . . . ?
N9 C10 C11 N12 -61.7(7) . . . . ?
C10 C11 N12 C13 57.9(7) . . . . ?
C10 C11 N12 C15 -174.7(5) . . . . ?
C11 N12 C13 C14 -56.0(7) . . . . ?
C15 N12 C13 C14 175.8(6) . . . . ?
C10 N9 C14 C13 -58.9(7) . . . . ?
C8 N9 C14 C13 179.0(6) . . . . ?
N12 C13 C14 N9 57.0(8) . . . . ?
C11 N12 C15 C16 -74.8(8) . . . . ?
C13 N12 C15 C16 50.6(8) . . . . ?
N12 C15 C16 C21 -92.3(8) . . . . ?
N12 C15 C16 C17 80.1(8) . . . . ?
C21 C16 C17 C18 5.0(10) . . . . ?
C15 C16 C17 C18 -167.4(6) . . . . ?
C16 C17 C18 C19 0.0(10) . . . . ?
C17 C18 C19 C20 -6.5(10) . . . . ?
C17 C18 C19 N22 167.8(6) . . . . ?
C18 C19 C20 C21 7.8(10) . . . . ?
N22 C19 C20 C21 -167.0(6) . . . . ?
C17 C16 C21 C20 -3.7(10) . . . . ?
C15 C16 C21 C20 169.0(6) . . . . ?
C19 C20 C21 C16 -2.6(11) . . . . ?
C20 C19 N22 N23 158.4(6) . . . . ?
C18 C19 N22 N23 -16.2(10) . . . . ?
C19 N22 N23 C24 -170.4(6) . . . . ?
N22 N23 C24 C25 163.4(6) . . . . ?
N22 N23 C24 C29 -8.2(10) . . . . ?
C29 C24 C25 C26 3.6(11) . . . . ?
N23 C24 C25 C26 -168.4(6) . . . . ?
C24 C25 C26 C27 0.0(11) . . . . ?
C25 C26 C27 C28 -3.6(10) . . . . ?
C25 C26 C27 C30 173.1(7) . . . . ?
C26 C27 C28 C29 3.7(10) . . . . ?
C30 C27 C28 C29 -172.9(6) . . . . ?
C27 C28 C29 C24 -0.2(10) . . . . ?
C25 C24 C29 C28 -3.6(10) . . . . ?
N23 C24 C29 C28 167.6(6) . . . . ?
C28 C27 C30 N31 87.6(9) . . . . ?
C26 C27 C30 N31 -88.9(8) . . . . ?
C27 C30 N31 C32 55.4(8) . . . . ?
C27 C30 N31 C36 -70.9(8) . . . . ?
C27 C30 N31 I44 172.3(6) . . . . ?
C30 N31 C32 C33 176.5(6) . . . . ?
C36 N31 C32 C33 -55.2(7) . . . . ?
I44 N31 C32 C33 72.2(6) . . . . ?
N31 C32 C33 N34 57.7(8) . . . . ?
C32 C33 N34 C35 -60.5(7) . . . . ?
C32 C33 N34 C37 175.0(6) . . . . ?
C33 N34 C35 C36 62.1(7) . . . . ?
C37 N34 C35 C36 -174.0(6) . . . . ?
C30 N31 C36 C35 -176.0(6) . . . . ?
C32 N31 C36 C35 56.3(7) . . . . ?
I44 N31 C36 C35 -71.3(6) . . . . ?
N34 C35 C36 N31 -60.4(8) . . . . ?
C35 N34 C37 C38 163.5(7) . . . . ?
C33 N34 C37 C38 -74.2(8) . . . . ?
N34 C37 C38 C39 106.6(9) . . . . ?
N34 C37 C38 C43 -74.1(10) . . . . ?
C43 C38 C39 C40 1.5(14) . . . . ?
C37 C38 C39 C40 -179.3(8) . . . . ?
C38 C39 C40 C41 -0.7(16) . . . . ?
C39 C40 C41 C42 -0.2(15) . . . . ?
C39 C40 C41 C1 -178.8(9) . . . . ?
C2 C1 C41 C42 45.2(16) . . . . ?
C2 C1 C41 C40 -136.2(11) . . . . ?
C40 C41 C42 C43 0.1(16) . . . . ?
C1 C41 C42 C43 178.7(10) . . . . ?
C41 C42 C43 C38 0.8(17) . . . . ?
C39 C38 C43 C42 -1.5(14) . . . . ?
C37 C38 C43 C42 179.2(9) . . . . ?
C30 N31 I44 C45 -8.1(14) . . . . ?
C32 N31 I44 C45 108.4(12) . . . . ?
C36 N31 I44 C45 -125.7(11) . . . . ?
N31 I44 C45 C54 -40.9(15) . . . . ?
N31 I44 C45 C46 139.1(10) . . . . ?
C54 C45 C46 F47 -178.6(7) . . . . ?
I44 C45 C46 F47 1.4(10) . . . . ?
C54 C45 C46 C48 -1.5(11) . . . . ?
I44 C45 C46 C48 178.4(6) . . . . ?
F47 C46 C48 F49 -0.8(11) . . . . ?
C45 C46 C48 F49 -178.0(7) . . . . ?
F47 C46 C48 C50 179.5(7) . . . . ?
C45 C46 C48 C50 2.4(12) . . . . ?
F49 C48 C50 C52 178.0(6) . . . . ?
C46 C48 C50 C52 -2.4(11) . . . . ?
F49 C48 C50 I51 -2.0(9) . . . . ?
C46 C48 C50 I51 177.6(6) . . . . ?
C48 C50 C52 F53 -179.6(6) . . . . ?
I51 C50 C52 F53 0.4(9) . . . . ?
C48 C50 C52 C54 1.6(10) . . . . ?
I51 C50 C52 C54 -178.4(5) . . . . ?
C46 C45 C54 F55 -179.0(6) . . . . ?
I44 C45 C54 F55 1.0(9) . . . . ?
C46 C45 C54 C52 0.8(10) . . . . ?
I44 C45 C54 C52 -179.2(5) . . . . ?
F53 C52 C54 F55 0.1(9) . . . . ?
C50 C52 C54 F55 178.9(6) . . . . ?
F53 C52 C54 C45 -179.7(6) . . . . ?
C50 C52 C54 C45 -0.9(11) . . . . ?
