#------------------------------------------------------------------------------
#$Date: 2020-04-05 12:13:49 +0200 (dom 05 de abr de 2020) $
#$Revision: 250200 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/59/7125983.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_7125983
loop_
_publ_author_name
'Carreira-Barral, Israel'
'Mielczarek, Marcin'
'Alonso-Carrillo, Daniel'
'Capurro, Valeria'
'Soto-Cerrato, Vanessa'
'Pérez Tomás, Ricardo'
'Caci, Emanuela'
'García-Valverde, María'
'Quesada, Roberto'
_publ_section_title
;
 Click-tambjamines as efficient and tunable bioactive anion transporters.
;
_journal_issue                   21
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3218
_journal_page_last               3221
_journal_paper_doi               10.1039/d0cc00643b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C20 H23 Cl N5 O, C4 H10 O, Cl, H2 O'
_chemical_formula_sum            'C24 H35 Cl2 N5 O3'
_chemical_formula_weight         512.47
_chemical_name_systematic        MM34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-01-23 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                99.4900(12)
_cell_angle_beta                 91.0584(12)
_cell_angle_gamma                110.6256(11)
_cell_formula_units_Z            2
_cell_length_a                   7.9219(2)
_cell_length_b                   9.5881(2)
_cell_length_c                   19.0533(5)
_cell_measurement_reflns_used    4815
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.72
_cell_measurement_theta_min      2.36
_cell_volume                     1331.31(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17573
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.723
_diffrn_reflns_theta_min         2.359
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_transmission_factor_max   1
_exptl_transmission_factor_min   0.822
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0356
_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/[σ²(Fo²)+(0.0344P)²+0.5458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4232
_reflns_number_total             4815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00643b2.cif
_cod_data_source_block           MM34
_cod_depositor_comments
'Adding full bibliography for 7125982--7125984.cif.'
_cod_database_code               7125983
_shelx_shelxl_version_number     2016/6
_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.
;
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
C1 C -0.5384(2) 0.10295(19) 0.21157(9) 0.0186(3) Uani 1 1 d . . . . .
C2 C -0.4212(2) 0.23653(19) 0.25306(9) 0.0200(3) Uani 1 1 d . . . . .
H2 H -0.381349 0.327843 0.234504 0.024 Uiso 1 1 calc R U . . .
C3 C -0.3631(2) 0.23491(19) 0.32186(9) 0.0192(3) Uani 1 1 d . . . . .
H3 H -0.282772 0.325043 0.351084 0.023 Uiso 1 1 calc R U . . .
C4 C -0.4238(2) 0.09953(18) 0.34753(8) 0.0168(3) Uani 1 1 d . . . . .
C5 C -0.5443(2) -0.03320(18) 0.30650(9) 0.0185(3) Uani 1 1 d . . . . .
H5 H -0.586367 -0.123997 0.325423 0.022 Uiso 1 1 calc R U . . .
C6 C -0.6027(2) -0.03178(19) 0.23747(9) 0.0195(3) Uani 1 1 d . . . . .
H6 H -0.685120 -0.121314 0.208553 0.023 Uiso 1 1 calc R U . . .
C7 C -0.3293(2) -0.02354(18) 0.43902(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C -0.2473(2) 0.03517(18) 0.50646(9) 0.0165(3) Uani 1 1 d . . . . .
C9 C -0.1822(2) -0.03799(18) 0.55571(8) 0.0161(3) Uani 1 1 d . . . . .
C10 C -0.2024(2) -0.19103(18) 0.54742(8) 0.0172(3) Uani 1 1 d . . . . .
H10 H -0.263624 -0.269577 0.508295 0.021 Uiso 1 1 calc R U . . .
C11 C -0.1139(2) -0.20411(18) 0.60852(9) 0.0171(3) Uani 1 1 d . . . . .
C12 C -0.1619(3) -0.46387(18) 0.57539(9) 0.0236(4) Uani 1 1 d . . . . .
H12A H -0.293962 -0.495311 0.569194 0.035 Uiso 1 1 calc R U . . .
H12B H -0.129810 -0.543261 0.592194 0.035 Uiso 1 1 calc R U . . .
H12C H -0.111212 -0.447329 0.529635 0.035 Uiso 1 1 calc R U . . .
C13 C -0.0429(2) -0.05983(18) 0.65364(8) 0.0162(3) Uani 1 1 d . . . . .
C14 C 0.0502(2) -0.02767(18) 0.71997(8) 0.0166(3) Uani 1 1 d . . . . .
H14 H 0.070027 -0.110158 0.735603 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2121(2) 0.12577(18) 0.83336(8) 0.0172(3) Uani 1 1 d . . . . .
H15 H 0.254002 0.038923 0.833740 0.021 Uiso 1 1 calc R U . . .
C16 C 0.0900(2) 0.12951(19) 0.89403(9) 0.0205(3) Uani 1 1 d . . . . .
H16A H -0.014672 0.032666 0.887147 0.025 Uiso 1 1 calc R U . . .
H16B H 0.043183 0.212415 0.893361 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1942(2) 0.1541(2) 0.96620(9) 0.0237(4) Uani 1 1 d . . . . .
H17A H 0.114752 0.161882 1.005016 0.028 Uiso 1 1 calc R U . . .
H17B H 0.230331 0.066084 0.968671 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3628(2) 0.2986(2) 0.97672(9) 0.0234(4) Uani 1 1 d . . . . .
H18A H 0.326026 0.387799 0.979520 0.028 Uiso 1 1 calc R U . . .
H18B H 0.432129 0.308907 1.022261 0.028 Uiso 1 1 calc R U . . .
C19 C 0.4829(2) 0.2947(2) 0.91515(9) 0.0237(4) Uani 1 1 d . . . . .
H19A H 0.588160 0.391162 0.921949 0.028 Uiso 1 1 calc R U . . .
H19B H 0.529080 0.211263 0.915194 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3783(2) 0.27154(19) 0.84351(9) 0.0204(3) Uani 1 1 d . . . . .
H20A H 0.457396 0.265589 0.804371 0.024 Uiso 1 1 calc R U . . .
H20B H 0.340117 0.358830 0.841840 0.024 Uiso 1 1 calc R U . . .
C21 C 0.1531(3) 0.6402(3) 0.93153(12) 0.0392(5) Uani 1 1 d . . . . .
H21A H 0.244640 0.634990 0.898344 0.059 Uiso 1 1 calc R U . . .
H21B H 0.157060 0.582383 0.969020 0.059 Uiso 1 1 calc R U . . .
H21C H 0.177722 0.746181 0.953195 0.059 Uiso 1 1 calc R U . . .
C22 C -0.0333(2) 0.5735(2) 0.89125(10) 0.0252(4) Uani 1 1 d . . . . .
H22A H -0.125683 0.573869 0.925497 0.030 Uiso 1 1 calc R U . . .
H22B H -0.056799 0.466783 0.869076 0.030 Uiso 1 1 calc R U . . .
C23 C -0.0524(2) 0.6607(2) 0.83329(10) 0.0233(4) Uani 1 1 d . . . . .
H23A H -0.030975 0.766806 0.855870 0.028 Uiso 1 1 calc R U . . .
H23B H 0.042599 0.662560 0.800016 0.028 Uiso 1 1 calc R U . . .
C24 C -0.2356(3) 0.5951(2) 0.79074(10) 0.0264(4) Uani 1 1 d . . . . .
H24A H -0.330509 0.595809 0.823719 0.032 Uiso 1 1 calc R U . . .
H24B H -0.238513 0.660937 0.756165 0.032 Uiso 1 1 calc R U . . .
N1 N -0.35435(18) 0.09492(15) 0.41648(7) 0.0169(3) Uani 1 1 d . . . . .
N2 N -0.2917(2) 0.22218(16) 0.46801(8) 0.0213(3) Uani 1 1 d . . . . .
N3 N -0.2271(2) 0.18530(16) 0.52280(8) 0.0209(3) Uani 1 1 d . . . . .
N4 N -0.08821(18) 0.03946(16) 0.61818(7) 0.0157(3) Uani 1 1 d . . . . .
N5 N 0.11432(19) 0.10308(16) 0.76382(7) 0.0181(3) Uani 1 1 d . . . . .
O1 O -0.08915(17) -0.32438(12) 0.62742(6) 0.0212(3) Uani 1 1 d . . . . .
O2 O -0.27654(18) 0.44399(15) 0.75286(7) 0.0281(3) Uani 1 1 d . . . . .
O1W O 0.4342(2) 0.35515(16) 0.64384(8) 0.0322(3) Uani 1 1 d . . . . .
Cl1 Cl -0.60222(6) 0.10344(5) 0.12348(2) 0.02535(11) Uani 1 1 d . . . . .
Cl2 Cl 0.07036(5) 0.37947(4) 0.70754(2) 0.02138(11) Uani 1 1 d . . . . .
H4N H -0.056(3) 0.130(3) 0.6331(11) 0.026 Uiso 1 1 d . U . . .
H5N H 0.099(3) 0.177(3) 0.7525(11) 0.026 Uiso 1 1 d . U . . .
H7 H -0.365(3) -0.119(3) 0.4110(11) 0.026 Uiso 1 1 d . U . . .
H1W H 0.340(3) 0.380(2) 0.6625(11) 0.026 Uiso 1 1 d . U . . .
H2W H 0.519(3) 0.385(2) 0.6785(12) 0.026 Uiso 1 1 d . U . . .
H1S H -0.185(3) 0.430(2) 0.7376(11) 0.026 Uiso 1 1 d . U . . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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
C6 C1 C2 122.02(15) . . ?
C6 C1 Cl1 119.01(13) . . ?
C2 C1 Cl1 118.96(13) . . ?
C3 C2 C1 119.14(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.10(16) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.65(15) . . ?
C5 C4 N1 119.04(14) . . ?
C3 C4 N1 119.25(15) . . ?
C4 C5 C6 119.32(15) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.75(16) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C8 104.19(14) . . ?
N1 C7 H7 122.5(13) . . ?
C8 C7 H7 133.3(13) . . ?
C7 C8 N3 109.08(14) . . ?
C7 C8 C9 128.98(15) . . ?
N3 C8 C9 121.91(15) . . ?
N4 C9 C10 110.43(14) . . ?
N4 C9 C8 121.88(14) . . ?
C10 C9 C8 127.69(15) . . ?
C11 C10 C9 105.67(14) . . ?
C11 C10 H10 127.2 . . ?
C9 C10 H10 127.2 . . ?
O1 C11 C10 130.62(15) . . ?
O1 C11 C13 120.66(14) . . ?
C10 C11 C13 108.71(14) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N4 127.82(15) . . ?
C14 C13 C11 125.93(14) . . ?
N4 C13 C11 106.25(14) . . ?
N5 C14 C13 127.73(15) . . ?
N5 C14 H14 116.1 . . ?
C13 C14 H14 116.1 . . ?
N5 C15 C16 111.27(13) . . ?
N5 C15 C20 109.60(13) . . ?
C16 C15 C20 110.97(13) . . ?
N5 C15 H15 108.3 . . ?
C16 C15 H15 108.3 . . ?
C20 C15 H15 108.3 . . ?
C15 C16 C17 110.65(14) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 110.84(14) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 110.86(14) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 111.10(14) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C15 110.01(13) . . ?
C19 C20 H20A 109.7 . . ?
C15 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C15 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 C22 C23 112.66(15) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 114.15(15) . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
O2 C24 C23 113.43(15) . . ?
O2 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
O2 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C7 N1 N2 111.05(13) . . ?
C7 N1 C4 127.90(14) . . ?
N2 N1 C4 120.92(13) . . ?
N3 N2 N1 106.90(13) . . ?
N2 N3 C8 108.78(14) . . ?
C9 N4 C13 108.93(14) . . ?
C9 N4 H4N 127.4(15) . . ?
C13 N4 H4N 123.6(15) . . ?
C14 N5 C15 123.61(14) . . ?
C14 N5 H5N 119.2(15) . . ?
C15 N5 H5N 117.2(16) . . ?
C11 O1 C12 115.29(13) . . ?
C24 O2 H1S 112.1(16) . . ?
H1W O1W H2W 106.0(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
C1 C6 1.388(2) . ?
C1 C2 1.389(2) . ?
C1 Cl1 1.7451(16) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 N1 1.428(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.353(2) . ?
C7 C8 1.365(2) . ?
C7 H7 0.92(2) . ?
C8 N3 1.372(2) . ?
C8 C9 1.447(2) . ?
C9 N4 1.345(2) . ?
C9 C10 1.400(2) . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 O1 1.3385(19) . ?
C11 C13 1.418(2) . ?
C12 O1 1.450(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.383(2) . ?
C13 N4 1.391(2) . ?
C14 N5 1.311(2) . ?
C14 H14 0.9500 . ?
C15 N5 1.467(2) . ?
C15 C16 1.525(2) . ?
C15 C20 1.526(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.530(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.530(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.528(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.526(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.519(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.526(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.518(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O2 1.429(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N1 N2 1.364(2) . ?
N2 N3 1.306(2) . ?
N4 H4N 0.82(2) . ?
N5 H5N 0.82(2) . ?
O2 H1S 0.83(2) . ?
O1W H1W 0.92(2) . ?
O1W H2W 0.87(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B N3 0.98 2.56 3.199(2) 123.2 1_545
C16 H16A Cl1 0.99 2.84 3.6954(17) 145.3 2_456
C20 H20A O2 0.99 2.53 3.335(2) 137.9 1_655
N4 H4N Cl2 0.82(2) 2.42(2) 3.2109(14) 163.3(19) .
N5 H5N Cl2 0.82(2) 2.33(2) 3.1413(14) 173(2) .
C7 H7 O1W 0.92(2) 2.20(2) 3.119(2) 172.1(18) 2_556
O1W H1W Cl2 0.92(2) 2.31(2) 3.2158(15) 165.9(18) .
O1W H2W O2 0.87(2) 1.99(2) 2.856(2) 176(2) 1_655
O2 H1S Cl2 0.83(2) 2.30(2) 3.1289(14) 173(2) .
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
C6 C1 C2 C3 1.5(3) . . . . ?
Cl1 C1 C2 C3 -176.81(13) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C2 C3 C4 N1 175.59(15) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
N1 C4 C5 C6 -175.58(14) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
Cl1 C1 C6 C5 176.83(12) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
N1 C7 C8 N3 0.60(18) . . . . ?
N1 C7 C8 C9 -177.44(16) . . . . ?
C7 C8 C9 N4 173.49(16) . . . . ?
N3 C8 C9 N4 -4.3(2) . . . . ?
C7 C8 C9 C10 -5.9(3) . . . . ?
N3 C8 C9 C10 176.29(16) . . . . ?
N4 C9 C10 C11 -0.40(18) . . . . ?
C8 C9 C10 C11 179.05(15) . . . . ?
C9 C10 C11 O1 -178.66(16) . . . . ?
C9 C10 C11 C13 0.70(18) . . . . ?
O1 C11 C13 C14 -2.2(3) . . . . ?
C10 C11 C13 C14 178.39(15) . . . . ?
O1 C11 C13 N4 178.69(14) . . . . ?
C10 C11 C13 N4 -0.74(18) . . . . ?
N4 C13 C14 N5 0.6(3) . . . . ?
C11 C13 C14 N5 -178.37(17) . . . . ?
N5 C15 C16 C17 -179.68(13) . . . . ?
C20 C15 C16 C17 -57.36(18) . . . . ?
C15 C16 C17 C18 56.05(19) . . . . ?
C16 C17 C18 C19 -55.6(2) . . . . ?
C17 C18 C19 C20 56.49(19) . . . . ?
C18 C19 C20 C15 -57.24(19) . . . . ?
N5 C15 C20 C19 -178.98(13) . . . . ?
C16 C15 C20 C19 57.73(18) . . . . ?
C21 C22 C23 C24 178.65(17) . . . . ?
C22 C23 C24 O2 -61.4(2) . . . . ?
C8 C7 N1 N2 -0.42(18) . . . . ?
C8 C7 N1 C4 175.34(15) . . . . ?
C5 C4 N1 C7 28.3(2) . . . . ?
C3 C4 N1 C7 -148.78(16) . . . . ?
C5 C4 N1 N2 -156.30(15) . . . . ?
C3 C4 N1 N2 26.6(2) . . . . ?
C7 N1 N2 N3 0.08(18) . . . . ?
C4 N1 N2 N3 -176.02(14) . . . . ?
N1 N2 N3 C8 0.30(18) . . . . ?
C7 C8 N3 N2 -0.58(19) . . . . ?
C9 C8 N3 N2 177.62(15) . . . . ?
C10 C9 N4 C13 -0.06(18) . . . . ?
C8 C9 N4 C13 -179.55(14) . . . . ?
C14 C13 N4 C9 -178.62(16) . . . . ?
C11 C13 N4 C9 0.49(17) . . . . ?
C13 C14 N5 C15 -179.84(15) . . . . ?
C16 C15 N5 C14 -101.11(18) . . . . ?
C20 C15 N5 C14 135.78(16) . . . . ?
C10 C11 O1 C12 1.7(2) . . . . ?
C13 C11 O1 C12 -177.56(15) . . . . ?
