#------------------------------------------------------------------------------
#$Date: 2022-09-30 04:09:59 +0300 (Fri, 30 Sep 2022) $
#$Revision: 278274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245590.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_7245590
loop_
_publ_author_name
'Viviano-Posadas, Alejandro O.'
'Romero-Mendoza, Ulises'
'Bazany-Rodríguez, Iván J.'
'Velázquez-Castillo, Rocío V.'
'Martínez-Otero, Diego'
'Bautista-Renedo, Joanatan M.'
'González-Rivas, Nelly'
'Galindo-Murillo, Rodrigo'
'Salomón-Flores, María K.'
'Dorazco-González, Alejandro'
_publ_section_title
;
 Efficient fluorescent recognition of ATP/GTP by a water-soluble
 bisquinolinium pyridine-2,6-dicarboxamide compound. Crystal structures,
 spectroscopic studies and interaction mode with DNA
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              27826
_journal_page_last               27838
_journal_paper_doi               10.1039/D2RA05040D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         '2(C33 H31 N5 O6), 4(C H4 O), 4(Br), 3(H2 O)'
_chemical_formula_sum            'C70 H84 Br4 N10 O19'
_chemical_formula_weight         1689.11
_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
;
2021-10-29 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                91.9737(5)
_cell_angle_beta                 100.2535(5)
_cell_angle_gamma                92.6788(5)
_cell_formula_units_Z            1
_cell_length_a                   10.06590(10)
_cell_length_b                   11.5585(2)
_cell_length_c                   16.0001(2)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.23
_cell_volume                     1828.10(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_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            46156
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_min         1.765
_diffrn_source                   'Incoatec ImuS'
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' SADABS-2016/2, Sheldrick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       Prism
_exptl_crystal_F_000             866
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         8342
_refine_ls_number_restraints     375
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0261
_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)+(0.0248P)²+2.1118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7683
_reflns_number_total             8342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05040d2.cif
_cod_data_source_block           mo_033DGA17_0m
_cod_database_code               7245590
_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. 
;
_shelx_estimated_absorpt_t_min   0.600
_shelx_estimated_absorpt_t_max   0.772
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
Br1 Br 0.66606(2) 0.43136(2) 0.17824(2) 0.02031(5) Uani 1 1 d D . . . .
Br2 Br 0.23053(2) 0.14971(2) 0.19499(2) 0.02388(5) Uani 1 1 d D . . . .
O1 O 0.04190(12) 0.47587(12) 0.37086(8) 0.0211(3) Uani 1 1 d . . . . .
O4 O 0.65702(12) 0.33001(11) 0.61384(8) 0.0175(2) Uani 1 1 d . . . . .
O7 O 0.47176(13) 0.31997(13) 0.29698(8) 0.0225(3) Uani 1 1 d D . . . .
H7A H 0.417(2) 0.2661(16) 0.2737(14) 0.027 Uiso 1 1 d D U . . .
H7B H 0.519(2) 0.3455(19) 0.2660(16) 0.027 Uiso 1 1 d D U . . .
O8 O 0.5708(6) 0.1284(5) 0.1668(7) 0.058(3) Uani 0.373(10) 1 d D U P A 1
H8A H 0.587(9) 0.196(3) 0.152(5) 0.069 Uiso 0.373(10) 1 d D U P A 1
H8B H 0.495(5) 0.117(6) 0.179(6) 0.069 Uiso 0.373(10) 1 d D U P A 1
O8A O 0.535(2) 0.1426(19) 0.112(2) 0.067(5) Uani 0.127(9) 1 d D U P B 2
H8C H 0.568(19) 0.211(6) 0.114(10) 0.080 Uiso 0.127(9) 1 d D U P B 2
H8D H 0.453(5) 0.139(17) 0.117(9) 0.080 Uiso 0.127(9) 1 d D U P B 2
O9 O 0.77473(18) 0.09050(13) 0.70626(10) 0.0350(4) Uani 1 1 d D . . . .
H9A H 0.775(3) 0.0267(19) 0.7324(18) 0.053 Uiso 1 1 d D U . . .
O10 O 0.52233(18) 0.08460(15) 0.60130(12) 0.0439(4) Uani 1 1 d D . . . .
H10A H 0.602(2) 0.099(3) 0.6360(18) 0.066 Uiso 1 1 d D U . . .
N1 N 0.36676(14) 0.38766(12) 0.46332(9) 0.0121(3) Uani 1 1 d . . . . .
N2 N 0.22382(14) 0.43741(13) 0.30936(9) 0.0133(3) Uani 1 1 d D . . . .
H2N H 0.3011(17) 0.4136(18) 0.3195(13) 0.016 Uiso 1 1 d D U . . .
N3 N 0.25622(14) 0.54746(13) 0.10432(9) 0.0149(3) Uani 1 1 d . . . . .
N4 N 0.61943(14) 0.30959(13) 0.46871(9) 0.0141(3) Uani 1 1 d D . . . .
H4N H 0.5630(19) 0.3181(18) 0.4244(11) 0.017 Uiso 1 1 d D U . . .
N5 N 0.89491(14) 0.22949(12) 0.36276(9) 0.0144(3) Uani 1 1 d . . . . .
C1 C 0.23935(16) 0.41784(14) 0.46092(10) 0.0126(3) Uani 1 1 d . . . . .
C2 C 0.18006(17) 0.42901(15) 0.53277(11) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.088087 0.447447 0.527868 0.019 Uiso 1 1 calc R U . . .
C3 C 0.25796(18) 0.41267(16) 0.61168(11) 0.0177(3) Uani 1 1 d . . . . .
H3 H 0.220922 0.420978 0.662045 0.021 Uiso 1 1 calc R U . . .
C4 C 0.39078(18) 0.38400(15) 0.61554(11) 0.0165(3) Uani 1 1 d . . . . .
H4 H 0.447564 0.374077 0.668673 0.020 Uiso 1 1 calc R U . . .
C5 C 0.43937(16) 0.37003(14) 0.53979(10) 0.0129(3) Uani 1 1 d . . . . .
C6 C 0.15798(17) 0.44630(15) 0.37635(10) 0.0144(3) Uani 1 1 d . . . . .
C7 C 0.18224(17) 0.48570(14) 0.23076(10) 0.0136(3) Uani 1 1 d . . . . .
C8 C 0.05561(17) 0.52567(15) 0.20135(11) 0.0146(3) Uani 1 1 d . . . . .
H8 H -0.014732 0.514925 0.233266 0.018 Uiso 1 1 calc R U . . .
C9 C 0.03128(17) 0.58238(15) 0.12387(10) 0.0143(3) Uani 1 1 d . . . . .
C10 C -0.09519(17) 0.63019(15) 0.09440(11) 0.0172(3) Uani 1 1 d . . . . .
H10 H -0.165864 0.621736 0.126304 0.021 Uiso 1 1 calc R U . . .
C11 C -0.11620(18) 0.68831(16) 0.02048(11) 0.0184(3) Uani 1 1 d . . . . .
H11 H -0.201108 0.720029 0.001356 0.022 Uiso 1 1 calc R U . . .
C12 C -0.01179(18) 0.70112(16) -0.02730(11) 0.0195(4) Uani 1 1 d . . . . .
H12 H -0.027192 0.742194 -0.078253 0.023 Uiso 1 1 calc R U . . .
C13 C 0.11185(18) 0.65536(16) -0.00162(11) 0.0178(3) Uani 1 1 d . . . . .
H13 H 0.181151 0.664224 -0.034553 0.021 Uiso 1 1 calc R U . . .
C14 C 0.13414(17) 0.59514(15) 0.07425(10) 0.0145(3) Uani 1 1 d . . . . .
C15 C 0.27992(17) 0.49647(15) 0.17855(10) 0.0151(3) Uani 1 1 d . . . . .
H15 H 0.366019 0.466354 0.196769 0.018 Uiso 1 1 calc R U . . .
C16 C 0.36895(18) 0.55531(17) 0.05609(11) 0.0190(4) Uani 1 1 d D . . . .
H16A H 0.330673 0.544390 -0.005260 0.023 Uiso 0.626(4) 1 calc R U P C 1
H16B H 0.428114 0.490503 0.071737 0.023 Uiso 0.626(4) 1 calc R U P C 1
H16C H 0.331678 0.560356 -0.005179 0.023 Uiso 0.374(4) 1 calc R U P C 2
H16D H 0.420137 0.484175 0.063423 0.023 Uiso 0.374(4) 1 calc R U P C 2
O2 O 0.5457(9) 0.6843(12) 0.0328(5) 0.0291(14) Uani 0.626(4) 1 d D U P C 1
C17 C 0.4545(7) 0.6664(5) 0.0696(3) 0.0240(10) Uani 0.626(4) 1 d D U P C 1
O3 O 0.4080(3) 0.7384(2) 0.12350(19) 0.0251(6) Uani 0.626(4) 1 d D U P C 1
C18 C 0.4889(4) 0.8471(3) 0.1449(2) 0.0295(7) Uani 0.626(4) 1 d D U P C 1
H18A H 0.431733 0.907816 0.162101 0.035 Uiso 0.626(4) 1 calc R U P C 1
H18B H 0.524680 0.873105 0.094471 0.035 Uiso 0.626(4) 1 calc R U P C 1
C19 C 0.6036(5) 0.8297(4) 0.2161(3) 0.0423(10) Uani 0.626(4) 1 d D U P C 1
H19A H 0.659156 0.768788 0.199065 0.063 Uiso 0.626(4) 1 calc R U P C 1
H19B H 0.567745 0.806823 0.266459 0.063 Uiso 0.626(4) 1 calc R U P C 1
H19C H 0.659099 0.902225 0.229261 0.063 Uiso 0.626(4) 1 calc R U P C 1
O2A O 0.5593(15) 0.686(2) 0.0509(8) 0.0265(19) Uani 0.374(4) 1 d D U P C 2
C17A C 0.4645(12) 0.6610(8) 0.0860(6) 0.0242(12) Uani 0.374(4) 1 d D U P C 2
O3A O 0.4516(5) 0.7154(4) 0.1600(3) 0.0248(8) Uani 0.374(4) 1 d D U P C 2
C18A C 0.5461(7) 0.8135(6) 0.1941(5) 0.0307(10) Uani 0.374(4) 1 d D U P C 2
H18C H 0.638012 0.795836 0.185181 0.037 Uiso 0.374(4) 1 calc R U P C 2
H18D H 0.548707 0.823145 0.256096 0.037 Uiso 0.374(4) 1 calc R U P C 2
C19A C 0.5082(7) 0.9238(6) 0.1536(5) 0.0430(15) Uani 0.374(4) 1 d D U P C 2
H19D H 0.508158 0.915521 0.092428 0.065 Uiso 0.374(4) 1 calc R U P C 2
H19E H 0.573690 0.986354 0.178769 0.065 Uiso 0.374(4) 1 calc R U P C 2
H19F H 0.417787 0.942292 0.162875 0.065 Uiso 0.374(4) 1 calc R U P C 2
C20 C 0.58266(17) 0.33445(14) 0.54512(10) 0.0133(3) Uani 1 1 d . . . . .
C21 C 0.74477(16) 0.26775(14) 0.45982(10) 0.0136(3) Uani 1 1 d . . . . .
C22 C 0.83352(17) 0.22118(15) 0.52408(11) 0.0152(3) Uani 1 1 d . . . . .
H22 H 0.811154 0.215618 0.579090 0.018 Uiso 1 1 calc R U . . .
C23 C 0.95723(17) 0.18190(15) 0.50816(11) 0.0148(3) Uani 1 1 d . . . . .
C24 C 1.05128(18) 0.13666(16) 0.57395(11) 0.0187(3) Uani 1 1 d . . . . .
H24 H 1.030144 0.130979 0.629261 0.022 Uiso 1 1 calc R U . . .
C25 C 1.17251(19) 0.10110(17) 0.55802(12) 0.0220(4) Uani 1 1 d . . . . .
H25 H 1.236275 0.072711 0.602667 0.026 Uiso 1 1 calc R U . . .
C26 C 1.20297(18) 0.10646(17) 0.47573(12) 0.0214(4) Uani 1 1 d . . . . .
H26 H 1.287627 0.081587 0.465755 0.026 Uiso 1 1 calc R U . . .
C27 C 1.11364(17) 0.14665(16) 0.40959(11) 0.0179(3) Uani 1 1 d . . . . .
H27 H 1.134980 0.148167 0.354124 0.021 Uiso 1 1 calc R U . . .
C28 C 0.98937(17) 0.18573(14) 0.42545(11) 0.0142(3) Uani 1 1 d . . . . .
C29 C 0.77964(17) 0.27003(15) 0.37874(11) 0.0153(3) Uani 1 1 d . . . . .
H29 H 0.719186 0.301468 0.333787 0.018 Uiso 1 1 calc R U . . .
C30 C 0.91564(18) 0.22970(16) 0.27363(11) 0.0173(3) Uani 1 1 d D . . . .
H30A H 1.010876 0.253625 0.272107 0.021 Uiso 0.831(13) 1 calc R U P D 1
H30B H 0.857107 0.286234 0.242208 0.021 Uiso 0.831(13) 1 calc R U P D 1
H30C H 1.011703 0.250763 0.272356 0.021 Uiso 0.169(13) 1 calc R U P D 2
H30D H 0.859944 0.288647 0.242965 0.021 Uiso 0.169(13) 1 calc R U P D 2
O5 O 0.8741(5) 0.0223(4) 0.2687(3) 0.0276(8) Uani 0.831(13) 1 d D U P D 1
C31 C 0.882(2) 0.1099(5) 0.2313(4) 0.0195(9) Uani 0.831(13) 1 d D U P D 1
O6 O 0.8687(11) 0.1186(7) 0.1477(3) 0.0228(10) Uani 0.831(13) 1 d D U P D 1
C32 C 0.8542(9) 0.0099(6) 0.0958(3) 0.0334(12) Uani 0.831(13) 1 d D U P D 1
H32A H 0.814560 -0.053231 0.125426 0.040 Uiso 0.831(13) 1 calc R U P D 1
H32B H 0.943464 -0.012767 0.084958 0.040 Uiso 0.831(13) 1 calc R U P D 1
C33 C 0.7632(7) 0.0313(3) 0.0142(2) 0.0538(15) Uani 0.831(13) 1 d D U P D 1
H33A H 0.803600 0.093954 -0.014350 0.081 Uiso 0.831(13) 1 calc R U P D 1
H33B H 0.675312 0.053458 0.025877 0.081 Uiso 0.831(13) 1 calc R U P D 1
H33C H 0.750995 -0.039472 -0.022452 0.081 Uiso 0.831(13) 1 calc R U P D 1
O5A O 0.831(2) 0.031(2) 0.2617(16) 0.033(4) Uani 0.169(13) 1 d D U P D 2
C31A C 0.877(11) 0.112(3) 0.229(2) 0.024(3) Uani 0.169(13) 1 d D U P D 2
O6A O 0.881(6) 0.117(3) 0.1468(18) 0.025(3) Uani 0.169(13) 1 d D U P D 2
C32A C 0.834(5) 0.007(3) 0.0980(14) 0.034(3) Uani 0.169(13) 1 d D U P D 2
H32C H 0.739974 -0.014487 0.102895 0.040 Uiso 0.169(13) 1 calc R U P D 2
H32D H 0.892462 -0.055868 0.119439 0.040 Uiso 0.169(13) 1 calc R U P D 2
C33A C 0.844(4) 0.0287(18) 0.0084(11) 0.053(4) Uani 0.169(13) 1 d D U P D 2
H33D H 0.821815 -0.043613 -0.026048 0.079 Uiso 0.169(13) 1 calc R U P D 2
H33E H 0.936571 0.056782 0.005334 0.079 Uiso 0.169(13) 1 calc R U P D 2
H33F H 0.780837 0.087088 -0.013283 0.079 Uiso 0.169(13) 1 calc R U P D 2
C34 C 0.8442(2) 0.17552(19) 0.76526(13) 0.0301(4) Uani 1 1 d . . . . .
H34A H 0.941710 0.165593 0.772319 0.045 Uiso 1 1 calc R U . . .
H34B H 0.814957 0.167432 0.820087 0.045 Uiso 1 1 calc R U . . .
H34C H 0.824447 0.252718 0.744424 0.045 Uiso 1 1 calc R U . . .
C35 C 0.4860(2) -0.03196(18) 0.61530(16) 0.0324(5) Uani 1 1 d . . . . .
H35A H 0.437501 -0.069540 0.562009 0.049 Uiso 1 1 calc R U . . .
H35B H 0.427481 -0.033924 0.658143 0.049 Uiso 1 1 calc R U . . .
H35C H 0.567735 -0.073113 0.635452 0.049 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 '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
H7A O7 H7B 113(2) . . ?
H8A O8 H8B 114(4) . . ?
H8C O8A H8D 112(2) . . ?
C34 O9 H9A 107(2) . . ?
C35 O10 H10A 104(2) . . ?
C5 N1 C1 116.93(14) . . ?
C6 N2 C7 124.59(14) . . ?
C6 N2 H2N 116.4(15) . . ?
C7 N2 H2N 117.8(15) . . ?
C15 N3 C14 122.15(14) . . ?
C15 N3 C16 116.96(14) . . ?
C14 N3 C16 120.85(14) . . ?
C20 N4 C21 123.95(14) . . ?
C20 N4 H4N 118.2(15) . . ?
C21 N4 H4N 117.8(15) . . ?
C29 N5 C28 122.14(14) . . ?
C29 N5 C30 116.88(14) . . ?
C28 N5 C30 120.95(14) . . ?
N1 C1 C2 123.50(15) . . ?
N1 C1 C6 118.16(14) . . ?
C2 C1 C6 118.28(14) . . ?
C3 C2 C1 118.65(15) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 118.60(15) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 118.52(16) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 123.72(15) . . ?
N1 C5 C20 118.57(14) . . ?
C4 C5 C20 117.71(15) . . ?
O1 C6 N2 124.10(15) . . ?
O1 C6 C1 120.77(15) . . ?
N2 C6 C1 115.12(14) . . ?
C8 C7 N2 125.92(15) . . ?
C8 C7 C15 117.88(15) . . ?
N2 C7 C15 116.18(15) . . ?
C7 C8 C9 119.84(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C14 120.51(15) . . ?
C8 C9 C10 121.16(15) . . ?
C14 C9 C10 118.32(15) . . ?
C11 C10 C9 120.65(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.02(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 121.34(16) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 118.98(16) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N3 C14 C13 122.19(15) . . ?
N3 C14 C9 117.12(15) . . ?
C13 C14 C9 120.68(15) . . ?
N3 C15 C7 122.33(15) . . ?
N3 C15 H15 118.8 . . ?
C7 C15 H15 118.8 . . ?
N3 C16 C17 115.7(3) . . ?
N3 C16 C17A 111.5(4) . . ?
N3 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
N3 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
N3 C16 H16C 109.3 . . ?
C17A C16 H16C 109.3 . . ?
N3 C16 H16D 109.3 . . ?
C17A C16 H16D 109.3 . . ?
H16C C16 H16D 108.0 . . ?
O2 C17 O3 127.9(7) . . ?
O2 C17 C16 122.0(8) . . ?
O3 C17 C16 110.0(4) . . ?
C17 O3 C18 114.5(3) . . ?
O3 C18 C19 109.6(3) . . ?
O3 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
O3 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2A C17A O3A 121.1(10) . . ?
O2A C17A C16 121.2(12) . . ?
O3A C17A C16 117.0(6) . . ?
C17A O3A C18A 119.2(5) . . ?
O3A C18A C19A 112.6(6) . . ?
O3A C18A H18C 109.1 . . ?
C19A C18A H18C 109.1 . . ?
O3A C18A H18D 109.1 . . ?
C19A C18A H18D 109.1 . . ?
H18C C18A H18D 107.8 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
O4 C20 N4 124.51(15) . . ?
O4 C20 C5 120.57(15) . . ?
N4 C20 C5 114.92(14) . . ?
C22 C21 N4 124.70(15) . . ?
C22 C21 C29 118.03(15) . . ?
N4 C21 C29 117.23(15) . . ?
C21 C22 C23 119.98(15) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.79(16) . . ?
C22 C23 C28 120.46(15) . . ?
C24 C23 C28 118.75(15) . . ?
C25 C24 C23 120.17(16) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.19(17) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 121.69(16) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 118.72(16) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
N5 C28 C27 122.39(15) . . ?
N5 C28 C23 117.18(15) . . ?
C27 C28 C23 120.43(15) . . ?
N5 C29 C21 122.14(15) . . ?
N5 C29 H29 118.9 . . ?
C21 C29 H29 118.9 . . ?
N5 C30 C31A 110.9(11) . . ?
N5 C30 C31 110.3(2) . . ?
N5 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
N5 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
N5 C30 H30C 109.5 . . ?
C31A C30 H30C 109.5 . . ?
N5 C30 H30D 109.5 . . ?
C31A C30 H30D 109.5 . . ?
H30C C30 H30D 108.0 . . ?
O5 C31 O6 126.6(4) . . ?
O5 C31 C30 124.6(5) . . ?
O6 C31 C30 108.8(5) . . ?
C31 O6 C32 117.0(6) . . ?
O6 C32 C33 106.9(6) . . ?
O6 C32 H32A 110.3 . . ?
C33 C32 H32A 110.3 . . ?
O6 C32 H32B 110.3 . . ?
C33 C32 H32B 110.3 . . ?
H32A C32 H32B 108.6 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O5A C31A O6A 125(2) . . ?
O5A C31A C30 124(3) . . ?
O6A C31A C30 110(2) . . ?
C31A O6A C32A 113(2) . . ?
O6A C32A C33A 106(2) . . ?
O6A C32A H32C 110.5 . . ?
C33A C32A H32C 110.5 . . ?
O6A C32A H32D 110.5 . . ?
C33A C32A H32D 110.5 . . ?
H32C C32A H32D 108.7 . . ?
C32A C33A H33D 109.5 . . ?
C32A C33A H33E 109.5 . . ?
H33D C33A H33E 109.5 . . ?
C32A C33A H33F 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
O9 C34 H34A 109.5 . . ?
O9 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O9 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O10 C35 H35A 109.5 . . ?
O10 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O10 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.222(2) . ?
O4 C20 1.219(2) . ?
O7 H7A 0.841(13) . ?
O7 H7B 0.80(2) . ?
O8 H8A 0.842(7) . ?
O8 H8B 0.83(4) . ?
O8A H8C 0.842(10) . ?
O8A H8D 0.842(10) . ?
O9 C34 1.408(3) . ?
O9 H9A 0.860(17) . ?
O10 C35 1.415(3) . ?
O10 H10A 0.892(18) . ?
N1 C5 1.336(2) . ?
N1 C1 1.339(2) . ?
N2 C6 1.360(2) . ?
N2 C7 1.397(2) . ?
N2 H2N 0.828(15) . ?
N3 C15 1.332(2) . ?
N3 C14 1.384(2) . ?
N3 C16 1.483(2) . ?
N4 C20 1.364(2) . ?
N4 C21 1.401(2) . ?
N4 H4N 0.838(15) . ?
N5 C29 1.334(2) . ?
N5 C28 1.381(2) . ?
N5 C30 1.478(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.507(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C20 1.507(2) . ?
C7 C8 1.384(2) . ?
C7 C15 1.403(2) . ?
C8 C9 1.410(2) . ?
C8 H8 0.9500 . ?
C9 C14 1.418(2) . ?
C9 C10 1.421(2) . ?
C10 C11 1.369(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.409(2) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.500(5) . ?
C16 C17A 1.527(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
O2 C17 1.188(6) . ?
C17 O3 1.337(6) . ?
O3 C18 1.461(4) . ?
C18 C19 1.497(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2A C17A 1.218(10) . ?
C17A O3A 1.351(9) . ?
O3A C18A 1.470(8) . ?
C18A C19A 1.485(9) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C21 C22 1.379(2) . ?
C21 C29 1.404(2) . ?
C22 C23 1.407(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.417(2) . ?
C23 C28 1.419(2) . ?
C24 C25 1.369(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.407(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.371(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.411(2) . ?
C27 H27 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31A 1.514(9) . ?
C30 C31 1.516(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 H30C 0.9900 . ?
C30 H30D 0.9900 . ?
O5 C31 1.201(6) . ?
C31 O6 1.328(5) . ?
O6 C32 1.469(5) . ?
C32 C33 1.490(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
O5A C31A 1.197(18) . ?
C31A O6A 1.332(16) . ?
O6A C32A 1.478(17) . ?
C32A C33A 1.482(18) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
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
O7 H7A Br2 0.841(13) 2.394(14) 3.2176(15) 166(2) .
O7 H7B Br1 0.80(2) 2.42(2) 3.2168(14) 177(2) .
O8 H8A Br1 0.842(7) 2.79(3) 3.577(6) 155(7) .
O8 H8B Br2 0.83(4) 2.76(4) 3.552(5) 161(6) .
O8A H8C Br1 0.842(10) 2.78(5) 3.58(2) 160(13) .
O8A H8D Br2 0.842(10) 2.76(5) 3.56(2) 158(12) .
O9 H9A Br2 0.860(17) 2.385(18) 3.2443(16) 178(3) 2_656
O10 H10A O9 0.892(18) 1.907(19) 2.781(2) 166(3) .
N2 H2N O7 0.828(15) 2.149(17) 2.9300(19) 157(2) .
N4 H4N O7 0.838(15) 2.082(16) 2.8912(19) 162(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
C5 N1 C1 C2 -1.3(2) . . . . ?
C5 N1 C1 C6 175.88(14) . . . . ?
N1 C1 C2 C3 2.7(3) . . . . ?
C6 C1 C2 C3 -174.55(16) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C1 N1 C5 C4 -1.6(2) . . . . ?
C1 N1 C5 C20 179.23(14) . . . . ?
C3 C4 C5 N1 3.0(3) . . . . ?
C3 C4 C5 C20 -177.76(15) . . . . ?
C7 N2 C6 O1 15.9(3) . . . . ?
C7 N2 C6 C1 -163.52(15) . . . . ?
N1 C1 C6 O1 -178.98(16) . . . . ?
C2 C1 C6 O1 -1.6(2) . . . . ?
N1 C1 C6 N2 0.4(2) . . . . ?
C2 C1 C6 N2 177.78(15) . . . . ?
C6 N2 C7 C8 -15.9(3) . . . . ?
C6 N2 C7 C15 162.53(16) . . . . ?
N2 C7 C8 C9 174.07(16) . . . . ?
C15 C7 C8 C9 -4.3(2) . . . . ?
C7 C8 C9 C14 2.3(3) . . . . ?
C7 C8 C9 C10 -176.38(16) . . . . ?
C8 C9 C10 C11 177.87(17) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C15 N3 C14 C13 175.97(17) . . . . ?
C16 N3 C14 C13 -1.6(3) . . . . ?
C15 N3 C14 C9 -3.2(2) . . . . ?
C16 N3 C14 C9 179.23(15) . . . . ?
C12 C13 C14 N3 -179.56(17) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C8 C9 C14 N3 1.5(2) . . . . ?
C10 C9 C14 N3 -179.83(15) . . . . ?
C8 C9 C14 C13 -177.70(16) . . . . ?
C10 C9 C14 C13 1.0(3) . . . . ?
C14 N3 C15 C7 1.1(3) . . . . ?
C16 N3 C15 C7 178.79(16) . . . . ?
C8 C7 C15 N3 2.7(3) . . . . ?
N2 C7 C15 N3 -175.81(16) . . . . ?
C15 N3 C16 C17 -94.7(3) . . . . ?
C14 N3 C16 C17 82.9(4) . . . . ?
C15 N3 C16 C17A -84.4(6) . . . . ?
C14 N3 C16 C17A 93.3(6) . . . . ?
N3 C16 C17 O2 -178.0(7) . . . . ?
N3 C16 C17 O3 -0.9(6) . . . . ?
O2 C17 O3 C18 -6.4(10) . . . . ?
C16 C17 O3 C18 176.7(4) . . . . ?
C17 O3 C18 C19 -84.5(5) . . . . ?
N3 C16 C17A O2A -176.0(12) . . . . ?
N3 C16 C17A O3A 13.4(12) . . . . ?
O2A C17A O3A C18A 6.0(17) . . . . ?
C16 C17A O3A C18A 176.5(7) . . . . ?
C17A O3A C18A C19A 81.3(9) . . . . ?
C21 N4 C20 O4 4.7(3) . . . . ?
C21 N4 C20 C5 -175.69(15) . . . . ?
N1 C5 C20 O4 171.82(15) . . . . ?
C4 C5 C20 O4 -7.4(2) . . . . ?
N1 C5 C20 N4 -7.8(2) . . . . ?
C4 C5 C20 N4 172.99(15) . . . . ?
C20 N4 C21 C22 15.8(3) . . . . ?
C20 N4 C21 C29 -166.49(16) . . . . ?
N4 C21 C22 C23 -179.86(16) . . . . ?
C29 C21 C22 C23 2.5(3) . . . . ?
C21 C22 C23 C24 178.30(17) . . . . ?
C21 C22 C23 C28 -2.4(3) . . . . ?
C22 C23 C24 C25 -178.57(18) . . . . ?
C28 C23 C24 C25 2.1(3) . . . . ?
C23 C24 C25 C26 -1.7(3) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C29 N5 C28 C27 -177.63(17) . . . . ?
C30 N5 C28 C27 4.5(2) . . . . ?
C29 N5 C28 C23 2.0(2) . . . . ?
C30 N5 C28 C23 -175.94(15) . . . . ?
C26 C27 C28 N5 178.78(17) . . . . ?
C26 C27 C28 C23 -0.8(3) . . . . ?
C22 C23 C28 N5 0.2(2) . . . . ?
C24 C23 C28 N5 179.49(16) . . . . ?
C22 C23 C28 C27 179.81(16) . . . . ?
C24 C23 C28 C27 -0.9(3) . . . . ?
C28 N5 C29 C21 -1.9(3) . . . . ?
C30 N5 C29 C21 176.05(16) . . . . ?
C22 C21 C29 N5 -0.4(3) . . . . ?
N4 C21 C29 N5 -178.20(15) . . . . ?
C29 N5 C30 C31A -97(5) . . . . ?
C28 N5 C30 C31A 81(5) . . . . ?
C29 N5 C30 C31 -99.6(9) . . . . ?
C28 N5 C30 C31 78.4(9) . . . . ?
N5 C30 C31 O5 -18(2) . . . . ?
N5 C30 C31 O6 164.6(11) . . . . ?
O5 C31 O6 C32 -6(3) . . . . ?
C30 C31 O6 C32 172.0(10) . . . . ?
C31 O6 C32 C33 146.4(13) . . . . ?
N5 C30 C31A O5A 3(12) . . . . ?
N5 C30 C31A O6A 172(7) . . . . ?
O5A C31A O6A C32A -6(15) . . . . ?
C30 C31A O6A C32A -176(6) . . . . ?
C31A O6A C32A C33A 180(7) . . . . ?
