#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:07:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180169 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/65/7106544.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_7106544
loop_
_publ_author_name
'Jung-Jae Lee'
'Jeffrey M. Baumes'
'Richard D. Connell'
'Allen G. Oliver'
'Bradley D. Smith'
_publ_section_title
;
 Squaraine [2]Catenanes: synthesis, structure and molecular dynamics
;
_journal_name_full               Chem.Commun.
_journal_page_first              7188
_journal_paper_doi               10.1039/c1cc10946d
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C42 H62 N2 O4, C48 H36 N6 O4, 2(C2 H3 N)'
_chemical_formula_sum            'C94 H104 N10 O8'
_chemical_formula_weight         1501.87
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.016(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.4062(18)
_cell_length_b                   15.2138(13)
_cell_length_c                   26.813(4)
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.62
_cell_measurement_theta_min      2.36
_cell_volume                     8095.4(16)
_computing_cell_refinement       'Bruker SAINT v7.68A'
_computing_data_collection       'Bruker APEX-II v2010-3'
_computing_data_reduction        'Bruker SAINT v7.68A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20247
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9860
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3208
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1030P)²+14.3329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.2262
_reflns_number_gt                2560
_reflns_number_total             4932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10946d.txt
_cod_data_source_block           nd1013
_cod_original_cell_volume        8095.5(15)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7106544
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.10915(16) 0.6307(2) 0.25724(14) 0.0315(10) Uani 1 1 d . . .
O2 O 0.17124(19) 0.4373(3) 0.54879(17) 0.0571(13) Uani 1 1 d . . .
N1 N 0.1153(2) 0.6037(3) 0.5155(2) 0.0435(13) Uani 1 1 d . . .
C1 C 0.0486(3) 0.6322(3) 0.2530(2) 0.0287(14) Uani 1 1 d . . .
C2 C 0.0162(2) 0.6329(3) 0.2921(2) 0.0254(13) Uani 1 1 d . . .
C3 C 0.0399(3) 0.6312(3) 0.3480(2) 0.0294(14) Uani 1 1 d . . .
C4 C 0.1098(3) 0.6299(3) 0.3789(2) 0.0315(14) Uani 1 1 d . . .
H4A H 0.1404 0.6338 0.3610 0.038 Uiso 1 1 calc R . .
C5 C 0.1343(3) 0.6236(3) 0.4327(3) 0.0380(15) Uani 1 1 d . . .
H5A H 0.1817 0.6236 0.4518 0.046 Uiso 1 1 calc R . .
C6 C 0.0907(3) 0.6168(4) 0.4620(2) 0.0359(15) Uani 1 1 d . . .
C7 C 0.0202(3) 0.6228(3) 0.4308(2) 0.0355(15) Uani 1 1 d . . .
H7A H -0.0108 0.6226 0.4485 0.043 Uiso 1 1 calc R . .
C8 C -0.0036(3) 0.6288(3) 0.3764(2) 0.0320(14) Uani 1 1 d . . .
H8A H -0.0509 0.6316 0.3570 0.038 Uiso 1 1 calc R . .
C9 C 0.0719(3) 0.6058(4) 0.5466(2) 0.0414(16) Uani 1 1 d . . .
H9A H 0.0931 0.5718 0.5802 0.050 Uiso 1 1 calc R . .
H9B H 0.0280 0.5782 0.5255 0.050 Uiso 1 1 calc R . .
C10 C 0.0607(3) 0.7007(4) 0.5601(3) 0.0539(19) Uani 1 1 d . . .
H10A H 0.0318 0.7012 0.5811 0.081 Uiso 1 1 calc R . .
H10B H 0.0389 0.7339 0.5268 0.081 Uiso 1 1 calc R . .
H10C H 0.1041 0.7278 0.5812 0.081 Uiso 1 1 calc R . .
C11 C 0.1870(3) 0.5928(4) 0.5464(3) 0.0542(19) Uani 1 1 d . . .
H11A H 0.1956 0.6019 0.5850 0.065 Uiso 1 1 calc R . .
H11B H 0.2121 0.6384 0.5354 0.065 Uiso 1 1 calc R . .
C12 C 0.2132(3) 0.5032(4) 0.5393(3) 0.056(2) Uani 1 1 d . . .
H12A H 0.2125 0.4974 0.5024 0.068 Uiso 1 1 calc R . .
H12B H 0.2602 0.4960 0.5650 0.068 Uiso 1 1 calc R . .
C13 C 0.1950(3) 0.3511(5) 0.5444(3) 0.067(2) Uani 1 1 d . . .
H13A H 0.2396 0.3415 0.5734 0.081 Uiso 1 1 calc R . .
H13B H 0.2002 0.3448 0.5094 0.081 Uiso 1 1 calc R . .
C14 C 0.1454(3) 0.2836(5) 0.5486(3) 0.067(2) Uani 1 1 d . A .
H14A H 0.1022 0.2898 0.5176 0.080 Uiso 1 1 calc R . .
H14B H 0.1367 0.2940 0.5819 0.080 Uiso 1 1 calc R . .
C15 C 0.1727(4) 0.1913(5) 0.5495(3) 0.086(3) Uani 1 1 d D . .
H15A H 0.2151 0.1854 0.5813 0.104 Uiso 1 1 calc R A .
H15B H 0.1836 0.1830 0.5170 0.104 Uiso 1 1 calc R . .
C16 C 0.1238(5) 0.1181(7) 0.5513(5) 0.076(4) Uiso 0.701(8) 1 d PD A -1
H16A H 0.1491 0.0621 0.5606 0.091 Uiso 0.701(8) 1 calc PR A -1
H16B H 0.1076 0.1317 0.5805 0.091 Uiso 0.701(8) 1 calc PR A -1
C17 C 0.0631(5) 0.1047(7) 0.4998(4) 0.079(4) Uiso 0.701(8) 1 d PD A -1
H17A H 0.0316 0.1535 0.4975 0.094 Uiso 0.701(8) 1 calc PR A -1
H17B H 0.0407 0.0501 0.5045 0.094 Uiso 0.701(8) 1 calc PR A -1
C18 C 0.0688(7) 0.0981(14) 0.4450(5) 0.113(10) Uiso 0.701(8) 1 d PD A -1
H18A H 0.0985 0.0481 0.4456 0.136 Uiso 0.701(8) 1 calc PR A -1
H18B H 0.0905 0.1523 0.4389 0.136 Uiso 0.701(8) 1 calc PR A -1
C19 C 0.0004(5) 0.0857(7) 0.3972(4) 0.081(4) Uiso 0.701(8) 1 d PD A -1
H19A H -0.0185 0.0286 0.4024 0.098 Uiso 0.701(8) 1 calc PR A -1
H19B H -0.0305 0.1320 0.4001 0.098 Uiso 0.701(8) 1 calc PR A -1
C20 C -0.0017(7) 0.0875(7) 0.3405(5) 0.087(4) Uiso 0.701(8) 1 d PD A -1
H20A H 0.0397 0.0576 0.3411 0.104 Uiso 0.701(8) 1 calc PR A -1
H20B H -0.0401 0.0501 0.3188 0.104 Uiso 0.701(8) 1 calc PR A -1
C21 C -0.0074(9) 0.1705(9) 0.3101(7) 0.166(7) Uiso 0.701(8) 1 d PD A -1
H21A H 0.0210 0.2148 0.3357 0.200 Uiso 0.701(8) 1 calc PR A -1
H21B H -0.0546 0.1908 0.2988 0.200 Uiso 0.701(8) 1 calc PR A -1
C22 C 0.0111(9) 0.1722(7) 0.2610(6) 0.061(4) Uiso 0.50 1 d PD A -1
H22 H 0.0225 0.2270 0.2497 0.074 Uiso 0.50 1 calc PR A -1
C23 C 0.0122(7) 0.1017(9) 0.2331(5) 0.066(4) Uiso 0.50 1 d PD A -1
H23 H -0.0116 0.0508 0.2365 0.079 Uiso 0.50 1 calc PR A -1
C24 C 0.0501(8) 0.0994(16) 0.1956(7) 0.071(8) Uiso 0.299(8) 1 d PD A -1
H24A H 0.0578 0.0401 0.1838 0.085 Uiso 0.299(8) 1 calc PR A -1
H24B H 0.0909 0.1367 0.2064 0.085 Uiso 0.299(8) 1 calc PR A -1
C25 C -0.0155(14) 0.1442(15) 0.1599(10) 0.22(3) Uiso 0.299(8) 1 d PD A -1
H25A H -0.0407 0.1645 0.1821 0.268 Uiso 0.299(8) 1 calc PR A -1
H25B H -0.0054 0.1959 0.1418 0.268 Uiso 0.299(8) 1 calc PR A -1
C26 C -0.0573(8) 0.0780(12) 0.1183(7) 0.042(6) Uiso 0.299(8) 1 d PD A -1
H26A H -0.1052 0.0833 0.1138 0.051 Uiso 0.299(8) 1 calc PR A -1
H26B H -0.0421 0.0177 0.1311 0.051 Uiso 0.299(8) 1 calc PR A -1
C27 C -0.051(2) 0.093(3) 0.0645(9) 0.094(17) Uiso 0.299(8) 1 d PD A -1
H27A H -0.0102 0.0629 0.0632 0.113 Uiso 0.299(8) 1 calc PR A -1
H27B H -0.0471 0.1567 0.0580 0.113 Uiso 0.299(8) 1 calc PR A -1
C28 C -0.1153(13) 0.0542(18) 0.0227(11) 0.096(10) Uiso 0.299(8) 1 d PD A -1
H28A H -0.1531 0.0609 0.0352 0.116 Uiso 0.299(8) 1 calc PR A -1
H28B H -0.1090 -0.0093 0.0179 0.116 Uiso 0.299(8) 1 calc PR A -1
C29 C -0.132(2) 0.1032(18) -0.0316(14) 0.17(2) Uiso 0.299(8) 1 d PD . -1
H29A H -0.1556 0.0598 -0.0599 0.203 Uiso 0.299(8) 1 calc PR A -1
H29B H -0.0879 0.1140 -0.0347 0.203 Uiso 0.299(8) 1 calc PR A -1
O3 O 0.21456(17) 0.3971(2) 0.17644(15) 0.0360(10) Uani 1 1 d . . .
O4 O 0.22366(17) 0.8670(2) 0.18852(16) 0.0428(11) Uani 1 1 d . . .
N2 N 0.14727(19) 0.4670(3) 0.21120(18) 0.0320(12) Uani 1 1 d . . .
H2A H 0.1336 0.5174 0.2197 0.038 Uiso 1 1 calc R . .
N3 N 0.15423(19) 0.7951(3) 0.22101(18) 0.0345(12) Uani 1 1 d . . .
H3A H 0.1395 0.7444 0.2281 0.041 Uiso 1 1 calc R . .
N4A N 0.2891(3) 0.5506(4) 0.1828(2) 0.0561(18) Uani 0.50 1 d P B 1
C4A C 0.2930(3) 0.7110(4) 0.1890(3) 0.0618(19) Uani 0.50 1 d P B 1
H4A1 H 0.3163 0.7640 0.1889 0.074 Uiso 0.50 1 calc PR B 1
C4B C 0.2891(3) 0.5506(4) 0.1828(2) 0.0561(18) Uani 0.50 1 d P B 2
H4B H 0.3091 0.4971 0.1779 0.067 Uiso 0.50 1 calc PR B 2
N4B N 0.2930(3) 0.7110(4) 0.1890(3) 0.0618(19) Uani 0.50 1 d P B 2
C31 C 0.0094(3) 0.4054(3) 0.3049(2) 0.0293(14) Uani 1 1 d . . .
C32 C 0.0222(3) 0.4100(3) 0.3607(2) 0.0326(15) Uani 1 1 d . . .
H32A H -0.0150 0.4122 0.3718 0.039 Uiso 1 1 calc R . .
C33 C 0.0853(3) 0.4115(4) 0.3987(3) 0.0386(15) Uani 1 1 d . . .
H33A H 0.0919 0.4148 0.4357 0.046 Uiso 1 1 calc R . .
C34 C 0.1415(3) 0.4080(4) 0.3826(3) 0.0416(16) Uani 1 1 d . . .
H34A H 0.1858 0.4076 0.4092 0.050 Uiso 1 1 calc R . .
C35 C 0.1327(3) 0.4053(3) 0.3306(3) 0.0360(15) Uani 1 1 d . . .
H35A H 0.1711 0.4043 0.3209 0.043 Uiso 1 1 calc R . .
C36 C 0.0666(2) 0.4040(3) 0.2889(2) 0.0284(14) Uani 1 1 d . . .
C37 C 0.0563(3) 0.3999(3) 0.2339(2) 0.0276(14) Uani 1 1 d . . .
C38 C 0.1155(3) 0.3843(3) 0.2173(2) 0.0326(14) Uani 1 1 d . . .
H38A H 0.1492 0.3473 0.2447 0.039 Uiso 1 1 calc R . .
H38B H 0.0999 0.3519 0.1827 0.039 Uiso 1 1 calc R . .
C39 C 0.1976(2) 0.4652(4) 0.1924(2) 0.0327(15) Uani 1 1 d . B .
C40 C 0.2293(2) 0.5529(4) 0.1903(2) 0.0350(15) Uani 1 1 d . . .
C41 C 0.2015(2) 0.6321(4) 0.1960(2) 0.0326(14) Uani 1 1 d . B .
H41A H 0.1595 0.6326 0.2005 0.039 Uiso 1 1 calc R . .
C42 C 0.2331(3) 0.7106(4) 0.1953(2) 0.0336(15) Uani 1 1 d . . .
C43 C 0.3182(3) 0.6306(5) 0.1827(3) 0.080(3) Uani 1 1 d . . .
H43A H 0.3599 0.6305 0.1779 0.096 Uiso 1 1 calc R B 1
C44 C 0.2041(3) 0.7978(4) 0.2015(2) 0.0362(15) Uani 1 1 d . B .
C45 C 0.1252(3) 0.8773(3) 0.2302(3) 0.0418(17) Uani 1 1 d . . .
H45A H 0.1151 0.9156 0.1983 0.050 Uiso 1 1 calc R . .
H45B H 0.1587 0.9079 0.2613 0.050 Uiso 1 1 calc R . .
C46 C 0.0609(3) 0.8631(3) 0.2409(3) 0.0360(15) Uani 1 1 d . . .
C47 C -0.0013(3) 0.8584(3) 0.1970(3) 0.0359(16) Uani 1 1 d . . .
C48 C -0.0635(3) 0.8584(3) 0.2066(3) 0.0353(15) Uani 1 1 d . . .
C49 C -0.1255(3) 0.8554(4) 0.1608(3) 0.0437(17) Uani 1 1 d . . .
H49A H -0.1670 0.8572 0.1660 0.052 Uiso 1 1 calc R . .
C50 C -0.1261(3) 0.8499(4) 0.1101(3) 0.0522(18) Uani 1 1 d . . .
H50A H -0.1680 0.8471 0.0805 0.063 Uiso 1 1 calc R . .
C51 C -0.0652(3) 0.8485(4) 0.1005(3) 0.0507(18) Uani 1 1 d . . .
H51A H -0.0662 0.8446 0.0649 0.061 Uiso 1 1 calc R . .
C52 C -0.0057(3) 0.8525(3) 0.1430(3) 0.0433(17) Uani 1 1 d . . .
H52A H 0.0348 0.8514 0.1363 0.052 Uiso 1 1 calc R . .
N1S N 0.3007(3) 0.6389(6) 0.4448(3) 0.104(3) Uani 1 1 d . . .
C1S C 0.2927(4) 0.6279(8) 0.4012(5) 0.121(4) Uani 1 1 d . . .
C2S C 0.2811(4) 0.6082(9) 0.3446(4) 0.176(6) Uani 1 1 d . . .
H2SA H 0.3211 0.6244 0.3373 0.264 Uiso 1 1 calc R . .
H2SB H 0.2423 0.6419 0.3210 0.264 Uiso 1 1 calc R . .
H2SC H 0.2722 0.5452 0.3379 0.264 Uiso 1 1 calc R . .
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'
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
C13 O2 C12 111.2(4) . . ?
C6 N1 C11 122.3(4) . . ?
C6 N1 C9 121.7(5) . . ?
C11 N1 C9 115.9(5) . . ?
O1 C1 C2 133.3(5) . . ?
O1 C1 C2 134.7(5) . 2 ?
C2 C1 C2 92.0(4) . 2 ?
O1 C1 C1 178.7(4) . 2 ?
C2 C1 C1 46.1(3) . 2 ?
C2 C1 C1 46.0(3) 2 2 ?
C3 C2 C1 134.1(5) . . ?
C3 C2 C1 137.9(5) . 2 ?
C1 C2 C1 88.0(4) . 2 ?
C2 C3 C8 122.4(5) . . ?
C2 C3 C4 120.7(4) . . ?
C8 C3 C4 116.8(5) . . ?
C5 C4 C3 122.3(5) . . ?
C4 C5 C6 121.5(5) . . ?
N1 C6 C7 122.8(5) . . ?
N1 C6 C5 121.4(5) . . ?
C7 C6 C5 115.9(5) . . ?
C8 C7 C6 121.6(5) . . ?
C7 C8 C3 121.7(5) . . ?
N1 C9 C10 110.2(4) . . ?
N1 C11 C12 113.1(5) . . ?
O2 C12 C11 108.8(5) . . ?
O2 C13 C14 109.6(5) . . ?
C13 C14 C15 110.6(5) . . ?
C14 C15 C16 114.1(7) . . ?
C14 C15 C29 128.2(19) . 2 ?
C16 C15 C29 24.2(14) . 2 ?
C17 C16 C15 115.4(8) . . ?
C16 C17 C18 122.5(10) . . ?
C17 C18 C19 114.4(10) . . ?
C20 C19 C18 119.6(9) . . ?
C21 C20 C19 122.4(11) . . ?
C20 C21 C22 120.0(12) . . ?
C23 C22 C21 123.4(13) . . ?
C22 C23 C24 121.8(15) . . ?
C22 C23 C25 104.0(12) . . ?
C24 C23 C25 51.0(8) . . ?
C23 C24 C25 79.0(15) . . ?
C26 C25 C24 108.2(10) . . ?
C26 C25 C23 113.2(18) . . ?
C24 C25 C23 50.0(8) . . ?
C25 C26 C27 110.8(10) . . ?
C26 C27 C28 104.6(18) . . ?
C27 C28 C29 109(3) . . ?
C28 C29 C15 127(2) . 2 ?
C39 N2 C38 119.4(4) . . ?
C44 N3 C45 119.1(4) . . ?
C43 N4A C40 115.3(5) . . ?
C42 C4A C43 116.4(5) . . ?
C37 C31 C32 122.1(5) 2 . ?
C37 C31 C36 120.2(5) 2 . ?
C32 C31 C36 117.7(5) . . ?
C33 C32 C31 122.7(5) . . ?
C32 C33 C34 119.4(6) . . ?
C35 C34 C33 120.9(6) . . ?
C34 C35 C36 121.6(5) . . ?
C37 C36 C35 122.5(5) . . ?
C37 C36 C31 119.7(5) . . ?
C35 C36 C31 117.8(5) . . ?
C31 C37 C36 119.7(4) 2 . ?
C31 C37 C38 120.5(5) 2 . ?
C36 C37 C38 119.7(5) . . ?
N2 C38 C37 111.9(4) . . ?
O3 C39 N2 122.1(5) . . ?
O3 C39 C40 122.4(5) . . ?
N2 C39 C40 115.5(5) . . ?
N4A C40 C41 120.4(5) . . ?
N4A C40 C39 116.2(5) . . ?
C41 C40 C39 123.4(4) . . ?
C42 C41 C40 121.5(4) . . ?
C4A C42 C41 119.9(5) . . ?
C4A C42 C44 117.4(5) . . ?
C41 C42 C44 122.7(4) . . ?
N4A C43 C4A 126.4(5) . . ?
O4 C44 N3 122.4(5) . . ?
O4 C44 C42 121.9(5) . . ?
N3 C44 C42 115.7(5) . . ?
N3 C45 C46 112.5(4) . . ?
C48 C46 C47 120.6(5) 2 . ?
C48 C46 C45 120.2(6) 2 . ?
C47 C46 C45 119.2(6) . . ?
C46 C47 C52 122.4(5) . . ?
C46 C47 C48 119.7(6) . . ?
C52 C47 C48 117.9(6) . . ?
C46 C48 C49 122.9(5) 2 . ?
C46 C48 C47 119.3(5) 2 . ?
C49 C48 C47 117.8(6) . . ?
C50 C49 C48 121.2(5) . . ?
C49 C50 C51 121.2(6) . . ?
C52 C51 C50 119.0(6) . . ?
C51 C52 C47 122.9(6) . . ?
N1S C1S C2S 176.6(14) . . ?
C5 C4 H4A 118.9 . . ?
C3 C4 H4A 118.9 . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C8 C7 H7A 119.2 . . ?
C6 C7 H7A 119.2 . . ?
C7 C8 H8A 119.1 . . ?
C3 C8 H8A 119.1 . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O2 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
O2 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O2 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O2 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C29 C15 H15A 114.2 2 . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C29 C15 H15B 84.8 2 . ?
H15A C15 H15B 107.6 . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 106.7 . . ?
C18 C17 H17A 106.7 . . ?
C16 C17 H17B 106.7 . . ?
C18 C17 H17B 106.7 . . ?
H17A C17 H17B 106.6 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 H19A 107.4 . . ?
C18 C19 H19A 107.4 . . ?
C20 C19 H19B 107.4 . . ?
C18 C19 H19B 107.4 . . ?
H19A C19 H19B 106.9 . . ?
C21 C20 H20A 106.7 . . ?
C19 C20 H20A 106.7 . . ?
C21 C20 H20B 106.7 . . ?
C19 C20 H20B 106.7 . . ?
H20A C20 H20B 106.6 . . ?
C20 C21 H21A 107.3 . . ?
C22 C21 H21A 107.3 . . ?
C20 C21 H21B 107.3 . . ?
C22 C21 H21B 107.3 . . ?
H21A C21 H21B 106.9 . . ?
C23 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C23 H23 113.5 . . ?
C23 C24 H24A 115.4 . . ?
C25 C24 H24A 115.4 . . ?
C23 C24 H24B 115.4 . . ?
C25 C24 H24B 115.4 . . ?
H24A C24 H24B 112.4 . . ?
C26 C25 H25A 110.0 . . ?
C24 C25 H25A 110.0 . . ?
C23 C25 H25A 61.7 . . ?
C26 C25 H25B 110.0 . . ?
C24 C25 H25B 110.0 . . ?
C23 C25 H25B 136.3 . . ?
H25A C25 H25B 108.4 . . ?
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 H27A 110.8 . . ?
C28 C27 H27A 110.8 . . ?
C26 C27 H27B 110.8 . . ?
C28 C27 H27B 110.8 . . ?
H27A C27 H27B 108.9 . . ?
C27 C28 H28A 109.9 . . ?
C29 C28 H28A 109.9 . . ?
C27 C28 H28B 109.9 . . ?
C29 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C28 C29 H29A 105.6 . . ?
C15 C29 H29A 105.6 2 . ?
C28 C29 H29B 105.6 . . ?
C15 C29 H29B 105.6 2 . ?
H29A C29 H29B 106.1 . . ?
C39 N2 H2A 120.3 . . ?
C38 N2 H2A 120.3 . . ?
C44 N3 H3A 120.4 . . ?
C45 N3 H3A 120.4 . . ?
C42 C4A H4A1 121.8 . . ?
C43 C4A H4A1 121.8 . . ?
C33 C32 H32A 118.7 . . ?
C31 C32 H32A 118.7 . . ?
C32 C33 H33A 120.3 . . ?
C34 C33 H33A 120.3 . . ?
C35 C34 H34A 119.6 . . ?
C33 C34 H34A 119.6 . . ?
C34 C35 H35A 119.2 . . ?
C36 C35 H35A 119.2 . . ?
N2 C38 H38A 109.2 . . ?
C37 C38 H38A 109.2 . . ?
N2 C38 H38B 109.2 . . ?
C37 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C42 C41 H41A 119.2 . . ?
C40 C41 H41A 119.2 . . ?
N4A C43 H43A 116.8 . . ?
C4A C43 H43A 116.8 . . ?
N3 C45 H45A 109.1 . . ?
C46 C45 H45A 109.1 . . ?
N3 C45 H45B 109.1 . . ?
C46 C45 H45B 109.1 . . ?
H45A C45 H45B 107.8 . . ?
C50 C49 H49A 119.4 . . ?
C48 C49 H49A 119.4 . . ?
C49 C50 H50A 119.4 . . ?
C51 C50 H50A 119.4 . . ?
C52 C51 H51A 120.5 . . ?
C50 C51 H51A 120.5 . . ?
C51 C52 H52A 118.5 . . ?
C47 C52 H52A 118.5 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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 C1 1.258(5) . ?
O2 C13 1.427(7) . ?
O2 C12 1.431(7) . ?
N1 C6 1.344(7) . ?
N1 C11 1.454(7) . ?
N1 C9 1.463(6) . ?
C1 C2 1.458(7) . ?
C1 C2 1.460(7) 2 ?
C1 C1 2.027(10) 2 ?
C2 C3 1.390(7) . ?
C2 C1 1.460(7) 2 ?
C3 C8 1.408(7) . ?
C3 C4 1.413(7) . ?
C4 C5 1.340(7) . ?
C5 C6 1.432(7) . ?
C6 C7 1.428(7) . ?
C7 C8 1.355(7) . ?
C9 C10 1.531(7) . ?
C11 C12 1.513(8) . ?
C13 C14 1.511(8) . ?
C14 C15 1.518(9) . ?
C15 C16 1.542(8) . ?
C15 C29 1.574(10) 2 ?
C16 C17 1.513(9) . ?
C17 C18 1.521(9) . ?
C18 C19 1.554(9) . ?
C19 C20 1.504(9) . ?
C20 C21 1.482(9) . ?
C21 C22 1.511(10) . ?
C22 C23 1.312(15) . ?
C23 C24 1.509(10) . ?
C23 C25 1.93(3) . ?
C24 C25 1.532(10) . ?
C25 C26 1.521(10) . ?
C26 C27 1.523(10) . ?
C27 C28 1.538(10) . ?
C28 C29 1.554(10) . ?
C29 C15 1.574(10) 2 ?
O3 C39 1.227(6) . ?
O4 C44 1.230(6) . ?
N2 C39 1.349(6) . ?
N2 C38 1.469(6) . ?
N3 C44 1.355(6) . ?
N3 C45 1.458(6) . ?
N4A C43 1.367(8) . ?
N4A C40 1.370(6) . ?
C4A C42 1.355(6) . ?
C4A C43 1.372(8) . ?
C31 C37 1.403(7) 2 ?
C31 C32 1.416(7) . ?
C31 C36 1.443(6) . ?
C32 C33 1.353(7) . ?
C33 C34 1.422(7) . ?
C34 C35 1.337(7) . ?
C35 C36 1.437(7) . ?
C36 C37 1.407(7) . ?
C37 C31 1.403(7) 2 ?
C37 C38 1.512(6) . ?
C39 C40 1.508(7) . ?
C40 C41 1.378(7) . ?
C41 C42 1.375(7) . ?
C42 C44 1.500(7) . ?
C45 C46 1.523(7) . ?
C46 C48 1.388(8) 2 ?
C46 C47 1.410(8) . ?
C47 C52 1.420(8) . ?
C47 C48 1.448(7) . ?
C48 C46 1.388(8) 2 ?
C48 C49 1.432(8) . ?
C49 C50 1.359(8) . ?
C50 C51 1.419(8) . ?
C51 C52 1.355(8) . ?
N1S C1S 1.129(11) . ?
C1S C2S 1.474(14) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
C4A H4A1 0.9500 . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9500 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C41 H41A 0.9500 . ?
C43 H43A 0.9500 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9500 . ?
C51 H51A 0.9500 . ?
C52 H52A 0.9500 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
N2 H2A O1 0.88 2.16 3.024(5) 168.2 .
N3 H3A O1 0.88 2.10 2.973(5) 171.1 .
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
O1 C1 C2 C3 -0.9(10) . . . . ?
C2 C1 C2 C3 178.5(4) 2 . . . ?
C1 C1 C2 C3 177.6(8) 2 . . . ?
O1 C1 C2 C1 -178.5(4) . . . 2 ?
C2 C1 C2 C1 0.8(5) 2 . . 2 ?
C1 C2 C3 C8 -177.3(5) . . . . ?
C1 C2 C3 C8 -0.9(10) 2 . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
C1 C2 C3 C4 177.9(5) 2 . . . ?
C2 C3 C4 C5 -176.4(5) . . . . ?
C8 C3 C4 C5 2.5(8) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C11 N1 C6 C7 176.5(5) . . . . ?
C9 N1 C6 C7 -7.8(8) . . . . ?
C11 N1 C6 C5 -2.2(8) . . . . ?
C9 N1 C6 C5 173.6(5) . . . . ?
C4 C5 C6 N1 174.9(5) . . . . ?
C4 C5 C6 C7 -3.8(8) . . . . ?
N1 C6 C7 C8 -174.6(5) . . . . ?
C5 C6 C7 C8 4.1(8) . . . . ?
C6 C7 C8 C3 -1.2(8) . . . . ?
C2 C3 C8 C7 176.7(5) . . . . ?
C4 C3 C8 C7 -2.1(8) . . . . ?
C6 N1 C9 C10 -82.7(7) . . . . ?
C11 N1 C9 C10 93.3(6) . . . . ?
C6 N1 C11 C12 -75.4(7) . . . . ?
C9 N1 C11 C12 108.6(6) . . . . ?
C13 O2 C12 C11 -178.1(5) . . . . ?
N1 C11 C12 O2 -51.5(7) . . . . ?
C12 O2 C13 C14 -173.9(5) . . . . ?
O2 C13 C14 C15 -174.5(6) . . . . ?
C13 C14 C15 C16 -177.5(7) . . . . ?
C13 C14 C15 C29 -154.3(18) . . . 2 ?
C14 C15 C16 C17 71.7(13) . . . . ?
C29 C15 C16 C17 -59(4) 2 . . . ?
C15 C16 C17 C18 47.5(18) . . . . ?
C16 C17 C18 C19 -179.2(10) . . . . ?
C17 C18 C19 C20 173.8(13) . . . . ?
C18 C19 C20 C21 -85.5(17) . . . . ?
C19 C20 C21 C22 161.9(14) . . . . ?
C20 C21 C22 C23 22(3) . . . . ?
C21 C22 C23 C24 -161.0(15) . . . . ?
C21 C22 C23 C25 146.5(17) . . . . ?
C22 C23 C24 C25 -82.1(16) . . . . ?
C23 C24 C25 C26 -105(2) . . . . ?
C22 C23 C25 C26 -145.3(16) . . . . ?
C24 C23 C25 C26 94.9(15) . . . . ?
C22 C23 C25 C24 119.9(16) . . . . ?
C24 C25 C26 C27 -100(3) . . . . ?
C23 C25 C26 C27 -154(2) . . . . ?
C25 C26 C27 C28 -155(2) . . . . ?
C26 C27 C28 C29 152(3) . . . . ?
C27 C28 C29 C15 -86(4) . . . 2 ?
C37 C31 C32 C33 177.0(5) 2 . . . ?
C36 C31 C32 C33 -1.3(8) . . . . ?
C31 C32 C33 C34 -0.2(8) . . . . ?
C32 C33 C34 C35 1.5(8) . . . . ?
C33 C34 C35 C36 -1.4(9) . . . . ?
C34 C35 C36 C37 -179.1(5) . . . . ?
C34 C35 C36 C31 -0.1(8) . . . . ?
C37 C31 C36 C37 2.0(6) 2 . . . ?
C32 C31 C36 C37 -179.6(5) . . . . ?
C37 C31 C36 C35 -177.0(5) 2 . . . ?
C32 C31 C36 C35 1.4(7) . . . . ?
C35 C36 C37 C31 -175.2(5) . . . 2 ?
C31 C36 C37 C31 5.8(6) . . . 2 ?
C35 C36 C37 C38 8.4(7) . . . . ?
C31 C36 C37 C38 -170.6(4) . . . . ?
C39 N2 C38 C37 -174.9(5) . . . . ?
C31 C37 C38 N2 93.9(6) 2 . . . ?
C36 C37 C38 N2 -89.7(6) . . . . ?
C38 N2 C39 O3 5.5(8) . . . . ?
C38 N2 C39 C40 -177.1(5) . . . . ?
C43 N4A C40 C41 1.4(9) . . . . ?
C43 N4A C40 C39 -177.9(6) . . . . ?
O3 C39 C40 N4A -16.3(8) . . . . ?
N2 C39 C40 N4A 166.3(5) . . . . ?
O3 C39 C40 C41 164.4(6) . . . . ?
N2 C39 C40 C41 -13.0(8) . . . . ?
N4A C40 C41 C42 -1.2(9) . . . . ?
C39 C40 C41 C42 178.0(5) . . . . ?
C43 C4A C42 C41 1.0(10) . . . . ?
C43 C4A C42 C44 -179.2(6) . . . . ?
C40 C41 C42 C4A -0.1(9) . . . . ?
C40 C41 C42 C44 -180.0(5) . . . . ?
C40 N4A C43 C4A -0.5(12) . . . . ?
C42 C4A C43 N4A -0.7(12) . . . . ?
C45 N3 C44 O4 -3.8(8) . . . . ?
C45 N3 C44 C42 177.6(5) . . . . ?
C4A C42 C44 O4 17.5(9) . . . . ?
C41 C42 C44 O4 -162.7(6) . . . . ?
C4A C42 C44 N3 -163.9(5) . . . . ?
C41 C42 C44 N3 15.9(8) . . . . ?
C44 N3 C45 C46 168.1(5) . . . . ?
N3 C45 C46 C48 95.6(6) . . . 2 ?
N3 C45 C46 C47 -87.0(6) . . . . ?
C48 C46 C47 C52 -172.5(5) 2 . . . ?
C45 C46 C47 C52 10.1(8) . . . . ?
C48 C46 C47 C48 6.8(7) 2 . . . ?
C45 C46 C47 C48 -170.6(4) . . . . ?
C46 C47 C48 C46 0.0(6) . . . 2 ?
C52 C47 C48 C46 179.3(5) . . . 2 ?
C46 C47 C48 C49 178.7(5) . . . . ?
C52 C47 C48 C49 -1.9(7) . . . . ?
C46 C48 C49 C50 -179.3(5) 2 . . . ?
C47 C48 C49 C50 1.9(8) . . . . ?
C48 C49 C50 C51 -1.0(9) . . . . ?
C49 C50 C51 C52 0.0(9) . . . . ?
C50 C51 C52 C47 -0.1(9) . . . . ?
C46 C47 C52 C51 -179.6(5) . . . . ?
C48 C47 C52 C51 1.0(8) . . . . ?
