#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017702.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017702
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'Young, David J.'
_publ_section_title
;
 Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded
 structure of the 1:1 proton-transfer salt of the diazo-dye precursor
 4-(phenyldiazenyl)aniline (aniline yellow) with
 <small>L</small>-tartaric acid
;
_journal_coeditor_code           FG3168
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o345
_journal_page_last               o348
_journal_paper_doi               10.1107/S0108270110020597
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H12 N3 + , C4 H5 O6 -'
_chemical_formula_moiety         'C12 H12 N3 + , C4 H5 O6 -'
_chemical_formula_sum            'C16 H17 N3 O6'
_chemical_formula_weight         347.33
_chemical_melting_point          467
_chemical_name_common
;
4-(phenyldiazenyl)anilinium hydrogen (2R,3R)-tartrate
;
_chemical_name_systematic
;
4-(phenyldiazenyl)anilinium
(2R,3R)-3-carboxy-2,3-dihydroxypropanoate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                91.754(3)
_cell_angle_beta                 91.308(3)
_cell_angle_gamma                108.135(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1710(3)
_cell_length_b                   7.4134(3)
_cell_length_c                   18.2438(6)
_cell_measurement_reflns_used    7191
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.15
_cell_measurement_theta_min      2.89
_cell_volume                     792.33(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Gemini-S CCD detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16695
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0495
_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)+(0.0802P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                3593
_reflns_number_total             4174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3168.cif
_cod_data_source_block           I
_cod_database_code               2017702
_cod_database_fobs_code          2017702
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1C -0.0628(5) 0.5384(4) 0.08229(15) 0.0322(8) Uani . . 1.000
N N4C -0.1760(4) 0.5383(3) 0.38852(12) 0.0195(6) Uani . . 1.000
N N11C 0.1379(5) 0.5723(4) 0.06254(15) 0.0347(8) Uani . . 1.000
C C1C -0.0825(5) 0.5374(4) 0.16033(17) 0.0272(8) Uani . . 1.000
C C2C -0.2964(11) 0.4571(11) 0.1863(4) 0.0281(14) Uiso . . 0.500
C C2E -0.2957(11) 0.5296(11) 0.1872(4) 0.0280(14) Uiso . . 0.500
C C3C -0.3319(11) 0.4563(11) 0.2614(3) 0.0246(13) Uiso . . 0.500
C C3E -0.3281(11) 0.5288(10) 0.2630(3) 0.0248(13) Uiso . . 0.500
C C4C -0.1479(4) 0.5351(3) 0.30893(15) 0.0203(7) Uani . . 1.000
C C5C 0.0709(10) 0.6190(10) 0.2837(3) 0.0249(12) Uiso . . 0.500
C C5E 0.0633(11) 0.5398(10) 0.2840(3) 0.0261(12) Uiso . . 0.500
C C6C 0.1044(11) 0.6185(10) 0.2089(3) 0.0257(12) Uiso . . 0.500
C C6E 0.0963(11) 0.5392(10) 0.2092(3) 0.0253(12) Uiso . . 0.500
C C11C 0.1642(5) 0.5787(4) -0.01519(16) 0.0286(9) Uani . . 1.000
C C21C -0.0058(11) 0.5805(11) -0.0652(3) 0.0272(13) Uiso . . 0.500
C C21E -0.0111(12) 0.5046(11) -0.0658(4) 0.0306(14) Uiso . . 0.500
C C31C 0.0419(12) 0.5946(11) -0.1387(4) 0.0290(13) Uiso . . 0.500
C C31E 0.0316(13) 0.5164(12) -0.1397(4) 0.0367(16) Uiso . . 0.500
C C41C 0.2509(6) 0.5998(5) -0.16274(18) 0.0369(10) Uani . . 1.000
C C51C 0.4195(12) 0.5862(10) -0.1126(4) 0.0320(13) Uiso . . 0.500
C C51E 0.4278(13) 0.6804(12) -0.1130(4) 0.0380(15) Uiso . . 0.500
C C61C 0.3743(11) 0.5748(10) -0.0377(4) 0.0307(13) Uiso . . 0.500
C C61E 0.3888(13) 0.6694(12) -0.0382(4) 0.0384(15) Uiso . . 0.500
N N1D 0.1669(5) 0.0823(4) 1.00283(14) 0.0313(8) Uani . . 1.000
N N4D 0.3820(4) 0.1221(3) 0.70360(12) 0.0198(6) Uani . . 1.000
N N11D -0.0375(5) 0.0488(4) 1.01770(15) 0.0329(8) Uani . . 1.000
C C1D 0.2072(5) 0.0879(4) 0.92596(16) 0.0262(8) Uani . . 1.000
C C2D 0.0388(10) 0.0771(10) 0.8706(3) 0.0209(12) Uiso . . 0.500
C C2F 0.0402(11) 0.0105(11) 0.8723(3) 0.0235(13) Uiso . . 0.500
C C3D 0.0959(10) 0.0889(9) 0.7979(3) 0.0186(11) Uiso . . 0.500
C C3F 0.0972(11) 0.0211(10) 0.7994(3) 0.0236(13) Uiso . . 0.500
C C4D 0.3178(4) 0.1069(4) 0.77999(15) 0.0196(7) Uani . . 1.000
C C5D 0.4805(10) 0.1031(9) 0.8320(3) 0.0246(12) Uiso . . 0.500
C C5F 0.4912(10) 0.1944(10) 0.8347(3) 0.0254(12) Uiso . . 0.500
C C6D 0.4246(10) 0.0911(9) 0.9050(3) 0.0248(12) Uiso . . 0.500
C C6F 0.4348(10) 0.1835(10) 0.9080(3) 0.0261(12) Uiso . . 0.500
C C11D -0.0770(5) 0.0432(4) 1.09485(16) 0.0280(8) Uani . . 1.000
C C21D 0.0920(6) 0.1248(5) 1.14872(16) 0.0329(14) Uiso . . 0.500
C C21F 0.0835(11) 0.0406(9) 1.1472(3) 0.0300(13) Uiso . . 0.500
C C31D 0.0351(12) 0.1183(12) 1.2218(4) 0.0366(15) Uiso . . 0.500
C C31F 0.0244(12) 0.0279(11) 1.2198(4) 0.0331(14) Uiso . . 0.500
C C41D -0.1885(6) 0.0245(5) 1.24124(16) 0.0390(10) Uani . . 1.000
C C51D -0.3557(13) -0.0581(12) 1.1884(4) 0.0390(15) Uiso . . 0.500
C C51F -0.3483(12) 0.0325(11) 1.1886(4) 0.0333(14) Uiso . . 0.500
C C61D -0.3000(12) -0.0492(11) 1.1149(4) 0.0347(14) Uiso . . 0.500
C C61F -0.2934(11) 0.0419(10) 1.1142(4) 0.0301(13) Uiso . . 0.500
O O2A -0.3622(3) 0.5088(3) 0.69950(11) 0.0228(5) Uani . . 1.000
O O3A 0.1018(3) 0.7150(3) 0.66547(12) 0.0276(6) Uani . . 1.000
O O11A -0.4098(3) 0.8420(3) 0.68346(12) 0.0260(6) Uani . . 1.000
O O12A -0.1931(3) 0.9075(3) 0.58533(11) 0.0258(6) Uani . . 1.000
O O41A -0.2114(3) 0.2534(3) 0.59407(12) 0.0249(6) Uani . . 1.000
O O42A 0.1255(4) 0.3572(3) 0.65412(15) 0.0391(8) Uani . . 1.000
C C1A -0.2955(4) 0.8008(4) 0.63381(14) 0.0179(7) Uani . . 1.000
C C2A -0.2911(4) 0.5935(3) 0.63153(14) 0.0176(7) Uani . . 1.000
C C3A -0.0536(4) 0.5847(3) 0.61653(15) 0.0178(7) Uani . . 1.000
C C4A -0.0376(4) 0.3851(4) 0.62462(14) 0.0187(7) Uani . . 1.000
O O2B 0.0297(3) -0.0729(3) 0.41205(12) 0.0250(6) Uani . . 1.000
O O3B 0.2806(3) 0.0322(3) 0.54840(10) 0.0231(5) Uani . . 1.000
O O11B 0.0018(3) 0.2667(3) 0.43520(13) 0.0280(6) Uani . . 1.000
O O12B 0.3787(3) 0.4087(3) 0.43645(13) 0.0288(6) Uani . . 1.000
O O41B 0.3136(3) -0.2980(3) 0.49378(12) 0.0263(6) Uani . . 1.000
O O42B 0.5627(3) -0.1540(3) 0.41079(11) 0.0235(6) Uani . . 1.000
C C1B 0.2011(5) 0.2653(4) 0.43131(15) 0.0195(7) Uani . . 1.000
C C2B 0.2408(4) 0.0740(3) 0.41817(14) 0.0173(7) Uani . . 1.000
C C3B 0.3850(4) 0.0350(3) 0.48092(14) 0.0164(7) Uani . . 1.000
C C4B 0.4333(4) -0.1496(4) 0.45930(15) 0.0174(7) Uani . . 1.000
H H2C -0.42140 0.40170 0.15280 0.0340 Uiso calc . 0.500
H H2E -0.41850 0.52500 0.15400 0.0340 Uiso calc . 0.500
H H3C -0.48030 0.40230 0.27950 0.0300 Uiso calc . 0.500
H H3E -0.47180 0.52390 0.28190 0.0300 Uiso calc . 0.500
H H5C 0.19510 0.67560 0.31730 0.0300 Uiso calc . 0.500
H H5E 0.18430 0.54340 0.31780 0.0310 Uiso calc . 0.500
H H6C 0.25270 0.67260 0.19070 0.0310 Uiso calc . 0.500
H H6E 0.23980 0.53990 0.19110 0.0300 Uiso calc . 0.500
H H21C -0.15400 0.57200 -0.04930 0.0330 Uiso calc . 0.500
H H21E -0.16150 0.44520 -0.05000 0.0370 Uiso calc . 0.500
H H31C -0.07310 0.60080 -0.17320 0.0350 Uiso calc . 0.500
H H31E -0.09020 0.46710 -0.17490 0.0440 Uiso calc . 0.500
H H41C 0.28230 0.61270 -0.21340 0.0440 Uiso calc R 1.000
H H42C -0.10420 0.66280 0.40940 0.0230 Uiso . R 1.000
H H43C -0.10720 0.47180 0.41060 0.0230 Uiso . R 1.000
H H44C -0.32420 0.50280 0.39770 0.0230 Uiso . R 1.000
H H51C 0.56370 0.58460 -0.12920 0.0380 Uiso calc . 0.500
H H51E 0.57610 0.74340 -0.12960 0.0460 Uiso calc . 0.500
H H61C 0.48660 0.56460 -0.00300 0.0370 Uiso calc . 0.500
H H61E 0.51040 0.72160 -0.00320 0.0460 Uiso calc . 0.500
H H2D -0.11400 0.06180 0.88350 0.0250 Uiso calc . 0.500
H H2F -0.11290 -0.04970 0.88530 0.0280 Uiso calc . 0.500
H H3D -0.01570 0.08470 0.76060 0.0220 Uiso calc . 0.500
H H3F -0.01770 -0.03170 0.76240 0.0280 Uiso calc . 0.500
H H5D 0.62970 0.10880 0.81800 0.0300 Uiso calc . 0.500
H H5F 0.64250 0.25890 0.82110 0.0310 Uiso calc . 0.500
H H6D 0.53490 0.08490 0.94120 0.0300 Uiso calc . 0.500
H H6F 0.54720 0.23930 0.94550 0.0310 Uiso calc . 0.500
H H21D 0.24480 0.18490 1.13540 0.0400 Uiso . . 0.500
H H21F 0.23360 0.04730 1.13390 0.0360 Uiso calc . 0.500
H H31D 0.14800 0.17760 1.25870 0.0440 Uiso calc . 0.500
H H31F 0.13440 0.02140 1.25610 0.0400 Uiso calc . 0.500
H H41D -0.22550 0.01760 1.29160 0.0470 Uiso calc R 1.000
H H42D 0.46920 0.23880 0.69710 0.0240 Uiso . R 1.000
H H43D 0.25720 0.09080 0.67210 0.0240 Uiso . R 1.000
H H44D 0.45720 0.05180 0.69310 0.0240 Uiso . R 1.000
H H51D -0.50760 -0.12050 1.20200 0.0470 Uiso calc . 0.500
H H51F -0.49590 0.03170 1.20260 0.0400 Uiso calc . 0.500
H H61D -0.41440 -0.10640 1.07810 0.0420 Uiso calc . 0.500
H H61F -0.40320 0.04730 1.07770 0.0360 Uiso calc . 0.500
H H2A -0.39880 0.52020 0.59150 0.0210 Uiso calc R 1.000
H H3A -0.01560 0.62400 0.56520 0.0210 Uiso calc R 1.000
H H41A -0.2060 0.15040 0.59690 0.0300 Uiso . R 1.000
H H21A -0.35990 0.59440 0.72470 0.0270 Uiso . R 1.000
H H31A 0.23760 0.74820 0.67020 0.0330 Uiso . R 1.000
H H2B 0.32300 0.07650 0.37140 0.0210 Uiso calc R 1.000
H H3B 0.53370 0.13980 0.48390 0.0200 Uiso calc R 1.000
H H21B -0.06320 -0.02630 0.41980 0.0300 Uiso . R 1.000
H H31B 0.14920 -0.00260 0.55870 0.0280 Uiso . R 1.000
H H41B 0.32850 -0.39200 0.47470 0.0320 Uiso . R 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A O2A H21A . . . 103.00 no
C3A O3A H31A . . . 133.00 no
C4A O41A H41A . . . 115.00 no
C2B O2B H21B . . . 107.00 no
C3B O3B H31B . . . 131.00 no
C4B O41B H41B . . . 109.00 no
N11C N1C C1C . . . 113.2(3) no
N1C N11C C11C . . . 114.7(3) no
H42C N4C H43C . . . 103.00 no
C4C N4C H44C . . . 109.00 no
H42C N4C H44C . . . 109.00 no
H43C N4C H44C . . . 112.00 no
C4C N4C H42C . . . 111.00 no
C4C N4C H43C . . . 113.00 no
N11D N1D C1D . . . 113.9(3) no
N1D N11D C11D . . . 113.7(3) no
H42D N4D H44D . . . 107.00 no
C4D N4D H44D . . . 111.00 no
C4D N4D H42D . . . 109.00 no
C4D N4D H43D . . . 112.00 no
H43D N4D H44D . . . 107.00 no
H42D N4D H43D . . . 110.00 no
N1C C1C C2E . . . 116.7(4) no
N1C C1C C6C . . . 122.6(4) no
N1C C1C C2C . . . 116.8(4) no
C2E C1C C6E . . . 119.8(4) no
N1C C1C C6E . . . 123.5(4) no
C2C C1C C6E . . . 114.7(5) no
C2E C1C C6C . . . 115.5(5) no
C2C C1C C6C . . . 120.6(5) no
C1C C2C C3E . . . 114.1(6) no
C1C C2C C3C . . . 120.5(6) no
C1C C2E C3C . . . 113.4(6) no
C1C C2E C3E . . . 120.0(6) no
C2C C3C C4C . . . 118.8(6) no
C2E C3E C4C . . . 118.3(6) no
N4C C4C C3C . . . 121.0(3) no
N4C C4C C5C . . . 117.3(3) no
N4C C4C C5E . . . 117.6(3) no
C3E C4C C5E . . . 123.0(4) no
C3E C4C C5C . . . 117.6(4) no
N4C C4C C3E . . . 119.4(3) no
C3C C4C C5E . . . 116.6(4) no
C3C C4C C5C . . . 121.7(4) no
C4C C5C C6E . . . 111.0(5) no
C4C C5C C6C . . . 119.0(5) no
C4C C5E C6E . . . 119.1(6) no
C1C C6C C5C . . . 119.4(6) no
C1C C6E C5E . . . 119.7(6) no
C21E C11C C61E . . . 120.5(5) no
N11C C11C C21E . . . 124.0(4) no
C21E C11C C61C . . . 114.6(5) no
C21C C11C C61C . . . 121.2(5) no
C21C C11C C61E . . . 114.5(5) no
N11C C11C C61E . . . 115.5(4) no
N11C C11C C21C . . . 124.3(4) no
N11C C11C C61C . . . 114.5(4) no
C11C C21C C31C . . . 119.2(6) no
C11C C21E C31E . . . 119.8(7) no
C21C C31C C41C . . . 121.2(6) no
C21E C31E C41C . . . 120.2(7) no
C31E C41C C51E . . . 120.9(5) no
C31C C41C C51C . . . 119.8(5) no
C41C C51C C61C . . . 119.6(6) no
C41C C51E C61E . . . 119.7(7) no
C41C C51E C61C . . . 109.1(6) no
C11C C61C C51C . . . 118.9(6) no
C1C C2C H2C . . . 120.00 no
C3C C2C H2C . . . 120.00 no
C1C C2E H2E . . . 120.00 no
C3E C2E H2E . . . 120.00 no
C2C C3C H3C . . . 121.00 no
C4C C3C H3C . . . 121.00 no
C4C C3E H3E . . . 121.00 no
C2E C3E H3E . . . 121.00 no
C6C C5C H5C . . . 120.00 no
C4C C5C H5E . . . 103.00 no
C4C C5C H5C . . . 121.00 no
C4C C5E H5E . . . 120.00 no
C6E C5E H5E . . . 121.00 no
C1C C6C H6C . . . 120.00 no
C5C C6C H6C . . . 120.00 no
C1C C6E H6E . . . 120.00 no
C5E C6E H6E . . . 120.00 no
C31C C21C H21C . . . 120.00 no
C11C C21C H21C . . . 120.00 no
C31E C21E H21E . . . 120.00 no
C11C C21E H21E . . . 120.00 no
C41C C31C H31C . . . 119.00 no
C21E C31E H31E . . . 120.00 no
C41C C31E H31E . . . 120.00 no
C51E C41C H41C . . . 118.00 no
C51C C41C H41C . . . 120.00 no
C31E C41C H41C . . . 121.00 no
C31C C41C H41C . . . 120.00 no
C41C C51C H51C . . . 120.00 no
C61C C51C H51C . . . 120.00 no
C41C C51E H51E . . . 120.00 no
C61E C51E H51E . . . 120.00 no
C11C C61C H61C . . . 121.00 no
C51C C61C H61E . . . 109.00 no
C51C C61C H61C . . . 121.00 no
C11C C61E H61E . . . 121.00 no
C51E C61E H61E . . . 121.00 no
N1D C1D C2D . . . 124.5(4) no
N1D C1D C2F . . . 123.9(4) no
C2D C1D C6D . . . 118.6(4) no
N1D C1D C6D . . . 116.7(3) no
C2F C1D C6F . . . 121.4(4) no
C1D C2D C3D . . . 120.2(6) no
C1D C2F C3F . . . 119.5(6) no
C2D C3D C4D . . . 119.1(5) no
C2F C3F C4D . . . 120.7(6) no
C3D C4D C5D . . . 122.0(4) no
N4D C4D C5D . . . 118.1(3) no
N4D C4D C3D . . . 119.9(3) no
N4D C4D C3F . . . 121.9(3) no
C4D C5D C6F . . . 111.5(5) no
C4D C5D C6D . . . 119.2(5) no
C4D C5F C6F . . . 118.9(6) no
C1D C6D C5D . . . 120.5(5) no
C1D C6F C5F . . . 118.9(5) no
N11D C11D C61D . . . 116.3(4) no
C21F C11D C61F . . . 120.8(5) no
N11D C11D C21D . . . 123.8(3) no
N11D C11D C21F . . . 123.9(4) no
C21D C11D C61D . . . 120.0(4) no
C11D C21D C31D . . . 119.5(4) no
C11D C21F C31F . . . 119.0(6) no
C21D C31D C41D . . . 120.0(6) no
C21F C31F C41D . . . 122.0(6) no
C31D C41D C51D . . . 120.8(5) no
C41D C51F C61F . . . 120.1(6) no
C11D C61D C51D . . . 120.4(7) no
C11D C61F C51F . . . 119.1(6) no
C1D C2D H2D . . . 120.00 no
C3D C2D H2D . . . 120.00 no
C1D C2F H2F . . . 120.00 no
C3F C2F H2F . . . 120.00 no
C2D C3D H3D . . . 120.00 no
C4D C3D H3D . . . 120.00 no
C2F C3F H3F . . . 120.00 no
C4D C3F H3F . . . 120.00 no
C4D C5D H5D . . . 120.00 no
C6D C5D H5D . . . 120.00 no
C4D C5F H5F . . . 121.00 no
C6F C5F H5F . . . 121.00 no
C1D C6D H6D . . . 120.00 no
C5D C6D H6D . . . 120.00 no
C1D C6F H6F . . . 121.00 no
C5F C6F H6F . . . 121.00 no
C31D C21D H21D . . . 120.00 no
C11D C21D H21D . . . 120.00 no
C11D C21F H21F . . . 121.00 no
C31F C21F H21F . . . 120.00 no
C21D C31D H31D . . . 120.00 no
C41D C31D H31D . . . 120.00 no
C21F C31F H31F . . . 119.00 no
C41D C31F H31F . . . 119.00 no
C51D C41D H41D . . . 120.00 no
C31D C41D H41D . . . 120.00 no
C31F C41D H41D . . . 121.00 no
C51F C41D H41D . . . 120.00 no
C41D C51D H51D . . . 120.00 no
C61D C51D H51D . . . 120.00 no
C61F C51F H51F . . . 120.00 no
C41D C51F H51F . . . 120.00 no
C51D C61D H61D . . . 120.00 no
C11D C61D H61D . . . 120.00 no
C11D C61F H61F . . . 121.00 no
C51F C61F H61F . . . 120.00 no
O11A C1A C2A . . . 115.3(2) no
O11A C1A O12A . . . 126.7(3) no
O12A C1A C2A . . . 118.0(2) no
C1A C2A C3A . . . 111.04(19) no
O2A C2A C3A . . . 109.2(2) no
O2A C2A C1A . . . 110.0(2) no
C2A C3A C4A . . . 111.85(19) no
O3A C3A C4A . . . 110.7(2) no
O3A C3A C2A . . . 108.1(2) no
O41A C4A O42A . . . 125.0(3) no
O42A C4A C3A . . . 122.0(2) no
O41A C4A C3A . . . 113.0(2) no
O2A C2A H2A . . . 109.00 no
C1A C2A H2A . . . 109.00 no
C3A C2A H2A . . . 109.00 no
C4A C3A H3A . . . 109.00 no
O3A C3A H3A . . . 109.00 no
C2A C3A H3A . . . 109.00 no
O11B C1B C2B . . . 117.8(2) no
O11B C1B O12B . . . 126.3(3) no
O12B C1B C2B . . . 115.8(3) no
O2B C2B C1B . . . 110.1(2) no
O2B C2B C3B . . . 109.38(19) no
C1B C2B C3B . . . 110.5(2) no
C2B C3B C4B . . . 106.4(2) no
O3B C3B C2B . . . 111.8(2) no
O3B C3B C4B . . . 114.4(2) no
O41B C4B O42B . . . 124.6(3) no
O41B C4B C3B . . . 114.4(2) no
O42B C4B C3B . . . 120.8(2) no
O2B C2B H2B . . . 109.00 no
C1B C2B H2B . . . 109.00 no
C3B C2B H2B . . . 109.00 no
O3B C3B H3B . . . 108.00 no
C2B C3B H3B . . . 108.00 no
C4B C3B H3B . . . 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2A C2A . . 1.423(3) no
O3A C3A . . 1.408(3) no
O11A C1A . . 1.248(3) no
O12A C1A . . 1.251(3) no
O41A C4A . . 1.305(3) no
O42A C4A . . 1.207(4) no
O2A H21A . . 0.7700 no
O3A H31A . . 0.8000 no
O41A H41A . . 0.7800 no
O2B C2B . . 1.414(3) no
O3B C3B . . 1.400(3) no
O11B C1B . . 1.237(4) no
O12B C1B . . 1.267(4) no
O41B C4B . . 1.307(3) no
O42B C4B . . 1.212(3) no
O2B H21B . . 0.7700 no
O3B H31B . . 0.8000 no
O41B H41B . . 0.8000 no
N1C C1C . . 1.432(4) no
N1C N11C . . 1.249(4) no
N4C C4C . . 1.467(4) no
N11C C11C . . 1.432(4) no
N4C H44C . . 0.8900 no
N4C H43C . . 0.8500 no
N4C H42C . . 0.9500 no
N1D C1D . . 1.430(4) no
N1D N11D . . 1.245(4) no
N4D C4D . . 1.456(4) no
N11D C11D . . 1.434(4) no
N4D H42D . . 0.8800 no
N4D H44D . . 0.8200 no
N4D H43D . . 0.9200 no
C1C C6E . . 1.399(7) no
C1C C2C . . 1.370(8) no
C1C C2E . . 1.399(8) no
C1C C6C . . 1.402(7) no
C2C C3C . . 1.392(9) no
C2E C3E . . 1.402(9) no
C3C C4C . . 1.376(7) no
C3E C4C . . 1.365(7) no
C4C C5E . . 1.381(7) no
C4C C5C . . 1.395(7) no
C5C C6C . . 1.385(8) no
C5E C6E . . 1.384(8) no
C11C C61E . . 1.419(9) no
C11C C21C . . 1.378(7) no
C11C C61C . . 1.378(8) no
C11C C21E . . 1.370(8) no
C21C C31C . . 1.380(9) no
C21E C31E . . 1.380(10) no
C31C C41C . . 1.361(9) no
C31E C41C . . 1.383(9) no
C41C C51E . . 1.374(9) no
C41C C51C . . 1.399(8) no
C51C C61C . . 1.401(10) no
C51E C61E . . 1.392(10) no
C2C H2C . . 0.9500 no
C2E H2E . . 0.9500 no
C3C H3C . . 0.9500 no
C3E H3E . . 0.9500 no
C5C H5C . . 0.9500 no
C5E H5E . . 0.9500 no
C6C H6C . . 0.9500 no
C6E H6E . . 0.9500 no
C21C H21C . . 0.9500 no
C21E H21E . . 0.9500 no
C31C H31C . . 0.9500 no
C31E H31E . . 0.9500 no
C41C H41C . . 0.9500 no
C51C H51C . . 0.9500 no
C51E H51E . . 0.9500 no
C61C H61C . . 0.9500 no
C61E H61E . . 0.9500 no
C1D C2F . . 1.379(7) no
C1D C2D . . 1.415(7) no
C1D C6F . . 1.414(7) no
C1D C6D . . 1.397(7) no
C2D C3D . . 1.379(8) no
C2F C3F . . 1.382(8) no
C3D C4D . . 1.382(7) no
C3F C4D . . 1.371(8) no
C4D C5F . . 1.429(7) no
C4D C5D . . 1.373(7) no
C5D C6D . . 1.382(8) no
C5F C6F . . 1.388(8) no
C11D C61F . . 1.386(8) no
C11D C21F . . 1.365(7) no
C11D C61D . . 1.396(8) no
C11D C21D . . 1.394(5) no
C21D C31D . . 1.385(8) no
C21F C31F . . 1.380(9) no
C31D C41D . . 1.398(9) no
C31F C41D . . 1.372(9) no
C41D C51F . . 1.377(8) no
C41D C51D . . 1.376(9) no
C51D C61D . . 1.390(10) no
C51F C61F . . 1.405(10) no
C2D H2D . . 0.9500 no
C2F H2F . . 0.9500 no
C3D H3D . . 0.9500 no
C3F H3F . . 0.9500 no
C5D H5D . . 0.9500 no
C5F H5F . . 0.9500 no
C6D H6D . . 0.9500 no
C6F H6F . . 0.9500 no
C21D H21D . . 0.9500 no
C21F H21F . . 0.9500 no
C31D H31D . . 0.9500 no
C31F H31F . . 0.9500 no
C41D H41D . . 0.9500 no
C51D H51D . . 0.9500 no
C51F H51F . . 0.9500 no
C61D H61D . . 0.9500 no
C61F H61F . . 0.9500 no
C1A C2A . . 1.545(4) no
C2A C3A . . 1.518(4) no
C3A C4A . . 1.525(4) no
C2A H2A . . 1.0000 no
C3A H3A . . 1.0000 no
C1B C2B . . 1.525(4) no
C2B C3B . . 1.523(4) no
C3B C4B . . 1.531(4) no
C2B H2B . . 1.0000 no
C3B H3B . . 1.0000 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2A H21A O11A . 0.77 2.11 2.601(3) 122 yes
O2B H21B O11B . 0.77 2.09 2.599(3) 124 yes
O2B H21B O42B 1_455 0.77 2.21 2.754(3) 129 yes
O3A H31A O11A 1_655 0.80 2.07 2.872(3) 178 yes
O3B H31B O12A 1_545 0.80 2.08 2.881(3) 180 yes
O41A H41A O12A 1_545 0.78 1.83 2.602(3) 170 yes
O41B H41B O12B 1_545 0.80 1.73 2.531(3) 176 yes
N4C H42C O2B 1_565 0.95 1.87 2.779(3) 158 yes
N4C H43C O11B . 0.85 1.91 2.724(3) 162 yes
N4C H44C O12B 1_455 0.89 1.91 2.785(3) 168 yes
N4D H42D O2A 1_655 0.88 1.95 2.814(3) 169 yes
N4D H43D O3B . 0.92 2.30 2.898(3) 122 yes
N4D H43D O42A . 0.92 2.39 2.847(3) 111 yes
N4D H44D O11A 1_645 0.82 1.98 2.781(3) 167 yes
C3A H3A O41B 1_565 1.00 2.37 3.167(3) 137 no
C3B H3B O41A 1_655 1.00 2.48 3.184(3) 127 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1C N1C N11C C11C . . . . -178.6(2) no
N11C N1C C1C C2C . . . . -164.5(4) no
N11C N1C C1C C6C . . . . 17.2(5) no
N1C N11C C11C C21C . . . . 10.7(6) no
N1C N11C C11C C61C . . . . -166.6(4) no
C1D N1D N11D C11D . . . . 180.0(2) no
N11D N1D C1D C2D . . . . 6.4(5) no
N11D N1D C1D C6D . . . . -169.0(4) no
N1D N11D C11D C61D . . . . -160.8(4) no
N1D N11D C11D C21D . . . . 19.7(4) no
C6C C1C C2C C3C . . . . 0.6(9) no
N1C C1C C6C C5C . . . . 177.4(5) no
N1C C1C C2C C3C . . . . -177.7(6) no
C2C C1C C6C C5C . . . . -0.8(9) no
C1C C2C C3C C4C . . . . -0.9(10) no
C2C C3C C4C N4C . . . . 179.9(5) no
C2C C3C C4C C5C . . . . 1.5(9) no
N4C C4C C5C C6C . . . . 179.9(5) no
C3C C4C C5C C6C . . . . -1.7(9) no
C4C C5C C6C C1C . . . . 1.3(9) no
N11C C11C C21C C31C . . . . 177.4(5) no
N11C C11C C61C C51C . . . . -178.1(5) no
C21C C11C C61C C51C . . . . 4.5(9) no
C61C C11C C21C C31C . . . . -5.5(9) no
C11C C21C C31C C41C . . . . 2.4(11) no
C21C C31C C41C C51C . . . . 1.5(10) no
C31C C41C C51C C61C . . . . -2.5(9) no
C41C C51C C61C C11C . . . . -0.5(10) no
N1D C1D C2D C3D . . . . 178.2(5) no
C6D C1D C2D C3D . . . . -6.4(8) no
N1D C1D C6D C5D . . . . -177.8(5) no
C2D C1D C6D C5D . . . . 6.5(8) no
C1D C2D C3D C4D . . . . 1.5(9) no
C2D C3D C4D N4D . . . . -179.2(5) no
C2D C3D C4D C5D . . . . 3.6(8) no
N4D C4D C5D C6D . . . . 179.2(5) no
C3D C4D C5D C6D . . . . -3.5(8) no
C4D C5D C6D C1D . . . . -1.7(9) no
N11D C11D C21D C31D . . . . 177.5(5) no
C61D C11D C21D C31D . . . . -2.0(7) no
N11D C11D C61D C51D . . . . -178.6(6) no
C21D C11D C61D C51D . . . . 0.9(9) no
C11D C21D C31D C41D . . . . 2.3(9) no
C21D C31D C41D C51D . . . . -1.7(10) no
C31D C41D C51D C61D . . . . 0.6(10) no
C41D C51D C61D C11D . . . . -0.3(11) no
O11A C1A C2A O2A . . . . -17.3(3) no
O11A C1A C2A C3A . . . . -138.4(2) no
O12A C1A C2A O2A . . . . 165.0(2) no
O12A C1A C2A C3A . . . . 44.0(3) no
O2A C2A C3A O3A . . . . -71.7(2) no
O2A C2A C3A C4A . . . . 50.5(3) no
C1A C2A C3A O3A . . . . 49.9(3) no
C1A C2A C3A C4A . . . . 172.0(2) no
O3A C3A C4A O41A . . . . 164.6(2) no
O3A C3A C4A O42A . . . . -18.0(4) no
C2A C3A C4A O41A . . . . 44.0(3) no
C2A C3A C4A O42A . . . . -138.6(3) no
O11B C1B C2B O2B . . . . 0.5(3) no
O11B C1B C2B C3B . . . . -120.4(3) no
O12B C1B C2B O2B . . . . -178.8(2) no
O12B C1B C2B C3B . . . . 60.3(3) no
O2B C2B C3B O3B . . . . -61.9(2) no
O2B C2B C3B C4B . . . . 63.7(3) no
C1B C2B C3B O3B . . . . 59.5(3) no
C1B C2B C3B C4B . . . . -174.9(2) no
O3B C3B C4B O41B . . . . 19.5(3) no
O3B C3B C4B O42B . . . . -164.8(2) no
C2B C3B C4B O41B . . . . -104.6(3) no
C2B C3B C4B O42B . . . . 71.2(3) no
