#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:13:36 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180382 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/51/7205146.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_7205146
loop_
_publ_author_name
'Wu, De-Hong'
'Ge, Jia-Zhen'
'Cai, Hong-Lin'
'Zhang, Wen'
'Xiong, Ren-Gen'
_publ_section_title
;
 Organic salt of hydrogen l-tartaric acid: a novel
 wide-temperature-range ferroelectrics with a reversible phase
 transition
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              319
_journal_paper_doi               10.1039/c0ce00109k
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C8 H12 N, C4 H5 O6'
_chemical_formula_sum            'C12 H17 N O6'
_chemical_formula_weight         271.27
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                95.276(2)
_cell_angle_beta                 91.966(2)
_cell_angle_gamma                107.856(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4649(16)
_cell_length_b                   11.9022(18)
_cell_length_c                   14.8739(11)
_cell_measurement_reflns_used    3613
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.4700
_cell_measurement_theta_min      2.7566
_cell_volume                     1249.8(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10388
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0362
_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)+(0.0323P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                4617
_reflns_number_total             5593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00109K.TXT
_cod_data_source_block           wudh_LTP(93K)
_cod_database_code               7205146
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7926(4) 0.1666(3) 0.51988(19) 0.0231(7) Uani 1 1 d . . .
H1A H 0.8947 0.2226 0.4945 0.035 Uiso 1 1 calc R . .
H1B H 0.8203 0.1694 0.5837 0.035 Uiso 1 1 calc R . .
H1C H 0.6786 0.1863 0.5098 0.035 Uiso 1 1 calc R . .
C2 C 0.7677(4) 0.0424(3) 0.47485(18) 0.0191(7) Uani 1 1 d . . .
H2A H 0.6597 -0.0124 0.4987 0.023 Uiso 1 1 calc R . .
H2B H 0.8779 0.0203 0.4916 0.023 Uiso 1 1 calc R . .
C3 C 0.7394(4) 0.0273(3) 0.37206(19) 0.0149(6) Uani 1 1 d . . .
C4 C 0.7149(4) -0.0837(2) 0.32471(19) 0.0164(6) Uani 1 1 d . . .
H4 H 0.7138 -0.1474 0.3567 0.020 Uiso 1 1 calc R . .
C5 C 0.6919(4) -0.1012(3) 0.23056(19) 0.0153(6) Uani 1 1 d . . .
H5 H 0.6753 -0.1758 0.1999 0.018 Uiso 1 1 calc R . .
C6 C 0.6941(4) -0.0058(2) 0.18330(18) 0.0115(6) Uani 1 1 d . . .
C7 C 0.7187(4) 0.1054(2) 0.22851(18) 0.0134(6) Uani 1 1 d . . .
H7 H 0.7204 0.1691 0.1963 0.016 Uiso 1 1 calc R . .
C8 C 0.7408(4) 0.1212(3) 0.32298(19) 0.0151(6) Uani 1 1 d . . .
H8 H 0.7567 0.1958 0.3534 0.018 Uiso 1 1 calc R . .
C9 C 0.2151(5) -0.0693(3) 0.2693(2) 0.0273(7) Uani 1 1 d . . .
H9A H 0.3210 -0.0906 0.2917 0.041 Uiso 1 1 calc R . .
H9B H 0.2142 -0.0719 0.2046 0.041 Uiso 1 1 calc R . .
H9C H 0.1005 -0.1242 0.2860 0.041 Uiso 1 1 calc R . .
C10 C 0.2302(4) 0.0550(3) 0.30969(18) 0.0216(7) Uani 1 1 d . . .
H10A H 0.1177 0.0728 0.2900 0.026 Uiso 1 1 calc R . .
H10B H 0.3369 0.1105 0.2855 0.026 Uiso 1 1 calc R . .
C11 C 0.2538(4) 0.0759(3) 0.41240(19) 0.0151(6) Uani 1 1 d . . .
C12 C 0.2796(4) 0.1890(3) 0.45507(19) 0.0178(6) Uani 1 1 d . . .
H12 H 0.2840 0.2505 0.4200 0.021 Uiso 1 1 calc R . .
C13 C 0.2990(4) 0.2127(2) 0.54900(18) 0.0145(6) Uani 1 1 d . . .
H13 H 0.3142 0.2888 0.5764 0.017 Uiso 1 1 calc R . .
C14 C 0.2953(4) 0.1216(2) 0.60070(18) 0.0121(6) Uani 1 1 d . . .
C15 C 0.2728(4) 0.0083(2) 0.56064(19) 0.0151(6) Uani 1 1 d . . .
H15 H 0.2715 -0.0526 0.5958 0.018 Uiso 1 1 calc R . .
C16 C 0.2523(4) -0.0130(3) 0.46661(19) 0.0164(6) Uani 1 1 d . . .
H16 H 0.2370 -0.0891 0.4394 0.020 Uiso 1 1 calc R . .
C17 C 0.3541(4) 0.6712(3) 0.52004(19) 0.0226(7) Uani 1 1 d . . .
H17A H 0.4746 0.6928 0.4943 0.034 Uiso 1 1 calc R . .
H17B H 0.3718 0.6694 0.5841 0.034 Uiso 1 1 calc R . .
H17C H 0.2915 0.7285 0.5090 0.034 Uiso 1 1 calc R . .
C18 C 0.2341(4) 0.5487(3) 0.47671(18) 0.0177(6) Uani 1 1 d . . .
H18A H 0.2885 0.4902 0.4965 0.021 Uiso 1 1 calc R . .
H18B H 0.1089 0.5316 0.4990 0.021 Uiso 1 1 calc R . .
C19 C 0.2146(4) 0.5340(3) 0.37374(18) 0.0142(6) Uani 1 1 d . . .
C20 C 0.1277(4) 0.4219(2) 0.32849(18) 0.0155(6) Uani 1 1 d . . .
H20 H 0.0817 0.3581 0.3620 0.019 Uiso 1 1 calc R . .
C21 C 0.1072(4) 0.4020(2) 0.23416(19) 0.0153(6) Uani 1 1 d . . .
H21 H 0.0496 0.3261 0.2051 0.018 Uiso 1 1 calc R . .
C22 C 0.1744(4) 0.4979(2) 0.18460(17) 0.0117(6) Uani 1 1 d . . .
C23 C 0.2595(4) 0.6112(2) 0.22777(18) 0.0145(6) Uani 1 1 d . . .
H23 H 0.3020 0.6752 0.1942 0.017 Uiso 1 1 calc R . .
C24 C 0.2809(4) 0.6283(3) 0.32246(18) 0.0154(6) Uani 1 1 d . . .
H24 H 0.3405 0.7040 0.3514 0.018 Uiso 1 1 calc R . .
C25 C 0.6340(5) 0.4241(3) 0.2734(2) 0.0284(8) Uani 1 1 d . . .
H25A H 0.6916 0.3699 0.2967 0.043 Uiso 1 1 calc R . .
H25B H 0.6363 0.4180 0.2087 0.043 Uiso 1 1 calc R . .
H25C H 0.5057 0.4047 0.2900 0.043 Uiso 1 1 calc R . .
C26 C 0.7412(4) 0.5490(3) 0.31256(18) 0.0215(7) Uani 1 1 d . . .
H26A H 0.6787 0.6021 0.2898 0.026 Uiso 1 1 calc R . .
H26B H 0.8665 0.5698 0.2902 0.026 Uiso 1 1 calc R . .
C27 C 0.7617(4) 0.5719(3) 0.41579(19) 0.0168(6) Uani 1 1 d . . .
C28 C 0.8568(4) 0.6853(3) 0.45711(19) 0.0186(6) Uani 1 1 d . . .
H28 H 0.9089 0.7456 0.4213 0.022 Uiso 1 1 calc R . .
C29 C 0.8757(4) 0.7106(2) 0.55038(19) 0.0166(6) Uani 1 1 d . . .
H29 H 0.9391 0.7871 0.5769 0.020 Uiso 1 1 calc R . .
C30 C 0.7990(4) 0.6203(2) 0.60331(18) 0.0123(6) Uani 1 1 d . . .
C31 C 0.7096(4) 0.5063(2) 0.56440(19) 0.0150(6) Uani 1 1 d . . .
H31 H 0.6628 0.4455 0.6006 0.018 Uiso 1 1 calc R . .
C32 C 0.6897(4) 0.4826(3) 0.4710(2) 0.0186(7) Uani 1 1 d . . .
H32 H 0.6273 0.4058 0.4448 0.022 Uiso 1 1 calc R . .
C33 C 0.6678(4) 0.2735(2) -0.00260(17) 0.0109(5) Uani 1 1 d . . .
C34 C 0.4601(3) 0.2692(2) -0.01664(17) 0.0110(5) Uani 1 1 d . . .
H34 H 0.4300 0.2713 -0.0810 0.013 Uiso 1 1 calc R . .
C35 C 0.3294(4) 0.1559(2) 0.01458(18) 0.0125(5) Uani 1 1 d . . .
H35 H 0.3249 0.0888 -0.0298 0.015 Uiso 1 1 calc R . .
C36 C 0.1315(4) 0.1630(2) 0.02283(17) 0.0107(5) Uani 1 1 d . . .
C37 C 1.1867(4) 0.7733(2) -0.00396(18) 0.0133(6) Uani 1 1 d . . .
C38 C 0.9796(3) 0.7715(2) -0.01731(17) 0.0105(5) Uani 1 1 d . . .
H38 H 0.9491 0.7749 -0.0814 0.013 Uiso 1 1 calc R . .
C39 C 0.8498(4) 0.6563(2) 0.01318(17) 0.0127(6) Uani 1 1 d . . .
H39 H 0.8475 0.5897 -0.0314 0.015 Uiso 1 1 calc R . .
C40 C 0.6506(4) 0.6605(2) 0.02152(18) 0.0119(6) Uani 1 1 d . . .
C41 C 0.3565(4) 0.4677(2) 0.75071(17) 0.0108(5) Uani 1 1 d . . .
C42 C 0.1422(3) 0.4379(2) 0.73262(18) 0.0100(5) Uani 1 1 d . . .
H42 H 0.1014 0.3810 0.6783 0.012 Uiso 1 1 calc R . .
C43 C 0.0387(3) 0.3822(2) 0.81306(17) 0.0102(5) Uani 1 1 d . . .
H43 H 0.0593 0.3053 0.8169 0.012 Uiso 1 1 calc R . .
C44 C -0.1722(4) 0.3598(2) 0.78958(17) 0.0110(5) Uani 1 1 d . . .
C45 C 0.8603(4) 0.9676(2) 0.75006(17) 0.0117(6) Uani 1 1 d . . .
C46 C 0.6468(3) 0.9368(2) 0.73183(18) 0.0118(5) Uani 1 1 d . . .
H46 H 0.6069 0.8799 0.6775 0.014 Uiso 1 1 calc R . .
C47 C 0.5415(4) 0.8807(2) 0.81243(17) 0.0109(5) Uani 1 1 d . . .
H47 H 0.5610 0.8034 0.8164 0.013 Uiso 1 1 calc R . .
C48 C 0.3327(4) 0.8599(2) 0.78777(17) 0.0111(6) Uani 1 1 d . . .
N1 N 0.6674(3) -0.0234(2) 0.08424(14) 0.0130(5) Uani 1 1 d . . .
H1D H 0.7512 -0.0559 0.0618 0.020 Uiso 1 1 calc R . .
H1E H 0.6834 0.0463 0.0631 0.020 Uiso 1 1 calc R . .
H1F H 0.5513 -0.0713 0.0678 0.020 Uiso 1 1 calc R . .
N2 N 0.3146(3) 0.14375(19) 0.69966(14) 0.0111(5) Uani 1 1 d . . .
H2C H 0.3543 0.2216 0.7161 0.017 Uiso 1 1 calc R . .
H2D H 0.3979 0.1113 0.7211 0.017 Uiso 1 1 calc R . .
H2E H 0.2034 0.1117 0.7219 0.017 Uiso 1 1 calc R . .
N3 N 0.8160(3) 0.6445(2) 0.70213(14) 0.0121(5) Uani 1 1 d . . .
H3A H 0.7032 0.6159 0.7238 0.018 Uiso 1 1 calc R . .
H3B H 0.8605 0.7225 0.7177 0.018 Uiso 1 1 calc R . .
H3C H 0.8947 0.6098 0.7249 0.018 Uiso 1 1 calc R . .
N4 N 0.1543(3) 0.4778(2) 0.08564(14) 0.0121(5) Uani 1 1 d . . .
H4A H 0.2385 0.4439 0.0657 0.018 Uiso 1 1 calc R . .
H4B H 0.1737 0.5470 0.0631 0.018 Uiso 1 1 calc R . .
H4C H 0.0385 0.4304 0.0680 0.018 Uiso 1 1 calc R . .
O1 O 0.7125(3) 0.18781(16) -0.04199(13) 0.0169(5) Uani 1 1 d . . .
O2 O 0.7739(3) 0.35920(16) 0.04782(12) 0.0148(4) Uani 1 1 d . . .
O3 O 0.4347(2) 0.37039(15) 0.03398(13) 0.0155(4) Uani 1 1 d . . .
H3 H 0.5329 0.4079 0.0636 0.023 Uiso 1 1 calc R . .
O4 O 0.4009(3) 0.13662(17) 0.09951(12) 0.0178(4) Uani 1 1 d . . .
H4D H 0.3188 0.1287 0.1358 0.027 Uiso 1 1 calc R . .
O5 O 0.0566(2) 0.18522(17) -0.05147(12) 0.0158(4) Uani 1 1 d . . .
H5A H -0.0450 0.1953 -0.0415 0.024 Uiso 1 1 calc R . .
O6 O 0.0562(3) 0.15034(16) 0.09441(12) 0.0190(4) Uani 1 1 d . . .
O7 O 1.2302(3) 0.68915(17) -0.04563(13) 0.0181(5) Uani 1 1 d . . .
O8 O 1.2926(3) 0.85787(16) 0.04745(13) 0.0159(4) Uani 1 1 d . . .
O9 O 0.9547(2) 0.87134(15) 0.03506(12) 0.0149(4) Uani 1 1 d . . .
H9 H 1.0505 0.9053 0.0676 0.022 Uiso 1 1 calc R . .
O10 O 0.9235(3) 0.63813(17) 0.09807(12) 0.0163(4) Uani 1 1 d . . .
H10 H 0.8380 0.6197 0.1323 0.024 Uiso 1 1 calc R . .
O11 O 0.5773(2) 0.68887(17) -0.05064(12) 0.0173(4) Uani 1 1 d . . .
H11 H 0.4690 0.6881 -0.0423 0.026 Uiso 1 1 calc R . .
O12 O 0.5696(3) 0.63732(16) 0.09085(12) 0.0194(5) Uani 1 1 d . . .
O13 O 0.4530(2) 0.57215(15) 0.74714(12) 0.0144(4) Uani 1 1 d . . .
O14 O 0.4174(2) 0.38270(15) 0.76634(12) 0.0150(4) Uani 1 1 d . . .
O15 O 0.0963(2) 0.54134(15) 0.71836(13) 0.0137(4) Uani 1 1 d . . .
H15A H 0.1922 0.5988 0.7251 0.021 Uiso 1 1 calc R . .
O16 O 0.1069(2) 0.45306(15) 0.89547(11) 0.0134(4) Uani 1 1 d . . .
H16A H 0.1110 0.5217 0.8900 0.020 Uiso 1 1 calc R . .
O17 O -0.2428(3) 0.43697(16) 0.83117(13) 0.0135(4) Uani 1 1 d . . .
H17 H -0.3547 0.4205 0.8148 0.020 Uiso 1 1 calc R . .
O18 O -0.2600(3) 0.27975(16) 0.73294(12) 0.0145(4) Uani 1 1 d . . .
O19 O 0.9564(2) 1.07244(15) 0.74521(12) 0.0148(4) Uani 1 1 d . . .
O20 O 0.9225(2) 0.88360(15) 0.76718(13) 0.0155(4) Uani 1 1 d . . .
O21 O 0.5987(2) 1.03966(16) 0.71748(13) 0.0148(4) Uani 1 1 d . . .
H21A H 0.6943 1.0973 0.7228 0.022 Uiso 1 1 calc R . .
O22 O 0.6108(2) 0.95199(15) 0.89428(11) 0.0130(4) Uani 1 1 d . . .
H22 H 0.6048 1.0190 0.8902 0.020 Uiso 1 1 calc R . .
O23 O 0.2610(3) 0.93510(16) 0.83135(13) 0.0150(4) Uani 1 1 d . . .
H23A H 0.1511 0.9216 0.8125 0.022 Uiso 1 1 calc R . .
O24 O 0.2466(3) 0.78215(16) 0.72876(12) 0.0147(4) Uani 1 1 d . . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 115.3(2) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C8 C3 C4 118.3(3) . . ?
C8 C3 C2 122.2(2) . . ?
C4 C3 C2 119.5(3) . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 N1 119.7(2) . . ?
C5 C6 N1 119.5(2) . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C3 C8 C7 121.0(3) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C10 C11 115.4(3) . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C16 C11 C12 117.6(3) . . ?
C16 C11 C10 123.1(3) . . ?
C12 C11 C10 119.3(3) . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 N2 120.2(2) . . ?
C15 C14 N2 118.8(2) . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 122.0(3) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C17 115.3(2) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C24 118.1(2) . . ?
C20 C19 C18 119.1(3) . . ?
C24 C19 C18 122.8(2) . . ?
C19 C20 C21 122.0(3) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 118.6(2) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 N4 120.2(2) . . ?
C21 C22 N4 119.0(2) . . ?
C22 C23 C24 119.4(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C19 C24 C23 121.0(3) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C25 C26 C27 116.1(3) . . ?
C25 C26 H26A 108.3 . . ?
C27 C26 H26A 108.3 . . ?
C25 C26 H26B 108.3 . . ?
C27 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
C28 C27 C32 118.0(3) . . ?
C28 C27 C26 119.6(3) . . ?
C32 C27 C26 122.4(3) . . ?
C29 C28 C27 121.6(3) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C30 C29 C28 118.9(3) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C31 C30 C29 120.8(3) . . ?
C31 C30 N3 119.0(2) . . ?
C29 C30 N3 120.2(2) . . ?
C30 C31 C32 119.6(3) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C31 C32 C27 121.0(3) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
O2 C33 O1 126.5(2) . . ?
O2 C33 C34 116.9(2) . . ?
O1 C33 C34 116.6(2) . . ?
O3 C34 C35 109.8(2) . . ?
O3 C34 C33 108.8(2) . . ?
C35 C34 C33 110.4(2) . . ?
O3 C34 H34 109.2 . . ?
C35 C34 H34 109.2 . . ?
C33 C34 H34 109.2 . . ?
O4 C35 C36 109.4(2) . . ?
O4 C35 C34 109.7(2) . . ?
C36 C35 C34 111.3(2) . . ?
O4 C35 H35 108.8 . . ?
C36 C35 H35 108.8 . . ?
C34 C35 H35 108.8 . . ?
O6 C36 O5 125.4(3) . . ?
O6 C36 C35 120.7(2) . . ?
O5 C36 C35 113.8(2) . . ?
O8 C37 O7 127.0(3) . . ?
O8 C37 C38 116.1(2) . . ?
O7 C37 C38 116.8(2) . . ?
O9 C38 C39 109.9(2) . . ?
O9 C38 C37 109.4(2) . . ?
C39 C38 C37 109.1(2) . . ?
O9 C38 H38 109.5 . . ?
C39 C38 H38 109.5 . . ?
C37 C38 H38 109.5 . . ?
O10 C39 C40 109.6(2) . . ?
O10 C39 C38 108.8(2) . . ?
C40 C39 C38 111.7(2) . . ?
O10 C39 H39 108.9 . . ?
C40 C39 H39 108.9 . . ?
C38 C39 H39 108.9 . . ?
O12 C40 O11 124.9(3) . . ?
O12 C40 C39 120.9(2) . . ?
O11 C40 C39 114.2(2) . . ?
O13 C41 O14 126.4(2) . . ?
O13 C41 C42 116.8(2) . . ?
O14 C41 C42 116.8(2) . . ?
O15 C42 C43 109.5(2) . . ?
O15 C42 C41 110.1(2) . . ?
C43 C42 C41 110.3(2) . . ?
O15 C42 H42 108.9 . . ?
C43 C42 H42 108.9 . . ?
C41 C42 H42 108.9 . . ?
O16 C43 C44 113.9(2) . . ?
O16 C43 C42 112.1(2) . . ?
C44 C43 C42 106.1(2) . . ?
O16 C43 H43 108.2 . . ?
C44 C43 H43 108.2 . . ?
C42 C43 H43 108.2 . . ?
O18 C44 O17 124.2(2) . . ?
O18 C44 C43 121.0(2) . . ?
O17 C44 C43 114.7(2) . . ?
O19 C45 O20 126.3(2) . . ?
O19 C45 C46 116.8(2) . . ?
O20 C45 C46 116.9(2) . . ?
O21 C46 C45 110.3(2) . . ?
O21 C46 C47 109.0(2) . . ?
C45 C46 C47 110.8(2) . . ?
O21 C46 H46 108.9 . . ?
C45 C46 H46 108.9 . . ?
C47 C46 H46 108.9 . . ?
O22 C47 C48 114.5(2) . . ?
O22 C47 C46 111.3(2) . . ?
C48 C47 C46 105.5(2) . . ?
O22 C47 H47 108.4 . . ?
C48 C47 H47 108.4 . . ?
C46 C47 H47 108.4 . . ?
O24 C48 O23 124.4(2) . . ?
O24 C48 C47 120.9(2) . . ?
O23 C48 C47 114.6(2) . . ?
C6 N1 H1D 109.5 . . ?
C6 N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C6 N1 H1F 109.5 . . ?
H1D N1 H1F 109.5 . . ?
H1E N1 H1F 109.5 . . ?
C14 N2 H2C 109.5 . . ?
C14 N2 H2D 109.5 . . ?
H2C N2 H2D 109.5 . . ?
C14 N2 H2E 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C30 N3 H3A 109.5 . . ?
C30 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C30 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C22 N4 H4A 109.5 . . ?
C22 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C22 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C34 O3 H3 109.5 . . ?
C35 O4 H4D 109.5 . . ?
C36 O5 H5A 109.5 . . ?
C38 O9 H9 109.5 . . ?
C39 O10 H10 109.5 . . ?
C40 O11 H11 109.5 . . ?
C42 O15 H15A 109.5 . . ?
C43 O16 H16A 109.5 . . ?
C44 O17 H17 109.5 . . ?
C46 O21 H21A 109.5 . . ?
C47 O22 H22 109.5 . . ?
C48 O23 H23A 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
C1 C2 1.519(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.523(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.388(4) . ?
C3 C4 1.395(4) . ?
C4 C5 1.394(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 N1 1.467(3) . ?
C7 C8 1.398(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.520(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.385(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(4) . ?
C14 N2 1.465(3) . ?
C15 C16 1.393(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.527(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.522(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.389(4) . ?
C19 C24 1.389(4) . ?
C20 C21 1.396(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C22 N4 1.464(3) . ?
C23 C24 1.401(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.507(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.529(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.390(4) . ?
C27 C32 1.390(4) . ?
C28 C29 1.385(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.377(4) . ?
C30 N3 1.465(3) . ?
C31 C32 1.385(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 O2 1.247(3) . ?
C33 O1 1.267(3) . ?
C33 C34 1.542(4) . ?
C34 O3 1.426(3) . ?
C34 C35 1.525(3) . ?
C34 H34 0.9800 . ?
C35 O4 1.420(3) . ?
C35 C36 1.514(4) . ?
C35 H35 0.9800 . ?
C36 O6 1.221(3) . ?
C36 O5 1.306(3) . ?
C37 O8 1.246(3) . ?
C37 O7 1.262(3) . ?
C37 C38 1.545(4) . ?
C38 O9 1.424(3) . ?
C38 C39 1.535(3) . ?
C38 H38 0.9800 . ?
C39 O10 1.421(3) . ?
C39 C40 1.512(4) . ?
C39 H39 0.9800 . ?
C40 O12 1.224(3) . ?
C40 O11 1.306(3) . ?
C41 O13 1.238(3) . ?
C41 O14 1.266(3) . ?
C41 C42 1.538(3) . ?
C42 O15 1.407(3) . ?
C42 C43 1.537(3) . ?
C42 H42 0.9800 . ?
C43 O16 1.406(3) . ?
C43 C44 1.536(3) . ?
C43 H43 0.9800 . ?
C44 O18 1.216(3) . ?
C44 O17 1.311(3) . ?
C45 O19 1.244(3) . ?
C45 O20 1.266(3) . ?
C45 C46 1.531(3) . ?
C46 O21 1.409(3) . ?
C46 C47 1.546(3) . ?
C46 H46 0.9800 . ?
C47 O22 1.403(3) . ?
C47 C48 1.528(4) . ?
C47 H47 0.9800 . ?
C48 O24 1.219(3) . ?
C48 O23 1.311(3) . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N1 H1F 0.8900 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
O3 H3 0.8200 . ?
O4 H4D 0.8200 . ?
O5 H5A 0.8200 . ?
O9 H9 0.8200 . ?
O10 H10 0.8200 . ?
O11 H11 0.8200 . ?
O15 H15A 0.8200 . ?
O16 H16A 0.8200 . ?
O17 H17 0.8200 . ?
O21 H21A 0.8200 . ?
O22 H22 0.8200 . ?
O23 H23A 0.8200 . ?
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
N1 H1D O9 0.89 2.00 2.879(3) 169.5 1_545
N1 H1E O1 0.89 2.37 3.217(3) 159.6 .
N1 H1F O8 0.89 1.86 2.730(3) 166.4 1_445
N2 H2C O14 0.89 1.90 2.784(3) 171.5 .
N2 H2D O21 0.89 1.94 2.781(3) 157.2 1_545
N2 H2E O19 0.89 1.81 2.677(3) 163.5 1_445
N3 H3A O13 0.89 1.83 2.708(3) 167.0 .
N3 H3B O20 0.89 1.90 2.778(3) 169.5 .
N3 H3C O15 0.89 1.92 2.746(3) 153.7 1_655
N4 H4A O3 0.89 1.97 2.860(3) 174.4 .
N4 H4B O7 0.89 2.40 3.250(3) 159.5 1_455
N4 H4B O10 0.89 2.48 2.936(3) 112.4 1_455
N4 H4C O2 0.89 1.90 2.767(3) 165.6 1_455
O3 H3 O2 0.82 2.07 2.579(3) 120.2 .
O3 H3 O12 0.82 2.65 3.051(3) 111.7 .
O4 H4D O6 0.82 2.13 2.627(3) 118.8 .
O5 H5A O1 0.82 1.78 2.587(3) 165.7 1_455
O9 H9 O8 0.82 2.08 2.578(3) 119.3 .
O10 H10 O12 0.82 2.15 2.637(3) 117.8 .
O11 H11 O7 0.82 1.79 2.596(3) 169.6 1_455
O15 H15A O13 0.82 2.09 2.589(2) 119.4 .
O15 H15A O24 0.82 2.09 2.726(3) 134.3 .
O16 H16A O7 0.82 2.05 2.723(3) 139.8 1_456
O17 H17 O14 0.82 1.73 2.548(3) 172.7 1_455
O21 H21A O18 0.82 2.08 2.710(3) 133.2 1_665
O21 H21A O19 0.82 2.09 2.590(2) 119.4 .
O22 H22 O1 0.82 2.07 2.740(3) 138.8 1_566
O23 H23A O20 0.82 1.72 2.540(3) 175.2 1_455
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
C1 C2 C3 C8 1.5(4) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C4 C5 C6 N1 -179.1(2) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
N1 C6 C7 C8 178.9(2) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C2 C3 C8 C7 178.6(3) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C9 C10 C11 C16 -3.2(4) . . . . ?
C9 C10 C11 C12 176.4(3) . . . . ?
C16 C11 C12 C13 -1.5(4) . . . . ?
C10 C11 C12 C13 179.0(3) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C12 C13 C14 N2 -179.8(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
N2 C14 C15 C16 179.3(2) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
C10 C11 C16 C15 -179.5(3) . . . . ?
C14 C15 C16 C11 0.1(4) . . . . ?
C17 C18 C19 C20 172.2(3) . . . . ?
C17 C18 C19 C24 -7.6(4) . . . . ?
C24 C19 C20 C21 0.5(4) . . . . ?
C18 C19 C20 C21 -179.3(3) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C20 C21 C22 N4 179.7(2) . . . . ?
C21 C22 C23 C24 1.3(4) . . . . ?
N4 C22 C23 C24 -178.7(3) . . . . ?
C20 C19 C24 C23 0.5(4) . . . . ?
C18 C19 C24 C23 -179.7(3) . . . . ?
C22 C23 C24 C19 -1.4(4) . . . . ?
C25 C26 C27 C28 -179.2(3) . . . . ?
C25 C26 C27 C32 1.4(4) . . . . ?
C32 C27 C28 C29 -1.8(4) . . . . ?
C26 C27 C28 C29 178.8(3) . . . . ?
C27 C28 C29 C30 0.4(4) . . . . ?
C28 C29 C30 C31 1.8(4) . . . . ?
C28 C29 C30 N3 -179.7(2) . . . . ?
C29 C30 C31 C32 -2.6(4) . . . . ?
N3 C30 C31 C32 178.9(2) . . . . ?
C30 C31 C32 C27 1.2(4) . . . . ?
C28 C27 C32 C31 1.0(4) . . . . ?
C26 C27 C32 C31 -179.6(3) . . . . ?
O2 C33 C34 O3 0.1(3) . . . . ?
O1 C33 C34 O3 178.6(2) . . . . ?
O2 C33 C34 C35 -120.5(2) . . . . ?
O1 C33 C34 C35 58.0(3) . . . . ?
O3 C34 C35 O4 -75.0(3) . . . . ?
C33 C34 C35 O4 45.1(3) . . . . ?
O3 C34 C35 C36 46.2(3) . . . . ?
C33 C34 C35 C36 166.3(2) . . . . ?
O4 C35 C36 O6 -1.4(3) . . . . ?
C34 C35 C36 O6 -122.7(3) . . . . ?
O4 C35 C36 O5 177.6(2) . . . . ?
C34 C35 C36 O5 56.2(3) . . . . ?
O8 C37 C38 O9 -0.3(3) . . . . ?
O7 C37 C38 O9 179.3(2) . . . . ?
O8 C37 C38 C39 -120.6(2) . . . . ?
O7 C37 C38 C39 59.0(3) . . . . ?
O9 C38 C39 O10 -73.7(3) . . . . ?
C37 C38 C39 O10 46.3(3) . . . . ?
O9 C38 C39 C40 47.5(3) . . . . ?
C37 C38 C39 C40 167.4(2) . . . . ?
O10 C39 C40 O12 -7.4(3) . . . . ?
C38 C39 C40 O12 -128.1(3) . . . . ?
O10 C39 C40 O11 173.4(2) . . . . ?
C38 C39 C40 O11 52.7(3) . . . . ?
O13 C41 C42 O15 -2.3(3) . . . . ?
O14 C41 C42 O15 178.8(2) . . . . ?
O13 C41 C42 C43 -123.4(2) . . . . ?
O14 C41 C42 C43 57.8(3) . . . . ?
O15 C42 C43 O16 -68.1(3) . . . . ?
C41 C42 C43 O16 53.3(3) . . . . ?
O15 C42 C43 C44 56.8(3) . . . . ?
C41 C42 C43 C44 178.2(2) . . . . ?
O16 C43 C44 O18 -162.8(2) . . . . ?
C42 C43 C44 O18 73.5(3) . . . . ?
O16 C43 C44 O17 21.0(3) . . . . ?
C42 C43 C44 O17 -102.8(3) . . . . ?
O19 C45 C46 O21 -3.4(3) . . . . ?
O20 C45 C46 O21 177.7(2) . . . . ?
O19 C45 C46 C47 -124.2(2) . . . . ?
O20 C45 C46 C47 56.9(3) . . . . ?
O21 C46 C47 O22 -68.9(3) . . . . ?
C45 C46 C47 O22 52.6(3) . . . . ?
O21 C46 C47 C48 55.9(3) . . . . ?
C45 C46 C47 C48 177.4(2) . . . . ?
O22 C47 C48 O24 -165.6(2) . . . . ?
C46 C47 C48 O24 71.6(3) . . . . ?
O22 C47 C48 O23 17.7(3) . . . . ?
C46 C47 C48 O23 -105.0(3) . . . . ?
