#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009127.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_2009127
loop_
_publ_author_name
'Bouma, B.'
'Kooijman, H.'
'Kroon, J.'
'Grech, E.'
'Brzezinski, B.'
_publ_section_title
;
 1,8-Bis(dimethylaminomethyl)naphthalene bis(squaric acid) dihydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1824
_journal_page_last               1826
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         '2C16 H23 N2 +, C4 O4 2-, 2H2 O'
_chemical_formula_sum            'C36 H50 N4 O6'
_chemical_formula_weight         634.80
_chemical_name_systematic
;
Bis(1-dimethylaminomethyl-8-dimethylammoniomethylnaphthalene)
3,4-dioxocyclobut-1-ene-1,2-diolate dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 101.299(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.361(6)
_cell_length_b                   8.144(4)
_cell_length_c                   20.158(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      19.40
_cell_measurement_theta_min      12.45
_cell_volume                     1668.0(13)
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_collection
'locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  Zr-filter
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6690
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block-shaped
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.177
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(F~o~^2^)+(0.0796P)^2^+0.0235P] where P = (F~o~^2^+2F~c~^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                2610
_reflns_number_total             3819
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    gd1043.cif
_[local]_cod_data_source_block   a038a
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'calc ' changed to
'calc' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009127
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0304(6) 0.0452(7) 0.0503(7) 0.0002(5) 0.0138(5) -0.0042(6)
N2 0.0401(6) 0.0379(7) 0.0380(6) -0.0025(5) 0.0139(5) 0.0002(5)
C1 0.0375(7) 0.0465(8) 0.0324(7) 0.0033(6) 0.0076(5) 0.0024(6)
C2 0.0551(10) 0.0542(10) 0.0467(9) 0.0135(8) 0.0122(7) 0.0117(7)
C3 0.0758(12) 0.0451(9) 0.0485(9) -0.0016(9) 0.0195(8) 0.0141(7)
C4 0.0547(9) 0.0547(10) 0.0368(8) -0.0131(8) 0.0121(7) 0.0056(7)
C5 0.0346(7) 0.0649(11) 0.0388(8) -0.0093(7) 0.0114(6) -0.0024(7)
C6 0.0330(7) 0.0663(11) 0.0514(9) 0.0068(7) 0.0123(6) -0.0023(8)
C7 0.0442(8) 0.0451(8) 0.0459(8) 0.0071(7) 0.0120(6) 0.0009(7)
C8 0.0362(7) 0.0389(8) 0.0321(6) -0.0009(6) 0.0096(5) -0.0039(6)
C9 0.0331(7) 0.0414(8) 0.0255(6) -0.0026(6) 0.0069(5) -0.0023(5)
C10 0.0409(7) 0.0490(9) 0.0250(6) -0.0059(6) 0.0078(5) -0.0009(6)
C11 0.0328(7) 0.0524(9) 0.0444(8) 0.0047(7) 0.0037(6) -0.0016(7)
C12 0.0577(10) 0.0534(10) 0.0633(11) -0.0031(8) 0.0212(8) -0.0145(8)
C13 0.0346(8) 0.0697(12) 0.0860(13) -0.0066(8) 0.0236(8) -0.0081(10)
C14 0.0429(8) 0.0359(7) 0.0411(7) -0.0017(6) 0.0149(6) -0.0039(6)
C15 0.0534(9) 0.0594(11) 0.0395(8) -0.0032(8) 0.0083(7) 0.0000(7)
C16 0.0648(11) 0.0533(10) 0.0599(10) -0.0124(9) 0.0296(9) 0.0048(8)
O1 0.0932(11) 0.0672(9) 0.1058(12) 0.0343(8) 0.0520(10) 0.0058(8)
O2 0.1001(12) 0.1034(12) 0.0772(10) 0.0334(10) 0.0377(9) 0.0478(9)
C17 0.0420(8) 0.0509(9) 0.0479(8) 0.0050(7) 0.0070(6) 0.0072(7)
C18 0.0392(8) 0.0428(8) 0.0559(9) 0.0029(7) 0.0109(7) -0.0022(7)
O3 0.1305(17) 0.1155(16) 0.0793(12) 0.0008(13) 0.0548(12) -0.0129(11)
loop_
_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_occupancy
_atom_site_type_symbol
N1 0.35190(12) -0.04955(17) 0.83365(7) 0.0412(4) Uani 1.000 N
N2 0.19114(12) 0.20131(16) 0.79069(6) 0.0378(4) Uani 1.000 N
C1 0.19702(14) -0.11212(19) 0.91317(7) 0.0387(4) Uani 1.000 C
C2 0.19636(17) -0.2724(2) 0.93441(8) 0.0517(6) Uani 1.000 C
C3 0.08508(19) -0.3508(2) 0.94876(9) 0.0555(6) Uani 1.000 C
C4 -0.02718(16) -0.2647(2) 0.94307(8) 0.0483(5) Uani 1.000 C
C5 -0.15530(14) -0.0165(2) 0.91864(7) 0.0455(5) Uani 1.000 C
C6 -0.16980(15) 0.1405(2) 0.89789(8) 0.0497(5) Uani 1.000 C
C7 -0.06413(14) 0.2204(2) 0.87805(8) 0.0446(5) Uani 1.000 C
C8 0.05650(13) 0.14815(18) 0.88004(7) 0.0353(4) Uani 1.000 C
C9 0.07721(12) -0.01830(18) 0.90406(6) 0.0332(4) Uani 1.000 C
C10 -0.03490(14) -0.09950(19) 0.92150(6) 0.0381(4) Uani 1.000 C
C11 0.33106(13) -0.0500(2) 0.90546(8) 0.0437(5) Uani 1.000 C
C12 0.32236(18) -0.2090(2) 0.79887(10) 0.0569(6) Uani 1.000 C
C13 0.48902(16) -0.0003(2) 0.83211(11) 0.0618(6) Uani 1.000 C
C14 0.15616(14) 0.25624(18) 0.85506(7) 0.0391(4) Uani 1.000 C
C15 0.07573(16) 0.1632(2) 0.73844(8) 0.0509(5) Uani 1.000 C
C16 0.27029(18) 0.3284(2) 0.76577(9) 0.0570(6) Uani 1.000 C
O1 0.36266(16) 0.18832(18) 0.53289(8) 0.0843(6) Uani 1.000 O
O2 0.50304(17) 0.1528(2) 0.40604(8) 0.0908(7) Uani 1.000 O
C17 0.50165(15) 0.0680(2) 0.45753(8) 0.0472(5) Uani 1.000 C
C18 0.43775(15) 0.0851(2) 0.51522(8) 0.0458(5) Uani 1.000 C
O3 0.3388(2) 0.0357(3) 0.65863(10) 0.1038(9) Uani 1.000 O
H1A 0.293(3) 0.035(4) 0.8118(15) 0.0620 Uiso 0.75(4) H
H2 0.27430 -0.33200 0.93950 0.0620 Uiso 1.000 H
H3 0.08860 -0.46040 0.96200 0.0670 Uiso 1.000 H
H4 -0.10130 -0.31490 0.95360 0.0580 Uiso 1.000 H
H5 -0.22560 -0.07110 0.93130 0.0550 Uiso 1.000 H
H6 -0.24900 0.19520 0.89680 0.0600 Uiso 1.000 H
H7 -0.07600 0.32810 0.86270 0.0540 Uiso 1.000 H
H11A 0.34240 0.06100 0.92310 0.0520 Uiso 1.000 H
H11B 0.39820 -0.11800 0.93260 0.0520 Uiso 1.000 H
H12A 0.23500 -0.24300 0.80190 0.0850 Uiso 1.000 H
H12B 0.38450 -0.28980 0.82000 0.0850 Uiso 1.000 H
H12C 0.32840 -0.19770 0.75220 0.0850 Uiso 1.000 H
H13A 0.50920 0.10060 0.85660 0.0930 Uiso 1.000 H
H13B 0.49830 0.01510 0.78610 0.0930 Uiso 1.000 H
H13C 0.54840 -0.08460 0.85270 0.0930 Uiso 1.000 H
H14A 0.12120 0.36690 0.84900 0.0470 Uiso 1.000 H
H14B 0.23570 0.26030 0.88960 0.0470 Uiso 1.000 H
H15A 0.02670 0.07590 0.75390 0.0760 Uiso 1.000 H
H15B 0.10370 0.12980 0.69780 0.0760 Uiso 1.000 H
H15C 0.02110 0.25890 0.72940 0.0760 Uiso 1.000 H
H16A 0.34400 0.35650 0.80080 0.0850 Uiso 1.000 H
H16B 0.21710 0.42420 0.75320 0.0850 Uiso 1.000 H
H16C 0.30150 0.28760 0.72710 0.0850 Uiso 1.000 H
H1B 0.243(9) 0.118(13) 0.797(4) 0.0620 Uiso 0.25(4) H
H3A 0.400(3) -0.032(4) 0.6518(16) 0.1250 Uiso 1.000 H
H3B 0.334(3) 0.112(4) 0.6290(16) 0.1250 Uiso 1.000 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 1 -7
-2 2 1
3 1 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H3A O3 H3B . 107(3) yes
C11 N1 C13 . 109.85(13) no
C12 N1 C13 . 109.74(13) no
C11 N1 C12 . 113.48(13) no
C14 N2 C16 . 109.58(12) no
C15 N2 C16 . 109.60(12) no
C14 N2 C15 . 112.85(12) no
C13 N1 H1A . 108.6(19) no
C11 N1 H1A . 104.1(18) no
C12 N1 H1A . 110.8(18) no
C14 N2 H1B . 111(5) no
C15 N2 H1B . 110(6) no
C16 N2 H1B . 103(6) no
C2 C1 C11 . 114.20(14) no
C9 C1 C11 . 126.53(13) yes
C2 C1 C9 . 119.18(14) no
C1 C2 C3 . 123.60(16) no
C2 C3 C4 . 118.66(15) no
C3 C4 C10 . 121.31(15) no
C6 C5 C10 . 120.84(14) no
C5 C6 C7 . 119.06(15) no
C6 C7 C8 . 123.43(15) no
C9 C8 C14 . 126.26(12) yes
C7 C8 C14 . 114.60(13) no
C7 C8 C9 . 119.14(13) no
C1 C9 C8 . 127.62(12) yes
C1 C9 C10 . 116.26(13) no
C8 C9 C10 . 116.12(12) no
C4 C10 C5 . 117.77(14) no
C4 C10 C9 . 120.91(14) no
C5 C10 C9 . 121.32(14) no
N1 C11 C1 . 114.01(12) yes
N2 C14 C8 . 114.49(12) yes
C3 C2 H2 . 118.19 no
C1 C2 H2 . 118.21 no
C2 C3 H3 . 120.69 no
C4 C3 H3 . 120.65 no
C3 C4 H4 . 119.38 no
C10 C4 H4 . 119.32 no
C10 C5 H5 . 119.56 no
C6 C5 H5 . 119.60 no
C7 C6 H6 . 120.47 no
C5 C6 H6 . 120.47 no
C6 C7 H7 . 118.31 no
C8 C7 H7 . 118.26 no
N1 C11 H11A . 108.69 no
N1 C11 H11B . 108.77 no
C1 C11 H11B . 108.79 no
H11A C11 H11B . 107.66 no
C1 C11 H11A . 108.74 no
N1 C12 H12A . 109.47 no
N1 C12 H12C . 109.48 no
H12A C12 H12B . 109.44 no
N1 C12 H12B . 109.45 no
H12B C12 H12C . 109.51 no
H12A C12 H12C . 109.48 no
N1 C13 H13B . 109.49 no
N1 C13 H13C . 109.45 no
H13A C13 H13B . 109.40 no
H13A C13 H13C . 109.45 no
H13B C13 H13C . 109.53 no
N1 C13 H13A . 109.50 no
N2 C14 H14A . 108.62 no
C8 C14 H14A . 108.63 no
C8 C14 H14B . 108.64 no
H14A C14 H14B . 107.61 no
N2 C14 H14B . 108.63 no
N2 C15 H15B . 109.48 no
N2 C15 H15C . 109.44 no
N2 C15 H15A . 109.45 no
H15A C15 H15C . 109.45 no
H15B C15 H15C . 109.48 no
H15A C15 H15B . 109.53 no
N2 C16 H16A . 109.46 no
N2 C16 H16B . 109.44 no
H16A C16 H16B . 109.45 no
H16A C16 H16C . 109.49 no
N2 C16 H16C . 109.47 no
H16B C16 H16C . 109.53 no
O2 C17 C18 3_656 135.51(16) yes
C18 C17 C18 3_656 90.61(13) no
O2 C17 C18 . 133.88(16) yes
O1 C18 C17 3_656 135.98(16) yes
C17 C18 C17 3_656 89.39(13) no
O1 C18 C17 . 134.63(16) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C18 . 1.244(2) no
O2 C17 . 1.249(2) no
O3 H3A . 0.87(3) no
O3 H3B . 0.86(3) no
N1 C11 . 1.505(2) no
N1 C13 . 1.482(2) no
N1 C12 . 1.479(2) no
N2 C15 . 1.464(2) no
N2 C14 . 1.483(2) no
N2 C16 . 1.469(2) no
N1 H1A . 0.97(3) no
N2 H1B . 0.86(10) no
C1 C11 . 1.514(2) no
C1 C2 . 1.374(2) no
C1 C9 . 1.438(2) no
C2 C3 . 1.397(3) no
C3 C4 . 1.344(3) no
C4 C10 . 1.411(2) no
C5 C6 . 1.345(2) no
C5 C10 . 1.410(2) no
C6 C7 . 1.398(2) no
C7 C8 . 1.375(2) no
C8 C14 . 1.516(2) no
C8 C9 . 1.441(2) no
C9 C10 . 1.439(2) no
C2 H2 . 0.9305 no
C3 H3 . 0.9303 no
C4 H4 . 0.9305 no
C5 H5 . 0.9307 no
C6 H6 . 0.9302 no
C7 H7 . 0.9302 no
C11 H11A . 0.9701 no
C11 H11B . 0.9699 no
C12 H12C . 0.9594 no
C12 H12A . 0.9599 no
C12 H12B . 0.9599 no
C13 H13B . 0.9592 no
C13 H13C . 0.9602 no
C13 H13A . 0.9603 no
C14 H14A . 0.9700 no
C14 H14B . 0.9696 no
C15 H15C . 0.9595 no
C15 H15B . 0.9603 no
C15 H15A . 0.9606 no
C16 H16C . 0.9599 no
C16 H16B . 0.9602 no
C16 H16A . 0.9607 no
C17 C18 3_656 1.454(2) no
C17 C18 . 1.453(2) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O2 3.193(3) . no
O1 O3 2.877(3) . no
O2 C13 3.188(3) 4_554 no
O2 O3 2.753(3) 3_656 no
O2 O1 3.193(3) . no
O2 C16 3.341(3) 4_554 no
O3 C16 3.384(3) . no
O3 C18 3.276(3) . no
O3 O1 2.877(3) . no
O3 C17 3.232(3) 3_656 no
O3 O2 2.753(3) 3_656 no
O1 H11B 2.9044 2_656 no
O1 H5 2.6035 2_556 no
O1 H3B 2.11(3) . no
O1 H4 2.7743 2_556 no
O2 H3B 2.91(3) 3_656 no
O2 H16A 2.4190 4_554 no
O2 H6 2.8905 4_654 no
O2 H13A 2.2485 4_554 no
O2 H14B 2.8148 4_554 no
O2 H3A 1.95(3) 3_656 no
O3 H13B 2.7745 . no
O3 H15B 2.8103 . no
O3 H16C 2.5440 . no
O3 H12C 2.6948 . no
N1 N2 2.671(2) . no
N1 C16 3.407(3) . no
N1 C14 3.293(3) . no
N2 N1 2.671(2) . no
N2 C11 3.214(3) . no
N1 H1B 1.83(10) . no
N2 H1A 1.72(3) . no
C2 C12 3.291(3) . no
C3 C6 3.492(3) 3_557 no
C4 C7 3.562(3) 3_557 no
C4 C6 3.592(3) 3_557 no
C5 C10 3.560(3) 3_557 no
C5 C9 3.518(3) 3_557 no
C6 C3 3.492(3) 3_557 no
C6 C4 3.592(3) 3_557 no
C7 C4 3.562(3) 3_557 no
C7 C15 3.440(3) . no
C9 C5 3.518(3) 3_557 no
C10 C10 3.503(3) 3_557 no
C10 C5 3.560(3) 3_557 no
C11 C14 3.133(3) . no
C11 N2 3.214(3) . no
C12 C2 3.291(3) . no
C13 O2 3.188(3) 4_555 no
C13 C16 3.592(3) . no
C14 C11 3.133(3) . no
C14 N1 3.293(3) . no
C15 C7 3.440(3) . no
C16 O2 3.341(3) 4_555 no
C16 O3 3.384(3) . no
C16 C13 3.592(3) . no
C16 N1 3.407(3) . no
C17 O3 3.232(3) 3_656 no
C18 O3 3.276(3) . no
C1 H12A 2.5822 . no
C2 H12A 2.7878 . no
C4 H15B 2.9237 2_546 no
C4 H3 3.0913 3_547 no
C7 H15A 3.0751 . no
C8 H15A 2.5689 . no
C8 H11A 3.0041 . no
C9 H15A 3.0666 . no
C11 H14B 2.7094 . no
C11 H1B 2.59(9) . no
C12 H1B 2.79(11) . no
C13 H1B 2.69(10) . no
C14 H11A 2.6638 . no
C14 H1A 2.55(3) . no
C15 H1A 2.65(3) . no
C16 H1A 2.56(3) . no
C17 H2 3.0066 4_544 no
C17 H2 2.9107 2_656 no
C17 H3B 3.04(3) 3_656 no
C17 H3A 2.62(3) 3_656 no
C18 H11B 3.0235 2_656 no
C18 H2 3.0204 2_656 no
C18 H3A 3.01(3) . no
C18 H2 2.9041 4_544 no
C18 H3B 2.73(3) . no
H1A N2 1.72(3) . no
H1A C15 2.65(3) . no
H1A C16 2.56(3) . no
H1A C14 2.55(3) . no
H1A H14B 2.5580 . no
H1B C13 2.69(10) . no
H1B H11A 2.5907 . no
H1B C12 2.79(11) . no
H1B N1 1.83(10) . no
H1B C11 2.59(9) . 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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 N1 C11 C1 . . . -175.28(13) no
C12 N1 C11 C1 . . . -52.02(18) no
C15 N2 C14 C8 . . . 48.22(17) no
C16 N2 C14 C8 . . . 170.66(13) no
C2 C1 C9 C8 . . . -177.61(14) no
C9 C1 C11 N1 . . . -83.48(18) yes
C2 C1 C9 C10 . . . 2.97(19) no
C2 C1 C11 N1 . . . 100.07(16) no
C11 C1 C2 C3 . . . 175.92(15) no
C9 C1 C2 C3 . . . -0.8(2) no
C11 C1 C9 C8 . . . 6.1(2) yes
C11 C1 C9 C10 . . . -173.33(13) no
C1 C2 C3 C4 . . . -1.5(3) no
C2 C3 C4 C10 . . . 1.5(2) no
C3 C4 C10 C9 . . . 0.8(2) no
C3 C4 C10 C5 . . . -178.31(15) no
C10 C5 C6 C7 . . . 1.0(2) no
C6 C5 C10 C9 . . . 1.6(2) no
C6 C5 C10 C4 . . . -179.33(14) no
C5 C6 C7 C8 . . . -1.6(2) no
C6 C7 C8 C14 . . . 179.00(14) no
C6 C7 C8 C9 . . . -0.4(2) no
C7 C8 C9 C10 . . . 2.79(19) no
C7 C8 C14 N2 . . . -111.82(15) no
C7 C8 C9 C1 . . . -176.63(14) no
C9 C8 C14 N2 . . . 67.50(18) yes
C14 C8 C9 C1 . . . 4.1(2) yes
C14 C8 C9 C10 . . . -176.51(12) no
C8 C9 C10 C5 . . . -3.44(18) no
C1 C9 C10 C4 . . . -2.99(18) no
C1 C9 C10 C5 . . . 176.05(12) no
C8 C9 C10 C4 . . . 177.52(13) no
O2 C17 C18 O1 . . . 0.5(4) no
O2 C17 C18 C17 . . 3_656 -179.7(2) no
C18 C17 C18 O1 3_656 . . -179.8(2) no
C18 C17 C18 C17 3_656 . 3_656 0.00(13) no
O2 C17 C18 O1 . 3_656 3_656 -0.2(4) no
O2 C17 C18 C17 . 3_656 3_656 179.66(19) no
C18 C17 C18 O1 . 3_656 3_656 -179.8(2) no
C18 C17 C18 C17 . 3_656 3_656 0.00(13) no