##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
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data_global
_audit_creation_method SHELXL-97
_journal_date_recd_electronic 2009-12-06
_journal_date_accepted 2009-12-11
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2010
_journal_volume 66
_journal_issue 1
_journal_page_first o163
_journal_page_last o164
_journal_paper_category QO
_journal_coeditor_code NG2704
_publ_contact_author_name 'Jasinski, Jerry P.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene, New Hampshire 03435, USA
;
_publ_contact_author_email jjasinski@keene.edu
_publ_contact_author_fax ?
_publ_contact_author_phone '603 358-2563'
_publ_section_title
;
Gabapentin-lactum--chloranilic acid (1/1)
;
loop_
_publ_author_name
_publ_author_address
'Jasinski, Jerry P.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
'Butcher, Ray J.'
;
Department of Chemistry
Howard University
525 College Street NW
Washington
DC 20059, USA
;
'Hakim AL-arique, Q. N. M.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
'Yathirajan, H. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
'Narayana, B.'
;
Department of Studies in Chemistry
Mangalore University
Mangalagangotri 574 199, India
;
data_I
_chemical_name_systematic
;
2-azaspiro[4.5]decan-3-one--chloranilic acid (1/1)
;
_chemical_name_common
;
Gabapentin-lactum--chloranilic acid (1/1)
;
_chemical_formula_moiety 'C9 H15 N O, C6 H2 Cl2 O4'
_chemical_formula_sum 'C15 H17 Cl2 N O5'
_chemical_formula_iupac 'C9 H15 N O, C6 H2 Cl2 O4'
_chemical_formula_weight 362.20
_chemical_melting_point ?
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 6.6127(9)
_cell_length_b 9.5800(11)
_cell_length_c 13.0724(13)
_cell_angle_alpha 102.679(9)
_cell_angle_beta 91.934(9)
_cell_angle_gamma 98.481(10)
_cell_volume 797.23(16)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3438
_cell_measurement_theta_min 4.7637
_cell_measurement_theta_max 73.9570
_cell_measurement_temperature 110(2)
_exptl_crystal_description 'irregular plate'
_exptl_crystal_colour 'red-brown'
_exptl_crystal_size_max 0.47
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.15
_exptl_crystal_density_diffrn 1.509
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 376
_exptl_absorpt_coefficient_mu 3.897
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_absorpt_correction_T_min 0.200
_exptl_absorpt_correction_T_max 0.557
_exptl_special_details
;
;
_diffrn_ambient_temperature 110(2)
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator 'graphite'
_diffrn_measurement_device_type
;
Goniometer Xcalibur diffractometer with a Ruby (Gemini Cu) detector
;
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 10.5081
_diffrn_reflns_number 5138
_diffrn_reflns_av_R_equivalents 0.0250
_diffrn_reflns_av_sigmaI/netI 0.0245
_diffrn_reflns_theta_min 4.79
_diffrn_reflns_theta_max 74.15
_diffrn_reflns_theta_full 67.50
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% <2%
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 3123
_reflns_number_gt 2731
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0472
_refine_ls_R_factor_gt 0.0422
_refine_ls_wR_factor_gt 0.1154
_refine_ls_wR_factor_ref 0.1190
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_refine_ls_number_reflns 3123
_refine_ls_number_parameters 210
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.4046P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.447
_refine_diff_density_min -0.396
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0181 0.0091
'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' 0.0311 0.0180
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0492 0.0322
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.3639 0.7018
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction 'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.07819(8) 0.35536(5) 0.25360(3) 0.02058(15) Uani d . 1 . .
Cl Cl2 0.30441(7) 0.39346(5) 0.73387(3) 0.01894(15) Uani d . 1 . .
O O1A 0.0035(2) 0.11592(14) 0.36708(11) 0.0185(3) Uani d . 1 . .
H H1A -0.0101 0.0550 0.4048 0.022 Uiso calc R 1 . .
O O2A 0.1030(2) 0.13961(14) 0.57058(11) 0.0198(3) Uani d . 1 . .
O O3A 0.3781(2) 0.63101(14) 0.62265(11) 0.0168(3) Uani d . 1 . .
H H3A 0.3800 0.6958 0.5885 0.020 Uiso calc R 1 . .
O O4A 0.2633(2) 0.61192(14) 0.41806(11) 0.0174(3) Uani d . 1 . .
C C1A 0.1342(3) 0.3619(2) 0.38385(15) 0.0142(4) Uani d . 1 . .
C C2A 0.0914(3) 0.2440(2) 0.42497(15) 0.0149(4) Uani d . 1 . .
C C3A 0.1454(3) 0.25105(19) 0.53885(15) 0.0142(4) Uani d . 1 . .
C C4A 0.2436(3) 0.3875(2) 0.60388(14) 0.0139(4) Uani d . 1 . .
C C5A 0.2870(3) 0.50807(19) 0.56472(15) 0.0134(4) Uani d . 1 . .
C C6A 0.2301(3) 0.50147(19) 0.45017(15) 0.0132(4) Uani d . 1 . .
O O1B 0.5433(2) 1.13507(14) 0.43096(11) 0.0189(3) Uani d . 1 . .
C C1B 0.4590(3) 1.03933(19) 0.35294(15) 0.0147(4) Uani d . 1 . .
N N2B 0.3806(3) 0.90640(16) 0.35775(12) 0.0158(3) Uani d . 1 . .
H H2BA 0.3923 0.8731 0.4149 0.019 Uiso calc R 1 . .
C C3B 0.2729(3) 0.8193(2) 0.26005(14) 0.0163(4) Uani d . 1 . .
H H3BA 0.1226 0.8081 0.2654 0.020 Uiso calc R 1 . .
H H3BB 0.3141 0.7220 0.2424 0.020 Uiso calc R 1 . .
C C4B 0.3395(3) 0.90694(19) 0.17620(14) 0.0155(4) Uani d . 1 . .
C C5B 0.1561(3) 0.9111(2) 0.10248(16) 0.0214(4) Uani d . 1 . .
H H5BA 0.0461 0.9484 0.1448 0.026 Uiso calc R 1 . .
H H5BB 0.1986 0.9785 0.0568 0.026 Uiso calc R 1 . .
C C6B 0.0727(4) 0.7610(2) 0.03391(17) 0.0288(5) Uani d . 1 . .
H H6BA 0.0190 0.6956 0.0791 0.035 Uiso calc R 1 . .
H H6BB -0.0418 0.7686 -0.0143 0.035 Uiso calc R 1 . .
C C7B 0.2397(4) 0.6977(3) -0.02991(17) 0.0320(5) Uani d . 1 . .
H H7BA 0.2827 0.7577 -0.0805 0.038 Uiso calc R 1 . .
H H7BB 0.1841 0.5986 -0.0705 0.038 Uiso calc R 1 . .
C C8B 0.4253(4) 0.6919(2) 0.04056(17) 0.0278(5) Uani d . 1 . .
H H8BA 0.5350 0.6579 -0.0036 0.033 Uiso calc R 1 . .
H H8BB 0.3866 0.6216 0.0847 0.033 Uiso calc R 1 . .
C C9B 0.5062(3) 0.8409(2) 0.11141(16) 0.0198(4) Uani d . 1 . .
H H9BA 0.5625 0.9073 0.0674 0.024 Uiso calc R 1 . .
H H9BB 0.6193 0.8318 0.1598 0.024 Uiso calc R 1 . .
C C10B 0.4297(3) 1.0593(2) 0.24256(15) 0.0175(4) Uani d . 1 . .
H H10A 0.5621 1.0955 0.2170 0.021 Uiso calc R 1 . .
H H10B 0.3340 1.1288 0.2394 0.021 Uiso calc R 1 . .
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
Cl1 0.0306(3) 0.0172(2) 0.0145(2) 0.00588(19) -0.00172(18) 0.00410(18)
Cl2 0.0277(3) 0.0151(2) 0.0153(2) 0.00428(18) -0.00131(18) 0.00606(17)
O1A 0.0265(7) 0.0099(6) 0.0176(7) -0.0005(5) 0.0004(6) 0.0026(5)
O2A 0.0281(8) 0.0111(6) 0.0211(7) 0.0016(6) 0.0049(6) 0.0057(5)
O3A 0.0228(7) 0.0093(6) 0.0179(7) -0.0007(5) -0.0029(5) 0.0048(5)
O4A 0.0214(7) 0.0131(7) 0.0194(7) 0.0022(5) 0.0020(5) 0.0076(5)
C1A 0.0154(9) 0.0149(9) 0.0141(9) 0.0062(7) 0.0023(7) 0.0042(7)
C2A 0.0144(9) 0.0112(8) 0.0183(9) 0.0032(7) 0.0023(7) 0.0008(7)
C3A 0.0154(9) 0.0107(9) 0.0184(9) 0.0048(7) 0.0048(7) 0.0047(7)
C4A 0.0168(9) 0.0125(9) 0.0138(9) 0.0051(7) 0.0017(7) 0.0042(7)
C5A 0.0112(9) 0.0113(9) 0.0184(9) 0.0036(7) 0.0014(7) 0.0037(7)
C6A 0.0122(8) 0.0108(9) 0.0179(9) 0.0043(7) 0.0027(7) 0.0044(7)
O1B 0.0276(8) 0.0112(6) 0.0166(7) -0.0010(5) -0.0015(6) 0.0036(5)
C1B 0.0170(9) 0.0110(8) 0.0166(9) 0.0029(7) 0.0014(7) 0.0037(7)
N2B 0.0236(8) 0.0109(7) 0.0130(8) 0.0012(6) -0.0001(6) 0.0044(6)
C3B 0.0245(10) 0.0116(8) 0.0123(9) 0.0004(7) 0.0009(7) 0.0032(7)
C4B 0.0224(10) 0.0106(9) 0.0138(9) 0.0024(7) 0.0013(7) 0.0038(7)
C5B 0.0251(10) 0.0216(10) 0.0192(10) 0.0078(8) -0.0004(8) 0.0058(8)
C6B 0.0350(12) 0.0279(12) 0.0208(10) 0.0012(9) -0.0075(9) 0.0034(9)
C7B 0.0492(15) 0.0252(11) 0.0174(10) 0.0041(10) -0.0010(10) -0.0022(8)
C8B 0.0413(13) 0.0195(10) 0.0229(10) 0.0115(9) 0.0078(9) 0.0002(8)
C9B 0.0245(10) 0.0173(9) 0.0193(9) 0.0054(8) 0.0042(8) 0.0060(8)
C10B 0.0268(10) 0.0112(9) 0.0155(9) 0.0030(7) 0.0024(8) 0.0049(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
Cl1 C1A . 1.7158(19) ?
Cl2 C4A . 1.7196(18) ?
O1A C2A . 1.330(2) ?
O1A H1A . 0.8400 ?
O2A C3A . 1.227(2) ?
O3A C5A . 1.301(2) ?
O3A H3A . 0.8400 ?
O4A C6A . 1.215(2) ?
C1A C2A . 1.352(3) ?
C1A C6A . 1.465(3) ?
C2A C3A . 1.504(3) ?
C3A C4A . 1.441(3) ?
C4A C5A . 1.361(3) ?
C5A C6A . 1.517(3) ?
O1B C1B . 1.262(2) ?
C1B N2B . 1.318(2) ?
C1B C10B . 1.507(2) ?
N2B C3B . 1.460(2) ?
N2B H2BA . 0.8800 ?
C3B C4B . 1.558(2) ?
C3B H3BA . 0.9900 ?
C3B H3BB . 0.9900 ?
C4B C5B . 1.534(3) ?
C4B C9B . 1.538(3) ?
C4B C10B . 1.546(2) ?
C5B C6B . 1.530(3) ?
C5B H5BA . 0.9900 ?
C5B H5BB . 0.9900 ?
C6B C7B . 1.523(3) ?
C6B H6BA . 0.9900 ?
C6B H6BB . 0.9900 ?
C7B C8B . 1.525(3) ?
C7B H7BA . 0.9900 ?
C7B H7BB . 0.9900 ?
C8B C9B . 1.531(3) ?
C8B H8BA . 0.9900 ?
C8B H8BB . 0.9900 ?
C9B H9BA . 0.9900 ?
C9B H9BB . 0.9900 ?
C10B H10A . 0.9900 ?
C10B H10B . 0.9900 ?
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_3
_geom_angle
_geom_angle_publ_flag
C2A O1A H1A . . 109.5 ?
C5A O3A H3A . . 109.5 ?
C2A C1A C6A . . 120.62(17) ?
C2A C1A Cl1 . . 121.97(15) ?
C6A C1A Cl1 . . 117.41(14) ?
O1A C2A C1A . . 122.13(17) ?
O1A C2A C3A . . 116.63(16) ?
C1A C2A C3A . . 121.23(16) ?
O2A C3A C4A . . 124.02(17) ?
O2A C3A C2A . . 117.66(17) ?
C4A C3A C2A . . 118.32(16) ?
C5A C4A C3A . . 121.67(17) ?
C5A C4A Cl2 . . 120.66(14) ?
C3A C4A Cl2 . . 117.67(14) ?
O3A C5A C4A . . 121.97(17) ?
O3A C5A C6A . . 118.01(16) ?
C4A C5A C6A . . 120.03(16) ?
O4A C6A C1A . . 123.11(17) ?
O4A C6A C5A . . 118.78(16) ?
C1A C6A C5A . . 118.10(15) ?
O1B C1B N2B . . 123.96(17) ?
O1B C1B C10B . . 125.82(16) ?
N2B C1B C10B . . 110.21(16) ?
C1B N2B C3B . . 114.19(15) ?
C1B N2B H2BA . . 122.9 ?
C3B N2B H2BA . . 122.9 ?
N2B C3B C4B . . 104.11(15) ?
N2B C3B H3BA . . 110.9 ?
C4B C3B H3BA . . 110.9 ?
N2B C3B H3BB . . 110.9 ?
C4B C3B H3BB . . 110.9 ?
H3BA C3B H3BB . . 109.0 ?
C5B C4B C9B . . 109.57(15) ?
C5B C4B C10B . . 111.96(15) ?
C9B C4B C10B . . 109.81(16) ?
C5B C4B C3B . . 111.08(16) ?
C9B C4B C3B . . 110.64(15) ?
C10B C4B C3B . . 103.66(14) ?
C6B C5B C4B . . 111.76(17) ?
C6B C5B H5BA . . 109.3 ?
C4B C5B H5BA . . 109.3 ?
C6B C5B H5BB . . 109.3 ?
C4B C5B H5BB . . 109.3 ?
H5BA C5B H5BB . . 107.9 ?
C7B C6B C5B . . 110.90(19) ?
C7B C6B H6BA . . 109.5 ?
C5B C6B H6BA . . 109.5 ?
C7B C6B H6BB . . 109.5 ?
C5B C6B H6BB . . 109.5 ?
H6BA C6B H6BB . . 108.0 ?
C6B C7B C8B . . 111.52(18) ?
C6B C7B H7BA . . 109.3 ?
C8B C7B H7BA . . 109.3 ?
C6B C7B H7BB . . 109.3 ?
C8B C7B H7BB . . 109.3 ?
H7BA C7B H7BB . . 108.0 ?
C7B C8B C9B . . 111.18(17) ?
C7B C8B H8BA . . 109.4 ?
C9B C8B H8BA . . 109.4 ?
C7B C8B H8BB . . 109.4 ?
C9B C8B H8BB . . 109.4 ?
H8BA C8B H8BB . . 108.0 ?
C8B C9B C4B . . 112.62(17) ?
C8B C9B H9BA . . 109.1 ?
C4B C9B H9BA . . 109.1 ?
C8B C9B H9BB . . 109.1 ?
C4B C9B H9BB . . 109.1 ?
H9BA C9B H9BB . . 107.8 ?
C1B C10B C4B . . 105.01(15) ?
C1B C10B H10A . . 110.7 ?
C4B C10B H10A . . 110.7 ?
C1B C10B H10B . . 110.7 ?
C4B C10B H10B . . 110.7 ?
H10A C10B H10B . . 108.8 ?
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
C6A C1A C2A O1A . . . . 179.69(16) ?
Cl1 C1A C2A O1A . . . . 0.0(3) ?
C6A C1A C2A C3A . . . . -1.6(3) ?
Cl1 C1A C2A C3A . . . . 178.76(13) ?
O1A C2A C3A O2A . . . . -0.8(3) ?
C1A C2A C3A O2A . . . . -179.58(18) ?
O1A C2A C3A C4A . . . . 179.11(16) ?
C1A C2A C3A C4A . . . . 0.3(3) ?
O2A C3A C4A C5A . . . . -179.95(18) ?
C2A C3A C4A C5A . . . . 0.2(3) ?
O2A C3A C4A Cl2 . . . . 0.0(3) ?
C2A C3A C4A Cl2 . . . . -179.94(13) ?
C3A C4A C5A O3A . . . . -179.05(16) ?
Cl2 C4A C5A O3A . . . . 1.1(3) ?
C3A C4A C5A C6A . . . . 0.6(3) ?
Cl2 C4A C5A C6A . . . . -179.28(13) ?
C2A C1A C6A O4A . . . . -176.63(18) ?
Cl1 C1A C6A O4A . . . . 3.0(3) ?
C2A C1A C6A C5A . . . . 2.3(3) ?
Cl1 C1A C6A C5A . . . . -178.02(13) ?
O3A C5A C6A O4A . . . . -3.2(3) ?
C4A C5A C6A O4A . . . . 177.16(17) ?
O3A C5A C6A C1A . . . . 177.86(15) ?
C4A C5A C6A C1A . . . . -1.8(3) ?
O1B C1B N2B C3B . . . . 174.06(18) ?
C10B C1B N2B C3B . . . . -5.0(2) ?
C1B N2B C3B C4B . . . . 14.0(2) ?
N2B C3B C4B C5B . . . . -136.89(16) ?
N2B C3B C4B C9B . . . . 101.19(17) ?
N2B C3B C4B C10B . . . . -16.48(19) ?
C9B C4B C5B C6B . . . . 55.7(2) ?
C10B C4B C5B C6B . . . . 177.77(17) ?
C3B C4B C5B C6B . . . . -66.9(2) ?
C4B C5B C6B C7B . . . . -57.1(2) ?
C5B C6B C7B C8B . . . . 55.9(2) ?
C6B C7B C8B C9B . . . . -54.4(3) ?
C7B C8B C9B C4B . . . . 54.4(2) ?
C5B C4B C9B C8B . . . . -54.5(2) ?
C10B C4B C9B C8B . . . . -177.91(16) ?
C3B C4B C9B C8B . . . . 68.3(2) ?
O1B C1B C10B C4B . . . . 174.58(18) ?
N2B C1B C10B C4B . . . . -6.4(2) ?
C5B C4B C10B C1B . . . . 133.80(17) ?
C9B C4B C10B C1B . . . . -104.25(17) ?
C3B C4B C10B C1B . . . . 13.99(19) ?
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
O1A H1A O2A 2_556 0.84 1.97 2.7493(19) 153.1
O1A H1A O2A . 0.84 2.20 2.671(2) 115.2
O3A H3A O1B 2_676 0.84 1.70 2.4807(19) 153.4
O3A H3A O4A . 0.84 2.26 2.7148(19) 114.0
N2B H2BA O1B 2_676 0.88 2.07 2.913(2) 161.3
N2B H2BA O4A . 0.88 2.53 3.091(2) 122.2