##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-05-03
_journal_date_accepted     2011-05-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      6
_journal_page_first     o1345
_journal_page_last     o1345
_journal_paper_category     QO
_journal_coeditor_code     XU5205
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Rauniticine-allo-oxindole B methanol monosolvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Salim, Fatimah'
;
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam
     Selangor
     Malaysia
;
    'Ahmad, Rohaya'
;
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam
     Selangor
     Malaysia
;
    'Ismail, Nor Hadiani'
;
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam
     Selangor
     Malaysia
;
    'Hazni, Hazrina'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-oxo-1,2,2',3',5',5'a,6',9'a,10',10'a-decahydrospiro[indole-3,1'-
pyrano[3,4-f]indolizine]-9'-carboxylic acid methanol monosolvate
;
_chemical_name_common
;
Rauniticine-allo-oxindole B methanol monosolvate
;
_chemical_formula_moiety     'C20 H22 N2 O4, C H4 O'
_chemical_formula_sum     'C21 H26 N2 O5'
_chemical_formula_iupac     'C20 H22 N2 O4, C H4 O'
_chemical_formula_weight     386.44
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.2330(3)
_cell_length_b     7.2110(2)
_cell_length_c     14.7678(4)
_cell_angle_alpha     90.00
_cell_angle_beta     99.313(3)
_cell_angle_gamma     90.00
_cell_volume     970.27(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4552
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     29.2
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.323
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     412
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2010)'
_exptl_absorpt_correction_T_min     0.9813
_exptl_absorpt_correction_T_max     0.9953
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                  'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     9109
_diffrn_reflns_av_R_equivalents     0.0393
_diffrn_reflns_av_sigmaI/netI     0.0362
_diffrn_reflns_theta_min     2.44
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2381
_reflns_number_gt     2181
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0435
_refine_ls_R_factor_gt     0.0374
_refine_ls_wR_factor_gt     0.0882
_refine_ls_wR_factor_ref     0.0927
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     2381
_refine_ls_number_parameters     266
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0455P)²+0.2288P] where P=(Fo²+2Fc²)/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     0.001
_refine_diff_density_max     0.205
_refine_diff_density_min     -0.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.30437(18) 1.0011(3) 0.98971(12) 0.0253(4) Uani d D 1 1 . .
    O O2 1.06782(16) 0.9207(3) 0.96906(11) 0.0226(4) Uani d . 1 1 . .
    O O3 1.42440(17) 0.5574(3) 0.85208(12) 0.0257(4) Uani d . 1 1 . .
    O O4 1.04085(17) 0.6078(3) 0.54863(11) 0.0214(4) Uani d . 1 1 . .
    O O5 1.20768(17) 1.2803(3) 1.08162(11) 0.0233(4) Uani d D 1 1 . .
    N N1 0.9975(2) 0.3485(3) 0.71523(12) 0.0181(4) Uani d . 1 1 . .
    N N2 0.8390(2) 0.7963(3) 0.52546(13) 0.0204(4) Uani d D 1 1 . .
    C C1 1.1933(2) 0.8909(3) 0.95551(14) 0.0180(5) Uani d . 1 1 . .
    C C2 1.2329(2) 0.7332(4) 0.90209(15) 0.0180(5) Uani d . 1 1 . .
    C C3 1.3739(2) 0.6984(4) 0.89692(15) 0.0224(5) Uani d . 1 1 . .
    H H3 1.4447 0.7818 0.9280 0.027 Uiso calc R 1 1 . .
    C C4 1.3173(3) 0.4343(4) 0.79913(16) 0.0218(5) Uani d . 1 1 . .
    H H4 1.2837 0.4902 0.7373 0.026 Uiso calc R 1 1 . .
    C C5 1.3986(3) 0.2554(4) 0.7878(2) 0.0339(6) Uani d . 1 1 . .
    H H5A 1.4810 0.2807 0.7553 0.051 Uiso calc R 1 1 . .
    H H5B 1.3316 0.1667 0.7525 0.051 Uiso calc R 1 1 . .
    H H5C 1.4359 0.2032 0.8484 0.051 Uiso calc R 1 1 . .
    C C6 1.1853(2) 0.4113(4) 0.84882(15) 0.0188(5) Uani d . 1 1 . .
    H H6 1.2229 0.3627 0.9117 0.023 Uiso calc R 1 1 . .
    C C9 1.0709(2) 0.2749(4) 0.80272(15) 0.0200(5) Uani d . 1 1 . .
    H H9A 1.1188 0.1557 0.7924 0.024 Uiso calc R 1 1 . .
    H H9B 0.9975 0.2512 0.8433 0.024 Uiso calc R 1 1 . .
    C C10 0.9215(2) 0.5222(3) 0.72771(15) 0.0163(5) Uani d . 1 1 . .
    H H10 0.8512 0.4990 0.7713 0.020 Uiso calc R 1 1 . .
    C C11 1.0279(2) 0.6712(3) 0.76820(14) 0.0168(5) Uani d . 1 1 . .
    H H11A 0.9735 0.7855 0.7786 0.020 Uiso calc R 1 1 . .
    H H11B 1.0963 0.7006 0.7251 0.020 Uiso calc R 1 1 . .
    C C12 1.1150(2) 0.6013(3) 0.86019(15) 0.0164(5) Uani d . 1 1 . .
    H H12 1.0443 0.5862 0.9043 0.020 Uiso calc R 1 1 . .
    C C13 0.8837(3) 0.2265(4) 0.66791(16) 0.0229(5) Uani d . 1 1 . .
    H H13A 0.8237 0.1735 0.7114 0.028 Uiso calc R 1 1 . .
    H H13B 0.9272 0.1239 0.6368 0.028 Uiso calc R 1 1 . .
    C C14 0.7913(3) 0.3531(4) 0.59816(15) 0.0201(5) Uani d . 1 1 . .
    H H14A 0.6853 0.3293 0.5968 0.024 Uiso calc R 1 1 . .
    H H14B 0.8151 0.3324 0.5359 0.024 Uiso calc R 1 1 . .
    C C15 0.8317(2) 0.5561(3) 0.63129(15) 0.0167(5) Uani d . 1 1 . .
    C C16 0.9193(2) 0.6518(3) 0.56509(15) 0.0179(5) Uani d . 1 1 . .
    C C17 0.7091(2) 0.8212(4) 0.56293(15) 0.0189(5) Uani d . 1 1 . .
    C C18 0.6022(2) 0.9545(4) 0.54169(16) 0.0223(5) Uani d . 1 1 . .
    H H18 0.6081 1.0452 0.4958 0.027 Uiso calc R 1 1 . .
    C C19 0.4849(3) 0.9504(4) 0.59050(16) 0.0242(5) Uani d . 1 1 . .
    H H19 0.4095 1.0408 0.5780 0.029 Uiso calc R 1 1 . .
    C C20 0.4765(2) 0.8163(4) 0.65720(16) 0.0239(5) Uani d . 1 1 . .
    H H20 0.3963 0.8172 0.6902 0.029 Uiso calc R 1 1 . .
    C C21 0.5849(2) 0.6802(4) 0.67598(15) 0.0205(5) Uani d . 1 1 . .
    H H21 0.5786 0.5875 0.7209 0.025 Uiso calc R 1 1 . .
    C C22 0.7016(2) 0.6830(3) 0.62794(14) 0.0165(5) Uani d . 1 1 . .
    C C23 1.2794(3) 1.4465(4) 1.11555(17) 0.0266(6) Uani d . 1 1 . .
    H H23A 1.2064 1.5366 1.1290 0.040 Uiso calc R 1 1 . .
    H H23B 1.3332 1.4979 1.0693 0.040 Uiso calc R 1 1 . .
    H H23C 1.3483 1.4195 1.1718 0.040 Uiso calc R 1 1 . .
    H H1 1.273(3) 1.083(4) 1.0219(19) 0.041(9) Uiso d D 1 1 . .
    H H5 1.1180(14) 1.304(5) 1.065(2) 0.043(9) Uiso d D 1 1 . .
    H H2 0.870(3) 0.878(3) 0.4885(16) 0.034(8) Uiso d D 1 1 . .
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 C1 . 1.331(3) ?
    O1 H1 . 0.84(3) ?
    O2 C1 . 1.227(3) ?
    O3 C3 . 1.338(3) ?
    O3 C4 . 1.458(3) ?
    O4 C16 . 1.228(3) ?
    O5 C23 . 1.421(3) ?
    O5 H5 . 0.84(3) ?
    N1 C9 . 1.458(3) ?
    N1 C13 . 1.459(3) ?
    N1 C10 . 1.462(3) ?
    N2 C16 . 1.356(3) ?
    N2 C17 . 1.411(3) ?
    N2 H2 . 0.88(3) ?
    C1 C2 . 1.464(3) ?
    C2 C3 . 1.340(3) ?
    C2 C12 . 1.502(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.515(4) ?
    C4 C6 . 1.530(3) ?
    C4 H4 . 1.0000 ?
    C5 H5A . 0.9800 ?
    C5 H5B . 0.9800 ?
    C5 H5C . 0.9800 ?
    C6 C9 . 1.522(3) ?
    C6 C12 . 1.537(3) ?
    C6 H6 . 1.0000 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.512(3) ?
    C10 C15 . 1.547(3) ?
    C10 H10 . 1.0000 ?
    C11 C12 . 1.547(3) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.529(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.569(3) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C22 . 1.505(3) ?
    C15 C16 . 1.530(3) ?
    C17 C18 . 1.377(3) ?
    C17 C22 . 1.393(3) ?
    C18 C19 . 1.395(3) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.392(4) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.397(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.383(3) ?
    C21 H21 . 0.9500 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
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
    C1 O1 H1 . . 109(2) ?
    C3 O3 C4 . . 117.88(17) ?
    C23 O5 H5 . . 108(3) ?
    C9 N1 C13 . . 113.6(2) ?
    C9 N1 C10 . . 111.33(18) ?
    C13 N1 C10 . . 104.68(17) ?
    C16 N2 C17 . . 111.6(2) ?
    C16 N2 H2 . . 125(2) ?
    C17 N2 H2 . . 122(2) ?
    O2 C1 O1 . . 121.6(2) ?
    O2 C1 C2 . . 123.3(2) ?
    O1 C1 C2 . . 115.10(19) ?
    C3 C2 C1 . . 120.4(2) ?
    C3 C2 C12 . . 120.3(2) ?
    C1 C2 C12 . . 119.10(19) ?
    O3 C3 C2 . . 126.2(2) ?
    O3 C3 H3 . . 116.9 ?
    C2 C3 H3 . . 116.9 ?
    O3 C4 C5 . . 105.80(19) ?
    O3 C4 C6 . . 109.42(18) ?
    C5 C4 C6 . . 114.1(2) ?
    O3 C4 H4 . . 109.1 ?
    C5 C4 H4 . . 109.1 ?
    C6 C4 H4 . . 109.1 ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C9 C6 C4 . . 113.91(19) ?
    C9 C6 C12 . . 110.48(18) ?
    C4 C6 C12 . . 109.8(2) ?
    C9 C6 H6 . . 107.5 ?
    C4 C6 H6 . . 107.5 ?
    C12 C6 H6 . . 107.5 ?
    N1 C9 C6 . . 110.5(2) ?
    N1 C9 H9A . . 109.5 ?
    C6 C9 H9A . . 109.5 ?
    N1 C9 H9B . . 109.5 ?
    C6 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 108.1 ?
    N1 C10 C11 . . 111.33(17) ?
    N1 C10 C15 . . 102.46(18) ?
    C11 C10 C15 . . 117.98(19) ?
    N1 C10 H10 . . 108.2 ?
    C11 C10 H10 . . 108.2 ?
    C15 C10 H10 . . 108.2 ?
    C10 C11 C12 . . 109.15(19) ?
    C10 C11 H11A . . 109.8 ?
    C12 C11 H11A . . 109.8 ?
    C10 C11 H11B . . 109.8 ?
    C12 C11 H11B . . 109.8 ?
    H11A C11 H11B . . 108.3 ?
    C2 C12 C6 . . 108.58(17) ?
    C2 C12 C11 . . 113.2(2) ?
    C6 C12 C11 . . 111.30(19) ?
    C2 C12 H12 . . 107.8 ?
    C6 C12 H12 . . 107.8 ?
    C11 C12 H12 . . 107.8 ?
    N1 C13 C14 . . 104.1(2) ?
    N1 C13 H13A . . 110.9 ?
    C14 C13 H13A . . 110.9 ?
    N1 C13 H13B . . 110.9 ?
    C14 C13 H13B . . 110.9 ?
    H13A C13 H13B . . 109.0 ?
    C13 C14 C15 . . 105.55(18) ?
    C13 C14 H14A . . 110.6 ?
    C15 C14 H14A . . 110.6 ?
    C13 C14 H14B . . 110.6 ?
    C15 C14 H14B . . 110.6 ?
    H14A C14 H14B . . 108.8 ?
    C22 C15 C16 . . 101.90(19) ?
    C22 C15 C10 . . 115.61(18) ?
    C16 C15 C10 . . 113.55(18) ?
    C22 C15 C14 . . 114.13(18) ?
    C16 C15 C14 . . 110.19(18) ?
    C10 C15 C14 . . 101.82(18) ?
    O4 C16 N2 . . 124.5(2) ?
    O4 C16 C15 . . 127.2(2) ?
    N2 C16 C15 . . 108.30(19) ?
    C18 C17 C22 . . 122.9(2) ?
    C18 C17 N2 . . 128.5(2) ?
    C22 C17 N2 . . 108.6(2) ?
    C17 C18 C19 . . 117.1(2) ?
    C17 C18 H18 . . 121.5 ?
    C19 C18 H18 . . 121.5 ?
    C20 C19 C18 . . 121.2(2) ?
    C20 C19 H19 . . 119.4 ?
    C18 C19 H19 . . 119.4 ?
    C19 C20 C21 . . 120.5(2) ?
    C19 C20 H20 . . 119.7 ?
    C21 C20 H20 . . 119.7 ?
    C22 C21 C20 . . 118.7(2) ?
    C22 C21 H21 . . 120.6 ?
    C20 C21 H21 . . 120.6 ?
    C21 C22 C17 . . 119.6(2) ?
    C21 C22 C15 . . 131.2(2) ?
    C17 C22 C15 . . 109.2(2) ?
    O5 C23 H23A . . 109.5 ?
    O5 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    O5 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
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
    O2 C1 C2 C3 . . . . -173.7(2) ?
    O1 C1 C2 C3 . . . . 5.8(3) ?
    O2 C1 C2 C12 . . . . 0.8(3) ?
    O1 C1 C2 C12 . . . . -179.7(2) ?
    C4 O3 C3 C2 . . . . 3.7(4) ?
    C1 C2 C3 O3 . . . . 178.6(2) ?
    C12 C2 C3 O3 . . . . 4.1(4) ?
    C3 O3 C4 C5 . . . . -158.8(2) ?
    C3 O3 C4 C6 . . . . -35.5(3) ?
    O3 C4 C6 C9 . . . . -176.11(19) ?
    C5 C4 C6 C9 . . . . -57.8(3) ?
    O3 C4 C6 C12 . . . . 59.4(2) ?
    C5 C4 C6 C12 . . . . 177.6(2) ?
    C13 N1 C9 C6 . . . . -178.73(19) ?
    C10 N1 C9 C6 . . . . -60.9(2) ?
    C4 C6 C9 N1 . . . . -68.4(3) ?
    C12 C6 C9 N1 . . . . 55.7(2) ?
    C9 N1 C10 C11 . . . . 62.3(2) ?
    C13 N1 C10 C11 . . . . -174.57(18) ?
    C9 N1 C10 C15 . . . . -170.65(18) ?
    C13 N1 C10 C15 . . . . -47.5(2) ?
    N1 C10 C11 C12 . . . . -57.0(2) ?
    C15 C10 C11 C12 . . . . -174.97(18) ?
    C3 C2 C12 C6 . . . . 20.8(3) ?
    C1 C2 C12 C6 . . . . -153.8(2) ?
    C3 C2 C12 C11 . . . . -103.4(3) ?
    C1 C2 C12 C11 . . . . 82.0(2) ?
    C9 C6 C12 C2 . . . . -177.57(17) ?
    C4 C6 C12 C2 . . . . -51.1(2) ?
    C9 C6 C12 C11 . . . . -52.3(2) ?
    C4 C6 C12 C11 . . . . 74.2(2) ?
    C10 C11 C12 C2 . . . . 175.10(18) ?
    C10 C11 C12 C6 . . . . 52.4(2) ?
    C9 N1 C13 C14 . . . . 162.01(19) ?
    C10 N1 C13 C14 . . . . 40.4(2) ?
    N1 C13 C14 C15 . . . . -17.1(2) ?
    N1 C10 C15 C22 . . . . 158.78(18) ?
    C11 C10 C15 C22 . . . . -78.6(3) ?
    N1 C10 C15 C16 . . . . -83.9(2) ?
    C11 C10 C15 C16 . . . . 38.7(3) ?
    N1 C10 C15 C14 . . . . 34.5(2) ?
    C11 C10 C15 C14 . . . . 157.11(19) ?
    C13 C14 C15 C22 . . . . -135.9(2) ?
    C13 C14 C15 C16 . . . . 110.2(2) ?
    C13 C14 C15 C10 . . . . -10.6(2) ?
    C17 N2 C16 O4 . . . . -175.5(2) ?
    C17 N2 C16 C15 . . . . 5.0(2) ?
    C22 C15 C16 O4 . . . . 174.9(2) ?
    C10 C15 C16 O4 . . . . 49.9(3) ?
    C14 C15 C16 O4 . . . . -63.6(3) ?
    C22 C15 C16 N2 . . . . -5.7(2) ?
    C10 C15 C16 N2 . . . . -130.7(2) ?
    C14 C15 C16 N2 . . . . 115.8(2) ?
    C16 N2 C17 C18 . . . . 178.7(2) ?
    C16 N2 C17 C22 . . . . -2.0(3) ?
    C22 C17 C18 C19 . . . . 1.9(3) ?
    N2 C17 C18 C19 . . . . -178.8(2) ?
    C17 C18 C19 C20 . . . . -0.4(3) ?
    C18 C19 C20 C21 . . . . -0.9(4) ?
    C19 C20 C21 C22 . . . . 0.9(3) ?
    C20 C21 C22 C17 . . . . 0.5(3) ?
    C20 C21 C22 C15 . . . . -178.8(2) ?
    C18 C17 C22 C21 . . . . -2.0(3) ?
    N2 C17 C22 C21 . . . . 178.6(2) ?
    C18 C17 C22 C15 . . . . 177.5(2) ?
    N2 C17 C22 C15 . . . . -1.9(2) ?
    C16 C15 C22 C21 . . . . -176.1(2) ?
    C10 C15 C22 C21 . . . . -52.5(3) ?
    C14 C15 C22 C21 . . . . 65.2(3) ?
    C16 C15 C22 C17 . . . . 4.5(2) ?
    C10 C15 C22 C17 . . . . 128.1(2) ?
    C14 C15 C22 C17 . . . . -114.2(2) ?
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
    O1 H1 O5 . 0.84(3) 1.83(3) 2.662(3) 173(4) yes
    O5 H5 O2 2_757 0.84(3) 1.91(3) 2.728(2) 165(4) yes
    N2 H2 O4 2_756 0.88(3) 1.97(3) 2.805(3) 158(3) yes
