##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# 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.                                        #
#                                                                            #
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr template and publCIF'
_journal_date_recd_electronic     2010-10-04
_journal_date_accepted     2010-10-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3356
_journal_page_last     o3356
_journal_paper_category     QO
_journal_coeditor_code     JH2217
_publ_contact_author_name     "Nicol\'o, Francesco"
_publ_contact_author_address
;
Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica
Universit\'a di Messina
via Salita Sperone 31
98166 Vill. Sant'Agata
Messina
Italy
;
_publ_contact_author_email     fnicolo@unime.it
_publ_contact_author_fax      4E307(9)
_publ_contact_author_phone      4E307(9)
_publ_section_title
;
A functionalized enol lactone containing a protected \a-amino acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Bruno, Giuseppe'
;
Dipartimento di Chimica Inorganica Chimica Analitica e Chimica Fisica
Universit\'a degli Studi di Messina
Via Salita Sperone 31
I-98166 Vill. S. Agata
Messina
Italy
;
    "Nicol\'o, Francesco"
;
Dipartimento di Chimica Inorganica Chimica Analitica e Chimica Fisica
Universit\'a degli Studi di Messina
Via Salita Sperone 31
I-98166 Vill. S. Agata
Messina
Italy
;
    'Cordaro, Massimiliano'
;
Dipartimento di Chimica Organica e Biologica
Universit\'a degli Studi di Messina
Via Salita Sperone 31
I-98166 Vill. S. Agata
Messina
Italy
;
    'Grassi, Giovanni'
;
Dipartimento di Chimica Organica e Biologica
Universit\'a degli Studi di Messina
Via Salita Sperone 31
I-98166 Vill. S. Agata
Messina
Italy
;
    'Risitano, Francesco'
;
Dipartimento di Chimica Organica e Biologica
Universit\'a degli Studi di Messina
Via Salita Sperone 31
I-98166 Vill. S. Agata
Messina
Italy
;
data_I
_chemical_name_systematic
;
<i>N</i>-(3,9-dimethyl-4-phenyl-2,5-dioxo-3,4-dihydro-
2<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromen-3-yl)-<i>N</i>-methylbenzamide
methanol monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C28 H23 N O5, C H4 O'
_chemical_formula_sum     'C29 H27 N O6'
_chemical_formula_weight     485.52
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.7435(14)
_cell_length_b     9.9056(17)
_cell_length_c     23.298(3)
_cell_angle_alpha     90
_cell_angle_beta     94.817(7)
_cell_angle_gamma     90
_cell_volume     2470.7(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     59
_cell_measurement_theta_min     7.74
_cell_measurement_theta_max     17.49
_cell_measurement_temperature     298(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.58
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.36
_exptl_crystal_density_diffrn     1.305
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1024
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(Kopfmann & Huber, 1968)'
_exptl_absorpt_correction_T_min     0.870
_exptl_absorpt_correction_T_max     0.968
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens P4'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9535
_diffrn_reflns_av_R_equivalents     0.0355
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     3
_diffrn_standards_interval_count     197
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    0 -3 -11
    2 -4 16
    -2 3 -10
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>-factors based on ALL data will be
even larger.
;
_reflns_number_total     4347
_reflns_number_gt     2843
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0852
_refine_ls_R_factor_gt     0.0494
_refine_ls_wR_factor_gt     0.1134
_refine_ls_wR_factor_ref     0.1318
_refine_ls_goodness_of_fit_ref     1.011
_refine_ls_restrained_S_all     1.011
_refine_ls_number_reflns     4347
_refine_ls_number_parameters     331
_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^)+(0.0533P)^2^+0.7913P] 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     0.181
_refine_diff_density_min     -0.309
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0036(8)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
_computing_data_collection     'XSCANS (Bruker, 1999)'
_computing_cell_refinement     'XSCANS (Bruker, 1999)'
_computing_data_reduction     'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution     'SIR97 (Altomare <i>et al.</i>, 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XPW (Siemens, 1996)'
_computing_publication_material
;
PARST97 (Nardelli, 1995) and SHELXL97 (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
    O O1 0.50718(15) 0.77955(19) 0.49310(6) 0.0560(5) Uani d . 1 . .
    C C2 0.6021(2) 0.8610(3) 0.51636(10) 0.0490(6) Uani d . 1 . .
    C C3 0.64762(19) 0.8378(2) 0.57594(9) 0.0440(6) Uani d . 1 . .
    C C4 0.5962(2) 0.7392(2) 0.60580(9) 0.0456(6) Uani d . 1 . .
    C C5 0.4958(2) 0.6556(3) 0.58143(10) 0.0483(6) Uani d . 1 . .
    C C6 0.4409(2) 0.5503(3) 0.61028(12) 0.0588(7) Uani d . 1 . .
    H H6 0.4684 0.5327 0.6485 0.071 Uiso calc R 1 . .
    C C7 0.3471(2) 0.4720(3) 0.58354(14) 0.0675(8) Uani d . 1 . .
    C C8 0.3087(2) 0.5014(3) 0.52619(15) 0.0735(9) Uani d . 1 . .
    H H8 0.2451 0.4500 0.5075 0.088 Uiso calc R 1 . .
    C C9 0.3612(2) 0.6034(3) 0.49630(12) 0.0655(8) Uani d . 1 . .
    H H9 0.3340 0.6203 0.4580 0.079 Uiso calc R 1 . .
    C C10 0.4550(2) 0.6802(3) 0.52418(10) 0.0512(6) Uani d . 1 . .
    O O11 0.64195(16) 0.9454(2) 0.48534(7) 0.0649(5) Uani d . 1 . .
    C C12 0.75139(19) 0.9241(3) 0.60261(9) 0.0442(6) Uani d . 1 . .
    H H12 0.7380 1.0154 0.5872 0.053 Uiso calc R 1 . .
    C C13 0.7374(2) 0.9318(3) 0.66888(9) 0.0447(6) Uani d . 1 . .
    C C14 0.7351(2) 0.7859(3) 0.68848(9) 0.0491(6) Uani d . 1 . .
    O O15 0.64021(15) 0.70590(17) 0.66098(6) 0.0538(4) Uani d . 1 . .
    C C16 0.2891(3) 0.3579(3) 0.61477(16) 0.0964(11) Uani d . 1 . .
    H H16A 0.2461 0.2984 0.5873 0.145 Uiso calc PR 0.50 . .
    H H16B 0.2310 0.3938 0.6399 0.145 Uiso calc PR 0.50 . .
    H H16C 0.3533 0.3087 0.6370 0.145 Uiso calc PR 0.50 . .
    H H16D 0.3075 0.3689 0.6555 0.145 Uiso calc PR 0.50 . .
    H H16E 0.3226 0.2735 0.6029 0.145 Uiso calc PR 0.50 . .
    H H16F 0.2003 0.3585 0.6058 0.145 Uiso calc PR 0.50 . .
    C C17 0.8802(2) 0.8790(3) 0.58752(9) 0.0493(6) Uani d . 1 . .
    C C18 0.9676(2) 0.9762(3) 0.57662(11) 0.0684(8) Uani d . 1 . .
    H H18 0.9468 1.0670 0.5789 0.082 Uiso calc R 1 . .
    C C19 1.0865(3) 0.9398(4) 0.56224(12) 0.0835(10) Uani d . 1 . .
    H H19 1.1443 1.0064 0.5552 0.100 Uiso calc R 1 . .
    C C20 1.1177(3) 0.8095(5) 0.55848(13) 0.0848(11) Uani d . 1 . .
    H H20 1.1971 0.7857 0.5490 0.102 Uiso calc R 1 . .
    C C21 1.0328(3) 0.7111(4) 0.56862(13) 0.0832(10) Uani d . 1 . .
    H H21 1.0546 0.6207 0.5658 0.100 Uiso calc R 1 . .
    C C22 0.9136(2) 0.7461(3) 0.58313(11) 0.0633(7) Uani d . 1 . .
    H H22 0.8563 0.6787 0.5899 0.076 Uiso calc R 1 . .
    C C23 0.8437(2) 1.0061(3) 0.70278(10) 0.0583(7) Uani d . 1 . .
    H H23A 0.8475 1.0973 0.6891 0.087 Uiso calc R 1 . .
    H H23B 0.9212 0.9613 0.6977 0.087 Uiso calc R 1 . .
    H H23C 0.8294 1.0067 0.7429 0.087 Uiso calc R 1 . .
    N N24 0.61573(15) 0.9977(2) 0.67699(7) 0.0444(5) Uani d . 1 . .
    C C25 0.5853(2) 1.1225(3) 0.64515(11) 0.0613(7) Uani d . 1 . .
    H H25A 0.6605 1.1728 0.6412 0.092 Uiso calc R 1 . .
    H H25B 0.5290 1.1756 0.6657 0.092 Uiso calc R 1 . .
    H H25C 0.5467 1.1007 0.6076 0.092 Uiso calc R 1 . .
    C C26 0.5548(2) 0.9634(3) 0.72315(10) 0.0490(6) Uani d . 1 . .
    O O27 0.59794(16) 0.8770(2) 0.75754(7) 0.0659(5) Uani d . 1 . .
    C C28 0.4305(2) 1.0259(3) 0.73030(10) 0.0502(6) Uani d . 1 . .
    C C29 0.3308(2) 1.0086(3) 0.68954(12) 0.0716(8) Uani d . 1 . .
    H H29 0.3414 0.9615 0.6558 0.086 Uiso calc R 1 . .
    C C30 0.2151(2) 1.0614(4) 0.69901(14) 0.0843(10) Uani d . 1 . .
    H H30 0.1477 1.0472 0.6719 0.101 Uiso calc R 1 . .
    C C31 0.1984(3) 1.1333(4) 0.74701(14) 0.0807(9) Uani d . 1 . .
    H H31 0.1206 1.1700 0.7526 0.097 Uiso calc R 1 . .
    C C32 0.2965(3) 1.1516(4) 0.78720(13) 0.0806(9) Uani d . 1 . .
    H H32 0.2856 1.2013 0.8203 0.097 Uiso calc R 1 . .
    C C33 0.4116(2) 1.0973(3) 0.77930(11) 0.0657(8) Uani d . 1 . .
    H H33 0.4773 1.1091 0.8075 0.079 Uiso calc R 1 . .
    O O34 0.81109(15) 0.7302(2) 0.72014(7) 0.0637(5) Uani d . 1 . .
    C C34 0.5741(5) 0.8527(5) 0.8947(2) 0.1397(17) Uani d . 1 . .
    H H34A 0.5325 0.7866 0.8698 0.210 Uiso calc R 1 . .
    H H34B 0.5214 0.9305 0.8969 0.210 Uiso calc R 1 . .
    H H34C 0.5915 0.8150 0.9325 0.210 Uiso calc R 1 . .
    O O35 0.6784(3) 0.8881(7) 0.87417(13) 0.208(2) Uani d . 1 . .
    H H35 0.6675 0.8947 0.8390 0.312 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
    O1 0.0512(9) 0.0702(12) 0.0453(9) 0.0038(9) -0.0040(7) -0.0002(9)
    C2 0.0414(12) 0.0628(17) 0.0433(12) 0.0088(12) 0.0060(10) -0.0008(13)
    C3 0.0388(11) 0.0561(15) 0.0378(11) 0.0061(11) 0.0068(9) 0.0007(11)
    C4 0.0450(12) 0.0535(15) 0.0383(11) 0.0068(12) 0.0044(9) -0.0019(11)
    C5 0.0400(12) 0.0528(15) 0.0533(14) 0.0048(11) 0.0110(10) -0.0051(12)
    C6 0.0509(14) 0.0589(17) 0.0680(16) 0.0005(13) 0.0135(12) -0.0055(14)
    C7 0.0489(15) 0.0576(18) 0.099(2) -0.0006(14) 0.0214(15) -0.0127(17)
    C8 0.0433(14) 0.074(2) 0.102(2) -0.0026(15) 0.0015(15) -0.0291(19)
    C9 0.0494(15) 0.076(2) 0.0696(17) 0.0070(15) -0.0045(13) -0.0197(16)
    C10 0.0397(12) 0.0585(17) 0.0553(14) 0.0072(12) 0.0041(11) -0.0069(13)
    O11 0.0640(11) 0.0864(14) 0.0446(9) -0.0029(10) 0.0072(8) 0.0148(10)
    C12 0.0405(12) 0.0535(15) 0.0390(11) 0.0011(11) 0.0058(9) 0.0027(11)
    C13 0.0387(12) 0.0575(16) 0.0382(11) 0.0040(11) 0.0043(9) -0.0002(11)
    C14 0.0447(12) 0.0655(17) 0.0373(11) 0.0055(13) 0.0060(10) 0.0006(12)
    O15 0.0619(10) 0.0573(11) 0.0417(8) -0.0035(9) 0.0011(7) 0.0069(8)
    C16 0.076(2) 0.076(2) 0.141(3) -0.0171(18) 0.029(2) -0.003(2)
    C17 0.0421(12) 0.0686(18) 0.0378(12) -0.0006(13) 0.0079(10) -0.0013(12)
    C18 0.0584(16) 0.086(2) 0.0632(16) -0.0079(16) 0.0182(13) -0.0048(16)
    C19 0.0550(17) 0.129(3) 0.0698(19) -0.015(2) 0.0224(14) -0.009(2)
    C20 0.0500(16) 0.138(3) 0.0687(19) 0.014(2) 0.0170(14) -0.014(2)
    C21 0.0671(19) 0.103(3) 0.081(2) 0.027(2) 0.0170(16) -0.0044(19)
    C22 0.0546(15) 0.073(2) 0.0631(16) 0.0080(15) 0.0110(12) -0.0009(14)
    C23 0.0463(13) 0.0765(19) 0.0518(13) -0.0025(14) 0.0015(11) -0.0070(14)
    N24 0.0397(10) 0.0542(12) 0.0397(9) 0.0036(9) 0.0068(8) 0.0038(9)
    C25 0.0583(15) 0.0686(19) 0.0586(15) 0.0116(14) 0.0158(12) 0.0123(14)
    C26 0.0455(13) 0.0591(16) 0.0427(12) 0.0009(12) 0.0049(10) -0.0023(12)
    O27 0.0669(11) 0.0826(14) 0.0501(10) 0.0178(11) 0.0156(8) 0.0156(10)
    C28 0.0417(12) 0.0607(16) 0.0490(13) -0.0030(12) 0.0091(10) 0.0024(12)
    C29 0.0502(15) 0.100(2) 0.0642(16) -0.0008(16) 0.0047(12) -0.0214(17)
    C30 0.0403(15) 0.128(3) 0.084(2) -0.0023(17) -0.0005(14) -0.011(2)
    C31 0.0505(16) 0.113(3) 0.081(2) 0.0139(17) 0.0204(15) -0.002(2)
    C32 0.0637(18) 0.107(3) 0.0732(19) 0.0124(18) 0.0176(15) -0.0207(18)
    C33 0.0503(14) 0.091(2) 0.0564(15) 0.0016(15) 0.0070(12) -0.0154(15)
    O34 0.0554(10) 0.0799(13) 0.0549(10) 0.0163(10) -0.0014(8) 0.0164(10)
    C34 0.159(4) 0.135(4) 0.128(4) 0.009(4) 0.024(3) 0.029(3)
    O35 0.140(3) 0.398(7) 0.0822(19) 0.048(4) -0.0186(19) 0.013(3)
_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
    O1 C10 . 1.369(3) yes
    O1 C2 . 1.376(3) yes
    C2 O11 . 1.206(3) yes
    C2 C3 . 1.451(3) yes
    C3 C4 . 1.344(3) yes
    C3 C12 . 1.498(3) yes
    C4 O15 . 1.372(3) yes
    C4 C5 . 1.438(3) yes
    C5 C10 . 1.390(3) yes
    C5 C6 . 1.398(3) ?
    C6 C7 . 1.379(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.396(4) ?
    C7 C16 . 1.507(4) ?
    C8 C9 . 1.375(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.381(4) ?
    C9 H9 . 0.9300 ?
    C12 C17 . 1.524(3) yes
    C12 C13 . 1.566(3) yes
    C12 H12 . 0.9800 ?
    C13 N24 . 1.488(3) yes
    C13 C14 . 1.516(4) yes
    C13 C23 . 1.523(3) yes
    C14 O34 . 1.189(3) yes
    C14 O15 . 1.403(3) yes
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C16 H16D . 0.9600 ?
    C16 H16E . 0.9600 ?
    C16 H16F . 0.9600 ?
    C17 C22 . 1.371(4) ?
    C17 C18 . 1.382(4) ?
    C18 C19 . 1.395(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.339(5) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.369(5) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.395(4) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
    N24 C26 . 1.349(3) yes
    N24 C25 . 1.464(3) yes
    C25 H25A . 0.9600 ?
    C25 H25B . 0.9600 ?
    C25 H25C . 0.9600 ?
    C26 O27 . 1.236(3) yes
    C26 C28 . 1.493(3) yes
    C28 C33 . 1.373(3) yes
    C28 C29 . 1.382(3) yes
    C29 C30 . 1.383(4) yes
    C29 H29 . 0.9300 ?
    C30 C31 . 1.351(4) yes
    C30 H30 . 0.9300 ?
    C31 C32 . 1.362(4) yes
    C31 H31 . 0.9300 ?
    C32 C33 . 1.374(4) yes
    C32 H32 . 0.9300 ?
    C33 H33 . 0.9300 ?
    C34 O35 . 1.302(5) yes
    C34 H34A . 0.9600 ?
    C34 H34B . 0.9600 ?
    C34 H34C . 0.9600 ?
    O35 H35 . 0.8200 ?
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
    C10 O1 C2 . . 122.43(19) yes
    O11 C2 O1 . . 117.3(2) yes
    O11 C2 C3 . . 125.1(2) yes
    O1 C2 C3 . . 117.6(2) yes
    C4 C3 C2 . . 119.4(2) yes
    C4 C3 C12 . . 121.6(2) yes
    C2 C3 C12 . . 119.0(2) yes
    C3 C4 O15 . . 122.4(2) yes
    C3 C4 C5 . . 122.8(2) yes
    O15 C4 C5 . . 114.8(2) yes
    C10 C5 C6 . . 118.7(2) yes
    C10 C5 C4 . . 116.3(2) yes
    C6 C5 C4 . . 124.9(2) yes
    C7 C6 C5 . . 121.6(3) ?
    C7 C6 H6 . . 119.2 ?
    C5 C6 H6 . . 119.2 ?
    C6 C7 C8 . . 117.5(3) ?
    C6 C7 C16 . . 121.4(3) ?
    C8 C7 C16 . . 121.2(3) ?
    C9 C8 C7 . . 122.5(3) ?
    C9 C8 H8 . . 118.8 ?
    C7 C8 H8 . . 118.8 ?
    C8 C9 C10 . . 118.8(3) ?
    C8 C9 H9 . . 120.6 ?
    C10 C9 H9 . . 120.6 ?
    O1 C10 C9 . . 117.6(2) yes
    O1 C10 C5 . . 121.5(2) yes
    C9 C10 C5 . . 120.9(3) yes
    C3 C12 C17 . . 113.34(19) yes
    C3 C12 C13 . . 107.90(17) yes
    C17 C12 C13 . . 113.96(17) yes
    C3 C12 H12 . . 107.1 ?
    C17 C12 H12 . . 107.1 ?
    C13 C12 H12 . . 107.1 ?
    N24 C13 C14 . . 110.10(18) yes
    N24 C13 C23 . . 110.53(19) yes
    C14 C13 C23 . . 109.6(2) yes
    N24 C13 C12 . . 107.74(16) yes
    C14 C13 C12 . . 104.82(19) yes
    C23 C13 C12 . . 113.90(18) yes
    O34 C14 O15 . . 117.1(2) yes
    O34 C14 C13 . . 127.0(2) yes
    O15 C14 C13 . . 115.49(19) yes
    C4 O15 C14 . . 118.16(18) yes
    C7 C16 H16A . . 109.5 ?
    C7 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C7 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C7 C16 H16D . . 109.5 ?
    H16A C16 H16D . . 141.1 ?
    H16B C16 H16D . . 56.3 ?
    H16C C16 H16D . . 56.3 ?
    C7 C16 H16E . . 109.5 ?
    H16A C16 H16E . . 56.3 ?
    H16B C16 H16E . . 141.1 ?
    H16C C16 H16E . . 56.3 ?
    H16D C16 H16E . . 109.5 ?
    C7 C16 H16F . . 109.5 ?
    H16A C16 H16F . . 56.3 ?
    H16B C16 H16F . . 56.3 ?
    H16C C16 H16F . . 141.1 ?
    H16D C16 H16F . . 109.5 ?
    H16E C16 H16F . . 109.5 ?
    C22 C17 C18 . . 118.0(2) ?
    C22 C17 C12 . . 123.1(2) ?
    C18 C17 C12 . . 118.8(2) ?
    C17 C18 C19 . . 120.9(3) ?
    C17 C18 H18 . . 119.5 ?
    C19 C18 H18 . . 119.5 ?
    C20 C19 C18 . . 120.3(3) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 120.1(3) ?
    C19 C20 H20 . . 120.0 ?
    C21 C20 H20 . . 120.0 ?
    C20 C21 C22 . . 120.3(3) ?
    C20 C21 H21 . . 119.9 ?
    C22 C21 H21 . . 119.9 ?
    C17 C22 C21 . . 120.5(3) ?
    C17 C22 H22 . . 119.8 ?
    C21 C22 H22 . . 119.8 ?
    C13 C23 H23A . . 109.5 ?
    C13 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C13 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C26 N24 C25 . . 121.0(2) yes
    C26 N24 C13 . . 118.76(19) yes
    C25 N24 C13 . . 117.86(18) yes
    N24 C25 H25A . . 109.5 ?
    N24 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    N24 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    O27 C26 N24 . . 120.7(2) yes
    O27 C26 C28 . . 120.3(2) yes
    N24 C26 C28 . . 118.9(2) yes
    C33 C28 C29 . . 118.3(2) ?
    C33 C28 C26 . . 120.2(2) ?
    C29 C28 C26 . . 121.4(2) ?
    C28 C29 C30 . . 119.9(3) ?
    C28 C29 H29 . . 120.0 ?
    C30 C29 H29 . . 120.0 ?
    C31 C30 C29 . . 121.0(3) ?
    C31 C30 H30 . . 119.5 ?
    C29 C30 H30 . . 119.5 ?
    C30 C31 C32 . . 119.4(3) ?
    C30 C31 H31 . . 120.3 ?
    C32 C31 H31 . . 120.3 ?
    C31 C32 C33 . . 120.6(3) ?
    C31 C32 H32 . . 119.7 ?
    C33 C32 H32 . . 119.7 ?
    C28 C33 C32 . . 120.7(3) ?
    C28 C33 H33 . . 119.6 ?
    C32 C33 H33 . . 119.6 ?
    O35 C34 H34A . . 109.5 ?
    O35 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    O35 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
    C34 O35 H35 . . 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
    C10 O1 C2 O11 . . . . 179.8(2) ?
    C10 O1 C2 C3 . . . . 0.6(3) ?
    O11 C2 C3 C4 . . . . -179.2(2) ?
    O1 C2 C3 C4 . . . . -0.1(3) ?
    O11 C2 C3 C12 . . . . 0.5(3) ?
    O1 C2 C3 C12 . . . . 179.67(19) ?
    C2 C3 C4 O15 . . . . 175.6(2) ?
    C12 C3 C4 O15 . . . . -4.2(3) ?
    C2 C3 C4 C5 . . . . -0.8(3) ?
    C12 C3 C4 C5 . . . . 179.5(2) ?
    C3 C4 C5 C10 . . . . 1.1(3) ?
    O15 C4 C5 C10 . . . . -175.52(19) ?
    C3 C4 C5 C6 . . . . 178.7(2) ?
    O15 C4 C5 C6 . . . . 2.0(3) ?
    C10 C5 C6 C7 . . . . -0.7(4) ?
    C4 C5 C6 C7 . . . . -178.2(2) ?
    C5 C6 C7 C8 . . . . 0.1(4) ?
    C5 C6 C7 C16 . . . . 179.5(2) ?
    C6 C7 C8 C9 . . . . 0.4(4) ?
    C16 C7 C8 C9 . . . . -178.9(3) ?
    C7 C8 C9 C10 . . . . -0.4(4) ?
    C2 O1 C10 C9 . . . . -179.3(2) ?
    C2 O1 C10 C5 . . . . -0.3(3) ?
    C8 C9 C10 O1 . . . . 178.8(2) ?
    C8 C9 C10 C5 . . . . -0.1(4) ?
    C6 C5 C10 O1 . . . . -178.3(2) ?
    C4 C5 C10 O1 . . . . -0.6(3) ?
    C6 C5 C10 C9 . . . . 0.7(3) ?
    C4 C5 C10 C9 . . . . 178.4(2) ?
    C4 C3 C12 C17 . . . . 98.8(2) ?
    C2 C3 C12 C17 . . . . -80.9(3) ?
    C4 C3 C12 C13 . . . . -28.3(3) ?
    C2 C3 C12 C13 . . . . 151.9(2) ?
    C3 C12 C13 N24 . . . . -62.3(2) ?
    C17 C12 C13 N24 . . . . 170.9(2) ?
    C3 C12 C13 C14 . . . . 55.0(2) ?
    C17 C12 C13 C14 . . . . -71.8(2) ?
    C3 C12 C13 C23 . . . . 174.7(2) ?
    C17 C12 C13 C23 . . . . 47.9(3) ?
    N24 C13 C14 O34 . . . . -130.1(2) ?
    C23 C13 C14 O34 . . . . -8.3(3) ?
    C12 C13 C14 O34 . . . . 114.3(2) ?
    N24 C13 C14 O15 . . . . 57.6(2) ?
    C23 C13 C14 O15 . . . . 179.33(17) ?
    C12 C13 C14 O15 . . . . -58.1(2) ?
    C3 C4 O15 C14 . . . . 5.6(3) ?
    C5 C4 O15 C14 . . . . -177.71(18) ?
    O34 C14 O15 C4 . . . . -144.9(2) ?
    C13 C14 O15 C4 . . . . 28.2(3) ?
    C3 C12 C17 C22 . . . . -38.0(3) ?
    C13 C12 C17 C22 . . . . 85.9(3) ?
    C3 C12 C17 C18 . . . . 140.8(2) ?
    C13 C12 C17 C18 . . . . -95.3(3) ?
    C22 C17 C18 C19 . . . . -0.7(4) ?
    C12 C17 C18 C19 . . . . -179.5(2) ?
    C17 C18 C19 C20 . . . . 0.3(5) ?
    C18 C19 C20 C21 . . . . 0.1(5) ?
    C19 C20 C21 C22 . . . . -0.2(5) ?
    C18 C17 C22 C21 . . . . 0.6(4) ?
    C12 C17 C22 C21 . . . . 179.4(2) ?
    C20 C21 C22 C17 . . . . -0.1(4) ?
    C14 C13 N24 C26 . . . . 35.9(3) ?
    C23 C13 N24 C26 . . . . -85.3(3) ?
    C12 C13 N24 C26 . . . . 149.6(2) ?
    C14 C13 N24 C25 . . . . -161.6(2) ?
    C23 C13 N24 C25 . . . . 77.2(2) ?
    C12 C13 N24 C25 . . . . -47.8(3) ?
    C25 N24 C26 O27 . . . . -163.2(2) ?
    C13 N24 C26 O27 . . . . -1.3(3) ?
    C25 N24 C26 C28 . . . . 20.1(3) ?
    C13 N24 C26 C28 . . . . -177.9(2) ?
    O27 C26 C28 C33 . . . . 61.0(4) ?
    N24 C26 C28 C33 . . . . -122.4(3) ?
    O27 C26 C28 C29 . . . . -116.1(3) ?
    N24 C26 C28 C29 . . . . 60.5(3) ?
    C33 C28 C29 C30 . . . . -0.8(4) ?
    C26 C28 C29 C30 . . . . 176.3(3) ?
    C28 C29 C30 C31 . . . . 1.9(5) ?
    C29 C30 C31 C32 . . . . -1.4(5) ?
    C30 C31 C32 C33 . . . . -0.2(5) ?
    C29 C28 C33 C32 . . . . -0.8(4) ?
    C26 C28 C33 C32 . . . . -177.9(3) ?
    C31 C32 C33 C28 . . . . 1.3(5) ?
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
    O35 H35 O27 . 0.82 1.99 2.784(3) 163 yes
    C9 H9 O35 4_575 0.93 2.46 3.320(4) 153 yes
    C19 H19 O11 3_776 0.93 2.60 3.403(3) 144 yes