##############################################################################
#                                                                            #
# 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 # 
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##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2012-11-10
_journal_date_accepted     2012-11-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      1
_journal_page_first     o23
_journal_page_last     o24
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812049082
_journal_coeditor_code     BT6853
_publ_contact_author_name     'Devadasan Velmurugan'
_publ_contact_author_address
;
CAS in Crystallography and Biophysics
University of madras
Maraimalai campus(guindy campus)
Chennai 600 025
India
;
_publ_contact_author_email     'shirai2011@gmail.com'
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;\
Ethyl
27-oxo-15-oxa-2,20-diazahexacyclo[18.6.1.0^1,8^.0^2,6^.0^9,14^.0^21,26^]\
heptacosa-9,11,13,21,23,25-hexaene-7-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Sibi Narayanan'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'Thothadri Srinivasan'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'Santhanagopalan Purushothaman'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'Raghavachary Raghunathan'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'Devadasan Velmurugan'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 27-oxo-15-oxa-2,20-
diazahexacyclo[18.6.1.0^1,8^.0^2,6^.0^9,14^.0^21,26^]heptacosa-
9,11,13,21,23,25-hexaene-7-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H30 N2 O4'
_chemical_formula_sum     'C27 H30 N2 O4'
_chemical_formula_iupac     'C27 H30 N2 O4'
_chemical_formula_weight     446.53
_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     8.9327(5)
_cell_length_b     10.0068(5)
_cell_length_c     14.6379(11)
_cell_angle_alpha     103.988(4)
_cell_angle_beta     95.023(4)
_cell_angle_gamma     113.775(3)
_cell_volume     1136.41(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5603
_cell_measurement_theta_min     1.5
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     'white crystalline'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.305
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     476
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.9742
_exptl_absorpt_correction_T_max     0.9784
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20472
_diffrn_reflns_av_R_equivalents     0.0253
_diffrn_reflns_av_sigmaI/netI     0.0231
_diffrn_reflns_theta_min     1.47
_diffrn_reflns_theta_max     28.29
_diffrn_reflns_theta_full     28.29
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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     5603
_reflns_number_gt     4378
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0588
_refine_ls_R_factor_gt     0.0454
_refine_ls_wR_factor_gt     0.1161
_refine_ls_wR_factor_ref     0.1250
_refine_ls_goodness_of_fit_ref     1.078
_refine_ls_restrained_S_all     1.076
_refine_ls_number_reflns     5603
_refine_ls_number_parameters     319
_refine_ls_number_restraints     40
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0559P)²+0.2150P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.233
_refine_diff_density_min     -0.217
_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' 0.0033 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     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    C C1A -0.0430(10) 1.0338(8) 0.2839(4) 0.0877(18) Uani d PDU 0.587(11) 1 A 1
    H H1A1 0.0125 1.0358 0.2306 0.132 Uiso calc PR 0.587(11) 1 A 1
    H H1A2 -0.0730 1.1174 0.2975 0.132 Uiso calc PR 0.587(11) 1 A 1
    H H1A3 -0.1420 0.9386 0.2680 0.132 Uiso calc PR 0.587(11) 1 A 1
    C C2A 0.0677(12) 1.0483(8) 0.3675(6) 0.089(3) Uani d PDU 0.587(11) 1 A 1
    H H2A1 0.0188 1.0599 0.4238 0.106 Uiso calc PR 0.587(11) 1 A 1
    H H2A2 0.1740 1.1376 0.3795 0.106 Uiso calc PR 0.587(11) 1 A 1
    C C1B 0.0656(17) 1.0966(9) 0.2980(6) 0.088(3) Uani d PDU 0.413(11) 1 A 2
    H H1B1 0.1845 1.1562 0.3183 0.131 Uiso calc PR 0.413(11) 1 A 2
    H H1B2 0.0130 1.1639 0.3003 0.131 Uiso calc PR 0.413(11) 1 A 2
    H H1B3 0.0393 1.0304 0.2334 0.131 Uiso calc PR 0.413(11) 1 A 2
    C C2B 0.0054(13) 1.0057(11) 0.3611(9) 0.072(3) Uani d PDU 0.413(11) 1 A 2
    H H2B1 -0.1149 0.9451 0.3426 0.086 Uiso calc PR 0.413(11) 1 A 2
    H H2B2 0.0346 1.0696 0.4274 0.086 Uiso calc PR 0.413(11) 1 A 2
    C C3 0.21727(18) 0.92280(15) 0.41102(10) 0.0423(3) Uani d . 1 1 A .
    C C4 0.26073(15) 0.78973(13) 0.38728(9) 0.0328(3) Uani d . 1 1 . .
    H H4 0.3792 0.8281 0.4159 0.039 Uiso calc R 1 1 . .
    C C5 0.15967(15) 0.66458(14) 0.43037(9) 0.0346(3) Uani d . 1 1 . .
    H H5 0.0410 0.6419 0.4175 0.042 Uiso calc R 1 1 . .
    C C6 0.22279(18) 0.69639(17) 0.53715(10) 0.0466(3) Uani d . 1 1 . .
    H H6A 0.2708 0.8051 0.5713 0.056 Uiso calc R 1 1 . .
    H H6B 0.1334 0.6416 0.5664 0.056 Uiso calc R 1 1 . .
    C C7 0.3552(2) 0.63749(19) 0.53718(11) 0.0550(4) Uani d . 1 1 . .
    H H7A 0.4601 0.7115 0.5293 0.066 Uiso calc R 1 1 . .
    H H7B 0.3743 0.6130 0.5960 0.066 Uiso calc R 1 1 . .
    C C8 0.2771(2) 0.49510(18) 0.45101(11) 0.0503(4) Uani d . 1 1 . .
    H H8A 0.3628 0.4711 0.4251 0.060 Uiso calc R 1 1 . .
    H H8B 0.2022 0.4082 0.4687 0.060 Uiso calc R 1 1 . .
    C C9 0.24212(14) 0.55059(13) 0.28972(9) 0.0314(2) Uani d . 1 1 . .
    C C10 0.40719(14) 0.54634(14) 0.28034(9) 0.0335(3) Uani d . 1 1 . .
    C C11 0.56843(16) 0.64768(16) 0.32716(11) 0.0433(3) Uani d . 1 1 . .
    H H11 0.5907 0.7389 0.3736 0.052 Uiso calc R 1 1 . .
    C C12 0.69804(17) 0.6109(2) 0.30370(12) 0.0531(4) Uani d . 1 1 . .
    H H12 0.8079 0.6793 0.3342 0.064 Uiso calc R 1 1 . .
    C C13 0.66598(19) 0.4754(2) 0.23631(12) 0.0552(4) Uani d . 1 1 . .
    H H13 0.7541 0.4521 0.2231 0.066 Uiso calc R 1 1 . .
    C C14 0.50416(19) 0.37281(19) 0.18772(11) 0.0491(4) Uani d . 1 1 . .
    H H14 0.4821 0.2810 0.1419 0.059 Uiso calc R 1 1 . .
    C C15 0.37664(16) 0.41162(15) 0.20968(9) 0.0373(3) Uani d . 1 1 . .
    C C16 0.11869(15) 0.40657(14) 0.20770(9) 0.0362(3) Uani d . 1 1 . .
    C C17 0.1341(2) 0.19559(16) 0.08382(11) 0.0528(4) Uani d . 1 1 . .
    H H17A 0.0135 0.1469 0.0769 0.063 Uiso calc R 1 1 . .
    H H17B 0.1753 0.1226 0.0927 0.063 Uiso calc R 1 1 . .
    C C18 0.1747(2) 0.23314(18) -0.00835(11) 0.0552(4) Uani d . 1 1 . .
    H H18A 0.1372 0.1376 -0.0597 0.066 Uiso calc R 1 1 . .
    H H18B 0.2953 0.2869 0.0004 0.066 Uiso calc R 1 1 . .
    C C19 0.0979(2) 0.33016(19) -0.04075(11) 0.0568(4) Uani d . 1 1 . .
    H H19A 0.0621 0.2915 -0.1103 0.068 Uiso calc R 1 1 . .
    H H19B -0.0013 0.3154 -0.0142 0.068 Uiso calc R 1 1 . .
    C C20 0.2087(2) 0.49895(18) -0.01325(10) 0.0531(4) Uani d . 1 1 . .
    H H20A 0.3192 0.5157 -0.0248 0.064 Uiso calc R 1 1 . .
    H H20B 0.1635 0.5445 -0.0528 0.064 Uiso calc R 1 1 . .
    C C21 0.33250(17) 0.72236(15) 0.12529(10) 0.0396(3) Uani d . 1 1 . .
    C C22 0.4290(2) 0.80905(19) 0.07220(11) 0.0536(4) Uani d . 1 1 . .
    H H22 0.4166 0.7651 0.0066 0.064 Uiso calc R 1 1 . .
    C C23 0.5431(2) 0.95975(19) 0.11637(12) 0.0592(4) Uani d . 1 1 . .
    H H23 0.6082 1.0165 0.0806 0.071 Uiso calc R 1 1 . .
    C C24 0.5606(2) 1.02605(18) 0.21268(12) 0.0565(4) Uani d . 1 1 . .
    H H24 0.6379 1.1274 0.2427 0.068 Uiso calc R 1 1 . .
    C C25 0.46165(18) 0.94020(16) 0.26501(11) 0.0473(3) Uani d . 1 1 . .
    H H25 0.4736 0.9863 0.3302 0.057 Uiso calc R 1 1 . .
    C C26 0.34589(15) 0.78868(14) 0.22383(9) 0.0350(3) Uani d . 1 1 . .
    C C27 0.23201(14) 0.69994(13) 0.28114(8) 0.0314(2) Uani d . 1 1 . .
    H H27 0.1165 0.6710 0.2510 0.038 Uiso calc R 1 1 . .
    N N1 0.18398(13) 0.53096(12) 0.37981(7) 0.0361(2) Uani d . 1 1 . .
    N N2 0.20527(14) 0.32851(12) 0.16915(8) 0.0398(3) Uani d . 1 1 . .
    O O1 0.28603(18) 1.03033(14) 0.48165(9) 0.0743(4) Uani d . 1 1 . .
    O O2 0.09278(16) 0.90670(14) 0.34755(9) 0.0684(3) Uani d D 1 1 . .
    O O3 0.22133(12) 0.57163(11) 0.08703(6) 0.0447(2) Uani d . 1 1 . .
    O O4 -0.03046(11) 0.36456(11) 0.18380(7) 0.0494(3) Uani d . 1 1 . .
_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
    C1A C2A . 1.443(6) ?
    C1A H1A1 . 0.9600 ?
    C1A H1A2 . 0.9600 ?
    C1A H1A3 . 0.9600 ?
    C2A O2 . 1.487(5) ?
    C2A H2A1 . 0.9700 ?
    C2A H2A2 . 0.9700 ?
    C1B C2B . 1.438(7) ?
    C1B H1B1 . 0.9600 ?
    C1B H1B2 . 0.9600 ?
    C1B H1B3 . 0.9600 ?
    C2B O2 . 1.478(6) ?
    C2B H2B1 . 0.9700 ?
    C2B H2B2 . 0.9700 ?
    C3 O1 . 1.1925(18) ?
    C3 O2 . 1.3145(18) ?
    C3 C4 . 1.5038(17) ?
    C4 C5 . 1.5333(16) ?
    C4 C27 . 1.5351(17) ?
    C4 H4 . 0.9800 ?
    C5 N1 . 1.4720(16) ?
    C5 C6 . 1.5241(19) ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.520(2) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.511(2) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 N1 . 1.4756(17) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 N1 . 1.4867(15) ?
    C9 C10 . 1.5093(15) ?
    C9 C16 . 1.5442(17) ?
    C9 C27 . 1.5669(16) ?
    C10 C11 . 1.3734(18) ?
    C10 C15 . 1.3934(18) ?
    C11 C12 . 1.3947(19) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.373(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.385(2) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.3827(18) ?
    C14 H14 . 0.9300 ?
    C15 N2 . 1.4011(17) ?
    C16 O4 . 1.2123(15) ?
    C16 N2 . 1.3701(16) ?
    C17 N2 . 1.4524(18) ?
    C17 C18 . 1.521(2) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 C19 . 1.530(2) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 C20 . 1.500(2) ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 O3 . 1.4440(16) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 O3 . 1.3643(16) ?
    C21 C22 . 1.3930(19) ?
    C21 C26 . 1.4064(18) ?
    C22 C23 . 1.380(2) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.370(2) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.3896(19) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.3843(19) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.5194(16) ?
    C27 H27 . 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
    C1A C2A O2 . . 107.4(5) ?
    C1A C2A H2A1 . . 110.2 ?
    O2 C2A H2A1 . . 110.2 ?
    C1A C2A H2A2 . . 110.2 ?
    O2 C2A H2A2 . . 110.2 ?
    H2A1 C2A H2A2 . . 108.5 ?
    C2B C1B H1B1 . . 109.5 ?
    C2B C1B H1B2 . . 109.5 ?
    H1B1 C1B H1B2 . . 109.5 ?
    C2B C1B H1B3 . . 109.5 ?
    H1B1 C1B H1B3 . . 109.5 ?
    H1B2 C1B H1B3 . . 109.5 ?
    C1B C2B O2 . . 103.0(6) ?
    C1B C2B H2B1 . . 111.2 ?
    O2 C2B H2B1 . . 111.2 ?
    C1B C2B H2B2 . . 111.2 ?
    O2 C2B H2B2 . . 111.2 ?
    H2B1 C2B H2B2 . . 109.1 ?
    O1 C3 O2 . . 123.36(13) ?
    O1 C3 C4 . . 123.34(14) ?
    O2 C3 C4 . . 113.27(12) ?
    C3 C4 C5 . . 111.85(10) ?
    C3 C4 C27 . . 118.71(10) ?
    C5 C4 C27 . . 102.81(9) ?
    C3 C4 H4 . . 107.6 ?
    C5 C4 H4 . . 107.6 ?
    C27 C4 H4 . . 107.6 ?
    N1 C5 C6 . . 105.91(10) ?
    N1 C5 C4 . . 103.94(9) ?
    C6 C5 C4 . . 115.22(11) ?
    N1 C5 H5 . . 110.5 ?
    C6 C5 H5 . . 110.5 ?
    C4 C5 H5 . . 110.5 ?
    C7 C6 C5 . . 103.05(11) ?
    C7 C6 H6A . . 111.2 ?
    C5 C6 H6A . . 111.2 ?
    C7 C6 H6B . . 111.2 ?
    C5 C6 H6B . . 111.2 ?
    H6A C6 H6B . . 109.1 ?
    C8 C7 C6 . . 102.04(12) ?
    C8 C7 H7A . . 111.4 ?
    C6 C7 H7A . . 111.4 ?
    C8 C7 H7B . . 111.4 ?
    C6 C7 H7B . . 111.4 ?
    H7A C7 H7B . . 109.2 ?
    N1 C8 C7 . . 105.66(11) ?
    N1 C8 H8A . . 110.6 ?
    C7 C8 H8A . . 110.6 ?
    N1 C8 H8B . . 110.6 ?
    C7 C8 H8B . . 110.6 ?
    H8A C8 H8B . . 108.7 ?
    N1 C9 C10 . . 116.46(9) ?
    N1 C9 C16 . . 106.22(9) ?
    C10 C9 C16 . . 101.89(9) ?
    N1 C9 C27 . . 104.52(9) ?
    C10 C9 C27 . . 115.18(9) ?
    C16 C9 C27 . . 112.44(9) ?
    C11 C10 C15 . . 119.80(11) ?
    C11 C10 C9 . . 131.67(12) ?
    C15 C10 C9 . . 108.54(10) ?
    C10 C11 C12 . . 118.65(14) ?
    C10 C11 H11 . . 120.7 ?
    C12 C11 H11 . . 120.7 ?
    C13 C12 C11 . . 121.05(14) ?
    C13 C12 H12 . . 119.5 ?
    C11 C12 H12 . . 119.5 ?
    C12 C13 C14 . . 120.93(13) ?
    C12 C13 H13 . . 119.5 ?
    C14 C13 H13 . . 119.5 ?
    C15 C14 C13 . . 117.71(14) ?
    C15 C14 H14 . . 121.1 ?
    C13 C14 H14 . . 121.1 ?
    C14 C15 C10 . . 121.80(13) ?
    C14 C15 N2 . . 127.97(13) ?
    C10 C15 N2 . . 110.23(10) ?
    O4 C16 N2 . . 125.24(12) ?
    O4 C16 C9 . . 126.60(11) ?
    N2 C16 C9 . . 108.07(10) ?
    N2 C17 C18 . . 113.75(12) ?
    N2 C17 H17A . . 108.8 ?
    C18 C17 H17A . . 108.8 ?
    N2 C17 H17B . . 108.8 ?
    C18 C17 H17B . . 108.8 ?
    H17A C17 H17B . . 107.7 ?
    C17 C18 C19 . . 115.73(13) ?
    C17 C18 H18A . . 108.3 ?
    C19 C18 H18A . . 108.3 ?
    C17 C18 H18B . . 108.3 ?
    C19 C18 H18B . . 108.3 ?
    H18A C18 H18B . . 107.4 ?
    C20 C19 C18 . . 116.20(14) ?
    C20 C19 H19A . . 108.2 ?
    C18 C19 H19A . . 108.2 ?
    C20 C19 H19B . . 108.2 ?
    C18 C19 H19B . . 108.2 ?
    H19A C19 H19B . . 107.4 ?
    O3 C20 C19 . . 110.62(13) ?
    O3 C20 H20A . . 109.5 ?
    C19 C20 H20A . . 109.5 ?
    O3 C20 H20B . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 108.1 ?
    O3 C21 C22 . . 123.50(13) ?
    O3 C21 C26 . . 116.04(11) ?
    C22 C21 C26 . . 120.46(13) ?
    C23 C22 C21 . . 120.37(14) ?
    C23 C22 H22 . . 119.8 ?
    C21 C22 H22 . . 119.8 ?
    C24 C23 C22 . . 120.23(14) ?
    C24 C23 H23 . . 119.9 ?
    C22 C23 H23 . . 119.9 ?
    C23 C24 C25 . . 119.26(15) ?
    C23 C24 H24 . . 120.4 ?
    C25 C24 H24 . . 120.4 ?
    C26 C25 C24 . . 122.54(14) ?
    C26 C25 H25 . . 118.7 ?
    C24 C25 H25 . . 118.7 ?
    C25 C26 C21 . . 117.12(12) ?
    C25 C26 C27 . . 121.56(11) ?
    C21 C26 C27 . . 121.25(11) ?
    C26 C27 C4 . . 114.73(10) ?
    C26 C27 C9 . . 117.37(9) ?
    C4 C27 C9 . . 101.60(9) ?
    C26 C27 H27 . . 107.5 ?
    C4 C27 H27 . . 107.5 ?
    C9 C27 H27 . . 107.5 ?
    C5 N1 C8 . . 108.13(10) ?
    C5 N1 C9 . . 110.23(9) ?
    C8 N1 C9 . . 120.66(10) ?
    C16 N2 C15 . . 110.85(10) ?
    C16 N2 C17 . . 123.63(11) ?
    C15 N2 C17 . . 124.23(11) ?
    C3 O2 C2B . . 124.6(5) ?
    C3 O2 C2A . . 111.3(3) ?
    C21 O3 C20 . . 117.33(11) ?
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
    O1 C3 C4 C5 . . . . 89.09(17) ?
    O2 C3 C4 C5 . . . . -89.09(14) ?
    O1 C3 C4 C27 . . . . -151.44(14) ?
    O2 C3 C4 C27 . . . . 30.38(16) ?
    C3 C4 C5 N1 . . . . 165.51(10) ?
    C27 C4 C5 N1 . . . . 37.05(11) ?
    C3 C4 C5 C6 . . . . -79.07(14) ?
    C27 C4 C5 C6 . . . . 152.47(10) ?
    N1 C5 C6 C7 . . . . 28.37(13) ?
    C4 C5 C6 C7 . . . . -85.91(13) ?
    C5 C6 C7 C8 . . . . -38.37(13) ?
    C6 C7 C8 N1 . . . . 34.89(14) ?
    N1 C9 C10 C11 . . . . -70.23(17) ?
    C16 C9 C10 C11 . . . . 174.70(13) ?
    C27 C9 C10 C11 . . . . 52.69(18) ?
    N1 C9 C10 C15 . . . . 110.05(12) ?
    C16 C9 C10 C15 . . . . -5.02(12) ?
    C27 C9 C10 C15 . . . . -127.02(11) ?
    C15 C10 C11 C12 . . . . -1.28(19) ?
    C9 C10 C11 C12 . . . . 179.03(12) ?
    C10 C11 C12 C13 . . . . -1.0(2) ?
    C11 C12 C13 C14 . . . . 1.7(2) ?
    C12 C13 C14 C15 . . . . -0.2(2) ?
    C13 C14 C15 C10 . . . . -2.1(2) ?
    C13 C14 C15 N2 . . . . 178.71(13) ?
    C11 C10 C15 C14 . . . . 2.89(19) ?
    C9 C10 C15 C14 . . . . -177.35(11) ?
    C11 C10 C15 N2 . . . . -177.82(11) ?
    C9 C10 C15 N2 . . . . 1.94(14) ?
    N1 C9 C16 O4 . . . . 60.93(16) ?
    C10 C9 C16 O4 . . . . -176.69(13) ?
    C27 C9 C16 O4 . . . . -52.82(17) ?
    N1 C9 C16 N2 . . . . -115.86(10) ?
    C10 C9 C16 N2 . . . . 6.52(12) ?
    C27 C9 C16 N2 . . . . 130.40(10) ?
    N2 C17 C18 C19 . . . . -66.50(18) ?
    C17 C18 C19 C20 . . . . 97.32(18) ?
    C18 C19 C20 O3 . . . . -76.86(17) ?
    O3 C21 C22 C23 . . . . -177.87(14) ?
    C26 C21 C22 C23 . . . . 2.2(2) ?
    C21 C22 C23 C24 . . . . -0.9(3) ?
    C22 C23 C24 C25 . . . . -0.4(3) ?
    C23 C24 C25 C26 . . . . 0.6(2) ?
    C24 C25 C26 C21 . . . . 0.6(2) ?
    C24 C25 C26 C27 . . . . -176.39(13) ?
    O3 C21 C26 C25 . . . . 178.04(12) ?
    C22 C21 C26 C25 . . . . -1.99(19) ?
    O3 C21 C26 C27 . . . . -4.92(17) ?
    C22 C21 C26 C27 . . . . 175.06(12) ?
    C25 C26 C27 C4 . . . . -2.05(16) ?
    C21 C26 C27 C4 . . . . -178.96(10) ?
    C25 C26 C27 C9 . . . . -121.25(13) ?
    C21 C26 C27 C9 . . . . 61.84(15) ?
    C3 C4 C27 C26 . . . . 67.92(14) ?
    C5 C4 C27 C26 . . . . -168.04(9) ?
    C3 C4 C27 C9 . . . . -164.39(10) ?
    C5 C4 C27 C9 . . . . -40.35(11) ?
    N1 C9 C27 C26 . . . . 155.06(10) ?
    C10 C9 C27 C26 . . . . 25.97(15) ?
    C16 C9 C27 C26 . . . . -90.16(12) ?
    N1 C9 C27 C4 . . . . 29.09(11) ?
    C10 C9 C27 C4 . . . . -99.99(11) ?
    C16 C9 C27 C4 . . . . 143.88(10) ?
    C6 C5 N1 C8 . . . . -6.82(13) ?
    C4 C5 N1 C8 . . . . 115.00(11) ?
    C6 C5 N1 C9 . . . . -140.65(10) ?
    C4 C5 N1 C9 . . . . -18.83(12) ?
    C7 C8 N1 C5 . . . . -17.71(14) ?
    C7 C8 N1 C9 . . . . 110.39(13) ?
    C10 C9 N1 C5 . . . . 121.72(11) ?
    C16 C9 N1 C5 . . . . -125.67(10) ?
    C27 C9 N1 C5 . . . . -6.59(12) ?
    C10 C9 N1 C8 . . . . -5.43(16) ?
    C16 C9 N1 C8 . . . . 107.18(12) ?
    C27 C9 N1 C8 . . . . -133.74(11) ?
    O4 C16 N2 C15 . . . . 177.33(12) ?
    C9 C16 N2 C15 . . . . -5.83(14) ?
    O4 C16 N2 C17 . . . . 9.9(2) ?
    C9 C16 N2 C17 . . . . -173.31(12) ?
    C14 C15 N2 C16 . . . . -178.20(13) ?
    C10 C15 N2 C16 . . . . 2.56(15) ?
    C14 C15 N2 C17 . . . . -10.8(2) ?
    C10 C15 N2 C17 . . . . 169.95(12) ?
    C18 C17 N2 C16 . . . . 96.75(16) ?
    C18 C17 N2 C15 . . . . -69.06(18) ?
    O1 C3 O2 C2B . . . . -9.2(4) ?
    C4 C3 O2 C2B . . . . 169.0(4) ?
    O1 C3 O2 C2A . . . . 8.6(5) ?
    C4 C3 O2 C2A . . . . -173.2(5) ?
    C1B C2B O2 C3 . . . . 106.8(10) ?
    C1B C2B O2 C2A . . . . 52.4(13) ?
    C1A C2A O2 C3 . . . . 167.2(7) ?
    C1A C2A O2 C2B . . . . -58.7(15) ?
    C22 C21 O3 C20 . . . . 1.99(19) ?
    C26 C21 O3 C20 . . . . -178.03(11) ?
    C19 C20 O3 C21 . . . . 173.01(12) ?
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
    C11 H11 O1 2_676 0.93 2.49 3.3957(19) 164.0
    C12 H12 O2 1_655 0.93 2.59 3.446(2) 152.9
    C13 H13 O4 1_655 0.93 2.47 3.3986(17) 174.6
