##############################################################################
#                                                                            #
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1912918'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2018-11-14
_journal_date_accepted     2019-04-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      6
_journal_page_first     751
_journal_page_last     754
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019005826
_journal_coeditor_code     ZP2034
_publ_contact_author_name     'Edwin Weber'
_publ_contact_author_address
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_contact_author_email     'edwin.weber@chemie.tu-freiberg.de'
_publ_contact_author_fax     '+493731393170'
_publ_contact_author_phone     '+493731392386'
_publ_section_title
;\
Crystal structure of dimethyl
N,N'-[(ethyne-1,2-diyl)bis(1,4-phenylenecarbonyl)]bis(L-\
alaninate)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Eißmann, Frank' .
;
TU Bergakademie Freiberg
Leipziger Str. 29
D-09596 Freiberg/Sachsen
Germany
;
    'Seichter, Wilhelm' .
;
TU Bergakademie Freiberg
Leipziger Str. 29
D-09596 Freiberg/Sachsen
Germany
;
    'Weber, Edwin' .
;
TU Bergakademie Freiberg
Leipziger Str. 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_section_synopsis
;
The title compound shows a molecular framework with the diphenylethyne unit
slightly deviating from planarity and the L-alanine moieties adopting a
distorted helical conformation. The crystal structure features a
two-dimensional network supported by N---H...O and C---H...O hydrogen bonding.
;
_chemical_name_systematic
;\
N,N'-[(Ethyne-1,2-diyl)bis(1,4-phenylenecarbonyl)]\
bis(L-alaninate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H24 N2 O6'
_chemical_formula_sum     'C24 H24 N2 O6'
_chemical_formula_iupac     'C24 H24 N2 O6'
_chemical_formula_weight     436.45
_chemical_melting_point     ?
_chemical_absolute_configuration     rm
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     4.9409(4)
_cell_length_b     39.015(3)
_cell_length_c     5.8447(4)
_cell_angle_alpha     90
_cell_angle_beta     100.905(3)
_cell_angle_gamma     90
_cell_volume     1106.34(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2881
_cell_measurement_theta_min     3.55
_cell_measurement_theta_max     26.53
_cell_measurement_temperature     153(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.310
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     460
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_absorpt_correction_T_min     0.9769
_exptl_absorpt_correction_T_max     0.9882
_diffrn_ambient_temperature     153(2)
_diffrn_source     'sealed x-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_device     'four-circle Kappa'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10506
_diffrn_reflns_av_R_equivalents     0.0344
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_theta_min     2.088
_diffrn_reflns_theta_max     28.519
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -52
_diffrn_reflns_limit_k_max     49
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_limit_l_max     7
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_reflns_number_total     5192
_reflns_number_gt     3859
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0785
_refine_ls_R_factor_gt     0.0545
_refine_ls_wR_factor_gt     0.1143
_refine_ls_wR_factor_ref     0.1247
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     5192
_refine_ls_number_parameters     302
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0519P)²+0.3338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.164
_refine_diff_density_min     -0.233
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
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, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.3228(6) 0.27103(7) 1.3737(5) 0.0359(7) Uani d 1 . .
    O O2 -0.1565(8) 0.36026(8) 1.6451(5) 0.0492(9) Uani d 1 . .
    O O3 0.0032(6) 0.34262(6) 1.3334(5) 0.0351(7) Uani d 1 . .
    O O4 0.6614(6) 0.01503(7) 0.0365(6) 0.0438(8) Uani d 1 . .
    O O5 0.5951(6) -0.06167(7) -0.1874(5) 0.0332(6) Uani d 1 . .
    O O6 0.4374(6) -0.05575(7) 0.1439(5) 0.0372(7) Uani d 1 . .
    N N1 0.1280(7) 0.27972(8) 1.5074(6) 0.0262(7) Uani d 1 . .
    H H1 0.301(4) 0.2773(9) 1.489(6) 0.016(9) Uiso d 1 . .
    N N2 0.2024(7) 0.00595(8) -0.0317(6) 0.0275(7) Uani d 1 . .
    H H2 0.039(5) 0.0127(12) -0.002(8) 0.044(13) Uiso d 1 . .
    C C1 0.3251(9) 0.31396(11) 1.8526(7) 0.0395(10) Uani d 1 . .
    H H1A 0.3866 0.2931 1.9401 0.059 Uiso calc 1 . .
    H H1B 0.2791 0.3314 1.9594 0.059 Uiso calc 1 . .
    H H1C 0.4728 0.3225 1.7771 0.059 Uiso calc 1 . .
    C C2 0.0727(8) 0.30608(9) 1.6691(7) 0.0279(8) Uani d 1 . .
    H H2A -0.0708 0.2968 1.7520 0.034 Uiso calc 1 . .
    C C3 -0.0422(8) 0.33900(9) 1.5482(7) 0.0283(8) Uani d 1 . .
    C C4 -0.1041(10) 0.37401(11) 1.2158(7) 0.0420(11) Uani d 1 . .
    H H4A -0.2869 0.3789 1.2501 0.063 Uiso calc 1 . .
    H H4B -0.1182 0.3713 1.0473 0.063 Uiso calc 1 . .
    H H4C 0.0206 0.3931 1.2708 0.063 Uiso calc 1 . .
    C C5 -0.0835(8) 0.26402(9) 1.3680(7) 0.0251(8) Uani d 1 . .
    C C6 -0.0077(8) 0.23641(9) 1.2131(7) 0.0272(9) Uani d 1 . .
    C C7 0.2173(9) 0.21521(9) 1.2828(7) 0.0299(9) Uani d 1 . .
    H H7 0.3311 0.2183 1.4316 0.036 Uiso calc 1 . .
    C C8 0.2781(8) 0.18931(10) 1.1366(7) 0.0312(9) Uani d 1 . .
    H H8 0.4310 0.1746 1.1878 0.037 Uiso calc 1 . .
    C C9 0.1184(8) 0.18472(9) 0.9175(7) 0.0293(8) Uani d 1 . .
    C C10 -0.1098(9) 0.20622(10) 0.8463(8) 0.0356(10) Uani d 1 . .
    H H10 -0.2211 0.2035 0.6960 0.043 Uiso calc 1 . .
    C C11 -0.1735(9) 0.23150(10) 0.9951(7) 0.0320(9) Uani d 1 . .
    H H11 -0.3313 0.2455 0.9477 0.038 Uiso calc 1 . .
    C C12 0.1832(9) 0.15849(9) 0.7647(7) 0.0309(9) Uani d 1 . .
    C C13 0.2348(9) 0.13652(10) 0.6362(7) 0.0327(9) Uani d 1 . .
    C C14 0.2895(9) 0.10953(10) 0.4845(7) 0.0308(9) Uani d 1 . .
    C C15 0.5208(9) 0.08859(11) 0.5503(8) 0.0402(11) Uani d 1 . .
    H H15 0.6465 0.0928 0.6918 0.048 Uiso calc 1 . .
    C C16 0.5651(9) 0.06161(11) 0.4073(8) 0.0414(11) Uani d 1 . .
    H H16 0.7246 0.0477 0.4506 0.050 Uiso calc 1 . .
    C C17 0.3828(8) 0.05450(9) 0.2040(7) 0.0275(8) Uani d 1 . .
    C C18 0.1575(9) 0.07580(10) 0.1360(8) 0.0353(10) Uani d 1 . .
    H H18 0.0335 0.0716 -0.0065 0.042 Uiso calc 1 . .
    C C19 0.1123(9) 0.10325(10) 0.2755(8) 0.0366(10) Uani d 1 . .
    H H19 -0.0417 0.1179 0.2269 0.044 Uiso calc 1 . .
    C C20 0.4274(8) 0.02379(9) 0.0616(7) 0.0287(9) Uani d 1 . .
    C C21 0.2291(10) -0.01405(12) -0.4265(7) 0.0432(11) Uani d 1 . .
    H H21A 0.0730 0.0008 -0.4902 0.065 Uiso calc 1 . .
    H H21B 0.2231 -0.0348 -0.5222 0.065 Uiso calc 1 . .
    H H21C 0.4019 -0.0018 -0.4272 0.065 Uiso calc 1 . .
    C C22 0.2127(8) -0.02395(9) -0.1792(6) 0.0266(8) Uani d 1 . .
    H H22 0.0349 -0.0365 -0.1866 0.032 Uiso calc 1 . .
    C C23 0.4398(8) -0.04847(9) -0.0795(6) 0.0260(8) Uani d 1 . .
    C C24 0.6460(10) -0.07959(11) 0.2541(7) 0.0441(11) Uani d 1 . .
    H H24A 0.6093 -0.1023 0.1831 0.066 Uiso calc 1 . .
    H H24B 0.6422 -0.0810 0.4209 0.066 Uiso calc 1 . .
    H H24C 0.8278 -0.0716 0.2330 0.066 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 C5 . 1.220(5) ?
    O2 C3 . 1.203(5) ?
    O3 C3 . 1.324(5) ?
    O3 C4 . 1.455(5) ?
    O4 C20 . 1.241(5) ?
    O5 C23 . 1.198(4) ?
    O6 C23 . 1.338(4) ?
    O6 C24 . 1.446(5) ?
    N1 C5 . 1.345(5) ?
    N1 C2 . 1.457(4) ?
    N1 H1 . 0.886(14) ?
    N2 C20 . 1.337(5) ?
    N2 C22 . 1.457(5) ?
    N2 H2 . 0.894(14) ?
    C1 C2 . 1.514(6) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 C3 . 1.523(5) ?
    C2 H2A . 1.0000 ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C5 C6 . 1.499(5) ?
    C6 C7 . 1.384(5) ?
    C6 C11 . 1.392(6) ?
    C7 C8 . 1.393(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.383(6) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.404(6) ?
    C9 C12 . 1.433(5) ?
    C10 C11 . 1.390(5) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.198(5) ?
    C13 C14 . 1.435(5) ?
    C14 C19 . 1.384(6) ?
    C14 C15 . 1.398(6) ?
    C15 C16 . 1.387(6) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.377(6) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.386(6) ?
    C17 C20 . 1.499(5) ?
    C18 C19 . 1.390(6) ?
    C18 H18 . 0.9500 ?
    C19 H19 . 0.9500 ?
    C21 C22 . 1.513(6) ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 C23 . 1.505(5) ?
    C22 H22 . 1.0000 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 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
    C3 O3 C4 . . 115.2(3) ?
    C23 O6 C24 . . 115.7(3) ?
    C5 N1 C2 . . 119.7(3) ?
    C5 N1 H1 . . 122(2) ?
    C2 N1 H1 . . 117(2) ?
    C20 N2 C22 . . 122.6(3) ?
    C20 N2 H2 . . 119(3) ?
    C22 N2 H2 . . 119(3) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C1 . . 111.9(3) ?
    N1 C2 C3 . . 113.2(3) ?
    C1 C2 C3 . . 110.0(3) ?
    N1 C2 H2A . . 107.2 ?
    C1 C2 H2A . . 107.2 ?
    C3 C2 H2A . . 107.2 ?
    O2 C3 O3 . . 123.5(4) ?
    O2 C3 C2 . . 122.0(3) ?
    O3 C3 C2 . . 114.5(3) ?
    O3 C4 H4A . . 109.5 ?
    O3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    O3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    O1 C5 N1 . . 121.8(3) ?
    O1 C5 C6 . . 122.1(4) ?
    N1 C5 C6 . . 116.0(3) ?
    C7 C6 C11 . . 119.2(3) ?
    C7 C6 C5 . . 122.0(4) ?
    C11 C6 C5 . . 118.7(3) ?
    C6 C7 C8 . . 120.5(4) ?
    C6 C7 H7 . . 119.7 ?
    C8 C7 H7 . . 119.7 ?
    C9 C8 C7 . . 120.7(4) ?
    C9 C8 H8 . . 119.6 ?
    C7 C8 H8 . . 119.6 ?
    C8 C9 C10 . . 118.9(4) ?
    C8 C9 C12 . . 120.9(4) ?
    C10 C9 C12 . . 120.2(4) ?
    C11 C10 C9 . . 120.2(4) ?
    C11 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    C10 C11 C6 . . 120.5(4) ?
    C10 C11 H11 . . 119.8 ?
    C6 C11 H11 . . 119.8 ?
    C13 C12 C9 . . 179.4(5) ?
    C12 C13 C14 . . 178.1(4) ?
    C19 C14 C15 . . 119.2(4) ?
    C19 C14 C13 . . 120.9(4) ?
    C15 C14 C13 . . 119.9(4) ?
    C16 C15 C14 . . 119.4(4) ?
    C16 C15 H15 . . 120.3 ?
    C14 C15 H15 . . 120.3 ?
    C17 C16 C15 . . 121.4(4) ?
    C17 C16 H16 . . 119.3 ?
    C15 C16 H16 . . 119.3 ?
    C16 C17 C18 . . 119.1(4) ?
    C16 C17 C20 . . 120.0(4) ?
    C18 C17 C20 . . 121.0(4) ?
    C17 C18 C19 . . 120.2(4) ?
    C17 C18 H18 . . 119.9 ?
    C19 C18 H18 . . 119.9 ?
    C14 C19 C18 . . 120.6(4) ?
    C14 C19 H19 . . 119.7 ?
    C18 C19 H19 . . 119.7 ?
    O4 C20 N2 . . 122.0(3) ?
    O4 C20 C17 . . 121.6(3) ?
    N2 C20 C17 . . 116.4(3) ?
    C22 C21 H21A . . 109.5 ?
    C22 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C22 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    N2 C22 C23 . . 112.7(3) ?
    N2 C22 C21 . . 112.0(3) ?
    C23 C22 C21 . . 111.2(3) ?
    N2 C22 H22 . . 106.8 ?
    C23 C22 H22 . . 106.8 ?
    C21 C22 H22 . . 106.8 ?
    O5 C23 O6 . . 123.2(4) ?
    O5 C23 C22 . . 125.0(3) ?
    O6 C23 C22 . . 111.6(3) ?
    O6 C24 H24A . . 109.5 ?
    O6 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    O6 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 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
    C5 N1 C2 C1 . . . . 164.9(3) ?
    C5 N1 C2 C3 . . . . -70.2(4) ?
    C4 O3 C3 O2 . . . . -2.1(6) ?
    C4 O3 C3 C2 . . . . -179.7(3) ?
    N1 C2 C3 O2 . . . . 162.9(4) ?
    C1 C2 C3 O2 . . . . -71.1(5) ?
    N1 C2 C3 O3 . . . . -19.4(5) ?
    C1 C2 C3 O3 . . . . 106.5(4) ?
    C2 N1 C5 O1 . . . . -0.6(5) ?
    C2 N1 C5 C6 . . . . -178.0(3) ?
    O1 C5 C6 C7 . . . . -142.9(4) ?
    N1 C5 C6 C7 . . . . 34.5(5) ?
    O1 C5 C6 C11 . . . . 35.5(6) ?
    N1 C5 C6 C11 . . . . -147.1(4) ?
    C11 C6 C7 C8 . . . . 0.2(6) ?
    C5 C6 C7 C8 . . . . 178.5(3) ?
    C6 C7 C8 C9 . . . . 1.3(6) ?
    C7 C8 C9 C10 . . . . -1.2(6) ?
    C7 C8 C9 C12 . . . . 178.9(4) ?
    C8 C9 C10 C11 . . . . -0.3(6) ?
    C12 C9 C10 C11 . . . . 179.6(4) ?
    C9 C10 C11 C6 . . . . 1.8(6) ?
    C7 C6 C11 C10 . . . . -1.8(6) ?
    C5 C6 C11 C10 . . . . 179.8(4) ?
    C19 C14 C15 C16 . . . . -1.2(7) ?
    C13 C14 C15 C16 . . . . 177.1(4) ?
    C14 C15 C16 C17 . . . . -1.4(7) ?
    C15 C16 C17 C18 . . . . 3.1(7) ?
    C15 C16 C17 C20 . . . . -176.0(4) ?
    C16 C17 C18 C19 . . . . -2.1(6) ?
    C20 C17 C18 C19 . . . . 177.0(4) ?
    C15 C14 C19 C18 . . . . 2.2(7) ?
    C13 C14 C19 C18 . . . . -176.1(4) ?
    C17 C18 C19 C14 . . . . -0.6(7) ?
    C22 N2 C20 O4 . . . . -3.3(6) ?
    C22 N2 C20 C17 . . . . 178.3(3) ?
    C16 C17 C20 O4 . . . . -38.6(6) ?
    C18 C17 C20 O4 . . . . 142.3(4) ?
    C16 C17 C20 N2 . . . . 139.8(4) ?
    C18 C17 C20 N2 . . . . -39.3(5) ?
    C20 N2 C22 C23 . . . . 46.3(5) ?
    C20 N2 C22 C21 . . . . -80.0(5) ?
    C24 O6 C23 O5 . . . . 3.1(5) ?
    C24 O6 C23 C22 . . . . 179.1(3) ?
    N2 C22 C23 O5 . . . . -134.7(4) ?
    C21 C22 C23 O5 . . . . -7.9(5) ?
    N2 C22 C23 O6 . . . . 49.4(4) ?
    C21 C22 C23 O6 . . . . 176.2(3) ?
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
    N1 H1 O1 1_655 0.886(14) 2.108(16) 2.982(4) 168(3)
    N2 H2 O4 1_455 0.894(14) 1.926(19) 2.799(4) 165(5)
    C1 H1C O2 1_655 0.98 2.58 3.532(6) 163.7
    C4 H4B O2 1_554 0.98 2.36 3.340(5) 175.8
    C21 H21B O6 1_554 0.98 2.53 3.315(5) 137.4
    C22 H22 O5 1_455 1.00 2.38 3.380(5) 174.4
    C24 H24B O5 1_556 0.98 2.46 3.394(5) 158.4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.977
_shelx_estimated_absorpt_T_max     0.988
