##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     'APEX2 v2014.11-0'
_journal_date_recd_electronic     2016-01-20
_journal_date_accepted     2016-02-15
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      2
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616002704
_journal_coeditor_code     ZP4002
_publ_contact_author_name
;
Mustafa R. Albayati
;
_publ_contact_author_address
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
_publ_contact_author_email     'shaabankamel@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Diethyl
3-amino-6-methyl-4-[(E)-2-phenylethenyl]thieno[2,3-b]pyridine-\
2,5-dicarboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Joel T. Mague'
;
Department of Chemistry,
Tulane University,
New Orleans,
LA 70118,
USA
;
    'Mohamed, Shaaban K.'
;
Chemistry and Environmental Division,
Manchester Metropolitan University,
Manchester M1 5GD,
England
Chemistry Department,
Faculty of Science,
Minia University,
61519 El-Minia,
Egypt
;
    'Akkurt, Mehmet'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Etify A. Bakhite'
;
Chemistry Department,
Faculty of Science,
Assiut  University,
Assiut 71516,
Egypt
;
    'Mustafa R. Albayati'
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
_publ_section_synopsis
;
The bicyclic core of the title compound is slightly folded [1.9(1)°], while
pairwise intermolecular N---H...O hydrogen bonding forms dimers across centers
of symmetry.
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1453514'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;\
Diethyl 3-amino-6-methyl-4-[(E)-2-phenylethenyl]thieno[2,3-b]\
pyridine-2,5-dicarboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H22 N2 O4 S'
_chemical_formula_sum     'C22 H22 N2 O4 S'
_chemical_formula_iupac     'C22 H22 N2 O4 S'
_chemical_formula_weight     410.47
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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     5.6473(2)
_cell_length_b     26.7798(9)
_cell_length_c     13.3219(4)
_cell_angle_alpha     90
_cell_angle_beta     99.743(2)
_cell_angle_gamma     90
_cell_volume     1985.66(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9033
_cell_measurement_theta_min     3.3006
_cell_measurement_theta_max     71.9828
_cell_measurement_temperature     150.(2)
_exptl_crystal_description     column
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.202
_exptl_crystal_size_mid     0.080
_exptl_crystal_size_min     0.045
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     1.717
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_shelx_estimated_absorpt_T_min     0.723
_shelx_estimated_absorpt_T_max     0.927
_exptl_absorpt_correction_T_min     0.81
_exptl_absorpt_correction_T_max     0.93
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.4167
_diffrn_reflns_number     14981
_diffrn_reflns_av_R_equivalents     0.0394
_diffrn_reflns_theta_min     3.300
_diffrn_reflns_theta_max     71.976
_diffrn_reflns_theta_full     70.000
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -33
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     14
_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 > 2sigma(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. H-atoms were placed in
calculated positions (C---H = 0.95 - 0.99 Å) and included as riding
contributions with isotropic displacement parameters 1.2 - 1.5 times those
of the attached carbon atoms.
;
_reflns_number_total     3830
_reflns_number_gt     3158
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0481
_refine_ls_R_factor_gt     0.0372
_refine_ls_wR_factor_gt     0.0876
_refine_ls_wR_factor_ref     0.0936
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     3830
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0443P)²+0.6171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_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     0.171
_refine_diff_density_min     -0.307
_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'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 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
    S S1 0.81665(7) 0.31695(2) 0.51587(3) 0.02555(12) Uani d 1 . .
    O O1 -0.0116(2) 0.37752(4) 0.80094(9) 0.0313(3) Uani d 1 . .
    O O2 0.1931(2) 0.31306(4) 0.88190(9) 0.0261(3) Uani d 1 . .
    O O3 1.0260(3) 0.45058(5) 0.44348(11) 0.0373(3) Uani d 1 . .
    O O4 1.1080(2) 0.37241(4) 0.39666(9) 0.0292(3) Uani d 1 . .
    N N1 0.5078(2) 0.28245(5) 0.63005(10) 0.0247(3) Uani d 1 . .
    N N2 0.6910(3) 0.45759(5) 0.57515(13) 0.0316(3) Uani d 1 . .
    H H2A 0.601(4) 0.4709(8) 0.6114(17) 0.039(6) Uiso d 1 . .
    H H2B 0.789(4) 0.4766(8) 0.5425(17) 0.043(6) Uiso d 1 . .
    C C1 0.4979(3) 0.50473(6) 0.84071(12) 0.0232(3) Uani d 1 . .
    C C2 0.6874(3) 0.52120(6) 0.91401(13) 0.0257(3) Uani d 1 . .
    H H2 0.8334 0.5028 0.9252 0.031 Uiso calc 1 . .
    C C3 0.6674(3) 0.56382(6) 0.97084(13) 0.0301(4) Uani d 1 . .
    H H3 0.7980 0.5742 1.0211 0.036 Uiso calc 1 . .
    C C4 0.4573(3) 0.59124(6) 0.95430(14) 0.0313(4) Uani d 1 . .
    H H4 0.4420 0.6203 0.9937 0.038 Uiso calc 1 . .
    C C5 0.2685(3) 0.57614(7) 0.87975(14) 0.0328(4) Uani d 1 . .
    H H5 0.1250 0.5953 0.8672 0.039 Uiso calc 1 . .
    C C6 0.2883(3) 0.53313(6) 0.82343(13) 0.0290(4) Uani d 1 . .
    H H6 0.1580 0.5230 0.7728 0.035 Uiso calc 1 . .
    C C7 0.5254(3) 0.45678(6) 0.79016(12) 0.0241(3) Uani d 1 . .
    H H7 0.6806 0.4421 0.8031 0.029 Uiso calc 1 . .
    C C8 0.3566(3) 0.43171(6) 0.72829(12) 0.0226(3) Uani d 1 . .
    H H8 0.2029 0.4464 0.7081 0.027 Uiso calc 1 . .
    C C9 0.4041(3) 0.38108(6) 0.69013(12) 0.0211(3) Uani d 1 . .
    C C10 0.5636(3) 0.37290(6) 0.62112(12) 0.0217(3) Uani d 1 . .
    C C11 0.6091(3) 0.32310(6) 0.59683(12) 0.0226(3) Uani d 1 . .
    C C12 0.3520(3) 0.29013(6) 0.69361(12) 0.0240(3) Uani d 1 . .
    C C13 0.3009(3) 0.33872(6) 0.72724(12) 0.0217(3) Uani d 1 . .
    C C14 0.2322(3) 0.24380(6) 0.72435(14) 0.0322(4) Uani d 1 . .
    H H14A 0.2435 0.2172 0.6749 0.048 Uiso calc 1 . .
    H H14B 0.0627 0.2509 0.7262 0.048 Uiso calc 1 . .
    H H14C 0.3122 0.2331 0.7920 0.048 Uiso calc 1 . .
    C C15 0.7021(3) 0.40730(6) 0.56948(12) 0.0228(3) Uani d 1 . .
    C C16 0.8451(3) 0.38195(6) 0.51149(12) 0.0242(3) Uani d 1 . .
    C C17 0.9986(3) 0.40561(6) 0.44930(13) 0.0255(3) Uani d 1 . .
    C C18 1.2648(3) 0.39335(7) 0.33177(13) 0.0296(4) Uani d 1 . .
    H H18A 1.4040 0.4101 0.3735 0.035 Uiso calc 1 . .
    H H18B 1.1768 0.4182 0.2845 0.035 Uiso calc 1 . .
    C C19 1.3474(4) 0.35096(8) 0.27367(17) 0.0456(5) Uani d 1 . .
    H H19A 1.4366 0.3270 0.3213 0.068 Uiso calc 1 . .
    H H19B 1.4520 0.3637 0.2278 0.068 Uiso calc 1 . .
    H H19C 1.2077 0.3344 0.2337 0.068 Uiso calc 1 . .
    C C20 0.1416(3) 0.34570(6) 0.80479(12) 0.0227(3) Uani d 1 . .
    C C21 0.0355(3) 0.31326(7) 0.95820(13) 0.0282(4) Uani d 1 . .
    H H21A -0.0058 0.3481 0.9729 0.034 Uiso calc 1 . .
    H H21B 0.1207 0.2983 1.0221 0.034 Uiso calc 1 . .
    C C22 -0.1910(3) 0.28440(7) 0.92170(14) 0.0335(4) Uani d 1 . .
    H H22A -0.2796 0.3003 0.8604 0.050 Uiso calc 1 . .
    H H22B -0.2910 0.2841 0.9751 0.050 Uiso calc 1 . .
    H H22C -0.1500 0.2501 0.9059 0.050 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
    S1 C11 . 1.7297(17) ?
    S1 C16 . 1.7498(16) ?
    O1 C20 . 1.209(2) ?
    O2 C20 . 1.3428(19) ?
    O2 C21 . 1.4601(19) ?
    O3 C17 . 1.218(2) ?
    O4 C17 . 1.346(2) ?
    O4 C18 . 1.451(2) ?
    N1 C12 . 1.336(2) ?
    N1 C11 . 1.339(2) ?
    N2 C15 . 1.351(2) ?
    N2 H2A . 0.84(2) ?
    N2 H2B . 0.92(2) ?
    C1 C6 . 1.393(2) ?
    C1 C2 . 1.393(2) ?
    C1 C7 . 1.470(2) ?
    C2 C3 . 1.385(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.381(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.389(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.389(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.331(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.488(2) ?
    C8 H8 . 0.9500 ?
    C9 C13 . 1.403(2) ?
    C9 C10 . 1.409(2) ?
    C10 C11 . 1.406(2) ?
    C10 C15 . 1.455(2) ?
    C12 C13 . 1.421(2) ?
    C12 C14 . 1.503(2) ?
    C13 C20 . 1.492(2) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 C16 . 1.386(2) ?
    C16 C17 . 1.443(2) ?
    C18 C19 . 1.492(3) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C21 C22 . 1.503(2) ?
    C21 H21A . 0.9900 ?
    C21 H21B . 0.9900 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 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
    C11 S1 C16 . . 90.11(8) ?
    C20 O2 C21 . . 116.82(13) ?
    C17 O4 C18 . . 115.82(13) ?
    C12 N1 C11 . . 116.63(14) ?
    C15 N2 H2A . . 119.6(15) ?
    C15 N2 H2B . . 119.4(14) ?
    H2A N2 H2B . . 121(2) ?
    C6 C1 C2 . . 118.27(15) ?
    C6 C1 C7 . . 123.63(15) ?
    C2 C1 C7 . . 118.00(15) ?
    C3 C2 C1 . . 121.34(16) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C4 C3 C2 . . 119.90(16) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C3 C4 C5 . . 119.62(16) ?
    C3 C4 H4 . . 120.2 ?
    C5 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 120.36(17) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C5 C6 C1 . . 120.48(16) ?
    C5 C6 H6 . . 119.8 ?
    C1 C6 H6 . . 119.8 ?
    C8 C7 C1 . . 127.15(15) ?
    C8 C7 H7 . . 116.4 ?
    C1 C7 H7 . . 116.4 ?
    C7 C8 C9 . . 121.31(14) ?
    C7 C8 H8 . . 119.3 ?
    C9 C8 H8 . . 119.3 ?
    C13 C9 C10 . . 116.98(14) ?
    C13 C9 C8 . . 120.46(14) ?
    C10 C9 C8 . . 122.44(14) ?
    C11 C10 C9 . . 117.36(14) ?
    C11 C10 C15 . . 110.97(14) ?
    C9 C10 C15 . . 131.64(14) ?
    N1 C11 C10 . . 126.14(15) ?
    N1 C11 S1 . . 120.07(12) ?
    C10 C11 S1 . . 113.79(12) ?
    N1 C12 C13 . . 122.07(15) ?
    N1 C12 C14 . . 114.88(14) ?
    C13 C12 C14 . . 123.03(15) ?
    C9 C13 C12 . . 120.71(15) ?
    C9 C13 C20 . . 118.53(14) ?
    C12 C13 C20 . . 120.75(14) ?
    C12 C14 H14A . . 109.5 ?
    C12 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C12 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    N2 C15 C16 . . 123.83(16) ?
    N2 C15 C10 . . 124.82(15) ?
    C16 C15 C10 . . 111.34(14) ?
    C15 C16 C17 . . 124.61(15) ?
    C15 C16 S1 . . 113.78(12) ?
    C17 C16 S1 . . 121.57(12) ?
    O3 C17 O4 . . 123.05(16) ?
    O3 C17 C16 . . 124.46(16) ?
    O4 C17 C16 . . 112.48(14) ?
    O4 C18 C19 . . 106.91(15) ?
    O4 C18 H18A . . 110.3 ?
    C19 C18 H18A . . 110.3 ?
    O4 C18 H18B . . 110.3 ?
    C19 C18 H18B . . 110.3 ?
    H18A C18 H18B . . 108.6 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O1 C20 O2 . . 123.53(15) ?
    O1 C20 C13 . . 124.74(15) ?
    O2 C20 C13 . . 111.70(13) ?
    O2 C21 C22 . . 111.01(14) ?
    O2 C21 H21A . . 109.4 ?
    C22 C21 H21A . . 109.4 ?
    O2 C21 H21B . . 109.4 ?
    C22 C21 H21B . . 109.4 ?
    H21A C21 H21B . . 108.0 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 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
    C6 C1 C2 C3 . . . . 1.9(3) ?
    C7 C1 C2 C3 . . . . -174.57(16) ?
    C1 C2 C3 C4 . . . . -0.9(3) ?
    C2 C3 C4 C5 . . . . -0.8(3) ?
    C3 C4 C5 C6 . . . . 1.4(3) ?
    C4 C5 C6 C1 . . . . -0.2(3) ?
    C2 C1 C6 C5 . . . . -1.4(3) ?
    C7 C1 C6 C5 . . . . 174.92(17) ?
    C6 C1 C7 C8 . . . . -5.4(3) ?
    C2 C1 C7 C8 . . . . 170.89(17) ?
    C1 C7 C8 C9 . . . . -174.13(16) ?
    C7 C8 C9 C13 . . . . 107.59(19) ?
    C7 C8 C9 C10 . . . . -68.3(2) ?
    C13 C9 C10 C11 . . . . -1.1(2) ?
    C8 C9 C10 C11 . . . . 174.93(14) ?
    C13 C9 C10 C15 . . . . -179.21(15) ?
    C8 C9 C10 C15 . . . . -3.1(3) ?
    C12 N1 C11 C10 . . . . -1.2(2) ?
    C12 N1 C11 S1 . . . . 178.99(12) ?
    C9 C10 C11 N1 . . . . 2.8(2) ?
    C15 C10 C11 N1 . . . . -178.75(15) ?
    C9 C10 C11 S1 . . . . -177.40(11) ?
    C15 C10 C11 S1 . . . . 1.06(17) ?
    C16 S1 C11 N1 . . . . 179.19(14) ?
    C16 S1 C11 C10 . . . . -0.63(13) ?
    C11 N1 C12 C13 . . . . -1.9(2) ?
    C11 N1 C12 C14 . . . . 176.71(14) ?
    C10 C9 C13 C12 . . . . -1.7(2) ?
    C8 C9 C13 C12 . . . . -177.87(14) ?
    C10 C9 C13 C20 . . . . 176.70(13) ?
    C8 C9 C13 C20 . . . . 0.6(2) ?
    N1 C12 C13 C9 . . . . 3.5(2) ?
    C14 C12 C13 C9 . . . . -175.08(15) ?
    N1 C12 C13 C20 . . . . -174.94(14) ?
    C14 C12 C13 C20 . . . . 6.5(2) ?
    C11 C10 C15 N2 . . . . 177.80(16) ?
    C9 C10 C15 N2 . . . . -4.0(3) ?
    C11 C10 C15 C16 . . . . -1.02(19) ?
    C9 C10 C15 C16 . . . . 177.15(16) ?
    N2 C15 C16 C17 . . . . -0.5(3) ?
    C10 C15 C16 C17 . . . . 178.33(15) ?
    N2 C15 C16 S1 . . . . -178.27(14) ?
    C10 C15 C16 S1 . . . . 0.57(18) ?
    C11 S1 C16 C15 . . . . 0.02(13) ?
    C11 S1 C16 C17 . . . . -177.82(14) ?
    C18 O4 C17 O3 . . . . 0.4(2) ?
    C18 O4 C17 C16 . . . . 179.71(13) ?
    C15 C16 C17 O3 . . . . 2.6(3) ?
    S1 C16 C17 O3 . . . . -179.77(15) ?
    C15 C16 C17 O4 . . . . -176.65(15) ?
    S1 C16 C17 O4 . . . . 0.9(2) ?
    C17 O4 C18 C19 . . . . -174.66(15) ?
    C21 O2 C20 O1 . . . . 7.0(2) ?
    C21 O2 C20 C13 . . . . -174.78(13) ?
    C9 C13 C20 O1 . . . . 43.9(2) ?
    C12 C13 C20 O1 . . . . -137.68(17) ?
    C9 C13 C20 O2 . . . . -134.31(14) ?
    C12 C13 C20 O2 . . . . 44.1(2) ?
    C20 O2 C21 C22 . . . . 80.53(18) ?
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
    N2 H2B O3 . 0.92(2) 2.15(2) 2.796(2) 127.0(18)
    N2 H2B O3 3_766 0.92(2) 2.20(2) 2.966(2) 140.2(19)
    C19 H19B Cg1 3_766 0.98 2.95 3.766(2) 141
    C22 H22A Cg2 1_455 0.98 2.95 3.9206(19) 170
    C7 H7 O1 1_655 0.95 2.46 3.352(2) 157
