##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# are given in the paper "The Crystallographic Information File (CIF):       #
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# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-09-19
_journal_date_accepted     2006-10-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     11
_journal_page_first     o5167
_journal_page_last     o5168
_journal_paper_category     EO
_journal_coeditor_code     AC2055
_publ_contact_author_name     'Sun Feng-xia'
_publ_contact_author_address
;  College of Chemical and Pharmaceutical Engineering,
Hebei University of Science and Technology
  Shijiazhuang 050018
  People's Republic of China
;
_publ_contact_author_email     fxsun001@163.com
_publ_contact_author_fax     '0086-311-88632176'
_publ_contact_author_phone     '0086-311-85683592'
_publ_section_title
;
Ethyl 5-(2-hydroxyethylcarbamoyl)-2,6-dimethyl-4-(3-nitrophenyl)-
1,4-dihydropyridine-3-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sun, Feng-Xia' .
; College of Chemical and Pharmaceutical Engineering,
Hebei University of Science and Technology
  Shijiazhuang 050018
  People's Republic of China
;
    'Yu, Yi-Feng' .
; College of Chemical and Pharmaceutical Engineering,
  Hebei University of Science and Technology
  Shijiazhuang 050018
  People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 5-(2-hydroxyethylcarbamoyl)-2,6-dimethyl-4-(3-nitrophenyl)-
1,4-dihydropyridine-3-carboxylate
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C19 H23 N3 O6'
_chemical_formula_sum     'C19 H23 N3 O6'
_chemical_formula_iupac     'C19 H23 N3 O6'
_chemical_formula_weight     389.40
_chemical_melting_point        .465E-305
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x, -y, z+1/2'
_cell_length_a     14.259(3)
_cell_length_b     14.935(3)
_cell_length_c     8.7829(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1870.4(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5970
_cell_measurement_theta_min     2.0
_cell_measurement_theta_max     27.9
_cell_measurement_temperature     113(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Jacobson, 1998)'
_exptl_absorpt_correction_T_min     0.9815
_exptl_absorpt_correction_T_max     0.9856
_exptl_special_details
;
;
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     confocal
_diffrn_measurement_device_type     'Rigaku Saturn'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     22635
_diffrn_reflns_av_R_equivalents     0.0442
_diffrn_reflns_av_sigmaI/netI     0.0267
_diffrn_reflns_theta_min     1.97
_diffrn_reflns_theta_max     27.88
_diffrn_reflns_theta_full     27.88
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     2376
_reflns_number_gt     2215
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0427
_refine_ls_R_factor_gt     0.0396
_refine_ls_wR_factor_gt     0.1004
_refine_ls_wR_factor_ref     0.1029
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.105
_refine_ls_number_reflns     2376
_refine_ls_number_parameters     280
_refine_ls_number_restraints     37
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0703P)²+0.107P] 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     0.000
_refine_diff_density_max     0.377
_refine_diff_density_min     -0.358
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.034(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'None, Friedel Pairs merged'
_refine_ls_abs_structure_Flack     ?
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     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     CrystalClear
_computing_data_reduction     CrystalClear
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CrystalStructure (Rigaku/MSC, 2005)'
_computing_publication_material     CrystalStructure
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 0.60229(11) 0.78841(11) 0.3496(2) 0.0226(4) Uani d . 1 . .
    O O2 0.48802(10) 0.87779(10) 0.2612(2) 0.0190(4) Uani d . 1 . .
    O O3 0.41200(12) 0.49150(11) 0.7379(2) 0.0238(4) Uani d . 1 . .
    O O5 0.80446(15) 0.66705(17) 0.9575(3) 0.0448(6) Uani d . 1 . .
    O O6 0.80209(14) 0.60324(15) 0.7394(3) 0.0441(6) Uani d . 1 . .
    N N1 0.29157(13) 0.70716(13) 0.4714(3) 0.0206(4) Uani d . 1 . .
    N N2 0.51375(16) 0.47801(13) 0.5431(3) 0.0232(5) Uani d D 1 A .
    N N3 0.76582(14) 0.64972(14) 0.8378(3) 0.0281(5) Uani d . 1 . .
    C C1 0.35217(15) 0.76673(14) 0.4057(3) 0.0168(4) Uani d . 1 . .
    C C2 0.44659(15) 0.75100(14) 0.4117(3) 0.0156(4) Uani d . 1 . .
    C C3 0.48731(15) 0.67124(14) 0.4966(3) 0.0161(4) Uani d . 1 . .
    H H3 0.5323 0.6399 0.4273 0.019 Uiso calc R 1 . .
    C C4 0.41131(16) 0.60472(15) 0.5428(3) 0.0174(5) Uani d . 1 . .
    C C5 0.31932(16) 0.62519(16) 0.5336(3) 0.0195(5) Uani d . 1 . .
    C C6 0.30303(15) 0.84488(15) 0.3323(3) 0.0214(5) Uani d . 1 . .
    H H6A 0.3157 0.8994 0.3908 0.032 Uiso calc R 1 . .
    H H6B 0.2353 0.8336 0.3303 0.032 Uiso calc R 1 . .
    H H6C 0.3261 0.8524 0.2280 0.032 Uiso calc R 1 . .
    C C7 0.23875(18) 0.56736(17) 0.5814(3) 0.0278(6) Uani d . 1 . .
    H H7A 0.2614 0.5067 0.6027 0.042 Uiso calc R 1 . .
    H H7B 0.1922 0.5652 0.4994 0.042 Uiso calc R 1 . .
    H H7C 0.2099 0.5923 0.6733 0.042 Uiso calc R 1 . .
    C C8 0.51879(14) 0.80617(14) 0.3402(3) 0.0162(4) Uani d . 1 . .
    C C9 0.55982(16) 0.93532(16) 0.1955(3) 0.0214(5) Uani d . 1 . .
    H H9A 0.6024 0.9001 0.1296 0.026 Uiso calc R 1 . .
    H H9B 0.5974 0.9639 0.2769 0.026 Uiso calc R 1 . .
    C C10 0.5094(2) 1.00456(19) 0.1043(4) 0.0311(6) Uani d . 1 . .
    H H10A 0.4710 0.9752 0.0264 0.047 Uiso calc R 1 . .
    H H10B 0.5552 1.0440 0.0550 0.047 Uiso calc R 1 . .
    H H10C 0.4690 1.0400 0.1715 0.047 Uiso calc R 1 . .
    C C11 0.44394(16) 0.51984(15) 0.6150(3) 0.0189(5) Uani d . 1 . .
    C C12 0.56635(19) 0.40470(18) 0.6122(4) 0.0347(7) Uani d D 1 . .
    H H12A 0.5256 0.3539 0.6225 0.042 Uiso d PR 0.735(4) A 1
    H H12B 0.5857 0.4223 0.7125 0.042 Uiso d PR 0.735(4) A 1
    H H12C 0.5428 0.3489 0.5737 0.042 Uiso d PR 0.265(4) A 2
    H H12D 0.5563 0.4055 0.7202 0.042 Uiso d PR 0.265(4) A 2
    C C14 0.53998(15) 0.69863(14) 0.6400(3) 0.0169(4) Uani d . 1 . .
    C C15 0.62852(16) 0.66335(15) 0.6722(3) 0.0188(5) Uani d . 1 . .
    H H15 0.6586 0.6243 0.6021 0.023 Uiso calc R 1 . .
    C C16 0.67181(16) 0.68634(16) 0.8085(3) 0.0224(5) Uani d . 1 . .
    C C17 0.63132(18) 0.74202(17) 0.9149(3) 0.0285(6) Uani d . 1 . .
    H H17 0.6624 0.7558 1.0077 0.034 Uiso calc R 1 . .
    C C18 0.54349(19) 0.77725(18) 0.8819(4) 0.0318(6) Uani d . 1 . .
    H H18 0.5137 0.8160 0.9527 0.038 Uiso calc R 1 . .
    C C19 0.49904(17) 0.75604(16) 0.7461(3) 0.0236(5) Uani d . 1 . .
    H H19 0.4393 0.7812 0.7248 0.028 Uiso calc R 1 . .
    C C13 0.6500(4) 0.3792(3) 0.5261(8) 0.0510(14) Uani d PDU 0.735(4) A 1
    H H13A 0.6871 0.3376 0.5900 0.061 Uiso calc PR 0.735(4) A 1
    H H13B 0.6292 0.3452 0.4354 0.061 Uiso calc PR 0.735(4) A 1
    O O4 0.70950(19) 0.4469(2) 0.4770(4) 0.0431(7) Uani d PDU 0.735(4) A 1
    H H4A 0.6865 0.4716 0.3997 0.065 Uiso calc PR 0.735(4) A 1
    C C13' 0.6706(5) 0.4112(7) 0.5828(11) 0.028(2) Uani d PDU 0.265(4) A 2
    H H13C 0.7058 0.3719 0.6534 0.034 Uiso calc PR 0.265(4) A 2
    H H13D 0.6927 0.4736 0.5961 0.034 Uiso calc PR 0.265(4) A 2
    O O4' 0.6840(5) 0.3805(6) 0.4170(9) 0.0431(7) Uani d PDU 0.265(4) A 2
    H H4'A 0.6640 0.4203 0.3577 0.065 Uiso calc PR 0.265(4) A 2
    H H2 0.530(2) 0.4936(19) 0.460(4) 0.026(8) Uiso d . 1 . .
    H H1 0.231(2) 0.7157(19) 0.450(4) 0.036(8) Uiso d . 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 C8 . 1.223(3) ?
    O2 C8 . 1.348(3) ?
    O2 C9 . 1.456(3) ?
    O3 C11 . 1.246(3) ?
    O5 N3 . 1.215(3) ?
    O6 N3 . 1.223(3) ?
    N1 C1 . 1.368(3) ?
    N1 C5 . 1.398(3) ?
    N1 H1 . 0.89(3) ?
    N2 C11 . 1.334(3) ?
    N2 C12 . 1.459(3) ?
    N2 H2 . 0.80(3) ?
    N3 C16 . 1.470(3) ?
    C1 C2 . 1.368(3) ?
    C1 C6 . 1.506(3) ?
    C2 C8 . 1.461(3) ?
    C2 C3 . 1.521(3) ?
    C3 C14 . 1.522(3) ?
    C3 C4 . 1.525(3) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.349(3) ?
    C4 C11 . 1.492(3) ?
    C5 C7 . 1.497(3) ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C9 C10 . 1.493(4) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C12 C13 . 1.463(5) ?
    C12 C13' . 1.512(7) ?
    C12 H12A . 0.9599 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C12 H12D . 0.9600 ?
    C14 C19 . 1.394(3) ?
    C14 C15 . 1.397(3) ?
    C15 C16 . 1.390(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.378(4) ?
    C17 C18 . 1.389(4) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.388(4) ?
    C18 H18 . 0.9500 ?
    C19 H19 . 0.9500 ?
    C13 O4 . 1.388(5) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    O4 H4A . 0.8400 ?
    C13' O4' . 1.539(9) ?
    C13' H13C . 0.9900 ?
    C13' H13D . 0.9900 ?
    O4' H4'A . 0.8400 ?
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
    C8 O2 C9 . . 116.31(16) ?
    C1 N1 C5 . . 123.76(19) ?
    C1 N1 H1 . . 115(2) ?
    C5 N1 H1 . . 118.8(19) ?
    C11 N2 C12 . . 122.5(2) ?
    C11 N2 H2 . . 121(2) ?
    C12 N2 H2 . . 117(2) ?
    O5 N3 O6 . . 122.7(2) ?
    O5 N3 C16 . . 119.0(2) ?
    O6 N3 C16 . . 118.2(2) ?
    C2 C1 N1 . . 119.60(19) ?
    C2 C1 C6 . . 127.4(2) ?
    N1 C1 C6 . . 113.00(19) ?
    C1 C2 C8 . . 125.49(19) ?
    C1 C2 C3 . . 121.95(19) ?
    C8 C2 C3 . . 112.56(18) ?
    C2 C3 C14 . . 112.56(18) ?
    C2 C3 C4 . . 111.68(18) ?
    C14 C3 C4 . . 107.78(19) ?
    C2 C3 H3 . . 108.2 ?
    C14 C3 H3 . . 108.2 ?
    C4 C3 H3 . . 108.2 ?
    C5 C4 C11 . . 121.4(2) ?
    C5 C4 C3 . . 121.8(2) ?
    C11 C4 C3 . . 116.43(19) ?
    C4 C5 N1 . . 119.8(2) ?
    C4 C5 C7 . . 126.8(2) ?
    N1 C5 C7 . . 113.4(2) ?
    C1 C6 H6A . . 109.5 ?
    C1 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C1 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C5 C7 H7A . . 109.5 ?
    C5 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C5 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O1 C8 O2 . . 121.6(2) ?
    O1 C8 C2 . . 122.3(2) ?
    O2 C8 C2 . . 116.07(18) ?
    O2 C9 C10 . . 106.44(19) ?
    O2 C9 H9A . . 110.4 ?
    C10 C9 H9A . . 110.4 ?
    O2 C9 H9B . . 110.4 ?
    C10 C9 H9B . . 110.4 ?
    H9A C9 H9B . . 108.6 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    O3 C11 N2 . . 121.6(2) ?
    O3 C11 C4 . . 122.9(2) ?
    N2 C11 C4 . . 115.4(2) ?
    N2 C12 C13 . . 113.6(3) ?
    N2 C12 C13' . . 112.7(4) ?
    C13 C12 C13' . . 29.2(4) ?
    N2 C12 H12A . . 108.8 ?
    C13 C12 H12A . . 109.6 ?
    C13' C12 H12A . . 131.4 ?
    N2 C12 H12B . . 108.9 ?
    C13 C12 H12B . . 108.2 ?
    C13' C12 H12B . . 81.8 ?
    H12A C12 H12B . . 107.7 ?
    N2 C12 H12C . . 109.0 ?
    C13 C12 H12C . . 82.9 ?
    C13' C12 H12C . . 109.9 ?
    H12A C12 H12C . . 30.1 ?
    H12B C12 H12C . . 131.4 ?
    N2 C12 H12D . . 109.0 ?
    C13 C12 H12D . . 129.5 ?
    C13' C12 H12D . . 108.4 ?
    H12A C12 H12D . . 80.0 ?
    H12B C12 H12D . . 29.8 ?
    H12C C12 H12D . . 107.8 ?
    C19 C14 C15 . . 118.4(2) ?
    C19 C14 C3 . . 120.8(2) ?
    C15 C14 C3 . . 120.8(2) ?
    C16 C15 C14 . . 118.8(2) ?
    C16 C15 H15 . . 120.6 ?
    C14 C15 H15 . . 120.6 ?
    C17 C16 C15 . . 123.2(2) ?
    C17 C16 N3 . . 119.2(2) ?
    C15 C16 N3 . . 117.6(2) ?
    C16 C17 C18 . . 117.7(2) ?
    C16 C17 H17 . . 121.2 ?
    C18 C17 H17 . . 121.2 ?
    C19 C18 C17 . . 120.3(2) ?
    C19 C18 H18 . . 119.8 ?
    C17 C18 H18 . . 119.8 ?
    C18 C19 C14 . . 121.6(2) ?
    C18 C19 H19 . . 119.2 ?
    C14 C19 H19 . . 119.2 ?
    O4 C13 C12 . . 118.0(4) ?
    O4 C13 H13A . . 107.8 ?
    C12 C13 H13A . . 107.8 ?
    O4 C13 H13B . . 107.8 ?
    C12 C13 H13B . . 107.8 ?
    H13A C13 H13B . . 107.1 ?
    C12 C13' O4' . . 105.3(6) ?
    C12 C13' H13C . . 110.7 ?
    O4' C13' H13C . . 110.7 ?
    C12 C13' H13D . . 110.7 ?
    O4' C13' H13D . . 110.7 ?
    H13C C13' H13D . . 108.8 ?
    C13' O4' H4'A . . 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 C1 C2 . . . . -6.2(4) ?
    C5 N1 C1 C6 . . . . 173.6(2) ?
    N1 C1 C2 C8 . . . . 176.7(2) ?
    C6 C1 C2 C8 . . . . -3.1(4) ?
    N1 C1 C2 C3 . . . . -3.2(3) ?
    C6 C1 C2 C3 . . . . 177.0(2) ?
    C1 C2 C3 C14 . . . . -110.0(2) ?
    C8 C2 C3 C14 . . . . 70.1(2) ?
    C1 C2 C3 C4 . . . . 11.4(3) ?
    C8 C2 C3 C4 . . . . -168.52(19) ?
    C2 C3 C4 C5 . . . . -11.8(3) ?
    C14 C3 C4 C5 . . . . 112.3(3) ?
    C2 C3 C4 C11 . . . . 174.82(19) ?
    C14 C3 C4 C11 . . . . -61.0(3) ?
    C11 C4 C5 N1 . . . . 177.1(2) ?
    C3 C4 C5 N1 . . . . 4.1(4) ?
    C11 C4 C5 C7 . . . . -4.3(4) ?
    C3 C4 C5 C7 . . . . -177.3(2) ?
    C1 N1 C5 C4 . . . . 5.8(4) ?
    C1 N1 C5 C7 . . . . -173.0(2) ?
    C9 O2 C8 O1 . . . . -3.4(3) ?
    C9 O2 C8 C2 . . . . 177.3(2) ?
    C1 C2 C8 O1 . . . . -179.9(2) ?
    C3 C2 C8 O1 . . . . 0.0(3) ?
    C1 C2 C8 O2 . . . . -0.6(3) ?
    C3 C2 C8 O2 . . . . 179.30(18) ?
    C8 O2 C9 C10 . . . . 175.5(2) ?
    C12 N2 C11 O3 . . . . -9.0(4) ?
    C12 N2 C11 C4 . . . . 167.6(2) ?
    C5 C4 C11 O3 . . . . -44.7(3) ?
    C3 C4 C11 O3 . . . . 128.7(2) ?
    C5 C4 C11 N2 . . . . 138.7(3) ?
    C3 C4 C11 N2 . . . . -47.9(3) ?
    C11 N2 C12 C13 . . . . -169.6(4) ?
    C11 N2 C12 C13' . . . . -137.9(5) ?
    C2 C3 C14 C19 . . . . 50.0(3) ?
    C4 C3 C14 C19 . . . . -73.6(3) ?
    C2 C3 C14 C15 . . . . -133.2(2) ?
    C4 C3 C14 C15 . . . . 103.2(2) ?
    C19 C14 C15 C16 . . . . 0.4(3) ?
    C3 C14 C15 C16 . . . . -176.4(2) ?
    C14 C15 C16 C17 . . . . 0.5(4) ?
    C14 C15 C16 N3 . . . . -178.7(2) ?
    O5 N3 C16 C17 . . . . 2.4(4) ?
    O6 N3 C16 C17 . . . . -177.2(2) ?
    O5 N3 C16 C15 . . . . -178.4(2) ?
    O6 N3 C16 C15 . . . . 2.0(3) ?
    C15 C16 C17 C18 . . . . -0.8(4) ?
    N3 C16 C17 C18 . . . . 178.4(2) ?
    C16 C17 C18 C19 . . . . 0.2(4) ?
    C17 C18 C19 C14 . . . . 0.7(4) ?
    C15 C14 C19 C18 . . . . -1.0(4) ?
    C3 C14 C19 C18 . . . . 175.9(2) ?
    N2 C12 C13 O4 . . . . 47.3(7) ?
    C13' C12 C13 O4 . . . . -47.4(8) ?
    N2 C12 C13' O4' . . . . -76.5(7) ?
    C13 C12 C13' O4' . . . . 21.5(6) ?
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 3_465 0.89(3) 2.04(3) 2.904(3) 163(3)
    N2 H2 O3 4_664 0.80(3) 2.13(4) 2.918(3) 168(3)
    O4' H4'A O3 4_664 0.84 2.00 2.829(9) 166.9
    O4 H4A O3 4_664 0.84 2.07 2.874(4) 159.3
