##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2005-03-16
_journal_date_accepted     2005-05-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      6
_journal_page_first     o1629
_journal_page_last     o1630
_journal_paper_category     EO
_publ_contact_author_name     'Professor Xin Zhang'
_publ_contact_author_address
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin
Weijin road No 241 ,Tianjin
China
;
_publ_contact_author_email     zxin_tj@eyou.com
_publ_contact_author_fax     '022-23540096'
_publ_contact_author_phone     '022-23540310'
_publ_section_title
;
Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydropyrazol-4-
ylidene)(phenyl)methyl]amino}-3-phenylpropanoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xin Zhang' .
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin
Weijin Road No. 241
Tianjin
People's Republic of China
;
    'Hua-Ling Zhu' .
;
Tianjin Agricultural College
Tianjin
Jinjing Road
Tianjin
People's Republic of China
;
    'Hai-Zhen Xu' .
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin
Weijin Road No. 241
Tianjin
People's Republic of China
;
    'Mei Dong' .
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin
Weijin Road No. 241
Tianjin
People's Republic of China
;
data_I
_chemical_name_systematic
;
Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydropyrazol-4-
ylidene)(phenyl)methyl]amino}-3-phenylpropanoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C28 H27 N3 O3'
_chemical_formula_sum     'C28 H27 N3 O3'
_chemical_formula_iupac     'C28 H27 N3 O3'
_chemical_formula_weight     453.53
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.521(3)
_cell_length_b     16.629(5)
_cell_length_c     14.080(4)
_cell_angle_alpha     90.00
_cell_angle_beta     105.315(5)
_cell_angle_gamma     90.00
_cell_volume     2375.9(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4184
_cell_measurement_theta_min     1.94
_cell_measurement_theta_max     26.42
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.268
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     960
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_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 SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12125
_diffrn_reflns_av_R_equivalents     0.0393
_diffrn_reflns_av_sigmaI/netI     0.0477
_diffrn_reflns_theta_min     2.01
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_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 > 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     4184
_reflns_number_gt     2661
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0948
_refine_ls_R_factor_gt     0.0511
_refine_ls_wR_factor_gt     0.1097
_refine_ls_wR_factor_ref     0.1298
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.012
_refine_ls_number_reflns     4184
_refine_ls_number_parameters     321
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0536P)²+0.8249P] 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     0.015
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.240
_refine_diff_density_min     -0.313
_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     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    N1 0.21200(17) 0.15615(12) 1.05366(13) 0.0387(5) Uani d . 1 . . N
    N2 0.33706(18) 0.19039(13) 1.09189(13) 0.0453(5) Uani d . 1 . . N
    N3 0.26208(19) 0.07896(12) 0.78347(13) 0.0437(5) Uani d . 1 A . N
    H3 0.1850 0.0738 0.7942 0.044(7) Uiso d R 1 . . H
    O1 0.09632(15) 0.09465(11) 0.90596(12) 0.0477(5) Uani d . 1 . . O
    O2 0.37415(19) -0.07743(13) 0.77333(15) 0.0709(6) Uani d . 1 . . O
    O3 0.45465(18) -0.02602(11) 0.65441(13) 0.0609(5) Uani d . 1 . . O
    C1 0.1979(2) 0.12586(14) 0.96010(16) 0.0361(5) Uani d . 1 . . C
    C2 0.3247(2) 0.13781(14) 0.94113(15) 0.0355(5) Uani d . 1 . . C
    C3 0.4033(2) 0.17905(15) 1.02618(16) 0.0412(6) Uani d . 1 . . C
    C4 0.5405(3) 0.2099(2) 1.0467(2) 0.0617(8) Uani d . 1 . . C
    H41 0.5555 0.2404 0.9919 0.078 Uiso d R 1 . . H
    H42 0.5586 0.2459 1.1005 0.086 Uiso d R 1 . . H
    H43 0.6038 0.1700 1.0516 0.098 Uiso d R 1 . . H
    C5 0.3553(2) 0.11119(14) 0.85624(16) 0.0358(5) Uani d . 1 . . C
    C6 0.2828(2) 0.04536(15) 0.69242(17) 0.0436(6) Uani d . 1 . . C
    H6 0.3209 0.0886 0.6541 0.049 Uiso d R 1 A . H
    C7 0.1529(2) 0.01398(16) 0.62672(19) 0.0511(7) Uani d . 1 A . C
    H71 0.1807 -0.0079 0.5686 0.060 Uiso d R 1 . . H
    H72 0.1224 -0.0313 0.6675 0.081 Uiso d R 1 . . H
    C8 0.0468(2) 0.07688(15) 0.59175(17) 0.0438(6) Uani d . 1 . . C
    C9 -0.0639(3) 0.07700(18) 0.62575(19) 0.0567(7) Uani d . 1 A . C
    H9 -0.0677 0.0380 0.6773 0.060 Uiso d R 1 . . H
    C10 -0.1639(3) 0.1319(2) 0.5901(2) 0.0682(9) Uani d . 1 . . C
    H10 -0.2403 0.1296 0.6147 0.086 Uiso d R 1 A . H
    C11 -0.1534(3) 0.18765(19) 0.5212(2) 0.0628(8) Uani d . 1 A . C
    H11 -0.2271 0.2278 0.4960 0.073 Uiso d R 1 . . H
    C12 -0.0437(3) 0.18888(17) 0.48694(19) 0.0559(7) Uani d . 1 . . C
    H12 -0.0339 0.2280 0.4415 0.065 Uiso d R 1 A . H
    C13 0.0565(3) 0.13388(17) 0.52144(18) 0.0506(7) Uani d . 1 A . C
    H13 0.1333 0.1353 0.4972 0.052 Uiso d R 1 . . H
    C14 0.3761(2) -0.02639(17) 0.71382(18) 0.0475(6) Uani d . 1 A . C
    C15 0.5255(6) -0.1040(4) 0.6516(5) 0.0556(19) Uiso d PD 0.50 A 2 C
    H150 0.4722 -0.1416 0.6052 0.067 Uiso calc PR 0.50 A 1 H
    H151 0.5535 -0.1288 0.7161 0.067 Uiso calc PR 0.50 A 1 H
    C16 0.6452(7) -0.0721(5) 0.6159(6) 0.099(2) Uiso d PD 0.50 A 1 C
    H16A 0.7159 -0.1104 0.6325 0.149 Uiso calc PR 0.50 A 1 H
    H16B 0.6745 -0.0217 0.6474 0.149 Uiso calc PR 0.50 A 1 H
    H16C 0.6187 -0.0646 0.5458 0.149 Uiso calc PR 0.50 A 1 H
    C151 0.5612(7) -0.0855(4) 0.6747(5) 0.060(2) Uiso d P 0.50 A 1 C
    H152 0.5306 -0.1363 0.6943 0.072 Uiso calc PR 0.50 A 2 H
    H153 0.6349 -0.0668 0.7271 0.072 Uiso calc PR 0.50 A 2 H
    C161 0.60236(16) -0.09546(11) 0.57947(12) 0.0726(19) Uiso d P 0.50 A 2 C
    H164 0.6503 -0.1449 0.5817 0.109 Uiso calc PR 0.50 A 2 H
    H165 0.6574 -0.0512 0.5720 0.109 Uiso calc PR 0.50 A 2 H
    H166 0.5254 -0.0966 0.5247 0.109 Uiso calc PR 0.50 A 2 H
    C17 0.49251(16) 0.11539(11) 0.84526(12) 0.0371(6) Uani d . 1 . . C
    C18 0.58424(16) 0.05823(11) 0.89219(12) 0.0522(7) Uani d . 1 . . C
    H18 0.5519 0.0119 0.9308 0.068 Uiso d R 1 . . H
    C19 0.7129(3) 0.06343(18) 0.8871(2) 0.0610(8) Uani d . 1 . . C
    H19 0.7748 0.0196 0.9188 0.074 Uiso d R 1 . . H
    C20 0.7532(3) 0.12559(19) 0.83800(19) 0.0587(8) Uani d . 1 . . C
    H20 0.8396 0.1316 0.8342 0.058 Uiso d R 1 . . H
    C21 0.6629(2) 0.18228(18) 0.79178(19) 0.0560(7) Uani d . 1 . . C
    H21 0.6879 0.2279 0.7611 0.077 Uiso d R 1 . . H
    C22 0.5325(2) 0.17726(15) 0.79387(17) 0.0452(6) Uani d . 1 . . C
    H22 0.4664 0.2174 0.7637 0.052 Uiso d R 1 . . H
    C23 0.1208(2) 0.15830(14) 1.11201(16) 0.0362(5) Uani d . 1 . . C
    C24 0.1409(2) 0.21183(15) 1.19036(17) 0.0463(6) Uani d . 1 . . C
    H24 0.2262 0.2453 1.2069 0.053 Uiso d R 1 . . H
    C25 0.0505(3) 0.21549(17) 1.24569(19) 0.0544(7) Uani d . 1 . . C
    H25 0.0710 0.2530 1.3033 0.077 Uiso d R 1 . . H
    C26 -0.0586(3) 0.16633(16) 1.22501(19) 0.0532(7) Uani d . 1 . . C
    H26 -0.1270 0.1671 1.2655 0.060 Uiso d R 1 . . H
    C27 -0.0772(3) 0.11233(16) 1.14806(19) 0.0505(7) Uani d . 1 . . C
    H27 -0.1623 0.0758 1.1284 0.062 Uiso d R 1 . . H
    C28 0.0122(2) 0.10787(15) 1.09169(18) 0.0455(6) Uani d . 1 . . C
    H28 0.0011 0.0694 1.0390 0.049 Uiso d R 1 . . H
_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
    N1 C1 . 1.381(3) ?
    N1 N2 . 1.404(2) ?
    N1 C23 . 1.419(3) ?
    N2 C3 . 1.311(3) ?
    N3 C5 . 1.330(3) y
    N3 C6 . 1.466(3) y
    N3 H3 . 0.87 ?
    O1 C1 . 1.250(3) y
    O2 C14 . 1.197(3) y
    O3 C14 . 1.322(3) ?
    O3 C151 . 1.465(7) ?
    O3 C15 . 1.501(7) ?
    C1 C2 . 1.442(3) y
    C2 C5 . 1.389(3) y
    C2 C3 . 1.437(3) ?
    C3 C4 . 1.486(3) ?
    C4 H41 . 0.97 ?
    C4 H42 . 0.94 ?
    C4 H43 . 0.93 ?
    C5 C17 . 1.494(3) ?
    C6 C14 . 1.524(3) y
    C6 C7 . 1.525(3) ?
    C6 H6 . 1.04 ?
    C7 C8 . 1.514(3) ?
    C7 H71 . 1.01 ?
    C7 H72 . 1.05 ?
    C8 C9 . 1.371(4) ?
    C8 C13 . 1.394(4) ?
    C9 C10 . 1.383(4) ?
    C9 H9 . 0.98 ?
    C10 C11 . 1.368(4) ?
    C10 H10 . 0.96 ?
    C11 C12 . 1.364(4) ?
    C11 H11 . 1.01 ?
    C12 C13 . 1.383(4) ?
    C12 H12 . 0.94 ?
    C13 H13 . 0.96 ?
    C15 C16 . 1.567(7) ?
    C15 H150 . 0.97 ?
    C15 H151 . 0.97 ?
    C16 H16A . 0.96 ?
    C16 H16B . 0.96 ?
    C16 H16C . 0.96 ?
    C151 C161 . 1.523(7) ?
    C151 H152 . 0.97 ?
    C151 H153 . 0.97 ?
    C161 H164 . 0.96 ?
    C161 H165 . 0.96 ?
    C161 H166 . 0.96 ?
    C17 C22 . 1.385(3) ?
    C17 C18 . 1.391 ?
    C18 C19 . 1.377(3) ?
    C18 H18 . 1.05 ?
    C19 C20 . 1.371(4) ?
    C19 H19 . 1.00 ?
    C20 C21 . 1.374(4) ?
    C20 H20 . 0.93 ?
    C21 C22 . 1.382(3) ?
    C21 H21 . 0.94 ?
    C22 H22 . 0.98 ?
    C23 C28 . 1.385(3) ?
    C23 C24 . 1.390(3) ?
    C24 C25 . 1.381(3) ?
    C24 H24 . 1.03 ?
    C25 C26 . 1.376(4) ?
    C25 H25 . 1.00 ?
    C26 C27 . 1.381(3) ?
    C26 H26 . 1.03 ?
    C27 C28 . 1.383(3) ?
    C27 H27 . 1.06 ?
    C28 H28 . 0.96 ?
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
    C1 N1 N2 . . 111.53(17) ?
    C1 N1 C23 . . 130.01(18) ?
    N2 N1 C23 . . 118.46(17) ?
    C3 N2 N1 . . 106.89(17) ?
    C5 N3 C6 . . 125.3(2) ?
    C5 N3 H3 . . 116.0 ?
    C6 N3 H3 . . 118.4 ?
    C14 O3 C151 . . 116.6(3) ?
    C14 O3 C15 . . 114.2(3) ?
    C151 O3 C15 . . 20.4(4) ?
    O1 C1 N1 . . 126.3(2) ?
    O1 C1 C2 . . 128.9(2) ?
    N1 C1 C2 . . 104.79(18) ?
    C5 C2 C3 . . 131.0(2) ?
    C5 C2 C1 . . 123.4(2) ?
    C3 C2 C1 . . 105.57(19) ?
    N2 C3 C2 . . 111.1(2) ?
    N2 C3 C4 . . 118.9(2) ?
    C2 C3 C4 . . 130.0(2) ?
    C3 C4 H41 . . 112.2 ?
    C3 C4 H42 . . 110.8 ?
    H41 C4 H42 . . 105.4 ?
    C3 C4 H43 . . 114.0 ?
    H41 C4 H43 . . 99.7 ?
    H42 C4 H43 . . 113.8 ?
    N3 C5 C2 . . 120.0(2) ?
    N3 C5 C17 . . 118.38(19) ?
    C2 C5 C17 . . 121.57(19) ?
    N3 C6 C14 . . 111.23(19) ?
    N3 C6 C7 . . 110.2(2) ?
    C14 C6 C7 . . 106.2(2) ?
    N3 C6 H6 . . 110.9 ?
    C14 C6 H6 . . 109.1 ?
    C7 C6 H6 . . 109.1 ?
    C8 C7 C6 . . 115.2(2) ?
    C8 C7 H71 . . 109.4 ?
    C6 C7 H71 . . 102.2 ?
    C8 C7 H72 . . 111.6 ?
    C6 C7 H72 . . 105.6 ?
    H71 C7 H72 . . 112.4 ?
    C9 C8 C13 . . 118.4(2) ?
    C9 C8 C7 . . 120.6(3) ?
    C13 C8 C7 . . 121.0(2) ?
    C8 C9 C10 . . 120.6(3) ?
    C8 C9 H9 . . 117.5 ?
    C10 C9 H9 . . 121.9 ?
    C11 C10 C9 . . 120.6(3) ?
    C11 C10 H10 . . 121.1 ?
    C9 C10 H10 . . 118.4 ?
    C12 C11 C10 . . 119.7(3) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 119.8 ?
    C11 C12 C13 . . 120.3(3) ?
    C11 C12 H12 . . 120.5 ?
    C13 C12 H12 . . 119.2 ?
    C12 C13 C8 . . 120.5(3) ?
    C12 C13 H13 . . 119.7 ?
    C8 C13 H13 . . 119.8 ?
    O2 C14 O3 . . 125.1(2) ?
    O2 C14 C6 . . 124.4(2) ?
    O3 C14 C6 . . 110.4(2) ?
    O3 C15 C16 . . 99.4(5) ?
    O3 C15 H150 . . 111.9 ?
    C16 C15 H150 . . 111.9 ?
    O3 C15 H151 . . 111.9 ?
    C16 C15 H151 . . 111.9 ?
    H150 C15 H151 . . 109.6 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O3 C151 C161 . . 106.5(4) ?
    O3 C151 H152 . . 110.4 ?
    C161 C151 H152 . . 110.4 ?
    O3 C151 H153 . . 110.4 ?
    C161 C151 H153 . . 110.4 ?
    H152 C151 H153 . . 108.6 ?
    C151 C161 H164 . . 109.5 ?
    C151 C161 H165 . . 109.5 ?
    H164 C161 H165 . . 109.5 ?
    C151 C161 H166 . . 109.5 ?
    H164 C161 H166 . . 109.5 ?
    H165 C161 H166 . . 109.5 ?
    C22 C17 C18 . . 119.17(12) ?
    C22 C17 C5 . . 121.58(18) ?
    C18 C17 C5 . . 119.16(11) ?
    C19 C18 C17 . . 120.04(15) ?
    C19 C18 H18 . . 122.0 ?
    C17 C18 H18 . . 117.9 ?
    C20 C19 C18 . . 120.8(2) ?
    C20 C19 H19 . . 121.5 ?
    C18 C19 H19 . . 117.6 ?
    C19 C20 C21 . . 119.3(3) ?
    C19 C20 H20 . . 123.1 ?
    C21 C20 H20 . . 117.6 ?
    C20 C21 C22 . . 121.0(3) ?
    C20 C21 H21 . . 121.8 ?
    C22 C21 H21 . . 117.2 ?
    C21 C22 C17 . . 119.7(2) ?
    C21 C22 H22 . . 123.1 ?
    C17 C22 H22 . . 117.1 ?
    C28 C23 C24 . . 119.7(2) ?
    C28 C23 N1 . . 120.8(2) ?
    C24 C23 N1 . . 119.4(2) ?
    C25 C24 C23 . . 119.5(2) ?
    C25 C24 H24 . . 122.5 ?
    C23 C24 H24 . . 117.9 ?
    C26 C25 C24 . . 121.0(2) ?
    C26 C25 H25 . . 122.1 ?
    C24 C25 H25 . . 116.8 ?
    C25 C26 C27 . . 119.3(2) ?
    C25 C26 H26 . . 122.8 ?
    C27 C26 H26 . . 117.9 ?
    C26 C27 C28 . . 120.6(2) ?
    C26 C27 H27 . . 120.9 ?
    C28 C27 H27 . . 118.4 ?
    C27 C28 C23 . . 119.8(2) ?
    C27 C28 H28 . . 121.1 ?
    C23 C28 H28 . . 119.1 ?
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
    C1 N1 N2 C3 . . . . -2.7(3) ?
    C23 N1 N2 C3 . . . . 178.4(2) ?
    N2 N1 C1 O1 . . . . -177.1(2) ?
    C23 N1 C1 O1 . . . . 1.6(4) ?
    N2 N1 C1 C2 . . . . 3.4(3) ?
    C23 N1 C1 C2 . . . . -177.8(2) ?
    O1 C1 C2 C5 . . . . -3.3(4) ?
    N1 C1 C2 C5 . . . . 176.2(2) ?
    O1 C1 C2 C3 . . . . 177.8(2) ?
    N1 C1 C2 C3 . . . . -2.8(2) ?
    N1 N2 C3 C2 . . . . 0.8(3) ?
    N1 N2 C3 C4 . . . . 179.6(2) ?
    C5 C2 C3 N2 . . . . -177.6(2) ?
    C1 C2 C3 N2 . . . . 1.3(3) ?
    C5 C2 C3 C4 . . . . 3.8(5) ?
    C1 C2 C3 C4 . . . . -177.4(3) ?
    C6 N3 C5 C2 . . . . -177.0(2) ?
    C6 N3 C5 C17 . . . . 1.1(3) ?
    C3 C2 C5 N3 . . . . -175.3(2) ?
    C1 C2 C5 N3 . . . . 6.0(4) ?
    C3 C2 C5 C17 . . . . 6.7(4) ?
    C1 C2 C5 C17 . . . . -172.0(2) ?
    C5 N3 C6 C14 . . . . 62.5(3) ?
    C5 N3 C6 C7 . . . . 180.0(2) ?
    N3 C6 C7 C8 . . . . 62.5(3) ?
    C14 C6 C7 C8 . . . . -177.0(2) ?
    C6 C7 C8 C9 . . . . -110.9(3) ?
    C6 C7 C8 C13 . . . . 71.7(3) ?
    C13 C8 C9 C10 . . . . 0.7(4) ?
    C7 C8 C9 C10 . . . . -176.7(2) ?
    C8 C9 C10 C11 . . . . -0.8(4) ?
    C9 C10 C11 C12 . . . . 0.4(4) ?
    C10 C11 C12 C13 . . . . 0.2(4) ?
    C11 C12 C13 C8 . . . . -0.3(4) ?
    C9 C8 C13 C12 . . . . -0.2(4) ?
    C7 C8 C13 C12 . . . . 177.2(2) ?
    C151 O3 C14 O2 . . . . -10.6(5) ?
    C15 O3 C14 O2 . . . . 11.9(5) ?
    C151 O3 C14 C6 . . . . 172.4(4) ?
    C15 O3 C14 C6 . . . . -165.2(3) ?
    N3 C6 C14 O2 . . . . 41.1(4) y
    C7 C6 C14 O2 . . . . -78.8(3) ?
    N3 C6 C14 O3 . . . . -141.8(2) ?
    C7 C6 C14 O3 . . . . 98.3(2) ?
    C14 O3 C15 C16 . . . . -156.9(4) ?
    C151 O3 C15 C16 . . . . -55.5(10) ?
    C14 O3 C151 C161 . . . . 159.0(3) ?
    C15 O3 C151 C161 . . . . 70.7(11) ?
    N3 C5 C17 C22 . . . . 83.2(3) ?
    C2 C5 C17 C22 . . . . -98.7(3) ?
    N3 C5 C17 C18 . . . . -100.26(19) ?
    C2 C5 C17 C18 . . . . 77.8(2) ?
    C22 C17 C18 C19 . . . . -0.14(18) ?
    C5 C17 C18 C19 . . . . -176.7(2) ?
    C17 C18 C19 C20 . . . . 1.5(3) ?
    C18 C19 C20 C21 . . . . -1.3(4) ?
    C19 C20 C21 C22 . . . . -0.2(4) ?
    C20 C21 C22 C17 . . . . 1.6(4) ?
    C18 C17 C22 C21 . . . . -1.4(3) ?
    C5 C17 C22 C21 . . . . 175.1(2) ?
    C1 N1 C23 C28 . . . . 19.0(4) ?
    N2 N1 C23 C28 . . . . -162.3(2) ?
    C1 N1 C23 C24 . . . . -160.9(2) ?
    N2 N1 C23 C24 . . . . 17.8(3) ?
    C28 C23 C24 C25 . . . . -1.6(4) ?
    N1 C23 C24 C25 . . . . 178.3(2) ?
    C23 C24 C25 C26 . . . . 0.7(4) ?
    C24 C25 C26 C27 . . . . 0.3(4) ?
    C25 C26 C27 C28 . . . . -0.5(4) ?
    C26 C27 C28 C23 . . . . -0.4(4) ?
    C24 C23 C28 C27 . . . . 1.4(4) ?
    N1 C23 C28 C27 . . . . -178.5(2) ?
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
    N3 H3 O1 . 0.87 2.06 2.770(2) 139
