##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'APEX2 v2014.7-1'
_journal_date_recd_electronic     2014-10-24
_journal_date_accepted     2014-10-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue     11
_journal_page_first     o1214
_journal_page_last     o1215
_journal_paper_category     HO
_journal_paper_doi     10.1107/S1600536814023502
_journal_coeditor_code     HB7306
_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
;\
Crystal structure of ethyl
(2Z)-2-cyano-3-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)amino]prop-\
2-enoate
;
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
;
    'Talaat I. El-Emary'
;
Department of Chemistry,
Faculty of Science,
Assiut University,
71515 Assiut,
Egypt
;
    'Mustafa R. Albayati'
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1031059'
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;\
Ethyl (2Z)-2-cyano-3-[(3-methyl-1-phenyl-1H-\
pyrazol-5-yl)amino]prop-2-enoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N4 O2'
_chemical_formula_sum     'C16 H16 N4 O2'
_chemical_formula_iupac     'C16 H16 N4 O2'
_chemical_formula_weight     296.33
_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     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.0656(2)
_cell_length_b     10.4085(3)
_cell_length_c     16.5551(4)
_cell_angle_alpha     86.9930(11)
_cell_angle_beta     81.5670(10)
_cell_angle_gamma     73.3900(11)
_cell_volume     1480.67(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9947
_cell_measurement_theta_min     2.70
_cell_measurement_theta_max     72.20
_cell_measurement_temperature     150(2)
_exptl_crystal_description     column
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.200
_exptl_crystal_size_mid     0.120
_exptl_crystal_size_min     0.074
_exptl_crystal_density_diffrn     1.329
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.743
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.866
_shelx_estimated_absorpt_T_max     0.947
_exptl_absorpt_correction_T_min     0.87
_exptl_absorpt_correction_T_max     0.95
_exptl_special_details     ?
_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     19446
_diffrn_reflns_av_R_equivalents     0.0327
_diffrn_reflns_theta_min     2.698
_diffrn_reflns_theta_max     72.225
_diffrn_reflns_theta_full     68.000
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_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. H-atoms attached to carbon were placed in calculated positions
(C---H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in
locations derived from a difference map and their parameters adjusted to give
N---H = 0.91 Å. All were included as riding contributions with isotropic
displacement parameters 1.2 - 1.5 times those of the attached atoms. The major
portion of the side chain in molecule 1 is disordered over two reasonably
resolved sites in a 4:1 ratio. The two components of the disorder were refined
subject to restraints that their geometries be comparable to one another and
to that of the corresponding ordered portion of molecule 2.
;
_reflns_number_total     5749
_reflns_number_gt     4534
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0563
_refine_ls_R_factor_gt     0.0421
_refine_ls_wR_factor_gt     0.1028
_refine_ls_wR_factor_ref     0.1118
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     5749
_refine_ls_number_parameters     422
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0503P)²+0.4804P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.234
_refine_diff_density_min     -0.216
_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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_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
    O O1 0.6238(3) 0.3465(3) 0.28680(16) 0.0306(5) Uani d 0.799(2) A 1
    O O2 0.77612(17) 0.15788(14) 0.22373(8) 0.0302(3) Uani d 0.799(2) A 1
    C C12 0.5735(15) 0.2907(8) 0.1590(4) 0.0254(15) Uani d 0.799(2) A 1
    C C13 0.6233(9) 0.1924(11) 0.0963(6) 0.0257(11) Uani d 0.799(2) A 1
    C C14 0.6579(3) 0.2695(2) 0.22932(15) 0.0253(5) Uani d 0.799(2) A 1
    C C15 0.8661(3) 0.1257(2) 0.29189(13) 0.0320(5) Uani d 0.799(2) A 1
    H H15A 0.8749 0.2093 0.3140 0.038 Uiso calc 0.799(2) A 1
    H H15B 0.9722 0.0690 0.2727 0.038 Uiso calc 0.799(2) A 1
    C C16 0.7883(3) 0.0527(2) 0.35783(14) 0.0395(5) Uani d 0.799(2) A 1
    H H16A 0.8495 0.0315 0.4034 0.059 Uiso calc 0.799(2) A 1
    H H16B 0.6838 0.1096 0.3772 0.059 Uiso calc 0.799(2) A 1
    H H16C 0.7808 -0.0305 0.3359 0.059 Uiso calc 0.799(2) A 1
    O O1A 0.5872(14) 0.3347(15) 0.2989(8) 0.0306(5) Uani d 0.201(2) A 2
    O O2A 0.6939(7) 0.1234(6) 0.2493(3) 0.0302(3) Uani d 0.201(2) A 2
    C C12A 0.562(7) 0.284(3) 0.164(2) 0.0254(15) Uani d 0.201(2) A 2
    C C13A 0.601(4) 0.190(5) 0.098(3) 0.0257(11) Uani d 0.201(2) A 2
    C C14A 0.6162(13) 0.2541(11) 0.2439(7) 0.0253(5) Uani d 0.201(2) A 2
    C C15A 0.7531(10) 0.0775(9) 0.3268(5) 0.0320(5) Uani d 0.201(2) A 2
    H H15C 0.7664 -0.0200 0.3337 0.038 Uiso calc 0.201(2) A 2
    H H15D 0.6767 0.1237 0.3726 0.038 Uiso calc 0.201(2) A 2
    C C16A 0.9041(11) 0.1054(10) 0.3289(6) 0.0395(5) Uani d 0.201(2) A 2
    H H16D 0.9413 0.0740 0.3812 0.059 Uiso calc 0.201(2) A 2
    H H16E 0.9802 0.0585 0.2841 0.059 Uiso calc 0.201(2) A 2
    H H16F 0.8906 0.2021 0.3230 0.059 Uiso calc 0.201(2) A 2
    N N1 0.23080(14) 0.71344(12) 0.25293(7) 0.0246(3) Uani d 1 . .
    N N2 0.12067(15) 0.82212(13) 0.22657(8) 0.0272(3) Uani d 1 . .
    N N3 0.40300(14) 0.50200(12) 0.20513(7) 0.0250(3) Uani d 1 . .
    H H3A 0.4491 0.4869 0.2513 0.030 Uiso d 1 . .
    N N4 0.65730(18) 0.11313(15) 0.04604(9) 0.0373(3) Uani d 1 . .
    C C1 0.25120(18) 0.70254(15) 0.33706(9) 0.0239(3) Uani d 1 . .
    C C2 0.12130(19) 0.73850(17) 0.39628(10) 0.0303(4) Uani d 1 . .
    H H2 0.0203 0.7707 0.3807 0.036 Uiso calc 1 . .
    C C3 0.1403(2) 0.72708(18) 0.47835(10) 0.0354(4) Uani d 1 . .
    H H3 0.0518 0.7520 0.5189 0.042 Uiso calc 1 . .
    C C4 0.2871(2) 0.67965(17) 0.50155(10) 0.0327(4) Uani d 1 . .
    H H4 0.2995 0.6708 0.5577 0.039 Uiso calc 1 . .
    C C5 0.41506(19) 0.64536(16) 0.44225(10) 0.0306(4) Uani d 1 . .
    H H5 0.5159 0.6127 0.4581 0.037 Uiso calc 1 . .
    C C6 0.39891(18) 0.65784(16) 0.35969(9) 0.0267(3) Uani d 1 . .
    H H6 0.4880 0.6360 0.3193 0.032 Uiso calc 1 . .
    C C7 0.11687(18) 0.79590(16) 0.14906(9) 0.0273(3) Uani d 1 . .
    C C8 0.22272(18) 0.67160(16) 0.12446(9) 0.0272(3) Uani d 1 . .
    H H8 0.2418 0.6312 0.0724 0.033 Uiso calc 1 . .
    C C9 0.29172(17) 0.62220(15) 0.19198(9) 0.0233(3) Uani d 1 . .
    C C10 0.0078(2) 0.89208(17) 0.09971(10) 0.0347(4) Uani d 1 . .
    H H10A -0.0727 0.8522 0.0886 0.052 Uiso calc 1 . .
    H H10B 0.0654 0.9119 0.0480 0.052 Uiso calc 1 . .
    H H10C -0.0409 0.9752 0.1302 0.052 Uiso calc 1 . .
    C C11 0.45577(17) 0.40469(15) 0.14963(9) 0.0251(3) Uani d 1 . .
    H H11 0.4090 0.4152 0.1011 0.030 Uiso calc 1 A 1
    O O3 0.66182(14) 0.82942(11) 0.26058(7) 0.0354(3) Uani d 1 . .
    O O4 0.79855(13) 0.63165(11) 0.20236(7) 0.0302(3) Uani d 1 . .
    N N5 0.23310(15) 1.18094(13) 0.23448(8) 0.0287(3) Uani d 1 . .
    N N6 0.12144(16) 1.28758(13) 0.20738(8) 0.0314(3) Uani d 1 . .
    N N7 0.42346(15) 0.97824(13) 0.18512(8) 0.0288(3) Uani d 1 . .
    H H7A 0.4804 0.9711 0.2269 0.035 Uiso d 1 . .
    N N8 0.65249(17) 0.57821(15) 0.03377(9) 0.0369(3) Uani d 1 . .
    C C17 0.26044(18) 1.17753(16) 0.31716(10) 0.0288(3) Uani d 1 . .
    C C18 0.2914(2) 1.05786(17) 0.36117(10) 0.0363(4) Uani d 1 . .
    H H18 0.2932 0.9768 0.3367 0.044 Uiso calc 1 . .
    C C19 0.3195(2) 1.05798(19) 0.44122(11) 0.0428(4) Uani d 1 . .
    H H19 0.3444 0.9758 0.4710 0.051 Uiso calc 1 . .
    C C20 0.3119(2) 1.1756(2) 0.47826(11) 0.0428(4) Uani d 1 . .
    H H20 0.3308 1.1746 0.5333 0.051 Uiso calc 1 . .
    C C21 0.2767(2) 1.29494(19) 0.43479(11) 0.0401(4) Uani d 1 . .
    H H21 0.2695 1.3765 0.4604 0.048 Uiso calc 1 . .
    C C22 0.2519(2) 1.29647(17) 0.35414(10) 0.0332(4) Uani d 1 . .
    H H22 0.2292 1.3786 0.3243 0.040 Uiso calc 1 . .
    C C23 0.12004(19) 1.26028(17) 0.12999(10) 0.0323(4) Uani d 1 . .
    C C24 0.2316(2) 1.13890(17) 0.10562(10) 0.0335(4) Uani d 1 . .
    H H24 0.2537 1.0985 0.0534 0.040 Uiso calc 1 . .
    C C25 0.30107(18) 1.09202(16) 0.17336(10) 0.0288(3) Uani d 1 . .
    C C26 0.0069(2) 1.35258(19) 0.08089(11) 0.0432(5) Uani d 1 . .
    H H26A -0.0709 1.3090 0.0704 0.065 Uiso calc 1 . .
    H H26B 0.0623 1.3738 0.0288 0.065 Uiso calc 1 . .
    H H26C -0.0448 1.4354 0.1112 0.065 Uiso calc 1 . .
    C C27 0.46945(18) 0.87682(16) 0.13317(9) 0.0283(3) Uani d 1 . .
    H H27 0.4135 0.8819 0.0883 0.034 Uiso calc 1 . .
    C C28 0.59263(18) 0.76496(16) 0.13985(9) 0.0270(3) Uani d 1 . .
    C C29 0.62621(18) 0.66170(16) 0.08068(9) 0.0282(3) Uani d 1 . .
    C C30 0.68579(18) 0.74789(15) 0.20653(9) 0.0269(3) Uani d 1 . .
    C C31 0.90350(19) 0.60631(17) 0.26367(10) 0.0316(4) Uani d 1 . .
    H H31A 0.9230 0.6914 0.2763 0.038 Uiso calc 1 . .
    H H31B 1.0041 0.5437 0.2414 0.038 Uiso calc 1 . .
    C C32 0.8387(2) 0.5478(2) 0.34076(11) 0.0393(4) Uani d 1 . .
    H H32A 0.7475 0.6149 0.3674 0.059 Uiso calc 1 . .
    H H32B 0.9178 0.5214 0.3776 0.059 Uiso calc 1 . .
    H H32C 0.8084 0.4690 0.3277 0.059 Uiso calc 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
    O1 C14 . 1.223(3) ?
    O2 C14 . 1.333(3) ?
    O2 C15 . 1.457(2) ?
    C12 C11 . 1.370(5) ?
    C12 C13 . 1.428(4) ?
    C12 C14 . 1.458(5) ?
    C13 N4 . 1.149(4) ?
    C15 C16 . 1.503(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    O1A C14A . 1.218(13) ?
    O2A C14A . 1.346(12) ?
    O2A C15A . 1.467(9) ?
    C12A C11 . 1.379(15) ?
    C12A C13A . 1.442(15) ?
    C12A C14A . 1.473(15) ?
    C13A N4 . 1.157(15) ?
    C15A C16A . 1.484(11) ?
    C15A H15C . 0.9900 ?
    C15A H15D . 0.9900 ?
    C16A H16D . 0.9800 ?
    C16A H16E . 0.9800 ?
    C16A H16F . 0.9800 ?
    N1 C9 . 1.3648(19) ?
    N1 N2 . 1.3773(17) ?
    N1 C1 . 1.4261(18) ?
    N2 C7 . 1.3331(19) ?
    N3 C11 . 1.3382(19) ?
    N3 C9 . 1.3945(19) ?
    N3 H3A . 0.9099 ?
    C1 C6 . 1.387(2) ?
    C1 C2 . 1.391(2) ?
    C2 C3 . 1.389(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.384(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.380(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.391(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.411(2) ?
    C7 C10 . 1.494(2) ?
    C8 C9 . 1.366(2) ?
    C8 H8 . 0.9500 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11 . 0.9500 ?
    O3 C30 . 1.2186(18) ?
    O4 C30 . 1.3396(19) ?
    O4 C31 . 1.4550(18) ?
    N5 C25 . 1.360(2) ?
    N5 N6 . 1.3772(18) ?
    N5 C17 . 1.423(2) ?
    N6 C23 . 1.329(2) ?
    N7 C27 . 1.329(2) ?
    N7 C25 . 1.400(2) ?
    N7 H7A . 0.9100 ?
    N8 C29 . 1.146(2) ?
    C17 C22 . 1.387(2) ?
    C17 C18 . 1.388(2) ?
    C18 C19 . 1.386(2) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.377(3) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.382(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.385(2) ?
    C21 H21 . 0.9500 ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.409(2) ?
    C23 C26 . 1.495(2) ?
    C24 C25 . 1.366(2) ?
    C24 H24 . 0.9500 ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    C27 C28 . 1.376(2) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.429(2) ?
    C28 C30 . 1.460(2) ?
    C31 C32 . 1.499(2) ?
    C31 H31A . 0.9900 ?
    C31 H31B . 0.9900 ?
    C32 H32A . 0.9800 ?
    C32 H32B . 0.9800 ?
    C32 H32C . 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
    C14 O2 C15 . . 117.05(16) ?
    C11 C12 C13 . . 119.8(6) ?
    C11 C12 C14 . . 122.0(4) ?
    C13 C12 C14 . . 118.1(6) ?
    N4 C13 C12 . . 177.2(9) ?
    O1 C14 O2 . . 124.0(3) ?
    O1 C14 C12 . . 123.4(3) ?
    O2 C14 C12 . . 112.7(2) ?
    O2 C15 C16 . . 110.05(19) ?
    O2 C15 H15A . . 109.7 ?
    C16 C15 H15A . . 109.7 ?
    O2 C15 H15B . . 109.7 ?
    C16 C15 H15B . . 109.7 ?
    H15A C15 H15B . . 108.2 ?
    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 ?
    C14A O2A C15A . . 116.5(7) ?
    C11 C12A C13A . . 115(3) ?
    C11 C12A C14A . . 120.2(13) ?
    C13A C12A C14A . . 125(3) ?
    N4 C13A C12A . . 168(4) ?
    O1A C14A O2A . . 125.2(13) ?
    O1A C14A C12A . . 124.6(14) ?
    O2A C14A C12A . . 110.1(11) ?
    O2A C15A C16A . . 111.0(8) ?
    O2A C15A H15C . . 109.4 ?
    C16A C15A H15C . . 109.4 ?
    O2A C15A H15D . . 109.4 ?
    C16A C15A H15D . . 109.4 ?
    H15C C15A H15D . . 108.0 ?
    C15A C16A H16D . . 109.5 ?
    C15A C16A H16E . . 109.5 ?
    H16D C16A H16E . . 109.5 ?
    C15A C16A H16F . . 109.5 ?
    H16D C16A H16F . . 109.5 ?
    H16E C16A H16F . . 109.5 ?
    C9 N1 N2 . . 110.60(12) ?
    C9 N1 C1 . . 129.64(12) ?
    N2 N1 C1 . . 119.23(12) ?
    C7 N2 N1 . . 104.92(12) ?
    C11 N3 C9 . . 122.93(13) ?
    C11 N3 H3A . . 115.4 ?
    C9 N3 H3A . . 121.6 ?
    C6 C1 C2 . . 120.28(14) ?
    C6 C1 N1 . . 120.43(14) ?
    C2 C1 N1 . . 119.29(14) ?
    C3 C2 C1 . . 119.57(15) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    C4 C3 C2 . . 120.55(15) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C5 C4 C3 . . 119.33(15) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 121.09(15) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 119.16(15) ?
    C1 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    N2 C7 C8 . . 111.68(13) ?
    N2 C7 C10 . . 120.50(14) ?
    C8 C7 C10 . . 127.81(14) ?
    C9 C8 C7 . . 104.81(13) ?
    C9 C8 H8 . . 127.6 ?
    C7 C8 H8 . . 127.6 ?
    N1 C9 C8 . . 107.99(13) ?
    N1 C9 N3 . . 120.92(13) ?
    C8 C9 N3 . . 131.09(14) ?
    C7 C10 H10A . . 109.5 ?
    C7 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C7 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N3 C11 C12 . . 123.6(2) ?
    N3 C11 C12A . . 123.0(7) ?
    N3 C11 H11 . . 118.2 ?
    C12 C11 H11 . . 118.2 ?
    C30 O4 C31 . . 117.32(12) ?
    C25 N5 N6 . . 110.68(13) ?
    C25 N5 C17 . . 130.18(13) ?
    N6 N5 C17 . . 119.14(13) ?
    C23 N6 N5 . . 104.99(13) ?
    C27 N7 C25 . . 121.93(13) ?
    C27 N7 H7A . . 115.7 ?
    C25 N7 H7A . . 122.3 ?
    C22 C17 C18 . . 120.14(15) ?
    C22 C17 N5 . . 119.02(15) ?
    C18 C17 N5 . . 120.82(15) ?
    C19 C18 C17 . . 119.25(16) ?
    C19 C18 H18 . . 120.4 ?
    C17 C18 H18 . . 120.4 ?
    C20 C19 C18 . . 120.91(17) ?
    C20 C19 H19 . . 119.5 ?
    C18 C19 H19 . . 119.5 ?
    C19 C20 C21 . . 119.51(17) ?
    C19 C20 H20 . . 120.2 ?
    C21 C20 H20 . . 120.2 ?
    C20 C21 C22 . . 120.45(17) ?
    C20 C21 H21 . . 119.8 ?
    C22 C21 H21 . . 119.8 ?
    C21 C22 C17 . . 119.69(16) ?
    C21 C22 H22 . . 120.2 ?
    C17 C22 H22 . . 120.2 ?
    N6 C23 C24 . . 111.52(15) ?
    N6 C23 C26 . . 120.31(15) ?
    C24 C23 C26 . . 128.16(16) ?
    C25 C24 C23 . . 104.98(15) ?
    C25 C24 H24 . . 127.5 ?
    C23 C24 H24 . . 127.5 ?
    N5 C25 C24 . . 107.81(14) ?
    N5 C25 N7 . . 121.23(14) ?
    C24 C25 N7 . . 130.93(15) ?
    C23 C26 H26A . . 109.5 ?
    C23 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C23 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    N7 C27 C28 . . 124.50(14) ?
    N7 C27 H27 . . 117.8 ?
    C28 C27 H27 . . 117.8 ?
    C27 C28 C29 . . 118.43(14) ?
    C27 C28 C30 . . 121.86(14) ?
    C29 C28 C30 . . 119.69(14) ?
    N8 C29 C28 . . 179.35(19) ?
    O3 C30 O4 . . 123.93(15) ?
    O3 C30 C28 . . 123.66(14) ?
    O4 C30 C28 . . 112.41(13) ?
    O4 C31 C32 . . 111.97(14) ?
    O4 C31 H31A . . 109.2 ?
    C32 C31 H31A . . 109.2 ?
    O4 C31 H31B . . 109.2 ?
    C32 C31 H31B . . 109.2 ?
    H31A C31 H31B . . 107.9 ?
    C31 C32 H32A . . 109.5 ?
    C31 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    C31 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 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
    C15 O2 C14 C12 . . . . -178.7(7) ?
    C11 C12 C14 O1 . . . . 4.9(17) ?
    C13 C12 C14 O1 . . . . -179.1(9) ?
    C11 C12 C14 O2 . . . . -174.8(10) ?
    C13 C12 C14 O2 . . . . 1.2(15) ?
    C14 O2 C15 C16 . . . . 84.3(2) ?
    C11 C12A C13A N4 . . . .  13E1(3)
                                     ?
    C14A C12A C13A N4 . . . .  -6E1(3)
                                      ?
    C15A O2A C14A O1A . . . . -2.7(15) ?
    C15A O2A C14A C12A . . . . -179(3) ?
    C11 C12A C14A O1A . . . . -8(8) ?
    C13A C12A C14A O1A . . . . 178(4) ?
    C11 C12A C14A O2A . . . . 168(4) ?
    C13A C12A C14A O2A . . . . -6(7) ?
    C14A O2A C15A C16A . . . . -83.1(10) ?
    C9 N1 N2 C7 . . . . -0.50(17) ?
    C1 N1 N2 C7 . . . . -172.92(13) ?
    C12A C13A N4 C13 . . . . -15(13) ?
    C9 N1 C1 C6 . . . . 49.5(2) ?
    N2 N1 C1 C6 . . . . -139.71(15) ?
    C9 N1 C1 C2 . . . . -131.12(17) ?
    N2 N1 C1 C2 . . . . 39.7(2) ?
    C6 C1 C2 C3 . . . . -1.2(2) ?
    N1 C1 C2 C3 . . . . 179.48(15) ?
    C1 C2 C3 C4 . . . . -0.3(3) ?
    C2 C3 C4 C5 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . 0.1(3) ?
    C2 C1 C6 C5 . . . . 2.1(2) ?
    N1 C1 C6 C5 . . . . -178.57(14) ?
    C4 C5 C6 C1 . . . . -1.5(2) ?
    N1 N2 C7 C8 . . . . 0.09(18) ?
    N1 N2 C7 C10 . . . . 179.26(14) ?
    N2 C7 C8 C9 . . . . 0.33(19) ?
    C10 C7 C8 C9 . . . . -178.75(16) ?
    N2 N1 C9 C8 . . . . 0.72(17) ?
    C1 N1 C9 C8 . . . . 172.13(15) ?
    N2 N1 C9 N3 . . . . -178.38(13) ?
    C1 N1 C9 N3 . . . . -7.0(2) ?
    C7 C8 C9 N1 . . . . -0.62(17) ?
    C7 C8 C9 N3 . . . . 178.36(16) ?
    C11 N3 C9 N1 . . . . 173.94(14) ?
    C11 N3 C9 C8 . . . . -4.9(3) ?
    C9 N3 C11 C12 . . . . 174.7(9) ?
    C9 N3 C11 C12A . . . . -178(4) ?
    C13 C12 C11 N3 . . . . -179.5(9) ?
    C14 C12 C11 N3 . . . . -3.5(17) ?
    C13 C12 C11 C12A . . . . 94(10) ?
    C14 C12 C11 C12A . . . . -90(9) ?
    C13A C12A C11 N3 . . . . 178(4) ?
    C14A C12A C11 N3 . . . . 4(8) ?
    C13A C12A C11 C12 . . . . -85(9) ?
    C25 N5 N6 C23 . . . . 1.57(18) ?
    C17 N5 N6 C23 . . . . -178.15(14) ?
    C25 N5 C17 C22 . . . . 143.45(17) ?
    N6 N5 C17 C22 . . . . -36.9(2) ?
    C25 N5 C17 C18 . . . . -38.2(3) ?
    N6 N5 C17 C18 . . . . 141.49(16) ?
    C22 C17 C18 C19 . . . . -2.5(3) ?
    N5 C17 C18 C19 . . . . 179.13(16) ?
    C17 C18 C19 C20 . . . . 2.2(3) ?
    C18 C19 C20 C21 . . . . -0.4(3) ?
    C19 C20 C21 C22 . . . . -1.2(3) ?
    C20 C21 C22 C17 . . . . 0.9(3) ?
    C18 C17 C22 C21 . . . . 1.0(3) ?
    N5 C17 C22 C21 . . . . 179.36(15) ?
    N5 N6 C23 C24 . . . . -1.36(19) ?
    N5 N6 C23 C26 . . . . 177.54(16) ?
    N6 C23 C24 C25 . . . . 0.7(2) ?
    C26 C23 C24 C25 . . . . -178.12(18) ?
    N6 N5 C25 C24 . . . . -1.20(19) ?
    C17 N5 C25 C24 . . . . 178.49(16) ?
    N6 N5 C25 N7 . . . . 176.97(14) ?
    C17 N5 C25 N7 . . . . -3.3(3) ?
    C23 C24 C25 N5 . . . . 0.33(19) ?
    C23 C24 C25 N7 . . . . -177.59(17) ?
    C27 N7 C25 N5 . . . . 165.61(15) ?
    C27 N7 C25 C24 . . . . -16.7(3) ?
    C25 N7 C27 C28 . . . . 177.38(15) ?
    N7 C27 C28 C29 . . . . 178.21(15) ?
    N7 C27 C28 C30 . . . . 0.0(3) ?
    C31 O4 C30 O3 . . . . -3.8(2) ?
    C31 O4 C30 C28 . . . . 177.29(13) ?
    C27 C28 C30 O3 . . . . 0.3(3) ?
    C29 C28 C30 O3 . . . . -177.87(15) ?
    C27 C28 C30 O4 . . . . 179.22(14) ?
    C29 C28 C30 O4 . . . . 1.0(2) ?
    C30 O4 C31 C32 . . . . 84.67(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
    _geom_hbond_publ_flag
    C15 H15B N2 1_645 0.99 2.63 3.455(2) 141 yes
    C16 H16C O3 1_545 0.98 2.52 3.430(3) 155 yes
    N3 H3A O1 . 0.91 1.96 2.677(4) 134 yes
    C10 H10C O2 1_465 0.98 2.55 3.506(2) 164 yes
    C11 H11 N8 2_665 0.95 2.37 3.306(2) 168 yes
    N7 H7A O3 . 0.91 2.00 2.7027(17) 133 yes
    C24 H24 N4 2_665 0.95 2.68 3.555(2) 153 yes
    C26 H26C O4 1_465 0.98 2.55 3.523(2) 172 yes
    C27 H27 N4 2_665 0.95 2.40 3.322(2) 164 yes
    C31 H31A N2 1_655 0.99 2.57 3.366(2) 138 yes
    C31 H31B N6 1_645 0.99 2.63 3.437(2) 139 yes
    C32 H32C O1 . 0.98 2.55 3.468(3) 155 yes
_shelxl_version_number     '2014-3'
