##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# 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     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2009-08-21
_journal_date_accepted     2009-08-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     10
_journal_page_first     o2318
_journal_page_last     o2318
_journal_paper_category     QO
_journal_coeditor_code     HK2761
_publ_contact_author_name     'Ping-Fang Han'
_publ_contact_author_address
;
State Key Laboratory of Materials-Oriented Chemcial Engineering,
College of Life Science and Pharmaceutical Engineering,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     hpf@njut.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86 25  83172097'
_publ_section_title
;\
7-Chloro-5-(2-ethoxyphenyl)-1-methyl-3-propyl-2,6-dihydro-1H-pyrazolo[4,\
3-d]pyrimidine
;
loop_
    _publ_author_name
    _publ_author_address
    'Ming-Qiu Zhou'
;
College of Biotechnology and Pharmaceutical Engineering,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Kai Zhu'
;
College of Biotechnology and Pharmaceutical Engineering,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Xiao-Ping Lv'
;
College of Biotechnology and Pharmaceutical Engineering,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Ping-Fang Han'
;
College of Biotechnology and Pharmaceutical Engineering,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Ping Wei'
;
College of Biotechnology and Pharmaceutical Engineering,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
7-Chloro-5-(2-ethoxyphenyl)-1-methyl-3-propyl-2,6-dihydro-
1H-pyrazolo[4,3-d]pyrimidine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H21 Cl N4 O'
_chemical_formula_sum     'C17 H21 Cl N4 O'
_chemical_formula_iupac     'C17 H21 Cl N4 O'
_chemical_formula_weight     332.83
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     4.6700(9)
_cell_length_b     11.647(2)
_cell_length_c     16.064(3)
_cell_angle_alpha     78.56(3)
_cell_angle_beta     86.75(3)
_cell_angle_gamma     79.81(3)
_cell_volume     842.7(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     13
_cell_measurement_temperature     294(2)
_exptl_crystal_description     blocK
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     0.237
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9324
_exptl_absorpt_correction_T_max     0.9767
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'ω/2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3470
_diffrn_reflns_av_R_equivalents     0.0330
_diffrn_reflns_av_sigmaI/netI     0.0337
_diffrn_reflns_theta_min     1.29
_diffrn_reflns_theta_max     25.27
_diffrn_reflns_theta_full     25.27
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
_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.
;
_reflns_number_total     3061
_reflns_number_gt     2353
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0811
_refine_ls_R_factor_gt     0.0636
_refine_ls_wR_factor_gt     0.1675
_refine_ls_wR_factor_ref     0.1823
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     3061
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w=1/[σ²(Fo²)+(0.1P)²+0.6P] 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     0.376
_refine_diff_density_min     -0.520
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    Cl Cl 0.45734(19) 0.18716(7) 0.56202(5) 0.0581(3) Uani d . 1 . .
    O O1 0.4864(5) 0.49028(18) 0.68108(14) 0.0528(6) Uani d . 1 . .
    N N1 0.6871(5) 0.2658(2) 0.68131(14) 0.0420(6) Uani d . 1 . .
    H H1A 0.5753 0.3313 0.6613 0.050 Uiso calc R 1 . .
    N N2 1.0314(5) 0.1732(2) 0.78486(14) 0.0414(6) Uani d . 1 . .
    N N3 1.1345(6) -0.1091(2) 0.72458(16) 0.0506(7) Uani d . 1 . .
    H H3A 1.2075 -0.1828 0.7269 0.061 Uiso calc R 1 . .
    N N4 0.9354(6) -0.0435(2) 0.66884(16) 0.0466(6) Uani d . 1 . .
    C C1 0.1508(7) 0.5709(3) 0.5722(2) 0.0605(9) Uani d . 1 . .
    H H1B 0.0284 0.6416 0.5443 0.091 Uiso calc R 1 . .
    H H1C 0.0335 0.5119 0.5956 0.091 Uiso calc R 1 . .
    H H1D 0.2893 0.5410 0.5319 0.091 Uiso calc R 1 . .
    C C2 0.3079(7) 0.5992(3) 0.6417(2) 0.0550(8) Uani d . 1 . .
    H H2B 0.4278 0.6587 0.6189 0.066 Uiso calc R 1 . .
    H H2C 0.1703 0.6297 0.6829 0.066 Uiso calc R 1 . .
    C C3 0.6554(7) 0.4882(3) 0.74759(19) 0.0452(7) Uani d . 1 . .
    C C4 0.6545(8) 0.5877(3) 0.7839(2) 0.0597(9) Uani d . 1 . .
    H H4A 0.5325 0.6587 0.7632 0.072 Uiso calc R 1 . .
    C C5 0.8344(9) 0.5806(3) 0.8503(2) 0.0671(10) Uani d . 1 . .
    H H5A 0.8325 0.6470 0.8744 0.081 Uiso calc R 1 . .
    C C6 1.0161(9) 0.4770(3) 0.8812(2) 0.0635(9) Uani d . 1 . .
    H H6A 1.1384 0.4735 0.9257 0.076 Uiso calc R 1 . .
    C C7 1.0177(7) 0.3782(3) 0.8465(2) 0.0528(8) Uani d . 1 . .
    H H7A 1.1418 0.3082 0.8683 0.063 Uiso calc R 1 . .
    C C8 0.8384(6) 0.3800(3) 0.77958(18) 0.0428(7) Uani d . 1 . .
    C C9 0.8566(6) 0.2674(2) 0.74811(17) 0.0393(6) Uani d . 1 . .
    C C10 1.0325(6) 0.0743(2) 0.75138(17) 0.0397(6) Uani d . 1 . .
    C C11 0.8671(6) 0.0690(2) 0.68347(17) 0.0398(6) Uani d . 1 . .
    C C12 0.6759(6) 0.1717(2) 0.64296(17) 0.0389(6) Uani d . 1 . .
    C C13 1.1973(6) -0.0409(3) 0.77464(19) 0.0443(7) Uani d . 1 . .
    C C14 0.8296(8) -0.0978(3) 0.6049(2) 0.0606(9) Uani d . 1 . .
    H H14A 0.9214 -0.1795 0.6116 0.091 Uiso calc R 1 . .
    H H14B 0.8752 -0.0562 0.5493 0.091 Uiso calc R 1 . .
    H H14C 0.6226 -0.0934 0.6116 0.091 Uiso calc R 1 . .
    C C15 1.3994(7) -0.0863(3) 0.84708(19) 0.0502(8) Uani d . 1 . .
    H H15A 1.4993 -0.0232 0.8551 0.060 Uiso calc R 1 . .
    H H15B 1.5449 -0.1506 0.8332 0.060 Uiso calc R 1 . .
    C C16 1.2456(9) -0.1304(5) 0.9283(2) 0.0868(14) Uani d . 1 . .
    H H16A 1.0974 -0.0661 0.9409 0.104 Uiso calc R 1 . .
    H H16B 1.1471 -0.1936 0.9197 0.104 Uiso calc R 1 . .
    C C17 1.4345(10) -0.1757(5) 1.0040(2) 0.0865(13) Uani d . 1 . .
    H H17A 1.3173 -0.2021 1.0527 0.130 Uiso calc R 1 . .
    H H17B 1.5283 -0.1132 1.0147 0.130 Uiso calc R 1 . .
    H H17C 1.5793 -0.2410 0.9932 0.130 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl 0.0624(5) 0.0586(5) 0.0533(5) -0.0064(4) -0.0254(4) -0.0076(4)
    O1 0.0595(13) 0.0387(11) 0.0578(13) 0.0041(10) -0.0213(11) -0.0087(9)
    N1 0.0438(13) 0.0384(13) 0.0421(13) -0.0020(10) -0.0136(11) -0.0050(10)
    N2 0.0417(13) 0.0432(13) 0.0385(12) -0.0065(10) -0.0090(10) -0.0040(10)
    N3 0.0554(16) 0.0390(13) 0.0539(15) 0.0040(12) -0.0135(12) -0.0079(11)
    N4 0.0530(15) 0.0395(13) 0.0472(14) -0.0013(11) -0.0119(12) -0.0106(11)
    C1 0.0518(19) 0.061(2) 0.063(2) 0.0071(16) -0.0128(16) -0.0078(17)
    C2 0.0521(19) 0.0433(17) 0.063(2) 0.0070(14) -0.0095(16) -0.0055(15)
    C3 0.0453(16) 0.0440(16) 0.0469(17) -0.0074(13) -0.0020(13) -0.0102(13)
    C4 0.065(2) 0.0452(18) 0.070(2) -0.0044(16) -0.0089(18) -0.0163(16)
    C5 0.081(3) 0.057(2) 0.072(2) -0.0113(19) -0.012(2) -0.0298(18)
    C6 0.074(2) 0.065(2) 0.057(2) -0.0163(19) -0.0199(18) -0.0194(17)
    C7 0.0583(19) 0.0499(18) 0.0516(18) -0.0076(15) -0.0168(15) -0.0102(14)
    C8 0.0430(16) 0.0428(16) 0.0432(15) -0.0088(13) -0.0052(13) -0.0068(12)
    C9 0.0376(14) 0.0407(15) 0.0383(14) -0.0069(12) -0.0037(12) -0.0037(12)
    C10 0.0399(15) 0.0404(15) 0.0374(14) -0.0049(12) -0.0043(12) -0.0044(12)
    C11 0.0409(15) 0.0400(15) 0.0379(14) -0.0066(12) -0.0045(12) -0.0048(12)
    C12 0.0376(14) 0.0413(15) 0.0377(14) -0.0097(12) -0.0031(12) -0.0040(12)
    C13 0.0419(16) 0.0431(16) 0.0441(16) -0.0004(12) -0.0055(13) -0.0042(13)
    C14 0.074(2) 0.0503(19) 0.061(2) -0.0034(17) -0.0181(18) -0.0203(16)
    C15 0.0476(17) 0.0463(17) 0.0524(18) 0.0036(13) -0.0128(14) -0.0060(14)
    C16 0.060(2) 0.135(4) 0.057(2) -0.028(2) -0.0162(19) 0.014(2)
    C17 0.081(3) 0.117(4) 0.055(2) -0.024(3) -0.015(2) 0.010(2)
_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
    Cl C12 . 1.660(3) ?
    O1 C2 . 1.439(4) ?
    O1 C3 . 1.358(4) ?
    N1 C9 . 1.374(3) ?
    N1 C12 . 1.369(4) ?
    N1 H1A . 0.8600 ?
    N2 C9 . 1.304(4) ?
    N2 C10 . 1.363(4) ?
    N3 N4 . 1.350(3) ?
    N3 C13 . 1.315(4) ?
    N3 H3A . 0.8600 ?
    N4 C11 . 1.356(4) ?
    N4 C14 . 1.458(4) ?
    C1 C2 . 1.489(5) ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C1 H1D . 0.9600 ?
    C2 H2B . 0.9700 ?
    C2 H2C . 0.9700 ?
    C3 C4 . 1.396(4) ?
    C3 C8 . 1.412(4) ?
    C4 C5 . 1.375(5) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.367(5) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.373(5) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.395(4) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.484(4) ?
    C10 C11 . 1.389(4) ?
    C10 C13 . 1.414(4) ?
    C11 C12 . 1.425(4) ?
    C13 C15 . 1.493(4) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 C16 . 1.497(5) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.496(5) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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 O1 C2 . . 120.4(2) ?
    C12 N1 C9 . . 127.4(2) ?
    C12 N1 H1A . . 116.3 ?
    C9 N1 H1A . . 116.3 ?
    C9 N2 C10 . . 114.6(2) ?
    C13 N3 N4 . . 108.1(2) ?
    C13 N3 H3A . . 125.9 ?
    N4 N3 H3A . . 125.9 ?
    N3 N4 C11 . . 110.3(2) ?
    N3 N4 C14 . . 119.5(2) ?
    C11 N4 C14 . . 130.2(3) ?
    C2 C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C2 C1 H1D . . 109.5 ?
    H1B C1 H1D . . 109.5 ?
    H1C C1 H1D . . 109.5 ?
    O1 C2 C1 . . 106.9(3) ?
    O1 C2 H2B . . 110.3 ?
    C1 C2 H2B . . 110.3 ?
    O1 C2 H2C . . 110.3 ?
    C1 C2 H2C . . 110.3 ?
    H2B C2 H2C . . 108.6 ?
    O1 C3 C4 . . 122.6(3) ?
    O1 C3 C8 . . 117.3(3) ?
    C4 C3 C8 . . 120.1(3) ?
    C5 C4 C3 . . 119.9(3) ?
    C5 C4 H4A . . 120.0 ?
    C3 C4 H4A . . 120.0 ?
    C6 C5 C4 . . 120.8(3) ?
    C6 C5 H5A . . 119.6 ?
    C4 C5 H5A . . 119.6 ?
    C5 C6 C7 . . 119.9(3) ?
    C5 C6 H6A . . 120.1 ?
    C7 C6 H6A . . 120.1 ?
    C6 C7 C8 . . 121.8(3) ?
    C6 C7 H7A . . 119.1 ?
    C8 C7 H7A . . 119.1 ?
    C7 C8 C3 . . 117.5(3) ?
    C7 C8 C9 . . 116.9(3) ?
    C3 C8 C9 . . 125.6(3) ?
    N2 C9 N1 . . 122.1(3) ?
    N2 C9 C8 . . 119.1(3) ?
    N1 C9 C8 . . 118.8(2) ?
    N2 C10 C11 . . 125.1(3) ?
    N2 C10 C13 . . 129.4(3) ?
    C11 C10 C13 . . 105.4(3) ?
    N4 C11 C10 . . 106.8(2) ?
    N4 C11 C12 . . 132.7(3) ?
    C10 C11 C12 . . 120.5(3) ?
    N1 C12 C11 . . 110.1(2) ?
    N1 C12 Cl . . 120.5(2) ?
    C11 C12 Cl . . 129.4(2) ?
    N3 C13 C10 . . 109.3(3) ?
    N3 C13 C15 . . 122.6(3) ?
    C10 C13 C15 . . 127.9(3) ?
    N4 C14 H14A . . 109.5 ?
    N4 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    N4 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 C16 . . 112.7(3) ?
    C13 C15 H15A . . 109.1 ?
    C16 C15 H15A . . 109.1 ?
    C13 C15 H15B . . 109.1 ?
    C16 C15 H15B . . 109.1 ?
    H15A C15 H15B . . 107.8 ?
    C17 C16 C15 . . 115.6(3) ?
    C17 C16 H16A . . 108.4 ?
    C15 C16 H16A . . 108.4 ?
    C17 C16 H16B . . 108.4 ?
    C15 C16 H16B . . 108.4 ?
    H16A C16 H16B . . 107.5 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 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
    C3 O1 C2 C1 . . . . -179.6(3) ?
    C2 O1 C3 C4 . . . . 3.4(5) ?
    C2 O1 C3 C8 . . . . -176.2(3) ?
    C12 N1 C9 N2 . . . . -1.2(5) ?
    C12 N1 C9 C8 . . . . 179.2(3) ?
    C9 N1 C12 C11 . . . . 1.1(4) ?
    C9 N1 C12 Cl . . . . -179.6(2) ?
    C10 N2 C9 N1 . . . . 0.4(4) ?
    C10 N2 C9 C8 . . . . 180.0(2) ?
    C9 N2 C10 C11 . . . . 0.3(4) ?
    C9 N2 C10 C13 . . . . 178.9(3) ?
    C13 N3 N4 C11 . . . . -0.4(3) ?
    C13 N3 N4 C14 . . . . 179.3(3) ?
    N4 N3 C13 C10 . . . . 0.2(3) ?
    N4 N3 C13 C15 . . . . 176.7(3) ?
    N3 N4 C11 C10 . . . . 0.3(3) ?
    C14 N4 C11 C10 . . . . -179.3(3) ?
    N3 N4 C11 C12 . . . . 179.1(3) ?
    C14 N4 C11 C12 . . . . -0.5(6) ?
    O1 C3 C4 C5 . . . . -178.9(3) ?
    C8 C3 C4 C5 . . . . 0.7(5) ?
    C3 C4 C5 C6 . . . . 0.3(6) ?
    C4 C5 C6 C7 . . . . -0.7(6) ?
    C5 C6 C7 C8 . . . . 0.2(6) ?
    C6 C7 C8 C3 . . . . 0.7(5) ?
    C6 C7 C8 C9 . . . . -179.3(3) ?
    O1 C3 C8 C7 . . . . 178.4(3) ?
    C4 C3 C8 C7 . . . . -1.2(5) ?
    O1 C3 C8 C9 . . . . -1.6(5) ?
    C4 C3 C8 C9 . . . . 178.8(3) ?
    C7 C8 C9 N2 . . . . 1.4(4) ?
    C3 C8 C9 N2 . . . . -178.6(3) ?
    C7 C8 C9 N1 . . . . -179.0(3) ?
    C3 C8 C9 N1 . . . . 1.1(4) ?
    N2 C10 C11 N4 . . . . 178.7(3) ?
    C13 C10 C11 N4 . . . . -0.2(3) ?
    N2 C10 C11 C12 . . . . -0.3(4) ?
    C13 C10 C11 C12 . . . . -179.1(3) ?
    N4 C11 C12 N1 . . . . -179.1(3) ?
    C10 C11 C12 N1 . . . . -0.4(4) ?
    N4 C11 C12 Cl . . . . 1.7(5) ?
    C10 C11 C12 Cl . . . . -179.6(2) ?
    N2 C10 C13 N3 . . . . -178.9(3) ?
    C11 C10 C13 N3 . . . . -0.1(3) ?
    N2 C10 C13 C15 . . . . 4.9(5) ?
    C11 C10 C13 C15 . . . . -176.3(3) ?
    N3 C13 C15 C16 . . . . -90.3(4) ?
    C10 C13 C15 C16 . . . . 85.5(4) ?
    C13 C15 C16 C17 . . . . -179.2(4) ?
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 H1A O1 . 0.86 1.91 2.616(3) 138.00
