##############################################################################
###                                                                        ###
###        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/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-07-11
_journal_date_accepted     2007-07-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3588
_journal_page_last     o3588
_journal_paper_category     QO
_journal_coeditor_code     CI2415
_publ_contact_author_name     'Neng-qiang Wang'
_publ_contact_author_address
;
College of Life Science,
Hunan University of Science and Technology,
Xiangtan, Hunan, 411201,
People's Republic of China
;
_publ_contact_author_email     nqwang@hnust.cn
_publ_section_title
;\
2-Chloro-N-cyclopropyl-9-(3,4,5,6-tetrahydro-2H-pyran-2-yl)-\
9H-purin-6-amine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Neng-Qiang Wang' .
;
College of Life Science,
Hunan University of Science and Technology,
Xiangtan, Hunan, 411201,
People's Republic of China
;
    'Ting-Ting Mao' .
;
Intensive Care Unit,
Zhejiang Provincial People's Hospital,
Hangzhou,
Zhejiang 310014
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Chloro-N-cyclopropyl-9-(3,4,5,6-tetrahydro-2H-pyran-2-yl)-
9H-purin-6-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H16 Cl N5 O'
_chemical_formula_sum     'C13 H16 Cl N5 O'
_chemical_formula_iupac     'C13 H16 Cl N5 O'
_chemical_formula_weight     293.76
_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     11.385(4)
_cell_length_b     11.686(4)
_cell_length_c     11.692(4)
_cell_angle_alpha     111.380(5)
_cell_angle_beta     96.954(4)
_cell_angle_gamma     94.531(5)
_cell_volume     1425.0(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     809
_cell_measurement_theta_min     2.831
_cell_measurement_theta_max     26.353
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.272
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9604
_exptl_absorpt_correction_T_max     0.9733
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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 APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6270
_diffrn_reflns_av_R_equivalents     0.0521
_diffrn_reflns_av_sigmaI/netI     0.0548
_diffrn_reflns_theta_min     1.82
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_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     5203
_reflns_number_gt     3410
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0901
_refine_ls_R_factor_gt     0.0662
_refine_ls_wR_factor_gt     0.1791
_refine_ls_wR_factor_ref     0.1966
_refine_ls_goodness_of_fit_ref     0.972
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     5203
_refine_ls_number_parameters     361
_refine_ls_number_restraints     18
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1257P)²] 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     0.430
_refine_diff_density_min     -0.387
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Bruker, 2005)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL'
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 Cl1 0.82375(8) 1.22208(8) 0.49371(7) 0.0679(3) Uani d . 1 . .
    N N1 0.6765(2) 1.0223(2) 0.3754(2) 0.0446(6) Uani d . 1 . .
    C C2 0.7559(2) 1.1004(3) 0.3569(3) 0.0435(7) Uani d . 1 . .
    N N3 0.7924(2) 1.1026(2) 0.2554(2) 0.0457(6) Uani d . 1 . .
    C C4 0.7344(2) 1.0042(3) 0.1565(3) 0.0396(6) Uani d . 1 . .
    C C5 0.6513(2) 0.9123(3) 0.1579(2) 0.0410(6) Uani d . 1 . .
    C C6 0.6234(2) 0.9227(3) 0.2749(3) 0.0411(6) Uani d . 1 . .
    N N7 0.6115(2) 0.8259(2) 0.0393(2) 0.0504(6) Uani d . 1 . .
    C C8 0.6701(3) 0.8670(3) -0.0301(3) 0.0530(8) Uani d . 1 . .
    H H8 0.6613 0.8266 -0.1160 0.064 Uiso calc R 1 . .
    N N9 0.7458(2) 0.9747(2) 0.0342(2) 0.0465(6) Uani d . 1 . .
    N N10 0.5473(2) 0.8376(2) 0.2888(2) 0.0488(6) Uani d . 1 . .
    H H10 0.5159 0.7747 0.2229 0.059 Uiso calc R 1 . .
    C C11 0.5135(3) 0.8424(3) 0.4043(3) 0.0512(8) Uani d . 1 . .
    H H11 0.4422 0.8819 0.4258 0.061 Uiso calc R 1 . .
    C C12 0.5288(3) 0.7332(3) 0.4394(3) 0.0663(10) Uani d . 1 . .
    H H12A 0.5655 0.6664 0.3852 0.080 Uiso calc R 1 . .
    H H12B 0.4676 0.7074 0.4793 0.080 Uiso calc R 1 . .
    C C13 0.6053(3) 0.8556(3) 0.5106(3) 0.0628(9) Uani d . 1 . .
    H H13A 0.5906 0.9033 0.5936 0.075 Uiso calc R 1 . .
    H H13B 0.6883 0.8623 0.4995 0.075 Uiso calc R 1 . .
    C C14 0.8143(3) 1.0476(3) -0.0185(3) 0.0495(7) Uani d . 1 . .
    H H14 0.8763 1.1050 0.0476 0.059 Uiso calc R 1 . .
    O O15 0.8690(2) 0.9658(2) -0.1059(2) 0.0680(7) Uani d . 1 . .
    C C16 0.9436(3) 1.0287(4) -0.1627(4) 0.0786(12) Uani d . 1 . .
    H H16A 0.9815 0.9682 -0.2230 0.094 Uiso calc R 1 . .
    H H16B 1.0060 1.0862 -0.0992 0.094 Uiso calc R 1 . .
    C C17 0.8755(4) 1.0963(5) -0.2247(4) 0.0972(17) Uani d . 1 . .
    H H17A 0.8176 1.0385 -0.2933 0.117 Uiso calc R 1 . .
    H H17B 0.9288 1.1405 -0.2579 0.117 Uiso calc R 1 . .
    C C18 0.8136(5) 1.1846(6) -0.1353(6) 0.139(2) Uani d U 1 . .
    H H18A 0.7613 1.2225 -0.1788 0.167 Uiso calc R 1 . .
    H H18B 0.8719 1.2498 -0.0741 0.167 Uiso calc R 1 . .
    C C19 0.7405(4) 1.1203(5) -0.0695(6) 0.122(2) Uani d U 1 . .
    H H19A 0.7101 1.1819 -0.0028 0.147 Uiso calc R 1 . .
    H H19B 0.6728 1.0662 -0.1280 0.147 Uiso calc R 1 . .
    Cl Cl2 0.13063(8) 0.24465(10) -0.34039(8) 0.0752(3) Uani d . 1 . .
    N N21 0.2902(2) 0.4357(2) -0.2234(2) 0.0481(6) Uani d . 1 . .
    C C22 0.2118(3) 0.3567(3) -0.2043(3) 0.0500(7) Uani d . 1 . .
    N N23 0.1835(2) 0.3502(2) -0.1010(2) 0.0501(6) Uani d . 1 . .
    C C24 0.2502(2) 0.4397(3) -0.0029(3) 0.0433(7) Uani d . 1 . .
    C C25 0.3371(2) 0.5292(3) -0.0051(3) 0.0420(6) Uani d . 1 . .
    C C26 0.3549(2) 0.5259(3) -0.1223(3) 0.0428(7) Uani d . 1 . .
    N N27 0.3872(2) 0.6087(2) 0.1140(2) 0.0471(6) Uani d . 1 . .
    C C28 0.3303(3) 0.5663(3) 0.1848(3) 0.0500(7) Uani d . 1 . .
    H H28 0.3454 0.6022 0.2712 0.060 Uiso calc R 1 . .
    N N29 0.2472(2) 0.4654(2) 0.1207(2) 0.0469(6) Uani d . 1 . .
    N N30 0.4314(2) 0.6108(2) -0.1362(2) 0.0476(6) Uani d . 1 . .
    H H30 0.4699 0.6686 -0.0698 0.057 Uiso calc R 1 . .
    C C31 0.4541(3) 0.6129(3) -0.2525(3) 0.0493(7) Uani d . 1 . .
    H H31 0.5140 0.5618 -0.2903 0.059 Uiso calc R 1 . .
    C C32 0.4517(3) 0.7314(3) -0.2715(3) 0.0650(9) Uani d . 1 . .
    H H32A 0.4313 0.8018 -0.2051 0.078 Uiso calc R 1 . .
    H H32B 0.5097 0.7520 -0.3176 0.078 Uiso calc R 1 . .
    C C33 0.3567(3) 0.6261(4) -0.3404(4) 0.0734(11) Uani d U 1 . .
    H H33A 0.2782 0.6322 -0.3162 0.088 Uiso calc R 1 . .
    H H33B 0.3566 0.5825 -0.4286 0.088 Uiso calc R 1 . .
    C C34 0.1686(3) 0.4008(3) 0.1736(3) 0.0517(8) Uani d . 1 . .
    H H34 0.1401 0.3167 0.1127 0.062 Uiso calc R 1 . .
    O O35 0.24039(19) 0.3944(2) 0.2761(2) 0.0628(6) Uani d . 1 . .
    C C36 0.1765(4) 0.3320(4) 0.3394(4) 0.0787(11) Uani d . 1 . .
    H H36A 0.2301 0.3297 0.4095 0.094 Uiso calc R 1 . .
    H H36B 0.1482 0.2472 0.2833 0.094 Uiso calc R 1 . .
    C C37 0.0730(4) 0.3954(4) 0.3849(4) 0.0780(11) Uani d . 1 . .
    H H37A 0.0286 0.3482 0.4225 0.094 Uiso calc R 1 . .
    H H37B 0.1018 0.4771 0.4480 0.094 Uiso calc R 1 . .
    C C38 -0.0070(3) 0.4075(4) 0.2807(4) 0.0864(13) Uani d . 1 . .
    H H38A -0.0683 0.4576 0.3134 0.104 Uiso calc R 1 . .
    H H38B -0.0460 0.3262 0.2244 0.104 Uiso calc R 1 . .
    C C39 0.0643(3) 0.4678(4) 0.2101(4) 0.0672(10) Uani d . 1 . .
    H H39A 0.0135 0.4654 0.1362 0.081 Uiso calc R 1 . .
    H H39B 0.0922 0.5539 0.2623 0.081 Uiso calc R 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
    Cl1 C2 . 1.746(3) ?
    N1 C2 . 1.326(3) ?
    N1 C6 . 1.349(3) ?
    C2 N3 . 1.312(3) ?
    N3 C4 . 1.349(3) ?
    C4 N9 . 1.368(3) ?
    C4 C5 . 1.380(4) ?
    C5 N7 . 1.380(4) ?
    C5 C6 . 1.405(4) ?
    C6 N10 . 1.335(3) ?
    N7 C8 . 1.303(4) ?
    C8 N9 . 1.368(4) ?
    C8 H8 . 0.93 ?
    N9 C14 . 1.453(3) ?
    N10 C11 . 1.431(3) ?
    N10 H10 . 0.86 ?
    C11 C13 . 1.477(5) ?
    C11 C12 . 1.492(5) ?
    C11 H11 . 0.98 ?
    C12 C13 . 1.502(5) ?
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 H13A . 0.97 ?
    C13 H13B . 0.97 ?
    C14 O15 . 1.372(4) ?
    C14 C19 . 1.464(5) ?
    C14 H14 . 0.98 ?
    O15 C16 . 1.449(4) ?
    C16 C17 . 1.459(6) ?
    C16 H16A . 0.97 ?
    C16 H16B . 0.97 ?
    C17 C18 . 1.469(7) ?
    C17 H17A . 0.97 ?
    C17 H17B . 0.97 ?
    C18 C19 . 1.526(5) ?
    C18 H18A . 0.97 ?
    C18 H18B . 0.97 ?
    C19 H19A . 0.97 ?
    C19 H19B . 0.97 ?
    Cl2 C22 . 1.742(3) ?
    N21 C22 . 1.329(4) ?
    N21 C26 . 1.345(4) ?
    C22 N23 . 1.312(4) ?
    N23 C24 . 1.332(4) ?
    C24 N29 . 1.370(4) ?
    C24 C25 . 1.391(4) ?
    C25 N27 . 1.382(4) ?
    C25 C26 . 1.396(4) ?
    C26 N30 . 1.336(3) ?
    N27 C28 . 1.315(3) ?
    C28 N29 . 1.362(4) ?
    C28 H28 . 0.93 ?
    N29 C34 . 1.457(3) ?
    N30 C31 . 1.424(4) ?
    N30 H30 . 0.86 ?
    C31 C33 . 1.475(5) ?
    C31 C32 . 1.482(4) ?
    C31 H31 . 0.98 ?
    C32 C33 . 1.479(5) ?
    C32 H32A . 0.97 ?
    C32 H32B . 0.97 ?
    C33 H33A . 0.97 ?
    C33 H33B . 0.97 ?
    C34 O35 . 1.395(4) ?
    C34 C39 . 1.494(4) ?
    C34 H34 . 0.98 ?
    O35 C36 . 1.431(4) ?
    C36 C37 . 1.491(5) ?
    C36 H36A . 0.97 ?
    C36 H36B . 0.97 ?
    C37 C38 . 1.487(6) ?
    C37 H37A . 0.97 ?
    C37 H37B . 0.97 ?
    C38 C39 . 1.528(5) ?
    C38 H38A . 0.97 ?
    C38 H38B . 0.97 ?
    C39 H39A . 0.97 ?
    C39 H39B . 0.97 ?
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
    C2 N1 C6 . . 117.1(2) ?
    N3 C2 N1 . . 131.9(3) ?
    N3 C2 Cl1 . . 114.7(2) ?
    N1 C2 Cl1 . . 113.4(2) ?
    C2 N3 C4 . . 109.3(2) ?
    N3 C4 N9 . . 127.3(2) ?
    N3 C4 C5 . . 127.0(2) ?
    N9 C4 C5 . . 105.7(2) ?
    N7 C5 C4 . . 111.0(2) ?
    N7 C5 C6 . . 132.5(3) ?
    C4 C5 C6 . . 116.6(3) ?
    N10 C6 N1 . . 119.8(2) ?
    N10 C6 C5 . . 122.2(3) ?
    N1 C6 C5 . . 118.1(2) ?
    C8 N7 C5 . . 103.5(2) ?
    N7 C8 N9 . . 114.3(3) ?
    N7 C8 H8 . . 122.8 ?
    N9 C8 H8 . . 122.8 ?
    C4 N9 C8 . . 105.5(2) ?
    C4 N9 C14 . . 127.6(2) ?
    C8 N9 C14 . . 126.7(2) ?
    C6 N10 C11 . . 125.4(2) ?
    C6 N10 H10 . . 117.3 ?
    C11 N10 H10 . . 117.3 ?
    N10 C11 C13 . . 120.4(3) ?
    N10 C11 C12 . . 117.5(3) ?
    C13 C11 C12 . . 60.8(2) ?
    N10 C11 H11 . . 115.6 ?
    C13 C11 H11 . . 115.6 ?
    C12 C11 H11 . . 115.6 ?
    C11 C12 C13 . . 59.1(2) ?
    C11 C12 H12A . . 117.9 ?
    C13 C12 H12A . . 117.9 ?
    C11 C12 H12B . . 117.9 ?
    C13 C12 H12B . . 117.9 ?
    H12A C12 H12B . . 115.0 ?
    C11 C13 C12 . . 60.1(2) ?
    C11 C13 H13A . . 117.8 ?
    C12 C13 H13A . . 117.8 ?
    C11 C13 H13B . . 117.8 ?
    C12 C13 H13B . . 117.8 ?
    H13A C13 H13B . . 114.9 ?
    O15 C14 N9 . . 106.4(2) ?
    O15 C14 C19 . . 112.9(3) ?
    N9 C14 C19 . . 112.4(3) ?
    O15 C14 H14 . . 108.3 ?
    N9 C14 H14 . . 108.3 ?
    C19 C14 H14 . . 108.3 ?
    C14 O15 C16 . . 111.5(3) ?
    O15 C16 C17 . . 112.1(3) ?
    O15 C16 H16A . . 109.2 ?
    C17 C16 H16A . . 109.2 ?
    O15 C16 H16B . . 109.2 ?
    C17 C16 H16B . . 109.2 ?
    H16A C16 H16B . . 107.9 ?
    C16 C17 C18 . . 109.6(4) ?
    C16 C17 H17A . . 109.7 ?
    C18 C17 H17A . . 109.7 ?
    C16 C17 H17B . . 109.7 ?
    C18 C17 H17B . . 109.7 ?
    H17A C17 H17B . . 108.2 ?
    C17 C18 C19 . . 111.1(4) ?
    C17 C18 H18A . . 109.4 ?
    C19 C18 H18A . . 109.4 ?
    C17 C18 H18B . . 109.4 ?
    C19 C18 H18B . . 109.4 ?
    H18A C18 H18B . . 108.0 ?
    C14 C19 C18 . . 110.3(3) ?
    C14 C19 H19A . . 109.6 ?
    C18 C19 H19A . . 109.6 ?
    C14 C19 H19B . . 109.6 ?
    C18 C19 H19B . . 109.6 ?
    H19A C19 H19B . . 108.1 ?
    C22 N21 C26 . . 117.3(2) ?
    N23 C22 N21 . . 131.2(3) ?
    N23 C22 Cl2 . . 114.8(2) ?
    N21 C22 Cl2 . . 114.0(2) ?
    C22 N23 C24 . . 110.0(2) ?
    N23 C24 N29 . . 128.1(3) ?
    N23 C24 C25 . . 126.7(3) ?
    N29 C24 C25 . . 105.2(2) ?
    N27 C25 C24 . . 111.2(2) ?
    N27 C25 C26 . . 132.3(3) ?
    C24 C25 C26 . . 116.5(3) ?
    N30 C26 N21 . . 119.7(3) ?
    N30 C26 C25 . . 122.0(3) ?
    N21 C26 C25 . . 118.2(3) ?
    C28 N27 C25 . . 103.2(2) ?
    N27 C28 N29 . . 114.3(3) ?
    N27 C28 H28 . . 122.9 ?
    N29 C28 H28 . . 122.9 ?
    C28 N29 C24 . . 106.2(2) ?
    C28 N29 C34 . . 126.6(2) ?
    C24 N29 C34 . . 127.2(2) ?
    C26 N30 C31 . . 125.0(3) ?
    C26 N30 H30 . . 117.5 ?
    C31 N30 H30 . . 117.5 ?
    N30 C31 C33 . . 120.0(3) ?
    N30 C31 C32 . . 118.0(3) ?
    C33 C31 C32 . . 60.0(2) ?
    N30 C31 H31 . . 115.8 ?
    C33 C31 H31 . . 115.8 ?
    C32 C31 H31 . . 115.8 ?
    C33 C32 C31 . . 59.7(2) ?
    C33 C32 H32A . . 117.8 ?
    C31 C32 H32A . . 117.8 ?
    C33 C32 H32B . . 117.8 ?
    C31 C32 H32B . . 117.8 ?
    H32A C32 H32B . . 114.9 ?
    C31 C33 C32 . . 60.2(2) ?
    C31 C33 H33A . . 117.7 ?
    C32 C33 H33A . . 117.7 ?
    C31 C33 H33B . . 117.7 ?
    C32 C33 H33B . . 117.7 ?
    H33A C33 H33B . . 114.9 ?
    O35 C34 N29 . . 105.0(2) ?
    O35 C34 C39 . . 111.9(3) ?
    N29 C34 C39 . . 111.4(3) ?
    O35 C34 H34 . . 109.5 ?
    N29 C34 H34 . . 109.5 ?
    C39 C34 H34 . . 109.5 ?
    C34 O35 C36 . . 112.4(3) ?
    O35 C36 C37 . . 111.4(3) ?
    O35 C36 H36A . . 109.3 ?
    C37 C36 H36A . . 109.3 ?
    O35 C36 H36B . . 109.3 ?
    C37 C36 H36B . . 109.3 ?
    H36A C36 H36B . . 108.0 ?
    C38 C37 C36 . . 110.7(3) ?
    C38 C37 H37A . . 109.5 ?
    C36 C37 H37A . . 109.5 ?
    C38 C37 H37B . . 109.5 ?
    C36 C37 H37B . . 109.5 ?
    H37A C37 H37B . . 108.1 ?
    C37 C38 C39 . . 110.4(3) ?
    C37 C38 H38A . . 109.6 ?
    C39 C38 H38A . . 109.6 ?
    C37 C38 H38B . . 109.6 ?
    C39 C38 H38B . . 109.6 ?
    H38A C38 H38B . . 108.1 ?
    C34 C39 C38 . . 110.1(3) ?
    C34 C39 H39A . . 109.6 ?
    C38 C39 H39A . . 109.6 ?
    C34 C39 H39B . . 109.6 ?
    C38 C39 H39B . . 109.6 ?
    H39A C39 H39B . . 108.2 ?
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 N1 C2 N3 . . . . 2.4(5) ?
    C6 N1 C2 Cl1 . . . . -177.4(2) ?
    N1 C2 N3 C4 . . . . -0.1(4) ?
    Cl1 C2 N3 C4 . . . . 179.67(19) ?
    C2 N3 C4 N9 . . . . 178.8(3) ?
    C2 N3 C4 C5 . . . . -1.4(4) ?
    N3 C4 C5 N7 . . . . -179.5(3) ?
    N9 C4 C5 N7 . . . . 0.4(3) ?
    N3 C4 C5 C6 . . . . 0.5(4) ?
    N9 C4 C5 C6 . . . . -179.6(2) ?
    C2 N1 C6 N10 . . . . 176.6(3) ?
    C2 N1 C6 C5 . . . . -3.2(4) ?
    N7 C5 C6 N10 . . . . 2.1(5) ?
    C4 C5 C6 N10 . . . . -177.9(3) ?
    N7 C5 C6 N1 . . . . -178.1(3) ?
    C4 C5 C6 N1 . . . . 1.9(4) ?
    C4 C5 N7 C8 . . . . -0.2(3) ?
    C6 C5 N7 C8 . . . . 179.9(3) ?
    C5 N7 C8 N9 . . . . -0.1(3) ?
    N3 C4 N9 C8 . . . . 179.4(3) ?
    C5 C4 N9 C8 . . . . -0.4(3) ?
    N3 C4 N9 C14 . . . . -6.0(5) ?
    C5 C4 N9 C14 . . . . 174.1(3) ?
    N7 C8 N9 C4 . . . . 0.4(4) ?
    N7 C8 N9 C14 . . . . -174.2(3) ?
    N1 C6 N10 C11 . . . . 0.9(4) ?
    C5 C6 N10 C11 . . . . -179.3(3) ?
    C6 N10 C11 C13 . . . . -55.2(4) ?
    C6 N10 C11 C12 . . . . -125.8(3) ?
    N10 C11 C12 C13 . . . . 111.3(3) ?
    N10 C11 C13 C12 . . . . -106.6(3) ?
    C4 N9 C14 O15 . . . . 138.7(3) ?
    C8 N9 C14 O15 . . . . -47.9(4) ?
    C4 N9 C14 C19 . . . . -97.2(4) ?
    C8 N9 C14 C19 . . . . 76.2(4) ?
    N9 C14 O15 C16 . . . . -178.2(3) ?
    C19 C14 O15 C16 . . . . 58.1(4) ?
    C14 O15 C16 C17 . . . . -59.6(5) ?
    O15 C16 C17 C18 . . . . 56.5(5) ?
    C16 C17 C18 C19 . . . . -52.5(6) ?
    O15 C14 C19 C18 . . . . -53.9(6) ?
    N9 C14 C19 C18 . . . . -174.2(4) ?
    C17 C18 C19 C14 . . . . 50.9(7) ?
    C26 N21 C22 N23 . . . . 0.7(5) ?
    C26 N21 C22 Cl2 . . . . 179.1(2) ?
    N21 C22 N23 C24 . . . . -1.4(5) ?
    Cl2 C22 N23 C24 . . . . -179.8(2) ?
    C22 N23 C24 N29 . . . . 179.2(3) ?
    C22 N23 C24 C25 . . . . 0.4(4) ?
    N23 C24 C25 N27 . . . . 179.0(3) ?
    N29 C24 C25 N27 . . . . 0.0(3) ?
    N23 C24 C25 C26 . . . . 1.1(4) ?
    N29 C24 C25 C26 . . . . -177.9(2) ?
    C22 N21 C26 N30 . . . . -177.2(3) ?
    C22 N21 C26 C25 . . . . 1.1(4) ?
    N27 C25 C26 N30 . . . . -0.9(5) ?
    C24 C25 C26 N30 . . . . 176.4(2) ?
    N27 C25 C26 N21 . . . . -179.2(3) ?
    C24 C25 C26 N21 . . . . -1.8(4) ?
    C24 C25 N27 C28 . . . . 0.0(3) ?
    C26 C25 N27 C28 . . . . 177.4(3) ?
    C25 N27 C28 N29 . . . . 0.0(3) ?
    N27 C28 N29 C24 . . . . 0.0(3) ?
    N27 C28 N29 C34 . . . . -178.2(3) ?
    N23 C24 N29 C28 . . . . -178.9(3) ?
    C25 C24 N29 C28 . . . . 0.0(3) ?
    N23 C24 N29 C34 . . . . -0.8(5) ?
    C25 C24 N29 C34 . . . . 178.2(3) ?
    N21 C26 N30 C31 . . . . -1.9(4) ?
    C25 C26 N30 C31 . . . . 179.9(3) ?
    C26 N30 C31 C33 . . . . 61.6(4) ?
    C26 N30 C31 C32 . . . . 131.3(3) ?
    N30 C31 C32 C33 . . . . -110.3(3) ?
    N30 C31 C33 C32 . . . . 107.1(3) ?
    C28 N29 C34 O35 . . . . -41.8(4) ?
    C24 N29 C34 O35 . . . . 140.4(3) ?
    C28 N29 C34 C39 . . . . 79.5(4) ?
    C24 N29 C34 C39 . . . . -98.3(4) ?
    N29 C34 O35 C36 . . . . -179.6(3) ?
    C39 C34 O35 C36 . . . . 59.4(4) ?
    C34 O35 C36 C37 . . . . -59.2(4) ?
    O35 C36 C37 C38 . . . . 55.5(5) ?
    C36 C37 C38 C39 . . . . -52.3(5) ?
    O35 C34 C39 C38 . . . . -55.3(4) ?
    N29 C34 C39 C38 . . . . -172.5(3) ?
    C37 C38 C39 C34 . . . . 51.9(5) ?
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
    N10 H10 N27 . 0.86 2.20 2.998(3) 155 yes
    N30 H30 N7 . 0.86 2.22 3.023(4) 155 yes
    C36 H36B O15 2_665 0.97 2.57 3.504(5) 162 yes
