##############################################################################
#                                                                            #
# 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_I
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_journal_date_recd_electronic     2013-10-10
_journal_date_accepted     2013-10-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue     11
_journal_page_first     o1669
_journal_page_last     o1669
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813028109
_journal_coeditor_code     FJ2646
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene, New Hampshire 03435, USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     '603 358-2563'
_publ_section_title
;
Bis{4-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-yl}methane
;
loop_
    _publ_author_name
    _publ_author_address
    'Kavitha, Channappa N.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
    'Jasinski, Jerry P.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
    'Anderson, Brian J. '
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
    'Yathirajan, H. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
    'Kaur, Manpreet'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
_database_code_depnum_ccdc_archive     'CCDC 966213'
_chemical_name_systematic
;
Bis{4-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-yl}methane
;
_chemical_name_common
;
Bis-[1-(benzo[1,3]dioxol-5-yl-methyl)piperazinyl]methane
;
_chemical_formula_moiety     'C25 H32 N4 O4'
_chemical_formula_sum     'C25 H32 N4 O4'
_chemical_formula_iupac     'C25 H32 N4 O4'
_chemical_formula_weight     452.55
_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     orthorhombic
_space_group_name_H-M_alt     'P n 21 a '
_space_group_name_Hall     'P -2ac -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
    'x+1/2, y, -z+1/2'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     38.8025(10)
_cell_length_b     9.7675(2)
_cell_length_c     6.09571(13)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2310.29(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5154
_cell_measurement_theta_min     4.5232
_cell_measurement_theta_max     72.4095
_cell_measurement_temperature     173(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     968
_exptl_absorpt_coefficient_mu     0.723
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.83569
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type     'Agilent Xcalibur (Eos, Gemini)'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.0416
_diffrn_reflns_number     13559
_diffrn_reflns_av_R_equivalents     0.0456
_diffrn_reflns_theta_min     4.558
_diffrn_reflns_theta_max     72.561
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -43
_diffrn_reflns_limit_h_max     48
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     7
_refine_special_details     ?
_reflns_number_total     4199
_reflns_number_gt     3869
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0454
_refine_ls_R_factor_gt     0.0411
_refine_ls_wR_factor_gt     0.1040
_refine_ls_wR_factor_ref     0.1077
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     4199
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0485P)²+0.6698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.215
_refine_diff_density_min     -0.165
_refine_ls_extinction_method     'SHELXL2012 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0016(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
Flack parameter determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004)
;
_refine_ls_abs_structure_Flack     -0.03(15)
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     'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction     'CrysAlis RED (Agilent, 2012)'
_computing_structure_solution     'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement     'SHELXL2012 (Sheldrick, 2008)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.31516(6) 0.5691(3) 1.0003(4) 0.0425(5) Uani d 1 . .
    O O2 0.31379(7) 0.7799(3) 0.8258(4) 0.0534(7) Uani d 1 . .
    O O3 0.75845(6) 0.5660(3) 0.1266(4) 0.0452(6) Uani d 1 . .
    O O4 0.77389(6) 0.4101(3) -0.1424(4) 0.0431(6) Uani d 1 . .
    N N1 0.50857(6) 0.5885(3) 0.2715(4) 0.0316(6) Uani d 1 . .
    N N2 0.43489(6) 0.5829(3) 0.2856(4) 0.0283(5) Uani d 1 . .
    N N3 0.56439(6) 0.5613(3) 0.1084(4) 0.0305(5) Uani d 1 . .
    N N4 0.62717(6) 0.6657(3) -0.0775(4) 0.0287(5) Uani d 1 . .
    C C0AA 0.54264(8) 0.5299(4) 0.2949(5) 0.0359(7) Uani d 1 . .
    C C2 0.48991(8) 0.5896(4) 0.4788(5) 0.0388(8) Uani d 1 . .
    H H2A 0.5031 0.6394 0.5879 0.047 Uiso calc 1 . .
    H H2B 0.4868 0.4965 0.5306 0.047 Uiso calc 1 . .
    C C3 0.45513(8) 0.6567(4) 0.4487(5) 0.0363(7) Uani d 1 . .
    H H3A 0.4429 0.6576 0.5875 0.044 Uiso calc 1 . .
    H H3B 0.4583 0.7508 0.4018 0.044 Uiso calc 1 . .
    C C4 0.45353(7) 0.5831(4) 0.0781(4) 0.0320(6) Uani d 1 . .
    H H4A 0.4566 0.6766 0.0279 0.038 Uiso calc 1 . .
    H H4B 0.4403 0.5341 -0.0317 0.038 Uiso calc 1 . .
    C C5 0.48843(8) 0.5158(3) 0.1056(5) 0.0335(7) Uani d 1 . .
    H H5A 0.4854 0.4211 0.1496 0.040 Uiso calc 1 . .
    H H5B 0.5007 0.5169 -0.0332 0.040 Uiso calc 1 . .
    C C6 0.40051(8) 0.6420(3) 0.2635(5) 0.0336(7) Uani d 1 . .
    H H6A 0.3892 0.6021 0.1368 0.040 Uiso calc 1 . .
    H H6B 0.4026 0.7397 0.2382 0.040 Uiso calc 1 . .
    C C7 0.37846(7) 0.6181(3) 0.4645(5) 0.0290(6) Uani d 1 . .
    C C8 0.37856(7) 0.4919(3) 0.5700(5) 0.0291(6) Uani d 1 . .
    H H8 0.3930 0.4234 0.5177 0.035 Uiso calc 1 . .
    C C9 0.35775(7) 0.4641(3) 0.7517(5) 0.0304(6) Uani d 1 . .
    H H9 0.3578 0.3789 0.8197 0.036 Uiso calc 1 . .
    C C10 0.33726(7) 0.5687(3) 0.8245(4) 0.0297(6) Uani d 1 . .
    C C11 0.30024(9) 0.7027(4) 1.0040(6) 0.0445(8) Uani d 1 . .
    H H11A 0.2754 0.6961 0.9910 0.053 Uiso calc 1 . .
    H H11B 0.3056 0.7478 1.1416 0.053 Uiso calc 1 . .
    C C12 0.33670(8) 0.6945(3) 0.7208(5) 0.0331(7) Uani d 1 . .
    C C13 0.35674(8) 0.7227(3) 0.5419(5) 0.0337(7) Uani d 1 . .
    H H13 0.3560 0.8079 0.4740 0.040 Uiso calc 1 . .
    C C14 0.59693(8) 0.4870(3) 0.1253(5) 0.0342(7) Uani d 1 . .
    H H14A 0.5924 0.3894 0.1294 0.041 Uiso calc 1 . .
    H H14B 0.6085 0.5122 0.2605 0.041 Uiso calc 1 . .
    C C15 0.62001(8) 0.5196(3) -0.0679(5) 0.0332(7) Uani d 1 . .
    H H15A 0.6415 0.4695 -0.0540 0.040 Uiso calc 1 . .
    H H15B 0.6089 0.4909 -0.2027 0.040 Uiso calc 1 . .
    C C16 0.59437(7) 0.7386(3) -0.0990(5) 0.0311(6) Uani d 1 . .
    H H16A 0.5830 0.7110 -0.2337 0.037 Uiso calc 1 . .
    H H16B 0.5986 0.8364 -0.1065 0.037 Uiso calc 1 . .
    C C17 0.57131(7) 0.7078(3) 0.0934(5) 0.0320(6) Uani d 1 . .
    H H17A 0.5823 0.7388 0.2275 0.038 Uiso calc 1 . .
    H H17B 0.5498 0.7570 0.0770 0.038 Uiso calc 1 . .
    C C18 0.65041(7) 0.7011(3) -0.2577(5) 0.0341(7) Uani d 1 . .
    H H18A 0.6544 0.7991 -0.2567 0.041 Uiso calc 1 . .
    H H18B 0.6395 0.6779 -0.3959 0.041 Uiso calc 1 . .
    C C19 0.68447(7) 0.6275(3) -0.2412(5) 0.0310(6) Uani d 1 . .
    C C20 0.70492(8) 0.6439(4) -0.0521(5) 0.0333(7) Uani d 1 . .
    H H20 0.6987 0.7043 0.0590 0.040 Uiso calc 1 . .
    C C21 0.73433(7) 0.5672(4) -0.0390(4) 0.0314(6) Uani d 1 . .
    C C22 0.78104(9) 0.4551(4) 0.0760(6) 0.0439(8) Uani d 1 . .
    H H22A 0.7775 0.3806 0.1787 0.053 Uiso calc 1 . .
    H H22B 0.8048 0.4848 0.0872 0.053 Uiso calc 1 . .
    C C23 0.74391(7) 0.4755(3) -0.2007(5) 0.0323(7) Uani d 1 . .
    C C24 0.72513(8) 0.4605(4) -0.3887(5) 0.0367(7) Uani d 1 . .
    H H24 0.7320 0.4014 -0.4999 0.044 Uiso calc 1 . .
    C C25 0.69508(8) 0.5383(3) -0.4056(5) 0.0325(7) Uani d 1 . .
    H H25 0.6817 0.5302 -0.5314 0.039 Uiso calc 1 . .
    H H0AA 0.5513(8) 0.564(4) 0.426(5) 0.031(9) Uiso d 1 . .
    H H0AB 0.5410(9) 0.429(4) 0.313(6) 0.040(10) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C10 . 1.373(3) ?
    O1 C11 . 1.428(4) ?
    O2 C11 . 1.422(4) ?
    O2 C12 . 1.377(4) ?
    O3 C21 . 1.377(3) ?
    O3 C22 . 1.427(4) ?
    O4 C22 . 1.429(4) ?
    O4 C23 . 1.374(4) ?
    N1 C0AA . 1.447(4) ?
    N1 C2 . 1.456(4) ?
    N1 C5 . 1.462(4) ?
    N2 C3 . 1.458(4) ?
    N2 C4 . 1.457(3) ?
    N2 C6 . 1.460(4) ?
    N3 C0AA . 1.449(4) ?
    N3 C14 . 1.460(4) ?
    N3 C17 . 1.459(4) ?
    N4 C15 . 1.455(4) ?
    N4 C16 . 1.464(4) ?
    N4 C18 . 1.462(4) ?
    C0AA H0AA . 0.93(3) ?
    C0AA H0AB . 0.99(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C2 C3 . 1.512(4) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C4 C5 . 1.515(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C6 C7 . 1.512(4) ?
    C7 C8 . 1.390(4) ?
    C7 C13 . 1.406(4) ?
    C8 H8 . 0.9300 ?
    C8 C9 . 1.397(4) ?
    C9 H9 . 0.9300 ?
    C9 C10 . 1.369(4) ?
    C10 C12 . 1.382(5) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.367(4) ?
    C13 H13 . 0.9300 ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C14 C15 . 1.513(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C16 C17 . 1.505(4) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C18 C19 . 1.508(4) ?
    C19 C20 . 1.409(4) ?
    C19 C25 . 1.390(4) ?
    C20 H20 . 0.9300 ?
    C20 C21 . 1.367(5) ?
    C21 C23 . 1.382(4) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    C23 C24 . 1.366(5) ?
    C24 H24 . 0.9300 ?
    C24 C25 . 1.396(5) ?
    C25 H25 . 0.9300 ?
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
    C10 O1 C11 . . 105.5(3) ?
    C12 O2 C11 . . 105.8(3) ?
    C21 O3 C22 . . 105.4(3) ?
    C23 O4 C22 . . 105.2(2) ?
    C0AA N1 C2 . . 111.8(2) ?
    C0AA N1 C5 . . 111.4(3) ?
    C2 N1 C5 . . 109.8(2) ?
    C3 N2 C6 . . 111.1(2) ?
    C4 N2 C3 . . 108.9(2) ?
    C4 N2 C6 . . 111.9(2) ?
    C0AA N3 C14 . . 110.1(2) ?
    C0AA N3 C17 . . 111.3(3) ?
    C14 N3 C17 . . 109.4(2) ?
    C15 N4 C16 . . 108.3(2) ?
    C15 N4 C18 . . 112.3(3) ?
    C16 N4 C18 . . 110.7(2) ?
    N1 C0AA N3 . . 111.8(3) ?
    N1 C0AA H0AA . . 106(2) ?
    N1 C0AA H0AB . . 110(2) ?
    N3 C0AA H0AA . . 113(2) ?
    N3 C0AA H0AB . . 109(2) ?
    H0AA C0AA H0AB . . 106(3) ?
    N1 C2 H2A . . 109.7 ?
    N1 C2 H2B . . 109.7 ?
    N1 C2 C3 . . 110.0(3) ?
    H2A C2 H2B . . 108.2 ?
    C3 C2 H2A . . 109.7 ?
    C3 C2 H2B . . 109.7 ?
    N2 C3 C2 . . 110.4(3) ?
    N2 C3 H3A . . 109.6 ?
    N2 C3 H3B . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.1 ?
    N2 C4 H4A . . 109.6 ?
    N2 C4 H4B . . 109.6 ?
    N2 C4 C5 . . 110.3(2) ?
    H4A C4 H4B . . 108.1 ?
    C5 C4 H4A . . 109.6 ?
    C5 C4 H4B . . 109.6 ?
    N1 C5 C4 . . 110.1(3) ?
    N1 C5 H5A . . 109.6 ?
    N1 C5 H5B . . 109.6 ?
    C4 C5 H5A . . 109.6 ?
    C4 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.2 ?
    N2 C6 H6A . . 109.1 ?
    N2 C6 H6B . . 109.1 ?
    N2 C6 C7 . . 112.4(2) ?
    H6A C6 H6B . . 107.9 ?
    C7 C6 H6A . . 109.1 ?
    C7 C6 H6B . . 109.1 ?
    C8 C7 C6 . . 120.7(3) ?
    C8 C7 C13 . . 119.4(3) ?
    C13 C7 C6 . . 119.9(3) ?
    C7 C8 H8 . . 118.7 ?
    C7 C8 C9 . . 122.5(3) ?
    C9 C8 H8 . . 118.7 ?
    C8 C9 H9 . . 121.7 ?
    C10 C9 C8 . . 116.6(3) ?
    C10 C9 H9 . . 121.7 ?
    O1 C10 C12 . . 110.2(3) ?
    C9 C10 O1 . . 128.2(3) ?
    C9 C10 C12 . . 121.6(3) ?
    O1 C11 H11A . . 109.9 ?
    O1 C11 H11B . . 109.9 ?
    O2 C11 O1 . . 108.8(2) ?
    O2 C11 H11A . . 109.9 ?
    O2 C11 H11B . . 109.9 ?
    H11A C11 H11B . . 108.3 ?
    O2 C12 C10 . . 109.7(3) ?
    C13 C12 O2 . . 128.0(3) ?
    C13 C12 C10 . . 122.4(3) ?
    C7 C13 H13 . . 121.2 ?
    C12 C13 C7 . . 117.5(3) ?
    C12 C13 H13 . . 121.2 ?
    N3 C14 H14A . . 109.5 ?
    N3 C14 H14B . . 109.5 ?
    N3 C14 C15 . . 110.6(3) ?
    H14A C14 H14B . . 108.1 ?
    C15 C14 H14A . . 109.5 ?
    C15 C14 H14B . . 109.5 ?
    N4 C15 C14 . . 110.5(3) ?
    N4 C15 H15A . . 109.5 ?
    N4 C15 H15B . . 109.5 ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 108.1 ?
    N4 C16 H16A . . 109.6 ?
    N4 C16 H16B . . 109.6 ?
    N4 C16 C17 . . 110.5(2) ?
    H16A C16 H16B . . 108.1 ?
    C17 C16 H16A . . 109.6 ?
    C17 C16 H16B . . 109.6 ?
    N3 C17 C16 . . 110.7(2) ?
    N3 C17 H17A . . 109.5 ?
    N3 C17 H17B . . 109.5 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 108.1 ?
    N4 C18 H18A . . 109.2 ?
    N4 C18 H18B . . 109.2 ?
    N4 C18 C19 . . 112.2(2) ?
    H18A C18 H18B . . 107.9 ?
    C19 C18 H18A . . 109.2 ?
    C19 C18 H18B . . 109.2 ?
    C20 C19 C18 . . 119.6(3) ?
    C25 C19 C18 . . 120.7(3) ?
    C25 C19 C20 . . 119.6(3) ?
    C19 C20 H20 . . 121.5 ?
    C21 C20 C19 . . 117.1(3) ?
    C21 C20 H20 . . 121.5 ?
    O3 C21 C23 . . 109.5(3) ?
    C20 C21 O3 . . 127.9(3) ?
    C20 C21 C23 . . 122.6(3) ?
    O3 C22 O4 . . 108.4(3) ?
    O3 C22 H22A . . 110.0 ?
    O3 C22 H22B . . 110.0 ?
    O4 C22 H22A . . 110.0 ?
    O4 C22 H22B . . 110.0 ?
    H22A C22 H22B . . 108.4 ?
    O4 C23 C21 . . 110.2(3) ?
    C24 C23 O4 . . 128.2(3) ?
    C24 C23 C21 . . 121.6(3) ?
    C23 C24 H24 . . 121.6 ?
    C23 C24 C25 . . 116.7(3) ?
    C25 C24 H24 . . 121.6 ?
    C19 C25 C24 . . 122.4(3) ?
    C19 C25 H25 . . 118.8 ?
    C24 C25 H25 . . 118.8 ?
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
    O1 C10 C12 O2 . . . . -0.7(4) ?
    O1 C10 C12 C13 . . . . 179.1(3) ?
    O2 C12 C13 C7 . . . . 179.6(3) ?
    O3 C21 C23 O4 . . . . 1.5(4) ?
    O3 C21 C23 C24 . . . . -177.3(3) ?
    O4 C23 C24 C25 . . . . 179.0(3) ?
    N1 C2 C3 N2 . . . . 59.5(4) ?
    N2 C4 C5 N1 . . . . -59.0(3) ?
    N2 C6 C7 C8 . . . . -42.1(4) ?
    N2 C6 C7 C13 . . . . 140.0(3) ?
    N3 C14 C15 N4 . . . . 59.2(3) ?
    N4 C16 C17 N3 . . . . -59.4(3) ?
    N4 C18 C19 C20 . . . . -58.0(4) ?
    N4 C18 C19 C25 . . . . 118.7(3) ?
    C0AA N1 C2 C3 . . . . 177.7(3) ?
    C0AA N1 C5 C4 . . . . -177.6(3) ?
    C0AA N3 C14 C15 . . . . -179.6(3) ?
    C0AA N3 C17 C16 . . . . 179.1(2) ?
    C2 N1 C0AA N3 . . . . -164.6(3) ?
    C2 N1 C5 C4 . . . . 58.0(3) ?
    C3 N2 C4 C5 . . . . 59.2(3) ?
    C3 N2 C6 C7 . . . . -69.1(3) ?
    C4 N2 C3 C2 . . . . -59.5(3) ?
    C4 N2 C6 C7 . . . . 169.0(3) ?
    C5 N1 C0AA N3 . . . . 72.2(3) ?
    C5 N1 C2 C3 . . . . -58.2(4) ?
    C6 N2 C3 C2 . . . . 176.9(2) ?
    C6 N2 C4 C5 . . . . -177.7(3) ?
    C6 C7 C8 C9 . . . . -177.8(3) ?
    C6 C7 C13 C12 . . . . 178.3(3) ?
    C7 C8 C9 C10 . . . . -0.9(4) ?
    C8 C7 C13 C12 . . . . 0.4(4) ?
    C8 C9 C10 O1 . . . . -178.6(3) ?
    C8 C9 C10 C12 . . . . 1.2(4) ?
    C9 C10 C12 O2 . . . . 179.4(3) ?
    C9 C10 C12 C13 . . . . -0.8(5) ?
    C10 O1 C11 O2 . . . . 0.5(3) ?
    C10 C12 C13 C7 . . . . -0.1(4) ?
    C11 O1 C10 C9 . . . . 179.9(3) ?
    C11 O1 C10 C12 . . . . 0.1(3) ?
    C11 O2 C12 C10 . . . . 1.0(4) ?
    C11 O2 C12 C13 . . . . -178.8(3) ?
    C12 O2 C11 O1 . . . . -0.9(4) ?
    C13 C7 C8 C9 . . . . 0.1(4) ?
    C14 N3 C0AA N1 . . . . -173.1(3) ?
    C14 N3 C17 C16 . . . . 57.2(3) ?
    C15 N4 C16 C17 . . . . 59.5(3) ?
    C15 N4 C18 C19 . . . . -58.6(3) ?
    C16 N4 C15 C14 . . . . -59.4(3) ?
    C16 N4 C18 C19 . . . . -179.8(3) ?
    C17 N3 C0AA N1 . . . . 65.3(3) ?
    C17 N3 C14 C15 . . . . -56.9(3) ?
    C18 N4 C15 C14 . . . . 178.0(2) ?
    C18 N4 C16 C17 . . . . -176.9(2) ?
    C18 C19 C20 C21 . . . . 175.4(3) ?
    C18 C19 C25 C24 . . . . -175.0(3) ?
    C19 C20 C21 O3 . . . . 179.3(3) ?
    C19 C20 C21 C23 . . . . -0.8(5) ?
    C20 C19 C25 C24 . . . . 1.7(5) ?
    C20 C21 C23 O4 . . . . -178.4(3) ?
    C20 C21 C23 C24 . . . . 2.9(5) ?
    C21 O3 C22 O4 . . . . 11.6(4) ?
    C21 C23 C24 C25 . . . . -2.5(5) ?
    C22 O3 C21 C20 . . . . 171.8(3) ?
    C22 O3 C21 C23 . . . . -8.1(3) ?
    C22 O4 C23 C21 . . . . 5.7(4) ?
    C22 O4 C23 C24 . . . . -175.6(3) ?
    C23 O4 C22 O3 . . . . -10.7(4) ?
    C23 C24 C25 C19 . . . . 0.2(5) ?
    C25 C19 C20 C21 . . . . -1.4(4) ?
