##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-12-11
_journal_date_accepted     2008-12-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      1
_journal_page_first     o208
_journal_page_last     o209
_journal_paper_category     QO
_journal_coeditor_code     HG2459
_publ_contact_author_name     'Hakan Arslan'
_publ_contact_author_address
;
Department of Natural Sciences,
Fayetteville State University,
Fayetteville, NC, 28301, USA
and
Department of Chemistry,
Faculty of Pharmacy,
Mersin University, Mersin,
TR 33169, Turkey
;
_publ_contact_author_email     'hakan.arslan.acad@gmail.com'
_publ_contact_author_fax     '+1-910-672-1159'
_publ_contact_author_phone     '+1-910-672-1532'
_publ_section_title
;
1-(4-<i>tert</i>-Butylbenzyl)-3-(3,4,5-trimethoxybenzyl)benzimidazolium bromide
monohydrate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Arslan, Hakan' .
;
Department of Natural Sciences,
Fayetteville State University,
Fayetteville, NC 28301, USA
and
Department of Chemistry,
Faculty of Pharmacy,
Mersin University, Mersin, TR 33169,
Turkey
;
    'VanDerveer, Don' .
;
Department of Chemistry,
Clemson University,
Clemson, SC 29634, USA
;
    'Demir, Serpil' .
;
Department of Chemistry,
Faculty of Science and Arts,
\.In\"on\"u University,
Malatya, TR 44280, Turkey
;
    '\"Ozdemir, \.Ismail' .
;
Department of Chemistry,
Faculty of Science and Arts,
\.In\"on\"u University,
Malatya, TR 44280, Turkey
;
    '\,Cetinkaya, Bekir' .
;
Department of Chemistry,
Faculty of Science,
Ege University,
Bornova-\.Izmir, TR 35100, Turkey
;
_publ_section_synopsis     .
_chemical_name_systematic
;
1-(4-<i>tert</i>-Butylbenzyl)-3-(3,4,5-trimethoxybenzyl)benzimidazolium bromide
monohydrate
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C28 H33 N2 O3 + , Br - , H2 O'
_chemical_formula_sum     'C28 H35 Br N2 O4'
_chemical_formula_iupac     'C28 H33 N2 O3 + , Br - , H2 O'
_chemical_formula_weight     543.49
_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     10.389(2)
_cell_length_b     10.436(2)
_cell_length_c     14.038(3)
_cell_angle_alpha     109.79(3)
_cell_angle_beta     90.70(3)
_cell_angle_gamma     103.57(3)
_cell_volume     1385.1(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4659
_cell_measurement_theta_min     3.2180
_cell_measurement_theta_max     26.4098
_cell_measurement_temperature     298(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.303
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     1.518
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(REQAB; Jacobson, 1998)
;
_exptl_absorpt_correction_T_min     0.5135
_exptl_absorpt_correction_T_max     0.6728
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Sealed Tube'
_diffrn_radiation_monochromator     'Graphite Monochromator'
_diffrn_measurement_device
;
Mercury CCD
;
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     14.6306
_diffrn_reflns_number     11938
_diffrn_reflns_av_R_equivalents     0.0223
_diffrn_reflns_av_sigmaI/netI     0.0254
_diffrn_reflns_theta_min     3.22
_diffrn_reflns_theta_max     25.04
_diffrn_reflns_theta_full     25.04
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_reflns_reduction_process     'Lp corrections applied'
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     4860
_reflns_number_gt     3921
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0547
_refine_ls_R_factor_gt     0.0417
_refine_ls_wR_factor_gt     0.1015
_refine_ls_wR_factor_ref     0.1124
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     4860
_refine_ls_number_parameters     328
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.6557P] where P=(Fo^2^+2Fc^2^)/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     0.309
_refine_diff_density_min     -0.545
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2001)'
_computing_cell_refinement     'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2001)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
           'SHELXTL (Sheldrick, 2008) and Mercury (Macrae <i>et al.</i>,  2006)'
_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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.75295(3) 0.93707(4) 0.51515(3) 0.06917(15) Uani d . 1 . .
    N N1 0.8315(2) 0.5830(2) 0.57685(15) 0.0384(5) Uani d . 1 . .
    N N2 1.0326(2) 0.7189(2) 0.62364(16) 0.0407(5) Uani d . 1 . .
    C C1 0.9118(3) 0.7064(3) 0.5843(2) 0.0439(6) Uani d . 1 . .
    H H1 0.8858 0.7766 0.5640 0.053 Uiso calc R 1 . .
    C C2 1.0322(2) 0.5974(2) 0.64403(18) 0.0363(5) Uani d . 1 . .
    C C3 1.1313(3) 0.5558(3) 0.6834(2) 0.0497(7) Uani d . 1 . .
    H H3 1.2196 0.6159 0.7050 0.060 Uiso calc R 1 . .
    C C4 1.0966(3) 0.4233(3) 0.6901(2) 0.0609(8) Uani d . 1 . .
    H H4 1.1626 0.3902 0.7168 0.073 Uiso calc R 1 . .
    C C5 0.9681(3) 0.3364(3) 0.6591(2) 0.0573(7) Uani d . 1 . .
    H H5 0.9483 0.2449 0.6650 0.069 Uiso calc R 1 . .
    C C6 0.8695(3) 0.3772(3) 0.6207(2) 0.0449(6) Uani d . 1 . .
    H H6 0.7811 0.3170 0.5997 0.054 Uiso calc R 1 . .
    C C7 0.9039(2) 0.5104(2) 0.61354(18) 0.0351(5) Uani d . 1 . .
    C C8 0.6876(2) 0.5379(3) 0.5428(2) 0.0454(6) Uani d . 1 . .
    H H8A 0.6617 0.4377 0.5084 0.054 Uiso calc R 1 . .
    H H8B 0.6699 0.5814 0.4955 0.054 Uiso calc R 1 . .
    C C9 0.6061(2) 0.5776(3) 0.6319(2) 0.0438(6) Uani d . 1 . .
    C C10 0.5443(3) 0.4785(3) 0.6729(2) 0.0456(6) Uani d . 1 . .
    H H10 0.5523 0.3835 0.6449 0.055 Uiso calc R 1 . .
    C C11 0.4705(3) 0.5178(3) 0.7550(2) 0.0521(7) Uani d . 1 . .
    C C12 0.4583(3) 0.6547(3) 0.7952(2) 0.0537(7) Uani d . 1 . .
    C C13 0.5222(3) 0.7534(3) 0.7543(2) 0.0553(7) Uani d . 1 . .
    C C14 0.5963(3) 0.7155(3) 0.6720(2) 0.0508(7) Uani d . 1 . .
    H H14 0.6399 0.7839 0.6435 0.061 Uiso calc R 1 . .
    C C15 0.4234(4) 0.2906(4) 0.7695(3) 0.0873(12) Uani d . 1 . .
    H H15A 0.3873 0.2414 0.6998 0.131 Uiso calc R 1 . .
    H H15B 0.3783 0.2416 0.8112 0.131 Uiso calc R 1 . .
    H H15C 0.5166 0.2951 0.7756 0.131 Uiso calc R 1 . .
    C C16 0.4304(4) 0.7401(6) 0.9699(3) 0.1083(17) Uani d . 1 . .
    H H16A 0.4738 0.6735 0.9805 0.162 Uiso calc R 1 . .
    H H16B 0.3620 0.7526 1.0150 0.162 Uiso calc R 1 . .
    H H16C 0.4944 0.8286 0.9835 0.162 Uiso calc R 1 . .
    C C17 0.5773(7) 0.9936(4) 0.7672(4) 0.119(2) Uani d . 1 . .
    H H17A 0.6705 0.9984 0.7736 0.179 Uiso calc R 1 . .
    H H17B 0.5622 1.0823 0.8082 0.179 Uiso calc R 1 . .
    H H17C 0.5478 0.9731 0.6973 0.179 Uiso calc R 1 . .
    C C18 1.1457(3) 0.8450(3) 0.6461(2) 0.0536(7) Uani d . 1 . .
    H H18A 1.1451 0.8826 0.5925 0.064 Uiso calc R 1 . .
    H H18B 1.2277 0.8182 0.6483 0.064 Uiso calc R 1 . .
    C C19 1.1387(3) 0.9570(3) 0.7460(2) 0.0450(6) Uani d . 1 . .
    C C20 1.0657(4) 1.0516(3) 0.7490(2) 0.0671(9) Uani d . 1 . .
    H H20 1.0205 1.0466 0.6873 0.081 Uiso calc R 1 . .
    C C21 1.0563(4) 1.1546(3) 0.8403(2) 0.0677(9) Uani d . 1 . .
    H H21 1.0048 1.2198 0.8403 0.081 Uiso calc R 1 . .
    C C22 1.1192(3) 1.1659(3) 0.9317(2) 0.0452(6) Uani d . 1 . .
    C C23 1.1931(3) 1.0704(3) 0.9268(2) 0.0532(7) Uani d . 1 . .
    H H23 1.2390 1.0752 0.9883 0.064 Uiso calc R 1 . .
    C C24 1.2033(3) 0.9667(3) 0.8350(2) 0.0533(7) Uani d . 1 . .
    H H24 1.2558 0.9019 0.8342 0.064 Uiso calc R 1 . .
    C C25 1.1111(3) 1.2836(3) 1.0308(2) 0.0591(8) Uani d . 1 . .
    C C26 0.9702(4) 1.3046(5) 1.0365(3) 0.0903(13) Uani d . 1 . .
    H H26A 0.9665 1.3779 1.0993 0.135 Uiso calc R 1 . .
    H H26B 0.9085 1.2186 1.0334 0.135 Uiso calc R 1 . .
    H H26C 0.9472 1.3306 0.9804 0.135 Uiso calc R 1 . .
    C C27 1.2089(5) 1.4190(4) 1.0328(4) 0.1013(15) Uani d . 1 . .
    H H27A 1.2976 1.4066 1.0315 0.152 Uiso calc R 1 . .
    H H27B 1.2037 1.4947 1.0937 0.152 Uiso calc R 1 . .
    H H27C 1.1868 1.4408 0.9745 0.152 Uiso calc R 1 . .
    C C28 1.1443(4) 1.2485(5) 1.1241(3) 0.0840(11) Uani d . 1 . .
    H H28A 1.2353 1.2435 1.1266 0.126 Uiso calc R 1 . .
    H H28B 1.0870 1.1594 1.1196 0.126 Uiso calc R 1 . .
    H H28C 1.1315 1.3204 1.1846 0.126 Uiso calc R 1 . .
    O O1 0.4055(2) 0.4294(3) 0.80195(18) 0.0717(6) Uani d . 1 . .
    O O2 0.3740(2) 0.6898(3) 0.86948(17) 0.0741(7) Uani d . 1 . .
    O O3 0.5058(3) 0.8868(3) 0.8002(2) 0.0870(8) Uani d . 1 . .
    O O4 0.5832(3) 0.1696(3) 0.4946(3) 0.0969(10) Uani d D 1 . .
    H H4A 0.499(2) 0.144(6) 0.501(4) 0.145 Uiso d D 1 . .
    H H4B 0.623(5) 0.107(5) 0.501(4) 0.145 Uiso d D 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
    Br1 0.0556(2) 0.0784(2) 0.0980(3) 0.02072(16) 0.01227(17) 0.0592(2)
    N1 0.0361(11) 0.0451(11) 0.0394(12) 0.0158(9) 0.0067(9) 0.0176(9)
    N2 0.0412(12) 0.0386(11) 0.0437(12) 0.0106(9) 0.0121(9) 0.0156(9)
    C1 0.0482(15) 0.0452(14) 0.0470(15) 0.0210(12) 0.0139(12) 0.0208(12)
    C2 0.0364(12) 0.0393(12) 0.0342(13) 0.0132(10) 0.0078(10) 0.0117(10)
    C3 0.0378(14) 0.0634(17) 0.0469(16) 0.0149(13) 0.0004(12) 0.0169(13)
    C4 0.0558(18) 0.073(2) 0.067(2) 0.0308(16) -0.0007(15) 0.0315(16)
    C5 0.067(2) 0.0494(16) 0.0648(19) 0.0205(15) 0.0037(15) 0.0284(14)
    C6 0.0463(15) 0.0391(13) 0.0477(15) 0.0082(11) 0.0045(12) 0.0148(11)
    C7 0.0348(12) 0.0396(12) 0.0330(12) 0.0147(10) 0.0060(10) 0.0119(10)
    C8 0.0360(13) 0.0599(16) 0.0433(15) 0.0190(12) 0.0027(11) 0.0173(12)
    C9 0.0329(13) 0.0567(15) 0.0432(14) 0.0176(12) 0.0004(11) 0.0155(12)
    C10 0.0366(13) 0.0535(15) 0.0483(16) 0.0120(12) 0.0020(11) 0.0195(12)
    C11 0.0363(14) 0.0673(18) 0.0546(17) 0.0098(13) 0.0039(12) 0.0260(14)
    C12 0.0355(14) 0.079(2) 0.0471(16) 0.0209(14) 0.0077(12) 0.0187(14)
    C13 0.0541(17) 0.0633(18) 0.0550(17) 0.0314(15) 0.0114(14) 0.0175(14)
    C14 0.0493(16) 0.0589(17) 0.0537(17) 0.0222(13) 0.0107(13) 0.0260(13)
    C15 0.091(3) 0.081(3) 0.099(3) 0.006(2) 0.019(2) 0.054(2)
    C16 0.078(3) 0.170(5) 0.054(2) 0.022(3) 0.013(2) 0.016(3)
    C17 0.195(6) 0.063(2) 0.112(4) 0.055(3) 0.059(4) 0.030(2)
    C18 0.0514(16) 0.0446(15) 0.0592(18) 0.0025(12) 0.0187(14) 0.0175(13)
    C19 0.0452(14) 0.0382(13) 0.0515(16) 0.0060(11) 0.0132(12) 0.0184(11)
    C20 0.097(3) 0.0610(19) 0.0488(18) 0.0340(18) -0.0027(17) 0.0174(14)
    C21 0.097(3) 0.0613(19) 0.0550(19) 0.0438(19) 0.0010(18) 0.0179(15)
    C22 0.0462(15) 0.0448(14) 0.0458(15) 0.0110(12) 0.0085(12) 0.0176(12)
    C23 0.0498(16) 0.0567(17) 0.0518(17) 0.0147(13) -0.0032(13) 0.0170(13)
    C24 0.0456(15) 0.0498(15) 0.0653(19) 0.0185(13) 0.0051(14) 0.0170(14)
    C25 0.0622(19) 0.0573(17) 0.0523(18) 0.0180(15) 0.0122(15) 0.0103(14)
    C26 0.091(3) 0.113(3) 0.072(3) 0.056(3) 0.024(2) 0.018(2)
    C27 0.127(4) 0.053(2) 0.093(3) 0.002(2) 0.024(3) 0.000(2)
    C28 0.087(3) 0.112(3) 0.0454(19) 0.032(2) 0.0076(18) 0.0146(19)
    O1 0.0604(14) 0.0848(16) 0.0758(16) 0.0089(12) 0.0203(12) 0.0416(13)
    O2 0.0492(12) 0.1158(19) 0.0554(14) 0.0316(13) 0.0177(10) 0.0202(13)
    O3 0.111(2) 0.0785(16) 0.0900(19) 0.0592(16) 0.0421(16) 0.0286(14)
    O4 0.0533(14) 0.0568(14) 0.174(3) 0.0082(12) -0.0014(18) 0.0367(17)
_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
    N1 C1 . 1.329(3) ?
    N1 C7 . 1.389(3) ?
    N1 C8 . 1.478(3) ?
    N2 C1 . 1.325(3) ?
    N2 C2 . 1.391(3) ?
    N2 C18 . 1.481(3) ?
    C1 H1 . 0.9600 ?
    C2 C3 . 1.382(4) ?
    C2 C7 . 1.393(3) ?
    C3 C4 . 1.380(4) ?
    C3 H3 . 0.9600 ?
    C4 C5 . 1.394(5) ?
    C4 H4 . 0.9600 ?
    C5 C6 . 1.368(4) ?
    C5 H5 . 0.9600 ?
    C6 C7 . 1.390(3) ?
    C6 H6 . 0.9600 ?
    C8 C9 . 1.513(4) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C9 C10 . 1.383(4) ?
    C9 C14 . 1.386(4) ?
    C10 C11 . 1.390(4) ?
    C10 H10 . 0.9600 ?
    C11 O1 . 1.369(3) ?
    C11 C12 . 1.385(4) ?
    C12 O2 . 1.380(3) ?
    C12 C13 . 1.385(4) ?
    C13 O3 . 1.374(4) ?
    C13 C14 . 1.392(4) ?
    C14 H14 . 0.9600 ?
    C15 O1 . 1.422(5) ?
    C15 H15A . 0.9599 ?
    C15 H15B . 0.9599 ?
    C15 H15C . 0.9599 ?
    C16 O2 . 1.394(5) ?
    C16 H16A . 0.9599 ?
    C16 H16B . 0.9599 ?
    C16 H16C . 0.9599 ?
    C17 O3 . 1.407(5) ?
    C17 H17A . 0.9599 ?
    C17 H17B . 0.9599 ?
    C17 H17C . 0.9599 ?
    C18 C19 . 1.507(4) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C19 C20 . 1.370(4) ?
    C19 C24 . 1.372(4) ?
    C20 C21 . 1.389(4) ?
    C20 H20 . 0.9600 ?
    C21 C22 . 1.388(4) ?
    C21 H21 . 0.9600 ?
    C22 C23 . 1.380(4) ?
    C22 C25 . 1.532(4) ?
    C23 C24 . 1.399(4) ?
    C23 H23 . 0.9600 ?
    C24 H24 . 0.9600 ?
    C25 C27 . 1.526(5) ?
    C25 C26 . 1.529(5) ?
    C25 C28 . 1.530(5) ?
    C26 H26A . 0.9599 ?
    C26 H26B . 0.9599 ?
    C26 H26C . 0.9599 ?
    C27 H27A . 0.9599 ?
    C27 H27B . 0.9599 ?
    C27 H27C . 0.9599 ?
    C28 H28A . 0.9599 ?
    C28 H28B . 0.9599 ?
    C28 H28C . 0.9599 ?
    O4 H4A . 0.87(2) ?
    O4 H4B . 0.88(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C7 . . 108.2(2) ?
    C1 N1 C8 . . 125.0(2) ?
    C7 N1 C8 . . 126.6(2) ?
    C1 N2 C2 . . 108.4(2) ?
    C1 N2 C18 . . 124.9(2) ?
    C2 N2 C18 . . 126.6(2) ?
    N2 C1 N1 . . 110.5(2) ?
    N2 C1 H1 . . 124.8 ?
    N1 C1 H1 . . 124.8 ?
    C3 C2 N2 . . 132.0(2) ?
    C3 C2 C7 . . 121.6(2) ?
    N2 C2 C7 . . 106.3(2) ?
    C4 C3 C2 . . 116.5(3) ?
    C4 C3 H3 . . 121.7 ?
    C2 C3 H3 . . 121.7 ?
    C3 C4 C5 . . 121.6(3) ?
    C3 C4 H4 . . 119.2 ?
    C5 C4 H4 . . 119.2 ?
    C6 C5 C4 . . 122.1(3) ?
    C6 C5 H5 . . 118.9 ?
    C4 C5 H5 . . 118.9 ?
    C5 C6 C7 . . 116.5(3) ?
    C5 C6 H6 . . 121.8 ?
    C7 C6 H6 . . 121.8 ?
    N1 C7 C6 . . 131.8(2) ?
    N1 C7 C2 . . 106.6(2) ?
    C6 C7 C2 . . 121.6(2) ?
    N1 C8 C9 . . 111.2(2) ?
    N1 C8 H8A . . 109.4 ?
    C9 C8 H8A . . 109.4 ?
    N1 C8 H8B . . 109.4 ?
    C9 C8 H8B . . 109.4 ?
    H8A C8 H8B . . 108.0 ?
    C10 C9 C14 . . 120.8(2) ?
    C10 C9 C8 . . 120.6(2) ?
    C14 C9 C8 . . 118.6(2) ?
    C9 C10 C11 . . 119.5(3) ?
    C9 C10 H10 . . 120.3 ?
    C11 C10 H10 . . 120.3 ?
    O1 C11 C12 . . 114.9(3) ?
    O1 C11 C10 . . 124.7(3) ?
    C12 C11 C10 . . 120.4(3) ?
    O2 C12 C11 . . 120.2(3) ?
    O2 C12 C13 . . 120.0(3) ?
    C11 C12 C13 . . 119.6(3) ?
    O3 C13 C12 . . 115.3(3) ?
    O3 C13 C14 . . 124.1(3) ?
    C12 C13 C14 . . 120.6(3) ?
    C9 C14 C13 . . 119.1(3) ?
    C9 C14 H14 . . 120.5 ?
    C13 C14 H14 . . 120.5 ?
    O1 C15 H15A . . 109.5 ?
    O1 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O1 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    O2 C16 H16A . . 109.5 ?
    O2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O3 C17 H17A . . 109.5 ?
    O3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    N2 C18 C19 . . 111.7(2) ?
    N2 C18 H18A . . 109.3 ?
    C19 C18 H18A . . 109.3 ?
    N2 C18 H18B . . 109.3 ?
    C19 C18 H18B . . 109.3 ?
    H18A C18 H18B . . 107.9 ?
    C20 C19 C24 . . 118.7(3) ?
    C20 C19 C18 . . 119.6(3) ?
    C24 C19 C18 . . 121.7(3) ?
    C19 C20 C21 . . 120.7(3) ?
    C19 C20 H20 . . 119.7 ?
    C21 C20 H20 . . 119.7 ?
    C22 C21 C20 . . 121.9(3) ?
    C22 C21 H21 . . 119.1 ?
    C20 C21 H21 . . 119.1 ?
    C23 C22 C21 . . 116.4(3) ?
    C23 C22 C25 . . 122.7(3) ?
    C21 C22 C25 . . 120.8(3) ?
    C22 C23 C24 . . 121.9(3) ?
    C22 C23 H23 . . 119.1 ?
    C24 C23 H23 . . 119.1 ?
    C19 C24 C23 . . 120.4(3) ?
    C19 C24 H24 . . 119.8 ?
    C23 C24 H24 . . 119.8 ?
    C27 C25 C26 . . 109.6(3) ?
    C27 C25 C28 . . 110.0(3) ?
    C26 C25 C28 . . 107.1(3) ?
    C27 C25 C22 . . 108.2(3) ?
    C26 C25 C22 . . 110.5(3) ?
    C28 C25 C22 . . 111.5(3) ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C25 C27 H27A . . 109.5 ?
    C25 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C25 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C25 C28 H28A . . 109.5 ?
    C25 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C25 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    C11 O1 C15 . . 117.4(3) ?
    C12 O2 C16 . . 116.4(3) ?
    C13 O3 C17 . . 117.6(3) ?
    H4A O4 H4B . . 110(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
    C2 N2 C1 N1 . . . . -0.4(3) ?
    C18 N2 C1 N1 . . . . -177.7(2) ?
    C7 N1 C1 N2 . . . . 0.1(3) ?
    C8 N1 C1 N2 . . . . 175.6(2) ?
    C1 N2 C2 C3 . . . . 179.0(3) ?
    C18 N2 C2 C3 . . . . -3.8(4) ?
    C1 N2 C2 C7 . . . . 0.6(3) ?
    C18 N2 C2 C7 . . . . 177.8(2) ?
    N2 C2 C3 C4 . . . . -177.6(3) ?
    C7 C2 C3 C4 . . . . 0.5(4) ?
    C2 C3 C4 C5 . . . . -0.3(4) ?
    C3 C4 C5 C6 . . . . -0.1(5) ?
    C4 C5 C6 C7 . . . . 0.2(4) ?
    C1 N1 C7 C6 . . . . -178.2(3) ?
    C8 N1 C7 C6 . . . . 6.3(4) ?
    C1 N1 C7 C2 . . . . 0.3(3) ?
    C8 N1 C7 C2 . . . . -175.2(2) ?
    C5 C6 C7 N1 . . . . 178.4(3) ?
    C5 C6 C7 C2 . . . . 0.0(4) ?
    C3 C2 C7 N1 . . . . -179.1(2) ?
    N2 C2 C7 N1 . . . . -0.5(2) ?
    C3 C2 C7 C6 . . . . -0.4(4) ?
    N2 C2 C7 C6 . . . . 178.2(2) ?
    C1 N1 C8 C9 . . . . -90.8(3) ?
    C7 N1 C8 C9 . . . . 84.0(3) ?
    N1 C8 C9 C10 . . . . -100.3(3) ?
    N1 C8 C9 C14 . . . . 78.9(3) ?
    C14 C9 C10 C11 . . . . 0.5(4) ?
    C8 C9 C10 C11 . . . . 179.7(2) ?
    C9 C10 C11 O1 . . . . -179.8(3) ?
    C9 C10 C11 C12 . . . . 0.3(4) ?
    O1 C11 C12 O2 . . . . -6.6(4) ?
    C10 C11 C12 O2 . . . . 173.3(3) ?
    O1 C11 C12 C13 . . . . 178.9(3) ?
    C10 C11 C12 C13 . . . . -1.2(4) ?
    O2 C12 C13 O3 . . . . 6.4(4) ?
    C11 C12 C13 O3 . . . . -179.1(3) ?
    O2 C12 C13 C14 . . . . -173.2(3) ?
    C11 C12 C13 C14 . . . . 1.4(5) ?
    C10 C9 C14 C13 . . . . -0.4(4) ?
    C8 C9 C14 C13 . . . . -179.7(3) ?
    O3 C13 C14 C9 . . . . 179.9(3) ?
    C12 C13 C14 C9 . . . . -0.5(4) ?
    C1 N2 C18 C19 . . . . 81.3(3) ?
    C2 N2 C18 C19 . . . . -95.5(3) ?
    N2 C18 C19 C20 . . . . -86.2(3) ?
    N2 C18 C19 C24 . . . . 93.5(3) ?
    C24 C19 C20 C21 . . . . -0.5(5) ?
    C18 C19 C20 C21 . . . . 179.1(3) ?
    C19 C20 C21 C22 . . . . -0.3(6) ?
    C20 C21 C22 C23 . . . . 0.8(5) ?
    C20 C21 C22 C25 . . . . 177.9(3) ?
    C21 C22 C23 C24 . . . . -0.6(4) ?
    C25 C22 C23 C24 . . . . -177.7(3) ?
    C20 C19 C24 C23 . . . . 0.7(4) ?
    C18 C19 C24 C23 . . . . -178.9(3) ?
    C22 C23 C24 C19 . . . . -0.1(4) ?
    C23 C22 C25 C27 . . . . 98.5(4) ?
    C21 C22 C25 C27 . . . . -78.4(4) ?
    C23 C22 C25 C26 . . . . -141.5(3) ?
    C21 C22 C25 C26 . . . . 41.6(4) ?
    C23 C22 C25 C28 . . . . -22.5(4) ?
    C21 C22 C25 C28 . . . . 160.6(3) ?
    C12 C11 O1 C15 . . . . -175.0(3) ?
    C10 C11 O1 C15 . . . . 5.2(5) ?
    C11 C12 O2 C16 . . . . 92.8(4) ?
    C13 C12 O2 C16 . . . . -92.7(4) ?
    C12 C13 O3 C17 . . . . 175.0(4) ?
    C14 C13 O3 C17 . . . . -5.5(6) ?
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
    O4 H4A Br1 2_666 0.87(3) 2.54(3) 3.393(3) 169(5)
    O4 H4B Br1 1_545 0.88(5) 2.52(5) 3.399(3) 176(5)
    C1 H1 Br1 . 0.96 2.65 3.587(3) 165
    C3 H3 O2 1_655 0.96 2.57 3.294(4) 132
    C6 H6 O4 . 0.96 2.38 3.305(5) 161
    C10 H10 O4 . 0.96 2.59 3.463(5) 152
    C14 H14 Br1 . 0.96 2.88 3.823(3) 167
    C18 H18A Br1 2_776 0.96 2.82 3.718(3) 155