##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-09-01
_journal_date_accepted     2009-11-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      1
_journal_page_first     o171
_journal_page_last     o172
_journal_paper_category     QO
_journal_coeditor_code     FL2265
_publ_contact_author_name     'Butcher, Ray J.'
_publ_contact_author_address
;
Department of Chemistry
Howard University
525 College Street NW
Washington DC 20059, USA
;
_publ_contact_author_email     rbutcher99@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '703 585-6631'
_publ_section_title
;
1-(5-Carboxypentyl)-2,3,3-trimethyl-3<i>H</i>-indol-1-ium bromide monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Winstead, Angela'
;
Department of Chemistry
Morgan State University
Baltimore, MD 21251, USA
;
    'Hart, Krystal'
;
Department of Chemistry
Morgan State University
Baltimore, MD 21251, USA
;
    'Hijji, Yousef M.'
;
Department of Chemistry
Morgan State University
Baltimore, MD 21251, USA
;
    'Jasinski, Jerry P.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
    'Butcher, Ray J.'
;
Department of Chemistry
Howard University
525 College Street NW
Washington
DC 20059, USA
;
data_I
_chemical_name_systematic
;
1-(5-Carboxypentyl)-2,3,3-trimethyl-3<i>H</i>-indol-1-ium bromide monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H24 N O2 +, Br -, H2 O'
_chemical_formula_sum     'C17 H26 Br N O3'
_chemical_formula_iupac     'C17 H24 N O2 +, Br -, H2 O'
_chemical_formula_weight     372.30
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.4528(3)
_cell_length_b     15.3367(2)
_cell_length_c     8.0810(2)
_cell_angle_alpha     90.00
_cell_angle_beta     99.437(2)
_cell_angle_gamma     90.00
_cell_volume     1766.98(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8515
_cell_measurement_theta_min     5.5454
_cell_measurement_theta_max     73.4782
_cell_measurement_temperature     200(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.399
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu     3.267
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_absorpt_correction_T_min     0.296
_exptl_absorpt_correction_T_max     0.676
_exptl_special_details
;
;
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini R'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     10.5081
_diffrn_reflns_number     13155
_diffrn_reflns_av_R_equivalents     0.0330
_diffrn_reflns_av_sigmaI/netI     0.0217
_diffrn_reflns_theta_min     5.77
_diffrn_reflns_theta_max     73.74
_diffrn_reflns_theta_full     67.50
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <2%
_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     3504
_reflns_number_gt     3049
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0429
_refine_ls_R_factor_gt     0.0365
_refine_ls_wR_factor_gt     0.0946
_refine_ls_wR_factor_ref     0.0977
_refine_ls_goodness_of_fit_ref     1.057
_refine_ls_restrained_S_all     1.056
_refine_ls_number_reflns     3504
_refine_ls_number_parameters     209
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+1.5238P] 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     0.519
_refine_diff_density_min     -0.426
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.6763 1.2805
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     '<i>CrysAlis Pro</i> (Oxford Diffraction, 2007)'
_computing_cell_refinement     '<i>CrysAlis Pro</i> (Oxford Diffraction, 2007)'
_computing_data_reduction     '<i>CrysAlis Pro</i> (Oxford Diffraction, 2007)'
_computing_structure_solution     '<i>SHELXS97</i> (Sheldrick, 2008)'
_computing_structure_refinement     '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_molecular_graphics     '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material     '<i>SHELXTL</i> (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 Br 0.168343(18) 0.871933(16) 0.50535(3) 0.03689(11) Uani d . 1 . .
    O O1 0.5587(2) 0.7918(2) 0.1347(5) 0.0893(10) Uani d . 1 . .
    O O2 0.42824(18) 0.81569(14) 0.2331(4) 0.0661(7) Uani d . 1 . .
    H H2O 0.3800 0.7873 0.2448 0.079 Uiso calc R 1 . .
    O O1W 0.28626(17) 0.7310(2) 0.3254(3) 0.0707(8) Uani d D 1 . .
    H H1W1 0.254(3) 0.764(3) 0.372(5) 0.106 Uiso d D 1 . .
    H H1W2 0.251(3) 0.714(3) 0.242(4) 0.106 Uiso d D 1 . .
    N N1 0.79026(13) 0.52889(12) 0.5047(2) 0.0254(4) Uani d . 1 . .
    C C1 0.76946(16) 0.56100(15) 0.6432(3) 0.0279(5) Uani d . 1 . .
    C C2 0.68861(18) 0.53476(18) 0.7221(3) 0.0379(6) Uani d . 1 . .
    H H2A 0.6566 0.4853 0.6607 0.057 Uiso calc R 1 . .
    H H2B 0.6449 0.5838 0.7192 0.057 Uiso calc R 1 . .
    H H2C 0.7106 0.5178 0.8389 0.057 Uiso calc R 1 . .
    C C3 0.84000(16) 0.63015(14) 0.7139(3) 0.0268(5) Uani d . 1 . .
    C C4 0.78975(19) 0.71914(16) 0.7114(3) 0.0367(6) Uani d . 1 . .
    H H4A 0.7579 0.7317 0.5972 0.055 Uiso calc R 1 . .
    H H4B 0.8359 0.7649 0.7478 0.055 Uiso calc R 1 . .
    H H4C 0.7435 0.7173 0.7875 0.055 Uiso calc R 1 . .
    C C5 0.88798(19) 0.60805(17) 0.8929(3) 0.0348(5) Uani d . 1 . .
    H H5A 0.9155 0.5496 0.8944 0.052 Uiso calc R 1 . .
    H H5B 0.8416 0.6097 0.9687 0.052 Uiso calc R 1 . .
    H H5C 0.9375 0.6508 0.9297 0.052 Uiso calc R 1 . .
    C C6 0.90648(16) 0.62789(13) 0.5885(3) 0.0252(4) Uani d . 1 . .
    C C7 0.98805(16) 0.67357(15) 0.5803(3) 0.0301(5) Uani d . 1 . .
    H H7A 1.0118 0.7148 0.6643 0.036 Uiso calc R 1 . .
    C C8 1.03446(17) 0.65748(16) 0.4452(3) 0.0327(5) Uani d . 1 . .
    H H8A 1.0904 0.6886 0.4369 0.039 Uiso calc R 1 . .
    C C9 1.00061(17) 0.59686(16) 0.3225(3) 0.0318(5) Uani d . 1 . .
    H H9A 1.0338 0.5873 0.2319 0.038 Uiso calc R 1 . .
    C C10 0.91882(16) 0.54979(15) 0.3296(3) 0.0281(5) Uani d . 1 . .
    H H10A 0.8952 0.5078 0.2470 0.034 Uiso calc R 1 . .
    C C11 0.87436(15) 0.56811(14) 0.4644(3) 0.0246(4) Uani d . 1 . .
    C C12 0.73635(17) 0.46508(15) 0.3907(3) 0.0320(5) Uani d . 1 . .
    H H12A 0.6940 0.4319 0.4522 0.038 Uiso calc R 1 . .
    H H12B 0.7800 0.4232 0.3508 0.038 Uiso calc R 1 . .
    C C13 0.67861(17) 0.51091(16) 0.2403(3) 0.0339(5) Uani d . 1 . .
    H H13A 0.7215 0.5454 0.1823 0.041 Uiso calc R 1 . .
    H H13B 0.6488 0.4661 0.1607 0.041 Uiso calc R 1 . .
    C C14 0.60247(18) 0.57112(19) 0.2847(3) 0.0391(6) Uani d . 1 . .
    H H14A 0.5631 0.5384 0.3527 0.047 Uiso calc R 1 . .
    H H14B 0.6323 0.6199 0.3540 0.047 Uiso calc R 1 . .
    C C15 0.5405(2) 0.6079(2) 0.1308(4) 0.0553(8) Uani d . 1 . .
    H H15A 0.5107 0.5590 0.0617 0.066 Uiso calc R 1 . .
    H H15B 0.5800 0.6403 0.0628 0.066 Uiso calc R 1 . .
    C C16 0.46391(19) 0.66849(18) 0.1732(4) 0.0430(6) Uani d . 1 . .
    H H16A 0.4067 0.6601 0.0888 0.052 Uiso calc R 1 . .
    H H16B 0.4486 0.6516 0.2838 0.052 Uiso calc R 1 . .
    C C17 0.4896(2) 0.7628(2) 0.1783(4) 0.0492(7) Uani 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
    Br 0.04080(17) 0.03133(16) 0.03975(18) -0.00006(10) 0.01018(12) 0.00063(10)
    O1 0.0628(16) 0.0726(18) 0.136(3) -0.0271(14) 0.0274(17) -0.0028(18)
    O2 0.0607(14) 0.0372(11) 0.097(2) 0.0081(10) 0.0028(13) -0.0153(12)
    O1W 0.0458(12) 0.102(2) 0.0635(16) 0.0124(13) 0.0056(11) -0.0374(15)
    N1 0.0266(9) 0.0221(8) 0.0263(10) -0.0014(7) 0.0009(7) 0.0013(7)
    C1 0.0300(11) 0.0264(11) 0.0259(11) 0.0015(9) 0.0005(9) 0.0053(9)
    C2 0.0355(13) 0.0415(14) 0.0380(14) -0.0016(10) 0.0105(11) 0.0069(11)
    C3 0.0325(11) 0.0237(11) 0.0238(11) -0.0012(8) 0.0033(9) -0.0004(8)
    C4 0.0450(14) 0.0296(12) 0.0366(14) 0.0056(10) 0.0100(11) -0.0002(10)
    C5 0.0439(14) 0.0343(12) 0.0244(12) -0.0008(10) 0.0004(10) 0.0014(10)
    C6 0.0317(11) 0.0205(10) 0.0225(11) 0.0018(8) 0.0015(9) 0.0015(8)
    C7 0.0334(11) 0.0232(11) 0.0319(13) -0.0025(9) 0.0003(9) 0.0005(9)
    C8 0.0302(11) 0.0282(11) 0.0394(14) -0.0014(9) 0.0051(10) 0.0082(10)
    C9 0.0348(12) 0.0313(12) 0.0306(13) 0.0075(9) 0.0089(10) 0.0065(10)
    C10 0.0347(12) 0.0244(11) 0.0239(11) 0.0050(9) 0.0010(9) 0.0006(9)
    C11 0.0275(10) 0.0210(10) 0.0243(11) 0.0008(8) 0.0015(8) 0.0045(8)
    C12 0.0327(11) 0.0234(11) 0.0374(13) -0.0030(9) -0.0020(10) -0.0040(10)
    C13 0.0330(12) 0.0330(12) 0.0332(13) 0.0007(9) -0.0018(10) -0.0069(10)
    C14 0.0352(13) 0.0426(14) 0.0381(14) 0.0067(11) 0.0023(11) -0.0017(11)
    C15 0.0538(18) 0.0570(18) 0.0493(18) 0.0244(15) -0.0087(14) -0.0133(15)
    C16 0.0363(13) 0.0373(14) 0.0526(17) 0.0073(11) -0.0014(12) -0.0026(12)
    C17 0.0405(15) 0.0418(15) 0.062(2) -0.0031(12) -0.0019(13) -0.0028(14)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C17 . 1.198(4) ?
    O2 C17 . 1.330(4) ?
    O2 H2O . 0.8400 ?
    O1W H1W1 . 0.812(19) ?
    O1W H1W2 . 0.817(19) ?
    N1 C1 . 1.302(3) ?
    N1 C11 . 1.440(3) ?
    N1 C12 . 1.476(3) ?
    C1 C2 . 1.476(3) ?
    C1 C3 . 1.516(3) ?
    C2 H2A . 0.9800 ?
    C2 H2B . 0.9800 ?
    C2 H2C . 0.9800 ?
    C3 C6 . 1.507(3) ?
    C3 C5 . 1.536(3) ?
    C3 C4 . 1.545(3) ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C5 H5A . 0.9800 ?
    C5 H5B . 0.9800 ?
    C5 H5C . 0.9800 ?
    C6 C11 . 1.382(3) ?
    C6 C7 . 1.382(3) ?
    C7 C8 . 1.394(4) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.389(4) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.394(3) ?
    C9 H9A . 0.9500 ?
    C10 C11 . 1.381(3) ?
    C10 H10A . 0.9500 ?
    C12 C13 . 1.528(3) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.524(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.518(4) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.526(4) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.493(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
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
    C17 O2 H2O . . 109.5 ?
    H1W1 O1W H1W2 . . 104(3) ?
    C1 N1 C11 . . 111.00(19) ?
    C1 N1 C12 . . 127.9(2) ?
    C11 N1 C12 . . 120.96(19) ?
    N1 C1 C2 . . 125.4(2) ?
    N1 C1 C3 . . 110.6(2) ?
    C2 C1 C3 . . 124.0(2) ?
    C1 C2 H2A . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    C1 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    C6 C3 C1 . . 101.18(18) ?
    C6 C3 C5 . . 112.9(2) ?
    C1 C3 C5 . . 111.86(19) ?
    C6 C3 C4 . . 111.20(19) ?
    C1 C3 C4 . . 109.1(2) ?
    C5 C3 C4 . . 110.3(2) ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C3 C5 H5A . . 109.5 ?
    C3 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C3 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C11 C6 C7 . . 119.3(2) ?
    C11 C6 C3 . . 109.15(19) ?
    C7 C6 C3 . . 131.6(2) ?
    C6 C7 C8 . . 118.1(2) ?
    C6 C7 H7A . . 120.9 ?
    C8 C7 H7A . . 120.9 ?
    C9 C8 C7 . . 121.3(2) ?
    C9 C8 H8A . . 119.4 ?
    C7 C8 H8A . . 119.4 ?
    C8 C9 C10 . . 121.3(2) ?
    C8 C9 H9A . . 119.4 ?
    C10 C9 H9A . . 119.4 ?
    C11 C10 C9 . . 115.8(2) ?
    C11 C10 H10A . . 122.1 ?
    C9 C10 H10A . . 122.1 ?
    C10 C11 C6 . . 124.3(2) ?
    C10 C11 N1 . . 127.7(2) ?
    C6 C11 N1 . . 108.0(2) ?
    N1 C12 C13 . . 110.80(19) ?
    N1 C12 H12A . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    N1 C12 H12B . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C14 C13 C12 . . 114.4(2) ?
    C14 C13 H13A . . 108.7 ?
    C12 C13 H13A . . 108.7 ?
    C14 C13 H13B . . 108.7 ?
    C12 C13 H13B . . 108.7 ?
    H13A C13 H13B . . 107.6 ?
    C15 C14 C13 . . 112.6(2) ?
    C15 C14 H14A . . 109.1 ?
    C13 C14 H14A . . 109.1 ?
    C15 C14 H14B . . 109.1 ?
    C13 C14 H14B . . 109.1 ?
    H14A C14 H14B . . 107.8 ?
    C14 C15 C16 . . 113.2(3) ?
    C14 C15 H15A . . 108.9 ?
    C16 C15 H15A . . 108.9 ?
    C14 C15 H15B . . 108.9 ?
    C16 C15 H15B . . 108.9 ?
    H15A C15 H15B . . 107.7 ?
    C17 C16 C15 . . 114.2(3) ?
    C17 C16 H16A . . 108.7 ?
    C15 C16 H16A . . 108.7 ?
    C17 C16 H16B . . 108.7 ?
    C15 C16 H16B . . 108.7 ?
    H16A C16 H16B . . 107.6 ?
    O1 C17 O2 . . 120.4(3) ?
    O1 C17 C16 . . 124.5(3) ?
    O2 C17 C16 . . 115.1(3) ?
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
    C11 N1 C1 C2 . . . . -179.2(2) ?
    C12 N1 C1 C2 . . . . 4.5(4) ?
    C11 N1 C1 C3 . . . . 1.0(2) ?
    C12 N1 C1 C3 . . . . -175.3(2) ?
    N1 C1 C3 C6 . . . . -1.7(2) ?
    C2 C1 C3 C6 . . . . 178.4(2) ?
    N1 C1 C3 C5 . . . . -122.2(2) ?
    C2 C1 C3 C5 . . . . 58.0(3) ?
    N1 C1 C3 C4 . . . . 115.6(2) ?
    C2 C1 C3 C4 . . . . -64.3(3) ?
    C1 C3 C6 C11 . . . . 1.9(2) ?
    C5 C3 C6 C11 . . . . 121.6(2) ?
    C4 C3 C6 C11 . . . . -113.9(2) ?
    C1 C3 C6 C7 . . . . -178.4(2) ?
    C5 C3 C6 C7 . . . . -58.7(3) ?
    C4 C3 C6 C7 . . . . 65.8(3) ?
    C11 C6 C7 C8 . . . . 0.4(3) ?
    C3 C6 C7 C8 . . . . -179.3(2) ?
    C6 C7 C8 C9 . . . . -0.5(4) ?
    C7 C8 C9 C10 . . . . 0.0(4) ?
    C8 C9 C10 C11 . . . . 0.5(3) ?
    C9 C10 C11 C6 . . . . -0.7(3) ?
    C9 C10 C11 N1 . . . . -179.0(2) ?
    C7 C6 C11 C10 . . . . 0.2(3) ?
    C3 C6 C11 C10 . . . . -180.0(2) ?
    C7 C6 C11 N1 . . . . 178.82(19) ?
    C3 C6 C11 N1 . . . . -1.4(2) ?
    C1 N1 C11 C10 . . . . 178.8(2) ?
    C12 N1 C11 C10 . . . . -4.6(3) ?
    C1 N1 C11 C6 . . . . 0.3(2) ?
    C12 N1 C11 C6 . . . . 176.90(19) ?
    C1 N1 C12 C13 . . . . 99.2(3) ?
    C11 N1 C12 C13 . . . . -76.8(3) ?
    N1 C12 C13 C14 . . . . -64.4(3) ?
    C12 C13 C14 C15 . . . . -174.0(2) ?
    C13 C14 C15 C16 . . . . -179.9(3) ?
    C14 C15 C16 C17 . . . . 94.4(4) ?
    C15 C16 C17 O1 . . . . 8.5(5) ?
    C15 C16 C17 O2 . . . . -172.8(3) ?
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
    O2 H2O O1W . 0.84 1.82 2.637(4) 165.6
    O1W H1W1 Br . 0.812(19) 2.431(19) 3.240(2) 175(5)
    O1W H1W2 Br 4_575 0.817(19) 2.47(2) 3.262(3) 165(5)
    C4 H4B Cg2 4_576 0.99 2.88 3.828(3) 162