#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224620.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224620
loop_
_publ_author_name
'Winstead, Angela'
'Hart, Krystal'
'Hijji, Yousef M.'
'Jasinski, Jerry P.'
'Butcher, Ray J.'
_publ_section_title
;
 1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide
 monohydrate
;
_journal_coeditor_code           FL2265
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o171
_journal_page_last               o172
_journal_paper_doi               10.1107/S1600536809049204
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H24 N O2 +, Br -, H2 O'
_chemical_formula_moiety         'C17 H24 N O2 +, Br -, H2 O'
_chemical_formula_sum            'C17 H26 Br N O3'
_chemical_formula_weight         372.30
_chemical_name_systematic
;
1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.437(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4528(3)
_cell_length_b                   15.3367(2)
_cell_length_c                   8.0810(2)
_cell_measurement_reflns_used    8515
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      73.4782
_cell_measurement_theta_min      5.5454
_cell_volume                     1766.98(6)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13155
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.74
_diffrn_reflns_theta_min         5.77
_diffrn_standards_decay_%        <2%
_exptl_absorpt_coefficient_mu    3.267
_exptl_absorpt_correction_T_max  0.676
_exptl_absorpt_correction_T_min  0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.426
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+1.5238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                3049
_reflns_number_total             3504
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2265.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224620
_cod_database_fobs_code          2224620
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'
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_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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655970
