#------------------------------------------------------------------------------
#$Date: 2018-08-15 05:24:26 +0300 (Wed, 15 Aug 2018) $
#$Revision: 209719 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/97/1549795.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_1549795
loop_
_publ_author_name
'da Costa Duarte, Rodrigo'
'Kommers Reimann, Louise'
'Severo Rodembusch, Fabiano'
'Gustavo Teixeira Alves Duarte, Luís'
_publ_section_title
;
 1-Butyl-2,3,3-trimethylindol-1-ium iodide
;
_journal_coeditor_code           HB4247
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x181130
_journal_paper_doi               10.1107/S2414314618011306
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C15 H22 N +, I -'
_chemical_formula_moiety         'C15 H22 N +, I -'
_chemical_formula_sum            'C15 H22 I N'
_chemical_formula_weight         343.23
_chemical_name_systematic
;
1-Butyl-2,3,3-trimethylindol-1-ium iodide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.631(12)
_cell_length_b                   11.614(8)
_cell_length_c                   16.976(11)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.203
_cell_measurement_theta_min      2.606
_cell_volume                     3082(4)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.400
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0190
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0198P)²+1.6747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0435
_refine_ls_wR_factor_ref         0.0472
_reflns_number_gt                3166
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4247sup1.cif
_cod_data_source_block           I
_cod_database_code               1549795
_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.
;
_shelx_estimated_absorpt_t_min   0.515
_shelx_estimated_absorpt_t_max   0.836
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 0.30279(12) 0.35676(13) 0.65813(9) 0.0198(3) Uani d 1
C C2 0.21170(11) 0.31229(14) 0.65947(9) 0.0199(3) Uani d 1
C C3 0.21293(11) 0.23111(13) 0.59009(9) 0.0179(3) Uani d 1
C C4 0.29095(10) 0.24303(13) 0.55103(9) 0.0165(3) Uani d 1
C C5 0.31022(11) 0.18740(14) 0.48120(9) 0.0201(3) Uani d 1
H H5 0.362745 0.199361 0.454265 0.024 Uiso calc 1
C C6 0.24721(12) 0.11220(14) 0.45275(9) 0.0222(4) Uani d 1
H H6 0.257625 0.070940 0.405389 0.027 Uiso calc 1
C C7 0.16967(12) 0.09619(14) 0.49194(10) 0.0229(4) Uani d 1
H H7 0.129118 0.043056 0.471549 0.028 Uiso calc 1
C C8 0.15075(11) 0.15720(15) 0.56079(10) 0.0218(3) Uani d 1
H H8 0.097231 0.148388 0.586626 0.026 Uiso calc 1
C C9 0.18792(12) 0.25620(17) 0.73851(10) 0.0286(4) Uani d 1
H H9A 0.230985 0.198271 0.752297 0.043 Uiso calc 1
H H9B 0.131775 0.219254 0.733967 0.043 Uiso calc 1
H H9C 0.185859 0.315308 0.779666 0.043 Uiso calc 1
C C10 0.15024(14) 0.41470(17) 0.64136(12) 0.0337(4) Uani d 1
H H10A 0.154360 0.472001 0.683564 0.050 Uiso calc 1
H H10B 0.091326 0.386260 0.637986 0.050 Uiso calc 1
H H10C 0.166415 0.450183 0.591146 0.050 Uiso calc 1
C C11 0.34125(13) 0.42907(15) 0.72083(10) 0.0280(4) Uani d 1
H H11A 0.365790 0.379431 0.761679 0.042 Uiso calc 1
H H11B 0.297002 0.478211 0.744126 0.042 Uiso calc 1
H H11C 0.386361 0.477354 0.698117 0.042 Uiso calc 1
C C12 0.43452(11) 0.34915(14) 0.57497(10) 0.0204(3) Uani d 1
H H12A 0.447583 0.428413 0.592736 0.024 Uiso calc 1
H H12B 0.440974 0.346896 0.516979 0.024 Uiso calc 1
C C13 0.49862(11) 0.26586(14) 0.61218(10) 0.0213(3) Uani d 1
H H13A 0.556043 0.301760 0.610894 0.026 Uiso calc 1
H H13B 0.482947 0.254517 0.668152 0.026 Uiso calc 1
C C14 0.50385(13) 0.14869(16) 0.57259(11) 0.0285(4) Uani d 1
H H14A 0.516312 0.159241 0.515870 0.034 Uiso calc 1
H H14B 0.447852 0.109433 0.577200 0.034 Uiso calc 1
C C15 0.57325(15) 0.0730(2) 0.60951(15) 0.0459(6) Uani d 1
H H15A 0.574132 -0.002022 0.583103 0.069 Uiso calc 1
H H15B 0.561002 0.062175 0.665637 0.069 Uiso calc 1
H H15C 0.629065 0.110399 0.603421 0.069 Uiso calc 1
N N1 0.34412(9) 0.32083(11) 0.59593(8) 0.0172(3) Uani d 1
I I1 0.42439(2) 0.38097(2) 0.32579(2) 0.02455(4) 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 0.0033 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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 C1 C2 124.28(15)
N1 C1 C2 111.60(14)
N1 C1 C11 124.09(17)
C1 C2 C9 112.64(14)
C1 C2 C10 108.42(15)
C3 C2 C1 100.91(13)
C3 C2 C9 114.81(15)
C3 C2 C10 109.30(14)
C9 C2 C10 110.27(15)
C4 C3 C2 108.68(14)
C8 C3 C2 131.06(16)
C8 C3 C4 120.19(15)
C3 C4 N1 108.31(14)
C5 C4 C3 123.46(15)
C5 C4 N1 128.23(15)
C4 C5 H5 122.2
C4 C5 C6 115.67(16)
C6 C5 H5 122.2
C5 C6 H6 119.0
C7 C6 C5 121.94(16)
C7 C6 H6 119.0
C6 C7 H7 119.5
C6 C7 C8 120.99(16)
C8 C7 H7 119.5
C3 C8 C7 117.67(16)
C3 C8 H8 121.2
C7 C8 H8 121.2
C2 C9 H9A 109.5
C2 C9 H9B 109.5
C2 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C2 C10 H10A 109.5
C2 C10 H10B 109.5
C2 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C1 C11 H11A 109.5
C1 C11 H11B 109.5
C1 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
H12A C12 H12B 107.8
C13 C12 H12A 109.1
C13 C12 H12B 109.1
N1 C12 H12A 109.1
N1 C12 H12B 109.1
N1 C12 C13 112.46(14)
C12 C13 H13A 108.6
C12 C13 H13B 108.6
H13A C13 H13B 107.6
C14 C13 C12 114.77(14)
C14 C13 H13A 108.6
C14 C13 H13B 108.6
C13 C14 H14A 109.3
C13 C14 H14B 109.3
C13 C14 C15 111.80(16)
H14A C14 H14B 107.9
C15 C14 H14A 109.3
C15 C14 H14B 109.3
C14 C15 H15A 109.5
C14 C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 N1 C4 109.97(14)
C1 N1 C12 126.15(14)
C4 N1 C12 123.79(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.515(3)
C1 C11 1.483(2)
C1 N1 1.306(2)
C2 C3 1.509(2)
C2 C9 1.537(2)
C2 C10 1.560(3)
C3 C4 1.395(2)
C3 C8 1.389(2)
C4 C5 1.383(2)
C4 N1 1.445(2)
C5 H5 0.9500
C5 C6 1.402(2)
C6 H6 0.9500
C6 C7 1.395(3)
C7 H7 0.9500
C7 C8 1.398(2)
C8 H8 0.9500
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9900
C12 H12B 0.9900
C12 C13 1.529(2)
C12 N1 1.494(2)
C13 H13A 0.9900
C13 H13B 0.9900
C13 C14 1.520(2)
C14 H14A 0.9900
C14 H14B 0.9900
C14 C15 1.530(3)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
C5 H5 I1 . 0.95 3.18 3.899(2) 134
C12 H12A I1 5_666 0.99 3.29 4.186(3) 151
C12 H12B I1 . 0.99 3.28 4.249(3) 167
C13 H13B I1 7_566 0.99 3.24 4.172(3) 158

_cod_database_fobs_code 1549795
