#------------------------------------------------------------------------------
#$Date: 2017-03-15 09:13:42 +0200 (Wed, 15 Mar 2017) $
#$Revision: 194252 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242076.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_2242076
loop_
_publ_author_name
'Kvyatkovskaya, Elisaveta A.'
'Zaytsev, Vladimir P.'
'Zubkov, Fedor I.'
'Dorovatovskii, Pavel V.'
'Zubavichus, Yan V.'
'Khrustalev, Victor N.'
_publ_section_title
;
 Interaction between maleic acid and N-R-furfurylamines:
 crystal structure of
 2-methyl-N-[(5-phenylfuran-2-yl)methyl]propan-2-aminium
 (2Z)-3-carboxyacrylate and
 N-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium
 (2Z)-3-carboxyprop-2-enoate
;
_journal_coeditor_code           HB7663
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              515
_journal_page_last               519
_journal_paper_doi               10.1107/S2056989017003541
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C9 H15 I N O +, C4 H3 O4 -'
_chemical_formula_moiety         'C9 H15 I N O +, C4 H3 O4 -'
_chemical_formula_sum            'C13 H18 I N O5'
_chemical_formula_weight         395.18
_chemical_name_systematic
;
N-[(5-Iodofuran-2-yl)methyl]-2-methylpropan-2-aminium
(2Z)-3-carboxyprop-2-enoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2015
_cell_angle_alpha                90
_cell_angle_beta                 93.17(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7501(12)
_cell_length_b                   28.272(6)
_cell_length_c                   9.6402(19)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      3.5
_cell_volume                     1564.8(6)
_computing_cell_refinement
;
iMosflm (Battye et al., 2011)
;
_computing_data_collection
;
Automar (MarXperts, 2015)
;
_computing_data_reduction
;
iMosflm (Battye et al., 2011)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21875
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.446
_diffrn_reflns_theta_min         3.494
_exptl_absorpt_coefficient_mu    4.691
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scala; Evans, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.941
_refine_diff_density_min         -1.208
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015a)
;
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0377P)²+3.0P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2714
_reflns_number_total             3146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7663sup1.cif
_cod_data_source_block           II
_cod_database_code               2242076
_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   0.561
_shelx_estimated_absorpt_t_max   0.937
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
I I1 0.75296(5) 0.48487(2) 0.86223(3) 0.05279(17) Uani d 1
O O1 0.4289(4) 0.56119(7) 0.7766(3) 0.0273(5) Uani d 1
O O2 0.6669(4) 0.62755(8) 0.4628(2) 0.0250(5) Uani d 1
O O3 0.4201(4) 0.64214(9) 0.2824(3) 0.0284(5) Uani d 1
O O4 0.7068(4) 0.65296(8) -0.1219(2) 0.0242(5) Uani d 1
O O5 0.4335(4) 0.65188(8) 0.0330(3) 0.0272(5) Uani d 1
H H5O 0.434(7) 0.6447(14) 0.153(5) 0.041 Uiso d 1
N N1 0.3606(4) 0.65833(8) 0.6639(3) 0.0172(5) Uani d 1
H H1A 0.436(6) 0.6486(12) 0.592(4) 0.021 Uiso d 1
H H1B 0.462(7) 0.6587(12) 0.735(4) 0.021 Uiso d 1
C C1 0.1674(5) 0.62389(10) 0.6907(4) 0.0227(7) Uani d 1
H H1C 0.1109 0.6293 0.7845 0.027 Uiso calc 1
H H1D 0.0355 0.6289 0.6219 0.027 Uiso calc 1
C C2 0.2549(5) 0.57433(10) 0.6802(4) 0.0247(7) Uani d 1
C C3 0.2006(7) 0.53816(12) 0.5920(5) 0.0379(9) Uani d 1
H H3 0.0876 0.5385 0.5163 0.045 Uiso calc 1
C C4 0.3478(8) 0.49932(12) 0.6355(5) 0.0425(10) Uani d 1
H H4 0.3511 0.4687 0.5950 0.051 Uiso calc 1
C C5 0.4796(6) 0.51500(11) 0.7450(4) 0.0307(9) Uani d 1
C C6 0.2890(5) 0.71010(10) 0.6427(3) 0.0189(7) Uani d 1
C C7 0.5174(5) 0.73740(10) 0.6298(4) 0.0236(7) Uani d 1
H H7A 0.6151 0.7339 0.7157 0.035 Uiso calc 1
H H7B 0.4829 0.7710 0.6137 0.035 Uiso calc 1
H H7C 0.6001 0.7248 0.5516 0.035 Uiso calc 1
C C8 0.1369(5) 0.71450(11) 0.5089(4) 0.0241(7) Uani d 1
H H8A 0.2219 0.7025 0.4310 0.036 Uiso calc 1
H H8B 0.0968 0.7478 0.4926 0.036 Uiso calc 1
H H8C -0.0061 0.6961 0.5171 0.036 Uiso calc 1
C C9 0.1632(5) 0.72673(10) 0.7693(4) 0.0225(7) Uani d 1
H H9A 0.0164 0.7094 0.7744 0.034 Uiso calc 1
H H9B 0.1308 0.7607 0.7611 0.034 Uiso calc 1
H H9C 0.2618 0.7208 0.8537 0.034 Uiso calc 1
C C10 0.6235(5) 0.63160(9) 0.3358(4) 0.0198(7) Uani d 1
C C11 0.8219(5) 0.62384(10) 0.2425(3) 0.0213(7) Uani d 1
H H11 0.9625 0.6131 0.2884 0.026 Uiso calc 1
C C12 0.8311(5) 0.62967(10) 0.1049(4) 0.0225(7) Uani d 1
H H12 0.9776 0.6225 0.0690 0.027 Uiso calc 1
C C13 0.6458(5) 0.64577(10) -0.0025(3) 0.0196(6) 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 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.0340 3.1360 '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
C5 O1 C2 105.2(3)
C10 O3 H5O 107.7(19)
C13 O5 H5O 107(2)
C1 N1 C6 116.4(2)
C1 N1 H1A 109(2)
C6 N1 H1A 109(2)
C1 N1 H1B 110(2)
C6 N1 H1B 105(2)
H1A N1 H1B 107(3)
C2 C1 N1 109.8(2)
C2 C1 H1C 109.7
N1 C1 H1C 109.7
C2 C1 H1D 109.7
N1 C1 H1D 109.7
H1C C1 H1D 108.2
C3 C2 O1 110.7(3)
C3 C2 C1 133.1(3)
O1 C2 C1 116.2(3)
C2 C3 C4 106.4(4)
C2 C3 H3 126.8
C4 C3 H3 126.8
C5 C4 C3 106.0(3)
C5 C4 H4 127.0
C3 C4 H4 127.0
C4 C5 O1 111.8(3)
C4 C5 I1 132.4(3)
O1 C5 I1 115.7(3)
C8 C6 C9 112.1(3)
C8 C6 N1 109.2(2)
C9 C6 N1 108.9(2)
C8 C6 C7 110.1(3)
C9 C6 C7 110.8(3)
N1 C6 C7 105.5(2)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C6 C9 H9A 109.5
C6 C9 H9B 109.5
H9A C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C10 O3 123.0(3)
O2 C10 C11 117.3(3)
O3 C10 C11 119.7(3)
C12 C11 C10 130.2(3)
C12 C11 H11 114.9
C10 C11 H11 114.9
C11 C12 C13 130.5(3)
C11 C12 H12 114.8
C13 C12 H12 114.8
O4 C13 O5 122.9(3)
O4 C13 C12 117.4(3)
O5 C13 C12 119.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C5 2.068(4)
O1 C5 1.376(4)
O1 C2 1.379(4)
O2 C10 1.241(4)
O3 C10 1.287(4)
O3 H5O 1.25(5)
O4 C13 1.238(4)
O5 C13 1.297(3)
O5 H5O 1.18(5)
N1 C1 1.510(4)
N1 C6 1.531(4)
N1 H1A 0.88(4)
N1 H1B 0.88(4)
C1 C2 1.494(4)
C1 H1C 0.9900
C1 H1D 0.9900
C2 C3 1.355(5)
C3 C4 1.435(6)
C3 H3 0.9500
C4 C5 1.341(6)
C4 H4 0.9500
C6 C8 1.523(5)
C6 C9 1.527(4)
C6 C7 1.535(4)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.507(4)
C11 C12 1.340(5)
C11 H11 0.9500
C12 C13 1.515(5)
C12 H12 0.9500
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
O5 H5O O3 . 1.18(5) 1.25(5) 2.425(3) 172(4)
N1 H1A O2 . 0.88(4) 1.97(4) 2.828(3) 167(3)
N1 H1B O4 1_556 0.88(4) 1.92(4) 2.792(4) 172(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
C6 N1 C1 C2 168.5(3)
C5 O1 C2 C3 -0.4(4)
C5 O1 C2 C1 -179.6(3)
N1 C1 C2 C3 -115.3(4)
N1 C1 C2 O1 63.7(4)
O1 C2 C3 C4 0.5(4)
C1 C2 C3 C4 179.6(3)
C2 C3 C4 C5 -0.5(4)
C3 C4 C5 O1 0.2(4)
C3 C4 C5 I1 -174.7(3)
C2 O1 C5 C4 0.1(4)
C2 O1 C5 I1 175.9(2)
C1 N1 C6 C8 -66.1(3)
C1 N1 C6 C9 56.6(4)
C1 N1 C6 C7 175.5(3)
O2 C10 C11 C12 -173.7(3)
O3 C10 C11 C12 6.0(5)
C10 C11 C12 C13 -0.3(5)
C11 C12 C13 O4 172.5(3)
C11 C12 C13 O5 -6.8(5)

_cod_database_fobs_code 2242076
