#------------------------------------------------------------------------------
#$Date: 2017-03-15 09:13:42 +0200 (Wed, 15 Mar 2017) $
#$Revision: 194252 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242075.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_2242075
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          'C15 H20 N O +, C4 H3 O4 -'
_chemical_formula_moiety         'C15 H20 N O +, C4 H3 O4 -'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_chemical_name_systematic
;
2-Methyl-N-[(5-phenylfuran-2-yl)methyl]propan-2-aminium
(2Z)-3-carboxyacrylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2015
_cell_angle_alpha                94.3870(10)
_cell_angle_beta                 94.5520(10)
_cell_angle_gamma                91.5780(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5177(4)
_cell_length_b                   9.8339(6)
_cell_length_c                   12.1951(7)
_cell_measurement_reflns_used    2186
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.47
_cell_measurement_theta_min      2.57
_cell_volume                     895.57(9)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_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      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14165
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.687
_diffrn_reflns_theta_min         2.078
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         6555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0530
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                3947
_reflns_number_total             6555
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7663sup1.cif
_cod_data_source_block           I
_cod_database_code               2242075
_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   0.973
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O O1 0.92461(12) 0.90909(9) 0.24482(7) 0.0223(2) Uani d 1
N N1 1.20595(14) 0.76402(11) 0.11610(9) 0.0175(2) Uani d 1
H H1A 1.2498(18) 0.6949(15) 0.1627(12) 0.021 Uiso d 1
H H1B 1.2370(19) 0.8484(15) 0.1545(12) 0.021 Uiso d 1
C C1 1.00641(17) 0.74679(14) 0.09978(11) 0.0223(3) Uani d 1
H H1C 0.9596 0.8102 0.0461 0.027 Uiso calc 1
H H1D 0.9736 0.6525 0.0691 0.027 Uiso calc 1
C C2 0.92419(17) 0.77432(13) 0.20536(11) 0.0216(3) Uani d 1
C C3 0.84120(18) 0.69612(15) 0.27361(12) 0.0264(3) Uani d 1
H H3 0.8233 0.5998 0.2652 0.032 Uiso calc 1
C C4 0.78576(19) 0.78600(15) 0.36059(12) 0.0272(3) Uani d 1
H H4 0.7229 0.7610 0.4210 0.033 Uiso calc 1
C C5 0.83939(17) 0.91370(14) 0.34107(11) 0.0222(3) Uani d 1
C C6 0.82740(17) 1.04880(14) 0.39825(11) 0.0229(3) Uani d 1
C C7 0.89734(18) 1.16539(15) 0.35647(12) 0.0262(3) Uani d 1
H H7 0.9550 1.1572 0.2898 0.031 Uiso calc 1
C C8 0.88348(19) 1.29304(16) 0.41130(12) 0.0296(3) Uani d 1
H H8 0.9325 1.3716 0.3824 0.036 Uiso calc 1
C C9 0.79823(19) 1.30640(16) 0.50820(12) 0.0302(3) Uani d 1
H H9 0.7881 1.3940 0.5454 0.036 Uiso calc 1
C C10 0.72778(19) 1.19148(16) 0.55059(11) 0.0286(3) Uani d 1
H H10 0.6689 1.2005 0.6167 0.034 Uiso calc 1
C C11 0.74308(18) 1.06376(16) 0.49678(11) 0.0260(3) Uani d 1
H H11 0.6960 0.9854 0.5269 0.031 Uiso calc 1
C C12 1.30888(17) 0.75667(13) 0.01359(11) 0.0200(3) Uani d 1
C C13 1.50545(18) 0.75962(15) 0.05686(12) 0.0265(3) Uani d 1
H H13A 1.5326 0.8418 0.1067 0.040 Uiso calc 1
H H13B 1.5804 0.7604 -0.0053 0.040 Uiso calc 1
H H13C 1.5294 0.6785 0.0969 0.040 Uiso calc 1
C C14 1.25942(19) 0.62298(14) -0.05538(12) 0.0262(3) Uani d 1
H H14A 1.1346 0.6240 -0.0853 0.039 Uiso calc 1
H H14B 1.2751 0.5465 -0.0089 0.039 Uiso calc 1
H H14C 1.3368 0.6126 -0.1163 0.039 Uiso calc 1
C C15 1.26620(19) 0.88007(15) -0.05105(12) 0.0262(3) Uani d 1
H H15A 1.2918 0.9639 -0.0029 0.039 Uiso calc 1
H H15B 1.1397 0.8753 -0.0779 0.039 Uiso calc 1
H H15C 1.3397 0.8804 -0.1139 0.039 Uiso calc 1
O O2 0.34880(14) 0.57638(10) 0.25174(8) 0.0310(2) Uani d 1
O O3 0.19310(13) 0.40290(11) 0.15970(8) 0.0306(2) Uani d 1
O O4 0.34720(13) -0.00091(10) 0.23666(8) 0.0279(2) Uani d 1
O O5 0.19913(12) 0.15695(10) 0.14960(8) 0.0255(2) Uani d 1
H H5O 0.190(2) 0.2747(18) 0.1531(13) 0.038 Uiso d 1
C C16 0.31067(18) 0.45314(14) 0.23545(11) 0.0226(3) Uani d 1
C C17 0.40964(18) 0.36056(14) 0.30859(11) 0.0235(3) Uani d 1
H H17 0.4830 0.4061 0.3680 0.028 Uiso calc 1
C C18 0.41217(18) 0.22465(14) 0.30440(11) 0.0226(3) Uani d 1
H H18 0.4888 0.1892 0.3602 0.027 Uiso calc 1
C C19 0.31356(17) 0.11924(14) 0.22580(11) 0.0210(3) 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C5 106.85(10)
C1 N1 C12 117.49(10)
C1 N1 H1A 108.0(8)
C12 N1 H1A 108.0(8)
C1 N1 H1B 109.6(9)
C12 N1 H1B 106.5(9)
H1A N1 H1B 106.6(12)
C2 C1 N1 111.02(10)
C2 C1 H1C 109.4
N1 C1 H1C 109.4
C2 C1 H1D 109.4
N1 C1 H1D 109.4
H1C C1 H1D 108.0
C3 C2 O1 109.83(12)
C3 C2 C1 134.49(13)
O1 C2 C1 115.65(12)
C2 C3 C4 106.78(13)
C2 C3 H3 126.6
C4 C3 H3 126.6
C5 C4 C3 107.10(12)
C5 C4 H4 126.4
C3 C4 H4 126.4
C4 C5 O1 109.43(12)
C4 C5 C6 134.61(13)
O1 C5 C6 115.96(12)
C7 C6 C11 118.51(13)
C7 C6 C5 121.38(12)
C11 C6 C5 120.11(13)
C8 C7 C6 120.65(13)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 120.20(15)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 119.80(14)
C10 C9 H9 120.1
C8 C9 H9 120.1
C11 C10 C9 120.17(13)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C6 120.67(14)
C10 C11 H11 119.7
C6 C11 H11 119.7
N1 C12 C15 108.92(10)
N1 C12 C14 109.41(11)
C15 C12 C14 111.64(11)
N1 C12 C13 105.08(10)
C15 C12 C13 111.28(11)
C14 C12 C13 110.29(11)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C16 O3 H5O 111.3(7)
C19 O5 H5O 111.7(8)
O2 C16 O3 123.38(13)
O2 C16 C17 116.77(12)
O3 C16 C17 119.85(12)
C18 C17 C16 130.78(13)
C18 C17 H17 114.6
C16 C17 H17 114.6
C17 C18 C19 130.28(12)
C17 C18 H18 114.9
C19 C18 H18 114.9
O4 C19 O5 123.00(12)
O4 C19 C18 117.33(12)
O5 C19 C18 119.67(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3747(16)
O1 C5 1.3796(15)
N1 C1 1.5007(16)
N1 C12 1.5198(16)
N1 H1A 0.968(15)
N1 H1B 0.936(15)
C1 C2 1.4817(18)
C1 H1C 0.9900
C1 H1D 0.9900
C2 C3 1.352(2)
C3 C4 1.424(2)
C3 H3 0.9500
C4 C5 1.353(2)
C4 H4 0.9500
C5 C6 1.4609(19)
C6 C7 1.396(2)
C6 C11 1.4022(19)
C7 C8 1.387(2)
C7 H7 0.9500
C8 C9 1.388(2)
C8 H8 0.9500
C9 C10 1.387(2)
C9 H9 0.9500
C10 C11 1.384(2)
C10 H10 0.9500
C11 H11 0.9500
C12 C15 1.5247(19)
C12 C14 1.5259(18)
C12 C13 1.5279(18)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
O2 C16 1.2351(17)
O3 C16 1.2866(17)
O3 H5O 1.257(17)
O4 C19 1.2300(16)
O5 C19 1.2979(16)
O5 H5O 1.160(17)
C16 C17 1.4947(19)
C17 C18 1.3343(18)
C17 H17 0.9500
C18 C19 1.4952(18)
C18 H18 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 . 1.160(17) 1.257(17) 2.4142(14) 175.3(15)
N1 H1A O2 1_655 0.968(15) 1.790(15) 2.7547(15) 174.9(13)
N1 H1B O4 1_665 0.936(15) 1.860(15) 2.7803(14) 167.4(13)
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
C12 N1 C1 C2 -172.59(11)
C5 O1 C2 C3 0.25(14)
C5 O1 C2 C1 178.57(11)
N1 C1 C2 C3 -109.20(17)
N1 C1 C2 O1 73.02(14)
O1 C2 C3 C4 0.17(15)
C1 C2 C3 C4 -177.70(14)
C2 C3 C4 C5 -0.53(16)
C3 C4 C5 O1 0.70(16)
C3 C4 C5 C6 -178.87(14)
C2 O1 C5 C4 -0.60(14)
C2 O1 C5 C6 179.06(11)
C4 C5 C6 C7 -179.94(15)
O1 C5 C6 C7 0.51(18)
C4 C5 C6 C11 -0.5(2)
O1 C5 C6 C11 179.98(11)
C11 C6 C7 C8 0.0(2)
C5 C6 C7 C8 179.45(13)
C6 C7 C8 C9 -0.6(2)
C7 C8 C9 C10 0.4(2)
C8 C9 C10 C11 0.3(2)
C9 C10 C11 C6 -0.9(2)
C7 C6 C11 C10 0.8(2)
C5 C6 C11 C10 -178.73(12)
C1 N1 C12 C15 67.55(14)
C1 N1 C12 C14 -54.73(14)
C1 N1 C12 C13 -173.13(11)
O2 C16 C17 C18 -172.20(14)
O3 C16 C17 C18 7.4(2)
C16 C17 C18 C19 -1.3(3)
C17 C18 C19 O4 176.22(14)
C17 C18 C19 O5 -3.2(2)

_cod_database_fobs_code 2242075
