#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/08/2010851.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_2010851
loop_
_publ_author_name
'Hosomi, Hiroyuki'
'Ohba, Shigeru'
'Ito, Yoshikatsu'
_publ_section_title
;
 Triethylammonium hydrogen fumarate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e139
_journal_page_last               e139
_journal_paper_doi               10.1107/S0108270100003267
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'C6 H16 N1 1+, C4 H3 O4 1-'
_chemical_formula_moiety         'C6 H16 N1 1+, C4 H3 O4 1-'
_chemical_formula_sum            'C10 H19 N O4'
_chemical_formula_weight         217.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.03(3)
_cell_angle_beta                 90.11(2)
_cell_angle_gamma                113.990(10)
_cell_formula_units_Z            4
_cell_length_a                   13.409(3)
_cell_length_b                   13.656(3)
_cell_length_c                   7.432(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.4
_cell_volume                     1237.5(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device_type  'Rigaku AFC5'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .016
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5071
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        4.4
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .6
_exptl_crystal_size_min          .4
_refine_diff_density_max         .21
_refine_diff_density_min         -.12
_refine_ls_extinction_coef       .026(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4850
_refine_ls_R_factor_gt           .045
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0510P)²+0.1858P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .117
_reflns_number_gt                3040
_reflns_number_total             4850
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0235.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C10 H19 N1 O4'
_cod_database_code               2010851
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_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
_atom_site_type_symbol
O1 .71490(10) .27340(10) .8165(2) .0790(5) Uani d . 1.00 . . O
O2 .54650(10) .15030(10) .7510(2) .0644(4) Uani d . 1.00 . . O
O3 .67830(10) .25050(10) .1407(2) .0724(5) Uani d . 1.00 . . O
O4 .85130(10) .36090(10) .2025(2) .0660(4) Uani d . 1.00 . . O
O5 .82330(10) -.16240(10) .4545(2) .0537(4) Uani d . 1.00 . . O
O6 .85790(10) -.14500(10) .7516(2) .0636(4) Uani d . 1.00 . . O
O7 .65490(10) -.32080(10) .4898(2) .0684(5) Uani d . 1.00 . . O
O8 .70920(10) -.43160(10) .3233(2) .0714(5) Uani d . 1.00 . . O
N9 .60030(10) -.13780(10) .9926(2) .0488(4) Uani d . 1.00 . . N
N10 .89920(10) -.35630(10) .1308(2) .0498(4) Uani d . 1.00 . . N
C11 .6366(2) .2156(2) .7091(2) .0509(5) Uani d . 1.00 . . C
C12 .6544(2) .2258(2) .5117(3) .0550(5) Uani d . 1.00 . . C
C13 .7388(2) .2973(2) .4453(2) .0519(5) Uani d . 1.00 . . C
C14 .7610(2) .3063(2) .2501(2) .0478(5) Uani d . 1.00 . . C
C15 .88120(10) -.11670(10) .6008(3) .0430(4) Uani d . 1.00 . . C
C16 .9843(2) -.02060(10) .5768(3) .0435(4) Uani d . 1.00 . . C
C17 .64430(10) -.4130(2) .4212(3) .0476(5) Uani d . 1.00 . . C
C18 .5417(2) -.5048(2) .4629(3) .0479(5) Uani d . 1.00 . . C
C19 .5884(2) -.0611(2) .8697(3) .0562(5) Uani d . 1.00 . . C
C20 .6635(3) -.0396(3) .7138(4) .0822(9) Uani d . 1.00 . . C
C21 .7063(2) -.0938(2) 1.1004(3) .0659(6) Uani d . 1.00 . . C
C22 .7241(3) .0054(3) 1.2208(4) .0799(8) Uani d . 1.00 . . C
C23 .5769(3) -.2453(2) .8914(3) .0673(6) Uani d . 1.00 . . C
C24 .5422(4) -.3348(3) 1.0123(5) .0980(10) Uani d . 1.00 . . C
C25 .9282(2) -.2414(2) .0972(4) .0572(6) Uani d . 1.00 . . C
C26 1.0368(3) -.1878(3) .0141(5) .0865(9) Uani d . 1.00 . . C
C27 .8772(2) -.4305(2) -.0402(3) .0646(6) Uani d . 1.00 . . C
C28 .7815(3) -.4362(3) -.1515(5) .0878(9) Uani d . 1.00 . . C
C29 .9795(2) -.3709(2) .2549(4) .0685(7) Uani d . 1.00 . . C
C30 .9897(3) -.3115(4) .4387(5) .1010(10) Uani d . 1.00 . . C
H3 .699(3) .260(2) .001(4) .12810(10) Uiso d . 1.00 . . H
H5 .744(3) -.242(2) .473(4) .12100(10) Uiso d . 1.00 . . H
H9 .546(2) -.149(2) 1.071(3) .05829(8) Uiso d . 1.00 . . H
H10 .838(2) -.376(2) .186(3) .05359(7) Uiso d . 1.00 . . H
H12 .599(2) .175(2) .435(3) .07964(10) Uiso d . 1.00 . . H
H13 .794(2) .349(2) .528(3) .06794(8) Uiso d . 1.00 . . H
H16 1.027(2) .012(2) .687(3) .05385(7) Uiso d . 1.00 . . H
H18 .540(2) -.570(2) .432(3) .04613(7) Uiso d . 1.00 . . H
H19A .602(2) .006(2) .945(3) .06567(8) Uiso d . 1.00 . . H
H19B .510(2) -.094(2) .824(3) .07506(9) Uiso d . 1.00 . . H
H20A .651(2) -.107(2) .644(4) .09170(10) Uiso d . 1.00 . . H
H20B .646(2) .010(3) .642(4) .11460(10) Uiso d . 1.00 . . H
H20C .744(3) -.009(3) .769(5) .1402(2) Uiso d . 1.00 . . H
H21A .763(2) -.081(2) 1.011(4) .08830(10) Uiso d . 1.00 . . H
H21B .701(2) -.152(2) 1.171(3) .07443(9) Uiso d . 1.00 . . H
H22A .665(2) -.001(2) 1.295(4) .08630(10) Uiso d . 1.00 . . H
H22B .789(3) .023(2) 1.302(4) .11080(10) Uiso d . 1.00 . . H
H22C .734(2) .066(2) 1.152(4) .10430(10) Uiso d . 1.00 . . H
H23A .646(2) -.237(2) .825(3) .08292(10) Uiso d . 1.00 . . H
H23B .516(2) -.257(2) .799(4) .08820(10) Uiso d . 1.00 . . H
H24A .529(2) -.399(3) .943(4) .10830(10) Uiso d . 1.00 . . H
H24B .608(3) -.317(3) 1.098(5) .1450(2) Uiso d . 1.00 . . H
H24C .485(3) -.338(3) 1.079(5) .1221(2) Uiso d . 1.00 . . H
H25A .926(2) -.207(2) .206(3) .07549(9) Uiso d . 1.00 . . H
H25B .873(2) -.244(2) .017(3) .06133(8) Uiso d . 1.00 . . H
H26A 1.037(3) -.228(3) -.104(5) .1308(2) Uiso d . 1.00 . . H
H26B 1.098(3) -.184(2) .097(4) .11480(10) Uiso d . 1.00 . . H
H26C 1.049(2) -.117(3) .005(4) .10650(10) Uiso d . 1.00 . . H
H27A .947(2) -.406(2) -.096(3) .06638(8) Uiso d . 1.00 . . H
H27B .867(2) -.500(3) .000(4) .10530(10) Uiso d . 1.00 . . H
H28A .768(3) -.493(3) -.243(5) .11630(10) Uiso d . 1.00 . . H
H28B .720(3) -.452(3) -.083(5) .1206(2) Uiso d . 1.00 . . H
H28C .801(3) -.363(3) -.195(5) .1533(2) Uiso d . 1.00 . . H
H29A 1.047(2) -.348(2) .193(3) .07096(8) Uiso d . 1.00 . . H
H29B .951(2) -.450(3) .267(4) .10680(10) Uiso d . 1.00 . . H
H30A .915(3) -.335(3) .483(5) .1386(2) Uiso d . 1.00 . . H
H30B 1.033(4) -.233(4) .422(6) .1818(3) Uiso d . 1.00 . . H
H30C 1.029(3) -.342(3) .523(5) .1442(2) Uiso d . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .002
;International Tables for Crystallography
(1992, Vol. C)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C)
;
N N .006 .003
;International Tables for Crystallography
(1992, Vol. C)
;
O O .011 .006
;International Tables for Crystallography
(1992, Vol. C)
;
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
C14 O3 H3 . . 111.0(10) no
C15 O5 H5 . . 114.0(10) no
C17 O7 H5 . . 118.0(10) no
C19 N9 C21 . . 114.1(2) no
C19 N9 C23 . . 111.1(2) no
C19 N9 H9 . . 104.0(10) no
C21 N9 C23 . . 112.5(2) no
C21 N9 H9 . . 107.0(10) no
C23 N9 H9 . . 105.0(10) no
C25 N10 C27 . . 113.1(2) no
C25 N10 C29 . . 113.9(2) no
C25 N10 H10 . . 105.0(10) no
C27 N10 C29 . . 110.9(2) no
C27 N10 H10 . . 106.0(10) no
C29 N10 H10 . . 106.0(10) no
O1 C11 O2 . . 126.1(2) yes
O1 C11 C12 . . 117.0(2) no
O2 C11 C12 . . 116.9(2) no
C11 C12 C13 . . 124.9(2) no
C11 C12 H12 . . 114.0(10) no
C13 C12 H12 . . 120.0(10) no
C12 C13 C14 . . 126.1(2) no
C12 C13 H13 . . 118.0(10) no
C14 C13 H13 . . 115.0(10) no
O3 C14 O4 . . 124.3(2) yes
O3 C14 C13 . . 115.0(2) no
O4 C14 C13 . . 120.7(2) no
O5 C15 O6 . . 125.60(10) yes
O5 C15 C16 . . 115.1(2) no
O6 C15 C16 . . 119.4(2) no
C15 C16 C16 . 2_756 125.1(2) no
C15 C16 H16 . . 113.0(10) no
C16 C16 H16 2_756 . 120.0(10) no
O7 C17 O8 . . 125.7(2) yes
O7 C17 C18 . . 115.6(2) no
O8 C17 C18 . . 118.7(2) no
C17 C18 C18 . 2_646 124.9(3) no
C17 C18 H18 . . 114.0(10) no
C18 C18 H18 2_646 . 120.0(10) no
N9 C19 C20 . . 114.2(3) no
N9 C19 H19A . . 106.0(10) no
N9 C19 H19B . . 106.0(10) no
C20 C19 H19A . . 110.0(10) no
C20 C19 H19B . . 110.0(10) no
H19A C19 H19B . . 108(2) no
C19 C20 H20A . . 109.0(10) no
C19 C20 H20B . . 106.0(10) no
C19 C20 H20C . . 107(2) no
H20A C20 H20B . . 112(2) no
H20A C20 H20C . . 106(2) no
H20B C20 H20C . . 115(2) no
N9 C21 C22 . . 113.4(3) no
N9 C21 H21A . . 105.0(10) no
N9 C21 H21B . . 103.0(10) no
C22 C21 H21A . . 111.0(10) no
C22 C21 H21B . . 110.0(10) no
H21A C21 H21B . . 111(2) no
C21 C22 H22A . . 113.0(10) no
C21 C22 H22B . . 109(2) no
C21 C22 H22C . . 111.0(10) no
H22A C22 H22B . . 107(2) no
H22A C22 H22C . . 104(2) no
H22B C22 H22C . . 109(2) no
N9 C23 C24 . . 112.7(2) no
N9 C23 H23A . . 106.0(10) no
N9 C23 H23B . . 105.0(10) no
C24 C23 H23A . . 112.0(10) no
C24 C23 H23B . . 110.0(10) no
H23A C23 H23B . . 108(2) no
C23 C24 H24A . . 108(2) no
C23 C24 H24B . . 104(2) no
C23 C24 H24C . . 112(2) no
H24A C24 H24B . . 109(3) no
H24A C24 H24C . . 112(2) no
H24B C24 H24C . . 108(3) no
N10 C25 C26 . . 114.3(3) no
N10 C25 H25A . . 105.0(10) no
N10 C25 H25B . . 104.0(10) no
C26 C25 H25A . . 111.0(10) no
C26 C25 H25B . . 109.0(10) no
H25A C25 H25B . . 111(2) no
C25 C26 H26A . . 109.0(10) no
C25 C26 H26B . . 110.0(10) no
C25 C26 H26C . . 107(2) no
H26A C26 H26B . . 110(3) no
H26A C26 H26C . . 113(2) no
H26B C26 H26C . . 104(2) no
N10 C27 C28 . . 113.2(3) no
N10 C27 H27A . . 103.0(10) no
N10 C27 H27B . . 104.0(10) no
C28 C27 H27A . . 117.0(10) no
C28 C27 H27B . . 112.0(10) no
H27A C27 H27B . . 103(2) no
C27 C28 H28A . . 105(2) no
C27 C28 H28B . . 110(2) no
C27 C28 H28C . . 107(2) no
H28A C28 H28B . . 108(2) no
H28A C28 H28C . . 115(3) no
H28B C28 H28C . . 108(3) no
N10 C29 C30 . . 112.4(3) no
N10 C29 H29A . . 105.0(10) no
N10 C29 H29B . . 106.0(10) no
C30 C29 H29A . . 113.0(10) no
C30 C29 H29B . . 109.0(10) no
H29A C29 H29B . . 110(2) no
C29 C30 H30A . . 106.0(10) no
C29 C30 H30B . . 105(2) no
C29 C30 H30C . . 106(2) no
H30A C30 H30B . . 119(4) no
H30A C30 H30C . . 104(3) no
H30B C30 H30C . . 113(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . . 1.255(2) yes
O2 C11 . . 1.235(2) yes
O3 C14 . . 1.293(2) yes
O3 H3 . . 1.08(3) no
O4 C14 . . 1.208(2) yes
O5 C15 . . 1.288(2) yes
O5 H5 . . 1.19(3) no
O6 C15 . . 1.217(2) yes
O7 C17 . . 1.268(3) yes
O7 H5 . . 1.26(3) no
O8 C17 . . 1.226(3) yes
N9 C19 . . 1.503(4) no
N9 C21 . . 1.497(3) no
N9 C23 . . 1.500(3) no
N9 H9 . . .90(2) no
N10 C25 . . 1.500(3) no
N10 C27 . . 1.503(3) no
N10 C29 . . 1.501(4) no
N10 H10 . . .87(2) no
C11 C12 . . 1.497(3) no
C12 C13 . . 1.290(3) no
C12 H12 . . .93(2) no
C13 C14 . . 1.487(3) no
C13 H13 . . .96(2) no
C15 C16 . . 1.493(2) no
C16 C16 . 2_756 1.312(4) no
C16 H16 . . .97(2) no
C17 C18 . . 1.493(2) no
C18 C18 . 2_646 1.296(4) no
C18 H18 . . .89(2) no
C19 C20 . . 1.506(4) no
C19 H19A . . .97(2) no
C19 H19B . . 1.00(3) no
C20 H20A . . .97(3) no
C20 H20B . . .99(4) no
C20 H20C . . 1.05(4) no
C21 C22 . . 1.488(4) no
C21 H21A . . .98(3) no
C21 H21B . . .97(3) no
C22 H22A . . .95(3) no
C22 H22B . . .99(3) no
C22 H22C . . .97(3) no
C23 C24 . . 1.500(5) no
C23 H23A . . 1.02(3) no
C23 H23B . . 1.02(3) no
C24 H24A . . .93(3) no
C24 H24B . . 1.01(4) no
C24 H24C . . .90(4) no
C25 C26 . . 1.502(4) no
C25 H25A . . .91(3) no
C25 H25B . . .94(3) no
C26 H26A . . .99(4) no
C26 H26B . . 1.01(4) no
C26 H26C . . .92(4) no
C27 C28 . . 1.496(5) no
C27 H27A . . .97(2) no
C27 H27B . . .98(4) no
C28 H28A . . .95(3) no
C28 H28B . . .93(4) no
C28 H28C . . 1.01(5) no
C29 C30 . . 1.502(5) no
C29 H29A . . .96(2) no
C29 H29B . . 1.01(3) no
C30 H30A . . .99(4) no
C30 H30B . . 1.00(5) no
C30 H30C . . 1.03(5) no
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
O3 H3 O1 1_554 1.08(3) 1.40(3) 2.481(2) 174(3)
O5 H5 O7 . 1.19(3) 1.26(3) 2.445(2) 175(4)
N9 H9 O2 2_657 .90(2) 1.81(2) 2.708(2) 170(2)
N10 H10 O8 . .87(2) 1.92(2) 2.781(2) 173(2)
