#------------------------------------------------------------------------------
#$Date: 2017-08-05 21:34:20 +0300 (Sat, 05 Aug 2017) $
#$Revision: 199568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/41/4514132.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4514132
loop_
_publ_author_name
'Malaspina, Lorraine A.'
'Edwards, Alison J.'
'Woińska, Magdalena'
'Jayatilaka, Dylan'
'Turner, Michael J.'
'Price, Jason R.'
'Herbst-Irmer, Regine'
'Sugimoto, Kunihisa'
'Nishibori, Eiji'
'Grabowsky, Simon'
_publ_contact_author
;
  Dr. Simon Grabowsky
  University of Bremen
  Institute for Inorganic Chemistry and Crystallography
  Leobener Str. NW2
  28359 Bremen
  Germany
;
_publ_section_title
;
 Predicting the Position of the Hydrogen Atom in the Short Intramolecular
 Hydrogen Bond of the Hydrogen Maleate Anion from Geometric Correlations
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3812
_journal_paper_doi               10.1021/acs.cgd.7b00390
_journal_volume                  17
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C4 H3 O4, C5 H7 N2'
_chemical_formula_sum            'C9 H10 N2 O4'
_chemical_formula_weight         210.19
_chemical_name_common            '4-aminopyridinium hydrogen maleate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     isomor
_audit_creation_date             2016-04-29
_audit_creation_method           CRYSTALS_ver_14.61
_cell_angle_alpha                90
_cell_angle_beta                 96.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8515(16)
_cell_length_b                   5.5447(11)
_cell_length_c                   10.921(2)
_cell_measurement_radiation      Synchrotron
_cell_measurement_reflns_used    14602
_cell_measurement_temperature    25
_cell_measurement_theta_max      26.191
_cell_measurement_theta_min      0.932
_cell_measurement_wavelength     0.3531
_cell_volume                     472.48(16)
_computing_cell_refinement       'LaueG (Piltz, 2011)'
_computing_data_collection       'MAATEL/ANSTO control program'
_computing_data_reduction
'argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      12
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      '39 images, exposure time  42 to  42 minutes'
_diffrn_measurement_device       'Laue image-plate diffractometer'
_diffrn_measurement_device_type  KOALA
_diffrn_measurement_method       Laue
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.85
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26407
_diffrn_reflns_reduction_process 'LaueG (Piltz, 2011)'
_diffrn_reflns_resolution_max    1.54
_diffrn_reflns_theta_full        70.78
_diffrn_reflns_theta_max         70.88
_diffrn_source                   'nuclear reactor'
_diffrn_source_details           'thermal neutrons, supermirror guides'
_diffrn_source_type
'OPAL reactor, ANSTO, Lucas Heights, Australia'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             130
_exptl_crystal_size_max          1.6
_exptl_crystal_size_mid          1.2
_exptl_crystal_size_min          0.9
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.70
_refine_ls_extinction_coef       2.0(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.0004462
_refine_ls_shift/su_mean         0.0000580
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.30 -2.59 0.685 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0229
_refine_ls_wR_factor_gt          0.0210
_refine_ls_wR_factor_ref         0.0209
_reflns_number_gt                1525
_reflns_number_total             1601
_reflns_threshold_expression     >2sigma(I)
_oxford_diffrn_Wilson_B_factor   0.64
_oxford_diffrn_Wilson_scale      0.24
_oxford_refine_ls_r_factor_ref   0.0256
_oxford_refine_ls_scale          2.066(4)
_oxford_reflns_number_all        1598
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            4APHmal_F.cif
_cod_data_source_block           4APHmal_neutron
_cod_depositor_comments
'Adding full bibliography for 4514126--4514133.cif.'
_cod_original_cell_volume        472.46(17)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4514132
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
C1 C 0.31213(12) 0.5000(3) 0.66852(8) 0.0053 1.0000 Uani
H1 H 0.2467(3) 0.2885(6) 0.8088(2) 0.0197 1.0000 Uani
N1 N 0.88540(10) 0.5488(2) 0.91599(7) 0.0076 1.0000 Uani
O1 O 0.32185(15) 0.4671(3) 0.78577(10) 0.0069 1.0000 Uani
C2 C 0.21875(13) 0.3215(3) 0.58158(9) 0.0061 1.0000 Uani
H2 H 0.2237(4) 0.3682(6) 0.4849(2) 0.0235 1.0000 Uani
N2 N 0.57981(9) 0.0061(2) 0.75446(6) 0.0068 1.0000 Uani
O2 O 0.16624(15) 0.1030(3) 0.82665(10) 0.0075 1.0000 Uani
C3 C 0.13120(13) 0.1201(3) 0.60427(9) 0.0058 1.0000 Uani
H3 H 0.0737(3) 0.0179(7) 0.5250(2) 0.0228 1.0000 Uani
O3 O 0.37948(15) 0.6745(3) 0.62080(10) 0.0073 1.0000 Uani
C4 C 0.09578(11) 0.0099(3) 0.72439(8) 0.0054 1.0000 Uani
H4 H 0.9363(3) 0.6715(6) 0.8604(2) 0.0206 1.0000 Uani
O4 O -0.00083(15) -0.1670(3) 0.72027(11) 0.0080 1.0000 Uani
C5 C 0.78550(12) 0.3727(3) 0.86409(8) 0.0052 1.0000 Uani
H5 H 0.8966(4) 0.5701(6) 1.0097(2) 0.0224 1.0000 Uani
C6 C 0.74945(12) 0.3558(3) 0.73372(9) 0.0062 1.0000 Uani
H6 H 0.8016(3) 0.4889(6) 0.6746(2) 0.0217 1.0000 Uani
C7 C 0.64671(13) 0.1734(3) 0.68291(9) 0.0063 1.0000 Uani
H7 H 0.6142(3) 0.1556(6) 0.5831(2) 0.0202 1.0000 Uani
C8 C 0.61152(12) 0.0163(3) 0.87873(9) 0.0065 1.0000 Uani
C9 C 0.71186(13) 0.1945(3) 0.93636(9) 0.0063 1.0000 Uani
H9 H 0.5533(4) -0.1236(6) 0.9300(2) 0.0231 1.0000 Uani
H10 H 0.7358(4) 0.1986(7) 1.0371(2) 0.0223 1.0000 Uani
H8 H 0.5012(3) -0.1309(6) 0.7115(2) 0.0189 1.0000 Uani
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 6.6484
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
H 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 -3.7409
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
N 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 9.3600
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
O 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 5.8050
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 120.35(10) yes
O1 C1 O3 123.09(11) yes
C2 C1 O3 116.55(9) yes
O1 H1 O2 177.0(2) no
H4 N1 C5 118.92(16) no
H4 N1 H5 121.4(2) no
C5 N1 H5 119.26(18) no
H1 O1 C1 110.54(15) no
C1 C2 H2 112.79(18) no
C1 C2 C3 130.64(9) yes
H2 C2 C3 116.57(18) no
C7 N2 C8 120.61(8) yes
C7 N2 H8 118.79(16) no
C8 N2 H8 120.60(16) no
H1 O2 C4 111.85(14) no
C2 C3 H3 117.35(17) no
C2 C3 C4 130.20(9) yes
H3 C3 C4 112.44(17) no
C3 C4 O2 119.20(10) yes
C3 C4 O4 117.60(10) yes
O2 C4 O4 123.20(11) yes
N1 C5 C6 120.90(9) yes
N1 C5 C9 121.71(8) yes
C6 C5 C9 117.39(9) yes
C5 C6 H6 120.10(17) no
C5 C6 C7 119.71(9) yes
H6 C6 C7 120.17(17) no
C6 C7 N2 121.29(8) yes
C6 C7 H7 122.02(18) no
N2 C7 H7 116.68(17) no
N2 C8 C9 121.49(9) yes
N2 C8 H9 116.48(18) no
C9 C8 H9 122.03(18) no
C5 C9 C8 119.49(9) yes
C5 C9 H10 120.44(19) no
C8 C9 H10 120.06(19) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.2872(15) yes
C1 C2 1.5043(15) yes
C1 O3 1.2445(15) yes
H1 O1 1.194(3) no
H1 O2 1.234(3) no
N1 H4 1.023(3) no
N1 C5 1.3381(12) yes
N1 H5 1.024(2) no
C2 H2 1.092(3) no
C2 C3 1.3489(14) yes
N2 C7 1.3561(13) yes
N2 C8 1.3534(12) yes
N2 H8 1.055(3) no
O2 C4 1.2968(15) yes
C3 H3 1.090(3) no
C3 C4 1.5009(14) yes
C4 O4 1.2377(15) yes
C5 C6 1.4234(14) yes
C5 C9 1.4263(14) yes
C6 H6 1.090(3) no
C6 C7 1.3716(15) yes
C7 H7 1.096(2) no
C8 C9 1.3720(15) yes
C8 H9 1.087(3) no
C9 H10 1.096(2) 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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O1 H1 O2 . 177.0(2) 1.194(3) 1.234(3) 2.4268(16) yes
N1 H4 O4 1_665 162.3(2) 1.023(3) 1.885(3) 2.8767(16) yes
N1 H5 O2 2_657 160.2(2) 1.024(2) 1.915(3) 2.8997(16) yes
C6 H6 O4 1_665 132.2(2) 1.090(3) 2.474(3) 3.3064(16) yes
C7 H7 O3 2_646 163.3(2) 1.096(2) 2.236(2) 3.3001(16) yes
C9 H10 O1 2_647 140.3(2) 1.096(2) 2.406(3) 3.3238(16) yes
N2 H8 C1 1_545 164.3(2) 1.055(3) 2.541(3) 3.5682(16) yes
N2 H8 O3 1_545 170.4(2) 1.055(3) 1.688(3) 2.7336(16) yes
