#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/37/2213757.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_2213757
loop_
_publ_author_name
'Sun, Zhi-Hua'
'Yu, Wen-Tao'
'Fan, Jian-Dong'
'Xu, Dong '
'Wang, Xin-Qiang'
_publ_section_title
;
 <small>L</small>-Argininium(+) maleate({-}) dihydrate
;
_journal_coeditor_code           ER2026
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2805
_journal_page_last               o2807
_journal_paper_doi               10.1107/S1600536807020612
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C6 H15 N4 O2 +, C4 H3 O4 -, 2H2 O'
_chemical_formula_moiety         'C6 H15 N4 O2 +, C4 H3 O4 -, 2(H2 O)'
_chemical_formula_sum            'C10 H22 N4 O8'
_chemical_formula_weight         326.32
_chemical_name_systematic
;
L-Argininium(+) maleate(-) dihydrate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.1550(10)
_cell_angle_beta                 97.2650(10)
_cell_angle_gamma                101.649(2)
_cell_formula_units_Z            1
_cell_length_a                   5.27100(10)
_cell_length_b                   8.0481(2)
_cell_length_c                   9.7942(2)
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      4.02
_cell_volume                     383.422(15)
_computing_cell_refinement       'APEX2 Software Suite'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2005)'
_computing_data_reduction        'APEX2 Software Suite'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX II CCD detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3711
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(APEX2 Software Suite; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ball
_exptl_crystal_F_000             174
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         1762
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                1697
_reflns_number_total             1762
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2026.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        383.42(2)
_cod_database_code               2213757
_cod_database_fobs_code          2213757
loop_
_symmetry_equiv_pos_as_xyz
'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_refinement_flags
_atom_site_occupancy
C C1 0.5124(4) 0.2367(3) 1.1719(2) 0.0340(4) Uani d . 1
N N3 0.4360(3) 0.2303(2) 1.03538(19) 0.0371(4) Uani d . 1
H H3 0.5434 0.2894 0.9964 0.045 Uiso calc R 1
C C2 0.1777(4) 0.1272(3) 0.9496(2) 0.0328(4) Uani d . 1
H H2C 0.0443 0.1862 0.9844 0.039 Uiso calc R 1
H H2D 0.1402 0.0100 0.9625 0.039 Uiso calc R 1
C C3 0.1611(4) 0.1056(3) 0.7893(2) 0.0361(4) Uani d . 1
H H3B 0.1615 0.2190 0.7727 0.043 Uiso calc R 1
H H3A 0.3128 0.0672 0.7575 0.043 Uiso calc R 1
C C4 -0.0919(4) -0.0327(3) 0.7043(2) 0.0338(4) Uani d . 1
H H4B -0.2383 0.0017 0.7458 0.041 Uiso calc R 1
H H4A -0.0821 -0.1463 0.7177 0.041 Uiso calc R 1
C C5 -0.1544(3) -0.0604(3) 0.5413(2) 0.0309(4) Uani d . 1
H H5 -0.3139 -0.1580 0.4988 0.037 Uiso calc R 1
C C6 -0.2084(4) 0.1066(3) 0.5100(2) 0.0322(4) Uani d . 1
C C10 0.6354(4) 0.7889(3) 0.1320(3) 0.0430(5) Uani d . 1
C C9 0.4657(5) 0.7478(3) -0.0122(2) 0.0419(5) Uani d . 1
H H9 0.5449 0.7996 -0.0751 0.050 Uiso calc R 1
C C8 0.2192(4) 0.6491(3) -0.0667(2) 0.0397(5) Uani d . 1
H H8 0.1538 0.6440 -0.1610 0.048 Uiso calc R 1
C C7 0.0314(4) 0.5456(3) -0.0001(2) 0.0377(4) Uani d . 1
N N1 0.7486(4) 0.3327(3) 1.2460(2) 0.0459(5) Uani d . 1
H H1A 0.7976 0.3352 1.3339 0.055 Uiso calc R 1
H H1B 0.8535 0.3926 1.2064 0.055 Uiso calc R 1
N N2 0.3535(4) 0.1452(3) 1.2346(2) 0.0465(5) Uani d . 1
H H2A 0.4045 0.1487 1.3225 0.056 Uiso calc R 1
H H2B 0.1992 0.0823 1.1874 0.056 Uiso calc R 1
N N4 0.0642(3) -0.1117(2) 0.46877(18) 0.0352(4) Uani d . 1
H H4AA 0.2068 -0.0204 0.4995 0.053 Uiso calc R 1
H H4BB 0.0140 -0.1399 0.3732 0.053 Uiso calc R 1
H H4CC 0.1020 -0.2054 0.4905 0.053 Uiso calc R 1
O O1 -0.0316(3) 0.2044(2) 0.47618(19) 0.0465(4) Uani d . 1
O O2 -0.4342(3) 0.1313(2) 0.52342(17) 0.0392(3) Uani d . 1
O O3 0.1045(3) 0.5427(3) 0.12759(19) 0.0522(4) Uani d . 1
O O4 -0.1896(3) 0.4639(2) -0.07398(19) 0.0510(4) Uani d . 1
O O5 0.8595(4) 0.8837(3) 0.1586(2) 0.0620(5) Uani d . 1
O O6 0.5485(4) 0.7220(3) 0.2274(2) 0.0567(5) Uani d . 1
O O7 0.1916(5) 0.6117(3) 0.5624(3) 0.0704(6) Uani d D 1
O O8 0.6324(5) 0.4954(3) 0.6468(2) 0.0698(6) Uani d D 1
H H8A 0.678(8) 0.498(6) 0.736(3) 0.092(12) Uiso d D 1
H H8B 0.582(10) 0.383(3) 0.596(5) 0.131(19) Uiso d D 1
H H6A 0.338(9) 0.632(6) 0.179(5) 0.091(11) Uiso d . 1
H H7A 0.344(6) 0.585(7) 0.583(6) 0.126(18) Uiso d D 1
H H7B 0.054(7) 0.527(5) 0.552(6) 0.14(2) Uiso d 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
_geom_angle_publ_flag
N2 C1 N1 119.20(18) y
N2 C1 N3 120.33(18) y
N1 C1 N3 120.46(18) y
C1 N3 C2 122.46(17) ?
C1 N3 H3 118.8 ?
C2 N3 H3 118.8 ?
N3 C2 C3 112.22(16) ?
N3 C2 H2C 109.2 ?
C3 C2 H2C 109.2 ?
N3 C2 H2D 109.2 ?
C3 C2 H2D 109.2 ?
H2C C2 H2D 107.9 ?
C4 C3 C2 108.94(15) ?
C4 C3 H3B 109.9 ?
C2 C3 H3B 109.9 ?
C4 C3 H3A 109.9 ?
C2 C3 H3A 109.9 ?
H3B C3 H3A 108.3 ?
C3 C4 C5 116.33(16) ?
C3 C4 H4B 108.2 ?
C5 C4 H4B 108.2 ?
C3 C4 H4A 108.2 ?
C5 C4 H4A 108.2 ?
H4B C4 H4A 107.4 ?
N4 C5 C6 109.19(15) ?
N4 C5 C4 111.67(15) ?
C6 C5 C4 111.72(16) ?
N4 C5 H5 108.0 ?
C6 C5 H5 108.0 ?
C4 C5 H5 108.0 ?
O1 C6 O2 126.16(19) y
O1 C6 C5 118.50(17) y
O2 C6 C5 115.34(17) y
O5 C10 O6 120.3(2) ?
O5 C10 C9 119.6(2) ?
O6 C10 C9 120.2(2) ?
C8 C9 C10 130.9(2) ?
C8 C9 H9 114.6 ?
C10 C9 H9 114.6 ?
C9 C8 C7 130.1(2) ?
C9 C8 H8 114.9 ?
C7 C8 H8 114.9 ?
O4 C7 O3 122.8(2) ?
O4 C7 C8 117.7(2) ?
O3 C7 C8 119.47(19) ?
C1 N1 H1A 120.0 ?
C1 N1 H1B 120.0 ?
H1A N1 H1B 120.0 ?
C1 N2 H2A 120.0 ?
C1 N2 H2B 120.0 ?
H2A N2 H2B 120.0 ?
C5 N4 H4AA 109.5 ?
C5 N4 H4BB 109.5 ?
H4AA N4 H4BB 109.5 ?
C5 N4 H4CC 109.5 ?
H4AA N4 H4CC 109.5 ?
H4BB N4 H4CC 109.5 ?
C7 O3 H6A 111.2(19) ?
C10 O6 H6A 109(2) ?
H7A O7 H7B 115(5) ?
H8A O8 H8B 106(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.324(3) y
C1 N1 1.321(3) y
C1 N3 1.330(2) y
N3 C2 1.454(3) ?
N3 H3 0.8600 ?
C2 C3 1.520(3) ?
C2 H2C 0.9700 ?
C2 H2D 0.9700 ?
C3 C4 1.521(3) ?
C3 H3B 0.9700 ?
C3 H3A 0.9700 ?
C4 C5 1.531(3) ?
C4 H4B 0.9700 ?
C4 H4A 0.9700 ?
C5 N4 1.496(3) ?
C5 C6 1.531(3) ?
C5 H5 0.9800 ?
C6 O1 1.235(2) y
C6 O2 1.262(2) y
C10 O5 1.222(3) y
C10 O6 1.288(3) y
C10 C9 1.485(3) y
C9 C8 1.333(3) ?
C9 H9 0.9300 ?
C8 C7 1.495(3) ?
C8 H8 0.9300 ?
C7 O4 1.235(3) ?
C7 O3 1.269(3) ?
N1 H1A 0.8600 ?
N1 H1B 0.8600 ?
N2 H2A 0.8600 ?
N2 H2B 0.8600 ?
N4 H4AA 0.8900 ?
N4 H4BB 0.8900 ?
N4 H4CC 0.8900 ?
O3 H6A 1.25(5) y
O6 H6A 1.15(5) y
O7 H7A 0.88(2) ?
O7 H7B 0.86(2) ?
O8 H8A 0.871(19) ?
O8 H8B 0.87(2) ?
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
_geom_hbond_publ_flag
N4 H4AA O2 1_655 0.89 1.98 2.843(2) 162 yes
N1 H1A O1 1_656 0.86 2.18 2.935(2) 147 yes
N1 H1B O3 1_656 0.86 1.98 2.843(2) 176 yes
N4 H4BB O5 1_445 0.89 2.23 3.079(3) 160 yes
N2 H2A O2 1_656 0.86 2.10 2.948(2) 171 yes
N2 H2B O5 1_446 0.86 2.08 2.862(3) 152 yes
N3 H3 O4 1_656 0.86 2.10 2.955(2) 172 yes
N4 H4CC O7 1_545 0.89 1.92 2.801(2) 173 yes
O3 H6A O6 1_555 1.28(4) 1.13(4) 2.407(2) 173(3) yes
O7 H7A O8 1_555 0.90(2) 1.91(2) 2.791(3) 165(5) yes
O7 H7B O1 1_555 0.87(2) 2.35(4) 3.081(3) 142(5) yes
O7 H7B O8 1_455 0.87(2) 2.57(5) 3.186(4) 129(5) yes
O8 H8A O4 1_656 0.87(3) 2.01(2) 2.873(3) 170(4) yes
O8 H8B O2 1_655 0.88(2) 1.97(3) 2.770(2) 152(5) yes
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
_geom_torsion_publ_flag
N2 C1 N3 C2 1.0(3) ?
N1 C1 N3 C2 -179.8(2) ?
C1 N3 C2 C3 -166.55(19) ?
N3 C2 C3 C4 168.85(17) ?
C2 C3 C4 C5 174.85(18) ?
C3 C4 C5 N4 57.3(2) ?
C3 C4 C5 C6 -65.3(2) ?
N4 C5 C6 O1 -22.4(2) ?
C4 C5 C6 O1 101.6(2) ?
N4 C5 C6 O2 158.32(16) ?
C4 C5 C6 O2 -77.7(2) ?
O5 C10 C9 C8 179.8(3) y
O6 C10 C9 C8 1.2(4) y
C10 C9 C8 C7 -0.4(4) y
C9 C8 C7 O4 179.9(2) y
C9 C8 C7 O3 -1.0(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655246
