#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227781.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_2227781
loop_
_publ_author_name
'Peng, Bing'
'Peng, Qingrong'
'Zhou, Wenfeng'
'Zhou, Zhiqiang'
_publ_section_title
;
 Guanidinium <small>L</small>-glutamate
;
_journal_coeditor_code           LH5125
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2679
_journal_paper_doi               10.1107/S1600536810036354
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C H6 N3 +, C5 H8 N O4 -'
_chemical_formula_moiety         'C H6 N3 +, C5 H8 N O4 -'
_chemical_formula_sum            'C6 H14 N4 O4'
_chemical_formula_weight         206.21
_chemical_name_common
;
Guanidinium L-glutamate
;
_chemical_name_systematic
;
bis(carbamimidoylazanium) (2R)-2-aminopentanedioate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.5520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7793(7)
_cell_length_b                   10.8729(10)
_cell_length_c                   10.0801(9)
_cell_measurement_reflns_used    2748
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.40
_cell_volume                     931.34(14)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5501
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.2149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2087
_reflns_number_total             2220
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5125.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2227781
_cod_database_fobs_code          2227781
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3633(2) 0.4498(2) -0.1328(2) 0.0157(4) Uani d . 1 . .
C C2 0.4808(2) 0.5516(2) -0.06507(19) 0.0152(4) Uani d . 1 . .
H H2 0.5234 0.5892 -0.1389 0.018 Uiso calc R 1 . .
C C3 0.6207(2) 0.5030(2) 0.0442(2) 0.0175(4) Uani d . 1 . .
H H3C 0.6924 0.5723 0.0803 0.021 Uiso calc R 1 . .
H H3D 0.6793 0.4434 0.0016 0.021 Uiso calc R 1 . .
C C4 0.5727(2) 0.4405(2) 0.1632(2) 0.0185(4) Uani d . 1 . .
H H4C 0.4937 0.3761 0.1264 0.022 Uiso calc R 1 . .
H H4D 0.5227 0.5020 0.2111 0.022 Uiso calc R 1 . .
C C5 0.7121(2) 0.3823(2) 0.2661(2) 0.0161(4) Uani d . 1 . .
C C6 0.6284(3) 0.5883(2) 0.6253(2) 0.0170(4) Uani d . 1 . .
C C7 0.5001(2) 0.5088(2) 0.5315(2) 0.0142(4) Uani d . 1 . .
H H7 0.5153 0.5159 0.4368 0.017 Uiso calc R 1 . .
C C8 0.3304(2) 0.5466(2) 0.52340(19) 0.0164(4) Uani d . 1 . .
H H8C 0.3259 0.6367 0.5357 0.020 Uiso calc R 1 . .
H H8D 0.2954 0.5067 0.5990 0.020 Uiso calc R 1 . .
C C9 0.2181(2) 0.5106(2) 0.3863(2) 0.0171(4) Uani d . 1 . .
H H9A 0.2379 0.4240 0.3655 0.020 Uiso calc R 1 . .
H H9B 0.1083 0.5165 0.3946 0.020 Uiso calc R 1 . .
C C10 0.2368(2) 0.5920(2) 0.2679(2) 0.0156(4) Uani d . 1 . .
C C11 0.9131(2) 0.7443(2) 0.4492(2) 0.0176(4) Uani d . 1 . .
C C12 0.9193(3) 0.7368(2) 0.9641(2) 0.0179(4) Uani d . 1 . .
N N1 0.3944(2) 0.65067(18) -0.01100(17) 0.0155(4) Uani d . 1 . .
H H1A 0.3351 0.6164 0.0415 0.023 Uiso calc R 1 . .
H H1B 0.3307 0.6918 -0.0823 0.023 Uiso calc R 1 . .
H H1C 0.4648 0.7040 0.0407 0.023 Uiso calc R 1 . .
N N2 0.5301(2) 0.37747(18) 0.57395(19) 0.0183(4) Uani d . 1 . .
H H2A 0.4960 0.3633 0.6507 0.027 Uiso calc R 1 . .
H H2B 0.6351 0.3617 0.5918 0.027 Uiso calc R 1 . .
H H2C 0.4774 0.3275 0.5052 0.027 Uiso calc R 1 . .
N N3 0.7857(2) 0.6972(2) 0.3634(2) 0.0240(4) Uani d . 1 . .
H H3A 0.7411 0.7361 0.2870 0.029 Uiso calc R 1 . .
H H3B 0.7461 0.6272 0.3832 0.029 Uiso calc R 1 . .
N N4 0.9733(2) 0.84922(19) 0.42024(19) 0.0204(4) Uani d . 1 . .
H H4A 1.0578 0.8797 0.4770 0.024 Uiso calc R 1 . .
H H4B 0.9288 0.8887 0.3441 0.024 Uiso calc R 1 . .
N N5 0.9797(2) 0.68433(19) 0.5639(2) 0.0215(4) Uani d . 1 . .
H H5A 1.0643 0.7145 0.6209 0.026 Uiso calc R 1 . .
H H5B 0.9394 0.6144 0.5829 0.026 Uiso calc R 1 . .
N N6 0.9603(2) 0.62410(19) 0.9389(2) 0.0242(4) Uani d . 1 . .
H H6A 0.9036 0.5832 0.8682 0.029 Uiso calc R 1 . .
H H6B 1.0442 0.5899 0.9926 0.029 Uiso calc R 1 . .
N N7 0.7924(2) 0.78798(19) 0.88260(19) 0.0222(4) Uani d . 1 . .
H H7A 0.7361 0.7467 0.8121 0.027 Uiso calc R 1 . .
H H7B 0.7648 0.8631 0.8991 0.027 Uiso calc R 1 . .
N N8 1.0012(2) 0.8000(2) 1.0716(2) 0.0248(5) Uani d . 1 . .
H H8A 1.0844 0.7668 1.1274 0.030 Uiso calc R 1 . .
H H8B 0.9721 0.8751 1.0868 0.030 Uiso calc R 1 . .
O O1 0.22034(18) 0.47085(14) -0.15334(15) 0.0197(3) Uani d . 1 . .
O O2 0.42560(19) 0.35290(15) -0.16612(15) 0.0206(3) Uani d . 1 . .
O O3 0.76473(19) 0.43703(16) 0.37806(16) 0.0221(4) Uani d . 1 . .
O O4 0.76678(19) 0.28334(16) 0.23297(16) 0.0236(4) Uani d . 1 . .
O O5 0.6030(2) 0.70163(15) 0.62702(17) 0.0234(4) Uani d . 1 . .
O O6 0.75073(18) 0.53379(16) 0.68837(16) 0.0225(4) Uani d . 1 . .
O O7 0.2657(2) 0.70271(16) 0.28796(17) 0.0277(4) Uani d . 1 . .
O O8 0.21550(17) 0.54149(15) 0.15054(14) 0.0184(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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 126.4(2) ?
O1 C1 C2 . . 118.4(2) ?
O2 C1 C2 . . 115.21(18) ?
N1 C2 C3 . . 112.11(16) ?
N1 C2 C1 . . 109.42(16) ?
C3 C2 C1 . . 113.44(18) ?
N1 C2 H2 . . 107.2 ?
C3 C2 H2 . . 107.2 ?
C1 C2 H2 . . 107.2 ?
C2 C3 C4 . . 112.99(17) ?
C2 C3 H3C . . 109.0 ?
C4 C3 H3C . . 109.0 ?
C2 C3 H3D . . 109.0 ?
C4 C3 H3D . . 109.0 ?
H3C C3 H3D . . 107.8 ?
C3 C4 C5 . . 112.67(17) ?
C3 C4 H4C . . 109.1 ?
C5 C4 H4C . . 109.1 ?
C3 C4 H4D . . 109.1 ?
C5 C4 H4D . . 109.1 ?
H4C C4 H4D . . 107.8 ?
O4 C5 O3 . . 124.40(19) ?
O4 C5 C4 . . 117.95(18) ?
O3 C5 C4 . . 117.6(2) ?
O6 C6 O5 . . 126.2(2) ?
O6 C6 C7 . . 116.6(2) ?
O5 C6 C7 . . 117.06(19) ?
N2 C7 C8 . . 111.79(18) ?
N2 C7 C6 . . 108.12(16) ?
C8 C7 C6 . . 115.78(18) ?
N2 C7 H7 . . 106.9 ?
C8 C7 H7 . . 106.9 ?
C6 C7 H7 . . 106.9 ?
C7 C8 C9 . . 112.17(17) ?
C7 C8 H8C . . 109.2 ?
C9 C8 H8C . . 109.2 ?
C7 C8 H8D . . 109.2 ?
C9 C8 H8D . . 109.2 ?
H8C C8 H8D . . 107.9 ?
C10 C9 C8 . . 112.69(17) ?
C10 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
O7 C10 O8 . . 123.2(2) ?
O7 C10 C9 . . 119.6(2) ?
O8 C10 C9 . . 117.14(19) ?
N4 C11 N5 . . 120.2(2) ?
N4 C11 N3 . . 120.4(2) ?
N5 C11 N3 . . 119.4(2) ?
N6 C12 N7 . . 119.7(2) ?
N6 C12 N8 . . 121.3(2) ?
N7 C12 N8 . . 119.0(2) ?
C2 N1 H1A . . 109.5 ?
C2 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C2 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C7 N2 H2A . . 109.5 ?
C7 N2 H2B . . 109.5 ?
H2A N2 H2B . . 109.5 ?
C7 N2 H2C . . 109.5 ?
H2A N2 H2C . . 109.5 ?
H2B N2 H2C . . 109.5 ?
C11 N3 H3A . . 120.0 ?
C11 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C11 N4 H4A . . 120.0 ?
C11 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
C11 N5 H5A . . 120.0 ?
C11 N5 H5B . . 120.0 ?
H5A N5 H5B . . 120.0 ?
C12 N6 H6A . . 120.0 ?
C12 N6 H6B . . 120.0 ?
H6A N6 H6B . . 120.0 ?
C12 N7 H7A . . 120.0 ?
C12 N7 H7B . . 120.0 ?
H7A N7 H7B . . 120.0 ?
C12 N8 H8A . . 120.0 ?
C12 N8 H8B . . 120.0 ?
H8A N8 H8B . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.241(3) ?
C1 O2 . 1.271(3) ?
C1 C2 . 1.549(3) ?
C2 N1 . 1.497(3) ?
C2 C3 . 1.524(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.527(3) ?
C3 H3C . 0.9900 ?
C3 H3D . 0.9900 ?
C4 C5 . 1.529(3) ?
C4 H4C . 0.9900 ?
C4 H4D . 0.9900 ?
C5 O4 . 1.257(3) ?
C5 O3 . 1.257(3) ?
C6 O6 . 1.251(3) ?
C6 O5 . 1.253(3) ?
C6 C7 . 1.541(3) ?
C7 N2 . 1.495(3) ?
C7 C8 . 1.528(3) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.533(3) ?
C8 H8C . 0.9900 ?
C8 H8D . 0.9900 ?
C9 C10 . 1.527(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 O7 . 1.237(3) ?
C10 O8 . 1.275(3) ?
C11 N4 . 1.321(3) ?
C11 N5 . 1.328(3) ?
C11 N3 . 1.332(3) ?
C12 N6 . 1.319(3) ?
C12 N7 . 1.329(3) ?
C12 N8 . 1.331(3) ?
N1 H1A . 0.9100 ?
N1 H1B . 0.9100 ?
N1 H1C . 0.9100 ?
N2 H2A . 0.9100 ?
N2 H2B . 0.9100 ?
N2 H2C . 0.9100 ?
N3 H3A . 0.8800 ?
N3 H3B . 0.8800 ?
N4 H4A . 0.8800 ?
N4 H4B . 0.8800 ?
N5 H5A . 0.8800 ?
N5 H5B . 0.8800 ?
N6 H6A . 0.8800 ?
N6 H6B . 0.8800 ?
N7 H7A . 0.8800 ?
N7 H7B . 0.8800 ?
N8 H8A . 0.8800 ?
N8 H8B . 0.8800 ?
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
N1 H1A O8 . 0.91 1.89 2.795(2) 178.5
N1 H1B O4 2_655 0.91 1.84 2.738(2) 170.3
N1 H1C O2 2_655 0.91 2.13 3.017(2) 164.8
N2 H2A O2 1_556 0.91 2.09 2.998(2) 173.0
N2 H2B O7 2_646 0.91 2.16 2.740(2) 120.4
N2 H2C O5 2_646 0.91 1.92 2.817(3) 169.6
N3 H3A O2 2_655 0.88 2.08 2.900(3) 153.8
N3 H3B O3 . 0.88 2.08 2.841(3) 144.8
N4 H4A O3 2_756 0.88 1.95 2.826(2) 172.5
N4 H4B O1 2_655 0.88 2.22 3.095(2) 170.2
N5 H5A O4 2_756 0.88 1.96 2.831(2) 171.6
N5 H5B O6 . 0.88 2.35 3.092(3) 142.1
N6 H6A O6 . 0.88 2.04 2.897(2) 164.8
N6 H6B O8 1_656 0.88 1.97 2.824(2) 164.4
N7 H7A O5 . 0.88 2.00 2.851(2) 163.3
N7 H7B O8 2_656 0.88 2.02 2.775(3) 143.0
N8 H8A O7 1_656 0.88 2.08 2.954(3) 169.5
N8 H8B O1 2_656 0.88 2.23 2.953(3) 139.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 N1 . . . . 11.3(3) ?
O2 C1 C2 N1 . . . . -170.89(17) ?
O1 C1 C2 C3 . . . . 137.29(19) ?
O2 C1 C2 C3 . . . . -44.9(2) ?
N1 C2 C3 C4 . . . . 63.7(2) ?
C1 C2 C3 C4 . . . . -60.8(2) ?
C2 C3 C4 C5 . . . . 174.99(19) ?
C3 C4 C5 O4 . . . . -75.2(3) ?
C3 C4 C5 O3 . . . . 104.4(2) ?
O6 C6 C7 N2 . . . . 18.9(3) ?
O5 C6 C7 N2 . . . . -163.9(2) ?
O6 C6 C7 C8 . . . . 145.18(19) ?
O5 C6 C7 C8 . . . . -37.6(3) ?
N2 C7 C8 C9 . . . . -83.4(2) ?
C6 C7 C8 C9 . . . . 152.21(18) ?
C7 C8 C9 C10 . . . . -73.5(2) ?
C8 C9 C10 O7 . . . . -36.4(3) ?
C8 C9 C10 O8 . . . . 146.12(19) ?
