#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220603.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_2220603
loop_
_publ_author_name
'Rodrigues, V. H.'
'Costa, M. M. R. R.'
'Dekola, T.'
'de Matos Gomes, E.'
_publ_section_title
;
 Bis[glycinium(0.5+)] perrhenate
;
_journal_coeditor_code           RN2049
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m19
_journal_paper_doi               10.1107/S160053680803849X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2(C2 H5.5 N O2) [Re O4]'
_chemical_formula_moiety         '2(C2 H5.5 N O2 0.5+), Re O4 -'
_chemical_formula_sum            'C4 H11 N2 O8 Re'
_chemical_formula_weight         401.35
_chemical_name_common            'glycinium glycine perrhenate'
_chemical_name_systematic
;
Bis[glycinium(0.5+)] perrhenate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 103.7152(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7095(5)
_cell_length_b                   8.1826(3)
_cell_length_c                   8.2909(3)
_cell_measurement_reflns_used    7839
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      40.108
_cell_measurement_theta_min      4.000
_cell_volume                     1035.36(6)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker--Nonius, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            78826
_diffrn_reflns_theta_full        45.33
_diffrn_reflns_theta_max         45.33
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.765
_exptl_absorpt_correction_T_max  0.31
_exptl_absorpt_correction_T_min  0.18
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    2.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.327
_refine_diff_density_min         -2.873
_refine_ls_extinction_coef       0.00614(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         8587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.001P)²+2.2865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                6232
_reflns_number_total             8587
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn2049.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220603
_cod_database_fobs_code          2220603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Re Re1 0.384633(5) 0.604894(11) 0.053166(13) 0.02896(3) Uani d . 1 . .
O O1 0.43021(16) 0.4923(4) 0.2269(3) 0.0636(7) Uani d . 1 . .
O O2 0.28327(14) 0.6733(3) 0.0625(4) 0.0633(8) Uani d . 1 . .
O O3 0.44936(16) 0.7699(3) 0.0397(5) 0.0685(9) Uani d . 1 . .
O O4 0.3784(2) 0.4775(4) -0.1121(3) 0.0698(8) Uani d . 1 . .
O O11 0.02851(12) 0.9119(2) 0.2663(2) 0.0343(4) Uani d . 1 . .
O O12 -0.02823(11) 0.7477(2) 0.0538(2) 0.0366(4) Uani d . 1 . .
H H12 -0.0747 0.7890 0.0614 0.055 Uiso calc PR 0.50 . .
C C11 0.03285(13) 0.7965(3) 0.1730(3) 0.0242(3) Uani d . 1 . .
C C12 0.11921(13) 0.7067(3) 0.1971(3) 0.0291(4) Uani d . 1 . .
H H12A 0.1608 0.7754 0.1588 0.035 Uiso calc R 1 . .
H H12B 0.1424 0.6864 0.3145 0.035 Uiso calc R 1 . .
N N11 0.11042(11) 0.5501(2) 0.1070(2) 0.0253(3) Uani d . 1 . .
H H11A 0.0761 0.4833 0.1479 0.038 Uiso calc R 1 . .
H H11B 0.1631 0.5048 0.1189 0.038 Uiso calc R 1 . .
H H11C 0.0868 0.5676 -0.0002 0.038 Uiso calc R 1 . .
O O21 0.24920(12) 0.3008(2) 0.0961(3) 0.0409(4) Uani d . 1 . .
O O22 0.16419(12) 0.1024(3) -0.0423(3) 0.0504(6) Uani d . 1 . .
H H22 0.1241 0.1641 -0.0353 0.076 Uiso calc PR 0.50 . .
C C21 0.23754(14) 0.1710(3) 0.0210(3) 0.0281(4) Uani d . 1 . .
C C22 0.31325(16) 0.0716(3) -0.0074(4) 0.0373(5) Uani d . 1 . .
H H22A 0.3076 -0.0399 0.0286 0.045 Uiso calc R 1 . .
H H22B 0.3109 0.0690 -0.1254 0.045 Uiso calc R 1 . .
N N21 0.39933(12) 0.1372(3) 0.0823(3) 0.0337(4) Uani d . 1 . .
H H21A 0.3923 0.2372 0.1194 0.051 Uiso calc R 1 . .
H H21B 0.4351 0.1417 0.0136 0.051 Uiso calc R 1 . .
H H21C 0.4224 0.0724 0.1676 0.051 Uiso calc R 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'
Re Re -1.0185 7.2310 '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
O4 Re1 O2 . . 111.10(15) ?
O4 Re1 O3 . . 110.60(15) ?
O2 Re1 O3 . . 108.64(11) ?
O4 Re1 O1 . . 106.21(17) ?
O2 Re1 O1 . . 110.24(14) ?
O3 Re1 O1 . . 110.03(15) ?
C11 O12 H12 . . 109.5 ?
O11 C11 O12 . . 125.87(19) ?
O11 C11 C12 . . 118.03(19) ?
O12 C11 C12 . . 116.08(18) ?
N11 C12 C11 . . 112.44(17) ?
N11 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
N11 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C12 N11 H11A . . 109.5 ?
C12 N11 H11B . . 109.5 ?
H11A N11 H11B . . 109.5 ?
C12 N11 H11C . . 109.5 ?
H11A N11 H11C . . 109.5 ?
H11B N11 H11C . . 109.5 ?
C21 O22 H22 . . 109.5 ?
O21 C21 O22 . . 127.1(2) ?
O21 C21 C22 . . 121.4(2) ?
O22 C21 C22 . . 111.5(2) ?
N21 C22 C21 . . 112.7(2) ?
N21 C22 H22A . . 109.0 ?
C21 C22 H22A . . 109.0 ?
N21 C22 H22B . . 109.0 ?
C21 C22 H22B . . 109.0 ?
H22A C22 H22B . . 107.8 ?
C22 N21 H21A . . 109.5 ?
C22 N21 H21B . . 109.5 ?
H21A N21 H21B . . 109.5 ?
C22 N21 H21C . . 109.5 ?
H21A N21 H21C . . 109.5 ?
H21B N21 H21C . . 109.5 ?
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
Re1 O4 . 1.706(3) ?
Re1 O2 . 1.707(2) ?
Re1 O3 . 1.710(2) ?
Re1 O1 . 1.717(3) ?
O11 C11 . 1.233(3) ?
O12 C11 . 1.267(3) ?
O12 H12 . 0.8200 ?
C11 C12 . 1.514(3) ?
C12 N11 . 1.473(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
N11 H11A . 0.8900 ?
N11 H11B . 0.8900 ?
N11 H11C . 0.8900 ?
O21 C21 . 1.223(3) ?
O22 C21 . 1.277(3) ?
O22 H22 . 0.8200 ?
C21 C22 . 1.505(3) ?
C22 N21 . 1.481(3) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
N21 H21A . 0.8900 ?
N21 H21B . 0.8900 ?
N21 H21C . 0.8900 ?
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
O12 H12 O22 3_565 0.82 1.64 2.445(2) 167.1
N11 H11A O11 2_545 0.89 2.02 2.869(2) 158.0
N11 H11B O21 . 0.89 2.18 3.003(2) 152.5
N11 H11B O2 . 0.89 2.47 3.000(3) 118.6
N11 H11C O11 4_575 0.89 1.94 2.830(3) 174.6
O22 H22 O12 3_565 0.82 1.64 2.445(2) 165.0
N21 H21A O21 . 0.89 2.27 2.738(3) 112.6
N21 H21A O1 . 0.89 2.29 3.136(4) 158.3
N21 H21B O3 3_665 0.89 2.10 2.896(3) 149.1
N21 H21B O1 4_565 0.89 2.60 3.274(4) 132.9
N21 H21C O4 4_566 0.89 2.14 2.794(3) 129.8
N21 H21C O1 2_645 0.89 2.37 3.012(3) 129.6
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
O11 C11 C12 N11 . . . . 166.3(2) ?
O12 C11 C12 N11 . . . . -15.7(3) ?
O21 C21 C22 N21 . . . . 7.3(4) ?
O22 C21 C22 N21 . . . . -172.9(2) ?
