#------------------------------------------------------------------------------
#$Date: 2015-05-30 05:58:27 +0300 (Sat, 30 May 2015) $
#$Revision: 137559 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240798.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_2240798
loop_
_publ_author_name
'Görbitz, Carl Henrik'
'Levchenko, Vladimir'
'Semjonovs, Jevgenijs'
'Sharif, Mohamed Yusuf'
_publ_section_title
;
 Crystal structure of seleno-<small>L</small>-cystine dihydrochloride
;
_journal_coeditor_code           WM5154
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              726
_journal_page_last               729
_journal_paper_doi               10.1107/S205698901501021X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C6 H14 N2 O4 Se2 2+, 2(Cl -)'
_chemical_formula_moiety         'C6 H14 N2 O4 Se2 2+, 2(Cl -)'
_chemical_formula_sum            'C6 H14 Cl2 N2 O4 Se2'
_chemical_formula_weight         407.02
_chemical_name_common            'Seleno-L-cystine dihydrochloride'
_chemical_name_systematic
;
(R,R)-1,1'-Dicarboxy-2,2'-(diselanediyl)diethanaminium dichloride
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.2190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.8045(16)
_cell_length_b                   5.2529(4)
_cell_length_c                   7.2719(6)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.20
_cell_measurement_theta_min      2.22
_cell_volume                     702.03(10)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Advance single-crystal CCD'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5° ω rotation'
_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  0.0243
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11089
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         40.208
_diffrn_reflns_theta_min         2.216
_exptl_absorpt_coefficient_mu    5.647
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         4.552
_refine_diff_density_min         -0.874
_refine_ls_abs_structure_details
;
Flack x determined using 1708 quotients
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.044(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         4209
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0169P)²+0.0040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0616
_reflns_number_gt                4080
_reflns_number_total             4209
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm5154sup1.cif
_cod_data_source_block           I
_cod_database_code               2240798
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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_occupancy
Se Se1 0.50147(2) 0.56610(5) 0.16037(2) 0.01306(4) Uani d 1
Cl Cl1 0.65288(2) 0.16979(8) 0.87546(6) 0.01345(7) Uani d 1
O O1 0.69775(8) 0.3451(3) 0.4104(2) 0.0158(2) Uani d 1
O O2 0.62968(9) 0.5697(5) 0.57259(19) 0.0225(3) Uani d 1
H H4 0.6356(18) 0.454(12) 0.644(6) 0.058(15) Uiso d 1
N N1 0.67823(8) 0.6777(3) 0.1266(2) 0.0125(2) Uani d 1
H H1 0.6681 0.8028 0.0384 0.019 Uiso calc 1
H H2 0.6563 0.5305 0.0787 0.019 Uiso calc 1
H H3 0.7272 0.6536 0.1591 0.019 Uiso calc 1
C C1 0.66257(8) 0.5306(3) 0.4320(2) 0.0125(3) Uani d 1
C C2 0.65058(9) 0.7531(3) 0.2961(2) 0.0114(2) Uani d 1
H H21 0.6808 0.8988 0.3574 0.014 Uiso calc 1
C C3 0.57160(9) 0.8414(3) 0.2457(3) 0.0123(2) Uani d 1
H H31 0.5667 0.9713 0.1451 0.015 Uiso calc 1
H H32 0.5592 0.9238 0.3573 0.015 Uiso calc 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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_3
_geom_angle
C3 Se1 Se1 2_655 100.88(5)
C1 O2 H4 . 112(4)
C2 N1 H1 . 109.5
C2 N1 H2 . 109.5
H1 N1 H2 . 109.5
C2 N1 H3 . 109.5
H1 N1 H3 . 109.5
H2 N1 H3 . 109.5
O1 C1 O2 . 125.92(18)
O1 C1 C2 . 123.24(17)
O2 C1 C2 . 110.84(16)
N1 C2 C1 . 107.72(14)
N1 C2 C3 . 112.00(14)
C1 C2 C3 . 113.22(14)
N1 C2 H21 . 107.9
C1 C2 H21 . 107.9
C3 C2 H21 . 107.9
C2 C3 Se1 . 113.96(12)
C2 C3 H31 . 108.8
Se1 C3 H31 . 108.8
C2 C3 H32 . 108.8
Se1 C3 H32 . 108.8
H31 C3 H32 . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Se1 C3 . 1.9671(18)
Se1 Se1 2_655 2.3213(4)
O1 C1 . 1.206(2)
O2 C1 . 1.319(2)
O2 H4 . 0.79(6)
N1 C2 . 1.490(2)
N1 H1 . 0.9100
N1 H2 . 0.9100
N1 H3 . 0.9100
C1 C2 . 1.516(2)
C2 C3 . 1.525(2)
C2 H21 . 1.0000
C3 H31 . 0.9900
C3 H32 . 0.9900
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 H1 Cl1 1_564 0.91 2.25 3.1425(16) 167.1
N1 H2 Cl1 1_554 0.91 2.40 3.2110(18) 149.2
N1 H3 Cl1 4_656 0.91 2.32 3.1794(15) 156.8
O2 H4 Cl1 . 0.79(6) 2.22(6) 3.0080(19) 172(4)
C2 H21 O1 1_565 1.00 2.39 3.292(2) 150.2
C2 H21 O1 4_656 1.00 2.55 3.216(2) 123.7
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 N1 . . 9.3(2)
O2 C1 C2 N1 . . -170.64(15)
O1 C1 C2 C3 . . 133.72(17)
O2 C1 C2 C3 . . -46.24(19)
N1 C2 C3 Se1 . . 70.66(16)
C1 C2 C3 Se1 . . -51.39(17)
C2 C3 Se1 Se1 . 2_655 -88.72(12)
C3 Se1 Se1 C3 2_655 2_655 -83.05(10)

_cod_database_fobs_code 2240798
