#------------------------------------------------------------------------------
#$Date: 2015-05-13 23:38:02 +0300 (Wed, 13 May 2015) $
#$Revision: 136437 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240647.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_2240647
loop_
_publ_author_name
'Görbitz, Carl Henrik'
'Paulsen, Jan Christian'
'Borgersen, Jon'
_publ_section_title
;
 Redetermined crystal structure of β-<small>DL</small>-methionine at 320K
;
_journal_coeditor_code           SU5129
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o398
_journal_page_last               o399
_journal_paper_doi               10.1107/S2056989015008749
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C5 H11 N O2 S'
_chemical_formula_moiety         'C5 H11 N O2 S'
_chemical_formula_sum            'C5 H11 N O2 S'
_chemical_formula_weight         149.21
_chemical_name_common            DL-methionine
_chemical_name_systematic
;
2-Amino-4-(methylsulfanyl)butanoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.224(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.774(2)
_cell_length_b                   4.6969(3)
_cell_length_c                   9.8939(7)
_cell_measurement_reflns_used    4136
_cell_measurement_temperature    320(2)
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      2.56
_cell_volume                     1476.22(17)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      320(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0314
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10516
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.541
_diffrn_reflns_theta_min         2.565
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0458P)²+1.6546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1567
_reflns_number_total             2060
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5129sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1476.20(18)
_cod_database_code               2240647
_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.
;
_shelxl_version_number           20.13
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
S S1 0.44096(2) 0.65785(16) 0.45693(7) 0.0684(2) Uani d 1
O O1 0.28350(4) 0.4246(2) 0.19616(11) 0.0316(3) Uani d 1
N N1 0.29732(4) 0.7975(3) 0.39652(12) 0.0252(3) Uani d 1
H H1 0.2705(6) 0.826(4) 0.3685(19) 0.038 Uiso d 1
H H2 0.2998(6) 0.627(5) 0.441(2) 0.038 Uiso d 1
H H3 0.3042(6) 0.926(4) 0.461(2) 0.038 Uiso d 1
C C1 0.30472(4) 0.6339(3) 0.16326(14) 0.0225(3) Uani d 1
C C2 0.32477(5) 0.8093(3) 0.27735(13) 0.0229(3) Uani d 1
H H21 0.3278 1.0073 0.2479 0.028 Uiso calc 1
O O2 0.31323(4) 0.7062(3) 0.04532(10) 0.0383(3) Uani d 1
C C3 0.36823(5) 0.6847(4) 0.31133(16) 0.0318(3) Uani d 1
H H31 0.3651 0.4828 0.3293 0.038 Uiso calc 1
H H32 0.3858 0.7044 0.2329 0.038 Uiso calc 1
C C4 0.39054(5) 0.8220(4) 0.43157(19) 0.0406(4) Uani d 1
H H41 0.3739 0.7986 0.5118 0.049 Uiso calc 1
H H42 0.3940 1.0242 0.4153 0.049 Uiso calc 1
C C5 0.45831(8) 0.8257(7) 0.6094(3) 0.0750(8) Uani d 1
H H51 0.4861 0.7596 0.6334 0.113 Uiso calc 1
H H52 0.4393 0.7799 0.6804 0.113 Uiso calc 1
H H53 0.4589 1.0282 0.5965 0.113 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'
S S 0.1246 0.1234 '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
C5 S1 C4 100.84(11)
C2 N1 H1 108.6(12)
C2 N1 H2 111.8(12)
H1 N1 H2 110.3(17)
C2 N1 H3 113.4(12)
H1 N1 H3 109.4(17)
H2 N1 H3 103.2(16)
O1 C1 O2 126.16(13)
O1 C1 C2 117.06(12)
O2 C1 C2 116.66(13)
N1 C2 C1 108.95(12)
N1 C2 C3 110.76(11)
C1 C2 C3 108.45(12)
N1 C2 H21 109.6
C1 C2 H21 109.6
C3 C2 H21 109.6
C4 C3 C2 114.47(13)
C4 C3 H31 108.6
C2 C3 H31 108.6
C4 C3 H32 108.6
C2 C3 H32 108.6
H31 C3 H32 107.6
C3 C4 S1 109.19(12)
C3 C4 H41 109.8
S1 C4 H41 109.8
C3 C4 H42 109.8
S1 C4 H42 109.8
H41 C4 H42 108.3
S1 C5 H51 109.5
S1 C5 H52 109.5
H51 C5 H52 109.5
S1 C5 H53 109.5
H51 C5 H53 109.5
H52 C5 H53 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.779(2)
S1 C4 1.7907(17)
O1 C1 1.2398(18)
N1 C2 1.4825(18)
N1 H1 0.90(2)
N1 H2 0.92(2)
N1 H3 0.90(2)
C1 O2 1.2504(18)
C1 C2 1.5258(19)
C2 C3 1.530(2)
C2 H21 0.9800
C3 C4 1.516(2)
C3 H31 0.9700
C3 H32 0.9700
C4 H41 0.9700
C4 H42 0.9700
C5 H51 0.9600
C5 H52 0.9600
C5 H53 0.9600
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 O1 4 0.90(2) 1.88(2) 2.7732(17) 173.7(19)
N1 H2 O2 6_566 0.92(2) 1.92(2) 2.8264(18) 171.0(18)
N1 H3 O2 6_576 0.90(2) 1.94(2) 2.7973(18) 159.2(18)
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
O1 C1 C2 N1 -31.43(17)
O2 C1 C2 N1 152.41(13)
O1 C1 C2 C3 89.21(16)
O2 C1 C2 C3 -86.95(16)
N1 C2 C3 C4 -55.52(18)
C1 C2 C3 C4 -175.03(14)
C2 C3 C4 S1 -179.16(12)
C3 C4 S1 C5 -174.55(16)
H1 N1 C2 C1 -44.4(13)
H2 N1 C2 C1 76.5(13)
H3 N1 C2 C1 -167.3(14)

_cod_database_fobs_code 2240647
