##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_database_code_depnum_ccdc_archive     'CCDC 1416394'
_chemical_name_systematic
;
(2S,3S)-2-[(2-Carbamoylethyl)azaniumyl]-3-methylpentanoate
;
_chemical_name_common     'N-(β-Carboxyethyl)-α-isoleucine'
_chemical_formula_moiety     'C9 H18 N2 O3'
_chemical_formula_sum     'C9 H18 N2 O3'
_chemical_formula_iupac     'C9 H18 N2 O3'
_chemical_formula_weight     202.25
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     5.2996(5)
_cell_length_b     9.0053(7)
_cell_length_c     23.211(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1107.75(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.213
_exptl_crystal_density_meas     1.21
_exptl_crystal_density_method     'floatation method'
_exptl_crystal_F_000     440
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.97
_exptl_absorpt_correction_T_max     0.99
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     22904
_diffrn_reflns_av_R_equivalents     0.0357
_diffrn_reflns_theta_min     2.426
_diffrn_reflns_theta_max     29.937
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -31
_diffrn_reflns_limit_l_max     32
_refine_special_details
;
Refined as a 2-component perfect inversion twin.
;
_reflns_number_total     3127
_reflns_number_gt     2538
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0624
_refine_ls_R_factor_gt     0.0423
_refine_ls_wR_factor_gt     0.0934
_refine_ls_wR_factor_ref     0.1015
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     3127
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0479P)²+0.1014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.302
_refine_diff_density_min     -0.192
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef     ?
_refine_ls_extinction_expression     ?
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack     0.5
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'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.2868(2) 0.54162(13) 0.74549(7) 0.0379(4) Uani d 1 . .
    O O2 0.2473(3) 0.77532(13) 0.71778(7) 0.0383(4) Uani d 1 . .
    O O3 0.6665(3) 0.6614(2) 0.94137(7) 0.0550(5) Uani d 1 . .
    N N1 0.7861(3) 0.57896(16) 0.76272(6) 0.0213(3) Uani d 1 . .
    N N2 1.0857(4) 0.6555(3) 0.95384(9) 0.0475(5) Uani d 1 . .
    C C5 0.7705(8) 0.7167(5) 0.55526(12) 0.0942(12) Uani d 1 . .
    H H5A 0.9472 0.7357 0.5606 0.141 Uiso calc 1 . .
    H H5B 0.7017 0.7884 0.5290 0.141 Uiso calc 1 . .
    H H5C 0.7479 0.6188 0.5398 0.141 Uiso calc 1 . .
    C C4 0.6370(5) 0.7281(3) 0.61215(10) 0.0506(6) Uani d 1 . .
    H H4A 0.4584 0.7101 0.6062 0.061 Uiso calc 1 . .
    H H4B 0.6555 0.8285 0.6267 0.061 Uiso calc 1 . .
    C C3 0.7352(4) 0.6194(2) 0.65736(8) 0.0329(4) Uani d 1 . .
    H H3 0.9199 0.6235 0.6558 0.040 Uiso calc 1 . .
    C C6 0.6603(6) 0.4612(3) 0.64363(10) 0.0571(7) Uani d 1 . .
    H H6A 0.7232 0.3961 0.6731 0.086 Uiso calc 1 . .
    H H6B 0.7304 0.4330 0.6071 0.086 Uiso calc 1 . .
    H H6C 0.4797 0.4540 0.6420 0.086 Uiso calc 1 . .
    C C2 0.6583(3) 0.66957(19) 0.71782(7) 0.0224(4) Uani d 1 . .
    H H2 0.7123 0.7729 0.7227 0.027 Uiso calc 1 . .
    C C1 0.3732(3) 0.66295(19) 0.72788(8) 0.0244(4) Uani d 1 . .
    C C7 0.7684(4) 0.6481(2) 0.82050(8) 0.0297(4) Uani d 1 . .
    H H7A 0.5926 0.6536 0.8319 0.036 Uiso calc 1 . .
    H H7B 0.8340 0.7485 0.8187 0.036 Uiso calc 1 . .
    C C8 0.9134(4) 0.5614(2) 0.86493(8) 0.0354(5) Uani d 1 . .
    H H8A 1.0912 0.5611 0.8551 0.042 Uiso calc 1 . .
    H H8B 0.8547 0.4594 0.8655 0.042 Uiso calc 1 . .
    C C9 0.8776(4) 0.6301(2) 0.92372(8) 0.0348(4) Uani d 1 . .
    H H1N1 0.723(4) 0.488(2) 0.7648(9) 0.029(5) Uiso d 1 . .
    H H2N1 0.947(4) 0.568(2) 0.7544(9) 0.027(5) Uiso d 1 . .
    H H2N2 1.228(6) 0.631(3) 0.9411(11) 0.051(7) Uiso d 1 . .
    H H1N2 1.082(6) 0.697(3) 0.9890(13) 0.064(9) Uiso d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    O1 C1 . 1.253(2) ?
    O2 C1 . 1.234(2) ?
    O3 C9 . 1.224(3) ?
    N1 C7 . 1.481(2) ?
    N1 C2 . 1.487(2) ?
    N1 H1N1 . 0.89(2) ?
    N1 H2N1 . 0.88(2) ?
    N2 C9 . 1.326(3) ?
    N2 H2N2 . 0.84(3) ?
    N2 H1N2 . 0.90(3) ?
    C5 C4 . 1.502(4) ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C4 C3 . 1.527(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C3 C6 . 1.513(3) ?
    C3 C2 . 1.530(2) ?
    C3 H3 . 0.9800 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C2 C1 . 1.530(2) ?
    C2 H2 . 0.9800 ?
    C7 C8 . 1.504(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.510(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
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
    C7 N1 C2 . . 112.03(13) ?
    C7 N1 H1N1 . . 108.3(13) ?
    C2 N1 H1N1 . . 111.9(14) ?
    C7 N1 H2N1 . . 107.9(14) ?
    C2 N1 H2N1 . . 110.4(14) ?
    H1N1 N1 H2N1 . . 106.1(19) ?
    C9 N2 H2N2 . . 121.0(18) ?
    C9 N2 H1N2 . . 122(2) ?
    H2N2 N2 H1N2 . . 117(3) ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C5 C4 C3 . . 113.6(2) ?
    C5 C4 H4A . . 108.9 ?
    C3 C4 H4A . . 108.9 ?
    C5 C4 H4B . . 108.9 ?
    C3 C4 H4B . . 108.9 ?
    H4A C4 H4B . . 107.7 ?
    C6 C3 C4 . . 111.70(19) ?
    C6 C3 C2 . . 113.68(17) ?
    C4 C3 C2 . . 110.48(17) ?
    C6 C3 H3 . . 106.9 ?
    C4 C3 H3 . . 106.9 ?
    C2 C3 H3 . . 106.9 ?
    C3 C6 H6A . . 109.5 ?
    C3 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C3 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N1 C2 C3 . . 111.07(14) ?
    N1 C2 C1 . . 108.74(14) ?
    C3 C2 C1 . . 113.06(15) ?
    N1 C2 H2 . . 107.9 ?
    C3 C2 H2 . . 107.9 ?
    C1 C2 H2 . . 107.9 ?
    O2 C1 O1 . . 125.42(16) ?
    O2 C1 C2 . . 118.20(15) ?
    O1 C1 C2 . . 116.38(15) ?
    N1 C7 C8 . . 111.73(14) ?
    N1 C7 H7A . . 109.3 ?
    C8 C7 H7A . . 109.3 ?
    N1 C7 H7B . . 109.3 ?
    C8 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 107.9 ?
    C7 C8 C9 . . 110.04(16) ?
    C7 C8 H8A . . 109.7 ?
    C9 C8 H8A . . 109.7 ?
    C7 C8 H8B . . 109.7 ?
    C9 C8 H8B . . 109.7 ?
    H8A C8 H8B . . 108.2 ?
    O3 C9 N2 . . 122.98(19) ?
    O3 C9 C8 . . 120.75(18) ?
    N2 C9 C8 . . 116.27(19) ?
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
    C5 C4 C3 C6 . . . . -71.2(3) ?
    C5 C4 C3 C2 . . . . 161.2(2) ?
    C7 N1 C2 C3 . . . . 165.30(14) ?
    C7 N1 C2 C1 . . . . -69.67(18) ?
    C6 C3 C2 N1 . . . . 62.6(2) ?
    C4 C3 C2 N1 . . . . -170.95(17) ?
    C6 C3 C2 C1 . . . . -60.0(2) ?
    C4 C3 C2 C1 . . . . 66.5(2) ?
    N1 C2 C1 O2 . . . . 144.24(16) ?
    C3 C2 C1 O2 . . . . -91.9(2) ?
    N1 C2 C1 O1 . . . . -36.3(2) ?
    C3 C2 C1 O1 . . . . 87.5(2) ?
    C2 N1 C7 C8 . . . . -176.01(15) ?
    N1 C7 C8 C9 . . . . -176.58(17) ?
    C7 C8 C9 O3 . . . . 48.8(3) ?
    C7 C8 C9 N2 . . . . -130.4(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
    N1 H1N1 O2 4_646 0.89(2) 1.96(2) 2.7772(19) 152(2)
    N1 H2N1 O1 1_655 0.88(2) 1.83(2) 2.7047(19) 174(2)
    N2 H1N2 O3 3_567 0.90(3) 2.11(3) 2.970(3) 161(3)
    N2 H2N2 O3 1_655 0.84(3) 2.34(3) 3.092(3) 149(2)
    C2 H2 O1 4_656 0.98 2.53 3.469(2) 160.4
data_New_Global_Publ_Block
_journal_date_recd_electronic     2015-07-28
_journal_date_accepted     2015-07-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      9
_journal_page_first     o665
_journal_page_last     o666
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015014498
_journal_coeditor_code     BG2563
_publ_contact_author_name     'R.V. Krishnakumar'
_publ_contact_author_address
;
Department of Physics
Thiagarajar College
Madurai 625 009
Tamil Nadu
India
;
_publ_contact_author_email     'mailtorvkk@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Redetermined crystal structure of N-(β-carboxyethyl)-α-isoleucine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chandrarekha, M.' .
;
Department of Physics
Thiagarajar College
Madurai 625 009
Tamil Nadu
India
;
    'Srinivasan, N.' .
;
Department of Physics
Thiagarajar College
Madurai 625 009
Tamil Nadu
India
;
    'Krishnakumar, R. V.' .
;
Department of Physics
Thiagarajar College
Madurai 625 009
Tamil Nadu
India
;
_publ_section_synopsis
;
Redetermination of the crystal structure of N-(β-Carboxyethyl)-α-isoleucine
shows that the molecule exists as a 'zwitterion' rather than unionized as
reported earlier by Nehls et al. (2013). Acta Cryst.E69,
o172--o173.
;
