#------------------------------------------------------------------------------
#$Date: 2016-02-20 01:53:41 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/46/2104692.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_2104692
loop_
_publ_author_name
'Görbitz, Carl Henrik'
_publ_section_title
;
 <small>L</small>-2-Aminobutyric acid: two fully ordered polymorphs
 with Z' = 4
;
_journal_coeditor_code           PS5004
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              253
_journal_page_last               259
_journal_paper_doi               10.1107/S0108768110005732
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C4 H9 N O2'
_chemical_formula_sum            'C4 H9 N O2'
_chemical_formula_weight         103.12
_chemical_name_common            L-Abu
_chemical_name_systematic
;
 (S)-2-aminobutyric acid
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 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                 100.295(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   9.646(2)
_cell_length_b                   5.2145(12)
_cell_length_c                   42.885(10)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.93
_cell_volume                     2122.3(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Apex II CCD diffractometer'
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            7238
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.7912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0440
_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)+(0.0531P)²+3.6316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                1852
_reflns_number_total             2083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ps5004.cif
_cod_data_source_block           II
_cod_original_cell_volume        2122.5(8)
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               2104692
_cod_database_fobs_code          2104692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A -0.0869(2) 0.7794(5) 0.03248(6) 0.0173(6) Uani d . 1 . .
O O2A 0.0039(3) 0.3905(5) 0.04313(7) 0.0235(7) Uani d . 1 . .
N N1A 0.1646(3) 0.9851(6) 0.02779(6) 0.0147(7) Uani d . 1 . .
H H1A 0.1327 0.9516 0.0069 0.022 Uiso calc R 1 . .
H H2A 0.2539 1.0481 0.0303 0.022 Uiso calc R 1 . .
H H3A 0.1075 1.1029 0.0347 0.022 Uiso calc R 1 . .
C C1A 0.0151(4) 0.6258(8) 0.03974(8) 0.0157(8) Uani d . 1 . .
C C2A 0.1642(3) 0.7444(7) 0.04644(8) 0.0160(8) Uani d . 1 . .
H H21A 0.2329 0.6204 0.0400 0.019 Uiso calc R 1 . .
C C3A 0.2086(4) 0.8080(9) 0.08173(8) 0.0256(9) Uani d . 1 . .
H H32A 0.2977 0.9066 0.0847 0.031 Uiso calc R 1 . .
H H31A 0.1359 0.9192 0.0883 0.031 Uiso calc R 1 . .
C C4A 0.2295(4) 0.5748(11) 0.10308(10) 0.0372(12) Uani d . 1 . .
H H41A 0.2625 0.6292 0.1250 0.056 Uiso calc R 1 . .
H H42A 0.2996 0.4610 0.0964 0.056 Uiso calc R 1 . .
H H43A 0.1399 0.4831 0.1016 0.056 Uiso calc R 1 . .
O O1B 0.4092(2) 0.2807(5) 0.02806(5) 0.0171(6) Uani d . 1 . .
O O2B 0.5037(3) -0.0834(5) 0.04897(7) 0.0253(7) Uani d . 1 . .
N N1B 0.6605(3) 0.5128(7) 0.03150(6) 0.0141(6) Uani d . 1 . .
H H1B 0.6329 0.4693 0.0108 0.021 Uiso calc R 1 . .
H H2B 0.7505 0.5731 0.0346 0.021 Uiso calc R 1 . .
H H3B 0.6024 0.6367 0.0368 0.021 Uiso calc R 1 . .
C C1B 0.5113(3) 0.1463(8) 0.04154(8) 0.0146(8) Uani d . 1 . .
C C2B 0.6537(3) 0.2824(8) 0.05180(8) 0.0155(8) Uani d . 1 . .
H H21B 0.7318 0.1621 0.0493 0.019 Uiso calc R 1 . .
C C3B 0.6679(4) 0.3597(8) 0.08685(8) 0.0211(9) Uani d . 1 . .
H H31B 0.5844 0.4625 0.0895 0.025 Uiso calc R 1 . .
H H32B 0.6677 0.2024 0.0998 0.025 Uiso calc R 1 . .
C C4B 0.7997(4) 0.5129(10) 0.09953(8) 0.0275(9) Uani d . 1 . .
H H41B 0.8093 0.5310 0.1226 0.041 Uiso calc R 1 . .
H H42B 0.7927 0.6831 0.0897 0.041 Uiso calc R 1 . .
H H43B 0.8824 0.4234 0.0945 0.041 Uiso calc R 1 . .
O O1C -0.1360(2) 0.1523(5) 0.21886(5) 0.0157(5) Uani d . 1 . .
O O2C -0.0733(3) 0.5268(5) 0.20093(6) 0.0232(6) Uani d . 1 . .
N N1C 0.1143(3) -0.0685(6) 0.21989(6) 0.0151(7) Uani d . 1 . .
H H1C 0.1128 -0.0502 0.2409 0.023 Uiso calc R 1 . .
H H3C 0.1990 -0.1337 0.2173 0.023 Uiso calc R 1 . .
H H2C 0.0443 -0.1773 0.2111 0.023 Uiso calc R 1 . .
C C1C -0.0498(4) 0.2987(8) 0.20865(8) 0.0155(8) Uani d . 1 . .
C C2C 0.0925(4) 0.1868(7) 0.20399(8) 0.0159(8) Uani d . 1 . .
H H21C 0.1690 0.3048 0.2142 0.019 Uiso calc R 1 . .
C C3C 0.1008(4) 0.1653(9) 0.16876(8) 0.0218(9) Uani d . 1 . .
H H31C 0.0963 0.3398 0.1596 0.026 Uiso calc R 1 . .
H H32C 0.1934 0.0911 0.1668 0.026 Uiso calc R 1 . .
C C4C -0.0146(4) 0.0026(10) 0.14943(8) 0.0279(9) Uani d . 1 . .
H H41C -0.0048 0.0061 0.1271 0.042 Uiso calc R 1 . .
H H42C -0.1069 0.0715 0.1516 0.042 Uiso calc R 1 . .
H H43C -0.0064 -0.1745 0.1572 0.042 Uiso calc R 1 . .
O O1D 0.3607(2) 0.6429(5) 0.21874(5) 0.0160(6) Uani d . 1 . .
O O2D 0.4339(3) 1.0372(5) 0.21033(6) 0.0238(6) Uani d . 1 . .
N N1D 0.6197(3) 0.4426(6) 0.22100(6) 0.0138(7) Uani d . 1 . .
H H1D 0.6245 0.4710 0.2421 0.021 Uiso calc R 1 . .
H H2D 0.5512 0.3250 0.2142 0.021 Uiso calc R 1 . .
H H3D 0.7040 0.3824 0.2175 0.021 Uiso calc R 1 . .
C C1D 0.4505(3) 0.8002(8) 0.21183(8) 0.0139(8) Uani d . 1 . .
C C2D 0.5857(3) 0.6874(7) 0.20336(8) 0.0141(8) Uani d . 1 . .
H H21D 0.6647 0.8114 0.2098 0.017 Uiso calc R 1 . .
C C3D 0.5697(4) 0.6341(8) 0.16771(8) 0.0201(8) Uani d . 1 . .
H H31D 0.6544 0.5416 0.1637 0.024 Uiso calc R 1 . .
H H32D 0.4873 0.5210 0.1611 0.024 Uiso calc R 1 . .
C C4D 0.5508(4) 0.8772(9) 0.14760(9) 0.0263(10) Uani d . 1 . .
H H41D 0.5433 0.8316 0.1252 0.039 Uiso calc R 1 . .
H H42D 0.6321 0.9902 0.1539 0.039 Uiso calc R 1 . .
H H43D 0.4648 0.9659 0.1507 0.039 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'
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
C2A N1A H1A . . 109.5 ?
C2A N1A H2A . . 109.5 ?
H1A N1A H2A . . 109.5 ?
C2A N1A H3A . . 109.5 ?
H1A N1A H3A . . 109.5 ?
H2A N1A H3A . . 109.5 ?
O2A C1A O1A . . 125.0(4) ?
O2A C1A C2A . . 118.1(4) ?
O1A C1A C2A . . 116.8(4) ?
N1A C2A C3A . . 108.7(3) ?
N1A C2A C1A . . 109.2(3) ?
C3A C2A C1A . . 110.9(3) ?
N1A C2A H21A . . 109.3 ?
C3A C2A H21A . . 109.3 ?
C1A C2A H21A . . 109.3 ?
C4A C3A C2A . . 114.0(4) ?
C4A C3A H32A . . 108.8 ?
C2A C3A H32A . . 108.8 ?
C4A C3A H31A . . 108.8 ?
C2A C3A H31A . . 108.8 ?
H32A C3A H31A . . 107.7 ?
C3A C4A H41A . . 109.5 ?
C3A C4A H42A . . 109.5 ?
H41A C4A H42A . . 109.5 ?
C3A C4A H43A . . 109.5 ?
H41A C4A H43A . . 109.5 ?
H42A C4A H43A . . 109.5 ?
C2B N1B H1B . . 109.5 ?
C2B N1B H2B . . 109.5 ?
H1B N1B H2B . . 109.5 ?
C2B N1B H3B . . 109.5 ?
H1B N1B H3B . . 109.5 ?
H2B N1B H3B . . 109.5 ?
O2B C1B O1B . . 125.1(4) ?
O2B C1B C2B . . 117.4(3) ?
O1B C1B C2B . . 117.3(3) ?
N1B C2B C3B . . 110.7(3) ?
N1B C2B C1B . . 109.5(3) ?
C3B C2B C1B . . 108.6(3) ?
N1B C2B H21B . . 109.3 ?
C3B C2B H21B . . 109.3 ?
C1B C2B H21B . . 109.3 ?
C4B C3B C2B . . 114.2(3) ?
C4B C3B H31B . . 108.7 ?
C2B C3B H31B . . 108.7 ?
C4B C3B H32B . . 108.7 ?
C2B C3B H32B . . 108.7 ?
H31B C3B H32B . . 107.6 ?
C3B C4B H41B . . 109.5 ?
C3B C4B H42B . . 109.5 ?
H41B C4B H42B . . 109.5 ?
C3B C4B H43B . . 109.5 ?
H41B C4B H43B . . 109.5 ?
H42B C4B H43B . . 109.5 ?
C2C N1C H1C . . 109.5 ?
C2C N1C H3C . . 109.5 ?
H1C N1C H3C . . 109.5 ?
C2C N1C H2C . . 109.5 ?
H1C N1C H2C . . 109.5 ?
H3C N1C H2C . . 109.5 ?
O2C C1C O1C . . 124.7(3) ?
O2C C1C C2C . . 116.9(3) ?
O1C C1C C2C . . 118.3(3) ?
N1C C2C C3C . . 110.9(3) ?
N1C C2C C1C . . 109.6(3) ?
C3C C2C C1C . . 111.2(3) ?
N1C C2C H21C . . 108.4 ?
C3C C2C H21C . . 108.4 ?
C1C C2C H21C . . 108.4 ?
C4C C3C C2C . . 114.6(3) ?
C4C C3C H31C . . 108.6 ?
C2C C3C H31C . . 108.6 ?
C4C C3C H32C . . 108.6 ?
C2C C3C H32C . . 108.6 ?
H31C C3C H32C . . 107.6 ?
C3C C4C H41C . . 109.5 ?
C3C C4C H42C . . 109.5 ?
H41C C4C H42C . . 109.5 ?
C3C C4C H43C . . 109.5 ?
H41C C4C H43C . . 109.5 ?
H42C C4C H43C . . 109.5 ?
C2D N1D H3D . . 109.5 ?
C2D N1D H2D . . 109.5 ?
H3D N1D H2D . . 109.5 ?
C2D N1D H1D . . 109.5 ?
H3D N1D H1D . . 109.5 ?
H2D N1D H1D . . 109.5 ?
O2D C1D O1D . . 124.5(3) ?
O2D C1D C2D . . 118.4(3) ?
O1D C1D C2D . . 117.0(3) ?
N1D C2D C1D . . 109.1(3) ?
N1D C2D C3D . . 108.9(3) ?
C1D C2D C3D . . 111.6(3) ?
N1D C2D H21D . . 109.0 ?
C1D C2D H21D . . 109.0 ?
C3D C2D H21D . . 109.0 ?
C4D C3D C2D . . 113.2(3) ?
C4D C3D H31D . . 108.9 ?
C2D C3D H31D . . 108.9 ?
C4D C3D H32D . . 108.9 ?
C2D C3D H32D . . 108.9 ?
H31D C3D H32D . . 107.8 ?
C3D C4D H41D . . 109.5 ?
C3D C4D H42D . . 109.5 ?
H41D C4D H42D . . 109.5 ?
C3D C4D H43D . . 109.5 ?
H41D C4D H43D . . 109.5 ?
H42D C4D H43D . . 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
O1A C1A . 1.264(5) ?
O2A C1A . 1.243(5) ?
N1A C2A . 1.489(5) ?
N1A H1A . 0.9100 ?
N1A H2A . 0.9100 ?
N1A H3A . 0.9100 ?
C1A C2A . 1.544(5) ?
C2A C3A . 1.534(5) ?
C2A H21A . 1.0000 ?
C3A C4A . 1.514(6) ?
C3A H32A . 0.9900 ?
C3A H31A . 0.9900 ?
C4A H41A . 0.9800 ?
C4A H42A . 0.9800 ?
C4A H43A . 0.9800 ?
O1B C1B . 1.261(4) ?
O2B C1B . 1.245(5) ?
N1B C2B . 1.492(5) ?
N1B H1B . 0.9100 ?
N1B H2B . 0.9100 ?
N1B H3B . 0.9100 ?
C1B C2B . 1.539(5) ?
C2B C3B . 1.538(5) ?
C2B H21B . 1.0000 ?
C3B C4B . 1.518(5) ?
C3B H31B . 0.9900 ?
C3B H32B . 0.9900 ?
C4B H41B . 0.9800 ?
C4B H42B . 0.9800 ?
C4B H43B . 0.9800 ?
O1C C1C . 1.263(4) ?
O2C C1C . 1.245(5) ?
N1C C2C . 1.494(5) ?
N1C H1C . 0.9100 ?
N1C H3C . 0.9100 ?
N1C H2C . 0.9100 ?
C1C C2C . 1.538(5) ?
C2C C3C . 1.531(5) ?
C2C H21C . 1.0000 ?
C3C C4C . 1.522(6) ?
C3C H31C . 0.9900 ?
C3C H32C . 0.9900 ?
C4C H41C . 0.9800 ?
C4C H42C . 0.9800 ?
C4C H43C . 0.9800 ?
O1D C1D . 1.266(4) ?
O2D C1D . 1.247(5) ?
N1D C2D . 1.490(5) ?
N1D H3D . 0.9100 ?
N1D H2D . 0.9100 ?
N1D H1D . 0.9100 ?
C1D C2D . 1.532(5) ?
C2D C3D . 1.534(5) ?
C2D H21D . 1.0000 ?
C3D C4D . 1.526(6) ?
C3D H31D . 0.9900 ?
C3D H32D . 0.9900 ?
C4D H41D . 0.9800 ?
C4D H42D . 0.9800 ?
C4D H43D . 0.9800 ?
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
N1A H1A O1A 2 0.91 1.89 2.775(4) 162.2
N1A H2A O1B 1_565 0.91 1.94 2.816(4) 160.2
N1A H3A O2A 1_565 0.91 1.87 2.769(4) 168.1
N1B H1B O1B 2_655 0.91 1.91 2.798(4) 163.3
N1B H2B O1A 1_655 0.91 1.92 2.799(4) 162.5
N1B H3B O2B 1_565 0.91 1.87 2.773(4) 172.6
N1C H1C O1D 4_545 0.91 1.98 2.824(4) 153.9
N1C H2C O2C 1_545 0.91 1.92 2.804(4) 163.7
N1C H3C O1D 1_545 0.91 1.94 2.821(4) 162.8
N1D H1D O1C 4 0.91 1.91 2.780(4) 159.6
N1D H2D O2D 1_545 0.91 1.87 2.756(4) 164.3
N1D H3D O1C 1_655 0.91 1.95 2.817(4) 159.2
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
N1A C2A C1A O1A . . . . -28.9(4) y
N1A C2A C3A C4A . . . . -173.1(3) y
N1B C2B C1B O1B . . . . -25.5(4) y
N1B C2B C3B C4B . . . . -55.7(4) y
N1C C2C C1C O1C . . . . -13.0(4) y
N1C C2C C3C C4C . . . . 64.4(4) y
N1D C2D C1D O1D . . . . -30.6(4) y
N1D C2D C3D C4D . . . . -173.7(3) y
O2A C1A C2A N1A . . . . 154.1(3) ?
O2A C1A C2A C3A . . . . -86.2(4) ?
O1A C1A C2A C3A . . . . 90.9(4) ?
C1A C2A C3A C4A . . . . 66.8(4) ?
O2B C1B C2B N1B . . . . 159.0(3) ?
O2B C1B C2B C3B . . . . -80.0(4) ?
O1B C1B C2B C3B . . . . 95.5(4) ?
C1B C2B C3B C4B . . . . -176.0(4) ?
O2C C1C C2C N1C . . . . 169.4(3) ?
O2C C1C C2C C3C . . . . -67.6(4) ?
O1C C1C C2C C3C . . . . 109.9(4) ?
C1C C2C C3C C4C . . . . -57.8(5) ?
O2D C1D C2D N1D . . . . 152.1(3) ?
O2D C1D C2D C3D . . . . -87.5(4) ?
O1D C1D C2D C3D . . . . 89.9(4) ?
C1D C2D C3D C4D . . . . 65.8(4) ?
