#------------------------------------------------------------------------------
#$Date: 2016-02-20 01:53:41 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/46/2104691.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_2104691
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           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.326(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.614(6)
_cell_length_b                   5.227(3)
_cell_length_c                   21.385(13)
_cell_measurement_pressure       101.0(10)
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.51
_cell_volume                     1057.2(11)
_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 0.976
_diffrn_measured_fraction_theta_max 0.909
_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  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6460
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.7486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'elongated plate'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          1.10
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0578
_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)+(0.0850P)²+0.4880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1647
_reflns_number_gt                2468
_reflns_number_total             2700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ps5004.cif
_cod_data_source_block           I
_cod_original_cell_volume        1057.1(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2104691
_cod_database_fobs_code          2104691
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.1618(2) 0.7249(5) 0.05862(11) 0.0189(5) Uani d . 1 . .
O O2A 0.2490(3) 0.3333(5) 0.08128(13) 0.0269(6) Uani d . 1 . .
N N1A 0.4156(3) 0.9310(5) 0.05725(12) 0.0165(6) Uani d . 1 . .
H H1A 0.3903 0.9014 0.0148 0.025 Uiso calc R 1 . .
H H2A 0.5047 0.9968 0.0655 0.025 Uiso calc R 1 . .
H H3A 0.3543 1.0444 0.0698 0.025 Uiso calc R 1 . .
C C1A 0.2622(3) 0.5696(7) 0.07523(15) 0.0162(6) Uani d . 1 . .
C C2A 0.4119(3) 0.6861(7) 0.09261(16) 0.0185(7) Uani d . 1 . .
H H21A 0.4815 0.5645 0.0794 0.022 Uiso calc R 1 . .
C C3A 0.4532(4) 0.7370(9) 0.16363(16) 0.0291(8) Uani d . 1 . .
H H31A 0.3766 0.8344 0.1781 0.035 Uiso calc R 1 . .
H H32A 0.5395 0.8443 0.1713 0.035 Uiso calc R 1 . .
C C4A 0.4810(4) 0.4918(11) 0.20304(18) 0.0413(11) Uani d . 1 . .
H H41A 0.5037 0.5357 0.2483 0.062 Uiso calc R 1 . .
H H42A 0.5607 0.3993 0.1908 0.062 Uiso calc R 1 . .
H H43A 0.3965 0.3833 0.1953 0.062 Uiso calc R 1 . .
O O1B 0.6611(2) 0.2229(5) 0.06230(11) 0.0197(5) Uani d . 1 . .
O O2B 0.7617(3) -0.1383(5) 0.10293(13) 0.0266(6) Uani d . 1 . .
N N1B 0.9102(3) 0.4579(6) 0.06143(12) 0.0150(5) Uani d . 1 . .
H H1B 0.8819 0.4100 0.0202 0.023 Uiso calc R 1 . .
H H2B 0.9993 0.5231 0.0667 0.023 Uiso calc R 1 . .
H H3B 0.8502 0.5791 0.0717 0.023 Uiso calc R 1 . .
C C1B 0.7664(3) 0.0909(7) 0.08684(14) 0.0164(6) Uani d . 1 . .
C C2B 0.9089(3) 0.2305(7) 0.10364(16) 0.0206(7) Uani d . 1 . .
H H21B 0.9874 0.1115 0.0983 0.025 Uiso calc R 1 . .
C C3B 0.9265(4) 0.3171(8) 0.17455(16) 0.0277(8) Uani d . 1 . .
H H31B 0.8420 0.4167 0.1801 0.033 Uiso calc R 1 . .
H H32B 0.9304 0.1630 0.2017 0.033 Uiso calc R 1 . .
C C4B 1.0564(4) 0.4770(10) 0.19724(17) 0.0330(9) Uani d . 1 . .
H H41B 1.0695 0.4971 0.2435 0.050 Uiso calc R 1 . .
H H42B 1.0447 0.6458 0.1770 0.050 Uiso calc R 1 . .
H H43B 1.1394 0.3921 0.1860 0.050 Uiso calc R 1 . .
O O1C 0.1142(2) 0.1140(5) 0.43818(10) 0.0187(5) Uani d . 1 . .
O O2C 0.1771(2) 0.4896(5) 0.40269(13) 0.0262(6) Uani d . 1 . .
N N1C 0.3644(3) -0.1063(6) 0.44032(12) 0.0165(5) Uani d . 1 . .
H H1C 0.4488 -0.1724 0.4347 0.025 Uiso calc R 1 . .
H H2C 0.2934 -0.2140 0.4231 0.025 Uiso calc R 1 . .
H H3C 0.3643 -0.0877 0.4826 0.025 Uiso calc R 1 . .
C C1C 0.2007(3) 0.2611(7) 0.41789(15) 0.0176(6) Uani d . 1 . .
C C2C 0.3426(3) 0.1488(6) 0.40840(15) 0.0174(6) Uani d . 1 . .
H H21C 0.4195 0.2660 0.4290 0.021 Uiso calc R 1 . .
C C3C 0.3509(4) 0.1284(8) 0.33786(16) 0.0264(8) Uani d . 1 . .
H H31C 0.3459 0.3027 0.3195 0.032 Uiso calc R 1 . .
H H32C 0.4439 0.0551 0.3338 0.032 Uiso calc R 1 . .
C C4C 0.2358(4) -0.0335(10) 0.29949(16) 0.0349(9) Uani d . 1 . .
H H41C 0.2479 -0.0364 0.2550 0.052 Uiso calc R 1 . .
H H42C 0.1432 0.0393 0.3023 0.052 Uiso calc R 1 . .
H H43C 0.2418 -0.2083 0.3163 0.052 Uiso calc R 1 . .
O O1D 0.6104(2) 0.6060(5) 0.43697(10) 0.0189(5) Uani d . 1 . .
O O2D 0.6838(2) 1.0001(5) 0.41945(13) 0.0272(6) Uani d . 1 . .
N N1D 0.8699(3) 0.4063(5) 0.44150(12) 0.0161(6) Uani d . 1 . .
H H1D 0.9521 0.3410 0.4327 0.024 Uiso calc R 1 . .
H H2D 0.7987 0.2920 0.4296 0.024 Uiso calc R 1 . .
H H3D 0.8797 0.4370 0.4840 0.024 Uiso calc R 1 . .
C C1D 0.6999(3) 0.7623(7) 0.42291(15) 0.0168(6) Uani d . 1 . .
C C2D 0.8361(3) 0.6502(6) 0.40584(15) 0.0161(6) Uani d . 1 . .
H H21D 0.9153 0.7740 0.4187 0.019 Uiso calc R 1 . .
C C3D 0.8199(3) 0.5966(7) 0.33422(15) 0.0223(7) Uani d . 1 . .
H H31D 0.9062 0.5093 0.3259 0.027 Uiso calc R 1 . .
H H32D 0.7391 0.4791 0.3213 0.027 Uiso calc R 1 . .
C C4D 0.7962(4) 0.8363(9) 0.29379(17) 0.0303(8) Uani d . 1 . .
H H41D 0.7890 0.7903 0.2489 0.045 Uiso calc R 1 . .
H H42D 0.8759 0.9538 0.3062 0.045 Uiso calc R 1 . .
H H43D 0.7086 0.9197 0.3002 0.045 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 . . 125.2(3) ?
O2A C1A C2A . . 118.2(3) ?
O1A C1A C2A . . 116.5(3) ?
N1A C2A C3A . . 109.3(3) ?
N1A C2A C1A . . 108.8(2) ?
C3A C2A C1A . . 112.0(3) ?
N1A C2A H21A . . 108.9 ?
C3A C2A H21A . . 108.9 ?
C1A C2A H21A . . 108.9 ?
C2A C3A C4A . . 113.1(3) ?
C2A C3A H31A . . 109.0 ?
C4A C3A H31A . . 109.0 ?
C2A C3A H32A . . 109.0 ?
C4A C3A H32A . . 109.0 ?
H31A C3A H32A . . 107.8 ?
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(3) ?
O2B C1B C2B . . 117.7(3) ?
O1B C1B C2B . . 117.0(3) ?
N1B C2B C1B . . 109.9(2) ?
N1B C2B C3B . . 110.2(3) ?
C1B C2B C3B . . 107.6(3) ?
N1B C2B H21B . . 109.7 ?
C1B C2B H21B . . 109.7 ?
C3B C2B H21B . . 109.7 ?
C4B C3B C2B . . 114.4(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 H2C . . 109.5 ?
H1C N1C H2C . . 109.5 ?
C2C N1C H3C . . 109.5 ?
H1C N1C H3C . . 109.5 ?
H2C N1C H3C . . 109.5 ?
O2C C1C O1C . . 124.8(3) ?
O2C C1C C2C . . 117.2(3) ?
O1C C1C C2C . . 117.9(3) ?
N1C C2C C3C . . 111.1(3) ?
N1C C2C C1C . . 109.7(2) ?
C3C C2C C1C . . 111.3(3) ?
N1C C2C H21C . . 108.2 ?
C3C C2C H21C . . 108.2 ?
C1C C2C H21C . . 108.2 ?
C4C C3C C2C . . 114.3(3) ?
C4C C3C H31C . . 108.7 ?
C2C C3C H31C . . 108.7 ?
C4C C3C H32C . . 108.7 ?
C2C C3C H32C . . 108.7 ?
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 H1D . . 109.5 ?
C2D N1D H2D . . 109.5 ?
H1D N1D H2D . . 109.5 ?
C2D N1D H3D . . 109.5 ?
H1D N1D H3D . . 109.5 ?
H2D N1D H3D . . 109.5 ?
O2D C1D O1D . . 125.0(3) ?
O2D C1D C2D . . 117.8(3) ?
O1D C1D C2D . . 117.1(3) ?
N1D C2D C1D . . 108.8(2) ?
N1D C2D C3D . . 109.1(3) ?
C1D C2D C3D . . 111.6(2) ?
N1D C2D H21D . . 109.1 ?
C1D C2D H21D . . 109.1 ?
C3D C2D H21D . . 109.1 ?
C4D C3D C2D . . 113.3(3) ?
C4D C3D H31D . . 108.9 ?
C2D C3D H31D . . 108.9 ?
C4D C3D H32D . . 108.9 ?
C2D C3D H32D . . 108.9 ?
H31D C3D H32D . . 107.7 ?
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 . 1.262(4) ?
O2A C1A . 1.251(4) ?
N1A C2A . 1.490(4) ?
N1A H1A . 0.9100 ?
N1A H2A . 0.9100 ?
N1A H3A . 0.9100 ?
C1A C2A . 1.545(4) ?
C2A C3A . 1.523(5) ?
C2A H21A . 1.0000 ?
C3A C4A . 1.531(5) ?
C3A H31A . 0.9900 ?
C3A H32A . 0.9900 ?
C4A H41A . 0.9800 ?
C4A H42A . 0.9800 ?
C4A H43A . 0.9800 ?
O1B C1B . 1.259(4) ?
O2B C1B . 1.249(4) ?
N1B C2B . 1.494(4) ?
N1B H1B . 0.9100 ?
N1B H2B . 0.9100 ?
N1B H3B . 0.9100 ?
C1B C2B . 1.537(4) ?
C2B C3B . 1.562(5) ?
C2B H21B . 1.0000 ?
C3B C4B . 1.509(5) ?
C3B H31B . 0.9900 ?
C3B H32B . 0.9900 ?
C4B H41B . 0.9800 ?
C4B H42B . 0.9800 ?
C4B H43B . 0.9800 ?
O1C C1C . 1.265(4) ?
O2C C1C . 1.248(5) ?
N1C C2C . 1.495(4) ?
N1C H1C . 0.9100 ?
N1C H2C . 0.9100 ?
N1C H3C . 0.9100 ?
C1C C2C . 1.532(4) ?
C2C C3C . 1.529(5) ?
C2C H21C . 1.0000 ?
C3C C4C . 1.513(5) ?
C3C H31C . 0.9900 ?
C3C H32C . 0.9900 ?
C4C H41C . 0.9800 ?
C4C H42C . 0.9800 ?
C4C H43C . 0.9800 ?
O1D C1D . 1.261(4) ?
O2D C1D . 1.253(4) ?
N1D C2D . 1.491(4) ?
N1D H1D . 0.9100 ?
N1D H2D . 0.9100 ?
N1D H3D . 0.9100 ?
C1D C2D . 1.536(4) ?
C2D C3D . 1.537(4) ?
C2D H21D . 1.0000 ?
C3D C4D . 1.516(5) ?
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 O1B 2_655 0.91 1.88 2.754(4) 160.0
N1A H2A O1B 1_565 0.91 1.92 2.796(4) 159.9
N1A H3A O2A 1_565 0.91 1.86 2.747(4) 164.9
N1B H1B O1A 2_645 0.91 1.92 2.814(4) 165.4
N1B H2B O1A 1_655 0.91 1.92 2.803(3) 163.5
N1B H3B O2B 1_565 0.91 1.89 2.781(4) 167.6
N1C H1C O1D 1_545 0.91 1.93 2.815(4) 163.1
N1C H2C O2C 1_545 0.91 1.91 2.799(4) 163.3
N1C H3C O1D 2_646 0.91 1.97 2.819(4) 154.1
N1D H1D O1C 1_655 0.91 1.95 2.813(3) 158.7
N1D H2D O2D 1_545 0.91 1.87 2.762(4) 164.9
N1D H3D O1C 2_656 0.91 1.90 2.771(4) 160.6
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
N1A C2A C1A O1A . . . . -27.4(4) y
N1A C2A C3A C4A . . . . -168.6(3) y
N1B C2B C1B O1B . . . . -26.7(4) y
N1B C2B C3B C4B . . . . -55.5(4) y
N1C C2C C1C O1C . . . . -13.5(4) y
N1C C2C C3C C4C . . . . 64.2(4) y
N1D C2D C1D O1D . . . . -30.4(4) y
N1D C2D C3D C4D . . . . -175.6(3) y
O2A C1A C2A N1A . . . . 155.7(3) ?
O2A C1A C2A C3A . . . . -83.4(4) ?
O1A C1A C2A C3A . . . . 93.5(4) ?
C1A C2A C3A C4A . . . . 70.8(4) ?
O2B C1B C2B N1B . . . . 158.7(3) ?
O2B C1B C2B C3B . . . . -81.4(4) ?
O1B C1B C2B C3B . . . . 93.2(3) ?
C1B C2B C3B C4B . . . . -175.2(3) ?
O2C C1C C2C N1C . . . . 169.1(3) ?
O2C C1C C2C C3C . . . . -67.5(4) ?
O1C C1C C2C C3C . . . . 109.9(3) ?
C1C C2C C3C C4C . . . . -58.4(4) ?
O2D C1D C2D N1D . . . . 152.3(3) ?
O2D C1D C2D C3D . . . . -87.3(4) ?
O1D C1D C2D C3D . . . . 90.0(4) ?
C1D C2D C3D C4D . . . . 64.1(4) ?
