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#$Date: 2025-08-21 02:19:08 +0200 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/4/50/16/4501605.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4501605
loop_
_publ_author_name
'Iwama, Sekai'
'Horiguchi, Masahiro'
'Sato, Hiroyasu'
'Uchida, Yoshiaki'
'Takahashi, Hiroki'
'Tsue, Hirohito'
'Tamura, Rui'
_publ_section_title
;
 Observation of the Preferential Enrichment Phenomenon for Essential
 \a-Amino Acids with a Racemic Crystal Structure
;
_journal_issue                   6
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              2668
_journal_paper_doi               10.1021/cg100152c
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C3 H7 N O2 '
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.09
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.0067(16)
_cell_length_b                   6.0290(6)
_cell_length_c                   5.8318(6)
_cell_measurement_reflns_used    2170
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.4
_cell_volume                     422.15(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      293.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3795
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             192.00
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     57
_refine_ls_number_reflns         526
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.0654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                364
_reflns_number_total             526
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cg100152c_si_004.cif
_cod_data_source_block           '_sc0565_rt_proc'
_cod_original_formula_sum        'C3 H7 N O2 '
_cod_database_code               4501605
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2+Z
3 1/2+X,1/2-Y,+Z
4 -X,-Y,1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O(1) O 0.4109(2) 0.9861(4) 0.0039(5) 0.0472(8) Uani 1.00 1 d .
O(2) O 0.3143(2) 0.6984(4) -0.1325(4) 0.0441(7) Uani 1.00 1 d .
N(1) N 0.3609(2) 0.8949(4) 0.4426(5) 0.0386(8) Uani 1.00 1 d .
C(1) C 0.3365(3) 0.7206(6) 0.2706(6) 0.0356(9) Uani 1.00 1 d .
C(2) C 0.3562(2) 0.8113(5) 0.0281(6) 0.0362(8) Uani 1.00 1 d .
C(3) C 0.4077(3) 0.5199(6) 0.3163(7) 0.0462(11) Uani 1.00 1 d .
H(1) H 0.4312 0.9392 0.4274 0.046 Uiso 1.00 1 c R
H(2) H 0.3506 0.8405 0.5828 0.046 Uiso 1.00 1 c R
H(3) H 0.3155 1.0096 0.4207 0.046 Uiso 1.00 1 c R
H(4) H 0.2580 0.6779 0.2847 0.043 Uiso 1.00 1 c R
H(5) H 0.4849 0.5603 0.3066 0.055 Uiso 1.00 1 c R
H(6) H 0.3916 0.4075 0.2044 0.055 Uiso 1.00 1 c R
H(7) H 0.3919 0.4638 0.4669 0.055 Uiso 1.00 1 c R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O(1) 0.0522(15) 0.0505(14) 0.0389(19) -0.0144(12) -0.0000(15) 0.0037(12)
O(2) 0.0511(15) 0.0517(15) 0.0297(13) -0.0075(13) -0.0021(14) -0.0001(14)
N(1) 0.0417(17) 0.0472(17) 0.0269(16) -0.0002(15) 0.0009(13) 0.0007(13)
C(1) 0.041(2) 0.040(2) 0.0249(19) -0.0009(16) -0.0012(15) -0.0013(18)
C(2) 0.0366(19) 0.0443(17) 0.028(2) 0.0069(16) -0.0006(16) 0.001(2)
C(3) 0.055(2) 0.047(2) 0.036(3) 0.0033(19) -0.0016(19) 0.0051(19)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
_geom_angle_publ_flag
N(1) C(1) C(2) 109.9(2) yes
N(1) C(1) C(3) 109.8(3) yes
C(2) C(1) C(3) 111.2(3) yes
O(1) C(2) O(2) 125.5(3) yes
O(1) C(2) C(1) 119.1(3) yes
O(2) C(2) C(1) 115.4(3) yes
C(1) N(1) H(1) 109.5 no
C(1) N(1) H(2) 109.5 no
C(1) N(1) H(3) 109.5 no
H(1) N(1) H(2) 109.5 no
H(1) N(1) H(3) 109.5 no
H(2) N(1) H(3) 109.5 no
N(1) C(1) H(4) 108.6 no
C(2) C(1) H(4) 108.6 no
C(3) C(1) H(4) 108.6 no
C(1) C(3) H(5) 109.5 no
C(1) C(3) H(6) 109.5 no
C(1) C(3) H(7) 109.5 no
H(5) C(3) H(6) 109.5 no
H(5) C(3) H(7) 109.5 no
H(6) C(3) H(7) 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.249(4) yes
O(2) C(2) 1.262(4) yes
N(1) C(1) 1.481(4) yes
C(1) C(2) 1.535(5) yes
C(1) C(3) 1.506(5) yes
N(1) H(1) 0.890 no
N(1) H(2) 0.890 no
N(1) H(3) 0.890 no
C(1) H(4) 0.980 no
C(3) H(5) 0.960 no
C(3) H(6) 0.960 no
C(3) H(7) 0.960 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) N(1) 2.855(4) 4_674
O(2) N(1) 2.803(4) 1_554
O(2) N(1) 2.821(4) 2_544
N(1) O(1) 2.855(4) 4_675
N(1) O(2) 2.803(4) 1_556
N(1) O(2) 2.821(4) 2_555
O(1) H(1) 1.999 4_674
O(1) H(2) 2.707 1_554
O(1) H(4) 2.662 2_554
O(1) H(6) 2.806 1_565
O(2) H(2) 1.919 1_554
O(2) H(3) 1.954 2_544
O(2) H(5) 2.894 4_664
O(2) H(6) 2.933 2_554
O(2) H(7) 2.886 1_554
N(1) H(4) 2.988 2_555
C(2) H(2) 2.603 1_554
C(2) H(3) 2.819 2_544
C(2) H(4) 2.963 2_554
H(1) O(1) 1.999 4_675
H(2) O(1) 2.707 1_556
H(2) O(2) 1.919 1_556
H(2) C(2) 2.603 1_556
H(2) H(4) 2.688 2_555
H(3) O(2) 1.954 2_555
H(3) C(2) 2.819 2_555
H(3) H(4) 2.513 2_555
H(3) H(6) 2.860 1_565
H(3) H(7) 2.900 1_565
H(4) O(1) 2.662 2_545
H(4) N(1) 2.988 2_544
H(4) C(2) 2.963 2_545
H(4) H(2) 2.688 2_544
H(4) H(3) 2.513 2_544
H(5) O(2) 2.894 4_665
H(5) H(6) 2.761 4_665
H(5) H(7) 2.477 4_664
H(6) O(1) 2.806 1_545
H(6) O(2) 2.933 2_545
H(6) H(3) 2.860 1_545
H(6) H(5) 2.761 4_664
H(7) O(2) 2.886 1_556
H(7) H(3) 2.900 1_545
H(7) H(5) 2.477 4_665
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
N(1) C(1) C(2) O(1) 15.8(4)
N(1) C(1) C(2) O(2) -164.2(2)
C(3) C(1) C(2) O(1) -106.0(3)
C(3) C(1) C(2) O(2) 74.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 7311725
