#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/76/2007694.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_2007694
loop_
_publ_author_name
'Eknoian, Michael W.'
'Webb, Thomas R.'
'Worley, S. Davis'
'Fleury, Jennifer R.'
'Maddox, Spencer D.'
_publ_section_title
;
 Two Oxazolidinone Derivatives
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1529
_journal_page_last               1532
_journal_paper_doi               10.1107/S0108270198005654
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C5 H9 N O3'
_chemical_formula_sum            'C5 H9 N O3'
_chemical_formula_weight         131.13
_chemical_name_systematic        '  4-hydroxymethyl-4-methyl-2-oxazolidinone'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.96(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.004(2)
_cell_length_b                   7.065(2)
_cell_length_c                   9.851(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      7.5
_cell_volume                     620.6(3)
_computing_cell_refinement       P3
_computing_data_collection       'P3 (Siemens, 1990a)'
_computing_data_reduction        'SHELXTL (Siemens, 1994)'
_computing_molecular_graphics    'XP in SHELXTL'
_computing_publication_material  'XCIF in SHELXTL'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       2\q-\w
_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  0.058
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1523
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   '\y scan of 6 reflections'
_exptl_absorpt_process_details   '(XEMP; Siemens, 1990b)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick diamond-shaped plate'
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_obs   1.119
_refine_ls_hydrogen_treatment
'H atoms: amido and hydroxyl H atoms refined, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_restrained_S_obs      1.119
_refine_ls_R_factor_all          0.073
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.1099P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.122
_refine_ls_wR_factor_obs         0.106
_reflns_number_observed          999
_reflns_number_total             1435
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            bk1395.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.1099P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.1099P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2007694
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 0.0661(10) 0.0472(9) 0.0554(9) -0.0126(7) 0.0020(7) -0.0017(7)
C1 0.0348(9) 0.0498(11) 0.0384(9) -0.0060(8) 0.0072(8) 0.0021(8)
N 0.0352(8) 0.0441(9) 0.0335(7) -0.0003(7) 0.0022(6) 0.0045(7)
C2 0.0325(8) 0.0408(10) 0.0343(8) 0.0020(7) 0.0032(7) -0.0015(7)
C3 0.0352(9) 0.0503(12) 0.0448(10) 0.0055(8) 0.0025(8) 0.0020(9)
O2 0.0399(7) 0.0566(9) 0.0454(7) -0.0017(6) -0.0089(6) -0.0009(6)
C4 0.0352(9) 0.0417(10) 0.0425(9) -0.0033(8) 0.0026(7) -0.0007(8)
O3 0.0410(7) 0.0497(8) 0.0394(7) 0.0092(6) 0.0096(5) 0.0042(6)
C5 0.0563(12) 0.0602(14) 0.0483(11) 0.0052(10) 0.0094(9) -0.0129(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.1765(2) -0.2455(2) 0.9134(2) 0.0569(4) Uani d . 1 . O
C1 0.1845(2) -0.0748(3) 0.9312(2) 0.0408(4) Uani d . 1 . C
N 0.2627(2) 0.0215(2) 1.03295(15) 0.0379(4) Uani d . 1 . N
H1A 0.334(2) -0.035(3) 1.081(2) 0.045 Uiso d . 1 . H
C2 0.2702(2) 0.2226(3) 1.0014(2) 0.0360(4) Uani d . 1 . C
C3 0.1350(2) 0.2354(3) 0.8884(2) 0.0437(5) Uani d . 1 . C
H3A 0.0488(2) 0.2879(3) 0.9243(2) 0.052 Uiso calc R 1 . H
H3B 0.1582(2) 0.3149(3) 0.8138(2) 0.052 Uiso calc R 1 . H
O2 0.10522(14) 0.0445(2) 0.84186(13) 0.0487(4) Uani d . 1 . O
C4 0.4175(2) 0.2673(3) 0.9476(2) 0.0400(4) Uani d . 1 . C
H4A 0.4124(2) 0.3944(3) 0.9100(2) 0.048 Uiso calc R 1 . H
H4B 0.4987(2) 0.2641(3) 1.0234(2) 0.048 Uiso calc R 1 . H
O3 0.44969(14) 0.1384(2) 0.84515(14) 0.0430(4) Uani d . 1 . O
H3C 0.412(2) 0.182(3) 0.770(2) 0.052 Uiso d . 1 . H
C5 0.2528(2) 0.3471(3) 1.1237(2) 0.0547(6) Uani d . 1 . C
H5A 0.1600(2) 0.3178(3) 1.1566(2) 0.082 Uiso calc R 1 . H
H5B 0.2527(2) 0.4777(3) 1.0966(2) 0.082 Uiso calc R 1 . H
H5C 0.3347(2) 0.3247(3) 1.1952(2) 0.082 Uiso calc R 1 . H
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
_geom_angle_publ_flag
O1 C1 N 129.0(2) yes
O1 C1 O2 120.6(2) yes
N C1 O2 110.4(2) yes
C1 N C2 111.93(15) yes
N C2 C5 112.5(2) yes
N C2 C4 110.09(14) yes
C5 C2 C4 110.2(2) yes
N C2 C3 99.02(14) yes
C5 C2 C3 112.52(15) yes
C4 C2 C3 112.04(15) yes
O2 C3 C2 105.67(14) yes
C1 O2 C3 108.64(14) yes
O3 C4 C2 112.76(14) yes
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 . 1.219(2) yes
C1 N . 1.330(2) yes
C1 O2 . 1.349(2) yes
N C2 . 1.457(2) yes
C2 C5 . 1.517(3) yes
C2 C4 . 1.528(2) yes
C2 C3 . 1.535(2) yes
C3 O2 . 1.438(2) yes
C4 O3 . 1.419(2) yes
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
N H1A O3 3_657 0.84(2) 2.12(2) 2.926(2) 162(2)
O3 H3C O1 2_556 0.83(2) 1.94(2) 2.765(2) 174(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 214802
2 PubChem 92140313
