#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/06/1100675.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_1100675
loop_
_publ_author_name
'Doi, Mitsunobu'
'Ijiri, Yoshio'
'Akagi, Masao'
'Uenishi, Miharu'
'Urata, Hidehito'
_publ_section_title
;
 Crystal Structure of 5'-Hydroxythalidomide In Vivo Metabolite of
 Thalidomide in Humans
;
_journal_name_full
;
 Analytical Sciences: X-ray Structure Analysis Online
;
_journal_page_first              x51
_journal_page_last               x52
_journal_paper_doi               10.2116/analscix.19.x51
_journal_volume                  19
_journal_year                    2003
_chemical_formula_moiety         'C13 H10 N2 O5'
_chemical_formula_sum            'C13 H10 N2 O5'
_chemical_formula_weight         274.23
_chemical_name_common            5hthalid
_chemical_name_systematic        5'-Hydroxythalidomide
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.7240(17)
_cell_length_b                   7.9633(6)
_cell_length_c                   13.6074(11)
_cell_measurement_reflns_used    4272
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.7
_cell_volume                     2341.4(3)
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measurement_device_type  'Bruker AXS, SMART APEX area detector'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'MacScience, M18XCE rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9927
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        0.08
_diffrn_standards_interval_count 9927
_diffrn_standards_interval_time  360
_diffrn_standards_number         135
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.8821
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.248
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+5.7973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                2661
_reflns_number_total             2770
_reflns_threshold_expression     I>2σ(I)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1100675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.02939(10) 0.6082(2) 0.63039(14) 0.0153(4) Uani 1 1 d . . .
O1 O 0.01652(7) 0.46223(19) 0.61661(12) 0.0213(4) Uani 1 1 d . . .
N2 N 0.08850(8) 0.6692(2) 0.66432(13) 0.0150(4) Uani 1 1 d . . .
C3 C 0.09019(10) 0.8447(3) 0.66399(14) 0.0151(4) Uani 1 1 d . . .
O3 O 0.13670(7) 0.92752(19) 0.68384(12) 0.0213(4) Uani 1 1 d . . .
C3A C 0.02551(9) 0.9003(3) 0.63583(14) 0.0141(4) Uani 1 1 d . . .
C4 C 0.00125(10) 1.0609(3) 0.62712(15) 0.0171(4) Uani 1 1 d . . .
H1 H 0.0266 1.1572 0.6400 0.021 Uiso 1 1 calc R . .
C5 C -0.06220(11) 1.0753(3) 0.59859(16) 0.0206(5) Uani 1 1 d . . .
H2 H -0.0805 1.1835 0.5916 0.025 Uiso 1 1 calc R . .
C6 C -0.09901(11) 0.9330(3) 0.58023(16) 0.0224(5) Uani 1 1 d . . .
H3 H -0.1421 0.9462 0.5615 0.027 Uiso 1 1 calc R . .
C7 C -0.07405(10) 0.7719(3) 0.58881(15) 0.0188(4) Uani 1 1 d . . .
H4 H -0.0991 0.6749 0.5761 0.023 Uiso 1 1 calc R . .
C7A C -0.01107(10) 0.7595(2) 0.61679(14) 0.0145(4) Uani 1 1 d . . .
N1' N 0.20422(8) 0.3992(2) 0.56697(12) 0.0151(4) Uani 1 1 d . . .
H5 H 0.2181 0.3819 0.5093 0.018 Uiso 1 1 calc R . .
C2' C 0.16300(9) 0.5297(3) 0.57195(15) 0.0156(4) Uani 1 1 d . . .
O2' O 0.14389(8) 0.6066(2) 0.49844(11) 0.0225(4) Uani 1 1 d . . .
C3' C 0.14497(9) 0.5700(3) 0.67457(14) 0.0138(4) Uani 1 1 d . . .
H6 H 0.1784 0.6430 0.7077 0.017 Uiso 1 1 calc R . .
C4' C 0.14231(9) 0.4122(3) 0.73765(14) 0.0154(4) Uani 1 1 d . . .
H7 H 0.1323 0.4429 0.8047 0.018 Uiso 1 1 calc R . .
H8 H 0.1095 0.3361 0.7076 0.018 Uiso 1 1 calc R . .
C5' C 0.20469(9) 0.3238(3) 0.74428(14) 0.0141(4) Uani 1 1 d . . .
H9 H 0.2355 0.4013 0.7801 0.017 Uiso 1 1 calc R . .
O5' O 0.20621(7) 0.17306(19) 0.79890(11) 0.0175(3) Uani 1 1 d . . .
H10 H 0.1799(13) 0.101(4) 0.765(2) 0.025(7) Uiso 1 1 d . . .
C6' C 0.22604(9) 0.2929(3) 0.64228(15) 0.0142(4) Uani 1 1 d . . .
O6' O 0.26113(7) 0.1789(2) 0.62674(11) 0.0225(4) Uani 1 1 d . . .
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'
