#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/15/2201566.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_2201566
loop_
_publ_author_name
'Yapp, Donald T. T.'
'Steed, Jonathan W.'
'Houghton, Peter J.'
_publ_section_title
;
 4-Hydroxy-N-methylproline
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o988
_journal_page_last               o989
_journal_paper_doi               10.1107/S160053680201406X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C6 H11 N O3'
_chemical_formula_moiety         'C6 H11 N O3'
_chemical_formula_sum            'C6 H11 N O3'
_chemical_formula_weight         145.16
_chemical_name_systematic
;
n-Methyl-4-hydroxyproline
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.684(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6709(6)
_cell_length_b                   5.7814(5)
_cell_length_c                   8.8881(6)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     336.85(5)
_computing_cell_refinement       'DENZO-SMN (Otwinoski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'XSeed (Barbour, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.874
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ and ω'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1732
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(Otwinowski & Minor, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.182
_refine_ls_abs_structure_details '(Flack, 1983), 323 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.3(11)
_refine_ls_extinction_coef       0.086(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1174
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0265
_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)+(0.0251P)²+0.0385P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0613
_reflns_number_gt                1112
_reflns_number_total             1174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6161.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2201566
_cod_database_fobs_code          2201566
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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
_atom_site_type_symbol
O1 0.65316(15) 0.4875(2) 0.77293(10) 0.0198(3) Uani d . 1 . . O
O2 0.60321(14) 0.69843(19) 0.97492(10) 0.0173(3) Uani d . 1 . . O
O3 0.12484(16) 0.9698(2) 0.45160(11) 0.0212(3) Uani d . 1 . . O
N1 0.23753(19) 0.8671(2) 0.82572(13) 0.0126(3) Uani d . 1 . . N
C1 0.5611(2) 0.6353(3) 0.83761(15) 0.0139(3) Uani d . 1 . . C
C2 0.3805(2) 0.7544(3) 0.73613(15) 0.0139(3) Uani d . 1 . . C
C3 0.4369(2) 0.9602(3) 0.64447(16) 0.0163(3) Uani d . 1 . . C
C4 0.2313(2) 1.0755(3) 0.58794(16) 0.0163(4) Uani d . 1 . . C
C5 0.1079(2) 1.0278(3) 0.71444(16) 0.0172(4) Uani d . 1 . . C
C6 0.1198(2) 0.7025(3) 0.90355(16) 0.0182(4) Uani d . 1 . . C
H6A 0.2142 0.6019 0.9717 0.027 Uiso calc R 1 . . H
H6B 0.0317 0.6081 0.8268 0.027 Uiso calc R 1 . . H
H6C 0.0356 0.7889 0.9636 0.027 Uiso calc R 1 . . H
H1 0.313(3) 0.967(4) 0.9043(19) 0.024(4) Uiso d . 1 . . H
H5A -0.023(3) 0.943(3) 0.6735(19) 0.020(4) Uiso d . 1 . . H
H3 0.205(3) 0.971(4) 0.385(2) 0.041(5) Uiso d . 1 . . H
H3B 0.522(3) 1.064(3) 0.7104(18) 0.021(4) Uiso d . 1 . . H
H2 0.304(2) 0.644(3) 0.6706(15) 0.008(4) Uiso d . 1 . . H
H5B 0.084(3) 1.164(4) 0.7692(19) 0.028(5) Uiso d . 1 . . H
H4 0.243(2) 1.237(4) 0.5758(17) 0.016(4) Uiso d . 1 . . H
H3A 0.499(3) 0.914(3) 0.5594(18) 0.023(5) Uiso d . 1 . . H
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 0.0196(5) 0.0205(7) 0.0204(5) 0.0055(5) 0.0068(4) 0.0023(5)
O2 0.0203(6) 0.0159(6) 0.0137(5) 0.0010(5) -0.0023(4) 0.0001(4)
O3 0.0197(5) 0.0311(7) 0.0120(5) -0.0011(6) 0.0009(4) -0.0004(5)
N1 0.0132(6) 0.0130(7) 0.0112(6) 0.0003(5) 0.0009(5) -0.0002(5)
C1 0.0131(7) 0.0123(8) 0.0166(7) -0.0027(6) 0.0036(6) 0.0031(6)
C2 0.0150(8) 0.0140(8) 0.0122(6) -0.0007(7) 0.0017(6) -0.0026(6)
C3 0.0186(8) 0.0170(8) 0.0132(7) 0.0000(7) 0.0027(6) 0.0020(6)
C4 0.0195(8) 0.0144(9) 0.0145(7) -0.0009(7) 0.0015(6) 0.0012(6)
C5 0.0174(8) 0.0198(10) 0.0139(7) 0.0053(7) 0.0014(6) 0.0012(6)
C6 0.0168(8) 0.0194(9) 0.0188(7) -0.0042(8) 0.0047(6) 0.0013(7)
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
C4 O3 H3 107.7(15)
C6 N1 C2 114.38(12)
C6 N1 C5 114.33(12)
C2 N1 C5 105.27(10)
C6 N1 H1 107.1(10)
C2 N1 H1 110.2(10)
C5 N1 H1 105.2(12)
O1 C1 O2 127.19(14)
O1 C1 C2 115.87(12)
O2 C1 C2 116.93(13)
N1 C2 C3 100.87(12)
N1 C2 C1 113.05(10)
C3 C2 C1 114.88(12)
N1 C2 H2 107.3(9)
C3 C2 H2 110.9(9)
C1 C2 H2 109.4(9)
C4 C3 C2 102.77(12)
C4 C3 H3B 108.9(10)
C2 C3 H3B 109.9(10)
C4 C3 H3A 110.6(10)
C2 C3 H3A 112.7(11)
H3B C3 H3A 111.6(14)
O3 C4 C3 111.67(13)
O3 C4 C5 107.20(13)
C3 C4 C5 104.59(12)
O3 C4 H4 111.5(10)
C3 C4 H4 112.3(10)
C5 C4 H4 109.3(9)
N1 C5 C4 105.69(12)
N1 C5 H5A 107.0(10)
C4 C5 H5A 111.6(9)
N1 C5 H5B 107.8(11)
C4 C5 H5B 112.8(11)
H5A C5 H5B 111.6(14)
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 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
O1 C1 . 1.2525(18) ?
O2 C1 . 1.2547(16) ?
O3 C4 . 1.4236(18) ?
N1 C6 . 1.4843(18) ?
N1 C2 . 1.4999(17) ?
N1 C5 . 1.508(2) ?
N1 H1 . 0.971(19) ?
C1 C2 . 1.528(2) ?
C2 C3 . 1.527(2) ?
C2 H2 . 0.948(15) ?
C3 C4 . 1.524(2) ?
C3 H3B . 0.948(18) ?
C3 H3A . 0.963(17) ?
C4 C5 . 1.536(2) ?
C4 H4 . 0.94(2) ?
C5 H5A . 1.01(2) ?
C5 H5B . 0.96(2) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 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
N1 H1 O2 2_657 0.971(19) 1.74(2) 2.6907(16) 164.7(18)
O3 H3 O1 2_656 0.87(2) 1.84(2) 2.6985(13) 173(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9943383
