#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239054.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_2239054
loop_
_publ_author_name
'Rosen, Gerald M.'
'Muralidharan, Sukumaran'
'Zavalij, Peter Y.'
'Kao, Joseph P. Y.'
_publ_section_title
;
 Dimethyl 5-acetyl-1-hydroxy-4-methyl-1<i>H</i>-pyrrole-2,3-dicarboxylate,
 an oxidation-resistant <i>N</i>-hydroxypyrrole
;
_journal_coeditor_code           LD2115
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o110
_journal_page_last               o111
_journal_paper_doi               10.1107/S1600536813034466
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H13 N O6'
_chemical_formula_moiety         'C11 H13 N O6'
_chemical_formula_sum            'C11 H13 N O6'
_chemical_formula_weight         255.22
_chemical_name_systematic
;
Dimethyl 5-acetyl-1-hydroxy-4-methyl-1<i>H</i>-pyrrole-2,3-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3893(8)
_cell_length_b                   15.1803(12)
_cell_length_c                   7.5789(6)
_cell_measurement_reflns_used    13127
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.4
_cell_volume                     1178.45(16)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2010)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2010)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2010)'
_computing_molecular_graphics
;
<i>XSHELL</i> (Bruker, 2010) and <i>Mercury</i> (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material  '<i>publCIF</i> (Westrip, 2010)'
_computing_structure_refinement  '<i>SHELXL2012</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19259
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+0.4962P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0643
_reflns_number_gt                2836
_reflns_number_total             3437
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ld2115sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239054
_cod_database_fobs_code          2239054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_symmetry_multiplicity
N N1 0.58967(7) 0.15991(5) 0.01532(11) 0.02245(15) Uani d 1 1
C C1 0.57608(9) 0.25121(6) 0.00825(12) 0.02170(17) Uani d 1 1
C C2 0.69238(9) 0.28546(6) 0.10473(12) 0.02101(16) Uani d 1 1
C C3 0.77256(8) 0.21282(6) 0.16540(12) 0.02102(16) Uani d 1 1
C C4 0.70478(8) 0.13542(6) 0.10655(12) 0.02093(17) Uani d 1 1
O O1 0.49892(7) 0.09969(5) -0.06513(11) 0.03059(16) Uani d 1 1
H H1 0.4367(15) 0.1346(10) -0.121(2) 0.055(4) Uiso d 1 1
C C5 0.45803(9) 0.28874(6) -0.09308(13) 0.02522(18) Uani d 1 1
O O5 0.37225(7) 0.23953(5) -0.17286(11) 0.03488(18) Uani d 1 1
C C6 0.44010(11) 0.38675(7) -0.10178(16) 0.0318(2) Uani d 1 1
H H61 0.3632(15) 0.3989(10) -0.190(2) 0.056(4) Uiso d 1 1
H H62 0.4261(14) 0.4098(10) 0.012(2) 0.048(4) Uiso d 1 1
H H63 0.5176(13) 0.4162(9) -0.1332(17) 0.039(4) Uiso d 1 1
C C7 0.72552(11) 0.38090(6) 0.13774(14) 0.02725(19) Uani d 1 1
H H71 0.8031(14) 0.3861(10) 0.227(2) 0.050(4) Uiso d 1 1
H H72 0.6559(14) 0.4127(9) 0.1794(18) 0.044(4) Uiso d 1 1
H H73 0.7376(13) 0.4103(9) 0.0300(19) 0.044(4) Uiso d 1 1
C C8 0.90325(9) 0.21540(6) 0.27407(13) 0.02425(18) Uani d 1 1
O O8 0.96516(8) 0.28077(5) 0.32002(13) 0.0425(2) Uani d 1 1
O O9 0.94825(7) 0.13382(5) 0.31885(10) 0.02999(16) Uani d 1 1
C C9 1.07658(11) 0.13084(9) 0.42886(18) 0.0394(3) Uani d 1 1
H H91 1.0973(16) 0.0679(11) 0.439(2) 0.062(5) Uiso d 1 1
H H92 1.1394(14) 0.1618(10) 0.3656(19) 0.046(4) Uiso d 1 1
H H93 1.0726(13) 0.1588(10) 0.543(2) 0.046(4) Uiso d 1 1
C C10 0.74086(8) 0.04013(6) 0.13628(12) 0.02129(17) Uani d 1 1
O O10 0.70851(7) -0.00387(4) 0.25304(10) 0.02722(15) Uani d 1 1
O O11 0.81287(7) 0.01306(5) 0.01819(10) 0.02943(16) Uani d 1 1
C C11 0.86684(14) -0.07523(8) 0.04835(18) 0.0383(3) Uani d 1 1
H H111 0.9238(14) -0.0816(9) -0.0377(19) 0.046(4) Uiso d 1 1
H H112 0.9172(15) -0.0775(11) 0.170(2) 0.060(5) Uiso d 1 1
H H113 0.7977(15) -0.1177(11) 0.037(2) 0.059(5) Uiso d 1 1
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
N1 0.0195(3) 0.0176(3) 0.0295(4) -0.0019(3) 0.0019(3) -0.0014(3)
C1 0.0216(4) 0.0181(4) 0.0260(4) 0.0008(3) 0.0056(3) 0.0002(3)
C2 0.0233(4) 0.0185(4) 0.0220(4) -0.0006(3) 0.0061(3) -0.0007(3)
C3 0.0203(4) 0.0196(4) 0.0232(4) -0.0016(3) 0.0038(3) -0.0009(3)
C4 0.0192(4) 0.0186(4) 0.0250(4) -0.0002(3) 0.0040(3) -0.0004(3)
O1 0.0225(3) 0.0219(3) 0.0438(4) -0.0053(3) -0.0046(3) -0.0031(3)
C5 0.0224(4) 0.0257(4) 0.0284(4) 0.0036(3) 0.0068(3) 0.0028(4)
O5 0.0246(3) 0.0322(4) 0.0446(4) 0.0018(3) -0.0036(3) 0.0005(3)
C6 0.0282(5) 0.0256(5) 0.0414(6) 0.0066(4) 0.0055(4) 0.0056(4)
C7 0.0338(5) 0.0184(4) 0.0291(5) -0.0026(4) 0.0039(4) -0.0019(4)
C8 0.0223(4) 0.0251(4) 0.0253(4) -0.0020(3) 0.0037(3) 0.0002(3)
O8 0.0323(4) 0.0298(4) 0.0591(5) -0.0082(3) -0.0103(4) -0.0025(4)
O9 0.0226(3) 0.0286(4) 0.0362(4) 0.0011(3) -0.0027(3) 0.0030(3)
C9 0.0268(5) 0.0473(7) 0.0399(6) 0.0063(5) -0.0063(4) 0.0017(5)
C10 0.0193(4) 0.0186(4) 0.0247(4) -0.0003(3) 0.0001(3) -0.0014(3)
O10 0.0305(3) 0.0218(3) 0.0303(3) -0.0020(3) 0.0079(3) 0.0013(3)
O11 0.0368(4) 0.0229(3) 0.0308(4) 0.0106(3) 0.0120(3) 0.0057(3)
C11 0.0488(7) 0.0259(5) 0.0442(6) 0.0169(5) 0.0190(6) 0.0075(5)
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 N1 O1 122.20(8)
C4 N1 C1 111.99(7)
O1 N1 C1 125.78(8)
N1 C1 C2 106.00(8)
N1 C1 C5 118.84(8)
C2 C1 C5 135.11(8)
C1 C2 C3 106.86(8)
C1 C2 C7 126.74(8)
C3 C2 C7 126.40(8)
C4 C3 C2 108.24(8)
C4 C3 C8 124.69(8)
C2 C3 C8 127.06(8)
N1 C4 C3 106.90(8)
N1 C4 C10 121.82(8)
C3 C4 C10 131.24(8)
N1 O1 H1 101.8(10)
O5 C5 C1 119.78(9)
O5 C5 C6 120.16(9)
C1 C5 C6 120.06(9)
C5 C6 H61 107.5(9)
C5 C6 H62 111.0(9)
H61 C6 H62 108.4(12)
C5 C6 H63 111.2(8)
H61 C6 H63 111.1(11)
H62 C6 H63 107.6(11)
C2 C7 H71 109.7(9)
C2 C7 H72 112.0(8)
H71 C7 H72 108.4(11)
C2 C7 H73 111.6(8)
H71 C7 H73 110.1(12)
H72 C7 H73 104.9(11)
O8 C8 O9 122.66(9)
O8 C8 C3 125.82(9)
O9 C8 C3 111.52(8)
C8 O9 C9 114.87(8)
O9 C9 H91 104.2(10)
O9 C9 H92 108.9(8)
H91 C9 H92 110.4(12)
O9 C9 H93 109.0(8)
H91 C9 H93 113.3(13)
H92 C9 H93 110.7(12)
O10 C10 O11 125.81(8)
O10 C10 C4 123.55(8)
O11 C10 C4 110.64(8)
C10 O11 C11 115.20(8)
O11 C11 H111 104.6(9)
O11 C11 H112 108.1(10)
H111 C11 H112 110.1(12)
O11 C11 H113 110.0(9)
H111 C11 H113 114.3(13)
H112 C11 H113 109.5(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.3304(11)
N1 O1 1.3799(10)
N1 C1 1.3932(11)
C1 C2 1.4033(12)
C1 C5 1.4503(13)
C2 C3 1.4118(12)
C2 C7 1.5005(13)
C3 C4 1.4037(12)
C3 C8 1.4661(12)
C4 C10 1.5018(12)
O1 H1 0.888(16)
C5 O5 1.2399(12)
C5 C6 1.4995(14)
C6 H61 0.968(15)
C6 H62 0.963(15)
C6 H63 0.985(14)
C7 H71 0.963(15)
C7 H72 0.965(14)
C7 H73 0.957(14)
C8 O8 1.2020(12)
C8 O9 1.3470(12)
O9 C9 1.4501(13)
C9 H91 0.980(17)
C9 H92 0.991(15)
C9 H93 0.971(15)
C10 O10 1.2007(11)
C10 O11 1.3242(11)
O11 C11 1.4561(12)
C11 H111 0.956(14)
C11 H112 0.981(16)
C11 H113 0.958(16)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O5 0.888(16) 1.746(16) 2.5583(11) 150.8(14)
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
C4 N1 C1 C2 -0.55(11)
O1 N1 C1 C2 -178.69(8)
C4 N1 C1 C5 177.39(8)
O1 N1 C1 C5 -0.75(14)
N1 C1 C2 C3 0.48(10)
C5 C1 C2 C3 -176.97(10)
N1 C1 C2 C7 -179.43(9)
C5 C1 C2 C7 3.13(17)
C1 C2 C3 C4 -0.26(10)
C7 C2 C3 C4 179.64(9)
C1 C2 C3 C8 -179.17(9)
C7 C2 C3 C8 0.73(15)
O1 N1 C4 C3 178.61(8)
C1 N1 C4 C3 0.39(11)
O1 N1 C4 C10 -3.29(14)
C1 N1 C4 C10 178.50(8)
C2 C3 C4 N1 -0.07(10)
C8 C3 C4 N1 178.87(8)
C2 C3 C4 C10 -177.93(9)
C8 C3 C4 C10 1.01(15)
N1 C1 C5 O5 -0.77(14)
C2 C1 C5 O5 176.43(10)
N1 C1 C5 C6 179.45(9)
C2 C1 C5 C6 -3.36(16)
C4 C3 C8 O8 176.89(10)
C2 C3 C8 O8 -4.37(16)
C4 C3 C8 O9 -3.19(13)
C2 C3 C8 O9 175.56(9)
O8 C8 O9 C9 0.77(15)
C3 C8 O9 C9 -179.15(9)
N1 C4 C10 O10 -82.60(12)
C3 C4 C10 O10 94.99(12)
N1 C4 C10 O11 97.95(10)
C3 C4 C10 O11 -84.45(12)
O10 C10 O11 C11 -6.69(15)
C4 C10 O11 C11 172.74(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086326