#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200227.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_2200227
loop_
_publ_author_name
'Kubo, Kanji '
' Tsuruta, Tetsuya '
'Mori, Akira'
_publ_section_title
;
 2-Butanoyloxy-5-nitrotropone
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o326
_journal_page_last               o327
_journal_paper_doi               10.1107/S1600536801003749
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C11 H11 N O5'
_chemical_formula_sum            'C11 H11 N O5'
_chemical_formula_weight         237.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.052(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8585(14)
_cell_length_b                   10.7092(11)
_cell_length_c                   8.3657(14)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.1
_cell_measurement_theta_min      9.1
_cell_volume                     1122.2(3)
_computing_cell_refinement       ' CAD-4 Software'
_computing_data_collection       ' CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        ' MolEN (Fair, 1990)'
_computing_molecular_graphics    'Xtal_GX (Hall & du Boulay, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    ' SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .000
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .073
_diffrn_reflns_av_sigmaI/netI    .1310
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2559
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        .1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .112
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  .981
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   ' (North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .23
_exptl_crystal_size_min          .23
_refine_diff_density_max         .19
_refine_diff_density_min         -.18
_refine_ls_extinction_coef       .018(3)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .954
_refine_ls_R_factor_all          .212
_refine_ls_R_factor_gt           .055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0673P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .168
_reflns_number_gt                953
_reflns_number_total             2450
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6006.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value ' psi-scan' changed to
'psi-scan' 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:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2200227
_cod_database_fobs_code          2200227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -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
N1 .2129(2) .1110(3) .4515(4) .0569(8) Uani d . 1 . . N
O1 .66475(19) .2185(2) .7017(3) .0744(8) Uani d . 1 . . O
O2 .65022(17) -.0067(2) .8162(3) .0640(7) Uani d . 1 . . O
O3 .15680(19) .0242(2) .4730(4) .0788(9) Uani d . 1 . . O
O4 .18189(18) .1968(2) .3565(3) .0739(8) Uani d . 1 . . O
O5 .6630(2) .1186(3) 1.0328(3) .0863(9) Uani d . 1 . . O
C1 .5734(3) .1770(3) .6764(4) .0522(9) Uani d . 1 . . C
C2 .5561(3) .0518(3) .7365(4) .0487(8) Uani d . 1 . . C
C3 .4674(2) -.0177(3) .7161(4) .0544(9) Uani d . 1 . . C
H3 .4760 -.0947 .7688 .065 Uiso calc R 1 . . H
C4 .3627(2) .0088(3) .6261(4) .0494(8) Uani d . 1 . . C
H4 .3126 -.0541 .6242 .059 Uiso calc R 1 . . H
C5 .3266(2) .1128(3) .5436(4) .0452(8) Uani d . 1 . . C
C6 .3820(3) .2241(3) .5300(4) .0615(10) Uani d . 1 . . C
H6 .3409 .2877 .4719 .074 Uiso calc R 1 . . H
C7 .4855(3) .2521(3) .5882(5) .0663(10) Uani d . 1 . . C
H7 .5037 .3338 .5685 .080 Uiso calc R 1 . . H
C8 .7031(3) .0443(4) .9621(5) .0616(10) Uani d . 1 . . C
C9 .8117(3) -.0124(4) 1.0177(6) .0858(13) Uani d . 1 . . C
H9A .8060 -.0867 1.0816 .103 Uiso calc R 1 . . H
H9B .8371 -.0381 .9221 .103 Uiso calc R 1 . . H
C10 .8914(4) .0733(7) 1.1180(5) .116(2) Uani d . 1 . . C
H10A .8634 .1045 1.2087 .139 Uiso calc R 1 . . H
H10B .9559 .0267 1.1637 .139 Uiso calc R 1 . . H
C11 .9185(4) .1800(5) 1.0241(11) .168(3) Uani d . 1 . . C
H11A .9697 .2321 1.0951 .252 Uiso calc R 1 . . H
H11B .8552 .2275 .9801 .252 Uiso calc R 1 . . H
H11C .9483 .1500 .9360 .252 Uiso calc R 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
N1 .0477(17) .0522(18) .067(2) .0098(16) .0056(15) -.0056(16)
O1 .0505(14) .083(2) .0864(18) -.0152(14) .0078(13) .0173(15)
O2 .0486(13) .0644(16) .0716(16) .0120(12) -.0016(12) .0002(13)
O3 .0464(14) .0535(16) .129(2) -.0075(13) .0032(15) .0043(15)
O4 .0616(16) .0751(19) .0762(18) .0141(14) -.0031(13) .0114(15)
O5 .0777(19) .122(3) .0578(16) .0102(18) .0132(14) -.0087(17)
C1 .049(2) .053(2) .055(2) -.0014(17) .0129(17) .0007(17)
C2 .046(2) .0495(19) .050(2) .0070(17) .0095(16) -.0001(16)
C3 .048(2) .047(2) .067(2) .0037(16) .0113(17) .0128(17)
C4 .0438(18) .0417(19) .063(2) -.0012(16) .0124(16) .0013(16)
C5 .0383(17) .0450(19) .0530(19) .0048(15) .0117(15) -.0034(17)
C6 .053(2) .042(2) .086(3) .0063(17) .0066(19) .0125(18)
C7 .058(2) .0401(18) .098(3) -.0049(18) .012(2) .013(2)
C8 .057(2) .070(3) .054(2) .003(2) .0060(19) .009(2)
C9 .063(3) .079(3) .102(3) .006(2) -.011(2) .019(2)
C10 .063(3) .202(6) .074(3) .012(4) -.004(2) -.034(4)
C11 .086(4) .085(4) .318(10) -.021(3) .016(5) -.023(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
O3 N1 O4 123.7(3)
O3 N1 C5 118.6(3)
O4 N1 C5 117.7(3)
C8 O2 C2 116.8(3)
O1 C1 C7 119.5(3)
O1 C1 C2 119.0(3)
C7 C1 C2 121.5(3)
C3 C2 O2 115.7(3)
C3 C2 C1 130.9(3)
O2 C2 C1 113.1(3)
C2 C3 C4 129.5(3)
C2 C3 H3 115.2
C4 C3 H3 115.2
C5 C4 C3 128.3(3)
C5 C4 H4 115.9
C3 C4 H4 115.9
C4 C5 C6 128.6(3)
C4 C5 N1 116.2(3)
C6 C5 N1 115.1(3)
C7 C6 C5 129.7(3)
C7 C6 H6 115.2
C5 C6 H6 115.2
C6 C7 C1 131.0(3)
C6 C7 H7 114.5
C1 C7 H7 114.5
O5 C8 O2 122.1(3)
O5 C8 C9 127.0(4)
O2 C8 C9 110.8(3)
C10 C9 C8 113.6(4)
C10 C9 H9A 108.8
C8 C9 H9A 108.8
C10 C9 H9B 108.8
C8 C9 H9B 108.8
H9A C9 H9B 107.7
C11 C10 C9 113.2(4)
C11 C10 H10A 108.9
C9 C10 H10A 108.9
C11 C10 H10B 108.9
C9 C10 H10B 108.9
H10A C10 H10B 107.7
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 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
N1 O3 . 1.215(3) no
N1 O4 . 1.221(3) no
N1 C5 . 1.491(4) no
O1 C1 . 1.230(4) no
O2 C8 . 1.370(4) ?
O2 C2 . 1.392(3) no
O5 C8 . 1.178(4) ?
C1 C7 . 1.447(4) no
C1 C2 . 1.466(5) no
C2 C3 . 1.339(4) no
C3 C4 . 1.415(4) no
C3 H3 . .9300 ?
C4 C5 . 1.337(4) no
C4 H4 . .9300 ?
C5 C6 . 1.406(4) no
C6 C7 . 1.343(4) no
C6 H6 . .9300 ?
C7 H7 . .9300 ?
C8 C9 . 1.497(5) ?
C9 C10 . 1.486(6) ?
C9 H9A . .9700 ?
C9 H9B . .9700 ?
C10 C11 . 1.473(8) ?
C10 H10A . .9700 ?
C10 H10B . .9700 ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
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
_geom_torsion_publ_flag
C8 O2 C2 C3 -117.9(3) ?
C8 O2 C2 C1 67.1(3) no
O1 C1 C2 C3 -174.8(4) ?
C7 C1 C2 C3 5.1(5) ?
O1 C1 C2 O2 -.8(4) ?
C7 C1 C2 O2 179.1(3) ?
O2 C2 C3 C4 -172.5(3) ?
C1 C2 C3 C4 1.4(6) ?
C2 C3 C4 C5 -2.4(6) ?
C3 C4 C5 C6 -2.7(6) ?
C3 C4 C5 N1 176.5(3) ?
O3 N1 C5 C4 9.3(4) ?
O4 N1 C5 C4 -169.7(3) no
O3 N1 C5 C6 -171.4(3) no
O4 N1 C5 C6 9.5(4) ?
C4 C5 C6 C7 3.9(6) ?
N1 C5 C6 C7 -175.3(4) ?
C5 C6 C7 C1 3.0(7) ?
O1 C1 C7 C6 171.7(4) ?
C2 C1 C7 C6 -8.2(6) ?
C2 O2 C8 O5 13.6(5) no
C2 O2 C8 C9 -169.4(3) no
O5 C8 C9 C10 -32.4(6) ?
O2 C8 C9 C10 150.8(4) no
C8 C9 C10 C11 -67.5(6) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132929
