#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/26/2202644.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_2202644
loop_
_publ_author_name
'Marx, Raimund'
'Glaser, Steffen'
'Bolte, Michael'
_publ_section_title
;
 Methyl N-(benzyloxycarbonyl)oxamate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1425
_journal_page_last               o1426
_journal_paper_doi               10.1107/S1600536803018774
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C11 H11 N O5'
_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 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.446(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0139(8)
_cell_length_b                   5.4828(5)
_cell_length_c                   24.701(3)
_cell_measurement_reflns_used    512
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      3.2
_cell_volume                     1080.4(2)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Siemens 1K CCD three-circle'
_diffrn_measurement_method       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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17271
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  'at end of data collection'
_diffrn_standards_number         123
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.202
_refine_ls_extinction_coef       0.0114(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0422
_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)+(0.0434P)²+0.2657P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                2248
_reflns_number_total             3064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6056.cif
_cod_data_source_block           I
_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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202644
_cod_database_fobs_code          2202644
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_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
C1 0.14106(17) -0.0537(2) 0.34404(5) 0.0263(3) Uani d . 1 . . C
H1A 0.0181 -0.0769 0.3387 0.032 Uiso calc R 1 . . H
H1B 0.1931 -0.2110 0.3559 0.032 Uiso calc R 1 . . H
O2 0.18237(11) 0.13170(16) 0.38516(3) 0.0237(2) Uani d . 1 . . O
C3 0.12055(15) 0.0899(2) 0.43214(5) 0.0203(3) Uani d . 1 . . C
O31 0.03334(11) -0.08206(17) 0.44151(4) 0.0276(2) Uani d . 1 . . O
N4 0.16544(13) 0.2661(2) 0.47111(4) 0.0209(2) Uani d . 1 . . N
H4 0.1215(19) 0.243(3) 0.5013(7) 0.034(4) Uiso d . 1 . . H
C5 0.26733(14) 0.4662(2) 0.46824(5) 0.0190(2) Uani d . 1 . . C
O51 0.34199(11) 0.52955(17) 0.43049(4) 0.0258(2) Uani d . 1 . . O
C6 0.27838(15) 0.6067(2) 0.52258(5) 0.0201(3) Uani d . 1 . . C
O61 0.20617(12) 0.54188(18) 0.56038(4) 0.0294(2) Uani d . 1 . . O
O7 0.37597(11) 0.80055(16) 0.52109(3) 0.0229(2) Uani d . 1 . . O
C8 0.39785(16) 0.9384(3) 0.57169(5) 0.0265(3) Uani d . 1 . . C
H8A 0.4714 1.0783 0.5672 0.040 Uiso calc R 1 . . H
H8B 0.4483 0.8332 0.6009 0.040 Uiso calc R 1 . . H
H8C 0.2886 0.9965 0.5810 0.040 Uiso calc R 1 . . H
C11 0.20499(15) 0.0259(2) 0.29166(5) 0.0202(3) Uani d . 1 . . C
C12 0.16574(16) -0.1226(3) 0.24647(5) 0.0258(3) Uani d . 1 . . C
H12 0.1038 -0.2685 0.2501 0.031 Uiso calc R 1 . . H
C13 0.21605(18) -0.0597(3) 0.19636(5) 0.0311(3) Uani d . 1 . . C
H13 0.1877 -0.1612 0.1657 0.037 Uiso calc R 1 . . H
C14 0.30793(18) 0.1515(3) 0.19085(5) 0.0314(3) Uani d . 1 . . C
H14 0.3433 0.1944 0.1565 0.038 Uiso calc R 1 . . H
C15 0.34800(17) 0.2995(3) 0.23544(5) 0.0287(3) Uani d . 1 . . C
H15 0.4111 0.4441 0.2316 0.034 Uiso calc R 1 . . H
C16 0.29631(15) 0.2378(2) 0.28601(5) 0.0238(3) Uani d . 1 . . C
H16 0.3236 0.3407 0.3165 0.029 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
O2 C1 C11 108.98(10)
O2 C1 H1A 109.9
C11 C1 H1A 109.9
O2 C1 H1B 109.9
C11 C1 H1B 109.9
H1A C1 H1B 108.3
C3 O2 C1 114.33(10)
O31 C3 O2 125.02(11)
O31 C3 N4 121.80(11)
O2 C3 N4 113.18(10)
C5 N4 C3 129.57(11)
C5 N4 H4 117.0(11)
C3 N4 H4 113.4(11)
O51 C5 N4 127.66(12)
O51 C5 C6 122.49(11)
N4 C5 C6 109.84(10)
O61 C6 O7 126.23(11)
O61 C6 C5 122.53(11)
O7 C6 C5 111.24(10)
C6 O7 C8 114.61(10)
O7 C8 H8A 109.5
O7 C8 H8B 109.5
H8A C8 H8B 109.5
O7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C16 C11 C12 119.34(11)
C16 C11 C1 123.84(11)
C12 C11 C1 116.81(11)
C13 C12 C11 120.60(12)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 119.98(13)
C12 C13 H13 120.0
C14 C13 H13 120.0
C15 C14 C13 119.88(12)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C16 120.36(13)
C14 C15 H15 119.8
C16 C15 H15 119.8
C11 C16 C15 119.85(12)
C11 C16 H16 120.1
C15 C16 H16 120.1
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
C1 O2 . 1.4529(15) y
C1 C11 . 1.5010(17) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
O2 C3 . 1.3243(14) y
C3 O31 . 1.2088(15) y
C3 N4 . 1.3868(16) y
N4 C5 . 1.3737(16) y
N4 H4 . 0.863(17) ?
C5 O51 . 1.2057(14) y
C5 C6 . 1.5430(17) y
C6 O61 . 1.1980(14) y
C6 O7 . 1.3221(15) y
O7 C8 . 1.4570(15) y
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C11 C16 . 1.3872(18) ?
C11 C12 . 1.3935(17) ?
C12 C13 . 1.3813(19) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.386(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3945(18) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
N4 H4 O31 3_556 0.863(17) 2.156(17) 2.9778(14) 158.9(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
C11 C1 O2 C3 175.02(10)
C1 O2 C3 O31 -1.71(18)
C1 O2 C3 N4 178.40(10)
O31 C3 N4 C5 177.35(12)
O2 C3 N4 C5 -2.75(18)
C3 N4 C5 O51 -1.0(2)
C3 N4 C5 C6 -179.91(11)
O51 C5 C6 O61 -178.88(12)
N4 C5 C6 O61 0.12(16)
O51 C5 C6 O7 0.91(16)
N4 C5 C6 O7 179.92(10)
O61 C6 O7 C8 1.92(18)
C5 C6 O7 C8 -177.86(9)
O2 C1 C11 C16 3.18(17)
O2 C1 C11 C12 -175.53(11)
C16 C11 C12 C13 -0.38(19)
C1 C11 C12 C13 178.39(12)
C11 C12 C13 C14 0.7(2)
C12 C13 C14 C15 -0.4(2)
C13 C14 C15 C16 -0.1(2)
C12 C11 C16 C15 -0.15(19)
C1 C11 C16 C15 -178.82(12)
C14 C15 C16 C11 0.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131507
