#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151378.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_7151378
loop_
_publ_author_name
'Heaney, Frances'
'Fenlon, Julie'
'McArdle, Patrick'
'Cunningham, Desmond'
_publ_section_title
;
 α-Keto amides as precursors to heterocycles---generation and
 cycloaddition reactions of piperazin-5-one nitrones
;
_journal_issue                   7
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1122
_journal_paper_doi               10.1039/b210943n
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C22 H23 N O5'
_chemical_formula_weight         381.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.21(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.243(6)
_cell_length_b                   8.697(4)
_cell_length_c                   15.245(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1919.8(18)
_computing_cell_refinement       'XDS (W.Kabsch, 2000)'
_computing_data_collection       'Marresearch MarControl software'
_computing_data_reduction        'XDS (W.Kabsch, 2000)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'Marresearch image plate'
_diffrn_measurement_method       '180 mm image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3086
_diffrn_reflns_theta_full        20.90
_diffrn_reflns_theta_max         20.90
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         1796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0731P)²+1.7815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                1310
_reflns_number_total             1796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b210943n.txt
_cod_data_source_block           11c
_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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 
;
_cod_original_cell_volume        1919.8(17)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7151378
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -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
O2 O -0.0013(3) 0.2181(4) 0.9660(2) 0.0582(11) Uani 1 1 d . . .
O13 O 0.2247(3) 0.1546(4) 0.9734(2) 0.0525(10) Uani 1 1 d . . .
N1 N 0.0536(3) 0.3195(5) 0.9278(3) 0.0481(12) Uani 1 1 d . . .
H1 H 0.005(5) 0.383(7) 0.893(4) 0.09(2) Uiso 1 1 d . . .
C3A C -0.0062(4) 0.1114(6) 0.8212(4) 0.0612(17) Uani 1 1 d . . .
H3A H -0.0432 0.1389 0.7581 0.080 Uiso 1 1 calc R . .
C6A C 0.0761(4) 0.2185(5) 0.8599(3) 0.0403(13) Uani 1 1 d . . .
O21 O 0.6273(3) -0.0246(5) 0.9003(3) 0.0710(13) Uani 1 1 d . . .
H21 H 0.671(4) -0.054(8) 0.939(4) 0.092 Uiso 1 1 calc R . .
O22 O 0.7005(3) 0.0319(4) 0.5692(3) 0.0637(12) Uani 1 1 d . . .
H22 H 0.667(4) 0.099(7) 0.536(3) 0.083 Uiso 1 1 calc R . .
O26 O 0.8783(4) -0.0813(7) 0.5923(4) 0.111(2) Uani 1 1 d . . .
H26 H 0.825(6) -0.031(8) 0.570(5) 0.144 Uiso 1 1 calc R . .
C3 C -0.0591(4) 0.1313(7) 0.8897(4) 0.0649(16) Uani 1 1 d . . .
H3B H -0.1166 0.1857 0.8612 0.084 Uiso 1 1 calc R . .
H3C H -0.0734 0.0319 0.9106 0.084 Uiso 1 1 calc R . .
C4 C 0.0414(6) -0.0473(7) 0.8260(5) 0.087(2) Uani 1 1 d . . .
H4A H 0.0046 -0.1274 0.8417 0.113 Uiso 1 1 calc R . .
H4B H 0.0500 -0.0724 0.7673 0.113 Uiso 1 1 calc R . .
C5 C 0.1280(4) -0.0324(5) 0.8962(3) 0.0389(13) Uani 1 1 d . . .
C6 C 0.1524(4) 0.1106(6) 0.9167(3) 0.0447(14) Uani 1 1 d . . .
C7 C 0.1100(4) 0.3163(5) 0.7947(3) 0.0417(13) Uani 1 1 d . . .
C8 C 0.0737(4) 0.3026(7) 0.6999(3) 0.0615(16) Uani 1 1 d . . .
H8 H 0.0301 0.2270 0.6742 0.080 Uiso 1 1 calc R . .
C9 C 0.1028(5) 0.4025(8) 0.6429(4) 0.077(2) Uani 1 1 d . . .
H9 H 0.0765 0.3955 0.5792 0.101 Uiso 1 1 calc R . .
C10 C 0.1683(5) 0.5086(7) 0.6787(5) 0.072(2) Uani 1 1 d . . .
H10 H 0.1868 0.5746 0.6397 0.093 Uiso 1 1 calc R . .
C11 C 0.2076(5) 0.5197(7) 0.7720(5) 0.077(2) Uani 1 1 d . . .
H11 H 0.2545 0.5906 0.7968 0.100 Uiso 1 1 calc R . .
C12 C 0.1775(5) 0.4249(6) 0.8297(4) 0.0685(19) Uani 1 1 d . . .
H12 H 0.2033 0.4348 0.8933 0.089 Uiso 1 1 calc R . .
C14 C 0.1828(5) -0.1646(7) 0.9342(5) 0.096(3) Uani 1 1 d . . .
H14A H 0.2077 -0.2076 0.8889 0.134 Uiso 1 1 calc R . .
H14B H 0.1450 -0.2399 0.9512 0.134 Uiso 1 1 calc R . .
H14C H 0.2325 -0.1349 0.9878 0.134 Uiso 1 1 calc R . .
C15 C 0.6462(4) -0.0134(6) 0.8184(3) 0.0505(14) Uani 1 1 d . . .
C16 C 0.7191(4) -0.0899(6) 0.8022(4) 0.0496(14) Uani 1 1 d . . .
H16 H 0.7571 -0.1524 0.8480 0.064 Uiso 1 1 calc R . .
C17 C 0.7362(4) -0.0747(5) 0.7194(4) 0.0498(14) Uani 1 1 d . . .
H17 H 0.7852 -0.1274 0.7091 0.065 Uiso 1 1 calc R . .
C18 C 0.6807(4) 0.0186(5) 0.6513(3) 0.0440(14) Uani 1 1 d . . .
C19 C 0.6071(4) 0.0957(5) 0.6664(3) 0.0456(14) Uani 1 1 d . . .
H19 H 0.5689 0.1580 0.6207 0.059 Uiso 1 1 calc R . .
C20 C 0.5911(4) 0.0789(6) 0.7503(4) 0.0518(15) Uani 1 1 d . . .
H20 H 0.5420 0.1312 0.7607 0.067 Uiso 1 1 calc R . .
C23 C 0.9369(4) -0.0376(7) 0.5440(4) 0.0618(16) Uani 1 1 d . . .
C24 C 0.9241(4) 0.0918(7) 0.4913(4) 0.0673(17) Uani 1 1 d . . .
H24 H 0.8731 0.1545 0.4852 0.087 Uiso 1 1 calc R . .
C25 C 0.9882(5) 0.1293(7) 0.4468(4) 0.076(2) Uani 1 1 d . . .
H25 H 0.9799 0.2174 0.4105 0.099 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 N1 106.2(3) . . ?
O2 N1 C6A 102.0(4) . . ?
C3 C3A C6A 102.3(4) . . ?
C3 C3A C4 114.2(4) . . ?
C6A C3A C4 102.1(5) . . ?
N1 C6A C7 109.1(4) . . ?
N1 C6A C3A 107.0(4) . . ?
C7 C6A C3A 119.7(4) . . ?
N1 C6A C6 105.7(4) . . ?
C7 C6A C6 111.0(4) . . ?
C3A C6A C6 103.4(4) . . ?
O2 C3 C3A 107.1(4) . . ?
C5 C4 C3A 105.4(4) . . ?
C6 C5 C4 113.2(5) . . ?
C6 C5 C14 125.5(6) . . ?
C4 C5 C14 121.2(5) . . ?
O13 C6 C5 126.1(5) . . ?
O13 C6 C6A 124.1(5) . . ?
C5 C6 C6A 109.7(5) . . ?
C12 C7 C8 118.1(5) . . ?
C12 C7 C6A 119.8(4) . . ?
C8 C7 C6A 122.1(5) . . ?
C7 C8 C9 119.8(6) . . ?
C10 C9 C8 121.0(6) . . ?
C9 C10 C11 120.1(5) . . ?
C10 C11 C12 119.7(6) . . ?
C7 C12 C11 121.2(6) . . ?
O21 C15 C20 118.6(4) . . ?
O21 C15 C16 122.6(5) . . ?
C20 C15 C16 118.8(4) . . ?
C17 C16 C15 120.8(5) . . ?
C16 C17 C18 120.0(5) . . ?
C17 C18 O22 118.3(4) . . ?
C17 C18 C19 119.8(4) . . ?
O22 C18 C19 121.9(5) . . ?
C20 C19 C18 119.2(5) . . ?
C15 C20 C19 121.2(5) . . ?
C24 C23 C25 120.3(5) . 3_756 ?
C24 C23 O26 123.2(5) . . ?
C25 C23 O26 116.5(6) 3_756 . ?
C23 C24 C25 119.3(6) . . ?
C23 C25 C24 120.4(5) 3_756 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.435(6) . ?
O2 N1 1.456(5) . ?
O13 C6 1.230(6) . ?
N1 C6A 1.476(6) . ?
C3A C3 1.516(7) . ?
C3A C6A 1.526(7) . ?
C3A C4 1.550(9) . ?
C6A C7 1.517(6) . ?
C6A C6 1.534(7) . ?
O21 C15 1.369(5) . ?
O22 C18 1.382(5) . ?
O26 C23 1.376(6) . ?
C4 C5 1.422(9) . ?
C5 C6 1.308(7) . ?
C5 C14 1.433(8) . ?
C7 C12 1.376(8) . ?
C7 C8 1.381(7) . ?
C8 C9 1.396(7) . ?
C9 C10 1.343(9) . ?
C10 C11 1.364(9) . ?
C11 C12 1.385(7) . ?
C15 C20 1.373(7) . ?
C15 C16 1.382(7) . ?
C16 C17 1.373(6) . ?
C17 C18 1.379(7) . ?
C18 C19 1.387(7) . ?
C19 C20 1.381(6) . ?
C23 C24 1.361(8) . ?
C23 C25 1.364(8) 3_756 ?
C24 C25 1.392(8) . ?
C25 C23 1.364(8) 3_756 ?
