#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028914.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4028914
loop_
_publ_author_name
'Piotrkowska, Barbara'
'Myślińska, Małgorzata'
'Gdaniec, Maria'
'Herman, Aleksander'
'Połoński, Tadeusz'
_publ_section_title
;
 Conformational Properties, Chiroptical Spectra, and Molecular
 Self-Assembly of 2,3-Piperazinodiones and Their Dithiono Analogues
;
_journal_issue                   7
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              2852
_journal_page_last               2861
_journal_paper_doi               10.1021/jo800037w
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C8 H12 N2 O2'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20
_chemical_melting_point_gt       573.15
_chemical_name_systematic
; 
(9R,10R)-2,3-Decahydrobenzopyrazinodione 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6090(3)
_cell_length_b                   6.6090(3)
_cell_length_c                   18.8339(15)
_cell_measurement_reflns_used    3827
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     822.64(8)
_computing_cell_refinement
;
CrysAlis CCD
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2007)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_molecular_graphics
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω 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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3290
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         4.33
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bipyramide
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.109(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   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0367
_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)+(0.0584P)²+0.0143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                483
_reflns_number_total             584
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo800037wsup1.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '> 300C' was changed to
'573.15' - it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     'P 4nw 2abw '
_cod_database_code               4028914
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
O2 O -0.1708(3) 0.7199(2) 0.06860(6) 0.0661(6) Uani 1 1 d .
N1 N 0.1021(2) 0.9239(2) 0.05773(7) 0.0384(5) Uani 1 1 d .
H1A H 0.1497 0.8855 0.0980 0.046 Uiso 1 1 calc R
C2 C -0.0731(3) 0.8473(3) 0.03602(9) 0.0396(5) Uani 1 1 d .
C3 C 0.2176(2) 1.0706(2) 0.01603(8) 0.0314(5) Uani 1 1 d .
H3A H 0.2859 0.9983 -0.0226 0.038 Uiso 1 1 calc R
C4 C 0.3767(3) 1.1770(3) 0.06030(9) 0.0463(6) Uani 1 1 d .
H4A H 0.4738 1.0789 0.0778 0.056 Uiso 1 1 calc R
H4B H 0.3132 1.2415 0.1008 0.056 Uiso 1 1 calc R
C5 C 0.4848(3) 1.3350(3) 0.01568(10) 0.0486(6) Uani 1 1 d .
H5A H 0.5582 1.2687 -0.0224 0.058 Uiso 1 1 calc R
H5B H 0.5820 1.4068 0.0449 0.058 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0803(11) 0.0655(11) 0.0525(8) 0.0146(8) 0.0048(7) -0.0332(9)
N1 0.0485(10) 0.0356(8) 0.0311(7) 0.0087(6) -0.0088(7) -0.0057(7)
C2 0.0485(11) 0.0371(9) 0.0331(8) 0.0004(8) 0.0037(8) -0.0092(9)
C3 0.0323(9) 0.0309(9) 0.0309(7) 0.0000(7) -0.0017(7) -0.0011(8)
C4 0.0451(12) 0.0466(12) 0.0472(10) 0.0007(9) -0.0156(9) -0.0072(9)
C5 0.0361(11) 0.0525(12) 0.0572(12) -0.0070(10) -0.0028(9) -0.0116(10)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C3 122.84(13) . .
C2 N1 H1A 118.6 . .
C3 N1 H1A 118.6 . .
O2 C2 N1 124.53(17) . .
O2 C2 C2 119.57(12) . 7_465
N1 C2 C2 115.90(9) . 7_465
N1 C3 C3 107.90(11) . 7_465
N1 C3 C4 111.99(12) . .
C3 C3 C4 111.74(11) 7_465 .
N1 C3 H3A 108.4 . .
C3 C3 H3A 108.4 7_465 .
C4 C3 H3A 108.4 . .
C3 C4 C5 109.94(13) . .
C3 C4 H4A 109.7 . .
C5 C4 H4A 109.7 . .
C3 C4 H4B 109.7 . .
C5 C4 H4B 109.7 . .
H4A C4 H4B 108.2 . .
C4 C5 C5 110.88(14) . 7_465
C4 C5 H5A 109.5 . .
C5 C5 H5A 109.5 7_465 .
C4 C5 H5B 109.5 . .
C5 C5 H5B 109.5 7_465 .
H5A C5 H5B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C2 1.226(2) .
N1 C2 1.328(2) .
N1 C3 1.463(2) .
N1 H1A 0.8600 .
C2 C2 1.547(4) 7_465
C3 C3 1.501(3) 7_465
C3 C4 1.515(2) .
C3 H3A 0.9800 .
C4 C5 1.519(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C5 1.520(4) 7_465
C5 H5A 0.9700 .
C5 H5B 0.9700 .
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
_geom_hbond_site_symmetry_A
C5 H5B O2 0.97 2.67 3.556(2) 151 1_665
N1 H1A O2 0.86 2.09 2.9291(18) 166 6_565
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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 N1 C2 O2 177.79(17) . . .
C3 N1 C2 C2 -1.5(3) . . 7_465
C2 N1 C3 C3 40.5(2) . . 7_465
C2 N1 C3 C4 163.84(17) . . .
N1 C3 C4 C5 -177.09(15) . . .
C3 C3 C4 C5 -55.9(2) 7_465 . .
C3 C4 C5 C5 56.5(2) . . 7_465
N1 C2 C2 N1 -20.0(4) . 7_465 7_465
O2 C2 C2 O2 -18.7(4) . 7_465 7_465
N1 C3 C3 N1 -56.6(2) . 7_465 7_465
