#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028915.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_4028915
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         'C5 H8 N2 O2'
_chemical_formula_sum            'C5 H8 N2 O2'
_chemical_formula_weight         128.13
_chemical_name_systematic
; 
(R)-5-Methyl-2,3-piperazynodione  
;
_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            8
_cell_length_a                   6.98100(10)
_cell_length_b                   6.98100(10)
_cell_length_c                   24.2018(7)
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     1179.46(4)
_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 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0077
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7224
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bipyramide
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0282
_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)+(0.0417P)²+0.2030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                719
_reflns_number_total             781
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo800037wsup2.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_Hall     'P 4nw 2abw '
_cod_database_code               4028915
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 0.9281(2) 0.4702(2) 0.47277(4) 0.0429(4) Uani 1 1 d .
O3 O 1.11058(17) 0.54466(18) 0.57137(4) 0.0328(3) Uani 1 1 d .
N1 N 0.6768(2) 0.3554(2) 0.52178(5) 0.0296(3) Uani 1 1 d .
H1A H 0.6267 0.3048 0.4928 0.036 Uiso 1 1 calc R
C2 C 0.8426(2) 0.4460(2) 0.51661(6) 0.0267(4) Uani 1 1 d .
C3 C 0.9362(2) 0.5169(2) 0.57035(6) 0.0239(3) Uani 1 1 d .
N4 N 0.82069(19) 0.53741(19) 0.61321(5) 0.0256(3) Uani 1 1 d .
H4A H 0.8700 0.5687 0.6445 0.031 Uiso 1 1 calc R
C5 C 0.6129(2) 0.5095(2) 0.61012(6) 0.0259(4) Uani 1 1 d .
H5A H 0.5542 0.6226 0.5931 0.031 Uiso 1 1 calc R
C6 C 0.5747(2) 0.3368(2) 0.57421(6) 0.0288(4) Uani 1 1 d .
H6A H 0.6167 0.2217 0.5931 0.035 Uiso 1 1 calc R
H6B H 0.4383 0.3257 0.5673 0.035 Uiso 1 1 calc R
C7 C 0.5315(3) 0.4831(3) 0.66783(6) 0.0370(4) Uani 1 1 d .
H7A H 0.5604 0.5939 0.6898 0.055 Uiso 1 1 calc R
H7B H 0.5876 0.3717 0.6845 0.055 Uiso 1 1 calc R
H7C H 0.3952 0.4671 0.6656 0.055 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 0.0501(8) 0.0580(9) 0.0204(5) -0.0040(5) 0.0075(5) -0.0102(7)
O3 0.0270(6) 0.0415(7) 0.0299(6) 0.0015(5) 0.0023(5) -0.0069(5)
N1 0.0335(8) 0.0340(8) 0.0214(6) -0.0050(5) -0.0045(5) -0.0033(6)
C2 0.0321(9) 0.0277(8) 0.0205(7) -0.0011(6) -0.0010(6) 0.0029(7)
C3 0.0290(8) 0.0224(7) 0.0202(6) 0.0025(6) -0.0002(6) -0.0014(6)
N4 0.0286(7) 0.0307(7) 0.0175(6) -0.0035(5) -0.0002(5) -0.0046(6)
C5 0.0251(8) 0.0258(8) 0.0267(8) -0.0002(7) 0.0028(6) 0.0002(6)
C6 0.0266(8) 0.0305(8) 0.0293(8) -0.0031(6) 0.0008(7) -0.0038(6)
C7 0.0380(10) 0.0392(10) 0.0336(9) -0.0051(7) 0.0121(7) -0.0055(8)
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
C2 N1 C6 123.40(12)
C2 N1 H1A 118.3
C6 N1 H1A 118.3
O2 C2 N1 124.83(14)
O2 C2 C3 118.69(14)
N1 C2 C3 116.43(13)
O3 C3 N4 124.72(14)
O3 C3 C2 119.16(13)
N4 C3 C2 116.08(13)
C3 N4 C5 123.34(12)
C3 N4 H4A 118.3
C5 N4 H4A 118.3
N4 C5 C6 108.05(13)
N4 C5 C7 109.84(12)
C6 C5 C7 111.50(13)
N4 C5 H5A 109.1
C6 C5 H5A 109.1
C7 C5 H5A 109.1
N1 C6 C5 110.06(13)
N1 C6 H6A 109.6
C5 C6 H6A 109.6
N1 C6 H6B 109.6
C5 C6 H6B 109.6
H6A C6 H6B 108.2
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C2 1.2289(18)
O3 C3 1.2331(19)
N1 C2 1.325(2)
N1 C6 1.4610(19)
N1 H1A 0.8600
C2 C3 1.537(2)
C3 N4 1.3215(19)
N4 C5 1.466(2)
N4 H4A 0.8600
C5 C6 1.510(2)
C5 C7 1.519(2)
C5 H5A 0.9800
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
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
N4 H4A O2 0.86 2.02 2.8599(16) 165.3 4_565
C7 H7A O3 0.96 2.56 3.353(2) 139.8 6_466
N1 H1A O3 0.86 2.14 2.9756(17) 164.0 7_546
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
C6 N1 C2 O2 -177.10(17)
C6 N1 C2 C3 5.8(2)
O2 C2 C3 O3 -20.5(2)
N1 C2 C3 O3 156.79(15)
O2 C2 C3 N4 161.68(16)
N1 C2 C3 N4 -21.0(2)
O3 C3 N4 C5 177.86(16)
C2 C3 N4 C5 -4.5(2)
C3 N4 C5 C6 40.83(19)
C3 N4 C5 C7 162.66(14)
C2 N1 C6 C5 31.3(2)
N4 C5 C6 N1 -51.43(16)
C7 C5 C6 N1 -172.23(13)
