#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/32/2103268.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_2103268
loop_
_publ_author_name
'Farrell, Dorcas M. M.'
'Ferguson, George'
'Lough, Alan J.'
'Glidewell, Christopher'
_publ_section_title
;
 Chiral versus racemic building blocks in supramolecular
 chemistry: tartrate salts of organic diamines
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              272
_journal_page_last               288
_journal_paper_doi               10.1107/S0108768101019632
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C4 H12 N2, C4 H4 O6'
_chemical_formula_sum            'C8 H16 N2 O6'
_chemical_formula_weight         236.23
_chemical_name_systematic
;
Piperazine--(2R,3R)-tartaric acid (1/1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 109.006(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4043(3)
_cell_length_b                   9.0860(5)
_cell_length_c                   9.3734(4)
_cell_measurement_reflns_used    1118
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.21
_cell_volume                     515.70(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3749
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.057(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0293P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                1061
_reflns_number_total             1241
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0130.cif
_cod_data_source_block           V
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-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 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               2103268
_cod_database_fobs_code          2103268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_type_symbol
N11 0.6752(3) 0.4588(3) 0.6733(2) 0.0218(5) Uani d . 1 N
N14 0.3480(3) 0.5406(3) 0.8060(2) 0.0203(5) Uani d . 1 N
C12 0.5186(4) 0.3465(4) 0.6953(3) 0.0231(6) Uani d . 1 C
C13 0.4443(4) 0.3900(3) 0.8269(3) 0.0223(6) Uani d . 1 C
C15 0.5076(4) 0.6521(3) 0.7870(3) 0.0233(6) Uani d . 1 C
C16 0.5784(4) 0.6098(3) 0.6534(3) 0.0232(6) Uani d . 1 C
O1 1.0097(3) 0.4036(2) -0.05976(19) 0.0243(5) Uani d . 1 O
O2 1.2387(3) 0.5818(2) 0.06616(18) 0.0242(5) Uani d . 1 O
O3 1.0608(3) 0.4915(3) 0.5164(2) 0.0334(5) Uani d . 1 O
O4 0.7004(3) 0.4618(3) 0.39278(19) 0.0276(5) Uani d . 1 O
O5 0.9700(3) 0.2861(2) 0.1863(2) 0.0231(4) Uani d . 1 O
O6 0.7233(3) 0.5573(2) 0.13543(18) 0.0243(5) Uani d . 1 O
C1 1.1092(4) 0.4756(3) 0.0577(3) 0.0190(5) Uani d . 1 C
C2 1.0706(4) 0.4270(3) 0.2039(3) 0.0191(6) Uani d . 1 C
C3 0.9288(4) 0.5406(3) 0.2516(3) 0.0198(5) Uani d . 1 C
C4 0.8949(4) 0.4936(3) 0.4004(3) 0.0220(6) Uani d . 1 C
H11A 0.7130 0.4344 0.5896 0.026 Uiso calc R 1 H
H11B 0.8020 0.4580 0.7556 0.026 Uiso calc R 1 H
H14A 0.3072 0.5650 0.8885 0.024 Uiso calc R 1 H
H14B 0.2232 0.5416 0.7223 0.024 Uiso calc R 1 H
H12A 0.5920 0.2492 0.7150 0.028 Uiso calc R 1 H
H12B 0.3889 0.3388 0.6026 0.028 Uiso calc R 1 H
H13A 0.3327 0.3188 0.8366 0.027 Uiso calc R 1 H
H13B 0.5720 0.3867 0.9212 0.027 Uiso calc R 1 H
H15A 0.6382 0.6565 0.8795 0.028 Uiso calc R 1 H
H15B 0.4374 0.7505 0.7701 0.028 Uiso calc R 1 H
H16A 0.4492 0.6133 0.5601 0.028 Uiso calc R 1 H
H16B 0.6891 0.6812 0.6428 0.028 Uiso calc R 1 H
H2 1.2171 0.4207 0.2853 0.023 Uiso calc R 1 H
H3 1.0075 0.6373 0.2678 0.024 Uiso calc R 1 H
H5 0.9205 0.2647 0.0942 0.035 Uiso calc R 1 H
H6 0.6203 0.5382 0.1696 0.036 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
N11 0.0205(10) 0.0287(14) 0.0179(9) 0.0003(9) 0.0089(8) -0.0012(10)
N14 0.0210(9) 0.0212(13) 0.0197(10) -0.0007(9) 0.0081(8) 0.0003(9)
C12 0.0273(12) 0.0206(14) 0.0229(12) 0.0005(11) 0.0101(10) -0.0017(11)
C13 0.0246(12) 0.0198(15) 0.0237(13) 0.0009(11) 0.0096(10) 0.0016(12)
C15 0.0258(12) 0.0207(16) 0.0248(13) -0.0007(11) 0.0101(10) -0.0013(11)
C16 0.0221(12) 0.0277(17) 0.0195(11) -0.0052(11) 0.0064(10) -0.0002(11)
O1 0.0252(9) 0.0284(12) 0.0197(8) -0.0009(8) 0.0079(7) -0.0019(8)
O2 0.0267(9) 0.0254(12) 0.0231(8) -0.0031(8) 0.0117(7) -0.0008(8)
O3 0.0275(10) 0.0515(16) 0.0189(9) 0.0023(10) 0.0046(7) -0.0008(9)
O4 0.0251(9) 0.0388(13) 0.0216(9) -0.0039(9) 0.0113(7) -0.0003(9)
O5 0.0290(9) 0.0197(10) 0.0218(9) -0.0021(8) 0.0100(8) -0.0005(8)
O6 0.0207(8) 0.0321(12) 0.0205(8) 0.0030(8) 0.0072(7) 0.0021(8)
C1 0.0166(11) 0.0203(14) 0.0206(12) 0.0022(10) 0.0068(9) -0.0012(11)
C2 0.0181(11) 0.0189(15) 0.0202(11) 0.0005(10) 0.0061(9) -0.0006(10)
C3 0.0184(10) 0.0211(14) 0.0199(11) 0.0002(10) 0.0062(9) -0.0021(11)
C4 0.0249(12) 0.0236(16) 0.0177(11) 0.0013(12) 0.0072(10) -0.0019(11)
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_publ_flag
C12 N11 C16 112.1(2) no
C12 N11 H11A 109.2 no
C16 N11 H11A 109.2 no
C12 N11 H11B 109.2 no
C16 N11 H11B 109.2 no
H11A N11 H11B 107.9 no
C13 N14 C15 111.7(2) no
C13 N14 H14A 109.3 no
C15 N14 H14A 109.3 no
C13 N14 H14B 109.3 no
C15 N14 H14B 109.3 no
H14A N14 H14B 107.9 no
N11 C12 C13 109.8(2) no
N11 C12 H12A 109.7 no
C13 C12 H12A 109.7 no
N11 C12 H12B 109.7 no
C13 C12 H12B 109.7 no
H12A C12 H12B 108.2 no
N14 C13 C12 111.1(2) no
N14 C13 H13A 109.4 no
C12 C13 H13A 109.4 no
N14 C13 H13B 109.4 no
C12 C13 H13B 109.4 no
H13A C13 H13B 108.0 no
N14 C15 C16 109.1(2) no
N14 C15 H15A 109.9 no
C16 C15 H15A 109.9 no
N14 C15 H15B 109.9 no
C16 C15 H15B 109.9 no
H15A C15 H15B 108.3 no
N11 C16 C15 110.8(2) no
N11 C16 H16A 109.5 no
C15 C16 H16A 109.5 no
N11 C16 H16B 109.5 no
C15 C16 H16B 109.5 no
H16A C16 H16B 108.1 no
C2 O5 H5 109.5 no
C3 O6 H6 109.5 no
O2 C1 O1 126.1(2) no
O2 C1 C2 117.3(2) no
O1 C1 C2 116.6(2) no
O5 C2 C3 110.6(2) no
O5 C2 C1 110.8(2) no
C3 C2 C1 110.5(2) no
O5 C2 H2 108.3 no
C3 C2 H2 108.3 no
C1 C2 H2 108.3 no
O6 C3 C2 109.8(2) no
O6 C3 C4 110.9(2) no
C2 C3 C4 110.4(2) no
O6 C3 H3 108.6 no
C2 C3 H3 108.6 no
C4 C3 H3 108.6 no
O3 C4 O4 126.3(2) no
O3 C4 C3 117.5(2) no
O4 C4 C3 116.2(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C12 1.491(4) no
N11 C16 1.492(4) no
N11 H11A 0.92 no
N11 H11B 0.92 no
N14 C13 1.487(4) no
N14 C15 1.491(3) no
N14 H14A 0.92 no
N14 H14B 0.92 no
C12 C13 1.512(3) no
C12 H12A 0.99 no
C12 H12B 0.99 no
C13 H13A 0.99 no
C13 H13B 0.99 no
C15 C16 1.514(3) no
C15 H15A 0.99 no
C15 H15B 0.99 no
C16 H16A 0.99 no
C16 H16B 0.99 no
O1 C1 1.261(3) no
O2 C1 1.258(3) no
O3 C4 1.249(3) no
O4 C4 1.258(3) no
O5 C2 1.419(3) no
O5 H5 0.84 no
O6 C3 1.416(3) no
O6 H6 0.84 no
C1 C2 1.535(3) no
C2 C3 1.534(4) no
C2 H2 1.00 no
C3 C4 1.541(3) no
C3 H3 1.00 no
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
_geom_hbond_publ_flag
N11 H11B O1 1_556 0.92 1.87 2.759(3) 161 y
N11 H11A O4 . 0.92 1.84 2.686(2) 152 y
N14 H14A O2 1_456 0.92 1.86 2.773(2) 170 y
N14 H14B O3 1_455 0.92 1.93 2.775(3) 153 y
O5 H5 O1 . 0.84 2.13 2.628(3) 118 y
O5 H5 O2 2_745 0.84 2.25 2.962(3) 143 y
O6 H6 O4 . 0.84 2.10 2.613(2) 119 y
O6 H6 O2 1_455 0.84 2.35 2.965(2) 130 y
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
C16 N11 C12 C13 -55.5(3) no
C15 N14 C13 C12 -57.7(3) no
N11 C12 C13 N14 55.2(3) no
C13 N14 C15 C16 57.7(3) no
C12 N11 C16 C15 57.2(3) no
N14 C15 C16 N11 -56.9(3) no
O2 C1 C2 O5 -164.9(2) no
O1 C1 C2 O5 14.2(3) no
O2 C1 C2 C3 72.2(3) no
O1 C1 C2 C3 -108.7(3) no
O5 C2 C3 O6 -64.1(2) no
C1 C2 C3 O6 58.9(3) no
O5 C2 C3 C4 58.4(3) no
C1 C2 C3 C4 -178.6(2) no
O6 C3 C4 O3 -171.9(2) no
C2 C3 C4 O3 66.2(3) no
O6 C3 C4 O4 7.8(4) no
C2 C3 C4 O4 -114.1(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188398
