#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:27:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180394 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/63/7206365.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_7206365
loop_
_publ_author_name
'Ugono, Onome'
'Rath, Nigam P.'
'Beatty, Alicia M.'
_publ_section_title
;
 Exceptions to the rule: new hydrogen-bonded networks from an old
 reliable
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              753
_journal_paper_doi               10.1039/c0ce00621a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C6 H18 N2, 2(C5 H3 N2 O4) '
_chemical_formula_sum            'C16 H24 N6 O8'
_chemical_formula_weight         428.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.342(4)
_cell_angle_beta                 85.338(5)
_cell_angle_gamma                85.904(4)
_cell_formula_units_Z            1
_cell_length_a                   4.5537(6)
_cell_length_b                   9.3845(11)
_cell_length_c                   11.1398(14)
_cell_measurement_reflns_used    4768
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      3.14
_cell_volume                     465.52(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12441
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.74
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0364
_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)+(0.0480P)²+0.1456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                2210
_reflns_number_total             2637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00621a.txt
_cod_data_source_block           Compound-7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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-1
_cod_database_code               7206365
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O -0.08752(18) 0.13084(8) 0.56858(7) 0.01475(18) Uani 1 1 d .
O2 O -0.40110(18) 0.30964(8) 0.48625(7) 0.01668(18) Uani 1 1 d .
O3 O 0.42372(18) 0.36322(8) 0.91918(7) 0.01602(18) Uani 1 1 d .
H3 H 0.5253 0.3841 0.9725 0.024 Uiso 1 1 calc R
O4 O 0.24057(18) 0.59344(8) 0.91187(7) 0.01512(18) Uani 1 1 d .
N1 N -0.2247(2) 0.48775(10) 0.64025(8) 0.01230(19) Uani 1 1 d .
H1 H -0.3593 0.5306 0.5912 0.015 Uiso 1 1 calc R
N2 N -0.1105(2) 0.55187(10) 0.72241(8) 0.01261(19) Uani 1 1 d .
N3 N 0.6699(2) 0.86008(10) 0.64426(8) 0.01254(19) Uani 1 1 d .
H3A H 0.7696 0.9383 0.6058 0.019 Uiso 1 1 calc R
H3B H 0.5684 0.8266 0.5891 0.019 Uiso 1 1 calc R
H3C H 0.8003 0.7888 0.6780 0.019 Uiso 1 1 calc R
C1 C -0.1115(2) 0.35003(11) 0.64053(9) 0.0112(2) Uani 1 1 d .
C2 C 0.0899(2) 0.32180(11) 0.72885(10) 0.0123(2) Uani 1 1 d .
H2 H 0.2080 0.2349 0.7519 0.015 Uiso 1 1 calc R
C3 C 0.0818(2) 0.44975(11) 0.77717(9) 0.0115(2) Uani 1 1 d .
C4 C -0.2070(2) 0.25590(11) 0.55860(9) 0.0109(2) Uani 1 1 d .
C5 C 0.2545(2) 0.47695(11) 0.87556(10) 0.0124(2) Uani 1 1 d .
C6 C 0.4594(2) 0.90358(12) 0.74236(10) 0.0128(2) Uani 1 1 d .
H6A H 0.3321 0.8225 0.7767 0.015 Uiso 1 1 calc R
H6B H 0.3311 0.9881 0.7071 0.015 Uiso 1 1 calc R
C7 C 0.6250(2) 0.94279(12) 0.84373(10) 0.0139(2) Uani 1 1 d .
H7A H 0.7430 1.0275 0.8098 0.017 Uiso 1 1 calc R
H7B H 0.7630 0.8603 0.8747 0.017 Uiso 1 1 calc R
C8 C 0.4171(2) 0.97898(12) 0.94994(9) 0.0133(2) Uani 1 1 d .
H8A H 0.2765 1.0602 0.9187 0.016 Uiso 1 1 calc R
H8B H 0.3019 0.8936 0.9850 0.016 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'
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
C5 O3 H3 109.5 .
N2 N1 C1 113.08(9) .
N2 N1 H1 123.5 .
C1 N1 H1 123.5 .
N1 N2 C3 103.99(9) .
C6 N3 H3A 109.5 .
C6 N3 H3B 109.5 .
H3A N3 H3B 109.5 .
C6 N3 H3C 109.5 .
H3A N3 H3C 109.5 .
H3B N3 H3C 109.5 .
N1 C1 C2 106.49(9) .
N1 C1 C4 123.03(9) .
C2 C1 C4 130.47(10) .
C1 C2 C3 104.61(9) .
C1 C2 H2 127.7 .
C3 C2 H2 127.7 .
N2 C3 C2 111.82(9) .
N2 C3 C5 121.31(9) .
C2 C3 C5 126.86(10) .
O1 C4 O2 126.16(10) .
O1 C4 C1 116.74(9) .
O2 C4 C1 117.11(9) .
O4 C5 O3 124.46(10) .
O4 C5 C3 123.38(10) .
O3 C5 C3 112.15(9) .
N3 C6 C7 110.61(9) .
N3 C6 H6A 109.5 .
C7 C6 H6A 109.5 .
N3 C6 H6B 109.5 .
C7 C6 H6B 109.5 .
H6A C6 H6B 108.1 .
C6 C7 C8 112.22(9) .
C6 C7 H7A 109.2 .
C8 C7 H7A 109.2 .
C6 C7 H7B 109.2 .
C8 C7 H7B 109.2 .
H7A C7 H7B 107.9 .
C8 C8 C7 112.10(11) 2_677
C8 C8 H8A 109.2 2_677
C7 C8 H8A 109.2 .
C8 C8 H8B 109.2 2_677
C7 C8 H8B 109.2 .
H8A C8 H8B 107.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.2476(13) .
O2 C4 1.2595(13) .
O3 C5 1.3117(13) .
O3 H3 0.8400 .
O4 C5 1.2297(13) .
N1 N2 1.3400(12) .
N1 C1 1.3563(13) .
N1 H1 0.8800 .
N2 C3 1.3448(14) .
N3 C6 1.4895(14) .
N3 H3A 0.9100 .
N3 H3B 0.9100 .
N3 H3C 0.9100 .
C1 C2 1.3766(14) .
C1 C4 1.4901(14) .
C2 C3 1.4008(14) .
C2 H2 0.9500 .
C3 C5 1.4687(14) .
C6 C7 1.5200(14) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.5271(15) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C8 1.521(2) 2_677
C8 H8A 0.9900 .
C8 H8B 0.9900 .
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_4
C1 N1 N2 C3 -0.31(12) .
N2 N1 C1 C2 0.10(13) .
N2 N1 C1 C4 179.09(9) .
N1 C1 C2 C3 0.14(12) .
C4 C1 C2 C3 -178.74(11) .
N1 N2 C3 C2 0.39(12) .
N1 N2 C3 C5 -179.44(9) .
C1 C2 C3 N2 -0.34(12) .
C1 C2 C3 C5 179.49(10) .
N1 C1 C4 O1 -179.40(10) .
C2 C1 C4 O1 -0.69(17) .
N1 C1 C4 O2 0.34(16) .
C2 C1 C4 O2 179.06(11) .
N2 C3 C5 O4 -1.72(17) .
C2 C3 C5 O4 178.47(11) .
N2 C3 C5 O3 178.41(10) .
C2 C3 C5 O3 -1.40(16) .
N3 C6 C7 C8 -176.45(9) .
C6 C7 C8 C8 -178.88(11) 2_677
