#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:54:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180160 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/56/7105608.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_7105608
loop_
_publ_author_name
'Drab, David M.'
'Shamshina, Julia L.'
'Smiglak, Marcin'
'Hines, C. Corey'
'Cordes, David B.'
'Rogers, Robin D.'
_publ_section_title
;
 A general design platform for ionic liquid ions based on bridged
 multi-heterocycles with flexible symmetry and charge
;
_journal_issue                   20
_journal_name_full               'Chemical Communications'
_journal_page_first              3544
_journal_paper_doi               10.1039/c002861d
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C5 H10 N7 Na O2'
_chemical_formula_weight         223.19
_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                91.350(2)
_cell_angle_beta                 91.457(2)
_cell_angle_gamma                105.267(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0435(8)
_cell_length_b                   8.2860(9)
_cell_length_c                   8.5121(10)
_cell_measurement_reflns_used    2480
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.39
_cell_volume                     478.86(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      178(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0104
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3297
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.9360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       elliptical
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0332
_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)+(0.0341P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                2031
_reflns_number_total             2182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002861d.txt
_cod_data_source_block           5
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105608
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.36223(8) 0.91628(6) -0.16959(6) 0.01994(14) Uani 1 1 d . . .
O1 O 0.39170(17) 0.81175(15) -0.41861(12) 0.0279(2) Uani 1 1 d . . .
H201 H 0.497(4) 0.822(3) -0.467(3) 0.049(6) Uiso 1 1 d . . .
H101 H 0.307(4) 0.825(3) -0.483(3) 0.058(7) Uiso 1 1 d . . .
O2 O 0.69566(15) 0.95284(13) -0.07514(11) 0.0207(2) Uani 1 1 d . . .
H202 H 0.795(3) 0.998(3) -0.123(2) 0.039(5) Uiso 1 1 d . . .
H102 H 0.711(3) 0.862(3) -0.057(3) 0.053(7) Uiso 1 1 d . . .
N1 N 0.26190(18) 0.64854(14) -0.04044(14) 0.0230(3) Uani 1 1 d . . .
N2 N 0.26371(18) 0.38845(14) 0.03240(13) 0.0221(2) Uani 1 1 d . . .
N3 N 0.28388(16) 0.49373(13) 0.16029(13) 0.0181(2) Uani 1 1 d . . .
N4 N 0.26072(17) 0.19505(15) 0.57623(13) 0.0215(2) Uani 1 1 d . . .
N5 N 0.19671(17) 0.11302(14) 0.70815(13) 0.0210(2) Uani 1 1 d . . .
N6 N 0.01268(17) 0.11166(14) 0.72726(13) 0.0204(2) Uani 1 1 d . . .
N7 N -0.04970(16) 0.19249(14) 0.60892(13) 0.0208(2) Uani 1 1 d . . .
C1 C 0.2818(2) 0.64587(16) 0.11480(16) 0.0218(3) Uani 1 1 d . . .
H1A H 0.294(2) 0.736(2) 0.188(2) 0.023(4) Uiso 1 1 d . . .
C2 C 0.2513(2) 0.48779(17) -0.08488(16) 0.0223(3) Uani 1 1 d . . .
H2A H 0.233(2) 0.445(2) -0.192(2) 0.024(4) Uiso 1 1 d . . .
C3 C 0.2971(2) 0.43282(17) 0.31908(16) 0.0216(3) Uani 1 1 d . . .
H3A H 0.395(3) 0.371(2) 0.318(2) 0.030(4) Uiso 1 1 d . . .
H3B H 0.344(3) 0.528(2) 0.386(2) 0.028(4) Uiso 1 1 d . . .
C4 C 0.0985(2) 0.32583(19) 0.36582(16) 0.0225(3) Uani 1 1 d . . .
H4A H 0.052(3) 0.238(2) 0.283(2) 0.035(5) Uiso 1 1 d . . .
H4B H 0.005(3) 0.390(2) 0.369(2) 0.037(5) Uiso 1 1 d . . .
C5 C 0.10591(19) 0.24092(15) 0.51867(15) 0.0172(2) Uani 1 1 d . . .
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'
Na Na 0.0362 0.0249 '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
O1 Na1 O2 98.37(4) . . ?
O1 Na1 O2 172.35(4) . 2_675 ?
O2 Na1 O2 87.47(4) . 2_675 ?
O1 Na1 N1 97.43(4) . . ?
O2 Na1 N1 90.36(4) . . ?
O2 Na1 N1 87.42(4) 2_675 . ?
O1 Na1 N5 87.99(4) . 1_564 ?
O2 Na1 N5 131.44(4) . 1_564 ?
O2 Na1 N5 84.43(4) 2_675 1_564 ?
N1 Na1 N5 136.74(5) . 1_564 ?
O1 Na1 Na1 142.05(4) . 2_675 ?
O2 Na1 Na1 43.93(3) . 2_675 ?
O2 Na1 Na1 43.55(3) 2_675 2_675 ?
N1 Na1 Na1 88.46(4) . 2_675 ?
N5 Na1 Na1 112.90(4) 1_564 2_675 ?
Na1 O2 Na1 92.53(4) . 2_675 ?
C1 N1 C2 102.40(11) . . ?
C1 N1 Na1 119.00(9) . . ?
C2 N1 Na1 134.17(9) . . ?
C2 N2 N3 102.39(11) . . ?
C1 N3 N2 109.69(11) . . ?
C1 N3 C3 129.44(12) . . ?
N2 N3 C3 120.83(10) . . ?
C5 N4 N5 104.79(11) . . ?
N6 N5 N4 109.26(10) . . ?
N6 N5 Na1 124.68(8) . 1_546 ?
N4 N5 Na1 122.67(8) . 1_546 ?
N5 N6 N7 109.58(10) . . ?
C5 N7 N6 104.66(10) . . ?
N1 C1 N3 110.76(12) . . ?
N2 C2 N1 114.76(12) . . ?
N3 C3 C4 110.36(11) . . ?
C5 C4 C3 113.38(11) . . ?
N4 C5 N7 111.71(11) . . ?
N4 C5 C4 125.22(12) . . ?
N7 C5 C4 122.94(11) . . ?
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
Na1 O1 2.3058(12) . ?
Na1 O2 2.4024(11) . ?
Na1 O2 2.4190(11) 2_675 ?
Na1 N1 2.4410(12) . ?
Na1 N5 2.4736(12) 1_564 ?
Na1 Na1 3.4836(11) 2_675 ?
O2 Na1 2.4190(11) 2_675 ?
N1 C1 1.3266(18) . ?
N1 C2 1.3584(18) . ?
N2 C2 1.3244(17) . ?
N2 N3 1.3595(16) . ?
N3 C1 1.3310(16) . ?
N3 C3 1.4631(16) . ?
N4 C5 1.3317(17) . ?
N4 N5 1.3515(15) . ?
N5 N6 1.3077(16) . ?
N5 Na1 2.4736(12) 1_546 ?
N6 N7 1.3492(15) . ?
N7 C5 1.3335(17) . ?
C3 C4 1.5141(19) . ?
C4 C5 1.4998(17) . ?
