#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/56/7105609.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_7105609
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            'C8 H10 N10'
_chemical_formula_weight         246.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 104.739(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1144(9)
_cell_length_b                   25.233(4)
_cell_length_c                   7.1186(11)
_cell_measurement_reflns_used    4080
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.22
_cell_measurement_theta_min      2.42
_cell_volume                     1062.2(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4766
_diffrn_reflns_theta_full        23.22
_diffrn_reflns_theta_max         23.22
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0330
_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)+(0.0421P)²+0.4401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                1449
_reflns_number_total             1509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002861d.txt
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/c
_cod_database_code               7105609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5230(2) 0.33120(5) 0.07682(17) 0.0215(3) Uani 1 1 d . . .
N2B N 0.9350(2) 0.41074(5) -0.59639(19) 0.0267(3) Uani 1 1 d . . .
H H 1.001(3) 0.3776(9) -0.542(3) 0.050(6) Uiso 1 1 d . . .
N2A N 0.1082(2) 0.26749(5) 0.1092(2) 0.0305(4) Uani 1 1 d . . .
N3 N 0.6272(2) 0.39031(5) -0.10094(18) 0.0270(3) Uani 1 1 d . . .
N3B N 1.0188(2) 0.43840(5) -0.7241(2) 0.0314(4) Uani 1 1 d . . .
N3A N -0.0211(2) 0.22400(5) 0.0625(2) 0.0331(4) Uani 1 1 d . . .
N4B N 0.8955(2) 0.48081(5) -0.7655(2) 0.0313(4) Uani 1 1 d . . .
N4A N 0.1094(2) 0.18315(5) 0.0568(2) 0.0311(3) Uani 1 1 d . . .
N5A N 0.3274(2) 0.19829(5) 0.0989(2) 0.0281(3) Uani 1 1 d . . .
N5B N 0.7323(2) 0.48139(5) -0.66670(19) 0.0283(3) Uani 1 1 d . . .
C1A C 0.3190(2) 0.24998(6) 0.1299(2) 0.0219(4) Uani 1 1 d . . .
C1B C 0.7602(2) 0.43737(6) -0.5630(2) 0.0232(4) Uani 1 1 d . . .
C2 C 0.6757(2) 0.34299(6) -0.0200(2) 0.0243(4) Uani 1 1 d . . .
H2A H 0.7990 0.3212 -0.0296 0.029 Uiso 1 1 calc R . .
C4 C 0.4360(3) 0.40929(6) -0.0556(2) 0.0302(4) Uani 1 1 d . . .
H4A H 0.3632 0.4422 -0.0956 0.036 Uiso 1 1 calc R . .
C5 C 0.3715(3) 0.37240(6) 0.0562(2) 0.0268(4) Uani 1 1 d . . .
H5A H 0.2451 0.3745 0.1106 0.032 Uiso 1 1 calc R . .
C6 C 0.5274(3) 0.28309(6) 0.1949(2) 0.0259(4) Uani 1 1 d . . .
H6A H 0.5450 0.2935 0.3320 0.031 Uiso 1 1 calc R . .
H6B H 0.6606 0.2615 0.1888 0.031 Uiso 1 1 calc R . .
C7 C 0.7557(3) 0.41674(7) -0.2224(2) 0.0368(4) Uani 1 1 d . . .
H7A H 0.8990 0.3974 -0.2129 0.044 Uiso 1 1 calc R . .
H7B H 0.7936 0.4533 -0.1744 0.044 Uiso 1 1 calc R . .
C8 C 0.6207(3) 0.41860(6) -0.4328(2) 0.0276(4) Uani 1 1 d . . .
H8A H 0.5617 0.3828 -0.4739 0.033 Uiso 1 1 calc R . .
H8B H 0.4898 0.4426 -0.4449 0.033 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
N1 0.0206(6) 0.0214(7) 0.0222(7) 0.0003(5) 0.0048(5) -0.0025(5)
N2B 0.0280(7) 0.0235(7) 0.0300(7) 0.0016(6) 0.0098(6) 0.0033(6)
N2A 0.0231(7) 0.0273(7) 0.0401(9) -0.0024(6) 0.0058(6) -0.0003(6)
N3 0.0254(7) 0.0278(7) 0.0267(7) 0.0025(6) 0.0047(6) -0.0073(6)
N3B 0.0320(8) 0.0329(8) 0.0317(8) 0.0000(6) 0.0127(6) -0.0001(6)
N3A 0.0237(7) 0.0341(8) 0.0404(9) -0.0025(6) 0.0062(6) -0.0044(6)
N4B 0.0353(8) 0.0286(8) 0.0315(8) 0.0022(6) 0.0109(6) -0.0021(6)
N4A 0.0284(8) 0.0270(7) 0.0361(8) -0.0001(6) 0.0051(6) -0.0055(6)
N5A 0.0257(7) 0.0236(7) 0.0347(8) 0.0016(6) 0.0069(6) -0.0004(5)
N5B 0.0311(8) 0.0239(7) 0.0306(8) 0.0024(6) 0.0093(6) 0.0014(6)
C1A 0.0218(8) 0.0230(8) 0.0211(8) 0.0028(6) 0.0058(6) 0.0005(6)
C1B 0.0231(8) 0.0205(8) 0.0248(8) -0.0016(6) 0.0039(6) 0.0003(6)
C2 0.0206(8) 0.0254(8) 0.0263(8) -0.0010(7) 0.0048(6) -0.0013(6)
C4 0.0315(9) 0.0222(8) 0.0350(10) 0.0016(7) 0.0051(7) 0.0016(7)
C5 0.0245(8) 0.0255(8) 0.0315(9) -0.0018(7) 0.0091(7) 0.0021(6)
C6 0.0239(8) 0.0263(8) 0.0264(8) 0.0049(7) 0.0042(7) -0.0013(6)
C7 0.0356(10) 0.0436(10) 0.0308(9) 0.0072(8) 0.0075(8) -0.0160(8)
C8 0.0245(8) 0.0279(8) 0.0306(9) 0.0017(7) 0.0073(7) 0.0010(7)
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'
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
C2 N1 C5 108.59(13) . . ?
C2 N1 C6 124.59(12) . . ?
C5 N1 C6 126.73(12) . . ?
C1B N2B N3B 108.61(13) . . ?
C1A N2A N3A 104.35(12) . . ?
C2 N3 C4 108.71(13) . . ?
C2 N3 C7 124.81(14) . . ?
C4 N3 C7 126.47(14) . . ?
N4B N3B N2B 106.39(12) . . ?
N4A N3A N2A 108.98(12) . . ?
N3B N4B N5B 110.56(12) . . ?
N3A N4A N5A 110.28(12) . . ?
C1A N5A N4A 103.79(12) . . ?
C1B N5B N4B 105.83(12) . . ?
N5A C1A N2A 112.60(13) . . ?
N5A C1A C6 122.36(13) . . ?
N2A C1A C6 124.89(14) . . ?
N5B C1B N2B 108.61(13) . . ?
N5B C1B C8 127.09(14) . . ?
N2B C1B C8 124.28(14) . . ?
N3 C2 N1 108.56(13) . . ?
C5 C4 N3 106.98(14) . . ?
C4 C5 N1 107.15(14) . . ?
N1 C6 C1A 113.17(12) . . ?
N3 C7 C8 110.94(13) . . ?
C1B C8 C7 111.77(13) . . ?
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
N1 C2 1.3275(19) . ?
N1 C5 1.375(2) . ?
N1 C6 1.4728(19) . ?
N2B C1B 1.334(2) . ?
N2B N3B 1.3460(19) . ?
N2A C1A 1.335(2) . ?
N2A N3A 1.3440(19) . ?
N3 C2 1.326(2) . ?
N3 C4 1.376(2) . ?
N3 C7 1.468(2) . ?
N3B N4B 1.2988(19) . ?
N3A N4A 1.3105(19) . ?
N4B N5B 1.3597(19) . ?
N4A N5A 1.3450(19) . ?
N5A C1A 1.326(2) . ?
N5B C1B 1.321(2) . ?
C1A C6 1.495(2) . ?
C1B C8 1.487(2) . ?
C4 C5 1.347(2) . ?
C7 C8 1.515(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653214
