#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:53:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/22/7212229.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_7212229
loop_
_publ_author_name
'Marivel, Samipillai'
'Braga, Dario'
'Grepioni, Fabrizia'
'Lampronti, Giulio I.'
_publ_section_title
;
 Mechanochemical preparation of adducts (co-crystals and molecular salts)
 of 1,4-diazabicyclo-[2.2.2]-octane with aromatic polycarboxylic acids
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2107
_journal_paper_doi               10.1039/b922915a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C12 H25 N4, C14 H9 N2 O8'
_chemical_formula_sum            'C26 H34 N6 O8'
_chemical_formula_weight         558.59
_chemical_name_common            'Dinicotinic acid DABCO'
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 116.450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   21.223(2)
_cell_length_b                   6.675(1)
_cell_length_c                   10.304(1)
_cell_measurement_temperature    293(2)
_cell_volume                     1306.9(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6270
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0655P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                981
_reflns_number_total             1695
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b922915a.txt
_cod_data_source_block           datam2
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7212229
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C1 C 0.28942(12) 0.0000 0.0137(2) 0.0348(6) Uani 1 2 d S
H1 H 0.3370 0.0000 0.0783 0.042 Uiso 1 2 calc SR
C2 C 0.24171(11) 0.0000 0.0705(2) 0.0292(5) Uani 1 2 d S
C3 C 0.17081(12) 0.0000 -0.0260(2) 0.0314(5) Uani 1 2 d S
H3 H 0.1369 0.0000 0.0079 0.038 Uiso 1 2 calc SR
C4 C 0.15090(11) 0.0000 -0.1736(2) 0.0298(5) Uani 1 2 d S
C5 C 0.20356(12) 0.0000 -0.2183(2) 0.0343(5) Uani 1 2 d S
H5 H 0.1902 0.0000 -0.3174 0.041 Uiso 1 2 calc SR
C6 C 0.26522(14) 0.0000 0.2316(2) 0.0393(6) Uani 1 2 d S
C7 C 0.07430(13) 0.0000 -0.2807(2) 0.0363(6) Uani 1 2 d S
N1 N 0.27208(10) 0.0000 -0.12807(19) 0.0390(5) Uani 1 2 d S
O1 O 0.33317(9) 0.0000 0.30601(16) 0.0566(5) Uani 1 2 d S
H1A H 0.3436 0.0088 0.3926 0.085 Uiso 0.50 1 calc PR
O2 O 0.22293(10) 0.0000 0.28173(18) 0.0559(5) Uani 1 2 d S
O3 O 0.02900(9) 0.0000 -0.23807(18) 0.0526(5) Uani 1 2 d S
O4 O 0.06258(8) 0.0000 -0.41423(17) 0.0565(5) Uani 1 2 d S
H4 H 0.0000 0.0000 -0.5000 0.068 Uiso 1 4 d S
C8 C 0.41180(10) 0.1815(3) 0.80880(17) 0.0391(4) Uani 1 1 d .
H8B H 0.3799(8) 0.175(2) 0.8525(17) 0.039(5) Uiso 1 1 d .
H8A H 0.4442(10) 0.299(3) 0.8426(19) 0.054(5) Uiso 1 1 d .
C9 C 0.36900(13) 0.1813(4) 0.64358(19) 0.0563(6) Uani 1 1 d .
H13B H 0.3822(11) 0.299(4) 0.600(2) 0.083(7) Uiso 1 1 d .
H13A H 0.3214(13) 0.173(4) 0.621(2) 0.086(8) Uiso 1 1 d .
C10 C 0.50461(12) 0.0000 0.7852(2) 0.0376(6) Uani 1 2 d S
H10A H 0.5350(9) -0.119(2) 0.8180(16) 0.038(4) Uiso 1 1 d .
C11 C 0.46081(15) 0.0000 0.6209(3) 0.0485(7) Uani 1 2 d S
H12A H 0.4707(11) 0.115(3) 0.578(2) 0.073(6) Uiso 1 1 d .
N2 N 0.45713(9) 0.0000 0.85531(17) 0.0325(5) Uani 1 2 d S
H2B H 0.5000 0.0000 1.0000 0.039 Uiso 1 4 d S
N3 N 0.38551(10) 0.0000 0.58269(18) 0.0389(5) Uani 1 2 d S
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'
O O 0.0106 0.0060 '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
N1 C1 C2 124.6(2) . .
N1 C1 H1 117.7 . .
C2 C1 H1 117.7 . .
C1 C2 C3 117.62(19) . .
C1 C2 C6 121.6(2) . .
C3 C2 C6 120.8(2) . .
C4 C3 C2 119.4(2) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C3 C4 C5 117.91(19) . .
C3 C4 C7 120.5(2) . .
C5 C4 C7 121.62(19) . .
N1 C5 C4 124.02(19) . .
N1 C5 H5 118.0 . .
C4 C5 H5 118.0 . .
O2 C6 O1 125.7(2) . .
O2 C6 C2 121.5(2) . .
O1 C6 C2 112.8(2) . .
O3 C7 O4 125.2(2) . .
O3 C7 C4 120.2(2) . .
O4 C7 C4 114.6(2) . .
C5 N1 C1 116.5(2) . .
C6 O1 H1A 109.5 . .
C7 O4 H4 113.79(17) . .
N2 C8 C9 109.62(14) . .
N2 C8 H8B 107.4(10) . .
C9 C8 H8B 109.0(9) . .
N2 C8 H8A 106.3(11) . .
C9 C8 H8A 111.4(10) . .
H8B C8 H8A 113.0(14) . .
N3 C9 C8 109.74(16) . .
N3 C9 H13B 106.7(13) . .
C8 C9 H13B 110.5(13) . .
N3 C9 H13A 106.6(15) . .
C8 C9 H13A 108.3(14) . .
H13B C9 H13A 115(2) . .
N2 C10 C11 109.34(19) . .
N2 C10 H10A 108.5(9) . .
C11 C10 H10A 111.3(9) . .
N3 C11 C10 110.55(19) . .
N3 C11 H12A 108.3(13) . .
C10 C11 H12A 111.2(13) . .
C10 N2 C8 109.05(11) . 6
C10 N2 C8 109.05(11) . .
C8 N2 C8 109.07(19) 6 .
C10 N2 H2B 105.53(14) . .
C8 N2 H2B 112.02(9) 6 .
C8 N2 H2B 112.02(9) . .
C11 N3 C9 108.83(14) . 6
C11 N3 C9 108.83(14) . .
C9 N3 C9 110.2(2) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.338(3) .
C1 C2 1.377(3) .
C1 H1 0.9300 .
C2 C3 1.386(3) .
C2 C6 1.505(3) .
C3 C4 1.385(3) .
C3 H3 0.9300 .
C4 C5 1.385(3) .
C4 C7 1.504(3) .
C5 N1 1.332(3) .
C5 H5 0.9300 .
C6 O2 1.219(3) .
C6 O1 1.297(3) .
C7 O3 1.222(3) .
C7 O4 1.285(3) .
O1 H1A 0.8200 .
O4 H4 1.2245(15) .
C8 N2 1.487(2) .
C8 C9 1.532(2) .
C8 H8B 0.967(16) .
C8 H8A 1.00(2) .
C9 N3 1.475(2) .
C9 H13B 1.01(2) .
C9 H13A 0.93(2) .
C10 N2 1.479(3) .
C10 C11 1.525(3) .
C10 H10A 0.983(16) .
C11 N3 1.466(3) .
C11 H12A 0.953(19) .
N2 C8 1.487(2) 6
N2 H2B 1.3572(16) .
N3 C9 1.475(2) 6
