#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:53:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/22/7212230.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_7212230
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         'C6 H13 N2, C7 H4 N O4'
_chemical_formula_sum            'C13 H17 N3 O4'
_chemical_formula_weight         279.30
_chemical_name_common            'Dipicolinic acid DABCO'
_chemical_name_systematic
;
?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.275(1)
_cell_length_b                   7.122(1)
_cell_length_c                   17.450(1)
_cell_measurement_reflns_used    4374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9265
_cell_measurement_theta_min      2.8553
_cell_volume                     1277.0(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.917
_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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7919
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98508
_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    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0400
_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)+(0.0833P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                1292
_reflns_number_total             1671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b922915a.txt
_cod_data_source_block           datam3
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7212230
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
C1 C 0.01761(15) 0.2500 0.50891(9) 0.0322(4) Uani 1 2 d S
C2 C -0.08460(16) 0.2500 0.45686(10) 0.0423(5) Uani 1 2 d S
H2 H -0.1704 0.2500 0.4739 0.048(5) Uiso 1 2 calc SR
C3 C -0.05705(19) 0.2500 0.37972(11) 0.0464(5) Uani 1 2 d S
H3 H -0.1236 0.2500 0.3436 0.053(6) Uiso 1 2 calc SR
C4 C 0.07110(18) 0.2500 0.35724(9) 0.0380(4) Uani 1 2 d S
H4 H 0.0925 0.2500 0.3055 0.045(5) Uiso 1 2 calc SR
C5 C 0.16864(15) 0.2500 0.41265(8) 0.0288(4) Uani 1 2 d S
C6 C 0.30957(16) 0.2500 0.38514(8) 0.0347(4) Uani 1 2 d S
C7 C -0.01832(16) 0.2500 0.59297(9) 0.0377(4) Uani 1 2 d S
N1 N 0.14343(12) 0.2500 0.48819(7) 0.0291(3) Uani 1 2 d S
O1 O -0.13228(12) 0.2500 0.61146(7) 0.0657(6) Uani 1 2 d S
O2 O 0.07662(11) 0.2500 0.64146(6) 0.0458(4) Uani 1 2 d S
H2A H 0.0432 0.2500 0.6907 0.050 Uiso 1 2 d S
O3 O 0.39934(11) 0.2500 0.43457(7) 0.0470(4) Uani 1 2 d S
O4 O 0.32830(14) 0.2500 0.31529(7) 0.0602(5) Uani 1 2 d S
C8 C 0.41286(13) 0.0795(2) 0.70249(8) 0.0448(4) Uani 1 1 d .
C9 C 0.36867(12) 0.0785(2) 0.61903(7) 0.0374(3) Uani 1 1 d .
C10 C 0.56606(15) 0.2500 0.58494(9) 0.0392(4) Uani 1 2 d S
C11 C 0.60650(16) 0.2500 0.66903(10) 0.0408(5) Uani 1 2 d S
N2 N 0.48967(12) 0.2500 0.71917(7) 0.0383(4) Uani 1 2 d S
N3 N 0.42036(12) 0.2500 0.58108(8) 0.0321(3) Uani 1 2 d S
H8A H 0.4645(17) -0.032(3) 0.7123(9) 0.068(5) Uiso 1 1 d .
H8B H 0.3366(15) 0.086(3) 0.7347(9) 0.068(5) Uiso 1 1 d .
H9A H 0.4026(15) -0.032(2) 0.5925(8) 0.051(4) Uiso 1 1 d .
H9B H 0.2768(14) 0.082(2) 0.6143(7) 0.044(4) Uiso 1 1 d .
H10A H 0.5969(14) 0.138(2) 0.5571(8) 0.045(4) Uiso 1 1 d .
H11A H 0.6578(13) 0.135(2) 0.6795(7) 0.047(4) Uiso 1 1 d .
H3A H 0.3997(18) 0.2500 0.5247(11) 0.042(5) Uiso 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 123.53(15) . .
N1 C1 C7 119.74(14) . .
C2 C1 C7 116.73(15) . .
C3 C2 C1 118.97(16) . .
C4 C3 C2 118.47(16) . .
C3 C4 C5 119.44(16) . .
N1 C5 C4 122.85(15) . .
N1 C5 C6 119.46(13) . .
C4 C5 C6 117.69(14) . .
O4 C6 O3 124.11(15) . .
O4 C6 C5 117.31(14) . .
O3 C6 C5 118.58(14) . .
O1 C7 O2 123.65(15) . .
O1 C7 C1 119.53(15) . .
O2 C7 C1 116.82(14) . .
C5 N1 C1 116.73(13) . .
N2 C8 C9 110.55(11) . .
N3 C9 C8 108.36(11) . .
N3 C10 C11 108.39(13) . .
N2 C11 C10 110.28(13) . .
C8 N2 C8 110.56(15) . 7_565
C8 N2 C11 108.40(8) . .
C8 N2 C11 108.40(8) 7_565 .
C9 N3 C9 110.39(13) . 7_565
C9 N3 C10 109.68(8) . .
C9 N3 C10 109.68(8) 7_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.342(2) .
C1 C2 1.388(2) .
C1 C7 1.513(2) .
C2 C3 1.376(3) .
C3 C4 1.374(3) .
C4 C5 1.393(2) .
C5 N1 1.3435(19) .
C5 C6 1.525(2) .
C6 O4 1.2339(19) .
C6 O3 1.263(2) .
C7 O1 1.215(2) .
C7 O2 1.291(2) .
C8 N2 1.4771(16) .
C8 C9 1.5256(18) .
C9 N3 1.4872(15) .
C10 N3 1.499(2) .
C10 C11 1.525(2) .
C11 N2 1.485(2) .
N2 C8 1.4771(16) 7_565
N3 C9 1.4872(15) 7_565
