#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/22/7212247.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_7212247
loop_
_publ_author_name
'Ye, Heng-Yun'
'Ge, Jia-Zhen'
'Chen, Fang'
'Xiong, Ren-Gen'
_publ_section_title
;
 Reversible phase transition of the 1 : 1 co-crystal of
 1,4-diazabicyclo-[2.2.2]octane (DABCO) and hydroquinone,
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1705
_journal_paper_doi               10.1039/b923314h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C6 H12 N2, C6 H6 O2 '
_chemical_formula_sum            'C12 H18 N2 O2'
_chemical_formula_weight         222.28
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 118.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.951(2)
_cell_length_b                   9.5070(19)
_cell_length_c                   11.672(2)
_cell_measurement_reflns_used    4953
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.41
_cell_volume                     1160.4(5)
_computing_cell_refinement       'crystalclear (Rigaku, 2005)'
_computing_data_collection       'crystalclear (Rigaku, 2005)'
_computing_data_reduction        'crystalclear (Rigaku, 2005)'
_computing_molecular_graphics
'SHELXtl (Sheldrick, 2008); diamond (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXtl (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXtl (Sheldrick, 2008)'
_computing_structure_solution    'SHELXtl (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Raxis-Rapid diffractometer'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5864
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'crystalclear (Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0522
_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)+(0.0612P)²+0.4180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                1007
_reflns_number_total             1334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b923314h.txt
_cod_data_source_block           298K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1160.4(4)
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7212247
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
N2 N 0.38096(12) 0.36036(14) 0.21759(12) 0.0420(4) Uani 1 1 d .
C9 C 0.45680(16) 0.4305(2) 0.34508(16) 0.0512(5) Uani 1 1 d .
H9B H 0.4478 0.3797 0.4122 0.061 Uiso 1 1 calc R
H9A H 0.4253 0.5254 0.3409 0.061 Uiso 1 1 calc R
C8 C 0.40156(15) 0.43543(19) 0.11938(15) 0.0506(5) Uani 1 1 d .
H8B H 0.3748 0.5326 0.1144 0.061 Uiso 1 1 calc R
H8A H 0.3500 0.3927 0.0341 0.061 Uiso 1 1 calc R
C7 C 0.42864(16) 0.21565(18) 0.22850(18) 0.0542(5) Uani 1 1 d .
H7B H 0.3822 0.1688 0.1445 0.065 Uiso 1 1 calc R
H7A H 0.4140 0.1640 0.2917 0.065 Uiso 1 1 calc R
O1 O 0.12184(13) 0.34462(17) 0.10058(13) 0.0751(5) Uani 1 1 d .
C3 C -0.06774(16) 0.34645(18) 0.11536(16) 0.0509(5) Uani 1 1 d .
H3A H -0.1143 0.3483 0.0244 0.061 Uiso 1 1 calc R
C5 C 0.13127(15) 0.34505(18) 0.31252(16) 0.0477(4) Uani 1 1 d .
H5A H 0.2202 0.3441 0.3555 0.057 Uiso 1 1 calc R
C4 C 0.06416(15) 0.34508(17) 0.17675(16) 0.0454(4) Uani 1 1 d .
H1 H 0.214(3) 0.354(2) 0.151(3) 0.104(9) Uiso 1 1 d .
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
N2 0.0385(7) 0.0497(8) 0.0402(7) -0.0022(5) 0.0210(6) -0.0013(5)
C9 0.0495(10) 0.0633(11) 0.0461(9) -0.0121(8) 0.0272(8) -0.0025(8)
C8 0.0456(9) 0.0611(11) 0.0439(8) 0.0118(7) 0.0206(7) 0.0082(7)
C7 0.0575(11) 0.0448(10) 0.0615(11) -0.0035(8) 0.0298(9) -0.0090(7)
O1 0.0453(8) 0.1347(14) 0.0506(8) -0.0170(7) 0.0273(6) -0.0038(8)
C3 0.0417(9) 0.0658(11) 0.0416(8) -0.0104(7) 0.0172(7) 0.0001(7)
C5 0.0325(8) 0.0586(10) 0.0482(9) 0.0023(7) 0.0164(7) -0.0009(7)
C4 0.0394(9) 0.0514(9) 0.0472(9) -0.0071(7) 0.0225(7) -0.0007(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'
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
_geom_angle_site_symmetry_3
C8 N2 C7 108.53(13) . .
C8 N2 C9 108.33(13) . .
C7 N2 C9 108.20(13) . .
N2 C9 C8 110.19(13) . 2_655
N2 C9 H9B 109.6 . .
C8 C9 H9B 109.6 2_655 .
N2 C9 H9A 109.6 . .
C8 C9 H9A 109.6 2_655 .
H9B C9 H9A 108.1 . .
N2 C8 C9 110.69(12) . 2_655
N2 C8 H8B 109.5 . .
C9 C8 H8B 109.5 2_655 .
N2 C8 H8A 109.5 . .
C9 C8 H8A 109.5 2_655 .
H8B C8 H8A 108.1 . .
N2 C7 C7 110.65(8) . 2_655
N2 C7 H7B 109.5 . .
C7 C7 H7B 109.5 2_655 .
N2 C7 H7A 109.5 . .
C7 C7 H7A 109.5 2_655 .
H7B C7 H7A 108.1 . .
C4 O1 H1 113.1(15) . .
C5 C3 C4 120.70(16) 2 .
C5 C3 H3A 119.6 2 .
C4 C3 H3A 119.6 . .
C3 C5 C4 120.82(15) 2 .
C3 C5 H5A 119.6 2 .
C4 C5 H5A 119.6 . .
O1 C4 C3 118.19(15) . .
O1 C4 C5 123.35(14) . .
C3 C4 C5 118.46(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C8 1.469(2) .
N2 C7 1.471(2) .
N2 C9 1.475(2) .
C9 C8 1.536(2) 2_655
C9 H9B 0.9700 .
C9 H9A 0.9700 .
C8 C9 1.536(2) 2_655
C8 H8B 0.9700 .
C8 H8A 0.9700 .
C7 C7 1.527(3) 2_655
C7 H7B 0.9700 .
C7 H7A 0.9700 .
O1 C4 1.363(2) .
O1 H1 0.97(3) .
C3 C5 1.380(2) 2
C3 C4 1.380(2) .
C3 H3A 0.9300 .
C5 C3 1.380(2) 2
C5 C4 1.387(2) .
C5 H5A 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N2 0.97(3) 1.76(3) 2.717(2) 170(2)
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_1
_geom_torsion_site_symmetry_4
C8 N2 C9 C8 -56.50(16) . 2_655
C7 N2 C9 C8 60.98(17) . 2_655
C7 N2 C8 C9 -56.12(17) . 2_655
C9 N2 C8 C9 61.14(16) . 2_655
C8 N2 C7 C7 60.4(2) . 2_655
C9 N2 C7 C7 -56.9(2) . 2_655
C5 C3 C4 O1 179.12(16) 2 .
C5 C3 C4 C5 -1.2(2) 2 .
C3 C5 C4 O1 179.58(16) 2 .
C3 C5 C4 C3 0.0(2) 2 .
