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#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/52/2205281.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2205281
loop_
_publ_author_name
'Bjernemose, Jens K.'
'Bond, Andrew D.'
_publ_section_title
;
 meso-1,2-Bis(pyridin-2-yl)ethane-1,2-diol
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o741
_journal_page_last               o742
_journal_paper_doi               10.1107/S1600536805005222
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_chemical_name_systematic
;
 meso-1,2-bis(pyridin-2-yl)-ethane-1,2-diol
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.196(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3155(14)
_cell_length_b                   8.108(2)
_cell_length_c                   11.737(3)
_cell_measurement_reflns_used    1853
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      3.83
_cell_volume                     505.8(2)
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker-Nonius, 2004)'
_computing_data_reduction        'SAINT v.7.06a (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ 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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6075
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         3.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS v.2.10 (Sheldrick, 2003)
 Ratio of minimum to maximum apparent transmission:  0.592890
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0588
_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)+(0.0396P)²+0.2558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1473
_reflns_number_gt                1026
_reflns_number_total             1236
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6145.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205281
_cod_database_fobs_code          2205281
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.2162(3) 0.1732(2) 0.49298(15) 0.0331(5) Uani d . 1 O
H1 0.3366 0.1713 0.4468 0.050 Uiso calc R 1 H
N1 0.3968(4) -0.1194(3) 0.66357(17) 0.0318(5) Uani d . 1 N
C1 0.1884(5) -0.0311(3) 0.6412(2) 0.0279(5) Uani d . 1 C
C2 0.0389(6) 0.0309(3) 0.7274(2) 0.0334(6) Uani d . 1 C
H2A -0.1091 0.0916 0.7098 0.040 Uiso calc R 1 H
C3 0.1081(6) 0.0033(3) 0.8400(2) 0.0363(6) Uani d . 1 C
H3A 0.0090 0.0458 0.9005 0.044 Uiso calc R 1 H
C4 0.3233(6) -0.0870(3) 0.8629(2) 0.0355(6) Uani d . 1 C
H4A 0.3747 -0.1079 0.9392 0.043 Uiso calc R 1 H
C5 0.4599(5) -0.1453(3) 0.7733(2) 0.0354(6) Uani d . 1 C
H5A 0.6074 -0.2075 0.7892 0.042 Uiso calc R 1 H
C6 0.1359(5) 0.0076(3) 0.5162(2) 0.0302(6) Uani d . 1 C
H6A 0.2362 -0.0697 0.4680 0.036 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0437(10) 0.0305(9) 0.0250(9) -0.0066(8) 0.0041(8) 0.0037(8)
N1 0.0324(11) 0.0366(11) 0.0265(9) 0.0023(9) 0.0010(9) 0.0053(9)
C1 0.0351(13) 0.0292(12) 0.0195(10) 0.0012(10) -0.0004(10) 0.0028(9)
C2 0.0400(15) 0.0358(14) 0.0245(12) 0.0068(11) 0.0029(11) 0.0008(10)
C3 0.0533(16) 0.0316(12) 0.0240(11) -0.0030(12) 0.0027(12) -0.0024(11)
C4 0.0537(17) 0.0356(14) 0.0170(10) -0.0097(13) -0.0083(11) 0.0075(10)
C5 0.0341(14) 0.0360(13) 0.0361(15) -0.0012(11) -0.0036(11) 0.0092(11)
C6 0.0404(14) 0.0322(12) 0.0179(10) 0.0034(10) 0.0042(10) 0.0013(9)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 O1 H1 . . 109.5
C1 N1 C5 . . 118.2(2)
N1 C1 C2 . . 121.8(2)
N1 C1 C6 . . 116.4(2)
C2 C1 C6 . . 121.7(2)
C1 C2 C3 . . 119.1(3)
C1 C2 H2A . . 120.5
C3 C2 H2A . . 120.5
C4 C3 C2 . . 119.1(3)
C4 C3 H3A . . 120.4
C2 C3 H3A . . 120.4
C5 C4 C3 . . 118.4(2)
C5 C4 H4A . . 120.8
C3 C4 H4A . . 120.8
N1 C5 C4 . . 123.5(3)
N1 C5 H5A . . 118.3
C4 C5 H5A . . 118.3
O1 C6 C6 . 3_556 108.4(3)
O1 C6 C1 . . 108.79(19)
C6 C6 C1 3_556 . 113.6(3)
O1 C6 H6A . . 108.6
C6 C6 H6A 3_556 . 108.6
C1 C6 H6A . . 108.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C6 . 1.435(3)
O1 H1 . 0.840
N1 C1 . 1.344(3)
N1 C5 . 1.347(3)
C1 C2 . 1.383(3)
C1 C6 . 1.525(3)
C2 C3 . 1.389(4)
C2 H2A . 0.950
C3 C4 . 1.384(4)
C3 H3A . 0.950
C4 C5 . 1.365(4)
C4 H4A . 0.950
C5 H5A . 0.950
C6 C6 3_556 1.498(5)
C6 H6A . 1.000
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 3_656 0.84 1.97 2.797(3) 168.5
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_site_symmetry_4
_geom_torsion
C5 N1 C1 C2 . -0.7(4)
C5 N1 C1 C6 . 175.0(2)
N1 C1 C2 C3 . 1.0(4)
C6 C1 C2 C3 . -174.5(2)
C1 C2 C3 C4 . -0.7(4)
C2 C3 C4 C5 . 0.1(4)
C1 N1 C5 C4 . 0.1(4)
C3 C4 C5 N1 . 0.1(4)
N1 C1 C6 O1 . -99.9(2)
C2 C1 C6 O1 . 75.8(3)
N1 C1 C6 C6 3_556 139.2(3)
C2 C1 C6 C6 3_556 -45.1(4)
