#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239360.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_2239360
loop_
_publ_author_name
'Dai, Jing-Wei'
'Li, Zhao-Yang'
'Sato, Osamu'
_publ_section_title
;
 1,10-Phenanthroline-5,6-dione ethanol monosolvate
;
_journal_coeditor_code           XU5783
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o573
_journal_paper_doi               10.1107/S1600536814008241
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H6 N2 O2, C2 H6 O'
_chemical_formula_moiety         'C12 H6 N2 O2, C2 H6 O'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_chemical_name_systematic
;
1,10-Phenanthroline-5,6-dione ethanol monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.47(3)
_cell_angle_beta                 101.68(3)
_cell_angle_gamma                109.83(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3064(15)
_cell_length_b                   9.1055(18)
_cell_length_c                   9.7291(19)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      3.1
_cell_volume                     584.6(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5059
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0395
_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)+(0.0709P)²+0.1180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2074
_reflns_number_total             2252
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5783sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        584.6(2)
_cod_database_code               2239360
_cod_database_fobs_code          2239360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
C C4 0.66468(17) 0.96363(14) 0.27101(12) 0.0211(3) Uani d . 1 1
C C11 0.69855(17) 0.93910(13) 0.52865(12) 0.0196(3) Uani d . 1 1
C C5 0.50156(18) 0.80403(14) 0.22423(12) 0.0237(3) Uani d . 1 1
C C7 0.54977(17) 0.78514(14) 0.49173(12) 0.0211(3) Uani d . 1 1
C C6 0.43997(17) 0.70995(13) 0.34035(13) 0.0239(3) Uani d . 1 1
C C12 0.75757(16) 1.02974(13) 0.41609(12) 0.0200(3) Uani d . 1 1
C C8 0.50365(18) 0.70329(14) 0.60099(13) 0.0250(3) Uani d . 1 1
H H8 0.4042 0.5987 0.5794 0.030 Uiso calc R 1 1
C C9 0.60544(18) 0.77748(15) 0.74108(13) 0.0270(3) Uani d . 1 1
H H9 0.5787 0.7248 0.8179 0.032 Uiso calc R 1 1
C C3 0.72616(18) 1.05260(15) 0.16952(13) 0.0252(3) Uani d . 1 1
H H3 0.6651 1.0108 0.0704 0.030 Uiso calc R 1 1
C C1 0.95979(18) 1.25750(14) 0.36088(14) 0.0262(3) Uani d . 1 1
H H1 1.0632 1.3603 0.3919 0.031 Uiso calc R 1 1
C C10 0.74812(18) 0.93131(15) 0.76688(13) 0.0261(3) Uani d . 1 1
H H10 0.8166 0.9818 0.8636 0.031 Uiso calc R 1 1
C C2 0.87625(19) 1.20164(15) 0.21448(14) 0.0272(3) Uani d . 1 1
H H2 0.9213 1.2644 0.1475 0.033 Uiso calc R 1 1
O O1 0.41332(14) 0.74720(11) 0.09901(9) 0.0331(3) Uani d . 1 1
O O2 0.30275(14) 0.58111(10) 0.30567(10) 0.0333(3) Uani d . 1 1
N N2 0.79532(15) 1.01274(12) 0.66490(10) 0.0237(2) Uani d . 1 1
N N1 0.90359(15) 1.17542(12) 0.46054(11) 0.0233(2) Uani d . 1 1
C C15 0.8686(2) 0.65765(16) 0.07549(14) 0.0336(3) Uani d . 1 1
H H15A 0.8325 0.7503 0.0621 0.050 Uiso calc R 1 1
H H15B 0.8372 0.5885 -0.0177 0.050 Uiso calc R 1 1
H H15C 1.0130 0.6934 0.1211 0.050 Uiso calc R 1 1
C C14 0.7508(2) 0.56671(15) 0.16901(14) 0.0312(3) Uani d . 1 1
O O3 0.76490(13) 0.66129(10) 0.30034(9) 0.0291(2) Uani d D 1 1
H H14A 0.598(3) 0.5214(19) 0.1167(17) 0.042(4) Uiso d . 1 1
H H14B 0.797(3) 0.479(2) 0.1910(18) 0.048(5) Uiso d . 1 1
H H3O 0.8864(17) 0.719(2) 0.3431(19) 0.058(5) Uiso d D 1 1
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
C3 C4 C12 118.58(11)
C3 C4 C5 119.93(11)
C12 C4 C5 121.48(11)
N2 C11 C7 122.79(11)
N2 C11 C12 116.36(10)
C7 C11 C12 120.85(11)
O1 C5 C4 122.47(12)
O1 C5 C6 119.54(11)
C4 C5 C6 117.97(10)
C8 C7 C11 118.69(11)
C8 C7 C6 119.96(11)
C11 C7 C6 121.35(11)
O2 C6 C7 122.90(12)
O2 C6 C5 119.48(11)
C7 C6 C5 117.60(10)
N1 C12 C4 122.28(11)
N1 C12 C11 117.04(10)
C4 C12 C11 120.68(11)
C9 C8 C7 118.69(11)
C9 C8 H8 120.7
C7 C8 H8 120.7
C8 C9 C10 118.31(11)
C8 C9 H9 120.8
C10 C9 H9 120.8
C2 C3 C4 119.37(12)
C2 C3 H3 120.3
C4 C3 H3 120.3
N1 C1 C2 124.01(11)
N1 C1 H1 118.0
C2 C1 H1 118.0
N2 C10 C9 124.42(12)
N2 C10 H10 117.8
C9 C10 H10 117.8
C3 C2 C1 117.99(11)
C3 C2 H2 121.0
C1 C2 H2 121.0
C10 N2 C11 117.08(11)
C1 N1 C12 117.77(11)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O3 C14 C15 114.19(11)
O3 C14 H14A 104.6(9)
C15 C14 H14A 109.3(9)
O3 C14 H14B 108.5(10)
C15 C14 H14B 109.8(10)
H14A C14 H14B 110.5(14)
C14 O3 H3O 111.5(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 C3 1.3950(17)
C4 C12 1.3995(17)
C4 C5 1.4818(18)
C11 N2 1.3436(16)
C11 C7 1.4037(17)
C11 C12 1.4899(16)
C5 O1 1.2171(15)
C5 C6 1.5411(17)
C7 C8 1.3972(17)
C7 C6 1.4843(18)
C6 O2 1.2128(16)
C12 N1 1.3448(16)
C8 C9 1.3813(18)
C8 H8 0.9500
C9 C10 1.3914(19)
C9 H9 0.9500
C3 C2 1.3776(19)
C3 H3 0.9500
C1 N1 1.3355(16)
C1 C2 1.3907(18)
C1 H1 0.9500
C10 N2 1.3357(16)
C10 H10 0.9500
C2 H2 0.9500
C15 C14 1.5026(18)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C14 O3 1.4225(15)
C14 H14A 1.040(18)
C14 H14B 0.995(18)
O3 H3O 0.850(10)
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
O3 H3O N1 2_776 0.850(10) 2.080(14) 2.8258(19) 146.2(18)
C1 H1 O2 1_665 0.95 2.53 3.3381(19) 143.1
