#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/02/2230247.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_2230247
loop_
_publ_author_name
'Cheng, Sit Foon'
'Ng, Seik Weng'
_publ_section_title
;
 1,10-Phenanthrolin-1-ium hydrogen
 <small>D</small>,<small>L</small>-tartrate dihydrate
;
_journal_coeditor_code           BT5536
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1306
_journal_paper_doi               10.1107/S1600536811015972
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H9 N2 +, C4 H5 O6 -, 2H2 O'
_chemical_formula_moiety         'C12 H9 N2 +, C4 H5 O6 -, 2(H2 O)'
_chemical_formula_sum            'C16 H18 N2 O8'
_chemical_formula_weight         366.32
_chemical_name_systematic
;
1,10-Phenanthrolin-1-ium hydrogen D,L-tartrate dihydrate
;
_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                98.0810(10)
_cell_angle_beta                 100.3500(10)
_cell_angle_gamma                103.9030(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0933(7)
_cell_length_b                   10.5849(11)
_cell_length_c                   11.4694(11)
_cell_measurement_reflns_used    2722
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.46
_cell_volume                     806.95(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7610
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1012P)²+0.1854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1598
_reflns_number_gt                2880
_reflns_number_total             3635
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5536.cif
_cod_data_source_block           I
_cod_database_code               2230247
_cod_database_fobs_code          2230247
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0272(2) 0.97612(14) 0.33939(12) 0.0172(3) Uani d . 1 1 . .
O O2 0.00294(19) 1.04199(14) 0.16223(12) 0.0167(3) Uani d . 1 1 . .
O O3 0.3922(2) 0.95680(14) 0.34847(12) 0.0163(3) Uani d . 1 1 . .
O O4 0.1832(2) 0.78094(13) 0.12086(12) 0.0154(3) Uani d . 1 1 . .
O O5 0.6410(2) 1.02428(13) 0.15147(12) 0.0153(3) Uani d . 1 1 . .
O O6 0.5609(2) 0.80301(14) 0.09605(13) 0.0192(3) Uani d . 1 1 . .
O O1W 0.2228(2) 0.90933(13) 0.55174(12) 0.0145(3) Uani d . 1 1 . .
O O2W 0.1595(2) 1.23818(15) 0.04324(13) 0.0174(3) Uani d . 1 1 . .
N N1 0.2289(2) 0.65380(16) 0.46822(15) 0.0143(3) Uani d . 1 1 . .
N N2 0.2713(2) 0.66417(16) 0.71074(15) 0.0171(4) Uani d . 1 1 . .
C C1 0.0952(3) 1.00580(17) 0.25142(16) 0.0125(4) Uani d . 1 1 . .
C C2 0.3085(3) 1.00188(18) 0.24666(16) 0.0124(4) Uani d . 1 1 . .
H H2A 0.3902 1.0934 0.2475 0.015 Uiso calc R 1 1 . .
C C3 0.3050(3) 0.91028(18) 0.12952(16) 0.0115(4) Uani d . 1 1 . .
H H3A 0.2505 0.9473 0.0594 0.014 Uiso calc R 1 1 . .
C C4 0.5161(3) 0.90552(18) 0.12418(16) 0.0122(4) Uani d . 1 1 . .
C C5 0.2130(3) 0.6578(2) 0.35202(18) 0.0184(4) Uani d . 1 1 . .
H H5A 0.2027 0.7366 0.3240 0.022 Uiso calc R 1 1 . .
C C6 0.2114(3) 0.5459(2) 0.27087(19) 0.0220(5) Uani d . 1 1 . .
H H6 0.2015 0.5487 0.1876 0.026 Uiso calc R 1 1 . .
C C7 0.2243(3) 0.4319(2) 0.31181(19) 0.0213(4) Uani d . 1 1 . .
H H7 0.2216 0.3552 0.2567 0.026 Uiso calc R 1 1 . .
C C8 0.2417(3) 0.42852(19) 0.43589(19) 0.0178(4) Uani d . 1 1 . .
C C9 0.2446(3) 0.54419(18) 0.51418(17) 0.0138(4) Uani d . 1 1 . .
C C10 0.2550(3) 0.3129(2) 0.4856(2) 0.0220(5) Uani d . 1 1 . .
H H10 0.2530 0.2340 0.4337 0.026 Uiso calc R 1 1 . .
C C11 0.2704(3) 0.3145(2) 0.6049(2) 0.0224(5) Uani d . 1 1 . .
H H11A 0.2778 0.2366 0.6356 0.027 Uiso calc R 1 1 . .
C C12 0.2757(3) 0.43249(19) 0.68601(19) 0.0173(4) Uani d . 1 1 . .
C C13 0.2645(3) 0.54791(18) 0.64134(18) 0.0149(4) Uani d . 1 1 . .
C C14 0.2935(3) 0.4390(2) 0.8110(2) 0.0227(5) Uani d . 1 1 . .
H H14 0.3004 0.3633 0.8456 0.027 Uiso calc R 1 1 . .
C C15 0.3006(3) 0.5558(2) 0.8818(2) 0.0236(5) Uani d . 1 1 . .
H H15 0.3135 0.5626 0.9665 0.028 Uiso calc R 1 1 . .
C C16 0.2888(3) 0.6661(2) 0.82806(18) 0.0210(4) Uani d . 1 1 . .
H H16 0.2936 0.7464 0.8787 0.025 Uiso calc R 1 1 . .
H H3 0.517(5) 1.006(3) 0.381(3) 0.048(9) Uiso d . 1 1 . .
H H4 0.066(4) 0.767(3) 0.067(3) 0.032(7) Uiso d . 1 1 . .
H H5 0.781(5) 1.020(3) 0.156(3) 0.057(10) Uiso d . 1 1 . .
H H11 0.145(5) 0.944(4) 0.593(4) 0.067(11) Uiso d . 1 1 . .
H H12 0.195(4) 0.938(3) 0.480(3) 0.039(8) Uiso d . 1 1 . .
H H21 0.120(5) 1.172(4) 0.074(3) 0.052(10) Uiso d . 1 1 . .
H H22 0.247(5) 1.223(3) 0.003(3) 0.037(8) Uiso d . 1 1 . .
H H1 0.233(5) 0.731(3) 0.520(3) 0.046(8) Uiso 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O3 H3 . . 111(2) ?
C3 O4 H4 . . 110.2(17) ?
C4 O5 H5 . . 111.6(19) ?
H11 O1W H12 . . 101(3) ?
H21 O2W H22 . . 109(3) ?
C5 N1 C9 . . 122.93(18) ?
C5 N1 H1 . . 117.6(19) ?
C9 N1 H1 . . 119.4(19) ?
C16 N2 C13 . . 116.48(17) ?
O1 C1 O2 . . 125.36(18) ?
O1 C1 C2 . . 119.50(17) ?
O2 C1 C2 . . 115.13(16) ?
O3 C2 C1 . . 109.60(14) ?
O3 C2 C3 . . 110.78(15) ?
C1 C2 C3 . . 109.30(14) ?
O3 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
O4 C3 C4 . . 109.91(14) ?
O4 C3 C2 . . 111.42(14) ?
C4 C3 C2 . . 109.66(14) ?
O4 C3 H3A . . 108.6 ?
C4 C3 H3A . . 108.6 ?
C2 C3 H3A . . 108.6 ?
O6 C4 O5 . . 124.72(17) ?
O6 C4 C3 . . 123.46(17) ?
O5 C4 C3 . . 111.81(15) ?
N1 C5 C6 . . 119.94(19) ?
N1 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C7 C6 C5 . . 119.74(19) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 119.99(19) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 118.09(19) ?
C9 C8 C10 . . 118.62(19) ?
C7 C8 C10 . . 123.30(19) ?
N1 C9 C8 . . 119.30(18) ?
N1 C9 C13 . . 119.82(17) ?
C8 C9 C13 . . 120.88(18) ?
C11 C10 C8 . . 121.05(19) ?
C11 C10 H10 . . 119.5 ?
C8 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.86(19) ?
C10 C11 H11A . . 119.6 ?
C12 C11 H11A . . 119.6 ?
C13 C12 C14 . . 117.29(18) ?
C13 C12 C11 . . 119.93(19) ?
C14 C12 C11 . . 122.78(18) ?
N2 C13 C12 . . 124.24(18) ?
N2 C13 C9 . . 117.11(17) ?
C12 C13 C9 . . 118.65(18) ?
C15 C14 C12 . . 118.92(19) ?
C15 C14 H14 . . 120.5 ?
C12 C14 H14 . . 120.5 ?
C14 C15 C16 . . 119.4(2) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
N2 C16 C15 . . 123.7(2) ?
N2 C16 H16 . . 118.1 ?
C15 C16 H16 . . 118.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.241(2) ?
O2 C1 . 1.269(2) ?
O3 C2 . 1.410(2) ?
O3 H3 . 0.89(3) ?
O4 C3 . 1.412(2) ?
O4 H4 . 0.91(3) ?
O5 C4 . 1.311(2) ?
O5 H5 . 1.00(3) ?
O6 C4 . 1.219(2) ?
O1W H11 . 0.90(4) ?
O1W H12 . 0.92(3) ?
O2W H21 . 0.84(4) ?
O2W H22 . 0.87(3) ?
N1 C5 . 1.325(3) ?
N1 C9 . 1.360(3) ?
N1 H1 . 0.93(3) ?
N2 C16 . 1.326(3) ?
N2 C13 . 1.354(2) ?
C1 C2 . 1.534(2) ?
C2 C3 . 1.535(2) ?
C2 H2A . 1.0000 ?
C3 C4 . 1.522(2) ?
C3 H3A . 1.0000 ?
C5 C6 . 1.395(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.372(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.412(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.406(3) ?
C8 C10 . 1.437(3) ?
C9 C13 . 1.434(3) ?
C10 C11 . 1.350(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.437(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.403(3) ?
C12 C14 . 1.407(3) ?
C14 C15 . 1.365(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.407(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
_geom_hbond_publ_flag
O3 H3 O1w 2_676 0.89(3) 1.82(3) 2.709(2) 175(3) yes
O4 H4 O2w 2_575 0.90(3) 1.84(3) 2.739(2) 172(3) yes
O5 H5 O2 1_655 0.99(3) 1.52(3) 2.508(2) 169(3) yes
O1w H12 O1 . 0.93(3) 1.97(3) 2.846(2) 157(3) yes
O1w H11 O1 2_576 0.90(4) 1.86(4) 2.753(2) 173(4) yes
O2w H21 O2 . 0.84(4) 1.93(4) 2.764(2) 168(3) yes
O2w H22 O6 2_675 0.87(3) 1.97(3) 2.835(2) 176(3) yes
N1 H1 O1w . 0.93(3) 1.89(3) 2.753(2) 153(3) yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 O3 . . . . 2.5(2) ?
O2 C1 C2 O3 . . . . -178.33(15) ?
O1 C1 C2 C3 . . . . 124.08(18) ?
O2 C1 C2 C3 . . . . -56.7(2) ?
O3 C2 C3 O4 . . . . 62.92(19) ?
C1 C2 C3 O4 . . . . -57.94(19) ?
O3 C2 C3 C4 . . . . -58.99(19) ?
C1 C2 C3 C4 . . . . -179.86(14) ?
O4 C3 C4 O6 . . . . 11.4(2) ?
C2 C3 C4 O6 . . . . 134.17(19) ?
O4 C3 C4 O5 . . . . -169.64(14) ?
C2 C3 C4 O5 . . . . -46.8(2) ?
C9 N1 C5 C6 . . . . 0.1(3) ?
N1 C5 C6 C7 . . . . 0.7(3) ?
C5 C6 C7 C8 . . . . -0.8(3) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C6 C7 C8 C10 . . . . 179.72(19) ?
C5 N1 C9 C8 . . . . -0.8(3) ?
C5 N1 C9 C13 . . . . 179.01(18) ?
C7 C8 C9 N1 . . . . 0.6(3) ?
C10 C8 C9 N1 . . . . -178.97(17) ?
C7 C8 C9 C13 . . . . -179.19(17) ?
C10 C8 C9 C13 . . . . 1.3(3) ?
C9 C8 C10 C11 . . . . -0.1(3) ?
C7 C8 C10 C11 . . . . -179.65(19) ?
C8 C10 C11 C12 . . . . -0.6(3) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C10 C11 C12 C14 . . . . -179.4(2) ?
C16 N2 C13 C12 . . . . -0.3(3) ?
C16 N2 C13 C9 . . . . 179.70(17) ?
C14 C12 C13 N2 . . . . 0.6(3) ?
C11 C12 C13 N2 . . . . -178.96(18) ?
C14 C12 C13 C9 . . . . -179.49(17) ?
C11 C12 C13 C9 . . . . 1.0(3) ?
N1 C9 C13 N2 . . . . -1.5(3) ?
C8 C9 C13 N2 . . . . 178.28(17) ?
N1 C9 C13 C12 . . . . 178.54(17) ?
C8 C9 C13 C12 . . . . -1.7(3) ?
C13 C12 C14 C15 . . . . -0.6(3) ?
C11 C12 C14 C15 . . . . 178.92(19) ?
C12 C14 C15 C16 . . . . 0.4(3) ?
C13 N2 C16 C15 . . . . 0.1(3) ?
C14 C15 C16 N2 . . . . -0.2(3) ?
