#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:00:51 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179462 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/59/4335922.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_4335922
loop_
_publ_author_name
'Ryoji Mitsuhashi'
'Takayoshi Suzuki'
'Yukinari Sunatsuki'
_publ_section_title
;
 Four-Electron Oxidative Dehydrogenation Induced by Proton-Coupled
 Electron Transfer in Ruthenium(III) Complex with
 2-(1,4,5,6-Tetrahydropyrimidin-2-yl)phenolate
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10183
_journal_page_last               10190
_journal_paper_doi               10.1021/ic401667v
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C10 H12 N2 O'
_chemical_formula_sum            'C10 H12 N2 O'
_chemical_formula_weight         176.22
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.326(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7896(11)
_cell_length_b                   7.1703(9)
_cell_length_c                   12.6538(13)
_cell_measurement_reflns_used    5635
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.28
_cell_volume                     870.93(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'ortep-3 for win'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      188(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8334
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.28
_diffrn_standards_number         8334
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0410
_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)+(0.0851P)²+0.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                1747
_reflns_number_total             1999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401667v_si_002_09.cif
_cod_data_source_block           H2thp
_cod_database_code               4335922
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_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
O1 O 0.38429(7) 0.15310(10) 0.11946(5) 0.0308(2) Uani 1 1 d
N1 N 0.52198(9) 0.24193(11) 0.45426(6) 0.0268(2) Uani 1 1 d
N2 N 0.57660(8) 0.18386(12) 0.28799(6) 0.0261(2) Uani 1 1 d
C1 C 0.29561(10) 0.18297(13) 0.18151(7) 0.0250(2) Uani 1 1 d
C2 C 0.14984(11) 0.18367(16) 0.13822(8) 0.0312(3) Uani 1 1 d
C3 C 0.05255(10) 0.21832(17) 0.20035(9) 0.0350(3) Uani 1 1 d
C4 C 0.09367(11) 0.25476(16) 0.31069(9) 0.0346(3) Uani 1 1 d
C5 C 0.23331(10) 0.25243(14) 0.35641(8) 0.0281(2) Uani 1 1 d
C6 C 0.33567(9) 0.21654(12) 0.29534(7) 0.0234(2) Uani 1 1 d
C7 C 0.48343(10) 0.21503(12) 0.34845(7) 0.0231(2) Uani 1 1 d
C8 C 0.66791(10) 0.24373(15) 0.50909(8) 0.0305(3) Uani 1 1 d
C9 C 0.75353(10) 0.12331(15) 0.44818(8) 0.0304(3) Uani 1 1 d
C10 C 0.72646(10) 0.17987(14) 0.32997(8) 0.0277(2) Uani 1 1 d
H1N H 0.4588(14) 0.2711(17) 0.4938(11) 0.036(3) Uiso 1 1 d
H2N H 0.5355(15) 0.163(2) 0.2162(13) 0.053(4) Uiso 1 1 d
H2 H 0.1211(14) 0.154(2) 0.0622(12) 0.048(4) Uiso 1 1 d
H3 H -0.0475(18) 0.218(2) 0.1655(13) 0.054(4) Uiso 1 1 d
H4 H 0.0221(15) 0.2802(19) 0.3548(12) 0.043(3) Uiso 1 1 d
H5 H 0.2614(14) 0.2773(19) 0.4321(11) 0.039(3) Uiso 1 1 d
H8A H 0.6703(13) 0.1949(18) 0.5800(11) 0.036(3) Uiso 1 1 d
H8B H 0.7003(12) 0.3732(19) 0.5132(9) 0.034(3) Uiso 1 1 d
H9A H 0.8543(13) 0.1347(18) 0.4793(10) 0.036(3) Uiso 1 1 d
H9B H 0.7259(11) -0.0096(18) 0.4540(9) 0.031(3) Uiso 1 1 d
H10A H 0.7650(12) 0.3058(18) 0.3215(9) 0.030(3) Uiso 1 1 d
H10B H 0.7669(11) 0.0903(17) 0.2869(9) 0.029(3) Uiso 1 1 d
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
C7 N1 C8 122.45(8)
C7 N1 H1N 120.4(8)
C8 N1 H1N 116.9(8)
C7 N2 C10 123.52(8)
C7 N2 H2N 112.2(9)
C10 N2 H2N 124.3(9)
O1 C1 C2 120.44(8)
O1 C1 C6 123.42(8)
C2 C1 C6 116.13(9)
C3 C2 C1 122.43(9)
C3 C2 H2 120.6(8)
C1 C2 H2 117.0(8)
C2 C3 C4 120.64(10)
C2 C3 H3 118.8(9)
C4 C3 H3 120.6(9)
C5 C4 C3 118.98(10)
C5 C4 H4 121.1(8)
C3 C4 H4 119.9(8)
C4 C5 C6 121.90(9)
C4 C5 H5 118.9(8)
C6 C5 H5 119.2(8)
C5 C6 C1 119.90(9)
C5 C6 C7 119.61(9)
C1 C6 C7 120.48(8)
N2 C7 N1 121.05(9)
N2 C7 C6 117.79(8)
N1 C7 C6 121.16(9)
N1 C8 C9 109.91(8)
N1 C8 H8A 106.5(8)
C9 C8 H8A 110.7(8)
N1 C8 H8B 108.1(7)
C9 C8 H8B 111.2(7)
H8A C8 H8B 110.4(10)
C8 C9 C10 109.95(8)
C8 C9 H9A 111.0(7)
C10 C9 H9A 109.6(7)
C8 C9 H9B 108.8(7)
C10 C9 H9B 109.3(7)
H9A C9 H9B 108.2(10)
N2 C10 C9 109.37(8)
N2 C10 H10A 108.6(7)
C9 C10 H10A 110.6(6)
N2 C10 H10B 107.4(7)
C9 C10 H10B 111.3(7)
H10A C10 H10B 109.5(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2976(12)
N1 C7 1.3318(12)
N1 C8 1.4605(12)
N1 H1N 0.893(14)
N2 C7 1.3195(12)
N2 C10 1.4592(12)
N2 H2N 0.931(15)
C1 C2 1.4246(14)
C1 C6 1.4369(13)
C2 C3 1.3715(15)
C2 H2 0.970(15)
C3 C4 1.3996(16)
C3 H3 0.992(17)
C4 C5 1.3759(14)
C4 H4 0.995(15)
C5 C6 1.4041(14)
C5 H5 0.960(14)
C6 C7 1.4705(13)
C8 C9 1.5152(14)
C8 H8A 0.960(14)
C8 H8B 0.979(13)
C9 C10 1.5219(14)
C9 H9A 0.991(13)
C9 H9B 0.997(13)
C10 H10A 0.993(13)
C10 H10B 0.975(12)
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
_geom_hbond_site_symmetry_A
N1 H1n O1 0.893(15) 1.953(15) 2.8036(12) 158.7(12) 4_566
N2 H2n O1 0.931(15) 1.727(15) 2.5620(10) 147.6(15) 1_555
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
O1 C1 C2 C3 -178.65(10)
C6 C1 C2 C3 1.40(14)
C1 C2 C3 C4 -0.07(17)
C2 C3 C4 C5 -1.01(17)
C3 C4 C5 C6 0.70(16)
C4 C5 C6 C1 0.69(14)
C4 C5 C6 C7 -179.76(9)
O1 C1 C6 C5 178.37(9)
C2 C1 C6 C5 -1.69(13)
O1 C1 C6 C7 -1.17(14)
C2 C1 C6 C7 178.77(8)
C10 N2 C7 N1 -1.26(14)
C10 N2 C7 C6 179.55(8)
C8 N1 C7 N2 1.68(14)
C8 N1 C7 C6 -179.15(8)
C5 C6 C7 N2 -178.89(8)
C1 C6 C7 N2 0.66(13)
C5 C6 C7 N1 1.92(13)
C1 C6 C7 N1 -178.54(8)
C7 N1 C8 C9 -27.98(12)
N1 C8 C9 C10 51.85(11)
C7 N2 C10 C9 26.96(12)
C8 C9 C10 N2 -51.16(11)
