#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:32:08 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179065 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/27/4302779.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_4302779
loop_
_publ_author_name
'Michael J. Rose'
'Pradip K. Mascharak'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry,
University of California, Santa Cruz,
1156 High Street,
Santa Cruz, CA 95064
USA
;
_publ_contact_author_email       pradip@chemsitry.ucsc.edu
_publ_contact_author_fax         '+1 831 459 2935'
_publ_contact_author_name        'Pradip Mascharak'
_publ_contact_author_phone       '+1 831 459 4251'
_publ_section_title
;
Photosensitization of Ruthenium Nitrosyls to Red Light with an
Isoelectronic Series of Heavy-Atom Chromophores: Experimental and Density
Functional Theory Studies on the Effects of O-, S- and Se-Substituted
Coordinated Dyes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6904
_journal_page_last               6917
_journal_paper_doi               10.1021/ic900899j
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C12 H6 N O2 Se'
_chemical_formula_weight         275.14
_chemical_name_systematic
; 
 ? 
;
_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                103.180(2)
_cell_angle_beta                 96.138(2)
_cell_angle_gamma                96.173(2)
_cell_formula_units_Z            4
_cell_length_a                   7.4489(12)
_cell_length_b                   10.9453(17)
_cell_length_c                   12.295(2)
_cell_measurement_reflns_used    9561
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.51
_cell_volume                     961.4(3)
_computing_cell_refinement       'Bruker SAINT v7.34'
_computing_data_collection       'Bruker APEX-II v2.1-4'
_computing_data_reduction        'Bruker SAINT v7.34'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       ω/2θ-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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0317
_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       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9562
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    3.885
_exptl_absorpt_correction_T_max  0.91397
_exptl_absorpt_correction_T_min  0.64702
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sheldrick, 2007'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.803
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.803
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3326
_reflns_number_total             3891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic900899j_si_002_2.cif
_cod_data_source_block           Seln
_cod_database_code               4302779
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.29637(4) 1.03960(3) 0.70151(2) 0.01782(11) Uani 1 1 d . . .
Se2 Se -0.26025(4) 0.67814(3) -0.19939(2) 0.02188(12) Uani 1 1 d . . .
O1 O 0.0608(3) 1.4504(2) 0.6396(2) 0.0227(5) Uani 1 1 d . . .
H1 H 0.068(11) 1.477(8) 0.712(8) 0.027 Uiso 0.50 1 d P . .
O2 O 0.4611(3) 0.5903(2) 0.5776(2) 0.0237(5) Uani 1 1 d . . .
H2 H 0.482(12) 0.543(8) 0.538(7) 0.028 Uiso 0.50 1 d P . .
O3 O 0.3810(3) 0.9261(2) -0.0779(2) 0.0262(6) Uani 1 1 d . . .
H3 H 0.449(12) 0.952(9) -0.048(7) 0.031 Uiso 0.50 1 d P . .
O4 O -0.9056(3) 0.4991(2) -0.1418(2) 0.0228(5) Uani 1 1 d . . .
H4 H -0.918(11) 0.486(7) -0.218(8) 0.027 Uiso 0.50 1 d P . .
N1 N 0.2318(3) 0.9900(2) 0.4276(2) 0.0193(5) Uani 1 1 d . . .
N2 N -0.2481(3) 0.7630(2) 0.0717(2) 0.0194(5) Uani 1 1 d . . .
C1 C 0.2138(4) 1.1424(3) 0.6088(2) 0.0162(6) Uani 1 1 d . . .
C2 C 0.1688(4) 1.2588(3) 0.6596(3) 0.0183(6) Uani 1 1 d . . .
H2A H 0.1788 1.2837 0.7378 0.022 Uiso 1 1 calc R . .
C3 C 0.1074(4) 1.3411(3) 0.5938(3) 0.0194(6) Uani 1 1 d . . .
C4 C 0.0951(4) 1.3027(3) 0.4744(3) 0.0218(7) Uani 1 1 d . . .
H4A H 0.0580 1.3564 0.4302 0.026 Uiso 1 1 calc R . .
C5 C 0.1377(4) 1.1872(3) 0.4252(3) 0.0215(6) Uani 1 1 d . . .
H5A H 0.1277 1.1631 0.3470 0.026 Uiso 1 1 calc R . .
C6 C 0.1974(4) 1.1010(3) 0.4884(3) 0.0183(6) Uani 1 1 d . . .
C7 C 0.2892(4) 0.8968(3) 0.4718(2) 0.0175(6) Uani 1 1 d . . .
C8 C 0.3146(4) 0.7840(3) 0.3929(3) 0.0213(6) Uani 1 1 d . . .
H8A H 0.2918 0.7801 0.3162 0.026 Uiso 1 1 calc R . .
C9 C 0.3705(4) 0.6832(3) 0.4255(3) 0.0211(6) Uani 1 1 d . . .
H9A H 0.3852 0.6117 0.3714 0.025 Uiso 1 1 calc R . .
C10 C 0.4074(4) 0.6851(3) 0.5429(3) 0.0198(6) Uani 1 1 d . . .
C11 C 0.3844(4) 0.7961(3) 0.6224(3) 0.0187(6) Uani 1 1 d . . .
H11A H 0.4086 0.7998 0.6990 0.022 Uiso 1 1 calc R . .
C12 C 0.3269(4) 0.8985(3) 0.5886(3) 0.0181(6) Uani 1 1 d . . .
C13 C -0.0734(4) 0.7725(3) -0.0875(3) 0.0188(6) Uani 1 1 d . . .
C14 C 0.0869(4) 0.8139(3) -0.1218(3) 0.0199(6) Uani 1 1 d . . .
H14A H 0.1003 0.7925 -0.1979 0.024 Uiso 1 1 calc R . .
C15 C 0.2312(4) 0.8885(3) -0.0431(3) 0.0221(7) Uani 1 1 d . . .
C16 C 0.2063(4) 0.9208(3) 0.0740(3) 0.0219(7) Uani 1 1 d . . .
H16A H 0.2982 0.9721 0.1271 0.026 Uiso 1 1 calc R . .
C17 C 0.0490(4) 0.8765(3) 0.1072(3) 0.0224(7) Uani 1 1 d . . .
H17A H 0.0372 0.8960 0.1835 0.027 Uiso 1 1 calc R . .
C18 C -0.0994(4) 0.8007(3) 0.0284(2) 0.0186(6) Uani 1 1 d . . .
C19 C -0.4020(4) 0.6965(3) 0.0120(2) 0.0172(6) Uani 1 1 d . . .
C20 C -0.5451(4) 0.6654(3) 0.0748(3) 0.0210(6) Uani 1 1 d . . .
H20A H -0.5241 0.6909 0.1531 0.025 Uiso 1 1 calc R . .
C21 C -0.7087(4) 0.6006(3) 0.0248(3) 0.0216(7) Uani 1 1 d . . .
H21A H -0.7976 0.5824 0.0687 0.026 Uiso 1 1 calc R . .
C22 C -0.7460(4) 0.5598(3) -0.0957(3) 0.0203(6) Uani 1 1 d . . .
C23 C -0.6081(4) 0.5881(3) -0.1608(3) 0.0200(6) Uani 1 1 d . . .
H23A H -0.6308 0.5631 -0.2391 0.024 Uiso 1 1 calc R . .
C24 C -0.4420(4) 0.6521(3) -0.1089(2) 0.0173(6) Uani 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'
Se Se -0.0929 2.2259 '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
_geom_angle_publ_flag
C12 Se1 C1 98.72(13) . . ?
C24 Se2 C13 99.69(13) . . ?
C3 O1 H1 122(5) . . ?
C10 O2 H2 116(8) . . ?
C15 O3 H3 125(9) . . ?
C22 O4 H4 111(5) . . ?
C6 N1 C7 124.5(3) . . ?
C19 N2 C18 125.4(3) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 Se1 118.2(2) . . ?
C6 C1 Se1 121.0(2) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
O1 C3 C2 121.9(3) . . ?
O1 C3 C4 119.0(3) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 H5A 118.6 . . ?
C6 C5 H5A 118.6 . . ?
N1 C6 C5 115.7(3) . . ?
N1 C6 C1 127.4(3) . . ?
C5 C6 C1 116.9(3) . . ?
N1 C7 C12 127.1(3) . . ?
N1 C7 C8 116.2(3) . . ?
C12 C7 C8 116.7(3) . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 H8A 118.8 . . ?
C7 C8 H8A 118.8 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
O2 C10 C11 119.6(3) . . ?
O2 C10 C9 122.5(3) . . ?
C11 C10 C9 117.8(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 Se1 117.6(2) . . ?
C7 C12 Se1 121.3(2) . . ?
C14 C13 C18 121.7(3) . . ?
C14 C13 Se2 117.6(2) . . ?
C18 C13 Se2 120.7(2) . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
O3 C15 C14 119.5(3) . . ?
O3 C15 C16 122.1(3) . . ?
C14 C15 C16 118.4(3) . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C18 122.2(3) . . ?
C16 C17 H17A 118.9 . . ?
C18 C17 H17A 118.9 . . ?
N2 C18 C13 126.8(3) . . ?
N2 C18 C17 116.6(3) . . ?
C13 C18 C17 116.6(3) . . ?
N2 C19 C20 116.6(3) . . ?
N2 C19 C24 127.4(3) . . ?
C20 C19 C24 115.9(3) . . ?
C21 C20 C19 122.7(3) . . ?
C21 C20 H20A 118.7 . . ?
C19 C20 H20A 118.7 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
O4 C22 C23 122.2(3) . . ?
O4 C22 C21 118.9(3) . . ?
C23 C22 C21 118.9(3) . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C23 C24 C19 122.0(3) . . ?
C23 C24 Se2 118.2(2) . . ?
C19 C24 Se2 119.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C12 1.878(3) . ?
Se1 C1 1.878(3) . ?
Se2 C24 1.880(3) . ?
Se2 C13 1.879(3) . ?
O1 C3 1.300(4) . ?
O1 H1 0.86(9) . ?
O2 C10 1.293(4) . ?
O2 H2 0.67(7) . ?
O3 C15 1.297(4) . ?
O3 H3 0.60(8) . ?
O4 C22 1.300(4) . ?
O4 H4 0.91(9) . ?
N1 C6 1.340(4) . ?
N1 C7 1.348(4) . ?
N2 C19 1.334(4) . ?
N2 C18 1.345(4) . ?
C1 C2 1.378(4) . ?
C1 C6 1.434(4) . ?
C2 C3 1.421(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.422(4) . ?
C4 C5 1.357(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.428(4) . ?
C5 H5A 0.9300 . ?
C7 C12 1.429(4) . ?
C7 C8 1.430(4) . ?
C8 C9 1.347(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.436(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.414(4) . ?
C11 C12 1.375(4) . ?
C11 H11A 0.9300 . ?
C13 C14 1.373(4) . ?
C13 C18 1.427(4) . ?
C14 C15 1.410(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.439(4) . ?
C16 C17 1.358(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.434(4) . ?
C17 H17A 0.9300 . ?
C19 C20 1.438(4) . ?
C19 C24 1.442(4) . ?
C20 C21 1.349(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.435(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.418(4) . ?
C23 C24 1.368(4) . ?
C23 H23A 0.9300 . ?
