#------------------------------------------------------------------------------
#$Date: 2018-08-23 02:53:49 +0300 (Thu, 23 Aug 2018) $
#$Revision: 210078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/23/4302302.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_4302302
loop_
_publ_author_name
'Zhang, Lei'
'Xi, Bin'
'Po-Chun Liu, Isiah'
'Choudhuri, M. M. R.'
'Crutchley, Robert J.'
'Updegraff, James B.'
'Protasiewicz, John D.'
'Ren, Tong'
_publ_section_title
;
 Spectroscopy and Electronic Structures of Ru₂(ap)₄-alkynyl Compounds
;
_journal_coden_ASTM              INOCAJ
_journal_issue                   12
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5187
_journal_page_last               5194
_journal_paper_doi               10.1021/ic9000973
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31
_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                75.868(3)
_cell_angle_beta                 86.406(3)
_cell_angle_gamma                83.215(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4091(14)
_cell_length_b                   10.027(3)
_cell_length_c                   12.418(3)
_cell_measurement_reflns_used    4957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.37
_cell_volume                     648.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker AXS APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7589
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'AXScale in APEX2 (Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.1960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2528
_reflns_number_total             2916
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4338544
_cod_data_source_file            ic9000973_si_001.cif
_cod_data_source_block           HBuOap
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4302302
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
O1 O 0.51878(15) -0.05196(8) 0.33730(7) 0.0198(2) Uani 1 1 d . . .
N1 N 0.24392(17) 0.34640(9) 0.05356(8) 0.0172(2) Uani 1 1 d . . .
H1A H 0.2088 0.4361 0.0457 0.021 Uiso 1 1 calc R . .
N2 N -0.06484(18) 0.36787(9) -0.06979(8) 0.0180(2) Uani 1 1 d . . .
C1 C 0.5551(2) 0.08154(11) 0.28323(9) 0.0166(2) Uani 1 1 d . . .
C2 C 0.3894(2) 0.14315(11) 0.19903(9) 0.0164(2) Uani 1 1 d . . .
H2A H 0.2631 0.0929 0.1835 0.020 Uiso 1 1 calc R . .
C3 C 0.4088(2) 0.27801(11) 0.13779(9) 0.0159(2) Uani 1 1 d . . .
C4 C 0.5914(2) 0.35238(11) 0.16360(9) 0.0176(2) Uani 1 1 d . . .
H4A H 0.6046 0.4450 0.1232 0.021 Uiso 1 1 calc R . .
C5 C 0.7516(2) 0.29063(12) 0.24780(9) 0.0195(2) Uani 1 1 d . . .
H5A H 0.8741 0.3420 0.2650 0.023 Uiso 1 1 calc R . .
C6 C 0.7387(2) 0.15450(12) 0.30843(9) 0.0186(2) Uani 1 1 d . . .
H6A H 0.8522 0.1127 0.3654 0.022 Uiso 1 1 calc R . .
C7 C 0.1318(2) 0.28864(11) -0.01774(9) 0.0157(2) Uani 1 1 d . . .
C8 C 0.2199(2) 0.15989(11) -0.03977(9) 0.0180(2) Uani 1 1 d . . .
H8A H 0.3644 0.1078 -0.0054 0.022 Uiso 1 1 calc R . .
C9 C 0.0927(2) 0.11080(11) -0.11209(9) 0.0195(2) Uani 1 1 d . . .
H9A H 0.1479 0.0235 -0.1273 0.023 Uiso 1 1 calc R . .
C10 C -0.1170(2) 0.18933(12) -0.16287(10) 0.0206(2) Uani 1 1 d . . .
H10A H -0.2106 0.1562 -0.2113 0.025 Uiso 1 1 calc R . .
C11 C -0.1835(2) 0.31697(12) -0.14013(9) 0.0200(2) Uani 1 1 d . . .
H11A H -0.3225 0.3725 -0.1767 0.024 Uiso 1 1 calc R . .
C12 C 0.6940(2) -0.12405(11) 0.41933(9) 0.0186(2) Uani 1 1 d . . .
H12A H 0.6854 -0.0777 0.4815 0.022 Uiso 1 1 calc R . .
H12B H 0.8652 -0.1235 0.3861 0.022 Uiso 1 1 calc R . .
C13 C 0.6315(2) -0.27174(11) 0.46193(9) 0.0191(2) Uani 1 1 d . . .
H13A H 0.4532 -0.2697 0.4888 0.023 Uiso 1 1 calc R . .
C14 C 0.7953(2) -0.34168(12) 0.56016(10) 0.0228(3) Uani 1 1 d . . .
H14A H 0.7682 -0.2890 0.6175 0.034 Uiso 1 1 calc R . .
H14B H 0.9708 -0.3449 0.5350 0.034 Uiso 1 1 calc R . .
H14C H 0.7519 -0.4360 0.5910 0.034 Uiso 1 1 calc R . .
C15 C 0.6672(2) -0.35153(12) 0.37102(10) 0.0253(3) Uani 1 1 d . . .
H15A H 0.5601 -0.3048 0.3092 0.038 Uiso 1 1 calc R . .
H15B H 0.6226 -0.4458 0.4011 0.038 Uiso 1 1 calc R . .
H15C H 0.8417 -0.3552 0.3444 0.038 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C12 117.43(8) . . ?
C7 N1 C3 127.24(9) . . ?
C7 N1 H1A 116.4 . . ?
C3 N1 H1A 116.4 . . ?
C11 N2 C7 117.71(9) . . ?
O1 C1 C6 124.45(10) . . ?
O1 C1 C2 114.87(9) . . ?
C6 C1 C2 120.68(10) . . ?
C3 C2 C1 120.15(10) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 119.38(10) . . ?
C2 C3 N1 122.67(10) . . ?
C4 C3 N1 117.87(10) . . ?
C5 C4 C3 119.73(10) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 121.71(10) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C1 C6 C5 118.32(10) . . ?
C1 C6 H6A 120.8 . . ?
C5 C6 H6A 120.8 . . ?
N2 C7 N1 114.79(9) . . ?
N2 C7 C8 121.81(10) . . ?
N1 C7 C8 123.33(10) . . ?
C9 C8 C7 118.73(10) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C8 C9 C10 119.87(10) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 117.39(10) . . ?
C11 C10 H10A 121.3 . . ?
C9 C10 H10A 121.3 . . ?
N2 C11 C10 124.36(11) . . ?
N2 C11 H11A 117.8 . . ?
C10 C11 H11A 117.8 . . ?
O1 C12 C13 108.77(9) . . ?
O1 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
O1 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 C15 111.69(9) . . ?
C12 C13 C14 108.33(9) . . ?
C15 C13 C14 111.05(9) . . ?
C12 C13 H13A 108.6 . . ?
C15 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
O1 C1 1.3742(13) . ?
O1 C12 1.4346(13) . ?
N1 C7 1.3741(14) . ?
N1 C3 1.4077(13) . ?
N1 H1A 0.8800 . ?
N2 C11 1.3419(14) . ?
N2 C7 1.3476(14) . ?
C1 C6 1.3932(16) . ?
C1 C2 1.3965(15) . ?
C2 C3 1.3926(15) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4017(16) . ?
C4 C5 1.3779(15) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3961(16) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.4069(15) . ?
C8 C9 1.3768(16) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3932(16) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3791(16) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.5168(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.5262(17) . ?
C13 C14 1.5282(15) . ?
C13 H13A 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 O1 C1 C6 -5.00(15) . . . . ?
C12 O1 C1 C2 175.74(9) . . . . ?
O1 C1 C2 C3 -179.58(9) . . . . ?
C6 C1 C2 C3 1.14(16) . . . . ?
C1 C2 C3 C4 -1.80(16) . . . . ?
C1 C2 C3 N1 -178.66(9) . . . . ?
C7 N1 C3 C2 -33.89(16) . . . . ?
C7 N1 C3 C4 149.21(11) . . . . ?
C2 C3 C4 C5 1.04(16) . . . . ?
N1 C3 C4 C5 178.04(9) . . . . ?
C3 C4 C5 C6 0.41(17) . . . . ?
O1 C1 C6 C5 -178.92(10) . . . . ?
C2 C1 C6 C5 0.30(16) . . . . ?
C4 C5 C6 C1 -1.07(17) . . . . ?
C11 N2 C7 N1 -179.64(9) . . . . ?
C11 N2 C7 C8 3.23(16) . . . . ?
C3 N1 C7 N2 163.24(10) . . . . ?
C3 N1 C7 C8 -19.67(17) . . . . ?
N2 C7 C8 C9 -3.56(16) . . . . ?
N1 C7 C8 C9 179.55(10) . . . . ?
C7 C8 C9 C10 0.83(16) . . . . ?
C8 C9 C10 C11 1.96(17) . . . . ?
C7 N2 C11 C10 -0.21(17) . . . . ?
C9 C10 C11 N2 -2.37(18) . . . . ?
C1 O1 C12 C13 -175.70(9) . . . . ?
O1 C12 C13 C15 65.15(12) . . . . ?
O1 C12 C13 C14 -172.24(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660726
