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#$Date: 2016-08-04 12:13:17 +0300 (Thu, 04 Aug 2016) $
#$Revision: 184825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/48/4344890.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_4344890
loop_
_publ_author_name
'Dwivedi, Ambikesh D.'
'Binnani, Chinky'
'Tyagi, Deepika'
'Rawat, Kuber S.'
'Li, Pei-Zhou'
'Zhao, Yanli'
'Mobin, Shaikh M.'
'Pathak, Biswarup'
'Singh, Sanjay K.'
_publ_section_title
;
 Troponate/Aminotroponate Ruthenium-Arene Complexes: Synthesis, Structure,
 and Ligand-Tuned Mechanistic Pathway for Direct C-H Bond Arylation with
 Aryl Chlorides in Water.
;
_journal_issue                   13
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6739
_journal_page_last               6749
_journal_paper_doi               10.1021/acs.inorgchem.6b01028
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C13 H17 N O'
_chemical_formula_weight         203.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/8
_cell_angle_alpha                90
_cell_angle_beta                 111.635(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1211(7)
_cell_length_b                   8.5610(5)
_cell_length_c                   12.4050(8)
_cell_measurement_reflns_used    378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      3.17
_cell_volume                     1196.57(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/8 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4562
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.228
_diffrn_reflns_theta_min         6.426
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.554
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0863P)²+0.1543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             2327
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b01028_si_002.cif
_cod_data_source_block           L3
_cod_original_cell_volume        1196.56(13)
_cod_database_code               4344890
_shelx_shelxl_version_number     2014/8
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.62299(10) 0.55040(15) 0.47576(10) 0.0762(4) Uani 1 1 d . .
N1 N 0.54531(11) 0.74004(16) 0.58741(12) 0.0630(4) Uani 1 1 d . .
H1A H 0.5075 0.6810 0.5294 0.076 Uiso 1 1 calc R U
C7 C 0.66295(12) 0.74049(17) 0.61942(12) 0.0527(4) Uani 1 1 d . .
C13 C 0.70212(12) 0.63097(17) 0.54740(12) 0.0541(4) Uani 1 1 d . .
C12 C 0.82125(14) 0.6170(2) 0.55568(15) 0.0645(4) Uani 1 1 d . .
H12 H 0.8320 0.5478 0.5026 0.077 Uiso 1 1 calc R U
C8 C 0.73664(15) 0.8311(2) 0.71096(14) 0.0669(5) Uani 1 1 d . .
H8 H 0.6973 0.8883 0.7496 0.080 Uiso 1 1 calc R U
C1 C 0.47232(15) 0.8261(2) 0.63747(17) 0.0694(5) Uani 1 1 d . .
H1 H 0.5119 0.9252 0.6683 0.083 Uiso 1 1 calc R U
C9 C 0.85859(16) 0.8503(2) 0.75402(17) 0.0780(5) Uani 1 1 d . .
H9 H 0.8877 0.9152 0.8185 0.094 Uiso 1 1 calc R U
C11 C 0.92423(15) 0.6869(2) 0.62790(18) 0.0761(5) Uani 1 1 d . .
H11 H 0.9920 0.6602 0.6136 0.091 Uiso 1 1 calc R U
C6 C 0.4582(2) 0.7347(3) 0.7360(2) 0.0892(6) Uani 1 1 d . .
H6A H 0.5349 0.7233 0.7981 0.107 Uiso 1 1 calc R U
H6B H 0.4283 0.6311 0.7089 0.107 Uiso 1 1 calc R U
C2 C 0.35430(18) 0.8613(3) 0.5421(2) 0.0952(7) Uani 1 1 d . .
H2A H 0.3174 0.7644 0.5060 0.114 Uiso 1 1 calc R U
H2B H 0.3672 0.9252 0.4832 0.114 Uiso 1 1 calc R U
C4 C 0.2560(3) 0.8531(4) 0.6876(4) 0.1610(17) Uani 1 1 d . .
H4A H 0.2074 0.9123 0.7202 0.193 Uiso 1 1 calc R U
H4B H 0.2147 0.7564 0.6566 0.193 Uiso 1 1 calc R U
C3 C 0.2717(2) 0.9468(4) 0.5896(4) 0.1403(13) Uani 1 1 d . .
H3A H 0.1950 0.9622 0.5280 0.168 Uiso 1 1 calc R U
H3B H 0.3045 1.0487 0.6183 0.168 Uiso 1 1 calc R U
C5 C 0.3733(3) 0.8162(3) 0.7819(3) 0.1324(13) Uani 1 1 d . .
H5A H 0.3599 0.7500 0.8393 0.159 Uiso 1 1 calc R U
H5B H 0.4094 0.9125 0.8200 0.159 Uiso 1 1 calc R U
C10 C 0.94276(16) 0.7902(3) 0.71798(19) 0.0825(6) Uani 1 1 d . .
H10 H 1.0206 0.8220 0.7580 0.099 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 C1 128.62(13)
C7 N1 H1A 115.7
C1 N1 H1A 115.7
N1 C7 C8 122.60(14)
N1 C7 C13 111.27(12)
C8 C7 C13 126.12(14)
O1 C13 C12 120.07(14)
O1 C13 C7 116.37(13)
C12 C13 C7 123.56(13)
C11 C12 C13 131.83(16)
C11 C12 H12 114.1
C13 C12 H12 114.1
C9 C8 C7 130.78(16)
C9 C8 H8 114.6
C7 C8 H8 114.6
N1 C1 C2 108.38(16)
N1 C1 C6 110.53(15)
C2 C1 C6 112.25(18)
N1 C1 H1 108.5
C2 C1 H1 108.5
C6 C1 H1 108.5
C10 C9 C8 130.83(18)
C10 C9 H9 114.6
C8 C9 H9 114.6
C12 C11 C10 130.17(17)
C12 C11 H11 114.9
C10 C11 H11 114.9
C1 C6 C5 111.1(2)
C1 C6 H6A 109.4
C5 C6 H6A 109.4
C1 C6 H6B 109.4
C5 C6 H6B 109.4
H6A C6 H6B 108.0
C1 C2 C3 111.1(2)
C1 C2 H2A 109.4
C3 C2 H2A 109.4
C1 C2 H2B 109.4
C3 C2 H2B 109.4
H2A C2 H2B 108.0
C5 C4 C3 111.7(2)
C5 C4 H4A 109.3
C3 C4 H4A 109.3
C5 C4 H4B 109.3
C3 C4 H4B 109.3
H4A C4 H4B 107.9
C2 C3 C4 110.4(2)
C2 C3 H3A 109.6
C4 C3 H3A 109.6
C2 C3 H3B 109.6
C4 C3 H3B 109.6
H3A C3 H3B 108.1
C4 C5 C6 112.5(3)
C4 C5 H5A 109.1
C6 C5 H5A 109.1
C4 C5 H5B 109.1
C6 C5 H5B 109.1
H5A C5 H5B 107.8
C9 C10 C11 126.38(17)
C9 C10 H10 116.8
C11 C10 H10 116.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.2478(18)
N1 C7 1.3317(19)
N1 C1 1.4548(19)
N1 H1A 0.8600
C7 C8 1.393(2)
C7 C13 1.488(2)
C13 C12 1.414(2)
C12 C11 1.376(2)
C12 H12 0.9300
C8 C9 1.384(2)
C8 H8 0.9300
C1 C2 1.513(3)
C1 C6 1.513(3)
C1 H1 0.9800
C9 C10 1.357(3)
C9 H9 0.9300
C11 C10 1.377(3)
C11 H11 0.9300
C6 C5 1.517(3)
C6 H6A 0.9700
C6 H6B 0.9700
C2 C3 1.524(3)
C2 H2A 0.9700
C2 H2B 0.9700
C4 C5 1.505(6)
C4 C3 1.526(5)
C4 H4A 0.9700
C4 H4B 0.9700
C3 H3A 0.9700
C3 H3B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C10 H10 0.9300
