#------------------------------------------------------------------------------
#$Date: 2012-12-14 08:43:15 +0200 (Fri, 14 Dec 2012) $
#$Revision: 69372 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/87/7108746.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_7108746
loop_
_publ_author_name
'Mallu Chenna Reddy'
'Masilamani Jeganmohan'
_publ_section_title
;
 Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of
 aryl carbamates with alkynes via C-H bond activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              481
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C14 H12 O3'
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 112.391(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.015(7)
_cell_length_b                   5.8478(19)
_cell_length_c                   17.370(6)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      1.91
_cell_volume                     2161.5(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.1097
_diffrn_reflns_av_sigmaI/netI    0.1000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18133
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.9873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0564
_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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1865
_reflns_number_gt                1151
_reflns_number_total             2703
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    c2cc37758f.txt
_[local]_cod_data_source_block   trail-1b
_[local]_cod_cif_authors_sg_H-M  'C2/c '
_cod_original_cell_volume        2161.6(12)
_cod_database_code               7108746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
C7 C 0.39308(12) 0.6839(5) 0.24180(17) 0.0314(7) Uani 1 1 d
C10 C 0.35228(13) 0.6773(5) 0.37477(18) 0.0354(7) Uani 1 1 d
C9 C 0.39167(14) 0.8563(5) 0.36794(19) 0.0379(7) Uani 1 1 d
C5 C 0.33593(13) 0.4970(5) 0.31635(18) 0.0360(7) Uani 1 1 d
C4 C 0.29630(15) 0.3219(6) 0.3241(2) 0.0426(8) Uani 1 1 d
C6 C 0.35838(13) 0.5062(5) 0.25060(18) 0.0359(7) Uani 1 1 d
C8 C 0.41120(13) 0.8603(5) 0.30305(18) 0.0330(7) Uani 1 1 d
C1 C 0.32795(16) 0.6736(6) 0.4388(2) 0.0459(8) Uani 1 1 d
C2 C 0.28974(15) 0.5025(6) 0.4433(2) 0.0498(9) Uani 1 1 d
C3 C 0.27426(15) 0.3234(7) 0.3857(2) 0.0482(9) Uani 1 1 d
O1 O 0.44831(10) 1.0299(4) 0.29297(13) 0.0417(6) Uani 1 1 d
C12 C 0.44225(13) 0.5278(5) 0.15183(18) 0.0310(7) Uani 1 1 d
C11 C 0.41105(13) 0.7013(5) 0.16813(17) 0.0319(7) Uani 1 1 d
C13 C 0.38930(18) 0.9121(6) 0.1162(2) 0.0390(8) Uani 1 1 d
C14 C 0.46591(13) 0.5142(5) 0.08486(17) 0.0318(7) Uani 1 1 d
O2 O 0.49765(10) 0.3467(3) 0.07975(12) 0.0385(5) Uani 1 1 d
O3 O 0.45303(10) 0.6843(3) 0.03278(13) 0.0396(6) Uani 1 1 d
H1 H 0.4069(13) 0.983(5) 0.4133(19) 0.047(8) Uiso 1 1 d
H7 H 0.4512(11) 0.396(4) 0.1860(15) 0.019(6) Uiso 1 1 d
H2 H 0.3394(13) 0.803(5) 0.4764(19) 0.045(9) Uiso 1 1 d
H3 H 0.2752(14) 0.533(5) 0.483(2) 0.047(9) Uiso 1 1 d
H6 H 0.4234(16) 0.992(5) 0.1139(19) 0.052(10) Uiso 1 1 d
H4 H 0.2844(13) 0.207(5) 0.2826(18) 0.040(9) Uiso 1 1 d
H5 H 0.3665(15) 1.012(6) 0.142(2) 0.063(10) Uiso 1 1 d
H8 H 0.3420(12) 0.380(4) 0.2054(18) 0.034(7) Uiso 1 1 d
H9 H 0.4733(17) 0.669(7) -0.006(2) 0.085(13) Uiso 1 1 d
H10 H 0.3619(16) 0.868(6) 0.059(2) 0.064(11) Uiso 1 1 d
H11 H 0.2473(17) 0.211(6) 0.387(2) 0.067(11) Uiso 1 1 d
H12 H 0.463(2) 1.147(9) 0.347(3) 0.139(19) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C7 0.0374(16) 0.0301(16) 0.0302(16) 0.0000(13) 0.0169(13) 0.0028(13)
C10 0.0368(16) 0.0387(17) 0.0327(17) 0.0035(14) 0.0156(14) 0.0035(14)
C9 0.0437(18) 0.0392(18) 0.0347(18) -0.0080(15) 0.0192(15) 0.0007(14)
C5 0.0353(16) 0.0394(17) 0.0342(17) 0.0019(14) 0.0142(14) 0.0019(14)
C4 0.0439(18) 0.0384(18) 0.045(2) 0.0056(17) 0.0161(16) -0.0005(16)
C6 0.0395(17) 0.0374(17) 0.0322(17) -0.0047(14) 0.0152(14) 0.0014(14)
C8 0.0367(16) 0.0309(16) 0.0351(17) 0.0011(13) 0.0177(14) 0.0027(13)
C1 0.054(2) 0.048(2) 0.044(2) -0.0035(18) 0.0277(17) -0.0006(18)
C2 0.0459(19) 0.066(2) 0.046(2) 0.0046(19) 0.0269(17) -0.0036(18)
C3 0.0414(19) 0.056(2) 0.052(2) 0.0077(18) 0.0229(17) -0.0067(17)
O1 0.0519(13) 0.0417(13) 0.0397(13) -0.0072(10) 0.0267(11) -0.0101(10)
C12 0.0400(16) 0.0280(16) 0.0281(16) 0.0005(13) 0.0166(13) -0.0005(13)
C11 0.0337(15) 0.0321(16) 0.0308(17) -0.0010(13) 0.0132(13) -0.0027(13)
C13 0.046(2) 0.0376(19) 0.037(2) 0.0009(15) 0.0200(17) 0.0034(16)
C14 0.0387(16) 0.0319(17) 0.0273(16) 0.0002(13) 0.0155(13) -0.0010(13)
O2 0.0534(13) 0.0384(12) 0.0337(12) 0.0052(9) 0.0278(10) 0.0089(10)
O3 0.0534(13) 0.0403(12) 0.0353(12) 0.0061(10) 0.0284(11) 0.0057(10)
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'
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
C6 C7 C8 119.2(2)
C6 C7 C11 121.2(3)
C8 C7 C11 119.6(2)
C5 C10 C9 119.7(3)
C5 C10 C1 118.3(3)
C9 C10 C1 122.0(3)
C8 C9 C10 120.3(3)
C4 C5 C10 118.6(3)
C4 C5 C6 123.4(3)
C10 C5 C6 118.0(3)
C3 C4 C5 121.6(3)
C7 C6 C5 122.0(3)
O1 C8 C9 122.6(3)
O1 C8 C7 116.8(2)
C9 C8 C7 120.7(3)
C2 C1 C10 120.9(3)
C1 C2 C3 120.5(3)
C4 C3 C2 120.2(3)
C11 C12 C14 127.2(3)
C12 C11 C7 118.6(2)
C12 C11 C13 125.6(3)
C7 C11 C13 115.8(2)
O2 C14 O3 122.5(2)
O2 C14 C12 120.4(3)
O3 C14 C12 117.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 C6 1.354(4)
C7 C8 1.425(4)
C7 C11 1.491(4)
C10 C5 1.412(4)
C10 C9 1.419(4)
C10 C1 1.423(4)
C9 C8 1.364(4)
C5 C4 1.411(4)
C5 C6 1.423(4)
C4 C3 1.347(4)
C8 O1 1.363(3)
C1 C2 1.354(4)
C2 C3 1.397(5)
C12 C11 1.334(4)
C12 C14 1.462(4)
C11 C13 1.497(4)
C14 O2 1.245(3)
C14 O3 1.301(3)