#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025772.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_4025772
loop_
_publ_author_name
'Guoyong Song'
'Dan Chen'
'Cheng-Ling Pan'
'Robert H. Crabtree'
'Xingwei Li'
_publ_section_title
;
 Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides
 and Alkynes: Synthesis of Polycyclic Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7487
_journal_page_last               7490
_journal_paper_doi               10.1021/jo101596d
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C35 H23 N O'
_chemical_formula_sum            'C35 H23 N O'
_chemical_formula_weight         473.54
_chemical_melting_point          ?
_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                 107.127(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.420(3)
_cell_length_b                   11.314(2)
_cell_length_c                   12.965(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2442.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT software (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scan'
_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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8721
_diffrn_reflns_theta_full        21.57
_diffrn_reflns_theta_max         21.57
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            coloursess
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0414
_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)+(0.0484P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                1885
_reflns_number_total             2828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101596d_si_004.cif
_cod_data_source_block           m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2441.9(8)
_cod_database_code               4025772
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64896(11) -0.18051(19) 0.14564(16) 0.0599(6) Uani 1 1 d . . .
N1 N 0.71508(13) -0.0048(2) 0.14658(17) 0.0405(6) Uani 1 1 d . . .
C1 C 0.64610(17) -0.0732(3) 0.1425(2) 0.0455(8) Uani 1 1 d . . .
C2 C 0.70670(16) 0.1122(3) 0.1044(2) 0.0405(7) Uani 1 1 d . . .
C3 C 0.64068(16) 0.1773(3) 0.1019(2) 0.0425(7) Uani 1 1 d . . .
C4 C 0.57417(16) 0.1204(3) 0.1285(2) 0.0440(7) Uani 1 1 d . . .
C5 C 0.57535(16) -0.0027(3) 0.1415(2) 0.0446(8) Uani 1 1 d . . .
C6 C 0.50976(19) -0.0612(3) 0.1599(2) 0.0571(9) Uani 1 1 d . . .
H6A H 0.5109 -0.1429 0.1682 0.069 Uiso 1 1 calc R . .
C7 C 0.4435(2) 0.0020(4) 0.1658(3) 0.0710(10) Uani 1 1 d . . .
H7A H 0.3994 -0.0371 0.1765 0.085 Uiso 1 1 calc R . .
C8 C 0.44287(19) 0.1241(4) 0.1559(3) 0.0716(10) Uani 1 1 d . . .
H8A H 0.3987 0.1667 0.1619 0.086 Uiso 1 1 calc R . .
C9 C 0.50631(18) 0.1831(3) 0.1373(2) 0.0583(9) Uani 1 1 d . . .
H9A H 0.5046 0.2649 0.1304 0.070 Uiso 1 1 calc R . .
C10 C 0.77219(16) 0.1466(2) 0.0593(2) 0.0419(7) Uani 1 1 d . . .
C11 C 0.84767(17) 0.0926(2) 0.1005(2) 0.0418(7) Uani 1 1 d . . .
C12 C 0.85835(16) 0.0022(2) 0.1837(2) 0.0398(7) Uani 1 1 d . . .
C13 C 0.79337(17) -0.0496(2) 0.2005(2) 0.0407(7) Uani 1 1 d . . .
C14 C 0.63507(16) 0.3058(3) 0.0758(2) 0.0451(8) Uani 1 1 d . . .
C15 C 0.68196(17) 0.3861(3) 0.1483(2) 0.0518(8) Uani 1 1 d . . .
H15A H 0.7176 0.3587 0.2121 0.062 Uiso 1 1 calc R . .
C16 C 0.67672(19) 0.5062(3) 0.1275(3) 0.0639(9) Uani 1 1 d . . .
H16A H 0.7084 0.5587 0.1773 0.077 Uiso 1 1 calc R . .
C17 C 0.6251(2) 0.5475(3) 0.0336(3) 0.0670(10) Uani 1 1 d . . .
H17A H 0.6216 0.6282 0.0193 0.080 Uiso 1 1 calc R . .
C18 C 0.5785(2) 0.4699(3) -0.0392(3) 0.0702(10) Uani 1 1 d . . .
H18A H 0.5438 0.4979 -0.1035 0.084 Uiso 1 1 calc R . .
C19 C 0.58270(19) 0.3509(3) -0.0180(2) 0.0642(9) Uani 1 1 d . . .
H19A H 0.5497 0.2995 -0.0677 0.077 Uiso 1 1 calc R . .
C20 C 0.75977(18) 0.2241(3) -0.0281(2) 0.0516(8) Uani 1 1 d . . .
H20A H 0.7091 0.2568 -0.0585 0.062 Uiso 1 1 calc R . .
C21 C 0.8214(2) 0.2526(3) -0.0699(2) 0.0630(9) Uani 1 1 d . . .
H21A H 0.8123 0.3038 -0.1284 0.076 Uiso 1 1 calc R . .
C22 C 0.8973(2) 0.2048(3) -0.0244(3) 0.0655(10) Uani 1 1 d . . .
H22A H 0.9395 0.2263 -0.0508 0.079 Uiso 1 1 calc R . .
C23 C 0.91007(18) 0.1259(3) 0.0592(2) 0.0550(9) Uani 1 1 d . . .
H23A H 0.9610 0.0941 0.0888 0.066 Uiso 1 1 calc R . .
C24 C 0.94264(16) -0.0223(3) 0.2509(2) 0.0429(7) Uani 1 1 d . . .
C25 C 0.97461(19) 0.0430(3) 0.3420(3) 0.0671(10) Uani 1 1 d . . .
H25A H 0.9415 0.0942 0.3655 0.080 Uiso 1 1 calc R . .
C26 C 1.0544(2) 0.0351(4) 0.4001(3) 0.0786(11) Uani 1 1 d . . .
H26A H 1.0745 0.0817 0.4612 0.094 Uiso 1 1 calc R . .
C27 C 1.1039(2) -0.0403(4) 0.3687(3) 0.0702(10) Uani 1 1 d . . .
H27A H 1.1579 -0.0457 0.4077 0.084 Uiso 1 1 calc R . .
C28 C 1.0733(2) -0.1076(3) 0.2795(3) 0.0758(11) Uani 1 1 d . . .
H28A H 1.1067 -0.1599 0.2578 0.091 Uiso 1 1 calc R . .
C29 C 0.99290(19) -0.0996(3) 0.2201(3) 0.0651(10) Uani 1 1 d . . .
H29A H 0.9729 -0.1467 0.1593 0.078 Uiso 1 1 calc R . .
C30 C 0.79879(16) -0.1439(3) 0.2821(2) 0.0422(7) Uani 1 1 d . . .
C31 C 0.76623(17) -0.1273(3) 0.3669(2) 0.0506(8) Uani 1 1 d . . .
H31A H 0.7400 -0.0569 0.3723 0.061 Uiso 1 1 calc R . .
C32 C 0.77269(18) -0.2146(3) 0.4429(2) 0.0605(9) Uani 1 1 d . . .
H32A H 0.7507 -0.2029 0.4994 0.073 Uiso 1 1 calc R . .
C33 C 0.81131(19) -0.3189(3) 0.4361(3) 0.0671(10) Uani 1 1 d . . .
H33A H 0.8150 -0.3778 0.4873 0.080 Uiso 1 1 calc R . .
C34 C 0.84448(18) -0.3358(3) 0.3535(3) 0.0644(9) Uani 1 1 d . . .
H34A H 0.8713 -0.4059 0.3492 0.077 Uiso 1 1 calc R . .
C35 C 0.83808(17) -0.2491(3) 0.2770(2) 0.0520(8) Uani 1 1 d . . .
H35A H 0.8605 -0.2613 0.2210 0.062 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 N1 C2 120.2(2) . . ?
C1 N1 C13 120.1(2) . . ?
C2 N1 C13 119.5(2) . . ?
O1 C1 N1 121.2(3) . . ?
O1 C1 C5 124.8(3) . . ?
N1 C1 C5 113.9(3) . . ?
C3 C2 N1 120.2(2) . . ?
C3 C2 C10 126.4(3) . . ?
N1 C2 C10 113.2(2) . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 C14 122.2(3) . . ?
C4 C3 C14 118.9(2) . . ?
C5 C4 C9 118.2(3) . . ?
C5 C4 C3 118.9(3) . . ?
C9 C4 C3 122.8(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 C1 117.9(3) . . ?
C4 C5 C1 121.6(3) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C4 120.5(3) . . ?
C8 C9 H9A 119.8 . . ?
C4 C9 H9A 119.8 . . ?
C20 C10 C11 119.0(3) . . ?
C20 C10 C2 122.2(3) . . ?
C11 C10 C2 118.6(3) . . ?
C23 C11 C10 118.9(3) . . ?
C23 C11 C12 121.9(3) . . ?
C10 C11 C12 119.2(2) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 C24 123.5(3) . . ?
C11 C12 C24 116.8(2) . . ?
C12 C13 N1 119.6(3) . . ?
C12 C13 C30 123.1(2) . . ?
N1 C13 C30 117.0(2) . . ?
C15 C14 C19 117.3(3) . . ?
C15 C14 C3 120.0(3) . . ?
C19 C14 C3 122.8(3) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C18 C19 C14 121.3(3) . . ?
C18 C19 H19A 119.4 . . ?
C14 C19 H19A 119.4 . . ?
C21 C20 C10 120.9(3) . . ?
C21 C20 H20A 119.5 . . ?
C10 C20 H20A 119.5 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21A 120.1 . . ?
C22 C21 H21A 120.1 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C11 121.0(3) . . ?
C22 C23 H23A 119.5 . . ?
C11 C23 H23A 119.5 . . ?
C25 C24 C29 117.5(3) . . ?
C25 C24 C12 118.9(3) . . ?
C29 C24 C12 123.2(3) . . ?
C24 C25 C26 121.9(3) . . ?
C24 C25 H25A 119.1 . . ?
C26 C25 H25A 119.1 . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C26 C27 C28 118.9(3) . . ?
C26 C27 H27A 120.5 . . ?
C28 C27 H27A 120.5 . . ?
C27 C28 C29 121.1(3) . . ?
C27 C28 H28A 119.5 . . ?
C29 C28 H28A 119.5 . . ?
C24 C29 C28 120.2(3) . . ?
C24 C29 H29A 119.9 . . ?
C28 C29 H29A 119.9 . . ?
C35 C30 C31 118.5(3) . . ?
C35 C30 C13 120.8(2) . . ?
C31 C30 C13 120.7(3) . . ?
C32 C31 C30 120.2(3) . . ?
C32 C31 H31A 119.9 . . ?
C30 C31 H31A 119.9 . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 H32A 119.7 . . ?
C31 C32 H32A 119.7 . . ?
C34 C33 C32 119.8(3) . . ?
C34 C33 H33A 120.1 . . ?
C32 C33 H33A 120.1 . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H34A 120.0 . . ?
C35 C34 H34A 120.0 . . ?
C34 C35 C30 121.0(3) . . ?
C34 C35 H35A 119.5 . . ?
C30 C35 H35A 119.5 . . ?
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 1.215(3) . ?
N1 C1 1.417(3) . ?
N1 C2 1.423(3) . ?
N1 C13 1.429(3) . ?
C1 C5 1.465(4) . ?
C2 C3 1.358(3) . ?
C2 C10 1.479(4) . ?
C3 C4 1.453(4) . ?
C3 C14 1.490(4) . ?
C4 C5 1.402(4) . ?
C4 C9 1.411(4) . ?
C5 C6 1.401(4) . ?
C6 C7 1.379(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.387(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.372(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C20 1.399(4) . ?
C10 C11 1.405(4) . ?
C11 C23 1.398(4) . ?
C11 C12 1.458(4) . ?
C12 C13 1.348(3) . ?
C12 C24 1.496(4) . ?
C13 C30 1.486(4) . ?
C14 C15 1.387(4) . ?
C14 C19 1.385(4) . ?
C15 C16 1.382(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.365(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.367(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.371(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.388(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.370(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 C25 1.365(4) . ?
C24 C29 1.377(4) . ?
C25 C26 1.375(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.358(4) . ?
C26 H26A 0.9300 . ?
C27 C28 1.356(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.388(4) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 C35 1.384(4) . ?
C30 C31 1.391(3) . ?
C31 C32 1.377(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.374(4) . ?
C32 H32A 0.9300 . ?
C33 C34 1.372(4) . ?
C33 H33A 0.9300 . ?
C34 C35 1.376(4) . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659297
