#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/88/4118863.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_4118863
loop_
_publ_author_name
'Nicolas Guimond'
'Christina Gouliaras'
'Keith Fagnou'
_publ_section_title
;
 Correction to Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond
 as a Handle for C-N Bond Formation and Catalyst Turnover
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18148
_journal_page_last               18148
_journal_paper_doi               10.1021/ja3096625
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.37
_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                106.306(2)
_cell_angle_beta                 93.996(2)
_cell_angle_gamma                118.475(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6156(3)
_cell_length_b                   9.7142(3)
_cell_length_c                   10.8697(3)
_cell_measurement_reflns_used    6158
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.55
_cell_volume                     831.28(5)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11698
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0394
_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)+(0.0694P)²+0.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                3357
_reflns_number_total             4058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3096625_si_003.cif
_cod_data_source_block           ab014
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' 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        831.28(4)
_cod_database_code               4118863
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
O1 O 0.77468(10) 0.13170(9) -0.00121(7) 0.03033(19) Uani 1 1 d .
O2 O 0.86845(11) 0.24484(11) -0.17668(9) 0.0376(2) Uani 1 1 d .
N1 N 0.86173(12) 0.09238(12) -0.19212(9) 0.0312(2) Uani 1 1 d .
C1 C 0.81329(12) 0.04158(13) -0.09810(10) 0.0264(2) Uani 1 1 d .
C2 C 0.79838(12) -0.11390(13) -0.09338(10) 0.0264(2) Uani 1 1 d .
C3 C 0.82559(15) -0.21590(15) -0.19518(11) 0.0353(3) Uani 1 1 d .
H3A H 0.8558 -0.1839 -0.2686 0.042 Uiso 1 1 calc R
C4 C 0.80880(17) -0.36289(16) -0.18964(13) 0.0416(3) Uani 1 1 d .
H4A H 0.8281 -0.4315 -0.2590 0.050 Uiso 1 1 calc R
C5 C 0.76386(17) -0.41112(15) -0.08326(12) 0.0392(3) Uani 1 1 d .
H5A H 0.7523 -0.5127 -0.0800 0.047 Uiso 1 1 calc R
C6 C 0.73595(14) -0.31144(14) 0.01798(11) 0.0319(2) Uani 1 1 d .
H6A H 0.7038 -0.3458 0.0900 0.038 Uiso 1 1 calc R
C7 C 0.75462(12) -0.16006(12) 0.01538(10) 0.0255(2) Uani 1 1 d .
C8 C 0.72879(12) -0.04949(12) 0.12125(10) 0.0247(2) Uani 1 1 d .
C9 C 0.74171(12) 0.09021(13) 0.10944(10) 0.0255(2) Uani 1 1 d .
C10 C 0.95349(17) 0.30965(18) -0.26801(15) 0.0445(3) Uani 1 1 d .
H10A H 0.9603 0.4159 -0.2599 0.067 Uiso 1 1 calc R
H10B H 0.8951 0.2290 -0.3581 0.067 Uiso 1 1 calc R
H10C H 1.0637 0.3287 -0.2490 0.067 Uiso 1 1 calc R
C11 C 0.68691(13) -0.09259(12) 0.24014(10) 0.0255(2) Uani 1 1 d .
C12 C 0.80011(14) -0.09353(14) 0.32670(11) 0.0301(2) Uani 1 1 d .
H12A H 0.9018 -0.0723 0.3074 0.036 Uiso 1 1 calc R
C13 C 0.76494(16) -0.12530(15) 0.44078(12) 0.0368(3) Uani 1 1 d .
H13A H 0.8433 -0.1242 0.5000 0.044 Uiso 1 1 calc R
C14 C 0.61645(17) -0.15862(16) 0.46901(12) 0.0409(3) Uani 1 1 d .
H14A H 0.5933 -0.1788 0.5479 0.049 Uiso 1 1 calc R
C15 C 0.50215(15) -0.16235(16) 0.38172(13) 0.0394(3) Uani 1 1 d .
H15A H 0.3991 -0.1877 0.3998 0.047 Uiso 1 1 calc R
C16 C 0.53659(14) -0.12937(14) 0.26775(11) 0.0317(2) Uani 1 1 d .
H16A H 0.4573 -0.1319 0.2084 0.038 Uiso 1 1 calc R
C17 C 0.72370(12) 0.21891(12) 0.20540(10) 0.0263(2) Uani 1 1 d .
C18 C 0.79742(15) 0.28116(14) 0.33929(11) 0.0329(2) Uani 1 1 d .
H18A H 0.8615 0.2418 0.3697 0.040 Uiso 1 1 calc R
C19 C 0.77768(17) 0.40022(15) 0.42823(12) 0.0400(3) Uani 1 1 d .
H19A H 0.8288 0.4426 0.5194 0.048 Uiso 1 1 calc R
C20 C 0.68377(16) 0.45811(14) 0.38522(13) 0.0408(3) Uani 1 1 d .
H20A H 0.6683 0.5377 0.4469 0.049 Uiso 1 1 calc R
C21 C 0.61292(15) 0.39953(15) 0.25232(13) 0.0386(3) Uani 1 1 d .
H21A H 0.5495 0.4398 0.2224 0.046 Uiso 1 1 calc R
C22 C 0.63407(14) 0.28192(14) 0.16226(12) 0.0332(2) Uani 1 1 d .
H22A H 0.5872 0.2441 0.0707 0.040 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
C1 O1 C9 120.96(8)
N1 O2 C10 107.37(8)
C1 N1 O2 110.97(9)
N1 C1 O1 120.29(9)
N1 C1 C2 120.42(9)
O1 C1 C2 119.29(9)
C3 C2 C7 120.13(10)
C3 C2 C1 121.13(10)
C7 C2 C1 118.73(9)
C4 C3 C2 120.21(11)
C3 C4 C5 120.31(11)
C6 C5 C4 120.02(11)
C5 C6 C7 120.66(10)
C6 C7 C2 118.65(9)
C6 C7 C8 122.52(9)
C2 C7 C8 118.83(9)
C9 C8 C7 119.31(9)
C9 C8 C11 120.57(9)
C7 C8 C11 120.11(9)
C8 C9 O1 122.40(9)
C8 C9 C17 127.71(9)
O1 C9 C17 109.89(8)
C16 C11 C12 119.06(10)
C16 C11 C8 120.92(9)
C12 C11 C8 120.01(9)
C13 C12 C11 120.25(10)
C14 C13 C12 120.42(11)
C15 C14 C13 119.53(11)
C14 C15 C16 120.52(11)
C11 C16 C15 120.19(11)
C18 C17 C22 119.00(10)
C18 C17 C9 120.92(10)
C22 C17 C9 120.07(10)
C19 C18 C17 120.23(11)
C18 C19 C20 120.44(12)
C21 C20 C19 119.69(11)
C20 C21 C22 120.20(12)
C21 C22 C17 120.37(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3638(12)
O1 C9 1.3831(12)
O2 N1 1.4120(12)
O2 C10 1.4226(14)
N1 C1 1.2787(13)
C1 C2 1.4637(14)
C2 C3 1.3952(15)
C2 C7 1.4009(14)
C3 C4 1.3778(17)
C4 C5 1.3872(17)
C5 C6 1.3825(16)
C6 C7 1.4028(14)
C7 C8 1.4628(14)
C8 C9 1.3464(14)
C8 C11 1.4910(13)
C9 C17 1.4766(14)
C11 C16 1.3911(15)
C11 C12 1.3935(15)
C12 C13 1.3861(15)
C13 C14 1.3833(18)
C14 C15 1.3809(19)
C15 C16 1.3877(16)
C17 C18 1.3927(15)
C17 C22 1.3947(15)
C18 C19 1.3840(16)
C19 C20 1.3868(19)
C20 C21 1.3807(19)
C21 C22 1.3880(16)
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
C10 O2 N1 C1 168.42(10)
O2 N1 C1 O1 0.61(14)
O2 N1 C1 C2 -179.50(9)
C9 O1 C1 N1 -171.90(9)
C9 O1 C1 C2 8.21(14)
N1 C1 C2 C3 -4.42(16)
O1 C1 C2 C3 175.47(10)
N1 C1 C2 C7 176.11(9)
O1 C1 C2 C7 -4.00(15)
C7 C2 C3 C4 0.33(18)
C1 C2 C3 C4 -179.14(11)
C2 C3 C4 C5 0.4(2)
C3 C4 C5 C6 -0.1(2)
C4 C5 C6 C7 -0.82(19)
C5 C6 C7 C2 1.48(17)
C5 C6 C7 C8 -179.06(10)
C3 C2 C7 C6 -1.23(16)
C1 C2 C7 C6 178.25(9)
C3 C2 C7 C8 179.29(10)
C1 C2 C7 C8 -1.24(15)
C6 C7 C8 C9 -177.03(10)
C2 C7 C8 C9 2.43(15)
C6 C7 C8 C11 2.33(15)
C2 C7 C8 C11 -178.20(9)
C7 C8 C9 O1 1.68(15)
C11 C8 C9 O1 -177.68(9)
C7 C8 C9 C17 -178.66(9)
C11 C8 C9 C17 1.98(16)
C1 O1 C9 C8 -7.21(15)
C1 O1 C9 C17 173.08(9)
C9 C8 C11 C16 64.29(14)
C7 C8 C11 C16 -115.07(11)
C9 C8 C11 C12 -114.57(12)
C7 C8 C11 C12 66.07(13)
C16 C11 C12 C13 -2.11(16)
C8 C11 C12 C13 176.77(10)
C11 C12 C13 C14 0.89(17)
C12 C13 C14 C15 0.88(18)
C13 C14 C15 C16 -1.41(19)
C12 C11 C16 C15 1.58(16)
C8 C11 C16 C15 -177.29(10)
C14 C15 C16 C11 0.18(18)
C8 C9 C17 C18 44.92(16)
O1 C9 C17 C18 -135.38(10)
C8 C9 C17 C22 -136.12(12)
O1 C9 C17 C22 43.57(13)
C22 C17 C18 C19 1.85(16)
C9 C17 C18 C19 -179.18(10)
C17 C18 C19 C20 0.34(18)
C18 C19 C20 C21 -1.62(19)
C19 C20 C21 C22 0.68(18)
C20 C21 C22 C17 1.54(17)
C18 C17 C22 C21 -2.79(16)
C9 C17 C22 C21 178.24(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660680
