#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:26:10 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/47/7124761.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_7124761
loop_
_publ_author_name
'Kaishap, Partha Pratim'
'Sarma, Bipul'
'Gogoi, Sanjib'
_publ_section_title
;
 The amide C-N bond of isatins as the directing group and the internal
 oxidant in Ru-catalyzed C-H activation and annulation reactions: access
 to 8-amido isocoumarins.
;
_journal_issue                   63
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9809
_journal_page_last               9812
_journal_paper_doi               10.1039/c6cc04461a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2016-04-22 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                93.626(2)
_cell_angle_beta                 92.834(2)
_cell_angle_gamma                94.652(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0877(4)
_cell_length_b                   8.9461(4)
_cell_length_c                   10.5339(5)
_cell_measurement_reflns_used    7433
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.90
_cell_volume                     756.99(6)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12347
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0447
_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)+(0.0646P)²+0.1892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                3143
_reflns_number_total             3439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc04461a2.cif
_cod_data_source_block           bs_sb2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7124761
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 0.28817(9) 0.30708(9) 0.35478(7) 0.02082(19) Uani 1 1 d .
O3 O 0.27131(10) 0.53301(11) 0.94378(7) 0.0307(2) Uani 1 1 d .
N1 N 0.21969(11) 0.44662(10) 0.73468(8) 0.0193(2) Uani 1 1 d .
C14 C 0.26620(18) 0.05922(17) -0.00325(12) 0.0360(3) Uani 1 1 d .
H14A H 0.2070 0.1413 -0.0306 0.054 Uiso 1 1 calc R
H14B H 0.1984 -0.0334 -0.0220 0.054 Uiso 1 1 calc R
H14C H 0.3672 0.0559 -0.0472 0.054 Uiso 1 1 calc R
C13 C 0.30744(16) 0.08122(14) 0.13979(11) 0.0282(3) Uani 1 1 d .
H13A H 0.3602 -0.0054 0.1680 0.034 Uiso 1 1 calc R
H13B H 0.2052 0.0874 0.1836 0.034 Uiso 1 1 calc R
C12 C 0.42248(13) 0.22322(12) 0.17609(10) 0.0211(2) Uani 1 1 d .
H12A H 0.5316 0.2097 0.1451 0.025 Uiso 1 1 calc R
H12B H 0.3794 0.3072 0.1351 0.025 Uiso 1 1 calc R
C8 C 0.43836(13) 0.25907(12) 0.31724(10) 0.0187(2) Uani 1 1 d .
C7 C 0.25748(13) 0.34800(12) 0.47732(10) 0.0188(2) Uani 1 1 d .
C6 C 0.39137(13) 0.34238(11) 0.57400(9) 0.0171(2) Uani 1 1 d .
C1 C 0.36918(13) 0.38693(11) 0.70428(10) 0.0178(2) Uani 1 1 d .
C10 C 0.18097(13) 0.51917(12) 0.84684(10) 0.0204(2) Uani 1 1 d .
C11 C 0.01412(14) 0.58260(14) 0.84048(10) 0.0244(2) Uani 1 1 d .
H11A H -0.0619 0.5243 0.8888 0.037 Uiso 1 1 calc R
H11B H -0.0277 0.5790 0.7533 0.037 Uiso 1 1 calc R
H11C H 0.0255 0.6850 0.8752 0.037 Uiso 1 1 calc R
C2 C 0.49650(14) 0.37147(12) 0.79533(10) 0.0206(2) Uani 1 1 d .
H2 H 0.4830 0.3974 0.8808 0.025 Uiso 1 1 calc R
C3 C 0.64398(14) 0.31695(12) 0.75756(10) 0.0222(2) Uani 1 1 d .
H3 H 0.7280 0.3066 0.8191 0.027 Uiso 1 1 calc R
C4 C 0.66977(13) 0.27762(12) 0.63112(10) 0.0206(2) Uani 1 1 d .
H4 H 0.7708 0.2438 0.6088 0.025 Uiso 1 1 calc R
C5 C 0.54353(13) 0.28884(11) 0.53697(10) 0.0177(2) Uani 1 1 d .
C9 C 0.56491(13) 0.24729(11) 0.40247(10) 0.0179(2) Uani 1 1 d .
C15 C 0.72706(13) 0.19116(12) 0.36175(10) 0.0196(2) Uani 1 1 d .
H15A H 0.8182 0.2505 0.4091 0.024 Uiso 1 1 calc R
H15B H 0.7377 0.2067 0.2721 0.024 Uiso 1 1 calc R
C16 C 0.74238(13) 0.02435(12) 0.38242(10) 0.0207(2) Uani 1 1 d .
H16A H 0.7326 0.0078 0.4720 0.025 Uiso 1 1 calc R
H16B H 0.6525 -0.0361 0.3345 0.025 Uiso 1 1 calc R
C17 C 0.90861(14) -0.02494(13) 0.33991(11) 0.0240(2) Uani 1 1 d .
H17A H 0.9150 -0.0154 0.2500 0.036 Uiso 1 1 calc R
H17B H 0.9177 -0.1278 0.3582 0.036 Uiso 1 1 calc R
H17C H 0.9977 0.0375 0.3848 0.036 Uiso 1 1 calc R
O2 O 0.11685(10) 0.38347(10) 0.49395(7) 0.0254(2) Uani 1 1 d .
H1A H 0.1449(19) 0.4458(17) 0.6664(15) 0.032(4) Uiso 1 1 d .
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
C7 O1 C8 123.88(8)
C10 N1 C1 128.60(9)
C10 N1 H1A 117.4(9)
C1 N1 H1A 113.6(9)
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
C14 C13 C12 112.35(10)
C14 C13 H13A 109.1
C12 C13 H13A 109.1
C14 C13 H13B 109.1
C12 C13 H13B 109.1
H13A C13 H13B 107.9
C8 C12 C13 112.05(9)
C8 C12 H12A 109.2
C13 C12 H12A 109.2
C8 C12 H12B 109.2
C13 C12 H12B 109.2
H12A C12 H12B 107.9
C9 C8 O1 121.26(9)
C9 C8 C12 130.93(10)
O1 C8 C12 107.78(8)
O2 C7 O1 115.26(9)
O2 C7 C6 127.09(9)
O1 C7 C6 117.64(9)
C5 C6 C1 120.50(9)
C5 C6 C7 118.78(9)
C1 C6 C7 120.71(9)
C2 C1 N1 122.76(9)
C2 C1 C6 119.08(10)
N1 C1 C6 118.16(9)
O3 C10 N1 124.32(10)
O3 C10 C11 121.87(10)
N1 C10 C11 113.81(9)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C3 C2 C1 119.62(10)
C3 C2 H2 120.2
C1 C2 H2 120.2
C4 C3 C2 122.12(10)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 119.98(10)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 118.65(9)
C4 C5 C9 121.81(9)
C6 C5 C9 119.54(9)
C8 C9 C5 118.82(9)
C8 C9 C15 121.17(9)
C5 C9 C15 120.00(9)
C9 C15 C16 113.78(8)
C9 C15 H15A 108.8
C16 C15 H15A 108.8
C9 C15 H15B 108.8
C16 C15 H15B 108.8
H15A C15 H15B 107.7
C17 C16 C15 111.15(9)
C17 C16 H16A 109.4
C15 C16 H16A 109.4
C17 C16 H16B 109.4
C15 C16 H16B 109.4
H16A C16 H16B 108.0
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3596(12)
O1 C8 1.3881(12)
O3 C10 1.2196(14)
N1 C10 1.3740(13)
N1 C1 1.4038(13)
N1 H1A 0.916(16)
C14 C13 1.5239(16)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C13 C12 1.5288(16)
C13 H13A 0.9700
C13 H13B 0.9700
C12 C8 1.4981(14)
C12 H12A 0.9700
C12 H12B 0.9700
C8 C9 1.3429(15)
C7 O2 1.2232(13)
C7 C6 1.4555(14)
C6 C5 1.4197(14)
C6 C1 1.4287(14)
C1 C2 1.3933(14)
C10 C11 1.5059(15)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C2 C3 1.3912(15)
C2 H2 0.9300
C3 C4 1.3862(15)
C3 H3 0.9300
C4 C5 1.4019(14)
C4 H4 0.9300
C5 C9 1.4640(14)
C9 C15 1.5136(14)
C15 C16 1.5356(14)
C15 H15A 0.9700
C15 H15B 0.9700
C16 C17 1.5275(14)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
