#------------------------------------------------------------------------------
#$Date: 2017-01-01 09:37:57 +0200 (Sun, 01 Jan 2017) $
#$Revision: 189728 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/92/7119200.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_7119200
loop_
_publ_author_name
'Patel, Pitambar'
'Borah, Gongutri'
_publ_section_title
;
 Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H
 carbenoid functionalization.
;
_journal_issue                   2
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              443
_journal_page_last               446
_journal_paper_doi               10.1039/c6cc08788d
_journal_volume                  53
_journal_year                    2016
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          399
_chemical_name_common            N-acetyoxyindole
_chemical_name_systematic
;
 ?
;
_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
_audit_update_record
;
2016-10-06 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.494(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4444(8)
_cell_length_b                   8.2789(9)
_cell_length_c                   13.8475(15)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.46
_cell_volume                     851.86(16)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21338
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.868
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9200
_exptl_absorpt_correction_T_min  0.8307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1300
_reflns_number_total             1505
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc08788d2.cif
_cod_data_source_block           aa
_cod_database_code               7119200
_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.
;
_shelxl_version_number           2014-3
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
C6 C 0.27105(14) 0.53212(16) 0.53336(9) 0.0383(4) Uani 1 1 d . .
C5 C 0.30224(17) 0.68194(17) 0.49296(10) 0.0440(4) Uani 1 1 d . .
C3 C 0.3581(2) 0.6360(2) 0.68894(12) 0.0596(5) Uani 1 1 d . .
H3 H 0.3775 0.6215 0.7554 0.071 Uiso 1 1 calc R U
C1 C 0.3616(2) 0.80936(19) 0.55123(13) 0.0582(5) Uani 1 1 d . .
H1 H 0.3822 0.9102 0.5244 0.070 Uiso 1 1 calc R U
C2 C 0.3900(2) 0.7848(2) 0.64997(13) 0.0621(5) Uani 1 1 d . .
H2 H 0.4307 0.8692 0.6898 0.075 Uiso 1 1 calc R U
C4 C 0.29763(17) 0.5060(2) 0.63223(10) 0.0495(4) Uani 1 1 d . .
H4 H 0.2759 0.4057 0.6594 0.059 Uiso 1 1 calc R U
N1 N 0.21085(13) 0.42169(13) 0.45823(7) 0.0385(3) Uani 1 1 d . .
C7 C 0.20619(17) 0.50197(19) 0.36771(9) 0.0447(4) Uani 1 1 d . .
O1 O 0.16302(15) 0.44189(14) 0.29027(7) 0.0632(4) Uani 1 1 d . .
C8 C 0.16155(18) 0.26027(17) 0.47398(10) 0.0459(4) Uani 1 1 d . .
O2 O 0.16490(19) 0.20958(16) 0.55594(8) 0.0761(4) Uani 1 1 d . .
C9 C 0.1062(2) 0.15717(19) 0.38969(11) 0.0573(4) Uani 1 1 d . .
H9A H 0.0686 0.0535 0.4120 0.086 Uiso 1 1 calc R U
H9B H 0.2060 0.1437 0.3496 0.086 Uiso 1 1 calc R U
H9C H 0.0082 0.2076 0.3529 0.086 Uiso 1 1 calc R U
C10 C 0.2614(2) 0.67439(19) 0.38573(11) 0.0535(4) Uani 1 1 d . .
H10A H 0.3668 0.7013 0.3512 0.064 Uiso 1 1 calc R U
H10B H 0.1646 0.7479 0.3658 0.064 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 0.0033 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
C5 C6 C4 121.33(13)
C5 C6 N1 109.26(11)
C4 C6 N1 129.41(13)
C1 C5 C6 120.14(14)
C1 C5 C10 130.37(14)
C6 C5 C10 109.49(12)
C2 C3 C4 122.05(15)
C5 C1 C2 119.17(16)
C3 C2 C1 120.03(15)
C6 C4 C3 117.28(15)
C8 N1 C7 126.17(11)
C8 N1 C6 124.43(10)
C7 N1 C6 109.39(11)
O1 C7 N1 125.66(14)
O1 C7 C10 126.45(13)
N1 C7 C10 107.88(11)
O2 C8 N1 119.00(12)
O2 C8 C9 121.84(14)
N1 C8 C9 119.16(12)
C5 C10 C7 103.96(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C5 1.3861(19)
C6 C4 1.3882(18)
C6 N1 1.4360(16)
C5 C1 1.384(2)
C5 C10 1.499(2)
C3 C2 1.372(3)
C3 C4 1.391(2)
C1 C2 1.386(2)
N1 C8 1.4064(18)
N1 C7 1.4173(17)
C7 O1 1.2076(16)
C7 C10 1.502(2)
C8 O2 1.2089(16)
C8 C9 1.4840(19)
