#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:59:58 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180283 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/69/7116946.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_7116946
loop_
_publ_author_name
'Yanli Xu'
'Weigao Hu'
'Xiaodong Tang'
'Jinwu Zhao'
'Wanqing Wu'
'Huanfeng Jiang'
_publ_section_title
;
 Palladium-catalyzed Csp2-H carbonylation of aromatic oximes: selective
 access to benzo[d][1,2]oxazin-1-ones and 3-methyleneisoindolin-1-ones
;
_journal_name_full               Chem.Commun.
_journal_page_first              6843
_journal_paper_doi               10.1039/C5cc01661D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C10 H9 N O'
_chemical_formula_weight         159.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-07-08 deposited with the CCDC.
2015-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   15.005(3)
_cell_length_b                   12.061(2)
_cell_length_c                   18.219(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3297.2(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23169
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0046(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0572
_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)+(0.1159P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                1569
_reflns_number_total             2874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01661d2.cif
_cod_data_source_block           xu1
_cod_original_cell_volume        3297.4(11)
_cod_database_code               7116946
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.01109(14) 0.22851(17) 0.46320(13) 0.0687(7) Uani 1 1 d . . .
H1A H 1.0233 0.1851 0.4993 0.082 Uiso 1 1 calc R . .
O1 O 1.08953(15) 0.13651(16) 0.37398(12) 0.0860(7) Uani 1 1 d . . .
C1 C 1.00399(17) 0.3043(2) 0.34986(16) 0.0629(7) Uani 1 1 d . . .
C2 C 0.95421(18) 0.3710(2) 0.39592(17) 0.0651(7) Uani 1 1 d . . .
C8 C 0.95792(17) 0.3249(2) 0.46982(16) 0.0661(7) Uani 1 1 d . . .
C7 C 1.04052(19) 0.2122(2) 0.39390(17) 0.0662(7) Uani 1 1 d . . .
C5 C 0.96977(19) 0.4184(2) 0.24858(19) 0.0797(9) Uani 1 1 d . . .
H5A H 0.9746 0.4356 0.1990 0.096 Uiso 1 1 calc R . .
C3 C 0.9121(2) 0.4638(2) 0.36761(19) 0.0811(9) Uani 1 1 d . . .
H3A H 0.8790 0.5104 0.3979 0.097 Uiso 1 1 calc R . .
C6 C 1.01224(18) 0.3261(2) 0.27612(17) 0.0746(8) Uani 1 1 d . . .
H6A H 1.0455 0.2800 0.2457 0.090 Uiso 1 1 calc R . .
C4 C 0.9201(2) 0.4856(2) 0.2942(2) 0.0841(9) Uani 1 1 d . . .
H4A H 0.8913 0.5472 0.2746 0.101 Uiso 1 1 calc R . .
O2 O 0.06645(14) 0.42755(15) 0.07374(12) 0.0822(7) Uani 1 1 d . . .
N2 N 0.15641(14) 0.50604(17) -0.01393(14) 0.0707(7) Uani 1 1 d . . .
H2A H 0.1403 0.4652 -0.0503 0.085 Uiso 1 1 calc R . .
C11 C 0.16810(17) 0.5797(2) 0.10016(17) 0.0640(7) Uani 1 1 d . . .
C18 C 0.22019(18) 0.5909(2) -0.01941(18) 0.0678(8) Uani 1 1 d . . .
C17 C 0.12282(18) 0.4955(2) 0.05514(17) 0.0673(7) Uani 1 1 d . . .
C16 C 0.22513(18) 0.6383(2) 0.05428(18) 0.0689(8) Uani 1 1 d . . .
C15 C 0.2757(2) 0.7241(2) 0.0827(2) 0.0820(9) Uani 1 1 d . . .
H15A H 0.3139 0.7647 0.0528 0.098 Uiso 1 1 calc R . .
C14 C 0.2680(2) 0.7477(3) 0.1560(2) 0.0870(10) Uani 1 1 d . . .
H14A H 0.3015 0.8053 0.1757 0.104 Uiso 1 1 calc R . .
C12 C 0.16113(19) 0.6032(2) 0.17325(18) 0.0779(9) Uani 1 1 d . . .
H12A H 0.1231 0.5627 0.2034 0.093 Uiso 1 1 calc R . .
C13 C 0.2120(2) 0.6882(2) 0.2011(2) 0.0866(10) Uani 1 1 d . . .
H13A H 0.2085 0.7057 0.2507 0.104 Uiso 1 1 calc R . .
C9 C 0.9211(2) 0.3614(2) 0.53085(18) 0.0805(9) Uani 1 1 d . . .
H9A H 0.8883 0.4266 0.5278 0.097 Uiso 1 1 calc R . .
C10 C 0.9271(2) 0.3076(3) 0.60456(19) 0.0998(11) Uani 1 1 d . . .
H10A H 0.8937 0.3501 0.6395 0.150 Uiso 1 1 calc R . .
H10B H 0.9884 0.3043 0.6196 0.150 Uiso 1 1 calc R . .
H10C H 0.9033 0.2339 0.6019 0.150 Uiso 1 1 calc R . .
C19 C 0.2656(2) 0.6167(2) -0.07870(19) 0.0827(9) Uani 1 1 d . . .
H19A H 0.3048 0.6762 -0.0748 0.099 Uiso 1 1 calc R . .
C20 C 0.2609(2) 0.5611(3) -0.1514(2) 0.0994(11) Uani 1 1 d . . .
H20A H 0.3012 0.5968 -0.1849 0.149 Uiso 1 1 calc R . .
H20B H 0.2013 0.5659 -0.1702 0.149 Uiso 1 1 calc R . .
H20C H 0.2773 0.4846 -0.1462 0.149 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
C7 N1 C8 112.5(2) . .
C6 C1 C2 122.1(3) . .
C6 C1 C7 130.0(3) . .
C2 C1 C7 108.0(3) . .
C1 C2 C3 119.4(3) . .
C1 C2 C8 108.6(2) . .
C3 C2 C8 132.0(3) . .
C9 C8 N1 125.6(3) . .
C9 C8 C2 129.5(3) . .
N1 C8 C2 104.8(2) . .
O1 C7 N1 125.5(3) . .
O1 C7 C1 128.4(3) . .
N1 C7 C1 106.1(2) . .
C6 C5 C4 120.3(3) . .
C4 C3 C2 118.6(3) . .
C1 C6 C5 118.0(3) . .
C3 C4 C5 121.6(3) . .
C17 N2 C18 112.7(2) . .
C12 C11 C16 121.9(3) . .
C12 C11 C17 130.6(3) . .
C16 C11 C17 107.4(3) . .
C19 C18 N2 125.7(3) . .
C19 C18 C16 129.5(3) . .
N2 C18 C16 104.7(2) . .
O2 C17 N2 125.0(3) . .
O2 C17 C11 128.8(3) . .
N2 C17 C11 106.2(2) . .
C15 C16 C11 119.6(3) . .
C15 C16 C18 131.6(3) . .
C11 C16 C18 108.9(2) . .
C14 C15 C16 118.3(3) . .
C15 C14 C13 121.7(3) . .
C11 C12 C13 118.1(3) . .
C12 C13 C14 120.4(3) . .
C8 C9 C10 126.0(3) . .
C18 C19 C20 127.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.352(4) .
N1 C8 1.415(3) .
O1 C7 1.227(3) .
C1 C6 1.375(4) .
C1 C2 1.382(4) .
C1 C7 1.476(4) .
C2 C3 1.386(4) .
C2 C8 1.458(4) .
C8 C9 1.317(4) .
C5 C6 1.377(4) .
C5 C4 1.380(4) .
C3 C4 1.368(4) .
O2 C17 1.226(3) .
N2 C17 1.362(4) .
N2 C18 1.405(3) .
C11 C12 1.365(4) .
C11 C16 1.389(4) .
C11 C17 1.472(4) .
C18 C19 1.314(4) .
C18 C16 1.461(4) .
C16 C15 1.383(4) .
C15 C14 1.370(5) .
C14 C13 1.378(5) .
C12 C13 1.376(4) .
C9 C10 1.494(4) .
C19 C20 1.487(5) .
