#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:47:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180316 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/30/7153093.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_7153093
loop_
_publ_author_name
'Vandavasi, Jaya Kishore'
'Kuo, Kung-Kai'
'Hu, Wan-Ping'
'Shen, Ho-Chanu'
'Lo, Wei-Sheng'
'Wang, Jeh-Jeng'
_publ_section_title
;
 A convenient method to construct (Z)-oxazines via 6-exo-dig
 iodocyclization and synthesis of indolin-3-one.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6520
_journal_page_last               6525
_journal_paper_doi               10.1039/c3ob41272e
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C21 H14 I N O'
_chemical_formula_sum            'C21 H14 I N O'
_chemical_formula_weight         423.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.672(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6456(3)
_cell_length_b                   20.4565(5)
_cell_length_c                   9.9640(3)
_cell_measurement_reflns_used    4337
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      29.0728
_cell_measurement_theta_min      2.9056
_cell_volume                     1696.71(9)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8278
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) 
(compiled Aug 27 2009,17:19:36) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0308
_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)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                2742
_reflns_number_total             3962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41272e.txt
_cod_data_source_block           hphh
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7153093
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I I 0.22524(3) 0.182324(9) 0.78009(2) 0.05487(9) Uani 1 1 d .
O O 0.1917(2) 0.06919(8) 0.96243(19) 0.0474(5) Uani 1 1 d .
N N 0.2153(3) -0.00187(10) 1.1492(3) 0.0465(6) Uani 1 1 d .
C1 C 0.1512(3) 0.04673(12) 1.2179(3) 0.0403(6) Uani 1 1 d .
C2 C 0.1248(4) 0.03108(13) 1.3457(3) 0.0518(8) Uani 1 1 d .
H2A H 0.1538 -0.0100 1.3844 0.062 Uiso 1 1 calc R
C3 C 0.0567(4) 0.07531(13) 1.4151(3) 0.0537(8) Uani 1 1 d .
H3A H 0.0381 0.0641 1.4998 0.064 Uiso 1 1 calc R
C4 C 0.0155(4) 0.13637(14) 1.3595(3) 0.0502(8) Uani 1 1 d .
H4A H -0.0325 0.1662 1.4061 0.060 Uiso 1 1 calc R
C5 C 0.0450(4) 0.15352(14) 1.2355(3) 0.0464(7) Uani 1 1 d .
H5A H 0.0175 0.1952 1.1995 0.056 Uiso 1 1 calc R
C6 C 0.1151(3) 0.10971(12) 1.1627(3) 0.0366(6) Uani 1 1 d .
C7 C 0.1511(3) 0.12377(11) 1.0304(3) 0.0355(6) Uani 1 1 d .
C8 C 0.2305(3) 0.01135(12) 1.0299(3) 0.0397(6) Uani 1 1 d .
C9 C 0.1532(3) 0.18046(12) 0.9659(3) 0.0376(6) Uani 1 1 d .
C10 C 0.1246(3) 0.24653(11) 1.0157(3) 0.0370(6) Uani 1 1 d .
C11 C -0.0258(4) 0.27524(13) 0.9763(3) 0.0457(7) Uani 1 1 d .
H11A H -0.1120 0.2527 0.9190 0.055 Uiso 1 1 calc R
C12 C -0.0483(4) 0.33809(15) 1.0227(3) 0.0571(9) Uani 1 1 d .
H12A H -0.1492 0.3575 0.9953 0.068 Uiso 1 1 calc R
C13 C 0.0768(5) 0.37091(14) 1.1077(3) 0.0579(9) Uani 1 1 d .
H13A H 0.0610 0.4125 1.1392 0.070 Uiso 1 1 calc R
C14 C 0.2260(4) 0.34300(15) 1.1471(4) 0.0582(8) Uani 1 1 d .
H14A H 0.3111 0.3657 1.2055 0.070 Uiso 1 1 calc R
C15 C 0.2512(4) 0.28148(13) 1.1008(3) 0.0477(7) Uani 1 1 d .
H15A H 0.3535 0.2633 1.1268 0.057 Uiso 1 1 calc R
C16 C 0.2944(3) -0.03557(12) 0.9456(3) 0.0418(7) Uani 1 1 d .
C17 C 0.3282(4) -0.01711(14) 0.8239(3) 0.0536(8) Uani 1 1 d .
H17A H 0.3077 0.0255 0.7914 0.064 Uiso 1 1 calc R
C18 C 0.3929(4) -0.06200(16) 0.7493(4) 0.0647(9) Uani 1 1 d .
H18A H 0.4165 -0.0493 0.6674 0.078 Uiso 1 1 calc R
C19 C 0.4216(4) -0.12464(17) 0.7964(4) 0.0673(10) Uani 1 1 d .
H19A H 0.4633 -0.1549 0.7458 0.081 Uiso 1 1 calc R
C20 C 0.3894(4) -0.14285(15) 0.9176(4) 0.0666(10) Uani 1 1 d .
H20A H 0.4105 -0.1855 0.9499 0.080 Uiso 1 1 calc R
C21 C 0.3258(4) -0.09866(13) 0.9930(3) 0.0544(8) Uani 1 1 d .
H21A H 0.3041 -0.1115 1.0756 0.065 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'
I I -0.4742 1.8119 '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
C8 O C7 121.1(2)
C8 N C1 117.7(2)
C6 C1 C2 119.8(2)
C6 C1 N 122.3(2)
C2 C1 N 117.9(2)
C3 C2 C1 120.7(3)
C3 C2 H2A 119.6
C1 C2 H2A 119.6
C2 C3 C4 119.9(3)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
C5 C4 C3 120.3(3)
C5 C4 H4A 119.9
C3 C4 H4A 119.9
C4 C5 C6 121.2(3)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C5 C6 C1 118.0(2)
C5 C6 C7 124.9(2)
C1 C6 C7 117.1(2)
C9 C7 O 115.1(2)
C9 C7 C6 129.9(2)
O C7 C6 115.0(2)
N C8 O 125.4(2)
N C8 C16 123.2(2)
O C8 C16 111.4(2)
C7 C9 C10 127.5(2)
C7 C9 I 119.11(18)
C10 C9 I 113.11(17)
C11 C10 C15 118.7(2)
C11 C10 C9 121.4(3)
C15 C10 C9 119.9(2)
C10 C11 C12 120.0(3)
C10 C11 H11A 120.0
C12 C11 H11A 120.0
C13 C12 C11 120.2(3)
C13 C12 H12A 119.9
C11 C12 H12A 119.9
C14 C13 C12 120.2(3)
C14 C13 H13A 119.9
C12 C13 H13A 119.9
C13 C14 C15 120.5(3)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C10 C15 C14 120.4(3)
C10 C15 H15A 119.8
C14 C15 H15A 119.8
C21 C16 C17 119.4(3)
C21 C16 C8 118.9(3)
C17 C16 C8 121.6(2)
C16 C17 C18 120.2(3)
C16 C17 H17A 119.9
C18 C17 H17A 119.9
C19 C18 C17 119.9(3)
C19 C18 H18A 120.0
C17 C18 H18A 120.0
C18 C19 C20 120.0(3)
C18 C19 H19A 120.0
C20 C19 H19A 120.0
C19 C20 C21 120.7(3)
C19 C20 H20A 119.7
C21 C20 H20A 119.7
C16 C21 C20 119.8(3)
C16 C21 H21A 120.1
C20 C21 H21A 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I C9 2.108(3)
O C8 1.357(3)
O C7 1.399(3)
N C8 1.260(3)
N C1 1.403(3)
C1 C6 1.403(3)
C1 C2 1.391(4)
C2 C3 1.365(4)
C2 H2A 0.9300
C3 C4 1.374(4)
C3 H3A 0.9300
C4 C5 1.373(4)
C4 H4A 0.9300
C5 C6 1.391(3)
C5 H5A 0.9300
C6 C7 1.462(3)
C7 C9 1.328(3)
C8 C16 1.477(4)
C9 C10 1.483(3)
C10 C11 1.384(4)
C10 C15 1.388(4)
C11 C12 1.397(4)
C11 H11A 0.9300
C12 C13 1.357(5)
C12 H12A 0.9300
C13 C14 1.368(5)
C13 H13A 0.9300
C14 C15 1.377(4)
C14 H14A 0.9300
C15 H15A 0.9300
C16 C21 1.376(4)
C16 C17 1.374(4)
C17 C18 1.391(4)
C17 H17A 0.9300
C18 C19 1.364(4)
C18 H18A 0.9300
C19 C20 1.363(5)
C19 H19A 0.9300
C20 C21 1.381(4)
C20 H20A 0.9300
C21 H21A 0.9300
