#------------------------------------------------------------------------------
#$Date: 2016-07-23 08:25:25 +0200 (Sat 23 de Jul de 2016) $
#$Revision: 184647 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/60/7226025.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_7226025
loop_
_publ_author_name
'Yao, Ching-Fa'
'Villuri, Bharath Kumar'
'Kotipalli, Trimurtulu'
'Kavala, Veerababurao'
'Ichake, Sachin S.'
'Bandi, Vijayalakshmi'
'Kuo, Chun-Wei'
_publ_section_title
;
 Synthesis of Spiro Isoindolinone-indolines and 1,2-Disubstituted Indoles
 from 2-Iodobenzamide derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA15002K
_journal_year                    2016
_chemical_formula_moiety         'C24 H21 N3 O2'
_chemical_formula_sum            'C24 H21 N3 O2'
_chemical_formula_weight         383.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.695(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.813(3)
_cell_length_b                   20.064(9)
_cell_length_c                   8.964(3)
_cell_measurement_reflns_used    1269
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.09
_cell_measurement_theta_min      2.49
_cell_volume                     1944.6(12)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.1028
_diffrn_reflns_av_sigmaI/netI    0.1244
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13224
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0724
_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)+(0.0838P)²+0.7453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.2088
_reflns_number_gt                1697
_reflns_number_total             3422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra15002k2.cif
_cod_data_source_block           a16869
_cod_original_cell_volume        1944.7(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7226025
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.0233(4) 0.0760(2) 0.7227(5) 0.0479(13) Uani 1 1 d .
C2 C 0.0035(4) 0.0931(2) 0.5655(5) 0.0435(12) Uani 1 1 d .
C3 C -0.0982(4) 0.1220(3) 0.4951(6) 0.0544(14) Uani 1 1 d .
H3 H -0.1680 0.1357 0.5507 0.065 Uiso 1 1 calc R
C4 C -0.0957(5) 0.1303(3) 0.3458(6) 0.0590(14) Uani 1 1 d .
H4 H -0.1643 0.1505 0.2964 0.071 Uiso 1 1 calc R
C5 C 0.0055(5) 0.1098(3) 0.2628(5) 0.0587(15) Uani 1 1 d .
H5 H 0.0043 0.1152 0.1575 0.070 Uiso 1 1 calc R
C6 C 0.1087(4) 0.0813(2) 0.3329(5) 0.0496(13) Uani 1 1 d .
H6 H 0.1780 0.0674 0.2769 0.060 Uiso 1 1 calc R
C7 C 0.1071(4) 0.0742(2) 0.4841(5) 0.0416(12) Uani 1 1 d .
C8 C 0.1979(4) 0.0456(2) 0.5889(5) 0.0365(11) Uani 1 1 d .
C9 C 0.1898(4) 0.0204(3) 0.8686(5) 0.0555(14) Uani 1 1 d .
H9A H 0.2718 0.0014 0.8513 0.083 Uiso 1 1 calc R
H9B H 0.1348 -0.0143 0.9070 0.083 Uiso 1 1 calc R
H9C H 0.1966 0.0566 0.9415 0.083 Uiso 1 1 calc R
C10 C 0.3106(4) 0.0237(2) 0.5530(5) 0.0403(11) Uani 1 1 d .
H10 H 0.3326 0.0291 0.4515 0.048 Uiso 1 1 calc R
C11 C 0.4060(4) -0.0078(2) 0.6509(4) 0.0348(11) Uani 1 1 d .
C12 C 0.4214(4) -0.0766(2) 0.6463(5) 0.0464(12) Uani 1 1 d .
H12 H 0.3724 -0.1019 0.5782 0.056 Uiso 1 1 calc R
C13 C 0.5054(4) -0.1094(2) 0.7373(5) 0.0460(12) Uani 1 1 d .
H13 H 0.5129 -0.1565 0.7333 0.055 Uiso 1 1 calc R
C14 C 0.5782(4) -0.0726(2) 0.8343(5) 0.0427(12) Uani 1 1 d .
H14 H 0.6351 -0.0947 0.8991 0.051 Uiso 1 1 calc R
C15 C 0.5690(4) -0.0041(2) 0.8377(4) 0.0397(11) Uani 1 1 d .
H15 H 0.6211 0.0205 0.9037 0.048 Uiso 1 1 calc R
C16 C 0.4844(4) 0.0300(2) 0.7460(4) 0.0350(11) Uani 1 1 d .
C17 C 0.5317(4) 0.1461(2) 0.8350(4) 0.0364(11) Uani 1 1 d .
C18 C 0.6593(4) 0.1421(2) 0.8612(4) 0.0422(12) Uani 1 1 d .
H18 H 0.7056 0.1076 0.8156 0.051 Uiso 1 1 calc R
C19 C 0.7189(5) 0.1878(3) 0.9527(5) 0.0504(13) Uani 1 1 d .
H19 H 0.8056 0.1840 0.9692 0.060 Uiso 1 1 calc R
C20 C 0.6548(5) 0.2385(3) 1.0201(5) 0.0513(13) Uani 1 1 d .
H20 H 0.6958 0.2689 1.0853 0.062 Uiso 1 1 calc R
C21 C 0.5291(5) 0.2444(2) 0.9910(5) 0.0462(13) Uani 1 1 d .
H21 H 0.4847 0.2801 1.0349 0.055 Uiso 1 1 calc R
C22 C 0.4659(4) 0.1994(2) 0.8992(4) 0.0340(11) Uani 1 1 d .
C23 C 0.3309(4) 0.2071(2) 0.8668(5) 0.0374(11) Uani 1 1 d .
C24 C 0.1261(4) 0.2394(3) 0.9529(5) 0.0536(14) Uani 1 1 d .
H24A H 0.0902 0.2571 1.0446 0.080 Uiso 1 1 calc R
H24B H 0.0878 0.1964 0.9289 0.080 Uiso 1 1 calc R
H24C H 0.1109 0.2707 0.8708 0.080 Uiso 1 1 calc R
N1 N 0.1399(3) 0.04598(19) 0.7303(4) 0.0427(10) Uani 1 1 d .
N2 N 0.4696(3) 0.09923(18) 0.7459(4) 0.0402(10) Uani 1 1 d .
H2 H 0.4147 0.1153 0.6822 0.048 Uiso 1 1 calc R
N3 N 0.2588(3) 0.23049(18) 0.9744(4) 0.0438(10) Uani 1 1 d .
H3A H 0.2924 0.2409 1.0612 0.053 Uiso 1 1 calc R
O1 O -0.0442(3) 0.08405(18) 0.8311(4) 0.0634(11) Uani 1 1 d .
O2 O 0.2853(3) 0.19204(15) 0.7423(3) 0.0442(8) Uani 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
O1 C1 N1 124.0(4)
O1 C1 C2 130.3(5)
N1 C1 C2 105.6(4)
C3 C2 C7 120.8(4)
C3 C2 C1 129.9(4)
C7 C2 C1 109.3(4)
C4 C3 C2 118.5(5)
C4 C3 H3 120.8
C2 C3 H3 120.8
C3 C4 C5 121.3(5)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C5 C6 120.6(5)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 118.1(4)
C7 C6 H6 120.9
C5 C6 H6 120.9
C6 C7 C2 120.7(4)
C6 C7 C8 131.4(4)
C2 C7 C8 107.9(4)
C10 C8 N1 129.0(4)
C10 C8 C7 125.4(4)
N1 C8 C7 105.6(4)
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 C11 128.7(4)
C8 C10 H10 115.7
C11 C10 H10 115.7
C12 C11 C16 118.6(4)
C12 C11 C10 119.1(4)
C16 C11 C10 122.2(4)
C13 C12 C11 122.2(4)
C13 C12 H12 118.9
C11 C12 H12 118.9
C12 C13 C14 119.0(4)
C12 C13 H13 120.5
C14 C13 H13 120.5
C15 C14 C13 120.4(4)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 121.4(4)
C14 C15 H15 119.3
C16 C15 H15 119.3
N2 C16 C15 124.0(4)
N2 C16 C11 117.7(4)
C15 C16 C11 118.3(4)
C18 C17 N2 121.5(4)
C18 C17 C22 118.4(4)
N2 C17 C22 120.1(4)
C19 C18 C17 120.9(4)
C19 C18 H18 119.6
C17 C18 H18 119.6
C20 C19 C18 121.1(5)
C20 C19 H19 119.5
C18 C19 H19 119.5
C19 C20 C21 118.6(5)
C19 C20 H20 120.7
C21 C20 H20 120.7
C20 C21 C22 121.9(5)
C20 C21 H21 119.0
C22 C21 H21 119.0
C21 C22 C17 119.0(4)
C21 C22 C23 121.2(4)
C17 C22 C23 119.7(4)
O2 C23 N3 120.1(4)
O2 C23 C22 121.5(4)
N3 C23 C22 118.4(4)
N3 C24 H24A 109.5
N3 C24 H24B 109.5
H24A C24 H24B 109.5
N3 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C1 N1 C8 111.5(4)
C1 N1 C9 121.6(3)
C8 N1 C9 126.9(4)
C16 N2 C17 127.8(4)
C16 N2 H2 116.1
C17 N2 H2 116.1
C23 N3 C24 122.1(4)
C23 N3 H3A 118.9
C24 N3 H3A 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.233(5)
C1 N1 1.398(5)
C1 C2 1.463(6)
C2 C3 1.389(6)
C2 C7 1.397(6)
C3 C4 1.349(6)
C3 H3 0.9500
C4 C5 1.393(6)
C4 H4 0.9500
C5 C6 1.396(6)
C5 H5 0.9500
C6 C7 1.363(6)
C6 H6 0.9500
C7 C8 1.467(6)
C8 C10 1.338(6)
C8 N1 1.422(5)
C9 N1 1.441(5)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.488(6)
C10 H10 0.9500
C11 C12 1.391(6)
C11 C16 1.416(6)
C12 C13 1.380(6)
C12 H12 0.9500
C13 C14 1.380(6)
C13 H13 0.9500
C14 C15 1.379(6)
C14 H14 0.9500
C15 C16 1.401(6)
C15 H15 0.9500
C16 N2 1.398(5)
C17 C18 1.399(6)
C17 N2 1.400(5)
C17 C22 1.411(6)
C18 C19 1.384(6)
C18 H18 0.9500
C19 C20 1.376(6)
C19 H19 0.9500
C20 C21 1.386(6)
C20 H20 0.9500
C21 C22 1.395(6)
C21 H21 0.9500
C22 C23 1.492(6)
C23 O2 1.252(5)
C23 N3 1.333(5)
C24 N3 1.457(5)
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
N2 H2 0.8800
N3 H3A 0.8800
