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#$Date: 2020-06-05 14:29:40 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157486.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_7157486
loop_
_publ_author_name
'Sreedharan, Ramdas'
'Rajeshwaran, Purushothaman'
'Panyam, Pradeep Kumar Reddy'
'Yadav, Saurabh'
'Nagaraja, C. M.'
'Gandhi, Thirumanavelan'
_publ_section_title
;
 Acylation of oxindoles using methyl/phenyl esters via the mixed Claisen
 condensation - an access to 3-alkylideneoxindoles.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3843
_journal_page_last               3847
_journal_paper_doi               10.1039/d0ob00789g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C16 H11 Br N O2'
_chemical_formula_weight         329.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc23spj4
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-10-18 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                83.964(5)
_cell_angle_beta                 73.197(5)
_cell_angle_gamma                73.333(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3268(14)
_cell_length_b                   9.2126(13)
_cell_length_c                   9.6765(16)
_cell_measurement_temperature    273(2)
_cell_volume                     680.55(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12915
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.199
_exptl_absorpt_coefficient_mu    3.020
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             330
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0543P)²+0.4185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2534
_reflns_number_total             2770
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00789g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7157486--7157487.cif.'
_cod_database_code               7157486
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.86502(4) 0.50203(4) 0.87246(3) 0.05713(15) Uani 1 1 d . . . . .
C1 C 0.7002(4) 0.3297(4) 0.3032(3) 0.0487(6) Uani 1 1 d . . . . .
H1A H 0.6806 0.4285 0.2576 0.073 Uiso 1 1 calc R U . . .
H1B H 0.7959 0.2604 0.2404 0.073 Uiso 1 1 calc R U . . .
H1C H 0.5973 0.2952 0.3224 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7756(4) 0.2148(3) 0.5283(3) 0.0429(6) Uani 1 1 d . . . . .
N1 N 0.7408(3) 0.3372(2) 0.4374(2) 0.0384(4) Uani 1 1 d . . . . .
O2 O 0.5213(3) 0.3335(3) 0.8149(3) 0.0622(6) Uani 1 1 d . . . . .
C8 C 0.7824(3) 0.6957(3) 0.6366(3) 0.0445(6) Uani 1 1 d . . . . .
H8 H 0.7947 0.7726 0.6846 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7083(3) 0.1240(3) 0.9009(3) 0.0357(5) Uani 1 1 d . . . . .
C4 C 0.7934(3) 0.4342(3) 0.6222(3) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.7766(4) 0.0868(2) 0.5083(3) 0.0678(7) Uani 1 1 d . . . . .
C5 C 0.7495(3) 0.4689(3) 0.4921(2) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.8095(3) 0.5485(3) 0.6937(3) 0.0381(5) Uani 1 1 d . . . . .
C3 C 0.8087(3) 0.2698(3) 0.6591(3) 0.0372(5) Uani 1 1 d . . . . .
C10 C 0.6652(3) 0.2493(3) 0.7961(3) 0.0392(5) Uani 1 1 d . . . . .
C12 C 0.5956(4) 0.1326(3) 1.0399(3) 0.0456(6) Uani 1 1 d . . . . .
H12 H 0.4986 0.2154 1.0646 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7192(3) 0.6146(3) 0.4332(3) 0.0408(5) Uani 1 1 d . . . . .
H6 H 0.6882 0.6366 0.3469 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8513(4) 0.0002(3) 0.8649(3) 0.0449(6) Uani 1 1 d . . . . .
H16 H 0.9276 -0.0064 0.7726 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7703(4) -0.1033(3) 1.1038(3) 0.0548(7) Uani 1 1 d . . . . .
H14 H 0.7923 -0.1796 1.1723 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6276(4) 0.0189(3) 1.1408(3) 0.0528(7) Uani 1 1 d . . . . .
H13 H 0.5527 0.0250 1.2336 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7373(3) 0.7266(3) 0.5087(3) 0.0454(6) Uani 1 1 d . . . . .
H7 H 0.7182 0.8254 0.4715 0.054 Uiso 1 1 calc R U . . .
C15 C 0.8807(4) -0.1144(3) 0.9672(4) 0.0560(8) Uani 1 1 d . . . . .
H15 H 0.9756 -0.1990 0.9429 0.067 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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
O1 C2 N1 125.3(3) . . ?
O1 C2 C3 126.7(3) . . ?
N1 C2 C3 108.0(2) . . ?
C2 N1 C5 111.1(2) . . ?
C2 N1 C1 123.9(2) . . ?
C5 N1 C1 125.0(2) . . ?
C7 C8 C9 119.3(2) . . ?
C16 C11 C12 119.5(2) . . ?
C16 C11 C10 122.8(2) . . ?
C12 C11 C10 117.7(2) . . ?
C9 C4 C5 118.8(2) . . ?
C9 C4 C3 132.2(2) . . ?
C5 C4 C3 109.0(2) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 N1 128.2(2) . . ?
C4 C5 N1 109.5(2) . . ?
C4 C9 C8 120.5(2) . . ?
C4 C9 Br1 118.74(19) . . ?
C8 C9 Br1 120.8(2) . . ?
C4 C3 C2 102.30(19) . . ?
C4 C3 C10 111.0(2) . . ?
C2 C3 C10 109.2(2) . . ?
O2 C10 C11 121.6(2) . . ?
O2 C10 C3 119.3(2) . . ?
C11 C10 C3 119.1(2) . . ?
C13 C12 C11 120.2(3) . . ?
C5 C6 C7 117.1(2) . . ?
C11 C16 C15 119.6(3) . . ?
C15 C14 C13 120.8(3) . . ?
C14 C13 C12 119.7(3) . . ?
C8 C7 C6 122.0(2) . . ?
C14 C15 C16 120.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.893(3) . ?
C1 N1 1.446(3) . ?
C2 O1 1.213(3) . ?
C2 N1 1.371(3) . ?
C2 C3 1.533(4) . ?
N1 C5 1.401(3) . ?
O2 C10 1.201(3) . ?
C8 C7 1.374(4) . ?
C8 C9 1.391(4) . ?
C11 C16 1.380(4) . ?
C11 C12 1.395(4) . ?
C11 C10 1.488(3) . ?
C4 C9 1.375(3) . ?
C4 C5 1.392(3) . ?
C4 C3 1.497(3) . ?
C5 C6 1.385(3) . ?
C3 C10 1.543(3) . ?
C12 C13 1.377(4) . ?
C6 C7 1.390(4) . ?
C16 C15 1.388(4) . ?
C14 C15 1.370(4) . ?
C14 C13 1.371(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 N1 C5 179.8(3) . . . . ?
C3 C2 N1 C5 0.9(3) . . . . ?
O1 C2 N1 C1 -0.1(5) . . . . ?
C3 C2 N1 C1 -179.0(2) . . . . ?
C9 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C6 177.3(2) . . . . ?
C9 C4 C5 N1 179.7(2) . . . . ?
C3 C4 C5 N1 -2.1(3) . . . . ?
C2 N1 C5 C6 -178.6(2) . . . . ?
C1 N1 C5 C6 1.3(4) . . . . ?
C2 N1 C5 C4 0.8(3) . . . . ?
C1 N1 C5 C4 -179.3(2) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C3 C4 C9 C8 -177.7(2) . . . . ?
C5 C4 C9 Br1 178.84(17) . . . . ?
C3 C4 C9 Br1 1.3(4) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C7 C8 C9 Br1 -178.12(19) . . . . ?
C9 C4 C3 C2 -179.7(3) . . . . ?
C5 C4 C3 C2 2.5(3) . . . . ?
C9 C4 C3 C10 63.9(3) . . . . ?
C5 C4 C3 C10 -113.8(2) . . . . ?
O1 C2 C3 C4 179.1(3) . . . . ?
N1 C2 C3 C4 -2.0(3) . . . . ?
O1 C2 C3 C10 -63.3(4) . . . . ?
N1 C2 C3 C10 115.6(2) . . . . ?
C16 C11 C10 O2 160.1(3) . . . . ?
C12 C11 C10 O2 -18.5(4) . . . . ?
C16 C11 C10 C3 -19.2(4) . . . . ?
C12 C11 C10 C3 162.2(2) . . . . ?
C4 C3 C10 O2 38.4(4) . . . . ?
C2 C3 C10 O2 -73.6(3) . . . . ?
C4 C3 C10 C11 -142.4(2) . . . . ?
C2 C3 C10 C11 105.6(3) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C13 179.1(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
N1 C5 C6 C7 -179.7(2) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C10 C11 C16 C15 -178.2(3) . . . . ?
C15 C14 C13 C12 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C11 C16 C15 C14 -1.3(5) . . . . ?
