#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:57:15 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153809.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_7153809
loop_
_publ_author_name
'Edeson, Steven J.'
'Jiang, Julong'
'Swanson, Stephen'
'Procopiou, Panayiotis A.'
'Adams, Harry'
'Meijer, Anthony J. H. M.'
'Harrity, Joseph P. A.'
_publ_section_title
;
 Studies on the stereochemical assignment of 3-acylidene 2-oxindoles.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3201
_journal_page_last               3210
_journal_paper_doi               10.1039/c4ob00496e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C16 H10 Cl N O2'
_chemical_formula_sum            'C16 H10 Cl N O2'
_chemical_formula_weight         283.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.268(5)
_cell_angle_beta                 99.008(5)
_cell_angle_gamma                100.544(5)
_cell_formula_units_Z            2
_cell_length_a                   5.3737(8)
_cell_length_b                   10.8985(17)
_cell_length_c                   11.5417(18)
_cell_measurement_reflns_used    5071
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.40
_cell_volume                     645.90(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8230
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         8230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0551
_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)+(0.1257P)²+0.8962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                7383
_reflns_number_total             8230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00496e3.cif
_cod_data_source_block           ohj268p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153809
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl -0.31908(9) 0.88484(4) 0.51572(5) 0.01940(16) Uani 1 1 d .
O1 O -0.1053(3) 0.56651(12) 0.14739(13) 0.0232(4) Uani 1 1 d .
O2 O 0.3555(3) 0.56086(12) 0.36517(13) 0.0172(3) Uani 1 1 d .
N1 N 0.3039(3) 0.59779(14) 0.56113(15) 0.0147(3) Uani 1 1 d .
H1N H 0.4051 0.5526 0.5903 0.018 Uiso 1 1 calc R
C1 C 0.6554(4) 0.8807(2) 0.0935(2) 0.0294(5) Uani 1 1 d .
H1 H 0.7910 0.9278 0.0671 0.035 Uiso 1 1 calc R
C2 C 0.5544(4) 0.7564(2) 0.0394(2) 0.0294(5) Uani 1 1 d .
H9 H 0.6236 0.7200 -0.0226 0.035 Uiso 1 1 calc R
C3 C 0.3494(4) 0.6851(2) 0.07713(19) 0.0227(5) Uani 1 1 d .
H3 H 0.2803 0.6016 0.0399 0.027 Uiso 1 1 calc R
C4 C 0.2493(4) 0.73963(17) 0.17066(17) 0.0150(4) Uani 1 1 d .
C5 C 0.0276(4) 0.66311(16) 0.20931(18) 0.0151(4) Uani 1 1 d .
C6 C -0.0428(4) 0.71415(16) 0.32565(18) 0.0153(4) Uani 1 1 d .
H4 H -0.1661 0.7640 0.3236 0.018 Uiso 1 1 calc R
C7 C 0.0611(3) 0.69198(16) 0.43100(18) 0.0132(4) Uani 1 1 d .
C8 C 0.0141(3) 0.72816(16) 0.55201(17) 0.0131(4) Uani 1 1 d .
C9 C 0.1654(3) 0.66901(16) 0.62803(18) 0.0143(4) Uani 1 1 d .
C10 C 0.1679(4) 0.68124(17) 0.74848(19) 0.0184(4) Uani 1 1 d .
H5 H 0.2701 0.6411 0.7967 0.022 Uiso 1 1 calc R
C11 C 0.0107(4) 0.75637(18) 0.79541(19) 0.0190(4) Uani 1 1 d .
H2 H 0.0067 0.7658 0.8764 0.023 Uiso 1 1 calc R
C12 C 0.2578(3) 0.60919(15) 0.44460(17) 0.0132(4) Uani 1 1 d .
C13 C -0.1349(3) 0.80421(16) 0.60298(18) 0.0143(4) Uani 1 1 d .
C14 C -0.1400(4) 0.81747(18) 0.72360(19) 0.0187(4) Uani 1 1 d .
H6 H -0.2438 0.8671 0.7565 0.022 Uiso 1 1 calc R
C15 C 0.3528(4) 0.86473(17) 0.2262(2) 0.0196(4) Uani 1 1 d .
H7 H 0.2864 0.9008 0.2894 0.023 Uiso 1 1 calc R
C16 C 0.5559(4) 0.9360(2) 0.1870(2) 0.0265(5) Uani 1 1 d .
H8 H 0.6241 1.0200 0.2232 0.032 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'
Cl Cl 0.1484 0.1585 '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
C12 N1 C9 111.44(16)
C12 N1 H1N 124.3
C9 N1 H1N 124.3
C2 C1 C16 120.4(2)
C2 C1 H1 119.8
C16 C1 H1 119.8
C1 C2 C3 120.4(2)
C1 C2 H9 119.8
C3 C2 H9 119.8
C4 C3 C2 119.46(19)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C15 120.17(18)
C3 C4 C5 119.07(17)
C15 C4 C5 120.76(18)
O1 C5 C4 122.34(19)
O1 C5 C6 119.65(17)
C4 C5 C6 117.86(15)
C7 C6 C5 123.82(17)
C7 C6 H4 118.1
C5 C6 H4 118.1
C6 C7 C8 132.31(17)
C6 C7 C12 122.63(18)
C8 C7 C12 104.96(16)
C13 C8 C9 117.53(18)
C13 C8 C7 135.18(18)
C9 C8 C7 107.28(16)
C10 C9 N1 127.45(18)
C10 C9 C8 123.22(18)
N1 C9 C8 109.33(17)
C9 C10 C11 117.25(19)
C9 C10 H5 121.4
C11 C10 H5 121.4
C14 C11 C10 121.4(2)
C14 C11 H2 119.3
C10 C11 H2 119.3
O2 C12 N1 126.53(17)
O2 C12 C7 126.54(17)
N1 C12 C7 106.93(16)
C14 C13 C8 120.88(19)
C14 C13 Cl1 118.82(16)
C8 C13 Cl1 120.30(16)
C13 C14 C11 119.72(19)
C13 C14 H6 120.1
C11 C14 H6 120.1
C4 C15 C16 120.0(2)
C4 C15 H7 120.0
C16 C15 H7 120.0
C1 C16 C15 119.45(19)
C1 C16 H8 120.3
C15 C16 H8 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.740(2)
O1 C5 1.215(2)
O2 C12 1.228(2)
N1 C12 1.357(3)
N1 C9 1.404(2)
N1 H1N 0.8600
C1 C2 1.379(3)
C1 C16 1.387(3)
C1 H1 0.9300
C2 C3 1.393(3)
C2 H9 0.9300
C3 C4 1.386(3)
C3 H3 0.9300
C4 C15 1.392(3)
C4 C5 1.491(3)
C5 C6 1.509(3)
C6 C7 1.330(3)
C6 H4 0.9300
C7 C8 1.469(3)
C7 C12 1.514(3)
C8 C13 1.387(3)
C8 C9 1.406(3)
C9 C10 1.375(3)
C10 C11 1.395(3)
C10 H5 0.9300
C11 C14 1.390(3)
C11 H2 0.9300
C13 C14 1.384(3)
C14 H6 0.9300
C15 C16 1.395(3)
C15 H7 0.9300
C16 H8 0.9300
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
C16 C1 C2 C3 0.7(3)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C15 0.1(3)
C2 C3 C4 C5 179.19(19)
C3 C4 C5 O1 -16.7(3)
C15 C4 C5 O1 162.39(19)
C3 C4 C5 C6 167.87(17)
C15 C4 C5 C6 -13.1(3)
O1 C5 C6 C7 96.6(2)
C4 C5 C6 C7 -87.8(2)
C5 C6 C7 C8 -177.52(17)
C5 C6 C7 C12 -1.8(3)
C6 C7 C8 C13 -6.0(3)
C12 C7 C8 C13 177.73(19)
C6 C7 C8 C9 175.02(18)
C12 C7 C8 C9 -1.28(18)
C12 N1 C9 C10 -179.01(17)
C12 N1 C9 C8 1.7(2)
C13 C8 C9 C10 1.3(3)
C7 C8 C9 C10 -179.47(16)
C13 C8 C9 N1 -179.32(15)
C7 C8 C9 N1 -0.10(19)
N1 C9 C10 C11 -179.18(17)
C8 C9 C10 C11 0.1(3)
C9 C10 C11 C14 -0.7(3)
C9 N1 C12 O2 178.05(16)
C9 N1 C12 C7 -2.43(19)
C6 C7 C12 O2 5.0(3)
C8 C7 C12 O2 -178.22(16)
C6 C7 C12 N1 -174.50(16)
C8 C7 C12 N1 2.25(18)
C9 C8 C13 C14 -2.1(3)
C7 C8 C13 C14 178.94(18)
C9 C8 C13 Cl1 177.86(12)
C7 C8 C13 Cl1 -1.1(3)
C8 C13 C14 C11 1.6(3)
Cl1 C13 C14 C11 -178.41(14)
C10 C11 C14 C13 -0.1(3)
C3 C4 C15 C16 0.7(3)
C5 C4 C15 C16 -178.38(18)
C2 C1 C16 C15 0.1(3)
C4 C15 C16 C1 -0.8(3)
