#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/76/1517662.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_1517662
loop_
_publ_author_name
'Reddy, Mallu Chenna'
'Jeganmohan, Masilamani'
_publ_section_title
;
 Ruthenium-Catalyzed Cyclization of Aromatic Nitriles with Alkenes:
 Stereoselective Synthesis of (Z)-3-Methyleneisoindolin-1-ones.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4866
_journal_page_last               4869
_journal_paper_doi               10.1021/ol502375p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H13 N O4 S'
_chemical_formula_sum            'C16 H13 N O4 S'
_chemical_formula_weight         315.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8157(16)
_cell_length_b                   10.5029(9)
_cell_length_c                   15.0591(15)
_cell_measurement_reflns_used    6046
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.21
_cell_measurement_theta_min      2.22
_cell_volume                     2976.0(5)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40742
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.165
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorbtion correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0397
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2163
_reflns_number_total             3043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol502375p_si_002.cif
_cod_data_source_block           compound3cg
_cod_depositor_comments          'Adding full bibliography for 1517662.cif.'
_cod_database_code               1517662
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.73363(3) -0.15996(5) 0.70454(3) 0.0399(2) Uani 1 1 d . U
O3 O 0.70113(9) -0.28426(13) 0.69801(10) 0.0512(4) Uani 1 1 d . U
O2 O 0.79576(8) -0.13476(16) 0.65184(10) 0.0538(4) Uani 1 1 d . U
O1 O 0.47978(9) 0.34777(17) 0.60958(18) 0.0871(8) Uani 1 1 d . U
O4 O 0.45877(10) -0.26925(17) 0.62010(16) 0.0809(7) Uani 1 1 d . U
N006 N 0.56937(10) -0.18744(18) 0.65358(15) 0.0538(5) Uani 1 1 d . U
H006 H 0.5908 -0.2583 0.6637 0.065 Uiso 1 1 calc R U
C8 C 0.54593(11) 0.0244(2) 0.63879(14) 0.0405(5) Uani 1 1 d . U
C11 C 0.75657(11) -0.1333(2) 0.81628(13) 0.0376(5) Uani 1 1 d . U
C10 C 0.67010(10) -0.04506(19) 0.68028(14) 0.0387(5) Uani 1 1 d . U
H10 H 0.6843 0.0397 0.6815 0.046 Uiso 1 1 calc R U
C7 C 0.60188(11) -0.06986(19) 0.65993(13) 0.0397(5) Uani 1 1 d . U
C5 C 0.48391(11) -0.0422(2) 0.61993(15) 0.0465(5) Uani 1 1 d . U
C12 C 0.72248(12) -0.2005(2) 0.88198(15) 0.0487(6) Uani 1 1 d . U
H12 H 0.6876 -0.2599 0.8680 0.058 Uiso 1 1 calc R U
C9 C 0.54905(12) 0.1559(2) 0.63621(16) 0.0473(6) Uani 1 1 d . U
H9 H 0.5908 0.1999 0.6485 0.057 Uiso 1 1 calc R U
C16 C 0.80873(12) -0.0451(2) 0.83639(16) 0.0519(6) Uani 1 1 d . U
H16 H 0.8318 -0.0008 0.7913 0.062 Uiso 1 1 calc R U
C6 C 0.49760(13) -0.1788(2) 0.62888(18) 0.0559(6) Uani 1 1 d . U
C4 C 0.42221(12) 0.0224(2) 0.59815(18) 0.0562(7) Uani 1 1 d . U
H4 H 0.3806 -0.0215 0.5852 0.067 Uiso 1 1 calc R U
C2 C 0.48606(12) 0.2194(2) 0.61415(18) 0.0570(7) Uani 1 1 d . U
C13 C 0.74122(14) -0.1779(3) 0.96967(16) 0.0596(7) Uani 1 1 d . U
H13 H 0.7190 -0.2229 1.0150 0.072 Uiso 1 1 calc R U
C14 C 0.79232(15) -0.0895(2) 0.98992(16) 0.0607(7) Uani 1 1 d . U
H14 H 0.8041 -0.0742 1.0489 0.073 Uiso 1 1 calc R U
C15 C 0.82610(14) -0.0237(2) 0.92361(18) 0.0615(7) Uani 1 1 d . U
H15 H 0.8609 0.0358 0.9378 0.074 Uiso 1 1 calc R U
C3 C 0.42401(12) 0.1527(2) 0.5961(2) 0.0609(7) Uani 1 1 d . U
H3 H 0.3828 0.1974 0.5824 0.073 Uiso 1 1 calc R U
C1 C 0.54025(17) 0.4223(3) 0.6243(3) 0.1094(15) Uani 1 1 d . U
H1A H 0.5553 0.4129 0.6849 0.164 Uiso 1 1 calc R U
H1B H 0.5292 0.5101 0.6128 0.164 Uiso 1 1 calc R U
H1C H 0.5777 0.3952 0.5853 0.164 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'
S S 0.1246 0.1234 '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
O2 S1 O3 118.23(10)
O2 S1 C10 108.40(10)
O3 S1 C10 108.79(10)
O2 S1 C11 107.41(10)
O3 S1 C11 108.21(10)
C10 S1 C11 105.03(10)
C2 O1 C1 118.6(2)
C7 N006 C6 112.76(19)
C9 C8 C5 122.2(2)
C9 C8 C7 130.1(2)
C5 C8 C7 107.73(18)
C12 C11 C16 121.2(2)
C12 C11 S1 119.50(18)
C16 C11 S1 119.33(16)
C7 C10 S1 124.74(17)
C10 C7 N006 127.7(2)
C10 C7 C8 126.75(19)
N006 C7 C8 105.55(18)
C4 C5 C8 120.4(2)
C4 C5 C6 130.5(2)
C8 C5 C6 109.1(2)
C11 C12 C13 118.6(2)
C8 C9 C2 116.5(2)
C15 C16 C11 119.2(2)
O4 C6 N006 124.1(2)
O4 C6 C5 131.0(2)
N006 C6 C5 104.9(2)
C3 C4 C5 118.3(2)
O1 C2 C3 114.8(2)
O1 C2 C9 124.0(2)
C3 C2 C9 121.2(2)
C14 C13 C12 120.4(2)
C13 C14 C15 120.3(2)
C14 C15 C16 120.3(2)
C4 C3 C2 121.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4375(16)
S1 O3 1.4450(16)
S1 C10 1.737(2)
S1 C11 1.760(2)
O1 C2 1.355(3)
O1 C1 1.399(4)
O4 C6 1.205(3)
N006 C7 1.381(3)
N006 C6 1.404(3)
C8 C9 1.383(3)
C8 C5 1.390(3)
C8 C7 1.480(3)
C11 C12 1.374(3)
C11 C16 1.383(3)
C10 C7 1.345(3)
C5 C4 1.384(3)
C5 C6 1.464(3)
C12 C13 1.387(3)
C9 C2 1.400(3)
C16 C15 1.372(3)
C4 C3 1.369(3)
C2 C3 1.389(3)
C13 C14 1.371(4)
C14 C15 1.371(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102366770
