#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/02/2220276.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220276
loop_
_publ_author_name
'Bartholomä, Mark Daniel'
'Ouellette, Wayne'
'Zubieta, Jon'
_publ_section_title
;
 2-(1,3-Dioxoisoindolin-2-yl)ethyl 4-methylbenzenesulfonate
;
_journal_coeditor_code           LH2734
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2395
_journal_paper_doi               10.1107/S1600536808037951
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H15 N O5 S'
_chemical_formula_moiety         'C17 H15 N O5 S'
_chemical_formula_sum            'C17 H15 N O5 S'
_chemical_formula_weight         345.36
_chemical_name_systematic
;
2-(1,3-Dioxoisoindolin-2-yl)ethyl 4-methylbenzenesulfonate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.121(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.6817(13)
_cell_length_b                   12.5642(12)
_cell_length_c                   19.3194(19)
_cell_measurement_reflns_used    9534
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.21
_cell_volume                     3173.8(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16184
_diffrn_reflns_theta_full        28.08
_diffrn_reflns_theta_max         28.08
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0.001
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9338
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SHELXL97; Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.406
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.245
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0519
_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)+(0.0413P)²+6.2623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3773
_reflns_number_total             3865
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2734.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220276
_cod_database_fobs_code          2220276
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.24768(3) -0.05689(4) 1.04905(2) 0.01844(13) Uani d . 1
O O1 0.27012(11) -0.16681(11) 1.06516(7) 0.0245(3) Uani d . 1
O O2 0.26255(12) 0.01842(12) 1.10672(7) 0.0269(3) Uani d . 1
O O3 0.13136(10) -0.04377(10) 1.00548(7) 0.0195(3) Uani d . 1
O O4 0.12124(10) -0.09920(11) 0.78928(7) 0.0214(3) Uani d . 1
O O5 0.01573(11) 0.16581(11) 0.91348(8) 0.0270(3) Uani d . 1
N N1 0.05468(11) 0.01454(12) 0.85773(8) 0.0179(3) Uani d . 1
C C1 0.31279(13) -0.01266(16) 0.98842(10) 0.0193(4) Uani d . 1
C C2 0.35460(15) -0.08611(17) 0.95184(11) 0.0243(4) Uani d . 1
H H2 0.3486 -0.1603 0.9592 0.029 Uiso calc R 1
C C3 0.40571(15) -0.04904(19) 0.90397(11) 0.0287(4) Uani d . 1
H H3 0.4350 -0.0988 0.8788 0.034 Uiso calc R 1
C C4 0.41464(15) 0.0590(2) 0.89231(11) 0.0294(5) Uani d . 1
C C5 0.46884(19) 0.0980(2) 0.83979(13) 0.0425(6) Uani d . 1
H H5A 0.5003 0.0376 0.8223 0.064 Uiso calc R 1
H H5B 0.5220 0.1491 0.8641 0.064 Uiso calc R 1
H H5C 0.4196 0.1328 0.7987 0.064 Uiso calc R 1
C C6 0.37176(16) 0.13104(18) 0.93012(12) 0.0286(4) Uani d . 1
H H6 0.3773 0.2052 0.9226 0.034 Uiso calc R 1
C C7 0.32129(15) 0.09635(16) 0.97844(11) 0.0236(4) Uani d . 1
H H7 0.2930 0.1460 1.0043 0.028 Uiso calc R 1
C C8 0.10819(13) -0.01011(15) 0.80845(9) 0.0169(3) Uani d . 1
C C9 0.14229(13) 0.09383(15) 0.78653(9) 0.0180(3) Uani d . 1
C C10 0.19546(15) 0.11612(16) 0.73773(10) 0.0218(4) Uani d . 1
H H10 0.2158 0.0612 0.7111 0.026 Uiso calc R 1
C C11 0.21815(16) 0.22272(17) 0.72909(11) 0.0270(4) Uani d . 1
H H11 0.2547 0.2410 0.6959 0.032 Uiso calc R 1
C C12 0.18807(17) 0.30273(17) 0.76836(11) 0.0276(4) Uani d . 1
H H12 0.2055 0.3745 0.7620 0.033 Uiso calc R 1
C C13 0.13283(15) 0.27955(16) 0.81683(10) 0.0232(4) Uani d . 1
H H13 0.1115 0.3341 0.8432 0.028 Uiso calc R 1
C C14 0.11061(13) 0.17402(15) 0.82475(9) 0.0182(3) Uani d . 1
C C15 0.05463(14) 0.12411(14) 0.87179(10) 0.0186(4) Uani d . 1
C C16 0.00646(14) -0.06579(15) 0.89112(10) 0.0191(4) Uani d . 1
H H16A -0.0302 -0.1175 0.8538 0.023 Uiso calc R 1
H H16B -0.0443 -0.0312 0.9112 0.023 Uiso calc R 1
C C17 0.08415(14) -0.12402(14) 0.95089(10) 0.0191(4) Uani d . 1
H H17A 0.0505 -0.1797 0.9720 0.023 Uiso calc R 1
H H17B 0.1364 -0.1581 0.9320 0.023 Uiso calc R 1
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
O1 S1 O2 119.84(9)
O1 S1 O3 109.64(8)
O2 S1 O3 103.69(8)
O1 S1 C1 109.41(9)
O2 S1 C1 109.05(9)
O3 S1 C1 103.97(8)
C17 O3 S1 118.36(11)
C8 N1 C15 112.32(15)
C8 N1 C16 123.05(15)
C15 N1 C16 124.62(15)
C2 C1 C7 121.40(18)
C2 C1 S1 119.74(15)
C7 C1 S1 118.85(15)
C1 C2 C3 118.6(2)
C1 C2 H2 120.7
C3 C2 H2 120.7
C4 C3 C2 121.3(2)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C6 118.61(19)
C3 C4 C5 120.9(2)
C6 C4 C5 120.5(2)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 C4 121.2(2)
C7 C6 H6 119.4
C4 C6 H6 119.4
C6 C7 C1 118.77(19)
C6 C7 H7 120.6
C1 C7 H7 120.6
O4 C8 N1 124.67(17)
O4 C8 C9 129.65(17)
N1 C8 C9 105.69(15)
C10 C9 C14 121.68(18)
C10 C9 C8 130.16(17)
C14 C9 C8 108.15(16)
C9 C10 C11 117.22(18)
C9 C10 H10 121.4
C11 C10 H10 121.4
C12 C11 C10 121.04(18)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 121.33(19)
C11 C12 H12 119.3
C13 C12 H12 119.3
C14 C13 C12 117.10(18)
C14 C13 H13 121.5
C12 C13 H13 121.5
C13 C14 C9 121.61(17)
C13 C14 C15 130.00(17)
C9 C14 C15 108.39(16)
O5 C15 N1 125.45(17)
O5 C15 C14 129.15(17)
N1 C15 C14 105.40(15)
N1 C16 C17 111.48(15)
N1 C16 H16A 109.3
C17 C16 H16A 109.3
N1 C16 H16B 109.3
C17 C16 H16B 109.3
H16A C16 H16B 108.0
O3 C17 C16 106.23(14)
O3 C17 H17A 110.5
C16 C17 H17A 110.5
O3 C17 H17B 110.5
C16 C17 H17B 110.5
H17A C17 H17B 108.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4290(15)
S1 O2 1.4299(14)
S1 O3 1.5747(14)
S1 C1 1.7574(18)
O3 C17 1.465(2)
O4 C8 1.209(2)
O5 C15 1.208(2)
N1 C8 1.396(2)
N1 C15 1.403(2)
N1 C16 1.456(2)
C1 C2 1.384(3)
C1 C7 1.393(3)
C2 C3 1.394(3)
C2 H2 0.9500
C3 C4 1.387(3)
C3 H3 0.9500
C4 C6 1.396(3)
C4 C5 1.504(3)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.385(3)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.489(3)
C9 C10 1.379(3)
C9 C14 1.392(3)
C10 C11 1.396(3)
C10 H10 0.9500
C11 C12 1.393(3)
C11 H11 0.9500
C12 C13 1.396(3)
C12 H12 0.9500
C13 C14 1.379(3)
C13 H13 0.9500
C14 C15 1.488(2)
C16 C17 1.509(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9900
C17 H17B 0.9900
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
O1 S1 O3 C17 -38.67(14)
O2 S1 O3 C17 -167.78(12)
C1 S1 O3 C17 78.22(14)
O1 S1 C1 C2 14.61(18)
O2 S1 C1 C2 147.43(15)
O3 S1 C1 C2 -102.45(16)
O1 S1 C1 C7 -165.23(15)
O2 S1 C1 C7 -32.41(18)
O3 S1 C1 C7 77.71(16)
C7 C1 C2 C3 -0.3(3)
S1 C1 C2 C3 179.90(15)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C6 0.5(3)
C2 C3 C4 C5 -179.22(19)
C3 C4 C6 C7 0.1(3)
C5 C4 C6 C7 179.75(19)
C4 C6 C7 C1 -0.7(3)
C2 C1 C7 C6 0.8(3)
S1 C1 C7 C6 -179.38(15)
C15 N1 C8 O4 177.95(17)
C16 N1 C8 O4 -1.1(3)
C15 N1 C8 C9 -2.38(19)
C16 N1 C8 C9 178.62(15)
O4 C8 C9 C10 1.6(3)
N1 C8 C9 C10 -178.05(18)
O4 C8 C9 C14 -178.67(18)
N1 C8 C9 C14 1.69(19)
C14 C9 C10 C11 1.2(3)
C8 C9 C10 C11 -179.09(18)
C9 C10 C11 C12 0.0(3)
C10 C11 C12 C13 -1.0(3)
C11 C12 C13 C14 0.8(3)
C12 C13 C14 C9 0.4(3)
C12 C13 C14 C15 179.45(18)
C10 C9 C14 C13 -1.4(3)
C8 C9 C14 C13 178.79(17)
C10 C9 C14 C15 179.32(16)
C8 C9 C14 C15 -0.45(19)
C8 N1 C15 O5 -178.31(18)
C16 N1 C15 O5 0.7(3)
C8 N1 C15 C14 2.1(2)
C16 N1 C15 C14 -178.90(16)
C13 C14 C15 O5 0.3(3)
C9 C14 C15 O5 179.49(19)
C13 C14 C15 N1 179.90(19)
C9 C14 C15 N1 -0.95(19)
C8 N1 C16 C17 76.8(2)
C15 N1 C16 C17 -102.06(19)
S1 O3 C17 C16 -146.02(12)
N1 C16 C17 O3 61.83(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 198002
