#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/54/7105443.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_7105443
loop_
_publ_author_name
'Smith, Keith'
'El-Hiti, Gamal A'
'Hegazy, Amany S'
_publ_section_title
;
 One-pot synthesis of substituted isoindolin-1-ones via lithiation and
 substitution of N'-benzyl-N,N-dimethylureas.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2790
_journal_page_last               2792
_journal_paper_doi               10.1039/b926983e
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.32
_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                83.877(2)
_cell_angle_beta                 77.311(2)
_cell_angle_gamma                68.559(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5240(3)
_cell_length_b                   9.4100(3)
_cell_length_c                   11.9960(5)
_cell_measurement_reflns_used    2539
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.87
_cell_volume                     770.92(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997'
_computing_molecular_graphics    'Ortep-99 for Windows (Farrugia, 1995)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-92 (A. Altomare et al., 1992)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5071
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0570
_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)+(0.0452P)²+0.4323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                2539
_reflns_number_total             3513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b926983e.txt
_cod_data_source_block           ks0810
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105443
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2151(3) 0.2870(2) 0.60320(16) 0.0218(4) Uani 1 1 d . . .
C2 C 0.2871(3) 0.1307(2) 0.65399(16) 0.0220(4) Uani 1 1 d . . .
C3 C 0.1840(3) 0.0471(3) 0.72304(18) 0.0309(5) Uani 1 1 d . . .
H3 H 0.0488 0.0855 0.7424 0.037 Uiso 1 1 calc R . .
C4 C 0.2911(3) -0.0954(3) 0.76155(19) 0.0333(5) Uani 1 1 d . . .
H4 H 0.2260 -0.1533 0.8087 0.040 Uiso 1 1 calc R . .
C5 C 0.4939(3) -0.1555(2) 0.73223(17) 0.0285(5) Uani 1 1 d . . .
H5 H 0.5616 -0.2526 0.7588 0.034 Uiso 1 1 calc R . .
C6 C 0.5950(3) -0.0697(2) 0.66302(16) 0.0224(4) Uani 1 1 d . . .
C7 C 0.4880(3) 0.0751(2) 0.62507(15) 0.0201(4) Uani 1 1 d . . .
C8 C 0.5583(3) 0.1959(2) 0.55858(16) 0.0197(4) Uani 1 1 d . . .
H8 H 0.6344 0.1588 0.4832 0.024 Uiso 1 1 calc R . .
C9 C 0.9066(3) -0.2588(3) 0.6731(2) 0.0375(6) Uani 1 1 d . . .
H9A H 0.8774 -0.2611 0.7552 0.056 Uiso 1 1 calc R . .
H9B H 1.0423 -0.2746 0.6468 0.056 Uiso 1 1 calc R . .
H9C H 0.8769 -0.3381 0.6457 0.056 Uiso 1 1 calc R . .
C10 C 0.6774(3) 0.2512(2) 0.62221(16) 0.0217(4) Uani 1 1 d . . .
H10 H 0.8000 0.1670 0.6270 0.026 Uiso 1 1 calc R . .
C11 C 0.5706(3) 0.2997(2) 0.74238(16) 0.0215(4) Uani 1 1 d . . .
C12 C 0.5876(3) 0.1938(2) 0.83348(17) 0.0258(4) Uani 1 1 d . . .
H12 H 0.6722 0.0938 0.8207 0.031 Uiso 1 1 calc R . .
C13 C 0.4821(3) 0.2337(2) 0.94246(17) 0.0280(5) Uani 1 1 d . . .
H13 H 0.4952 0.1609 1.0020 0.034 Uiso 1 1 calc R . .
C14 C 0.3561(3) 0.3834(2) 0.96254(17) 0.0273(5) Uani 1 1 d . . .
C15 C 0.3384(3) 0.4913(2) 0.87379(18) 0.0285(5) Uani 1 1 d . . .
H15 H 0.2554 0.5917 0.8871 0.034 Uiso 1 1 calc R . .
C16 C 0.4455(3) 0.4489(2) 0.76442(17) 0.0265(5) Uani 1 1 d . . .
H16 H 0.4330 0.5219 0.7051 0.032 Uiso 1 1 calc R . .
C17 C 0.1370(3) 0.5686(3) 1.09920(19) 0.0371(6) Uani 1 1 d . . .
H17A H 0.2176 0.6301 1.0825 0.056 Uiso 1 1 calc R . .
H17B H 0.0778 0.5743 1.1789 0.056 Uiso 1 1 calc R . .
H17C H 0.0373 0.6054 1.0542 0.056 Uiso 1 1 calc R . .
O1 O 0.0450(2) 0.37467(16) 0.61120(12) 0.0284(3) Uani 1 1 d . . .
O2 O 0.7916(2) -0.11306(15) 0.63091(12) 0.0292(4) Uani 1 1 d . . .
O3 O 0.7209(2) 0.37137(16) 0.55327(12) 0.0266(3) Uani 1 1 d . . .
H3A H 0.8183 0.3795 0.5676 0.040 Uiso 1 1 calc R . .
O4 O 0.2535(2) 0.41330(18) 1.07237(12) 0.0362(4) Uani 1 1 d . . .
N1 N 0.3741(2) 0.31693(18) 0.54696(13) 0.0223(4) Uani 1 1 d . . .
H1 H 0.3677 0.4000 0.5077 0.027 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'
O O 0.0106 0.0060 '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'
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 C1 N1 126.01(19) . . ?
O1 C1 C2 127.69(18) . . ?
N1 C1 C2 106.29(17) . . ?
C7 C2 C3 121.98(19) . . ?
C7 C2 C1 108.27(17) . . ?
C3 C2 C1 129.72(19) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 119.93(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O2 C6 C7 116.07(17) . . ?
O2 C6 C5 125.75(18) . . ?
C7 C6 C5 118.16(18) . . ?
C2 C7 C6 120.64(18) . . ?
C2 C7 C8 109.82(16) . . ?
C6 C7 C8 129.41(18) . . ?
N1 C8 C7 101.28(14) . . ?
N1 C8 C10 111.33(15) . . ?
C7 C8 C10 113.04(15) . . ?
N1 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
C10 C8 H8 110.3 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 C11 112.75(15) . . ?
O3 C10 C8 106.44(15) . . ?
C11 C10 C8 112.10(15) . . ?
O3 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C8 C10 H10 108.5 . . ?
C16 C11 C12 117.88(18) . . ?
C16 C11 C10 121.28(18) . . ?
C12 C11 C10 120.76(17) . . ?
C13 C12 C11 121.68(19) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.54(19) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
O4 C14 C15 123.99(19) . . ?
O4 C14 C13 116.08(18) . . ?
C15 C14 C13 119.92(18) . . ?
C14 C15 C16 119.72(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 121.24(19) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 O2 C9 117.45(16) . . ?
C10 O3 H3A 109.5 . . ?
C14 O4 C17 117.80(17) . . ?
C1 N1 C8 114.12(16) . . ?
C1 N1 H1 122.9 . . ?
C8 N1 H1 122.9 . . ?
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
C1 O1 1.232(2) . ?
C1 N1 1.348(2) . ?
C1 C2 1.483(3) . ?
C2 C7 1.382(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 O2 1.358(2) . ?
C6 C7 1.392(3) . ?
C7 C8 1.506(3) . ?
C8 N1 1.461(2) . ?
C8 C10 1.544(3) . ?
C8 H8 0.9800 . ?
C9 O2 1.436(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O3 1.422(2) . ?
C10 C11 1.515(3) . ?
C10 H10 0.9800 . ?
C11 C16 1.390(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9300 . ?
C14 O4 1.373(2) . ?
C14 C15 1.384(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O4 1.431(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O3 H3A 0.8200 . ?
N1 H1 0.8600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23953929
