#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153848.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_7153848
loop_
_publ_author_name
'Pratap Reddy Gajulapalli, V.'
'Vinayagam, Poopathy'
'Kesavan, Venkitasamy'
_publ_section_title
;
 Organocatalytic asymmetric decarboxylative cyanomethylation of isatins
 using l-proline derived bifunctional thiourea.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4186
_journal_page_last               4191
_journal_paper_doi               10.1039/c4ob00271g
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6964(3)
_cell_length_b                   12.6163(5)
_cell_length_c                   12.8565(7)
_cell_measurement_reflns_used    6242
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      3.16
_cell_volume                     923.96(8)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10767
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0310
_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)+(0.0529P)²+0.0443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                1978
_reflns_number_total             2129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00271g2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7153848.cif.'
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7153848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
C1 C 0.7056(2) 0.17659(10) 0.63717(9) 0.0328(3) Uani 1 1 d .
C2 C 0.6901(2) 0.12383(8) 0.80640(9) 0.0302(2) Uani 1 1 d .
C3 C 0.7458(3) 0.07705(10) 0.89997(9) 0.0387(3) Uani 1 1 d .
H3 H 0.8837 0.0386 0.9087 0.046 Uiso 1 1 calc R
C4 C 0.5867(3) 0.08991(11) 0.98053(10) 0.0476(4) Uani 1 1 d .
H4 H 0.6189 0.0592 1.0447 0.057 Uiso 1 1 calc R
C5 C 0.3833(3) 0.14649(12) 0.96836(11) 0.0490(4) Uani 1 1 d .
H5 H 0.2795 0.1529 1.0238 0.059 Uiso 1 1 calc R
C6 C 0.3307(3) 0.19434(11) 0.87382(10) 0.0413(3) Uani 1 1 d .
H6 H 0.1940 0.2337 0.8655 0.050 Uiso 1 1 calc R
C7 C 0.4860(2) 0.18189(9) 0.79318(9) 0.0293(2) Uani 1 1 d .
C8 C 0.47793(19) 0.22323(9) 0.68355(9) 0.0281(2) Uani 1 1 d .
C9 C 0.4835(2) 0.34467(10) 0.67706(11) 0.0396(3) Uani 1 1 d .
H9A H 0.4787 0.3658 0.6045 0.048 Uiso 1 1 calc R
H9B H 0.3445 0.3729 0.7107 0.048 Uiso 1 1 calc R
C10 C 0.6910(3) 0.39045(10) 0.72558(11) 0.0463(4) Uani 1 1 d .
N1 N 0.81520(19) 0.12143(8) 0.71193(9) 0.0360(2) Uani 1 1 d D
N2 N 0.8553(4) 0.42437(13) 0.76176(11) 0.0735(5) Uani 1 1 d .
O1 O 0.77119(17) 0.18814(9) 0.54793(7) 0.0496(3) Uani 1 1 d .
O2 O 0.27866(16) 0.18446(8) 0.63156(7) 0.0403(2) Uani 1 1 d .
H2 H 0.2764 0.2075 0.5719 0.061 Uiso 1 1 calc R
H1 H 0.952(2) 0.0936(13) 0.7047(13) 0.049(4) Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0308(6) 0.0381(5) 0.0294(6) 0.0023(5) 0.0018(5) -0.0010(5)
C2 0.0331(6) 0.0300(5) 0.0275(6) 0.0002(4) -0.0009(5) -0.0036(4)
C3 0.0472(8) 0.0351(5) 0.0339(6) 0.0043(5) -0.0084(6) 0.0004(5)
C4 0.0711(10) 0.0460(7) 0.0258(6) 0.0064(5) -0.0027(6) -0.0118(7)
C5 0.0552(9) 0.0629(9) 0.0288(7) -0.0011(6) 0.0096(6) -0.0087(7)
C6 0.0383(7) 0.0528(7) 0.0329(6) -0.0051(5) 0.0057(5) -0.0015(6)
C7 0.0302(6) 0.0310(5) 0.0269(5) 0.0008(4) -0.0011(5) -0.0040(5)
C8 0.0238(5) 0.0332(5) 0.0274(5) 0.0011(4) -0.0010(5) -0.0012(4)
C9 0.0439(7) 0.0346(6) 0.0404(7) 0.0054(5) -0.0081(6) 0.0025(5)
C10 0.0642(10) 0.0347(6) 0.0399(7) 0.0053(5) -0.0052(7) -0.0098(7)
N1 0.0300(5) 0.0456(5) 0.0325(5) 0.0049(4) 0.0022(5) 0.0092(4)
N2 0.0904(12) 0.0645(9) 0.0656(10) 0.0043(8) -0.0197(8) -0.0370(9)
O1 0.0429(6) 0.0767(7) 0.0293(5) 0.0103(4) 0.0090(4) 0.0109(5)
O2 0.0314(5) 0.0562(5) 0.0334(5) 0.0050(4) -0.0063(4) -0.0119(4)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 126.58(12)
O1 C1 C8 125.24(11)
N1 C1 C8 108.18(10)
C3 C2 C7 121.83(12)
C3 C2 N1 128.88(11)
C7 C2 N1 109.28(10)
C2 C3 C4 116.88(13)
C2 C3 H3 121.6
C4 C3 H3 121.6
C5 C4 C3 121.93(12)
C5 C4 H4 119.0
C3 C4 H4 119.0
C4 C5 C6 120.57(14)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 118.17(13)
C7 C6 H6 120.9
C5 C6 H6 120.9
C6 C7 C2 120.62(11)
C6 C7 C8 130.46(11)
C2 C7 C8 108.92(10)
O2 C8 C7 110.48(9)
O2 C8 C9 109.77(9)
C7 C8 C9 113.37(10)
O2 C8 C1 111.23(9)
C7 C8 C1 101.78(9)
C9 C8 C1 110.01(10)
C10 C9 C8 112.92(11)
C10 C9 H9A 109.0
C8 C9 H9A 109.0
C10 C9 H9B 109.0
C8 C9 H9B 109.0
H9A C9 H9B 107.8
N2 C10 C9 178.29(18)
C1 N1 C2 111.82(10)
C1 N1 H1 123.8(11)
C2 N1 H1 124.1(11)
C8 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2153(14)
C1 N1 1.3408(16)
C1 C8 1.5441(16)
C2 C3 1.3769(16)
C2 C7 1.3848(17)
C2 N1 1.4084(17)
C3 C4 1.386(2)
C3 H3 0.9300
C4 C5 1.370(2)
C4 H4 0.9300
C5 C6 1.390(2)
C5 H5 0.9300
C6 C7 1.3720(17)
C6 H6 0.9300
C7 C8 1.5036(16)
C8 O2 1.4052(14)
C8 C9 1.5346(16)
C9 C10 1.456(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 N2 1.130(2)
N1 H1 0.860(13)
O2 H2 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 2.03 2.8126(13) 160.3 3_456
N1 H1 O2 0.860(13) 2.379(16) 2.9445(14) 123.7(14) 1_655
N1 H1 N2 0.860(13) 2.439(15) 3.1334(18) 138.3(14) 4_746
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
C7 C2 C3 C4 0.56(17)
N1 C2 C3 C4 -178.29(12)
C2 C3 C4 C5 -0.1(2)
C3 C4 C5 C6 -0.7(2)
C4 C5 C6 C7 1.0(2)
C5 C6 C7 C2 -0.49(19)
C5 C6 C7 C8 179.96(12)
C3 C2 C7 C6 -0.28(17)
N1 C2 C7 C6 178.78(11)
C3 C2 C7 C8 179.36(10)
N1 C2 C7 C8 -1.58(12)
C6 C7 C8 O2 -60.71(16)
C2 C7 C8 O2 119.70(10)
C6 C7 C8 C9 62.98(17)
C2 C7 C8 C9 -116.61(11)
C6 C7 C8 C1 -178.92(12)
C2 C7 C8 C1 1.48(11)
O1 C1 C8 O2 61.10(16)
N1 C1 C8 O2 -118.56(10)
O1 C1 C8 C7 178.77(13)
N1 C1 C8 C7 -0.89(12)
O1 C1 C8 C9 -60.76(16)
N1 C1 C8 C9 119.58(11)
O2 C8 C9 C10 -177.55(11)
C7 C8 C9 C10 58.38(15)
C1 C8 C9 C10 -54.83(14)
C8 C9 C10 N2 53(6)
O1 C1 N1 C2 -179.66(13)
C8 C1 N1 C2 -0.01(13)
C3 C2 N1 C1 179.98(12)
C7 C2 N1 C1 1.01(14)
