#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:16 +0300 (Mon, 04 May 2020) $
#$Revision: 251474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038238.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_4038238
loop_
_publ_author_name
'Pradhan, Sourav'
'Roy, Subhasish'
'Banerjee, Sonbidya'
'De, Pinaki Bhusan'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Oxidative C-H/N-H Annulation of Aromatic Amides with Dialkyl Malonates:
 Access to Isoindolinones and Dihydrobenzoindoles.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5741
_journal_page_last               5749
_journal_paper_doi               10.1021/acs.joc.0c00466
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C25 H24 N2 O5'
_chemical_formula_sum            'C25 H24 N2 O5'
_chemical_formula_weight         432.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                92.062(3)
_cell_angle_beta                 112.040(3)
_cell_angle_gamma                110.021(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2898(8)
_cell_length_b                   11.6784(9)
_cell_length_c                   12.1295(10)
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.95
_cell_measurement_theta_min      2.38
_cell_volume                     1125.43(17)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(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  0.0742
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46466
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.844
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0601P)²+0.4889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2803
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00466_si_001.cif
_cod_data_source_block           PS-4H_0m_a
_cod_depositor_comments          'Adding full bibliography for 4038238.cif.'
_cod_database_code               4038238
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.70541(18) 0.82933(14) 0.83782(13) 0.0456(4) Uani 1 1 d . . . . .
O002 O 0.54124(19) 0.69445(16) 0.61445(13) 0.0540(4) Uani 1 1 d . . . . .
O003 O 0.9624(2) 0.83063(14) 0.94669(14) 0.0560(4) Uani 1 1 d . . . . .
O004 O 0.7276(2) 0.70162(17) 0.53724(15) 0.0626(5) Uani 1 1 d . . . . .
N005 N 0.9701(2) 0.70763(17) 0.75559(16) 0.0465(5) Uani 1 1 d . . . . .
O006 O 1.2099(2) 0.78511(19) 0.7308(2) 0.0869(7) Uani 1 1 d . . . . .
C007 C 0.8365(3) 0.79997(18) 0.85508(19) 0.0403(5) Uani 1 1 d . . . . .
N008 N 0.9427(3) 0.94317(18) 0.7187(2) 0.0635(6) Uani 1 1 d . . . . .
C1 C 0.7336(3) 0.57556(19) 0.78234(18) 0.0434(5) Uani 1 1 d . . . . .
C00A C 0.6898(3) 0.70354(19) 0.6209(2) 0.0425(5) Uani 1 1 d . . . . .
C00B C 0.8053(3) 0.70269(19) 0.75050(19) 0.0414(5) Uani 1 1 d . . . . .
C00C C 1.0627(3) 0.9182(2) 0.7014(2) 0.0486(6) Uani 1 1 d . . . . .
C00D C 0.8543(3) 0.5247(2) 0.80819(19) 0.0480(6) Uani 1 1 d . . . . .
C00E C 0.9961(3) 0.5989(2) 0.7927(2) 0.0509(6) Uani 1 1 d . . . . .
C00F C 0.7145(3) 0.9066(2) 0.9406(2) 0.0525(6) Uani 1 1 d . . . . .
H00F H 0.832407 0.955633 0.994368 0.063 Uiso 1 1 calc R U . . .
C00G C 1.0833(3) 0.7986(2) 0.7289(2) 0.0537(6) Uani 1 1 d . . . . .
C00H C 0.8330(4) 0.4088(2) 0.8452(2) 0.0631(7) Uani 1 1 d . . . . .
C00I C 0.4107(3) 0.6866(3) 0.4954(2) 0.0626(7) Uani 1 1 d . . . . .
H00I H 0.424923 0.643342 0.431873 0.075 Uiso 1 1 calc R U . . .
C00J C 0.5852(3) 0.5143(2) 0.7919(2) 0.0596(7) Uani 1 1 d . . . . .
H00J H 0.503435 0.547784 0.775160 0.072 Uiso 1 1 calc R U . . .
C00K C 1.1718(3) 0.9982(3) 0.6611(2) 0.0625(7) Uani 1 1 d . . . . .
H00K H 1.254133 0.977800 0.649526 0.075 Uiso 1 1 calc R U . . .
C00L C 1.1269(4) 0.5607(3) 0.8131(2) 0.0669(7) Uani 1 1 d . . . . .
H00L H 1.222399 0.607500 0.802183 0.080 Uiso 1 1 calc R U . . .
C00M C 1.1566(4) 1.1081(3) 0.6385(2) 0.0713(8) Uani 1 1 d . . . . .
H00M H 1.228907 1.163403 0.611074 0.086 Uiso 1 1 calc R U . . .
C00N C 1.0357(4) 1.1370(2) 0.6560(3) 0.0733(8) Uani 1 1 d . . . . .
H00N H 1.023582 1.211427 0.640722 0.088 Uiso 1 1 calc R U . . .
C00O C 0.5616(4) 0.3985(3) 0.8280(3) 0.0750(8) Uani 1 1 d . . . . .
H00O H 0.461312 0.354834 0.834412 0.090 Uiso 1 1 calc R U . . .
C00P C 0.9680(5) 0.3705(3) 0.8674(3) 0.0814(10) Uani 1 1 d . . . . .
H00P H 0.962495 0.295265 0.892149 0.098 Uiso 1 1 calc R U . . .
C00Q C 0.6798(5) 0.3480(2) 0.8540(3) 0.0761(9) Uani 1 1 d . . . . .
H00Q H 0.658648 0.271473 0.878161 0.091 Uiso 1 1 calc R U . . .
C00R C 0.6316(4) 0.8212(3) 1.0076(3) 0.0798(9) Uani 1 1 d . . . . .
H00A H 0.515847 0.774206 0.954808 0.120 Uiso 1 1 calc R U . . .
H00B H 0.637900 0.869203 1.076405 0.120 Uiso 1 1 calc R U . . .
H00C H 0.688040 0.765683 1.034391 0.120 Uiso 1 1 calc R U . . .
C00S C 1.1069(5) 0.4441(3) 0.8524(3) 0.0827(10) Uani 1 1 d . . . . .
H00S H 1.194426 0.416673 0.868852 0.099 Uiso 1 1 calc R U . . .
C00T C 0.6276(4) 0.9914(3) 0.8874(3) 0.0802(9) Uani 1 1 d . . . . .
H00D H 0.681786 1.039474 0.841336 0.120 Uiso 1 1 calc R U . . .
H00E H 0.633465 1.045967 0.951462 0.120 Uiso 1 1 calc R U . . .
H00G H 0.511942 0.942937 0.835474 0.120 Uiso 1 1 calc R U . . .
C00U C 0.9315(4) 1.0522(3) 0.6972(3) 0.0793(9) Uani 1 1 d . . . . .
H00U H 0.849722 1.071744 0.710589 0.095 Uiso 1 1 calc R U . . .
C00V C 0.2472(4) 0.6116(3) 0.5004(3) 0.0903(11) Uani 1 1 d . . . . .
H00H H 0.247017 0.532108 0.518272 0.135 Uiso 1 1 calc R U . . .
H00R H 0.156381 0.600145 0.423573 0.135 Uiso 1 1 calc R U . . .
H00T H 0.233394 0.654264 0.562434 0.135 Uiso 1 1 calc R U . . .
C00W C 0.4300(5) 0.8165(3) 0.4758(3) 0.1060(12) Uani 1 1 d . . . . .
H00V H 0.414085 0.858115 0.537367 0.159 Uiso 1 1 calc R U . . .
H00W H 0.347616 0.813446 0.397600 0.159 Uiso 1 1 calc R U . . .
H00$ H 0.540674 0.860744 0.480051 0.159 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'
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
C007 O001 C00F 116.92(17) . . ?
C00A O002 C00I 118.29(18) . . ?
C00G N005 C00E 122.7(2) . . ?
C00G N005 C00B 127.44(18) . . ?
C00E N005 C00B 109.84(18) . . ?
O003 C007 O001 126.1(2) . . ?
O003 C007 C00B 120.0(2) . . ?
O001 C007 C00B 113.31(18) . . ?
C00C N008 C00U 117.5(2) . . ?
C00J C1 C00D 120.6(2) . . ?
C00J C1 C00B 132.0(2) . . ?
C00D C1 C00B 107.32(19) . . ?
O004 C00A O002 125.8(2) . . ?
O004 C00A C00B 123.2(2) . . ?
O002 C00A C00B 110.69(18) . . ?
N005 C00B C1 102.49(16) . . ?
N005 C00B C00A 110.22(17) . . ?
C1 C00B C00A 109.09(17) . . ?
N005 C00B C007 109.16(17) . . ?
C1 C00B C007 106.11(16) . . ?
C00A C00B C007 118.51(17) . . ?
N008 C00C C00K 122.7(2) . . ?
N008 C00C C00G 119.1(2) . . ?
C00K C00C C00G 118.2(2) . . ?
C1 C00D C00E 112.9(2) . . ?
C1 C00D C00H 122.9(2) . . ?
C00E C00D C00H 124.2(2) . . ?
C00L C00E C00D 120.1(2) . . ?
C00L C00E N005 132.5(3) . . ?
C00D C00E N005 107.39(19) . . ?
O001 C00F C00R 107.63(19) . . ?
O001 C00F C00T 106.2(2) . . ?
C00R C00F C00T 113.4(2) . . ?
O001 C00F H00F 109.8 . . ?
C00R C00F H00F 109.8 . . ?
C00T C00F H00F 109.8 . . ?
O006 C00G N005 119.3(2) . . ?
O006 C00G C00C 118.4(2) . . ?
N005 C00G C00C 122.3(2) . . ?
C00Q C00H C00P 129.2(3) . . ?
C00Q C00H C00D 115.2(3) . . ?
C00P C00H C00D 115.5(3) . . ?
O002 C00I C00V 105.4(2) . . ?
O002 C00I C00W 108.1(2) . . ?
C00V C00I C00W 114.2(3) . . ?
O002 C00I H00I 109.7 . . ?
C00V C00I H00I 109.7 . . ?
C00W C00I H00I 109.7 . . ?
C1 C00J C00O 117.2(3) . . ?
C1 C00J H00J 121.4 . . ?
C00O C00J H00J 121.4 . . ?
C00M C00K C00C 118.6(3) . . ?
C00M C00K H00K 120.7 . . ?
C00C C00K H00K 120.7 . . ?
C00E C00L C00S 115.8(3) . . ?
C00E C00L H00L 122.1 . . ?
C00S C00L H00L 122.1 . . ?
C00N C00M C00K 120.1(3) . . ?
C00N C00M H00M 119.9 . . ?
C00K C00M H00M 119.9 . . ?
C00M C00N C00U 117.9(3) . . ?
C00M C00N H00N 121.1 . . ?
C00U C00N H00N 121.1 . . ?
C00Q C00O C00J 122.5(3) . . ?
C00Q C00O H00O 118.8 . . ?
C00J C00O H00O 118.8 . . ?
C00S C00P C00H 119.9(3) . . ?
C00S C00P H00P 120.1 . . ?
C00H C00P H00P 120.1 . . ?
C00O C00Q C00H 121.5(2) . . ?
C00O C00Q H00Q 119.3 . . ?
C00H C00Q H00Q 119.3 . . ?
C00F C00R H00A 109.5 . . ?
C00F C00R H00B 109.5 . . ?
H00A C00R H00B 109.5 . . ?
C00F C00R H00C 109.5 . . ?
H00A C00R H00C 109.5 . . ?
H00B C00R H00C 109.5 . . ?
C00P C00S C00L 124.5(3) . . ?
C00P C00S H00S 117.8 . . ?
C00L C00S H00S 117.8 . . ?
C00F C00T H00D 109.5 . . ?
C00F C00T H00E 109.5 . . ?
H00D C00T H00E 109.5 . . ?
C00F C00T H00G 109.5 . . ?
H00D C00T H00G 109.5 . . ?
H00E C00T H00G 109.5 . . ?
N008 C00U C00N 123.2(3) . . ?
N008 C00U H00U 118.4 . . ?
C00N C00U H00U 118.4 . . ?
C00I C00V H00H 109.5 . . ?
C00I C00V H00R 109.5 . . ?
H00H C00V H00R 109.5 . . ?
C00I C00V H00T 109.5 . . ?
H00H C00V H00T 109.5 . . ?
H00R C00V H00T 109.5 . . ?
C00I C00W H00V 109.5 . . ?
C00I C00W H00W 109.5 . . ?
H00V C00W H00W 109.5 . . ?
C00I C00W H00$ 109.5 . . ?
H00V C00W H00$ 109.5 . . ?
H00W C00W H00$ 109.5 . . ?
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
O001 C007 1.321(2) . ?
O001 C00F 1.470(3) . ?
O002 C00A 1.319(3) . ?
O002 C00I 1.471(3) . ?
O003 C007 1.200(2) . ?
O004 C00A 1.194(3) . ?
N005 C00G 1.362(3) . ?
N005 C00E 1.429(3) . ?
N005 C00B 1.490(3) . ?
O006 C00G 1.231(3) . ?
C007 C00B 1.542(3) . ?
N008 C00C 1.329(3) . ?
N008 C00U 1.340(3) . ?
C1 C00J 1.370(3) . ?
C1 C00D 1.384(3) . ?
C1 C00B 1.534(3) . ?
C00A C00B 1.538(3) . ?
C00C C00K 1.377(3) . ?
C00C C00G 1.505(3) . ?
C00D C00E 1.392(3) . ?
C00D C00H 1.414(3) . ?
C00E C00L 1.375(3) . ?
C00F C00R 1.500(4) . ?
C00F C00T 1.500(4) . ?
C00F H00F 0.9800 . ?
C00H C00Q 1.403(4) . ?
C00H C00P 1.408(4) . ?
C00I C00V 1.496(4) . ?
C00I C00W 1.503(4) . ?
C00I H00I 0.9800 . ?
C00J C00O 1.407(4) . ?
C00J H00J 0.9300 . ?
C00K C00M 1.366(4) . ?
C00K H00K 0.9300 . ?
C00L C00S 1.434(4) . ?
C00L H00L 0.9300 . ?
C00M C00N 1.361(4) . ?
C00M H00M 0.9300 . ?
C00N C00U 1.382(4) . ?
C00N H00N 0.9300 . ?
C00O C00Q 1.361(4) . ?
C00O H00O 0.9300 . ?
C00P C00S 1.365(5) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00A 0.9600 . ?
C00R H00B 0.9600 . ?
C00R H00C 0.9600 . ?
C00S H00S 0.9300 . ?
C00T H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00T H00G 0.9600 . ?
C00U H00U 0.9300 . ?
C00V H00H 0.9600 . ?
C00V H00R 0.9600 . ?
C00V H00T 0.9600 . ?
C00W H00V 0.9600 . ?
C00W H00W 0.9600 . ?
C00W H00$ 0.9600 . ?
