TiCl4/DMAP mediated Z-selective knovenagel condensation of isatins with nitroacetates and related compounds
Zhu, Luyi; Yan, Peipei; Zhang, Lvye; Chen, Zhangtao; Zeng, Xiaofei; Zhong, Guofu; RSC Advances 7 (2017) 51352–; doi:10.1039/C7RA09951G

data_7229498
_publ_section_title
;
 TiCl4/DMAP mediated Z-selective knovenagel condensation of isatins with
 nitroacetates and related compounds
;
_journal_issue                   81
_journal_name_full               'RSC Advances'
_journal_page_first              51352
_journal_paper_doi               10.1039/C7RA09951G
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C13 H12 N2 O5'
_chemical_formula_sum            'C13 H12 N2 O5'
_chemical_formula_weight         276.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2014-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-08-28 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                70.661(10)
_cell_angle_beta                 81.940(8)
_cell_angle_gamma                64.185(11)
_cell_formula_units_Z            2
_cell_length_a                   8.4937(9)
_cell_length_b                   8.6840(10)
_cell_length_c                   10.0187(9)
_cell_measurement_reflns_used    1981
_cell_measurement_temperature    294.30(10)
_cell_measurement_theta_max      30.0160
_cell_measurement_theta_min      3.9460
_cell_volume                     627.68(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.30(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0530309000
_diffrn_orient_matrix_UB_12      0.0641597000
_diffrn_orient_matrix_UB_13      -0.0592569000
_diffrn_orient_matrix_UB_21      0.0677934000
_diffrn_orient_matrix_UB_22      -0.0351655000
_diffrn_orient_matrix_UB_23      -0.0460255000
_diffrn_orient_matrix_UB_31      -0.0346072000
_diffrn_orient_matrix_UB_32      -0.0609260000
_diffrn_orient_matrix_UB_33      -0.0003052000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5506
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.19
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0447
_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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                2496
_reflns_number_total             3203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra09951g2.cif
_cod_data_source_block           g140421b
_cod_original_cell_volume        627.68(11)
_cod_database_code               7229498
_chemical_oxdiff_formula         C100H100N22O2
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C13(H13a,H13b,H13c)
;