Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels-Alder reaction of 3-vinylindoles and methyleneindolinones
Haifeng Zheng; Peng He; Yangbin Liu; Yulong Zhang; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 50 (2014) 8794–; doi:10.1039/C4cc03135K

data_7115364
_publ_section_title
;
 Efficient synthesis of carbazolespirooxindole skeletons via asymmetric
 Diels-Alder reaction of 3-vinylindoles and methyleneindolinones
;
_journal_name_full               Chem.Commun.
_journal_page_first              8794
_journal_paper_doi               10.1039/C4cc03135K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C26 H25 Br N2 O5, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C26.5 H26 Br Cl N2 O5'
_chemical_formula_weight         567.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2ac 2ac'
_space_group_name_H-M_alt        'P 21 2 21'
_symmetry_space_group_name_Hall  'P 2ac 2ac'
_symmetry_space_group_name_H-M   'P 21 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   48.787(5)
_cell_length_b                   11.8679(7)
_cell_length_c                   9.6762(6)
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6570
_cell_measurement_theta_min      3.1720
_cell_volume                     5602.5(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.9926
_diffrn_measured_fraction_theta_max 0.7646
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0131440000
_diffrn_orient_matrix_UB_12      0.0244471000
_diffrn_orient_matrix_UB_13      0.0083512000
_diffrn_orient_matrix_UB_21      0.0056047000
_diffrn_orient_matrix_UB_22      -0.0540974000
_diffrn_orient_matrix_UB_23      0.0133472000
_diffrn_orient_matrix_UB_31      0.0025384000
_diffrn_orient_matrix_UB_32      -0.0072853000
_diffrn_orient_matrix_UB_33      -0.0716449000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.1734
_diffrn_reflns_av_unetI/netI     0.1928
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15053
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         10207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1796
_refine_ls_R_factor_gt           0.1069
_refine_ls_shift/su_max          1.629
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1182P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2797
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                4763
_reflns_number_total             10207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc03135k2.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2017-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C26 H25 Br N2 O5), C H2 Cl2'
_cod_original_formula_sum        'C53 H52 Br2 Cl2 N4 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1135.70
_cod_database_code               7115364
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h20n2o3br1
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.691
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C34(H34), C36(H36)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C37(H37A,H37B), C53(H53A,H53B)
2.d Aromatic/amide H refined with riding coordinates:
 N3(H3A), C2(H2), C3(H3), C5(H5), C12(H12), C16(H16), C17(H17), C18(H18),
 C19(H19), C28(H28), C29(H29), C31(H31), C38(H38), C42(H42), C43(H43), C44(H44),
  C45(H45)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C47(H47A,H47B,H47C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,
 H52B,H52C)
;
_shelx_res_checksum              4763
_shelx_hkl_checksum              96632