Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates.
Gee, Yi Sing; Rivinoja, Daniel J.; Wales, Steven M.; Gardiner, Michael G.; Ryan, John H.; Hyland, Christopher J. T.; The Journal of organic chemistry 82 (2017) 13517–13529; doi:10.1021/acs.joc.7b02624

data_4033251
_publ_section_title
;
 Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with
 2-Vinylcyclopropane-1,1-dicarboxylates.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13517
_journal_page_last               13529
_journal_paper_doi               10.1021/acs.joc.7b02624
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H24 N2 O10 S'
_chemical_formula_sum            'C25 H24 N2 O10 S'
_chemical_formula_weight         544.54
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                95.944(10)
_cell_angle_beta                 100.270(12)
_cell_angle_gamma                107.515(14)
_cell_formula_units_Z            2
_cell_length_a                   8.5498(19)
_cell_length_b                   9.5122(13)
_cell_length_c                   16.619(2)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      4.94
_cell_volume                     1250.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  ShelXT
_computing_structure_solution    ShelXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.9838
_diffrn_measured_fraction_theta_max 0.9838
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41132
_diffrn_reflns_theta_full        72.8100
_diffrn_reflns_theta_max         72.81
_diffrn_reflns_theta_min         2.74
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0817 before and 0.0565 after correction. The Ratio of minimum to maximum transmission is 0.9055. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4463
_exptl_crystal_description       prism
_exptl_crystal_F_000             570.7376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.4185
_refine_diff_density_min         -0.9591
_refine_diff_density_rms         0.0846
_refine_ls_d_res_high            0.8070
_refine_ls_d_res_low             16.1215
_refine_ls_goodness_of_fit_ref   1.0466
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0466
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+2.2242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4340
_reflns_number_total             4913
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo7b02624_si_002.cif
_cod_data_source_block           17mg010b_0m
_cod_depositor_comments
'Adding full bibliography for 4033251--4033252.cif.'
_cod_database_code               4033251
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b)
2.c Me refined with riding coordinates:
 C20(H20a,H20b,H20c), C25(H25a,H25b,H25c)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C13(H13), C14(H14), C10(H10), C16(H16), C17(H17), C22(H22)
2.e X=CH2 refined with riding coordinates:
 C23(H23a,H23b)
2.f Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
2.g Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'