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_4033252
_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         'C26 H22 F6 N2 O8 S'
_chemical_formula_sum            'C26 H22 F6 N2 O8 S'
_chemical_formula_weight         636.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                90
_cell_angle_beta                 96.80(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.893(2)
_cell_length_b                   19.835(4)
_cell_length_c                   12.801(3)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.75
_cell_measurement_theta_min      4.15
_cell_volume                     2746.4(10)
_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  'olex2.refine (Bourhis et al., 2015)'
_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 0.9882
_diffrn_measured_fraction_theta_max 0.9882
_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     1.54178
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25858
_diffrn_reflns_theta_full        66.3754
_diffrn_reflns_theta_max         66.38
_diffrn_reflns_theta_min         4.13
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0941 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8375. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5393
_exptl_crystal_description       prism
_exptl_crystal_F_000             1310.9303
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.2791
_refine_diff_density_min         -0.4724
_refine_diff_density_rms         0.0690
_refine_ls_d_res_high            0.8415
_refine_ls_d_res_low             10.7020
_refine_ls_goodness_of_fit_ref   1.0521
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0521
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0394P)^2^+1.7289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -12
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -8
_reflns_number_gt                4167
_reflns_number_total             4761
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo7b02624_si_003.cif
_cod_data_source_block           17mg03_0m
_cod_depositor_comments
'Adding full bibliography for 4033251--4033252.cif.'
_cod_original_cell_volume        2746.3(10)
_cod_database_code               4033252
_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 Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C20(H20a,H20b), C23(H23a,H23b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17),
 C25(H25)
2.d X=CH2 refined with riding coordinates:
 C26(H26a,H26b)
2.e Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_olex2_submission_special_instructions 'No special instructions were received'