Directing group assisted ZnI2-catalyzed cyclopropanation of indoles via 2-furylcarbenoids
Chen, Wei; Ji, Dong-Sheng; Luo, Yong-Chun; Wang, Zhu-Yin; Xu, Peng-Fei; Organic Chemistry Frontiers 5 (2018) 1768–; doi:10.1039/C8QO00232K

data_1554290
_publ_section_title
;
 Directing group assisted ZnI2-catalyzed cyclopropanation of indoles via
 2-furylcarbenoids
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1768
_journal_paper_doi               10.1039/C8QO00232K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C26 H21 N3 O2'
_chemical_formula_sum            'C26 H21 N3 O2'
_chemical_formula_weight         407.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-09-15 deposited with the CCDC.
2018-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.473(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6842(9)
_cell_length_b                   19.978(2)
_cell_length_c                   13.7517(18)
_cell_measurement_reflns_used    788
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      21.3640
_cell_measurement_theta_min      3.8350
_cell_volume                     2088.0(4)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8858
_diffrn_measurement_details
;
  1 omega  -15.00   12.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  120.0000 18

  2 omega   -6.00   22.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -60.0000 19

  3 omega   45.00   93.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000  -90.0000 32

  4 omega  -41.00   98.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000   90.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0158405000
_diffrn_orient_matrix_UB_12      0.0171140000
_diffrn_orient_matrix_UB_13      -0.0429941000
_diffrn_orient_matrix_UB_21      0.0200009000
_diffrn_orient_matrix_UB_22      0.0296087000
_diffrn_orient_matrix_UB_23      0.0279224000
_diffrn_orient_matrix_UB_31      0.0897922000
_diffrn_orient_matrix_UB_32      -0.0095996000
_diffrn_orient_matrix_UB_33      0.0093965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.1411
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8159
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70701
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0299P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                1995
_reflns_number_total             4101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00232k2.cif
_cod_data_source_block           chenwei_1209
_cod_database_code               1554290
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_olex2_date_sample_data_collection 2016-12-09
_olex2_submission_special_instructions 'No special instructions were received'