Visible-Light Induced Direct Synthesis of Polysubstituted Furans from Cyclopropyl Ketones.
Feng, Liyan; Yan, Hang; Yang, Chao; Chen, Dafa; Xia, Wujiong; The Journal of organic chemistry 81 (2016) 7008–7022; doi:10.1021/acs.joc.6b00436

data_4036765
_publ_section_title
;
 Visible-Light Induced Direct Synthesis of Polysubstituted Furans from
 Cyclopropyl Ketones.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7008
_journal_page_last               7022
_journal_paper_doi               10.1021/acs.joc.6b00436
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 Br O2'
_chemical_formula_sum            'C17 H13 Br O2'
_chemical_formula_weight         329.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
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Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
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_cell_length_a                   5.5202(2)
_cell_length_b                   13.6425(5)
_cell_length_c                   20.1076(9)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3000
_cell_measurement_theta_min      3.8070
_cell_volume                     1440.03(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
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;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   14.00   88.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630   57.0000  120.0000 148

  2 omega  -26.00   46.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -37.0000  -30.0000 144

  3 omega    5.00   78.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630   57.0000  -90.0000 146

  4 omega   -2.00   62.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -99.0000 -180.0000 128

  5 omega   25.00   62.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -99.0000   30.0000 74

  6 omega  -50.00   -7.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9630  -57.0000  -30.0000 86

  7 omega  -24.00    1.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6661  -86.0000  -67.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0438055000
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_diffrn_orient_matrix_UB_13      0.0326892000
_diffrn_orient_matrix_UB_21      0.0549779000
_diffrn_orient_matrix_UB_22      0.0443448000
_diffrn_orient_matrix_UB_23      -0.0047158000
_diffrn_orient_matrix_UB_31      -0.1076102000
_diffrn_orient_matrix_UB_32      0.0095865000
_diffrn_orient_matrix_UB_33      -0.0168871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9568
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.988
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description
;
;
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
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_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.320
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5267
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_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0874
_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
'w=1/[\s^2^(Fo^2^)+(0.0861P)^2^+1.3348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             5267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00436_si_002.cif
_cod_data_source_block           xiawj20150122-2
_cod_database_code               4036765
_chemical_oxdiff_formula         'C H O Br'
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.599
_reflns_odcompleteness_completeness 99.90
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C29(H29),
  C30(H30), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              79729
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_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-01-22
_olex2_submission_special_instructions 'No special instructions were received'