Iodine-Catalyzed Nazarov Cyclizations.
Koenig, Jonas J.; Arndt, Thiemo; Gildemeister, Nora; Neudörfl, Jörg-M; Breugst, Martin; The Journal of organic chemistry 84 (2019) 7587–7605; doi:10.1021/acs.joc.9b01083

data_4037582
_publ_section_title
;
 Iodine-Catalyzed Nazarov Cyclizations.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7587
_journal_page_last               7605
_journal_paper_doi               10.1021/acs.joc.9b01083
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H24 O7'
_chemical_formula_sum            'C20 H24 O7'
_chemical_formula_weight         376.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8437(2)
_cell_length_b                   11.9146(3)
_cell_length_c                   20.1565(6)
_cell_measurement_reflns_used    9606
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.06
_cell_measurement_theta_min      4.39
_cell_volume                     1883.72(9)
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_collection       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14487
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.054
_diffrn_reflns_theta_min         4.310
_diffrn_source                   'micro focus'
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.39(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0321P)^2^+0.4646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3497
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01083_si_005.cif
_cod_data_source_block           4e
_cod_database_code               4037582
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.921
_shelx_res_checksum              18158
_shelx_hkl_checksum              73798