7-Step total synthesis of (+)-EBC-329: Photoisomerisation reveals new seco-casbane family member
Vanden Berg, Timothy J.; Pinkerton, David M.; Williams, Craig M.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01400G

data_7155841
_publ_section_title
;
 7-Step total synthesis of (+)-EBC-329: Photoisomerisation reveals new
 seco-casbane family member
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01400G
_journal_year                    2017
_chemical_formula_moiety         'C4 H5 I O2'
_chemical_formula_sum            'C4 H5 I O2'
_chemical_formula_weight         211.98
_chemical_melting_point          383
_chemical_name_systematic
;
(Z)-3-iodobut-2-enoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-07 deposited with the CCDC.
2017-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.051(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1646(6)
_cell_length_b                   5.8851(4)
_cell_length_c                   14.5753(14)
_cell_measurement_reflns_used    583
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      24.5150
_cell_measurement_theta_min      3.7220
_cell_volume                     613.69(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
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_computing_data_collection
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CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2796
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.280
_diffrn_reflns_theta_min         3.735
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.294
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Deuterochloroform'
_exptl_crystal_size_max          0.4000
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.1000
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    heteroxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1426
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0295P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                972
_reflns_number_total             1426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01400g3.cif
_cod_data_source_block           1327tjv-02-041
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
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_cod_database_code               7155841
_shelx_res_checksum              42477