Synthetic access to non-canonical strigolactones - Syntheses of carlactonic acid and methyl carlactonoate.
Dieckmann, Michael Christian; Dakas, Pierre-Yves; De Mesmaeker, Alain; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02465

data_4033264
_publ_section_title
;
 Synthetic access to non-canonical strigolactones - Syntheses of
 carlactonic acid and methyl carlactonoate.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02465
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H7 I1 O4'
_chemical_formula_sum            'C8 H7 I O4'
_chemical_formula_weight         294.05
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2017-09-08 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   33.7382(8)
_cell_length_b                   26.6877(8)
_cell_length_c                   4.17233(11)
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    117
_cell_measurement_theta_max      60.8450
_cell_measurement_theta_min      4.1880
_cell_volume                     3756.74(17)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      117
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4172
_diffrn_reflns_theta_full        58.8557
_diffrn_reflns_theta_max         61.261
_diffrn_reflns_theta_min         4.224
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    26.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.53
_refine_ls_abs_structure_details 'Flack (1983), 532 Friedel-pairs'
_refine_ls_abs_structure_Flack   1.00(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9423
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1360
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.0009780
_refine_ls_shift/su_mean         0.0000397
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.474E+04 0.125E+05 0.435E+04 0.374E+04 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1608
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1608
_reflns_limit_h_max              38
_reflns_limit_h_min              0
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              4
_reflns_limit_l_min              -4
_reflns_number_gt                1336
_reflns_number_total             1366
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.99
_oxford_diffrn_Wilson_scale      0.68
_oxford_refine_ls_r_factor_ref   0.0685
_oxford_refine_ls_scale          1.219(13)
_oxford_reflns_number_all        1360
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo7b02465_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        3756.74(10)
_cod_original_sg_symbol_H-M      'F d d 2 '
_cod_original_formula_sum        'C8 H7 I1 O4'
_cod_database_code               4033264