Total synthesis of (–)-nakadomarin A
Andrew F. Kyle; Pavol Jakubec; Dane M. Cockfield; Ed Cleator; John Skidmore; Darren J. Dixon; Chem.Commun. 47 (2011) 10037–10039; doi:10.1039/c1cc13665h

data_7106822
_publ_section_title
;
 Total synthesis of (--)-nakadomarin A
;
_journal_name_full               Chem.Commun.
_journal_page_first              10037
_journal_page_last               10039
_journal_paper_doi               10.1039/c1cc13665h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H20 N2 O7'
_chemical_formula_sum            'C16 H20 N2 O7'
_chemical_formula_weight         352.34
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-10-15
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 109.6310(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5453(3)
_cell_length_b                   6.9928(2)
_cell_length_c                   13.4491(4)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     845.53(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      150
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5923
_diffrn_reflns_theta_full        26.280
_diffrn_reflns_theta_max         27.093
_diffrn_reflns_theta_min         5.173
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.29
_refine_ls_extinction_coef       180(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9348
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.0001134
_refine_ls_shift/su_mean         0.0000556
_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:
10.5 14.7 6.96 1.84
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0926
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0926
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1676
_reflns_number_total             1988
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.85
_oxford_diffrn_Wilson_scale      1.64
_oxford_refine_ls_r_factor_ref   0.0500
_oxford_refine_ls_scale          0.794(4)
_oxford_reflns_number_all        1988
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 008DJD10
_cod_data_source_file            c1cc13665h.txt
_cod_data_source_block           11
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7106822