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_7106823
_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             10-11-04
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 96.0302(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0669(2)
_cell_length_b                   15.7455(4)
_cell_length_c                   12.0613(3)
_cell_measurement_reflns_used    3777
_cell_measurement_temperature    123
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1712.38(7)
_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      123
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15585
_diffrn_reflns_theta_full        26.646
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         5.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.44
_refine_ls_extinction_coef       770(60)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9620
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.0226392
_refine_ls_shift/su_mean         0.0005859
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.19P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0978
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0978
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2716
_reflns_number_total             4032
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.97
_oxford_diffrn_Wilson_scale      5.65
_oxford_refine_ls_r_factor_ref   0.0794
_oxford_refine_ls_scale          0.4375(9)
_oxford_reflns_number_all        4032
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 009DJD10
_cod_data_source_file            c1cc13665h.txt
_cod_data_source_block           12
_cod_depositor_comments
;
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 21 '
_cod_database_code               7106823
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S) H ( 52,X'S)
RIDE C ( 9,X'S) H ( 93,X'S) H ( 92,X'S) H ( 91,X'S)
RIDE C ( 11,X'S) H ( 111,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S)
RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S)
RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) H ( 243,X'S)
RIDE C ( 25,X'S) H ( 253,X'S) H ( 252,X'S) H ( 251,X'S)
RIDE C ( 29,X'S) H ( 291,X'S)
RIDE C ( 30,X'S) H ( 301,X'S) H ( 302,X'S)
RIDE C ( 35,X'S) H ( 353,X'S) H ( 352,X'S) H ( 351,X'S)
RIDE C ( 36,X'S) H ( 361,X'S)
RIDE C ( 42,X'S) H ( 421,X'S) H ( 422,X'S)
RIDE C ( 46,X'S) H ( 461,X'S) H ( 462,X'S)
RIDE C ( 49,X'S) H ( 491,X'S) H ( 492,X'S) H ( 493,X'S)
RIDE C ( 50,X'S) H ( 503,X'S) H ( 502,X'S) H ( 501,X'S)
RIDE C ( 380,X'S) H (3801,X'S)
RIDE C ( 381,X'S) H (3811,X'S)
RIDE C ( 391,X'S) H (3911,X'S)
RIDE C ( 400,X'S) H (4001,X'S)
RIDE C ( 410,X'S) H (4101,X'S)
RIDE C ( 411,X'S) H (4111,X'S)
RIDE C(370,X'S,U'S) C(371,X'S,U'S)
EQUIVALENCE PART(1001,OCC) PART(1002,OCC)
WEIGHT -1 PART(1001,OCC)
END
;
_iucr_refine_instruction_details_restraints
;
SAME C(370) C(380) O(390) C(400) C(410) AND C(371) C(411) O(401) C(391) C(381)
DELU 0.01 C(370) C(380) O(390) C(400) C(410) AND
CONT C(371) C(411) O(401) C(391) C(381)
SIMU 0.01 C(370) C(380) O(390) C(400) C(410) AND
CONT C(371) C(411) O(401) C(391) C(381)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;