Structure-Based Organic Synthesis of a Tricyclic N-Malayamycin Analogue
Stephen Hanessian; Dougal J. Ritson; Journal of Organic Chemistry 71 (2006) 9807–9817; doi:10.1021/jo061904r

data_4022194
_publ_section_title
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 Structure-Based Organic Synthesis of a Tricyclic N-Malayamycin Analogue
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9807
_journal_page_last               9817
_journal_paper_doi               10.1021/jo061904r
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_sum            'C13 H20 N4 O8'
_chemical_formula_weight         360.33
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.85(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3388(14)
_cell_length_b                   5.1216(14)
_cell_length_c                   15.230(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      20.00
_cell_volume                     803.6(3)
_computing_cell_refinement       'CAD4 Program (Nonius 1989)'
_computing_data_collection       'CAD4 Program (Nonius 1989)'
_computing_data_reduction        'Local Program'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Enraf-Nonius-CAD4
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15131
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        -0.23
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  0.9300
_exptl_absorpt_correction_T_min  0.5800
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'No absorption correction applied'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1127P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                2311
_reflns_number_total             3023
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo061904rsi20060922_043407.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (42
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (64
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (96 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022194