Asymmetric synthesis of (-)-martinellic Acid.
Davies, Stephen G.; Fletcher, Ai M.; Lee, James A.; Lorkin, Thomas J. A.; Roberts, Paul M.; Thomson, James E.; Organic letters 15 (2013) 2050–2053; doi:10.1021/ol4007508

data_1511960
_publ_section_title
;
 Asymmetric synthesis of (-)-martinellic Acid.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2050
_journal_page_last               2053
_journal_paper_doi               10.1021/ol4007508
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H27 Br1 N2 O5'
_chemical_formula_sum            'C25 H27 Br N2 O5'
_chemical_formula_weight         515.40
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6810(2)
_cell_length_b                   12.7183(2)
_cell_length_c                   19.2223(4)
_cell_measurement_reflns_used    2951
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2366.76(8)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.058
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5258
_diffrn_reflns_theta_full        26.648
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         5.250
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.69
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9336
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.0008457
_refine_ls_shift/su_mean         0.0000303
_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: 
 26.1 41.3 25.7 11.6 2.93 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0763
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0763
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                4476
_reflns_number_total             3028
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.86
_oxford_diffrn_Wilson_scale      8.05
_oxford_refine_ls_r_factor_ref   0.0468
_oxford_refine_ls_scale          0.3563(3)
_oxford_reflns_number_all        5258
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol4007508_si_001.cif
_cod_data_source_block           11
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_formula_sum        'C25 H27 Br1 N2 O5'
_cod_database_code               1511960