Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction.
Di Maso, Michael J.; Nepomuceno, Gabriella M.; St Peter, Michael A.; Gitre, Haley H.; Martin, Kevin S.; Shaw, Jared T.; Organic letters 18 (2016) 1740–1743; doi:10.1021/acs.orglett.6b00413

data_1555504
_publ_section_title
;
 Synthesis of (+-)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich
 Reaction.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1740
_journal_page_last               1743
_journal_paper_doi               10.1021/acs.orglett.6b00413
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C33 H37 Cl N2 O6'
_chemical_formula_sum            'C33 H37 Cl N2 O6'
_chemical_formula_weight         593.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.269(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.162(5)
_cell_length_b                   15.406(3)
_cell_length_c                   16.174(4)
_cell_measurement_reflns_used    9284
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.65
_cell_volume                     5919(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38353
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.630
_diffrn_reflns_theta_min         1.575
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0420 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9087.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             2216
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.252
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+5.0870P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6423
_reflns_number_total             6868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00413_si_001.cif
_cod_data_source_block           mjd010_0m
_cod_database_code               1555504
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C3(H3), C27(H27), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6), C9(H9), C10(H10), C13(H13), C16(H16), C17(H17),
 C11(H11), C21(H21), C24(H24), C25(H25), C22(H22)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C28(H28A,H28B,H28C), C32(H32A,H32B,
 H32C), C30(H30A,H30B,H30C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              24046
_shelx_hkl_checksum              33588
_olex2_submission_original_sample_id MJD010
_olex2_submission_special_instructions 'No special instructions were received'