Synthesis of the tricyclic core of manzamine A.
Pathak, Ravindra B.; Dobson, Benjamin C.; Ghosh, Nandita; Ageel, Khalid A.; Alshawish, Madeha R.; Saruengkhanphasit, Rungroj; Coldham, Iain; Organic & biomolecular chemistry 13 (2015) 3331–3340; doi:10.1039/c4ob02582b

data_7154309
_publ_section_title
;
 Synthesis of the tricyclic core of manzamine A.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3331
_journal_page_last               3340
_journal_paper_doi               10.1039/c4ob02582b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C25 H28 Br N O6 S'
_chemical_formula_weight         550.45
_chemical_melting_point          426.5(5)
_chemical_name_systematic
'4-Bromobenzoic acid 2-Ethoxycarbonyl-2-[3-methylene-1-(toluene-4-sulfonyl)-piperidin-4-yl]-ethyl ester '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-09-19 deposited with the CCDC.
2015-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.010(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.1472(17)
_cell_length_b                   5.7177(5)
_cell_length_c                   22.9157(19)
_cell_measurement_reflns_used    3690
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.99
_cell_volume                     2484.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24369
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  0.9322
_exptl_absorpt_correction_T_min  0.5829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0012(2)
_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   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0376P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                3175
_reflns_number_total             5697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02582b2.cif
_cod_data_source_block           ohj129_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '426-427' was changed to '426.5(5)' -
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7154309.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7154309