Synthesis and biological evaluation of palmyrolide A macrocycles as sodium channel blockers towards neuroprotection.
Philkhana, Satish Chandra; Mehrotra, Suneet; Murray, Thomas F.; Reddy, D. Srinivasa; Organic & biomolecular chemistry 14 (2016) 8457–8473; doi:10.1039/c6ob01372d

data_7155238
_publ_section_title
;
 Synthesis and biological evaluation of palmyrolide A macrocycles as
 sodium channel blockers towards neuroprotection.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8457
_journal_page_last               8473
_journal_paper_doi               10.1039/c6ob01372d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H33 N O3'
_chemical_formula_sum            'C19 H33 N O3'
_chemical_formula_weight         323.46
_chemical_name_systematic
(14R,16R,E)-16-(tert-butyl)-14-methyl-1-oxa-8-azacyclohexadec-10-ene-2,9-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-19 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.393(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.998(3)
_cell_length_b                   8.740(2)
_cell_length_c                   18.751(5)
_cell_measurement_reflns_used    1600
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.64
_cell_measurement_theta_min      2.24
_cell_volume                     1904.6(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_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  0.1555
_diffrn_reflns_av_unetI/netI     0.1778
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36143
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         1.121
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2006)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       NEEDLES
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate-hexane'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.3(10)
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         9449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0644P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1757
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5015
_reflns_number_total             9449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01372d2.cif
_cod_data_source_block           Compound_18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'SYN' changed to 'syn'
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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' 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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155237--7155239.cif.
;
_cod_database_code               7155238
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              97144