C-3 alkyl/arylalkyl-2,3-dideoxy hex-2-enopyranosides as antitubercular agents: synthesis, biological evaluation, and QSAR study.
Saquib, Mohammad; Gupta, Manish K.; Sagar, Ram; Prabhakar, Yenamandra S.; Shaw, Arun K.; Kumar, Rishi; Maulik, Prakas R.; Gaikwad, Anil N.; Sinha, Sudhir; Srivastava, Anil K.; Chaturvedi, Vinita; Srivastava, Ranjana; Srivastava, Brahm S.; Journal of medicinal chemistry 50 (2007) 2942–2950; doi:10.1021/jm070110h

data_1505027
_publ_contact_author             'Dr. Yenamandra S. Prabhakar'
_publ_section_title
;
 C-3 alkyl/arylalkyl-2,3-dideoxy hex-2-enopyranosides as antitubercular
 agents: synthesis, biological evaluation, and QSAR study.
;
_journal_issue                   13
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              2942
_journal_page_last               2950
_journal_paper_doi               10.1021/jm070110h
_journal_volume                  50
_journal_year                    2007
_chemical_formula_sum            'C22 H29 N O6'
_chemical_formula_weight         403.46
_chemical_melting_point          401
_chemical_name_systematic
; 
 4-[(2-tert-butoxymethyl-3-hydroxy-6-isopropoxy-3,6-dihydro-2H-
pyran-4-yl)hydroxy-methyl]-benzonitrile 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 115.40(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.443(2)
_cell_length_b                   5.797(1)
_cell_length_c                   15.243(2)
_cell_measurement_reflns_used    81
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.033
_cell_measurement_theta_min      5.917
_cell_volume                     1152.9(3)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4 diffractometer'
_diffrn_measurement_method       \q-2\q
_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  0.1133
_diffrn_reflns_av_sigmaI/netI    0.0750
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2992
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        nil
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_colour            reddish
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_preparation
;
 By slow evaporation from acetone and hexane (3:1) solution at RT.   
;
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0875
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1598P)^2^+0.3960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2265
_refine_ls_wR_factor_ref         0.2551
_reflns_number_gt                1804
_reflns_number_total             2664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm070110hsi20070430_055541.cif
_cod_data_source_block           compd4dr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constrained' was replaced with
the value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1505027