Synthesis of HIV-1 capsid protein assembly inhibitor (CAP-1) and its analogues based on a biomass approach
Romashov, Leonid V.; Ananikov, Valentine P.; Org. Biomol. Chem.  (2016) –; doi:10.1039/C6OB01731B

data_7155289
_publ_section_title
;
 Synthesis of HIV-1 capsid protein assembly inhibitor (CAP-1) and its
 analogues based on a biomass approach
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C6OB01731B
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H24 Cl N3 O2 S'
_chemical_formula_sum            'C18 H24 Cl N3 O2 S'
_chemical_formula_weight         381.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-02 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.08(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   38.822(8)
_cell_length_b                   4.5920(9)
_cell_length_c                   10.705(2)
_cell_measurement_reflns_used    500
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      2.0
_cell_volume                     1884.5(7)
_computing_cell_refinement       iMosflm
_computing_data_collection       Automar
_computing_data_reduction        iMosflm
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13010
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.476
_diffrn_reflns_theta_min         1.450
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.185(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+0.7148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                3288
_reflns_number_total             3654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01731b2.cif
_cod_data_source_block           CAP1
_cod_database_code               7155289
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.921
_shelx_res_checksum              20294