A stereo configuration-activity study of 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency inhibitors of HIV-1 variants.
Wu, Shaotong; Yin, Qianqian; Zhao, Liang; Fan, Ningning; Tang, Xiaowan; Zhao, Jianxiong; Sheng, Tao; Guo, Ying; Tian, Chao; Zhang, Zhili; Xu, Weisi; Liu, Zhenming; Jiang, Shibo; Ma, Liying; Liu, Junyi; Wang, Xiaowei; Organic & biomolecular chemistry 14 (2016) 1413–1420; doi:10.1039/c5ob02154e

data_7154843
_publ_section_title
;
 A stereo configuration-activity study of
 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency
 inhibitors of HIV-1 variants.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1413
_journal_page_last               1420
_journal_paper_doi               10.1039/c5ob02154e
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ss
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.41
_chemical_melting_point          159
_chemical_name_common            5e
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-12-04 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   11.71049(13)
_cell_length_b                   11.80555(11)
_cell_length_c                   52.7036(5)
_cell_measurement_reflns_used    69569
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      73.833
_cell_measurement_theta_min      3.837
_cell_volume                     7286.21(13)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -65
_diffrn_reflns_number            69569
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.833
_diffrn_reflns_theta_min         3.837
_exptl_absorpt_coefficient_mu    0.570
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 5937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     849
_refine_ls_number_reflns         14519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0675P)^2^+1.0541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                13896
_reflns_number_total             14519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02154e2.cif
_cod_data_source_block           exp_4139
_cod_depositor_comments
;
     Adding full bibliography for 7154843.cif.

2017-03-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C80 H100 N4 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1245.63
_cod_database_code               7154843
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.945
_shelxl_version_number           2013-3
_shelx_res_checksum              69620