Synthesis of D-Ring Annulated Pyridosteroids from β-Formyl Enamides and Their Biological Evaluations.
Nongthombam, Geetmani Singh; Borah, Kasmika; Muinao, Thingreila; Silla, Yumnam; Pal, Mintu; Deka Boruah, Hari Prasanna; Boruah, Romesh Chandra; ACS combinatorial science 21 (2019) 11–27; doi:10.1021/acscombsci.8b00140

data_4515842
_publ_section_title
;
 Synthesis of D-Ring Annulated Pyridosteroids from \b-Formyl Enamides and
 Their Biological Evaluations.
;
_journal_issue                   1
_journal_name_full               'ACS combinatorial science'
_journal_page_first              11
_journal_page_last               27
_journal_paper_doi               10.1021/acscombsci.8b00140
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H39 N O4'
_chemical_formula_sum            'C33 H39 N O4'
_chemical_formula_weight         513.68
_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_Int_Tables_number      4
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.428(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.7787(6)
_cell_length_b                   5.9377(2)
_cell_length_c                   16.8849(7)
_cell_measurement_reflns_used    8799
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.51
_cell_volume                     1413.66(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47829
_diffrn_reflns_theta_full        28.7138
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2067
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             552.2625
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.5181
_refine_diff_density_min         -0.3321
_refine_diff_density_rms         0.0585
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.0(14)
_refine_ls_d_res_high            0.7397
_refine_ls_d_res_low             16.1098
_refine_ls_goodness_of_fit_ref   1.0335
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     346
_refine_ls_number_reflns         7218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0335
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.2600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.985
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                5339
_reflns_number_total             7218
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            co8b00140_si_002.cif
_cod_data_source_block           rcb
_cod_database_code               4515842
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C(H), C4(H4), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C8(H8a,H8b), C9(H9a,H9b), C11(H11a,H11b), C12(H12a,H12b),
 C17(H17a,H17b), C1a(H1aa,H1ab), C1j(H1ja,H1jb)
2.c Aromatic/amide H refined with riding coordinates:
 C1g(H1g), C1k(H1k), C1i(H1i), C1d(H1d), C1e(H1e), C1b(H1b), C7(H7)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C1c(H1ca,H1cb,H1cc), C1l(H1la,H1lb,H1lc), C1m(H1ma,H1mb,
 H1mc)
;