Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and d-homoandrostane. Tandem "click" reaction/Cu-catalyzed d-homo rearrangement.
Kotovshchikov, Yury N.; Latyshev, Gennadij V.; Lukashev, Nikolay V.; Beletskaya, Irina P.; Organic & biomolecular chemistry 12 (2014) 3707–3720; doi:10.1039/c4ob00404c

data_7153875
_publ_section_title
;
 Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane
 and d-homoandrostane. Tandem &quot;click&quot; reaction/Cu-catalyzed
 d-homo rearrangement.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3707
_journal_page_last               3720
_journal_paper_doi               10.1039/c4ob00404c
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H37 N3 O3'
_chemical_formula_sum            'C29 H37 N3 O3'
_chemical_formula_weight         475.62
_chemical_melting_point_gt       564
_chemical_melting_point_lt       566
_chemical_name_systematic
; 
 3\b--hydroxy--16\b--(4--phenyl--1<i>H</i>--1,2,3--triazol--1--yl)--
17\a--hydroxy--17\b--methyl--D--homoandrost--5--en--17a--one 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.91340(10)
_cell_length_b                   19.9075(4)
_cell_length_c                   23.6392(5)
_cell_measurement_reflns_used    14050
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      69.66
_cell_measurement_theta_min      4.35
_cell_volume                     2782.83(9)
_computing_cell_refinement       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_collection       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_reduction        '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_molecular_graphics    '<i>Ortep--3</i> (Farrugia,   1997)'
_computing_publication_material  '<i>WinGX</i>    (Farrugia,   1999)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick,  2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick,  2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      '3497 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3036
_diffrn_reflns_theta_full        70.10
_diffrn_reflns_theta_max         70.10
_diffrn_reflns_theta_min         4.44
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.2541
_exptl_absorpt_correction_T_min  0.9392
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
 Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_preparation       CH~2~Cl~2~--CH~3~OH
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0534P)^2^P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1835
_reflns_number_total             3036
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ob00404c2.cif
_cod_data_source_block           r210
_cod_database_code               7153875
_exptl_absorpt_factor_mur        0.063