Crystal structure of (<i>S</i>)-2-[(3<i>S</i>,8<i>S</i>,9<i>S</i>,10<i>R</i>,13<i>S</i>,14<i>S</i>,17<i>R</i>)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthren-17-yl]-<i>N</i>-methoxy-<i>N</i>-methylpropanamide (Fernholz Weinreb amide)
Viktorsson, Elvar Ørn; Åstrand, Ove Alexander Høgmoen; Haseeb, Rasha Sabah; Görbitz, Carl Henrik; Rongved, Pål; Acta Crystallographica Section E 71 (2015) 275–277; doi:10.1107/S2056989015001747

data_2240435
_publ_section_title
;
 Crystal structure of
 (<i>S</i>)-2-[(3<i>S</i>,8<i>S</i>,9<i>S</i>,10<i>R</i>,13<i>S</i>,14<i>S</i>,17<i>R</i>)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthren-17-yl]-<i>N</i>-methoxy-<i>N</i>-methylpropanamide
 (Fernholz Weinreb amide)
;
_journal_coeditor_code           HB7343
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              275
_journal_page_last               277
_journal_paper_doi               10.1107/S2056989015001747
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C24 H39 N O3'
_chemical_formula_moiety         'C24 H39 N O3'
_chemical_formula_sum            'C24 H39 N O3'
_chemical_formula_weight         389.56
_chemical_name_systematic
(<i>S</i>)-2-[(3<i>S</i>,8<i>S</i>,9<i>S</i>,10<i>R</i>,13<i>S</i>,14<i>S</i>,17<i>R</i>)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthren-17-yl]-<i>N</i>-methoxy-<i>N</i>-methylpropanamide
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7256(4)
_cell_length_b                   19.0030(9)
_cell_length_c                   29.8162(15)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.25
_cell_volume                     4377.3(4)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Vantage single-crystal CCD'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5\% \w rotation'
_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  0.0886
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            44800
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.054
_diffrn_reflns_theta_min         2.250
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       'flat needle'
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         7739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.1501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                5760
_reflns_number_total             7739
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb7343sup1.cif
_cod_data_source_block           I
_cod_database_code               2240435
_cod_database_fobs_code          2240435
_shelx_hkl_checksum              32698
_shelx_res_checksum              56091
_shelxl_version_number           .2013