Resonance-assisted amide protonation in dutasteride hydrochloride salt
Nanubolu, Jagadeesh Babu; Sridhar, Balasubramanian; Ravikumar, Krishnan; CrystEngComm 14 (2012) 2571–; doi:10.1039/c2ce06421a

data_7207574
_publ_section_title
;
 Resonance-assisted amide protonation in dutasteride hydrochloride salt
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2571
_journal_paper_doi               10.1039/c2ce06421a
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H31 F6 N2 O2 +, Cl -, H2 O, C2 H6 O'
_chemical_formula_sum            'C29 H39 Cl F6 N2 O4'
_chemical_formula_weight         629.07
_chemical_name_common
;
Dutasteride chloride hydrate ethanol solvate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.7460(10)
_cell_angle_beta                 88.6870(10)
_cell_angle_gamma                86.1930(10)
_cell_formula_units_Z            1
_cell_length_a                   7.9357(7)
_cell_length_b                   9.1050(8)
_cell_length_c                   11.1952(9)
_cell_measurement_reflns_used    3522
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.33
_cell_volume                     774.85(11)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7533
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0461P)^2^+0.1410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                5048
_reflns_number_total             5376
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ce06421a.txt
_cod_data_source_block           aj_(salt)
_cod_database_code               7207574