#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226345.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226345
loop_
_publ_author_name
'Wang, Zhi-Mei'
'Zhao, Jian'
'Xu, Gang'
_publ_section_title
;
 Prasugrel, a new medicine for preventing blockages in the arteries
;
_journal_coeditor_code           YA2121
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1354
_journal_paper_doi               10.1107/S1600536810017095
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H20 F N O3 S'
_chemical_formula_moiety         'C20 H20 F N O3 S'
_chemical_formula_sum            'C20 H20 F N O3 S'
_chemical_formula_weight         373.43
_chemical_name_common            Prasugrel
_chemical_name_systematic
;
5-[(2-cyclopropylcarbonyl)(2-fluorophenyl)methyl]-4,5,6,7-
tetrahydrothieno[3,2-c]pyridin-2-yl acetate
;
_space_group_IT_number           2
_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                112.938(5)
_cell_angle_beta                 90.644(5)
_cell_angle_gamma                92.591(6)
_cell_formula_units_Z            2
_cell_length_a                   7.910(2)
_cell_length_b                   9.943(3)
_cell_length_c                   12.450(4)
_cell_measurement_reflns_used    1069
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      21.9
_cell_measurement_theta_min      2.2
_cell_volume                     900.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.059
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5345
_diffrn_reflns_theta_full        25.2
_diffrn_reflns_theta_max         25.2
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.21
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.133
_refine_ls_R_factor_gt           0.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0117P)²+3.2142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.186
_refine_ls_wR_factor_ref         0.198
_reflns_number_gt                2379
_reflns_number_total             3201
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2121.cif
_cod_data_source_block           I
_cod_original_cell_volume        900.3(5)
_cod_database_code               2226345
_cod_database_fobs_code          2226345
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.98277(19) 0.7094(2) 0.12388(13) 0.0633(5) Uani d . 1 . .
F F1 0.8924(5) 0.9710(5) -0.3950(4) 0.0885(12) Uani d . 1 . .
C C1 1.4971(8) 0.5727(9) 0.2034(6) 0.080(2) Uani d . 1 . .
H H1A 1.5091 0.5806 0.2825 0.120 Uiso calc R 1 . .
H H1B 1.5907 0.6251 0.1861 0.120 Uiso calc R 1 . .
H H1C 1.4953 0.4716 0.1514 0.120 Uiso calc R 1 . .
C C2 1.3386(8) 0.6352(8) 0.1886(5) 0.074(2) Uani d . 1 . .
C C3 1.1688(7) 0.6812(7) 0.0487(5) 0.0526(15) Uani d . 1 . .
C C4 1.1564(7) 0.7042(6) -0.0503(5) 0.0533(15) Uani d . 1 . .
H H4A 1.2443 0.6929 -0.1016 0.064 Uiso calc R 1 . .
C C5 0.9935(7) 0.7477(6) -0.0677(4) 0.0482(13) Uani d . 1 . .
C C6 0.8868(7) 0.7542(7) 0.0175(4) 0.0528(15) Uani d . 1 . .
C C7 0.7093(7) 0.8012(8) 0.0226(5) 0.0643(18) Uani d . 1 . .
H H7A 0.6854 0.8667 0.1014 0.077 Uiso calc R 1 . .
H H7B 0.6301 0.7167 -0.0004 0.077 Uiso calc R 1 . .
C C8 0.6913(7) 0.8786(7) -0.0600(5) 0.0625(17) Uani d . 1 . .
H H8A 0.5732 0.8971 -0.0675 0.075 Uiso calc R 1 . .
H H8B 0.7554 0.9719 -0.0289 0.075 Uiso calc R 1 . .
C C9 0.9400(7) 0.7866(7) -0.1670(5) 0.0538(15) Uani d . 1 . .
H H9A 0.9894 0.8825 -0.1555 0.065 Uiso calc R 1 . .
H H9B 0.9814 0.7164 -0.2392 0.065 Uiso calc R 1 . .
C C10 0.7071(7) 0.8485(6) -0.2608(5) 0.0491(14) Uani d . 1 . .
H H10A 0.7532 0.9498 -0.2343 0.059 Uiso calc R 1 . .
C C11 0.7730(6) 0.7596(6) -0.3819(4) 0.0437(13) Uani d . 1 . .
C C12 0.8627(7) 0.8249(6) -0.4420(5) 0.0475(13) Uani d . 1 . .
C C13 0.9202(7) 0.7512(7) -0.5530(5) 0.0574(16) Uani d . 1 . .
H H13A 0.9813 0.8007 -0.5910 0.069 Uiso calc R 1 . .
C C14 0.8856(8) 0.6067(8) -0.6044(5) 0.0620(16) Uani d . 1 . .
H H14A 0.9245 0.5550 -0.6787 0.074 Uiso calc R 1 . .
C C15 0.7937(9) 0.5342(8) -0.5491(6) 0.0714(19) Uani d . 1 . .
H H15A 0.7685 0.4341 -0.5863 0.086 Uiso calc R 1 . .
C C16 0.7382(9) 0.6108(7) -0.4370(5) 0.0679(18) Uani d . 1 . .
H H16A 0.6771 0.5613 -0.3990 0.082 Uiso calc R 1 . .
C C17 0.5147(7) 0.8444(7) -0.2809(5) 0.0517(14) Uani d . 1 . .
C C18 0.4630(8) 0.9356(7) -0.3427(5) 0.0654(17) Uani d . 1 . .
H H18A 0.5474 1.0094 -0.3454 0.079 Uiso calc R 1 . .
C C19 0.2829(9) 0.9711(9) -0.3429(6) 0.089(2) Uani d . 1 . .
H H19A 0.2054 0.9357 -0.2987 0.106 Uiso calc R 1 . .
H H19B 0.2590 1.0659 -0.3429 0.106 Uiso calc R 1 . .
C C20 0.3480(9) 0.8650(9) -0.4476(6) 0.085(2) Uani d . 1 . .
H H20A 0.3651 0.8935 -0.5130 0.102 Uiso calc R 1 . .
H H20B 0.3115 0.7632 -0.4688 0.102 Uiso calc R 1 . .
N N1 0.7541(5) 0.7875(5) -0.1760(4) 0.0494(12) Uani d . 1 . .
O O1 1.2404(8) 0.6812(10) 0.2594(4) 0.168(4) Uani d . 1 . .
O O2 1.3121(5) 0.6278(5) 0.0798(3) 0.0711(13) Uani d . 1 . .
O O3 0.4151(5) 0.7686(5) -0.2536(4) 0.0692(12) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 C6 . . 90.2(3) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 O2 . . 121.5(6) ?
O1 C2 C1 . . 125.3(6) ?
O2 C2 C1 . . 113.1(5) ?
C4 C3 O2 . . 122.4(5) ?
C4 C3 S1 . . 112.7(4) ?
O2 C3 S1 . . 124.6(4) ?
C3 C4 C5 . . 112.1(5) ?
C3 C4 H4A . . 123.9 ?
C5 C4 H4A . . 123.9 ?
C6 C5 C4 . . 113.0(5) ?
C6 C5 C9 . . 121.4(5) ?
C4 C5 C9 . . 125.6(5) ?
C5 C6 C7 . . 124.1(5) ?
C5 C6 S1 . . 112.0(4) ?
C7 C6 S1 . . 123.9(4) ?
C6 C7 C8 . . 108.0(5) ?
C6 C7 H7A . . 110.1 ?
C8 C7 H7A . . 110.1 ?
C6 C7 H7B . . 110.1 ?
C8 C7 H7B . . 110.1 ?
H7A C7 H7B . . 108.4 ?
N1 C8 C7 . . 110.0(5) ?
N1 C8 H8A . . 109.7 ?
C7 C8 H8A . . 109.7 ?
N1 C8 H8B . . 109.7 ?
C7 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
N1 C9 C5 . . 111.1(4) ?
N1 C9 H9A . . 109.4 ?
C5 C9 H9A . . 109.4 ?
N1 C9 H9B . . 109.4 ?
C5 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
N1 C10 C11 . . 111.6(4) ?
N1 C10 C17 . . 112.8(5) ?
C11 C10 C17 . . 104.1(4) ?
N1 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
C17 C10 H10A . . 109.4 ?
C12 C11 C16 . . 116.7(5) ?
C12 C11 C10 . . 121.3(5) ?
C16 C11 C10 . . 121.9(5) ?
F1 C12 C11 . . 119.3(5) ?
F1 C12 C13 . . 116.8(5) ?
C11 C12 C13 . . 123.9(6) ?
C14 C13 C12 . . 118.3(6) ?
C14 C13 H13A . . 120.9 ?
C12 C13 H13A . . 120.9 ?
C13 C14 C15 . . 120.9(6) ?
C13 C14 H14A . . 119.6 ?
C15 C14 H14A . . 119.6 ?
C14 C15 C16 . . 119.7(7) ?
C14 C15 H15A . . 120.1 ?
C16 C15 H15A . . 120.1 ?
C11 C16 C15 . . 120.5(6) ?
C11 C16 H16A . . 119.7 ?
C15 C16 H16A . . 119.7 ?
O3 C17 C18 . . 122.7(5) ?
O3 C17 C10 . . 123.7(5) ?
C18 C17 C10 . . 113.6(5) ?
C17 C18 C19 . . 119.3(6) ?
C17 C18 C20 . . 117.3(6) ?
C19 C18 C20 . . 57.8(4) ?
C17 C18 H18A . . 116.5 ?
C19 C18 H18A . . 116.5 ?
C20 C18 H18A . . 116.5 ?
C20 C19 C18 . . 61.4(5) ?
C20 C19 H19A . . 117.6 ?
C18 C19 H19A . . 117.6 ?
C20 C19 H19B . . 117.6 ?
C18 C19 H19B . . 117.6 ?
H19A C19 H19B . . 114.7 ?
C19 C20 C18 . . 60.8(4) ?
C19 C20 H20A . . 117.7 ?
C18 C20 H20A . . 117.7 ?
C19 C20 H20B . . 117.7 ?
C18 C20 H20B . . 117.7 ?
H20A C20 H20B . . 114.8 ?
C10 N1 C9 . . 109.7(4) ?
C10 N1 C8 . . 109.8(4) ?
C9 N1 C8 . . 108.6(4) ?
C2 O2 C3 . . 121.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C3 . 1.727(5) ?
S1 C6 . 1.731(5) ?
F1 C12 . 1.346(6) ?
C1 C2 . 1.464(8) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O1 . 1.150(7) ?
C2 O2 . 1.342(7) ?
C3 C4 . 1.342(7) ?
C3 O2 . 1.385(6) ?
C4 C5 . 1.418(7) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.346(7) ?
C5 C9 . 1.494(7) ?
C6 C7 . 1.494(7) ?
C7 C8 . 1.515(8) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.480(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N1 . 1.474(6) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N1 . 1.460(7) ?
C10 C11 . 1.531(7) ?
C10 C17 . 1.535(7) ?
C10 H10A . 0.9800 ?
C11 C12 . 1.355(7) ?
C11 C16 . 1.380(8) ?
C12 C13 . 1.381(8) ?
C13 C14 . 1.338(8) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.368(9) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.392(8) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
C17 O3 . 1.206(7) ?
C17 C18 . 1.467(8) ?
C18 C19 . 1.483(8) ?
C18 C20 . 1.492(9) ?
C18 H18A . 0.9800 ?
C19 C20 . 1.438(9) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5293653
