#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/76/2017686.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_2017686
loop_
_publ_author_name
'Ravikumar, Krishnan'
'Sridhar, Balasubramanian'
_publ_section_title
;
 Two polymorphs of safinamide, a selective and reversible inhibitor of
 monoamine oxidase B
;
_journal_coeditor_code           SF3130
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o317
_journal_page_last               o320
_journal_paper_doi               10.1107/S0108270110019384
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H19 F N2 O2'
_chemical_formula_moiety         'C17 H19 F N2 O2'
_chemical_formula_sum            'C17 H19 F N2 O2'
_chemical_formula_weight         302.34
_chemical_name_common            Safinamide
_chemical_name_systematic
;
2(S)-[4-(3-Fluorobenzyloxy) benzylamino] propionamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6297(9)
_cell_length_b                   8.1015(12)
_cell_length_c                   29.268(4)
_cell_measurement_reflns_used    5921
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.78
_cell_volume                     1572.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al.,
2008)'
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15166
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0431
_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/[σ²(Fo²)+(0.0658P)²+0.2636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1573
_reflns_number_total             1636
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3130.cif
_cod_data_source_block           II
_cod_database_code               2017686
_cod_database_fobs_code          2017686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C C1 -0.1171(5) 0.4371(4) -0.02528(9) 0.0495(7) Uani d . 1 . .
C C2 -0.2923(5) 0.3716(4) -0.04292(9) 0.0520(7) Uani d . 1 . .
H H2 -0.4162 0.3948 -0.0295 0.062 Uiso calc R 1 . .
C C3 -0.2811(5) 0.2712(4) -0.08073(10) 0.0541(8) Uani d . 1 . .
C C4 -0.1047(6) 0.2333(4) -0.10173(11) 0.0619(9) Uani d . 1 . .
H H4 -0.1017 0.1654 -0.1273 0.074 Uiso calc R 1 . .
C C5 0.0688(6) 0.2983(5) -0.08393(12) 0.0687(10) Uani d . 1 . .
H H5 0.1921 0.2738 -0.0975 0.082 Uiso calc R 1 . .
C C6 0.0627(5) 0.4006(5) -0.04589(11) 0.0630(9) Uani d . 1 . .
H H6 0.1817 0.4446 -0.0343 0.076 Uiso calc R 1 . .
C C7 -0.1350(5) 0.5511(4) 0.01517(10) 0.0561(8) Uani d . 1 . .
H H7A -0.2003 0.6529 0.0060 0.067 Uiso calc R 1 . .
H H7B -0.2169 0.4996 0.0387 0.067 Uiso calc R 1 . .
C C8 0.0697(5) 0.6838(4) 0.07106(10) 0.0524(8) Uani d . 1 . .
C C9 0.2585(6) 0.6969(4) 0.09069(11) 0.0621(9) Uani d . 1 . .
H H9 0.3667 0.6383 0.0786 0.074 Uiso calc R 1 . .
C C10 0.2863(6) 0.7973(4) 0.12828(11) 0.0632(9) Uani d . 1 . .
H H10 0.4138 0.8053 0.1413 0.076 Uiso calc R 1 . .
C C11 0.1288(6) 0.8859(4) 0.14691(9) 0.0548(8) Uani d . 1 . .
C C12 -0.0589(5) 0.8686(4) 0.12731(10) 0.0580(8) Uani d . 1 . .
H H12 -0.1675 0.9256 0.1398 0.070 Uiso calc R 1 . .
C C13 -0.0904(5) 0.7689(4) 0.08958(10) 0.0570(8) Uani d . 1 . .
H H13 -0.2185 0.7595 0.0769 0.068 Uiso calc R 1 . .
C C14 0.1626(6) 1.0039(4) 0.18580(9) 0.0611(9) Uani d . 1 . .
H H14A 0.2914 1.0585 0.1816 0.073 Uiso calc R 1 . .
H H14B 0.0584 1.0879 0.1851 0.073 Uiso calc R 1 . .
C C15 0.1719(4) 1.0422(3) 0.26796(9) 0.0375(6) Uani d . 1 . .
H H15 0.0413 1.0983 0.2703 0.045 Uiso calc R 1 . .
C C16 0.3358(4) 1.1737(3) 0.26122(8) 0.0339(5) Uani d . 1 . .
C C17 0.2095(7) 0.9497(4) 0.31239(9) 0.0648(10) Uani d . 1 . .
H H17A 0.1037 0.8706 0.3172 0.097 Uiso calc R 1 . .
H H17B 0.2116 1.0266 0.3373 0.097 Uiso calc R 1 . .
H H17C 0.3368 0.8936 0.3107 0.097 Uiso calc R 1 . .
F F1 -0.4535(3) 0.2103(3) -0.09842(8) 0.0809(7) Uani d . 1 . .
N N1 0.1607(3) 0.9244(3) 0.23036(7) 0.0337(5) Uani d . 1 . .
H H1N 0.262(4) 0.853(3) 0.2338(8) 0.027(6) Uiso d . 1 . .
N N2 0.2709(4) 1.3273(3) 0.25989(9) 0.0446(6) Uani d . 1 . .
H H2N 0.144(6) 1.344(4) 0.2631(10) 0.049(8) Uiso d . 1 . .
H H3N 0.359(5) 1.402(4) 0.2545(9) 0.038(7) Uiso d . 1 . .
O O1 0.0592(3) 0.5858(3) 0.03269(7) 0.0640(6) Uani d . 1 . .
O O2 0.5132(3) 1.1349(2) 0.25693(8) 0.0516(5) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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
C6 C1 C2 . . 119.1(3) ?
C6 C1 C7 . . 123.2(3) ?
C2 C1 C7 . . 117.7(3) ?
C3 C2 C1 . . 118.9(3) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
F1 C3 C4 . . 118.3(3) ?
F1 C3 C2 . . 118.6(3) ?
C4 C3 C2 . . 123.0(3) ?
C3 C4 C5 . . 117.7(3) ?
C3 C4 H4 . . 121.1 ?
C5 C4 H4 . . 121.1 ?
C4 C5 C6 . . 120.7(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 120.5(3) ?
C1 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
O1 C7 C1 . . 109.6(3) ?
O1 C7 H7A . . 109.8 ?
C1 C7 H7A . . 109.8 ?
O1 C7 H7B . . 109.8 ?
C1 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.2 ?
C13 C8 O1 . . 124.8(3) ?
C13 C8 C9 . . 119.8(3) ?
O1 C8 C9 . . 115.4(3) ?
C10 C9 C8 . . 119.8(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C11 C10 C9 . . 121.4(3) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C12 C11 C10 . . 117.8(3) ?
C12 C11 C14 . . 121.0(3) ?
C10 C11 C14 . . 121.2(3) ?
C11 C12 C13 . . 121.9(3) ?
C11 C12 H12 . . 119.1 ?
C13 C12 H12 . . 119.1 ?
C8 C13 C12 . . 119.3(3) ?
C8 C13 H13 . . 120.3 ?
C12 C13 H13 . . 120.3 ?
N1 C14 C11 . . 113.3(2) ?
N1 C14 H14A . . 108.9 ?
C11 C14 H14A . . 108.9 ?
N1 C14 H14B . . 108.9 ?
C11 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
N1 C15 C17 . . 109.4(2) ?
N1 C15 C16 . . 113.1(2) ?
C17 C15 C16 . . 109.6(2) ?
N1 C15 H15 . . 108.2 ?
C17 C15 H15 . . 108.2 ?
C16 C15 H15 . . 108.2 ?
O2 C16 N2 . . 123.6(2) ?
O2 C16 C15 . . 121.1(2) ?
N2 C16 C15 . . 115.4(2) ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 N1 C15 . . 112.8(2) ?
C14 N1 H1N . . 112.3(16) ?
C15 N1 H1N . . 107.4(16) ?
C16 N2 H2N . . 118(2) ?
C16 N2 H3N . . 116.6(19) ?
H2N N2 H3N . . 125(3) ?
C8 O1 C7 . . 117.1(2) ?
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
C1 C6 . 1.368(5) ?
C1 C2 . 1.378(4) ?
C1 C7 . 1.506(4) ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.9300 ?
C3 F1 . 1.348(4) ?
C3 C4 . 1.357(5) ?
C4 C5 . 1.368(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.414(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C13 . 1.377(5) ?
C8 O1 . 1.377(4) ?
C8 C9 . 1.382(5) ?
C9 C10 . 1.380(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.379(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(5) ?
C11 C14 . 1.503(4) ?
C12 C13 . 1.384(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 N1 . 1.454(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 N1 . 1.458(3) ?
C15 C17 . 1.521(4) ?
C15 C16 . 1.535(3) ?
C15 H15 . 0.9800 ?
C16 O2 . 1.223(3) ?
C16 N2 . 1.318(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 H1N . 0.89(3) ?
N2 H2N . 0.86(4) ?
N2 H3N . 0.85(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O2 3_645 0.89(3) 2.33(3) 3.212(3) 171(2)
N2 H2N N1 3 0.86(4) 2.13(4) 2.981(3) 171(3)
N2 H3N O2 3_655 0.85(3) 2.10(3) 2.916(3) 160(3)
C6 H6 O1 . 0.93 2.41 2.746(4) 101
C5 H5 F1 1_655 0.93 2.41 3.274(4) 155
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.0(4) ?
C7 C1 C2 C3 . . . . 178.0(3) ?
C1 C2 C3 F1 . . . . -178.6(3) ?
C1 C2 C3 C4 . . . . 0.0(5) ?
F1 C3 C4 C5 . . . . 178.8(3) ?
C2 C3 C4 C5 . . . . 0.3(5) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
C2 C1 C6 C5 . . . . -0.3(5) ?
C7 C1 C6 C5 . . . . -178.1(3) ?
C4 C5 C6 C1 . . . . 0.5(6) ?
C6 C1 C7 O1 . . . . -10.9(5) ?
C2 C1 C7 O1 . . . . 171.2(3) ?
C13 C8 C9 C10 . . . . -1.0(5) ?
O1 C8 C9 C10 . . . . 177.6(3) ?
C8 C9 C10 C11 . . . . -0.1(5) ?
C9 C10 C11 C12 . . . . 1.3(5) ?
C9 C10 C11 C14 . . . . -175.7(3) ?
C10 C11 C12 C13 . . . . -1.4(5) ?
C14 C11 C12 C13 . . . . 175.7(3) ?
O1 C8 C13 C12 . . . . -177.5(3) ?
C9 C8 C13 C12 . . . . 1.0(5) ?
C11 C12 C13 C8 . . . . 0.2(5) ?
C12 C11 C14 N1 . . . . 98.5(4) ?
C10 C11 C14 N1 . . . . -84.5(4) ?
N1 C15 C16 O2 . . . . -59.6(3) ?
C17 C15 C16 O2 . . . . 62.8(3) ?
N1 C15 C16 N2 . . . . 119.6(3) ?
C17 C15 C16 N2 . . . . -118.0(3) ?
C11 C14 N1 C15 . . . . -173.8(3) ?
C17 C15 N1 C14 . . . . -169.3(3) ?
C16 C15 N1 C14 . . . . -46.8(3) ?
C13 C8 O1 C7 . . . . -9.8(4) ?
C9 C8 O1 C7 . . . . 171.7(3) ?
C1 C7 O1 C8 . . . . -177.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 116349
