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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/54/7235471.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7235471
loop_
_publ_author_name
'Leonard, Matthew J.'
'Lingham, Anthony R.'
'Niere, Julie O.'
'Jackson, Neale R. C.'
'McKay, Peter G.'
'Hügel, Helmut M.'
_publ_section_title
;
 Alternative synthesis of the anti-baldness compound RU58841
;
_journal_issue                   27
_journal_name_full               'RSC Adv.'
_journal_page_first              14143
_journal_paper_doi               10.1039/C4RA00332B
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C12 H10 F3 N3 O3, C3 H7 N O'
_chemical_formula_sum            'C15 H17 F3 N4 O4'
_chemical_formula_weight         374.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens
'H2N from delta-F; other H atoms placed geometrically'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.965(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.373(4)
_cell_length_b                   11.959(4)
_cell_length_c                   11.210(3)
_cell_measurement_reflns_used    1824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.55
_cell_volume                     1714.8(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'apex2 ccd'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9117
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    'freely refined; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0420
_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)+(0.0310P)²+0.3988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2588
_reflns_number_total             3366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra00332b2.cif
_cod_data_source_block           ml018_new
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235471
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.10569(9) 0.53329(10) 0.41725(9) 0.0338(3) Uani 1 1 d .
F2 F 0.16143(9) 0.70136(10) 0.43904(9) 0.0302(3) Uani 1 1 d .
F3 F 0.03439(8) 0.65369(11) 0.50706(10) 0.0335(3) Uani 1 1 d .
O1 O 0.46088(10) 0.34636(12) 0.95795(11) 0.0267(3) Uani 1 1 d .
O2 O 0.59556(10) 0.14479(12) 0.97077(13) 0.0311(4) Uani 1 1 d .
O3 O 0.48408(11) 0.11372(13) 1.07239(11) 0.0316(4) Uani 1 1 d .
N1 N 0.19374(13) 0.88092(15) 0.66610(15) 0.0290(4) Uani 1 1 d .
N2 N 0.32790(12) 0.33794(14) 0.77714(13) 0.0178(3) Uani 1 1 d .
H2N H 0.2945(15) 0.2931(18) 0.7167(18) 0.022(5) Uiso 1 1 d .
N3 N 0.50620(12) 0.13803(13) 0.97790(14) 0.0218(4) Uani 1 1 d .
C1 C 0.30051(13) 0.45059(16) 0.76102(15) 0.0166(4) Uani 1 1 d .
C2 C 0.23046(13) 0.48032(16) 0.64546(15) 0.0167(4) Uani 1 1 d .
H2 H 0.2036 0.4254 0.5860 0.020 Uiso 1 1 calc R
C3 C 0.20138(13) 0.58960(16) 0.61977(15) 0.0175(4) Uani 1 1 d .
C4 C 0.23976(13) 0.67262(16) 0.70907(15) 0.0168(4) Uani 1 1 d .
C5 C 0.30663(13) 0.64211(16) 0.82491(15) 0.0183(4) Uani 1 1 d .
H5 H 0.3312 0.6966 0.8855 0.022 Uiso 1 1 calc R
C6 C 0.33697(13) 0.53263(16) 0.85114(15) 0.0179(4) Uani 1 1 d .
H6 H 0.3817 0.5136 0.9289 0.022 Uiso 1 1 calc R
C7 C 0.12642(14) 0.61900(16) 0.49576(16) 0.0202(4) Uani 1 1 d .
C8 C 0.21422(14) 0.78847(18) 0.68457(15) 0.0207(4) Uani 1 1 d .
C9 C 0.40537(13) 0.29333(16) 0.87179(15) 0.0171(4) Uani 1 1 d .
C10 C 0.41665(13) 0.16629(16) 0.86073(15) 0.0173(4) Uani 1 1 d .
C11 C 0.45010(15) 0.13509(17) 0.74713(16) 0.0252(4) Uani 1 1 d .
H11A H 0.4673 0.0570 0.7505 0.038 Uiso 1 1 calc R
H11B H 0.5102 0.1784 0.7459 0.038 Uiso 1 1 calc R
H11C H 0.3940 0.1500 0.6730 0.038 Uiso 1 1 calc R
C12 C 0.31950(14) 0.10465(17) 0.86702(16) 0.0220(4) Uani 1 1 d .
H12A H 0.2635 0.1193 0.7927 0.033 Uiso 1 1 calc R
H12B H 0.2999 0.1298 0.9384 0.033 Uiso 1 1 calc R
H12C H 0.3334 0.0258 0.8740 0.033 Uiso 1 1 calc R
O4 O 0.20600(10) 0.27225(12) 1.05612(11) 0.0265(3) Uani 1 1 d .
N4 N 0.10379(11) 0.38202(14) 0.90301(13) 0.0204(4) Uani 1 1 d .
C13 C 0.16869(14) 0.36406(17) 1.01608(16) 0.0222(4) Uani 1 1 d .
H13 H 0.1875 0.4252 1.0691 0.027 Uiso 1 1 calc R
C14 C 0.06296(15) 0.49305(17) 0.86528(16) 0.0251(4) Uani 1 1 d .
H14A H 0.0903 0.5446 0.9326 0.038 Uiso 1 1 calc R
H14B H -0.0119 0.4917 0.8444 0.038 Uiso 1 1 calc R
H14C H 0.0835 0.5163 0.7939 0.038 Uiso 1 1 calc R
C15 C 0.07137(14) 0.29250(17) 0.81308(16) 0.0239(4) Uani 1 1 d .
H15A H 0.1006 0.2231 0.8505 0.036 Uiso 1 1 calc R
H15B H 0.0955 0.3077 0.7420 0.036 Uiso 1 1 calc R
H15C H -0.0035 0.2873 0.7870 0.036 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N2 C1 126.37(16)
C9 N2 H2N 117.7(13)
C1 N2 H2N 115.8(13)
O3 N3 O2 124.31(15)
O3 N3 C10 118.09(15)
O2 N3 C10 117.56(15)
C6 C1 N2 124.38(15)
C6 C1 C2 119.30(17)
N2 C1 C2 116.32(16)
C3 C2 C1 120.48(17)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 120.33(15)
C2 C3 C7 119.38(16)
C4 C3 C7 120.28(17)
C5 C4 C3 118.91(17)
C5 C4 C8 118.92(16)
C3 C4 C8 122.16(15)
C6 C5 C4 121.13(17)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 119.79(15)
C5 C6 H6 120.1
C1 C6 H6 120.1
F1 C7 F2 106.84(14)
F1 C7 F3 106.39(15)
F2 C7 F3 106.10(15)
F1 C7 C3 112.81(16)
F2 C7 C3 112.57(15)
F3 C7 C3 111.67(14)
N1 C8 C4 179.4(2)
O1 C9 N2 124.59(18)
O1 C9 C10 122.05(15)
N2 C9 C10 113.35(15)
C12 C10 C11 112.79(15)
C12 C10 N3 108.60(14)
C11 C10 N3 108.49(14)
C12 C10 C9 111.86(15)
C11 C10 C9 111.83(15)
N3 C10 C9 102.67(13)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C13 N4 C15 121.63(17)
C13 N4 C14 120.78(16)
C15 N4 C14 117.59(14)
O4 C13 N4 124.95(18)
O4 C13 H13 117.5
N4 C13 H13 117.5
N4 C14 H14A 109.5
N4 C14 H14B 109.5
H14A C14 H14B 109.5
N4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N4 C15 H15A 109.5
N4 C15 H15B 109.5
H15A C15 H15B 109.5
N4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.327(2)
F2 C7 1.329(2)
F3 C7 1.339(2)
O1 C9 1.211(2)
O2 N3 1.223(2)
O3 N3 1.215(2)
N1 C8 1.143(3)
N2 C9 1.357(2)
N2 C1 1.394(2)
N2 H2N 0.88(2)
N3 C10 1.535(2)
C1 C6 1.391(2)
C1 C2 1.405(2)
C2 C3 1.370(3)
C2 H2 0.9300
C3 C4 1.397(3)
C3 C7 1.499(2)
C4 C5 1.393(2)
C4 C8 1.434(3)
C5 C6 1.377(3)
C5 H5 0.9300
C6 H6 0.9300
C9 C10 1.535(3)
C10 C12 1.513(3)
C10 C11 1.514(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
O4 C13 1.235(2)
N4 C13 1.328(2)
N4 C15 1.448(2)
N4 C14 1.451(3)
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339300
