#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/11/90/7119028.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_7119028
loop_
_publ_author_name
'Li, Yu'
'Xia, Guiquan'
'Guo, Qi'
'Wu, Li'
'Chen, Shizhen'
'Yang, Zhigang'
'Wang, Wei'
'Zhang, Zhong-Yin'
'Zhou, Xin'
'Jiang, Zhong-Xing'
_publ_section_title
;
 Design, synthesis and evaluation of novel (19)F magnetic resonance
 sensitive protein tyrosine phosphatase inhibitors.
;
_journal_issue                   8
_journal_name_full               MedChemComm
_journal_page_first              1672
_journal_page_last               1680
_journal_paper_doi               10.1039/C6MD00277C
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C19 H19 F6 N O4'
_chemical_formula_weight         439.35
_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
_audit_update_record
;
2016-03-23 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                101.841(3)
_cell_angle_beta                 100.386(3)
_cell_angle_gamma                97.192(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7617(14)
_cell_length_b                   9.9794(18)
_cell_length_c                   13.124(2)
_cell_measurement_reflns_used    51
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      7.5
_cell_volume                     964.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  bruker
_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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6145
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0051(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0426
_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)+(0.0331P)²+0.3907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2635
_reflns_number_total             3992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6md00277c2.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7119028.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.1902(3) -0.02159(18) 0.68351(14) 0.0352(4) Uani 1 1 d .
C2 C 0.2355(3) -0.07017(18) 0.58338(14) 0.0400(5) Uani 1 1 d .
C3 C 0.2602(3) 0.01693(19) 0.51743(14) 0.0406(5) Uani 1 1 d .
H3 H 0.2918 -0.0170 0.4531 0.049 Uiso 1 1 calc R
C4 C 0.2389(2) 0.15700(18) 0.54493(13) 0.0335(4) Uani 1 1 d .
C5 C 0.2673(2) 0.25175(18) 0.47979(14) 0.0376(4) Uani 1 1 d .
H5 H 0.3039 0.2228 0.4163 0.045 Uiso 1 1 calc R
C6 C 0.2408(3) 0.38481(19) 0.51069(15) 0.0391(4) Uani 1 1 d .
C7 C 0.1856(3) 0.4307(2) 0.60611(17) 0.0517(6) Uani 1 1 d .
H7 H 0.1664 0.5217 0.6254 0.062 Uiso 1 1 calc R
C8 C 0.1602(3) 0.34327(19) 0.67001(16) 0.0464(5) Uani 1 1 d .
H8 H 0.1244 0.3749 0.7333 0.056 Uiso 1 1 calc R
C9 C 0.1872(2) 0.20467(17) 0.64203(14) 0.0341(4) Uani 1 1 d .
C10 C 0.1663(2) 0.11338(18) 0.70900(14) 0.0369(4) Uani 1 1 d .
H10 H 0.1347 0.1463 0.7735 0.044 Uiso 1 1 calc R
C11 C 0.1767(3) -0.11682(18) 0.76048(15) 0.0428(5) Uani 1 1 d .
C12 C 0.0456(4) -0.0812(2) 0.83292(18) 0.0557(6) Uani 1 1 d .
C13 C 0.3616(4) -0.1090(3) 0.82882(19) 0.0621(6) Uani 1 1 d .
C14 C 0.3158(3) 0.45454(19) 0.35830(15) 0.0418(5) Uani 1 1 d .
H14A H 0.2293 0.3803 0.3090 0.050 Uiso 1 1 calc R
H14B H 0.4305 0.4244 0.3677 0.050 Uiso 1 1 calc R
C15 C 0.3260(2) 0.58531(19) 0.31582(14) 0.0372(4) Uani 1 1 d .
C16 C 0.4132(4) 0.4527(2) 0.15711(18) 0.0633(7) Uani 1 1 d .
H16A H 0.4118 0.3809 0.1970 0.076 Uiso 1 1 calc R
H16B H 0.5334 0.4750 0.1472 0.076 Uiso 1 1 calc R
C17 C 0.2915(4) 0.3965(3) 0.0500(2) 0.0888(9) Uani 1 1 d .
H17A H 0.1712 0.3786 0.0587 0.133 Uiso 1 1 calc R
H17B H 0.3239 0.3117 0.0156 0.133 Uiso 1 1 calc R
H17C H 0.3013 0.4632 0.0072 0.133 Uiso 1 1 calc R
C18 C 0.3816(3) 0.7033(2) 0.17988(17) 0.0522(6) Uani 1 1 d .
H18A H 0.4565 0.6943 0.1280 0.063 Uiso 1 1 calc R
H18B H 0.4396 0.7811 0.2386 0.063 Uiso 1 1 calc R
C19 C 0.2061(4) 0.7340(3) 0.1292(2) 0.0836(9) Uani 1 1 d .
H19A H 0.1490 0.6585 0.0700 0.125 Uiso 1 1 calc R
H19B H 0.2251 0.8179 0.1048 0.125 Uiso 1 1 calc R
H19C H 0.1321 0.7454 0.1806 0.125 Uiso 1 1 calc R
F1 F -0.1091(2) -0.06777(16) 0.77681(12) 0.0773(4) Uani 1 1 d .
F2 F 0.1023(2) 0.03495(13) 0.90784(10) 0.0730(4) Uani 1 1 d .
F3 F 0.0122(2) -0.18176(14) 0.88316(12) 0.0869(5) Uani 1 1 d .
F4 F 0.4331(2) 0.02002(16) 0.88345(12) 0.0881(5) Uani 1 1 d .
F5 F 0.3608(2) -0.18682(16) 0.89997(12) 0.0923(5) Uani 1 1 d .
F6 F 0.4721(2) -0.15397(19) 0.76821(14) 0.0949(6) Uani 1 1 d .
N1 N 0.3663(2) 0.57645(16) 0.21984(13) 0.0450(4) Uani 1 1 d .
O1 O 0.2531(3) -0.20709(13) 0.55832(11) 0.0617(5) Uani 1 1 d .
H1 H 0.2648 -0.2285 0.4965 0.093 Uiso 1 1 calc R
O2 O 0.2645(2) 0.48808(13) 0.45697(11) 0.0508(4) Uani 1 1 d .
O3 O 0.2964(2) 0.69483(14) 0.36594(10) 0.0488(4) Uani 1 1 d .
O4 O 0.1102(2) -0.25596(13) 0.70979(12) 0.0619(5) Uani 1 1 d .
H4 H 0.1322 -0.2724 0.6501 0.093 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
C10 C1 C2 117.46(16)
C10 C1 C11 121.83(16)
C2 C1 C11 120.66(15)
C3 C2 O1 122.69(16)
C3 C2 C1 121.05(16)
O1 C2 C1 116.25(16)
C2 C3 C4 121.33(16)
C3 C4 C9 118.02(16)
C3 C4 C5 123.08(16)
C9 C4 C5 118.89(16)
C6 C5 C4 119.72(16)
C5 C6 O2 126.35(17)
C5 C6 C7 121.09(17)
O2 C6 C7 112.56(16)
C8 C7 C6 120.30(18)
C7 C8 C9 120.82(18)
C10 C9 C8 121.59(16)
C10 C9 C4 119.25(16)
C8 C9 C4 119.15(16)
C1 C10 C9 122.81(16)
O4 C11 C1 113.75(15)
O4 C11 C12 102.62(16)
C1 C11 C12 113.21(17)
O4 C11 C13 108.20(17)
C1 C11 C13 109.09(17)
C12 C11 C13 109.73(18)
F2 C12 F1 106.9(2)
F2 C12 F3 106.35(17)
F1 C12 F3 106.9(2)
F2 C12 C11 114.20(19)
F1 C12 C11 111.18(18)
F3 C12 C11 110.88(19)
F6 C13 F5 106.5(2)
F6 C13 F4 107.6(2)
F5 C13 F4 106.49(19)
F6 C13 C11 110.62(19)
F5 C13 C11 112.9(2)
F4 C13 C11 112.42(19)
O2 C14 C15 106.87(15)
O3 C15 N1 120.65(17)
O3 C15 C14 121.91(16)
N1 C15 C14 117.43(16)
N1 C16 C17 113.8(2)
N1 C18 C19 113.50(19)
C15 N1 C16 124.40(17)
C15 N1 C18 117.66(16)
C16 N1 C18 117.65(16)
C6 O2 C14 118.21(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C10 1.364(2)
C1 C2 1.426(2)
C1 C11 1.530(2)
C2 C3 1.367(2)
C2 O1 1.368(2)
C3 C4 1.409(2)
C4 C9 1.412(2)
C4 C5 1.422(2)
C5 C6 1.359(2)
C6 O2 1.375(2)
C6 C7 1.403(3)
C7 C8 1.349(3)
C8 C9 1.409(2)
C9 C10 1.404(2)
C11 O4 1.398(2)
C11 C12 1.538(3)
C11 C13 1.533(3)
C12 F2 1.324(2)
C12 F1 1.328(3)
C12 F3 1.333(2)
C13 F6 1.329(3)
C13 F5 1.332(2)
C13 F4 1.333(3)
C14 O2 1.410(2)
C14 C15 1.519(2)
C15 O3 1.226(2)
C15 N1 1.340(2)
C16 N1 1.463(3)
C16 C17 1.499(3)
C18 N1 1.466(2)
C18 C19 1.501(3)
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
C10 C1 C2 C3 2.3(3)
C11 C1 C2 C3 -175.32(19)
C10 C1 C2 O1 -177.97(18)
C11 C1 C2 O1 4.4(3)
O1 C2 C3 C4 179.18(18)
C1 C2 C3 C4 -1.1(3)
C2 C3 C4 C9 -1.4(3)
C2 C3 C4 C5 178.50(19)
C3 C4 C5 C6 178.77(19)
C9 C4 C5 C6 -1.4(3)
C4 C5 C6 O2 179.27(18)
C4 C5 C6 C7 0.0(3)
C5 C6 C7 C8 1.0(3)
O2 C6 C7 C8 -178.4(2)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C10 178.2(2)
C7 C8 C9 C4 -1.0(3)
C3 C4 C9 C10 2.6(3)
C5 C4 C9 C10 -177.29(17)
C3 C4 C9 C8 -178.27(19)
C5 C4 C9 C8 1.9(3)
C2 C1 C10 C9 -1.0(3)
C11 C1 C10 C9 176.56(18)
C8 C9 C10 C1 179.46(19)
C4 C9 C10 C1 -1.4(3)
C10 C1 C11 O4 147.39(19)
C2 C1 C11 O4 -35.1(3)
C10 C1 C11 C12 30.8(3)
C2 C1 C11 C12 -151.74(19)
C10 C1 C11 C13 -91.7(2)
C2 C1 C11 C13 85.8(2)
O4 C11 C12 F2 164.95(18)
C1 C11 C12 F2 -72.0(2)
C13 C11 C12 F2 50.1(2)
O4 C11 C12 F1 -74.0(2)
C1 C11 C12 F1 49.0(2)
C13 C11 C12 F1 171.15(17)
O4 C11 C12 F3 44.8(2)
C1 C11 C12 F3 167.86(18)
C13 C11 C12 F3 -70.0(2)
O4 C11 C13 F6 62.0(2)
C1 C11 C13 F6 -62.2(2)
C12 C11 C13 F6 173.23(18)
O4 C11 C13 F5 -57.2(2)
C1 C11 C13 F5 178.55(18)
C12 C11 C13 F5 54.0(2)
O4 C11 C13 F4 -177.75(18)
C1 C11 C13 F4 58.0(2)
C12 C11 C13 F4 -66.5(2)
O2 C14 C15 O3 1.5(3)
O2 C14 C15 N1 -177.52(16)
O3 C15 N1 C16 176.4(2)
C14 C15 N1 C16 -4.6(3)
O3 C15 N1 C18 2.8(3)
C14 C15 N1 C18 -178.19(17)
C17 C16 N1 C15 120.6(2)
C17 C16 N1 C18 -65.8(3)
C19 C18 N1 C15 -82.3(3)
C19 C18 N1 C16 103.7(2)
C5 C6 O2 C14 2.2(3)
C7 C6 O2 C14 -178.44(18)
C15 C14 O2 C6 178.17(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 134148396
