#------------------------------------------------------------------------------
#$Date: 2020-06-03 05:53:35 +0300 (Wed, 03 Jun 2020) $
#$Revision: 252561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240593.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_7240593
loop_
_publ_author_name
'Poirier, Marion'
'Pujol-Giménez, Jonai'
'Manatschal, Cristina'
'Bühlmann, Sven'
'Embaby, Ahmed'
'Javor, Sacha'
'Hediger, Matthias A.'
'Reymond, Jean-Louis'
_publ_section_title
;
 Pyrazolyl-pyrimidones inhibit the function of human solute carrier
 protein SLC11A2 (hDMT1) by metal chelation
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D0MD00085J
_journal_year                    2020
_chemical_formula_sum            'C14 H18 N4 O'
_chemical_formula_weight         258.32
_chemical_name_systematic
2-(3-ethyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)-6-methylpyrimidin-4(3H)-one
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-12-12T15:01:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-01-10 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8002(2)
_cell_length_b                   9.62410(10)
_cell_length_c                   14.3730(2)
_cell_measurement_reflns_used    6648
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.047
_cell_measurement_theta_min      2.152
_cell_volume                     2600.58(5)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0006431
_diffrn_orient_matrix_UB_12      -0.067915
_diffrn_orient_matrix_UB_13      -0.0191959
_diffrn_orient_matrix_UB_21      0.0377157
_diffrn_orient_matrix_UB_22      0.001185
_diffrn_orient_matrix_UB_23      0.0002959
_diffrn_orient_matrix_UB_31      0.0000361
_diffrn_orient_matrix_UB_32      -0.0286619
_diffrn_orient_matrix_UB_33      0.0454544
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14668
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.142
_diffrn_reflns_theta_min         2.167
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3237
_exptl_crystal_size_mid          0.2243
_exptl_crystal_size_min          0.1952
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0388P)²+0.7943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0
_reflns_number_gt                2475
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0md00085j3.cif
_cod_data_source_block           16jlr003
_cod_database_code               7240593
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32895(5) 0.40608(13) 0.55695(8) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.33173(6) 0.25811(13) 0.56533(8) 0.0257(3) Uani 1 1 d . . . . .
H2 H 0.2903 0.2045 0.5535 0.031 Uiso 1 1 calc R U . . .
C3 C 0.39320(6) 0.19342(13) 0.59005(8) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.39838(7) 0.03954(14) 0.60058(11) 0.0389(3) Uani 1 1 d . . . . .
H4A H 0.3522 -0.0027 0.5867 0.058 Uiso 1 1 calc R U . . .
H4B H 0.4122 0.0169 0.6646 0.058 Uiso 1 1 calc R U . . .
H4C H 0.4342 0.0034 0.5574 0.058 Uiso 1 1 calc R U . . .
C5 C 0.45257(5) 0.39743(12) 0.60208(7) 0.0219(2) Uani 1 1 d . . . . .
C6 C 0.57846(5) 0.44168(12) 0.65706(8) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.61271(5) 0.56417(13) 0.67384(8) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.56502(6) 0.67151(12) 0.64874(8) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.58026(6) 0.82284(13) 0.65962(9) 0.0310(3) Uani 1 1 d . . . . .
H9A H 0.5511 0.8611 0.711 0.037 Uiso 1 1 calc R U . . .
H9B H 0.5672 0.8724 0.6017 0.037 Uiso 1 1 calc R U . . .
C10 C 0.65944(6) 0.84645(14) 0.68068(9) 0.0325(3) Uani 1 1 d . . . . .
H10A H 0.6871 0.839 0.6223 0.039 Uiso 1 1 calc R U . . .
H10B H 0.6661 0.9414 0.7057 0.039 Uiso 1 1 calc R U . . .
C11 C 0.68753(6) 0.74099(14) 0.75077(9) 0.0345(3) Uani 1 1 d . . . . .
H11A H 0.6582 0.7447 0.8079 0.041 Uiso 1 1 calc R U . . .
H11B H 0.737 0.7654 0.7678 0.041 Uiso 1 1 calc R U . . .
C12 C 0.68585(6) 0.59378(14) 0.71109(9) 0.0307(3) Uani 1 1 d . . . . .
H12A H 0.7214 0.5849 0.6606 0.037 Uiso 1 1 calc R U . . .
H12B H 0.6979 0.5259 0.7604 0.037 Uiso 1 1 calc R U . . .
C13 C 0.60540(6) 0.29629(13) 0.66679(9) 0.0302(3) Uani 1 1 d . . . . .
H13A H 0.5672 0.2373 0.6929 0.036 Uiso 1 1 calc R U . . .
H13B H 0.6456 0.2955 0.7112 0.036 Uiso 1 1 calc R U . . .
C14 C 0.62994(7) 0.23485(14) 0.57458(10) 0.0387(3) Uani 1 1 d . . . . .
H14A H 0.5894 0.2288 0.5318 0.058 Uiso 1 1 calc R U . . .
H14B H 0.6494 0.1417 0.5852 0.058 Uiso 1 1 calc R U . . .
H14C H 0.6667 0.2945 0.5474 0.058 Uiso 1 1 calc R U . . .
N1 N 0.39396(5) 0.47024(11) 0.57753(7) 0.0244(2) Uani 1 1 d . . . . .
N2 N 0.45580(5) 0.26377(10) 0.60862(7) 0.0261(2) Uani 1 1 d . . . . .
N3 N 0.51192(4) 0.47945(10) 0.62245(6) 0.0232(2) Uani 1 1 d . . . . .
N4 N 0.50383(5) 0.62169(10) 0.61767(7) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.27745(4) 0.47820(10) 0.53604(7) 0.0373(2) Uani 1 1 d . . . . .
H1 H 0.3975(7) 0.5616(16) 0.5754(10) 0.038(4) Uiso 1 1 d . . . . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0976
-1 0 0 0.0976
0 0 1 0.1121
0 0 -1 0.1121
0 1 0 0.1658
0 -1 0 0.1578
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 119.36(11) . . ?
O1 C1 C2 127.73(10) . . ?
N1 C1 C2 112.91(10) . . ?
C3 C2 C1 120.59(10) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 N2 123.31(11) . . ?
C2 C3 C4 122.44(11) . . ?
N2 C3 C4 114.24(10) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 N1 124.98(10) . . ?
N2 C5 N3 120.65(10) . . ?
N1 C5 N3 114.36(10) . . ?
C7 C6 N3 105.13(10) . . ?
C7 C6 C13 129.22(10) . . ?
N3 C6 C13 125.55(10) . . ?
C6 C7 C8 106.66(9) . . ?
C6 C7 C12 131.18(11) . . ?
C8 C7 C12 122.16(11) . . ?
N4 C8 C7 111.85(10) . . ?
N4 C8 C9 123.75(11) . . ?
C7 C8 C9 124.35(10) . . ?
C8 C9 C10 110.55(10) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 111.56(10) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
C10 C11 C12 111.32(11) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
C7 C12 C11 109.13(10) . . ?
C7 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C7 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C6 C13 C14 112.63(10) . . ?
C6 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C6 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 C1 122.51(10) . . ?
C5 N1 H1 117.7(9) . . ?
C1 N1 H1 119.8(9) . . ?
C5 N2 C3 115.69(10) . . ?
N4 N3 C6 112.06(9) . . ?
N4 N3 C5 117.52(9) . . ?
C6 N3 C5 130.06(10) . . ?
C8 N4 N3 104.29(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2287(14) . ?
C1 N1 1.4009(14) . ?
C1 C2 1.4302(17) . ?
C2 C3 1.3599(16) . ?
C2 H2 0.95 . ?
C3 N2 1.3837(14) . ?
C3 C4 1.4919(17) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 N2 1.2913(15) . ?
C5 N1 1.3526(14) . ?
C5 N3 1.3978(13) . ?
C6 C7 1.3648(16) . ?
C6 N3 1.3944(13) . ?
C6 C13 1.4946(17) . ?
C7 C8 1.4146(16) . ?
C7 C12 1.5029(14) . ?
C8 N4 1.3240(14) . ?
C8 C9 1.4925(17) . ?
C9 C10 1.5360(15) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5245(19) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.5276(18) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.5228(19) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N1 H1 0.882(15) . ?
N3 N4 1.3790(14) . ?
