#------------------------------------------------------------------------------
#$Date: 2019-11-24 22:46:02 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239644 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/69/4516946.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_4516946
loop_
_publ_author_name
'Kuleshova, Olena'
'Khilya, Olga'
'Volovenko, Yulian'
'Mallet-Ladeira, Sonia'
'Dyakonenko, Viktoriya'
'Gras, Emmanuel'
_publ_section_title
;
 Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and
 Their Further Transformations.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              8911
_journal_page_last               8927
_journal_paper_doi               10.1021/acsomega.7b01419
_journal_volume                  2
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H17 N5 S'
_chemical_formula_sum            'C14 H17 N5 S'
_chemical_formula_weight         287.39
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 110.7050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6381(4)
_cell_length_b                   12.9175(5)
_cell_length_c                   12.0791(4)
_cell_measurement_reflns_used    8617
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.39
_cell_measurement_wavelength     0.71073
_cell_volume                     1406.72(9)
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa Nonius'
_diffrn_measurement_method       ω-φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16450
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         2.395
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0336
_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)+(0.0548P)²+0.2542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1
_reflns_Friedel_coverage         0
_reflns_number_gt                3717
_reflns_number_total             4265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao7b01419_si_002.cif
_cod_data_source_block           11a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4516946
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
H5A H 0.2894(17) 0.1878(13) 0.5611(14) 0.042(4) Uiso 1 1 d . .
H4A H -0.2307(17) -0.0671(12) 0.2915(14) 0.040(4) Uiso 1 1 d . .
H2B H -0.3205(19) 0.1293(13) -0.0716(15) 0.047(5) Uiso 1 1 d . .
H2A H -0.4509(17) 0.0792(11) -0.0620(13) 0.032(4) Uiso 1 1 d . .
C1 C 0.03517(11) 0.20488(8) -0.06026(9) 0.0239(2) Uani 1 1 d . .
C2 C 0.01475(14) 0.26295(9) -0.16241(11) 0.0335(2) Uani 1 1 d . .
H2 H -0.082091 0.280545 -0.214368 0.04 Uiso 1 1 calc R U
C3 C 0.13836(16) 0.29426(10) -0.18625(12) 0.0395(3) Uani 1 1 d . .
H3 H 0.126009 0.334083 -0.255211 0.047 Uiso 1 1 calc R U
C4 C 0.28097(15) 0.26840(10) -0.11084(12) 0.0384(3) Uani 1 1 d . .
H4 H 0.363963 0.290114 -0.129956 0.046 Uiso 1 1 calc R U
C5 C 0.30376(13) 0.21195(10) -0.00910(11) 0.0323(2) Uani 1 1 d . .
H5 H 0.40108 0.19519 0.042609 0.039 Uiso 1 1 calc R U
C6 C 0.17931(11) 0.18017(8) 0.01554(9) 0.0238(2) Uani 1 1 d . .
C7 C -0.02546(10) 0.11326(7) 0.07197(9) 0.01998(18) Uani 1 1 d . .
C8 C -0.11936(10) 0.06351(7) 0.12553(8) 0.02002(18) Uani 1 1 d . .
C9 C -0.27777(10) 0.06028(7) 0.07502(8) 0.02011(18) Uani 1 1 d . .
C10 C -0.08435(11) 0.00354(8) 0.22843(8) 0.02148(19) Uani 1 1 d . .
C11 C 0.06124(12) -0.02150(8) 0.32265(9) 0.0252(2) Uani 1 1 d . .
H11A H 0.135302 -0.036412 0.285169 0.03 Uiso 1 1 calc R U
H11B H 0.050031 -0.084558 0.365307 0.03 Uiso 1 1 calc R U
C12 C 0.11831(12) 0.06725(8) 0.41166(9) 0.0255(2) Uani 1 1 d . .
H12A H 0.112882 0.132782 0.367827 0.031 Uiso 1 1 calc R U
H12B H 0.052931 0.074156 0.458657 0.031 Uiso 1 1 calc R U
C13 C 0.27683(12) 0.05074(9) 0.49525(9) 0.0280(2) Uani 1 1 d . .
H13A H 0.2879 -0.020498 0.527438 0.034 Uiso 1 1 calc R U
H13B H 0.345548 0.05898 0.451318 0.034 Uiso 1 1 calc R U
C14 C 0.47409(14) 0.12432(12) 0.66314(11) 0.0406(3) Uani 1 1 d . .
H14A H 0.501021 0.05707 0.702455 0.061 Uiso 1 1 calc R U
H14B H 0.49671 0.179259 0.722871 0.061 Uiso 1 1 calc R U
H14C H 0.530839 0.135839 0.611057 0.061 Uiso 1 1 calc R U
N1 N -0.07838(9) 0.16674(7) -0.02661(8) 0.02401(18) Uani 1 1 d . .
N2 N -0.36653(10) 0.10986(8) -0.02616(8) 0.02589(19) Uani 1 1 d . .
N3 N -0.33473(9) 0.00436(7) 0.14089(7) 0.02268(18) Uani 1 1 d . .
N4 N -0.21335(10) -0.02912(7) 0.23414(8) 0.02370(18) Uani 1 1 d . .
N5 N 0.31504(11) 0.12552(8) 0.59288(8) 0.0292(2) Uani 1 1 d . .
S1 S 0.16946(3) 0.10582(2) 0.13202(2) 0.02515(8) Uani 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'
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
N1 C1 C2 124.79(10)
N1 C1 C6 115.46(9)
C2 C1 C6 119.73(10)
C3 C2 C1 118.60(12)
C3 C2 H2 120.7
C1 C2 H2 120.7
C2 C3 C4 121.14(12)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 121.25(11)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 117.88(11)
C4 C5 H5 121.1
C6 C5 H5 121.1
C5 C6 C1 121.39(10)
C5 C6 S1 129.33(9)
C1 C6 S1 109.25(8)
N1 C7 C8 122.60(9)
N1 C7 S1 114.70(7)
C8 C7 S1 122.69(7)
C10 C8 C9 104.38(8)
C10 C8 C7 130.87(9)
C9 C8 C7 124.62(9)
N3 C9 N2 121.72(9)
N3 C9 C8 111.41(8)
N2 C9 C8 126.83(9)
N4 C10 C8 106.47(9)
N4 C10 C11 122.10(9)
C8 C10 C11 131.39(9)
C10 C11 C12 112.26(8)
C10 C11 H11A 109.2
C12 C11 H11A 109.2
C10 C11 H11B 109.2
C12 C11 H11B 109.2
H11A C11 H11B 107.9
C13 C12 C11 112.82(9)
C13 C12 H12A 109
C11 C12 H12A 109
C13 C12 H12B 109
C11 C12 H12B 109
H12A C12 H12B 107.8
N5 C13 C12 110.45(9)
N5 C13 H13A 109.6
C12 C13 H13A 109.6
N5 C13 H13B 109.6
C12 C13 H13B 109.6
H13A C13 H13B 108.1
N5 C14 H14A 109.5
N5 C14 H14B 109.5
H14A C14 H14B 109.5
N5 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 C1 111.04(8)
C9 N2 H2B 113.9(11)
C9 N2 H2A 114.1(10)
H2B N2 H2A 114.9(15)
C9 N3 N4 104.44(8)
C10 N4 N3 113.30(9)
C10 N4 H4A 129.2(10)
N3 N4 H4A 117.4(10)
C14 N5 C13 111.85(10)
C14 N5 H5A 109.5(10)
C13 N5 H5A 107.2(10)
C6 S1 C7 89.54(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3858(13)
C1 C2 1.3972(15)
C1 C6 1.4038(15)
C2 C3 1.3814(18)
C2 H2 0.95
C3 C4 1.395(2)
C3 H3 0.95
C4 C5 1.3781(18)
C4 H4 0.95
C5 C6 1.3958(15)
C5 H5 0.95
C6 S1 1.7337(11)
C7 N1 1.3137(13)
C7 C8 1.4369(14)
C7 S1 1.7610(10)
C8 C10 1.4008(13)
C8 C9 1.4305(13)
C9 N3 1.3286(13)
C9 N2 1.3770(13)
C10 N4 1.3376(13)
C10 C11 1.4965(13)
C11 C12 1.5345(14)
C11 H11A 0.99
C11 H11B 0.99
C12 C13 1.5194(14)
C12 H12A 0.99
C12 H12B 0.99
C13 N5 1.4670(14)
C13 H13A 0.99
C13 H13B 0.99
C14 N5 1.4665(15)
C14 H14A 0.98
C14 H14B 0.98
C14 H14C 0.98
N2 H2B 0.856(18)
N2 H2A 0.869(15)
N3 N4 1.3757(12)
N4 H4A 0.911(17)
N5 H5A 0.888(16)
