Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations.
Kuleshova, Olena; Khilya, Olga; Volovenko, Yulian; Mallet-Ladeira, Sonia; Dyakonenko, Viktoriya; Gras, Emmanuel; ACS omega 2 (2017) 8911–8927; doi:10.1021/acsomega.7b01419

data_4516941
_publ_contact_author
;
  Dyakonenko V.V.
  STC "Institute for Single Crystals"
  National Academy of Sciences of Ukraine
  60 Nauki ave.
  Kharkiv, 61001
  Ukraine
;
_publ_section_title
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 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_formula_moiety         'C14 H14 N4'
_chemical_formula_sum            'C14 H14 N4'
_chemical_formula_weight         238.29
_space_group_crystal_system      tetragonal
_space_group_IT_number           133
_space_group_name_Hall           '-P 4ac 2b'
_space_group_name_H-M_alt        'P 42/n b c :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.5736(3)
_cell_length_b                   14.5736(3)
_cell_length_c                   22.9510(13)
_cell_measurement_reflns_used    2128
_cell_measurement_temperature    293
_cell_measurement_theta_max      23.7470
_cell_measurement_theta_min      3.2250
_cell_volume                     4874.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -98.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3049    0.0000    0.0000 86

  2 omega  -44.00   42.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3049   57.0000    0.0000 86

  3 omega  -19.00   10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3049  -99.0000 -120.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0142679000
_diffrn_orient_matrix_UB_12      0.0336767000
_diffrn_orient_matrix_UB_13      0.0204473000
_diffrn_orient_matrix_UB_21      -0.0386397000
_diffrn_orient_matrix_UB_22      0.0101878000
_diffrn_orient_matrix_UB_23      -0.0176178000
_diffrn_orient_matrix_UB_31      -0.0259817000
_diffrn_orient_matrix_UB_32      -0.0336003000
_diffrn_orient_matrix_UB_33      0.0150419000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16729
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0545P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1438
_reflns_number_total             2807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01419_si_002.cif
_cod_data_source_block           7a
_cod_original_sg_symbol_H-M      'P 42/n b c'
_cod_database_code               4516941
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C12A = C11-C12B = C13-C12A = C13-C12B
 1.535 with sigma of 0.005
 C11-C12A \\sim C11-C12B
 with sigma of 0.005
 C13-C12A \\sim C13-C12B
 with sigma of 0.005
3. Others
 Fixed Sof: H11C(0.5) H11D(0.5) H11A(0.5) H11B(0.5) C12A(0.5) H12A(0.5)
 H12B(0.5) C12B(0.5) H12C(0.5) H12D(0.5) H13C(0.5) H13D(0.5) H13A(0.5) H13B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11C,H11D), C11(H11A,H11B), C12A(H12A,H12B), C12B(H12C,H12D), C13(H13C,
 H13D), C13(H13A,H13B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'