#------------------------------------------------------------------------------
#$Date: 2019-11-24 22:46:02 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239644 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/69/4516947.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_4516947
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         'C16 H20 N6 O, 0.5(C6 H12), H2 O'
_chemical_formula_sum            'C19 H28 N6 O2'
_chemical_formula_weight         372.47
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 110.663(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4490(5)
_cell_length_b                   19.1742(7)
_cell_length_c                   10.5635(5)
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.919
_cell_measurement_theta_min      3.799
_cell_measurement_wavelength     0.71073
_cell_volume                     1980.27(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (A. Altomare, 1993)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            37526
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0808P)²+1.6755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                3019
_reflns_number_total             3620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b01419_si_002.cif
_cod_data_source_block           15a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516947
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
C1 C 1.0157(2) 0.86310(11) 0.3247(2) 0.0251(5) Uani 1 1 d .
C2 C 0.8987(2) 0.86889(12) 0.3598(2) 0.0337(5) Uani 1 1 d .
H2 H 0.8258 0.8985 0.3091 0.04 Uiso 1 1 calc R
C3 C 0.8893(3) 0.83184(14) 0.4674(2) 0.0397(6) Uani 1 1 d .
H3 H 0.8096 0.8355 0.4906 0.048 Uiso 1 1 calc R
C4 C 0.9970(3) 0.78874(13) 0.5427(2) 0.0384(6) Uani 1 1 d .
H4 H 0.9897 0.763 0.6168 0.046 Uiso 1 1 calc R
C5 C 1.1131(3) 0.78304(12) 0.5111(2) 0.0340(5) Uani 1 1 d .
H5 H 1.1863 0.7542 0.5643 0.041 Uiso 1 1 calc R
C6 C 1.1243(2) 0.81970(11) 0.4000(2) 0.0259(5) Uani 1 1 d .
C7 C 1.0304(2) 0.89939(10) 0.2098(2) 0.0233(4) Uani 1 1 d .
C8 C 1.2446(2) 0.84733(10) 0.2624(2) 0.0226(4) Uani 1 1 d .
C9 C 1.3652(2) 0.83807(11) 0.2254(2) 0.0236(4) Uani 1 1 d .
C10 C 1.4547(2) 0.78109(11) 0.2646(2) 0.0264(5) Uani 1 1 d .
C11 C 1.6491(3) 0.73789(13) 0.1988(3) 0.0396(6) Uani 1 1 d .
H11A H 1.6893 0.7146 0.2865 0.059 Uiso 1 1 calc R
H11B H 1.7212 0.7616 0.1761 0.059 Uiso 1 1 calc R
H11C H 1.6046 0.7032 0.129 0.059 Uiso 1 1 calc R
C12 C 1.4171(2) 0.87822(11) 0.1412(2) 0.0241(5) Uani 1 1 d .
C13 C 1.3715(2) 0.94693(11) 0.0725(2) 0.0265(5) Uani 1 1 d .
H13A H 1.45 0.9795 0.0998 0.032 Uiso 1 1 calc R
H13B H 1.3001 0.9667 0.1035 0.032 Uiso 1 1 calc R
C14 C 1.3145(2) 0.94150(11) -0.0822(2) 0.0282(5) Uani 1 1 d .
H14A H 1.2923 0.989 -0.1205 0.034 Uiso 1 1 calc R
H14B H 1.3867 0.9224 -0.1129 0.034 Uiso 1 1 calc R
C15 C 1.1886(2) 0.89648(12) -0.1382(2) 0.0295(5) Uani 1 1 d .
H15A H 1.1573 0.8965 -0.2383 0.035 Uiso 1 1 calc R
H15B H 1.2116 0.8479 -0.1068 0.035 Uiso 1 1 calc R
C16 C 0.9434(2) 0.88810(14) -0.1658(3) 0.0397(6) Uani 1 1 d .
H16A H 0.917 0.8961 -0.2633 0.06 Uiso 1 1 calc R
H16B H 0.8736 0.9077 -0.1339 0.06 Uiso 1 1 calc R
H16C H 0.9516 0.8379 -0.1476 0.06 Uiso 1 1 calc R
C17 C 0.6184(7) 0.5035(4) -0.0506(6) 0.138(2) Uani 1 1 d .
H17A H 0.7095 0.4837 -0.0387 0.165 Uiso 1 1 calc R
H17B H 0.5975 0.5401 -0.121 0.165 Uiso 1 1 calc R
C18 C 0.6197(5) 0.5351(3) 0.0829(5) 0.116(2) Uani 1 1 d .
H18A H 0.6643 0.5011 0.1556 0.139 Uiso 1 1 calc R
H18B H 0.6787 0.577 0.101 0.139 Uiso 1 1 calc R
C19 C 0.4919(6) 0.5549(2) 0.0951(6) 0.1020(15) Uani 1 1 d .
H19A H 0.4565 0.5969 0.0393 0.122 Uiso 1 1 calc R
H19B H 0.5081 0.5674 0.1905 0.122 Uiso 1 1 calc R
N1 N 1.24046(18) 0.81161(9) 0.36836(18) 0.0270(4) Uani 1 1 d .
N2 N 1.14471(17) 0.89021(9) 0.18175(17) 0.0225(4) Uani 1 1 d .
N3 N 1.4497(2) 0.72426(11) 0.3393(2) 0.0364(5) Uani 1 1 d .
N4 N 1.54850(18) 0.78870(9) 0.20585(19) 0.0286(4) Uani 1 1 d .
N5 N 1.52691(18) 0.84861(9) 0.12916(19) 0.0285(4) Uani 1 1 d .
N6 N 1.07636(18) 0.92220(10) -0.09428(19) 0.0261(4) Uani 1 1 d .
O1 O 0.93521(15) 0.93814(8) 0.13389(15) 0.0290(4) Uani 1 1 d .
O2 O 0.3078(2) 0.12782(10) 0.02443(19) 0.0428(5) Uani 1 1 d .
H102 H 0.224(3) 0.1077(16) -0.026(3) 0.055(8) Uiso 1 1 d .
H3A H 1.402(3) 0.7310(14) 0.392(3) 0.041(7) Uiso 1 1 d .
H3B H 1.527(3) 0.6971(15) 0.375(3) 0.042(7) Uiso 1 1 d .
H202 H 0.355(3) 0.1288(16) -0.027(3) 0.055(9) Uiso 1 1 d .
H6A H 1.064(3) 0.9702(15) -0.106(3) 0.036(7) Uiso 1 1 d .
H6B H 1.100(3) 0.9141(13) -0.002(3) 0.035(7) 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_
_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
C2 C1 C6 120.2(2) . .
C2 C1 C7 122.82(19) . .
C6 C1 C7 117.01(18) . .
C3 C2 C1 120.1(2) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C2 C3 C4 120.0(2) . .
C2 C3 H3 120 . .
C4 C3 H3 120 . .
C5 C4 C3 120.8(2) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 120.3(2) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
N1 C6 C1 122.28(19) . .
N1 C6 C5 119.06(19) . .
C1 C6 C5 118.7(2) . .
O1 C7 N2 119.75(18) . .
O1 C7 C1 121.10(18) . .
N2 C7 C1 119.13(18) . .
N1 C8 N2 126.38(19) . .
N1 C8 C9 116.92(18) . .
N2 C8 C9 116.66(18) . .
C10 C9 C12 104.22(18) . .
C10 C9 C8 124.42(19) . .
C12 C9 C8 131.28(19) . .
N4 C10 N3 122.74(19) . .
N4 C10 C9 107.36(18) . .
N3 C10 C9 129.7(2) . .
N4 C11 H11A 109.5 . .
N4 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N4 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N5 C12 C9 111.23(18) . .
N5 C12 C13 117.92(18) . .
C9 C12 C13 130.80(18) . .
C12 C13 C14 113.22(17) . .
C12 C13 H13A 108.9 . .
C14 C13 H13A 108.9 . .
C12 C13 H13B 108.9 . .
C14 C13 H13B 108.9 . .
H13A C13 H13B 107.7 . .
C15 C14 C13 114.45(17) . .
C15 C14 H14A 108.6 . .
C13 C14 H14A 108.6 . .
C15 C14 H14B 108.6 . .
C13 C14 H14B 108.6 . .
H14A C14 H14B 107.6 . .
N6 C15 C14 111.21(18) . .
N6 C15 H15A 109.4 . .
C14 C15 H15A 109.4 . .
N6 C15 H15B 109.4 . .
C14 C15 H15B 109.4 . .
H15A C15 H15B 108 . .
N6 C16 H16A 109.5 . .
N6 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
N6 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 C19 109.2(5) . 3_665
C18 C17 H17A 109.8 . .
C19 C17 H17A 109.8 3_665 .
C18 C17 H17B 109.8 . .
C19 C17 H17B 109.8 3_665 .
H17A C17 H17B 108.3 . .
C19 C18 C17 118.8(4) . .
C19 C18 H18A 107.6 . .
C17 C18 H18A 107.6 . .
C19 C18 H18B 107.6 . .
C17 C18 H18B 107.6 . .
H18A C18 H18B 107 . .
C18 C19 C17 113.3(4) . 3_665
C18 C19 H19A 108.9 . .
C17 C19 H19A 108.9 3_665 .
C18 C19 H19B 108.9 . .
C17 C19 H19B 108.9 3_665 .
H19A C19 H19B 107.7 . .
C8 N1 C6 116.15(18) . .
C7 N2 C8 119.05(17) . .
C10 N3 H3A 113.4(18) . .
C10 N3 H3B 119.1(17) . .
H3A N3 H3B 116(2) . .
C10 N4 N5 111.61(16) . .
C10 N4 C11 127.64(19) . .
N5 N4 C11 119.99(18) . .
C12 N5 N4 105.58(17) . .
C16 N6 C15 113.28(18) . .
C16 N6 H6A 107.9(16) . .
C15 N6 H6A 111.9(16) . .
C16 N6 H6B 108.6(16) . .
C15 N6 H6B 108.6(16) . .
H6A N6 H6B 106(2) . .
H102 O2 H202 107(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.402(3) .
C1 C6 1.406(3) .
C1 C7 1.453(3) .
C2 C3 1.373(3) .
C2 H2 0.95 .
C3 C4 1.396(4) .
C3 H3 0.95 .
C4 C5 1.372(3) .
C4 H4 0.95 .
C5 C6 1.407(3) .
C5 H5 0.95 .
C6 N1 1.377(3) .
C7 O1 1.273(3) .
C7 N2 1.341(3) .
C8 N1 1.325(3) .
C8 N2 1.365(3) .
C8 C9 1.457(3) .
C9 C10 1.402(3) .
C9 C12 1.421(3) .
C10 N4 1.341(3) .
C10 N3 1.357(3) .
C11 N4 1.454(3) .
C11 H11A 0.98 .
C11 H11B 0.98 .
C11 H11C 0.98 .
C12 N5 1.326(3) .
C12 C13 1.498(3) .
C13 C14 1.532(3) .
C13 H13A 0.99 .
C13 H13B 0.99 .
C14 C15 1.509(3) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 N6 1.489(3) .
C15 H15A 0.99 .
C15 H15B 0.99 .
C16 N6 1.479(3) .
C16 H16A 0.98 .
C16 H16B 0.98 .
C16 H16C 0.98 .
C17 C18 1.530(8) .
C17 C19 1.555(8) 3_665
C17 H17A 0.99 .
C17 H17B 0.99 .
C18 C19 1.437(7) .
C18 H18A 0.99 .
C18 H18B 0.99 .
C19 C17 1.555(8) 3_665
C19 H19A 0.99 .
C19 H19B 0.99 .
N3 H3A 0.88(3) .
N3 H3B 0.92(3) .
N4 N5 1.378(3) .
N6 H6A 0.93(3) .
N6 H6B 0.92(3) .
O2 H102 0.93(3) .
O2 H202 0.86(4) .
