#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151497.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_7151497
loop_
_publ_author_name
'Blake, Alexander J.'
'Clarke, David'
'Mares, Richard W.'
'McNab, Hamish'
_publ_section_title
;
 Synthesis and chemistry of 3-tert-butyl-1,5-diaminopyrazole.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4268
_journal_page_last               4274
_journal_paper_doi               10.1039/b306058f
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C11 H16 N4 O'
_chemical_formula_sum            'C11 H16 N4 O'
_chemical_formula_weight         220.28
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens
'N-H from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_audit_creation_method           'SHELXL-97 plus manual editing'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.483(5)
_cell_length_b                   9.356(4)
_cell_length_c                   12.297(3)
_cell_measurement_reflns_used    37
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      12
_cell_volume                     1183.4(8)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1987a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987b)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       omega/2theta
_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  0.085
_diffrn_reflns_av_sigmaI/netI    0.095
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2457
_diffrn_reflns_theta_full        22.58
_diffrn_reflns_theta_max         22.58
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       lath
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    'distance restrained; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1554
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.139
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.099P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.136
_refine_ls_wR_factor_ref         0.171
_reflns_number_gt                869
_reflns_number_total             1554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306058f.txt
_cod_data_source_block           BUN4ME
_cod_database_code               7151497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4702(3) 0.0843(3) 0.3111(3) 0.0451(9) Uani 1 1 d D . .
H1 H 0.5605 0.1038 0.3001 0.068 Uiso 1 1 d RD . .
C2 C 0.4344(4) -0.0424(5) 0.3504(3) 0.0497(11) Uani 1 1 d . . .
O2 O 0.5144(3) -0.1311(3) 0.3890(3) 0.0691(10) Uani 1 1 d . . .
C3 C 0.2908(4) -0.0633(5) 0.3406(4) 0.0567(12) Uani 1 1 d . . .
H3A H 0.2499 -0.0591 0.2628 0.068 Uiso 1 1 calc R . .
H3B H 0.2756 -0.1581 0.3674 0.068 Uiso 1 1 calc R . .
C4 C 0.2273(4) 0.0436(5) 0.4026(3) 0.0458(11) Uani 1 1 d . . .
C4M C 0.1724(5) -0.0055(6) 0.4983(4) 0.0698(14) Uani 1 1 d . . .
H4M1 H 0.1133 -0.0831 0.4757 0.105 Uiso 1 1 calc R . .
H4M2 H 0.1268 0.0720 0.5249 0.105 Uiso 1 1 calc R . .
H4M3 H 0.2415 -0.0371 0.5563 0.105 Uiso 1 1 calc R . .
N5 N 0.2146(3) 0.1769(4) 0.3784(3) 0.0465(9) Uani 1 1 d . . .
N6 N 0.2723(3) 0.2244(3) 0.2924(2) 0.0392(8) Uani 1 1 d . . .
N7 N 0.2197(3) 0.3469(3) 0.2428(2) 0.0408(9) Uani 1 1 d . . .
C8 C 0.3049(4) 0.3914(4) 0.1827(3) 0.0380(10) Uani 1 1 d . . .
C81 C 0.2824(4) 0.5280(4) 0.1173(3) 0.0446(11) Uani 1 1 d . . .
C82 C 0.1573(5) 0.6001(5) 0.1310(5) 0.0781(16) Uani 1 1 d . . .
H82A H 0.0851 0.5387 0.1028 0.117 Uiso 1 1 calc R . .
H82B H 0.1477 0.6886 0.0906 0.117 Uiso 1 1 calc R . .
H82C H 0.1596 0.6188 0.2081 0.117 Uiso 1 1 calc R . .
C83 C 0.2834(7) 0.4989(6) -0.0034(4) 0.0885(18) Uani 1 1 d . . .
H83A H 0.2127 0.4365 -0.0332 0.133 Uiso 1 1 calc R . .
H83B H 0.3642 0.4545 -0.0099 0.133 Uiso 1 1 calc R . .
H83C H 0.2741 0.5874 -0.0437 0.133 Uiso 1 1 calc R . .
C84 C 0.3962(5) 0.6268(5) 0.1626(5) 0.0862(17) Uani 1 1 d . . .
H84A H 0.3856 0.7156 0.1229 0.103 Uiso 1 1 calc R . .
H84B H 0.4761 0.5824 0.1537 0.103 Uiso 1 1 calc R . .
H84C H 0.3984 0.6444 0.2399 0.103 Uiso 1 1 calc R . .
C9 C 0.4108(4) 0.2975(4) 0.1935(3) 0.0442(11) Uani 1 1 d . . .
H9 H 0.4817 0.3045 0.1586 0.053 Uiso 1 1 calc R . .
C9A C 0.3889(3) 0.1945(4) 0.2650(3) 0.0382(10) 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 0.0000 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'
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
C2 N1 C9A 127.1(3) . . ?
C2 N1 H1 122.7 . . ?
C9A N1 H1 109.4 . . ?
O2 C2 N1 121.3(4) . . ?
O2 C2 C3 123.4(4) . . ?
N1 C2 C3 115.2(4) . . ?
C4 C3 C2 114.3(4) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N5 C4 C4M 116.5(4) . . ?
N5 C4 C3 124.8(4) . . ?
C4M C4 C3 118.6(4) . . ?
C4 C4M H4M1 109.5 . . ?
C4 C4M H4M2 109.5 . . ?
H4M1 C4M H4M2 109.5 . . ?
C4 C4M H4M3 109.5 . . ?
H4M1 C4M H4M3 109.5 . . ?
H4M2 C4M H4M3 109.5 . . ?
C4 N5 N6 116.5(3) . . ?
C9A N6 N7 111.6(3) . . ?
C9A N6 N5 131.9(3) . . ?
N7 N6 N5 114.3(3) . . ?
C8 N7 N6 104.8(3) . . ?
N7 C8 C9 110.8(3) . . ?
N7 C8 C81 120.7(3) . . ?
C9 C8 C81 128.5(3) . . ?
C8 C81 C83 110.0(3) . . ?
C8 C81 C82 111.7(3) . . ?
C83 C81 C82 111.1(4) . . ?
C8 C81 C84 106.8(4) . . ?
C83 C81 C84 108.3(4) . . ?
C82 C81 C84 108.8(4) . . ?
C81 C82 H82A 109.5 . . ?
C81 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
C81 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
C81 C83 H83A 109.5 . . ?
C81 C83 H83B 109.5 . . ?
H83A C83 H83B 109.5 . . ?
C81 C83 H83C 109.5 . . ?
H83A C83 H83C 109.5 . . ?
H83B C83 H83C 109.5 . . ?
C81 C84 H84A 109.5 . . ?
C81 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C81 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
C9A C9 C8 106.1(3) . . ?
C9A C9 H9 127.0 . . ?
C8 C9 H9 127.0 . . ?
C9 C9A N6 106.7(3) . . ?
C9 C9A N1 128.8(3) . . ?
N6 C9A N1 124.3(3) . . ?
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
N1 C2 1.360(5) . ?
N1 C9A 1.386(5) . ?
N1 H1 1.00 . ?
C2 O2 1.210(5) . ?
C2 C3 1.500(6) . ?
C3 C4 1.490(6) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 N5 1.283(5) . ?
C4 C4M 1.480(6) . ?
C4M H4M1 0.96 . ?
C4M H4M2 0.96 . ?
C4M H4M3 0.96 . ?
N5 N6 1.389(4) . ?
N6 C9A 1.358(5) . ?
N6 N7 1.363(4) . ?
N7 C8 1.331(4) . ?
C8 C9 1.402(5) . ?
C8 C81 1.504(5) . ?
C81 C83 1.511(6) . ?
C81 C82 1.513(6) . ?
C81 C84 1.526(7) . ?
C82 H82A 0.96 . ?
C82 H82B 0.96 . ?
C82 H82C 0.96 . ?
C83 H83A 0.96 . ?
C83 H83B 0.96 . ?
C83 H83C 0.96 . ?
C84 H84A 0.96 . ?
C84 H84B 0.96 . ?
C84 H84C 0.96 . ?
C9 C9A 1.354(5) . ?
C9 H9 0.93 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N7 1.00 1.99 2.968(4) 167 4_665
N1 H1 N5 1.00 2.67 3.380(5) 128 4_665
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1 C2 O2 -180.0(4) . . . . ?
C9A N1 C2 C3 0.9(6) . . . . ?
O2 C2 C3 C4 119.7(5) . . . . ?
N1 C2 C3 C4 -61.1(5) . . . . ?
C2 C3 C4 N5 67.6(6) . . . . ?
C2 C3 C4 C4M -113.4(5) . . . . ?
C4M C4 N5 N6 176.6(3) . . . . ?
C3 C4 N5 N6 -4.3(6) . . . . ?
C4 N5 N6 C9A -41.5(6) . . . . ?
C4 N5 N6 N7 157.2(3) . . . . ?
C9A N6 N7 C8 1.0(4) . . . . ?
N5 N6 N7 C8 166.1(3) . . . . ?
N6 N7 C8 C9 0.3(4) . . . . ?
N6 N7 C8 C81 -178.3(3) . . . . ?
N7 C8 C81 C83 -123.6(4) . . . . ?
C9 C8 C81 C83 58.1(5) . . . . ?
N7 C8 C81 C82 0.2(5) . . . . ?
C9 C8 C81 C82 -178.1(4) . . . . ?
N7 C8 C81 C84 119.1(4) . . . . ?
C9 C8 C81 C84 -59.2(5) . . . . ?
N7 C8 C9 C9A -1.4(4) . . . . ?
C81 C8 C9 C9A 177.0(4) . . . . ?
C8 C9 C9A N6 1.9(4) . . . . ?
C8 C9 C9A N1 -173.4(4) . . . . ?
N7 N6 C9A C9 -1.8(4) . . . . ?
N5 N6 C9A C9 -163.5(4) . . . . ?
N7 N6 C9A N1 173.7(3) . . . . ?
N5 N6 C9A N1 12.0(6) . . . . ?
C2 N1 C9A C9 -155.7(4) . . . . ?
C2 N1 C9A N6 29.8(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141418
