#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/71/2017151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017151
loop_
_publ_author_name
'Castillo, Juan C.'
'Abonía, Rodrigo'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Seven 5-benzylamino-3-tert-butyl-1-phenyl-1H-pyrazoles:
 unexpected isomorphisms, and hydrogen-bonded supramolecular structures
 in zero, one and two dimensions
;
_journal_coeditor_code           SK3324
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o303
_journal_page_last               o310
_journal_paper_doi               10.1107/S0108270109018964
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H25 N3'
_chemical_formula_moiety         'C21 H25 N3'
_chemical_formula_sum            'C21 H25 N3'
_chemical_formula_weight         319.44
_chemical_name_systematic
;
3-tert-butyl-5-(4-methylbenzylamino)-1-phenyl-1H-pyrazole
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7749(13)
_cell_length_b                   10.7749(13)
_cell_length_c                   30.868(3)
_cell_measurement_reflns_used    2412
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.98
_cell_volume                     3583.7(7)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22266
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0515
_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/[σ²(Fo²)+(0.0473P)²+0.8586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                1598
_reflns_number_total             2412
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3324.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3583.6(7)
_cod_database_code               2017151
_cod_database_fobs_code          2017151
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'-y, -x, -z+1/2'
'y, x, -z'
'y+1/2, -x+1/2, z+1/4'
'-y+1/2, x+1/2, z+3/4'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.6755(2) 0.1622(2) 0.46533(7) 0.0207(6) Uani d . 1 . .
N N2 0.7693(2) 0.0822(2) 0.45423(7) 0.0206(6) Uani d . 1 . .
C C3 0.7206(3) 0.0090(3) 0.42443(8) 0.0202(7) Uani d . 1 . .
C C4 0.5959(3) 0.0387(3) 0.41657(9) 0.0221(7) Uani d . 1 . .
H H4 0.5414 -0.0005 0.3966 0.026 Uiso calc R 1 . .
C C5 0.5690(3) 0.1356(3) 0.44345(8) 0.0190(6) Uani d . 1 . .
C C11 0.6954(3) 0.2449(3) 0.50004(8) 0.0197(7) Uani d . 1 . .
C C12 0.6366(3) 0.3584(3) 0.50237(9) 0.0234(7) Uani d . 1 . .
H H12 0.5832 0.3848 0.4797 0.028 Uiso calc R 1 . .
C C13 0.6562(3) 0.4331(3) 0.53798(9) 0.0291(8) Uani d . 1 . .
H H13 0.6145 0.5106 0.5400 0.035 Uiso calc R 1 . .
C C14 0.7349(3) 0.3968(3) 0.57046(9) 0.0300(8) Uani d . 1 . .
H H14 0.7471 0.4485 0.5950 0.036 Uiso calc R 1 . .
C C15 0.7958(3) 0.2859(3) 0.56735(9) 0.0293(8) Uani d . 1 . .
H H15 0.8514 0.2613 0.5897 0.035 Uiso calc R 1 . .
C C16 0.7774(3) 0.2094(3) 0.53224(8) 0.0256(7) Uani d . 1 . .
H H16 0.8207 0.1328 0.5301 0.031 Uiso calc R 1 . .
C C31 0.8006(3) -0.0872(3) 0.40309(8) 0.0218(7) Uani d . 1 . .
C C32 0.7220(3) -0.1920(3) 0.38577(11) 0.0366(9) Uani d . 1 . .
H H32A 0.6773 -0.2315 0.4097 0.055 Uiso calc R 1 . .
H H32B 0.7754 -0.2533 0.3716 0.055 Uiso calc R 1 . .
H H32C 0.6622 -0.1591 0.3648 0.055 Uiso calc R 1 . .
C C33 0.8954(4) -0.1373(4) 0.43462(10) 0.0441(10) Uani d . 1 . .
H H33A 0.9448 -0.0685 0.4463 0.066 Uiso calc R 1 . .
H H33B 0.9502 -0.1959 0.4197 0.066 Uiso calc R 1 . .
H H33C 0.8528 -0.1798 0.4584 0.066 Uiso calc R 1 . .
C C34 0.8705(3) -0.0266(3) 0.36534(10) 0.0383(9) Uani d . 1 . .
H H34A 0.8107 0.0076 0.3446 0.057 Uiso calc R 1 . .
H H34B 0.9222 -0.0890 0.3509 0.057 Uiso calc R 1 . .
H H34C 0.9234 0.0403 0.3764 0.057 Uiso calc R 1 . .
N N51 0.4617(2) 0.2027(2) 0.44928(7) 0.0221(6) Uani d . 1 . .
H H51 0.4505 0.2182 0.4770 0.027 Uiso d R 1 . .
C C51 0.2467(3) 0.2452(3) 0.43416(9) 0.0228(7) Uani d . 1 . .
C C52 0.1322(3) 0.2013(3) 0.44692(9) 0.0281(8) Uani d . 1 . .
H H52 0.1201 0.1146 0.4505 0.034 Uiso calc R 1 . .
C C53 0.0347(3) 0.2821(3) 0.45460(9) 0.0292(8) Uani d . 1 . .
H H53 -0.0434 0.2500 0.4634 0.035 Uiso calc R 1 . .
C C54 0.0491(3) 0.4084(3) 0.44962(9) 0.0255(8) Uani d . 1 . .
C C55 0.1625(3) 0.4516(3) 0.43583(8) 0.0246(7) Uani d . 1 . .
H H55 0.1738 0.5381 0.4314 0.030 Uiso calc R 1 . .
C C56 0.2606(3) 0.3714(3) 0.42826(9) 0.0257(8) Uani d . 1 . .
H H56 0.3382 0.4036 0.4189 0.031 Uiso calc R 1 . .
C C57 0.3535(3) 0.1596(3) 0.42651(10) 0.0286(8) Uani d . 1 . .
H H571 0.3318 0.0752 0.4366 0.034 Uiso calc R 1 . .
H H572 0.3716 0.1553 0.3951 0.034 Uiso calc R 1 . .
C C58 -0.0538(3) 0.4969(4) 0.46037(11) 0.0385(9) Uani d . 1 . .
H H58A -0.0282 0.5503 0.4845 0.058 Uiso calc R 1 . .
H H58B -0.1280 0.4500 0.4687 0.058 Uiso calc R 1 . .
H H58C -0.0723 0.5483 0.4350 0.058 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 N2 . . 111.4(2) ?
C5 N1 C11 . . 129.6(2) ?
N2 N1 C11 . . 118.3(2) ?
C3 N2 N1 . . 104.9(2) ?
N2 C3 C4 . . 111.4(3) ?
N2 C3 C31 . . 119.4(3) ?
C4 C3 C31 . . 129.2(3) ?
C5 C4 C3 . . 105.8(3) ?
C5 C4 H4 . . 127.1 ?
C3 C4 H4 . . 127.1 ?
N1 C5 C4 . . 106.4(3) ?
N1 C5 N51 . . 122.2(2) ?
C4 C5 N51 . . 131.3(3) ?
C12 C11 C16 . . 120.1(3) ?
C12 C11 N1 . . 122.0(3) ?
C16 C11 N1 . . 117.9(3) ?
C11 C12 C13 . . 119.3(3) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C15 C14 C13 . . 119.7(3) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.7(3) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 119.5(3) ?
C15 C16 H16 . . 120.3 ?
C11 C16 H16 . . 120.3 ?
C3 C31 C32 . . 110.5(3) ?
C3 C31 C33 . . 110.6(2) ?
C32 C31 C33 . . 109.9(3) ?
C3 C31 C34 . . 108.8(2) ?
C32 C31 C34 . . 109.0(2) ?
C33 C31 C34 . . 108.0(3) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 H33A . . 109.5 ?
C31 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C31 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C31 C34 H34A . . 109.5 ?
C31 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C31 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C5 N51 C57 . . 116.6(2) ?
C5 N51 H51 . . 110.0 ?
C57 N51 H51 . . 115.2 ?
N51 C57 C51 . . 110.4(2) ?
N51 C57 H571 . . 109.6 ?
C51 C57 H571 . . 109.6 ?
N51 C57 H572 . . 109.6 ?
C51 C57 H572 . . 109.6 ?
H571 C57 H572 . . 108.1 ?
C52 C51 C56 . . 118.2(3) ?
C52 C51 C57 . . 121.5(3) ?
C56 C51 C57 . . 120.3(3) ?
C51 C52 C53 . . 120.8(3) ?
C51 C52 H52 . . 119.6 ?
C53 C52 H52 . . 119.6 ?
C54 C53 C52 . . 121.0(3) ?
C54 C53 H53 . . 119.5 ?
C52 C53 H53 . . 119.5 ?
C55 C54 C53 . . 118.0(3) ?
C55 C54 C58 . . 120.6(3) ?
C53 C54 C58 . . 121.3(3) ?
C54 C55 C56 . . 121.3(3) ?
C54 C55 H55 . . 119.4 ?
C56 C55 H55 . . 119.4 ?
C51 C56 C55 . . 120.7(3) ?
C51 C56 H56 . . 119.7 ?
C55 C56 H56 . . 119.7 ?
C54 C58 H58A . . 109.5 ?
C54 C58 H58B . . 109.5 ?
H58A C58 H58B . . 109.5 ?
C54 C58 H58C . . 109.5 ?
H58A C58 H58C . . 109.5 ?
H58B C58 H58C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 . 1.362(4) ?
N1 N2 . 1.371(3) ?
N1 C11 . 1.410(3) ?
N2 C3 . 1.320(3) ?
C3 C4 . 1.402(4) ?
C3 C31 . 1.501(4) ?
C4 C5 . 1.365(4) ?
C4 H4 . 0.9500 ?
C5 N51 . 1.376(4) ?
C11 C12 . 1.379(4) ?
C11 C16 . 1.384(4) ?
C12 C13 . 1.378(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.370(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.367(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.376(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C31 C32 . 1.509(4) ?
C31 C33 . 1.510(4) ?
C31 C34 . 1.534(4) ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 H33A . 0.9800 ?
C33 H33B . 0.9800 ?
C33 H33C . 0.9800 ?
C34 H34A . 0.9800 ?
C34 H34B . 0.9800 ?
C34 H34C . 0.9800 ?
N51 C57 . 1.438(4) ?
N51 H51 . 0.8800 ?
C57 C51 . 1.493(4) ?
C57 H571 . 0.9900 ?
C57 H572 . 0.9900 ?
C51 C52 . 1.379(4) ?
C51 C56 . 1.380(4) ?
C52 C53 . 1.385(5) ?
C52 H52 . 0.9500 ?
C53 C54 . 1.378(4) ?
C53 H53 . 0.9500 ?
C54 C55 . 1.375(4) ?
C54 C58 . 1.500(4) ?
C55 C56 . 1.385(4) ?
C55 H55 . 0.9500 ?
C56 H56 . 0.9500 ?
C58 H58A . 0.9800 ?
C58 H58B . 0.9800 ?
C58 H58C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12 N51 . 0.95 2.54 3.009(4) 111 no
N51 H51 <i>Cg</i>3 6_556 0.88 2.95 3.718(2) 147 no
C55 H55 <i>Cg</i>2 6_556 0.95 2.70 3.444(3) 136 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C3 . . . . 1.9(3) ?
C11 N1 N2 C3 . . . . 173.7(2) ?
N1 N2 C3 C4 . . . . -1.1(3) ?
N1 N2 C3 C31 . . . . 176.9(2) ?
N2 C3 C4 C5 . . . . -0.1(3) ?
C31 C3 C4 C5 . . . . -177.8(3) ?
N2 N1 C5 C4 . . . . -1.9(3) ?
C11 N1 C5 C4 . . . . -172.6(3) ?
N2 N1 C5 N51 . . . . 179.7(2) ?
C11 N1 C5 N51 . . . . 9.0(4) ?
C3 C4 C5 N1 . . . . 1.2(3) ?
C3 C4 C5 N51 . . . . 179.4(3) ?
C5 N1 C11 C12 . . . . -38.2(4) ?
N2 N1 C11 C12 . . . . 151.7(3) ?
C5 N1 C11 C16 . . . . 142.2(3) ?
N2 N1 C11 C16 . . . . -28.0(4) ?
C16 C11 C12 C13 . . . . -2.9(4) ?
N1 C11 C12 C13 . . . . 177.4(3) ?
C11 C12 C13 C14 . . . . 1.3(5) ?
C12 C13 C14 C15 . . . . 0.7(5) ?
C13 C14 C15 C16 . . . . -1.0(5) ?
C14 C15 C16 C11 . . . . -0.7(5) ?
C12 C11 C16 C15 . . . . 2.6(4) ?
N1 C11 C16 C15 . . . . -177.7(3) ?
N2 C3 C31 C32 . . . . 155.9(3) ?
C4 C3 C31 C32 . . . . -26.5(4) ?
N2 C3 C31 C33 . . . . 33.9(4) ?
C4 C3 C31 C33 . . . . -148.5(3) ?
N2 C3 C31 C34 . . . . -84.6(3) ?
C4 C3 C31 C34 . . . . 93.0(4) ?
N1 C5 N51 C57 . . . . -175.7(3) ?
C4 C5 N51 C57 . . . . 6.3(4) ?
C5 N51 C57 C51 . . . . -177.0(3) ?
N51 C57 C51 C52 . . . . -130.1(3) ?
N51 C57 C51 C56 . . . . 50.4(4) ?
C56 C51 C52 C53 . . . . -1.5(5) ?
C57 C51 C52 C53 . . . . 178.9(3) ?
C51 C52 C53 C54 . . . . 0.2(5) ?
C52 C53 C54 C55 . . . . 1.5(5) ?
C52 C53 C54 C58 . . . . -176.4(3) ?
C53 C54 C55 C56 . . . . -1.7(4) ?
C58 C54 C55 C56 . . . . 176.1(3) ?
C52 C51 C56 C55 . . . . 1.3(4) ?
C57 C51 C56 C55 . . . . -179.2(2) ?
C54 C55 C56 C51 . . . . 0.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654165
