#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/71/2017154.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_2017154
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          'C20 H22 Br N3'
_chemical_formula_moiety         'C20 H22 Br N3'
_chemical_formula_sum            'C20 H22 Br N3'
_chemical_formula_weight         384.32
_chemical_name_systematic
;
5-(4-bromobenzyl)-3-tert-butyl-1-phenyl-1H-pyrazole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.634(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.1981(6)
_cell_length_b                   7.3960(9)
_cell_length_c                   24.171(4)
_cell_measurement_reflns_used    4071
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.85
_cell_volume                     3569.9(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 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28981
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.309
_exptl_absorpt_correction_T_max  0.785
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.631
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0477
_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)+(0.0569P)²+13.3406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                2871
_reflns_number_total             4071
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3324.cif
_cod_data_source_block           V
_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_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017154
_cod_database_fobs_code          2017154
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.80342(13) 0.5250(4) 0.26616(11) 0.0161(5) Uani d . 1 . .
N N2 0.84310(13) 0.4995(4) 0.31685(10) 0.0173(5) Uani d . 1 . .
C C3 0.80086(16) 0.4875(4) 0.35294(13) 0.0177(6) Uani d . 1 . .
C C4 0.73400(16) 0.5064(4) 0.32722(13) 0.0176(6) Uani d . 1 . .
H H4 0.6948 0.5015 0.3446 0.021 Uiso calc R 1 . .
C C5 0.73765(15) 0.5331(4) 0.27197(13) 0.0153(6) Uani d . 1 . .
C C11 0.83441(16) 0.5489(4) 0.21827(13) 0.0169(6) Uani d . 1 . .
C C12 0.80415(16) 0.4858(4) 0.16672(13) 0.0185(6) Uani d . 1 . .
H H12 0.7625 0.4241 0.1632 0.022 Uiso calc R 1 . .
C C13 0.83556(17) 0.5141(5) 0.12051(14) 0.0224(7) Uani d . 1 . .
H H13 0.8148 0.4741 0.0848 0.027 Uiso calc R 1 . .
C C14 0.89664(18) 0.5996(5) 0.12568(15) 0.0261(8) Uani d . 1 . .
H H14 0.9177 0.6196 0.0936 0.031 Uiso calc R 1 . .
C C15 0.92702(18) 0.6559(5) 0.17759(16) 0.0279(8) Uani d . 1 . .
H H15 0.9696 0.7127 0.1814 0.033 Uiso calc R 1 . .
C C16 0.89611(17) 0.6304(5) 0.22403(14) 0.0224(7) Uani d . 1 . .
H H16 0.9173 0.6690 0.2598 0.027 Uiso calc R 1 . .
C C31 0.82519(17) 0.4664(4) 0.41454(13) 0.0196(7) Uani d . 1 . .
C C32 0.90061(17) 0.4395(5) 0.42545(15) 0.0264(8) Uani d . 1 . .
H H32A 0.9120 0.3255 0.4085 0.040 Uiso calc R 1 . .
H H32B 0.9158 0.4356 0.4659 0.040 Uiso calc R 1 . .
H H32C 0.9226 0.5400 0.4090 0.040 Uiso calc R 1 . .
C C33 0.8068(2) 0.6369(5) 0.44358(15) 0.0307(8) Uani d . 1 . .
H H33A 0.8271 0.7418 0.4279 0.046 Uiso calc R 1 . .
H H33B 0.8235 0.6283 0.4837 0.046 Uiso calc R 1 . .
H H33C 0.7580 0.6507 0.4379 0.046 Uiso calc R 1 . .
C C34 0.79148(19) 0.3058(5) 0.43727(15) 0.0293(8) Uani d . 1 . .
H H34A 0.7428 0.3215 0.4297 0.044 Uiso calc R 1 . .
H H34B 0.8059 0.2967 0.4777 0.044 Uiso calc R 1 . .
H H34C 0.8039 0.1951 0.4190 0.044 Uiso calc R 1 . .
N N51 0.68844(13) 0.5587(4) 0.22681(11) 0.0188(6) Uani d . 1 . .
H H51 0.7007 0.6478 0.2064 0.023 Uiso d R 1 . .
C C51 0.57057(15) 0.5712(5) 0.18715(13) 0.0166(6) Uani d . 1 . .
C C52 0.51577(17) 0.6843(5) 0.17890(14) 0.0235(7) Uani d . 1 . .
H H52 0.5119 0.7781 0.2051 0.028 Uiso calc R 1 . .
C C53 0.46654(17) 0.6638(5) 0.13350(15) 0.0266(8) Uani d . 1 . .
H H53 0.4282 0.7397 0.1289 0.032 Uiso calc R 1 . .
C C44 0.47381(17) 0.5321(5) 0.09504(14) 0.0220(7) Uani d . 1 . .
Br Br54 0.40667(2) 0.50388(6) 0.033022(16) 0.03814(16) Uani d . 1 . .
C C55 0.52881(16) 0.4213(5) 0.10105(14) 0.0208(7) Uani d . 1 . .
H H55 0.5337 0.3327 0.0735 0.025 Uiso calc R 1 . .
C C56 0.57672(16) 0.4397(4) 0.14735(14) 0.0182(7) Uani d . 1 . .
H H56 0.6145 0.3616 0.1522 0.022 Uiso calc R 1 . .
C C57 0.62110(15) 0.5897(5) 0.23852(13) 0.0189(7) Uani d . 1 . .
H H571 0.6182 0.7127 0.2542 0.023 Uiso calc R 1 . .
H H572 0.6109 0.5018 0.2670 0.023 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'
Br Br -0.2901 2.4595 '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 . . 111.3(2) ?
C5 N1 C11 . . 130.0(3) ?
N2 N1 C11 . . 118.6(3) ?
C3 N2 N1 . . 104.6(3) ?
N2 C3 C4 . . 112.1(3) ?
N2 C3 C31 . . 121.1(3) ?
C4 C3 C31 . . 126.7(3) ?
C5 C4 C3 . . 105.0(3) ?
C5 C4 H4 . . 127.5 ?
C3 C4 H4 . . 127.5 ?
N1 C5 C4 . . 107.0(3) ?
N1 C5 N51 . . 121.7(3) ?
C4 C5 N51 . . 131.2(3) ?
C16 C11 C12 . . 120.7(3) ?
C16 C11 N1 . . 118.7(3) ?
C12 C11 N1 . . 120.5(3) ?
C13 C12 C11 . . 118.9(3) ?
C13 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C14 C13 C12 . . 120.7(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 119.6(3) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.5(3) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C11 C16 C15 . . 119.6(3) ?
C11 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C3 C31 C34 . . 110.0(3) ?
C3 C31 C33 . . 107.8(3) ?
C34 C31 C33 . . 109.3(3) ?
C3 C31 C32 . . 110.8(3) ?
C34 C31 C32 . . 109.2(3) ?
C33 C31 C32 . . 109.7(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 . . 117.1(3) ?
C5 N51 H51 . . 108.5 ?
C57 N51 H51 . . 110.0 ?
N51 C57 C51 . . 111.6(3) ?
N51 C57 H571 . . 109.3 ?
C51 C57 H571 . . 109.3 ?
N51 C57 H572 . . 109.3 ?
C51 C57 H572 . . 109.3 ?
H571 C57 H572 . . 108.0 ?
C52 C51 C56 . . 118.6(3) ?
C52 C51 C57 . . 120.0(3) ?
C56 C51 C57 . . 121.4(3) ?
C53 C52 C51 . . 121.2(3) ?
C53 C52 H52 . . 119.4 ?
C51 C52 H52 . . 119.4 ?
C44 C53 C52 . . 118.8(3) ?
C44 C53 H53 . . 120.6 ?
C52 C53 H53 . . 120.6 ?
C53 C44 C55 . . 121.4(3) ?
C53 C44 Br54 . . 118.9(3) ?
C55 C44 Br54 . . 119.7(3) ?
C44 C55 C56 . . 119.2(3) ?
C44 C55 H55 . . 120.4 ?
C56 C55 H55 . . 120.4 ?
C55 C56 C51 . . 120.7(3) ?
C55 C56 H56 . . 119.7 ?
C51 C56 H56 . . 119.7 ?
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 . 1.358(4) ?
N1 N2 . 1.373(4) ?
N1 C11 . 1.408(4) ?
N2 C3 . 1.312(4) ?
C3 C4 . 1.406(4) ?
C3 C31 . 1.504(4) ?
C4 C5 . 1.363(4) ?
C4 H4 . 0.9500 ?
C5 N51 . 1.375(4) ?
C11 C16 . 1.372(5) ?
C11 C12 . 1.384(5) ?
C12 C13 . 1.381(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.375(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.376(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.377(5) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C31 C34 . 1.513(5) ?
C31 C33 . 1.516(5) ?
C31 C32 . 1.519(5) ?
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 . 1.449(4) ?
N51 H51 . 0.8797 ?
C57 C51 . 1.490(4) ?
C57 H571 . 0.9900 ?
C57 H572 . 0.9900 ?
C51 C52 . 1.378(5) ?
C51 C56 . 1.386(5) ?
C52 C53 . 1.374(5) ?
C52 H52 . 0.9500 ?
C53 C44 . 1.370(5) ?
C53 H53 . 0.9500 ?
C44 C55 . 1.370(5) ?
C44 Br54 . 1.876(3) ?
C55 C56 . 1.372(5) ?
C55 H55 . 0.9500 ?
C56 H56 . 0.9500 ?
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 2.51 2.980(4) 111 no
N51 H51 <i>Cg</i>1 4_655 0.88 2.72 3.504(3) 148 no
C15 H15 <i>Cg</i>3 5_555 0.95 2.95 3.687(4) 135 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 . . . . 1.6(3) ?
C11 N1 N2 C3 . . . . 178.0(3) ?
N1 N2 C3 C4 . . . . -0.6(3) ?
N1 N2 C3 C31 . . . . -177.5(3) ?
N2 C3 C4 C5 . . . . -0.6(4) ?
C31 C3 C4 C5 . . . . 176.0(3) ?
N2 N1 C5 C4 . . . . -2.1(3) ?
C11 N1 C5 C4 . . . . -177.9(3) ?
N2 N1 C5 N51 . . . . 179.7(3) ?
C11 N1 C5 N51 . . . . 3.9(5) ?
C3 C4 C5 N1 . . . . 1.6(3) ?
C3 C4 C5 N51 . . . . 179.6(3) ?
C5 N1 C11 C16 . . . . 144.7(3) ?
N2 N1 C11 C16 . . . . -30.9(4) ?
C5 N1 C11 C12 . . . . -37.4(5) ?
N2 N1 C11 C12 . . . . 147.0(3) ?
C16 C11 C12 C13 . . . . -3.1(5) ?
N1 C11 C12 C13 . . . . 179.1(3) ?
C11 C12 C13 C14 . . . . 1.5(5) ?
C12 C13 C14 C15 . . . . 0.6(5) ?
C13 C14 C15 C16 . . . . -1.3(5) ?
C12 C11 C16 C15 . . . . 2.5(5) ?
N1 C11 C16 C15 . . . . -179.6(3) ?
C14 C15 C16 C11 . . . . -0.3(5) ?
N2 C3 C31 C34 . . . . -127.6(3) ?
C4 C3 C31 C34 . . . . 56.0(4) ?
N2 C3 C31 C33 . . . . 113.3(3) ?
C4 C3 C31 C33 . . . . -63.0(4) ?
N2 C3 C31 C32 . . . . -6.8(4) ?
C4 C3 C31 C32 . . . . 176.9(3) ?
N1 C5 N51 C57 . . . . -171.9(3) ?
C4 C5 N51 C57 . . . . 10.4(5) ?
C5 N51 C57 C51 . . . . -166.3(3) ?
N51 C57 C51 C52 . . . . -142.8(3) ?
N51 C57 C51 C56 . . . . 38.3(4) ?
C56 C51 C52 C53 . . . . 2.6(5) ?
C57 C51 C52 C53 . . . . -176.4(3) ?
C51 C52 C53 C44 . . . . -2.3(5) ?
C52 C53 C44 C55 . . . . 0.1(5) ?
C52 C53 C44 Br54 . . . . 180.0(3) ?
C53 C44 C55 C56 . . . . 1.7(5) ?
Br54 C44 C55 C56 . . . . -178.2(2) ?
C44 C55 C56 C51 . . . . -1.4(5) ?
C52 C51 C56 C55 . . . . -0.8(5) ?
C57 C51 C56 C55 . . . . 178.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654168
