#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012775.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_2012775
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o314
_journal_page_last  o317
_publ_section_title
;
5-[N-(Benzotriazol-1-ylmethyl)amino]-3-tert-butyl-1-phenylpyrazole:
sheets built from N---H...N, C---H...N and C---H...\p(pyrazole)
interactions
;
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Cobo, Justo'
  'Nogueras, Manuel'
  'S\'anchez, Adolfo'
  'Rengifo, Emerson'
  'Abonia, Rodrigo'
_chemical_formula_moiety  'C20 H22 N6'
_chemical_formula_sum  'C20 H22 N6'
_chemical_formula_iupac  'C20 H22 N6'
_chemical_formula_weight  346.44
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  7.2380(5)
_cell_length_b  11.9743(9)
_cell_length_c  21.2062(16)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1837.9(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.252
_diffrn_ambient_temperature  120(2)
loop_
_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
_atom_site_type_symbol
  N1 1.0596(2) 0.24099(13) 0.27065(8) 0.0232(4) Uani d . 1 . . N
  N2 1.0770(3) 0.35277(14) 0.28072(9) 0.0277(4) Uani d . 1 . . N
  N3 1.1066(3) 0.40159(15) 0.22666(9) 0.0292(4) Uani d . 1 . . N
  C1 1.1076(3) 0.32159(17) 0.18008(10) 0.0262(4) Uani d . 1 . . C
  C2 1.0753(3) 0.21782(16) 0.20807(10) 0.0231(4) Uani d . 1 . . C
  C3 1.0613(3) 0.11871(17) 0.17269(11) 0.0297(5) Uani d . 1 . . C
  C4 1.0815(4) 0.1306(2) 0.10877(11) 0.0371(6) Uani d . 1 . . C
  C5 1.1170(4) 0.2350(2) 0.07999(12) 0.0401(6) Uani d . 1 . . C
  C6 1.1313(3) 0.3311(2) 0.11493(11) 0.0341(5) Uani d . 1 . . C
  C7 1.0200(3) 0.16520(16) 0.32334(10) 0.0233(4) Uani d . 1 . . C
  N4 0.8337(3) 0.12756(14) 0.32493(9) 0.0265(4) Uani d . 1 . . N
  C8 0.6961(3) 0.18721(16) 0.35393(9) 0.0202(4) Uani d . 1 . . C
  N5 0.5259(2) 0.14256(13) 0.36389(8) 0.0228(4) Uani d . 1 . . N
  N6 0.4122(3) 0.21445(14) 0.39701(8) 0.0239(4) Uani d . 1 . . N
  C9 0.5151(3) 0.30470(15) 0.40625(9) 0.0207(4) Uani d . 1 . . C
  C10 0.6939(3) 0.29314(16) 0.38047(9) 0.0214(4) Uani d . 1 . . C
  C11 0.4373(3) 0.40699(16) 0.43919(9) 0.0236(4) Uani d . 1 . . C
  C12 0.4214(4) 0.50269(16) 0.39123(10) 0.0293(5) Uani d . 1 . . C
  C13 0.5717(4) 0.4412(2) 0.49206(10) 0.0343(5) Uani d . 1 . . C
  C14 0.2459(3) 0.38334(19) 0.46731(11) 0.0336(5) Uani d . 1 . . C
  C15 0.4674(3) 0.03169(16) 0.34969(9) 0.0216(4) Uani d . 1 . . C
  C16 0.4088(3) -0.03790(19) 0.39807(10) 0.0279(5) Uani d . 1 . . C
  C17 0.3577(3) -0.14699(19) 0.38388(12) 0.0341(5) Uani d . 1 . . C
  C18 0.3679(3) -0.18606(19) 0.32264(12) 0.0345(5) Uani d . 1 . . C
  C19 0.4245(3) -0.1168(2) 0.27497(11) 0.0335(5) Uani d . 1 . . C
  C20 0.4728(3) -0.00664(18) 0.28800(10) 0.0274(5) Uani d . 1 . . C
  H3 1.0393 0.0482 0.1918 0.036 Uiso calc R 1 . . H
  H4 1.0713 0.0663 0.0828 0.045 Uiso calc R 1 . . H
  H5 1.1313 0.2387 0.0355 0.048 Uiso calc R 1 . . H
  H6 1.1562 0.4011 0.0956 0.041 Uiso calc R 1 . . H
  H71 1.1027 0.0996 0.3203 0.028 Uiso calc R 1 . . H
  H72 1.0481 0.2040 0.3634 0.028 Uiso calc R 1 . . H
  H4A 0.8058 0.0638 0.3067 0.032 Uiso calc R 1 . . H
  H10 0.7914 0.3463 0.3811 0.026 Uiso calc R 1 . . H
  H12A 0.3356 0.4812 0.3576 0.035 Uiso calc R 1 . . H
  H12B 0.5432 0.5181 0.3731 0.035 Uiso calc R 1 . . H
  H12C 0.3751 0.5698 0.4125 0.035 Uiso calc R 1 . . H
  H13A 0.5756 0.3825 0.5242 0.041 Uiso calc R 1 . . H
  H13B 0.5296 0.5112 0.5113 0.041 Uiso calc R 1 . . H
  H13C 0.6956 0.4518 0.4744 0.041 Uiso calc R 1 . . H
  H14A 0.1601 0.3629 0.4335 0.040 Uiso calc R 1 . . H
  H14B 0.2004 0.4503 0.4889 0.040 Uiso calc R 1 . . H
  H14C 0.2549 0.3217 0.4976 0.040 Uiso calc R 1 . . H
  H16 0.4036 -0.0114 0.4403 0.034 Uiso calc R 1 . . H
  H17 0.3155 -0.1950 0.4165 0.041 Uiso calc R 1 . . H
  H18 0.3354 -0.2612 0.3136 0.041 Uiso calc R 1 . . H
  H19 0.4308 -0.1441 0.2330 0.040 Uiso calc R 1 . . H
  H20 0.5091 0.0420 0.2548 0.033 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  N1 0.0228(9) 0.0116(7) 0.0353(9) -0.0020(7) 0.0011(8) -0.0019(7)
  N2 0.0291(9) 0.0114(8) 0.0427(10) -0.0012(7) 0.0004(8) -0.0021(7)
  N3 0.0308(10) 0.0168(8) 0.0399(10) -0.0021(7) 0.0000(9) 0.0029(8)
  C1 0.0216(10) 0.0179(9) 0.0391(11) -0.0018(8) -0.0003(9) 0.0056(9)
  C2 0.0199(10) 0.0168(9) 0.0327(10) 0.0003(8) 0.0011(9) 0.0020(8)
  C3 0.0320(12) 0.0170(9) 0.0400(11) -0.0006(9) 0.0049(10) -0.0024(9)
  C4 0.0400(14) 0.0320(12) 0.0394(12) -0.0009(11) 0.0033(11) -0.0093(10)
  C5 0.0416(14) 0.0467(15) 0.0320(11) -0.0006(12) 0.0036(11) 0.0017(11)
  C6 0.0323(12) 0.0311(11) 0.0389(12) -0.0024(10) -0.0009(10) 0.0098(10)
  C7 0.0225(10) 0.0164(8) 0.0309(10) 0.0005(8) 0.0012(9) 0.0006(8)
  N4 0.0250(9) 0.0138(7) 0.0406(10) -0.0024(7) 0.0066(8) -0.0075(8)
  C8 0.0229(9) 0.0152(9) 0.0223(8) 0.0004(8) 0.0002(8) 0.0011(8)
  N5 0.0223(8) 0.0160(8) 0.0300(8) 0.0005(7) 0.0021(7) -0.0055(7)
  N6 0.0261(9) 0.0174(8) 0.0284(8) 0.0020(7) 0.0033(8) -0.0047(7)
  C9 0.0283(11) 0.0143(8) 0.0195(8) 0.0016(8) -0.0013(8) -0.0001(7)
  C10 0.0275(10) 0.0134(8) 0.0233(9) 0.0002(8) -0.0008(8) -0.0008(8)
  C11 0.0299(11) 0.0169(9) 0.0241(9) 0.0036(8) 0.0001(9) -0.0033(8)
  C12 0.0370(13) 0.0171(9) 0.0336(10) 0.0050(9) 0.0023(10) 0.0003(8)
  C13 0.0432(14) 0.0303(11) 0.0294(10) 0.0029(11) -0.0035(10) -0.0112(9)
  C14 0.0366(13) 0.0226(11) 0.0416(12) 0.0033(10) 0.0119(10) -0.0052(10)
  C15 0.0186(9) 0.0162(9) 0.0301(10) -0.0011(7) -0.0006(8) -0.0034(8)
  C16 0.0286(11) 0.0255(10) 0.0297(10) -0.0039(9) 0.0016(9) -0.0035(8)
  C17 0.0332(12) 0.0234(11) 0.0455(13) -0.0062(10) 0.0026(10) 0.0038(10)
  C18 0.0277(11) 0.0208(10) 0.0549(14) -0.0053(9) -0.0026(11) -0.0081(11)
  C19 0.0345(13) 0.0298(12) 0.0363(11) -0.0038(10) -0.0028(10) -0.0136(10)
  C20 0.0301(11) 0.0241(10) 0.0281(10) -0.0038(9) -0.0014(9) -0.0032(8)
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
  C1 C2 . 1.397(3) y
  C2 C3 . 1.408(3) y
  C3 C4 . 1.371(3) y
  C4 C5 . 1.415(4) y
  C5 C6 . 1.373(4) y
  C6 C1 . 1.397(3) y
  C1 N3 . 1.376(3) y
  C2 N1 . 1.361(3) y
  N1 N2 . 1.361(2) y
  N2 N3 . 1.305(3) y
  N1 C7 . 1.468(3) y
  C7 N4 . 1.422(3) y
  N4 C8 . 1.372(3) y
  C8 N5 . 1.359(3) y
  N5 N6 . 1.383(2) y
  N6 C9 . 1.327(3) y
  C9 C10 . 1.412(3) y
  C10 C8 . 1.388(3) y
  C3 H3 . 0.9500 no
  C4 H4 . 0.9500 no
  C5 H5 . 0.9500 no
  C6 H6 . 0.9500 no
  C7 H71 . 0.9900 no
  C7 H72 . 0.9900 no
  N4 H4A . 0.8800 no
  N5 C15 . 1.426(2) no
  C9 C11 . 1.518(3) no
  C10 H10 . 0.9500 no
  C11 C14 . 1.535(3) no
  C11 C12 . 1.536(3) no
  C11 C13 . 1.540(3) no
  C12 H12A . 0.9800 no
  C12 H12B . 0.9800 no
  C12 H12C . 0.9800 no
  C13 H13A . 0.9800 no
  C13 H13B . 0.9800 no
  C13 H13C . 0.9800 no
  C14 H14A . 0.9800 no
  C14 H14B . 0.9800 no
  C14 H14C . 0.9800 no
  C15 C20 . 1.387(3) no
  C15 C16 . 1.388(3) no
  C16 C17 . 1.390(3) no
  C16 H16 . 0.9500 no
  C17 C18 . 1.382(4) no
  C17 H17 . 0.9500 no
  C18 C19 . 1.370(3) no
  C18 H18 . 0.9500 no
  C19 C20 . 1.393(3) no
  C19 H19 . 0.9500 no
  C20 H20 . 0.9500 no
_cod_database_code 2012775