#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202281.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_2202281
loop_
_publ_author_name
'Yin, Caixia'
'Huo, Fangjun'
'Gao, Fei'
'Guo, Jianping'
'Yang, Pin'
_publ_section_title
;
2,6-Bis(3,5-dimethylpyrazol-1-ylmethyl)-4-methylphenol
;
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1740
_journal_page_last               o1741
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C19 H24 N4 O'
_chemical_formula_moiety         'C19 H24 N4 O'
_chemical_formula_sum            'C19 H24 N4 O'
_chemical_formula_weight         324.42
_chemical_melting_point          398
_chemical_name_common
2,6-Bis(3,5-dimethylpyrazol-1-ylmethyl)-4-methylphenol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 105.085(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.508(3)
_cell_length_b                   18.747(6)
_cell_length_c                   10.116(3)
_cell_measurement_temperature    183(2)
_cell_volume                     1741.0(9)
_diffrn_ambient_temperature      183(2)
_exptl_crystal_density_diffrn    1.238
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_chemical_melting_point' value '398(K)' was changed to '398' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2202281
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_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
O1 0.2708(2) 0.08831(13) 0.5687(2) 0.0366(7) Uani d . 1 . . O
H1 0.2145 0.1115 0.5055 0.055 Uiso calc R 1 . . H
N1 0.1360(3) 0.17047(17) 0.3439(3) 0.0335(8) Uani d . 1 . . N
N2 0.2350(3) 0.15631(17) 0.2719(3) 0.0315(8) Uani d . 1 . . N
N3 0.6118(3) 0.08598(19) 0.9238(3) 0.0364(8) Uani d . 1 . . N
N4 0.6772(3) 0.02299(18) 0.9730(3) 0.0401(9) Uani d . 1 . . N
C1 -0.0176(4) 0.2723(2) 0.3672(4) 0.0522(12) Uani d . 1 . . C
H1A -0.1030 0.2839 0.2923 0.078 Uiso calc R 1 . . H
H1B 0.0224 0.3162 0.4151 0.078 Uiso calc R 1 . . H
H1C -0.0463 0.2398 0.4315 0.078 Uiso calc R 1 . . H
C2 0.0948(4) 0.2375(2) 0.3107(4) 0.0342(10) Uani d . 1 . . C
C3 0.1690(4) 0.2652(2) 0.2222(4) 0.0398(10) Uani d . 1 . . C
H3 0.1598 0.3120 0.1848 0.048 Uiso calc R 1 . . H
C4 0.2587(4) 0.2122(2) 0.1986(3) 0.0345(10) Uani d . 1 . . C
C5 0.3644(4) 0.2108(2) 0.1134(4) 0.0537(12) Uani d . 1 . . C
H5A 0.4623 0.2011 0.1717 0.081 Uiso calc R 1 . . H
H5B 0.3639 0.2570 0.0680 0.081 Uiso calc R 1 . . H
H5C 0.3369 0.1732 0.0441 0.081 Uiso calc R 1 . . H
C6 0.3121(4) 0.0884(2) 0.2961(3) 0.0364(10) Uani d . 1 . . C
H6A 0.3501 0.0767 0.2163 0.055 Uiso calc R 1 . . H
H6B 0.2433 0.0502 0.3053 0.055 Uiso calc R 1 . . H
C7 0.4371(4) 0.09051(19) 0.4238(3) 0.0295(9) Uani d . 1 . . C
C8 0.5804(4) 0.09084(19) 0.4164(4) 0.0344(9) Uani d . 1 . . C
H8 0.5998 0.0910 0.3289 0.041 Uiso calc R 1 . . H
C9 0.6964(4) 0.09093(19) 0.5325(4) 0.0326(9) Uani d . 1 . . C
C10 0.6646(4) 0.08986(19) 0.6586(4) 0.0335(9) Uani d . 1 . . C
H10 0.7425 0.0901 0.7395 0.040 Uiso calc R 1 . . H
C11 0.5225(4) 0.0884(2) 0.6706(3) 0.0301(9) Uani d . 1 . . C
C12 0.4094(4) 0.09049(19) 0.5520(4) 0.0293(9) Uani d . 1 . . C
C13 0.8517(3) 0.0902(2) 0.5213(4) 0.0454(11) Uani d . 1 . . C
H13B 0.9131 0.1179 0.5966 0.068 Uiso calc R 1 . . H
H13A 0.8557 0.1113 0.4337 0.068 Uiso calc R 1 . . H
H13C 0.8869 0.0409 0.5262 0.068 Uiso calc R 1 . . H
C14 0.4862(4) 0.0847(2) 0.8074(3) 0.0411(11) Uani d . 1 . . C
H14B 0.4223 0.1254 0.8144 0.062 Uiso calc R 1 . . H
H14A 0.4308 0.0403 0.8107 0.062 Uiso calc R 1 . . H
C15 0.6394(4) 0.2176(2) 0.9457(4) 0.0600(13) Uani d . 1 . . C
H15A 0.5334 0.2216 0.9290 0.090 Uiso calc R 1 . . H
H15B 0.6675 0.2294 0.8617 0.090 Uiso calc R 1 . . H
H15C 0.6870 0.2506 1.0187 0.090 Uiso calc R 1 . . H
C16 0.6853(4) 0.1431(2) 0.9878(4) 0.0420(11) Uani d . 1 . . C
C17 0.8017(4) 0.1164(2) 1.0833(4) 0.0477(12) Uani d . 1 . . C
H17 0.8744 0.1429 1.1463 0.057 Uiso calc R 1 . . H
C18 0.7930(4) 0.0427(2) 1.0704(4) 0.0434(11) Uani d . 1 . . C
C19 0.8926(4) -0.0130(3) 1.1507(4) 0.0702(15) Uani d . 1 . . C
H19C 0.8694 -0.0595 1.1058 0.105 Uiso calc R 1 . . H
H19B 0.8796 -0.0155 1.2436 0.105 Uiso calc R 1 . . H
H19A 0.9938 -0.0006 1.1553 0.105 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
O1 0.0330(14) 0.0419(18) 0.0338(15) 0.0056(13) 0.0066(12) 0.0067(13)
N1 0.0284(17) 0.039(2) 0.0323(19) 0.0064(16) 0.0067(15) 0.0067(16)
N2 0.0354(19) 0.031(2) 0.0273(18) 0.0057(16) 0.0064(15) 0.0020(16)
N3 0.0399(19) 0.040(2) 0.0280(18) 0.0012(19) 0.0058(15) 0.0009(18)
N4 0.043(2) 0.041(2) 0.035(2) 0.0032(18) 0.0073(16) 0.0037(18)
C1 0.051(3) 0.056(3) 0.055(3) 0.015(2) 0.022(2) 0.010(2)
C2 0.031(2) 0.037(3) 0.032(2) 0.003(2) 0.0042(18) 0.004(2)
C3 0.041(2) 0.034(3) 0.043(3) 0.004(2) 0.009(2) 0.011(2)
C4 0.034(2) 0.045(3) 0.024(2) 0.005(2) 0.0062(18) 0.010(2)
C5 0.056(3) 0.063(3) 0.046(3) 0.016(2) 0.021(2) 0.020(2)
C6 0.040(2) 0.033(2) 0.033(2) 0.008(2) 0.0043(18) -0.001(2)
C7 0.036(2) 0.023(2) 0.028(2) 0.0058(19) 0.0056(18) -0.0009(18)
C8 0.043(2) 0.025(2) 0.036(2) 0.004(2) 0.0122(19) 0.0048(19)
C9 0.035(2) 0.024(2) 0.039(2) -0.0034(19) 0.0101(19) 0.002(2)
C10 0.035(2) 0.031(2) 0.032(2) -0.002(2) 0.0037(18) 0.0040(19)
C11 0.036(2) 0.026(2) 0.027(2) 0.0002(19) 0.0068(18) 0.0008(18)
C12 0.027(2) 0.020(2) 0.043(2) 0.0005(18) 0.0124(19) 0.0016(19)
C13 0.042(2) 0.049(3) 0.046(3) -0.003(2) 0.012(2) 0.001(2)
C14 0.033(2) 0.050(3) 0.038(2) 0.002(2) 0.0057(19) 0.004(2)
C15 0.065(3) 0.047(3) 0.076(3) -0.003(3) 0.033(3) -0.006(3)
C16 0.050(3) 0.041(3) 0.041(3) -0.005(2) 0.022(2) -0.008(2)
C17 0.040(3) 0.067(4) 0.032(3) -0.015(2) 0.003(2) -0.010(2)
C18 0.042(3) 0.054(3) 0.032(2) -0.001(2) 0.004(2) 0.006(2)
C19 0.054(3) 0.094(4) 0.056(3) 0.013(3) 0.003(2) 0.029(3)
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
O1 C12 . 1.372(4) ?
O1 H1 . 0.8400 ?
N1 C2 . 1.333(4) ?
N1 N2 . 1.358(3) ?
N2 C4 . 1.337(4) ?
N2 C6 . 1.458(4) ?
N3 C16 . 1.348(5) ?
N3 N4 . 1.367(4) ?
N3 C14 . 1.442(4) ?
N4 C18 . 1.325(4) ?
C1 C2 . 1.488(5) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.378(5) ?
C3 C4 . 1.370(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.485(4) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.511(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.384(4) ?
C7 C12 . 1.389(4) ?
C8 C9 . 1.386(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(4) ?
C9 C13 . 1.509(4) ?
C10 C11 . 1.387(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.387(4) ?
C11 C14 . 1.512(4) ?
C13 H13B . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14B . 0.9900 ?
C14 H14A . 0.9900 ?
C15 C16 . 1.492(5) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.361(5) ?
C17 C18 . 1.388(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.499(5) ?
C19 H19C . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19A . 0.9800 ?