data_2002946
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     1999
_journal_volume     B55
_journal_page_first     441
_journal_page_last     447
_publ_section_title
;
3(5),4-Dimethyl and 3,4,5-Trimethylpyrazoles at 200K
;
loop_
    _publ_author_name
    'Infantes, L.'
    'Foces-Foces, C.'
    'Elguero,J.'
_chemical_name_systematic     '4,5-dimethylpyrazole'
_chemical_formula_moiety     'C5 H8 N2'
_chemical_formula_sum     'C5 H8 N2'
_chemical_formula_weight     96.132
_chemical_melting_point     331
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    +x,+y,+z
    -x,-y,-z
_cell_length_a     14.4170(10)
_cell_length_b     12.0200(10)
_cell_length_c     12.0420(10)
_cell_angle_alpha     119.990(7)
_cell_angle_beta     105.991(7)
_cell_angle_gamma     87.224(10)
_cell_volume     1727.5(3)
_cell_formula_units_Z     12
_cell_measurement_reflns_used     74
_cell_measurement_theta_min     4.2
_cell_measurement_theta_max     44.1
_cell_measurement_temperature     200
_exptl_crystal_description     sheet
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.109
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.556
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     200
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_source     xray_tube
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Philips PW1100 diffractometer'
_diffrn_measurement_method     '\w/2\q scans'
_diffrn_reflns_number     5733
_diffrn_reflns_av_R_equivalents     0
_diffrn_reflns_av_sigmaI/netI     .000
_diffrn_reflns_theta_min     3.21
_diffrn_reflns_theta_max     64.84
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_reduction_process     perpendicular_monochr_Lp
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     90
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    0 3 -3
    0 -3 3
_reflns_number_total     5733
_reflns_number_observed     4543
_reflns_observed_criterion     I>2\s(I)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     .087
_refine_ls_R_factor_obs     .075
_refine_ls_wR_factor_all     .105
_refine_ls_wR_factor_obs     .092
_refine_ls_goodness_of_fit_all     .856
_refine_ls_goodness_of_fit_obs     .848
_refine_ls_number_reflns     4543
_refine_ls_number_parameters     571
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     'w = k/[(A+B Fo)^2^(C+D(sin\q)/\l)]'
_refine_ls_shift/esd_max     .03
_refine_ls_shift/esd_mean     .001
_refine_diff_density_max     .30
_refine_diff_density_min     -.42
_refine_ls_extinction_method     Zachariasen
_refine_ls_extinction_coef    84.E1(2)
_refine_ls_abs_structure_details     none
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C ? .017 .009 IntTabIV
    H ? 0 0 IntTabIV
    N ? .029 .018 IntTabIV
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_calc_attached_atom
    N11 .1263(2) .9490(2) .8749(2) .0450(10) Uani No No
    N12 .1136(2) .9932(2) .7889(2) .0506(10) Uani No No
    C13 .1079(2) 1.1196(3) .8621(3) .0491(12) Uani No No
    C14 .1158(2) 1.1562(3) .9940(3) .0451(11) Uani No No
    C15 .1278(2) 1.0442(3) .9983(3) .0427(10) Uani No No
    C16 .1128(3) 1.2893(3) 1.1064(4) .0668(15) Uani No No
    C17 .1391(3) 1.0208(4) 1.1120(3) .0616(16) Uani No No
    N21 .1299(2) .5914(2) .6354(2) .0452(10) Uani No No
    N22 .1363(2) .6765(2) .7654(2) .0484(10) Uani No No
    C23 .1340(2) .6044(3) .8202(3) .0505(12) Uani No No
    C24 .1265(2) .4734(3) .7272(3) .0439(11) Uani No No
    C25 .1241(2) .4697(2) .6105(3) .0420(10) Uani No No
    C26 .1226(3) .3620(4) .7502(5) .0667(17) Uani No No
    C27 .1155(3) .3567(3) .4732(3) .0626(15) Uani No No
    N31 .1239(2) .8333(2) .5196(2) .0442(9) Uani No No
    N32 .1331(2) .7061(2) .4767(2) .0512(11) Uani No No
    C33 .1394(3) .6544(3) .3524(3) .0505(12) Uani No No
    C34 .1343(2) .7467(3) .3136(3) .0441(11) Uani No No
    C35 .1249(2) .8601(2) .4235(3) .0408(10) Uani No No
    C36 .1388(4) .7278(4) .1823(4) .0657(18) Uani No No
    C37 .1167(3) .9936(3) .4459(4) .0554(13) Uani No No
    N41 .3811(2) -.0505(2) .1160(2) .0446(10) Uani No No
    N42 .3864(2) -.0946(2) .2009(2) .0483(10) Uani No No
    C43 .3902(2) -.2224(3) .1292(3) .0494(12) Uani No No
    C44 .3875(2) -.2608(2) -.0010(3) .0452(10) Uani No No
    C45 .3816(2) -.1483(3) -.0062(3) .0439(11) Uani No No
    C46 .3901(3) -.3945(3) -.1122(4) .0696(15) Uani No No
    C47 .3755(3) -.1264(4) -.1193(4) .0640(16) Uani No No
    N51 .3696(2) .3030(2) .3534(2) .0463(10) Uani No No
    N52 .3767(2) .2238(2) .2280(2) .0519(11) Uani No No
    C53 .3812(3) .2986(3) .1774(3) .0524(13) Uani No No
    C54 .3778(2) .4279(3) .2703(3) .0446(11) Uani No No
    C55 .3703(2) .4253(2) .3809(3) .0412(10) Uani No No
    C56 .3819(4) .5420(4) .2518(5) .0706(19) Uani No No
    C57 .3642(3) .5338(3) .5135(3) .0578(13) Uani No No
    N61 .3736(2) .0632(2) .4689(2) .0459(10) Uani No No
    N62 .3595(2) .1887(2) .5099(2) .0520(11) Uani No No
    C63 .3517(2) .2405(3) .6341(3) .0487(12) Uani No No
    C64 .3602(2) .1496(3) .6739(3) .0432(11) Uani No No
    C65 .3740(2) .0374(3) .5654(3) .0415(10) Uani No No
    C66 .3551(3) .1666(4) .8041(3) .0612(16) Uani No No
    C67 .3876(3) -.0944(3) .5478(4) .0599(14) Uani No No
    H11 .122(3) .866(4) .842(4) .031(9) Uiso No No
    H13 .103(4) 1.170(6) .821(6) .069(16) Uiso No No
    H161 .112(4) 1.354(6) 1.068(6) .074(17) Uiso No No
    H162 .058(5) 1.294(6) 1.146(7) .081(18) Uiso No No
    H163 .169(5) 1.318(6) 1.182(6) .073(17) Uiso No No
    H171 .166(5) .943(7) 1.097(7) .082(19) Uiso No No
    H172 .199(5) 1.090(7) 1.196(7) .09(2) Uiso No No
    H173 .092(5) 1.032(7) 1.140(7) .09(2) Uiso No No
    H21 .137(4) .631(5) .582(5) .057(13) Uiso No No
    H23 .132(4) .663(5) .916(6) .062(14) Uiso No No
    H261 .117(7) .404(10) .851(11) .15(4) Uiso No No
    H262 .062(6) .294(8) .686(8) .10(2) Uiso No No
    H263 .173(4) .308(6) .736(5) .062(14) Uiso No No
    H271 .085(4) .366(6) .395(7) .075(17) Uiso No No
    H272 .183(6) .322(7) .463(7) .10(2) Uiso No No
    H273 .077(5) .293(7) .461(7) .09(2) Uiso No No
    H31 .119(6) .892(8) .629(8) .12(3) Uiso No No
    H33 .148(3) .574(4) .306(4) .025(8) Uiso No No
    H361 .127(6) .627(8) .118(8) .12(3) Uiso No No
    H362 .087(5) .759(6) .139(7) .079(18) Uiso No No
    H363 .190(5) .778(7) .195(7) .08(2) Uiso No No
    H371 .128(7) 1.065(9) .549(10) .13(3) Uiso No No
    H372 .166(7) 1.005(9) .400(10) .14(3) Uiso No No
    H373 .049(6) .999(7) .381(8) .10(2) Uiso No No
    H41 .375(4) .040(5) .140(5) .060(14) Uiso No No
    H43 .394(4) -.272(5) .174(5) .058(13) Uiso No No
    H461 .406(7) -.452(9) -.071(10) .14(3) Uiso No No
    H462 .334(7) -.443(9) -.195(10) .13(3) Uiso No No
    H463 .432(6) -.406(8) -.169(8) .11(3) Uiso No No
    H471 .355(7) -.033(10) -.090(10) .14(3) Uiso No No
    H472 .425(6) -.158(8) -.158(8) .11(3) Uiso No No
    H473 .316(5) -.181(6) -.204(7) .082(18) Uiso No No
    H51 .366(4) .244(6) .393(6) .072(16) Uiso No No
    H53 .393(4) .266(5) .089(5) .057(13) Uiso No No
    H561 .383(5) .517(7) .148(8) .10(2) Uiso No No
    H562 .338(4) .594(6) .284(6) .067(15) Uiso No No
    H563 .447(6) .603(7) .327(8) .10(2) Uiso No No
    H571 .339(6) .502(8) .567(9) .12(3) Uiso No No
    H572 .420(5) .602(6) .566(7) .080(18) Uiso No No
    H573 .317(6) .602(8) .504(8) .12(3) Uiso No No
    H61 .364(5) -.004(7) .359(7) .09(2) Uiso No No
    H63 .344(3) .329(4) .683(4) .030(9) Uiso No No
    H661 .350(7) .260(9) .865(9) .13(3) Uiso No No
    H662 .305(4) .116(6) .787(6) .063(15) Uiso No No
    H663 .413(4) .132(5) .845(5) .054(12) Uiso No No
    H671 .408(6) -.139(9) .469(10) .12(3) Uiso No No
    H672 .451(5) -.097(6) .617(7) .09(2) Uiso No No
    H673 .328(5) -.132(7) .556(7) .09(2) Uiso No No
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
    N11 .0693(15) .0294(11) .0338(11) .0081(9) .0138(10) .0151(9)
    N12 .0784(17) .0406(12) .0329(11) .0112(11) .0187(11) .0179(10)
    C13 .0732(19) .0384(13) .0377(14) .0113(12) .0178(12) .0202(12)
    C14 .0559(16) .0357(13) .0321(13) .0040(11) .0108(11) .0097(11)
    C15 .0528(15) .0420(13) .0306(12) .0048(10) .0111(10) .0169(11)
    C16 .080(2) .0439(17) .0446(17) .0103(15) .0133(16) .0025(14)
    C17 .075(2) .075(2) .0440(17) .0092(18) .0147(15) .0381(17)
    N21 .0673(15) .0388(11) .0335(11) .0105(10) .0162(10) .0209(9)
    N22 .0743(16) .0358(11) .0356(12) .0107(10) .0171(11) .0183(9)
    C23 .0706(19) .0480(15) .0386(14) .0116(13) .0200(12) .0244(12)
    C24 .0567(15) .0384(13) .0453(14) .0089(11) .0162(11) .0269(11)
    C25 .0534(15) .0337(12) .0388(14) .0078(10) .0125(11) .0189(11)
    C26 .087(3) .0548(18) .087(3) .0163(18) .034(2) .053(2)
    C27 .085(2) .0431(16) .0434(17) .0108(16) .0168(15) .0112(13)
    N31 .0658(14) .0368(11) .0312(11) .0114(9) .0143(9) .0185(9)
    N32 .0848(18) .0414(12) .0359(12) .0159(11) .0240(11) .0231(10)
    C33 .078(2) .0404(15) .0325(13) .0156(13) .0195(12) .0175(12)
    C34 .0622(16) .0479(14) .0270(12) .0104(11) .0156(11) .0213(11)
    C35 .0525(15) .0372(13) .0346(12) .0059(10) .0100(10) .0209(10)
    C36 .095(3) .079(2) .0421(17) .027(2) .0316(17) .0405(17)
    C37 .067(2) .0422(15) .0602(19) .0080(13) .0095(15) .0331(14)
    N41 .0658(15) .0315(11) .0370(11) .0091(9) .0164(10) .0174(9)
    N42 .0720(16) .0382(11) .0343(11) .0067(10) .0179(10) .0170(9)
    C43 .0708(19) .0379(13) .0448(15) .0076(12) .0196(13) .0234(12)
    C44 .0555(15) .0333(13) .0377(13) .0032(10) .0148(11) .0107(11)
    C45 .0551(15) .0419(13) .0309(12) .0066(11) .0121(11) .0161(11)
    C46 .089(3) .0362(15) .057(2) .0056(15) .0272(18) .0014(14)
    C47 .086(2) .071(2) .0455(17) .0121(18) .0215(17) .0360(16)
    N51 .0706(15) .0370(11) .0370(12) .0114(10) .0190(10) .0216(9)
    N52 .0848(18) .0375(11) .0393(12) .0095(11) .0249(12) .0204(10)
    C53 .084(2) .0417(14) .0391(15) .0122(13) .0255(14) .0226(12)
    C54 .0612(16) .0361(13) .0469(15) .0115(11) .0214(12) .0261(12)
    C55 .0520(14) .0348(12) .0353(13) .0076(10) .0119(10) .0173(10)
    C56 .105(3) .0540(18) .086(3) .028(2) .048(2) .051(2)
    C57 .073(2) .0449(15) .0411(15) .0133(14) .0173(14) .0115(13)
    N61 .0649(15) .0404(11) .0330(11) .0068(10) .0161(10) .0181(9)
    N62 .0822(18) .0438(12) .0379(12) .0103(11) .0242(11) .0232(10)
    C63 .0709(19) .0384(14) .0334(13) .0078(12) .0172(12) .0151(11)
    C64 .0560(15) .0456(14) .0285(12) .0034(11) .0109(10) .0197(10)
    C65 .0503(14) .0386(13) .0361(13) .0042(10) .0096(10) .0207(11)
    C66 .077(2) .079(2) .0377(15) .0099(18) .0182(14) .0364(16)
    C67 .071(2) .0473(16) .067(2) .0093(14) .0145(16) .0363(16)