data_2013871 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2004 _journal_volume 60 _journal_page_first o194 _journal_page_last o195 _publ_section_title ; 5-Amino-3-tert-butyl-1-(4-nitrophenyl)-1H-pyrazole forms hydrogen-bonded sheets of alternating R^2^~2~(20) and R^6^~6~(32) rings ; loop_ _publ_author_name 'Low, John N.' 'Cobo, Justo' 'Abonia, Rodrigo' 'Quiroga, Jairo' 'Glidewell, Christopher' _chemical_formula_moiety 'C13 H16 N4 O2' _chemical_formula_sum 'C13 H16 N4 O2' _chemical_formula_iupac 'C13 H16 N4 O2' _chemical_formula_weight 260.30 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 5.9581(2) _cell_length_b 18.3064(11) _cell_length_c 12.0776(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.4150(12) _cell_angle_gamma 90.00 _cell_volume 1314.98(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.315 _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 0.1283(2) 0.28405(8) 0.47981(12) 0.0220(4) Uani d . 1 . . N N2 -0.0010(2) 0.24448(9) 0.55116(12) 0.0230(4) Uani d . 1 . . N C3 -0.1270(3) 0.20118(10) 0.48495(16) 0.0224(4) Uani d . 1 . . C C4 -0.0870(3) 0.21303(11) 0.37242(16) 0.0249(5) Uani d . 1 . . C C5 0.0753(3) 0.26618(11) 0.37125(15) 0.0237(4) Uani d . 1 . . C N5 0.1812(3) 0.29677(10) 0.28533(13) 0.0306(4) Uani d . 1 . . N C11 0.2811(3) 0.33687(10) 0.52501(15) 0.0216(4) Uani d . 1 . . C C12 0.4827(3) 0.35070(11) 0.47563(16) 0.0243(4) Uani d . 1 . . C C13 0.6273(3) 0.40335(10) 0.51985(16) 0.0252(5) Uani d . 1 . . C C14 0.5694(3) 0.44051(10) 0.61374(16) 0.0233(4) Uani d . 1 . . C N14 0.7185(3) 0.49841(9) 0.65867(15) 0.0299(4) Uani d . 1 . . N O141 0.8857(2) 0.51414(8) 0.60916(13) 0.0390(4) Uani d . 1 . . O O142 0.6673(3) 0.52972(9) 0.74362(14) 0.0451(4) Uani d . 1 . . O C15 0.3728(3) 0.42629(11) 0.66465(17) 0.0267(5) Uani d . 1 . . C C16 0.2286(3) 0.37361(11) 0.62040(15) 0.0236(5) Uani d . 1 . . C C31 -0.2820(3) 0.14534(10) 0.53212(16) 0.0252(5) Uani d . 1 . . C C32 -0.1497(4) 0.07485(12) 0.5542(2) 0.0397(6) Uani d . 1 . . C C33 -0.3742(4) 0.17272(13) 0.63963(18) 0.0373(6) Uani d . 1 . . C C34 -0.4792(4) 0.12980(13) 0.44822(19) 0.0408(6) Uani d . 1 . . C H4 -0.1581 0.1891 0.3100 0.030 Uiso calc R 1 . . H H5A 0.1182 0.2843 0.2203 0.037 Uiso d R 1 . . H H5B 0.2177 0.3433 0.2910 0.037 Uiso d R 1 . . H H12 0.5201 0.3240 0.4119 0.029 Uiso calc R 1 . . H H13 0.7641 0.4139 0.4865 0.030 Uiso calc R 1 . . H H15 0.3373 0.4524 0.7293 0.032 Uiso calc R 1 . . H H16 0.0938 0.3625 0.6551 0.028 Uiso calc R 1 . . H H32A -0.0937 0.0568 0.4846 0.059 Uiso calc R 1 . . H H32B -0.2480 0.0380 0.5848 0.059 Uiso calc R 1 . . H H32C -0.0224 0.0845 0.6073 0.059 Uiso calc R 1 . . H H33A -0.2501 0.1791 0.6958 0.056 Uiso calc R 1 . . H H33B -0.4812 0.1370 0.6661 0.056 Uiso calc R 1 . . H H33C -0.4505 0.2196 0.6261 0.056 Uiso calc R 1 . . H H34A -0.5587 0.1755 0.4297 0.061 Uiso calc R 1 . . H H34B -0.5828 0.0953 0.4805 0.061 Uiso calc R 1 . . H H34C -0.4223 0.1087 0.3808 0.061 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 0.0240(8) 0.0251(10) 0.0169(8) -0.0029(7) 0.0014(6) 0.0017(7) N2 0.0227(8) 0.0241(10) 0.0226(9) -0.0014(7) 0.0029(6) 0.0032(7) C3 0.0201(10) 0.0216(11) 0.0255(11) 0.0047(8) 0.0007(8) -0.0016(9) C4 0.0256(10) 0.0273(12) 0.0217(11) -0.0007(8) 0.0005(8) -0.0045(9) C5 0.0250(10) 0.0265(12) 0.0197(10) 0.0016(8) 0.0018(7) 0.0003(9) N5 0.0375(10) 0.0350(11) 0.0192(9) -0.0100(8) 0.0019(7) -0.0014(8) C11 0.0231(10) 0.0215(11) 0.0199(10) 0.0009(8) -0.0020(7) 0.0017(8) C12 0.0243(10) 0.0248(12) 0.0238(10) 0.0029(8) 0.0017(8) 0.0000(9) C13 0.0216(10) 0.0248(12) 0.0292(12) 0.0021(8) 0.0012(8) 0.0037(9) C14 0.0245(10) 0.0187(11) 0.0259(11) 0.0007(8) -0.0052(8) -0.0017(9) N14 0.0292(10) 0.0244(10) 0.0354(11) 0.0018(7) -0.0046(8) -0.0023(8) O141 0.0293(8) 0.0360(10) 0.0518(10) -0.0064(7) 0.0038(7) -0.0028(8) O142 0.0492(10) 0.0425(11) 0.0436(10) -0.0092(8) 0.0036(7) -0.0178(9) C15 0.0289(11) 0.0267(12) 0.0242(11) 0.0039(9) -0.0011(8) -0.0027(9) C16 0.0228(10) 0.0254(12) 0.0228(11) 0.0021(8) 0.0020(7) 0.0023(9) C31 0.0264(11) 0.0219(11) 0.0276(11) -0.0012(8) 0.0037(8) 0.0008(9) C32 0.0395(13) 0.0270(13) 0.0534(15) 0.0045(10) 0.0097(10) 0.0070(11) C33 0.0372(12) 0.0377(14) 0.0385(13) -0.0059(10) 0.0140(10) -0.0021(11) C34 0.0332(12) 0.0425(15) 0.0464(15) -0.0121(10) -0.0008(10) 0.0031(12) 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 N2 . 1.393(2) y N2 C3 . 1.327(2) y C3 C4 . 1.411(3) y C4 C5 . 1.373(3) y C5 N1 . 1.370(2) y N1 C11 . 1.415(2) y C3 C31 . 1.512(3) no C4 H4 . 0.95 no C5 N5 . 1.366(2) y N5 H5A . 0.88 no N5 H5B . 0.88 no C11 C16 . 1.386(3) no C11 C12 . 1.396(3) no C12 C13 . 1.379(3) no C12 H12 . 0.95 no C13 C14 . 1.384(3) no C13 H13 . 0.95 no C14 C15 . 1.380(3) no C14 N14 . 1.466(2) y N14 O141 . 1.226(2) y N14 O142 . 1.229(2) y C15 C16 . 1.378(3) no C15 H15 . 0.95 no C16 H16 . 0.95 no C31 C33 . 1.524(3) no C31 C32 . 1.527(3) no C31 C34 . 1.532(3) no C32 H32A . 0.98 no C32 H32B . 0.98 no C32 H32C . 0.98 no C33 H33A . 0.98 no C33 H33B . 0.98 no C33 H33C . 0.98 no C34 H34A . 0.98 no C34 H34B . 0.98 no C34 H34C . 0.98 no