#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/08/2210873.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_2210873
loop_
_publ_author_name
'Zhang, Li-Ming'
'He, Zhi-Min '
_publ_section_title
;
 5-Amino-1-(2-hydroxyethyl)-1H-pyrazole
;
_journal_coeditor_code           BH2051
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5108
_journal_page_last               o5109
_journal_paper_doi               10.1107/S1600536806042061
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C5 H9 N3 O'
_chemical_formula_moiety         'C5 H9 N3 O'
_chemical_formula_sum            'C5 H9 N3 O'
_chemical_formula_weight         127.15
_chemical_melting_point          .379E-305
_chemical_name_systematic        5-Amino-1-(2-hydroxyethyl)pyrazole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.774(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.977(2)
_cell_length_b                   5.5467(14)
_cell_length_c                   12.562(3)
_cell_measurement_reflns_used    1169
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      4.02
_cell_volume                     619.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3003
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.63
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.165
_refine_ls_extinction_coef       0.045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1094
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0417P)²+0.0839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                853
_reflns_number_total             1094
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2051.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               2210873
_cod_database_fobs_code          2210873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O O1 0.17221(12) 0.1734(2) 0.58285(9) 0.0529(4) Uani d D 1
H H1 0.2487(19) 0.096(4) 0.5984(15) 0.079 Uiso d D 1
N N1 0.00693(13) 0.3657(2) 0.74470(9) 0.0350(4) Uani d . 1
N N2 0.05615(14) 0.4198(2) 0.85014(9) 0.0394(4) Uani d . 1
N N3 -0.15422(17) 0.0992(3) 0.63531(12) 0.0461(4) Uani d D 1
C C1 0.19681(17) 0.4116(3) 0.62165(12) 0.0448(5) Uani d . 1
H H1A 0.2253 0.5138 0.5651 0.054 Uiso calc R 1
H H1B 0.2781 0.4129 0.6810 0.054 Uiso calc R 1
C C2 0.05562(17) 0.5066(3) 0.65862(11) 0.0398(4) Uani d . 1
H H2A 0.0726 0.6716 0.6829 0.048 Uiso calc R 1
H H2B -0.0240 0.5084 0.5982 0.048 Uiso calc R 1
C C3 -0.08801(15) 0.1754(3) 0.73550(12) 0.0345(4) Uani d . 1
C C4 -0.10492(17) 0.1050(3) 0.83809(12) 0.0406(4) Uani d . 1
H H4 -0.1642 -0.0199 0.8584 0.049 Uiso calc R 1
C C5 -0.01432(17) 0.2606(3) 0.90483(12) 0.0410(4) Uani d . 1
H H5 -0.0040 0.2544 0.9794 0.049 Uiso calc R 1
H H3A -0.0928(18) 0.083(3) 0.5894(13) 0.057(6) Uiso d D 1
H H3B -0.2097(19) -0.030(3) 0.6385(14) 0.062(6) Uiso d D 1
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 0.0387(7) 0.0626(9) 0.0566(8) 0.0053(6) 0.0035(6) -0.0139(6)
N1 0.0380(7) 0.0355(7) 0.0310(7) 0.0002(6) 0.0024(5) -0.0010(5)
N2 0.0440(8) 0.0398(8) 0.0329(7) -0.0002(6) -0.0001(6) -0.0024(6)
N3 0.0441(9) 0.0466(9) 0.0464(9) -0.0046(7) 0.0020(7) -0.0106(7)
C1 0.0383(9) 0.0542(11) 0.0411(9) -0.0081(8) 0.0022(7) 0.0044(8)
C2 0.0456(10) 0.0369(9) 0.0357(9) -0.0006(7) 0.0004(7) 0.0046(7)
C3 0.0295(8) 0.0329(8) 0.0405(9) 0.0027(6) 0.0028(6) -0.0046(6)
C4 0.0364(9) 0.0390(9) 0.0475(10) -0.0018(7) 0.0097(7) 0.0041(7)
C5 0.0436(9) 0.0455(10) 0.0344(8) 0.0057(8) 0.0069(7) 0.0024(7)
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 O1 H1 108.7(15)
C3 N1 N2 111.74(12)
C3 N1 C2 127.44(12)
N2 N1 C2 120.82(12)
C5 N2 N1 103.89(12)
C3 N3 H3A 114.1(12)
C3 N3 H3B 112.6(12)
H3A N3 H3B 111.5(17)
O1 C1 C2 109.57(13)
O1 C1 H1A 109.8
C2 C1 H1A 109.8
O1 C1 H1B 109.8
C2 C1 H1B 109.8
H1A C1 H1B 108.2
N1 C2 C1 113.16(13)
N1 C2 H2A 108.9
C1 C2 H2A 108.9
N1 C2 H2B 108.9
C1 C2 H2B 108.9
H2A C2 H2B 107.8
N1 C3 C4 106.87(13)
N1 C3 N3 120.32(14)
C4 C3 N3 132.67(15)
C3 C4 C5 105.04(13)
C3 C4 H4 127.5
C5 C4 H4 127.5
N2 C5 C4 112.44(14)
N2 C5 H5 123.8
C4 C5 H5 123.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.415(2)
O1 H1 0.810(15)
N1 C3 1.3516(19)
N1 N2 1.3717(16)
N1 C2 1.4490(18)
N2 C5 1.330(2)
N3 C3 1.3834(19)
N3 H3A 0.855(14)
N3 H3B 0.877(14)
C1 C2 1.503(2)
C1 H1A 0.9700
C1 H1B 0.9700
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.375(2)
C4 C5 1.388(2)
C4 H4 0.9300
C5 H5 0.9300
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
O1 H1 N2 2_546 0.810(15) 2.035(15) 2.8422(18) 175(2) y
N3 H3A O1 3_556 0.855(14) 2.606(17) 3.1149(19) 119.3(14) y
N3 H3A O1 . 0.855(14) 2.443(16) 3.117(2) 136.1(15) y
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
C3 N1 N2 C5 -1.41(15)
C2 N1 N2 C5 178.07(13)
C3 N1 C2 C1 -90.70(18)
N2 N1 C2 C1 89.90(16)
O1 C1 C2 N1 60.44(17)
N2 N1 C3 C4 1.43(16)
C2 N1 C3 C4 -178.01(13)
N2 N1 C3 N3 177.53(13)
C2 N1 C3 N3 -1.9(2)
N1 C3 C4 C5 -0.82(17)
N3 C3 C4 C5 -176.24(16)
N1 N2 C5 C4 0.86(16)
C3 C4 C5 N2 -0.04(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 283510
