#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/53/2205374.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_2205374
loop_
_publ_author_name
'Radosavljević Evans, Ivana'
'Mészáros Szécsényi, Katalin'
'Leovac, Vukadin, M.'
_publ_section_title
;
 1-(Hydroxymethyl)-3,5-dimethylpyrazole
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o625
_journal_page_last               o626
_journal_paper_doi               10.1107/S1600536805003971
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H10 N2 O1'
_chemical_formula_moiety         'C6 H10 N2 O1'
_chemical_formula_sum            'C6 H10 N2 O'
_chemical_formula_weight         126.16
_chemical_name_systematic
;
1-(hydroxymethyl)-3,5-dimethylpyrazole
;
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 107.3960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2877(2)
_cell_length_b                   11.9265(3)
_cell_length_c                   8.1586(2)
_cell_measurement_reflns_used    6570
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.25
_cell_measurement_theta_min      3.1
_cell_volume                     676.68(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ATOMS (Dowty, 2000)'
_computing_publication_material  CRYSTALS
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13356
_diffrn_reflns_theta_full        33.106
_diffrn_reflns_theta_max         34.49
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Chebychev polynomial, (Watkin, 1994; Prince, 1982):
w = 1.0/[A₀T₀(x) + A₁T₁(x) ... + Aₙ₋₁]Tₙ₋₁(x)],
where Ai are the Chebychev coefficients listed below and
x = Fc/Fₘₐₓ; method = Robust Weighting (Prince, 1982);
W = w[1-(\dF/6\sF)²]²; Ai are 3.44 4.59 1.31
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.104
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                2113
_reflns_number_total             2742
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk6045.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C6 H10 N2 O1'
_cod_database_code               2205374
_cod_database_fobs_code          2205374
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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_occupancy
_atom_site_type_symbol
O1 -0.02535(9) -0.04616(6) 0.23811(8) 0.0220 Uani 1.0000 O
N1 0.26298(10) 0.04284(6) 0.40283(9) 0.0190 Uani 1.0000 N
N2 0.25525(10) 0.08755(6) 0.55433(9) 0.0189 Uani 1.0000 N
C1 0.16421(12) -0.06190(7) 0.34201(12) 0.0226 Uani 1.0000 C
C2 0.36052(11) 0.10985(8) 0.32329(10) 0.0211 Uani 1.0000 C
C3 0.42099(11) 0.20151(7) 0.42920(12) 0.0218 Uani 1.0000 C
C4 0.35202(11) 0.18413(7) 0.57094(11) 0.0194 Uani 1.0000 C
C5 0.38717(15) 0.08069(11) 0.15405(13) 0.0317 Uani 1.0000 C
C6 0.37831(13) 0.25601(8) 0.72617(13) 0.0280 Uani 1.0000 C
H1 -0.101(2) -0.0516(14) 0.304(2) 0.040(4) Uiso 1.0000 H
H2 0.237(2) -0.0995(12) 0.2760(19) 0.028(3) Uiso 1.0000 H
H3 0.166(2) -0.1056(13) 0.446(2) 0.033(4) Uiso 1.0000 H
H4 0.362(3) 0.3355(17) 0.692(2) 0.053(5) Uiso 1.0000 H
H5 0.508(3) 0.2465(15) 0.808(3) 0.055(5) Uiso 1.0000 H
H6 0.277(3) 0.2393(16) 0.783(2) 0.051(5) Uiso 1.0000 H
H7 0.265(3) 0.0639(15) 0.071(2) 0.047(5) Uiso 1.0000 H
H8 0.496(2) 0.2622(12) 0.408(2) 0.031(3) Uiso 1.0000 H
H9 0.480(3) 0.0133(16) 0.167(2) 0.048(4) Uiso 1.0000 H
H10 0.455(3) 0.1415(17) 0.119(3) 0.059(5) Uiso 1.0000 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 0.0180(2) 0.0279(3) 0.0187(3) -0.0024(2) 0.0034(2) -0.0020(2)
N1 0.0176(3) 0.0203(3) 0.0181(3) -0.0014(2) 0.0041(2) -0.0009(2)
N2 0.0180(3) 0.0193(3) 0.0190(3) -0.0019(2) 0.0049(2) -0.0013(2)
C1 0.0191(3) 0.0201(3) 0.0260(4) 0.0000(2) 0.0028(3) -0.0044(3)
C2 0.0164(3) 0.0278(4) 0.0183(3) 0.0008(3) 0.0038(2) 0.0043(3)
C3 0.0174(3) 0.0225(3) 0.0242(3) -0.0022(2) 0.0042(3) 0.0053(3)
C4 0.0158(3) 0.0188(3) 0.0222(3) -0.0013(2) 0.0033(2) -0.0003(3)
C5 0.0273(4) 0.0490(6) 0.0191(4) 0.0018(4) 0.0075(3) 0.0018(4)
C6 0.0247(4) 0.0270(4) 0.0313(4) -0.0050(3) 0.0068(3) -0.0095(3)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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
_geom_angle_publ_flag
C4 C6 H5 111.2(11) no
C4 C6 H6 110.7(11) no
H5 C6 H6 110.5(15) no
C4 C6 H4 109.8(11) no
H5 C6 H4 108.1(14) no
H6 C6 H4 106.2(15) no
C1 O1 H1 107.9(11) no
N1 N2 C4 105.40(7) yes
N2 N1 C1 119.71(7) yes
N2 N1 C2 111.90(7) yes
C1 N1 C2 128.31(7) yes
N1 C1 O1 112.93(7) yes
N1 C1 H2 106.8(9) no
O1 C1 H2 109.3(9) no
N1 C1 H3 106.2(9) no
O1 C1 H3 110.4(8) no
H2 C1 H3 111.2(12) no
C2 C3 C4 105.78(7) yes
C2 C3 H8 125.3(9) no
C4 C3 H8 128.9(9) no
C3 C2 N1 106.36(7) yes
C3 C2 C5 131.14(8) yes
N1 C2 C5 122.49(8) yes
C6 C4 C3 128.72(8) yes
C6 C4 N2 120.72(8) yes
C3 C4 N2 110.55(7) yes
C2 C5 H7 110.6(11) no
C2 C5 H10 108.5(12) no
H7 C5 H10 113.3(16) no
C2 C5 H9 110.3(11) no
H7 C5 H9 110.4(15) no
H10 C5 H9 103.5(14) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.4007(10) yes
N1 C1 1.4530(11) yes
N1 C2 1.3568(11) yes
N2 N1 1.3627(10) yes
N2 C4 1.3362(10) yes
C2 C5 1.4918(13) yes
C3 C2 1.3814(13) yes
C3 C4 1.4073(12) yes
C6 C4 1.4934(12) yes
C6 H5 0.988(19) no
C6 H6 1.000(18) no
C6 H4 0.98(2) no
O1 H1 0.878(17) no
C1 H2 0.972(14) no
C1 H3 0.995(16) no
C3 H8 0.952(15) no
C5 H7 0.963(18) no
C5 H10 0.97(2) no
C5 H9 1.038(19) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 87016
