#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/44/2214406.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_2214406
loop_
_publ_author_name
'Peter A. Wood'
'Ross S. Forgan'
'Simon Parsons'
'Elna Pidcock'
'Peter A. Tasker'
_publ_section_title
;
 3-Hydroxysalicylaldoxime
;
_journal_coeditor_code           WK2053
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3131
_journal_page_last               o3131
_journal_paper_doi               10.1107/S1600536807020922
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H7 N1 O3'
_chemical_formula_moiety         'C7 H7 N1 O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_chemical_name_systematic        3-Hydroxysalicylaldoxime
_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'
_atom_sites_solution_hydrogens   'geom/difmap (OH)'
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                90
_cell_angle_beta                 114.531(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4603(10)
_cell_length_b                   3.7507(3)
_cell_length_c                   14.8398(11)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    150
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     681.57(9)
_computing_cell_refinement       SAINT
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  CRYSTALS
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8183
_diffrn_reflns_theta_full        26.111
_diffrn_reflns_theta_max         26.643
_diffrn_reflns_theta_min         2.776
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9869
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1424
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000103
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
51.1 83.1 48.9 19.2 3.34
Prince, E. (1982). Mathematical Techniques in Crystallography and Materials
Science. New York: Springer-Verlag.
Watkin, D. J. (1994). Acta Cryst. A50, 411--437.
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1173
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                904
_reflns_number_total             1424
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk2053.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'monoclinic'' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C7 H7 N1 O3'
_cod_database_code               2214406
_cod_database_fobs_code          2214406
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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_occupancy
O O1 0.44009(11) 0.2386(5) 0.06215(10) 0.0333 Uani 1.0000
N N2 0.39503(12) 0.3040(5) 0.13107(11) 0.0266 Uani 1.0000
C C3 0.30117(14) 0.4508(5) 0.08998(13) 0.0258 Uani 1.0000
C C4 0.23874(15) 0.5415(5) 0.14676(13) 0.0240 Uani 1.0000
C C5 0.28033(14) 0.4911(5) 0.24936(13) 0.0226 Uani 1.0000
O O5 0.38212(10) 0.3513(4) 0.30415(10) 0.0277 Uani 1.0000
C C6 0.21770(14) 0.5813(5) 0.30083(13) 0.0241 Uani 1.0000
O O6 0.25519(12) 0.5341(4) 0.40046(10) 0.0335 Uani 1.0000
C C7 0.11473(15) 0.7240(5) 0.25057(15) 0.0272 Uani 1.0000
C C8 0.07223(15) 0.7703(5) 0.14860(15) 0.0279 Uani 1.0000
C C9 0.13386(15) 0.6814(5) 0.09742(14) 0.0276 Uani 1.0000
H H1 0.501(2) 0.135(8) 0.099(2) 0.0512 Uiso 1.0000
H H3 0.2687 0.4989 0.0202 0.0300 Uiso 1.0000
H H5 0.410(2) 0.296(7) 0.261(2) 0.0424 Uiso 1.0000
H H6 0.315(2) 0.444(8) 0.423(2) 0.0511 Uiso 1.0000
H H7 0.0735 0.7879 0.2870 0.0341 Uiso 1.0000
H H8 0.0024 0.8643 0.1144 0.0319 Uiso 1.0000
H H9 0.1071 0.7129 0.0287 0.0318 Uiso 1.0000
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 0.0246(7) 0.0531(10) 0.0249(7) 0.0044(7) 0.0129(6) 0.0003(7)
N2 0.0258(8) 0.0353(10) 0.0224(8) -0.0004(7) 0.0136(6) -0.0014(7)
C3 0.0262(9) 0.0291(10) 0.0207(8) -0.0015(8) 0.0084(7) 0.0015(7)
C4 0.0237(9) 0.0232(9) 0.0260(9) -0.0023(7) 0.0112(7) 0.0000(7)
C5 0.0178(8) 0.0229(10) 0.0249(9) -0.0022(7) 0.0065(7) -0.0002(7)
O5 0.0201(6) 0.0395(9) 0.0225(6) 0.0029(6) 0.0078(5) 0.0002(6)
C6 0.0235(9) 0.0254(9) 0.0240(9) -0.0029(8) 0.0104(7) -0.0012(8)
O6 0.0288(7) 0.0516(10) 0.0210(7) 0.0063(7) 0.0111(6) 0.0014(7)
C7 0.0262(9) 0.0254(9) 0.0333(10) -0.0018(8) 0.0156(8) -0.0028(8)
C8 0.0206(9) 0.0267(10) 0.0335(10) 0.0038(8) 0.0085(8) 0.0021(8)
C9 0.0276(9) 0.0266(10) 0.0250(9) 0.0015(8) 0.0073(7) 0.0033(8)
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
N2 O1 H1 101.7(18) no
O1 N2 C3 111.52(14) no
N2 C3 C4 121.25(16) no
N2 C3 H3 120.9 no
C4 C3 H3 117.8 no
C3 C4 C5 122.11(17) no
C3 C4 C9 119.06(16) no
C5 C4 C9 118.83(17) no
C4 C5 O5 123.05(16) no
C4 C5 C6 120.23(17) no
O5 C5 C6 116.72(16) no
C5 O5 H5 106.0(17) no
C5 C6 O6 121.87(17) no
C5 C6 C7 119.86(17) no
O6 C6 C7 118.27(16) no
C6 O6 H6 111.2(19) no
C6 C7 C8 120.29(17) no
C6 C7 H7 118.8 no
C8 C7 H7 120.9 no
C7 C8 C9 120.02(18) no
C7 C8 H8 120.4 no
C9 C8 H8 119.5 no
C4 C9 C8 120.75(18) no
C4 C9 H9 117.8 no
C8 C9 H9 121.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N2 1.4103(19) no
O1 H1 0.87(3) no
N2 C3 1.277(2) no
C3 C4 1.456(2) no
C3 H3 0.959 no
C4 C5 1.400(3) no
C4 C9 1.395(3) no
C5 O5 1.374(2) no
C5 C6 1.394(2) no
O5 H5 0.89(2) no
C6 O6 1.361(2) no
C6 C7 1.380(3) no
O6 H6 0.81(3) no
C7 C8 1.389(3) no
C7 H7 0.952 no
C8 C9 1.378(3) no
C8 H8 0.932 no
C9 H9 0.938 no
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 O5 3_645 0.87(2) 1.95(2) 2.7984(18) 167(3) yes
O5 H5 N2 . 0.89(3) 1.85(3) 2.651(2) 148(3) yes
O6 H6 O1 4_555 0.81(3) 2.16(2) 2.8353(18) 141(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15619822
