#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/55/2205584.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_2205584
loop_
_publ_author_name
'Maria Gdaniec'
_publ_section_title
;
 O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylaminium chloride
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1187
_journal_page_last               o1189
_journal_paper_doi               10.1107/S1600536805009347
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C7 H5 F5 N O +, Cl -'
_chemical_formula_moiety         'C7 H5 F5 N O +, Cl -'
_chemical_formula_sum            'C7 H5 Cl F5 N O'
_chemical_formula_weight         249.57
_chemical_name_systematic
;
O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylaminium chloride
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.939(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.994(3)
_cell_length_b                   5.4020(8)
_cell_length_c                   9.0305(15)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     960.7(3)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2004)'
_computing_molecular_graphics
;
Stereochemical Workstation Operation Manual (Siemens, 1989) and
MERCURY (Bruno et al., 2002)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Kuma KM4CCD κ-geometry'
_diffrn_measurement_method       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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3889
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.14
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0436P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                1042
_reflns_number_total             1702
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6061.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205584
_cod_database_fobs_code          2205584
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'
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_type_symbol
Cl1 0.43596(3) 0.49780(16) 0.64572(7) 0.0221(2) Uani d . 1 Cl
N1 0.59161(11) 0.5006(7) 0.7027(3) 0.0199(5) Uani d . 1 N
O1 0.66373(8) 0.5146(4) 0.71519(19) 0.0232(5) Uani d . 1 O
F2 0.78437(9) 0.8558(4) 1.01187(19) 0.0328(5) Uani d . 1 F
F3 0.91761(9) 0.8765(4) 0.9974(2) 0.0383(5) Uani d . 1 F
F4 0.97437(8) 0.5267(4) 0.84078(18) 0.0393(5) Uani d . 1 F
F5 0.89702(9) 0.1485(4) 0.70502(19) 0.0374(5) Uani d . 1 F
F6 0.76461(9) 0.1228(3) 0.72276(19) 0.0300(5) Uani d . 1 F
C1 0.77027(12) 0.4886(7) 0.8679(3) 0.0162(6) Uani d . 1 C
C2 0.81110(15) 0.6768(6) 0.9345(3) 0.0217(7) Uani d . 1 C
C3 0.87928(15) 0.6903(6) 0.9280(3) 0.0239(8) Uani d . 1 C
C4 0.90836(13) 0.5140(7) 0.8506(3) 0.0238(7) Uani d . 1 C
C5 0.86958(16) 0.3222(6) 0.7817(3) 0.0251(8) Uani d . 1 C
C6 0.80141(15) 0.3122(6) 0.7918(3) 0.0209(7) Uani d . 1 C
C7 0.69560(13) 0.4771(7) 0.8702(3) 0.0219(7) Uani d . 1 C
H7B 0.6832 0.3175 0.9065 0.026(9) Uiso calc R 1 H
H7A 0.6823 0.6058 0.9341 0.011(7) Uiso calc R 1 H
H1A 0.5747(17) 0.647(7) 0.748(4) 0.047(11) Uiso d . 1 H
H1B 0.5743(15) 0.502(7) 0.591(4) 0.051(10) Uiso d . 1 H
H1C 0.5814(19) 0.335(8) 0.749(4) 0.061(13) Uiso d . 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
Cl1 0.0215(4) 0.0218(4) 0.0225(4) 0.0015(4) 0.0024(3) -0.0001(4)
N1 0.0123(12) 0.0231(15) 0.0238(13) 0.0024(16) 0.0021(10) -0.0028(17)
O1 0.0124(9) 0.0379(13) 0.0187(10) 0.0016(12) 0.0010(7) 0.0015(12)
F2 0.0361(11) 0.0318(11) 0.0306(11) 0.0028(9) 0.0064(8) -0.0122(9)
F3 0.0323(11) 0.0440(13) 0.0369(11) -0.0164(10) 0.0010(9) -0.0072(10)
F4 0.0173(9) 0.0672(15) 0.0341(10) -0.0007(11) 0.0065(7) 0.0049(12)
F5 0.0321(11) 0.0490(13) 0.0327(11) 0.0135(10) 0.0104(9) -0.0106(10)
F6 0.0302(11) 0.0287(11) 0.0304(10) -0.0013(9) 0.0028(8) -0.0078(9)
C1 0.0155(13) 0.0205(16) 0.0131(13) 0.0014(17) 0.0037(11) 0.0042(17)
C2 0.0275(18) 0.0203(19) 0.0177(16) 0.0042(15) 0.0050(13) 0.0006(14)
C3 0.0243(18) 0.027(2) 0.0185(17) -0.0085(16) -0.0030(14) 0.0016(15)
C4 0.0143(14) 0.038(2) 0.0188(14) -0.0030(19) 0.0026(11) 0.0084(19)
C5 0.0262(18) 0.031(2) 0.0191(17) 0.0117(16) 0.0070(14) 0.0025(15)
C6 0.0222(17) 0.0217(19) 0.0167(16) -0.0041(15) -0.0024(13) 0.0011(14)
C7 0.0185(14) 0.033(2) 0.0135(13) 0.0021(18) -0.0001(11) 0.0007(17)
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 N1 H1A 110(2)
O1 N1 H1B 104.3(17)
H1A N1 H1B 109(3)
O1 N1 H1C 107(2)
H1A N1 H1C 116(2)
H1B N1 H1C 111(3)
N1 O1 C7 109.79(18)
C2 C1 C6 116.2(2)
C2 C1 C7 122.8(3)
C6 C1 C7 120.9(3)
F2 C2 C1 119.7(3)
F2 C2 C3 117.8(3)
C1 C2 C3 122.5(3)
F3 C3 C4 119.8(3)
F3 C3 C2 120.4(3)
C4 C3 C2 119.7(3)
F4 C4 C3 120.5(3)
F4 C4 C5 119.6(3)
C3 C4 C5 119.9(3)
F5 C5 C4 120.8(3)
F5 C5 C6 120.2(3)
C4 C5 C6 119.0(3)
F6 C6 C5 117.7(3)
F6 C6 C1 119.7(3)
C5 C6 C1 122.6(3)
O1 C7 C1 104.7(2)
O1 C7 H7B 110.8
C1 C7 H7B 110.8
O1 C7 H7A 110.8
C1 C7 H7A 110.8
H7B C7 H7A 108.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.429(3)
N1 H1A 0.98(4)
N1 H1B 1.01(3)
N1 H1C 1.02(4)
O1 C7 1.448(3)
F2 C2 1.355(3)
F3 C3 1.351(3)
F4 C4 1.340(3)
F5 C5 1.338(3)
F6 C6 1.349(3)
C1 C2 1.376(4)
C1 C6 1.384(4)
C1 C7 1.498(3)
C2 C3 1.376(4)
C3 C4 1.369(4)
C4 C5 1.377(4)
C5 C6 1.383(4)
C7 H7B 0.9700
C7 H7A 0.9700
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
N1 H1A Cl1 2_656 0.98(4) 2.15(4) 3.107(3) 165(3)
N1 H1B Cl1 3_666 1.01(3) 2.11(3) 3.099(3) 166(2)
N1 H1C Cl1 2_646 1.02(4) 2.11(4) 3.133(3) 177(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2056260
