#------------------------------------------------------------------------------
#$Date: 2019-11-23 09:49:49 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/54/7235430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7235430
loop_
_publ_author_name
'Tarai, Arup'
'Baruah, Jubaraj B.'
_publ_section_title
;
 A study on fluoride detection and assembly of hydroxyaromatic aldoximes
 caused by tetrabutylammonium fluoride
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2301
_journal_paper_doi               10.1039/C4CE02311K
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C14 H13 N2 O6, C16 H36 N'
_chemical_formula_sum            'C30 H49 N3 O6'
_chemical_formula_weight         547.72
_chemical_name_systematic
; 
 2 4 dihydroxy aromatic aldoxime
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.931(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2317(7)
_cell_length_b                   9.6547(4)
_cell_length_c                   20.2299(8)
_cell_measurement_temperature    296(2)
_cell_volume                     3122.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1010
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17739
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      5.457
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+7.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                1431
_reflns_number_total             2711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce02311k2.cif
_cod_data_source_block           publication_text
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_original_formula_sum        'C30 H49  N3 O6'
_cod_database_code               7235430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.0002(7) 0.3462(14) 0.3111(7) 0.068(4) Uani 1 1 d D
O2 O 0.7512(9) 0.6093(17) 0.2631(7) 0.073(4) Uani 1 1 d D
O3 O 0.6350(10) 0.7765(19) 0.4022(9) 0.092(5) Uani 1 1 d D
N2 N 0.0000 0.887(2) 0.2500 0.059(6) Uani 1 2 d S
N1 N 0.6894(10) 0.7083(17) 0.3659(8) 0.065(4) Uani 1 1 d .
C5 C 0.9408(11) 0.4205(19) 0.3320(10) 0.054(5) Uani 1 1 d .
C4 C 0.8740(11) 0.4759(18) 0.2869(9) 0.054(5) Uani 1 1 d .
H4 H 0.8701 0.4595 0.2412 0.064 Uiso 1 1 calc R
C3 C 0.8138(10) 0.5551(19) 0.3099(9) 0.053(5) Uani 1 1 d .
C1 C 0.7534(12) 0.656(2) 0.4039(10) 0.063(5) Uani 1 1 d .
H1A H 0.7588 0.6675 0.4501 0.076 Uiso 1 1 calc RD
C2 C 0.8165(11) 0.5796(19) 0.3785(9) 0.053(5) Uani 1 1 d .
C6 C 0.9442(11) 0.445(2) 0.4002(10) 0.064(5) Uani 1 1 d .
H6 H 0.9879 0.4083 0.4311 0.077 Uiso 1 1 calc R
C7 C 0.8834(11) 0.523(2) 0.4221(10) 0.063(5) Uani 1 1 d .
H7 H 0.8872 0.5385 0.4679 0.075 Uiso 1 1 calc R
C14 C 0.0629(13) 0.792(2) 0.2923(11) 0.075(6) Uani 1 1 d .
H14A H 0.0323 0.7268 0.3154 0.089 Uiso 1 1 calc R
H14B H 0.0913 0.7388 0.2622 0.089 Uiso 1 1 calc R
C8 C -0.0414(14) 0.983(2) 0.2938(12) 0.082(7) Uani 1 1 d .
H8A H 0.0015 1.0427 0.3181 0.098 Uiso 1 1 calc R
H8B H -0.0803 1.0417 0.2646 0.098 Uiso 1 1 calc R
C11 C 0.1276(16) 0.860(3) 0.3431(13) 0.103(8) Uani 1 1 d .
H11A H 0.1002 0.9146 0.3731 0.124 Uiso 1 1 calc R
H11B H 0.1605 0.9221 0.3205 0.124 Uiso 1 1 calc R
C9 C -0.104(2) 1.029(4) 0.3948(17) 0.152(15) Uani 1 1 d .
H9A H -0.0527 1.0812 0.4087 0.183 Uiso 1 1 calc R
H9B H -0.1457 1.0930 0.3725 0.183 Uiso 1 1 calc R
C10 C -0.0873(18) 0.917(3) 0.3434(14) 0.109(9) Uani 1 1 d .
H10A H -0.0543 0.8422 0.3664 0.131 Uiso 1 1 calc R
H10B H -0.1399 0.8792 0.3205 0.131 Uiso 1 1 calc R
C12 C 0.1860(17) 0.755(3) 0.3843(14) 0.117(10) Uani 1 1 d .
H12A H 0.2116 0.6986 0.3536 0.140 Uiso 1 1 calc R
H12B H 0.2305 0.8053 0.4123 0.140 Uiso 1 1 calc R
C15 C 0.149(2) 0.665(3) 0.4259(18) 0.150(13) Uani 1 1 d .
H15A H 0.1214 0.7187 0.4556 0.226 Uiso 1 1 calc R
H15B H 0.1912 0.6083 0.4517 0.226 Uiso 1 1 calc R
H15C H 0.1086 0.6069 0.3985 0.226 Uiso 1 1 calc R
C16 C -0.130(3) 0.979(5) 0.450(2) 0.24(3) Uani 1 1 d .
H16A H -0.1855 0.9433 0.4379 0.360 Uiso 1 1 calc R
H16B H -0.1295 1.0523 0.4822 0.360 Uiso 1 1 calc R
H16C H -0.0929 0.9065 0.4692 0.360 Uiso 1 1 calc R
H3A H 0.599(11) 0.80(2) 0.372(9) 0.10(10) Uiso 1 1 d D
H2A H 0.725(13) 0.67(2) 0.284(11) 0.10(9) Uiso 1 1 d D
H1 H 1.0000 0.356(17) 0.2500 0.13(11) Uiso 1 2 d SD
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 N2 C8 104(2) . 2
C8 N2 C14 112.0(12) . 2
C8 N2 C14 111.2(12) 2 2
C8 N2 C14 111.2(12) . .
C8 N2 C14 112.0(12) 2 .
C14 N2 C14 106(2) 2 .
C1 N1 O3 112.9(16) . .
O1 C5 C6 119.9(17) . .
O1 C5 C4 121.6(17) . .
C6 C5 C4 118.4(17) . .
C3 C4 C5 120.4(17) . .
O2 C3 C4 117.5(16) . .
O2 C3 C2 121.0(16) . .
C4 C3 C2 121.5(17) . .
N1 C1 C2 123.0(18) . .
C7 C2 C3 116.8(16) . .
C7 C2 C1 120.3(17) . .
C3 C2 C1 122.9(17) . .
C7 C6 C5 120.2(18) . .
C6 C7 C2 122.5(18) . .
C11 C14 N2 116.6(18) . .
C10 C8 N2 117.0(19) . .
C14 C11 C12 112(2) . .
C16 C9 C10 115(3) . .
C8 C10 C9 108(2) . .
C15 C12 C11 116(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.33(2) .
O2 C3 1.37(2) .
O3 N1 1.41(2) .
N2 C8 1.52(2) .
N2 C8 1.52(2) 2
N2 C14 1.52(2) 2
N2 C14 1.52(2) .
N1 C1 1.29(2) .
C5 C6 1.39(3) .
C5 C4 1.40(2) .
C4 C3 1.38(2) .
C3 C2 1.40(2) .
C1 C2 1.43(2) .
C2 C7 1.39(2) .
C6 C7 1.38(2) .
C14 C11 1.49(3) .
C8 C10 1.49(3) .
C11 C12 1.53(3) .
C9 C16 1.35(5) .
C9 C10 1.56(4) .
C12 C15 1.41(3) .
