#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/54/7235431.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_7235431
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         'C16 H36 N, 2(C7 H7 N O3), F'
_chemical_formula_sum            'C30 H50 F N3 O6'
_chemical_formula_weight         567.73
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 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                 101.203(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5189(7)
_cell_length_b                   9.4321(7)
_cell_length_c                   18.7965(14)
_cell_measurement_temperature    296(2)
_cell_volume                     1655.5(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 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18857
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0383
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1766
_reflns_number_total             2989
_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      Pc
_cod_database_code               7235431
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
C6 C 0.2818(2) 0.1093(2) 0.06309(12) 0.0578(6) Uani 1 1 d .
C1 C 0.3113(3) 0.2556(3) 0.06586(12) 0.0617(6) Uani 1 1 d .
C5 C 0.2209(2) 0.0472(2) 0.11765(12) 0.0629(6) Uani 1 1 d .
C4 C 0.1931(3) 0.1324(3) 0.17428(12) 0.0729(7) Uani 1 1 d .
H4 H 0.1534 0.0916 0.2109 0.087 Uiso 1 1 calc R
C2 C 0.2823(3) 0.3356(3) 0.12245(14) 0.0696(7) Uani 1 1 d .
H2 H 0.3025 0.4321 0.1243 0.084 Uiso 1 1 calc R
C7 C 0.1880(3) -0.1037(3) 0.11648(14) 0.0722(7) Uani 1 1 d .
H7 H 0.1433 -0.1418 0.1520 0.087 Uiso 1 1 calc R
C3 C 0.2230(3) 0.2737(3) 0.17697(13) 0.0765(8) Uani 1 1 d .
H3 H 0.2038 0.3285 0.2151 0.092 Uiso 1 1 calc R
C11 C 0.5450(4) 0.8480(3) 0.81980(18) 0.0955(10) Uani 1 1 d .
H11 H 0.4765 0.8920 0.7847 0.115 Uiso 1 1 calc R
O2 O 0.3150(2) 0.03588(16) 0.00678(8) 0.0755(5) Uani 1 1 d .
H2A H 0.3080 -0.0493 0.0140 0.113 Uiso 1 1 calc R
O1 O 0.3706(2) 0.30859(16) 0.01126(10) 0.0790(5) Uani 1 1 d .
H1 H 0.3491 0.3925 0.0050 0.118 Uiso 1 1 calc R
O3 O 0.1823(3) -0.32520(17) 0.07523(11) 0.0921(6) Uani 1 1 d .
H3A H 0.2154 -0.3741 0.0464 0.138 Uiso 1 1 calc R
N1 N 0.2195(2) -0.18381(19) 0.06766(12) 0.0717(6) Uani 1 1 d .
C14 C 0.7484(3) 0.7204(2) 0.92518(13) 0.0636(6) Uani 1 1 d .
C13 C 0.7890(3) 0.7715(3) 0.86241(13) 0.0698(7) Uani 1 1 d .
C9 C 0.6072(3) 0.7290(2) 0.93403(13) 0.0681(7) Uani 1 1 d .
C12 C 0.6842(4) 0.8363(3) 0.80963(15) 0.0937(9) Uani 1 1 d .
H12 H 0.7088 0.8717 0.7675 0.112 Uiso 1 1 calc R
C15 C 0.9325(3) 0.7548(3) 0.84917(15) 0.0811(8) Uani 1 1 d .
H15 H 0.9538 0.7905 0.8064 0.097 Uiso 1 1 calc R
C10 C 0.5070(3) 0.7950(3) 0.88147(17) 0.0805(8) Uani 1 1 d .
H10 H 0.4130 0.8036 0.8879 0.097 Uiso 1 1 calc R
O5 O 0.84367(19) 0.6581(2) 0.97989(10) 0.0868(5) Uani 1 1 d .
H5 H 0.9186 0.6418 0.9660 0.130 Uiso 1 1 calc R
O6 O 1.1591(3) 0.6824(3) 0.87036(13) 0.1094(7) Uani 1 1 d .
H6 H 1.2217 0.6549 0.9039 0.164 Uiso 1 1 calc R
O4 O 0.5760(2) 0.6714(2) 0.99560(11) 0.0948(6) Uani 1 1 d D
N2 N 1.0307(3) 0.6931(2) 0.89383(13) 0.0783(6) Uani 1 1 d .
C24 C 0.6397(3) 0.1983(2) -0.06202(12) 0.0634(6) Uani 1 1 d .
H24A H 0.6559 0.1141 -0.0889 0.076 Uiso 1 1 calc R
H24B H 0.5582 0.1794 -0.0394 0.076 Uiso 1 1 calc R
C28 C 0.9015(3) 0.2622(3) -0.03347(13) 0.0669(6) Uani 1 1 d .
H28A H 0.8846 0.3544 -0.0564 0.080 Uiso 1 1 calc R
H28B H 0.9826 0.2717 0.0064 0.080 Uiso 1 1 calc R
C20 C 0.7371(3) 0.3435(2) 0.04575(12) 0.0660(6) Uani 1 1 d .
H20A H 0.7198 0.4285 0.0163 0.079 Uiso 1 1 calc R
H20B H 0.6489 0.3208 0.0618 0.079 Uiso 1 1 calc R
C19 C 0.8032(3) 0.0860(3) 0.04116(13) 0.0681(6) Uani 1 1 d .
H19A H 0.8210 0.0114 0.0085 0.082 Uiso 1 1 calc R
H19B H 0.8907 0.0997 0.0767 0.082 Uiso 1 1 calc R
C25 C 0.6011(3) 0.3195(3) -0.11530(13) 0.0763(7) Uani 1 1 d .
H25A H 0.5895 0.4060 -0.0891 0.092 Uiso 1 1 calc R
H25B H 0.6779 0.3342 -0.1417 0.092 Uiso 1 1 calc R
C30 C 1.0595(3) 0.2178(3) -0.12279(14) 0.0861(8) Uani 1 1 d .
H30A H 1.1434 0.2354 -0.0854 0.103 Uiso 1 1 calc R
H30B H 1.0288 0.3077 -0.1457 0.103 Uiso 1 1 calc R
C26 C 0.4641(3) 0.2870(3) -0.16798(14) 0.0848(8) Uani 1 1 d .
H26A H 0.3892 0.2677 -0.1409 0.102 Uiso 1 1 calc R
H26B H 0.4778 0.2020 -0.1949 0.102 Uiso 1 1 calc R
C29 C 0.9420(3) 0.1596(3) -0.08821(15) 0.0803(8) Uani 1 1 d .
H29A H 0.9733 0.0708 -0.0642 0.096 Uiso 1 1 calc R
H29B H 0.8585 0.1401 -0.1255 0.096 Uiso 1 1 calc R
C21 C 0.8499(3) 0.3765(3) 0.11158(14) 0.0837(8) Uani 1 1 d .
H21A H 0.9377 0.4050 0.0967 0.100 Uiso 1 1 calc R
H21B H 0.8698 0.2925 0.1416 0.100 Uiso 1 1 calc R
C18 C 0.6880(3) 0.0361(3) 0.08035(14) 0.0761(7) Uani 1 1 d .
H18A H 0.6601 0.1138 0.1084 0.091 Uiso 1 1 calc R
H18B H 0.6044 0.0074 0.0451 0.091 Uiso 1 1 calc R
C17 C 0.7378(3) -0.0859(3) 0.12988(15) 0.0862(8) Uani 1 1 d .
H17A H 0.8182 -0.0553 0.1667 0.103 Uiso 1 1 calc R
H17B H 0.7713 -0.1611 0.1022 0.103 Uiso 1 1 calc R
C31 C 1.0993(4) 0.1187(5) -0.17872(17) 0.1161(11) Uani 1 1 d .
H31A H 1.0144 0.0904 -0.2121 0.174 Uiso 1 1 calc R
H31B H 1.1460 0.0364 -0.1550 0.174 Uiso 1 1 calc R
H31C H 1.1630 0.1663 -0.2047 0.174 Uiso 1 1 calc R
C16 C 0.6213(4) -0.1442(3) 0.16690(17) 0.1060(10) Uani 1 1 d .
H16A H 0.5495 -0.1906 0.1316 0.159 Uiso 1 1 calc R
H16B H 0.5784 -0.0678 0.1888 0.159 Uiso 1 1 calc R
H16C H 0.6625 -0.2111 0.2036 0.159 Uiso 1 1 calc R
C27 C 0.4158(4) 0.4060(4) -0.22095(17) 0.1202(11) Uani 1 1 d .
H27A H 0.4909 0.4284 -0.2466 0.180 Uiso 1 1 calc R
H27B H 0.3939 0.4882 -0.1950 0.180 Uiso 1 1 calc R
H27C H 0.3319 0.3770 -0.2549 0.180 Uiso 1 1 calc R
C22 C 0.7983(4) 0.4945(3) 0.15457(15) 0.1072(11) Uani 1 1 d .
H22A H 0.7638 0.5716 0.1216 0.129 Uiso 1 1 calc R
H22B H 0.7174 0.4597 0.1739 0.129 Uiso 1 1 calc R
C23 C 0.9053(6) 0.5520(4) 0.2151(2) 0.166(2) Uani 1 1 d .
H23A H 0.9870 0.5855 0.1971 0.249 Uiso 1 1 calc R
H23B H 0.9347 0.4789 0.2504 0.249 Uiso 1 1 calc R
H23C H 0.8640 0.6291 0.2373 0.249 Uiso 1 1 calc R
N3 N 0.7707(2) 0.22235(18) -0.00241(9) 0.0595(5) Uani 1 1 d .
F1 F 0.32049(15) 0.57057(14) 0.98217(8) 0.0839(4) Uani 1 1 d .
H4A H 0.491(3) 0.642(5) 0.980(2) 0.151(17) Uiso 1 1 d D
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
O2 C6 C5 123.47(19)
O2 C6 C1 117.1(2)
C5 C6 C1 119.4(2)
O1 C1 C2 123.9(2)
O1 C1 C6 116.2(2)
C2 C1 C6 119.8(2)
C4 C5 C6 118.9(2)
C4 C5 C7 120.0(2)
C6 C5 C7 121.1(2)
C3 C4 C5 121.4(2)
C1 C2 C3 120.7(2)
N1 C7 C5 120.8(2)
C4 C3 C2 119.7(2)
C10 C11 C12 120.3(3)
C7 N1 O3 113.3(2)
O5 C14 C9 116.9(2)
O5 C14 C13 122.2(2)
C9 C14 C13 120.9(2)
C14 C13 C12 118.2(3)
C14 C13 C15 122.3(2)
C12 C13 C15 119.5(3)
O4 C9 C10 123.6(3)
O4 C9 C14 117.1(2)
C10 C9 C14 119.4(2)
C11 C12 C13 120.4(3)
N2 C15 C13 122.4(3)
C11 C10 C9 120.6(3)
C15 N2 O6 113.9(2)
C25 C24 N3 115.57(19)
C29 C28 N3 115.9(2)
C21 C20 N3 116.33(19)
C18 C19 N3 115.80(19)
C26 C25 C24 110.3(2)
C29 C30 C31 112.6(3)
C25 C26 C27 113.3(3)
C30 C29 C28 111.6(2)
C20 C21 C22 109.7(2)
C17 C18 C19 111.7(2)
C18 C17 C16 113.0(3)
C23 C22 C21 115.8(3)
C28 N3 C24 111.64(17)
C28 N3 C19 108.63(17)
C24 N3 C19 108.72(16)
C28 N3 C20 108.86(17)
C24 N3 C20 108.13(17)
C19 N3 C20 110.86(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 O2 1.353(3)
C6 C5 1.401(3)
C6 C1 1.407(3)
C1 O1 1.359(3)
C1 C2 1.375(3)
C5 C4 1.399(3)
C5 C7 1.457(3)
C4 C3 1.362(4)
C2 C3 1.391(4)
C7 N1 1.269(3)
C11 C10 1.374(5)
C11 C12 1.380(5)
O3 N1 1.394(2)
C14 O5 1.365(3)
C14 C9 1.388(3)
C14 C13 1.397(3)
C13 C12 1.403(4)
C13 C15 1.444(4)
C9 O4 1.363(3)
C9 C10 1.381(4)
C15 N2 1.270(3)
O6 N2 1.381(3)
C24 C25 1.518(3)
C24 N3 1.523(3)
C28 C29 1.516(4)
C28 N3 1.521(3)
C20 C21 1.505(3)
C20 N3 1.530(3)
C19 C18 1.510(3)
C19 N3 1.524(3)
C25 C26 1.508(4)
C30 C29 1.502(4)
C30 C31 1.509(4)
C26 C27 1.512(4)
C21 C22 1.513(4)
C18 C17 1.498(3)
C17 C16 1.522(4)
C22 C23 1.476(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339271
