#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/40/2224091.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_2224091
loop_
_publ_author_name
'Yang, Yun-Xia'
'Li, Qi'
'Ng, Seik Weng'
_publ_section_title
;
 Tetra-n-propylammonium acetate--boric acid (1/1)
;
_journal_coeditor_code           XU2651
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2958
_journal_paper_doi               10.1107/S1600536809044225
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H28 N +, C2 H3 O2 -, B H3 O3'
_chemical_formula_moiety         'C12 H28 N +, C2 H3 O2 -, B H3 O3'
_chemical_formula_sum            'C14 H34 B N O5'
_chemical_formula_weight         307.23
_chemical_name_systematic
;
Tetra-n-propylammonium acetate--boric acid (1/1)
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.4594(3)
_cell_length_b                   16.7680(3)
_cell_length_c                   14.4526(3)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.2
_cell_volume                     3988.79(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19907
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.132
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0888P)²+0.6196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1833
_reflns_number_gt                2803
_reflns_number_total             4581
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2651.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224091
_cod_database_fobs_code          2224091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.65031(7) 0.26154(7) 0.38659(8) 0.0628(3) Uani d D 1 . .
H H1 0.5997(7) 0.2504(13) 0.3918(13) 0.083(6) Uiso d D 1 . .
O O2 0.60919(9) 0.39766(8) 0.38631(11) 0.0822(4) Uani d D 1 . .
H H2 0.5628(10) 0.3765(17) 0.396(2) 0.131(11) Uiso d D 1 . .
O O3 0.74569(8) 0.36496(8) 0.37814(10) 0.0783(4) Uani d D 1 . .
H H3 0.7800(12) 0.3273(10) 0.3834(16) 0.104(8) Uiso d D 1 . .
O O4 0.49799(8) 0.22127(8) 0.39542(12) 0.0942(5) Uani d . 1 . .
O O5 0.46002(8) 0.34620(9) 0.41629(12) 0.0923(5) Uani d . 1 . .
N N1 0.57206(9) 0.42369(8) 0.68832(9) 0.0628(4) Uani d . 1 . .
C C1 0.48754(11) 0.42868(11) 0.64651(13) 0.0732(5) Uani d . 1 . .
H H1A 0.4724 0.4845 0.6421 0.088 Uiso calc R 1 . .
H H1B 0.4898 0.4076 0.5840 0.088 Uiso calc R 1 . .
C C2 0.42181(13) 0.38518(18) 0.69837(19) 0.1086(8) Uani d . 1 . .
H H2A 0.4354 0.3290 0.7024 0.130 Uiso calc R 1 . .
H H2B 0.4179 0.4061 0.7608 0.130 Uiso calc R 1 . .
C C3 0.34159(15) 0.39487(19) 0.6499(2) 0.1243(10) Uani d . 1 . .
H H3A 0.3001 0.3675 0.6841 0.186 Uiso calc R 1 . .
H H3B 0.3452 0.3728 0.5888 0.186 Uiso calc R 1 . .
H H3C 0.3283 0.4505 0.6459 0.186 Uiso calc R 1 . .
C C4 0.57384(13) 0.45737(12) 0.78584(12) 0.0750(5) Uani d . 1 . .
H H4A 0.5387 0.4250 0.8245 0.090 Uiso calc R 1 . .
H H4B 0.6287 0.4522 0.8097 0.090 Uiso calc R 1 . .
C C5 0.54799(17) 0.54338(15) 0.79533(16) 0.1045(8) Uani d . 1 . .
H H5A 0.5782 0.5761 0.7520 0.125 Uiso calc R 1 . .
H H5B 0.4907 0.5484 0.7809 0.125 Uiso calc R 1 . .
C C6 0.5634(2) 0.5719(2) 0.8927(2) 0.1579(16) Uani d . 1 . .
H H6A 0.5471 0.6266 0.8982 0.237 Uiso calc R 1 . .
H H6B 0.6203 0.5672 0.9066 0.237 Uiso calc R 1 . .
H H6C 0.5327 0.5399 0.9353 0.237 Uiso calc R 1 . .
C C7 0.62782(12) 0.46947(10) 0.62404(12) 0.0693(5) Uani d . 1 . .
H H7A 0.6252 0.4450 0.5633 0.083 Uiso calc R 1 . .
H H7B 0.6072 0.5234 0.6182 0.083 Uiso calc R 1 . .
C C8 0.71601(13) 0.47402(14) 0.65287(17) 0.0922(6) Uani d . 1 . .
H H8A 0.7204 0.5036 0.7103 0.111 Uiso calc R 1 . .
H H8B 0.7367 0.4206 0.6635 0.111 Uiso calc R 1 . .
C C9 0.76609(17) 0.51429(15) 0.5795(2) 0.1162(9) Uani d . 1 . .
H H9A 0.8216 0.5173 0.5995 0.174 Uiso calc R 1 . .
H H9B 0.7456 0.5671 0.5690 0.174 Uiso calc R 1 . .
H H9C 0.7630 0.4842 0.5231 0.174 Uiso calc R 1 . .
C C10 0.59924(11) 0.33770(10) 0.69796(12) 0.0647(4) Uani d . 1 . .
H H10A 0.6521 0.3372 0.7276 0.078 Uiso calc R 1 . .
H H10B 0.5616 0.3106 0.7390 0.078 Uiso calc R 1 . .
C C11 0.60502(16) 0.29084(12) 0.61010(14) 0.0875(7) Uani d . 1 . .
H H11A 0.6441 0.3158 0.5691 0.105 Uiso calc R 1 . .
H H11B 0.5527 0.2907 0.5793 0.105 Uiso calc R 1 . .
C C12 0.63080(17) 0.20624(12) 0.62980(17) 0.0967(7) Uani d . 1 . .
H H12A 0.6343 0.1771 0.5727 0.145 Uiso calc R 1 . .
H H12B 0.5916 0.1813 0.6696 0.145 Uiso calc R 1 . .
H H12C 0.6829 0.2064 0.6596 0.145 Uiso calc R 1 . .
C C13 0.44575(11) 0.27397(13) 0.40662(15) 0.0781(5) Uani d . 1 . .
C C14 0.35937(14) 0.24694(18) 0.4140(3) 0.1411(12) Uani d . 1 . .
H H14A 0.3351 0.2698 0.4682 0.212 Uiso calc R 1 . .
H H14B 0.3577 0.1898 0.4183 0.212 Uiso calc R 1 . .
H H14C 0.3299 0.2639 0.3601 0.212 Uiso calc R 1 . .
B B1 0.66733(12) 0.34081(11) 0.38298(13) 0.0591(5) Uani d . 1 . .
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
B1 O1 H1 . . 114.6(15) ?
B1 O2 H2 . . 110(2) ?
B1 O3 H3 . . 113.9(16) ?
C7 N1 C10 . . 111.08(13) ?
C7 N1 C4 . . 111.66(15) ?
C10 N1 C4 . . 105.23(12) ?
C7 N1 C1 . . 106.44(13) ?
C10 N1 C1 . . 111.05(14) ?
C4 N1 C1 . . 111.49(13) ?
C2 C1 N1 . . 115.70(16) ?
C2 C1 H1A . . 108.4 ?
N1 C1 H1A . . 108.4 ?
C2 C1 H1B . . 108.4 ?
N1 C1 H1B . . 108.4 ?
H1A C1 H1B . . 107.4 ?
C3 C2 C1 . . 110.3(2) ?
C3 C2 H2A . . 109.6 ?
C1 C2 H2A . . 109.6 ?
C3 C2 H2B . . 109.6 ?
C1 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.1 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C5 C4 N1 . . 115.72(15) ?
C5 C4 H4A . . 108.4 ?
N1 C4 H4A . . 108.4 ?
C5 C4 H4B . . 108.4 ?
N1 C4 H4B . . 108.4 ?
H4A C4 H4B . . 107.4 ?
C6 C5 C4 . . 109.9(2) ?
C6 C5 H5A . . 109.7 ?
C4 C5 H5A . . 109.7 ?
C6 C5 H5B . . 109.7 ?
C4 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 N1 . . 115.99(15) ?
C8 C7 H7A . . 108.3 ?
N1 C7 H7A . . 108.3 ?
C8 C7 H7B . . 108.3 ?
N1 C7 H7B . . 108.3 ?
H7A C7 H7B . . 107.4 ?
C9 C8 C7 . . 110.8(2) ?
C9 C8 H8A . . 109.5 ?
C7 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 N1 . . 116.12(13) ?
C11 C10 H10A . . 108.3 ?
N1 C10 H10A . . 108.3 ?
C11 C10 H10B . . 108.3 ?
N1 C10 H10B . . 108.3 ?
H10A C10 H10B . . 107.4 ?
C10 C11 C12 . . 110.60(16) ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O5 C13 O4 . . 125.24(18) ?
O5 C13 C14 . . 117.86(19) ?
O4 C13 C14 . . 116.8(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O2 B1 O3 . . 117.74(16) ?
O2 B1 O1 . . 122.85(17) ?
O3 B1 O1 . . 119.39(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 B1 . 1.359(2) ?
O1 H1 . 0.856(9) ?
O2 B1 . 1.352(2) ?
O2 H2 . 0.853(10) ?
O3 B1 . 1.354(2) ?
O3 H3 . 0.851(9) ?
O4 C13 . 1.244(2) ?
O5 C13 . 1.242(2) ?
N1 C7 . 1.515(2) ?
N1 C10 . 1.516(2) ?
N1 C4 . 1.519(2) ?
N1 C1 . 1.519(2) ?
C1 C2 . 1.505(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.503(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.510(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.508(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C8 . 1.512(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.503(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.496(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.508(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.496(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 O4 . 0.860(10) 1.750(10) 2.600(2) 175(2) yes
O2 H2 O5 . 0.850(10) 1.790(10) 2.638(2) 172(3) yes
O3 H3 O1 2_655 0.850(10) 1.880(10) 2.729(2) 174(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . 178.63(18) ?
C10 N1 C1 C2 . . . . 57.6(2) ?
C4 N1 C1 C2 . . . . -59.4(2) ?
N1 C1 C2 C3 . . . . 180.0(2) ?
C7 N1 C4 C5 . . . . 60.1(2) ?
C10 N1 C4 C5 . . . . -179.33(19) ?
C1 N1 C4 C5 . . . . -58.9(2) ?
N1 C4 C5 C6 . . . . -172.4(2) ?
C10 N1 C7 C8 . . . . -60.1(2) ?
C4 N1 C7 C8 . . . . 57.0(2) ?
C1 N1 C7 C8 . . . . 178.90(16) ?
N1 C7 C8 C9 . . . . 174.83(18) ?
C7 N1 C10 C11 . . . . -57.4(2) ?
C4 N1 C10 C11 . . . . -178.41(18) ?
C1 N1 C10 C11 . . . . 60.8(2) ?
N1 C10 C11 C12 . . . . -178.76(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655937
