##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_1
_audit_creation_method     'WinGX routine-INITIALISE'
_journal_date_recd_electronic     2017-12-12
_journal_date_accepted     2018-02-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2018
_journal_volume     74
_journal_issue      4
_journal_page_first     411
_journal_page_last     417
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229618002681
_journal_coeditor_code     WQ3141
_publ_contact_author_name     'Lamia, Bendjeddou'
_publ_contact_author_address
;
Unité de Recherche Chimie de l'Environnement et Moléculaire Structurale,
CHEMS
Faculté des Sciences Exactes
Campus Chaabet Ersas
Université Constantine I
25000 Constantine
Algeria
;
_publ_contact_author_email     bendjeddoulamia@gmail.com
_publ_contact_author_fax     '00 (213) 31 61 46 44'
_publ_contact_author_phone     '00 (213) 31 61 46 44'
_publ_section_title
;
Synthesis, structure characterization, photoluminescence properties and TD--DFT
calculations for two new borates.
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hadjadj, Nasreddine' .
;
Unité de Recherche Chimie de l'Environnement et Moléculaire Structurale
CHEMS
Faculté des Sciences Exactes
Campus Chaabet Ersas
Université Frères Mentouri Constantine 1
25000 Constantine
Algeria
Centre de Recherche en Biotechnologie
Ali Mendjli Nouvelle Ville UV 03 BP E73
Constantine
Algeria
;
    'Dems, Mohamed AbdEsselem' .
;\
Laboratoire de Chimie des Matériaux et des Vivants: \
Activité, Réactivité
Université Hadj-Lakhdar Batna
Algeria
Centre de Recherche en Biotechnologie
Ali Mendjli Nouvelle Ville UV 03 BP E73
Constantine
Algeria
;
    'Merazig, Hocine' .
;
Unité de Recherche Chimie de l'Environnement et Moléculaire Structurale
CHEMS
Faculté des Sciences Exactes
Campus Chaabet Ersas
Université Frères Mentouri Constantine 1
25000 Constantine
Algeria
;
    'Bendjeddou, Lamia' .
;
Unité de Recherche Chimie de l'Environnement et Moléculaire Structurale
CHEMS
Faculté des Sciences Exactes
Campus Chaabet Ersas
Université Frères Mentouri Constantine 1
25000 Constantine
Algeria
;
_publ_section_synopsis
;
The synthesis and structural determination of the diethylammonium and
propylammonium salts of bis(salicylato)borate are repoted. The crystal
structures are stabilized by N---H...O, C---H...O and C---H...π/N---H...O
hydrogen bonds. The salts displays a strong blue-light emission with maxima
around 490 nm which appears to be derived from the ICT excited state.
;
_database_code_depnum_ccdc_archive     'CCDC 1824121'
_chemical_name_systematic
;
Diethylammonium bis(2-oxidobenzoato-κ²O¹,O²)borate
;
_chemical_formula_moiety     'C4 H12 N +, C14 H8 B O6 -'
_chemical_formula_sum     'C18 H20 B N O6'
_chemical_formula_weight     357.16
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.050(5)
_cell_length_b     10.006(5)
_cell_length_c     11.082(5)
_cell_angle_alpha     69.207(5)
_cell_angle_beta     79.497(5)
_cell_angle_gamma     82.267(5)
_cell_volume     919.8(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     13321
_cell_measurement_theta_min     2.810
_cell_measurement_theta_max     26.06
_cell_measurement_temperature     293
_cell_special_details     ?
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.2
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.290
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     none
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13321
_diffrn_reflns_av_R_equivalents     0.0386
_diffrn_reflns_theta_min     2.81
_diffrn_reflns_theta_max     26.06
_diffrn_reflns_theta_full     26.06
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3606
_reflns_number_gt     2284
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0867
_refine_ls_R_factor_gt     0.0432
_refine_ls_wR_factor_gt     0.0912
_refine_ls_wR_factor_ref     0.1087
_refine_ls_goodness_of_fit_ref     1.009
_refine_ls_restrained_S_all     1.009
_refine_ls_number_reflns     3606
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0458P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.189
_refine_diff_density_min     -0.186
_refine_ls_extinction_method     none
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_structure_solution
;
SIR2002 (Burla et al., 2003)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), Mercury (Macrae et al., 2008) and
POVRay (Persistence of Vision, 2004)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O1 0.83098(16) 0.87636(14) 0.66089(11) 0.0421(5) Uani . . 1.000
    O O2 0.72121(14) 0.73657(13) 0.56181(12) 0.0360(4) Uani . . 1.000
    O O3 0.72312(14) 0.99002(13) 0.46970(11) 0.0364(4) Uani . . 1.000
    O O4 0.95483(14) 0.83694(13) 0.46664(11) 0.0346(4) Uani . . 1.000
    O O5 0.62009(15) 0.53441(13) 0.67911(12) 0.0398(5) Uani . . 1.000
    O O6 1.08247(15) 0.82111(15) 0.28245(13) 0.0433(5) Uani . . 1.000
    C C1 0.7364(2) 0.6487(2) 0.78710(18) 0.0377(7) Uani . . 1.000
    C C2 0.8033(2) 0.7708(2) 0.77583(18) 0.0375(7) Uani . . 1.000
    C C3A 0.8301(11) 0.7962(12) 0.8873(10) 0.0390(18) Uani . . 0.67(2)
    C C4A 0.7914(10) 0.6917(7) 1.0076(6) 0.0517(18) Uani . . 0.67(2)
    C C5A 0.7236(13) 0.5703(7) 1.0212(7) 0.063(2) Uani . . 0.67(2)
    C C6A 0.6926(12) 0.5499(9) 0.9109(9) 0.046(2) Uani . . 0.67(2)
    C C7 0.68974(19) 0.63418(18) 0.67348(17) 0.0282(6) Uani . . 1.000
    C C8 0.84761(19) 0.95780(18) 0.27212(16) 0.0269(6) Uani . . 1.000
    C C9 0.7320(2) 1.02006(18) 0.34000(17) 0.0294(6) Uani . . 1.000
    C C10 0.6242(2) 1.1175(2) 0.27304(19) 0.0389(7) Uani . . 1.000
    C C11 0.6333(2) 1.1505(2) 0.1409(2) 0.0442(7) Uani . . 1.000
    C C12 0.7473(2) 1.0871(2) 0.07208(19) 0.0425(7) Uani . . 1.000
    C C13 0.8527(2) 0.9911(2) 0.13810(17) 0.0360(7) Uani . . 1.000
    C C14 0.9697(2) 0.86598(19) 0.33957(17) 0.0314(6) Uani . . 1.000
    B B1 0.8077(3) 0.8624(2) 0.5416(2) 0.0331(7) Uani . . 1.000
    C C5B 0.810(4) 0.533(3) 1.0020(17) 0.101(8) Uani . . 0.33(2)
    C C3B 0.873(4) 0.762(3) 0.878(3) 0.086(8) Uani . . 0.33(2)
    C C4B 0.874(4) 0.655(3) 0.9903(17) 0.105(9) Uani . . 0.33(2)
    C C6B 0.756(3) 0.526(3) 0.901(2) 0.069(6) Uani . . 0.33(2)
    N N1 0.69787(16) 0.32588(16) 0.56209(14) 0.0325(5) Uani . . 1.000
    C C15 0.8622(3) 0.4782(2) 0.3760(2) 0.0494(8) Uani . . 1.000
    C C16 0.7489(2) 0.3670(2) 0.41928(18) 0.0416(7) Uani . . 1.000
    C C17 0.5678(2) 0.2349(2) 0.61138(19) 0.0407(7) Uani . . 1.000
    C C18 0.5242(3) 0.1990(2) 0.7550(2) 0.0533(8) Uani . . 1.000
    H H3A 0.87170 0.87910 0.88050 0.0460 Uiso calc . 0.67(2)
    H H11 0.56180 1.21640 0.09670 0.0530 Uiso calc R 1.000
    H H12 0.75200 1.10950 -0.01740 0.0510 Uiso calc R 1.000
    H H13 0.92880 0.94740 0.09290 0.0430 Uiso calc R 1.000
    H H4A 0.81210 0.70400 1.08210 0.0620 Uiso calc . 0.67(2)
    H H5A 0.69890 0.50290 1.10340 0.0760 Uiso calc . 0.67(2)
    H H6A 0.64280 0.47080 0.91930 0.0550 Uiso calc . 0.67(2)
    H H10 0.54640 1.15990 0.31790 0.0470 Uiso calc R 1.000
    H H3B 0.92570 0.84040 0.86780 0.1020 Uiso calc . 0.33(2)
    H H4B 0.91600 0.66200 1.05830 0.1270 Uiso calc . 0.33(2)
    H H5B 0.80550 0.45550 1.07980 0.1200 Uiso calc . 0.33(2)
    H H6B 0.72860 0.43810 0.90510 0.0830 Uiso calc . 0.33(2)
    H HA 0.67250 0.40630 0.58230 0.0390 Uiso calc R 1.000
    H HB 0.77570 0.27850 0.60410 0.0390 Uiso calc R 1.000
    H H15A 0.89670 0.50090 0.28420 0.0740 Uiso calc R 1.000
    H H15B 0.94630 0.44130 0.42320 0.0740 Uiso calc R 1.000
    H H15C 0.81600 0.56320 0.39280 0.0740 Uiso calc R 1.000
    H H16A 0.66290 0.40500 0.37300 0.0500 Uiso calc R 1.000
    H H16B 0.79400 0.28290 0.39830 0.0500 Uiso calc R 1.000
    H H17A 0.59420 0.14720 0.59130 0.0490 Uiso calc R 1.000
    H H17B 0.48270 0.28540 0.56760 0.0490 Uiso calc R 1.000
    H H18A 0.50380 0.28580 0.77550 0.0800 Uiso calc R 1.000
    H H18B 0.60510 0.14140 0.79880 0.0800 Uiso calc R 1.000
    H H18C 0.43550 0.14660 0.78310 0.0800 Uiso calc R 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C2 O1 . . 1.342(2) yes
    B1 O1 . . 1.433(3) yes
    C7 O2 . . 1.309(2) yes
    B1 O2 . . 1.500(3) yes
    C9 O3 . . 1.349(2) yes
    B1 O3 . . 1.445(3) yes
    C14 O4 . . 1.318(2) yes
    B1 O4 . . 1.478(3) yes
    C7 O5 . . 1.228(2) yes
    C14 O6 . . 1.219(2) yes
    C16 N1 . . 1.487(2) yes
    C17 N1 . . 1.488(3) yes
    HB N1 . . 0.9000 no
    HA N1 . . 0.9000 no
    C6B C1 . . 1.43(2) no
    C7 C1 . . 1.458(3) no
    C2 C1 . . 1.392(3) no
    C6A C1 . . 1.400(10) no
    C3B C2 . . 1.37(3) no
    C3A C2 . . 1.414(11) no
    C4A C3A . . 1.390(13) no
    C4B C3B . . 1.32(4) no
    C5A C4A . . 1.383(12) no
    C5B C4B . . 1.38(5) no
    C6A C5A . . 1.390(13) no
    C6B C5B . . 1.33(4) no
    C13 C8 . . 1.395(3) no
    C9 C8 . . 1.385(3) no
    C14 C8 . . 1.471(3) no
    C10 C9 . . 1.396(3) no
    C11 C10 . . 1.371(3) no
    C12 C11 . . 1.389(3) no
    C13 C12 . . 1.370(3) no
    H3A C3A . . 0.9300 no
    H3B C3B . . 0.9300 no
    H4A C4A . . 0.9300 no
    H4B C4B . . 0.9300 no
    H5A C5A . . 0.9300 no
    H5B C5B . . 0.9300 no
    H6A C6A . . 0.9300 no
    H6B C6B . . 0.9300 no
    H10 C10 . . 0.9300 no
    H11 C11 . . 0.9300 no
    H12 C12 . . 0.9300 no
    H13 C13 . . 0.9300 no
    C16 C15 . . 1.506(3) no
    C18 C17 . . 1.490(3) no
    H15A C15 . . 0.9600 no
    H15B C15 . . 0.9600 no
    H15C C15 . . 0.9600 no
    H16A C16 . . 0.9700 no
    H16B C16 . . 0.9700 no
    H17A C17 . . 0.9700 no
    H17B C17 . . 0.9700 no
    H18A C18 . . 0.9600 no
    H18B C18 . . 0.9600 no
    H18C C18 . . 0.9600 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 B1 . . . 121.52(16) yes
    C7 O2 B1 . . . 124.92(15) yes
    C9 O3 B1 . . . 117.58(15) yes
    C14 O4 B1 . . . 120.97(15) yes
    C16 N1 C17 . . . 114.80(15) yes
    C17 N1 HB . . . 109.00 no
    C16 N1 HB . . . 109.00 no
    C17 N1 HA . . . 109.00 no
    C16 N1 HA . . . 109.00 no
    HA N1 HB . . . 107.00 no
    C6A C1 C7 . . . 119.2(4) no
    C2 C1 C6A . . . 119.7(4) no
    C2 C1 C6B . . . 116.3(12) no
    C2 C1 C7 . . . 120.38(17) no
    C6B C1 C7 . . . 120.9(12) no
    C1 C2 C3B . . . 116.1(13) no
    C1 C2 C3A . . . 121.2(5) no
    O1 C2 C1 . . . 121.75(17) yes
    O1 C2 C3A . . . 116.7(5) yes
    O1 C2 C3B . . . 120.2(14) yes
    C2 C3A C4A . . . 117.0(9) no
    C2 C3B C4B . . . 127(3) no
    C3A C4A C5A . . . 122.8(8) no
    C3B C4B C5B . . . 117(3) no
    C4A C5A C6A . . . 119.4(7) no
    C4B C5B C6B . . . 119(2) no
    C1 C6A C5A . . . 119.8(8) no
    C1 C6B C5B . . . 123(3) no
    O2 C7 O5 . . . 119.77(16) yes
    O2 C7 C1 . . . 116.84(16) yes
    O5 C7 C1 . . . 123.36(17) yes
    C13 C8 C14 . . . 120.50(16) no
    C9 C8 C13 . . . 119.47(17) no
    C9 C8 C14 . . . 119.88(15) no
    O3 C9 C8 . . . 121.12(16) yes
    O3 C9 C10 . . . 119.27(17) yes
    C8 C9 C10 . . . 119.60(16) no
    C9 C10 C11 . . . 119.81(18) no
    C10 C11 C12 . . . 121.13(18) no
    C11 C12 C13 . . . 118.95(18) no
    C8 C13 C12 . . . 121.02(18) no
    O4 C14 C8 . . . 116.77(16) yes
    O4 C14 O6 . . . 120.34(17) yes
    O6 C14 C8 . . . 122.85(16) yes
    C2 C3A H3A . . . 122.00 no
    C4A C3A H3A . . . 121.00 no
    C2 C3B H3B . . . 116.00 no
    C4B C3B H3B . . . 116.00 no
    C3A C4A H4A . . . 119.00 no
    C5A C4A H4A . . . 119.00 no
    C5B C4B H4B . . . 122.00 no
    C3B C4B H4B . . . 122.00 no
    C4A C5A H5A . . . 120.00 no
    C6A C5A H5A . . . 120.00 no
    C4B C5B H5B . . . 120.00 no
    C6B C5B H5B . . . 120.00 no
    C5A C6A H6A . . . 120.00 no
    C1 C6A H6A . . . 120.00 no
    C5B C6B H6B . . . 118.00 no
    C1 C6B H6B . . . 119.00 no
    C9 C10 H10 . . . 120.00 no
    C11 C10 H10 . . . 120.00 no
    C10 C11 H11 . . . 119.00 no
    C12 C11 H11 . . . 119.00 no
    C13 C12 H12 . . . 121.00 no
    C11 C12 H12 . . . 121.00 no
    C12 C13 H13 . . . 119.00 no
    C8 C13 H13 . . . 119.00 no
    N1 C16 C15 . . . 110.53(16) yes
    N1 C17 C18 . . . 111.18(17) yes
    C16 C15 H15A . . . 109.00 no
    C16 C15 H15B . . . 109.00 no
    H15A C15 H15C . . . 109.00 no
    H15B C15 H15C . . . 109.00 no
    C16 C15 H15C . . . 110.00 no
    H15A C15 H15B . . . 109.00 no
    N1 C16 H16A . . . 110.00 no
    C15 C16 H16B . . . 110.00 no
    N1 C16 H16B . . . 110.00 no
    C15 C16 H16A . . . 110.00 no
    H16A C16 H16B . . . 108.00 no
    N1 C17 H17B . . . 109.00 no
    C18 C17 H17A . . . 109.00 no
    N1 C17 H17A . . . 109.00 no
    H17A C17 H17B . . . 108.00 no
    C18 C17 H17B . . . 109.00 no
    C17 C18 H18A . . . 109.00 no
    H18B C18 H18C . . . 109.00 no
    H18A C18 H18C . . . 109.00 no
    H18A C18 H18B . . . 110.00 no
    C17 C18 H18B . . . 109.00 no
    C17 C18 H18C . . . 109.00 no
    O1 B1 O4 . . . 109.52(19) yes
    O2 B1 O3 . . . 107.50(18) yes
    O2 B1 O4 . . . 105.24(15) yes
    O3 B1 O4 . . . 112.28(15) yes
    O1 B1 O3 . . . 108.88(16) yes
    O1 B1 O2 . . . 113.45(16) 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
    B1 O1 C2 C1 . . . . -6.6(3) no
    B1 O1 C2 C3A . . . . -179.9(5) no
    C2 O1 B1 O2 . . . . 12.2(3) no
    C2 O1 B1 O3 . . . . 131.84(18) no
    C2 O1 B1 O4 . . . . -105.0(2) no
    B1 O2 C7 O5 . . . . -178.83(18) no
    B1 O2 C7 C1 . . . . 3.2(3) no
    C7 O2 B1 O1 . . . . -10.8(3) no
    C7 O2 B1 O3 . . . . -131.24(17) no
    C7 O2 B1 O4 . . . . 108.90(18) no
    B1 O3 C9 C8 . . . . -18.1(3) no
    B1 O3 C9 C10 . . . . 163.06(19) no
    C9 O3 B1 O1 . . . . 158.45(16) no
    C9 O3 B1 O2 . . . . -78.3(2) no
    C9 O3 B1 O4 . . . . 37.0(2) no
    B1 O4 C14 O6 . . . . -166.55(18) no
    B1 O4 C14 C8 . . . . 15.6(3) no
    C14 O4 B1 O1 . . . . -157.80(16) no
    C14 O4 B1 O2 . . . . 79.9(2) no
    C14 O4 B1 O3 . . . . -36.7(2) no
    C16 N1 C17 C18 . . . . -179.94(17) no
    C17 N1 C16 C15 . . . . 170.41(17) no
    C7 C1 C2 O1 . . . . -2.0(3) no
    C7 C1 C2 C3A . . . . 171.1(5) no
    C2 C1 C6A C5A . . . . -3.5(11) no
    C7 C1 C6A C5A . . . . -173.8(7) no
    C2 C1 C7 O2 . . . . 3.5(3) no
    C2 C1 C7 O5 . . . . -174.32(18) no
    C6A C1 C2 C3A . . . . 1.0(8) no
    C6A C1 C7 O5 . . . . -4.1(6) no
    C6A C1 C2 O1 . . . . -172.1(5) no
    C6A C1 C7 O2 . . . . 173.7(5) no
    C1 C2 C3A C4A . . . . 2.1(11) no
    O1 C2 C3A C4A . . . . 175.5(7) no
    C2 C3A C4A C5A . . . . -2.8(14) no
    C3A C4A C5A C6A . . . . 0.3(15) no
    C4A C5A C6A C1 . . . . 2.9(15) no
    C14 C8 C9 O3 . . . . -4.8(3) no
    C14 C8 C9 C10 . . . . 174.07(18) no
    C9 C8 C13 C12 . . . . 1.6(3) no
    C14 C8 C13 C12 . . . . -173.79(18) no
    C9 C8 C14 O4 . . . . 6.1(3) no
    C9 C8 C14 O6 . . . . -171.75(19) no
    C13 C8 C14 O4 . . . . -178.51(17) no
    C13 C8 C14 O6 . . . . 3.7(3) no
    C13 C8 C9 C10 . . . . -1.4(3) no
    C13 C8 C9 O3 . . . . 179.76(17) no
    C8 C9 C10 C11 . . . . 0.2(3) no
    O3 C9 C10 C11 . . . . 179.04(18) no
    C9 C10 C11 C12 . . . . 0.9(3) no
    C10 C11 C12 C13 . . . . -0.6(3) no
    C11 C12 C13 C8 . . . . -0.6(3) 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
    N1 HA O5 . 0.9000 1.9100 2.779(3) 162.00 yes
    N1 HB O6 2_766 0.9000 1.8900 2.783(3) 171.00 yes
    C17 H17A O3 1_545 0.9700 2.4700 3.383(3) 157.00 yes
    C18 H18C Cg1 2_666 0.9600 2.676 3.573(3) 155.41(3) yes
data_2
_database_code_depnum_ccdc_archive     'CCDC 1824122'
_chemical_name_systematic
;
Propylammonium bis(2-oxidobenzoato-κ²O¹,O²)borate
;
_chemical_formula_moiety     'C3 H10 N +, C14 H8 B O6 -'
_chemical_formula_sum     'C17 H18 B N O6'
_chemical_formula_iupac     'C3 H10 N +, C14 H8 B O6 -'
_chemical_formula_weight     343.13
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, 1/2-y,1/2+z'
_cell_length_a     11.529(5)
_cell_length_b     8.885(5)
_cell_length_c     17.216(5)
_cell_angle_alpha     90.000
_cell_angle_beta     108.308(5)
_cell_angle_gamma     90.000
_cell_volume     1674.3(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     13759
_cell_measurement_theta_min     2.95
_cell_measurement_theta_max     25.03
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.361
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     none
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     13759
_diffrn_reflns_av_R_equivalents     0.0212
_diffrn_reflns_theta_min     2.95
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2937
_reflns_number_gt     2395
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.059
_refine_ls_R_factor_gt     0.0497
_refine_ls_wR_factor_gt     0.1409
_refine_ls_wR_factor_ref     0.1535
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     2937
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[Σ²(FO²)+(0.0934P)²+0.2978P] where P=(FO²+2FC²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.227
_refine_diff_density_min     -0.248
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_structure_solution
;
SIR2002 (Burla et al.,  2003)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), Mercury (Macrae et al.,
2008)
and POVRay (Persistence of Vision, 2004)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O1 0.73685(11) 0.37010(14) 0.31029(7) 0.0493(4) Uani . . 1.000
    O O2 0.62630(9) 0.50406(13) 0.18544(7) 0.0442(4) Uani . . 1.000
    O O3 0.52299(10) 0.37165(14) 0.26389(6) 0.0445(4) Uani . . 1.000
    O O4 0.63604(10) 0.23584(13) 0.18857(7) 0.0455(4) Uani . . 1.000
    O O5 0.71769(12) 0.66275(16) 0.12628(8) 0.0592(4) Uani . . 1.000
    O O6 0.54284(13) 0.08825(14) 0.08470(7) 0.0560(4) Uani . . 1.000
    C C1 0.84223(14) 0.52620(19) 0.24101(10) 0.0433(5) Uani . . 1.000
    C C2 0.84163(14) 0.43206(19) 0.30517(10) 0.0437(5) Uani . . 1.000
    C C3 0.95041(17) 0.4028(2) 0.36734(12) 0.0589(6) Uani . . 1.000
    C C4 1.05781(17) 0.4655(3) 0.36401(15) 0.0689(7) Uani . . 1.000
    C C5 1.05973(18) 0.5586(3) 0.30045(15) 0.0697(8) Uani . . 1.000
    C C6 0.95227(17) 0.5898(2) 0.23930(14) 0.0584(7) Uani . . 1.000
    C C7 0.72606(15) 0.56923(19) 0.17959(10) 0.0424(5) Uani . . 1.000
    C C8 0.41897(14) 0.24106(18) 0.14018(9) 0.0411(5) Uani . . 1.000
    C C9 0.41691(14) 0.33136(19) 0.20576(9) 0.0396(5) Uani . . 1.000
    C C10 0.30679(16) 0.3794(2) 0.21366(11) 0.0512(6) Uani . . 1.000
    C C11 0.19952(17) 0.3388(3) 0.15534(13) 0.0646(7) Uani . . 1.000
    C C12 0.20020(18) 0.2509(3) 0.08903(14) 0.0699(8) Uani . . 1.000
    C C13 0.30898(17) 0.2018(2) 0.08171(11) 0.0568(6) Uani . . 1.000
    C C14 0.53601(16) 0.18277(18) 0.13487(9) 0.0426(5) Uani . . 1.000
    B B1 0.63163(16) 0.3710(2) 0.23856(11) 0.0411(6) Uani . . 1.000
    N N1 0.52463(13) 0.22527(16) -0.07278(8) 0.0473(5) Uani . . 1.000
    C C15 0.8480(2) 0.3759(3) 0.02313(19) 0.0926(10) Uani . . 1.000
    C C16 0.74249(17) 0.2653(3) -0.00065(13) 0.0635(7) Uani . . 1.000
    C C17 0.62215(17) 0.3379(2) -0.04290(13) 0.0592(6) Uani . . 1.000
    H H3 0.95040 0.34100 0.41090 0.0710 Uiso calc . 1.000
    H H4 1.13030 0.44470 0.40530 0.0830 Uiso calc . 1.000
    H H5 1.13300 0.60020 0.29880 0.0840 Uiso calc . 1.000
    H H6 0.95300 0.65350 0.19660 0.0700 Uiso calc . 1.000
    H H10 0.30550 0.43840 0.25800 0.0610 Uiso calc . 1.000
    H H11 0.12540 0.37070 0.16050 0.0780 Uiso calc . 1.000
    H H12 0.12700 0.22530 0.04960 0.0840 Uiso calc . 1.000
    H H13 0.30940 0.14200 0.03750 0.0680 Uiso calc . 1.000
    H HA 0.45430 0.27170 -0.09760 0.0710 Uiso calc . 1.000
    H HB 0.51750 0.17200 -0.03080 0.0710 Uiso calc . 1.000
    H HC 0.54320 0.16400 -0.10810 0.0710 Uiso calc . 1.000
    H H15A 0.92250 0.32310 0.04990 0.1390 Uiso calc . 1.000
    H H15B 0.83370 0.45010 0.05960 0.1390 Uiso calc . 1.000
    H H15C 0.85460 0.42460 -0.02510 0.1390 Uiso calc . 1.000
    H H16A 0.75860 0.18940 -0.03650 0.0760 Uiso calc . 1.000
    H H16B 0.73770 0.21490 0.04820 0.0760 Uiso calc . 1.000
    H H17A 0.60110 0.40550 -0.00520 0.0710 Uiso calc . 1.000
    H H17B 0.62880 0.39700 -0.08870 0.0710 Uiso calc . 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C2 O1 . . 1.355(2) yes
    B1 O1 . . 1.434(2) yes
    C7 O2 . . 1.320(2) yes
    B1 O2 . . 1.484(2) yes
    C9 O3 . . 1.363(2) yes
    B1 O3 . . 1.450(2) yes
    C14 O4 . . 1.318(2) yes
    B1 O4 . . 1.488(2) yes
    C7 O5 . . 1.219(2) yes
    C14 O6 . . 1.225(2) yes
    C17 N1 . . 1.472(3) yes
    HB N1 . . 0.8900 no
    HC N1 . . 0.8900 no
    HA N1 . . 0.8900 no
    C6 C1 . . 1.398(3) no
    C7 C1 . . 1.473(3) no
    C2 C1 . . 1.387(2) no
    C3 C2 . . 1.394(3) no
    C4 C3 . . 1.375(3) no
    C5 C4 . . 1.377(4) no
    C6 C5 . . 1.379(3) no
    C13 C8 . . 1.393(3) no
    C14 C8 . . 1.475(3) no
    C9 C8 . . 1.391(2) no
    C10 C9 . . 1.386(3) no
    C11 C10 . . 1.374(3) no
    C12 C11 . . 1.385(3) no
    C13 C12 . . 1.371(3) no
    H3 C3 . . 0.9300 no
    H4 C4 . . 0.9300 no
    H5 C5 . . 0.9300 no
    H6 C6 . . 0.9300 no
    H10 C10 . . 0.9300 no
    H11 C11 . . 0.9300 no
    H12 C12 . . 0.9300 no
    H13 C13 . . 0.9300 no
    C16 C15 . . 1.517(4) no
    C17 C16 . . 1.495(3) no
    H15A C15 . . 0.9600 no
    H15B C15 . . 0.9600 no
    H15C C15 . . 0.9600 no
    H16A C16 . . 0.9700 no
    H16B C16 . . 0.9700 no
    H17A C17 . . 0.9700 no
    H17B C17 . . 0.9700 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 B1 . . . 118.16(13) yes
    C7 O2 B1 . . . 121.89(13) yes
    C9 O3 B1 . . . 116.04(12) yes
    C14 O4 B1 . . . 120.88(14) yes
    HA N1 HB . . . 110.00 no
    HA N1 HC . . . 109.00 no
    HB N1 HC . . . 109.00 no
    C17 N1 HC . . . 109.00 no
    C17 N1 HA . . . 109.00 no
    C17 N1 HB . . . 109.00 no
    C6 C1 C7 . . . 120.45(16) no
    C2 C1 C6 . . . 119.48(16) no
    C2 C1 C7 . . . 119.83(15) no
    O1 C2 C1 . . . 121.61(15) yes
    C1 C2 C3 . . . 119.71(16) no
    O1 C2 C3 . . . 118.66(15) yes
    C2 C3 C4 . . . 119.81(18) no
    C3 C4 C5 . . . 121.1(2) no
    C4 C5 C6 . . . 119.5(2) no
    C1 C6 C5 . . . 120.44(19) no
    O2 C7 C1 . . . 116.70(14) yes
    O2 C7 O5 . . . 119.46(16) yes
    O5 C7 C1 . . . 123.82(17) yes
    C9 C8 C14 . . . 120.13(14) no
    C9 C8 C13 . . . 119.14(16) no
    C13 C8 C14 . . . 120.67(15) no
    C8 C9 C10 . . . 120.46(15) no
    O3 C9 C8 . . . 120.49(15) yes
    O3 C9 C10 . . . 119.05(14) yes
    C9 C10 C11 . . . 119.30(17) no
    C10 C11 C12 . . . 120.9(2) no
    C11 C12 C13 . . . 119.8(2) no
    C8 C13 C12 . . . 120.36(18) no
    O4 C14 C8 . . . 116.55(14) yes
    O6 C14 C8 . . . 123.18(16) yes
    O4 C14 O6 . . . 120.27(17) yes
    C4 C3 H3 . . . 120.00 no
    C2 C3 H3 . . . 120.00 no
    C3 C4 H4 . . . 119.00 no
    C5 C4 H4 . . . 119.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C5 C6 H6 . . . 120.00 no
    C1 C6 H6 . . . 120.00 no
    C11 C10 H10 . . . 120.00 no
    C9 C10 H10 . . . 120.00 no
    C12 C11 H11 . . . 120.00 no
    C10 C11 H11 . . . 120.00 no
    C11 C12 H12 . . . 120.00 no
    C13 C12 H12 . . . 120.00 no
    C8 C13 H13 . . . 120.00 no
    C12 C13 H13 . . . 120.00 no
    C15 C16 C17 . . . 113.3(2) no
    N1 C17 C16 . . . 111.52(16) yes
    C16 C15 H15C . . . 109.00 no
    H15A C15 H15B . . . 109.00 no
    H15B C15 H15C . . . 109.00 no
    C16 C15 H15A . . . 109.00 no
    H15A C15 H15C . . . 109.00 no
    C16 C15 H15B . . . 109.00 no
    C15 C16 H16A . . . 109.00 no
    C17 C16 H16A . . . 109.00 no
    C17 C16 H16B . . . 109.00 no
    H16A C16 H16B . . . 108.00 no
    C15 C16 H16B . . . 109.00 no
    N1 C17 H17B . . . 109.00 no
    C16 C17 H17A . . . 109.00 no
    N1 C17 H17A . . . 109.00 no
    H17A C17 H17B . . . 108.00 no
    C16 C17 H17B . . . 109.00 no
    O1 B1 O3 . . . 108.55(13) yes
    O1 B1 O4 . . . 108.69(14) yes
    O2 B1 O4 . . . 106.79(13) yes
    O3 B1 O4 . . . 111.53(14) yes
    O2 B1 O3 . . . 108.04(13) yes
    O1 B1 O2 . . . 113.28(14) 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
    B1 O1 C2 C1 . . . . 15.9(2) no
    B1 O1 C2 C3 . . . . -165.78(16) no
    C2 O1 B1 O2 . . . . -32.2(2) no
    C2 O1 B1 O3 . . . . -152.24(14) no
    C2 O1 B1 O4 . . . . 86.29(17) no
    B1 O2 C7 O5 . . . . 168.78(15) no
    B1 O2 C7 C1 . . . . -13.1(2) no
    C7 O2 B1 O1 . . . . 31.8(2) no
    C7 O2 B1 O3 . . . . 152.13(14) no
    C7 O2 B1 O4 . . . . -87.78(17) no
    B1 O3 C9 C8 . . . . 24.3(2) no
    B1 O3 C9 C10 . . . . -156.82(15) no
    C9 O3 B1 O1 . . . . -162.62(13) no
    C9 O3 B1 O2 . . . . 74.17(17) no
    C9 O3 B1 O4 . . . . -42.91(18) no
    B1 O4 C14 O6 . . . . 167.70(15) no
    B1 O4 C14 C8 . . . . -13.4(2) no
    C14 O4 B1 O1 . . . . 158.21(14) no
    C14 O4 B1 O2 . . . . -79.25(17) no
    C14 O4 B1 O3 . . . . 38.58(19) no
    C6 C1 C2 O1 . . . . 178.71(16) no
    C6 C1 C2 C3 . . . . 0.4(3) no
    C7 C1 C2 O1 . . . . 4.3(2) no
    C7 C1 C2 C3 . . . . -174.01(16) no
    C2 C1 C6 C5 . . . . 0.5(3) no
    C7 C1 C6 C5 . . . . 174.88(19) no
    C2 C1 C7 O2 . . . . -5.6(2) no
    C2 C1 C7 O5 . . . . 172.42(17) no
    C6 C1 C7 O2 . . . . 180.00(17) no
    C6 C1 C7 O5 . . . . -1.9(3) no
    O1 C2 C3 C4 . . . . -179.37(18) no
    C1 C2 C3 C4 . . . . -1.0(3) no
    C2 C3 C4 C5 . . . . 0.7(3) no
    C3 C4 C5 C6 . . . . 0.2(4) no
    C4 C5 C6 C1 . . . . -0.8(3) no
    C13 C8 C9 O3 . . . . -179.97(16) no
    C13 C8 C9 C10 . . . . 1.2(2) no
    C14 C8 C9 O3 . . . . 2.6(2) no
    C14 C8 C9 C10 . . . . -176.27(15) no
    C9 C8 C13 C12 . . . . -0.4(3) no
    C14 C8 C13 C12 . . . . 177.06(18) no
    C9 C8 C14 O4 . . . . -8.3(2) no
    C9 C8 C14 O6 . . . . 170.60(16) no
    C13 C8 C14 O4 . . . . 174.32(15) no
    C13 C8 C14 O6 . . . . -6.8(2) no
    O3 C9 C10 C11 . . . . -179.84(18) no
    C8 C9 C10 C11 . . . . -1.0(3) no
    C9 C10 C11 C12 . . . . 0.0(3) no
    C10 C11 C12 C13 . . . . 0.9(4) no
    C11 C12 C13 C8 . . . . -0.6(3) no
    C15 C16 C17 N1 . . . . 173.86(18) 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
    N1 HA O2 3_665 0.8900 2.5000 3.233(3) 140.00 yes
    N1 HA O5 3_665 0.8900 1.9700 2.833(3) 161.00 yes
    N1 HB O6 . 0.8900 2.0600 2.919(2) 163.00 yes
    N1 HC O3 4_554 0.8900 2.1700 2.935(2) 144.00 yes
