#------------------------------------------------------------------------------
#$Date: 2021-06-05 08:47:09 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/31/1563168.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_1563168
loop_
_publ_author_name
'Peppel, Tim'
'Köckerling, Martin'
_publ_section_title
;
 (S)-Alanine ethyl ester tetracyanidoborate,
 (C₅H₁₂NO)[B(CN)₄]
;
_journal_coeditor_code           HB4385
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x210562
_journal_paper_doi               10.1107/S2414314621005629
_journal_volume                  6
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C5 H12 N O2 +, C4 N4 B -'
_chemical_formula_moiety         'C5 H12 N O2 +, C4 N4 B -'
_chemical_formula_sum            'C9 H12 B N5 O2'
_chemical_formula_weight         233.05
_chemical_name_common
;
(S)-Alanine ethyl ester tetracyanidoborate
;
_chemical_name_systematic
;
1-Ethoxy-1-oxopropan-2-aminium tetracyanoborate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'ciftab-2016 (M. Köckerling, 2016)'
_cell_angle_alpha                90
_cell_angle_beta                 111.468(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0590(10)
_cell_length_b                   8.7467(4)
_cell_length_c                   18.8550(10)
_cell_measurement_reflns_used    2564
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.528
_cell_measurement_theta_min      4.282
_cell_volume                     2618.2(2)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX2 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2019)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11976
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.040
_diffrn_reflns_theta_min         4.371
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.240
_refine_ls_abs_structure_details
;
Flack x determined using 1751 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         7354
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0649P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                5158
_reflns_number_total             7354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4385sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2618.2(3)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1563168
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop  which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           201.4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.4401(2) 0.0236(3) 0.3575(2) 0.0267(6) Uani d 1 . .
C C1 0.4986(2) 0.1670(3) 0.3916(2) 0.0327(6) Uani d 1 . .
N N1 0.5418(2) 0.2686(3) 0.4167(2) 0.0494(7) Uani d 1 . .
C C2 0.4971(2) -0.1273(3) 0.3745(2) 0.0281(5) Uani d 1 . .
N N2 0.5371(2) -0.2346(3) 0.38550(10) 0.0405(6) Uani d 1 . .
C C3 0.3940(2) 0.0381(3) 0.2677(2) 0.0326(6) Uani d 1 . .
N N3 0.3621(2) 0.0434(3) 0.2032(2) 0.0505(7) Uani d 1 . .
C C4 0.3729(2) 0.0061(3) 0.3968(2) 0.0343(6) Uani d 1 . .
N N4 0.3242(2) -0.0082(4) 0.4246(2) 0.0524(7) Uani d 1 . .
B B2 0.4421(2) 0.4179(3) 0.8626(2) 0.0288(6) Uani d 1 . .
C C5 0.4893(2) 0.5759(3) 0.8893(2) 0.0378(6) Uani d 1 . .
N N5 0.5235(2) 0.6898(3) 0.9064(2) 0.0574(8) Uani d 1 . .
C C6 0.5081(2) 0.2830(3) 0.8927(2) 0.0345(6) Uani d 1 . .
N N6 0.5555(2) 0.1866(3) 0.9158(2) 0.0505(7) Uani d 1 . .
C C7 0.4013(2) 0.4174(4) 0.7723(2) 0.0396(7) Uani d 1 . .
N N7 0.3728(2) 0.4224(4) 0.7078(2) 0.0680(10) Uani d 1 . .
C C8 0.3709(2) 0.3968(3) 0.8974(2) 0.0304(5) Uani d 1 . .
N N8 0.3198(2) 0.3818(3) 0.9222(2) 0.0423(6) Uani d 1 . .
C C9 0.1899(2) 0.2660(3) 0.0774(2) 0.0485(8) Uani d 1 . .
H H9A 0.1933 0.2721 0.1304 0.073 Uiso calc 1 . .
H H9B 0.2436 0.2290 0.0762 0.073 Uiso calc 1 . .
H H9C 0.1447 0.1952 0.0491 0.073 Uiso calc 1 . .
C C10 0.1714(2) 0.4213(3) 0.04170(10) 0.0284(5) Uani d 1 . .
H H10A 0.1168 0.4582 0.0436 0.034 Uiso calc 1 . .
N N9 0.16510(10) 0.4193(2) -0.03920(10) 0.0251(4) Uani d 1 . .
H H9D 0.1236 0.3536 -0.0663 0.038 Uiso calc 1 . .
H H9E 0.2150 0.3881 -0.0414 0.038 Uiso calc 1 . .
H H9F 0.1529 0.5149 -0.0592 0.038 Uiso calc 1 . .
C C11 0.2398(2) 0.5319(3) 0.08480(10) 0.0290(5) Uani d 1 . .
O O1 0.28580(10) 0.5932(2) 0.05890(10) 0.0390(5) Uani d 1 . .
O O2 0.24290(10) 0.5455(2) 0.15600(10) 0.0417(5) Uani d 1 . .
C C12 0.3156(2) 0.6236(4) 0.2100(2) 0.0534(9) Uani d 1 . .
H H12A 0.3004 0.6699 0.2511 0.064 Uiso calc 1 . .
H H12B 0.3340 0.7064 0.1838 0.064 Uiso calc 1 . .
C C13 0.3855(2) 0.5119(6) 0.2431(2) 0.0690(10) Uani d 1 . .
H H13A 0.4347 0.5646 0.2791 0.103 Uiso calc 1 . .
H H13B 0.4003 0.4663 0.2022 0.103 Uiso calc 1 . .
H H13C 0.3674 0.4313 0.2699 0.103 Uiso calc 1 . .
C C14 0.6152(2) 0.5843(4) 0.5570(2) 0.0447(7) Uani d 1 . .
H H14A 0.6329 0.6107 0.6111 0.067 Uiso calc 1 . .
H H14B 0.5816 0.4904 0.5470 0.067 Uiso calc 1 . .
H H14C 0.5813 0.6678 0.5261 0.067 Uiso calc 1 . .
C C15 0.6923(2) 0.5598(3) 0.53650(10) 0.0262(5) Uani d 1 . .
H H15A 0.7255 0.6569 0.5462 0.031 Uiso calc 1 . .
N N10 0.66670(10) 0.5199(2) 0.45470(10) 0.0228(4) Uani d 1 . .
H H10B 0.7135 0.5058 0.4430 0.034 Uiso calc 1 . .
H H10C 0.6352 0.5971 0.4258 0.034 Uiso calc 1 . .
H H10D 0.6358 0.4323 0.4451 0.034 Uiso calc 1 . .
C C16 0.7477(2) 0.4339(3) 0.58360(10) 0.0246(5) Uani d 1 . .
O O3 0.76100(10) 0.3169(2) 0.55810(10) 0.0429(5) Uani d 1 . .
O O4 0.7763(2) 0.4724(3) 0.65590(10) 0.0500(6) Uani d 1 . .
C C17 0.8324(2) 0.3692(4) 0.7118(2) 0.0477(8) Uani d 1 . .
H H17A 0.8557 0.2922 0.6864 0.057 Uiso calc 1 . .
H H17B 0.8015 0.3151 0.7397 0.057 Uiso calc 1 . .
C C18 0.9012(2) 0.4620(6) 0.7653(2) 0.0650(10) Uani d 1 . .
H H18A 0.9405 0.3952 0.8037 0.097 Uiso calc 1 . .
H H18B 0.8776 0.5372 0.7904 0.097 Uiso calc 1 . .
H H18C 0.9313 0.5153 0.7371 0.097 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0014 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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
C4 B1 C1 . . 110.0(2)
C4 B1 C3 . . 110.2(2)
C1 B1 C3 . . 111.2(2)
C4 B1 C2 . . 108.5(2)
C1 B1 C2 . . 109.0(2)
C3 B1 C2 . . 107.8(2)
N1 C1 B1 . . 178.8(3)
N2 C2 B1 . . 179.0(3)
N3 C3 B1 . . 177.5(3)
N4 C4 B1 . . 179.1(3)
C7 B2 C6 . . 111.0(2)
C7 B2 C5 . . 108.4(2)
C6 B2 C5 . . 108.9(2)
C7 B2 C8 . . 110.0(2)
C6 B2 C8 . . 108.3(2)
C5 B2 C8 . . 110.2(2)
N5 C5 B2 . . 177.8(3)
N6 C6 B2 . . 178.7(3)
N7 C7 B2 . . 177.6(4)
N8 C8 B2 . . 179.8(3)
C10 C9 H9A . . 109.5
C10 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C10 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
N9 C10 C9 . . 112.0(2)
N9 C10 C11 . . 108.2(2)
C9 C10 C11 . . 110.3(2)
N9 C10 H10A . . 108.8
C9 C10 H10A . . 108.8
C11 C10 H10A . . 108.8
C10 N9 H9D . . 109.5
C10 N9 H9E . . 109.5
H9D N9 H9E . . 109.5
C10 N9 H9F . . 109.5
H9D N9 H9F . . 109.5
H9E N9 H9F . . 109.5
O1 C11 O2 . . 125.8(2)
O1 C11 C10 . . 124.3(2)
O2 C11 C10 . . 109.8(2)
C11 O2 C12 . . 117.2(2)
O2 C12 C13 . . 109.4(3)
O2 C12 H12A . . 109.8
C13 C12 H12A . . 109.8
O2 C12 H12B . . 109.8
C13 C12 H12B . . 109.8
H12A C12 H12B . . 108.2
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C15 C14 H14A . . 109.5
C15 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C15 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N10 C15 C16 . . 108.8(2)
N10 C15 C14 . . 110.3(2)
C16 C15 C14 . . 111.6(2)
N10 C15 H15A . . 108.7
C16 C15 H15A . . 108.7
C14 C15 H15A . . 108.7
C15 N10 H10B . . 109.5
C15 N10 H10C . . 109.5
H10B N10 H10C . . 109.5
C15 N10 H10D . . 109.5
H10B N10 H10D . . 109.5
H10C N10 H10D . . 109.5
O3 C16 O4 . . 126.0(2)
O3 C16 C15 . . 124.2(2)
O4 C16 C15 . . 109.8(2)
C16 O4 C17 . . 119.4(2)
O4 C17 C18 . . 107.6(3)
O4 C17 H17A . . 110.2
C18 C17 H17A . . 110.2
O4 C17 H17B . . 110.2
C18 C17 H17B . . 110.2
H17A C17 H17B . . 108.5
C17 C18 H18A . . 109.5
C17 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C17 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 C4 . 1.585(4)
B1 C1 . 1.585(4)
B1 C3 . 1.591(4)
B1 C2 . 1.600(4)
C1 N1 . 1.142(4)
C2 N2 . 1.135(3)
C3 N3 . 1.137(3)
C4 N4 . 1.138(4)
B2 C7 . 1.585(4)
B2 C6 . 1.586(4)
B2 C5 . 1.586(4)
B2 C8 . 1.590(4)
C5 N5 . 1.140(4)
C6 N6 . 1.139(4)
C7 N7 . 1.134(4)
C8 N8 . 1.138(3)
C9 C10 . 1.497(4)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 N9 . 1.489(3)
C10 C11 . 1.505(4)
C10 H10A . 1.0000
N9 H9D . 0.9100
N9 H9E . 0.9100
N9 H9F . 0.9100
C11 O1 . 1.192(3)
C11 O2 . 1.330(3)
O2 C12 . 1.455(3)
C12 C13 . 1.490(6)
C12 H12A . 0.9900
C12 H12B . 0.9900
C13 H13A . 0.9800
C13 H13B . 0.9800
C13 H13C . 0.9800
C14 C15 . 1.514(4)
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C15 N10 . 1.482(3)
C15 C16 . 1.510(3)
C15 H15A . 1.0000
N10 H10B . 0.9100
N10 H10C . 0.9100
N10 H10D . 0.9100
C16 O3 . 1.188(3)
C16 O4 . 1.312(3)
O4 C17 . 1.451(3)
C17 C18 . 1.479(5)
C17 H17A . 0.9900
C17 H17B . 0.9900
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800
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
N9 H9F N6 3_454 0.91 2.16 2.920(3) 141 y
N10 H10B N4 3 0.91 2.05 2.953(3) 174 y
N10 H10D N1 . 0.91 2.07 2.961(3) 166 y
N9 H9E N8 1_554 0.91 2.14 3.001(3) 158 y
N10 H10C N2 1_565 0.91 2.15 3.015(3) 159 y
N9 H9D N5 3_444 0.91 2.14 3.017(3) 161 y
N9 H9F N3 4 0.91 2.64 3.147(3) 116 y
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
N9 C10 C11 O1 . . . . -7.2(3)
C9 C10 C11 O1 . . . . 115.7(3)
N9 C10 C11 O2 . . . . 175.3(2)
C9 C10 C11 O2 . . . . -61.9(3)
O1 C11 O2 C12 . . . . -9.5(4)
C10 C11 O2 C12 . . . . 168.1(2)
C11 O2 C12 C13 . . . . -86.1(3)
N10 C15 C16 O3 . . . . -6.3(3)
C14 C15 C16 O3 . . . . 115.6(3)
N10 C15 C16 O4 . . . . 175.1(2)
C14 C15 C16 O4 . . . . -63.0(3)
O3 C16 O4 C17 . . . . 2.5(4)
C15 C16 O4 C17 . . . . -178.9(3)
C16 O4 C17 C18 . . . . 136.5(3)

_cod_database_fobs_code 1563168
