#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:32:48 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230903 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/14/7231475.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_7231475
loop_
_publ_author_name
'Escudero-Adán, Eduardo C'
'Bauzá, Antonio'
'Lecomte, Claude'
'Frontera, Antonio'
'Ballester, Pablo'
_publ_section_title
;
 Boron triel bonding: a weak electrostatic interaction lacking
 electron-density descriptors.
;
_journal_issue                   37
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              24192
_journal_page_last               24200
_journal_paper_doi               10.1039/c8cp04401e
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C6 H4 N2 O4'
_chemical_formula_weight         168.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0201(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.66357(3)
_cell_length_b                   5.37326(3)
_cell_length_c                   10.91612(7)
_cell_measurement_reflns_used    53740
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      65.1240
_cell_measurement_theta_min      3.5890
_cell_volume                     331.991(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2014
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            69397
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         55.161
_diffrn_reflns_theta_min         3.735
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       block
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     63
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0634P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4093
_reflns_number_total             4276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cp04401e2.cif
_cod_data_source_block           14DNB_BNI_b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7231471--7231476.cif.
;
_cod_database_code               7231475
_shelx_shelxl_version_number     2014/7
_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   0.975
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_file
;

    14DNB_BNI_b.res created by SHELXL-2014/7


TITL 14DNB_BNI_b in P2(1)/n
CELL 0.71073   5.663572   5.373264  10.916121  90.0000  92.0201  90.0000
ZERR    2.00   0.000033   0.000033   0.000068   0.0000   0.0005   0.0000
LATT 1
SYMM -x+1/2, y+1/2,-z+1/2
SFAC C  H  N  O
UNIT 12 8 4 8
LIST 4
REM P2(1)/n (#14 in standard setting)
L.S. 20
acta
conf
BOND
FMAP 2
PLAN 20
shel 99 0.43297
REM omit 2 4 5
REM omit 3 0 3
REM omit 0 3 5
REM omit -2 0 10
REM omit 0 1 4
REM omit -4 2 2
size 0.35 0.3 0.2
rem shel 2.0 0.0

WGHT    0.063400    0.012900
FVAR       1.26805
N1    3    0.689159    0.105206    0.143482    11.00000    0.01583    0.01128 =
         0.01302   -0.00020   -0.00169    0.00197
O1    4    0.565426    0.014950    0.222161    11.00000    0.02001    0.01810 =
         0.02118    0.00758   -0.00001   -0.00139
O2    4    0.890339    0.035762    0.123309    11.00000    0.02105    0.02133 =
         0.01834    0.00134    0.00112    0.01122
C1    1    0.590359    0.310480    0.068640    11.00000    0.01181    0.01123 =
         0.01168   -0.00011   -0.00037    0.00144
C2    1    0.379748    0.417775    0.103294    11.00000    0.01263    0.01489 =
         0.01306    0.00160    0.00192    0.00212
C3    1    0.712966    0.387204   -0.032896    11.00000    0.01209    0.01478 =
         0.01344    0.00061    0.00151    0.00325
H2    2    0.299689    0.368296    0.170130    11.00000    0.03201
H3    2    0.866348    0.305880   -0.050783    11.00000    0.03772
HKLF 4

REM  14DNB_BNI_b in P2(1)/n
REM R1 =  0.0288 for    4093 Fo > 4sig(Fo)  and  0.0296 for all    4276 data
REM     63 parameters refined using      0 restraints

END

WGHT      0.0607      0.0144

REM Highest difference peak  0.607,  deepest hole -0.481,  1-sigma level  0.064
Q1    1   0.6483  0.3422  0.0220  11.00000  0.05    0.61
Q2    1   0.4893  0.3623  0.0854  11.00000  0.05    0.57
Q3    1   0.3373  0.5190  0.0693  11.00000  0.05    0.53
Q4    1   0.8367 -0.0160  0.1088  11.00000  0.05    0.51
Q5    1   0.6484  0.1957  0.1102  11.00000  0.05    0.45
Q6    1   0.6346  0.0680  0.1799  11.00000  0.05    0.34
Q7    1   0.8973 -0.0403  0.1548  11.00000  0.05    0.31
Q8    1   0.7724  0.0843  0.1317  11.00000  0.05    0.29
Q9    1   0.7993  0.3154 -0.0553  11.00000  0.05    0.27
Q10   1   0.9091  0.0941  0.0838  11.00000  0.05    0.27
Q11   1   0.6016 -0.0563  0.2441  11.00000  0.05    0.25
Q12   1   0.4870  0.0526  0.2168  11.00000  0.05    0.24
Q13   1   0.5866 -0.0225  0.1900  11.00000  0.05    0.21
Q14   1   0.3534  0.3874  0.1399  11.00000  0.05    0.21
Q15   1   0.7407  0.1081 -0.0877  11.00000  0.05    0.09
Q16   1   1.0080  0.1821  0.2371  11.00000  0.05    0.07
Q17   1   0.3612 -0.0115  0.0967  11.00000  0.05    0.07
Q18   1   0.8753  0.1423  0.3021  11.00000  0.05    0.07
Q19   1   1.2021  0.3344 -0.1110  11.00000  0.05    0.07
Q20   1   1.1220  0.3614 -0.1047  11.00000  0.05    0.06
;
_shelx_res_checksum              85831
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
N1 N 0.68916(4) 0.10521(4) 0.14348(2) 0.01343(3) Uani 1 1 d
O1 O 0.56543(4) 0.01495(5) 0.22216(2) 0.01978(4) Uani 1 1 d
O2 O 0.89034(4) 0.03576(5) 0.12331(2) 0.02023(4) Uani 1 1 d
C1 C 0.59036(3) 0.31048(4) 0.06864(2) 0.01159(3) Uani 1 1 d
C2 C 0.37975(4) 0.41777(4) 0.10329(2) 0.01349(4) Uani 1 1 d
C3 C 0.71297(4) 0.38720(4) -0.03290(2) 0.01341(4) Uani 1 1 d
H2 H 0.2997(17) 0.3683(19) 0.1701(9) 0.032(2) Uiso 1 1 d
H3 H 0.8663(15) 0.3059(19) -0.0508(9) 0.038(2) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.01583(7) 0.01128(6) 0.01302(6) -0.00020(4) -0.00169(5) 0.00197(4)
O1 0.02001(8) 0.01810(8) 0.02118(8) 0.00758(6) -0.00001(6) -0.00139(6)
O2 0.02105(8) 0.02133(8) 0.01834(7) 0.00134(6) 0.00112(6) 0.01122(6)
C1 0.01181(6) 0.01123(6) 0.01168(6) -0.00011(4) -0.00037(4) 0.00144(4)
C2 0.01263(6) 0.01489(7) 0.01306(7) 0.00160(5) 0.00192(5) 0.00212(5)
C3 0.01209(6) 0.01478(7) 0.01344(7) 0.00061(5) 0.00151(5) 0.00325(5)
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'
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_3
O2 N1 O1 124.23(2) .
O2 N1 C1 117.77(2) .
O1 N1 C1 118.00(2) .
C2 C1 C3 123.469(19) .
C2 C1 N1 118.246(19) .
C3 C1 N1 118.285(18) .
C1 C2 C3 118.234(19) 3_665
C1 C3 C2 118.296(19) 3_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O2 1.2262(3) .
N1 O1 1.2273(3) .
N1 C1 1.4714(3) .
C1 C2 1.3893(3) .
C1 C3 1.3910(3) .
C2 C3 1.3914(3) 3_665
C3 C2 1.3914(3) 3_665
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
_geom_torsion_site_symmetry_4
O2 N1 C1 C2 -169.66(2) .
O1 N1 C1 C2 10.17(3) .
O2 N1 C1 C3 10.20(3) .
O1 N1 C1 C3 -169.96(2) .
C3 C1 C2 C3 -0.21(4) 3_665
N1 C1 C2 C3 179.651(19) 3_665
C2 C1 C3 C2 0.21(4) 3_665
N1 C1 C3 C2 -179.650(19) 3_665
