#------------------------------------------------------------------------------
#$Date: 2020-05-07 00:16:59 +0300 (Thu, 07 May 2020) $
#$Revision: 251828 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/04/7240464.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_7240464
loop_
_publ_author_name
'Wallis, John D.'
'Garner, Alun Christopher'
'Yang, Songjie'
_publ_section_title
;
 N-H···O Hydrogen Bonding to the Alkoxy Oxygen of a
 Carboxylic Ester Group: Crystal Structures of Methyl 2,6-Diaminobenzoate
 and Its Derivatives.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00495B
_journal_year                    2020
_chemical_formula_sum            'C8 H12 B2 F8 N2 O2'
_chemical_formula_weight         341.82
_chemical_melting_point          484.0(10)
_chemical_name_systematic
;
Methyl2,6-dinitrobenzoate bis HBF4 salt
;
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-04-01 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.379(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1001(4)
_cell_length_b                   10.8475(7)
_cell_length_c                   16.4165(11)
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2360
_cell_measurement_theta_min      4.1030
_cell_volume                     1260.68(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6957
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.372
_diffrn_reflns_theta_min         3.047
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.3349
_exptl_crystal_size_mid          0.1509
_exptl_crystal_size_min          0.1331
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0440
_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)+(0.0315P)²+0.2125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2368
_reflns_number_total             2966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00495b2.cif
_cod_data_source_block           bf4absH
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '483-485' was changed to
'484.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240464
_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.
;
_shelxl_version_number           2014-3
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.41716(14) 0.30171(9) 0.01871(6) 0.0174(3) Uani 1 1 d . . . . .
F2 F 0.42408(14) 0.34702(9) -0.11621(6) 0.0182(3) Uani 1 1 d . . . . .
F3 F 0.66838(14) 0.40683(9) -0.02709(7) 0.0180(3) Uani 1 1 d . . . . .
F4 F 0.62858(15) 0.20344(9) -0.05661(7) 0.0216(3) Uani 1 1 d . . . . .
F5 F 1.07428(15) 0.38768(10) 0.09352(7) 0.0228(3) Uani 1 1 d . . . . .
F6 F 1.06141(16) 0.32146(10) 0.22311(7) 0.0259(3) Uani 1 1 d . . . . .
F7 F 0.82115(15) 0.27277(9) 0.12811(7) 0.0247(3) Uani 1 1 d . . . . .
F8 F 0.85578(14) 0.46987(9) 0.17146(7) 0.0162(2) Uani 1 1 d . . . . .
O1 O -0.19660(16) 0.39527(10) -0.20945(7) 0.0128(3) Uani 1 1 d . . . . .
O2 O -0.04654(17) 0.33261(10) -0.31818(7) 0.0129(3) Uani 1 1 d . . . . .
N1 N 0.0284(2) 0.33565(14) -0.07288(11) 0.0121(3) Uani 1 1 d . . . . .
N2 N -0.0357(2) 0.08358(14) -0.32574(10) 0.0111(3) Uani 1 1 d . . . . .
C1 C -0.0123(2) 0.21158(15) -0.19980(11) 0.0096(4) Uani 1 1 d . . . . .
C2 C 0.0416(2) 0.21807(15) -0.11607(11) 0.0105(4) Uani 1 1 d . . . . .
C3 C 0.1152(2) 0.11815(15) -0.07271(11) 0.0124(4) Uani 1 1 d . . . . .
H3 H 0.1507 0.1255 -0.0159 0.015 Uiso 1 1 calc R U . . .
C4 C 0.1371(2) 0.00686(16) -0.11222(11) 0.0132(4) Uani 1 1 d . . . . .
H4 H 0.1861 -0.0627 -0.0825 0.016 Uiso 1 1 calc R U . . .
C5 C 0.0875(2) -0.00294(15) -0.19526(12) 0.0120(4) Uani 1 1 d . . . . .
H5 H 0.1029 -0.0790 -0.2227 0.014 Uiso 1 1 calc R U . . .
C6 C 0.0154(2) 0.09854(15) -0.23789(11) 0.0098(4) Uani 1 1 d . . . . .
C7 C -0.0980(2) 0.32315(15) -0.24231(11) 0.0102(4) Uani 1 1 d . . . . .
C8 C -0.1114(3) 0.44219(16) -0.36309(12) 0.0158(4) Uani 1 1 d . . . . .
H8A H -0.2498 0.4436 -0.3683 0.024 Uiso 1 1 calc R U . . .
H8B H -0.0638 0.4409 -0.4176 0.024 Uiso 1 1 calc R U . . .
H8C H -0.0642 0.5159 -0.3336 0.024 Uiso 1 1 calc R U . . .
B1 B 0.5355(3) 0.31290(18) -0.04509(13) 0.0139(4) Uani 1 1 d . . . . .
B2 B 0.9516(3) 0.36019(19) 0.15515(14) 0.0142(4) Uani 1 1 d . . . . .
H11 H -0.086(3) 0.3531(19) -0.0654(13) 0.024(6) Uiso 1 1 d . . . . .
H12 H 0.076(3) 0.401(2) -0.1043(14) 0.029(6) Uiso 1 1 d . . . . .
H13 H 0.093(3) 0.3332(19) -0.0244(14) 0.023(6) Uiso 1 1 d . . . . .
H21 H -0.168(3) 0.088(2) -0.3383(14) 0.034(6) Uiso 1 1 d . . . . .
H22 H 0.021(3) 0.141(2) -0.3567(15) 0.033(6) Uiso 1 1 d . . . . .
H23 H 0.005(3) 0.007(2) -0.3417(13) 0.026(6) Uiso 1 1 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 116.06(13) . . ?
C2 N1 H11 111.1(14) . . ?
C2 N1 H12 110.2(13) . . ?
H11 N1 H12 107.3(19) . . ?
C2 N1 H13 111.1(14) . . ?
H11 N1 H13 108(2) . . ?
H12 N1 H13 109.0(19) . . ?
C6 N2 H21 112.1(14) . . ?
C6 N2 H22 112.5(14) . . ?
H21 N2 H22 108(2) . . ?
C6 N2 H23 108.6(14) . . ?
H21 N2 H23 107.9(19) . . ?
H22 N2 H23 107.4(19) . . ?
C6 C1 C2 116.50(15) . . ?
C6 C1 C7 124.41(16) . . ?
C2 C1 C7 119.08(15) . . ?
C3 C2 C1 122.15(16) . . ?
C3 C2 N1 118.07(16) . . ?
C1 C2 N1 119.72(15) . . ?
C2 C3 C4 119.71(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.89(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.59(16) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 122.14(17) . . ?
C5 C6 N2 117.61(15) . . ?
C1 C6 N2 120.24(15) . . ?
O1 C7 O2 125.49(16) . . ?
O1 C7 C1 122.95(16) . . ?
O2 C7 C1 111.54(14) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F4 B1 F1 110.48(15) . . ?
F4 B1 F3 109.42(15) . . ?
F1 B1 F3 109.75(15) . . ?
F4 B1 F2 110.94(16) . . ?
F1 B1 F2 108.18(15) . . ?
F3 B1 F2 108.03(14) . . ?
F7 B2 F6 112.14(16) . . ?
F7 B2 F8 108.72(15) . . ?
F6 B2 F8 110.86(16) . . ?
F7 B2 F5 110.51(16) . . ?
F6 B2 F5 107.58(15) . . ?
F8 B2 F5 106.90(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.397(2) . ?
F2 B1 1.409(2) . ?
F3 B1 1.404(2) . ?
F4 B1 1.379(2) . ?
F5 B2 1.416(2) . ?
F6 B2 1.377(2) . ?
F7 B2 1.375(2) . ?
F8 B2 1.406(2) . ?
O1 C7 1.205(2) . ?
O2 C7 1.328(2) . ?
O2 C8 1.455(2) . ?
N1 C2 1.466(2) . ?
N1 H11 0.85(2) . ?
N1 H12 0.95(2) . ?
N1 H13 0.89(2) . ?
N2 C6 1.469(2) . ?
N2 H21 0.95(2) . ?
N2 H22 0.92(2) . ?
N2 H23 0.92(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.400(2) . ?
C1 C7 1.502(2) . ?
C2 C3 1.377(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8C F6 0.98 2.53 3.443(2) 155.0 3_665
N2 H23 F2 0.92(2) 1.95(2) 2.8699(18) 175(2) 2_544
N2 H23 F3 0.92(2) 2.63(2) 3.1707(19) 118.0(16) 2_544
N1 H13 F1 0.89(2) 2.38(2) 3.063(2) 133.8(18) .
N1 H13 F5 0.89(2) 2.04(2) 2.784(2) 140.9(19) 1_455
N2 H22 F1 0.92(2) 2.21(2) 2.8373(19) 125.1(18) 4_565
N2 H22 F7 0.92(2) 2.36(2) 3.1168(19) 139.9(19) 4_565
N2 H22 O2 0.92(2) 2.23(2) 2.7056(19) 111.5(17) .
N2 H21 F5 0.95(2) 2.09(2) 2.9937(19) 160(2) 4_465
N2 H21 F6 0.95(2) 2.44(2) 3.1996(19) 136.8(18) 4_465
N1 H12 F5 0.95(2) 2.54(2) 3.1009(19) 117.5(16) 3_665
N1 H12 F8 0.95(2) 1.87(2) 2.8195(19) 173.8(19) 3_665
N1 H11 F3 0.85(2) 1.98(2) 2.8262(19) 169(2) 1_455
N1 H11 F4 0.85(2) 2.61(2) 3.210(2) 128.5(17) 1_455
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(2) . . . . ?
C7 C1 C2 C3 177.80(15) . . . . ?
C6 C1 C2 N1 176.06(15) . . . . ?
C7 C1 C2 N1 -5.0(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
N1 C2 C3 C4 -177.35(15) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 N2 -179.81(15) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C7 C1 C6 C5 -177.16(15) . . . . ?
C2 C1 C6 N2 -179.54(14) . . . . ?
C7 C1 C6 N2 1.6(2) . . . . ?
C8 O2 C7 O1 2.2(2) . . . . ?
C8 O2 C7 C1 -175.97(14) . . . . ?
C6 C1 C7 O1 145.37(17) . . . . ?
C2 C1 C7 O1 -33.4(2) . . . . ?
C6 C1 C7 O2 -36.4(2) . . . . ?
C2 C1 C7 O2 144.77(15) . . . . ?
