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#$Date: 2022-11-16 11:24:05 +0200 (Wed, 16 Nov 2022) $
#$Revision: 279317 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106113.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_8106113
loop_
_publ_author_name
'Tombul, Mustafa'
'Güven, Kutalmış'
'Bulut, Adnan'
'Svoboda, Ingrid'
'Fuess, Hartmut'
_publ_section_title
;
 Crystal structure of dimethylammonium bis(naphthalene-2,3-diolato)borate,
 C22H20BNO4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              247
_journal_page_last               249
_journal_paper_doi               10.1515/ncrs-2017-0250
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C20 H12 B O4, C2 H8 N'
_chemical_formula_sum            'C22 H20 B N O4'
_chemical_formula_weight         373.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 92.889(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.303(4)
_cell_length_b                   8.2703(6)
_cell_length_c                   7.3876(6)
_cell_measurement_reflns_used    3030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.778
_cell_measurement_theta_min      2.537
_cell_volume                     1971.1(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.4012
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type
;  
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer 
with Sapphire CCD Detector.
;
_diffrn_measurement_method
;  
Rotation method data acquisition using omega scans.
;
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6269
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.745
_diffrn_reflns_theta_min         2.542
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0978
_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)+(0.0504P)²+3.7626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1804
_refine_ls_wR_factor_ref         0.2063
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1363
_reflns_number_total             2126
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0250_suppl.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106113
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.02858(6) 0.9098(3) 0.1461(3) 0.0427(6) Uani 1 1 d . . . . .
O2 O 0.02738(7) 0.7117(3) 0.3700(3) 0.0471(7) Uani 1 1 d . . . . .
C1 C 0.06797(10) 0.8594(4) 0.1921(4) 0.0392(8) Uani 1 1 d . . . . .
N1 N 0.000000 0.2266(4) 0.250000 0.0534(11) Uani 1 2 d S T P . .
H1A H 0.004554 0.163085 0.155800 0.064 Uiso 0.5 1 calc R U P . .
H1B H -0.004554 0.163086 0.344200 0.064 Uiso 0.5 1 calc R U P . .
C2 C 0.10387(10) 0.9096(4) 0.1256(5) 0.0514(9) Uani 1 1 d . . . . .
H2 H 0.103936 0.991314 0.039222 0.062 Uiso 1 1 calc R U . . .
C10 C 0.06710(10) 0.7381(4) 0.3243(4) 0.0421(8) Uani 1 1 d . . . . .
C9 C 0.10223(11) 0.6641(4) 0.3887(5) 0.0538(9) Uani 1 1 d . . . . .
H9 H 0.101198 0.583004 0.475492 0.065 Uiso 1 1 calc R U . . .
C8 C 0.14065(11) 0.7127(5) 0.3211(5) 0.0562(10) Uani 1 1 d . . . . .
C3 C 0.14155(11) 0.8361(5) 0.1890(5) 0.0561(10) Uani 1 1 d . . . . .
B1 B 0.000000 0.8107(6) 0.250000 0.0414(12) Uani 1 2 d S T P . .
C4 C 0.18036(12) 0.8822(6) 0.1251(7) 0.0803(13) Uani 1 1 d D U . . .
H4 H 0.181499 0.963630 0.038685 0.096 Uiso 1 1 calc R U . . .
C7 C 0.17842(13) 0.6403(6) 0.3828(7) 0.0813(14) Uani 1 1 d D U . . .
H7 H 0.178312 0.558870 0.469571 0.098 Uiso 1 1 calc R U . . .
C11 C 0.03717(12) 0.3231(5) 0.2921(5) 0.0673(12) Uani 1 1 d . . . . .
H11A H 0.041439 0.396642 0.194271 0.101 Uiso 1 1 calc R U . . .
H11B H 0.060729 0.252816 0.308111 0.101 Uiso 1 1 calc R U . . .
H11C H 0.033753 0.383102 0.401560 0.101 Uiso 1 1 calc R U . . .
C5 C 0.21604(14) 0.8097(7) 0.1876(8) 0.0957(16) Uani 1 1 d D U . . .
H5 H 0.241240 0.841570 0.143513 0.115 Uiso 1 1 calc R U . . .
C6 C 0.21501(14) 0.6889(7) 0.3161(8) 0.0958(17) Uani 1 1 d D U . . .
H6 H 0.239594 0.639904 0.357864 0.115 Uiso 1 1 calc R U . . .
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'
B B 0.0013 0.0007 '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
C1 O1 B1 107.4(2) . .
C10 O2 B1 107.9(2) . .
C2 C1 O1 128.6(3) . .
C2 C1 C10 121.5(3) . .
O1 C1 C10 109.9(3) . .
C11 N1 C11 113.8(4) 2 .
C11 N1 H1A 108.8 2 .
C11 N1 H1A 108.8 . .
C11 N1 H1B 108.8 2 .
C11 N1 H1B 108.8 . .
H1A N1 H1B 107.7 . .
C1 C2 C3 119.2(3) . .
C1 C2 H2 120.4 . .
C3 C2 H2 120.4 . .
C9 C10 O2 128.6(3) . .
C9 C10 C1 121.5(3) . .
O2 C10 C1 109.9(3) . .
C10 C9 C8 118.8(3) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
C7 C8 C3 118.7(4) . .
C7 C8 C9 121.5(4) . .
C3 C8 C9 119.7(3) . .
C8 C3 C4 118.3(4) . .
C8 C3 C2 119.3(3) . .
C4 C3 C2 122.3(4) . .
O2 B1 O2 112.3(4) 2 .
O2 B1 O1 104.46(12) 2 2
O2 B1 O1 111.61(12) . 2
O2 B1 O1 111.60(12) 2 .
O2 B1 O1 104.46(12) . .
O1 B1 O1 112.6(4) 2 .
C5 C4 C3 121.2(5) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C6 C7 C8 120.6(5) . .
C6 C7 H7 119.7 . .
C8 C7 H7 119.7 . .
N1 C11 H11A 109.5 . .
N1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C4 C5 C6 120.2(5) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C7 C6 C5 120.9(4) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.366(3) .
O1 B1 1.478(3) .
O2 C10 1.361(4) .
O2 B1 1.470(3) .
C1 C2 1.347(4) .
C1 C10 1.401(4) .
N1 C11 1.462(4) 2
N1 C11 1.462(4) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
C2 C3 1.419(5) .
C2 H2 0.9300 .
C10 C9 1.354(4) .
C9 C8 1.419(5) .
C9 H9 0.9300 .
C8 C7 1.414(5) .
C8 C3 1.414(5) .
C3 C4 1.414(5) .
B1 O2 1.469(3) 2
B1 O1 1.478(3) 2
C4 C5 1.359(6) .
C4 H4 0.9300 .
C7 C6 1.364(6) .
C7 H7 0.9300 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C5 C6 1.380(7) .
C5 H5 0.9300 .
C6 H6 0.9300 .
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
B1 O1 C1 C2 176.7(3) . . . .
B1 O1 C1 C10 -2.2(3) . . . .
O1 C1 C2 C3 -177.8(3) . . . .
C10 C1 C2 C3 1.0(5) . . . .
B1 O2 C10 C9 -174.5(3) . . . .
B1 O2 C10 C1 5.2(3) . . . .
C2 C1 C10 C9 -1.2(5) . . . .
O1 C1 C10 C9 177.8(3) . . . .
C2 C1 C10 O2 179.1(3) . . . .
O1 C1 C10 O2 -1.9(4) . . . .
O2 C10 C9 C8 -179.7(3) . . . .
C1 C10 C9 C8 0.7(5) . . . .
C10 C9 C8 C7 180.0(3) . . . .
C10 C9 C8 C3 -0.1(5) . . . .
C7 C8 C3 C4 -0.3(6) . . . .
C9 C8 C3 C4 179.7(4) . . . .
C7 C8 C3 C2 179.9(4) . . . .
C9 C8 C3 C2 -0.1(5) . . . .
C1 C2 C3 C8 -0.3(5) . . . .
C1 C2 C3 C4 179.8(3) . . . .
C10 O2 B1 O2 114.8(2) . . . 2
C10 O2 B1 O1 -128.3(3) . . . 2
C10 O2 B1 O1 -6.3(3) . . . .
C1 O1 B1 O2 -116.4(3) . . . 2
C1 O1 B1 O2 5.1(3) . . . .
C1 O1 B1 O1 126.4(2) . . . 2
C8 C3 C4 C5 0.4(6) . . . .
C2 C3 C4 C5 -179.8(4) . . . .
C3 C8 C7 C6 0.1(6) . . . .
C9 C8 C7 C6 -180.0(4) . . . .
C3 C4 C5 C6 -0.2(8) . . . .
C8 C7 C6 C5 0.1(8) . . . .
C4 C5 C6 C7 -0.1(8) . . . .
