#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/26/7202660.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_7202660
loop_
_publ_author_name
'Tan, Wei'
'Zhang, Deqing'
'Wang, Zhuo'
'Liu, Caiming'
'Zhu, Daoben'
_publ_section_title
;
 4-(N,N-Dimethylamine)benzonitrile (DMABN) derivatives with boronic
 acid and boronate groups: new fluorescent sensors for saccharides and
 fluoride ion
;
_journal_issue                   19
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1964
_journal_paper_doi               10.1039/b618183j
_journal_volume                  17
_journal_year                    2007
_chemical_formula_sum            'C15 H21 B N2 O2'
_chemical_formula_weight         272.15
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3178(14)
_cell_length_b                   10.551(2)
_cell_length_c                   20.587(4)
_cell_measurement_reflns_used    1355
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.04
_cell_measurement_theta_min      2.17
_cell_volume                     1589.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8938
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs(Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.5656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                1279
_reflns_number_total             1637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B618183J.txt
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7202660
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0437(8) -0.1592(5) 0.0974(2) 0.0835(15) Uani 1 1 d . . .
N2 N 0.8502(7) 0.0951(5) 0.00612(19) 0.0761(13) Uani 1 1 d . . .
O1 O 0.2255(5) 0.0415(3) 0.20610(14) 0.0654(10) Uani 1 1 d . . .
O2 O 0.4238(5) 0.2015(4) 0.19671(16) 0.0813(12) Uani 1 1 d . . .
B1 B 0.3585(7) 0.0932(5) 0.1710(2) 0.0475(12) Uani 1 1 d . . .
C1 C 0.4380(6) 0.0385(4) 0.10533(18) 0.0488(11) Uani 1 1 d . . .
C2 C 0.3531(7) -0.0572(4) 0.06892(19) 0.0518(11) Uani 1 1 d . . .
C3 C 0.4364(8) -0.1013(5) 0.0129(2) 0.0634(14) Uani 1 1 d . . .
H3A H 0.3800 -0.1650 -0.0110 0.076 Uiso 1 1 calc R . .
C4 C 0.5994(8) -0.0533(5) -0.0080(2) 0.0690(15) Uani 1 1 d . . .
H4A H 0.6521 -0.0852 -0.0457 0.083 Uiso 1 1 calc R . .
C5 C 0.6902(7) 0.0446(4) 0.02690(19) 0.0559(12) Uani 1 1 d . . .
C6 C 0.6026(7) 0.0858(4) 0.08404(19) 0.0538(12) Uani 1 1 d . . .
H6A H 0.6591 0.1483 0.1087 0.065 Uiso 1 1 calc R . .
C7 C 0.1811(9) -0.1120(5) 0.0865(2) 0.0602(13) Uani 1 1 d . . .
C8 C 0.9488(9) 0.1829(6) 0.0460(3) 0.0884(18) Uani 1 1 d . . .
H8A H 0.8764 0.2577 0.0525 0.133 Uiso 1 1 calc R . .
H8B H 1.0613 0.2054 0.0250 0.133 Uiso 1 1 calc R . .
H8C H 0.9748 0.1445 0.0872 0.133 Uiso 1 1 calc R . .
C9 C 0.9393(10) 0.0501(7) -0.0520(3) 0.106(2) Uani 1 1 d . . .
H9A H 0.9687 -0.0381 -0.0471 0.159 Uiso 1 1 calc R . .
H9B H 1.0495 0.0975 -0.0591 0.159 Uiso 1 1 calc R . .
H9C H 0.8591 0.0609 -0.0885 0.159 Uiso 1 1 calc R . .
C10 C 0.3430(6) 0.2204(4) 0.2597(2) 0.0530(11) Uani 1 1 d . . .
C11 C 0.4894(9) 0.1924(7) 0.3087(3) 0.101(2) Uani 1 1 d . . .
H11C H 0.5837 0.2554 0.3057 0.152 Uiso 1 1 calc R . .
H11D H 0.5404 0.1102 0.3003 0.152 Uiso 1 1 calc R . .
H11A H 0.4376 0.1938 0.3516 0.152 Uiso 1 1 calc R . .
C12 C 0.2889(9) 0.3576(5) 0.2658(3) 0.094(2) Uani 1 1 d . . .
H12A H 0.3965 0.4096 0.2658 0.141 Uiso 1 1 calc R . .
H12B H 0.2233 0.3699 0.3057 0.141 Uiso 1 1 calc R . .
H12C H 0.2123 0.3808 0.2299 0.141 Uiso 1 1 calc R . .
C13 C 0.1806(7) 0.1256(5) 0.2590(2) 0.0583(13) Uani 1 1 d . . .
C14 C 0.1644(13) 0.0487(7) 0.3204(3) 0.125(3) Uani 1 1 d . . .
H14A H 0.0619 -0.0077 0.3170 0.187 Uiso 1 1 calc R . .
H14C H 0.1468 0.1046 0.3567 0.187 Uiso 1 1 calc R . .
H14D H 0.2741 0.0004 0.3267 0.187 Uiso 1 1 calc R . .
C15 C 0.0002(8) 0.1860(8) 0.2408(4) 0.117(3) Uani 1 1 d . . .
H15A H -0.0943 0.1229 0.2413 0.175 Uiso 1 1 calc R . .
H15B H 0.0092 0.2220 0.1981 0.175 Uiso 1 1 calc R . .
H15C H -0.0287 0.2516 0.2715 0.175 Uiso 1 1 calc R . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0000 '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
C5 N2 C8 120.6(4) . . ?
C5 N2 C9 121.5(5) . . ?
C8 N2 C9 117.4(5) . . ?
B1 O1 C13 109.0(3) . . ?
B1 O2 C10 109.0(3) . . ?
O1 B1 O2 113.2(4) . . ?
O1 B1 C1 125.8(4) . . ?
O2 B1 C1 121.0(4) . . ?
C6 C1 C2 118.6(4) . . ?
C6 C1 B1 117.6(4) . . ?
C2 C1 B1 123.8(4) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 C7 117.5(4) . . ?
C1 C2 C7 123.0(4) . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
N2 C5 C6 122.3(5) . . ?
N2 C5 C4 122.0(4) . . ?
C6 C5 C4 115.7(5) . . ?
C1 C6 C5 123.6(4) . . ?
C1 C6 H6A 118.2 . . ?
C5 C6 H6A 118.2 . . ?
N1 C7 C2 176.3(5) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 106.6(4) . . ?
O2 C10 C12 108.5(4) . . ?
C11 C10 C12 108.7(5) . . ?
O2 C10 C13 102.5(3) . . ?
C11 C10 C13 115.2(4) . . ?
C12 C10 C13 114.7(4) . . ?
C10 C11 H11C 109.5 . . ?
C10 C11 H11D 109.5 . . ?
H11C C11 H11D 109.5 . . ?
C10 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11D C11 H11A 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C14 108.7(4) . . ?
O1 C13 C15 105.7(4) . . ?
C14 C13 C15 111.5(6) . . ?
O1 C13 C10 103.2(3) . . ?
C14 C13 C10 113.5(4) . . ?
C15 C13 C10 113.5(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
C13 C14 H14D 109.5 . . ?
H14A C14 H14D 109.5 . . ?
H14C C14 H14D 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
N1 C7 1.144(7) . ?
N2 C5 1.356(7) . ?
N2 C8 1.433(7) . ?
N2 C9 1.443(6) . ?
O1 B1 1.330(6) . ?
O1 C13 1.443(5) . ?
O2 B1 1.348(6) . ?
O2 C10 1.439(5) . ?
B1 C1 1.580(6) . ?
C1 C6 1.375(6) . ?
C1 C2 1.403(6) . ?
C2 C3 1.384(6) . ?
C2 C7 1.432(8) . ?
C3 C4 1.366(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.422(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.408(6) . ?
C6 H6A 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.501(7) . ?
C10 C12 1.506(7) . ?
C10 C13 1.553(6) . ?
C11 H11C 0.9600 . ?
C11 H11D 0.9600 . ?
C11 H11A 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.507(7) . ?
C13 C15 1.513(8) . ?
C14 H14A 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21143137
2 PubChem 53426396
