#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:12:45 +0300 (Wed, 05 Apr 2017) $
#$Revision: 194950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/98/7119857.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_7119857
loop_
_publ_author_name
'Lakshmi, Vellanki'
'Haketa, Yohei'
'Yamakado, Ryohei'
'Yasuda, Nobuhiro'
'Maeda, Hiromitsu'
_publ_section_title
;
 Dimension-controlled assemblies of anion-responsive π-electronic systems
 bearing aryl substituents with fan-shaped geometries.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3834
_journal_page_last               3837
_journal_paper_doi               10.1039/c7cc01551h
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C15 H17 B F2 N2 O2'
_chemical_formula_weight         306.11
_chemical_melting_point          ?
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-21 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.853(7)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   11.382(4)
_cell_length_b                   13.964(5)
_cell_length_c                   27.457(9)
_cell_measurement_reflns_used    20846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.030
_cell_measurement_theta_min      1.461
_cell_volume                     4362(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Mercury CCD2'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6999
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20846
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.831
_diffrn_reflns_theta_max         27.030
_diffrn_reflns_theta_min         1.461
_diffrn_source                   'synchrotron radiation SPring-8 BL02B1'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1150
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0970
_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)+(0.1734P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2773
_reflns_number_total             4937
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc01551h2.cif
_cod_data_source_block           ydkr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

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

 Adding full bibliography for 7119857--7119860.cif.
;
_cod_original_cell_volume        4362(2)
_cod_database_code               7119857
_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   0.990
_shelx_estimated_absorpt_t_max   0.995
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
C1 C 0.4627(4) 0.2480(4) 0.62326(15) 0.0529(12) Uani 1 1 d . . .
H1 H 0.3814 0.2710 0.6232 0.079 Uiso 1 1 calc R U .
H1A H 0.5085 0.2793 0.6496 0.079 Uiso 1 1 calc R U .
H1B H 0.4638 0.1785 0.6283 0.079 Uiso 1 1 calc R U .
C2 C 0.5150(3) 0.2709(3) 0.57567(15) 0.0433(10) Uani 1 1 d . . .
C3 C 0.5467(3) 0.3582(3) 0.55708(15) 0.0456(11) Uani 1 1 d . . .
H3 H 0.5414 0.4182 0.5732 0.055 Uiso 1 1 calc R U .
C4 C 0.5881(3) 0.3432(3) 0.51021(14) 0.0388(9) Uani 1 1 d . . .
C5 C 0.6294(4) 0.4206(3) 0.47663(17) 0.0503(11) Uani 1 1 d . . .
H5 H 0.6289 0.4824 0.4936 0.075 Uiso 1 1 calc R U .
H5A H 0.5767 0.4238 0.4477 0.075 Uiso 1 1 calc R U .
H5B H 0.7093 0.4062 0.4667 0.075 Uiso 1 1 calc R U .
C6 C 0.5830(3) 0.2450(3) 0.50222(13) 0.0346(9) Uani 1 1 d . . .
C7 C 0.6128(3) 0.1880(3) 0.46174(13) 0.0330(8) Uani 1 1 d . . .
C8 C 0.6553(3) 0.2224(3) 0.41874(12) 0.0327(8) Uani 1 1 d . . .
H8 H 0.6652 0.2893 0.4142 0.039 Uiso 1 1 calc R U .
C9 C 0.6832(3) 0.1597(3) 0.38248(12) 0.0306(8) Uani 1 1 d . . .
C10 C 0.7318(3) 0.1865(3) 0.33723(12) 0.0309(8) Uani 1 1 d . . .
C11 C 0.7728(3) 0.2720(3) 0.31891(14) 0.0356(9) Uani 1 1 d . . .
C12 C 0.7713(4) 0.3693(3) 0.34350(15) 0.0438(10) Uani 1 1 d . . .
H12 H 0.8083 0.4167 0.3226 0.066 Uiso 1 1 calc R U .
H12A H 0.8148 0.3658 0.3748 0.066 Uiso 1 1 calc R U .
H12B H 0.6899 0.3882 0.3489 0.066 Uiso 1 1 calc R U .
C13 C 0.8174(3) 0.2525(3) 0.27408(14) 0.0418(10) Uani 1 1 d . . .
H13 H 0.8519 0.2981 0.2532 0.050 Uiso 1 1 calc R U .
C14 C 0.8042(3) 0.1571(3) 0.26437(13) 0.0356(9) Uani 1 1 d . . .
C15 C 0.8387(4) 0.0969(3) 0.22241(14) 0.0438(10) Uani 1 1 d . . .
H15 H 0.8022 0.0336 0.2248 0.066 Uiso 1 1 calc R U .
H15A H 0.9244 0.0899 0.2229 0.066 Uiso 1 1 calc R U .
H15B H 0.8122 0.1276 0.1919 0.066 Uiso 1 1 calc R U .
C16 C 0.3090(4) 0.1605(4) 0.45306(14) 0.0607(15) Uani 1 1 d . . .
H16 H 0.2230 0.1560 0.4519 0.091 Uiso 1 1 calc R U .
H16A H 0.3346 0.1997 0.4811 0.091 Uiso 1 1 calc R U .
H16B H 0.3429 0.0963 0.4563 0.091 Uiso 1 1 calc R U .
C17 C 0.3490(3) 0.2056(4) 0.40745(14) 0.0460(11) Uani 1 1 d . . .
C18 C 0.3537(3) 0.2998(3) 0.39294(14) 0.0455(11) Uani 1 1 d . . .
H18 H 0.3309 0.3535 0.4117 0.055 Uiso 1 1 calc R U .
C19 C 0.3976(3) 0.3032(3) 0.34597(13) 0.0378(9) Uani 1 1 d . . .
C20 C 0.4186(3) 0.2104(3) 0.33250(12) 0.0304(8) Uani 1 1 d . . .
C21 C 0.4619(3) 0.1673(2) 0.28969(11) 0.0263(7) Uani 1 1 d . . .
C22 C 0.5000 0.2173(3) 0.2500 0.0284(10) Uani 1 2 d S T P
H22 H 0.5000 0.2853 0.2500 0.034 Uiso 1 2 calc R U P
C23 C 0.4101(4) 0.3918(3) 0.31715(15) 0.0463(10) Uani 1 1 d . . .
H23 H 0.4922 0.3992 0.3081 0.069 Uiso 1 1 calc R U .
H23A H 0.3867 0.4470 0.3366 0.069 Uiso 1 1 calc R U .
H23B H 0.3597 0.3879 0.2876 0.069 Uiso 1 1 calc R U .
N1 N 0.5398(3) 0.2049(3) 0.54312(11) 0.0390(8) Uani 1 1 d . . .
H1C H 0.5296 0.1430 0.5473 0.047 Uiso 1 1 calc R U .
N2 N 0.7537(3) 0.1173(2) 0.30343(11) 0.0339(7) Uani 1 1 d . . .
H2 H 0.7373 0.0561 0.3066 0.041 Uiso 1 1 calc R U .
N3 N 0.3887(3) 0.1527(2) 0.37063(10) 0.0357(7) Uani 1 1 d . . .
H3A H 0.3946 0.0898 0.3709 0.043 Uiso 1 1 calc R U .
F1 F 0.6834(2) -0.04697(16) 0.44811(8) 0.0449(6) Uani 1 1 d . . .
F2 F 0.5033(2) -0.01371(17) 0.41650(8) 0.0452(6) Uani 1 1 d . . .
F3 F 0.5925(2) -0.04168(16) 0.26668(8) 0.0465(6) Uani 1 1 d . . .
B1 B 0.6132(4) 0.0243(3) 0.43031(16) 0.0371(10) Uani 1 1 d . . .
B2 B 0.5000 0.0159(4) 0.2500 0.0380(14) Uani 1 2 d S T P
O1 O 0.6661(2) 0.06654(18) 0.38683(9) 0.0378(7) Uani 1 1 d . . .
O2 O 0.5961(2) 0.09513(19) 0.46841(9) 0.0378(6) Uani 1 1 d . . .
O3 O 0.4610(2) 0.07269(18) 0.29072(9) 0.0368(6) Uani 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 0.0030 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 0.0015 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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
N1 C2 C3 107.7(4) . .
N1 C2 C1 123.0(4) . .
C3 C2 C1 129.4(4) . .
C2 C3 C4 108.0(4) . .
C6 C4 C3 106.2(4) . .
C6 C4 C5 128.6(4) . .
C3 C4 C5 125.2(4) . .
N1 C6 C4 106.9(3) . .
N1 C6 C7 121.2(4) . .
C4 C6 C7 131.9(4) . .
O2 C7 C8 121.0(3) . .
O2 C7 C6 113.7(3) . .
C8 C7 C6 125.3(4) . .
C9 C8 C7 119.8(4) . .
O1 C9 C8 121.6(3) . .
O1 C9 C10 113.6(3) . .
C8 C9 C10 124.8(3) . .
N2 C10 C11 107.0(3) . .
N2 C10 C9 119.3(3) . .
C11 C10 C9 133.5(4) . .
C13 C11 C10 107.1(4) . .
C13 C11 C12 125.9(4) . .
C10 C11 C12 127.0(4) . .
C14 C13 C11 109.1(3) . .
N2 C14 C13 107.0(3) . .
N2 C14 C15 120.7(4) . .
C13 C14 C15 132.2(4) . .
N3 C17 C18 106.9(4) . .
N3 C17 C16 121.5(5) . .
C18 C17 C16 131.6(4) . .
C17 C18 C19 108.5(4) . .
C20 C19 C18 106.7(4) . .
C20 C19 C23 128.7(3) . .
C18 C19 C23 124.5(4) . .
C19 C20 N3 107.4(3) . .
C19 C20 C21 133.8(3) . .
N3 C20 C21 118.8(3) . .
O3 C21 C22 121.8(3) . .
O3 C21 C20 113.8(3) . .
C22 C21 C20 124.4(3) . .
C21 C22 C21 119.0(4) 2_655 .
C2 N1 C6 111.2(4) . .
C14 N2 C10 109.8(3) . .
C17 N3 C20 110.4(4) . .
F1 B1 F2 109.3(3) . .
F1 B1 O2 109.3(3) . .
F2 B1 O2 108.2(3) . .
F1 B1 O1 109.5(3) . .
F2 B1 O1 108.5(3) . .
O2 B1 O1 112.1(3) . .
F3 B2 F3 109.4(4) 2_655 .
F3 B2 O3 108.02(13) 2_655 2_655
F3 B2 O3 108.80(14) . 2_655
F3 B2 O3 108.79(14) 2_655 .
F3 B2 O3 108.02(13) . .
O3 B2 O3 113.8(4) 2_655 .
C9 O1 B1 122.1(3) . .
C7 O2 B1 122.9(3) . .
C21 O3 B2 121.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.488(6) .
C2 N1 1.321(5) .
C2 C3 1.375(7) .
C3 C4 1.401(6) .
C4 C6 1.391(6) .
C4 C5 1.505(6) .
C6 N1 1.361(5) .
C6 C7 1.417(5) .
C7 O2 1.325(5) .
C7 C8 1.376(5) .
C8 C9 1.370(5) .
C9 O1 1.321(4) .
C9 C10 1.426(5) .
C10 N2 1.369(5) .
C10 C11 1.382(5) .
C11 C13 1.374(5) .
C11 C12 1.518(5) .
C13 C14 1.365(6) .
C14 N2 1.353(4) .
C14 C15 1.489(5) .
C16 C17 1.486(6) .
C17 N3 1.342(5) .
C17 C18 1.376(7) .
C18 C19 1.399(5) .
C19 C20 1.371(5) .
C19 C23 1.477(6) .
C20 N3 1.373(5) .
C20 C21 1.423(5) .
C21 O3 1.321(4) .
C21 C22 1.376(4) .
C22 C21 1.376(4) 2_655
F1 B1 1.357(5) .
F2 B1 1.400(5) .
F3 B2 1.391(4) .
B1 O2 1.457(5) .
B1 O1 1.477(5) .
B2 F3 1.391(4) 2_655
B2 O3 1.452(4) 2_655
B2 O3 1.452(4) .
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_4
N1 C2 C3 C4 2.4(4) . .
C1 C2 C3 C4 -178.0(4) . .
C2 C3 C4 C6 -1.5(4) . .
C2 C3 C4 C5 178.6(4) . .
C3 C4 C6 N1 0.1(4) . .
C5 C4 C6 N1 180.0(4) . .
C3 C4 C6 C7 179.8(4) . .
C5 C4 C6 C7 -0.4(7) . .
N1 C6 C7 O2 -1.0(5) . .
C4 C6 C7 O2 179.4(4) . .
N1 C6 C7 C8 179.0(3) . .
C4 C6 C7 C8 -0.6(6) . .
O2 C7 C8 C9 -1.3(5) . .
C6 C7 C8 C9 178.7(3) . .
C7 C8 C9 O1 2.7(5) . .
C7 C8 C9 C10 -177.6(3) . .
O1 C9 C10 N2 1.1(5) . .
C8 C9 C10 N2 -178.7(3) . .
O1 C9 C10 C11 -173.4(4) . .
C8 C9 C10 C11 6.9(6) . .
N2 C10 C11 C13 0.7(4) . .
C9 C10 C11 C13 175.6(4) . .
N2 C10 C11 C12 -178.4(3) . .
C9 C10 C11 C12 -3.5(7) . .
C10 C11 C13 C14 0.3(4) . .
C12 C11 C13 C14 179.4(4) . .
C11 C13 C14 N2 -1.2(4) . .
C11 C13 C14 C15 -178.3(4) . .
N3 C17 C18 C19 0.0(4) . .
C16 C17 C18 C19 -179.2(4) . .
C17 C18 C19 C20 0.2(4) . .
C17 C18 C19 C23 177.0(4) . .
C18 C19 C20 N3 -0.3(4) . .
C23 C19 C20 N3 -176.9(4) . .
C18 C19 C20 C21 179.4(4) . .
C23 C19 C20 C21 2.8(7) . .
C19 C20 C21 O3 -175.6(4) . .
N3 C20 C21 O3 4.1(4) . .
C19 C20 C21 C22 3.5(6) . .
N3 C20 C21 C22 -176.8(3) . .
O3 C21 C22 C21 0.1(2) . 2_655
C20 C21 C22 C21 -179.0(4) . 2_655
C3 C2 N1 C6 -2.4(4) . .
C1 C2 N1 C6 178.0(3) . .
C4 C6 N1 C2 1.4(4) . .
C7 C6 N1 C2 -178.3(3) . .
C13 C14 N2 C10 1.6(4) . .
C15 C14 N2 C10 179.2(3) . .
C11 C10 N2 C14 -1.4(4) . .
C9 C10 N2 C14 -177.2(3) . .
C18 C17 N3 C20 -0.2(4) . .
C16 C17 N3 C20 179.1(3) . .
C19 C20 N3 C17 0.3(4) . .
C21 C20 N3 C17 -179.5(3) . .
C8 C9 O1 B1 1.6(5) . .
C10 C9 O1 B1 -178.1(3) . .
F1 B1 O1 C9 -127.9(4) . .
F2 B1 O1 C9 112.9(4) . .
O2 B1 O1 C9 -6.5(5) . .
C8 C7 O2 B1 -4.4(5) . .
C6 C7 O2 B1 175.6(3) . .
F1 B1 O2 C7 129.4(3) . .
F2 B1 O2 C7 -111.7(4) . .
O1 B1 O2 C7 7.9(5) . .
C22 C21 O3 B2 -0.2(4) . .
C20 C21 O3 B2 179.0(2) . .
F3 B2 O3 C21 -120.4(4) 2_655 .
F3 B2 O3 C21 121.0(4) . .
O3 B2 O3 C21 0.1(2) 2_655 .
