#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:33:20 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158224.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_7158224
loop_
_publ_author_name
'Maeda, Hiromitsu'
'Haketa, Yohei'
'Murata, Tomoki'
'Ohta, Eriko'
'Murata, Tai'
'Yasuda, Nobuhiro'
_publ_section_title
;
 Self-assemblies of anionic-unit-introduced anion-responsive π-electronic
 molecules
;
_journal_issue                   34
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              7369
_journal_page_last               7373
_journal_paper_doi               10.1039/D1OB01094H
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 B F N2 O4'
_chemical_formula_sum            'C18 H14 B F N2 O4'
_chemical_formula_weight         352.12
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.961(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8897(3)
_cell_length_b                   15.6222(7)
_cell_length_c                   18.0449(8)
_cell_measurement_reflns_used    17257
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      29.236
_cell_measurement_theta_min      1.973
_cell_volume                     1648.07(13)
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_collection       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless ω scans'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.81088
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17257
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        29.113
_diffrn_reflns_theta_max         29.236
_diffrn_reflns_theta_min         1.973
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0134(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0457
_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)+(0.0511P)²+1.1165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2656
_reflns_number_total             3011
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01094h2.cif
_cod_data_source_block           ydkr_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158218--7158229.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158224
_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.
;
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
C1 C -0.1588(3) 0.73552(12) 0.77812(11) 0.0292(5) Uani 1 1 d . . . . .
H1 H -0.2960 0.7681 0.7720 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0244(4) 0.72015(13) 0.84463(11) 0.0311(5) Uani 1 1 d . . . . .
H2 H -0.0519 0.7402 0.8924 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1605(4) 0.66948(12) 0.82887(11) 0.0284(4) Uani 1 1 d . . . . .
H3 H 0.2815 0.6492 0.8641 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1350(3) 0.65452(11) 0.75294(10) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.2667(3) 0.60783(11) 0.70492(10) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.4753(3) 0.56848(11) 0.72843(11) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.5473 0.5759 0.7780 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5764(3) 0.51792(11) 0.67782(10) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.7771(3) 0.46722(11) 0.69729(11) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.9070(3) 0.45094(12) 0.76491(12) 0.0280(4) Uani 1 1 d . . . . .
H9 H 0.8749 0.4697 0.8126 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0952(3) 0.40162(12) 0.74988(12) 0.0300(5) Uani 1 1 d . . . . .
H10 H 1.2139 0.3806 0.7856 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0763(3) 0.38920(12) 0.67388(12) 0.0289(5) Uani 1 1 d . . . . .
H11 H 1.1814 0.3586 0.6479 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4775(3) 0.66989(11) 0.56297(10) 0.0212(4) Uani 1 1 d . . . . .
C13 C 0.4006(3) 0.75082(12) 0.58184(11) 0.0253(4) Uani 1 1 d . . . . .
H13 H 0.2632 0.7553 0.6042 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5194(3) 0.82445(12) 0.56872(11) 0.0267(4) Uani 1 1 d . . . . .
H14 H 0.4628 0.8787 0.5816 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7216(3) 0.81903(12) 0.53665(10) 0.0236(4) Uani 1 1 d . . . . .
C16 C 0.8480(3) 0.89790(12) 0.52192(10) 0.0260(4) Uani 1 1 d . . . . .
C17 C 0.8027(3) 0.73928(12) 0.51700(10) 0.0252(4) Uani 1 1 d . . . . .
H17 H 0.9400 0.7353 0.4945 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6815(3) 0.66581(11) 0.53056(10) 0.0224(4) Uani 1 1 d . . . . .
H18 H 0.7383 0.6116 0.5176 0.027 Uiso 1 1 calc R U . . .
N1 N -0.0615(3) 0.69621(10) 0.72301(9) 0.0251(4) Uani 1 1 d . . . . .
H1A H -0.1154 0.6971 0.6754 0.030 Uiso 1 1 calc R U . . .
N2 N 0.8832(3) 0.42785(10) 0.64238(9) 0.0253(4) Uani 1 1 d . . . . .
H2A H 0.8330 0.4279 0.5944 0.030 Uiso 1 1 calc R U . . .
O1 O 0.1751(2) 0.60381(8) 0.63483(7) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.4908(2) 0.51434(8) 0.60706(7) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.7737(3) 0.96780(9) 0.54988(9) 0.0379(4) Uani 1 1 d . . . . .
H3A H 0.8475 1.0098 0.5364 0.057 Uiso 1 1 calc R U . . .
O4 O 1.0128(2) 0.89562(9) 0.48494(8) 0.0329(4) Uani 1 1 d . . . . .
B1 B 0.3335(4) 0.58488(13) 0.57846(12) 0.0226(5) Uani 1 1 d . . . . .
F1 F 0.20001(18) 0.55489(7) 0.51509(6) 0.0259(3) 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 0.0045 0.0022 '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 0.0085 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0146 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0231 0.0137 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0022 0.0009 '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
N1 C1 C2 108.16(18) . . ?
N1 C1 H1 125.9 . . ?
C2 C1 H1 125.9 . . ?
C1 C2 C3 107.47(18) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C4 C3 C2 107.63(18) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 N1 107.08(16) . . ?
C3 C4 C5 133.30(18) . . ?
N1 C4 C5 119.61(17) . . ?
O1 C5 C6 121.04(17) . . ?
O1 C5 C4 114.69(16) . . ?
C6 C5 C4 124.27(17) . . ?
C5 C6 C7 118.78(18) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
O2 C7 C6 121.04(17) . . ?
O2 C7 C8 115.01(16) . . ?
C6 C7 C8 123.95(18) . . ?
N2 C8 C9 107.55(17) . . ?
N2 C8 C7 120.22(17) . . ?
C9 C8 C7 132.13(18) . . ?
C8 C9 C10 107.21(18) . . ?
C8 C9 H9 126.4 . . ?
C10 C9 H9 126.4 . . ?
C11 C10 C9 107.43(18) . . ?
C11 C10 H10 126.3 . . ?
C9 C10 H10 126.3 . . ?
N2 C11 C10 108.60(18) . . ?
N2 C11 H11 125.7 . . ?
C10 C11 H11 125.7 . . ?
C13 C12 C18 117.55(16) . . ?
C13 C12 B1 120.51(16) . . ?
C18 C12 B1 121.94(16) . . ?
C14 C13 C12 121.66(18) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.91(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C17 119.83(17) . . ?
C14 C15 C16 119.97(17) . . ?
C17 C15 C16 120.18(17) . . ?
O4 C16 O3 123.61(17) . . ?
O4 C16 C15 120.98(17) . . ?
O3 C16 C15 115.41(17) . . ?
C18 C17 C15 119.61(17) . . ?
C18 C17 H17 120.2 . . ?
C15 C17 H17 120.2 . . ?
C17 C18 C12 121.42(17) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?
C1 N1 C4 109.65(16) . . ?
C1 N1 H1A 125.2 . . ?
C4 N1 H1A 125.2 . . ?
C11 N2 C8 109.19(17) . . ?
C11 N2 H2A 125.4 . . ?
C8 N2 H2A 125.4 . . ?
C5 O1 B1 116.62(15) . . ?
C7 O2 B1 116.96(14) . . ?
C16 O3 H3A 109.5 . . ?
F1 B1 O1 106.87(15) . . ?
F1 B1 O2 107.57(15) . . ?
O1 B1 O2 108.94(15) . . ?
F1 B1 C12 113.02(16) . . ?
O1 B1 C12 109.84(15) . . ?
O2 B1 C12 110.46(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
C1 N1 1.354(2) . ?
C1 C2 1.376(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 N1 1.380(2) . ?
C4 C5 1.431(3) . ?
C5 O1 1.315(2) . ?
C5 C6 1.393(3) . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.316(2) . ?
C7 C8 1.431(3) . ?
C8 N2 1.379(2) . ?
C8 C9 1.383(3) . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.351(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(3) . ?
C12 C18 1.400(3) . ?
C12 B1 1.618(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.395(3) . ?
C15 C16 1.480(3) . ?
C16 O4 1.243(2) . ?
C16 O3 1.301(2) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
O1 B1 1.491(2) . ?
O2 B1 1.491(2) . ?
O3 H3A 0.8400 . ?
B1 F1 1.388(2) . ?
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
N1 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 N1 0.5(2) . . . . ?
C2 C3 C4 C5 -179.8(2) . . . . ?
C3 C4 C5 O1 175.45(19) . . . . ?
N1 C4 C5 O1 -4.9(2) . . . . ?
C3 C4 C5 C6 -4.2(3) . . . . ?
N1 C4 C5 C6 175.43(16) . . . . ?
O1 C5 C6 C7 -5.7(3) . . . . ?
C4 C5 C6 C7 173.89(17) . . . . ?
C5 C6 C7 O2 7.2(3) . . . . ?
C5 C6 C7 C8 -173.20(17) . . . . ?
O2 C7 C8 N2 8.0(2) . . . . ?
C6 C7 C8 N2 -171.60(16) . . . . ?
O2 C7 C8 C9 -176.18(18) . . . . ?
C6 C7 C8 C9 4.2(3) . . . . ?
N2 C8 C9 C10 0.6(2) . . . . ?
C7 C8 C9 C10 -175.64(19) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 N2 -0.8(2) . . . . ?
C18 C12 C13 C14 0.5(3) . . . . ?
B1 C12 C13 C14 -179.52(18) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C17 0.7(3) . . . . ?
C13 C14 C15 C16 179.44(17) . . . . ?
C14 C15 C16 O4 -170.88(18) . . . . ?
C17 C15 C16 O4 7.8(3) . . . . ?
C14 C15 C16 O3 8.9(3) . . . . ?
C17 C15 C16 O3 -172.41(18) . . . . ?
C14 C15 C17 C18 -0.8(3) . . . . ?
C16 C15 C17 C18 -179.47(17) . . . . ?
C15 C17 C18 C12 0.7(3) . . . . ?
C13 C12 C18 C17 -0.5(3) . . . . ?
B1 C12 C18 C17 179.49(17) . . . . ?
C2 C1 N1 C4 0.5(2) . . . . ?
C3 C4 N1 C1 -0.6(2) . . . . ?
C5 C4 N1 C1 179.65(16) . . . . ?
C10 C11 N2 C8 1.2(2) . . . . ?
C9 C8 N2 C11 -1.1(2) . . . . ?
C7 C8 N2 C11 175.64(16) . . . . ?
C6 C5 O1 B1 -21.6(2) . . . . ?
C4 C5 O1 B1 158.76(15) . . . . ?
C6 C7 O2 B1 18.9(2) . . . . ?
C8 C7 O2 B1 -160.76(15) . . . . ?
C5 O1 B1 F1 159.95(14) . . . . ?
C5 O1 B1 O2 44.0(2) . . . . ?
C5 O1 B1 C12 -77.10(19) . . . . ?
C7 O2 B1 F1 -158.17(14) . . . . ?
C7 O2 B1 O1 -42.7(2) . . . . ?
C7 O2 B1 C12 78.05(19) . . . . ?
C13 C12 B1 F1 100.1(2) . . . . ?
C18 C12 B1 F1 -79.9(2) . . . . ?
C13 C12 B1 O1 -19.1(2) . . . . ?
C18 C12 B1 O1 160.88(16) . . . . ?
C13 C12 B1 O2 -139.33(17) . . . . ?
C18 C12 B1 O2 40.7(2) . . . . ?
