#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/37/1553774.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_1553774
loop_
_publ_author_name
'Kubota, Yasuhiro'
'Tsukamoto, Masahiro'
'Ohnishi, Katsuhiro'
'Jin, Jiye'
'Funabiki, Kazumasa'
'Matsui, Masaki'
_publ_section_title
;
 Synthesis and fluorescence properties of novel squarylium--boron
 complexes
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1522
_journal_paper_doi               10.1039/C7QO00225D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C20 H23 B F2 N2 O2'
_chemical_formula_weight         372.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-08 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                73.19(6)
_cell_angle_beta                 69.99(5)
_cell_angle_gamma                72.45(4)
_cell_formula_units_Z            2
_cell_length_a                   9.003(10)
_cell_length_b                   10.762(12)
_cell_length_c                   11.631(12)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.370
_cell_measurement_theta_min      2.471
_cell_volume                     987.6(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9489
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.370
_diffrn_reflns_theta_min         2.471
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0596
_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)+(0.1079P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3039
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7qo00225d2.cif
_cod_data_source_block           CrystalClear
_cod_database_code               1553774
_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   0.982
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.39391(15) 0.83053(13) 0.38163(13) 0.0510(3) Uani 1 1 d . .
F1 F 0.12374(13) 0.93723(13) 0.38148(12) 0.0661(4) Uani 1 1 d . .
O2 O 0.76153(17) 1.07423(14) 0.31298(15) 0.0625(4) Uani 1 1 d . .
F2 F 0.27133(17) 0.79044(13) 0.25317(14) 0.0754(4) Uani 1 1 d . .
N2 N 0.83561(18) 0.82131(15) 0.53048(15) 0.0429(4) Uani 1 1 d . .
H2 H 0.877(3) 0.892(2) 0.489(3) 0.077(8) Uiso 1 1 d . .
C9 C 0.70536(19) 0.79313(16) 0.51081(16) 0.0398(4) Uani 1 1 d . .
N1 N 0.32887(18) 1.00995(16) 0.19530(14) 0.0466(4) Uani 1 1 d . .
C7 C 0.6305(2) 0.87959(17) 0.42130(16) 0.0401(4) Uani 1 1 d . .
C8 C 0.5030(2) 0.89427(17) 0.36719(16) 0.0405(4) Uani 1 1 d . .
C5 C 0.53227(19) 1.01316(17) 0.27869(16) 0.0400(4) Uani 1 1 d . .
C11 C 0.7991(2) 0.62603(17) 0.65900(16) 0.0430(4) Uani 1 1 d . .
C12 C 0.8931(2) 0.72233(17) 0.61758(16) 0.0430(4) Uani 1 1 d . .
C10 C 0.6814(2) 0.66902(18) 0.59246(17) 0.0438(4) Uani 1 1 d . .
C6 C 0.6645(2) 1.00763(18) 0.33188(17) 0.0435(4) Uani 1 1 d . .
C4 C 0.44806(19) 1.07351(17) 0.18945(16) 0.0420(4) Uani 1 1 d . .
C3 C 0.4576(2) 1.1820(2) 0.08542(18) 0.0509(4) Uani 1 1 d . .
C1 C 0.2675(2) 1.0766(2) 0.09718(18) 0.0543(5) Uani 1 1 d . .
C17 C 1.0341(2) 0.7240(2) 0.6578(2) 0.0592(5) Uani 1 1 d . .
H17 H 1.0557 0.6453 0.7200 0.089 Uiso 1 1 calc R U
H17A H 1.1281 0.7265 0.5868 0.089 Uiso 1 1 calc R U
H17B H 1.0085 0.8014 0.6923 0.089 Uiso 1 1 calc R U
C18 C 0.8299(3) 0.49726(19) 0.75119(19) 0.0557(5) Uani 1 1 d . .
H18 H 0.7332 0.4616 0.7833 0.067 Uiso 1 1 calc R U
H18A H 0.8495 0.5154 0.8211 0.067 Uiso 1 1 calc R U
C2 C 0.3465(2) 1.1813(2) 0.02618(19) 0.0569(5) Uani 1 1 d . .
C16 C 0.5682(3) 1.2749(2) 0.0510(2) 0.0674(6) Uani 1 1 d . .
H16 H 0.6301 1.2494 0.1103 0.101 Uiso 1 1 calc R U
H16A H 0.6405 1.2706 -0.0312 0.101 Uiso 1 1 calc R U
H16B H 0.5048 1.3643 0.0520 0.101 Uiso 1 1 calc R U
C20 C 0.5540(3) 0.6001(2) 0.6029(2) 0.0690(6) Uani 1 1 d . .
H20 H 0.4911 0.6526 0.5463 0.103 Uiso 1 1 calc R U
H20A H 0.6051 0.5142 0.5822 0.103 Uiso 1 1 calc R U
H20B H 0.4843 0.5895 0.6870 0.103 Uiso 1 1 calc R U
C19 C 0.9742(3) 0.3916(2) 0.6959(3) 0.0724(7) Uani 1 1 d . .
H19 H 0.9871 0.3123 0.7594 0.109 Uiso 1 1 calc R U
H19A H 0.9547 0.3713 0.6279 0.109 Uiso 1 1 calc R U
H19B H 1.0711 0.4251 0.6658 0.109 Uiso 1 1 calc R U
B1 B 0.2761(2) 0.8907(2) 0.3017(2) 0.0481(5) Uani 1 1 d . .
C13 C 0.1340(3) 1.0396(3) 0.0728(3) 0.0741(7) Uani 1 1 d . .
H13 H 0.1084 1.0988 -0.0008 0.111 Uiso 1 1 calc R U
H13A H 0.1692 0.9497 0.0604 0.111 Uiso 1 1 calc R U
H13B H 0.0393 1.0466 0.1431 0.111 Uiso 1 1 calc R U
C14 C 0.3162(3) 1.2745(3) -0.0937(2) 0.0761(7) Uani 1 1 d . .
H14 H 0.4186 1.2927 -0.1503 0.091 Uiso 1 1 calc R U
H14A H 0.2745 1.2302 -0.1337 0.091 Uiso 1 1 calc R U
C15 C 0.2012(5) 1.4018(4) -0.0736(4) 0.1379(17) Uani 1 1 d . .
H15 H 0.1872 1.4560 -0.1524 0.207 Uiso 1 1 calc R U
H15A H 0.0985 1.3850 -0.0193 0.207 Uiso 1 1 calc R U
H15B H 0.2428 1.4475 -0.0360 0.207 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'
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
C8 O1 B1 118.20(16)
C12 N2 C9 110.13(16)
C7 C9 N2 120.12(17)
C7 C9 C10 133.13(17)
N2 C9 C10 106.71(16)
C1 N1 C4 106.77(17)
C1 N1 B1 128.68(17)
C4 N1 B1 124.46(15)
C9 C7 C8 141.04(17)
C9 C7 C6 131.63(17)
C8 C7 C6 87.30(15)
O1 C8 C5 127.13(16)
O1 C8 C7 137.69(17)
C5 C8 C7 95.17(15)
O1 C8 C6 174.46(15)
C5 C8 C6 47.35(11)
C7 C8 C6 47.84(11)
C4 C5 C8 122.30(17)
C4 C5 C6 149.22(17)
C8 C5 C6 88.36(15)
C12 C11 C10 107.66(17)
C12 C11 C18 124.72(17)
C10 C11 C18 127.50(17)
N2 C12 C11 108.48(17)
N2 C12 C17 122.45(18)
C11 C12 C17 129.07(17)
C11 C10 C9 107.02(16)
C11 C10 C20 127.80(18)
C9 C10 C20 125.18(18)
O2 C6 C5 136.89(18)
O2 C6 C7 133.98(17)
C5 C6 C7 89.13(15)
O2 C6 C8 178.77(16)
C5 C6 C8 44.29(11)
C7 C6 C8 44.86(10)
C5 C4 N1 114.97(17)
C5 C4 C3 135.62(17)
N1 C4 C3 109.27(16)
C2 C3 C4 106.17(18)
C2 C3 C16 129.3(2)
C4 C3 C16 124.53(18)
N1 C1 C2 110.08(19)
N1 C1 C13 122.7(2)
C2 C1 C13 127.2(2)
C11 C18 C19 113.77(19)
C3 C2 C1 107.66(19)
C3 C2 C14 126.7(2)
C1 C2 C14 125.7(2)
F2 B1 F1 110.80(18)
F2 B1 O1 107.00(17)
F1 B1 O1 107.01(18)
F2 B1 N1 111.17(19)
F1 B1 N1 109.09(17)
O1 B1 N1 111.69(16)
C15 C14 C2 113.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.300(2)
O1 B1 1.524(3)
F1 B1 1.406(3)
O2 C6 1.217(2)
F2 B1 1.372(3)
N2 C12 1.353(3)
N2 C9 1.399(3)
C9 C7 1.395(3)
C9 C10 1.426(3)
N1 C1 1.357(3)
N1 C4 1.411(3)
N1 B1 1.565(3)
C7 C8 1.437(3)
C7 C6 1.511(3)
C8 C5 1.422(3)
C8 C6 2.036(3)
C5 C4 1.388(3)
C5 C6 1.498(3)
C11 C12 1.408(3)
C11 C10 1.412(3)
C11 C18 1.503(3)
C12 C17 1.502(3)
C10 C20 1.498(3)
C4 C3 1.416(3)
C3 C2 1.398(3)
C3 C16 1.500(3)
C1 C2 1.414(3)
C1 C13 1.508(3)
C18 C19 1.535(3)
C2 C14 1.521(3)
C14 C15 1.472(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
C12 N2 C9 C7 -177.73(15)
C12 N2 C9 C10 0.53(19)
N2 C9 C7 C8 178.68(19)
C10 C9 C7 C8 1.0(4)
N2 C9 C7 C6 1.0(3)
C10 C9 C7 C6 -176.66(17)
B1 O1 C8 C5 -3.7(2)
B1 O1 C8 C7 177.67(19)
C9 C7 C8 O1 2.1(4)
C6 C7 C8 O1 -179.7(2)
C9 C7 C8 C5 -176.8(2)
C6 C7 C8 C5 1.46(13)
C9 C7 C8 C6 -178.2(3)
O1 C8 C5 C4 -3.4(3)
C7 C8 C5 C4 175.68(16)
C6 C8 C5 C4 177.2(2)
O1 C8 C5 C6 179.48(17)
C7 C8 C5 C6 -1.47(13)
C9 N2 C12 C11 -0.74(19)
C9 N2 C12 C17 179.52(17)
C10 C11 C12 N2 0.66(19)
C18 C11 C12 N2 176.83(16)
C10 C11 C12 C17 -179.62(18)
C18 C11 C12 C17 -3.5(3)
C12 C11 C10 C9 -0.33(19)
C18 C11 C10 C9 -176.36(17)
C12 C11 C10 C20 179.58(19)
C18 C11 C10 C20 3.6(3)
C7 C9 C10 C11 177.83(18)
N2 C9 C10 C11 -0.10(19)
C7 C9 C10 C20 -2.1(3)
N2 C9 C10 C20 179.98(18)
C4 C5 C6 O2 5.3(4)
C8 C5 C6 O2 -179.5(2)
C4 C5 C6 C7 -173.9(3)
C8 C5 C6 C7 1.39(12)
C4 C5 C6 C8 -175.3(3)
C9 C7 C6 O2 -2.1(3)
C8 C7 C6 O2 179.4(2)
C9 C7 C6 C5 177.13(18)
C8 C7 C6 C5 -1.38(12)
C9 C7 C6 C8 178.5(2)
C8 C5 C4 N1 1.5(2)
C6 C5 C4 N1 175.9(2)
C8 C5 C4 C3 -173.70(18)
C6 C5 C4 C3 0.7(4)
C1 N1 C4 C5 -176.01(15)
B1 N1 C4 C5 7.1(2)
C1 N1 C4 C3 0.44(19)
B1 N1 C4 C3 -176.41(16)
C5 C4 C3 C2 173.7(2)
N1 C4 C3 C2 -1.7(2)
C5 C4 C3 C16 -6.1(3)
N1 C4 C3 C16 178.48(18)
C4 N1 C1 C2 1.0(2)
B1 N1 C1 C2 177.64(17)
C4 N1 C1 C13 -178.92(18)
B1 N1 C1 C13 -2.2(3)
C12 C11 C18 C19 -75.5(2)
C10 C11 C18 C19 99.9(2)
C4 C3 C2 C1 2.2(2)
C16 C3 C2 C1 -177.9(2)
C4 C3 C2 C14 -177.1(2)
C16 C3 C2 C14 2.7(4)
N1 C1 C2 C3 -2.0(2)
C13 C1 C2 C3 177.85(19)
N1 C1 C2 C14 177.32(19)
C13 C1 C2 C14 -2.8(4)
C8 O1 B1 F2 132.57(18)
C8 O1 B1 F1 -108.62(19)
C8 O1 B1 N1 10.7(2)
C1 N1 B1 F2 51.4(3)
C4 N1 B1 F2 -132.51(18)
C1 N1 B1 F1 -71.1(3)
C4 N1 B1 F1 105.0(2)
C1 N1 B1 O1 170.78(17)
C4 N1 B1 O1 -13.1(2)
C3 C2 C14 C15 -84.5(3)
C1 C2 C14 C15 96.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304027
