#------------------------------------------------------------------------------ #$Date: 2021-08-19 01:10:36 +0300 (Thu, 19 Aug 2021) $ #$Revision: 268124 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564369.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_1564369 loop_ _publ_author_name 'Li, Xiaopei' 'Wang, Dongdong' 'Zhang, Yongjie' 'Lu, Wenqi' 'Yang, Songqiu' 'Hou, Guangjin' 'Zhao, Zhenchao' 'Qin, Haijuan' 'Zhang, Yahui' 'Li, Minmin' 'Qing, Guangyan' _publ_section_title ; A novel aggregation--induced enhanced emission aromatic molecule: 2-aminophenylboronic acid dimer ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC03765J _journal_year 2021 _chemical_formula_moiety 'C12 H12 B2 N2 O2' _chemical_formula_sum 'C12 H12 B2 N2 O2' _chemical_formula_weight 237.86 _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yac' _space_group_name_H-M_alt 'P 1 2/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-03-03 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335) ; _audit_update_record ; 2020-08-19 deposited with the CCDC. 2021-08-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.040(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.0331(6) _cell_length_b 5.0718(3) _cell_length_c 15.8131(8) _cell_measurement_reflns_used 2387 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.99 _cell_measurement_theta_min 2.76 _cell_volume 1125.29(10) _computing_cell_refinement 'SAINT V8.40A (?, 2016)' _computing_data_reduction 'SAINT V8.40A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 120.0 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_unetI/netI 0.0497 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9851 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.265 _diffrn_reflns_theta_min 2.334 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_correction_T_min 0.6353 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0736 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8514. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear light white' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.404 _exptl_crystal_description block _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.284 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2790 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0482 _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/[\s^2^(Fo^2^)+(0.0426P)^2^+0.4979P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.1204 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1961 _reflns_number_total 2790 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03765j4.cif _cod_data_source_block 1 _cod_database_code 1564369 _shelx_shelxl_version_number 2016/6 _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_max 0.991 _shelx_estimated_absorpt_t_min 0.986 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2.a Rotating group: N1(H1A) 2.b Aromatic/amide H refined with riding coordinates: C5(H5), C2(H2B), C3(H3), C4(H4) ; _shelx_res_file ; TITL 1_a.res in P2/n 1.res created by SHELXL-2016/6 at 11:08:34 on 03-Mar-2020 REM Old TITL 1 in P2/n REM SHELXT solution in P2/n REM R1 0.125, Rweak 0.002, Alpha 0.020, Orientation as input REM Formula found by SHELXT: C14 N2 O2 CELL 0.71073 15.0331 5.0718 15.8131 90 111.04 90 ZERR 4 0.0006 0.0003 0.0008 0 0.002 0 LATT 1 SYMM 0.5-X,+Y,0.5-Z SFAC C H B N O UNIT 48 48 8 8 8 L.S. 40 PLAN 20 SIZE 0.15 0.15 0.1 TEMP -153.15 BOND $H list 4 fmap 2 acta SHEL 999 0.75 REM REM REM WGHT 0.042600 0.497900 FVAR 0.67792 O1 5 0.727131 0.122580 0.362646 11.00000 0.02013 0.01810 = 0.02127 -0.00194 0.00892 -0.00054 O2 5 0.881760 0.244420 0.368406 11.00000 0.02341 0.02204 = 0.02699 -0.00158 0.01313 -0.00189 N2 4 0.648623 0.360956 0.446792 11.00000 0.01861 0.01938 = 0.02484 -0.00269 0.00904 0.00017 N1 4 0.620678 -0.229068 0.234138 11.00000 0.02727 0.02171 = 0.02474 -0.00627 0.01376 -0.00276 AFIX 7 H1A 2 0.616547 -0.382255 0.206636 11.00000 -1.20000 AFIX 0 C12 1 0.806581 0.506413 0.461942 11.00000 0.02170 0.01562 = 0.01967 0.00337 0.00718 0.00149 C6 1 0.559432 -0.031335 0.344333 11.00000 0.02030 0.01631 = 0.01921 0.00268 0.00740 0.00197 C8 1 0.723317 0.720412 0.549924 11.00000 0.02398 0.02066 = 0.02307 -0.00080 0.00834 0.00270 C7 1 0.725962 0.530894 0.486832 11.00000 0.02114 0.01589 = 0.01898 0.00192 0.00502 0.00007 C11 1 0.882644 0.680222 0.501141 11.00000 0.02053 0.01931 = 0.02371 0.00377 0.00646 0.00174 C1 1 0.551150 -0.215075 0.274799 11.00000 0.02185 0.01836 = 0.01894 0.00459 0.00828 0.00210 C5 1 0.484886 -0.029433 0.378192 11.00000 0.02565 0.02216 = 0.02470 -0.00257 0.01149 -0.00047 AFIX 43 H5 2 0.487893 0.092886 0.424638 11.00000 -1.20000 AFIX 0 C10 1 0.879822 0.871099 0.562766 11.00000 0.02156 0.01838 = 0.02250 0.00025 0.00045 -0.00139 C9 1 0.800044 0.887956 0.587586 11.00000 0.02797 0.01917 = 0.02217 -0.00303 0.00518 0.00256 C2 1 0.471942 -0.380772 0.241911 11.00000 0.02749 0.01937 = 0.01987 -0.00171 0.00596 -0.00133 AFIX 43 H2B 2 0.466718 -0.499647 0.193932 11.00000 -1.20000 AFIX 0 C3 1 0.401138 -0.373800 0.278327 11.00000 0.02236 0.02483 = 0.02703 0.00046 0.00617 -0.00411 AFIX 43 H3 2 0.348220 -0.489976 0.256246 11.00000 -1.20000 AFIX 0 C4 1 0.407276 -0.197234 0.347122 11.00000 0.02402 0.02911 = 0.03248 -0.00124 0.01415 -0.00401 AFIX 43 H4 2 0.358884 -0.191502 0.372583 11.00000 -1.20000 AFIX 0 B2 3 0.807049 0.282205 0.395850 11.00000 0.02062 0.01707 = 0.01796 0.00287 0.00663 0.00119 B1 3 0.647185 0.155166 0.385851 11.00000 0.02026 0.01725 = 0.01931 0.00254 0.00783 0.00095 H1B 2 0.679074 -0.191999 0.272645 11.00000 0.03474 H11 2 0.939354 0.663015 0.484735 11.00000 0.02433 H2A 2 0.596831 0.396512 0.461546 11.00000 0.03106 H8 2 0.665817 0.728111 0.566644 11.00000 0.03209 H9 2 0.797089 1.021731 0.632080 11.00000 0.02866 H10 2 0.934082 0.986763 0.590892 11.00000 0.03387 H2 2 0.878168 0.089814 0.335943 11.00000 0.06274 HKLF 4 REM 1_a.res in P2/n REM R1 = 0.0482 for 1961 Fo > 4sig(Fo) and 0.0792 for all 2790 data REM 192 parameters refined using 0 restraints END WGHT 0.0426 0.4998 REM Highest difference peak 0.284, deepest hole -0.226, 1-sigma level 0.051 Q1 1 0.8025 0.4377 0.4199 11.00000 0.05 0.28 Q2 1 0.6140 0.0072 0.3740 11.00000 0.05 0.22 Q3 1 0.7203 0.6517 0.5081 11.00000 0.05 0.22 Q4 1 0.4347 -0.0491 0.3469 11.00000 0.05 0.21 Q5 1 0.5624 -0.1481 0.3202 11.00000 0.05 0.21 Q6 1 0.6823 0.4646 0.4563 11.00000 0.05 0.21 Q7 1 0.5277 -0.0292 0.3587 11.00000 0.05 0.21 Q8 1 0.7653 0.5185 0.4739 11.00000 0.05 0.20 Q9 1 0.8379 0.8672 0.5725 11.00000 0.05 0.20 Q10 1 0.7739 0.7495 0.5919 11.00000 0.05 0.20 Q11 1 0.3860 -0.2361 0.2958 11.00000 0.05 0.19 Q12 1 0.8786 0.8330 0.5109 11.00000 0.05 0.19 Q13 1 0.8528 0.5324 0.4948 11.00000 0.05 0.19 Q14 1 0.8262 0.6247 0.4552 11.00000 0.05 0.19 Q15 1 0.5407 -0.0797 0.2898 11.00000 0.05 0.19 Q16 1 0.5219 -0.3447 0.2755 11.00000 0.05 0.18 Q17 1 0.4816 0.5728 0.4421 11.00000 0.05 0.18 Q18 1 0.7600 0.8355 0.5554 11.00000 0.05 0.17 Q19 1 0.5250 -0.5162 0.3387 11.00000 0.05 0.17 Q20 1 0.6062 0.2007 0.5268 11.00000 0.05 0.17 ; _shelx_res_checksum 5560 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, 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 0.72713(7) 0.1226(2) 0.36265(7) 0.0194(3) Uani 1 1 d . . . . . O2 O 0.88176(8) 0.2444(2) 0.36841(8) 0.0230(3) Uani 1 1 d . . . . . N2 N 0.64862(10) 0.3610(3) 0.44679(9) 0.0206(3) Uani 1 1 d . . . . . N1 N 0.62068(11) -0.2291(3) 0.23414(10) 0.0234(3) Uani 1 1 d . . . . . H1A H 0.616547 -0.382255 0.206636 0.028 Uiso 1 1 d GR . . . . C12 C 0.80658(11) 0.5064(3) 0.46194(11) 0.0191(3) Uani 1 1 d . . . . . C6 C 0.55943(11) -0.0313(3) 0.34433(10) 0.0185(3) Uani 1 1 d . . . . . C8 C 0.72332(12) 0.7204(3) 0.54992(11) 0.0226(4) Uani 1 1 d . . . . . C7 C 0.72596(11) 0.5309(3) 0.48683(11) 0.0193(3) Uani 1 1 d . . . . . C11 C 0.88264(11) 0.6802(3) 0.50114(11) 0.0216(4) Uani 1 1 d . . . . . C1 C 0.55115(11) -0.2151(3) 0.27480(11) 0.0195(3) Uani 1 1 d . . . . . C5 C 0.48489(11) -0.0294(3) 0.37819(11) 0.0235(4) Uani 1 1 d . . . . . H5 H 0.487893 0.092886 0.424638 0.028 Uiso 1 1 calc R . . . . C10 C 0.87982(12) 0.8711(3) 0.56277(11) 0.0229(4) Uani 1 1 d . . . . . C9 C 0.80004(12) 0.8880(4) 0.58759(12) 0.0242(4) Uani 1 1 d . . . . . C2 C 0.47194(11) -0.3808(3) 0.24191(11) 0.0229(4) Uani 1 1 d . . . . . H2B H 0.466718 -0.499647 0.193932 0.028 Uiso 1 1 calc R . . . . C3 C 0.40114(12) -0.3738(4) 0.27833(12) 0.0255(4) Uani 1 1 d . . . . . H3 H 0.348220 -0.489976 0.256246 0.031 Uiso 1 1 calc R . . . . C4 C 0.40728(12) -0.1972(4) 0.34712(12) 0.0274(4) Uani 1 1 d . . . . . H4 H 0.358884 -0.191502 0.372583 0.033 Uiso 1 1 calc R . . . . B2 B 0.80705(13) 0.2822(4) 0.39585(12) 0.0186(4) Uani 1 1 d . . . . . B1 B 0.64718(12) 0.1552(4) 0.38585(12) 0.0187(4) Uani 1 1 d . . . . . H1B H 0.6791(14) -0.192(4) 0.2726(14) 0.035(6) Uiso 1 1 d . . . . . H11 H 0.9394(12) 0.663(4) 0.4847(12) 0.024(5) Uiso 1 1 d . . . . . H2A H 0.5968(13) 0.397(4) 0.4615(13) 0.031(5) Uiso 1 1 d . . . . . H8 H 0.6658(14) 0.728(4) 0.5666(12) 0.032(5) Uiso 1 1 d . . . . . H9 H 0.7971(12) 1.022(4) 0.6321(12) 0.029(5) Uiso 1 1 d . . . . . H10 H 0.9341(14) 0.987(4) 0.5909(13) 0.034(5) Uiso 1 1 d . . . . . H2 H 0.8782(16) 0.090(5) 0.3359(17) 0.063(8) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0201(6) 0.0181(6) 0.0213(6) -0.0019(5) 0.0089(5) -0.0005(5) O2 0.0234(6) 0.0220(7) 0.0270(6) -0.0016(5) 0.0131(5) -0.0019(5) N2 0.0186(7) 0.0194(7) 0.0248(7) -0.0027(6) 0.0090(6) 0.0002(6) N1 0.0273(8) 0.0217(8) 0.0247(8) -0.0063(6) 0.0138(6) -0.0028(6) C12 0.0217(8) 0.0156(8) 0.0197(8) 0.0034(6) 0.0072(7) 0.0015(6) C6 0.0203(8) 0.0163(8) 0.0192(8) 0.0027(6) 0.0074(6) 0.0020(6) C8 0.0240(9) 0.0207(9) 0.0231(8) -0.0008(7) 0.0083(7) 0.0027(7) C7 0.0211(8) 0.0159(8) 0.0190(8) 0.0019(6) 0.0050(6) 0.0001(6) C11 0.0205(8) 0.0193(9) 0.0237(8) 0.0038(7) 0.0065(7) 0.0017(7) C1 0.0219(8) 0.0184(8) 0.0189(8) 0.0046(7) 0.0083(6) 0.0021(6) C5 0.0257(8) 0.0222(9) 0.0247(9) -0.0026(7) 0.0115(7) -0.0005(7) C10 0.0216(8) 0.0184(9) 0.0225(8) 0.0003(7) 0.0005(7) -0.0014(7) C9 0.0280(9) 0.0192(9) 0.0222(8) -0.0030(7) 0.0052(7) 0.0026(7) C2 0.0275(9) 0.0194(9) 0.0199(8) -0.0017(7) 0.0060(7) -0.0013(7) C3 0.0224(8) 0.0248(9) 0.0270(9) 0.0005(7) 0.0062(7) -0.0041(7) C4 0.0240(9) 0.0291(10) 0.0325(10) -0.0012(8) 0.0142(8) -0.0040(7) B2 0.0206(9) 0.0171(9) 0.0180(9) 0.0029(7) 0.0066(7) 0.0012(7) B1 0.0203(9) 0.0173(9) 0.0193(9) 0.0025(7) 0.0078(7) 0.0010(7) 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' 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 B2 O1 B1 123.08(13) . . ? B2 O2 H2 114.0(14) . . ? C7 N2 B1 124.62(14) . . ? C7 N2 H2A 114.2(12) . . ? B1 N2 H2A 121.1(12) . . ? H1A N1 H1B 113.6 . . ? C1 N1 H1A 109.7 . . ? C1 N1 H1B 112.8(13) . . ? C7 C12 B2 117.85(14) . . ? C11 C12 C7 117.97(15) . . ? C11 C12 B2 124.14(14) . . ? C1 C6 B1 123.46(14) . . ? C5 C6 C1 116.22(15) . . ? C5 C6 B1 120.27(14) . . ? C7 C8 H8 118.0(11) . . ? C9 C8 C7 119.82(15) . . ? C9 C8 H8 122.2(11) . . ? N2 C7 C12 118.49(14) . . ? C8 C7 N2 120.93(14) . . ? C8 C7 C12 120.58(15) . . ? C12 C11 H11 118.5(11) . . ? C10 C11 C12 121.68(15) . . ? C10 C11 H11 119.9(11) . . ? N1 C1 C6 120.99(14) . . ? C2 C1 N1 118.15(15) . . ? C2 C1 C6 120.80(14) . . ? C6 C5 H5 118.4 . . ? C4 C5 C6 123.14(16) . . ? C4 C5 H5 118.4 . . ? C11 C10 C9 119.24(16) . . ? C11 C10 H10 120.7(11) . . ? C9 C10 H10 120.0(11) . . ? C8 C9 C10 120.70(16) . . ? C8 C9 H9 118.9(10) . . ? C10 C9 H9 120.4(11) . . ? C1 C2 H2B 119.6 . . ? C3 C2 C1 120.75(16) . . ? C3 C2 H2B 119.6 . . ? C2 C3 H3 120.0 . . ? C2 C3 C4 119.99(16) . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.07(15) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? O1 B2 C12 118.16(14) . . ? O2 B2 O1 120.09(15) . . ? O2 B2 C12 121.73(15) . . ? O1 B1 N2 117.72(15) . . ? O1 B1 C6 119.84(15) . . ? N2 B1 C6 122.44(14) . . ? 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 O1 B2 1.386(2) . ? O1 B1 1.3867(19) . ? O2 B2 1.355(2) . ? O2 H2 0.93(3) . ? N2 C7 1.402(2) . ? N2 B1 1.415(2) . ? N2 H2A 0.908(19) . ? N1 H1A 0.8816 . ? N1 C1 1.4119(19) . ? N1 H1B 0.89(2) . ? C12 C7 1.408(2) . ? C12 C11 1.400(2) . ? C12 B2 1.546(2) . ? C6 C1 1.412(2) . ? C6 C5 1.405(2) . ? C6 B1 1.563(2) . ? C8 C7 1.396(2) . ? C8 C9 1.383(2) . ? C8 H8 0.991(19) . ? C11 C10 1.385(2) . ? C11 H11 0.980(17) . ? C1 C2 1.396(2) . ? C5 H5 0.9500 . ? C5 C4 1.384(2) . ? C10 C9 1.392(2) . ? C10 H10 0.97(2) . ? C9 H9 0.990(19) . ? C2 H2B 0.9500 . ? C2 C3 1.381(2) . ? C3 H3 0.9500 . ? C3 C4 1.386(2) . ? C4 H4 0.9500 . ?