#------------------------------------------------------------------------------ #$Date: 2020-04-17 04:47:05 +0300 (Fri, 17 Apr 2020) $ #$Revision: 250878 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157470.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_7157470 loop_ _publ_author_name 'Gunnlaugsson, Thorfinnur' 'Scanlan, Eoin M.' 'Elena Calatrava-P\'erez, Elena' 'Achermann, Stefan' 'Stricker, Lucas' 'McManus, Gavin' 'Delente, Jason' 'Lynes, Amy Danielle' 'Henwood, Adam' 'Lovitt, June' 'Hawes, Chris Samuel' 'Byrne, Kevin' 'Schmitt, Wolfgang' 'Kotova, Oxana' _publ_section_title ; Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00033G _journal_year 2020 _chemical_formula_moiety 'C14 H10 Br N O2' _chemical_formula_sum 'C14 H10 Br N O2' _chemical_formula_weight 304.14 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-11-28 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-28 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.273(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.7872(9) _cell_length_b 11.4491(7) _cell_length_c 7.3967(5) _cell_measurement_reflns_used 3627 _cell_measurement_temperature 100 _cell_measurement_theta_max 51.05 _cell_measurement_theta_min 5.06 _cell_volume 1145.05(13) _computing_cell_refinement 'SAINT v8.38A (Bruker, 2016)' _computing_data_collection 'APEX 3 (Bruker, 2017) ' _computing_data_reduction 'SAINT v8.37A (Bruker, 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 99.99 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type APEX2 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'Kappa diffractometer' _diffrn_measurement_device_type 'Bruker APEX2 Kappa Duo' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'focusing mirrors' _diffrn_radiation_detector APEX2 _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 10189 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 51.851 _diffrn_reflns_theta_max 51.851 _diffrn_reflns_theta_min 3.268 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.837 _exptl_absorpt_correction_T_max 0.7503 _exptl_absorpt_correction_T_min 0.6205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0900 before and 0.0686 after correction. The Ratio of minimum to maximum transmission is 0.8270. The \l/2 correction factor is Not present. ; _exptl.absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). "Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination" J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _refine_diff_density_max 1.935 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.165 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 1274 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.179 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0957 _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^)+(0.0331P)^2^+33.4781P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2070 _refine_ls_wR_factor_ref 0.2110 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1130 _reflns_number_total 1274 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00033g2.cif _cod_data_source_block 6 _cod_database_code 7157470 _shelx_shelxl_version_number 2016/4 _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 0.794 _shelx_estimated_absorpt_t_min 0.445 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C10(H10), C11(H11) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL JIL046_6 in P2(1)/c jil046_6.res created by SHELXL-2016/4 at 11:30:09 on 28-Nov-2019 CELL 1.54178 13.7872 11.4491 7.3967 90 101.2732 90 ZERR 4 0.0009 0.0007 0.0005 0 0.0033 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 56 40 4 4 8 L.S. 20 0 0 PLAN 20 SIZE 0.11 0.2 0.05 TEMP -173.16 BOND $H list 4 fmap 2 53 acta REM REM REM WGHT 0.033100 33.478100 FVAR 0.11032 BR1 3 0.315561 -0.091103 0.497189 11.00000 0.04971 0.03680 = 0.05206 0.00301 0.01645 0.00972 O1 5 0.056574 0.418759 0.262323 11.00000 0.03555 0.04379 = 0.03900 0.00155 0.00369 0.00278 N1 4 0.203257 0.498537 0.386240 11.00000 0.03869 0.03403 = 0.05060 0.00570 0.01513 -0.00786 C1 1 0.116894 0.665498 0.494809 11.00000 0.06158 0.03566 = 0.04655 -0.00038 0.02219 0.00082 AFIX 137 H1A 2 0.083188 0.738909 0.453446 11.00000 -1.50000 H1B 2 0.168361 0.680150 0.604053 11.00000 -1.50000 H1C 2 0.068889 0.609475 0.525623 11.00000 -1.50000 AFIX 0 O2 5 0.348921 0.577753 0.523622 11.00000 0.04504 0.03826 = 0.04892 -0.01204 0.02096 -0.01128 C2 1 0.163794 0.615816 0.341772 11.00000 0.04542 0.02491 = 0.05258 0.00938 0.01609 0.01029 AFIX 23 H2A 2 0.113691 0.612940 0.226018 11.00000 -1.20000 H2B 2 0.217911 0.668007 0.321472 11.00000 -1.20000 AFIX 0 C3 1 0.302844 0.491079 0.483521 11.00000 0.03096 0.04229 = 0.01402 -0.01696 0.01041 -0.00475 C4 1 0.344354 0.370722 0.524013 11.00000 0.02292 0.04857 = 0.02864 0.00031 0.00522 -0.01062 C5 1 0.438349 0.359715 0.609205 11.00000 0.05220 0.02576 = 0.04373 0.00444 0.01782 -0.00054 AFIX 43 H5 2 0.477213 0.427861 0.641318 11.00000 -1.20000 AFIX 0 C6 1 0.480746 0.250603 0.652091 11.00000 0.03169 0.05353 = 0.04593 -0.00433 0.01126 -0.00530 AFIX 43 H6 2 0.547504 0.244844 0.715452 11.00000 -1.20000 AFIX 0 PART 1 C7 1 0.427136 0.152464 0.603789 11.00000 0.02763 0.05761 = 0.03216 0.01157 0.01015 0.00516 AFIX 43 H7 2 0.456546 0.078099 0.633371 11.00000 -1.20000 AFIX 0 PART 0 C8 1 0.325953 0.160024 0.507987 11.00000 0.04182 0.02580 = 0.02518 0.00721 0.01959 -0.00739 C9 1 0.263190 0.062319 0.456496 11.00000 0.04936 0.02737 = 0.03836 0.00618 0.02610 0.01112 C10 1 0.166667 0.074504 0.369334 11.00000 0.02890 0.03163 = 0.04567 -0.00294 0.00112 -0.00024 AFIX 43 H10 2 0.126933 0.007420 0.333928 11.00000 -1.20000 AFIX 0 C11 1 0.126828 0.186262 0.332657 11.00000 0.03333 0.03537 = 0.03748 -0.00748 0.01233 -0.01107 AFIX 43 H11 2 0.059373 0.194863 0.274709 11.00000 -1.20000 AFIX 0 C12 1 0.185433 0.285685 0.380544 11.00000 0.05383 0.01634 = 0.03618 -0.00409 0.02867 -0.00440 C13 1 0.141974 0.403548 0.335377 11.00000 0.02189 0.04337 = 0.03352 0.00046 0.00547 -0.00491 C14 1 0.281858 0.270951 0.471762 11.00000 0.02802 0.05757 = 0.02455 0.00513 0.01096 0.00570 HKLF 4 REM JIL046_6 in P2(1)/c REM R1 = 0.0957 for 1130 Fo > 4sig(Fo) and 0.1040 for all 1274 data REM 164 parameters refined using 0 restraints END WGHT 0.0332 33.4710 REM Highest difference peak 1.935, deepest hole -0.686, 1-sigma level 0.165 Q1 1 0.3902 -0.0404 0.5570 11.00000 0.05 1.93 Q2 1 0.3162 0.5870 0.7377 11.00000 0.05 1.58 Q3 1 0.3191 0.5832 0.2509 11.00000 0.05 0.93 Q4 1 0.3364 0.0853 0.7546 11.00000 0.05 0.57 Q5 1 0.0548 0.5851 0.5449 11.00000 0.05 0.49 Q6 1 0.1023 0.0863 0.2754 11.00000 0.05 0.47 Q7 1 0.0769 0.5140 0.0636 11.00000 0.05 0.47 Q8 1 0.3150 0.3382 0.7271 11.00000 0.05 0.46 Q9 1 0.3220 -0.1634 0.4988 11.00000 0.05 0.46 Q10 1 0.3559 0.0825 0.5291 11.00000 0.05 0.45 Q11 1 0.3986 0.2760 0.6064 11.00000 0.05 0.45 Q12 1 0.2854 0.4136 0.2411 11.00000 0.05 0.43 Q13 1 0.2134 -0.0225 0.4579 11.00000 0.05 0.42 Q14 1 0.2067 -0.0386 0.4225 11.00000 0.05 0.42 Q15 1 0.0239 0.7468 0.5445 11.00000 0.05 0.40 Q16 1 -0.0702 0.6039 0.4392 11.00000 0.05 0.40 Q17 1 0.2391 0.0256 0.2255 11.00000 0.05 0.40 Q18 1 0.2957 0.5780 0.4861 11.00000 0.05 0.39 Q19 1 0.0582 -0.0814 0.3370 11.00000 0.05 0.38 Q20 1 0.2625 0.1480 0.4622 11.00000 0.05 0.38 ; _shelx_res_checksum 10010 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Br1 Br 0.31556(13) -0.09110(14) 0.4972(2) 0.0453(7) Uani 1 1 d . . . . . O1 O 0.0566(7) 0.4188(9) 0.2623(13) 0.040(3) Uani 1 1 d . . . . . N1 N 0.2033(9) 0.4985(11) 0.3862(17) 0.040(3) Uani 1 1 d . . . . . C1 C 0.1169(12) 0.6655(14) 0.495(2) 0.046(4) Uani 1 1 d . . . . . H1A H 0.083188 0.738909 0.453446 0.070 Uiso 1 1 calc GR . . . . H1B H 0.168361 0.680150 0.604053 0.070 Uiso 1 1 calc GR . . . . H1C H 0.068889 0.609475 0.525623 0.070 Uiso 1 1 calc GR . . . . O2 O 0.3489(7) 0.5778(9) 0.5236(14) 0.042(3) Uani 1 1 d . . . . . C2 C 0.1638(12) 0.6158(12) 0.342(2) 0.040(4) Uani 1 1 d . . . . . H2A H 0.113691 0.612940 0.226018 0.048 Uiso 1 1 calc R . . . . H2B H 0.217911 0.668007 0.321472 0.048 Uiso 1 1 calc R . . . . C3 C 0.3028(10) 0.4911(13) 0.4835(18) 0.028(3) Uani 1 1 d . . . . . C4 C 0.3444(10) 0.3707(13) 0.5240(19) 0.033(4) Uani 1 1 d . . . . . C5 C 0.4383(12) 0.3597(13) 0.609(2) 0.039(4) Uani 1 1 d . . . . . H5 H 0.477213 0.427861 0.641318 0.047 Uiso 1 1 calc R . . . . C6 C 0.4807(11) 0.2506(15) 0.652(2) 0.043(4) Uani 1 1 d . . . . . H6 H 0.547504 0.244844 0.715452 0.052 Uiso 1 1 calc R . . A . C7 C 0.4271(10) 0.1525(15) 0.6038(19) 0.039(4) Uani 1 1 d . . . B 1 H7 H 0.456546 0.078099 0.633371 0.046 Uiso 1 1 calc R . . B 1 C8 C 0.3260(11) 0.1600(12) 0.5080(19) 0.029(3) Uani 1 1 d . . . . . C9 C 0.2632(11) 0.0623(12) 0.456(2) 0.036(4) Uani 1 1 d . . . . . C10 C 0.1667(10) 0.0745(13) 0.369(2) 0.036(4) Uani 1 1 d . . . . . H10 H 0.126933 0.007420 0.333928 0.043 Uiso 1 1 calc R . . . . C11 C 0.1268(11) 0.1863(13) 0.333(2) 0.035(4) Uani 1 1 d . . . . . H11 H 0.059373 0.194863 0.274709 0.042 Uiso 1 1 calc R . . . . C12 C 0.1854(11) 0.2857(12) 0.381(2) 0.033(4) Uani 1 1 d . . . . . C13 C 0.1420(10) 0.4035(13) 0.3354(19) 0.033(4) Uani 1 1 d . . . . . C14 C 0.2819(10) 0.2710(14) 0.4718(19) 0.036(4) Uani 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 Br1 0.0497(11) 0.0368(10) 0.0521(11) 0.0030(9) 0.0165(8) 0.0097(8) O1 0.036(6) 0.044(7) 0.039(6) 0.002(5) 0.004(5) 0.003(5) N1 0.039(8) 0.034(8) 0.051(8) 0.006(6) 0.015(7) -0.008(6) C1 0.062(11) 0.036(10) 0.047(10) 0.000(8) 0.022(8) 0.001(8) O2 0.045(7) 0.038(7) 0.049(7) -0.012(6) 0.021(5) -0.011(6) C2 0.045(9) 0.025(9) 0.053(10) 0.009(7) 0.016(8) 0.010(7) C3 0.031(9) 0.042(10) 0.014(7) -0.017(7) 0.010(6) -0.005(8) C4 0.023(9) 0.049(10) 0.029(8) 0.000(7) 0.005(7) -0.011(7) C5 0.052(11) 0.026(9) 0.044(9) 0.004(8) 0.018(8) -0.001(8) C6 0.032(9) 0.054(12) 0.046(10) -0.004(9) 0.011(8) -0.005(9) C7 0.028(9) 0.058(11) 0.032(9) 0.012(8) 0.010(7) 0.005(8) C8 0.042(9) 0.026(9) 0.025(8) 0.007(7) 0.020(7) -0.007(7) C9 0.049(10) 0.027(9) 0.038(9) 0.006(7) 0.026(8) 0.011(8) C10 0.029(9) 0.032(10) 0.046(9) -0.003(8) 0.001(7) 0.000(7) C11 0.033(8) 0.035(10) 0.037(9) -0.007(7) 0.012(7) -0.011(8) C12 0.054(11) 0.016(8) 0.036(9) -0.004(7) 0.029(8) -0.004(7) C13 0.022(9) 0.043(10) 0.034(8) 0.000(8) 0.005(7) -0.005(8) C14 0.028(9) 0.058(11) 0.025(8) 0.005(8) 0.011(7) 0.006(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C7a C6 C5 120.2(15) . . ? C7a C6 H6 119.9 . . ? C3 N1 C2 116.7(12) . . ? C13 N1 C2 118.7(12) . . ? C13 N1 C3 124.6(12) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? N1 C2 C1 111.7(12) . . ? N1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C1 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N1 C3 C4 116.7(13) . . ? O2 C3 N1 119.6(13) . . ? O2 C3 C4 123.7(13) . . ? C5 C4 C3 118.7(13) . . ? C5 C4 C14 121.9(14) . . ? C14 C4 C3 119.4(12) . . ? C4 C5 H5 119.3 . . ? C4 C5 C6 121.3(15) . . ? C6 C5 H5 119.3 . . ? C5 C6 H6 119.9 . . ? C9 C8 C7 124.5(14) . . ? C14 C8 C7 119.2(14) . . ? C14 C8 C9 116.2(13) . . ? C8 C9 Br1 119.5(11) . . ? C10 C9 Br1 118.3(12) . . ? C10 C9 C8 122.1(13) . . ? C9 C10 H10 120.2 . . ? C9 C10 C11 119.6(14) . . ? C11 C10 H10 120.2 . . ? C10 C11 H11 119.7 . . ? C10 C11 C12 120.6(14) . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 119.6(14) . . ? C14 C12 C11 118.5(14) . . ? C14 C12 C13 121.9(13) . . ? O1 C13 N1 119.9(14) . . ? O1 C13 C12 123.1(14) . . ? N1 C13 C12 117.0(12) . . ? C8 C14 C4 116.8(13) . . ? C12 C14 C4 120.3(14) . . ? C12 C14 C8 122.8(14) . . ? C6 C7a H7 119.8 . . ? C6 C7a C8 120.5(15) . . ? C8 C7a H7 119.8 . . ? 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 C7a H7 0.9500 . ? C7a C8 1.44(2) . ? Br1 C9 1.901(14) . ? O1 C13 1.208(16) . ? N1 C2 1.462(18) . ? N1 C3 1.423(18) . ? N1 C13 1.383(18) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.52(2) . ? O2 C3 1.184(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.50(2) . ? C4 C5 1.33(2) . ? C4 C14 1.44(2) . ? C5 H5 0.9500 . ? C5 C6 1.39(2) . ? C6 H6 0.9500 . ? C6 C7 1.35(2) . ? C8 C9 1.42(2) . ? C8 C14 1.41(2) . ? C9 C10 1.37(2) . ? C10 H10 0.9500 . ? C10 C11 1.40(2) . ? C11 H11 0.9500 . ? C11 C12 1.401(19) . ? C12 C13 1.49(2) . ? C12 C14 1.38(2) . ?