#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:54 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247595.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_7247595 loop_ _publ_author_name 'Kawahata, Masatoshi' 'Yamamoto, Haruka' 'Tominaga, Masahide' 'Yamaguchi, Kentaro' _publ_section_title ; Multiple intermolecular interactions in guest inclusion by acyclic host compounds ; _journal_issue 44 _journal_name_full CrystEngComm _journal_page_first 6137 _journal_page_last 6143 _journal_paper_doi 10.1039/D3CE00775H _journal_volume 25 _journal_year 2023 _chemical_formula_sum 'C22 H22 N2 O6' _chemical_formula_weight 410.41 _space_group_crystal_system orthorhombic _space_group_IT_number 63 _space_group_name_Hall '-C 2c 2' _space_group_name_H-M_alt 'C m c m' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-06-06 deposited with the CCDC. 2023-10-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.6173(6) _cell_length_b 13.6049(11) _cell_length_c 20.3294(17) _cell_measurement_reflns_used 9043 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 78.10 _cell_measurement_theta_min 6.86 _cell_volume 1830.2(3) _computing_cell_refinement 'SAINT (Bruker AXS, 2015)' _computing_data_collection 'APEX3 (Bruker AXS, 2015)' _computing_data_reduction 'SAINT (Bruker AXS, 2015)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXLE (H\"ubschle et al., 2011)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.24 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'BrukerD8 goniometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0173 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 11088 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 78.085 _diffrn_reflns_theta_min 6.863 _diffrn_source 'rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_correction_T_min 0.8526 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.489 _exptl_crystal_description prismatic _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.246 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1079 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0389 _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^)+(0.0624P)^2^+1.1549P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.1149 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1028 _reflns_number_total 1079 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00775h2.cif _cod_data_source_block 2a _cod_depositor_comments 'Adding full bibliography for 7247591--7247596.cif.' _cod_database_code 7247595 _shelx_shelxl_version_number 2018/3 _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 0.915 _shelx_estimated_absorpt_t_max 0.931 _shelx_res_file ; TITL dom1_cmcm_a.res in Cmcm v181130_tom1.res created by SHELXL-2018/3 at 07:29:55 on 08-Dec-2022 REM Old TITL dom1_cmcm in Cmcm REM SHELXT solution in Cmcm: R1 0.179, Rweak 0.004, Alpha 0.027 REM 0.691 for 47 systematic absences, Orientation as input REM Formula found by SHELXT: C12 O3 CELL 1.54178 6.6173 13.6049 20.3294 90.000 90.000 90.000 ZERR 4.000 0.0006 0.0011 0.0017 0.000 0.000 0.000 LATT 7 SYMM -X, -Y, 1/2+Z SYMM -X, Y, 1/2-Z SYMM X, -Y, -Z SFAC C H N O UNIT 88 88 8 24 TEMP -173.000 SIZE 0.08 0.10 0.10 REM yellow prismatic L.S. 10 ACTA CONF WPDB -2 BOND $H LIST 4 FMAP 2 PLAN 10 WGHT 0.062400 1.154900 FVAR 0.48255 C1 1 0.500000 0.649049 0.687321 10.50000 0.04177 0.01971 = 0.01171 0.00041 0.00000 0.00000 C2 1 0.310144 0.582905 0.688462 11.00000 0.04593 0.02710 = 0.01364 0.00012 -0.00163 -0.00528 AFIX 23 H2A 2 0.187232 0.624390 0.688432 11.00000 -1.20000 H2B 2 0.307462 0.541210 0.648560 11.00000 -1.20000 AFIX 0 C3 1 0.311562 0.517526 0.750000 10.50000 0.05648 0.02582 = 0.01524 0.00000 0.00000 -0.01174 AFIX 13 H3 2 0.188295 0.475005 0.749999 10.50000 -1.20000 AFIX 0 C4 1 0.500000 0.452451 0.750000 10.25000 0.07678 0.02010 = 0.01501 0.00000 0.00000 0.00000 AFIX 23 H4A 2 0.500000 0.409815 0.789463 10.25000 -1.20000 H4B 2 0.499999 0.409815 0.710537 10.25000 -1.20000 AFIX 0 C5 1 0.500000 0.712352 0.750000 10.25000 0.04170 0.01913 = 0.01371 0.00000 0.00000 0.00000 AFIX 23 H5A 2 0.620974 0.755166 0.750000 10.25000 -1.20000 H5B 2 0.379026 0.755166 0.750000 10.25000 -1.20000 AFIX 0 C6 1 0.500000 0.712342 0.625288 10.50000 0.03801 0.02169 = 0.01491 0.00113 0.00000 0.00000 C7 1 0.500000 0.667616 0.564056 10.50000 0.03906 0.01966 = 0.01661 0.00101 0.00000 0.00000 AFIX 43 H7 2 0.500000 0.597922 0.561166 10.50000 -1.20000 AFIX 0 C8 1 0.500000 0.723618 0.506656 10.50000 0.03914 0.02278 = 0.01502 -0.00079 0.00000 0.00000 C9 1 0.500000 0.826980 0.508156 10.50000 0.03999 0.02278 = 0.01713 0.00413 0.00000 0.00000 C10 1 0.500000 0.871707 0.569698 10.50000 0.04956 0.01838 = 0.02204 0.00132 0.00000 0.00000 AFIX 43 H10 2 0.500000 0.941386 0.572744 10.50000 -1.20000 AFIX 0 C11 1 0.500000 0.815815 0.626400 10.50000 0.04765 0.02313 = 0.01608 -0.00215 0.00000 0.00000 AFIX 43 H11 2 0.500000 0.848418 0.667724 10.50000 -1.20000 AFIX 0 N1 3 0.500000 0.671410 0.444400 10.50000 0.04674 0.02404 = 0.01470 0.00080 0.00000 0.00000 O1 4 0.500000 0.581919 0.444288 10.50000 0.07571 0.02069 = 0.01947 -0.00160 0.00000 0.00000 O2 4 0.500000 0.720155 0.392448 10.50000 0.06183 0.02909 = 0.01401 0.00394 0.00000 0.00000 O3 4 0.500000 0.885284 0.454548 10.50000 0.06071 0.02200 = 0.01728 0.00468 0.00000 0.00000 H1 2 0.500000 0.840388 0.420516 10.50000 -1.50000 HKLF 4 REM dom1_cmcm_a.res in Cmcm REM wR2 = 0.1149, GooF = S = 1.101, Restrained GooF = 1.101 for all data REM R1 = 0.0389 for 1028 Fo > 4sig(Fo) and 0.0403 for all 1079 data REM 92 parameters refined using 0 restraints END WGHT 0.0624 1.1549 REM Highest difference peak 0.246, deepest hole -0.217, 1-sigma level 0.047 Q1 1 0.5000 0.6827 0.6581 10.50000 0.05 0.25 Q2 1 0.5000 0.7733 0.5062 10.50000 0.05 0.24 Q3 1 0.3796 0.6321 0.6895 11.00000 0.05 0.22 Q4 1 0.6507 0.8862 0.4546 11.00000 0.05 0.22 Q5 1 0.3113 0.5500 0.7782 11.00000 0.05 0.21 Q6 1 0.3630 0.4687 0.7500 10.50000 0.05 0.21 Q7 1 0.5000 0.6987 0.5385 10.50000 0.05 0.21 Q8 1 0.5000 0.8407 0.5972 10.50000 0.05 0.20 Q9 1 0.5000 0.6816 0.7194 10.50000 0.05 0.19 Q10 1 0.5000 0.8437 0.5405 10.50000 0.05 0.19 ; _shelx_res_checksum 43754 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.500000 0.64905(11) 0.68732(7) 0.0244(4) Uani 1 2 d S T P . . C2 C 0.3101(2) 0.58290(8) 0.68846(5) 0.0289(3) Uani 1 1 d . . . . . H2A H 0.187232 0.624390 0.688432 0.035 Uiso 1 1 calc R U . . . H2B H 0.307462 0.541210 0.648560 0.035 Uiso 1 1 calc R U . . . C3 C 0.3116(3) 0.51753(11) 0.750000 0.0325(4) Uani 1 2 d S T P . . H3 H 0.188295 0.475005 0.749999 0.039 Uiso 1 2 calc R U P . . C4 C 0.500000 0.45245(16) 0.750000 0.0373(6) Uani 1 4 d S T P . . H4A H 0.500000 0.409815 0.789463 0.045 Uiso 0.5 2 calc R U P . . H4B H 0.499999 0.409815 0.710537 0.045 Uiso 0.5 2 calc R U P . . C5 C 0.500000 0.71235(15) 0.750000 0.0248(5) Uani 1 4 d S T P . . H5A H 0.620974 0.755166 0.750000 0.030 Uiso 0.5 2 calc R U P . . H5B H 0.379026 0.755166 0.750000 0.030 Uiso 0.5 2 calc R U P . . C6 C 0.500000 0.71234(11) 0.62529(7) 0.0249(4) Uani 1 2 d S T P . . C7 C 0.500000 0.66762(11) 0.56406(7) 0.0251(4) Uani 1 2 d S T P . . H7 H 0.500000 0.597922 0.561166 0.030 Uiso 1 2 calc R U P . . C8 C 0.500000 0.72362(10) 0.50666(8) 0.0256(4) Uani 1 2 d S T P . . C9 C 0.500000 0.82698(11) 0.50816(7) 0.0266(4) Uani 1 2 d S T P . . C10 C 0.500000 0.87171(11) 0.56970(8) 0.0300(4) Uani 1 2 d S T P . . H10 H 0.500000 0.941386 0.572744 0.036 Uiso 1 2 calc R U P . . C11 C 0.500000 0.81581(11) 0.62640(8) 0.0290(4) Uani 1 2 d S T P . . H11 H 0.500000 0.848418 0.667724 0.035 Uiso 1 2 calc R U P . . N1 N 0.500000 0.67141(10) 0.44440(6) 0.0285(3) Uani 1 2 d S T P . . O1 O 0.500000 0.58192(8) 0.44429(6) 0.0386(4) Uani 1 2 d S T P . . O2 O 0.500000 0.72016(8) 0.39245(5) 0.0350(3) Uani 1 2 d S T P . . O3 O 0.500000 0.88528(8) 0.45455(6) 0.0333(3) Uani 1 2 d S T P . . H1 H 0.500000 0.8404(19) 0.4205(12) 0.050 Uiso 1 2 d S U P . . 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 C1 0.0418(9) 0.0197(7) 0.0117(7) 0.0004(5) 0.000 0.000 C2 0.0459(7) 0.0271(6) 0.0136(5) 0.0001(3) -0.0016(4) -0.0053(5) C3 0.0565(11) 0.0258(7) 0.0152(7) 0.000 0.000 -0.0117(7) C4 0.0768(19) 0.0201(10) 0.0150(10) 0.000 0.000 0.000 C5 0.0417(12) 0.0191(9) 0.0137(9) 0.000 0.000 0.000 C6 0.0380(8) 0.0217(7) 0.0149(7) 0.0011(5) 0.000 0.000 C7 0.0391(8) 0.0197(7) 0.0166(7) 0.0010(5) 0.000 0.000 C8 0.0391(9) 0.0228(8) 0.0150(7) -0.0008(5) 0.000 0.000 C9 0.0400(8) 0.0228(8) 0.0171(7) 0.0041(5) 0.000 0.000 C10 0.0496(10) 0.0184(7) 0.0220(8) 0.0013(6) 0.000 0.000 C11 0.0477(9) 0.0231(8) 0.0161(7) -0.0021(6) 0.000 0.000 N1 0.0467(8) 0.0240(7) 0.0147(6) 0.0008(5) 0.000 0.000 O1 0.0757(10) 0.0207(6) 0.0195(6) -0.0016(4) 0.000 0.000 O2 0.0618(8) 0.0291(6) 0.0140(5) 0.0039(4) 0.000 0.000 O3 0.0607(8) 0.0220(6) 0.0173(6) 0.0047(4) 0.000 0.000 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' 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 C6 C1 C5 111.62(12) . . ? C6 C1 C2 109.92(7) . . ? C5 C1 C2 108.28(8) . . ? C6 C1 C2 109.92(7) . 12_655 ? C5 C1 C2 108.28(8) . 12_655 ? C2 C1 C2 108.75(13) . 12_655 ? C3 C2 C1 110.16(10) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 109.90(10) . 10_557 ? C4 C3 C2 109.90(10) . . ? C2 C3 C2 109.17(12) 10_557 . ? C4 C3 H3 109.3 . . ? C2 C3 H3 109.3 10_557 . ? C2 C3 H3 109.3 . . ? C3 C4 C3 109.25(18) 3_656 . ? C3 C4 H4A 109.8 3_656 . ? C3 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 3_656 . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C1 C5 C1 111.89(16) 10_557 . ? C1 C5 H5A 109.2 10_557 . ? C1 C5 H5A 109.2 . . ? C1 C5 H5B 109.2 10_557 . ? C1 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C11 116.97(13) . . ? C7 C6 C1 119.62(13) . . ? C11 C6 C1 123.41(13) . . ? C6 C7 C8 120.81(14) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C9 121.90(13) . . ? C7 C8 N1 117.56(13) . . ? C9 C8 N1 120.54(13) . . ? O3 C9 C10 118.01(14) . . ? O3 C9 C8 124.81(14) . . ? C10 C9 C8 117.18(14) . . ? C11 C10 C9 120.65(14) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 122.49(14) . . ? C10 C11 H11 118.8 . . ? C6 C11 H11 118.8 . . ? O1 N1 O2 122.02(13) . . ? O1 N1 C8 119.41(12) . . ? O2 N1 C8 118.57(13) . . ? C9 O3 H1 102.5(16) . . ? 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 C6 1.5270(19) . ? C1 C5 1.5380(17) . ? C1 C2 1.5455(15) . ? C1 C2 1.5456(15) 12_655 ? C2 C3 1.5350(13) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.529(2) . ? C3 H3 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.386(2) . ? C6 C11 1.408(2) . ? C7 C8 1.394(2) . ? C7 H7 0.9500 . ? C8 C9 1.407(2) . ? C8 N1 1.4513(18) . ? C9 O3 1.3479(17) . ? C9 C10 1.391(2) . ? C10 C11 1.381(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N1 O1 1.2175(18) . ? N1 O2 1.2471(17) . ? O3 H1 0.92(3) . ? 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 C6 C1 C2 C3 178.81(10) . . . . ? C5 C1 C2 C3 -59.02(13) . . . . ? C2 C1 C2 C3 58.43(14) 12_655 . . . ? C1 C2 C3 C4 -59.87(13) . . . . ? C1 C2 C3 C2 60.74(17) . . . 10_557 ? C2 C3 C4 C3 -60.09(9) 10_557 . . 3_656 ? C2 C3 C4 C3 60.08(9) . . . 3_656 ? C6 C1 C5 C1 180.000(0) . . . 10_557 ? C2 C1 C5 C1 58.88(8) . . . 10_557 ? C2 C1 C5 C1 -58.88(8) 12_655 . . 10_557 ? C5 C1 C6 C7 180.000(1) . . . . ? C2 C1 C6 C7 -59.84(8) . . . . ? C2 C1 C6 C7 59.84(8) 12_655 . . . ? C5 C1 C6 C11 0.000(1) . . . . ? C2 C1 C6 C11 120.16(8) . . . . ? C2 C1 C6 C11 -120.16(8) 12_655 . . . ? C11 C6 C7 C8 0.000(1) . . . . ? C1 C6 C7 C8 180.000(1) . . . . ? C6 C7 C8 C9 0.000(1) . . . . ? C6 C7 C8 N1 180.000(1) . . . . ? C7 C8 C9 O3 180.000(1) . . . . ? N1 C8 C9 O3 0.000(1) . . . . ? C7 C8 C9 C10 0.000(1) . . . . ? N1 C8 C9 C10 180.000(1) . . . . ? O3 C9 C10 C11 180.000(1) . . . . ? C8 C9 C10 C11 0.000(1) . . . . ? C9 C10 C11 C6 0.000(1) . . . . ? C7 C6 C11 C10 0.000(1) . . . . ? C1 C6 C11 C10 180.000(1) . . . . ? C7 C8 N1 O1 0.000(1) . . . . ? C9 C8 N1 O1 180.000(1) . . . . ? C7 C8 N1 O2 180.000(1) . . . . ? C9 C8 N1 O2 0.000(1) . . . . ?