#------------------------------------------------------------------------------ #$Date: 2024-09-19 03:55:14 +0300 (Thu, 19 Sep 2024) $ #$Revision: 294792 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249351.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_7249351 loop_ _publ_author_name 'Heiner, Benjamin R.' 'Handy, Kaitlyn' 'Devlin, Angela' 'Soucek, Jewel' 'Pittsford, Alexander M.' 'Turner, David' 'Petersen, Jacob' 'Oliver, Allen Grayson' 'Corcelli, Steven A.' 'Kandel, S. Alex' _publ_section_title ; Enantiopure molecules form apparently racemic monolayers of chiral cyclic pentamers ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/D4CP02094D _journal_year 2024 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C9 H9 N O2' _chemical_formula_sum 'C9 H9 N O2' _chemical_formula_weight 163.17 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-05-17 deposited with the CCDC. 2024-09-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.824(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.3771(2) _cell_length_b 5.7567(2) _cell_length_c 12.4675(5) _cell_measurement_reflns_used 2671 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 70.31 _cell_measurement_theta_min 3.67 _cell_volume 377.73(2) _computing_cell_refinement 'Bruker SAINT (Bruker, 2015)' _computing_data_collection 'Bruker APEX-3 (Bruker, 2015)' _computing_data_reduction 'Bruker SAINT (Bruker, 2015)' _computing_molecular_graphics 'Bruker XP (Bruker, 2015)' _computing_publication_material 'CIFTAB (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 7.41 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker PHOTON-II' _diffrn_measurement_method 'combination of \w and \f-scans ' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_unetI/netI 0.0482 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5982 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.425 _diffrn_reflns_theta_min 3.622 _diffrn_source 'Incoatec micro-focus' _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8311 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS (Krause et al., 2015)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.435 _exptl_crystal_description plate _exptl_crystal_F_000 172 _exptl_crystal_size_max 0.118 _exptl_crystal_size_mid 0.091 _exptl_crystal_size_min 0.019 _refine_diff_density_max 0.277 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details ; Flack x determined using 530 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 1419 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0547P)^2^+0.0269P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0968 _refine_ls_wR_factor_ref 0.1000 _reflns_Friedel_coverage 0.787 _reflns_Friedel_fraction_full 0.976 _reflns_Friedel_fraction_max 0.969 _reflns_number_gt 1306 _reflns_number_total 1419 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cp02094d2.cif _cod_data_source_block dt2001 _cod_original_cell_volume 377.74(2) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7249351 _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 0.907 _shelx_estimated_absorpt_t_max 0.984 _diffrn_source_monochromator 'MONTEL Multi-layer' _shelx_res_file ; TITL dt2001 in P2(1) dt2001.res created by SHELXL-2018/3 at 11:32:43 on 21-Jul-2020 CELL 1.54178 5.37710 5.75670 12.46750 90.0000 101.8236 90.0000 ZERR 2.00 0.00020 0.00020 0.00050 0.0000 0.0029 0.0000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H N O UNIT 18 18 2 4 TEMP -153.170 SIZE 0.019 0.091 0.118 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 20 WPDB -2 EQIV $1 -x, y+1/2, -z+1 EQIV $2 x, y+1, z HTAB N1 O1 HTAB N1 O1_$1 HTAB N1 O2_$2 CONF ACTA WGHT 0.054700 0.026900 FVAR 0.55977 O1 4 0.134986 0.267129 0.536241 11.00000 0.02374 0.01767 = 0.03199 -0.00094 -0.00217 -0.00089 O2 4 0.505646 0.082986 0.595127 11.00000 0.02197 0.01686 = 0.02810 -0.00246 0.00598 0.00056 N1 3 0.297287 0.674712 0.620533 11.00000 0.01818 0.01729 = 0.02118 -0.00077 0.00276 -0.00151 H1NA 2 0.169583 0.633858 0.564703 11.00000 0.01784 H1NB 2 0.370980 0.798003 0.600102 11.00000 0.02833 C2 1 0.481309 0.473300 0.644906 11.00000 0.01681 0.01658 = 0.02433 0.00088 0.00347 0.00184 AFIX 13 H2 2 0.642167 0.511356 0.620216 11.00000 -1.20000 AFIX 0 C3 1 0.536174 0.441019 0.770844 11.00000 0.02259 0.01891 = 0.02663 -0.00213 0.00091 0.00309 AFIX 23 H3A 2 0.509817 0.277521 0.790479 11.00000 -1.20000 H3B 2 0.712605 0.487069 0.803936 11.00000 -1.20000 AFIX 0 C3A 1 0.347443 0.599092 0.808359 11.00000 0.01897 0.01752 = 0.02569 -0.00071 0.00079 -0.00298 C4 1 0.299732 0.631517 0.912759 11.00000 0.02586 0.02309 = 0.02537 0.00282 0.00026 0.00227 AFIX 43 H4 2 0.390361 0.546049 0.973542 11.00000 -1.20000 AFIX 0 C5 1 0.114393 0.793650 0.925730 11.00000 0.02821 0.02779 = 0.02426 -0.00190 0.00562 0.00014 AFIX 43 H5 2 0.078912 0.818687 0.996406 11.00000 -1.20000 AFIX 0 C6 1 -0.017678 0.917752 0.837625 11.00000 0.02403 0.02380 = 0.03306 -0.00172 0.00791 0.00351 AFIX 43 H6 2 -0.142740 1.026674 0.848699 11.00000 -1.20000 AFIX 0 C7 1 0.028795 0.886439 0.732737 11.00000 0.02055 0.01970 = 0.02630 0.00184 -0.00066 0.00091 AFIX 43 H7 2 -0.061548 0.970722 0.671488 11.00000 -1.20000 AFIX 0 C7A 1 0.213717 0.725872 0.722759 11.00000 0.01833 0.01699 = 0.02313 -0.00242 0.00229 -0.00502 C8 1 0.359242 0.255534 0.585370 11.00000 0.02050 0.01857 = 0.01914 0.00193 0.00556 -0.00324 HKLF 4 REM dt2001 in P2(1) REM wR2 = 0.1000, GooF = S = 1.091, Restrained GooF = 1.091 for all data REM R1 = 0.0408 for 1306 Fo > 4sig(Fo) and 0.0464 for all 1419 data REM 117 parameters refined using 1 restraints END WGHT 0.0546 0.0272 REM Highest difference peak 0.277, deepest hole -0.195, 1-sigma level 0.047 Q1 1 0.3361 0.7306 0.7746 11.00000 0.05 0.28 Q2 1 0.4608 0.5562 0.7967 11.00000 0.05 0.21 Q3 1 0.6156 0.4570 0.7001 11.00000 0.05 0.19 Q4 1 0.4260 0.1164 0.6317 11.00000 0.05 0.16 Q5 1 0.4402 0.3922 0.5936 11.00000 0.05 0.16 Q6 1 0.4090 0.6587 0.8692 11.00000 0.05 0.15 Q7 1 0.4187 0.5997 0.9632 11.00000 0.05 0.14 Q8 1 0.6309 0.1026 0.6658 11.00000 0.05 0.14 Q9 1 0.6286 0.0891 0.5427 11.00000 0.05 0.14 Q10 1 0.2157 0.5859 0.7569 11.00000 0.05 0.14 Q11 1 0.1081 0.8252 0.7261 11.00000 0.05 0.13 Q12 1 0.5750 0.5365 1.0631 11.00000 0.05 0.13 Q13 1 -0.2009 1.1991 0.8615 11.00000 0.05 0.13 Q14 1 0.1198 0.8741 0.8802 11.00000 0.05 0.13 Q15 1 0.4193 0.0549 0.5350 11.00000 0.05 0.12 Q16 1 0.0854 0.4043 0.5391 11.00000 0.05 0.12 Q17 1 -0.0174 0.7880 0.8727 11.00000 0.05 0.12 Q18 1 0.0353 0.7555 0.9946 11.00000 0.05 0.12 Q19 1 0.3021 0.5496 0.8770 11.00000 0.05 0.12 Q20 1 0.5867 -0.0728 0.5957 11.00000 0.05 0.12 ; _shelx_res_checksum 4381 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 O1 O 0.1350(4) 0.2671(4) 0.53624(19) 0.0256(5) Uani 1 1 d . . . . . O2 O 0.5056(4) 0.0830(4) 0.59513(18) 0.0222(5) Uani 1 1 d . . . . . N1 N 0.2973(5) 0.6747(4) 0.6205(2) 0.0191(6) Uani 1 1 d . . . . . H1NA H 0.170(7) 0.634(7) 0.565(3) 0.018(8) Uiso 1 1 d . . . . . H1NB H 0.371(8) 0.798(8) 0.600(3) 0.028(10) Uiso 1 1 d . . . . . C2 C 0.4813(5) 0.4733(5) 0.6449(2) 0.0193(6) Uani 1 1 d . . . . . H2 H 0.642167 0.511356 0.620216 0.023 Uiso 1 1 calc R U . . . C3 C 0.5362(6) 0.4410(5) 0.7708(3) 0.0233(7) Uani 1 1 d . . . . . H3A H 0.509817 0.277521 0.790479 0.028 Uiso 1 1 calc R U . . . H3B H 0.712605 0.487069 0.803936 0.028 Uiso 1 1 calc R U . . . C3A C 0.3474(5) 0.5991(5) 0.8084(2) 0.0213(6) Uani 1 1 d . . . . . C4 C 0.2997(6) 0.6315(5) 0.9128(3) 0.0255(7) Uani 1 1 d . . . . . H4 H 0.390361 0.546049 0.973542 0.031 Uiso 1 1 calc R U . . . C5 C 0.1144(6) 0.7936(6) 0.9257(3) 0.0267(7) Uani 1 1 d . . . . . H5 H 0.078912 0.818687 0.996406 0.032 Uiso 1 1 calc R U . . . C6 C -0.0177(6) 0.9178(5) 0.8376(3) 0.0267(7) Uani 1 1 d . . . . . H6 H -0.142740 1.026674 0.848699 0.032 Uiso 1 1 calc R U . . . C7 C 0.0288(6) 0.8864(5) 0.7327(3) 0.0230(7) Uani 1 1 d . . . . . H7 H -0.061548 0.970722 0.671488 0.028 Uiso 1 1 calc R U . . . C7A C 0.2137(5) 0.7259(5) 0.7228(2) 0.0198(6) Uani 1 1 d . . . . . C8 C 0.3592(5) 0.2555(5) 0.5854(2) 0.0192(6) 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 O1 0.0237(11) 0.0177(11) 0.0320(12) -0.0009(9) -0.0022(9) -0.0009(9) O2 0.0220(10) 0.0169(10) 0.0281(11) -0.0025(8) 0.0060(8) 0.0006(8) N1 0.0182(13) 0.0173(13) 0.0212(12) -0.0008(10) 0.0028(10) -0.0015(10) C2 0.0168(14) 0.0166(14) 0.0243(15) 0.0009(12) 0.0035(11) 0.0018(11) C3 0.0226(15) 0.0189(16) 0.0266(16) -0.0021(12) 0.0009(11) 0.0031(11) C3A 0.0190(13) 0.0175(15) 0.0257(15) -0.0007(12) 0.0008(11) -0.0030(12) C4 0.0259(16) 0.0231(17) 0.0254(16) 0.0028(13) 0.0003(12) 0.0023(13) C5 0.0282(17) 0.0278(18) 0.0243(15) -0.0019(12) 0.0056(12) 0.0001(13) C6 0.0240(16) 0.0238(18) 0.0331(17) -0.0017(13) 0.0079(13) 0.0035(12) C7 0.0206(15) 0.0197(15) 0.0263(16) 0.0018(13) -0.0007(11) 0.0009(12) C7A 0.0183(14) 0.0170(16) 0.0231(14) -0.0024(11) 0.0023(11) -0.0050(11) C8 0.0205(14) 0.0186(14) 0.0191(13) 0.0019(12) 0.0056(10) -0.0032(13) 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 C7A N1 C2 106.5(2) . . ? C7A N1 H1NA 114(2) . . ? C2 N1 H1NA 109(2) . . ? C7A N1 H1NB 109(3) . . ? C2 N1 H1NB 111(3) . . ? H1NA N1 H1NB 108(4) . . ? N1 C2 C8 109.4(2) . . ? N1 C2 C3 106.0(2) . . ? C8 C2 C3 111.5(2) . . ? N1 C2 H2 110.0 . . ? C8 C2 H2 110.0 . . ? C3 C2 H2 110.0 . . ? C3A C3 C2 104.0(2) . . ? C3A C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C3A C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C7A C3A C4 119.4(3) . . ? C7A C3A C3 111.1(3) . . ? C4 C3A C3 129.6(3) . . ? C3A C4 C5 118.1(3) . . ? C3A C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C7A C7 C6 116.2(3) . . ? C7A C7 H7 121.9 . . ? C6 C7 H7 121.9 . . ? C3A C7A C7 124.0(3) . . ? C3A C7A N1 111.4(3) . . ? C7 C7A N1 124.6(3) . . ? O1 C8 O2 128.1(3) . . ? O1 C8 C2 118.2(3) . . ? O2 C8 C2 113.7(2) . . ? 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 C8 1.237(4) . ? O2 C8 1.258(4) . ? N1 C7A 1.466(4) . ? N1 C2 1.514(4) . ? N1 H1NA 0.90(4) . ? N1 H1NB 0.88(5) . ? C2 C8 1.534(4) . ? C2 C3 1.548(4) . ? C2 H2 1.0000 . ? C3 C3A 1.507(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3A C7A 1.369(4) . ? C3A C4 1.390(5) . ? C4 C5 1.399(4) . ? C4 H4 0.9500 . ? C5 C6 1.379(5) . ? C5 H5 0.9500 . ? C6 C7 1.392(5) . ? C6 H6 0.9500 . ? C7 C7A 1.382(4) . ? C7 H7 0.9500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1NA O1 0.90(4) 2.14(4) 2.645(3) 114(3) . yes N1 H1NA O1 0.90(4) 2.00(4) 2.765(3) 141(3) 2_556 yes N1 H1NB O2 0.88(5) 1.80(5) 2.650(3) 163(4) 1_565 yes 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 C7A N1 C2 C8 110.3(2) . . . . ? C7A N1 C2 C3 -10.0(3) . . . . ? N1 C2 C3 C3A 9.1(3) . . . . ? C8 C2 C3 C3A -109.8(3) . . . . ? C2 C3 C3A C7A -5.0(3) . . . . ? C2 C3 C3A C4 176.1(3) . . . . ? C7A C3A C4 C5 0.2(4) . . . . ? C3 C3A C4 C5 179.0(3) . . . . ? C3A C4 C5 C6 0.1(5) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C5 C6 C7 C7A -0.2(5) . . . . ? C4 C3A C7A C7 -0.5(5) . . . . ? C3 C3A C7A C7 -179.6(3) . . . . ? C4 C3A C7A N1 177.7(3) . . . . ? C3 C3A C7A N1 -1.3(3) . . . . ? C6 C7 C7A C3A 0.5(4) . . . . ? C6 C7 C7A N1 -177.5(3) . . . . ? C2 N1 C7A C3A 7.3(3) . . . . ? C2 N1 C7A C7 -174.5(3) . . . . ? N1 C2 C8 O1 -5.5(4) . . . . ? C3 C2 C8 O1 111.4(3) . . . . ? N1 C2 C8 O2 175.5(2) . . . . ? C3 C2 C8 O2 -67.6(3) . . . . ?