#------------------------------------------------------------------------------ #$Date: 2024-12-06 22:49:49 +0200 (Fri, 06 Dec 2024) $ #$Revision: 296706 $ #$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 M.' 'Devlin, Angela M.' 'Soucek, Jewel L.' 'Pittsford, Alexander M.' 'Turner, David A.' 'Petersen, Jacob P.' 'Oliver, Allen G.' 'Corcelli, Steven A.' 'Kandel, S. Alex' _publ_section_title ; Enantiopure molecules form apparently racemic monolayers of chiral cyclic pentamers. ; _journal_issue 39 _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_page_first 25430 _journal_page_last 25438 _journal_paper_doi 10.1039/d4cp02094d _journal_volume 26 _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_depositor_comments 'Adding full bibliography for 7249351.cif.' _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) . . . . ?