#------------------------------------------------------------------------------ #$Date: 2020-02-21 04:18:22 +0200 (Fri, 21 Feb 2020) $ #$Revision: 248356 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557360.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_1557360 loop_ _publ_author_name 'Blake, Timothy R.' 'Ho, Wilson C.' 'Turlington, Christopher R.' 'Zang, Xiaoyu' 'Huttner, Melanie A.' 'Wender, Paul A.' 'Waymouth, Robert M.' _publ_section_title ; Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC05267D _journal_year 2020 _chemical_formula_moiety 'C8 H14 N2 O4' _chemical_formula_sum 'C8 H14 N2 O4' _chemical_formula_weight 202.21 _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 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-10-17 deposited with the CCDC. 2020-02-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.599(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.6483(5) _cell_length_b 9.0345(7) _cell_length_c 9.1851(9) _cell_measurement_reflns_used 3792 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.10 _cell_measurement_theta_min 3.21 _cell_volume 455.57(7) _computing_cell_refinement 'BRUKER APEX III' _computing_data_collection 'BRUKER APEX III' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker D8 Venture Diffractometer' _diffrn_measurement_method OMEGA-PHI _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_unetI/netI 0.0133 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 8400 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.137 _diffrn_reflns_theta_min 3.208 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldick, 1996)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.474 _exptl_crystal_description Needle _exptl_crystal_F_000 216 _exptl_crystal_size_max 0.091 _exptl_crystal_size_mid 0.089 _exptl_crystal_size_min 0.068 _exptl_transmission_factor_max 0.7455 _exptl_transmission_factor_min 0.6918 _refine_diff_density_max 0.329 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 65 _refine_ls_number_reflns 1012 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0329 _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^)+(0.0523P)^2^+0.1576P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.0944 _reflns_Friedel_coverage 0.000 _reflns_number_gt 902 _reflns_number_total 1012 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05267d2.cif _cod_data_source_block TRB_Dimer _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557360 _publcif_datablock.id {5722391e-43e7-42a9-b361-58b87a21098f} _shelx_shelxl_version_number 2014/7 _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_res_file ; mo_TRB_1216_Crystal_1_0ma_a.res created by SHELXL-2014/7 TITL mo_TRB_1216_Crystal_1_0ma_a.res in P2(1)/c CELL 0.71073 5.6483 9.0345 9.1851 90.000 103.599 90.000 ZERR 2.000 0.0005 0.0007 0.0009 0.000 0.004 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 16 28 4 8 REM Old TITL mo_TRB_1216_Crystal_1_0ma in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.122, Rweak 0.003, Alpha 0.014, Orientation as input REM Formula found by SHELXT: C4 N2 O L.S. 50 ACTA BOND $H FMAP 2 PLAN 5 TEMP -193.110 WGHT 0.052300 0.157600 FVAR 1.41272 O4 4 0.790051 0.660433 0.868374 11.00000 0.01845 0.02161 = 0.01660 0.00179 0.00536 -0.00409 N1 3 0.461368 0.512795 0.843359 11.00000 0.01579 0.01507 = 0.01090 0.00070 0.00327 0.00003 C6 1 0.652418 0.585180 0.925469 11.00000 0.01544 0.01279 = 0.01447 0.00056 0.00398 0.00247 C9 1 0.292504 0.425716 0.906254 11.00000 0.01511 0.01706 = 0.01396 0.00044 0.00299 -0.00220 AFIX 23 H9A 2 0.287392 0.324189 0.865074 11.00000 -1.20000 H9B 2 0.127710 0.468692 0.871087 11.00000 -1.20000 AFIX 0 C5 1 0.400394 0.529484 0.679567 11.00000 0.01835 0.01850 = 0.01115 0.00074 0.00303 0.00071 AFIX 23 H5A 2 0.321500 0.437878 0.632454 11.00000 -1.20000 H5B 2 0.551430 0.545084 0.644551 11.00000 -1.20000 AFIX 0 C4 1 0.229454 0.660315 0.632551 11.00000 0.02132 0.02500 = 0.01502 0.00560 0.00604 0.00499 AFIX 23 H4A 2 0.065671 0.636995 0.647702 11.00000 -1.20000 H4B 2 0.292552 0.748671 0.693075 11.00000 -1.20000 AFIX 0 O2 4 0.216526 0.687709 0.478558 11.00000 0.02828 0.04417 = 0.01755 0.01289 0.00828 0.01471 AFIX 147 H2 2 0.088910 0.735295 0.441274 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_TRB_1216_Crystal_1_0ma_a.res in P2(1)/c REM R1 = 0.0329 for 902 Fo > 4sig(Fo) and 0.0376 for all 1012 data REM 65 parameters refined using 0 restraints END WGHT 0.0520 0.1577 REM Highest difference peak 0.329, deepest hole -0.163, 1-sigma level 0.045 Q1 1 0.6727 0.5753 1.0080 11.00000 0.05 0.33 Q2 1 0.3120 0.5972 0.6601 11.00000 0.05 0.32 Q3 1 0.4214 0.5225 0.7651 11.00000 0.05 0.29 Q4 1 0.5680 0.5331 0.8796 11.00000 0.05 0.24 Q5 1 0.3772 0.4700 0.8765 11.00000 0.05 0.22 ; _shelx_res_checksum 57706 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 O4 O 0.79005(14) 0.66043(9) 0.86837(9) 0.0187(2) Uani 1 1 d . . . . . N1 N 0.46137(16) 0.51279(10) 0.84336(10) 0.0139(2) Uani 1 1 d . . . . . C6 C 0.65242(19) 0.58518(11) 0.92547(12) 0.0142(3) Uani 1 1 d . . . . . C9 C 0.29250(19) 0.42572(12) 0.90625(12) 0.0154(3) Uani 1 1 d . . . . . H9A H 0.2874 0.3242 0.8651 0.019 Uiso 1 1 calc R U . . . H9B H 0.1277 0.4687 0.8711 0.019 Uiso 1 1 calc R U . . . C5 C 0.40039(19) 0.52948(12) 0.67957(11) 0.0161(3) Uani 1 1 d . . . . . H5A H 0.3215 0.4379 0.6325 0.019 Uiso 1 1 calc R U . . . H5B H 0.5514 0.5451 0.6446 0.019 Uiso 1 1 calc R U . . . C4 C 0.2295(2) 0.66031(13) 0.63255(13) 0.0202(3) Uani 1 1 d . . . . . H4A H 0.0657 0.6370 0.6477 0.024 Uiso 1 1 calc R U . . . H4B H 0.2926 0.7487 0.6931 0.024 Uiso 1 1 calc R U . . . O2 O 0.21653(17) 0.68771(11) 0.47856(10) 0.0295(3) Uani 1 1 d . . . . . H2 H 0.0889 0.7353 0.4413 0.044 Uiso 1 1 calc R U . . . 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 O4 0.0184(4) 0.0216(4) 0.0166(4) 0.0018(3) 0.0054(3) -0.0041(3) N1 0.0158(5) 0.0151(4) 0.0109(4) 0.0007(3) 0.0033(3) 0.0000(3) C6 0.0154(5) 0.0128(5) 0.0145(5) 0.0006(4) 0.0040(4) 0.0025(4) C9 0.0151(5) 0.0171(5) 0.0140(5) 0.0004(4) 0.0030(4) -0.0022(4) C5 0.0183(5) 0.0185(5) 0.0111(5) 0.0007(4) 0.0030(4) 0.0007(4) C4 0.0213(6) 0.0250(6) 0.0150(5) 0.0056(4) 0.0060(4) 0.0050(4) O2 0.0283(5) 0.0442(6) 0.0176(5) 0.0129(4) 0.0083(4) 0.0147(4) 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' 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 C6 N1 C9 123.98(9) . . ? C6 N1 C5 119.49(9) . . ? C9 N1 C5 116.33(9) . . ? O4 C6 N1 122.34(10) . . ? O4 C6 C9 118.14(9) . 3_667 ? N1 C6 C9 119.52(9) . 3_667 ? N1 C9 C6 116.47(9) . 3_667 ? N1 C9 H9A 108.2 . . ? C6 C9 H9A 108.2 3_667 . ? N1 C9 H9B 108.2 . . ? C6 C9 H9B 108.2 3_667 . ? H9A C9 H9B 107.3 . . ? N1 C5 C4 110.49(8) . . ? N1 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? N1 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? O2 C4 C5 107.35(9) . . ? O2 C4 H4A 110.2 . . ? C5 C4 H4A 110.2 . . ? O2 C4 H4B 110.2 . . ? C5 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? C4 O2 H2 109.5 . . ? 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 O4 C6 1.2383(13) . ? N1 C6 1.3335(14) . ? N1 C9 1.4565(14) . ? N1 C5 1.4701(13) . ? C6 C9 1.5065(14) 3_667 ? C9 C6 1.5064(14) 3_667 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C5 C4 1.5231(15) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C4 O2 1.4208(13) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? O2 H2 0.8400 . ?