#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:16:59 +0300 (Thu, 07 May 2020) $ #$Revision: 251828 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240462.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_7240462 loop_ _publ_author_name 'Wallis, John D.' 'Garner, Alun Christopher' 'Yang, Songjie' _publ_section_title ; N-H···O Hydrogen Bonding to the Alkoxy Oxygen of a Carboxylic Ester Group: Crystal Structures of Methyl 2,6-Diaminobenzoate and Its Derivatives. ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00495B _journal_year 2020 _chemical_formula_sum 'C8 H10 N2 O2' _chemical_formula_weight 166.18 _chemical_melting_point 353.0(10) _chemical_name_systematic ; methyl 2,6-diaminobenzoate ; _chemical_properties_physical Air-sensitive _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 difmap _audit_creation_method SHELXL-2014 _audit_update_record ; 2020-04-01 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.202(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.4015(6) _cell_length_b 11.0987(11) _cell_length_c 13.6141(17) _cell_measurement_reflns_used 1468 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.2190 _cell_measurement_theta_min 3.5410 _cell_volume 809.72(16) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SHELXS _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9832 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.840 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.840 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3599 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.840 _diffrn_reflns_theta_full 27.000 _diffrn_reflns_theta_max 29.380 _diffrn_reflns_theta_min 3.016 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.363 _exptl_crystal_description 'thick plate' _exptl_crystal_F_000 352 _exptl_crystal_recrystallization_method 'Slow crystallisation from oil under nitrogen' _exptl_crystal_size_max 0.3349 _exptl_crystal_size_mid 0.1509 _exptl_crystal_size_min 0.1331 _refine_diff_density_max 0.344 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1884 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0453 _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^)+(0.0500P)^2^+0.2298P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1101 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1556 _reflns_number_total 1884 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00495b2.cif _cod_data_source_block dibaclc _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '352-354' was changed to '353.0(10)' -- the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240462 _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; REM P2(1)/c (#14 in standard setting) REM diaminobase in P2(1)/c REM R1 = 0.0600 for 1464 Fo > 4sig(Fo) and 0.0831 for all 1899 data REM 149 parameters refined using 0 restraints REM Highest difference peak 0.271, deepest hole -0.195, 1-sigma level 0.047 REM diaminobase in P2(1)/c REM R1 = 0.0605 for 1472 Fo > 4sig(Fo) and 0.0835 for all 1899 data REM 149 parameters refined using 0 restraints REM Highest difference peak 0.274, deepest hole -0.196, 1-sigma level 0.048 REM diaminobase in P2(1)/c REM R1 = 0.0453 for 1556 Fo > 4sig(Fo) and 0.0579 for all 1884 data REM 149 parameters refined using 0 restraints REM Highest difference peak 0.345, deepest hole -0.220, 1-sigma level 0.043 REM diaminobase in P2(1)/c REM R1 = 0.0453 for 1556 Fo > 4sig(Fo) and 0.0579 for all 1884 data REM 149 parameters refined using 0 restraints REM Highest difference peak 0.344, deepest hole -0.220, 1-sigma level 0.043 TITL diaminobase in P2(1)/c CELL 0.71073 5.4015 11.0987 13.6141 90.000 97.202 90.000 ZERR 4.0000 0.0006 0.0011 0.0017 0.000 0.012 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 32 40 8 8 MERG 2 FMAP 2 GRID PLAN 20 TEMP -173 CONF HTAB N2 O2 HTAB N1 O1 EQIV $1 -x+2, y+1/2, -z+1/2 HTAB C3 O2_$1 EQIV $2 x, -y+3/2, z-1/2 HTAB N2 O1_$2 HTAB N1 N2_$1 MPLA 4 C7 O1 O2 C8 MPLA 6 C1 C2 C3 C4 C5 C6 BOND $H L.S. 4 ACTA 54 WGHT 0.050000 0.229800 FVAR 9.35561 O1 4 0.630512 0.859614 0.406192 11.00000 0.03467 0.03015 = 0.01440 -0.00257 0.00663 -0.00957 O2 4 0.473908 0.718256 0.300558 11.00000 0.02381 0.02400 = 0.01647 -0.00191 0.00674 -0.00596 N1 3 1.003013 0.992116 0.364879 11.00000 0.03187 0.03118 = 0.02789 -0.00768 0.00988 -0.01618 N2 3 0.595486 0.704156 0.120713 11.00000 0.02273 0.02674 = 0.01236 -0.00148 0.00305 0.00062 C1 1 0.785317 0.845991 0.249642 11.00000 0.01764 0.01814 = 0.01529 0.00358 0.00323 0.00312 C2 1 0.974432 0.934586 0.275732 11.00000 0.02063 0.01893 = 0.01991 0.00305 0.00323 0.00259 C3 1 1.140452 0.964823 0.208069 11.00000 0.01946 0.01962 = 0.02926 0.00359 0.00615 0.00065 C4 1 1.115522 0.912676 0.115901 11.00000 0.02041 0.02603 = 0.02698 0.00757 0.01198 0.00562 C5 1 0.931292 0.828939 0.087396 11.00000 0.02458 0.02696 = 0.01789 0.00228 0.00704 0.00620 C6 1 0.764983 0.793052 0.152625 11.00000 0.01762 0.01821 = 0.01522 0.00340 0.00191 0.00607 C7 1 0.626727 0.812124 0.324966 11.00000 0.01746 0.01893 = 0.01458 0.00270 -0.00006 0.00156 C8 1 0.328111 0.678992 0.376226 11.00000 0.02770 0.03291 = 0.02011 -0.00161 0.00894 -0.01133 H82 2 0.444842 0.648497 0.432700 11.00000 0.02841 H21 2 0.463040 0.693241 0.153943 11.00000 0.03148 H11 2 0.894594 0.978166 0.406022 11.00000 0.03755 H5 2 0.915713 0.793002 0.022420 11.00000 0.03062 H4 2 1.229015 0.932514 0.070512 11.00000 0.02641 H3 2 1.261791 1.023509 0.226058 11.00000 0.02295 H83 2 0.222406 0.619839 0.346295 11.00000 0.03438 H22 2 0.574531 0.693578 0.054639 11.00000 0.02453 H81 2 0.227838 0.747282 0.396289 11.00000 0.03003 H12 2 1.116615 1.043759 0.373917 11.00000 0.02967 HKLF 4 REM diaminobase in P2(1)/c REM R1 = 0.0453 for 1556 Fo > 4sig(Fo) and 0.0579 for all 1884 data REM 149 parameters refined using 0 restraints END WGHT 0.0500 0.2298 REM Highest difference peak 0.344, deepest hole -0.220, 1-sigma level 0.043 Q1 1 0.6957 0.8351 0.2804 11.00000 0.05 0.34 Q2 1 1.0754 0.9395 0.2478 11.00000 0.05 0.29 Q3 1 0.7309 0.8406 0.1946 11.00000 0.05 0.28 Q4 1 0.8451 0.8179 0.1166 11.00000 0.05 0.25 Q5 1 0.8568 0.9015 0.2590 11.00000 0.05 0.24 Q6 1 0.9070 0.8725 0.2701 11.00000 0.05 0.23 Q7 1 0.9651 0.8942 0.1015 11.00000 0.05 0.18 Q8 1 1.0707 0.9607 0.1594 11.00000 0.05 0.16 Q9 1 0.6434 0.7718 0.1307 11.00000 0.05 0.15 Q10 1 0.3196 0.5809 0.3740 11.00000 0.05 0.15 Q11 1 0.6959 0.9289 0.4099 11.00000 0.05 0.14 Q12 1 1.1117 0.9259 0.1718 11.00000 0.05 0.14 Q13 1 0.7207 0.8189 0.3817 11.00000 0.05 0.14 Q14 1 0.4586 0.7856 0.2904 11.00000 0.05 0.13 Q15 1 0.3793 0.7202 0.2473 11.00000 0.05 0.13 Q16 1 1.0340 0.9394 0.3197 11.00000 0.05 0.13 Q17 1 0.6933 0.8872 0.4783 11.00000 0.05 0.13 Q18 1 0.4235 0.7614 0.1048 11.00000 0.05 0.13 Q19 1 0.8758 0.8249 0.0449 11.00000 0.05 0.12 Q20 1 0.3884 0.8066 0.1688 11.00000 0.05 0.12 ; _shelx_res_checksum 47627 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 O1 O 0.6305(2) 0.85961(10) 0.40619(7) 0.0261(3) Uani 1 1 d . . . . . O2 O 0.47391(18) 0.71826(9) 0.30056(7) 0.0211(3) Uani 1 1 d . . . . . N1 N 1.0030(3) 0.99212(13) 0.36488(10) 0.0298(3) Uani 1 1 d . . . . . N2 N 0.5955(2) 0.70416(11) 0.12071(9) 0.0205(3) Uani 1 1 d . . . . . C1 C 0.7853(2) 0.84599(12) 0.24964(9) 0.0169(3) Uani 1 1 d . . . . . C2 C 0.9744(3) 0.93459(13) 0.27573(10) 0.0198(3) Uani 1 1 d . . . . . C3 C 1.1405(3) 0.96482(14) 0.20807(11) 0.0225(3) Uani 1 1 d . . . . . C4 C 1.1155(3) 0.91268(14) 0.11590(11) 0.0237(3) Uani 1 1 d . . . . . C5 C 0.9313(3) 0.82894(14) 0.08740(10) 0.0228(3) Uani 1 1 d . . . . . C6 C 0.7650(2) 0.79305(12) 0.15262(9) 0.0170(3) Uani 1 1 d . . . . . C7 C 0.6267(2) 0.81212(12) 0.32497(9) 0.0172(3) Uani 1 1 d . . . . . C8 C 0.3281(3) 0.67899(16) 0.37623(11) 0.0264(4) Uani 1 1 d . . . . . H82 H 0.445(3) 0.6485(15) 0.4327(13) 0.028(4) Uiso 1 1 d . . . . . H21 H 0.463(3) 0.6932(16) 0.1539(13) 0.031(5) Uiso 1 1 d . . . . . H11 H 0.895(4) 0.9782(17) 0.4060(14) 0.038(5) Uiso 1 1 d . . . . . H5 H 0.916(3) 0.7930(15) 0.0224(13) 0.031(5) Uiso 1 1 d . . . . . H4 H 1.229(3) 0.9325(15) 0.0705(12) 0.026(4) Uiso 1 1 d . . . . . H3 H 1.262(3) 1.0235(16) 0.2261(11) 0.023(4) Uiso 1 1 d . . . . . H83 H 0.222(3) 0.6198(17) 0.3463(13) 0.034(5) Uiso 1 1 d . . . . . H22 H 0.575(3) 0.6936(15) 0.0546(13) 0.025(4) Uiso 1 1 d . . . . . H81 H 0.228(3) 0.7473(16) 0.3963(13) 0.030(4) Uiso 1 1 d . . . . . H12 H 1.117(3) 1.0438(16) 0.3739(13) 0.030(5) Uiso 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 0.0347(6) 0.0302(6) 0.0144(5) -0.0026(4) 0.0066(4) -0.0096(5) O2 0.0238(5) 0.0240(5) 0.0165(5) -0.0019(4) 0.0067(4) -0.0060(4) N1 0.0319(8) 0.0312(7) 0.0279(7) -0.0077(6) 0.0099(6) -0.0162(6) N2 0.0227(6) 0.0267(7) 0.0124(5) -0.0015(5) 0.0030(5) 0.0006(5) C1 0.0176(7) 0.0181(7) 0.0153(6) 0.0036(5) 0.0032(5) 0.0031(5) C2 0.0206(7) 0.0189(7) 0.0199(6) 0.0030(6) 0.0032(5) 0.0026(6) C3 0.0195(7) 0.0196(7) 0.0293(7) 0.0036(6) 0.0062(6) 0.0007(6) C4 0.0204(7) 0.0260(8) 0.0270(7) 0.0076(6) 0.0120(6) 0.0056(6) C5 0.0246(7) 0.0270(8) 0.0179(6) 0.0023(6) 0.0070(6) 0.0062(6) C6 0.0176(6) 0.0182(7) 0.0152(6) 0.0034(5) 0.0019(5) 0.0061(5) C7 0.0175(7) 0.0189(7) 0.0146(6) 0.0027(5) -0.0001(5) 0.0016(5) C8 0.0277(8) 0.0329(9) 0.0201(7) -0.0016(7) 0.0089(6) -0.0113(7) 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 C7 O2 C8 115.55(11) . . ? C2 N1 H11 118.5(12) . . ? C2 N1 H12 116.8(12) . . ? H11 N1 H12 124.4(17) . . ? C6 N2 H21 118.4(11) . . ? C6 N2 H22 113.8(11) . . ? H21 N2 H22 118.4(15) . . ? C2 C1 C6 118.63(12) . . ? C2 C1 C7 117.68(12) . . ? C6 C1 C7 123.66(13) . . ? N1 C2 C3 117.50(14) . . ? N1 C2 C1 122.74(13) . . ? C3 C2 C1 119.75(13) . . ? C4 C3 C2 120.08(14) . . ? C4 C3 H3 121.2(10) . . ? C2 C3 H3 118.6(10) . . ? C3 C4 C5 121.67(13) . . ? C3 C4 H4 120.0(10) . . ? C5 C4 H4 118.3(10) . . ? C4 C5 C6 120.73(13) . . ? C4 C5 H5 120.9(10) . . ? C6 C5 H5 118.4(10) . . ? N2 C6 C5 117.26(12) . . ? N2 C6 C1 123.60(12) . . ? C5 C6 C1 119.09(13) . . ? O1 C7 O2 119.84(12) . . ? O1 C7 C1 125.26(13) . . ? O2 C7 C1 114.86(11) . . ? O2 C8 H82 107.8(10) . . ? O2 C8 H83 105.1(11) . . ? H82 C8 H83 113.3(15) . . ? O2 C8 H81 109.4(10) . . ? H82 C8 H81 111.4(14) . . ? H83 C8 H81 109.5(15) . . ? 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 C7 1.2229(16) . ? O2 C7 1.3448(16) . ? O2 C8 1.4404(17) . ? N1 C2 1.3629(19) . ? N1 H11 0.87(2) . ? N1 H12 0.837(19) . ? N2 C6 1.3786(18) . ? N2 H21 0.901(18) . ? N2 H22 0.900(17) . ? C1 C2 1.430(2) . ? C1 C6 1.4372(18) . ? C1 C7 1.4652(18) . ? C2 C3 1.4044(19) . ? C3 C4 1.373(2) . ? C3 H3 0.935(17) . ? C4 C5 1.381(2) . ? C4 H4 0.949(17) . ? C5 C6 1.3979(19) . ? C5 H5 0.964(17) . ? C8 H82 0.991(17) . ? C8 H83 0.930(19) . ? C8 H81 0.990(18) . ? 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 N2 H21 O2 0.901(18) 2.009(18) 2.6180(15) 123.6(15) . N1 H11 O1 0.87(2) 1.94(2) 2.6098(18) 132.3(16) . C3 H3 O2 0.935(17) 2.640(17) 3.5108(18) 155.2(13) 2_755 N2 H22 O1 0.900(17) 2.163(17) 3.0339(15) 162.7(15) 4_575 N1 H12 N2 0.837(19) 2.359(19) 3.1896(19) 171.6(16) 2_755 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 N1 178.05(13) . . . . ? C7 C1 C2 N1 -3.5(2) . . . . ? C6 C1 C2 C3 -2.2(2) . . . . ? C7 C1 C2 C3 176.28(12) . . . . ? N1 C2 C3 C4 -177.88(14) . . . . ? C1 C2 C3 C4 2.3(2) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 N2 -176.41(13) . . . . ? C4 C5 C6 C1 1.0(2) . . . . ? C2 C1 C6 N2 177.78(12) . . . . ? C7 C1 C6 N2 -0.6(2) . . . . ? C2 C1 C6 C5 0.52(19) . . . . ? C7 C1 C6 C5 -177.84(13) . . . . ? C8 O2 C7 O1 -1.59(19) . . . . ? C8 O2 C7 C1 176.26(12) . . . . ? C2 C1 C7 O1 5.6(2) . . . . ? C6 C1 C7 O1 -176.02(13) . . . . ? C2 C1 C7 O2 -172.11(11) . . . . ? C6 C1 C7 O2 6.27(19) . . . . ?