#------------------------------------------------------------------------------ #$Date: 2020-04-21 05:23:19 +0300 (Tue, 21 Apr 2020) $ #$Revision: 250974 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240359.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_7240359 loop_ _publ_author_name 'Dhawa, Tanumoy' 'Hazra, Ananta' 'Barma, Arpita' 'Pal, Kunal' 'Karmakar, Parimal' 'Roy, Partha' _publ_section_title ; 4-Methyl-2,6-diformylphenol based biocompatible chemosensors for pH: discrimination between normal cells and cancer cells ; _journal_issue 26 _journal_name_full 'RSC Advances' _journal_page_first 15501 _journal_paper_doi 10.1039/D0RA00754D _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C14 H12 N2 O2' _chemical_formula_sum 'C14 H12 N2 O2' _chemical_formula_weight 240.26 _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-01-13 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 29.004(4) _cell_length_b 37.698(6) _cell_length_c 4.4554(7) _cell_measurement_reflns_used 900 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.004 _cell_measurement_theta_min 2.05 _cell_volume 4871.5(13) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'BRUKER D8 QUEST AREA DETECTOR' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1135 _diffrn_reflns_av_unetI/netI 0.0882 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 16785 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.004 _diffrn_reflns_theta_min 1.772 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.310 _exptl_crystal_description Block _exptl_crystal_F_000 2000 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.186 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 417 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -1.0(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.223 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2663 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.223 _refine_ls_R_factor_all 0.1715 _refine_ls_R_factor_gt 0.0919 _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^)+(0.0282P)^2^+9.7713P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1377 _refine_ls_wR_factor_ref 0.1637 _reflns_Friedel_coverage 0.764 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 1559 _reflns_number_total 2670 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra00754d2.cif _cod_data_source_block shelx _cod_original_cell_volume 4871.7(13) _cod_database_code 7240359 _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_res_file ; TITL SIR92 run in space group F d d 2 shelx.res created by SHELXL-2018/3 at 20:51:06 on 14-Nov-2019 CELL 0.71073 29.0045 37.6985 4.4554 90.000 90.000 90.000 ZERR 16.00 0.0043 0.0062 0.0007 0.000 0.000 0.000 LATT -4 SYMM - X, - Y, Z SYMM 1/4 - X, 1/4 + Y, 1/4 + Z SYMM 1/4 + X, 1/4 - Y, 1/4 + Z SFAC C H N O UNIT 240 192 16 32 MERG 2 OMIT -3.00 55.00 FMAP 2 PLAN 2 ACTA BOND $H CONF L.S. 100 TEMP 0.00 WGHT 0.028200 9.771300 FVAR 0.25168 O2 4 0.744007 0.052120 0.644841 11.00000 0.05288 0.05674 = 0.09069 -0.01788 0.02205 -0.01403 N1 3 0.820082 0.059083 0.346149 11.00000 0.04891 0.05063 = 0.04265 -0.00049 0.00272 -0.00383 O1 4 0.650657 0.091101 1.217274 11.00000 0.05320 0.07480 = 0.16381 -0.01110 0.05115 -0.00615 C2 1 0.768427 0.152371 1.003176 11.00000 0.04765 0.04692 = 0.04929 -0.00049 0.00295 -0.00076 C4 1 0.721321 0.099434 0.964060 11.00000 0.03519 0.05022 = 0.06283 0.00242 0.01034 0.00081 C7 1 0.791941 0.103655 0.680756 11.00000 0.03941 0.04804 = 0.04021 0.00312 0.00177 -0.00204 C3 1 0.729939 0.132924 1.081338 11.00000 0.04555 0.05115 = 0.05433 -0.00260 0.00765 0.00932 AFIX 43 H3 2 0.709066 0.142571 1.217143 11.00000 -1.20000 AFIX 0 C6 1 0.752524 0.084681 0.760861 11.00000 0.04220 0.04327 = 0.05824 -0.00025 -0.00207 -0.00227 N2 3 0.922134 0.051035 -0.152741 11.00000 0.06664 0.07022 = 0.08047 -0.01710 0.02073 -0.00457 C11 1 0.849731 0.010438 0.061155 11.00000 0.06228 0.05238 = 0.05903 0.00493 0.00416 -0.01113 AFIX 43 H11 2 0.824977 -0.003218 0.126356 11.00000 -1.20000 AFIX 0 C8 1 0.799139 0.137140 0.804523 11.00000 0.04701 0.04944 = 0.05005 0.00034 0.00384 -0.01077 AFIX 43 H8 2 0.825537 0.149663 0.751518 11.00000 -1.20000 AFIX 0 C10 1 0.853968 0.045361 0.148130 11.00000 0.04704 0.04480 = 0.03705 0.00478 -0.00438 -0.00038 C9 1 0.825505 0.089358 0.473255 11.00000 0.04490 0.05473 = 0.04013 0.00208 0.00590 -0.00881 AFIX 43 H9 2 0.851830 0.102509 0.430615 11.00000 -1.20000 AFIX 0 C14 1 0.890116 0.064519 0.029794 11.00000 0.05573 0.05165 = 0.07079 -0.01667 0.00943 -0.00361 AFIX 43 H14 2 0.892352 0.088391 0.080371 11.00000 -1.20000 AFIX 0 C13 1 0.917690 0.016894 -0.223056 11.00000 0.06726 0.06801 = 0.07002 -0.01829 0.01640 0.01345 AFIX 43 H13 2 0.939767 0.006672 -0.347284 11.00000 -1.20000 AFIX 0 C12 1 0.882656 -0.003745 -0.122991 11.00000 0.08459 0.04831 = 0.06566 -0.01433 0.00381 0.00068 AFIX 43 H12 2 0.881007 -0.027466 -0.179320 11.00000 -1.20000 AFIX 0 C1 1 0.777011 0.189011 1.125604 11.00000 0.07412 0.05872 = 0.07615 -0.01637 0.01335 -0.00598 AFIX 33 H1A 2 0.805368 0.198082 1.045253 11.00000 -1.50000 H1B 2 0.752064 0.204359 1.069144 11.00000 -1.50000 H1C 2 0.779072 0.187951 1.340467 11.00000 -1.50000 AFIX 0 C5 1 0.680472 0.079983 1.057704 11.00000 0.05005 0.06543 = 0.12427 -0.01787 0.03411 -0.00988 AFIX 43 H5 2 0.677271 0.056889 0.987320 11.00000 -1.20000 AFIX 0 H2 2 0.767182 0.047980 0.506733 11.00000 0.07101 HKLF 4 REM SIR92 run in space group F d d 2 REM wR2 = 0.1637, GooF = S = 1.223, Restrained GooF = 1.223 for all data REM R1 = 0.0919 for 1559 Fo > 4sig(Fo) and 0.1715 for all 2663 data REM 167 parameters refined using 1 restraints END WGHT 0.0269 8.4033 REM Highest difference peak 0.186, deepest hole -0.181, 1-sigma level 0.040 Q1 1 0.8821 0.0054 0.0675 11.00000 0.05 0.19 Q2 1 0.6171 0.0832 1.1137 11.00000 0.05 0.17 ; _shelx_res_checksum 26662 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 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 O2 O 0.74401(15) 0.05212(12) 0.6448(12) 0.0668(16) Uani 1 1 d . . . . . N1 N 0.82008(16) 0.05908(14) 0.3461(11) 0.0474(13) Uani 1 1 d . . . . . O1 O 0.65066(15) 0.09110(12) 1.2173(15) 0.097(2) Uani 1 1 d . . . . . C2 C 0.7684(2) 0.15237(15) 1.0032(14) 0.0480(16) Uani 1 1 d . . . . . C4 C 0.72132(19) 0.09943(16) 0.9641(16) 0.0494(17) Uani 1 1 d . . . . . C7 C 0.79194(18) 0.10366(15) 0.6808(13) 0.0426(15) Uani 1 1 d . . . . . C3 C 0.72994(19) 0.13292(16) 1.0813(15) 0.0503(17) Uani 1 1 d . . . . . H3 H 0.709066 0.142571 1.217143 0.060 Uiso 1 1 calc R U . . . C6 C 0.7525(2) 0.08468(16) 0.7609(14) 0.0479(17) Uani 1 1 d . . . . . N2 N 0.92213(19) 0.05104(16) -0.1527(16) 0.0724(19) Uani 1 1 d . . . . . C11 C 0.8497(2) 0.01044(17) 0.0612(16) 0.0579(19) Uani 1 1 d . . . . . H11 H 0.824977 -0.003218 0.126356 0.069 Uiso 1 1 calc R U . . . C8 C 0.7991(2) 0.13714(15) 0.8045(14) 0.0488(16) Uani 1 1 d . . . . . H8 H 0.825537 0.149663 0.751518 0.059 Uiso 1 1 calc R U . . . C10 C 0.8540(2) 0.04536(16) 0.1481(13) 0.0430(15) Uani 1 1 d . . . . . C9 C 0.82550(19) 0.08936(17) 0.4733(13) 0.0466(16) Uani 1 1 d . . . . . H9 H 0.851830 0.102509 0.430615 0.056 Uiso 1 1 calc R U . . . C14 C 0.8901(2) 0.06452(17) 0.0298(16) 0.0594(19) Uani 1 1 d . . . . . H14 H 0.892352 0.088391 0.080371 0.071 Uiso 1 1 calc R U . . . C13 C 0.9177(2) 0.0169(2) -0.2231(19) 0.068(2) Uani 1 1 d . . . . . H13 H 0.939767 0.006672 -0.347284 0.082 Uiso 1 1 calc R U . . . C12 C 0.8827(3) -0.00375(19) -0.1230(16) 0.066(2) Uani 1 1 d . . . . . H12 H 0.881007 -0.027466 -0.179320 0.079 Uiso 1 1 calc R U . . . C1 C 0.7770(2) 0.18901(17) 1.1256(17) 0.070(2) Uani 1 1 d . . . . . H1A H 0.805368 0.198082 1.045253 0.104 Uiso 1 1 calc R U . . . H1B H 0.752064 0.204359 1.069144 0.104 Uiso 1 1 calc R U . . . H1C H 0.779072 0.187951 1.340467 0.104 Uiso 1 1 calc R U . . . C5 C 0.6805(2) 0.07998(19) 1.058(2) 0.080(3) Uani 1 1 d . . . . . H5 H 0.677271 0.056889 0.987320 0.096 Uiso 1 1 calc R U . . . H2 H 0.767(2) 0.0480(16) 0.507(17) 0.07(2) 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 O2 0.053(3) 0.057(3) 0.091(4) -0.018(3) 0.022(3) -0.014(2) N1 0.049(3) 0.051(3) 0.043(3) 0.000(3) 0.003(3) -0.004(2) O1 0.053(3) 0.075(4) 0.164(6) -0.011(4) 0.051(4) -0.006(3) C2 0.048(4) 0.047(4) 0.049(4) 0.000(3) 0.003(3) -0.001(3) C4 0.035(3) 0.050(4) 0.063(5) 0.002(4) 0.010(3) 0.001(3) C7 0.039(3) 0.048(4) 0.040(4) 0.003(3) 0.002(3) -0.002(3) C3 0.046(4) 0.051(4) 0.054(4) -0.003(3) 0.008(3) 0.009(3) C6 0.042(3) 0.043(4) 0.058(5) 0.000(3) -0.002(3) -0.002(3) N2 0.067(4) 0.070(4) 0.080(5) -0.017(4) 0.021(4) -0.005(3) C11 0.062(4) 0.052(4) 0.059(5) 0.005(4) 0.004(4) -0.011(3) C8 0.047(4) 0.049(4) 0.050(4) 0.000(3) 0.004(3) -0.011(3) C10 0.047(4) 0.045(4) 0.037(4) 0.005(3) -0.004(3) 0.000(3) C9 0.045(3) 0.055(4) 0.040(4) 0.002(3) 0.006(3) -0.009(3) C14 0.056(4) 0.052(4) 0.071(5) -0.017(4) 0.009(4) -0.004(3) C13 0.067(5) 0.068(5) 0.070(6) -0.018(4) 0.016(4) 0.013(4) C12 0.085(5) 0.048(4) 0.066(5) -0.014(4) 0.004(5) 0.001(4) C1 0.074(5) 0.059(4) 0.076(6) -0.016(4) 0.013(4) -0.006(4) C5 0.050(4) 0.065(5) 0.124(8) -0.018(5) 0.034(5) -0.010(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 O2 H2 106(4) . . ? C9 N1 C10 120.9(5) . . ? C3 C2 C8 117.6(5) . . ? C3 C2 C1 122.0(6) . . ? C8 C2 C1 120.5(5) . . ? C3 C4 C6 119.3(5) . . ? C3 C4 C5 119.8(6) . . ? C6 C4 C5 120.9(6) . . ? C8 C7 C6 119.1(6) . . ? C8 C7 C9 119.3(5) . . ? C6 C7 C9 121.6(6) . . ? C2 C3 C4 122.2(6) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? O2 C6 C7 121.1(6) . . ? O2 C6 C4 119.4(5) . . ? C7 C6 C4 119.5(6) . . ? C13 N2 C14 116.4(6) . . ? C12 C11 C10 118.7(6) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C2 C8 C7 122.3(5) . . ? C2 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C11 C10 C14 117.5(6) . . ? C11 C10 N1 117.5(6) . . ? C14 C10 N1 125.0(6) . . ? N1 C9 C7 122.1(5) . . ? N1 C9 H9 119.0 . . ? C7 C9 H9 119.0 . . ? N2 C14 C10 124.2(6) . . ? N2 C14 H14 117.9 . . ? C10 C14 H14 117.9 . . ? N2 C13 C12 123.4(7) . . ? N2 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C13 C12 C11 119.8(7) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C5 C4 125.7(7) . . ? O1 C5 H5 117.2 . . ? C4 C5 H5 117.2 . . ? 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 O2 C6 1.355(7) . ? O2 H2 0.92(7) . ? N1 C9 1.284(7) . ? N1 C10 1.418(7) . ? O1 C5 1.195(8) . ? C2 C3 1.380(7) . ? C2 C8 1.381(8) . ? C2 C1 1.506(8) . ? C4 C3 1.389(8) . ? C4 C6 1.396(8) . ? C4 C5 1.454(8) . ? C7 C8 1.393(7) . ? C7 C6 1.395(7) . ? C7 C9 1.447(8) . ? C3 H3 0.9300 . ? N2 C13 1.331(8) . ? N2 C14 1.335(8) . ? C11 C12 1.368(9) . ? C11 C10 1.378(8) . ? C11 H11 0.9300 . ? C8 H8 0.9300 . ? C10 C14 1.378(8) . ? C9 H9 0.9300 . ? C14 H14 0.9300 . ? C13 C12 1.355(9) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C5 H5 0.9300 . ? 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 C8 C2 C3 C4 -0.9(9) . . . . ? C1 C2 C3 C4 178.6(6) . . . . ? C6 C4 C3 C2 0.2(10) . . . . ? C5 C4 C3 C2 179.2(6) . . . . ? C8 C7 C6 O2 179.6(6) . . . . ? C9 C7 C6 O2 -0.5(9) . . . . ? C8 C7 C6 C4 -0.4(9) . . . . ? C9 C7 C6 C4 179.4(6) . . . . ? C3 C4 C6 O2 -179.6(6) . . . . ? C5 C4 C6 O2 1.4(10) . . . . ? C3 C4 C6 C7 0.5(9) . . . . ? C5 C4 C6 C7 -178.5(6) . . . . ? C3 C2 C8 C7 1.0(9) . . . . ? C1 C2 C8 C7 -178.5(6) . . . . ? C6 C7 C8 C2 -0.4(9) . . . . ? C9 C7 C8 C2 179.8(6) . . . . ? C12 C11 C10 C14 3.5(9) . . . . ? C12 C11 C10 N1 -178.2(6) . . . . ? C9 N1 C10 C11 169.1(6) . . . . ? C9 N1 C10 C14 -12.7(9) . . . . ? C10 N1 C9 C7 -178.7(5) . . . . ? C8 C7 C9 N1 -178.1(6) . . . . ? C6 C7 C9 N1 2.1(9) . . . . ? C13 N2 C14 C10 0.6(11) . . . . ? C11 C10 C14 N2 -2.9(10) . . . . ? N1 C10 C14 N2 178.9(6) . . . . ? C14 N2 C13 C12 1.0(12) . . . . ? N2 C13 C12 C11 -0.3(12) . . . . ? C10 C11 C12 C13 -2.0(10) . . . . ? C3 C4 C5 O1 5.3(13) . . . . ? C6 C4 C5 O1 -175.7(8) . . . . ?