#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:10:02 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257956 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240428.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_7240428 loop_ _publ_author_name 'Hulushe, Siya T.' 'Manyeruke, Meloddy H.' 'Louzada, Marcel' 'Rigin, Sergei' 'Hosten, Eric C.' 'Watkins, Gareth M.' _publ_section_title ; Exploring intermolecular contacts in multi-substituted benzaldehyde derivatives: X-ray, Hirshfeld surface and lattice energy analyses ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 16861 _journal_page_last 16874 _journal_paper_doi 10.1039/C9RA10752E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C11 H10 O3' _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 _chemical_melting_point 326 _chemical_name_common 3-methoxy-2-(prop-2-ynyloxy)benzaldehyde _chemical_name_systematic 3-methoxy-2-(prop-2-ynoxy)benzaldehyde _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-02-22 deposited with the CCDC. 2020-04-02 downloaded from the CCDC. ; _cell_angle_alpha 65.896(2) _cell_angle_beta 85.990(2) _cell_angle_gamma 70.155(2) _cell_formula_units_Z 2 _cell_length_a 7.7110(4) _cell_length_b 7.9405(4) _cell_length_c 9.1857(5) _cell_measurement_reflns_used 6757 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 28.31 _cell_measurement_theta_min 2.82 _cell_volume 481.36(4) _computing_cell_refinement 'APEX2 v2011.4-1 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service v2011.4.0.0' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 2012)' _computing_publication_material 'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (H\"ubschle, 2011)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 200(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_unetI/netI 0.0117 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12649 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.363 _diffrn_reflns_theta_min 2.437 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9474 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_crystal_colour 'pale brown' _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 200 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane/water' _exptl_crystal_size_max 0.607 _exptl_crystal_size_mid 0.379 _exptl_crystal_size_min 0.232 _refine_diff_density_max 0.184 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.029 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2396 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0366 _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^)+(0.0443P)^2^+0.0905P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0951 _refine_ls_wR_factor_ref 0.1024 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1985 _reflns_number_total 2396 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10752e2.cif _cod_data_source_block ia355 _cod_depositor_comments 'Adding full bibliography for 7240424--7240429.cif.' _cod_database_code 7240428 _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 0.944 _shelx_estimated_absorpt_t_max 0.978 _shelx_res_file ; TITL ia355_a.res in P-1 ia355.res created by SHELXL-2018/3 at 16:07:25 on 18-Feb-2019 REM Old TITL ia355_p_P-1 in P-1 REM SHELXT solution in P-1: R1 0.164, Rweak 0.006, Alpha 0.043 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C10 N O3 CELL 0.71073 7.7110 7.9405 9.1857 65.896 85.990 70.155 ZERR 2.00 0.0004 0.0004 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H O UNIT 22 20 6 EQIV $1 -x,1-y,2-z HTAB C1 O2 HTAB C2 O3 HTAB C4 O1_$1 ACTA BOND $H CONF FMAP 2 HTAB L.S. 100 LIST 4 PLAN -20 SIZE 0.232 0.379 0.607 TEMP -73.150 REM WGHT 0.044300 0.090300 REM WGHT 0.044300 0.090500 REM WGHT 0.044300 0.090500 WGHT 0.044300 0.090500 FVAR 0.51828 O1 3 0.308763 0.661019 0.868052 11.00000 0.07622 0.05625 = 0.07610 -0.04005 0.01006 -0.02887 O2 3 0.445654 0.195240 0.758089 11.00000 0.03966 0.03046 = 0.04287 -0.00945 -0.00807 -0.00885 O3 3 0.338277 0.215520 0.477594 11.00000 0.05486 0.04779 = 0.04347 -0.02200 -0.00485 -0.01174 C1 1 0.361163 0.527018 0.825331 11.00000 0.05328 0.04007 = 0.05486 -0.02001 0.00199 -0.02168 AFIX 43 H1 2 0.445104 0.404844 0.896536 11.00000 -1.20000 AFIX 0 C2 1 0.342590 0.065865 0.833829 11.00000 0.06190 0.03261 = 0.04238 -0.00934 -0.00723 -0.01998 AFIX 23 H2A 2 0.428679 -0.064958 0.904022 11.00000 -1.20000 H2B 2 0.282168 0.050223 0.750829 11.00000 -1.20000 AFIX 0 C3 1 0.202487 0.139176 0.928343 11.00000 0.05598 0.04638 = 0.03403 -0.00309 -0.00828 -0.02492 C4 1 0.087000 0.198241 1.002770 11.00000 0.06349 0.07259 = 0.04123 -0.01005 0.00019 -0.02562 AFIX 163 H4 2 -0.006612 0.246118 1.063100 11.00000 -1.20000 AFIX 0 C5 1 0.281700 0.221445 0.330331 11.00000 0.05546 0.07191 = 0.04317 -0.02950 0.00695 -0.02785 AFIX 137 H5A 2 0.334493 0.304690 0.241896 11.00000 -1.50000 H5B 2 0.146429 0.275426 0.313610 11.00000 -1.50000 H5C 2 0.325348 0.088286 0.334418 11.00000 -1.50000 AFIX 0 C11 1 0.302663 0.542468 0.670474 11.00000 0.03270 0.03344 = 0.04468 -0.01266 0.00527 -0.01356 C12 1 0.343900 0.374656 0.641735 11.00000 0.02895 0.03071 = 0.03861 -0.00876 0.00013 -0.00949 C13 1 0.289089 0.388195 0.493928 11.00000 0.03267 0.03998 = 0.03927 -0.01341 0.00223 -0.01090 C14 1 0.193362 0.571257 0.377056 11.00000 0.04089 0.05133 = 0.03788 -0.00758 -0.00165 -0.01148 AFIX 43 H14 2 0.154153 0.582490 0.276709 11.00000 -1.20000 AFIX 0 C15 1 0.154472 0.738270 0.405842 11.00000 0.04317 0.03777 = 0.05174 0.00075 0.00026 -0.00608 AFIX 43 H15 2 0.090066 0.863129 0.324201 11.00000 -1.20000 AFIX 0 C16 1 0.207506 0.726020 0.550245 11.00000 0.03997 0.03203 = 0.05737 -0.01182 0.00756 -0.01049 AFIX 43 H16 2 0.179771 0.841526 0.568501 11.00000 -1.20000 AFIX 0 HKLF 4 REM ia355_a.res in P-1 REM wR2 = 0.1024, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.0366 for 1985 Fo > 4sig(Fo) and 0.0456 for all 2396 data REM 128 parameters refined using 0 restraints END WGHT 0.0443 0.0905 REM Instructions for potential hydrogen bonds HTAB C2 O3 REM Highest difference peak 0.184, deepest hole -0.189, 1-sigma level 0.029 Q1 1 0.3567 0.4734 0.6431 11.00000 0.05 0.18 Q2 1 0.2458 0.4908 0.4372 11.00000 0.05 0.18 Q3 1 0.2535 0.6222 0.6172 11.00000 0.05 0.18 Q4 1 0.3290 0.3826 0.5655 11.00000 0.05 0.17 Q5 1 0.3087 0.5418 0.7428 11.00000 0.05 0.17 Q6 1 0.0960 0.1933 0.9183 11.00000 0.05 0.15 Q7 1 0.2868 0.4595 0.6763 11.00000 0.05 0.14 Q8 1 0.2296 0.7379 0.7951 11.00000 0.05 0.13 Q9 1 0.3729 0.3154 0.6779 11.00000 0.05 0.12 Q10 1 0.1370 0.7227 0.4996 11.00000 0.05 0.11 Q11 1 0.2368 0.1284 0.8611 11.00000 0.05 0.11 Q12 1 0.1630 0.2155 0.3186 11.00000 0.05 0.11 Q13 1 0.1398 0.6391 0.4145 11.00000 0.05 0.10 Q14 1 0.4862 -0.0393 0.9010 11.00000 0.05 0.10 Q15 1 0.2344 0.7262 0.4686 11.00000 0.05 0.10 Q16 1 0.1003 0.2828 0.9817 11.00000 0.05 0.09 Q17 1 0.3349 0.0212 0.7647 11.00000 0.05 0.09 Q18 1 0.3584 0.0628 0.3637 11.00000 0.05 0.09 Q19 1 0.3106 0.3340 0.4819 11.00000 0.05 0.09 Q20 1 0.3782 0.1524 0.8087 11.00000 0.05 0.09 ; _shelx_res_checksum 88458 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.30876(14) 0.66102(14) 0.86805(12) 0.0635(3) Uani 1 1 d . . . . . O2 O 0.44565(10) 0.19524(10) 0.75809(9) 0.0399(2) Uani 1 1 d . . . . . O3 O 0.33828(12) 0.21552(12) 0.47759(10) 0.0487(2) Uani 1 1 d . . . . . C1 C 0.36116(17) 0.52702(17) 0.82533(15) 0.0475(3) Uani 1 1 d . . . . . H1 H 0.445104 0.404844 0.896536 0.057 Uiso 1 1 calc R U . . . C2 C 0.34259(17) 0.06586(15) 0.83383(13) 0.0460(3) Uani 1 1 d . . . . . H2A H 0.428679 -0.064958 0.904022 0.055 Uiso 1 1 calc R U . . . H2B H 0.282168 0.050223 0.750829 0.055 Uiso 1 1 calc R U . . . C3 C 0.20249(18) 0.13918(17) 0.92834(13) 0.0474(3) Uani 1 1 d . . . . . C4 C 0.0870(2) 0.1982(2) 1.00277(16) 0.0628(4) Uani 1 1 d . . . . . H4 H -0.006612 0.246118 1.063100 0.075 Uiso 1 1 calc R U . . . C5 C 0.28170(18) 0.2214(2) 0.33033(15) 0.0532(3) Uani 1 1 d . . . . . H5A H 0.334493 0.304690 0.241896 0.080 Uiso 1 1 calc R U . . . H5B H 0.146429 0.275426 0.313610 0.080 Uiso 1 1 calc R U . . . H5C H 0.325348 0.088286 0.334418 0.080 Uiso 1 1 calc R U . . . C11 C 0.30266(14) 0.54247(15) 0.67047(13) 0.0376(2) Uani 1 1 d . . . . . C12 C 0.34390(13) 0.37466(14) 0.64173(12) 0.0347(2) Uani 1 1 d . . . . . C13 C 0.28909(14) 0.38820(15) 0.49393(12) 0.0387(2) Uani 1 1 d . . . . . C14 C 0.19336(16) 0.57126(18) 0.37706(14) 0.0480(3) Uani 1 1 d . . . . . H14 H 0.154153 0.582490 0.276709 0.058 Uiso 1 1 calc R U . . . C15 C 0.15447(17) 0.73827(17) 0.40584(15) 0.0529(3) Uani 1 1 d . . . . . H15 H 0.090066 0.863129 0.324201 0.063 Uiso 1 1 calc R U . . . C16 C 0.20751(15) 0.72602(16) 0.55024(15) 0.0461(3) Uani 1 1 d . . . . . H16 H 0.179771 0.841526 0.568501 0.055 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 O1 0.0762(7) 0.0562(5) 0.0761(7) -0.0401(5) 0.0101(5) -0.0289(5) O2 0.0397(4) 0.0305(4) 0.0429(4) -0.0094(3) -0.0081(3) -0.0088(3) O3 0.0549(5) 0.0478(4) 0.0435(4) -0.0220(4) -0.0049(4) -0.0117(4) C1 0.0533(7) 0.0401(6) 0.0549(7) -0.0200(5) 0.0020(5) -0.0217(5) C2 0.0619(7) 0.0326(5) 0.0424(6) -0.0093(4) -0.0072(5) -0.0200(5) C3 0.0560(7) 0.0464(6) 0.0340(5) -0.0031(5) -0.0083(5) -0.0249(5) C4 0.0635(8) 0.0726(9) 0.0412(6) -0.0100(6) 0.0002(6) -0.0256(7) C5 0.0555(7) 0.0719(8) 0.0432(6) -0.0295(6) 0.0069(5) -0.0279(6) C11 0.0327(5) 0.0334(5) 0.0447(6) -0.0127(4) 0.0053(4) -0.0136(4) C12 0.0289(4) 0.0307(5) 0.0386(5) -0.0088(4) 0.0001(4) -0.0095(4) C13 0.0327(5) 0.0400(5) 0.0393(5) -0.0134(4) 0.0022(4) -0.0109(4) C14 0.0409(6) 0.0513(6) 0.0379(5) -0.0076(5) -0.0017(4) -0.0115(5) C15 0.0432(6) 0.0378(6) 0.0517(7) 0.0008(5) 0.0003(5) -0.0061(5) C16 0.0400(6) 0.0320(5) 0.0574(7) -0.0118(5) 0.0076(5) -0.0105(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' 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 C12 O2 C2 114.44(8) . . ? C13 O3 C5 117.76(9) . . ? O1 C1 C11 123.97(11) . . ? O1 C1 H1 118.0 . . ? C11 C1 H1 118.0 . . ? O2 C2 C3 112.06(9) . . ? O2 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? O2 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 178.71(13) . . ? C3 C4 H4 180.0 . . ? O3 C5 H5A 109.5 . . ? O3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C12 C11 C16 119.64(10) . . ? C12 C11 C1 120.11(9) . . ? C16 C11 C1 120.24(10) . . ? O2 C12 C11 119.28(9) . . ? O2 C12 C13 120.20(9) . . ? C11 C12 C13 120.47(9) . . ? O3 C13 C14 125.31(10) . . ? O3 C13 C12 115.75(9) . . ? C14 C13 C12 118.94(10) . . ? C13 C14 C15 120.30(11) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 121.05(10) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 119.59(11) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? 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 C1 1.2151(14) . ? O2 C12 1.3792(11) . ? O2 C2 1.4367(13) . ? O3 C13 1.3614(13) . ? O3 C5 1.4279(13) . ? C1 C11 1.4668(16) . ? C1 H1 0.9500 . ? C2 C3 1.4541(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.1720(19) . ? C4 H4 0.9500 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C11 C12 1.3908(14) . ? C11 C16 1.3982(15) . ? C12 C13 1.4013(15) . ? C13 C14 1.3849(15) . ? C14 C15 1.3870(18) . ? C14 H14 0.9500 . ? C15 C16 1.3710(18) . ? C15 H15 0.9500 . ? C16 H16 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 C1 H1 O2 0.95 2.47 2.8025(13) 100 . yes C2 H2B O3 0.99 2.40 2.9889(14) 118 . yes C4 H4 O1 0.95 2.32 3.1986(19) 154 2_567 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 C12 O2 C2 C3 -66.77(11) . . . . ? O1 C1 C11 C12 -169.14(11) . . . . ? O1 C1 C11 C16 11.76(18) . . . . ? C2 O2 C12 C11 109.86(10) . . . . ? C2 O2 C12 C13 -72.62(12) . . . . ? C16 C11 C12 O2 176.85(9) . . . . ? C1 C11 C12 O2 -2.26(15) . . . . ? C16 C11 C12 C13 -0.67(15) . . . . ? C1 C11 C12 C13 -179.78(9) . . . . ? C5 O3 C13 C14 -2.26(16) . . . . ? C5 O3 C13 C12 178.57(9) . . . . ? O2 C12 C13 O3 1.76(14) . . . . ? C11 C12 C13 O3 179.25(9) . . . . ? O2 C12 C13 C14 -177.46(9) . . . . ? C11 C12 C13 C14 0.03(15) . . . . ? O3 C13 C14 C15 -178.45(10) . . . . ? C12 C13 C14 C15 0.69(17) . . . . ? C13 C14 C15 C16 -0.78(18) . . . . ? C14 C15 C16 C11 0.14(18) . . . . ? C12 C11 C16 C15 0.58(16) . . . . ? C1 C11 C16 C15 179.69(10) . . . . ?