#------------------------------------------------------------------------------ #$Date: 2022-10-07 18:24:22 +0100 (Fri, 07 Oct 2022) $ #$Revision: 278488 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500130.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_3500130 loop_ _publ_author_name 'Maris, Thierry' 'Lalibert\'e, Dominic' 'Wuest, James D.' _publ_section_references ; APEX2 (2006) version 2.1-0; Bruker Molecular Analysis Research Tool. Bruker AXS Inc., Madison, WI 53719-1173. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2007). SADABS, Bruker Area Detector Absorption Corrections. Bruker AXS Inc., Madison, WI 53719-1173. Sheldrick, G.M. (2008). Acta Cryst. A71, 3-8. Sheldrick, G.M. (2008). Acta Cryst. C71, 3-8. Spek, A.L. (2008). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. XPREP (2005) Version 2005/2; X-ray data Preparation and Reciprocal space Exploration Program. Bruker AXS Inc., Madison, WI 53719-1173. ; _publ_section_title ; tetrakis[(3,5-dimethoxybenzyloxy) methyl]methane ; _journal_name_full 'Personal communication to COD' _journal_year 2022 _chemical_formula_moiety 'C41 H52 O12' _chemical_formula_sum 'C41 H52 O12' _chemical_formula_weight 736.82 _chemical_name_common ; tetrakis[(3,5-dimethoxybenzyloxy) methyl]methane ; _space_group_crystal_system tetragonal _space_group_IT_number 88 _space_group_name_Hall '-I 4ad' _space_group_name_H-M_alt 'I 41/a :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2020-04-08 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 26.1308(2) _cell_length_b 26.1308(2) _cell_length_c 5.4539(1) _cell_measurement_reflns_used 7070 _cell_measurement_temperature 150 _cell_measurement_theta_max 67.457 _cell_measurement_theta_min 3.383 _cell_volume 3724.02(8) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'APEX2 v2.1-0 (Bruker AXS, 2006a)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150.15 _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method \w _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_unetI/netI 0.0175 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 28301 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.190 _diffrn_reflns_theta_min 3.383 _diffrn_source 'rotating anode' _exptl_absorpt_coefficient_mu 0.791 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_correction_T_min 0.8627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2007/4 (Bruker,2007/4) was used for absorption correction. wR2(int) was 0.0778 before and 0.0586 after correction. The Ratio of minimum to maximum transmission is 0.8889. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1576 _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total). ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.125 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 1701 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0312 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+1.9461P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.0807 _refine_special_details ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B) 2.b Aromatic/amide H refined with riding coordinates: C9(H9), C7(H7), C5(H5) 2.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C10(H10A,H10B,H10C) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1463 _reflns_number_total 1701 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jw1358.cif _cod_data_source_block jw1358 _cod_original_cell_volume 3724.02(9) _cod_original_sg_symbol_H-M 'I 41/a' _cod_database_code 3500130 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y+1/2, z' 3 '-y+3/4, x+1/4, z+1/4' 4 'y+1/4, -x+1/4, z+1/4' 5 'x+1/2, y+1/2, z+1/2' 6 '-x+1/2, -y+1, z+1/2' 7 '-y+5/4, x+3/4, z+3/4' 8 'y+3/4, -x+3/4, z+3/4' 9 '-x, -y, -z' 10 'x, y-1/2, -z' 11 'y-3/4, -x-1/4, -z-1/4' 12 '-y-1/4, x-1/4, -z-1/4' 13 '-x+1/2, -y+1/2, -z+1/2' 14 'x+1/2, y, -z+1/2' 15 'y-1/4, -x+1/4, -z+1/4' 16 '-y+1/4, x+1/4, -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 O1 O 0.96585(3) 0.16493(3) 0.64379(15) 0.0271(2) Uani 1 1 d . . . . . O2 O 0.84198(3) 0.07852(3) 0.11366(16) 0.0330(2) Uani 1 1 d . . . . . O3 O 0.93085(3) -0.05836(3) 0.50146(18) 0.0359(2) Uani 1 1 d . . . . . C1 C 1.000000 0.250000 0.625000 0.0203(5) Uani 1 4 d S T P . . C2 C 0.98475(4) 0.20534(4) 0.7911(2) 0.0225(3) Uani 1 1 d . . . . . H2A H 1.014822 0.193516 0.885931 0.027 Uiso 1 1 calc R U . . . H2B H 0.958059 0.216515 0.908277 0.027 Uiso 1 1 calc R U . . . C4 C 0.93171(4) 0.08074(4) 0.6163(2) 0.0260(3) Uani 1 1 d . . . . . C9 C 0.89742(4) 0.09587(4) 0.4386(2) 0.0271(3) Uani 1 1 d . . . . . H9 H 0.888721 0.130994 0.421640 0.033 Uiso 1 1 calc R U . . . C8 C 0.87557(4) 0.05958(4) 0.2840(2) 0.0261(3) Uani 1 1 d . . . . . C6 C 0.92153(4) -0.00681(4) 0.4921(2) 0.0271(3) Uani 1 1 d . . . . . C7 C 0.88780(4) 0.00813(4) 0.3068(2) 0.0275(3) Uani 1 1 d . . . . . H7 H 0.873498 -0.016471 0.198380 0.033 Uiso 1 1 calc R U . . . C11 C 0.82109(5) 0.04309(5) -0.0575(2) 0.0327(3) Uani 1 1 d . . . . . H11A H 0.848911 0.026795 -0.149345 0.049 Uiso 1 1 calc R U . . . H11B H 0.798460 0.061204 -0.171519 0.049 Uiso 1 1 calc R U . . . H11C H 0.801536 0.016882 0.030438 0.049 Uiso 1 1 calc R U . . . C5 C 0.94383(4) 0.02889(4) 0.6465(2) 0.0272(3) Uani 1 1 d . . . . . H5 H 0.966996 0.018383 0.770931 0.033 Uiso 1 1 calc R U . . . C3 C 0.95645(5) 0.11984(4) 0.7807(2) 0.0302(3) Uani 1 1 d . . . . . H3A H 0.933630 0.127625 0.920732 0.036 Uiso 1 1 calc R U . . . H3B H 0.989049 0.106205 0.846192 0.036 Uiso 1 1 calc R U . . . C10 C 0.95560(5) -0.07749(5) 0.7156(3) 0.0375(3) Uani 1 1 d . . . . . H10A H 0.990139 -0.063052 0.726685 0.056 Uiso 1 1 calc R U . . . H10B H 0.957782 -0.114875 0.706263 0.056 Uiso 1 1 calc R U . . . H10C H 0.935896 -0.067680 0.861099 0.056 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 0.0371(5) 0.0205(4) 0.0238(4) 0.0019(3) -0.0028(4) -0.0072(3) O2 0.0368(5) 0.0275(4) 0.0345(5) -0.0021(4) -0.0087(4) 0.0010(3) O3 0.0410(5) 0.0201(4) 0.0466(6) 0.0009(4) -0.0026(4) 0.0030(3) C1 0.0205(6) 0.0205(6) 0.0198(11) 0.000 0.000 0.000 C2 0.0234(5) 0.0228(6) 0.0214(6) -0.0006(5) -0.0010(4) -0.0020(4) C4 0.0274(6) 0.0236(6) 0.0272(6) 0.0017(5) 0.0040(5) -0.0033(4) C9 0.0302(6) 0.0205(5) 0.0306(7) 0.0013(5) 0.0020(5) -0.0009(4) C8 0.0244(6) 0.0275(6) 0.0265(7) 0.0022(5) 0.0021(5) -0.0005(4) C6 0.0259(6) 0.0205(6) 0.0349(7) 0.0018(5) 0.0067(5) 0.0001(4) C7 0.0278(6) 0.0244(6) 0.0303(7) -0.0031(5) 0.0041(5) -0.0030(4) C11 0.0301(6) 0.0364(7) 0.0316(7) -0.0065(6) -0.0024(5) -0.0008(5) C5 0.0262(6) 0.0255(6) 0.0298(7) 0.0039(5) 0.0018(5) -0.0011(4) C3 0.0389(7) 0.0234(6) 0.0281(7) 0.0046(5) -0.0024(5) -0.0053(5) C10 0.0394(7) 0.0262(6) 0.0470(8) 0.0096(6) 0.0042(6) 0.0058(5) 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' 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 C2 O1 C3 112.44(9) . . C8 O2 C11 117.08(9) . . C6 O3 C10 117.14(10) . . C2 C1 C2 107.39(8) . 2_755 C2 C1 C2 107.39(8) 15_666 16_646 C2 C1 C2 110.52(4) . 16_646 C2 C1 C2 110.52(4) 2_755 15_666 C2 C1 C2 110.52(4) 2_755 16_646 C2 C1 C2 110.52(4) . 15_666 O1 C2 C1 108.88(8) . . O1 C2 H2A 109.9 . . O1 C2 H2B 109.9 . . C1 C2 H2A 109.9 . . C1 C2 H2B 109.9 . . H2A C2 H2B 108.3 . . C9 C4 C5 120.47(11) . . C9 C4 C3 120.24(10) . . C5 C4 C3 119.29(11) . . C4 C9 H9 120.1 . . C4 C9 C8 119.84(10) . . C8 C9 H9 120.1 . . O2 C8 C9 115.30(10) . . O2 C8 C7 123.94(11) . . C7 C8 C9 120.76(11) . . O3 C6 C7 114.47(10) . . O3 C6 C5 124.39(11) . . C5 C6 C7 121.13(10) . . C8 C7 C6 118.77(11) . . C8 C7 H7 120.6 . . C6 C7 H7 120.6 . . O2 C11 H11A 109.5 . . O2 C11 H11B 109.5 . . O2 C11 H11C 109.5 . . H11A C11 H11B 109.5 . . H11A C11 H11C 109.5 . . H11B C11 H11C 109.5 . . C4 C5 H5 120.5 . . C6 C5 C4 119.00(11) . . C6 C5 H5 120.5 . . O1 C3 C4 108.97(10) . . O1 C3 H3A 109.9 . . O1 C3 H3B 109.9 . . C4 C3 H3A 109.9 . . C4 C3 H3B 109.9 . . H3A C3 H3B 108.3 . . O3 C10 H10A 109.5 . . O3 C10 H10B 109.5 . . O3 C10 H10C 109.5 . . H10A C10 H10B 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C2 1.4158(13) . O1 C3 1.4164(13) . O2 C8 1.3704(14) . O2 C11 1.4236(15) . O3 C6 1.3697(13) . O3 C10 1.4256(16) . C1 C2 1.5303(11) 2_755 C1 C2 1.5303(11) . C1 C2 1.5303(11) 16_646 C1 C2 1.5303(11) 15_666 C2 H2A 0.9900 . C2 H2B 0.9900 . C4 C9 1.3779(17) . C4 C5 1.4010(16) . C4 C3 1.5052(16) . C9 H9 0.9500 . C9 C8 1.3916(16) . C8 C7 1.3874(16) . C6 C7 1.3967(18) . C6 C5 1.3854(17) . C7 H7 0.9500 . C11 H11A 0.9800 . C11 H11B 0.9800 . C11 H11C 0.9800 . C5 H5 0.9500 . C3 H3A 0.9900 . C3 H3B 0.9900 . C10 H10A 0.9800 . C10 H10B 0.9800 . C10 H10C 0.9800 . 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 O2 C8 C7 C6 -178.24(10) . . . . O3 C6 C7 C8 179.38(10) . . . . O3 C6 C5 C4 179.13(11) . . . . C2 O1 C3 C4 174.47(9) . . . . C2 C1 C2 O1 53.97(10) 15_666 . . . C2 C1 C2 O1 174.59(10) 2_755 . . . C2 C1 C2 O1 -64.78(10) 16_646 . . . C4 C9 C8 O2 179.98(10) . . . . C4 C9 C8 C7 0.14(17) . . . . C9 C4 C5 C6 1.14(17) . . . . C9 C4 C3 O1 -36.06(15) . . . . C9 C8 C7 C6 1.59(17) . . . . C7 C6 C5 C4 0.63(17) . . . . C11 O2 C8 C9 176.37(10) . . . . C11 O2 C8 C7 -3.79(16) . . . . C5 C4 C9 C8 -1.53(17) . . . . C5 C4 C3 O1 144.08(11) . . . . C5 C6 C7 C8 -1.98(17) . . . . C3 O1 C2 C1 173.10(8) . . . . C3 C4 C9 C8 178.62(11) . . . . C3 C4 C5 C6 -179.00(11) . . . . C10 O3 C6 C7 -166.68(11) . . . . C10 O3 C6 C5 14.73(17) . . . . _cod_database_fobs_code 3500130