#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010273.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010273 loop_ _publ_author_name 'M. Gary Newton' 'Richard K. Hill' _publ_section_title ; A C~20~ 2:3 formaldehyde--cyclohexanone adduct ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1969 _journal_page_last 1971 _journal_paper_doi 10.1107/S0108270194005743 _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C20 H30 O3' _chemical_formula_sum 'C20 H30 O3' _chemical_formula_weight 318.46 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source ; Cromer \& Waber (1974) for non-H atoms and Stewart, Davidson \& Simpson (1965) for H atoms ; _cell_angle_alpha 90 _cell_angle_beta 95.965(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.9470(10) _cell_length_b 7.3850(10) _cell_length_c 17.8170(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 40.0 _cell_measurement_theta_min 20.0 _cell_volume 1694.3(3) _computing_cell_refinement ' CAD-4 Software' _computing_data_collection ' CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction ' TEXSAN (Molecular Structure Corporation, 1992)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR88 (Burla et al., 1989)' _diffrn_ambient_temperature 296.2 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 2636 _diffrn_reflns_theta_max 74.90 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% -0.68 _diffrn_standards_interval_count 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.248 _exptl_crystal_description needle _exptl_crystal_F_000 696.00 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max -0.22 _refine_diff_density_min 0.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 4.160 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 1968 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.048 _refine_ls_shift/esd_max 0.00 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_obs 0.056 _reflns_number_observed 1968 _reflns_number_total 2636 _reflns_observed_criterion I>3\s(I) _cod_data_source_file cr1137.cif _cod_data_source_block 2:3_Formaldehyde-Cyclohexanone_Adduct _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 53 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_original_cell_volume 1694.2(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2010273 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -z' 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0290(8) 0.0530(8) 0.0570(10) -0.0046(6) 0.0030(7) 0.0104(7) O(2) 0.0351(8) 0.0530(8) 0.0364(9) -0.0092(5) -0.0002(7) 0.0042(5) O(3) 0.0299(8) 0.0398(7) 0.0374(9) 0.0017(5) 0.0036(6) 0.0000(5) C(1a) 0.0180(10) 0.0239(9) 0.0310(10) -0.0005(6) 0.0047(9) 0.0056(7) C(2a) 0.0300(10) 0.0460(10) 0.066(2) -0.0050(8) 0.0120(10) 0.0144(10) C(3a) 0.0280(10) 0.0600(10) 0.073(2) -0.0060(10) 0.0120(10) 0.0080(10) C(4a) 0.031(2) 0.075(2) 0.054(2) 0.0100(10) 0.0160(10) -0.0010(10) C(5a) 0.045(2) 0.0510(10) 0.050(2) 0.0140(10) 0.0100(10) -0.0069(10) C(6a) 0.0420(10) 0.0460(10) 0.0390(10) 0.0017(8) 0.0090(10) -0.0034(8) C(7a) 0.055(2) 0.0380(10) 0.051(2) -0.0029(9) 0.0100(10) -0.0099(8) C(1b) 0.0290(10) 0.0417(10) 0.0370(10) -0.0049(7) 0.0019(9) 0.0057(7) C(2b) 0.0490(10) 0.0450(10) 0.041(2) -0.0146(9) 0.0030(10) -0.0027(8) C(3b) 0.046(2) 0.072(2) 0.033(2) -0.0230(10) 0.0010(10) -0.0060(10) C(4b) 0.041(2) 0.083(2) 0.022(2) -0.0090(10) -0.0020(10) 0.0160(10) C(5b) 0.0390(10) 0.0630(10) 0.048(2) -0.0050(10) -0.0030(10) 0.0270(10) C(6b) 0.0290(10) 0.0355(9) 0.0440(10) -0.0011(7) 0.0023(9) 0.0094(8) C(7b) 0.0320(10) 0.0352(10) 0.071(2) 0.0026(7) 0.0050(10) 0.0034(9) C(1c) 0.0150(10) 0.0234(9) 0.0260(10) -0.0038(7) 0.0025(9) -0.0027(7) C(2c) 0.0300(10) 0.0440(10) 0.061(2) 0.0030(8) 0.0050(10) -0.0115(9) C(3c) 0.041(2) 0.0470(10) 0.088(3) -0.0010(10) -0.002(2) -0.0300(10) C(4c) 0.050(2) 0.084(2) 0.060(3) -0.013(2) 0.003(2) -0.046(2) C(5c) 0.035(2) 0.073(2) 0.032(2) -0.0080(10) -0.0060(10) -0.0060(10) C(6c) 0.0350(10) 0.0670(10) 0.034(2) -0.0057(10) 0.0020(10) 0.0011(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) -0.01190(10) 0.1955(2) 0.93650(10) 0.0465 Uani ? ? O(2) 0.13130(10) 0.0897(2) 1.01215(9) 0.0376 Uani ? ? O(3) 0.29550(10) 0.2066(2) 1.00363(9) 0.0357 Uani ? ? C(1a) 0.2712(2) 0.2419(2) 0.92370(10) 0.0241 Uani ? ? C(2a) 0.3479(2) 0.3886(3) 0.9027(2) 0.0470 Uani ? ? C(3a) 0.4604(2) 0.3297(3) 0.9211(2) 0.0534 Uani ? ? C(4a) 0.4834(2) 0.1500(4) 0.8839(2) 0.0525 Uani ? ? C(5a) 0.4062(2) 0.0061(3) 0.9036(2) 0.0482 Uani ? ? C(6a) 0.2947(2) 0.0664(3) 0.88130(10) 0.0421 Uani ? ? C(7a) 0.2164(2) -0.0848(3) 0.8932(2) 0.0476 Uani ? ? C(1b) 0.0918(2) 0.1396(2) 0.93670(10) 0.0361 Uani ? ? C(2b) 0.1029(2) -0.0246(3) 0.8858(2) 0.0452 Uani ? ? C(3b) 0.0569(3) 0.0199(4) 0.8064(2) 0.0503 Uani ? ? C(4b) 0.1019(3) 0.1914(4) 0.7728(2) 0.0488 Uani ? ? C(5b) 0.1137(2) 0.3479(3) 0.8296(2) 0.0502 Uani ? ? C(6b) 0.1551(2) 0.3006(2) 0.91100(10) 0.0362 Uani ? ? C(7b) 0.1383(2) 0.4598(2) 0.9639(2) 0.0461 Uani ? ? C(1c) 0.2094(2) 0.2115(2) 1.04590(10) 0.0217 Uani ? ? C(2c) 0.1634(2) 0.4028(3) 1.0465(2) 0.0447 Uani ? ? C(3c) 0.2415(2) 0.5293(3) 1.0920(2) 0.0590 Uani ? ? C(4c) 0.2734(3) 0.4605(5) 1.1695(3) 0.0646 Uani ? ? C(5c) 0.3214(3) 0.2693(4) 1.1674(2) 0.0474 Uani ? ? C(6c) 0.2437(2) 0.1403(3) 1.1239(2) 0.0455 Uani ? ? H(1) -0.0531 0.0863 0.9503 0.0566 Uani ? ? H(2) 0.3394 0.5143 0.9291 0.0348 Uani ? ? H(3) 0.3403 0.4125 0.8448 0.0654 Uani ? ? H(4) 0.4771 0.3145 0.9773 0.0567 Uani ? ? H(5) 0.5125 0.4338 0.9022 0.0781 Uani ? ? H(6) 0.5516 0.1131 0.9069 0.0772 Uani ? ? H(7) 0.4778 0.1636 0.8354 0.0564 Uani ? ? H(8) 0.4077 -0.0136 0.9530 0.0427 Uani ? ? H(9) 0.4171 -0.0969 0.8833 0.0845 Uani ? ? H(10) 0.2894 0.0983 0.8237 0.0525 Uani ? ? H(11) 0.2331 -0.1394 0.9398 0.0574 Uani ? ? H(12) 0.2245 -0.1797 0.8568 0.0632 Uani ? ? H(13) 0.0573 -0.1247 0.9011 0.0580 Uani ? ? H(14) 0.0097 0.0345 0.8054 0.0680 Uani ? ? H(15) 0.0586 -0.0677 0.7757 0.0963 Uani ? ? H(16) 0.0669 0.2220 0.7338 0.0842 Uani ? ? H(17) 0.1530 0.1633 0.7533 0.0425 Uani ? ? H(18) 0.0469 0.3992 0.8381 0.0761 Uani ? ? H(19) 0.1594 0.4488 0.8105 0.0722 Uani ? ? H(20) 0.0596 0.4970 0.9559 0.0631 Uani ? ? H(21) 0.1852 0.5644 0.9458 0.0591 Uani ? ? H(22) 0.0958 0.4005 1.0733 0.0416 Uani ? ? H(23) 0.2114 0.6347 1.0834 0.1041 Uani ? ? H(24) 0.2957 0.5345 1.0613 0.0498 Uani ? ? H(25) 0.2365 0.4534 1.1914 0.0526 Uani ? ? H(26) 0.3237 0.5343 1.2070 0.1447 Uani ? ? H(27) 0.3395 0.2284 1.2133 0.0794 Uani ? ? H(28) 0.3698 0.2667 1.1429 0.0520 Uani ? ? H(29) 0.2793 0.0079 1.1190 0.0941 Uani ? ? H(30) 0.1847 0.1282 1.1531 0.0605 Uani ? ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C 0.018 0.009 H 0.000 0.000 O 0.049 0.032 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 1 -3 -2 3 2 -3 0 -5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C(1b) O(2) C(1c) 113.40(10) yes C(1a) O(3) C(1c) 114.6(2) yes O(3) C(1a) C(2a) 106.6(2) yes O(3) C(1a) C(6a) 107.20(10) yes O(3) C(1a) C(6b) 107.5(2) yes C(2a) C(1a) C(6a) 107.8(2) yes C(2a) C(1a) C(6b) 113.9(2) yes C(6a) C(1a) C(6b) 113.5(2) yes C(1a) C(2a) C(3a) 111.9(2) yes C(2a) C(3a) C(4a) 112.4(2) yes C(3a) C(4a) C(5a) 110.1(2) yes C(4a) C(5a) C(6a) 111.3(2) yes C(1a) C(6a) C(5a) 110.3(2) yes C(1a) C(6a) C(7a) 112.0(2) yes C(5a) C(6a) C(7a) 111.8(2) yes C(6a) C(7a) C(2b) 114.8(2) yes O(1) C(1b) O(2) 109.0(2) yes O(1) C(1b) C(2b) 112.3(2) yes O(1) C(1b) C(6b) 108.10(10) yes O(2) C(1b) C(2b) 107.8(2) yes O(2) C(1b) C(6b) 109.1(2) yes C(2b) C(1b) C(6b) 110.5(2) yes C(7a) C(2b) C(1b) 109.1(2) yes C(7a) C(2b) C(3b) 115.1(2) yes C(1b) C(2b) C(3b) 109.3(2) yes C(2b) C(3b) C(4b) 114.5(2) yes C(3b) C(4b) C(5b) 112.2(3) yes C(4b) C(5b) C(6b) 117.0(2) yes C(1a) C(6b) C(1b) 106.10(10) yes C(1a) C(6b) C(5b) 116.0(2) yes C(1a) C(6b) C(7b) 108.7(2) yes C(1b) C(6b) C(5b) 108.2(2) yes C(1b) C(6b) C(7b) 107.2(2) yes C(5b) C(6b) C(7b) 110.3(2) yes C(6b) C(7b) C(2c) 110.4(2) yes O(2) C(1c) O(3) 108.8(2) yes O(2) C(1c) C(2c) 108.8(2) yes O(2) C(1c) C(6c) 107.1(2) yes O(3) C(1c) C(2c) 110.9(2) yes O(3) C(1c) C(6c) 108.0(2) yes C(2c) C(1c) C(6c) 113.0(2) yes C(7b) C(2c) C(1c) 106.9(2) yes C(7b) C(2c) C(3c) 113.6(2) yes C(1c) C(2c) C(3c) 109.2(2) yes C(2c) C(3c) C(4c) 112.6(3) yes C(3c) C(4c) C(5c) 111.3(3) yes C(4c) C(5c) C(6c) 109.5(3) yes C(1c) C(6c) C(5c) 111.4(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O(1) C(1b) ? ? 1.405(3) yes O(2) C(1b) ? ? 1.436(3) yes O(2) C(1c) ? ? 1.437(2) yes O(3) C(1a) ? ? 1.450(3) yes O(3) C(1c) ? ? 1.409(3) yes C(1a) C(2a) ? ? 1.542(3) yes C(1a) C(6a) ? ? 1.546(3) yes C(1a) C(6b) ? ? 1.557(3) yes C(2a) C(3a) ? ? 1.522(4) yes C(3a) C(4a) ? ? 1.526(4) yes C(4a) C(5a) ? ? 1.525(4) yes C(5a) C(6a) ? ? 1.523(4) yes C(6a) C(7a) ? ? 1.537(3) yes C(7a) C(2b) ? ? 1.528(4) yes C(1b) C(2b) ? ? 1.529(3) yes C(1b) C(6b) ? ? 1.540(3) yes C(2b) C(3b) ? ? 1.512(4) yes C(3b) C(4b) ? ? 1.541(4) yes C(4b) C(5b) ? ? 1.534(5) yes C(5b) C(6b) ? ? 1.533(4) yes C(6b) C(7b) ? ? 1.536(3) yes C(7b) C(2c) ? ? 1.533(4) yes C(1c) C(2c) ? ? 1.533(3) yes C(1c) C(6c) ? ? 1.509(4) yes C(2c) C(3c) ? ? 1.544(3) yes C(3c) C(4c) ? ? 1.489(6) yes C(4c) C(5c) ? ? 1.545(5) yes C(5c) C(6c) ? ? 1.536(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 6934995