#------------------------------------------------------------------------------ #$Date: 2024-07-05 20:53:48 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293238 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159890.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_7159890 loop_ _publ_author_name 'Barik, Rasmita' 'Nanda, Samik' _publ_section_title ; Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one. ; _journal_issue 22 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4478 _journal_page_last 4487 _journal_paper_doi 10.1039/d4ob00393d _journal_volume 22 _journal_year 2024 _chemical_formula_sum 'C15 H24 O2' _chemical_formula_weight 236.4 _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_update_record ; 2023-10-16 deposited with the CCDC. 2024-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.0794(2) _cell_length_b 13.0587(4) _cell_length_c 17.7262(6) _cell_measurement_reflns_used 6094 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.78 _cell_measurement_theta_min 2.78 _cell_volume 1407.27(8) _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker Photon III' _diffrn_measurement_method 'Bruker Photon III' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.0222 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 17469 _diffrn_reflns_theta_full 27.1 _diffrn_reflns_theta_max 27.1 _diffrn_reflns_theta_min 2.78 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.7066 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour White _exptl_crystal_density_diffrn 1.1156 _exptl_crystal_description Cuboid _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.34 _refine_diff_density_min -0.25 _refine_ls_abs_structure_details ' 1293 of Friedel pairs used in the refinement' _refine_ls_extinction_coef 27000(6000) _refine_ls_extinction_method 'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)' _refine_ls_goodness_of_fit_gt 2.68 _refine_ls_goodness_of_fit_ref 2.51 _refine_ls_hydrogen_treatment mixed _refine_ls_number_constraints 92 _refine_ls_number_parameters 154 _refine_ls_number_reflns 3092 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0463 _refine_ls_shift/su_max 0.0489 _refine_ls_shift/su_mean 0.0102 _refine_ls_structure_factor_coef F _refine_ls_weighting_details w=1/(\s^2^(F)+0.0001F^2^) _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.0552 _reflns_number_gt 2640 _reflns_number_total 3092 _reflns_threshold_expression I>3\s(I) _cod_data_source_file d4ob00393d2.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas Adding full bibliography for 7159890--7159891.cif. ; _cod_original_sg_symbol_Hall 'P 2xab;2ybc;2zac' _cod_database_code 7159890 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x+1/2,-y,z+1/2 3 -x,y+1/2,-z+1/2 4 x+1/2,-y+1/2,-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5645(3) 0.49426(15) 0.26438(9) Uani 0.0519(6) 4 1 d . . . H1c1 H 0.497304 0.476976 0.217056 Uiso 0.0623 4 1 d . . . H2c1 H 0.712975 0.470079 0.259571 Uiso 0.0623 4 1 d . . . C2 C 0.4512(3) 0.43723(14) 0.32694(10) Uani 0.0470(6) 4 1 d . . . H1c2 H 0.293375 0.436285 0.325967 Uiso 0.0564 4 1 d . . . C3 C 0.5482(3) 0.38803(13) 0.38345(10) Uani 0.0461(6) 4 1 d . . . C3a C 0.7936(4) 0.37278(18) 0.38920(13) Uani 0.0666(8) 4 1 d . . . H1c3a H 0.823546 0.308493 0.41338 Uiso 0.0799 4 1 d . . . H2c3a H 0.856706 0.372783 0.339563 Uiso 0.0799 4 1 d . . . H3c3a H 0.856642 0.427358 0.418334 Uiso 0.0799 4 1 d . . . C4 C 0.4207(3) 0.34613(13) 0.44976(10) Uani 0.0518(6) 4 1 d . . . H1c4 H 0.471132 0.278173 0.461055 Uiso 0.0621 4 1 d . . . H2c4 H 0.267966 0.340862 0.436596 Uiso 0.0621 4 1 d . . . C5 C 0.4455(4) 0.41397(13) 0.51991(10) Uani 0.0498(6) 4 1 d . . . H1c5 H 0.41043 0.374866 0.564162 Uiso 0.0598 4 1 d . . . H2c5 H 0.597119 0.432779 0.526011 Uiso 0.0598 4 1 d . . . C6 C 0.3039(3) 0.51038(14) 0.51784(10) Uani 0.0452(6) 4 1 d . . . H1c6 H 0.269027 0.52482 0.4661 Uiso 0.0542 4 1 d . . . O6a O 0.1118(3) 0.48961(14) 0.56241(8) Uani 0.0659(6) 4 1 d . . . H1o6a H 0.029(5) 0.535(2) 0.5540(16) Uiso 0.089(10) 4 1 d . . . C7 C 0.4195(4) 0.60832(14) 0.54569(10) Uani 0.0482(6) 4 1 d . . . H1c7 H 0.313447 0.662758 0.547259 Uiso 0.0579 4 1 d . . . C7a C 0.5013(4) 0.59994(18) 0.62697(11) Uani 0.0685(9) 4 1 d . . . H1c7a H 0.384701 0.575085 0.658554 Uiso 0.0822 4 1 d . . . H2c7a H 0.623272 0.553311 0.629068 Uiso 0.0822 4 1 d . . . H3c7a H 0.547501 0.666167 0.644356 Uiso 0.0822 4 1 d . . . C8 C 0.5978(3) 0.63751(13) 0.49057(10) Uani 0.0458(6) 4 1 d . . . O8a O 0.7940(3) 0.63781(11) 0.50735(8) Uiso 0.0623(4) 4 1 d . . . C9 C 0.5240(3) 0.65657(13) 0.41234(10) Uani 0.0435(6) 4 1 d . . . H1c9 H 0.383488 0.688313 0.404289 Uiso 0.0522 4 1 d . . . C10 C 0.6440(3) 0.63156(13) 0.35332(10) Uani 0.0441(6) 4 1 d . . . H1c10 H 0.799225 0.62458 0.361814 Uiso 0.053 4 1 d . . . C11 C 0.5655(3) 0.61273(14) 0.27425(9) Uani 0.0465(6) 4 1 d . . . C11a C 0.3358(4) 0.65574(19) 0.26054(11) Uani 0.0645(8) 4 1 d . . . H1c11a H 0.292698 0.64236 0.209379 Uiso 0.0774 4 1 d . . . H2c11a H 0.233432 0.623654 0.29434 Uiso 0.0774 4 1 d . . . H3c11a H 0.336559 0.728292 0.269275 Uiso 0.0774 4 1 d . . . C11b C 0.7235(4) 0.65936(19) 0.21607(12) Uani 0.0653(8) 4 1 d . . . H1c11b H 0.676301 0.641063 0.16617 Uiso 0.0783 4 1 d . . . H2c11b H 0.723602 0.732559 0.221078 Uiso 0.0783 4 1 d . . . H3c11b H 0.869277 0.633616 0.224574 Uiso 0.0783 4 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _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 C1 C 0.0532(11) 0.0641(12) 0.0386(9) 0.0033(10) -0.0020(9) -0.0058(8) C2 C 0.0438(11) 0.0491(10) 0.0480(10) -0.0031(9) -0.0030(9) -0.0088(8) C3 C 0.0506(11) 0.0381(9) 0.0497(10) -0.0017(9) -0.0027(9) -0.0085(7) C3a C 0.0573(14) 0.0688(15) 0.0736(15) 0.0099(12) -0.0029(11) 0.0056(11) C4 C 0.0587(13) 0.0385(9) 0.0582(11) -0.0077(9) -0.0030(10) 0.0025(8) C5 C 0.0594(13) 0.0451(10) 0.0449(10) -0.0022(10) -0.0066(9) 0.0083(7) C6 C 0.0457(11) 0.0543(11) 0.0355(9) 0.0014(9) -0.0031(8) 0.0051(7) O6a O 0.0549(10) 0.0828(11) 0.0599(9) 0.0017(9) 0.0103(7) 0.0139(8) C7 C 0.0589(13) 0.0463(10) 0.0394(9) 0.0067(10) -0.0037(9) 0.0000(7) C7a C 0.0927(19) 0.0712(14) 0.0416(10) -0.0055(13) -0.0115(11) -0.0036(10) C8 C 0.0539(11) 0.0361(9) 0.0475(10) 0.0010(9) -0.0075(9) -0.0010(7) C9 C 0.0480(11) 0.0374(9) 0.0451(10) 0.0068(8) -0.0032(9) 0.0037(7) C10 C 0.0411(10) 0.0428(10) 0.0486(10) 0.0011(8) -0.0037(8) 0.0056(7) C11 C 0.0410(10) 0.0599(11) 0.0384(9) 0.0064(9) 0.0000(8) 0.0066(7) C11a C 0.0527(12) 0.0926(16) 0.0481(11) 0.0195(12) -0.0040(10) 0.0104(11) C11b C 0.0648(14) 0.0728(15) 0.0582(12) 0.0070(12) 0.0092(11) 0.0187(11) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H1c1 C1 H2c1 . . . 104.17 ? H1c1 C1 C2 . . . 109.41 ? H1c1 C1 C11 . . . 109.51 ? H2c1 C1 C2 . . . 109.44 ? H2c1 C1 C11 . . . 109.49 ? C2 C1 C11 . . . 114.32(13) ? C1 C2 H1c2 . . . 116.85 ? C1 C2 C3 . . . 126.35(17) ? H1c2 C2 C3 . . . 116.8 ? C2 C3 C3a . . . 123.66(17) ? C2 C3 C4 . . . 122.32(17) ? C3a C3 C4 . . . 113.98(15) ? C3 C3a H1c3a . . . 109.45 ? C3 C3a H2c3a . . . 109.44 ? C3 C3a H3c3a . . . 109.51 ? H1c3a C3a H2c3a . . . 109.46 ? H1c3a C3a H3c3a . . . 109.47 ? H2c3a C3a H3c3a . . . 109.5 ? C3 C4 H1c4 . . . 109.43 ? C3 C4 H2c4 . . . 109.38 ? C3 C4 C5 . . . 111.78(13) ? H1c4 C4 H2c4 . . . 107.09 ? H1c4 C4 C5 . . . 109.54 ? H2c4 C4 C5 . . . 109.5 ? C4 C5 H1c5 . . . 109.42 ? C4 C5 H2c5 . . . 109.48 ? C4 C5 C6 . . . 113.69(16) ? H1c5 C5 H2c5 . . . 104.89 ? H1c5 C5 C6 . . . 109.5 ? H2c5 C5 C6 . . . 109.5 ? C5 C6 H1c6 . . . 108.06 ? C5 C6 O6a . . . 106.82(13) ? C5 C6 C7 . . . 114.81(16) ? H1c6 C6 O6a . . . 112.54 ? H1c6 C6 C7 . . . 104.16 ? O6a C6 C7 . . . 110.56(14) ? C6 O6a H1o6a . . . 106(2) ? C6 C7 H1c7 . . . 108.51 ? C6 C7 C7a . . . 113.05(15) ? C6 C7 C8 . . . 109.26(14) ? H1c7 C7 C7a . . . 104.15 ? H1c7 C7 C8 . . . 108.3 ? C7a C7 C8 . . . 113.26(19) ? C7 C7a H1c7a . . . 109.49 ? C7 C7a H2c7a . . . 109.44 ? C7 C7a H3c7a . . . 109.42 ? H1c7a C7a H2c7a . . . 109.54 ? H1c7a C7a H3c7a . . . 109.49 ? H2c7a C7a H3c7a . . . 109.45 ? C7 C8 O8a . . . 122.81(17) ? C7 C8 C9 . . . 115.60(16) ? O8a C8 C9 . . . 121.35(16) ? C8 C9 H1c9 . . . 118.77 ? C8 C9 C10 . . . 122.37(16) ? H1c9 C9 C10 . . . 118.86 ? C9 C10 H1c10 . . . 116.33 ? C9 C10 C11 . . . 127.33(17) ? H1c10 C10 C11 . . . 116.34 ? C1 C11 C10 . . . 105.64(12) ? C1 C11 C11a . . . 110.14(16) ? C1 C11 C11b . . . 108.76(15) ? C10 C11 C11a . . . 112.33(14) ? C10 C11 C11b . . . 111.26(15) ? C11a C11 C11b . . . 108.63(15) ? C11 C11a H1c11a . . . 109.53 ? C11 C11a H2c11a . . . 109.46 ? C11 C11a H3c11a . . . 109.46 ? H1c11a C11a H2c11a . . . 109.51 ? H1c11a C11a H3c11a . . . 109.48 ? H2c11a C11a H3c11a . . . 109.39 ? C11 C11b H1c11b . . . 109.43 ? C11 C11b H2c11b . . . 109.52 ? C11 C11b H3c11b . . . 109.47 ? H1c11b C11b H2c11b . . . 109.46 ? H1c11b C11b H3c11b . . . 109.42 ? H2c11b C11b H3c11b . . . 109.53 ? 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 C1 H1c1 . . 0.9601 ? C1 H2c1 . . 0.9602 ? C1 C2 . . 1.503(2) ? C1 C11 . . 1.5560(19) ? C2 H1c2 . . 0.9597 ? C2 C3 . . 1.328(2) ? C3 C3a . . 1.509(3) ? C3 C4 . . 1.512(2) ? C3a H1c3a . . 0.9602 ? C3a H2c3a . . 0.9599 ? C3a H3c3a . . 0.9598 ? C4 H1c4 . . 0.9595 ? C4 H2c4 . . 0.96 ? C4 C5 . . 1.534(2) ? C5 H1c5 . . 0.9603 ? C5 H2c5 . . 0.9599 ? C5 C6 . . 1.526(2) ? C6 H1c6 . . 0.9593 ? C6 O6a . . 1.436(2) ? C6 C7 . . 1.540(2) ? O6a H1o6a . . 0.79(3) ? C7 H1c7 . . 0.9603 ? C7 C7a . . 1.528(3) ? C7 C8 . . 1.508(3) ? C7a H1c7a . . 0.9593 ? C7a H2c7a . . 0.9599 ? C7a H3c7a . . 0.9604 ? C8 O8a . . 1.229(3) ? C8 C9 . . 1.480(2) ? C9 H1c9 . . 0.9599 ? C9 C10 . . 1.316(2) ? C10 H1c10 . . 0.9601 ? C10 C11 . . 1.501(2) ? C11 C11a . . 1.525(3) ? C11 C11b . . 1.535(3) ? C11a H1c11a . . 0.9593 ? C11a H2c11a . . 0.9603 ? C11a H3c11a . . 0.9606 ? C11b H1c11b . . 0.9607 ? C11b H2c11b . . 0.9594 ? C11b H3c11b . . 0.9599 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O6a H1o6a O8a . . 1_455 0.79(3) 2.13(3) 2.904(2) 166(3) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? loop_ _restr_angle_atom_site_label_1 _restr_angle_site_symmetry_1 _restr_angle_atom_site_label_2 _restr_angle_site_symmetry_2 _restr_angle_atom_site_label_3 _restr_angle_site_symmetry_3 _restr_angle_target _restr_angle_target_weight_param ? ? ? ? ? ? ? ? loop_ _restr_distance_atom_site_label_1 _restr_distance_site_symmetry_1 _restr_distance_atom_site_label_2 _restr_distance_site_symmetry_2 _restr_distance_target _restr_distance_target_weight_param ? ? ? ? ? ? loop_ _restr_equal_angle_atom_site_label_1 _restr_equal_angle_site_symmetry_1 _restr_equal_angle_atom_site_label_2 _restr_equal_angle_site_symmetry_2 _restr_equal_angle_atom_site_label_3 _restr_equal_angle_site_symmetry_3 _restr_equal_angle_class_class_id _restr_equal_angle_class_target_weight_param ? ? ? ? ? ? ? ? loop_ _restr_equal_distance_atom_site_label_1 _restr_equal_distance_site_symmetry_1 _restr_equal_distance_atom_site_label_2 _restr_equal_distance_site_symmetry_2 _restr_equal_distance_class_class_id _restr_equal_distance_class_target_weight_param ? ? ? ? ? ? loop_ _restr_equal_torsion_atom_site_label_1 _restr_equal_torsion_site_symmetry_1 _restr_equal_torsion_atom_site_label_2 _restr_equal_torsion_site_symmetry_2 _restr_equal_torsion_atom_site_label_3 _restr_equal_torsion_site_symmetry_3 _restr_equal_torsion_atom_site_label_4 _restr_equal_torsion_site_symmetry_4 _restr_equal_torsion_class_class_id _restr_equal_torsion_class_target_weight_param ? ? ? ? ? ? ? ? ? ? loop_ _restr_torsion_atom_site_label_1 _restr_torsion_site_symmetry_1 _restr_torsion_atom_site_label_2 _restr_torsion_site_symmetry_2 _restr_torsion_atom_site_label_3 _restr_torsion_site_symmetry_3 _restr_torsion_atom_site_label_4 _restr_torsion_site_symmetry_4 _restr_torsion_angle_target _restr_torsion_weight_param ? ? ? ? ? ? ? ? ? ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 ? ? ? ? ? ? ? ? ? ? ? loop_ _twin_refln_datum_id _twin_refln_individual_id _twin_refln_index_h _twin_refln_index_k _twin_refln_index_l _twin_refln_F_squared_calc _twin_refln_F_squared_meas _twin_refln_F_squared_sigma _twin_refln_include_status ? ? ? ? ? ? ? ? ? loop_ _jana_atom_site_adp_c_label _jana_atom_site_adp_c_type_symbol _jana_atom_site_adp_c_111 _jana_atom_site_adp_c_112 _jana_atom_site_adp_c_113 _jana_atom_site_adp_c_122 _jana_atom_site_adp_c_123 _jana_atom_site_adp_c_133 _jana_atom_site_adp_c_222 _jana_atom_site_adp_c_223 _jana_atom_site_adp_c_233 _jana_atom_site_adp_c_333 ? ? ? ? ? ? ? ? ? ? ? ? loop_ _jana_atom_site_adp_d_label _jana_atom_site_adp_d_type_symbol _jana_atom_site_adp_d_1111 _jana_atom_site_adp_d_1112 _jana_atom_site_adp_d_1113 _jana_atom_site_adp_d_1122 _jana_atom_site_adp_d_1123 _jana_atom_site_adp_d_1133 _jana_atom_site_adp_d_1222 _jana_atom_site_adp_d_1223 _jana_atom_site_adp_d_1233 _jana_atom_site_adp_d_1333 _jana_atom_site_adp_d_2222 _jana_atom_site_adp_d_2223 _jana_atom_site_adp_d_2233 _jana_atom_site_adp_d_2333 _jana_atom_site_adp_d_3333 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? loop_ _jana_atom_site_adp_e_label _jana_atom_site_adp_e_type_symbol _jana_atom_site_adp_e_11111 _jana_atom_site_adp_e_11112 _jana_atom_site_adp_e_11113 _jana_atom_site_adp_e_11122 _jana_atom_site_adp_e_11123 _jana_atom_site_adp_e_11133 _jana_atom_site_adp_e_11222 _jana_atom_site_adp_e_11223 _jana_atom_site_adp_e_11233 _jana_atom_site_adp_e_11333 _jana_atom_site_adp_e_12222 _jana_atom_site_adp_e_12223 _jana_atom_site_adp_e_12233 _jana_atom_site_adp_e_12333 _jana_atom_site_adp_e_13333 _jana_atom_site_adp_e_22222 _jana_atom_site_adp_e_22223 _jana_atom_site_adp_e_22233 _jana_atom_site_adp_e_22333 _jana_atom_site_adp_e_23333 _jana_atom_site_adp_e_33333 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? loop_ _jana_atom_site_adp_f_label _jana_atom_site_adp_f_type_symbol _jana_atom_site_adp_f_111111 _jana_atom_site_adp_f_111112 _jana_atom_site_adp_f_111113 _jana_atom_site_adp_f_111122 _jana_atom_site_adp_f_111123 _jana_atom_site_adp_f_111133 _jana_atom_site_adp_f_111222 _jana_atom_site_adp_f_111223 _jana_atom_site_adp_f_111233 _jana_atom_site_adp_f_111333 _jana_atom_site_adp_f_112222 _jana_atom_site_adp_f_112223 _jana_atom_site_adp_f_112233 _jana_atom_site_adp_f_112333 _jana_atom_site_adp_f_113333 _jana_atom_site_adp_f_122222 _jana_atom_site_adp_f_122223 _jana_atom_site_adp_f_122233 _jana_atom_site_adp_f_122333 _jana_atom_site_adp_f_123333 _jana_atom_site_adp_f_133333 _jana_atom_site_adp_f_222222 _jana_atom_site_adp_f_222223 _jana_atom_site_adp_f_222233 _jana_atom_site_adp_f_222333 _jana_atom_site_adp_f_223333 _jana_atom_site_adp_f_233333 _jana_atom_site_adp_f_333333 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?