Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products.
Yin, Zhiyong; Maczka, Michael; Schnakenburg, Gregor; Schulz, Stefan; Dickschat, Jeroen S.; Organic & biomolecular chemistry 22 (2024) 5748–5758; doi:10.1039/d4ob00934g

data_7160000
_publ_section_title
;
 Enantioselective synthesis of all stereoisomers of geosmin and of
 biosynthetically related natural products.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5748
_journal_page_last               5758
_journal_paper_doi               10.1039/d4ob00934g
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H20 O'
_chemical_formula_sum            'C12 H20 O'
_chemical_formula_weight         180.28
_chemical_name_systematic        SGS-4
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-21 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   36.7093(10)
_cell_length_b                   26.4549(9)
_cell_length_c                   6.8153(2)
_cell_measurement_reflns_used    39213
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.78
_cell_measurement_theta_min      3.98
_cell_volume                     6618.6(3)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.189.0 (STOE, 2022)
;
_computing_data_reduction
;
X-Area Integrate 2.5.11.0 (STOE, 2022)
X-Area LANA 2.7.9.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
 2471 frames, detector distance = 60 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            77736
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.744
_diffrn_reflns_theta_min         4.819
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 3497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.00056(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         11933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0766
_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^)+(0.1139P)^2^+4.4557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2194
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                9654
_reflns_number_total             11933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00934g2.cif
_cod_data_source_block           ent-19
_cod_depositor_comments
'Adding full bibliography for 7159997--7160000.cif.'
_cod_database_code               7160000
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.751
_olex2_refinement_description
;
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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C10A(H10A), C1B(H1B), C10B(H10B), C1C(H1C), C10C(H10C), C1D(H1D),
 C10D(H10D), C1E(H1E), C10E(H10E), C1F(H1F), C10F(H10F)
2.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,
 H9AB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C9B(H9BA,H9BB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C7C(H7CA,H7CB), C8C(H8CA,H8CB),
  C9C(H9CA,H9CB), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C7D(H7DA,H7DB), C8D(H8DA,
 H8DB), C9D(H9DA,H9DB), C2E(H2EA,H2EB), C3E(H3EA,H3EB), C7E(H7EA,H7EB),
 C8E(H8EA,H8EB), C9E(H9EA,H9EB), C2F(H2FA,H2FB), C3F(H3FA,H3FB), C7F(H7FA,H7FB),
  C8F(H8FA,H8FB), C9F(H9FA,H9FB)
2.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C6B(H6B), C6C(H6C), C6D(H6D), C6E(H6E), C6F(H6F)
2.d Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C11B(H11D,H11E,H11F), C12B(H12D,
 H12E,H12F), C11C(H11G,H11H,H11I), C12C(H12G,H12H,H12I), C11D(H11J,H11K,H11L),
 C12D(H12J,H12K,H12L), C11E(H11M,H11N,H11O), C12E(H12M,H12N,H12O), C11F(H11P,
 H11Q,H11R), C12F(H12P,H12Q,H12R)
2.e Idealised tetrahedral OH refined as rotating group:
 OA(HA), OB(HB), OC(HC), OD(HD), OE(HE), OF(HF)
;
_shelx_res_checksum              33876
_olex2_submission_special_instructions 'No special instructions were received'