Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist.
Roach, Jeremy J.; Sasano, Yusuke; Schmid, Cullen L.; Zaidi, Saheem; Katritch, Vsevolod; Stevens, Raymond C.; Bohn, Laura M.; Shenvi, Ryan A.; ACS central science 3 (2017) 1329–1336; doi:10.1021/acscentsci.7b00488

data_4516789
_publ_section_title
;
 Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of
 20-nor-Salvinorin A, a Potent \k-OR Agonist.
;
_journal_issue                   12
_journal_name_full               'ACS central science'
_journal_page_first              1329
_journal_page_last               1336
_journal_paper_doi               10.1021/acscentsci.7b00488
_journal_volume                  3
_journal_year                    2017
_chemical_formula_moiety         'C16 H22 O5'
_chemical_formula_sum            'C16 H22 O5'
_chemical_formula_weight         294.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
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_cell_formula_units_Z            8
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_cell_length_b                   6.0100(2)
_cell_length_c                   36.8552(13)
_cell_measurement_reflns_used    6436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      2.69
_cell_volume                     3349.0(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
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_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24496
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
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_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.503
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
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_exptl_absorpt_correction_T_min  0.4619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1025 before and 0.0397 after correction. The Ratio of minimum to maximum transmission is 0.9411. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6136
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_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0395P)^2^+3.9072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4668
_reflns_number_total             6136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oc7b00488_si_004.cif
_cod_data_source_block           reint_a_sq
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4516789
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_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:
 C3(H3), C4(H4A), C10(H10), C14(H14), C3'(H3'), C4'(H4'A), C10'(H10'),
 C14'(H14')
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C6'(H6'A,H6'B),
 C7'(H7'A,H7'B), C11'(H11C,H11D), C12'(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C2'(H2')
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C1'(H1'A,H1'B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C9'(H9'A,H9'B,H9'C), C16'(H16D,H16E,H16F)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4'(H4')
;
_shelx_res_checksum              89104
_shelx_hkl_checksum              82729
_shelx_fab_checksum              56765
_olex2_submission_special_instructions 'No special instructions were received'