Scalable Synthesis of (-)-Thapsigargin.
Chu, Hang; Smith, Joel M.; Felding, Jakob; Baran, Phil S.; ACS central science 3 (2017) 47–51; doi:10.1021/acscentsci.6b00313

data_4516781
_publ_section_title
;
 Scalable Synthesis of (-)-Thapsigargin.
;
_journal_issue                   1
_journal_name_full               'ACS central science'
_journal_page_first              47
_journal_page_last               51
_journal_paper_doi               10.1021/acscentsci.6b00313
_journal_volume                  3
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C H2 Cl2), C36 H29 N3 O13'
_chemical_formula_sum            'C38 H33 Cl4 N3 O13'
_chemical_formula_weight         881.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                82.0520(10)
_cell_angle_beta                 77.374(2)
_cell_angle_gamma                88.5010(10)
_cell_formula_units_Z            1
_cell_length_a                   8.2491(2)
_cell_length_b                   10.4883(2)
_cell_length_c                   11.6077(3)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      6.03
_cell_volume                     970.58(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.10-0 (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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24090
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        64.982
_diffrn_reflns_theta_max         64.982
_diffrn_reflns_theta_min         3.939
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.387
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0889 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.6272.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2858 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0425
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                6131
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oc6b00313_si_002.cif
_cod_data_source_block           baran561_a
_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               4516781
_shelx_estimated_absorpt_t_max   0.440
_shelx_estimated_absorpt_t_min   0.392
_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
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C8(H8A,H8B), C37(H37A,H37B), C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C12(H12), C29(H29), C25(H25), C35(H35), C15(H15), C5(H5), C33(H33),
 C36(H36), C1(H1), C4(H4), C32(H32), C2(H2), C28(H28), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              48992
_shelx_hkl_checksum              54423
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'