Efficient construction of the A/C/D tricyclic skeleton of palhinine A
Duan, Shuangshuang; Long, Dan; Zhao, Changgui; Zhao, Gaoyuan; Yuan, Ziyun; Xie, Xingang; Fang, Jianguo; She, Xuegong; Organic Chemistry Frontiers 3 (2016) 1137–; doi:10.1039/C6QO00222F

data_1553482
_publ_section_title
;
 Efficient construction of the A/C/D tricyclic skeleton of palhinine A
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1137
_journal_paper_doi               10.1039/C6QO00222F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C23 H27 N O6 S'
_chemical_formula_sum            'C23 H27 N O6 S'
_chemical_formula_weight         445.51
_chemical_melting_point          482.0(10)
_chemical_name_systematic
(7aR,9aS,11R)-9a-methoxy-4-tosyl-3,4,5,6,9a,11-hexahydro-1H-7a,11-methanobenzofuro[3,3a-e]azonine-7,10(2H,8H)-dione
_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             2015-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.152(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2306(9)
_cell_length_b                   9.8924(12)
_cell_length_c                   26.999(4)
_cell_measurement_reflns_used    837
_cell_measurement_temperature    293.78(10)
_cell_measurement_theta_max      18.6060
_cell_measurement_theta_min      3.6690
_cell_volume                     2176.1(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      293.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   72.00   97.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000   60.0000 17

  2 omega  -46.00   77.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000  -60.0000 82

  3 omega   -9.00   90.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   90.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0161835000
_diffrn_orient_matrix_UB_12      0.0209315000
_diffrn_orient_matrix_UB_13      -0.0239636000
_diffrn_orient_matrix_UB_21      0.0363399000
_diffrn_orient_matrix_UB_22      0.0602807000
_diffrn_orient_matrix_UB_23      0.0106496000
_diffrn_orient_matrix_UB_31      0.0773864000
_diffrn_orient_matrix_UB_32      -0.0326330000
_diffrn_orient_matrix_UB_33      0.0042432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.1872
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9071
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.651
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.2471
_refine_ls_R_factor_gt           0.1529
_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^)+(0.1233P)^2^+15.0480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3522
_refine_ls_wR_factor_ref         0.4085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1755
_reflns_number_total             4061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00222f2.cif
_cod_data_source_block           wangzm0615_2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '481-483' was changed to
'482.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2176.0(5)
_cod_database_code               1553482
_chemical_oxdiff_formula         'C14 S4 H8'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B),
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-15
_olex2_submission_special_instructions 'No special instructions were received'