First total synthesis of concavine
Saint-Dizier, François; Simpkins, Nigel S.; Chem. Sci. 8 (2017) 3384–; doi:10.1039/C6SC05627J

data_1545478
_publ_section_title
;
 First total synthesis of concavine
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3384
_journal_paper_doi               10.1039/C6SC05627J
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C22 H31 N O3 S, C H2 Cl2'
_chemical_formula_sum            'C23 H33 Cl2 N O3 S'
_chemical_formula_weight         474.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-21 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0555(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.9274(3)
_cell_length_b                   5.87596(8)
_cell_length_c                   29.0682(4)
_cell_measurement_reflns_used    8423
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9660
_cell_measurement_theta_min      3.2300
_cell_volume                     4599.29(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9843
_diffrn_measurement_details
;
  1 omega -115.00  -20.00   1.0000    4.0576
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -38.0000  -90.0000 95

  2 omega  -95.00   -2.00   1.0000    4.0576
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  125.0000   90.0000 93

  3 omega -115.00  -20.00   1.0000    4.0576
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -38.0000 -180.0000 95

  4 omega   61.00  178.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000    0.0000 117

  5 omega   32.00   91.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  -30.0000 59

  6 omega   35.00   99.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   30.0000 64

  7 omega   25.00  109.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000    0.0000 84

  8 omega   32.00   91.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   30.0000 59

  9 omega   25.00  109.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -90.0000 84

 10 omega   35.00   99.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 64

 11 omega -113.00  -16.00   1.0000    4.0576
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -57.0000    0.0000 97

 12 omega  -50.00   30.00   1.0000    4.0576
omega____ theta____ kappa____ phi______ frames
    -      -42.4357   38.0000    0.0000 80

 13 omega -115.00  -20.00   1.0000    4.0576
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -38.0000   60.0000 95

 14 omega   83.00  178.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000 -180.0000 95

 15 omega   35.00   99.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  120.0000 64

 16 omega   79.00  177.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 98

 17 omega   79.00  177.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   30.0000 98

 18 omega   25.00   95.00   1.0000   16.2302
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  150.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0464061000
_diffrn_orient_matrix_UB_12      0.0041989000
_diffrn_orient_matrix_UB_13      0.0310309000
_diffrn_orient_matrix_UB_21      0.0330952000
_diffrn_orient_matrix_UB_22      -0.0445277000
_diffrn_orient_matrix_UB_23      -0.0422750000
_diffrn_orient_matrix_UB_31      0.0049759000
_diffrn_orient_matrix_UB_32      0.2582425000
_diffrn_orient_matrix_UB_33      -0.0077712000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19675
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         3.041
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.587
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.1388
_exptl_crystal_size_mid          0.0867
_exptl_crystal_size_min          0.0464
_refine_diff_density_max         0.844
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0754
_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^)+(0.1255P)^2^+21.3406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3878
_reflns_number_total             4194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05627j2.cif
_cod_data_source_block           23
_cod_depositor_comments          'Adding full bibliography for 1545478.cif.'
_cod_database_code               1545478
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C22 H31 N O3 S'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C3(H3), C5A(H5AA), C10A(H10C)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B), C101(H10D,H10E)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              11157
_olex2_submission_special_instructions 'No special instructions were received'