A biosynthesis-inspired approach to over twenty diverse natural product-like scaffolds.
Firth, James D.; Craven, Philip G. E.; Lilburn, Matthew; Pahl, Axel; Marsden, Stephen P.; Nelson, Adam; Chemical communications (Cambridge, England) 52 (2016) 9837–9840; doi:10.1039/c6cc04662b

data_7124790
_publ_section_title
;
 A biosynthesis-inspired approach to over twenty diverse natural
 product-like scaffolds.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9837
_journal_page_last               9840
_journal_paper_doi               10.1039/c6cc04662b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_chemical_name_systematic
'Ethyl (2R*,3S*,5aS*,9aS*,9bR*)-5-benzyl-2-ethenyl-4-oxo-2H,3H,4H,5H,5aH,6H,7H,9bH-furo[3,2-d]indole-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-05-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9172(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.06181(17)
_cell_length_b                   9.47232(16)
_cell_length_c                   18.5215(2)
_cell_measurement_reflns_used    6665
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.3120
_cell_measurement_theta_min      4.0180
_cell_volume                     1922.20(5)
_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      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
  1 omega  -47.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  120.0000 80

  2 omega  -15.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  150.0000 27

  3 omega  -60.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  150.0000 27

  4 omega -106.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  150.0000 90

  5 omega   16.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7089   65.0000  152.2519 27

  6 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   30.0000 26

  7 omega  136.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000    0.0000 41

  8 omega  123.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   90.0000 45

  9 omega  139.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000  150.0000 32

 10 omega   98.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000  150.0000 26

 11 omega   89.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   90.0000 29

 12 omega   73.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   60.0000 25

 13 omega   84.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  101.0955 37

 14 omega   71.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   29.0189 35

 15 omega   70.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -30.0000 26

 16 omega  105.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 25

 17 omega  122.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -120.0000 55

 18 omega   75.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -120.0000 31

 19 omega   61.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -120.0000 27

 20 omega   61.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -56.0000 -165.6941 33

 21 omega   58.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 28

 22 omega   64.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  -29.9824 49

 23 omega   54.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   30.0000 34

 24 omega   60.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   60.0535 53

 25 omega   49.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  150.0000 26

 26 omega   43.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 46
;
_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      0.0752335000
_diffrn_orient_matrix_UB_12      -0.0009650000
_diffrn_orient_matrix_UB_13      -0.0640845000
_diffrn_orient_matrix_UB_21      -0.1181409000
_diffrn_orient_matrix_UB_22      0.0166163000
_diffrn_orient_matrix_UB_23      -0.0540029000
_diffrn_orient_matrix_UB_31      0.0127427000
_diffrn_orient_matrix_UB_32      0.1617629000
_diffrn_orient_matrix_UB_33      0.0052501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11845
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.451
_diffrn_reflns_theta_min         4.035
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.874
_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    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0654P)^2^+0.5183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3389
_reflns_number_total             3807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04662b2.cif
_cod_data_source_block           jdf3_464a_cu
_cod_database_code               7124790
_chemical_oxdiff_formula         'C88 H100 N4 O16'
_reflns_odcompleteness_completeness 98.15
_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), C4(H4), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C13(H13A,H13B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C18(H18)
2.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-30
_olex2_submission_special_instructions 'No special instructions were received'