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_7124791
_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         'C21 H22 F3 N O4'
_chemical_formula_sum            'C21 H22 F3 N O4'
_chemical_formula_weight         409.39
_chemical_name_systematic
'Methyl (1R*,2R*,5S*,8S*,9R*,10S*)-7-oxo-5-{[4-(trifluoromethyl)phenyl]methyl}-13-oxa-6-azatetracyclo[8.2.1.0^1^,8.0^2^,6]tridecane-9-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-18
_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                78.173(2)
_cell_angle_beta                 76.486(2)
_cell_angle_gamma                89.949(2)
_cell_formula_units_Z            8
_cell_length_a                   11.7112(3)
_cell_length_b                   15.2229(4)
_cell_length_c                   22.2156(6)
_cell_measurement_reflns_used    21806
_cell_measurement_temperature    119.99(18)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      4.5800
_cell_volume                     3764.55(18)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega -107.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -65.0000   42.7718 96

  2 omega -107.00  -12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -62.0000 -128.7230 95

  3 omega  -64.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -180.0000 94

  4 omega  -64.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000    0.0000 94

  5 omega  -26.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589  -64.0000 -156.7581 95

  6 omega   16.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   64.0000 -152.4784 95

  7 omega   15.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   65.0000  136.3918 96

  8 omega   15.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   65.0000   22.5721 96

  9 omega  -26.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589  -64.0000    8.6219 95

 10 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -64.0000    8.1232 96

 11 omega   83.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242   30.0000   60.0000 94

 12 omega   83.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242   30.0000  150.0000 94

 13 omega   31.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -30.0000 -120.0000 59

 14 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000   77.5114 96

 15 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000 -168.5889 96

 16 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000   44.2077 96

 17 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -64.0000  106.3265 96

 18 omega   31.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -30.0000  -60.0000 59

 19 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  -96.7013 96

 20 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  -67.7277 96

 21 omega   25.00  144.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -15.0000  120.0000 119

 22 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000 -131.7962 96

 23 omega   31.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -30.0000   30.0000 59

 24 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  -25.8588 96

 25 omega   35.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0242  -65.0000  149.0744 96

 26 omega   17.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   57.0000  -90.0000 94

 27 omega   16.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   64.0000   81.9619 95

 28 omega   22.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   37.0000    0.0000 92

 29 omega   22.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   37.0000  -90.0000 92

 30 omega   15.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   65.0000  -91.5379 96

 31 omega   22.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   37.0000   60.0000 92

 32 omega   16.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   64.0000  -54.4079 95
;
_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      -0.0410824000
_diffrn_orient_matrix_UB_12      -0.0005371000
_diffrn_orient_matrix_UB_13      0.0712124000
_diffrn_orient_matrix_UB_21      -0.0879226000
_diffrn_orient_matrix_UB_22      0.0721568000
_diffrn_orient_matrix_UB_23      -0.0141505000
_diffrn_orient_matrix_UB_31      -0.0945002000
_diffrn_orient_matrix_UB_32      -0.0742283000
_diffrn_orient_matrix_UB_33      0.0071542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.675
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.877
_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    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1050
_refine_ls_number_reflns         20977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0603
_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^)+(0.1090P)^2^+1.5254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17075
_reflns_number_total             20977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04662b2.cif
_cod_data_source_block           jdf3_509b_cu_a_twin1_hklf4
_cod_original_cell_volume        3764.56(18)
_cod_database_code               7124791
_chemical_oxdiff_formula         'C21 H22 F3 N1 O4'
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7305(8) 0.2695(8)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C10(H10), C13(H13), C66(H66), C67(H67), C71(H71),
 C73(H73), C76(H76), C24(H24), C25(H25), C29(H29), C31(H31), C34(H34), C45(H45),
  C46(H46), C50(H50), C52(H52), C55(H55)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C68(H68A,H68B), C69(H69A,H69B), C74(H74A,H74B), C75(H75A,H75B), C77(H77A,H77B),
  C26(H26A,H26B), C27(H27A,H27B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,
 H35B), C47(H47A,H47B), C48(H48A,H48B), C53(H53A,H53B), C54(H54A,H54B),
 C56(H56A,H56B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20), C79(H79), C80(H80), C82(H82),
 C83(H83), C37(H37), C38(H38), C40(H40), C41(H41), C58(H58), C59(H59), C61(H61),
  C62(H62)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C64(H64A,H64B,H64C), C22(H22A,H22B,H22C), C43(H43A,H43B,H43C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'