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_7124794
_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 (1R*,2R*,5S*,6R*,7S*)-3-benzyl-2-(but-3-en-1-yl)-4-oxo-10-oxa-3-azatricyclo[5.2.1.0^1^,5]dec-8-ene-6-carboxylate'
_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             2015-12-01
_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                 90.065(8)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   9.8686(9)
_cell_length_b                   23.9445(18)
_cell_length_c                   33.107(2)
_cell_measurement_reflns_used    2778
_cell_measurement_temperature    119.98(14)
_cell_measurement_theta_max      54.1130
_cell_measurement_theta_min      5.3660
_cell_volume                     7823.1(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      119.98(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -115.00  -29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000 -120.0000 86

  2 omega  -32.00   29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 61

  3 omega    2.00   33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -180.0000 31

  4 omega   38.00   64.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 26

  5 omega   96.00  123.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000   60.0000 27

  6 omega   40.00   74.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 34

  7 omega   34.00   66.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 32

  8 omega   72.00   98.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   60.0000 26

  9 omega   33.00   90.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -180.0000 57

 10 omega   67.00   94.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000    0.0000 27

 11 omega  112.00  144.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000    0.0000 32

 12 omega   45.00   77.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 32

 13 omega   92.00  119.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 27

 14 omega   34.00   87.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 53

 15 omega   84.00  121.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -60.0000 37

 16 omega  104.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 27

 17 omega   73.00  128.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   60.0000 55

 18 omega  150.00  178.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   60.0000 28

 19 omega   34.00   76.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 42
;
_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      -0.0083600000
_diffrn_orient_matrix_UB_12      -0.0320143000
_diffrn_orient_matrix_UB_13      -0.0403125000
_diffrn_orient_matrix_UB_21      0.1000214000
_diffrn_orient_matrix_UB_22      -0.0439019000
_diffrn_orient_matrix_UB_23      0.0164114000
_diffrn_orient_matrix_UB_31      -0.1194923000
_diffrn_orient_matrix_UB_32      -0.0344712000
_diffrn_orient_matrix_UB_33      0.0164886000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25119
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        54.239
_diffrn_reflns_theta_max         54.239
_diffrn_reflns_theta_min         3.246
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.902
_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    1.248
_exptl_crystal_description       needle
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     974
_refine_ls_number_reflns         8978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0730
_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^)+(0.0731P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6725
_reflns_number_total             8978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04662b2.cif
_cod_data_source_block           jdf3_432b_cu
_cod_original_cell_volume        7823.1(11)
_cod_database_code               7124794
_chemical_oxdiff_formula         'C352 H432 N16 O64'
_reflns_odcompleteness_completeness 93.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5629(16) 0.4371(16)
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:
 C2(H2), C4(H4), C18(H18), C19(H19), C68(H68), C70(H70), C84(H84), C85(H85),
 C24(H24), C26(H26), C40(H40), C41(H41), C46(H46), C48(H48), C62(H62), C63(H63)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C13(H13A,H13B), C21(H21A,H21B), C71(H71A,H71B),
 C78(H78A,H78B), C79(H79A,H79B), C87(H87A,H87B), C27(H27A,H27B), C34(H34A,H34B),
  C35(H35A,H35B), C43(H43A,H43B), C49(H49A,H49B), C56(H56A,H56B), C57(H57A,
 H57B), C65(H65A,H65B)
3.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C), C88(H88A,H88B,H88C), C44(H44A,H44B,H44C), C66(H66A,H66B,
 H66C)
3.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C16(H16), C17(H17),
 C73(H73), C74(H74), C75(H75), C76(H76), C77(H77), C80(H80), C82(H82), C83(H83),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C36(H36), C38(H38),
 C39(H39), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C58(H58), C60(H60),
  C61(H61)
3.e X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C81(H81A,H81B), C37(H37A,H37B), C59(H59A,H59B)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-18
_olex2_submission_special_instructions 'No special instructions were received'