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_7124792
_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 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_name_systematic
'Ethyl (1R*,2R*,5S*,6R*,7S*)-3-[(2,4-dimethoxyphenyl)methyl]-4-oxo-2-(prop-2-en-1-yl)-10-oxa-3-azatricyclo[5.2.1.0^1^,5]dec-8-ene-6-carboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.8332(4)
_cell_length_b                   9.84289(14)
_cell_length_c                   16.7747(3)
_cell_measurement_reflns_used    11151
_cell_measurement_temperature    120.00(12)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      4.8800
_cell_volume                     3770.02(11)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(12)
_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 0.998
_diffrn_measurement_details
;
  1 omega  -17.00   25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 42

  2 omega  -33.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -150.0000 64

  3 omega  -64.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 91

  4 omega   40.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   30.0000 44

  5 omega   60.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -150.0000 26

  6 omega  112.00  162.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -120.0000 50

  7 omega   37.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   90.0000 39

  8 omega   71.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  -60.0000 26

  9 omega  107.00  133.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -30.0000 26

 10 omega  146.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -30.0000 32

 11 omega   47.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  150.0000 26

 12 omega   52.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000 -180.0000 42

 13 omega  118.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   60.0000 59

 14 omega   43.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000    0.0000 54

 15 omega  102.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000  -30.0000 44

 16 omega   74.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000  -30.0000 26

 17 omega   39.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   90.0000 28

 18 omega   48.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 42

 19 omega  111.00  152.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000    0.0000 41

 20 omega   51.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 26

 21 omega   93.00  142.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -120.0000 49

 22 omega   64.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -180.0000 26

 23 omega   45.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  150.0000 26

 24 omega   32.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -150.0000 49

 25 omega  119.00  145.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -150.0000 26

 26 omega   85.00  160.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000 -120.0000 75

 27 omega  102.00  147.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   60.0000 45

 28 omega   35.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -30.0000 36

 29 omega   91.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 25

 30 omega   38.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -51.0000  146.2998 62
;
_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      -0.0530062000
_diffrn_orient_matrix_UB_12      0.0010454000
_diffrn_orient_matrix_UB_13      0.0569025000
_diffrn_orient_matrix_UB_21      0.0198165000
_diffrn_orient_matrix_UB_22      -0.1372350000
_diffrn_orient_matrix_UB_23      0.0350158000
_diffrn_orient_matrix_UB_31      0.0368058000
_diffrn_orient_matrix_UB_32      0.0753547000
_diffrn_orient_matrix_UB_33      0.0629011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30290
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.395
_diffrn_reflns_theta_min         4.893
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.245
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0640P)^2^+0.9356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3356
_reflns_number_total             3855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04662b2.cif
_cod_data_source_block           jdf2_382b_cu
_cod_original_cell_volume        3770.04(11)
_cod_database_code               7124792
_chemical_oxdiff_formula         'C21 H23 N1 O4'
_reflns_odcompleteness_completeness 99.92
_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. Rigid body (RIGU) restrains
 C15A, C15B, C16A, C16B, C17A, C21A, C21B, C17B, C18A, C20A, C20B, C19A, C19A,
 C21A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C16A(0.5) C15A(0.5) H15A(0.5) H15B(0.5) C17A(0.5) H17A(0.5)
 C18A(0.5) H18A(0.5) C21A(0.5) H21A(0.5) C20A(0.5) H20A(0.5) C19A(0.5)
 H19A(0.5) C20B(0.5) H20B(0.5) C21B(0.5) H21B(0.5) C19B(0.5) H19B(0.5)
 C18B(0.5) H18B(0.5) C16B(0.5) C17B(0.5) H17B(0.5) C15B(0.5) H15C(0.5) H15D(0.5)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C9(H9), C11(H11), C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15A(H15A,H15B), C2(H2A,H2B), C15B(H15C,H15D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C17A(H17A), C18A(H18A), C21A(H21A), C20A(H20A),
 C19A(H19A), C20B(H20B), C21B(H21B), C19B(H19B), C18B(H18B), C17B(H17B)
4.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-09-10
_olex2_submission_special_instructions 'No special instructions were received'