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_7124789
_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*,2S*,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      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_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                 92.5884(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.12275(8)
_cell_length_b                   19.6409(2)
_cell_length_c                   11.31395(11)
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.2520
_cell_measurement_theta_min      6.9480
_cell_volume                     1803.16(3)
_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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega   -5.00   29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -60.0000 34

  2 omega  -53.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -180.0000 83

  3 omega    3.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -120.0000 30

  4 omega  -33.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  120.0000 46

  5 omega  135.00  161.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  120.0000 26

  6 omega   50.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   90.0000 26

  7 omega   34.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -90.0000 32

  8 omega   38.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000 -180.0000 59

  9 omega  128.00  160.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000 -180.0000 32

 10 omega   88.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  150.0000 88

 11 omega   37.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000    0.0000 52

 12 omega   37.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   60.0000 60

 13 omega   35.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000  -60.0000 46

 14 omega  140.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   90.0000 35

 15 omega   66.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000   90.0000 40

 16 omega   72.00  130.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   90.0000 58

 17 omega   86.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000 -180.0000 26

 18 omega   70.00  126.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000    0.0000 56

 19 omega  104.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -180.0000 25

 20 omega   52.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000 -150.0000 25

 21 omega   79.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   40.9904 30
;
_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      -0.0821679000
_diffrn_orient_matrix_UB_12      0.0467071000
_diffrn_orient_matrix_UB_13      -0.0949425000
_diffrn_orient_matrix_UB_21      -0.1238546000
_diffrn_orient_matrix_UB_22      -0.0569351000
_diffrn_orient_matrix_UB_23      -0.0339467000
_diffrn_orient_matrix_UB_31      -0.1178415000
_diffrn_orient_matrix_UB_32      0.0271865000
_diffrn_orient_matrix_UB_33      0.0917503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5250
_diffrn_reflns_point_group_measured_fraction_full 0.739
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.353
_diffrn_reflns_theta_min         4.502
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.910
_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    1.302
_exptl_crystal_description       irregular
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0575P)^2^+0.5516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.459
_reflns_Friedel_fraction_full    0.483
_reflns_Friedel_fraction_max     0.455
_reflns_number_gt                2640
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04662b2.cif
_cod_data_source_block           jdf2_382a_cu
_cod_database_code               7124789
_chemical_oxdiff_formula         'C21 H23 N1 O4'
_reflns_odcompleteness_completeness 99.52
_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:
 C4(H4), C5(H5), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.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'