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_7124795
_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 H28 N2 O4'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46
_chemical_name_systematic
'Ethyl (1R*,2S*,10S*,11R*,12S*)-5-benzyl-9-oxo-15-oxa-5,8-diazatetracyclo[10.2.1.0^1^,^1^\%.0^2^,8]pentadecane-11-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-19
_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                 94.3265(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.67334(14)
_cell_length_b                   11.20885(18)
_cell_length_c                   18.6086(2)
_cell_measurement_reflns_used    8503
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.3810
_cell_measurement_theta_min      4.5850
_cell_volume                     2011.93(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 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega  -35.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   30.0000 68

  2 omega  -31.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  150.0000 64

  3 omega   22.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4589   57.0000   90.0000 35

  4 omega   50.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 32

  5 omega   42.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000   30.0000 41

  6 omega   42.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   30.0000 30

  7 omega   37.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 35

  8 omega   88.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  -58.5319 27

  9 omega   92.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -60.0000 26

 10 omega   67.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000  -73.9609 27

 11 omega   60.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  -94.7755 58

 12 omega   81.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -180.0000 26

 13 omega  125.00  151.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000 -120.0000 26

 14 omega  133.00  160.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -30.0000 27

 15 omega  136.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000    0.0000 30

 16 omega  124.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   90.0000 29

 17 omega   98.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000  -30.0000 26

 18 omega   86.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000    0.0000 25

 19 omega   87.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000   60.0000 27

 20 omega   38.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 60

 21 omega   45.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -65.0000   -7.5474 73

 22 omega   49.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -150.0000 34

 23 omega   43.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000 -150.0000 63

 24 omega   29.00   54.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -15.0000 -180.0000 25

 25 omega   81.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000 -120.0000 82

 26 omega  -24.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.4589  -57.0000  -60.0000 90
;
_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      -0.0432678000
_diffrn_orient_matrix_UB_12      0.1322992000
_diffrn_orient_matrix_UB_13      0.0003144000
_diffrn_orient_matrix_UB_21      0.0939143000
_diffrn_orient_matrix_UB_22      0.0254356000
_diffrn_orient_matrix_UB_23      -0.0614843000
_diffrn_orient_matrix_UB_31      -0.1217173000
_diffrn_orient_matrix_UB_32      -0.0273231000
_diffrn_orient_matrix_UB_33      -0.0557731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14342
_diffrn_reflns_point_group_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.354
_diffrn_reflns_theta_min         2.111
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   analytical
_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)
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    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0693P)^2^+0.2017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.552
_reflns_Friedel_fraction_full    0.637
_reflns_Friedel_fraction_max     0.600
_reflns_number_gt                6178
_reflns_number_total             6546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04662b2.cif
_cod_data_source_block           jdf2_400a_cu
_cod_database_code               7124795
_chemical_oxdiff_formula         'C22 H28 N2 O4'
_reflns_odcompleteness_completeness 98.76
_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:
 C26(H26), C27(H27), C31(H31), C33(H33), C11(H11), C4(H4), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C28(H28A,H28B), C29(H29A,H29B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C2(H2A,H2B), C12(H12A,
 H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C6(H6A,H6B), C16(H16A,
 H16B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C22(H22), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-19
_olex2_submission_special_instructions 'No special instructions were received'