Realisation of small molecule libraries based on frameworks distantly related to natural products.
Aimon, Anthony; Karageorgis, George; Masters, Jacob; Dow, Mark; Craven, Philip G. E.; Ohsten, Martin; Willaume, Anthony; Morgentin, Rémy; Ruiz-Llamas, Nicolas; Lemoine, Hugues; Kalliokoski, Tuomo; Eatherton, Andrew J.; Foley, Daniel J.; Marsden, Stephen P.; Nelson, Adam; Organic & biomolecular chemistry 16 (2018) 3160–3167; doi:10.1039/c8ob00688a

data_7156192
_publ_section_title
;
 Realisation of small molecule libraries based on frameworks distantly
 related to natural products.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3160
_journal_page_last               3167
_journal_paper_doi               10.1039/c8ob00688a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C22 H29 F N2 O4'
_chemical_formula_sum            'C22 H29 F N2 O4'
_chemical_formula_weight         404.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-10-02 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.984(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7014(2)
_cell_length_b                   14.4421(3)
_cell_length_c                   14.1016(4)
_cell_measurement_reflns_used    7487
_cell_measurement_temperature    119.99(17)
_cell_measurement_theta_max      74.3060
_cell_measurement_theta_min      4.4620
_cell_volume                     2084.36(9)
_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      119.99(17)
_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 0.997
_diffrn_measurement_details
;
  1 omega  -33.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -150.0000 55

  2 omega  -48.00   -1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -180.0000 47

  3 omega  -80.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000    0.0000  -60.0000 117

  4 omega   77.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -150.0000 58

  5 omega   99.00  125.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000 -180.0000 26

  6 omega   85.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000 -150.0000 90

  7 omega  139.00  165.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -60.0000 26

  8 omega  150.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000   30.0000 26

  9 omega  119.00  168.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   90.0000 49

 10 omega  108.00  145.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000  -30.0000 37

 11 omega  102.00  127.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -60.0000 25

 12 omega   84.00  136.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000   30.0000 52

 13 omega   93.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   30.0000 25

 14 omega   64.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 26

 15 omega  104.00  129.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   60.0000 25

 16 omega   56.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   30.0000 75

 17 omega   59.00  124.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  108.4734 65

 18 omega   55.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 25

 19 omega   42.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   30.0000 38

 20 omega   54.00  122.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 68

 21 omega   52.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000 -180.0000 46

 22 omega   40.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -180.0000 39
;
_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      0.0763796000
_diffrn_orient_matrix_UB_12      -0.0911254000
_diffrn_orient_matrix_UB_13      0.0049040000
_diffrn_orient_matrix_UB_21      0.0856812000
_diffrn_orient_matrix_UB_22      0.0252244000
_diffrn_orient_matrix_UB_23      0.1050605000
_diffrn_orient_matrix_UB_31      -0.0973922000
_diffrn_orient_matrix_UB_32      -0.0493166000
_diffrn_orient_matrix_UB_33      0.0446542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14166
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.387
_diffrn_reflns_theta_min         4.320
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.928
_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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0420P)^2^+0.6121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3739
_reflns_number_total             4241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00688a2.cif
_cod_data_source_block           aa581_cu
_cod_depositor_comments          'Adding full bibliography for 7156192.cif.'
_cod_original_cell_volume        2084.35(9)
_cod_database_code               7156192
_chemical_oxdiff_formula         'C22 H29 F1 N2 O4'
_reflns_odcompleteness_completeness 99.97
_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:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-16
_olex2_submission_special_instructions 'No special instructions were received'