Modular synthesis of thirty lead-like scaffolds suitable for CNS drug discovery
Mayol-Llinàs, Joan; Farnaby, William; Nelson, Adam; Chemical Communications  (2017) –; doi:10.1039/C7CC06078E

data_7120849
_publ_section_title
;
 Modular synthesis of thirty lead-like scaffolds suitable for CNS drug
 discovery
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC06078E
_journal_year                    2017
_chemical_formula_moiety         'C9 H13 N O3'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_name_systematic
;
 (4aR*,7aS*)-4a-(Prop-2-en-1-yl)-hexahydro-2H-furo[3,4-e][1,3]oxazin-2-one
;
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2017-08-03 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.65800(10)
_cell_length_b                   9.53160(10)
_cell_length_c                   12.1849(2)
_cell_measurement_reflns_used    3539
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.4770
_cell_measurement_theta_min      3.6140
_cell_volume                     886.29(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6191
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9864
_diffrn_measured_fraction_theta_max 0.9593
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00 -18.00   1.00    1.00    --  -38.50 -37.00   0.00   92
  2  \w    -64.00  30.00   1.00    1.00    --  -38.50  57.00 150.00   94
  3  \w    -59.00  33.00   1.00    1.00    --  -38.50  37.00   0.00   92
  4  \w     35.00 127.00   1.00    1.00    --  104.98 -45.00  30.00   92
  5  \w     83.00 175.00   1.00    1.00    --  104.98  45.00 -60.00   92
  6  \w     65.00 178.00   1.00    1.00    --  104.98  15.00  60.00  113
  7  \w     36.00 132.00   1.00    1.00    --  104.98 -65.00 -15.93   96
  8  \w     36.00 132.00   1.00    1.00    --  104.98 -65.00  11.82   96
  9  \w     16.00 112.00   1.00    1.00    --   42.96  63.00 118.89   96
 10  \w     18.00 111.00   1.00    1.00    --   42.96  57.00-120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2013103000
_diffrn_orient_matrix_UB_12      0.0088632000
_diffrn_orient_matrix_UB_13      -0.0160198000
_diffrn_orient_matrix_UB_21      -0.0058970000
_diffrn_orient_matrix_UB_22      0.0376299000
_diffrn_orient_matrix_UB_23      0.1225157000
_diffrn_orient_matrix_UB_31      0.0128488000
_diffrn_orient_matrix_UB_32      0.1570504000
_diffrn_orient_matrix_UB_33      -0.0286378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4943
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.677
_diffrn_reflns_theta_min         5.798
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             392.000
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0381P)^2^+0.2977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1590
_reflns_number_total             1726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06078e2.cif
_cod_data_source_block           jml313_cu
_cod_database_code               7120849
_chemical_oxdiff_formula         'C36 H52 N4 O12'
_reflns_odcompleteness_completeness 98.64
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.686