Synthesis and evaluation of novel quinuclidinone derivatives as potential anti-proliferative agents
Soni, Jigar Y.; Sanghvi, Shridhar; Devkar, Ranjitsinh V.; Thakore, Sonal; RSC Adv.  (2015) –; doi:10.1039/C5RA15127A

data_7222233
_publ_section_title
;
 Synthesis and evaluation of novel quinuclidinone derivatives as potential
 anti-proliferative agents
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA15127A
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17.5 H15 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-02-27 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.221(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.8724(3)
_cell_length_b                   8.1184(3)
_cell_length_c                   17.0501(10)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9940
_cell_measurement_theta_min      5.2030
_cell_volume                     810.65(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   11.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 25

  2 omega  -27.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000    0.0000 56

  3 omega -109.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -50.0000   30.0000 76

  4 omega   86.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 32

  5 omega  -11.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000   30.0000 93

  6 omega   24.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  -30.0000 68

  7 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 26

  8 omega   47.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 46

  9 omega   93.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  120.0000 43

 10 omega   44.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -60.0000 54

 11 omega   88.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 26

 12 omega   42.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 50

 13 omega   42.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  -30.0000 87

 14 omega  149.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  -30.0000 27

 15 omega   85.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000 -150.0000 40

 16 omega  120.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 25

 17 omega   71.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 33

 18 omega  108.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -180.0000 55

 19 omega   44.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 56

 20 omega   67.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 26

 21 omega   61.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  150.0000 25

 22 omega  117.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -180.0000 30

 23 omega   67.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2465333000
_diffrn_orient_matrix_UB_12      -0.0041504000
_diffrn_orient_matrix_UB_13      0.0251079000
_diffrn_orient_matrix_UB_21      -0.0912914000
_diffrn_orient_matrix_UB_22      0.0193009000
_diffrn_orient_matrix_UB_23      -0.0865775000
_diffrn_orient_matrix_UB_31      -0.0041303000
_diffrn_orient_matrix_UB_32      -0.1887548000
_diffrn_orient_matrix_UB_33      -0.0094066000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3740
_diffrn_reflns_theta_full        73.10
_diffrn_reflns_theta_max         73.10
_diffrn_reflns_theta_min         5.20
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2183
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.490
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0850
_refine_ls_shift/su_max          3.281
_refine_ls_shift/su_mean         0.271
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1573P)^2^+0.0026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2430
_refine_ls_wR_factor_ref         0.2507
_reflns_number_gt                2009
_reflns_number_total             2183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra15127a2.cif
_cod_data_source_block           exp_617
_cod_original_cell_volume        810.64(7)
_cod_database_code               7222233
_audit_block_doi                 10.5517/cc1494yj
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 89.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C18-C1AA \\sim C1AA-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C18: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C5(H5A,H5B), C8(H8A,H8B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'