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_7222232
_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_formula_moiety         'C21 H19 Br N2 O2'
_chemical_formula_sum            'C21 H19 Br N2 O2'
_chemical_formula_weight         411.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2014-09-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                75.954(6)
_cell_angle_beta                 80.580(5)
_cell_angle_gamma                74.016(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1410(4)
_cell_length_b                   9.6496(7)
_cell_length_c                   11.1631(8)
_cell_measurement_reflns_used    3847
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.3290
_cell_measurement_theta_min      4.1010
_cell_volume                     913.33(11)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 0.9308
_diffrn_measured_fraction_theta_max 0.9915
_diffrn_measurement_details
;
  1 omega  -99.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214  -57.0000   90.0000 99

  2 omega  -55.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214  -57.0000    0.0000 47

  3 omega -115.00  -48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214 -178.0000 -180.0000 67

  4 omega   11.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   38.0000 -120.0000 41

  5 omega  -30.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   38.0000 -120.0000 38

  6 omega  -99.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214  -57.0000    0.0000 33

  7 omega -152.00  -86.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000 -111.0000  120.0000 66

  8 omega -129.00  -68.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  178.0000   90.0000 61

  9 omega -152.00  -70.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  -38.0000  -30.0000 82

 10 omega  -39.00    8.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000  -30.0000 47

 11 omega  -56.00    6.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   21.0000 -120.0000 62

 12 omega  -21.00    5.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  104.0000   60.0000 26

 13 omega  -51.00    5.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   43.0000  120.0000 56

 14 omega  -56.00  -25.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  -38.0000  -30.0000 31

 15 omega  -74.00  -34.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
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 16 omega   67.00  132.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607   64.0000 -150.0000 65

 17 omega   57.00  150.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  178.0000  120.0000 93

 18 omega   39.00  106.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  -64.0000 -120.0000 67

 19 omega   87.00  147.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  142.0000 -104.0000 60

 20 omega   88.00  114.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  178.0000    0.0000 26

 21 omega   86.00  112.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  120.0000 26

 22 omega   43.00  101.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000  150.0000 58

 23 omega  119.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000 -180.0000 59

 24 omega   68.00   94.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000   30.0000 26

 25 omega  135.00  166.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000  -30.0000 31

 26 omega  108.00  134.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000  -90.0000 26

 27 omega   41.00   97.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000    0.0000  -90.0000 56

 28 omega  129.00  155.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000    0.0000  -90.0000 26

 29 omega   57.00  113.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000    0.0000 56

 30 omega   44.00  111.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -150.0000 67

 31 omega   45.00   80.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000    0.0000 35

 32 omega  112.00  174.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000   60.0000 62

 33 omega   91.00  177.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   65.0000   90.0000 86

 34 omega   44.00   94.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000  -30.0000 50

 35 omega  123.00  165.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000   30.0000 42

 36 omega   69.00   95.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  -60.0000 26

 37 omega   50.00   90.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -65.0000  -90.0000 40

 38 omega   49.00   74.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   90.0000 25

 39 omega   51.00   93.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000 -180.0000 42

 40 omega  153.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  150.0000 25

 41 omega   80.00  109.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   90.0000 29

 42 omega   73.00  103.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000  -90.0000 30

 43 omega   97.00  122.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -128.0000   10.0000 25

 44 omega   83.00  110.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -180.0000 27

 45 omega   52.00   90.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   30.0000 38

 46 omega   48.00   74.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -128.0000   10.0000 26

 47 omega   49.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000   60.0000 49

 48 omega   52.00  151.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -65.0000   60.0000 99

 49 omega   71.00   99.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000 -180.0000 28

 50 omega   86.00  112.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  120.0000 26

 51 omega   42.00  112.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -120.0000 70

 52 omega   47.00   73.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   60.0000 26

 53 omega  124.00  149.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   65.0000   30.0000 25

 54 omega  114.00  177.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  120.0000 63

 55 omega   78.00  103.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  150.0000 25

 56 omega  110.00  135.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -89.0000  120.0000 25

 57 omega   88.00  125.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  150.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0429915000
_diffrn_orient_matrix_UB_12      -0.0966698000
_diffrn_orient_matrix_UB_13      -0.0979719000
_diffrn_orient_matrix_UB_21      -0.0041369000
_diffrn_orient_matrix_UB_22      0.1387372000
_diffrn_orient_matrix_UB_23      -0.1039850000
_diffrn_orient_matrix_UB_31      0.1708902000
_diffrn_orient_matrix_UB_32      -0.0154456000
_diffrn_orient_matrix_UB_33      0.0068107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6973
_diffrn_reflns_theta_full        75.4347
_diffrn_reflns_theta_max         75.43
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39417
_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_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4955
_exptl_crystal_description       needle
_exptl_crystal_F_000             419.7381
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.6467
_refine_diff_density_min         -0.5938
_refine_diff_density_rms         0.0729
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             10.7709
_refine_ls_goodness_of_fit_ref   1.0518
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0518
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.1735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3290
_reflns_number_total             3753
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra15127a2.cif
_cod_data_source_block           exp_592
_cod_database_code               7222232
_chemical_oxdiff_formula         'C H O N Br'
_reflns_odcompleteness_completeness 93.08
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C8(H8a,H8b), C7(H7a,H7b), C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 N18(H18), C15(H15), C24(H24), C9(H9), C25(H25), C14(H14), C21(H21), C22(H22),
 C12(H12), C11(H11)
;