Model system for irreversible inhibition of Nek2: thiol addition to ethynylpurines and related substituted heterocycles.
Lebraud, Honorine; Coxon, Christopher R.; Archard, Victoria S.; Bawn, Carlo M.; Carbain, Benoit; Matheson, Christopher J.; Turner, David M.; Cano, Celine; Griffin, Roger J.; Hardcastle, Ian R.; Baisch, Ulrich; Harrington, Ross W.; Golding, Bernard T.; Organic & biomolecular chemistry 12 (2014) 141–148; doi:10.1039/c3ob41806e

data_7153643
_publ_section_title
;
 Model system for irreversible inhibition of Nek2: thiol addition to
 ethynylpurines and related substituted heterocycles.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              141
_journal_page_last               148
_journal_paper_doi               10.1039/c3ob41806e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C16 H14 N6 O'
_chemical_formula_sum            'C16 H14 N6 O'
_chemical_formula_weight         306.33
_chemical_name_systematic
2-(3-((6-Ethynyl-9-methyl-9H-purin-2-yl)amino)phenyl)acetamide
_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             2013-07-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.57(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.838(4)
_cell_length_b                   4.7845(9)
_cell_length_c                   14.873(4)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      60.7430
_cell_measurement_theta_min      2.1980
_cell_volume                     1428.4(6)
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9757
_diffrn_measurement_details
;
  1 omega  -24.00   13.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.9244  -99.0000   90.0000 37

  2 omega    9.00   50.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.9244 -119.0000  130.0000 41

  3 omega   39.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        1.9244   38.0000  -90.0000 39

  4 omega  -24.00   14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        1.9244   38.0000  -90.0000 38

  5 omega  -22.00   43.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        1.9244  -99.0000  -90.0000 65

  6 omega -120.00  -75.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  125.0000  150.0000 45

  7 omega -111.00  -86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000  125.0000    0.0000 25

  8 omega -126.00 -100.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000 -119.0000  -34.0000 26

  9 omega  -25.00    1.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.0000   30.0000  -60.0000 26

 10 omega    8.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158  -30.0000  -30.0000 61

 11 omega   66.00  156.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158   30.0000 -120.0000 90

 12 omega   31.00  110.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158  -77.0000 -150.0000 79

 13 omega   22.00  112.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158  -77.0000  -30.0000 90

 14 omega   35.00   75.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158  -45.0000  120.0000 40

 15 omega   54.00  154.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158   30.0000  -30.0000 100

 16 omega   23.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158 -125.0000 -180.0000 68

 17 omega   20.00   75.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6158  -45.0000   30.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0418686000
_diffrn_orient_matrix_UB_12      0.0503992000
_diffrn_orient_matrix_UB_13      -0.0695718000
_diffrn_orient_matrix_UB_21      -0.0125630000
_diffrn_orient_matrix_UB_22      -0.3036234000
_diffrn_orient_matrix_UB_23      -0.0347209000
_diffrn_orient_matrix_UB_31      -0.0629668000
_diffrn_orient_matrix_UB_32      0.0943605000
_diffrn_orient_matrix_UB_33      -0.0745111000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7158
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.424
_diffrn_reflns_theta_min         2.201
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   analytical
_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)
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)
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2948
_exptl_crystal_size_mid          0.1308
_exptl_crystal_size_min          0.0371
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0811P)^2^+0.0035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1481
_reflns_number_total             2226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ob41806e.txt
_cod_data_source_block           rjg120010new
_cod_original_cell_volume        1428.3(6)
_cod_database_code               7153643
_chemical_oxdiff_formula         'C16 H14 N6 O1'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C13(H13)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelxl_version_number           2013-3