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_7153642
_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, 0.5(C H4 O)'
_chemical_formula_sum            'C16.5 H16 N6 O1.5'
_chemical_formula_weight         322.35
_chemical_name_systematic
2-(3-((6-Ethynyl-7-methyl-7H-purin-2-yl)amino)phenyl)acetamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 117.831(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3730(7)
_cell_length_b                   14.1912(4)
_cell_length_c                   16.2612(7)
_cell_measurement_reflns_used    10793
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      28.5804
_cell_measurement_theta_min      2.8649
_cell_volume                     3137.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details
;
  1 omega  -19.00    8.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850   85.0000   19.0000 27

  2 omega  -14.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000  -30.0000 102

  3 omega    7.00   51.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -99.0000   30.0000 44

  4 omega    6.00   33.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -41.0000 -147.0000 27

  5 omega   -3.00   22.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -85.0000  160.0000 25

  6 omega   22.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000   90.0000 64
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0495166000
_diffrn_orient_matrix_UB_12      0.0081315000
_diffrn_orient_matrix_UB_13      0.0336082000
_diffrn_orient_matrix_UB_21      -0.0164256000
_diffrn_orient_matrix_UB_22      0.0245660000
_diffrn_orient_matrix_UB_23      0.0281588000
_diffrn_orient_matrix_UB_31      -0.0000436000
_diffrn_orient_matrix_UB_32      -0.0427740000
_diffrn_orient_matrix_UB_33      0.0225700000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22860
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.643
_diffrn_reflns_theta_min         2.871
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0480P)^2^+1.5879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5641
_reflns_number_total             6971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ob41806e.txt
_cod_data_source_block           rjg120009
_cod_original_formula_sum        'C16.50 H16 N6 O1.50'
_cod_database_code               7153642
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C24(H24), C27(H27), C4(H4), C5(H5), C6(H6),
 C8(H8A), C11(H11)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C16(H16A,H16B,H16C)
;
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.973
_shelxl_version_number           2013-3