Functionalised dihydroazo pyrimidine derivatives from Morita-Baylis-Hillman Acetates: Synthesis and studies against Acetylcholinesterase inhibitors.
Eeda, Koti Reddy; Chandran, Remya; Sajith, Ayyiliath M.; V, Dileep K; Sadasivan, C.; Shaik, Anwar; RSC Adv.  (2016) –; doi:10.1039/C6RA12507G

data_7226141
_publ_section_title
;
 Functionalised dihydroazo pyrimidine derivatives from
 Morita-Baylis-Hillman Acetates: Synthesis and studies against
 Acetylcholinesterase inhibitors.
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA12507G
_journal_year                    2016
_chemical_formula_moiety         'C15 H16 N4 O3'
_chemical_formula_sum            'C15 H16 N4 O3'
_chemical_formula_weight         300.32
_chemical_name_systematic        NEW
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-05-02 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                82.835(8)
_cell_angle_beta                 83.414(8)
_cell_angle_gamma                81.361(9)
_cell_formula_units_Z            2
_cell_length_a                   7.5410(8)
_cell_length_b                   7.7485(8)
_cell_length_c                   13.2889(12)
_cell_measurement_reflns_used    2589
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0350
_cell_measurement_theta_min      3.2320
_cell_volume                     758.03(13)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w     47.00  83.00   1.00   12.50    --   26.06  57.00 -60.00   36
  2  \w     -1.00  94.00   1.00   12.50    --   26.06  77.00-120.00   95
  3  \w     67.00  98.00   1.00   12.50    --   26.06 179.00 -90.00   31
  4  \w    -89.00  22.00   1.00   12.50    --  -21.68   0.00 -90.00  111
  5  \w    -20.00  65.00   1.00   12.50    --   26.06 -99.00 120.00   85
  6  \w     13.00  65.00   1.00   12.50    --   26.06 -99.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068471000
_diffrn_orient_matrix_UB_12      0.0330796000
_diffrn_orient_matrix_UB_13      0.0466200000
_diffrn_orient_matrix_UB_21      0.0598421000
_diffrn_orient_matrix_UB_22      0.0571737000
_diffrn_orient_matrix_UB_23      -0.0256357000
_diffrn_orient_matrix_UB_31      -0.0742354000
_diffrn_orient_matrix_UB_32      0.0656802000
_diffrn_orient_matrix_UB_33      -0.0095557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.675
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0859P)^2^+0.0076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             2664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra12507g2.cif
_cod_data_source_block           red
_cod_database_code               7226141
_reflns_odcompleteness_completeness 60.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6C(H6C)
2.b Secondary CH2 refined with riding coordinates:
 C2C(H2CA,H2CB)
2.c Aromatic/amide H refined with riding coordinates:
 N4N(H4N), C13C(H13C), C5C(H5C), C8C(H8C), C12C(H12C), C9C(H9C), C14C(H14C)
2.d Idealised Me refined as rotating group:
 C11C(H11A,H11B,H11C), C1C(H1CA,H1CB,H1CC)
;
_shelx_res_checksum              43098
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.775