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_7226140
_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         'C19 H15 Br Cl N3 O2'
_chemical_formula_sum            'C19 H15 Br Cl N3 O2'
_chemical_formula_weight         432.70
_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             2016-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-12 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                69.068(9)
_cell_angle_beta                 83.892(7)
_cell_angle_gamma                81.991(7)
_cell_formula_units_Z            2
_cell_length_a                   5.4739(4)
_cell_length_b                   11.7125(11)
_cell_length_c                   15.0667(15)
_cell_measurement_reflns_used    2494
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.7830
_cell_measurement_theta_min      2.7480
_cell_volume                     891.75(15)
_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      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -30.00  53.00   1.00    5.00    --  -14.38  57.00 -60.00   83
  2  \w     55.00  81.00   1.00    5.00    --   18.60  57.00   0.00   26
  3  \w     -2.00  25.00   1.00    5.00    --  -14.38 -99.00-180.00   27
  4  \w    -20.00  19.00   1.00    5.00    --  -14.38 -99.00 -60.00   39
  5  \w    -82.00  11.00   1.00    5.00    --  -14.38 -77.00  60.00   93
  6  \w    -41.00  49.00   1.00    5.00    --  -14.38  77.00-180.00   90
;
_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      0.0104460000
_diffrn_orient_matrix_UB_12      0.0555650000
_diffrn_orient_matrix_UB_13      -0.0390985000
_diffrn_orient_matrix_UB_21      0.0289495000
_diffrn_orient_matrix_UB_22      -0.0339079000
_diffrn_orient_matrix_UB_23      -0.0311600000
_diffrn_orient_matrix_UB_31      -0.1274365000
_diffrn_orient_matrix_UB_32      0.0041722000
_diffrn_orient_matrix_UB_33      -0.0071031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6091
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.739
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89855
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0753P)^2^+0.3464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2320
_reflns_number_total             3153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra12507g2.cif
_cod_data_source_block           red
_cod_depositor_comments
;

2018-03-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C19 H15 Br Cl N3 O2)'
_cod_original_formula_sum        'C38 H30 Br2 Cl2 N6 O4'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     865.40
_cod_database_code               7226140
_chemical_oxdiff_formula         'C16 H12 N2 O1'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00Q(H00C,H00D,H00G)
;
_shelx_res_checksum              28712
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.852