Two step, one-pot sequential synthesis of functionalized hybrid polyheterocyclic scaffolds via a solid state melt reaction (SSMR)
Bakthadoss, Manickam; Srinivasan, Jayakumar; Hussain, Mir Ashiq; Sharada, Duddu S.; RSC Advances 9 (2019) 24314–; doi:10.1039/C9RA02590A

data_7233354
_publ_section_title
;
 Two step, one-pot sequential synthesis of functionalized hybrid
 polyheterocyclic scaffolds via a solid state melt reaction (SSMR)
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              24314
_journal_paper_doi               10.1039/C9RA02590A
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C36 H27 Br N2 O4'
_chemical_formula_sum            'C35 H27 Br N2 O4'
_chemical_formula_weight         630.11
_chemical_name_common            'Heptacyclic Benzo[a]phenazinone'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-28 deposited with the CCDC.    2019-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                70.525(9)
_cell_angle_beta                 84.720(8)
_cell_angle_gamma                84.754(8)
_cell_formula_units_Z            2
_cell_length_a                   10.8736(11)
_cell_length_b                   11.2191(11)
_cell_length_c                   12.8583(13)
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1481
_cell_measurement_theta_min      3.7640
_cell_volume                     1469.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
  1 omega  -43.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  -60.0000 90

  2 omega  -22.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -60.0000 44

  3 omega  -83.00    4.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000   30.0000 87

  4 omega  -79.00   26.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   90.0000 105

  5 omega  -22.00   25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  120.0000 47

  6 omega  -93.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000   30.0000 58

  7 omega    9.00   43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366 -144.0000  107.0000 34

  8 omega   -2.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  -60.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0292237000
_diffrn_orient_matrix_UB_12      0.0512800000
_diffrn_orient_matrix_UB_13      -0.0407913000
_diffrn_orient_matrix_UB_21      0.0300849000
_diffrn_orient_matrix_UB_22      -0.0222687000
_diffrn_orient_matrix_UB_23      -0.0419685000
_diffrn_orient_matrix_UB_31      -0.0505016000
_diffrn_orient_matrix_UB_32      -0.0372863000
_diffrn_orient_matrix_UB_33      0.0035988000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15946
_diffrn_reflns_theta_full        29.21
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.1816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1773
_reflns_number_gt                3538
_reflns_number_total             6803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ra02590a2.cif
_cod_data_source_block           mb-2-29-03-14
_cod_database_code               7233354
_chemical_oxdiff_formula         'C12 H14 N2 Cl2'
_reflns_odcompleteness_completeness 99.15
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'