Benzo[α]phenoxazines and Benzo[α]phenothiazine from Vitamin K3: Synthesis, Molecular structures, DFT studies and Cytotoxic activity
Chadar, Dattatray; Rao, Soniya S.; Khan, Ayesha; Gejji, Shridhar P.; Bhat, Kiesar; Weyhermueller, Thomas; Salunke-Gawali, Sunita Arun; RSC Adv.  (2015) –; doi:10.1039/C5RA08496B

data_7220904
_publ_section_title
;
 Benzo[\a]phenoxazines and Benzo[\a]phenothiazine from Vitamin K3:
 Synthesis, Molecular structures, DFT studies and Cytotoxic activity
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA08496B
_journal_year                    2015
_chemical_formula_moiety         'C17 H11 N O S'
_chemical_formula_sum            'C17 H11 N O S'
_chemical_formula_weight         277.33
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                FNG-SX-501-06
_audit_creation_date             2014-07-30
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-12-15 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.902(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.172(3)
_cell_length_b                   3.8385(8)
_cell_length_c                   22.105(4)
_cell_measurement_reflns_used    20766
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9999
_cell_measurement_theta_min      2.6823
_cell_volume                     1225.0(4)
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15404
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.724
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.99571
_exptl_absorpt_correction_T_min  0.94895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0666P)^2^+2.0711P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2479
_reflns_number_total             3243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra08496b2.cif
_cod_data_source_block           8900
_cod_database_code               7220904
_shelx_estimated_absorpt_t_min   0.904
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2013-2
_shelx_res_checksum              69163
_shelx_hkl_checksum              96722