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_7220905
_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_sum            'C17 H10 Cl N O2'
_chemical_formula_weight         295.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                CEC-CA-094
_audit_creation_date             2014-07-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7569(9)
_cell_length_b                   9.660(2)
_cell_length_c                   28.117(5)
_cell_measurement_reflns_used    5533
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.4013
_cell_measurement_theta_min      2.5583
_cell_volume                     1292.0(4)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            35695
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.210
_diffrn_reflns_theta_min         3.028
_diffrn_source                   1\mS
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.99706
_exptl_absorpt_correction_T_min  0.95811
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0416P)^2^+0.2274P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3275
_reflns_number_total             3840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra08496b2.cif
_cod_data_source_block           8901
_cod_database_code               7220905
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-2
_shelx_res_checksum              33650
_shelx_hkl_checksum              92252