Identification of unusual C–Cl•••π contacts in 2-(alkylamino)-3-chloro-1,4-naphthoquinones: Effect of N-substituents on crystal packings, fluorescence, redox and anti-microbial properties
Singh, Vinay Kumar; Verma, Sanjay Kumar; Kadu, Rahul Vilasrao; Mobin, Shaikh M.; RSC Adv.  (2015) –; doi:10.1039/C5RA02295A

data_7220215
_publ_section_title
;
 Identification of unusual C--Cl&#x2022;&#x2022;&#x2022;\p contacts in
 2-(alkylamino)-3-chloro-1,4-naphthoquinones: Effect of N-substituents on
 crystal packings, fluorescence, redox and anti-microbial properties
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA02295A
_journal_year                    2015
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.898(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0576(4)
_cell_length_b                   11.4615(7)
_cell_length_c                   23.3465(11)
_cell_measurement_reflns_used    2361
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.9983
_cell_measurement_theta_min      3.1589
_cell_volume                     1352.60(15)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       \w/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8228
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.9368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+1.5511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1858
_reflns_number_gt                1904
_reflns_number_total             2368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra02295a2.cif
_cod_data_source_block           msu009
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7220215