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_7220217
_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_absolute_configuration unk
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_audit_creation_date             2014-02-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8597(13)
_cell_length_b                   24.115(4)
_cell_length_c                   5.0303(7)
_cell_measurement_reflns_used    632
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.2453
_cell_measurement_theta_min      3.3725
_cell_volume                     1317.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_details
;
  1 omega   13.00   61.00   1.0000    7.2500
omega____ theta____ kappa____ phi______ frames
    -       19.7923 -104.0000  133.0000 48

  2 omega  -49.00   58.00   1.0000    7.2500
omega____ theta____ kappa____ phi______ frames
    -       19.7923    0.0000  -30.0000 107
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0001206000
_diffrn_orient_matrix_UB_12      -0.0282465000
_diffrn_orient_matrix_UB_13      -0.0389324000
_diffrn_orient_matrix_UB_21      -0.0641399000
_diffrn_orient_matrix_UB_22      0.0016921000
_diffrn_orient_matrix_UB_23      -0.0261240000
_diffrn_orient_matrix_UB_31      0.0126727000
_diffrn_orient_matrix_UB_32      0.0079064000
_diffrn_orient_matrix_UB_33      -0.1329962000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3769
_diffrn_reflns_theta_full        27.9190
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'reddish red'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.3275
_exptl_crystal_description       needle
_exptl_crystal_F_000             552.2713
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2752
_refine_diff_density_min         -0.3278
_refine_diff_density_rms         0.0700
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -3(4)
_refine_ls_d_res_high            0.7590
_refine_ls_d_res_low             6.0287
_refine_ls_goodness_of_fit_ref   1.1178
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1178
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.5958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.273
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              30
_reflns_limit_k_min              -29
_reflns_limit_l_max              3
_reflns_limit_l_min              -6
_reflns_number_gt                1366
_reflns_number_total             1366
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra02295a2.cif
_cod_data_source_block           vks4
_cod_database_code               7220217
_chemical_oxdiff_formula         'C16 H12 N2 O2'
_reflns_odcompleteness_completeness 99.57
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C8(H8), C6(H6), C13(H13), C14(H14), C7(H7), C16(H16),
 C17(H17), C15(H15)
;