##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2009-09-24
_journal_date_accepted     2009-10-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2853
_journal_page_last     o2853
_journal_paper_category     QO
_journal_coeditor_code     HG2573
_publ_contact_author_name     'Zhao, Gan-Qing'
_publ_contact_author_address
;
  School of Chemistry and Chemical Engineering
    Pingdingshan University
    Pingdingshan 467000
    People's Republic of China
;
_publ_contact_author_email     zgq1118@163.com
_publ_contact_author_fax     '86 375 4910185'
_publ_contact_author_phone     '86 375 4910032'
_publ_section_title
;
Benzyl 3-(10-oxo-9,10-dihydrophenanthren-9-ylidene)dithiocarbazate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Liu, Qiao-Ru' .
; School of Chemistry and Chemical Engineering
    Pingdingshan University
    Pingdingshan 467000
    People's Republic of China
;
    'Chu, Song-Mao' .
; School of Chemistry and Chemical Engineering
    Pingdingshan University
    Pingdingshan 467000
    People's Republic of China
;
    'Zhao, Gan-Qing' .
;
  School of Chemistry and Chemical Engineering
    Pingdingshan University
    Pingdingshan 467000
    People's Republic of China
;
    'Chen, Li-Hua' .
; School of Chemistry and Chemical Engineering
    Pingdingshan University
    Pingdingshan 467000
    People's Republic of China
;
    'Han, Yong-Jun' .
; School of Chemistry and Chemical Engineering
    Pingdingshan University
    Pingdingshan 467000
    People's Republic of China
;
data_I
_chemical_name_systematic
;
Benzyl 3-(10-oxo-9,10-dihydrophenanthren-9-ylidene)dithiocarbazate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H16 N2 O S2'
_chemical_formula_sum     'C22 H16 N2 O S2'
_chemical_formula_iupac     'C22 H16 N2 O S2'
_chemical_formula_weight     388.49
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.4945(19)
_cell_length_b     5.6978(7)
_cell_length_c     22.816(3)
_cell_angle_alpha     90.00
_cell_angle_beta     93.610(2)
_cell_angle_gamma     90.00
_cell_volume     1880.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3545
_cell_measurement_theta_min     2.21
_cell_measurement_theta_max     27.06
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.372
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     808
_exptl_absorpt_coefficient_mu     0.298
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9160
_exptl_absorpt_correction_T_max     0.9429
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9220
_diffrn_reflns_av_R_equivalents     0.0215
_diffrn_reflns_av_sigmaI/netI     0.0226
_diffrn_reflns_theta_min     2.21
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
loop_
    _diffrn_measured_fraction_theta_max
    0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3316
_reflns_number_gt     2638
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0474
_refine_ls_R_factor_gt     0.0359
_refine_ls_wR_factor_gt     0.0909
_refine_ls_wR_factor_ref     0.0984
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_restrained_S_all     1.056
_refine_ls_number_reflns     3316
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0436P)²+0.4502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.162
_refine_diff_density_min     -0.216
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.12004(12) 0.9543(3) 0.10487(7) 0.0410(4) Uani d . 1 . .
    C C2 0.07744(12) 0.7660(3) 0.13826(7) 0.0404(4) Uani d . 1 . .
    C C3 0.13280(14) 0.6058(3) 0.17087(8) 0.0505(5) Uani d . 1 . .
    H H3 0.1968 0.6203 0.1718 0.061 Uiso calc R 1 . .
    C C4 0.09428(15) 0.4277(3) 0.20145(8) 0.0570(5) Uani d . 1 . .
    H H4 0.1320 0.3226 0.2230 0.068 Uiso calc R 1 . .
    C C5 -0.00057(15) 0.4045(3) 0.20025(8) 0.0551(5) Uani d . 1 . .
    H H5 -0.0269 0.2837 0.2209 0.066 Uiso calc R 1 . .
    C C6 -0.05593(14) 0.5600(3) 0.16850(7) 0.0496(5) Uani d . 1 . .
    H H6 -0.1198 0.5422 0.1679 0.060 Uiso calc R 1 . .
    C C7 -0.01904(12) 0.7447(3) 0.13706(7) 0.0413(4) Uani d . 1 . .
    C C8 -0.07862(12) 0.9126(3) 0.10288(7) 0.0428(4) Uani d . 1 . .
    C C9 -0.17451(14) 0.8986(4) 0.10096(9) 0.0601(5) Uani d . 1 . .
    H H9 -0.2023 0.7801 0.1217 0.072 Uiso calc R 1 . .
    C C10 -0.22943(14) 1.0568(4) 0.06899(10) 0.0663(6) Uani d . 1 . .
    H H10 -0.2934 1.0431 0.0684 0.080 Uiso calc R 1 . .
    C C11 -0.19058(14) 1.2346(4) 0.03787(9) 0.0594(5) Uani d . 1 . .
    H H11 -0.2279 1.3411 0.0165 0.071 Uiso calc R 1 . .
    C C12 -0.09620(13) 1.2524(3) 0.03891(8) 0.0496(5) Uani d . 1 . .
    H H12 -0.0693 1.3716 0.0179 0.059 Uiso calc R 1 . .
    C C13 -0.04017(12) 1.0942(3) 0.07096(7) 0.0407(4) Uani d . 1 . .
    C C14 0.06035(12) 1.1237(3) 0.07105(7) 0.0427(4) Uani d . 1 . .
    C C15 0.34732(13) 1.1176(4) 0.07602(8) 0.0513(5) Uani d . 1 . .
    C C16 0.51902(14) 0.9484(5) 0.11012(11) 0.0836(8) Uani d . 1 . .
    H H16A 0.5363 0.9037 0.0713 0.100 Uiso calc R 1 . .
    H H16B 0.5310 1.1148 0.1154 0.100 Uiso calc R 1 . .
    C C17 0.57478(13) 0.8104(4) 0.15607(10) 0.0635(6) Uani d . 1 . .
    C C18 0.61629(15) 0.6028(5) 0.14199(11) 0.0716(6) Uani d . 1 . .
    H H18 0.6081 0.5433 0.1041 0.086 Uiso calc R 1 . .
    C C19 0.67014(17) 0.4821(5) 0.18405(14) 0.0816(7) Uani d . 1 . .
    H H19 0.6984 0.3422 0.1743 0.098 Uiso calc R 1 . .
    C C20 0.68202(17) 0.5671(6) 0.23965(13) 0.0863(8) Uani d . 1 . .
    H H20 0.7184 0.4851 0.2677 0.104 Uiso calc R 1 . .
    C C21 0.64071(19) 0.7725(6) 0.25452(12) 0.0867(8) Uani d . 1 . .
    H H21 0.6489 0.8302 0.2926 0.104 Uiso calc R 1 . .
    C C22 0.58678(16) 0.8938(5) 0.21272(12) 0.0777(7) Uani d . 1 . .
    H H22 0.5583 1.0329 0.2229 0.093 Uiso calc R 1 . .
    N N1 0.20996(10) 0.9575(3) 0.10711(6) 0.0466(4) Uani d . 1 . .
    N N2 0.25374(10) 1.1215(3) 0.07714(7) 0.0524(4) Uani d . 1 . .
    H H2 0.2225 1.2296 0.0586 0.063 Uiso calc R 1 . .
    O O1 0.09460(9) 1.2850(2) 0.04354(6) 0.0577(4) Uani d . 1 . .
    S S1 0.39768(3) 0.88888(10) 0.11712(2) 0.06204(18) Uani d . 1 . .
    S S2 0.39996(4) 1.31825(12) 0.03859(3) 0.0741(2) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N1 . 1.301(2) ?
    C1 C2 . 1.474(2) ?
    C1 C14 . 1.480(2) ?
    C2 C3 . 1.398(2) ?
    C2 C7 . 1.402(2) ?
    C3 C4 . 1.370(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.380(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.371(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.399(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.478(2) ?
    C8 C9 . 1.390(3) ?
    C8 C13 . 1.401(2) ?
    C9 C10 . 1.380(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.378(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.371(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.390(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.467(2) ?
    C14 O1 . 1.235(2) ?
    C15 N2 . 1.358(2) ?
    C15 S2 . 1.6432(19) ?
    C15 S1 . 1.739(2) ?
    C16 C17 . 1.505(3) ?
    C16 S1 . 1.808(2) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C18 . 1.374(3) ?
    C17 C22 . 1.378(3) ?
    C18 C19 . 1.382(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.359(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.367(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.380(3) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    N1 N2 . 1.341(2) ?
    N2 H2 . 0.8600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 C2 . . 116.18(15) ?
    N1 C1 C14 . . 124.21(16) ?
    C2 C1 C14 . . 119.60(15) ?
    C3 C2 C7 . . 119.49(16) ?
    C3 C2 C1 . . 120.34(16) ?
    C7 C2 C1 . . 120.17(15) ?
    C4 C3 C2 . . 121.05(18) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C3 C4 C5 . . 119.87(18) ?
    C3 C4 H4 . . 120.1 ?
    C5 C4 H4 . . 120.1 ?
    C6 C5 C4 . . 119.87(18) ?
    C6 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    C5 C6 C7 . . 121.82(18) ?
    C5 C6 H6 . . 119.1 ?
    C7 C6 H6 . . 119.1 ?
    C6 C7 C2 . . 117.90(16) ?
    C6 C7 C8 . . 121.88(16) ?
    C2 C7 C8 . . 120.22(15) ?
    C9 C8 C13 . . 117.11(17) ?
    C9 C8 C7 . . 121.96(17) ?
    C13 C8 C7 . . 120.92(15) ?
    C10 C9 C8 . . 121.44(19) ?
    C10 C9 H9 . . 119.3 ?
    C8 C9 H9 . . 119.3 ?
    C11 C10 C9 . . 120.78(19) ?
    C11 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 119.6 ?
    C12 C11 C10 . . 119.03(19) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C11 C12 C13 . . 120.71(18) ?
    C11 C12 H12 . . 119.6 ?
    C13 C12 H12 . . 119.6 ?
    C12 C13 C8 . . 120.93(16) ?
    C12 C13 C14 . . 118.28(16) ?
    C8 C13 C14 . . 120.78(15) ?
    O1 C14 C13 . . 121.05(16) ?
    O1 C14 C1 . . 120.66(16) ?
    C13 C14 C1 . . 118.29(15) ?
    N2 C15 S2 . . 119.68(15) ?
    N2 C15 S1 . . 112.82(14) ?
    S2 C15 S1 . . 127.49(12) ?
    C17 C16 S1 . . 108.87(15) ?
    C17 C16 H16A . . 109.9 ?
    S1 C16 H16A . . 109.9 ?
    C17 C16 H16B . . 109.9 ?
    S1 C16 H16B . . 109.9 ?
    H16A C16 H16B . . 108.3 ?
    C18 C17 C22 . . 119.0(2) ?
    C18 C17 C16 . . 120.7(2) ?
    C22 C17 C16 . . 120.3(2) ?
    C17 C18 C19 . . 120.2(2) ?
    C17 C18 H18 . . 119.9 ?
    C19 C18 H18 . . 119.9 ?
    C20 C19 C18 . . 120.3(3) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 120.3(3) ?
    C19 C20 H20 . . 119.8 ?
    C21 C20 H20 . . 119.8 ?
    C20 C21 C22 . . 119.7(3) ?
    C20 C21 H21 . . 120.2 ?
    C22 C21 H21 . . 120.2 ?
    C17 C22 C21 . . 120.5(3) ?
    C17 C22 H22 . . 119.7 ?
    C21 C22 H22 . . 119.7 ?
    C1 N1 N2 . . 119.66(15) ?
    N1 N2 C15 . . 120.22(16) ?
    N1 N2 H2 . . 119.9 ?
    C15 N2 H2 . . 119.9 ?
    C15 S1 C16 . . 100.92(10) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N2 H2 O1 . 0.86 1.89 2.560(2) 134 yes
    C12 H12 O1 3_585 0.93 2.42 3.239(2) 147 yes
    C5 H5 Cg1 2_545 0.93 2.76 3.559(2) 144 yes
