##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-09-09
_journal_date_accepted     2010-09-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     10
_journal_page_first     m1280
_journal_page_last     m1280
_journal_paper_category     QM
_journal_coeditor_code     ZS2065
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;\
6,7-Dihydro-5H-1,4-diazepino[1,2,3,4-lmn][1,10]phenanthroline-4,\
8-diium tris(thiocyanato-κN)cuprate(I)
;
loop_
    _publ_author_name
    _publ_author_address
    'Xu, Na'
;
Department of Chemistry
Zhengzhou University
Zhengzhou 450052
People's Republic of China
;
    'Niu, Yun-Yin'
;
Department of Chemistry
Zhengzhou University
Zhengzhou 450052
People's Republic of China
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6,7-Dihydro-5H-1,4-diazepino[1,2,3,4-lmn][1,10]phenanthroline-
4,8-diium tris(thiocyanato-κN)cuprate(I)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H14 N2 2+, C3 Cu N3 S3 2-'
_chemical_formula_sum     'C18 H14 Cu N5 S3'
_chemical_formula_iupac     '(C15 H14 N2) [Cu (N C S)3]'
_chemical_formula_weight     460.06
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     17.2687(4)
_cell_length_b     6.5825(2)
_cell_length_c     17.2702(4)
_cell_angle_alpha     90.00
_cell_angle_beta     107.803(2)
_cell_angle_gamma     90.00
_cell_volume     1869.12(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2549
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     27.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Brown
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.02
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.635
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     1.517
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.7029
_exptl_absorpt_correction_T_max     0.9703
_diffrn_ambient_temperature     100(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 SMART APEX CCD-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15488
_diffrn_reflns_av_R_equivalents     0.0479
_diffrn_reflns_av_sigmaI/netI     0.0482
_diffrn_reflns_theta_min     1.24
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_reflns_number_total     4303
_reflns_number_gt     3657
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0465
_refine_ls_R_factor_gt     0.0342
_refine_ls_wR_factor_gt     0.0690
_refine_ls_wR_factor_ref     0.0745
_refine_ls_goodness_of_fit_ref     0.994
_refine_ls_restrained_S_all     0.994
_refine_ls_number_reflns     4303
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0347P)²] 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     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.377
_refine_diff_density_min     -0.365
_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'
    'Cu' 'Cu' 0.3201 1.2651
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    Cu Cu1 0.58165(3) 0.28784(6) 0.33388(3) 0.01689(10) Uani d . 1 . .
    S S1 0.30831(6) 0.32947(13) 0.33202(7) 0.0244(2) Uani d . 1 . .
    S S2 0.81220(7) 0.20364(14) 0.55830(7) 0.0380(2) Uani d . 1 . .
    S S3 0.57925(7) 0.23791(13) 0.06016(7) 0.0262(2) Uani d . 1 . .
    N N1 0.06515(15) 0.3406(4) 0.21244(15) 0.0115(5) Uani d . 1 . .
    N N2 -0.03925(18) 0.2372(4) 0.31533(17) 0.0138(6) Uani d . 1 . .
    N N3 0.47097(19) 0.3174(4) 0.33561(18) 0.0180(6) Uani d . 1 . .
    N N4 0.67485(17) 0.2767(4) 0.42593(16) 0.0194(5) Uani d . 1 . .
    N N5 0.58441(19) 0.2614(4) 0.2234(2) 0.0184(7) Uani d . 1 . .
    C C1 0.1136(2) 0.3304(4) 0.1650(2) 0.0181(7) Uani d . 1 . .
    H H1 0.1702 0.3554 0.1879 0.022 Uiso calc R 1 . .
    C C2 0.0825(3) 0.2840(5) 0.0826(2) 0.0215(9) Uani d . 1 . .
    H H2 0.1181 0.2658 0.0508 0.026 Uiso calc R 1 . .
    C C3 0.0010(3) 0.2649(5) 0.0479(2) 0.0222(9) Uani d . 1 . .
    H H3 -0.0208 0.2456 -0.0091 0.027 Uiso calc R 1 . .
    C C4 -0.0516(2) 0.2736(4) 0.0965(2) 0.0158(8) Uani d . 1 . .
    C C5 -0.1377(3) 0.2680(4) 0.0618(3) 0.0219(8) Uani d . 1 . .
    H H5 -0.1611 0.2509 0.0048 0.026 Uiso calc R 1 . .
    C C6 -0.1863(3) 0.2870(5) 0.1097(3) 0.0224(8) Uani d . 1 . .
    H H6 -0.2434 0.2995 0.0856 0.027 Uiso calc R 1 . .
    C C7 -0.1528(2) 0.2885(4) 0.1957(2) 0.0181(8) Uani d . 1 . .
    C C8 -0.2032(2) 0.2962(5) 0.2473(2) 0.0216(9) Uani d . 1 . .
    H H8 -0.2604 0.3089 0.2240 0.026 Uiso calc R 1 . .
    C C9 -0.1704(2) 0.2855(5) 0.3296(3) 0.0223(9) Uani d . 1 . .
    H H9 -0.2035 0.3044 0.3640 0.027 Uiso calc R 1 . .
    C C10 -0.0880(2) 0.2466(4) 0.3622(2) 0.0176(8) Uani d . 1 . .
    H H10 -0.0656 0.2261 0.4192 0.021 Uiso calc R 1 . .
    C C11 -0.0685(2) 0.2773(4) 0.2317(2) 0.0122(7) Uani d . 1 . .
    C C12 -0.0164(2) 0.2952(4) 0.1818(2) 0.0136(7) Uani d . 1 . .
    C C13 0.09703(17) 0.4419(4) 0.29339(17) 0.0145(6) Uani d . 1 . .
    H H13A 0.0576 0.5464 0.2984 0.017 Uiso calc R 1 . .
    H H13B 0.1487 0.5116 0.2965 0.017 Uiso calc R 1 . .
    C C14 0.11182(19) 0.2948(5) 0.3639(2) 0.0163(6) Uani d . 1 . .
    H H14A 0.1165 0.3712 0.4145 0.020 Uiso calc R 1 . .
    H H14B 0.1637 0.2221 0.3711 0.020 Uiso calc R 1 . .
    C C15 0.04293(18) 0.1418(5) 0.34912(18) 0.0143(7) Uani d . 1 . .
    H H15A 0.0499 0.0369 0.3107 0.017 Uiso calc R 1 . .
    H H15B 0.0460 0.0735 0.4011 0.017 Uiso calc R 1 . .
    C C16 0.4032(2) 0.3236(4) 0.3330(2) 0.0137(7) Uani d . 1 . .
    C C17 0.7321(2) 0.2479(5) 0.4813(2) 0.0168(6) Uani d . 1 . .
    C C18 0.5820(2) 0.2508(4) 0.1556(2) 0.0164(8) Uani d . 1 . .
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
    Cu1 N4 . 1.886(2) ?
    Cu1 N3 . 1.930(3) ?
    Cu1 N5 . 1.930(3) ?
    S1 C16 . 1.634(4) ?
    S2 C17 . 1.626(3) ?
    S3 C18 . 1.637(4) ?
    N1 C1 . 1.340(4) ?
    N1 C12 . 1.378(4) ?
    N1 C13 . 1.494(4) ?
    N2 C10 . 1.336(4) ?
    N2 C11 . 1.401(4) ?
    N2 C15 . 1.497(4) ?
    N3 C16 . 1.158(4) ?
    N4 C17 . 1.161(3) ?
    N5 C18 . 1.161(5) ?
    C1 C2 . 1.393(5) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.356(6) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.413(5) ?
    C3 H3 . 0.9500 ?
    C4 C12 . 1.418(5) ?
    C4 C5 . 1.423(5) ?
    C5 C6 . 1.353(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.419(6) ?
    C6 H6 . 0.9500 ?
    C7 C11 . 1.400(5) ?
    C7 C8 . 1.424(5) ?
    C8 C9 . 1.361(6) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.385(6) ?
    C9 H9 . 0.9500 ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.429(4) ?
    C13 C14 . 1.515(4) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.519(4) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
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
    N4 Cu1 N3 . . 125.77(14) ?
    N4 Cu1 N5 . . 123.83(15) ?
    N3 Cu1 N5 . . 110.37(9) ?
    C1 N1 C12 . . 120.7(3) ?
    C1 N1 C13 . . 118.3(3) ?
    C12 N1 C13 . . 119.9(2) ?
    C10 N2 C11 . . 121.4(3) ?
    C10 N2 C15 . . 118.7(3) ?
    C11 N2 C15 . . 118.7(3) ?
    C16 N3 Cu1 . . 175.2(3) ?
    C17 N4 Cu1 . . 172.8(2) ?
    C18 N5 Cu1 . . 176.2(3) ?
    N1 C1 C2 . . 121.2(3) ?
    N1 C1 H1 . . 119.4 ?
    C2 C1 H1 . . 119.4 ?
    C3 C2 C1 . . 119.7(3) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 120.2(3) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C3 C4 C12 . . 118.1(3) ?
    C3 C4 C5 . . 121.8(3) ?
    C12 C4 C5 . . 120.1(3) ?
    C6 C5 C4 . . 120.2(5) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C7 . . 120.7(5) ?
    C5 C6 H6 . . 119.7 ?
    C7 C6 H6 . . 119.7 ?
    C11 C7 C6 . . 120.0(3) ?
    C11 C7 C8 . . 118.4(3) ?
    C6 C7 C8 . . 121.6(3) ?
    C9 C8 C7 . . 120.8(3) ?
    C9 C8 H8 . . 119.6 ?
    C7 C8 H8 . . 119.6 ?
    C8 C9 C10 . . 118.9(3) ?
    C8 C9 H9 . . 120.6 ?
    C10 C9 H9 . . 120.6 ?
    N2 C10 C9 . . 121.4(4) ?
    N2 C10 H10 . . 119.3 ?
    C9 C10 H10 . . 119.3 ?
    C7 C11 N2 . . 117.8(3) ?
    C7 C11 C12 . . 119.2(4) ?
    N2 C11 C12 . . 122.9(4) ?
    N1 C12 C4 . . 119.0(3) ?
    N1 C12 C11 . . 122.9(3) ?
    C4 C12 C11 . . 118.0(4) ?
    N1 C13 C14 . . 113.0(2) ?
    N1 C13 H13A . . 109.0 ?
    C14 C13 H13A . . 109.0 ?
    N1 C13 H13B . . 109.0 ?
    C14 C13 H13B . . 109.0 ?
    H13A C13 H13B . . 107.8 ?
    C13 C14 C15 . . 110.9(2) ?
    C13 C14 H14A . . 109.4 ?
    C15 C14 H14A . . 109.4 ?
    C13 C14 H14B . . 109.4 ?
    C15 C14 H14B . . 109.4 ?
    H14A C14 H14B . . 108.0 ?
    N2 C15 C14 . . 112.8(2) ?
    N2 C15 H15A . . 109.0 ?
    C14 C15 H15A . . 109.0 ?
    N2 C15 H15B . . 109.0 ?
    C14 C15 H15B . . 109.0 ?
    H15A C15 H15B . . 107.8 ?
    N3 C16 S1 . . 178.3(3) ?
    N4 C17 S2 . . 179.0(3) ?
    N5 C18 S3 . . 179.4(3) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C12 N1 C1 C2 . . . . 3.3(5) ?
    C13 N1 C1 C2 . . . . -164.4(3) ?
    N1 C1 C2 C3 . . . . 5.5(5) ?
    C1 C2 C3 C4 . . . . -5.8(5) ?
    C2 C3 C4 C12 . . . . -2.2(4) ?
    C2 C3 C4 C5 . . . . 175.7(3) ?
    C3 C4 C5 C6 . . . . -176.6(3) ?
    C12 C4 C5 C6 . . . . 1.2(4) ?
    C4 C5 C6 C7 . . . . -7.5(4) ?
    C5 C6 C7 C11 . . . . 2.2(4) ?
    C5 C6 C7 C8 . . . . -176.2(3) ?
    C11 C7 C8 C9 . . . . -2.4(5) ?
    C6 C7 C8 C9 . . . . 176.1(3) ?
    C7 C8 C9 C10 . . . . -6.4(5) ?
    C11 N2 C10 C9 . . . . 3.6(4) ?
    C15 N2 C10 C9 . . . . -163.9(3) ?
    C8 C9 C10 N2 . . . . 5.9(5) ?
    C6 C7 C11 N2 . . . . -167.1(3) ?
    C8 C7 C11 N2 . . . . 11.4(4) ?
    C6 C7 C11 C12 . . . . 9.3(4) ?
    C8 C7 C11 C12 . . . . -172.2(3) ?
    C10 N2 C11 C7 . . . . -12.3(4) ?
    C15 N2 C11 C7 . . . . 155.2(3) ?
    C10 N2 C11 C12 . . . . 171.5(3) ?
    C15 N2 C11 C12 . . . . -21.0(4) ?
    C1 N1 C12 C4 . . . . -11.3(4) ?
    C13 N1 C12 C4 . . . . 156.1(3) ?
    C1 N1 C12 C11 . . . . 171.5(3) ?
    C13 N1 C12 C11 . . . . -21.1(4) ?
    C3 C4 C12 N1 . . . . 10.7(4) ?
    C5 C4 C12 N1 . . . . -167.2(3) ?
    C3 C4 C12 C11 . . . . -172.0(3) ?
    C5 C4 C12 C11 . . . . 10.1(4) ?
    C7 C11 C12 N1 . . . . 162.0(3) ?
    N2 C11 C12 N1 . . . . -21.8(4) ?
    C7 C11 C12 C4 . . . . -15.2(4) ?
    N2 C11 C12 C4 . . . . 161.0(3) ?
    C1 N1 C13 C14 . . . . -111.1(3) ?
    C12 N1 C13 C14 . . . . 81.2(3) ?
    N1 C13 C14 C15 . . . . -42.1(4) ?
    C10 N2 C15 C14 . . . . -110.8(3) ?
    C11 N2 C15 C14 . . . . 81.4(3) ?
    C13 C14 C15 N2 . . . . -43.3(4) ?
