##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_journal_date_recd_electronic     2005-03-24
_journal_date_accepted     2005-04-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      5
_journal_page_first     o1456
_journal_page_last     o1458
_journal_paper_category     EO
_publ_contact_author_name     'Dr Isao Fujii'
_publ_contact_author_address
;  Department of Biological Science and Technology
   Tokai University
   317 Nishino
   Numazu
   Shizuoka 410-0321
   Japan
;
_publ_contact_author_email     fujii@wing.ncc.u-tokai.ac.jp
_publ_contact_author_fax     '+81-55-968-1156'
_publ_contact_author_phone     '+81-55-968-1211 ex.4315'
_publ_section_title
;
4-Chloro-3-nitrocoumarin: an unusual non-bonding C---Cl...O=C interaction
;
loop_
    _publ_author_name
    _publ_author_address
    'Fujii, Isao'
;
  Department of Biological Science and Technology
   Tokai University
  317 Nishino
  Numazu
  Shizuoka 410-0321
  Japan
;
    'Mano, Yoshihiro'
;
  Department of Biological Science and Technology
   Tokai University
  317 Nishino
  Numazu
  Shizuoka 410-0321
  Japan
;
    'Hirayama, Noriaki'
;
  School of Medical Science
  Tokai University
  Boseidai
  Isehara
  Kanagawa 259-1193
  Japan
;
data_I
_chemical_name_systematic     '4-chloro-3-nitro-2H- chromen-2-one'
_chemical_name_common     4-chloro-3-nitrocoumarin
_chemical_formula_moiety     'C9 H4 Cl N O4 '
_chemical_formula_sum     'C9 H4 Cl N O4 '
_chemical_formula_iupac     'C9 H4 Cl N O4 '
_chemical_formula_weight     225.59
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/c 1'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    x,y,z
    -x,1/2+y,1/2-z
    -x,-y,-z
    x,1/2-y,1/2+z
_cell_length_a     8.5110(4)
_cell_length_b     13.5260(10)
_cell_length_c     8.6612(5)
_cell_angle_alpha     90
_cell_angle_beta     114.119(5)
_cell_angle_gamma     90
_cell_volume     910.00(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     30.0
_cell_measurement_theta_max     35.0
_cell_measurement_temperature     297.2
_exptl_crystal_description     'rod'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.646
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     456.0
_exptl_absorpt_coefficient_mu     3.713
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.433
_exptl_absorpt_correction_T_max     0.478
_diffrn_ambient_temperature     24
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'ω/2θ scans'
_diffrn_reflns_number     2084
_diffrn_reflns_av_R_equivalents     0.032
_diffrn_reflns_theta_max     74.86
_diffrn_reflns_theta_full     74.86
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     3
_diffrn_standards_interval_count     300
_diffrn_standards_decay_%     none
_refine_special_details
;
Refinement using reflections with F² > -10.0 sigma(F²). The weighted
R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are
based on F. The threshold expression of F² > 2.0 sigma(F²) is used only
for calculating R-factor (gt).
;
_reflns_number_total     1876
_reflns_number_gt     1727
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     0.0471
_refine_ls_wR_factor_ref     0.1984
_refine_ls_goodness_of_fit_ref     1.206
_refine_ls_number_reflns     1876
_refine_ls_number_parameters     137
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                    'w = 1/[σ²(Fo²) + (0.157(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_shift/su_max     0.0003
_refine_diff_density_max     0.34
_refine_diff_density_min     -0.43
_refine_ls_extinction_method     'type 2 Gaussian isotropic (Zachariasen, 1967)'
_refine_ls_extinction_coef     0.39(6)
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
    'N' 'N' 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
    'O' 'O' 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
    'H' 'H' 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
    'Cl' 'Cl' 0.364 0.702
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1988)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_structure_solution     'SIR88 (Burla et al., 1989)'
_computing_structure_refinement     'TEXSAN'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'TEXSAN'
loop_
    _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
    _atom_site_type_symbol
    Cl4 0.48318(6) 0.53267(4) 0.70590(7) 0.0588(2) Uani d . 1.00 . . Cl
    O1 0.0943(2) 0.29460(10)
                           0.4628(2) 0.0512(4) Uani d . 1.00 . . O
    O2 0.2479(2) 0.18910(10)
                           0.6613(2) 0.0644(5) Uani d . 1.00 . . O
    O31 0.4867(4) 0.3193(3) 0.9598(3) 0.1260(10)
                                               Uani d . 1.00 . . O
    O32 0.6406(3) 0.3048(2) 0.8216(3) 0.0882(7) Uani d . 1.00 . . O
    N3 0.5066(2) 0.32350(10)
                           0.8317(2) 0.0560(5) Uani d . 1.00 . . N
    C2 0.2346(3) 0.27100(10)
                           0.6051(2) 0.0449(5) Uani d . 1.00 . . C
    C3 0.3588(2) 0.35010(10)
                           0.6775(2) 0.0418(4) Uani d . 1.00 . . C
    C4 0.3365(2) 0.44140(10)
                           0.6111(2) 0.0404(4) Uani d . 1.00 . . C
    C41 0.1877(2) 0.46280(10)
                            0.4585(2) 0.0408(5) Uani d . 1.00 . . C
    C5 0.1554(3) 0.5538(2) 0.3737(3) 0.0568(6) Uani d . 1.00 . . C
    C6 0.0120(4) 0.5651(2) 0.2250(3) 0.0693(7) Uani d . 1.00 . . C
    C7 -0.1028(4) 0.4875(2) 0.1593(3) 0.0704(7) Uani d . 1.00 . . C
    C8 -0.0756(3) 0.3978(2) 0.2400(3) 0.0599(6) Uani d . 1.00 . . C
    C11 0.0705(2) 0.38650(10)
                            0.3882(2) 0.0437(5) Uani d . 1.00 . . C
    H5 0.2325 0.6073 0.4184 0.0684 Uiso calc . 1.00 . . H
    H6 -0.0099 0.6265 0.1674 0.0832 Uiso calc . 1.00 . . H
    H7 -0.2015 0.4966 0.0561 0.0843 Uiso calc . 1.00 . . H
    H8 -0.1553 0.3452 0.1957 0.0720 Uiso calc . 1.00 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl4 0.0559(5) 0.0475(5) 0.0649(5) -0.0141(2) 0.0163(3) -0.0122(2)
    O1 0.0460(8) 0.0391(7) 0.0570(8) -0.0034(5) 0.0093(6) -0.0047(5)
    O2 0.0650(10)
                0.0415(8) 0.0840(10)
                                   -0.0004(6) 0.0272(9) 0.0135(7)
    O31 0.097(2) 0.227(3) 0.0478(10) 0.024(2) 0.0220(10)
                                                       0.0370(10)
    O32 0.0502(10) 0.122(2) 0.0760(10)
                                     0.0220(10)
                                              0.0095(8) 0.0090(10)
    N3 0.0504(10) 0.0620(10)
                           0.0451(8) 0.0000(8) 0.0085(7) 0.0060(7)
    C2 0.0443(9) 0.0388(9) 0.0506(9) 0.0011(7) 0.0184(7) 0.0017(7)
    C3 0.0395(9) 0.0448(9) 0.0384(8) 0.0013(6) 0.0132(7) 0.0010(6)
    C4 0.0437(9) 0.0387(9) 0.0394(8) -0.0047(7) 0.0177(7) -0.0057(6)
    C41 0.0440(10) 0.0398(10) 0.0398(9) 0.0053(6) 0.0182(8) 0.0013(6)
    C5 0.0630(10)
                0.0480(10)
                         0.0630(10)
                                  0.0087(9) 0.0280(10)
                                                     0.0136(9)
    C6 0.081(2) 0.069(2) 0.0600(10)
                                  0.0260(10)
                                           0.0300(10)
                                                    0.0250(10)
    C7 0.0650(10)
                0.090(2) 0.0430(10)
                                  0.0310(10)
                                           0.0090(10)
                                                    0.0090(10)
    C8 0.0470(10)
                0.0690(10)
                         0.0500(10)
                                  0.0070(9) 0.0056(8) -0.0098(9)
    C11 0.0438(9) 0.0436(9) 0.0393(9) 0.0060(7) 0.0124(7) -0.0023(6)
_geom_special_details
;
 ?
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl4 C4 . . 1.709(2) yes
    O1 C2 . . 1.358(2) n
    O1 C11 . . 1.377(2) n
    O2 C2 . . 1.197(2) n
    O31 N3 . . 1.190(3) n
    O32 N3 . . 1.207(3) n
    N3 C3 . . 1.457(2) n
    C2 C3 . . 1.454(3) yes
    C3 C4 . . 1.342(3) yes
    C4 C41 . . 1.438(3) yes
    C41 C5 . . 1.402(3) n
    C41 C11 . . 1.390(3) n
    C5 C6 . . 1.374(4) n
    C6 C7 . . 1.388(4) n
    C7 C8 . . 1.372(4) n
    C8 C11 . . 1.383(3) n
    C5 H5 . . 0.946 n
    C7 H7 . . 0.952 n
    C6 H6 . . 0.947 n
    C8 H8 . . 0.948 n
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cl4 O2 2.981(2) . 2_656 yes
    Cl4 O31 3.443(3) . 3_667 ?
    O1 O2 3.371(2) . 4_554 ?
    O1 C6 3.448(3) . 2_545 ?
    O2 C11 3.100(2) . 4_555 ?
    O2 O31 3.176(3) . 4_554 ?
    O2 C8 3.310(3) . 4_555 ?
    O2 C41 3.490(2) . 4_555 ?
    O2 C6 3.585(3) . 2_545 ?
    O31 C2 3.144(3) . 4_555 ?
    O31 O32 3.316(3) . 4_555 ?
    O31 C3 3.415(3) . 4_555 ?
    O32 C5 3.454(3) . 3_666 ?
    C4 C7 3.474(3) . 3_566 ?
    C5 C11 3.441(3) . 3_566 ?
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 C11 . . . 122.90(10)
                             n
    O31 N3 O32 . . . 123.8(2) n
    O31 N3 C3 . . . 117.9(2) n
    O32 N3 C3 . . . 118.2(2) n
    O1 C2 O2 . . . 119.2(2) n
    O1 C2 C3 . . . 115.70(10)
                            n
    O2 C2 C3 . . . 125.1(2) n
    N3 C3 C2 . . . 114.6(2) yes
    N3 C3 C4 . . . 122.6(2) yes
    C2 C3 C4 . . . 122.8(2) n
    Cl4 C4 C3 . . . 120.70(10)
                             yes
    Cl4 C4 C41 . . . 119.50(10)
                              yes
    C3 C4 C41 . . . 119.8(2) n
    C4 C41 C5 . . . 124.7(2) n
    C4 C41 C11 . . . 117.2(2) n
    C5 C41 C11 . . . 118.1(2) n
    C41 C5 C6 . . . 119.8(2) n
    C5 C6 C7 . . . 120.5(2) n
    C6 C7 C8 . . . 121.1(2) n
    C7 C8 C11 . . . 118.1(2) n
    O1 C11 C41 . . . 121.5(2) n
    O1 C11 C8 . . . 116.0(2) n
    C41 C11 C8 . . . 122.4(2) n
    C41 C5 H5 . . . 120.15 n
    C6 C7 H7 . . . 119.36 n
    C6 C5 H5 . . . 120.03 n
    C8 C7 H7 . . . 119.58 n
    C5 C6 H6 . . . 119.94 n
    C7 C8 H8 . . . 120.85 n
    C7 C6 H6 . . . 119.56 n
    C11 C8 H8 . . . 121.03 n
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
    Cl4 C4 C3 N3 . . . . 0.1(2) n
    Cl4 C4 C3 C2 . . . . 177.70(10)
                                  n
    Cl4 C4 C41 C5 . . . . 3.1(3) n
    Cl4 C4 C41 C11 . . . . -178.80(10)
                                     n
    O1 C2 C3 N3 . . . . 179.0(2) n
    O1 C2 C3 C4 . . . . 1.2(3) n
    O1 C11 C41 C4 . . . . 0.9(3) n
    O1 C11 C41 C5 . . . . 179.2(2) n
    O1 C11 C8 C7 . . . . -178.7(2) n
    O2 C2 O1 C11 . . . . -178.8(2) n
    O2 C2 C3 N3 . . . . -1.1(3) n
    O2 C2 C3 C4 . . . . -178.8(2) n
    O31 N3 C3 C2 . . . . -76.8(3) n
    O31 N3 C3 C4 . . . . 101.0(3) yes
    O32 N3 C3 C2 . . . . 101.5(2) yes
    O32 N3 C3 C4 . . . . -80.7(3) n
    N3 C3 C4 C41 . . . . 180.0(2) n
    C2 O1 C11 C41 . . . . -2.2(3) n
    C2 O1 C11 C8 . . . . 177.5(2) n
    C2 C3 C4 C41 . . . . -2.4(3) n
    C3 C2 O1 C11 . . . . 1.1(3) n
    C3 C4 C41 C5 . . . . -176.8(2) n
    C3 C4 C41 C11 . . . . 1.3(2) n
    C4 C41 C5 C6 . . . . 177.6(2) n
    C4 C41 C11 C8 . . . . -178.8(2) n
    C41 C5 C6 C7 . . . . 1.0(4) n
    C41 C11 C8 C7 . . . . 1.0(3) n
    C5 C41 C11 C8 . . . . -0.5(3) n
    C5 C6 C7 C8 . . . . -0.5(4) n
    C6 C5 C41 C11 . . . . -0.5(3) n
    C6 C7 C8 C11 . . . . -0.5(4) n
    C6 C7 C8 C11 . . . . -0.5(4) n
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
    C5 H5 Cl4 . 0.95 2.73 3.096(3) 104 no
    C6 H6 O1 2_555 0.95 2.51 3.449(3) 172 yes
