##############################################################################
###                                                                        ###
###        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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##############################################################################
                                             
data_global
_audit_creation_method     'manual editing of SHELXTL-NT created .cif'
_journal_date_recd_electronic     2001-10-10
_journal_date_accepted     2001-11-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue     12
_journal_page_first     o1163
_journal_page_last     o1165
_journal_paper_category     EO
_publ_contact_author_name     'Dr Prakas R Maulik'
_publ_contact_author_address
;
Molecular and Structural Biology Division
Central Drug Research Institute
Chattar Manzil Palace
Post Box No. 173
Lucknow 226 001
India
;
_publ_contact_author_email     maulik_prakas@yahoo.com
_publ_contact_author_fax     '91(0522)223405'
_publ_contact_author_phone     '91(0522)212411-18'
_publ_section_title
;
1,3-Bis(8-chlorotheophyllin-7-yl)propane: no intramolecular stacking
;
_publ_section_title_footnote
;
CDRI communication No. 6120.
;
loop_
    _publ_author_name
    _publ_author_address
    'Maulik, Prakas R.'
;
Molecular and Structural Biology Division
Central Drug Research Institute
Lucknow 226 001
India
;
    'Avasthi, Kamlakar'
;
Medicinal Chemistry Division
Central Drug Research Institute
Lucknow 226001
India
;
    'Sarkhel, Sanjay'
;
Molecular and Structural Biology Division
Central Drug Research Institute
Lucknow 226001
India
;
    'Sharon, Ashoke'
;
Molecular and Structural Biology Division
Central Drug Research Institute
Lucknow 226001
India
;
    'Rawat, Diwan S.'
;
Medicinal Chemistry Division
Central Drug Research Institute
Lucknow 226001
India
;
    'Bal, Chandralata'
;
Medicinal Chemistry Division
Central Drug Research Institute
Lucknow 226001
India
;
data_I
_chemical_name_systematic
;
1,3-bis(8-chlorotheophyllin-7-yl)propane
;
_chemical_name_common     1,3-bis(8-chlorotheophyllin-7-yl)propane
_chemical_formula_moiety     'C17 H18 Cl2 N8 O4'
_chemical_formula_sum     'C17 H18 Cl2 N8 O4'
_chemical_formula_iupac     'C17 H18 Cl2 N8 O4'
_chemical_formula_weight     469.29
_chemical_melting_point     180
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'I 2/a'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y, -z'
    'x+1/2, y+1/2, z+1/2'
    '-x+1, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y, z'
    '-x+1/2, -y+1/2, -z+1/2'
    'x, -y+1/2, z+1/2'
_cell_length_a     19.9290(10)
_cell_length_b     4.3417(2)
_cell_length_c     22.788(2)
_cell_angle_alpha     90.00
_cell_angle_beta     91.400(10)
_cell_angle_gamma     90.00
_cell_volume     1970.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     35
_cell_measurement_theta_min     5.2
_cell_measurement_theta_max     12.5
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max      .35
_exptl_crystal_size_mid      .25
_exptl_crystal_size_min      .14
_exptl_crystal_density_diffrn     1.582
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     968
_exptl_absorpt_coefficient_mu      .375
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker P4'
_diffrn_measurement_method     θ-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2379
_diffrn_reflns_av_R_equivalents      .014
_diffrn_reflns_av_sigmaI/netI      .026
_diffrn_reflns_theta_min     1.79
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max      .999
_diffrn_measured_fraction_theta_full      .999
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     1
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     0
_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 > 2sigma(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     1724
_reflns_number_gt     1436
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .047
_refine_ls_R_factor_gt      .037
_refine_ls_wR_factor_ref      .098
_refine_ls_goodness_of_fit_ref     1.07
_refine_ls_restrained_S_all     1.07
_refine_ls_number_reflns     1724
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0508P)²+0.8204P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max      .20
_refine_diff_density_min      -.27
_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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl'  .1484  .1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'XSCANS (Siemens, 1996)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXTL-NT (Bruker, 1997)'
_computing_structure_refinement     'SHELXTL-NT'
_computing_molecular_graphics     'SHELXTL-NT'
_computing_publication_material     'SHELXTL-NT'
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
    Cl1  .32994(2)  .27327(15)  .34767(3)  .0603(2) Uani d . 1 . . Cl
    O1  -.01634(7)  -.2310(3)  .33147(7)  .0541(4) Uani d . 1 . . O
    O2  .08167(7)  .4415(4)  .46294(6)  .0598(4) Uani d . 1 . . O
    N1  .03258(7)  .1034(4)  .39686(7)  .0410(4) Uani d . 1 . . N
    C2  .03373(9)  -.0926(4)  .34834(8)  .0395(4) Uani d . 1 . . C
    N3  .09361(7)  -.1233(4)  .31994(6)  .0394(4) Uani d . 1 . . N
    C4  .14951(8)  .0304(4)  .34123(7)  .0341(4) Uani d . 1 . . C
    C5  .14660(9)  .2154(4)  .38948(7)  .0342(4) Uani d . 1 . . C
    C6  .08699(9)  .2707(4)  .42072(8)  .0397(5) Uani d . 1 . . C
    N7  .21098(7)  .3334(4)  .39704(6)  .0357(4) Uani d . 1 . . N
    C8  .24671(9)  .2057(5)  .35374(8)  .0394(5) Uani d . 1 . . C
    N9  .21176(7)  .0216(4)  .31853(6)  .0416(4) Uani d . 1 . . N
    C10  .23461(10)  .5265(4)  .44602(7)  .0385(4) Uani d . 1 . . C
    H10A  .2005  .6774  .4550  .046 Uiso calc R 1 . . H
    H10B  .2747  .6362  .4349  .046 Uiso calc R 1 . . H
    C11  .2500  .3316(6)  .5000  .0398(6) Uani d S 1 . . C
    H11A  .2118  .2001  .5076  .048 Uiso calc PR  .50 . . H
    H11B  .2882  .2001  .4924  .048 Uiso calc PR  .50 . . H
    C12  -.03232(10)  .1371(6)  .42521(10)  .0597(6) Uani d . 1 . . C
    H12A  -.0647  .2194  .3975  .090 Uiso calc R 1 . . H
    H12B  -.0275  .2746  .4580  .090 Uiso calc R 1 . . H
    H12C  -.0472  -.0605  .4386  .090 Uiso calc R 1 . . H
    C13  .09598(11)  -.3047(5)  .26595(8)  .0496(5) Uani d . 1 . . C
    H13A  .0717  -.4934  .2709  .074 Uiso calc R 1 . . H
    H13B  .1418  -.3503  .2574  .074 Uiso calc R 1 . . H
    H13C  .0760  -.1894  .2341  .074 Uiso calc R 1 . . 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
    Cl1  .0401(3)  .0828(5)  .0583(4)  -.0075(3)  .0046(2)  -.0088(3)
    O1  .0465(8)  .0605(9)  .0545(9)  -.0111(7)  -.0127(7)  .0014(7)
    O2  .0575(9)  .0707(11)  .0517(9)  .0000(8)  .0100(7)  -.0259(8)
    N1  .0375(8)  .0448(9)  .0406(8)  .0033(7)  -.0008(7)  .0006(8)
    C2  .0410(10)  .0403(10)  .0368(9)  .0016(9)  -.0085(8)  .0060(9)
    N3  .0451(8)  .0396(9)  .0330(8)  .0004(7)  -.0084(7)  -.0050(7)
    C4  .0389(9)  .0341(10)  .0288(8)  .0041(8)  -.0059(7)  .0011(8)
    C5  .0380(9)  .0357(10)  .0285(9)  .0019(8)  -.0063(7)  -.0004(8)
    C6  .0429(10)  .0401(11)  .0360(10)  .0039(8)  -.0013(8)  .0011(9)
    N7  .0413(8)  .0363(8)  .0290(7)  .0006(7)  -.0065(6)  -.0004(6)
    C8  .0399(10)  .0452(11)  .0331(9)  .0027(8)  -.0013(8)  .0010(8)
    N9  .0430(8)  .0483(10)  .0336(8)  .0035(7)  -.0007(6)  -.0061(7)
    C10  .0498(10)  .0326(10)  .0326(9)  -.0032(8)  -.0093(8)  -.0008(8)
    C11  .0517(15)  .0317(14)  .0355(14)  .000  -.0116(11)  .000
    C12  .0436(11)  .0729(16)  .0629(14)  .0033(11)  .0076(10)  -.0027(13)
    C13  .0651(13)  .0487(12)  .0344(10)  -.0003(10)  -.0107(9)  -.0081(9)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    Cl1 C8 . 1.6932(19) ?
    O1 C2 . 1.219(2) ?
    O2 C6 . 1.221(2) ?
    N1 C2 . 1.396(3) ?
    N1 C6 . 1.404(2) ?
    N1 C12 . 1.467(2) ?
    C2 N3 . 1.378(2) ?
    N3 C4 . 1.377(2) ?
    N3 C13 . 1.462(2) ?
    C4 N9 . 1.356(2) ?
    C4 C5 . 1.364(2) ?
    C5 N7 . 1.388(2) ?
    C5 C6 . 1.420(3) ?
    N7 C8 . 1.350(3) ?
    N7 C10 . 1.465(2) ?
    C8 N9 . 1.319(2) ?
    C10 C11 . 1.518(2) ?
    C11 C10 2_556 1.518(2) ?
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
    C2 N1 C6 . . 126.50(16) ?
    C2 N1 C12 . . 116.19(17) ?
    C6 N1 C12 . . 117.31(17) ?
    O1 C2 N3 . . 121.05(18) ?
    O1 C2 N1 . . 121.42(18) ?
    N3 C2 N1 . . 117.53(16) ?
    C4 N3 C2 . . 119.35(15) ?
    C4 N3 C13 . . 121.00(16) ?
    C2 N3 C13 . . 119.56(16) ?
    N9 C4 C5 . . 112.41(16) ?
    N9 C4 N3 . . 126.28(16) ?
    C5 C4 N3 . . 121.31(17) ?
    C4 C5 N7 . . 105.08(16) ?
    C4 C5 C6 . . 123.79(17) ?
    N7 C5 C6 . . 131.08(16) ?
    O2 C6 N1 . . 122.56(18) ?
    O2 C6 C5 . . 125.97(18) ?
    N1 C6 C5 . . 111.47(16) ?
    C8 N7 C5 . . 105.08(15) ?
    C8 N7 C10 . . 128.79(16) ?
    C5 N7 C10 . . 125.80(15) ?
    N9 C8 N7 . . 114.40(16) ?
    N9 C8 Cl1 . . 123.98(15) ?
    N7 C8 Cl1 . . 121.59(15) ?
    C8 N9 C4 . . 103.02(15) ?
    N7 C10 C11 . . 110.69(15) ?
    C10 C11 C10 2_556 . 112.3(2) ?
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
    C6 N1 C2 O1 . . . . 179.05(17) ?
    C12 N1 C2 O1 . . . . -1.2(3) ?
    C6 N1 C2 N3 . . . . -1.2(3) ?
    C12 N1 C2 N3 . . . . 178.51(17) ?
    O1 C2 N3 C4 . . . . -178.29(17) ?
    N1 C2 N3 C4 . . . . 2.0(3) ?
    O1 C2 N3 C13 . . . . 5.0(3) ?
    N1 C2 N3 C13 . . . . -174.74(16) ?
    C2 N3 C4 N9 . . . . 179.48(17) ?
    C13 N3 C4 N9 . . . . -3.9(3) ?
    C2 N3 C4 C5 . . . .  -.8(3) ?
    C13 N3 C4 C5 . . . . 175.87(17) ?
    N9 C4 C5 N7 . . . .  .8(2) ?
    N3 C4 C5 N7 . . . . -178.94(15) ?
    N9 C4 C5 C6 . . . . 178.40(17) ?
    N3 C4 C5 C6 . . . . -1.4(3) ?
    C2 N1 C6 O2 . . . . 178.92(19) ?
    C12 N1 C6 O2 . . . .  -.8(3) ?
    C2 N1 C6 C5 . . . .  -.7(3) ?
    C12 N1 C6 C5 . . . . 179.56(17) ?
    C4 C5 C6 O2 . . . . -177.62(19) ?
    N7 C5 C6 O2 . . . .  -.7(3) ?
    C4 C5 C6 N1 . . . . 2.0(3) ?
    N7 C5 C6 N1 . . . . 178.90(17) ?
    C4 C5 N7 C8 . . . . -1.07(19) ?
    C6 C5 N7 C8 . . . . -178.38(19) ?
    C4 C5 N7 C10 . . . . -174.92(16) ?
    C6 C5 N7 C10 . . . . 7.8(3) ?
    C5 N7 C8 N9 . . . . 1.0(2) ?
    C10 N7 C8 N9 . . . . 174.64(16) ?
    C5 N7 C8 Cl1 . . . . -177.28(13) ?
    C10 N7 C8 Cl1 . . . . -3.7(3) ?
    N7 C8 N9 C4 . . . .  -.5(2) ?
    Cl1 C8 N9 C4 . . . . 177.74(14) ?
    C5 C4 N9 C8 . . . .  -.2(2) ?
    N3 C4 N9 C8 . . . . 179.53(17) ?
    C8 N7 C10 C11 . . . . -93.3(2) ?
    C5 N7 C10 C11 . . . . 79.1(2) ?
    N7 C10 C11 C10 . . . 2_556 -172.11(17) ?
