#------------------------------------------------------------------------------
#$Date: 2015-03-03 03:23:01 +0200 (Tue, 03 Mar 2015) $
#$Revision: 132625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/40/2004089.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004089
loop_
_publ_author_name
'Zaitu, S.'
'Miwa, Y.'
'Taga, T.'
_publ_section_title
;
 1:1 Molecular Complex of Theophylline and <i>p</i>-Nitroaniline
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2390
_journal_page_last               2392
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C13 H14 N6 O4'
_chemical_formula_weight         318.29
_chemical_name_common            'theophilline p-nitroaniline complex'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 116.59(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.693(2)
_cell_length_b                   9.178(1)
_cell_length_c                   22.982(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295.0
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      17.9
_cell_volume                     1451.0(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction        'MSC/AFC Diffractometer Control Software'
_computing_molecular_graphics    KPPXRAY
_computing_publication_material  'EDCIF-J (Osaki & Taga, 1993)'
_computing_structure_refinement
;
KPPXRAY (Taga, Masuda, Higashi & Iizuka, 1991) including a modified
version of ORFLS (Busing, Martin & Levy, 1962)
;
_computing_structure_solution    'MULTAN88 (Main et al., 1988)'
_diffrn_ambient_temperature      295.0
_diffrn_measurement_device       'Rigaku AFC-5'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphaite
_diffrn_radiation_source         rotarix
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2834
_diffrn_reflns_reduction_process NSC/AFC
_diffrn_reflns_theta_max         60
_diffrn_reflns_theta_min         1
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.90
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.4568
_exptl_crystal_density_meas      1.43
_exptl_crystal_density_method    flotation
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.80
_refine_ls_hydrogen_treatment    'refxyz, all from D map'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         1780
_refine_ls_R_factor_obs          0.070
_refine_ls_shift/esd_max         0.05
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'calc w = 1/[\s^2^(F) + 0.023F^2^]'
_refine_ls_wR_factor_obs         0.075
_reflns_number_observed          1780
_reflns_number_total             2621
_reflns_observed_criterion       F>3\s(F)
_[local]_cod_data_source_file    as1190.cif
_[local]_cod_data_source_block   THEOPNA
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1451.0
_cod_database_code               2004089
loop_
_symmetry_equiv_pos_as_xyz
# Original symmetry operators (space group 'P m c b'):
## +X,+Y,+Z
## -X,-Y,-Z
## -X,1/2+Y,1/2-Z
## -X,1/2-Y,1/2+Z

# Symmetry operators for 'P 1 21/c 1':
X,Y,Z
-X,-Y,-Z
-X,1/2+Y,1/2-Z
X,1/2-Y,1/2+Z

_cod_depositor_comments
;

  Replacing the original symmetry operators, which were for the
  spacegroup 'P m c b', with the symmetry operators for the declared
  space group 'P 1 21/c 1'. After such change, the computed brutto
  formulae match the declared one an the packing seems right.

  Saulius Gra\<zulis
  2014-06-18

;
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
_atom_site_thermal_displace_type
N(1) 0.0012(4) 0.2614(3) -0.0718(1) 4.3(1) bij
C(2) 0.0330(6) 0.1112(4) -0.0677(2) 4.7(1) bij
N(3) -0.0907(5) 0.0289(3) -0.1193(2) 4.4(1) bij
C(4) -0.2398(6) 0.0960(3) -0.1710(2) 4.2(1) bij
C(5) -0.2649(5) 0.2419(3) -0.1740(2) 4.1(1) bij
C(6) -0.1446(5) 0.3381(4) -0.1235(2) 4.2(1) bij
N(7) -0.4270(5) 0.2673(3) -0.2316(1) 4.6(1) bij
C(8) -0.4889(6) 0.1377(4) -0.2591(2) 4.9(1) bij
N(9) -0.3779(5) 0.0279(3) -0.2235(1) 4.6(1) bij
O(10) 0.1657(4) 0.0566(3) -0.0202(1) 6.0(1) bij
C(11) 0.1377(8) 0.3481(5) -0.0162(2) 6.0(2) bij
O(12) -0.1595(4) 0.4700(2) -0.1219(1) 5.5(1) bij
C(13) -0.0649(9) -0.1300(5) -0.1186(3) 6.4(2) bij
C(14) 0.5837(6) -0.1073(4) 0.1103(2) 4.8(1) bij
C(15) 0.7458(6) -0.1492(4) 0.1664(2) 5.2(1) bij
C(16) 0.7967(6) -0.2919(4) 0.1791(2) 5.1(1) bij
C(17) 0.6849(6) -0.3977(4) 0.1358(2) 4.7(1) bij
C(18) 0.5218(6) -0.3592(4) 0.0798(2) 5.2(1) bij
C(19) 0.4709(6) -0.2162(4) 0.0667(2) 5.1(1) bij
N(20) 0.5302(6) 0.0353(4) 0.0970(2) 6.3(1) bij
N(21) 0.7388(6) -0.5499(4) 0.1480(2) 6.0(1) bij
O(22) 0.6367(6) -0.6399(3) 0.1081(2) 9.1(2) bij
O(23) 0.8807(5) -0.5835(3) 0.1975(2) 8.2(1) bij
H7 -0.488(5) 0.366(3) -0.249(1) 4.4(8) Biso
H8 -0.611(5) 0.123(3) -0.304(2) 4.9(9) Biso
H11A 0.105(5) 0.454(4) -0.023(2) 5.5(9) Biso
H11B 0.276(6) 0.335(4) -0.010(2) 6(1) Biso
H11C 0.135(5) 0.316(4) 0.026(2) 6(1) Biso
H13A -0.165(6) -0.177(4) -0.159(2) 6(1) Biso
H13B -0.076(6) -0.175(4) -0.079(2) 6(1) Biso
H13C 0.069(6) -0.156(4) -0.114(2) 6(1) Biso
H15 0.823(5) -0.070(3) 0.199(2) 5.0(9) Biso
H16 0.919(5) -0.321(3) 0.220(2) 4.9(8) Biso
H18 0.443(5) -0.439(4) 0.047(2) 4.9(8) Biso
H19 0.350(5) -0.186(4) 0.025(2) 5.1(9) Biso
H20A 0.606(5) 0.116(4) 0.127(2) 6(1) Biso
H20B 0.411(6) 0.063(4) 0.055(2) 5(1) Biso
loop_
_atom_site_aniso_label
N(1)
C(2)
N(3)
C(4)
C(5)
C(6)
N(7)
C(8)
N(9)
O(10)
C(11)
O(12)
C(13)
C(14)
C(15)
C(16)
C(17)
C(18)
C(19)
N(20)
N(21)
O(22)
O(23)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 International_Tables_Vol_IV_Table_2.2B
O 0.047 0.032 International_Tables_Vol_IV_Table_2.2B
H 0.000 0.000 International_Tables_Vol_IV_Table_2.2B
N 0.029 0.018 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) N(1) C(6) 127.0(3) yes
C(2) N(1) C(11) 116.1(3) yes
C(6) N(1) C(11) 116.9(3) yes
N(1) C(2) N(3) 117.0(3) yes
N(1) C(2) O(10) 121.2(3) yes
N(3) C(2) O(10) 121.9(3) yes
C(2) N(3) C(4) 119.3(3) yes
C(2) N(3) C(13) 120.0(3) yes
C(4) N(3) C(13) 120.7(3) yes
N(3) C(4) C(5) 122.3(3) yes
N(3) C(4) N(9) 125.7(3) yes
C(5) C(4) N(9) 112.1(3) yes
C(4) C(5) C(6) 123.2(3) yes
C(4) C(5) N(7) 105.4(3) yes
C(6) C(5) N(7) 131.3(3) yes
N(1) C(6) C(5) 111.2(3) yes
N(1) C(6) O(12) 121.5(3) yes
C(5) C(6) O(12) 127.3(3) yes
C(5) N(7) C(8) 106.5(3) yes
N(7) C(8) N(9) 112.8(3) yes
C(4) N(9) C(8) 103.2(3) yes
C(15) C(14) C(19) 118.4(3) yes
C(15) C(14) N(20) 122.0(3) yes
C(19) C(14) N(20) 119.6(3) yes
C(14) C(15) C(16) 121.2(3) yes
C(15) C(16) C(17) 119.7(3) yes
C(16) C(17) C(18) 120.3(3) yes
C(16) C(17) N(21) 120.4(3) yes
C(18) C(17) N(21) 119.3(3) yes
C(17) C(18) C(19) 120.2(3) yes
C(14) C(19) C(18) 120.1(3) yes
C(17) N(21) O(22) 118.3(3) yes
C(17) N(21) O(23) 119.1(3) yes
O(22) N(21) O(23) 122.6(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(2) 1.396(5) yes
N(1) C(6) 1.404(4) yes
N(1) C(11) 1.472(5) yes
C(2) N(3) 1.368(5) yes
C(2) O(10) 1.220(4) yes
N(3) C(4) 1.374(5) yes
N(3) C(13) 1.471(5) yes
C(4) C(5) 1.350(4) yes
C(4) N(9) 1.352(4) yes
C(5) C(6) 1.422(5) yes
C(5) N(7) 1.373(4) yes
C(6) O(12) 1.218(4) yes
N(7) C(8) 1.331(4) yes
C(8) N(9) 1.337(4) yes
C(14) C(15) 1.388(5) yes
C(14) C(19) 1.406(5) yes
C(14) N(20) 1.365(5) yes
C(15) C(16) 1.361(5) yes
C(16) C(17) 1.381(5) yes
C(17) C(18) 1.382(5) yes
C(17) N(21) 1.448(5) yes
C(18) C(19) 1.364(5) yes
N(21) O(22) 1.223(5) yes
N(21) O(23) 1.212(5) yes
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
_geom_torsion_publ_flag
N(1) C(2) N(3) C(4) -1.4(7) no
N(1) C(2) N(3) C(13) 179.5(5) no
C(2) N(1) C(6) C(5) 0.6(7) no
C(2) N(1) C(6) O(12) 179.8(5) no
C(2) N(3) C(4) C(5) 2.6(8) no
C(2) N(3) C(4) N(9) -176.6(5) no
N(3) C(4) C(5) C(6) -2.2(8) no
N(3) C(4) C(5) N(7) -179.5(5) no
N(3) C(4) N(9) C(8) 179.4(5) no
C(4) C(5) C(6) N(1) 0.6(7) no
C(4) C(5) C(6) O(12) -178.6(5) no
C(4) C(5) N(7) C(8) 0.3(6) no
C(5) C(4) N(9) C(8) 0.2(5) no
C(5) N(7) C(8) N(9) -0.2(5) no
C(6) N(1) C(2) N(3) -0.2(6) no
C(6) N(1) C(2) O(10) 179.6(5) no
C(6) C(5) N(7) C(8) -176.8(5) no
N(7) C(5) C(6) N(1) 177.2(5) no
N(7) C(5) C(6) O(12) -2.0(9) no
N(7) C(8) N(9) C(4) 0.0(6) no
N(9) C(4) C(5) C(6) 177.1(5) no
N(9) C(4) C(5) N(7) -0.3(6) no
O(10) C(2) N(3) C(4) 178.8(5) no
O(10) C(2) N(3) C(13) -0.3(8) no
C(11) N(1) C(2) N(3) -179.1(5) no
C(11) N(1) C(2) O(10) 0.7(7) no
C(11) N(1) C(6) C(5) 179.5(4) no
C(11) N(1) C(6) O(12) -1.3(7) no
C(13) N(3) C(4) C(5) -178.3(6) no
C(13) N(3) C(4) N(9) 2.6(9) no
C(14) C(15) C(16) C(17) -0.5(8) no
C(15) C(14) C(19) C(18) -0.2(6) no
C(15) C(16) C(17) C(18) -0.1(7) no
C(15) C(16) C(17) N(21) 178.9(5) no
C(16) C(17) C(18) C(19) 0.5(8) no
C(16) C(17) N(21) O(22) -179.3(6) no
C(16) C(17) N(21) O(23) 1.8(8) no
C(17) C(18) C(19) C(14) -0.3(7) no
C(18) C(17) N(21) O(22) -0.3(8) no
C(18) C(17) N(21) O(23) -179.2(5) no
C(19) C(14) C(15) C(16) 0.6(8) no
N(20) C(14) C(15) C(16) 179.7(5) no
N(20) C(14) C(19) C(18) -179.3(5) no
N(21) C(17) C(18) C(19) -178.6(5) no
_journal_paper_doi 10.1107/S010827019500864X