#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/67/2006729.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_2006729
loop_
_publ_author_name
'Karczmarzyk, Zbigniew'
'Pawłowski, Maciej'
_publ_section_title
;
 8-Amino-7-(4-morpholinobutyl)theophylline
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1650
_journal_page_last               1653
_journal_paper_doi               10.1107/S0108270197006483
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C15 H24 N6 O3'
_chemical_formula_weight         336.40
_chemical_name_systematic
;
8-Amino-7-(4-morpholinobutyl)-1,3-dimethyl-3,7-dihydro-1H-purine-
2,6-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.211(2)
_cell_length_b                   8.2850(10)
_cell_length_c                   19.539(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      10
_cell_volume                     1631.1(5)
_computing_data_collection       'Kuma KM-4 software'
_computing_molecular_graphics    'XP SHELXTL-Plus (Sheldrick, 1989)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Kuma KM-4 four-circle diffractometer'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2409
_diffrn_reflns_theta_max         60.01
_diffrn_reflns_theta_min         4.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.0071(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.007
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_restrained_S_obs      1.039
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1017P)²+0.6782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1514
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                2053
_reflns_number_total             2325
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1110.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.6782P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.6782P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2006729
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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .1749(2) -.2595(2) .05823(9) .0437(5) Uani d . 1 . N
N3 .2442(2) .0065(2) .04404(10) .0434(5) Uani d . 1 . N
N7 -.0440(2) .0495(2) .11752(10) .0423(5) Uani d . 1 . N
N8 -.0716(2) .3321(2) .12491(12) .0550(6) Uani d . 1 . N
H81 -.041(3) .432(4) .1163(16) .083 Uiso d . 1 . H
H82 -.150(3) .328(4) .1402(16) .083 Uiso d . 1 . H
N9 .1064(2) .2119(2) .08104(10) .0450(5) Uani d . 1 . N
N14 -.3272(2) .3348(2) .18777(9) .0447(5) Uani d . 1 . N
O2 .3597(2) -.2039(2) .01078(10) .0623(5) Uani d . 1 . O
O6 -.0098(2) -.3221(2) .10589(9) .0549(5) Uani d . 1 . O
O17 -.3457(2) .6784(2) .18859(10) .0650(5) Uani d . 1 . O
C1 .1974(3) -.4321(3) .04855(14) .0555(7) Uani d . 1 . C
H11 .1296(3) -.4932(3) .06559(14) .083 Uiso calc R 1 . H
H12 .2827(3) -.4619(3) .07362(14) .083 Uiso calc R 1 . H
H13 .1946(3) -.4542(3) .00011(14) .083 Uiso calc R 1 . H
C2 .2658(2) -.1552(3) .03577(11) .0437(6) Uani d . 1 . C
C3 .3358(3) .1239(3) .02301(15) .0605(7) Uani d . 1 . C
H31 .4053(3) .0686(3) .00482(15) .091 Uiso calc R 1 . H
H32 .3735(3) .1874(3) .06239(15) .091 Uiso calc R 1 . H
H33 .2890(3) .1932(3) -.01208(15) .091 Uiso calc R 1 . H
C4 .1370(2) .0568(2) .07173(11) .0394(5) Uani d . 1 . C
C5 .0491(2) -.0488(2) .09286(11) .0389(5) Uani d . 1 . C
C6 .0627(2) -.2165(2) .08745(11) .0407(5) Uani d . 1 . C
C7 -.1629(2) .0047(3) .14557(12) .0462(6) Uani d . 1 . C
H71 -.1772(2) -.1106(3) .13991(12) .069 Uiso calc R 1 . H
H72 -.2389(2) .0594(3) .11937(12) .069 Uiso calc R 1 . H
C8 -.0054(2) .2034(2) .10793(12) .0424(5) Uani d . 1 . C
C11 -.1533(2) .0475(3) .22153(12) .0517(6) Uani d . 1 . C
H111 -.1054(2) .1485(3) .23023(12) .077 Uiso calc R 1 . H
H112 -.1027(2) -.0354(3) .24921(12) .077 Uiso calc R 1 . H
C12 -.2880(3) .0641(3) .24453(14) .0601(7) Uani d . 1 . C
H121 -.3286(3) -.0419(3) .24378(14) .090 Uiso calc R 1 . H
H122 -.2746(3) .1020(3) .29212(14) .090 Uiso calc R 1 . H
C13 -.3835(2) .1776(3) .20072(14) .0553(7) Uani d . 1 . C
H131 -.4148(2) .1261(3) .15650(14) .083 Uiso calc R 1 . H
H132 -.4598(2) .1944(3) .22369(14) .083 Uiso calc R 1 . H
C15 -.4211(2) .4247(3) .13748(13) .0532(6) Uani d . 1 . C
H151 -.5054(2) .4325(3) .15406(13) .080 Uiso calc R 1 . H
H152 -.4358(2) .3668(3) .09376(13) .080 Uiso calc R 1 . H
C16 -.3716(3) .5902(3) .12603(14) .0607(7) Uani d . 1 . C
H161 -.2908(3) .5824(3) .10604(14) .091 Uiso calc R 1 . H
H162 -.4372(3) .6471(3) .09333(14) .091 Uiso calc R 1 . H
C18 -.2507(3) .5955(3) .2365(2) .0672(8) Uani d . 1 . C
H181 -.2328(3) .6566(3) .2793(2) .101 Uiso calc R 1 . H
H182 -.1685(3) .5869(3) .2179(2) .101 Uiso calc R 1 . H
C19 -.2980(3) .4295(3) .25147(13) .0586(7) Uani d . 1 . C
H191 -.2302(3) .3753(3) .28393(13) .088 Uiso calc R 1 . H
H192 -.3772(3) .4380(3) .27271(13) .088 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 N1 C6 126.9(2) ?
C2 N1 C1 116.1(2) ?
C6 N1 C1 117.0(2) ?
C4 N3 C2 120.0(2) ?
C4 N3 C3 120.2(2) ?
C2 N3 C3 119.8(2) ?
C8 N7 C5 105.7(2) yes
C8 N7 C7 124.7(2) yes
C5 N7 C7 129.5(2) yes
C8 N9 C4 103.7(2) yes
C15 N14 C13 109.7(2) ?
C15 N14 C19 108.7(2) ?
C13 N14 C19 111.3(2) ?
C18 O17 C16 109.5(2) ?
O2 C2 N3 121.6(2) yes
O2 C2 N1 122.2(2) yes
N3 C2 N1 116.2(2) yes
N9 C4 N3 124.5(2) ?
N9 C4 C5 113.2(2) ?
N3 C4 C5 122.3(2) ?
C4 C5 N7 104.4(2) ?
C4 C5 C6 122.4(2) ?
N7 C5 C6 133.2(2) ?
O6 C6 C5 127.5(2) yes
O6 C6 N1 120.3(2) yes
C5 C6 N1 112.2(2) yes
N7 C7 C11 112.5(2) ?
N8 C8 N9 123.9(2) ?
N8 C8 N7 123.2(2) ?
N9 C8 N7 113.0(2) ?
C7 C11 C12 113.1(2) ?
C13 C12 C11 114.8(2) ?
N14 C13 C12 114.5(2) ?
N14 C15 C16 111.6(2) ?
O17 C16 C15 111.5(2) ?
O17 C18 C19 111.5(2) ?
N14 C19 C18 110.7(2) ?
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
N1 C2 . 1.390(3) yes
N1 C6 . 1.407(3) yes
N1 C1 . 1.466(3) yes
N3 C4 . 1.362(3) yes
N3 C2 . 1.372(3) yes
N3 C3 . 1.454(3) yes
N7 C8 . 1.357(3) yes
N7 C5 . 1.396(3) yes
N7 C7 . 1.459(3) ?
N8 C8 . 1.333(3) yes
N9 C8 . 1.333(3) yes
N9 C4 . 1.342(3) yes
N14 C15 . 1.461(3) ?
N14 C13 . 1.462(3) ?
N14 C19 . 1.461(3) ?
O2 C2 . 1.213(3) yes
O6 C6 . 1.237(3) yes
O17 C18 . 1.412(3) ?
O17 C16 . 1.412(3) ?
C4 C5 . 1.364(3) yes
C5 C6 . 1.402(3) yes
C7 C11 . 1.514(3) ?
C11 C12 . 1.521(3) ?
C12 C13 . 1.516(4) ?
C15 C16 . 1.490(3) ?
C18 C19 . 1.502(4) ?
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
C4 N3 C2 O2 179.4(2)
C3 N3 C2 O2 -0.4(4)
C4 N3 C2 N1 -1.2(3)
C3 N3 C2 N1 179.0(2)
C6 N1 C2 O2 -179.6(2)
C1 N1 C2 O2 -1.3(3)
C6 N1 C2 N3 1.0(3)
C1 N1 C2 N3 179.3(2)
C8 N9 C4 N3 179.0(2)
C8 N9 C4 C5 -0.9(3)
C2 N3 C4 N9 -179.1(2)
C3 N3 C4 N9 0.8(3)
C2 N3 C4 C5 0.8(3)
C3 N3 C4 C5 -179.3(2)
N9 C4 C5 N7 -0.1(3)
N3 C4 C5 N7 180.0(2)
N9 C4 C5 C6 179.8(2)
N3 C4 C5 C6 -0.2(3)
C8 N7 C5 C4 1.1(2)
C7 N7 C5 C4 178.6(2)
C8 N7 C5 C6 -178.8(2)
C7 N7 C5 C6 -1.2(4)
C4 C5 C6 O6 178.8(2)
N7 C5 C6 O6 -1.4(4)
C4 C5 C6 N1 -0.1(3)
N7 C5 C6 N1 179.7(2)
C2 N1 C6 O6 -179.3(2)
C1 N1 C6 O6 2.4(3)
C2 N1 C6 C5 -0.4(3)
C1 N1 C6 C5 -178.6(2)
C8 N7 C7 C11 -68.6(3)
C5 N7 C7 C11 114.2(2)
C4 N9 C8 N8 -179.5(2)
C4 N9 C8 N7 1.6(3)
C5 N7 C8 N8 179.4(2)
C7 N7 C8 N8 1.6(4)
C5 N7 C8 N9 -1.7(3)
C7 N7 C8 N9 -179.5(2)
N7 C7 C11 C12 157.6(2)
C7 C11 C12 C13 -52.6(3)
C15 N14 C13 C12 172.1(2)
C19 N14 C13 C12 -67.6(3)
C11 C12 C13 N14 -48.8(3)
C13 N14 C15 C16 176.3(2)
C19 N14 C15 C16 54.5(2)
C18 O17 C16 C15 58.7(3)
N14 C15 C16 O17 -57.6(3)
C16 O17 C18 C19 -59.2(3)
C15 N14 C19 C18 -54.5(3)
C13 N14 C19 C18 -175.4(2)
O17 C18 C19 N14 58.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21137402
