#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224628.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_2224628
loop_
_publ_author_name
'Jotani, Mukesh M.'
'Shah, Rina D.'
'Jasinski, Jerry P.'
_publ_section_title
7-(4-Methoxyphenyl)-5-methyl-9-phenyl-7H-pyrrolo[2',3':4,5]pyrimido[1,6-d]tetrazole
_journal_coeditor_code           GW2072
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o212
_journal_page_last               o213
_journal_paper_doi               10.1107/S1600536809053653
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H16 N6 O'
_chemical_formula_moiety         'C20 H16 N6 O'
_chemical_formula_sum            'C20 H16 N6 O'
_chemical_formula_weight         356.39
_chemical_name_systematic
;
7-(4-Methoxyphenyl)-5-methyl-9-phenyl-7H-
pyrrolo[2',3':4,5]pyrimido[1,6-d]tetrazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.217(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.738(2)
_cell_length_b                   7.032(3)
_cell_length_c                   19.4350(3)
_cell_measurement_reflns_used    5176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.26
_cell_measurement_theta_min      2.17
_cell_volume                     1761.9(8)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP32 and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2003)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            42323
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.202
_refine_ls_extinction_coef       0.0104(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.2469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                3694
_reflns_number_total             5137
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gw2072.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224628
_cod_database_fobs_code          2224628
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'
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
N N1 0.49323(7) 0.66669(14) 0.35550(5) 0.0364(2) Uani d . 1 . .
N N2 0.64444(8) 0.71967(13) 0.46114(6) 0.0390(2) Uani d . 1 . .
N N3 0.60830(8) 0.78499(13) 0.56626(5) 0.0387(2) Uani d . 1 . .
N N4 0.63253(10) 0.82763(16) 0.63905(6) 0.0503(3) Uani d . 1 . .
N N5 0.54477(10) 0.84057(18) 0.64892(6) 0.0553(3) Uani d . 1 . .
N N6 0.46241(9) 0.80796(15) 0.58676(5) 0.0461(3) Uani d . 1 . .
O O1 0.67511(8) 0.63011(14) 0.14173(5) 0.0557(3) Uani d . 1 . .
C C1 0.54006(9) 0.70521(14) 0.42843(6) 0.0342(2) Uani d . 1 . .
C C2 0.46308(9) 0.72839(14) 0.45931(6) 0.0322(2) Uani d . 1 . .
C C3 0.36448(9) 0.70460(14) 0.40206(6) 0.0331(2) Uani d . 1 . .
C C4 0.38831(9) 0.66682(16) 0.34039(6) 0.0372(2) Uani d . 1 . .
H H4 0.3383 0.6437 0.2933 0.045 Uiso calc R 1 . .
C C5 0.67850(10) 0.75945(15) 0.53047(7) 0.0400(3) Uani d . 1 . .
C C6 0.50261(9) 0.77276(14) 0.53513(6) 0.0350(2) Uani d . 1 . .
C C7 0.79065(11) 0.7757(2) 0.57366(8) 0.0538(3) Uani d . 1 . .
H H7A 0.8307 0.7651 0.5408 0.081 Uiso calc R 1 . .
H H7B 0.8109 0.6735 0.6102 0.081 Uiso calc R 1 . .
H H7C 0.8044 0.8991 0.5986 0.081 Uiso calc R 1 . .
C C8 0.25890(9) 0.71760(15) 0.40362(6) 0.0348(2) Uani d . 1 . .
C C9 0.17475(10) 0.73306(18) 0.33836(7) 0.0437(3) Uani d . 1 . .
H H9 0.1867 0.7361 0.2931 0.052 Uiso calc R 1 . .
C C10 0.07452(11) 0.7441(2) 0.33822(8) 0.0531(3) Uani d . 1 . .
H H10 0.0183 0.7540 0.2931 0.064 Uiso calc R 1 . .
C C11 0.05569(11) 0.7407(2) 0.40303(9) 0.0572(4) Uani d . 1 . .
H H11 -0.0134 0.7493 0.4030 0.069 Uiso calc R 1 . .
C C12 0.13717(12) 0.7249(2) 0.46801(9) 0.0559(4) Uani d . 1 . .
H H12 0.1242 0.7217 0.5129 0.067 Uiso calc R 1 . .
C C13 0.23768(11) 0.71372(18) 0.46865(7) 0.0444(3) Uani d . 1 . .
H H13 0.2932 0.7032 0.5141 0.053 Uiso calc R 1 . .
C C14 0.54240(9) 0.65119(16) 0.30183(6) 0.0352(2) Uani d . 1 . .
C C15 0.50818(9) 0.76648(17) 0.24049(6) 0.0409(3) Uani d . 1 . .
H H15 0.4533 0.8542 0.2348 0.049 Uiso calc R 1 . .
C C16 0.55355(10) 0.75407(18) 0.18782(7) 0.0437(3) Uani d . 1 . .
H H16 0.5294 0.8320 0.1454 0.052 Uiso calc R 1 . .
C C17 0.63448(9) 0.62818(17) 0.19641(6) 0.0397(3) Uani d . 1 . .
C C18 0.66942(9) 0.51457(18) 0.25825(7) 0.0430(3) Uani d . 1 . .
H H18 0.7254 0.4291 0.2646 0.052 Uiso calc R 1 . .
C C19 0.62275(9) 0.52564(17) 0.31077(6) 0.0413(3) Uani d . 1 . .
H H19 0.6461 0.4467 0.3530 0.050 Uiso calc R 1 . .
C C20 0.75810(14) 0.5043(3) 0.14708(10) 0.0782(6) Uani d . 1 . .
H H20A 0.8168 0.5324 0.1918 0.117 Uiso calc R 1 . .
H H20B 0.7795 0.5207 0.1043 0.117 Uiso calc R 1 . .
H H20C 0.7354 0.3728 0.1488 0.117 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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'
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
C1 N1 C4 . . 107.82(9) ?
C1 N1 C14 . . 126.90(10) ?
C4 N1 C14 . . 124.89(9) ?
C5 N2 C1 . . 116.55(11) ?
C6 N3 N4 . . 108.19(10) ?
C6 N3 C5 . . 125.97(10) ?
N4 N3 C5 . . 125.83(11) ?
N5 N4 N3 . . 105.27(10) ?
N4 N5 N6 . . 112.98(11) ?
C6 N6 N5 . . 105.53(11) ?
C17 O1 C20 . . 118.22(10) ?
N2 C1 N1 . . 122.92(10) ?
N2 C1 C2 . . 128.74(10) ?
N1 C1 C2 . . 108.33(10) ?
C1 C2 C6 . . 113.45(10) ?
C1 C2 C3 . . 107.80(9) ?
C6 C2 C3 . . 138.71(11) ?
C4 C3 C2 . . 104.68(10) ?
C4 C3 C8 . . 124.54(10) ?
C2 C3 C8 . . 130.77(10) ?
N1 C4 C3 . . 111.35(10) ?
N1 C4 H4 . . 124.3 ?
C3 C4 H4 . . 124.3 ?
N2 C5 N3 . . 119.19(11) ?
N2 C5 C7 . . 122.47(12) ?
N3 C5 C7 . . 118.33(11) ?
N6 C6 N3 . . 108.03(10) ?
N6 C6 C2 . . 135.87(11) ?
N3 C6 C2 . . 116.10(10) ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C13 C8 C9 . . 117.35(11) ?
C13 C8 C3 . . 122.51(11) ?
C9 C8 C3 . . 120.13(10) ?
C10 C9 C8 . . 121.33(12) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C11 C10 C9 . . 120.20(14) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 119.60(13) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C11 C12 C13 . . 120.58(13) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.93(13) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
C19 C14 C15 . . 120.24(10) ?
C19 C14 N1 . . 121.15(10) ?
C15 C14 N1 . . 118.61(10) ?
C16 C15 C14 . . 119.92(11) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.19(11) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
O1 C17 C18 . . 124.85(11) ?
O1 C17 C16 . . 115.35(10) ?
C18 C17 C16 . . 119.78(11) ?
C19 C18 C17 . . 119.91(11) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C14 C19 C18 . . 119.94(11) ?
C14 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
O1 C20 H20A . . 109.5 ?
O1 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O1 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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 C1 . 1.3661(14) ?
N1 C4 . 1.3680(15) ?
N1 C14 . 1.4294(14) ?
N2 C5 . 1.2951(16) ?
N2 C1 . 1.3567(15) ?
N3 C6 . 1.3691(16) ?
N3 N4 . 1.3699(14) ?
N3 C5 . 1.3819(17) ?
N4 N5 . 1.2879(17) ?
N5 N6 . 1.3591(16) ?
N6 C6 . 1.3254(15) ?
O1 C17 . 1.3606(13) ?
O1 C20 . 1.4183(17) ?
C1 C2 . 1.3942(16) ?
C2 C6 . 1.4178(15) ?
C2 C3 . 1.4351(15) ?
C3 C4 . 1.3730(15) ?
C3 C8 . 1.4640(16) ?
C4 H4 . 0.9500 ?
C5 C7 . 1.4824(18) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C13 . 1.3920(17) ?
C8 C9 . 1.3942(17) ?
C9 C10 . 1.3783(18) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.371(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.372(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.379(2) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C19 . 1.3768(16) ?
C14 C15 . 1.3828(16) ?
C15 C16 . 1.3730(17) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.3854(17) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.3835(16) ?
C18 C19 . 1.3825(16) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
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
C13 H13 N6 . 0.95 2.38 3.2159(18) 146.4
C12 H12 O1 4_576 0.95 2.57 3.3902(17) 144.1
C7 H7B Cg4 3_666 0.96 2.90 3.620(2) 132
C7 H7C Cg4 3_676 0.96 2.69 3.554(2) 150
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 N3 N4 N5 . . . . -0.45(12) ?
C5 N3 N4 N5 . . . . 179.34(10) ?
N3 N4 N5 N6 . . . . 0.33(14) ?
N4 N5 N6 C6 . . . . -0.08(14) ?
C5 N2 C1 N1 . . . . 179.05(10) ?
C5 N2 C1 C2 . . . . 0.35(17) ?
C4 N1 C1 N2 . . . . -178.52(10) ?
C14 N1 C1 N2 . . . . -5.42(17) ?
C4 N1 C1 C2 . . . . 0.41(12) ?
C14 N1 C1 C2 . . . . 173.51(10) ?
N2 C1 C2 C6 . . . . -0.04(16) ?
N1 C1 C2 C6 . . . . -178.89(9) ?
N2 C1 C2 C3 . . . . 178.25(10) ?
N1 C1 C2 C3 . . . . -0.60(11) ?
C1 C2 C3 C4 . . . . 0.54(11) ?
C6 C2 C3 C4 . . . . 178.17(12) ?
C1 C2 C3 C8 . . . . -178.67(10) ?
C6 C2 C3 C8 . . . . -1.0(2) ?
C1 N1 C4 C3 . . . . -0.06(13) ?
C14 N1 C4 C3 . . . . -173.33(10) ?
C2 C3 C4 N1 . . . . -0.30(12) ?
C8 C3 C4 N1 . . . . 178.97(9) ?
C1 N2 C5 N3 . . . . -0.24(15) ?
C1 N2 C5 C7 . . . . 178.70(10) ?
C6 N3 C5 N2 . . . . -0.17(16) ?
N4 N3 C5 N2 . . . . -179.92(10) ?
C6 N3 C5 C7 . . . . -179.15(10) ?
N4 N3 C5 C7 . . . . 1.10(16) ?
N5 N6 C6 N3 . . . . -0.22(12) ?
N5 N6 C6 C2 . . . . 179.99(12) ?
N4 N3 C6 N6 . . . . 0.42(12) ?
C5 N3 C6 N6 . . . . -179.37(10) ?
N4 N3 C6 C2 . . . . -179.74(9) ?
C5 N3 C6 C2 . . . . 0.47(15) ?
C1 C2 C6 N6 . . . . 179.44(12) ?
C3 C2 C6 N6 . . . . 1.9(2) ?
C1 C2 C6 N3 . . . . -0.34(13) ?
C3 C2 C6 N3 . . . . -177.88(11) ?
C4 C3 C8 C13 . . . . 165.29(11) ?
C2 C3 C8 C13 . . . . -15.64(17) ?
C4 C3 C8 C9 . . . . -14.18(16) ?
C2 C3 C8 C9 . . . . 164.89(11) ?
C13 C8 C9 C10 . . . . 0.00(17) ?
C3 C8 C9 C10 . . . . 179.50(11) ?
C8 C9 C10 C11 . . . . 0.3(2) ?
C9 C10 C11 C12 . . . . -0.5(2) ?
C10 C11 C12 C13 . . . . 0.4(2) ?
C11 C12 C13 C8 . . . . -0.2(2) ?
C9 C8 C13 C12 . . . . -0.05(17) ?
C3 C8 C13 C12 . . . . -179.54(11) ?
C1 N1 C14 C19 . . . . 55.88(16) ?
C4 N1 C14 C19 . . . . -132.14(12) ?
C1 N1 C14 C15 . . . . -123.61(12) ?
C4 N1 C14 C15 . . . . 48.36(16) ?
C19 C14 C15 C16 . . . . 0.85(18) ?
N1 C14 C15 C16 . . . . -179.66(11) ?
C14 C15 C16 C17 . . . . -0.88(19) ?
C20 O1 C17 C18 . . . . 1.4(2) ?
C20 O1 C17 C16 . . . . -179.88(14) ?
C15 C16 C17 O1 . . . . -178.74(12) ?
C15 C16 C17 C18 . . . . 0.1(2) ?
O1 C17 C18 C19 . . . . 179.42(12) ?
C16 C17 C18 C19 . . . . 0.70(19) ?
C15 C14 C19 C18 . . . . -0.04(18) ?
N1 C14 C19 C18 . . . . -179.52(11) ?
C17 C18 C19 C14 . . . . -0.73(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744134
