#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023866.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023866
loop_
_publ_author_name
'Igor Čerňa'
'Radek Pohl'
'Blanka Klepetářová'
'Michal Hocek'
_publ_contact_author_address
; 
Institute of Organic Chemistry and Biochemistry
Academy of Sciences of the Czech Republic
Flemingovo nam. 2
16010 Prague 6
Czech Republic
;
_publ_contact_author_email       hocek@uochb.cas.cz
_publ_contact_author_fax         '+420 220183559'
_publ_contact_author_name        'Michal Hocek'
_publ_contact_author_phone       '+420 220183324'
_publ_section_title
;
 Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines
 by a Combination of the Suzuki Cross-coupling,
 N-Arylation, and Direct C-H Arylation Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9048
_journal_page_last               9054
_journal_paper_doi               10.1021/jo8018126
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C21 H21 N5 O4, C H Cl3'
_chemical_formula_sum            'C22 H22 Cl3 N5 O4'
_chemical_formula_weight         526.81
_chemical_name_systematic
9-(4-methoxyphenyl)-8-(3,4,5-trimethoxyphenyl)-9H-purin-6-amine
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-08-13
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 91.195(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1515(12)
_cell_length_b                   13.1309(11)
_cell_length_c                   18.5570(17)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    298
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     2473.1(4)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29663
_diffrn_reflns_theta_full        73.710
_diffrn_reflns_theta_max         78.414
_diffrn_reflns_theta_min         4.125
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.687
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       41(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1339
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000254
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 6.72 0.893 4.57 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0780
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0567
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2510
_reflns_number_total             5219
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            jo8018126_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023866
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl32 Cl 0.61153(19) 0.45985(14) 0.20165(11) 0.1413 1.0000 Uani . . . . . .
Cl33 Cl 0.43437(16) 0.46544(14) 0.31788(7) 0.1144 1.0000 Uani . . . . . .
Cl34 Cl 0.58683(19) 0.64296(13) 0.28216(8) 0.1249 1.0000 Uani . . . . . .
O17 O 0.3363(3) 0.71922(19) 0.50584(14) 0.0649 1.0000 Uani . . . . . .
O19 O 0.3686(3) 0.8266(2) 0.62718(13) 0.0612 1.0000 Uani . . . . . .
O21 O 0.2713(3) 1.0142(2) 0.63985(13) 0.0685 1.0000 Uani . . . . . .
O29 O 0.3058(3) 1.4336(2) 0.53195(16) 0.0749 1.0000 Uani . . . . . .
N1 N -0.0559(3) 1.0932(2) 0.17280(16) 0.0598 1.0000 Uani . . . . . .
N3 N 0.0329(3) 1.2029(2) 0.26576(16) 0.0554 1.0000 Uani . . . . . .
N7 N 0.0649(3) 0.9491(2) 0.33291(15) 0.0496 1.0000 Uani . . . . . .
N9 N 0.1097(3) 1.1080(2) 0.37127(14) 0.0475 1.0000 Uani . . . . . .
N10 N -0.0648(4) 0.9187(2) 0.18296(17) 0.0700 1.0000 Uani . . . . . .
C2 C -0.0211(4) 1.1833(3) 0.2012(2) 0.0600 1.0000 Uani . . . . . .
C4 C 0.0541(3) 1.1171(2) 0.30324(18) 0.0483 1.0000 Uani . . . . . .
C5 C 0.0261(3) 1.0192(2) 0.28094(18) 0.0467 1.0000 Uani . . . . . .
C6 C -0.0320(4) 1.0082(3) 0.21159(19) 0.0531 1.0000 Uani . . . . . .
C8 C 0.1142(3) 1.0044(3) 0.38630(18) 0.0475 1.0000 Uani . . . . . .
C11 C 0.1758(4) 0.9595(3) 0.45167(18) 0.0488 1.0000 Uani . . . . . .
C12 C 0.2236(3) 0.8611(3) 0.44687(19) 0.0500 1.0000 Uani . . . . . .
C13 C 0.2860(3) 0.8157(3) 0.50513(18) 0.0479 1.0000 Uani . . . . . .
C14 C 0.3004(3) 0.8685(3) 0.56987(17) 0.0480 1.0000 Uani . . . . . .
C15 C 0.2518(4) 0.9670(3) 0.57466(18) 0.0510 1.0000 Uani . . . . . .
C16 C 0.1877(4) 1.0126(3) 0.51642(18) 0.0519 1.0000 Uani . . . . . .
C18 C 0.3421(5) 0.6668(4) 0.4391(2) 0.0877 1.0000 Uani . . . . . .
C20 C 0.2902(5) 0.7676(4) 0.6733(2) 0.0873 1.0000 Uani . . . . . .
C22 C 0.2530(5) 1.1219(3) 0.6425(2) 0.0747 1.0000 Uani . . . . . .
C23 C 0.1580(3) 1.1928(2) 0.41316(17) 0.0469 1.0000 Uani . . . . . .
C24 C 0.2888(4) 1.2191(3) 0.41185(19) 0.0547 1.0000 Uani . . . . . .
C25 C 0.3354(4) 1.2999(3) 0.4520(2) 0.0597 1.0000 Uani . . . . . .
C26 C 0.2499(4) 1.3550(3) 0.49461(19) 0.0526 1.0000 Uani . . . . . .
C27 C 0.1182(4) 1.3284(3) 0.49651(19) 0.0541 1.0000 Uani . . . . . .
C28 C 0.0731(4) 1.2474(3) 0.45505(19) 0.0520 1.0000 Uani . . . . . .
C30 C 0.2222(6) 1.4945(4) 0.5746(3) 0.0987 1.0000 Uani . . . . . .
C31 C 0.5059(5) 0.5353(4) 0.2492(2) 0.0763 1.0000 Uani . . . . . .
H21 H -0.0405 1.2404 0.1725 0.0718 1.0000 Uiso R . . . . .
H101 H -0.0563 0.8628 0.2068 0.0838 1.0000 Uiso R . . . . .
H102 H -0.0952 0.9179 0.1398 0.0841 1.0000 Uiso R . . . . .
H121 H 0.2157 0.8256 0.4035 0.0596 1.0000 Uiso R . . . . .
H161 H 0.1499 1.0773 0.5205 0.0617 1.0000 Uiso R . . . . .
H181 H 0.3880 0.6034 0.4471 0.1305 1.0000 Uiso R . . . . .
H182 H 0.3887 0.7082 0.4046 0.1307 1.0000 Uiso R . . . . .
H183 H 0.2533 0.6537 0.4220 0.1311 1.0000 Uiso R . . . . .
H201 H 0.2395 0.7177 0.6462 0.1311 1.0000 Uiso R . . . . .
H202 H 0.3460 0.7328 0.7075 0.1311 1.0000 Uiso R . . . . .
H203 H 0.2300 0.8114 0.6990 0.1312 1.0000 Uiso R . . . . .
H221 H 0.3114 1.1555 0.6095 0.1117 1.0000 Uiso R . . . . .
H222 H 0.2730 1.1450 0.6909 0.1118 1.0000 Uiso R . . . . .
H223 H 0.1623 1.1382 0.6301 0.1119 1.0000 Uiso R . . . . .
H241 H 0.3467 1.1818 0.3835 0.0661 1.0000 Uiso R . . . . .
H251 H 0.4244 1.3168 0.4503 0.0719 1.0000 Uiso R . . . . .
H271 H 0.0584 1.3651 0.5259 0.0643 1.0000 Uiso R . . . . .
H281 H -0.0157 1.2286 0.4556 0.0619 1.0000 Uiso R . . . . .
H301 H 0.1495 1.5214 0.5447 0.1478 1.0000 Uiso R . . . . .
H302 H 0.1868 1.4547 0.6135 0.1478 1.0000 Uiso R . . . . .
H303 H 0.2720 1.5507 0.5944 0.1477 1.0000 Uiso R . . . . .
H311 H 0.4367 0.5580 0.2165 0.0917 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 . O17 . C18 . 117.6(3) yes
C14 . O19 . C20 . 114.1(3) yes
C15 . O21 . C22 . 117.5(3) yes
C26 . O29 . C30 . 117.6(3) yes
C2 . N1 . C6 . 118.6(3) yes
C2 . N3 . C4 . 111.3(3) yes
C5 . N7 . C8 . 104.8(3) yes
C4 . N9 . C8 . 106.3(3) yes
C4 . N9 . C23 . 123.8(3) yes
C8 . N9 . C23 . 129.8(3) yes
C6 . N10 . H101 . 121.9 no
C6 . N10 . H102 . 118.0 no
H101 . N10 . H102 . 120.1 no
N1 . C2 . N3 . 128.6(3) yes
N1 . C2 . H21 . 115.7 no
N3 . C2 . H21 . 115.7 no
N9 . C4 . N3 . 127.5(3) yes
N9 . C4 . C5 . 105.8(3) yes
N3 . C4 . C5 . 126.8(3) yes
N7 . C5 . C4 . 110.9(3) yes
N7 . C5 . C6 . 132.4(3) yes
C4 . C5 . C6 . 116.6(3) yes
C5 . C6 . N1 . 118.0(3) yes
C5 . C6 . N10 . 123.4(3) yes
N1 . C6 . N10 . 118.6(3) yes
N9 . C8 . N7 . 112.2(3) yes
N9 . C8 . C11 . 124.6(3) yes
N7 . C8 . C11 . 123.1(3) yes
C8 . C11 . C12 . 117.6(3) yes
C8 . C11 . C16 . 122.5(3) yes
C12 . C11 . C16 . 119.9(3) yes
C11 . C12 . C13 . 120.7(3) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 119.4 no
C12 . C13 . O17 . 125.1(3) yes
C12 . C13 . C14 . 120.0(3) yes
O17 . C13 . C14 . 114.9(3) yes
C13 . C14 . O19 . 120.8(3) yes
C13 . C14 . C15 . 119.2(3) yes
O19 . C14 . C15 . 119.9(3) yes
C14 . C15 . O21 . 115.6(3) yes
C14 . C15 . C16 . 120.9(3) yes
O21 . C15 . C16 . 123.4(3) yes
C11 . C16 . C15 . 119.2(3) yes
C11 . C16 . H161 . 119.7 no
C15 . C16 . H161 . 121.0 no
O17 . C18 . H181 . 108.3 no
O17 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 110.1 no
O17 . C18 . H183 . 108.6 no
H181 . C18 . H183 . 110.0 no
H182 . C18 . H183 . 110.4 no
O19 . C20 . H201 . 110.8 no
O19 . C20 . H202 . 109.3 no
H201 . C20 . H202 . 108.8 no
O19 . C20 . H203 . 109.9 no
H201 . C20 . H203 . 108.9 no
H202 . C20 . H203 . 109.1 no
O21 . C22 . H221 . 110.3 no
O21 . C22 . H222 . 108.5 no
H221 . C22 . H222 . 109.0 no
O21 . C22 . H223 . 109.6 no
H221 . C22 . H223 . 110.0 no
H222 . C22 . H223 . 109.4 no
N9 . C23 . C24 . 120.3(3) yes
N9 . C23 . C28 . 119.9(3) yes
C24 . C23 . C28 . 119.8(3) yes
C23 . C24 . C25 . 120.4(3) yes
C23 . C24 . H241 . 119.9 no
C25 . C24 . H241 . 119.7 no
C24 . C25 . C26 . 119.9(4) yes
C24 . C25 . H251 . 119.2 no
C26 . C25 . H251 . 120.9 no
C25 . C26 . O29 . 115.2(3) yes
C25 . C26 . C27 . 119.9(3) yes
O29 . C26 . C27 . 124.9(3) yes
C26 . C27 . C28 . 119.3(3) yes
C26 . C27 . H271 . 120.9 no
C28 . C27 . H271 . 119.9 no
C27 . C28 . C23 . 120.7(3) yes
C27 . C28 . H281 . 120.2 no
C23 . C28 . H281 . 119.1 no
O29 . C30 . H301 . 109.9 no
O29 . C30 . H302 . 110.4 no
H301 . C30 . H302 . 109.4 no
O29 . C30 . H303 . 109.2 no
H301 . C30 . H303 . 108.8 no
H302 . C30 . H303 . 109.2 no
Cl33 . C31 . Cl34 . 111.8(3) yes
Cl33 . C31 . Cl32 . 110.3(3) yes
Cl34 . C31 . Cl32 . 110.7(3) yes
Cl33 . C31 . H311 . 108.3 no
Cl34 . C31 . H311 . 107.6 no
Cl32 . C31 . H311 . 108.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl32 . C31 . 1.717(5) yes
Cl33 . C31 . 1.741(5) yes
Cl34 . C31 . 1.740(5) yes
O17 . C13 . 1.366(4) yes
O17 . C18 . 1.419(5) yes
O19 . C14 . 1.372(4) yes
O19 . C20 . 1.413(5) yes
O21 . C15 . 1.370(4) yes
O21 . C22 . 1.428(5) yes
O29 . C26 . 1.361(4) yes
O29 . C30 . 1.419(5) yes
N1 . C2 . 1.340(5) yes
N1 . C6 . 1.346(4) yes
N3 . C2 . 1.333(5) yes
N3 . C4 . 1.339(4) yes
N7 . C5 . 1.385(4) yes
N7 . C8 . 1.318(4) yes
N9 . C4 . 1.377(4) yes
N9 . C8 . 1.389(4) yes
N9 . C23 . 1.439(4) yes
N10 . C6 . 1.329(4) yes
N10 . H101 . 0.861 no
N10 . H102 . 0.852 no
C2 . H21 . 0.937 no
C4 . C5 . 1.379(5) yes
C5 . C6 . 1.412(5) yes
C8 . C11 . 1.476(4) yes
C11 . C12 . 1.384(5) yes
C11 . C16 . 1.392(5) yes
C12 . C13 . 1.377(5) yes
C12 . H121 . 0.933 no
C13 . C14 . 1.392(5) yes
C14 . C15 . 1.388(5) yes
C15 . C16 . 1.385(5) yes
C16 . H161 . 0.936 no
C18 . H181 . 0.964 no
C18 . H182 . 0.970 no
C18 . H183 . 0.965 no
C20 . H201 . 0.968 no
C20 . H202 . 0.958 no
C20 . H203 . 0.970 no
C22 . H221 . 0.967 no
C22 . H222 . 0.967 no
C22 . H223 . 0.968 no
C23 . C24 . 1.373(5) yes
C23 . C28 . 1.374(5) yes
C24 . C25 . 1.375(5) yes
C24 . H241 . 0.935 no
C25 . C26 . 1.390(5) yes
C25 . H251 . 0.932 no
C26 . C27 . 1.383(5) yes
C27 . C28 . 1.386(5) yes
C27 . H271 . 0.954 no
C28 . H281 . 0.935 no
C30 . H301 . 0.979 no
C30 . H302 . 0.966 no
C30 . H303 . 0.963 no
C31 . H311 . 0.966 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N10 . H101 . N3 3_545 163 0.86 2.17 3.005(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658796
