#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150909.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_7150909
loop_
_publ_author_name
'Kuchař, Martin'
'Pohl, Radek'
'Klepetářová, Blanka'
'Votruba, Ivan'
'Hocek, Michal'
_publ_section_title
;
 Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by
 cross-coupling reactions or cyclopropanations
;
_journal_issue                   13
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2377
_journal_page_last               2387
_journal_paper_doi               10.1039/b802833h
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N5 O1'
_chemical_formula_sum            'C20 H23 N5 O'
_chemical_formula_weight         349.44
_chemical_name_common
9-Benzyl-6-(2-(diethylcarbamoyl)cyclopropyl)purine
_chemical_name_systematic
9-Benzyl-6-[2-(diethylcarbamoyl)cyclopropyl]purine
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-02-07
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2791(2)
_cell_length_b                   16.20300(10)
_cell_length_c                   4.98
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1797.72(2)
_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      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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  0.032
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            26954
_diffrn_reflns_theta_full        74.396
_diffrn_reflns_theta_max         76.697
_diffrn_reflns_theta_min         3.968
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 1507 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       24(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0836
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.000574
_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:
2.28 1.47 0.608
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0402
_refine_ls_wR_factor_gt          0.0328
_refine_ls_wR_factor_ref         0.0328
_reflns_limit_h_max              27
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              6
_reflns_limit_l_min              -5
_reflns_number_gt                2807
_reflns_number_total             3604
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            b802833h.txt
_cod_data_source_block           CRYSTALS1_cif
_cod_original_formula_sum        'C20 H23 N5 O1'
_cod_database_code               7150909
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z
-x,-y,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
O21 O 0.71005(5) 0.45761(7) 0.3884(3) 0.0346 1.0000 Uani . . . . . .
N1 N 0.57477(6) 0.70738(8) 0.5710(3) 0.0319 1.0000 Uani . . . . . .
N3 N 0.55737(6) 0.83684(8) 0.3461(3) 0.0327 1.0000 Uani . . . . . .
N7 N 0.69444(6) 0.75605(8) 0.0795(3) 0.0314 1.0000 Uani . . . . . .
N9 N 0.63601(6) 0.86892(7) 0.0243(3) 0.0294 1.0000 Uani . . . . . .
N22 N 0.62040(6) 0.40009(8) 0.2919(3) 0.0302 1.0000 Uani . . . . . .
C2 C 0.54419(8) 0.77654(10) 0.5197(4) 0.0338 1.0000 Uani . . . . . .
C4 C 0.60850(7) 0.82164(9) 0.2167(3) 0.0273 1.0000 Uani . . . . . .
C5 C 0.64492(7) 0.75185(9) 0.2486(3) 0.0268 1.0000 Uani . . . . . .
C6 C 0.62596(7) 0.69361(9) 0.4360(3) 0.0281 1.0000 Uani . . . . . .
C8 C 0.68701(7) 0.82635(10) -0.0486(4) 0.0317 1.0000 Uani . . . . . .
C10 C 0.61690(8) 0.95005(9) -0.0755(3) 0.0311 1.0000 Uani . . . . . .
C11 C 0.61962(7) 1.01511(10) 0.1423(3) 0.0295 1.0000 Uani . . . . . .
C12 C 0.67489(8) 1.04658(10) 0.2232(4) 0.0350 1.0000 Uani . . . . . .
C13 C 0.67800(8) 1.10541(10) 0.4266(4) 0.0393 1.0000 Uani . . . . . .
C14 C 0.62547(8) 1.13182(10) 0.5503(4) 0.0369 1.0000 Uani . . . . . .
C15 C 0.57066(8) 1.10169(10) 0.4690(4) 0.0378 1.0000 Uani . . . . . .
C16 C 0.56770(8) 1.04358(10) 0.2632(4) 0.0351 1.0000 Uani . . . . . .
C17 C 0.66021(7) 0.61717(9) 0.4885(3) 0.0294 1.0000 Uani . . . . . .
C18 C 0.65239(8) 0.57293(10) 0.7493(4) 0.0332 1.0000 Uani . . . . . .
C19 C 0.62434(7) 0.53691(9) 0.5003(3) 0.0282 1.0000 Uani . . . . . .
C20 C 0.65473(7) 0.46216(10) 0.3877(4) 0.0297 1.0000 Uani . . . . . .
C23 C 0.55472(7) 0.40095(11) 0.2778(3) 0.0338 1.0000 Uani . . . . . .
C24 C 0.52501(8) 0.37363(13) 0.5367(4) 0.0438 1.0000 Uani . . . . . .
C25 C 0.65094(8) 0.32323(10) 0.2140(4) 0.0327 1.0000 Uani . . . . . .
C26 C 0.67870(8) 0.32791(12) -0.0612(4) 0.0407 1.0000 Uani . . . . . .
H21 H 0.5082 0.7847 0.6238 0.0389 1.0000 Uiso R . . . . .
H81 H 0.7140 0.8475 -0.1846 0.0370 1.0000 Uiso R . . . . .
H101 H 0.6430 0.9669 -0.2298 0.0378 1.0000 Uiso R . . . . .
H102 H 0.5753 0.9451 -0.1433 0.0364 1.0000 Uiso R . . . . .
H121 H 0.7104 1.0277 0.1376 0.0410 1.0000 Uiso R . . . . .
H131 H 0.7154 1.1258 0.4770 0.0473 1.0000 Uiso R . . . . .
H141 H 0.6285 1.1707 0.7012 0.0448 1.0000 Uiso R . . . . .
H151 H 0.5348 1.1206 0.5532 0.0433 1.0000 Uiso R . . . . .
H161 H 0.5291 1.0240 0.2087 0.0428 1.0000 Uiso R . . . . .
H171 H 0.6995 0.6146 0.4027 0.0336 1.0000 Uiso R . . . . .
H181 H 0.6882 0.5460 0.8248 0.0393 1.0000 Uiso R . . . . .
H182 H 0.6262 0.5962 0.8885 0.0382 1.0000 Uiso R . . . . .
H191 H 0.5806 0.5427 0.4786 0.0313 1.0000 Uiso R . . . . .
H231 H 0.5417 0.4590 0.2314 0.0393 1.0000 Uiso R . . . . .
H232 H 0.5435 0.3640 0.1319 0.0396 1.0000 Uiso R . . . . .
H241 H 0.4807 0.3730 0.5162 0.0642 1.0000 Uiso R . . . . .
H242 H 0.5358 0.4121 0.6844 0.0639 1.0000 Uiso R . . . . .
H243 H 0.5397 0.3186 0.5896 0.0649 1.0000 Uiso R . . . . .
H251 H 0.6837 0.3088 0.3432 0.0396 1.0000 Uiso R . . . . .
H252 H 0.6206 0.2771 0.2151 0.0386 1.0000 Uiso R . . . . .
H261 H 0.6997 0.2747 -0.0969 0.0597 1.0000 Uiso R . . . . .
H262 H 0.7075 0.3743 -0.0717 0.0601 1.0000 Uiso R . . . . .
H263 H 0.6470 0.3380 -0.1979 0.0591 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'
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
C2 . N1 . C6 . 118.48(14) yes
C2 . N3 . C4 . 111.43(14) yes
C5 . N7 . C8 . 103.65(13) yes
C4 . N9 . C8 . 105.84(13) yes
C4 . N9 . C10 . 127.37(14) yes
C8 . N9 . C10 . 126.74(14) yes
C20 . N22 . C23 . 125.14(14) yes
C20 . N22 . C25 . 117.48(13) yes
C23 . N22 . C25 . 117.22(13) yes
N3 . C2 . N1 . 128.65(16) yes
N3 . C2 . H21 . 115.4 no
N1 . C2 . H21 . 115.9 no
N9 . C4 . N3 . 128.11(14) yes
N9 . C4 . C5 . 105.74(14) yes
N3 . C4 . C5 . 126.14(15) yes
C4 . C5 . N7 . 110.59(14) yes
C4 . C5 . C6 . 116.58(14) yes
N7 . C5 . C6 . 132.83(14) yes
C5 . C6 . N1 . 118.71(14) yes
C5 . C6 . C17 . 121.99(15) yes
N1 . C6 . C17 . 119.30(14) yes
N9 . C8 . N7 . 114.17(14) yes
N9 . C8 . H81 . 121.3 no
N7 . C8 . H81 . 124.5 no
N9 . C10 . C11 . 111.69(13) yes
N9 . C10 . H101 . 109.6 no
C11 . C10 . H101 . 109.7 no
N9 . C10 . H102 . 108.3 no
C11 . C10 . H102 . 109.8 no
H101 . C10 . H102 . 107.8 no
C10 . C11 . C12 . 119.86(15) yes
C10 . C11 . C16 . 120.70(15) yes
C12 . C11 . C16 . 119.44(16) yes
C11 . C12 . C13 . 120.35(17) yes
C11 . C12 . H121 . 119.3 no
C13 . C12 . H121 . 120.4 no
C12 . C13 . C14 . 119.39(17) yes
C12 . C13 . H131 . 118.9 no
C14 . C13 . H131 . 121.7 no
C13 . C14 . C15 . 120.52(17) yes
C13 . C14 . H141 . 118.6 no
C15 . C14 . H141 . 120.8 no
C14 . C15 . C16 . 119.87(16) yes
C14 . C15 . H151 . 120.0 no
C16 . C15 . H151 . 120.1 no
C15 . C16 . C11 . 120.39(16) yes
C15 . C16 . H161 . 118.4 no
C11 . C16 . H161 . 121.2 no
C6 . C17 . C18 . 119.72(15) yes
C6 . C17 . C19 . 116.75(13) yes
C18 . C17 . C19 . 59.77(11) yes
C6 . C17 . H171 . 115.0 no
C18 . C17 . H171 . 117.7 no
C19 . C17 . H171 . 116.8 no
C17 . C18 . C19 . 61.25(11) yes
C17 . C18 . H181 . 116.8 no
C19 . C18 . H181 . 118.6 no
C17 . C18 . H182 . 120.0 no
C19 . C18 . H182 . 118.9 no
H181 . C18 . H182 . 112.5 no
C17 . C19 . C18 . 58.98(10) yes
C17 . C19 . C20 . 115.97(13) yes
C18 . C19 . C20 . 115.74(14) yes
C17 . C19 . H191 . 115.6 no
C18 . C19 . H191 . 117.6 no
C20 . C19 . H191 . 119.0 no
C19 . C20 . N22 . 118.60(14) yes
C19 . C20 . O21 . 119.93(14) yes
N22 . C20 . O21 . 121.45(15) yes
N22 . C23 . C24 . 113.13(14) yes
N22 . C23 . H231 . 107.9 no
C24 . C23 . H231 . 109.9 no
N22 . C23 . H232 . 106.7 no
C24 . C23 . H232 . 110.0 no
H231 . C23 . H232 . 109.1 no
C23 . C24 . H241 . 110.5 no
C23 . C24 . H242 . 109.9 no
H241 . C24 . H242 . 108.8 no
C23 . C24 . H243 . 110.3 no
H241 . C24 . H243 . 110.4 no
H242 . C24 . H243 . 106.9 no
N22 . C25 . C26 . 112.79(14) yes
N22 . C25 . H251 . 111.4 no
C26 . C25 . H251 . 107.3 no
N22 . C25 . H252 . 108.5 no
C26 . C25 . H252 . 108.5 no
H251 . C25 . H252 . 108.1 no
C25 . C26 . H261 . 108.2 no
C25 . C26 . H262 . 110.7 no
H261 . C26 . H262 . 110.1 no
C25 . C26 . H263 . 109.8 no
H261 . C26 . H263 . 110.7 no
H262 . C26 . H263 . 107.4 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
O21 . C20 . 1.2347(19) yes
N1 . C2 . 1.336(2) yes
N1 . C6 . 1.343(2) yes
N3 . C2 . 1.337(2) yes
N3 . C4 . 1.332(2) yes
N7 . C5 . 1.389(2) yes
N7 . C8 . 1.316(2) yes
N9 . C4 . 1.371(2) yes
N9 . C8 . 1.378(2) yes
N9 . C10 . 1.4684(18) yes
N22 . C20 . 1.351(2) yes
N22 . C23 . 1.465(2) yes
N22 . C25 . 1.471(2) yes
C2 . H21 . 0.964 no
C4 . C5 . 1.401(2) yes
C5 . C6 . 1.392(2) yes
C6 . C17 . 1.478(2) yes
C8 . H81 . 0.968 no
C10 . C11 . 1.513(2) yes
C10 . H101 . 1.001 no
C10 . H102 . 0.990 no
C11 . C12 . 1.392(2) yes
C11 . C16 . 1.383(2) yes
C12 . C13 . 1.392(3) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.390(3) yes
C13 . H131 . 0.931 no
C14 . C15 . 1.376(2) yes
C14 . H141 . 0.982 no
C15 . C16 . 1.393(2) yes
C15 . H151 . 0.953 no
C16 . H161 . 0.956 no
C17 . C18 . 1.493(2) yes
C17 . C19 . 1.527(2) yes
C17 . H171 . 0.975 no
C18 . C19 . 1.505(2) yes
C18 . H181 . 0.983 no
C18 . H182 . 0.981 no
C19 . C20 . 1.496(2) yes
C19 . H191 . 0.985 no
C23 . C24 . 1.515(2) yes
C23 . H231 . 1.011 no
C23 . H232 . 0.975 no
C24 . H241 . 0.992 no
C24 . H242 . 0.993 no
C24 . H243 . 0.985 no
C25 . C26 . 1.504(3) yes
C25 . H251 . 1.000 no
C25 . H252 . 1.007 no
C26 . H261 . 0.997 no
C26 . H262 . 0.990 no
C26 . H263 . 0.994 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25937957
2 PubChem 24895587
