#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/06/7150640.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_7150640
loop_
_publ_author_name
'Klečka, Martin'
'Pohl, Radek'
'Klepetářová, Blanka'
'Hocek, Michal'
_publ_section_title
;
 Direct C--H borylation and C--H arylation of
 pyrrolo[2,3-d]pyrimidines: synthesis of 6,8-disubstituted
 7-deazapurines
;
_journal_issue                   5
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              866
_journal_page_last               868
_journal_paper_doi               10.1039/b900218a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C26 H21 N3'
_chemical_formula_sum            'C26 H21 N3'
_chemical_formula_weight         375.47
_chemical_name_common
(7-benzyl-4-phenyl-6-p-tolyl-7H-pyrrolo(2,3-d)pyrimidine)
_chemical_name_systematic
(7-benzyl-4-phenyl-6-p-tolyl-7H-pyrrolo[2,3-d]pyrimidine)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-09-25
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                101.076(14)
_cell_angle_beta                 114.026(17)
_cell_angle_gamma                104.117(15)
_cell_formula_units_Z            2
_cell_length_a                   9.8513(18)
_cell_length_b                   10.4417(18)
_cell_length_c                   11.565(2)
_cell_measurement_reflns_used    7082
_cell_measurement_temperature    298
_cell_measurement_theta_max      78
_cell_measurement_theta_min      4
_cell_volume                     995.1(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 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31243
_diffrn_reflns_theta_full        73.259
_diffrn_reflns_theta_max         78.773
_diffrn_reflns_theta_min         4.433
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       72(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000253
_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:
9.84 1.91 7.31
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0769
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0610
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2354
_reflns_number_total             4195
_reflns_threshold_expression     I>2.0σ(I)
_oxford_refine_ls_r_factor_ref   0.0501
_oxford_refine_ls_scale          8.80(3)
_oxford_reflns_number_all        4179
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            b900218a.txt
_cod_data_source_block           2
_cod_database_code               7150640
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C11 C 1.1384(3) 1.1026(3) 0.3462(3) 0.0681 1.0000 Uani . . . . . . .
C12 C 1.2754(3) 1.1505(3) 0.3360(3) 0.0773 1.0000 Uani . . . . . . .
C13 C 1.3417(3) 1.2890(3) 0.3539(3) 0.0728 1.0000 Uani . . . . . . .
C14 C 1.2720(3) 1.3794(3) 0.3840(3) 0.0765 1.0000 Uani . . . . . . .
C15 C 1.1345(3) 1.3323(3) 0.3938(3) 0.0676 1.0000 Uani . . . . . . .
N1 N 0.8753(2) 1.24672(19) 0.4356(2) 0.0587 1.0000 Uani . . . . . . .
N3 N 0.6390(2) 1.0833(2) 0.4117(2) 0.0598 1.0000 Uani . . . . . . .
N9 N 0.5963(2) 0.84362(18) 0.31841(18) 0.0516 1.0000 Uani . . . . . . .
C2 C 0.7419(3) 1.2107(3) 0.4458(3) 0.0628 1.0000 Uani . . . . . . .
C4 C 0.6815(2) 0.9838(2) 0.3617(2) 0.0501 1.0000 Uani . . . . . . .
C5 C 0.8187(2) 1.0046(2) 0.3444(2) 0.0495 1.0000 Uani . . . . . . .
C6 C 0.9168(2) 1.1444(2) 0.3844(2) 0.0507 1.0000 Uani . . . . . . .
C7 C 0.8116(3) 0.8667(2) 0.2883(2) 0.0553 1.0000 Uani . . . . . . .
C8 C 0.6778(2) 0.7715(2) 0.2741(2) 0.0516 1.0000 Uani . . . . . . .
C10 C 1.0642(2) 1.1923(2) 0.3738(2) 0.0514 1.0000 Uani . . . . . . .
C16 C 0.6267(2) 0.6194(2) 0.2259(2) 0.0520 1.0000 Uani . . . . . . .
C17 C 0.7419(3) 0.5583(3) 0.2613(2) 0.0617 1.0000 Uani . . . . . . .
C18 C 0.6996(3) 0.4147(3) 0.2150(3) 0.0673 1.0000 Uani . . . . . . .
C19 C 0.5429(3) 0.3272(2) 0.1331(3) 0.0612 1.0000 Uani . . . . . . .
C20 C 0.4289(3) 0.3880(2) 0.0961(2) 0.0611 1.0000 Uani . . . . . . .
C21 C 0.4683(3) 0.5312(2) 0.1406(2) 0.0580 1.0000 Uani . . . . . . .
C22 C 0.4950(4) 0.1710(3) 0.0864(3) 0.0837 1.0000 Uani . . . . . . .
C23 C 0.4536(3) 0.7876(2) 0.3309(2) 0.0555 1.0000 Uani . . . . . . .
C24 C 0.2994(2) 0.7670(2) 0.2116(2) 0.0553 1.0000 Uani . . . . . . .
C25 C 0.2941(3) 0.8301(3) 0.1169(3) 0.0761 1.0000 Uani . . . . . . .
C26 C 0.1506(4) 0.8121(4) 0.0105(3) 0.0956 1.0000 Uani . . . . . . .
C27 C 0.0111(4) 0.7303(4) -0.0022(3) 0.0980 1.0000 Uani . . . . . . .
C28 C 0.0152(4) 0.6674(4) 0.0922(4) 0.1064 1.0000 Uani . . . . . . .
C29 C 0.1577(3) 0.6845(3) 0.1978(3) 0.0823 1.0000 Uani . . . . . . .
H21 H 0.7139 1.2877 0.4817 0.0739 1.0000 Uiso R . . . . . .
H71 H 0.8854 0.8431 0.2651 0.0678 1.0000 Uiso R . . . . . .
H151 H 1.0860 1.3945 0.4144 0.0802 1.0000 Uiso R . . . . . .
H141 H 1.3183 1.4776 0.3982 0.0926 1.0000 Uiso R . . . . . .
H131 H 1.4367 1.3219 0.3453 0.0871 1.0000 Uiso R . . . . . .
H121 H 1.3205 1.0856 0.3172 0.0953 1.0000 Uiso R . . . . . .
H111 H 1.0951 1.0069 0.3348 0.0821 1.0000 Uiso R . . . . . .
H171 H 0.8519 0.6180 0.3197 0.0708 1.0000 Uiso R . . . . . .
H181 H 0.7814 0.3740 0.2428 0.0797 1.0000 Uiso R . . . . . .
H201 H 0.3215 0.3309 0.0384 0.0715 1.0000 Uiso R . . . . . .
H211 H 0.3860 0.5715 0.1102 0.0674 1.0000 Uiso R . . . . . .
H223 H 0.4317 0.1308 -0.0101 0.1277 1.0000 Uiso R . . . . . .
H221 H 0.5901 0.1475 0.1118 0.1269 1.0000 Uiso R . . . . . .
H222 H 0.4364 0.1278 0.1271 0.1274 1.0000 Uiso R . . . . . .
H231 H 0.4648 0.8522 0.4114 0.0669 1.0000 Uiso R . . . . . .
H232 H 0.4496 0.6968 0.3449 0.0666 1.0000 Uiso R . . . . . .
H251 H 0.3911 0.8864 0.1243 0.0887 1.0000 Uiso R . . . . . .
H261 H 0.1514 0.8582 -0.0526 0.1144 1.0000 Uiso R . . . . . .
H271 H -0.0875 0.7156 -0.0740 0.1113 1.0000 Uiso R . . . . . .
H281 H -0.0823 0.6128 0.0844 0.1196 1.0000 Uiso R . . . . . .
H291 H 0.1593 0.6380 0.2614 0.0962 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'
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
C12 . C11 . C10 . 121.3(2) yes
C12 . C11 . H111 . 119.2 no
C10 . C11 . H111 . 119.5 no
C11 . C12 . C13 . 120.3(3) yes
C11 . C12 . H121 . 117.8 no
C13 . C12 . H121 . 121.9 no
C12 . C13 . C14 . 119.2(2) yes
C12 . C13 . H131 . 120.1 no
C14 . C13 . H131 . 120.7 no
C13 . C14 . C15 . 120.9(2) yes
C13 . C14 . H141 . 120.1 no
C15 . C14 . H141 . 119.0 no
C14 . C15 . C10 . 120.8(2) yes
C14 . C15 . H151 . 121.0 no
C10 . C15 . H151 . 118.2 no
C2 . N1 . C6 . 118.6(2) yes
C2 . N3 . C4 . 112.10(18) yes
C4 . N9 . C8 . 107.92(16) yes
C4 . N9 . C23 . 122.99(18) yes
C8 . N9 . C23 . 128.88(18) yes
N1 . C2 . N3 . 128.6(2) yes
N1 . C2 . H21 . 116.6 no
N3 . C2 . H21 . 114.9 no
N9 . C4 . N3 . 124.08(18) yes
N9 . C4 . C5 . 109.71(18) yes
N3 . C4 . C5 . 126.2(2) yes
C4 . C5 . C6 . 115.6(2) yes
C4 . C5 . C7 . 104.92(18) yes
C6 . C5 . C7 . 139.4(2) yes
C5 . C6 . N1 . 118.87(19) yes
C5 . C6 . C10 . 125.59(19) yes
N1 . C6 . C10 . 115.54(19) yes
C5 . C7 . C8 . 108.68(18) yes
C5 . C7 . H71 . 126.9 no
C8 . C7 . H71 . 124.4 no
N9 . C8 . C7 . 108.77(18) yes
N9 . C8 . C16 . 123.83(18) yes
C7 . C8 . C16 . 127.37(19) yes
C6 . C10 . C11 . 122.7(2) yes
C6 . C10 . C15 . 119.8(2) yes
C11 . C10 . C15 . 117.5(2) yes
C8 . C16 . C17 . 118.6(2) yes
C8 . C16 . C21 . 123.5(2) yes
C17 . C16 . C21 . 117.8(2) yes
C16 . C17 . C18 . 120.7(2) yes
C16 . C17 . H171 . 118.7 no
C18 . C17 . H171 . 120.6 no
C17 . C18 . C19 . 121.6(2) yes
C17 . C18 . H181 . 119.5 no
C19 . C18 . H181 . 118.9 no
C18 . C19 . C20 . 117.7(2) yes
C18 . C19 . C22 . 122.0(2) yes
C20 . C19 . C22 . 120.3(2) yes
C19 . C20 . C21 . 121.8(2) yes
C19 . C20 . H201 . 119.5 no
C21 . C20 . H201 . 118.7 no
C16 . C21 . C20 . 120.3(2) yes
C16 . C21 . H211 . 119.5 no
C20 . C21 . H211 . 120.1 no
C19 . C22 . H223 . 111.8 no
C19 . C22 . H221 . 109.0 no
H223 . C22 . H221 . 107.3 no
C19 . C22 . H222 . 111.7 no
H223 . C22 . H222 . 109.1 no
H221 . C22 . H222 . 107.8 no
N9 . C23 . C24 . 114.70(18) yes
N9 . C23 . H231 . 108.0 no
C24 . C23 . H231 . 109.0 no
N9 . C23 . H232 . 107.9 no
C24 . C23 . H232 . 108.8 no
H231 . C23 . H232 . 108.3 no
C23 . C24 . C25 . 122.5(2) yes
C23 . C24 . C29 . 119.2(2) yes
C25 . C24 . C29 . 118.3(2) yes
C24 . C25 . C26 . 121.2(3) yes
C24 . C25 . H251 . 119.2 no
C26 . C25 . H251 . 119.6 no
C25 . C26 . C27 . 120.1(3) yes
C25 . C26 . H261 . 118.9 no
C27 . C26 . H261 . 121.0 no
C26 . C27 . C28 . 119.1(3) yes
C26 . C27 . H271 . 121.7 no
C28 . C27 . H271 . 119.2 no
C27 . C28 . C29 . 120.9(3) yes
C27 . C28 . H281 . 118.8 no
C29 . C28 . H281 . 120.3 no
C24 . C29 . C28 . 120.4(3) yes
C24 . C29 . H291 . 119.4 no
C28 . C29 . H291 . 120.2 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
C11 . C12 . 1.382(3) yes
C11 . C10 . 1.386(3) yes
C11 . H111 . 0.945 no
C12 . C13 . 1.369(4) yes
C12 . H121 . 0.934 no
C13 . C14 . 1.367(4) yes
C13 . H131 . 0.968 no
C14 . C15 . 1.383(3) yes
C14 . H141 . 0.965 no
C15 . C10 . 1.384(3) yes
C15 . H151 . 0.945 no
N1 . C2 . 1.336(3) yes
N1 . C6 . 1.351(3) yes
N3 . C2 . 1.329(3) yes
N3 . C4 . 1.331(3) yes
N9 . C4 . 1.369(3) yes
N9 . C8 . 1.398(3) yes
N9 . C23 . 1.462(3) yes
C2 . H21 . 0.984 no
C4 . C5 . 1.417(3) yes
C5 . C6 . 1.403(3) yes
C5 . C7 . 1.433(3) yes
C6 . C10 . 1.479(3) yes
C7 . C8 . 1.369(3) yes
C7 . H71 . 0.939 no
C8 . C16 . 1.459(3) yes
C16 . C17 . 1.393(3) yes
C16 . C21 . 1.397(3) yes
C17 . C18 . 1.383(4) yes
C17 . H171 . 0.966 no
C18 . C19 . 1.380(4) yes
C18 . H181 . 0.970 no
C19 . C20 . 1.381(3) yes
C19 . C22 . 1.501(4) yes
C20 . C21 . 1.383(3) yes
C20 . H201 . 0.941 no
C21 . H211 . 0.974 no
C22 . H223 . 0.968 no
C22 . H221 . 0.969 no
C22 . H222 . 0.967 no
C23 . C24 . 1.510(3) yes
C23 . H231 . 0.986 no
C23 . H232 . 0.986 no
C24 . C25 . 1.371(3) yes
C24 . C29 . 1.377(3) yes
C25 . C26 . 1.383(4) yes
C25 . H251 . 0.952 no
C26 . C27 . 1.362(4) yes
C26 . H261 . 0.950 no
C27 . C28 . 1.370(5) yes
C27 . H271 . 0.938 no
C28 . C29 . 1.376(4) yes
C28 . H281 . 0.947 no
C29 . H291 . 0.953 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
C11 . H111 . C7 . 128 0.95 2.59 3.259(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653373
