#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:23:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/88/4028876.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_4028876
loop_
_publ_author_name
'Jian-Ping Li'
'Yu Huang'
'Ming-Sheng Xie'
'Gui-Rong Qu'
'Hong-Ying Niu'
'Hai-Xia Wang'
'Bo-Wen Qin'
'Hai-Ming Guo'
_publ_section_title
;
 One-Pot Synthesis of 7,9-Dialkylpurin-8-one Analogues: Broad Substrate
 Scope
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12629
_journal_page_last               12636
_journal_paper_doi               10.1021/jo402248d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.057(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.732(3)
_cell_length_b                   9.1276(14)
_cell_length_c                   10.1906(16)
_cell_measurement_reflns_used    1911
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.04
_cell_measurement_theta_min      2.51
_cell_volume                     1648.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6090
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.3258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1198
_reflns_number_total             1532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402248d_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        1648.9(4)
_cod_database_code               4028876
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.16910(7) 0.11575(15) 0.73178(14) 0.0539(4) Uani 1 1 d .
C2 C 0.20031(8) 0.06060(17) 0.87237(15) 0.0678(4) Uani 1 1 d .
H2 H 0.1696 0.0126 0.9066 0.081 Uiso 1 1 calc R
C3 C 0.27609(8) 0.0757(2) 0.96242(17) 0.0789(5) Uani 1 1 d .
H3 H 0.2962 0.0383 1.0569 0.095 Uiso 1 1 calc R
C4 C 0.32182(9) 0.1454(2) 0.91350(19) 0.0793(5) Uani 1 1 d .
H4 H 0.3732 0.1539 0.9739 0.095 Uiso 1 1 calc R
C5 C 0.29198(9) 0.20270(19) 0.7755(2) 0.0802(5) Uani 1 1 d .
H5 H 0.3230 0.2513 0.7425 0.096 Uiso 1 1 calc R
C6 C 0.21541(8) 0.18841(17) 0.68472(17) 0.0693(4) Uani 1 1 d .
H6 H 0.1953 0.2283 0.5913 0.083 Uiso 1 1 calc R
C7 C 0.08637(7) 0.09324(16) 0.63206(14) 0.0611(4) Uani 1 1 d .
H7A H 0.0738 0.1444 0.5409 0.073 Uiso 1 1 calc R
H7B H 0.0772 -0.0103 0.6101 0.073 Uiso 1 1 calc R
C8 C 0.0000 0.0544(2) 0.7500 0.0558(5) Uani 1 2 d S
C9 C 0.02385(6) 0.29092(13) 0.71574(12) 0.0476(3) Uani 1 1 d .
C10 C 0.04866(7) 0.41965(15) 0.68125(14) 0.0565(4) Uani 1 1 d .
H10 H 0.0807 0.4197 0.6363 0.068 Uiso 1 1 calc R
C11 C 0.02380(7) 0.54907(15) 0.71641(16) 0.0637(4) Uani 1 1 d .
H11 H 0.0394 0.6380 0.6944 0.076 Uiso 1 1 calc R
N1 N 0.03715(5) 0.14503(11) 0.69458(11) 0.0531(3) Uani 1 1 d .
O1 O 0.0000 -0.07976(15) 0.7500 0.0734(4) Uani 1 2 d S
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 118.39(13) . .
C6 C1 C7 121.23(12) . .
C2 C1 C7 120.37(13) . .
C3 C2 C1 120.94(15) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C4 C3 C2 120.16(15) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 119.91(15) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C4 C5 C6 120.02(16) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C1 C6 C5 120.56(15) . .
C1 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
N1 C7 C1 113.16(10) . .
N1 C7 H7A 108.9 . .
C1 C7 H7A 108.9 . .
N1 C7 H7B 108.9 . .
C1 C7 H7B 108.9 . .
H7A C7 H7B 107.8 . .
O1 C8 N1 126.82(8) . 2_556
O1 C8 N1 126.82(8) . .
N1 C8 N1 106.36(16) 2_556 .
C10 C9 N1 131.64(12) . .
C10 C9 C9 121.40(8) . 2_556
N1 C9 C9 106.96(7) . 2_556
C9 C10 C11 117.12(12) . .
C9 C10 H10 121.4 . .
C11 C10 H10 121.4 . .
C11 C11 C10 121.49(8) 2_556 .
C11 C11 H11 119.3 2_556 .
C10 C11 H11 119.3 . .
C8 N1 C9 109.86(11) . .
C8 N1 C7 124.15(12) . .
C9 N1 C7 125.89(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3747(19) .
C1 C2 1.3821(19) .
C1 C7 1.5108(18) .
C2 C3 1.375(2) .
C2 H2 0.9300 .
C3 C4 1.365(2) .
C3 H3 0.9300 .
C4 C5 1.367(2) .
C4 H4 0.9300 .
C5 C6 1.388(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N1 1.4547(16) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 O1 1.225(2) .
C8 N1 1.3798(15) 2_556
C8 N1 1.3798(15) .
C9 C10 1.3765(17) .
C9 N1 1.3922(16) .
C9 C9 1.397(2) 2_556
C10 C11 1.3853(19) .
C10 H10 0.9300 .
C11 C11 1.384(3) 2_556
C11 H11 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.1(2) . .
C7 C1 C2 C3 177.60(13) . .
C1 C2 C3 C4 -0.2(2) . .
C2 C3 C4 C5 1.2(3) . .
C3 C4 C5 C6 -0.8(3) . .
C2 C1 C6 C5 1.5(2) . .
C7 C1 C6 C5 -177.19(13) . .
C4 C5 C6 C1 -0.6(2) . .
C6 C1 C7 N1 -126.36(14) . .
C2 C1 C7 N1 54.98(17) . .
N1 C9 C10 C11 179.26(12) . .
C9 C9 C10 C11 -0.5(2) 2_556 .
C9 C10 C11 C11 0.1(2) . 2_556
O1 C8 N1 C9 -179.65(6) . .
N1 C8 N1 C9 0.35(6) 2_556 .
O1 C8 N1 C7 -3.15(12) . .
N1 C8 N1 C7 176.85(12) 2_556 .
C10 C9 N1 C8 179.32(11) . .
C9 C9 N1 C8 -0.90(14) 2_556 .
C10 C9 N1 C7 2.9(2) . .
C9 C9 N1 C7 -177.33(11) 2_556 .
C1 C7 N1 C8 -104.99(13) . .
C1 C7 N1 C9 70.95(16) . .
