#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/75/2207562.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_2207562
loop_
_publ_author_name
'Yong Sun'
'Yang-Gen Hu'
_publ_section_title
3-(4-Methylphenyl)-2-morpholinobenzo[4,5]furo[3,2-d]pyrimidin-4(3H)-one
_journal_coeditor_code           HK6056
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4233
_journal_page_last               o4235
_journal_paper_doi               10.1107/S1600536805037918
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C21 H19 N3 O3'
_chemical_formula_moiety         'C21 H19 N3 O3'
_chemical_formula_sum            'C21 H19 N3 O3'
_chemical_formula_weight         361.39
_chemical_melting_point          466
_chemical_name_systematic
;
3-(4-Methylphenyl)-2-morpholinobenzo[4,5]furo[3,2-d]pyrimidin-4(3H)-one
;
_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                 125.5620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.8042(16)
_cell_length_b                   10.9268(8)
_cell_length_c                   17.7465(12)
_cell_measurement_reflns_used    3724
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.16
_cell_volume                     3597.3(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14758
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0501
_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)+(0.0618P)²+0.7865P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                2780
_reflns_number_total             3923
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk6056.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2207562
_cod_database_fobs_code          2207562
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_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_type_symbol
C1 -0.06140(11) 1.24268(18) 0.28387(13) 0.0553(5) Uani d . 1 C
H1 -0.0206 1.2803 0.3342 0.066 Uiso calc R 1 H
C2 -0.11861(13) 1.3111(2) 0.21474(14) 0.0671(6) Uani d . 1 C
H2 -0.1168 1.3960 0.2188 0.081 Uiso calc R 1 H
C3 -0.17914(12) 1.2542(2) 0.13892(14) 0.0713(6) Uani d . 1 C
H3 -0.2170 1.3025 0.0935 0.086 Uiso calc R 1 H
C4 -0.18475(11) 1.1297(2) 0.12903(13) 0.0639(6) Uani d . 1 C
H4 -0.2252 1.0923 0.0781 0.077 Uiso calc R 1 H
C5 -0.12712(10) 1.06257(18) 0.19876(12) 0.0515(5) Uani d . 1 C
C6 -0.06644(9) 1.11571(16) 0.27612(12) 0.0465(4) Uani d . 1 C
C7 -0.02138(9) 1.01357(15) 0.33176(11) 0.0425(4) Uani d . 1 C
C8 -0.05730(9) 0.91152(16) 0.28412(11) 0.0453(4) Uani d . 1 C
C9 -0.03136(9) 0.79129(16) 0.31572(11) 0.0425(4) Uani d . 1 C
C10 0.07169(9) 0.90490(14) 0.44772(11) 0.0396(4) Uani d . 1 C
C11 0.16069(10) 1.00865(16) 0.58875(13) 0.0564(5) Uani d . 1 C
H11A 0.1214 1.0420 0.5890 0.068 Uiso calc R 1 H
H11B 0.1744 1.0690 0.5615 0.068 Uiso calc R 1 H
C12 0.22368(12) 0.9813(2) 0.68605(14) 0.0731(6) Uani d . 1 C
H12A 0.2393 1.0562 0.7221 0.088 Uiso calc R 1 H
H12B 0.2089 0.9243 0.7139 0.088 Uiso calc R 1 H
C13 0.25989(10) 0.81958(18) 0.63821(14) 0.0640(6) Uani d . 1 C
H13A 0.2455 0.7620 0.6663 0.077 Uiso calc R 1 H
H13B 0.3001 0.7843 0.6410 0.077 Uiso calc R 1 H
C14 0.19794(9) 0.83969(17) 0.53858(12) 0.0517(5) Uani d . 1 C
H14A 0.2130 0.8927 0.5089 0.062 Uiso calc R 1 H
H14B 0.1829 0.7621 0.5060 0.062 Uiso calc R 1 H
C15 0.06837(9) 0.65706(15) 0.53064(11) 0.0462(4) Uani d . 1 C
H15 0.0565 0.7187 0.5557 0.055 Uiso calc R 1 H
C16 0.06368(9) 0.67807(14) 0.45087(11) 0.0398(4) Uani d . 1 C
C17 0.08116(9) 0.58697(16) 0.41331(11) 0.0479(4) Uani d . 1 C
H17 0.0783 0.6011 0.3596 0.057 Uiso calc R 1 H
C18 0.10289(10) 0.47465(16) 0.45657(12) 0.0511(5) Uani d . 1 C
H18 0.1145 0.4130 0.4311 0.061 Uiso calc R 1 H
C19 0.10801(9) 0.45087(15) 0.53710(12) 0.0473(4) Uani d . 1 C
C20 0.09072(10) 0.54445(16) 0.57344(12) 0.0504(4) Uani d . 1 C
H20 0.0942 0.5312 0.6277 0.061 Uiso calc R 1 H
C21 0.12914(12) 0.32632(17) 0.58111(15) 0.0651(6) Uani d . 1 C
H21A 0.1205 0.3216 0.6280 0.098 Uiso calc R 1 H
H21B 0.1794 0.3126 0.6087 0.098 Uiso calc R 1 H
H21C 0.1010 0.2651 0.5348 0.098 Uiso calc R 1 H
N1 0.03722(7) 0.79546(12) 0.40418(9) 0.0408(3) Uani d . 1 N
N2 0.04476(7) 1.01322(12) 0.41493(9) 0.0442(3) Uani d . 1 N
N3 0.13733(7) 0.89601(12) 0.53389(9) 0.0438(3) Uani d . 1 N
O1 -0.12301(6) 0.93638(12) 0.20149(8) 0.0550(3) Uani d . 1 O
O2 -0.06073(7) 0.69479(11) 0.27873(8) 0.0562(4) Uani d . 1 O
O3 0.28198(7) 0.93070(13) 0.68882(9) 0.0722(4) Uani d . 1 O
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_publ_flag
C2 C1 C6 118.1(2) ?
C2 C1 H1 121.0 ?
C6 C1 H1 121.0 ?
C1 C2 C3 120.7(2) ?
C1 C2 H2 119.7 ?
C3 C2 H2 119.7 ?
C4 C3 C2 122.25(19) ?
C4 C3 H3 118.9 ?
C2 C3 H3 118.9 ?
C3 C4 C5 116.4(2) ?
C3 C4 H4 121.8 ?
C5 C4 H4 121.8 ?
C4 C5 O1 124.88(19) ?
C4 C5 C6 123.11(19) ?
O1 C5 C6 112.00(15) ?
C5 C6 C1 119.48(16) ?
C5 C6 C7 104.83(16) ?
C1 C6 C7 135.70(17) ?
C8 C7 N2 124.13(15) ?
C8 C7 C6 106.14(16) ?
N2 C7 C6 129.72(16) ?
C7 C8 O1 112.97(15) ?
C7 C8 C9 123.82(15) ?
O1 C8 C9 123.20(15) ?
O2 C9 C8 128.21(16) ?
O2 C9 N1 121.72(15) ?
C8 C9 N1 110.03(14) ?
N2 C10 N3 118.77(14) ?
N2 C10 N1 124.37(15) ?
N3 C10 N1 116.77(13) ?
N3 C11 C12 109.42(15) yes
N3 C11 H11A 109.8 ?
C12 C11 H11A 109.8 ?
N3 C11 H11B 109.8 ?
C12 C11 H11B 109.8 ?
H11A C11 H11B 108.2 ?
O3 C12 C11 111.69(17) yes
O3 C12 H12A 109.3 ?
C11 C12 H12A 109.3 ?
O3 C12 H12B 109.3 ?
C11 C12 H12B 109.3 ?
H12A C12 H12B 107.9 ?
O3 C13 C14 111.36(15) yes
O3 C13 H13A 109.4 ?
C14 C13 H13A 109.4 ?
O3 C13 H13B 109.4 ?
C14 C13 H13B 109.4 ?
H13A C13 H13B 108.0 ?
N3 C14 C13 109.69(15) yes
N3 C14 H14A 109.7 ?
C13 C14 H14A 109.7 ?
N3 C14 H14B 109.7 ?
C13 C14 H14B 109.7 ?
H14A C14 H14B 108.2 ?
C16 C15 C20 119.90(15) ?
C16 C15 H15 120.0 ?
C20 C15 H15 120.0 ?
C15 C16 C17 120.36(15) ?
C15 C16 N1 119.46(14) ?
C17 C16 N1 120.13(14) ?
C18 C17 C16 119.01(16) ?
C18 C17 H17 120.5 ?
C16 C17 H17 120.5 ?
C17 C18 C19 121.84(16) ?
C17 C18 H18 119.1 ?
C19 C18 H18 119.1 ?
C20 C19 C18 117.73(16) ?
C20 C19 C21 121.31(17) ?
C18 C19 C21 120.93(16) ?
C15 C20 C19 121.16(16) ?
C15 C20 H20 119.4 ?
C19 C20 H20 119.4 ?
C19 C21 H21A 109.5 ?
C19 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C19 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C10 N1 C9 122.62(13) ?
C10 N1 C16 121.88(13) ?
C9 N1 C16 115.01(13) ?
C10 N2 C7 114.98(14) ?
C10 N3 C11 114.58(13) ?
C10 N3 C14 117.88(13) ?
C11 N3 C14 110.35(14) yes
C5 O1 C8 104.05(13) ?
C12 O3 C13 109.42(15) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.380(3) ?
C1 C6 1.392(3) ?
C1 H1 0.9300 ?
C2 C3 1.394(3) ?
C2 H2 0.9300 ?
C3 C4 1.368(3) ?
C3 H3 0.9300 ?
C4 C5 1.380(2) ?
C4 H4 0.9300 ?
C5 O1 1.381(2) yes
C5 C6 1.388(3) yes
C6 C7 1.448(2) yes
C7 C8 1.350(2) yes
C7 N2 1.365(2) yes
C8 O1 1.3833(19) yes
C8 C9 1.416(2) ?
C9 O2 1.2165(19) yes
C9 N1 1.434(2) yes
C10 N2 1.3042(19) yes
C10 N3 1.388(2) yes
C10 N1 1.392(2) ?
C11 N3 1.464(2) yes
C11 C12 1.500(3) yes
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 O3 1.414(3) yes
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 O3 1.417(2) yes
C13 C14 1.505(2) yes
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 N3 1.470(2) yes
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.375(2) ?
C15 C20 1.379(2) ?
C15 H15 0.9300 ?
C16 C17 1.379(2) ?
C16 N1 1.4541(19) ?
C17 C18 1.378(2) ?
C17 H17 0.9300 ?
C18 C19 1.389(2) ?
C18 H18 0.9300 ?
C19 C20 1.383(2) ?
C19 C21 1.502(2) ?
C20 H20 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
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
_geom_hbond_publ_flag
C17 H17 O2 2 0.93 2.47 3.372(2) 164 yes
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_publ_flag
C6 C1 C2 C3 -0.8(3) ?
C1 C2 C3 C4 -0.3(3) ?
C2 C3 C4 C5 0.3(3) ?
C3 C4 C5 O1 179.49(17) ?
C3 C4 C5 C6 0.8(3) ?
C4 C5 C6 C1 -2.0(3) ?
O1 C5 C6 C1 179.21(15) ?
C4 C5 C6 C7 178.22(16) ?
O1 C5 C6 C7 -0.61(19) ?
C2 C1 C6 C5 1.9(3) ?
C2 C1 C6 C7 -178.35(18) ?
C5 C6 C7 C8 0.67(18) ?
C1 C6 C7 C8 -179.11(19) ?
C5 C6 C7 N2 179.65(16) ?
C1 C6 C7 N2 -0.1(3) ?
N2 C7 C8 O1 -179.58(14) ?
C6 C7 C8 O1 -0.52(19) ?
N2 C7 C8 C9 1.5(3) ?
C6 C7 C8 C9 -179.48(16) ?
C7 C8 C9 O2 177.97(17) ?
O1 C8 C9 O2 -0.9(3) ?
C7 C8 C9 N1 0.2(2) ?
O1 C8 C9 N1 -178.69(14) ?
N3 C11 C12 O3 58.5(2) yes
O3 C13 C14 N3 -57.6(2) yes
C20 C15 C16 C17 0.1(3) ?
C20 C15 C16 N1 177.48(15) ?
C15 C16 C17 C18 0.4(3) ?
N1 C16 C17 C18 -176.99(15) ?
C16 C17 C18 C19 -0.3(3) ?
C17 C18 C19 C20 -0.2(3) ?
C17 C18 C19 C21 177.68(17) ?
C16 C15 C20 C19 -0.7(3) ?
C18 C19 C20 C15 0.7(3) ?
C21 C19 C20 C15 -177.18(17) ?
N2 C10 N1 C9 2.4(2) ?
N3 C10 N1 C9 178.99(14) ?
N2 C10 N1 C16 -169.11(15) ?
N3 C10 N1 C16 7.4(2) ?
O2 C9 N1 C10 -179.94(15) ?
C8 C9 N1 C10 -2.0(2) ?
O2 C9 N1 C16 -7.9(2) ?
C8 C9 N1 C16 170.11(13) ?
C15 C16 N1 C10 60.1(2) ?
C17 C16 N1 C10 -122.48(17) ?
C15 C16 N1 C9 -112.02(17) ?
C17 C16 N1 C9 65.4(2) ?
N3 C10 N2 C7 -177.21(14) ?
N1 C10 N2 C7 -0.7(2) ?
C8 C7 N2 C10 -1.2(2) ?
C6 C7 N2 C10 180.00(16) ?
N2 C10 N3 C11 14.5(2) ?
N1 C10 N3 C11 -162.29(15) ?
N2 C10 N3 C14 -117.96(17) ?
N1 C10 N3 C14 65.3(2) ?
C12 C11 N3 C10 168.81(17) ?
C12 C11 N3 C14 -55.3(2) yes
C13 C14 N3 C10 -170.65(15) ?
C13 C14 N3 C11 55.07(19) yes
C4 C5 O1 C8 -178.50(17) ?
C6 C5 O1 C8 0.31(18) ?
C7 C8 O1 C5 0.15(19) ?
C9 C8 O1 C5 179.12(16) ?
C11 C12 O3 C13 -60.5(2) yes
C14 C13 O3 C12 59.9(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126873
