#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/10/2211072.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_2211072
loop_
_publ_author_name
'Yang-Gen Hu'
'Jun Zhu'
'Ai-Hua Zheng'
_publ_section_title
3-n-Butyl-2-(4-methylphenoxy)-3H-benzo[4,5]furo[3,2-d]pyrimidin-4-one
_journal_coeditor_code           IS2080
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4904
_journal_page_last               o4905
_journal_paper_doi               10.1107/S1600536806041304
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.5600(10)
_cell_angle_beta                 99.420(2)
_cell_angle_gamma                92.042(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0852(8)
_cell_length_b                   9.6504(9)
_cell_length_c                   10.3936(9)
_cell_measurement_reflns_used    3793
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.68
_cell_volume                     884.64(14)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7602
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0911P)²+0.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                3145
_reflns_number_total             3794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2080.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2211072
_cod_database_fobs_code          2211072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
C C1 -0.0893(3) 1.0217(3) 0.2015(2) 0.0765(6) Uani d . 1
H H1A -0.1169 1.1119 0.2413 0.115 Uiso calc R 1
H H1B -0.1761 0.9572 0.1772 0.115 Uiso calc R 1
H H1C -0.0480 1.0312 0.1239 0.115 Uiso calc R 1
C C2 0.02557(18) 0.96656(18) 0.29899(16) 0.0494(4) Uani d . 1
C C3 0.03984(19) 0.82317(18) 0.29216(17) 0.0520(4) Uani d . 1
H H3 -0.0238 0.7607 0.2273 0.062 Uiso calc R 1
C C4 0.11924(19) 1.05711(17) 0.39754(18) 0.0524(4) Uani d . 1
H H4 0.1101 1.1537 0.4049 0.063 Uiso calc R 1
C C5 0.14623(19) 0.77042(16) 0.37931(16) 0.0483(4) Uani d . 1
H H5 0.1547 0.6739 0.3735 0.058 Uiso calc R 1
C C6 0.22689(18) 1.00681(16) 0.48585(17) 0.0477(4) Uani d . 1
H H6 0.2899 1.0688 0.5517 0.057 Uiso calc R 1
C C7 0.23897(16) 0.86432(16) 0.47461(14) 0.0404(3) Uani d . 1
C C8 0.45649(16) 0.74628(15) 0.54222(14) 0.0374(3) Uani d . 1
C C9 0.66719(17) 0.62919(15) 0.64305(14) 0.0402(3) Uani d . 1
C C10 0.69115(16) 0.59738(14) 0.50995(14) 0.0380(3) Uani d . 1
C C11 0.60371(15) 0.64248(14) 0.40741(13) 0.0349(3) Uani d . 1
C C12 0.50861(18) 0.75283(17) 0.78757(14) 0.0440(4) Uani d . 1
H H12A 0.5221 0.6748 0.8355 0.053 Uiso calc R 1
H H12B 0.4050 0.7761 0.7819 0.053 Uiso calc R 1
C C13 0.60893(19) 0.87912(18) 0.86393(14) 0.0484(4) Uani d . 1
H H13A 0.5965 0.8915 0.9560 0.058 Uiso calc R 1
H H13B 0.7121 0.8584 0.8606 0.058 Uiso calc R 1
C C14 0.5811(2) 1.01651(18) 0.81504(16) 0.0513(4) Uani d . 1
H H14A 0.4775 1.0372 0.8158 0.062 Uiso calc R 1
H H14B 0.5980 1.0069 0.7243 0.062 Uiso calc R 1
C C15 0.6822(2) 1.1383(2) 0.89986(19) 0.0628(5) Uani d . 1
H H15A 0.6556 1.1571 0.9865 0.094 Uiso calc R 1
H H15B 0.6703 1.2206 0.8594 0.094 Uiso calc R 1
H H15C 0.7844 1.1139 0.9072 0.094 Uiso calc R 1
C C16 0.66863(16) 0.59438(14) 0.29160(14) 0.0377(3) Uani d . 1
C C17 0.79165(17) 0.52216(15) 0.33722(14) 0.0403(3) Uani d . 1
C C18 0.88459(19) 0.45767(17) 0.25671(17) 0.0485(4) Uani d . 1
H H18 0.9654 0.4098 0.2896 0.058 Uiso calc R 1
C C19 0.8512(2) 0.46805(19) 0.12511(17) 0.0535(4) Uani d . 1
H H19 0.9111 0.4258 0.0673 0.064 Uiso calc R 1
C C20 0.7304(2) 0.53982(18) 0.07552(16) 0.0537(4) Uani d . 1
H H20 0.7119 0.5449 -0.0142 0.064 Uiso calc R 1
C C21 0.63766(19) 0.60352(17) 0.15704(14) 0.0463(4) Uani d . 1
H H21 0.5569 0.6511 0.1235 0.056 Uiso calc R 1
N N1 0.54088(14) 0.70876(12) 0.65215(11) 0.0382(3) Uani d . 1
N N2 0.48074(13) 0.71851(12) 0.42171(11) 0.0372(3) Uani d . 1
O O1 0.34035(12) 0.81808(12) 0.57416(10) 0.0487(3) Uani d . 1
O O2 0.74313(14) 0.59674(13) 0.74117(11) 0.0555(3) Uani d . 1
O O3 0.80803(12) 0.52362(11) 0.47195(10) 0.0443(3) Uani d . 1
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 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C4 C2 C3 118.10(15) ?
C4 C2 C1 121.05(17) ?
C3 C2 C1 120.86(17) ?
C5 C3 C2 121.77(15) ?
C5 C3 H3 119.1 ?
C2 C3 H3 119.1 ?
C2 C4 C6 121.19(15) ?
C2 C4 H4 119.4 ?
C6 C4 H4 119.4 ?
C7 C5 C3 118.27(14) ?
C7 C5 H5 120.9 ?
C3 C5 H5 120.9 ?
C7 C6 C4 118.95(15) ?
C7 C6 H6 120.5 ?
C4 C6 H6 120.5 ?
C6 C7 C5 121.71(14) ?
C6 C7 O1 116.66(13) ?
C5 C7 O1 121.29(13) ?
N2 C8 O1 122.04(13) ?
N2 C8 N1 126.68(14) ?
O1 C8 N1 111.27(12) ?
O2 C9 N1 121.79(14) ?
O2 C9 C10 127.24(15) ?
N1 C9 C10 110.96(12) ?
C11 C10 O3 113.02(12) ?
C11 C10 C9 123.18(14) ?
O3 C10 C9 123.74(13) ?
C10 C11 N2 123.40(13) ?
C10 C11 C16 105.99(13) ?
N2 C11 C16 130.61(12) ?
N1 C12 C13 112.31(12) ?
N1 C12 H12A 109.1 ?
C13 C12 H12A 109.1 ?
N1 C12 H12B 109.1 ?
C13 C12 H12B 109.1 ?
H12A C12 H12B 107.9 ?
C14 C13 C12 115.44(13) ?
C14 C13 H13A 108.4 ?
C12 C13 H13A 108.4 ?
C14 C13 H13B 108.4 ?
C12 C13 H13B 108.4 ?
H13A C13 H13B 107.5 ?
C13 C14 C15 112.03(14) ?
C13 C14 H14A 109.2 ?
C15 C14 H14A 109.2 ?
C13 C14 H14B 109.2 ?
C15 C14 H14B 109.2 ?
H14A C14 H14B 107.9 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C17 C16 C21 118.78(14) ?
C17 C16 C11 104.87(12) ?
C21 C16 C11 136.35(14) ?
C18 C17 O3 124.53(14) ?
C18 C17 C16 123.66(14) ?
O3 C17 C16 111.81(13) ?
C19 C18 C17 116.26(16) ?
C19 C18 H18 121.9 ?
C17 C18 H18 121.9 ?
C18 C19 C20 122.02(16) ?
C18 C19 H19 119.0 ?
C20 C19 H19 119.0 ?
C21 C20 C19 121.21(16) ?
C21 C20 H20 119.4 ?
C19 C20 H20 119.4 ?
C20 C21 C16 118.07(15) ?
C20 C21 H21 121.0 ?
C16 C21 H21 121.0 ?
C8 N1 C9 121.79(12) y
C8 N1 C12 122.53(13) ?
C9 N1 C12 115.65(11) ?
C8 N2 C11 113.94(12) y
C8 O1 C7 119.94(11) ?
C10 O3 C17 104.31(11) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.507(2) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C4 1.379(2) ?
C2 C3 1.386(2) ?
C3 C5 1.384(2) ?
C3 H3 0.9300 ?
C4 C6 1.387(2) ?
C4 H4 0.9300 ?
C5 C7 1.373(2) ?
C5 H5 0.9300 ?
C6 C7 1.370(2) ?
C6 H6 0.9300 ?
C7 O1 1.4102(17) ?
C8 N2 1.2932(19) y
C8 O1 1.3394(19) ?
C8 N1 1.3766(17) y
C9 O2 1.2269(17) ?
C9 N1 1.411(2) y
C9 C10 1.420(2) ?
C10 C11 1.3631(18) ?
C10 O3 1.3741(18) y
C11 N2 1.3729(18) y
C11 C16 1.442(2) ?
C12 N1 1.4810(18) ?
C12 C13 1.519(2) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.512(2) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 C15 1.521(2) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 C17 1.397(2) ?
C16 C21 1.399(2) ?
C17 C18 1.377(2) ?
C17 O3 1.3814(17) y
C18 C19 1.373(2) ?
C18 H18 0.9300 ?
C19 C20 1.392(3) ?
C19 H19 0.9300 ?
C20 C21 1.380(2) ?
C20 H20 0.9300 ?
C21 H21 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
C4 C2 C3 C5 -1.2(3)
C1 C2 C3 C5 178.90(17)
C3 C2 C4 C6 1.3(3)
C1 C2 C4 C6 -178.79(17)
C2 C3 C5 C7 0.1(3)
C2 C4 C6 C7 -0.4(3)
C4 C6 C7 C5 -0.8(2)
C4 C6 C7 O1 -174.21(14)
C3 C5 C7 C6 0.9(2)
C3 C5 C7 O1 174.03(15)
O2 C9 C10 C11 -177.46(15)
N1 C9 C10 C11 1.5(2)
O2 C9 C10 O3 -0.4(2)
N1 C9 C10 O3 178.57(12)
O3 C10 C11 N2 -179.84(12)
C9 C10 C11 N2 -2.5(2)
O3 C10 C11 C16 -0.05(16)
C9 C10 C11 C16 177.28(13)
N1 C12 C13 C14 69.18(18)
C12 C13 C14 C15 177.90(14)
C10 C11 C16 C17 0.42(15)
N2 C11 C16 C17 -179.81(14)
C10 C11 C16 C21 -179.70(16)
N2 C11 C16 C21 0.1(3)
C21 C16 C17 C18 -0.6(2)
C11 C16 C17 C18 179.33(14)
C21 C16 C17 O3 179.43(12)
C11 C16 C17 O3 -0.66(16)
O3 C17 C18 C19 -179.62(14)
C16 C17 C18 C19 0.4(2)
C17 C18 C19 C20 0.1(3)
C18 C19 C20 C21 -0.4(3)
C19 C20 C21 C16 0.2(3)
C17 C16 C21 C20 0.3(2)
C11 C16 C21 C20 -179.61(16)
N2 C8 N1 C9 -1.5(2)
O1 C8 N1 C9 178.36(12)
N2 C8 N1 C12 176.39(13)
O1 C8 N1 C12 -3.73(19)
O2 C9 N1 C8 179.39(13)
C10 C9 N1 C8 0.33(19)
O2 C9 N1 C12 1.3(2)
C10 C9 N1 C12 -177.71(12)
C13 C12 N1 C8 -99.25(16)
C13 C12 N1 C9 78.78(16)
O1 C8 N2 C11 -179.20(12)
N1 C8 N2 C11 0.7(2)
C10 C11 N2 C8 1.3(2)
C16 C11 N2 C8 -178.43(14)
N2 C8 O1 C7 0.8(2)
N1 C8 O1 C7 -179.10(12)
C6 C7 O1 C8 -118.93(15)
C5 C7 O1 C8 67.60(19)
C11 C10 O3 C17 -0.35(16)
C9 C10 O3 C17 -177.65(13)
C18 C17 O3 C10 -179.36(14)
C16 C17 O3 C10 0.63(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126167
