#------------------------------------------------------------------------------
#$Date: 2018-01-18 14:15:39 +0200 (Thu, 18 Jan 2018) $
#$Revision: 205369 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/87/1548720.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_1548720
loop_
_publ_author_name
'Agnieszka Skotnicka'
'Erkki Kolehmainen'
'Przemyslaw Czelen'
'Arto Valkonen'
'Ryszard Gawinecki'
_publ_section_title
;
 Synthesis and Structural Characterization of Substituted
 2-Phenacylbenzoxazoles
;
_journal_name_full               'International Journal of Molecular Sciences'
_journal_page_first              4444
_journal_page_last               4460
_journal_paper_doi               10.3390/ijms14034444
_journal_volume                  14
_journal_year                    2013
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_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'
_cell_angle_alpha                108.347(3)
_cell_angle_beta                 104.143(3)
_cell_angle_gamma                93.746(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2713(3)
_cell_length_b                   11.0619(4)
_cell_length_c                   11.1918(4)
_cell_volume                     931.17(6)
_diffrn_ambient_temperature      123
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    0.699
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             388
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3677
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1027
_cod_data_source_file            IJMS-14-04444-2.cif
_cod_data_source_block           2
_cod_original_cell_volume        931.18(6)
_cod_database_code               1548720
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.30880(10) 0.03290(10) 0.74890(10) 1.000 0.0338(6) . . . .
O12 O Uani 0.14640(10) 0.08300(10) 0.37950(10) 1.000 0.0285(6) . . . .
O13 O Uani 0.38650(10) 0.22280(10) 0.43860(10) 1.000 0.0354(6) . . . .
N3 N Uani 0.17490(10) 0.16640(10) 0.65620(10) 1.000 0.0304(6) . . . .
C2 C Uani 0.2520(2) 0.06680(10) 0.63850(10) 1.000 0.0302(6) . . . .
C4 C Uani 0.1135(2) 0.30620(10) 0.86400(10) 1.000 0.0364(6) . . . .
C5 C Uani 0.1379(2) 0.31940(10) 0.99470(10) 1.000 0.0418(6) . . . .
C6 C Uani 0.2228(2) 0.2354(2) 1.04860(10) 1.000 0.0428(6) . . . .
C7 C Uani 0.2862(2) 0.13420(10) 0.97430(10) 1.000 0.0396(6) . . . .
C8 C Uani 0.2597(2) 0.12270(10) 0.84440(10) 1.000 0.0319(6) . . . .
C9 C Uani 0.1769(2) 0.20530(10) 0.78850(10) 1.000 0.0298(6) . . . .
C10 C Uani 0.2875(2) -0.01800(10) 0.52380(10) 1.000 0.0286(6) . . . .
C11 C Uani 0.24130(10) -0.01170(10) 0.40280(10) 1.000 0.0271(6) . . . .
C13 C Uani 0.2348(2) 0.20050(10) 0.40310(10) 1.000 0.0276(6) . . . .
C14 C Uani 0.1217(2) 0.29290(10) 0.37600(10) 1.000 0.0269(6) . . . .
C15 C Uani -0.0529(2) 0.26210(10) 0.34430(10) 1.000 0.0288(6) . . . .
C16 C Uani -0.1571(2) 0.35010(10) 0.31880(10) 1.000 0.0304(6) . . . .
C17 C Uani -0.0821(2) 0.46970(10) 0.32550(10) 1.000 0.0339(6) . . . .
C18 C Uani 0.0921(2) 0.50050(10) 0.35640(10) 1.000 0.0342(6) . . . .
C19 C Uani 0.1950(2) 0.41260(10) 0.38220(10) 1.000 0.0310(6) . . . .
C20 C Uani -0.3456(2) 0.31730(10) 0.2889(2) 1.000 0.0393(6) . . . .
C21 C Uani 0.2720(2) -0.10180(10) 0.28500(10) 1.000 0.0278(6) . . . .
C22 C Uani 0.3512(2) -0.20840(10) 0.29230(10) 1.000 0.0301(6) . . . .
C23 C Uani 0.3797(2) -0.29610(10) 0.18210(10) 1.000 0.0326(6) . . . .
C24 C Uani 0.3274(2) -0.27660(10) 0.06270(10) 1.000 0.0373(6) . . . .
C25 C Uani 0.2495(2) -0.17130(10) 0.05380(10) 1.000 0.0386(6) . . . .
C26 C Uani 0.2218(2) -0.08390(10) 0.16440(10) 1.000 0.0326(6) . . . .
C27 C Uani 0.4674(2) -0.40890(10) 0.1951(2) 1.000 0.0400(6) . . . .
H4 H Uiso 0.05600 0.36350 0.82760 1.000 0.0440 . . . .
H5 H Uiso 0.09580 0.38720 1.04890 1.000 0.0500 . . . .
H6 H Uiso 0.23750 0.24800 1.13880 1.000 0.0510 . . . .
H7 H Uiso 0.34400 0.07680 1.01050 1.000 0.0470 . . . .
H10 H Uiso 0.34970 -0.08480 0.53500 1.000 0.0340 . . . .
H15 H Uiso -0.10150 0.18010 0.33990 1.000 0.0340 . . . .
H17 H Uiso -0.15130 0.53100 0.30860 1.000 0.0400 . . . .
H18 H Uiso 0.14080 0.58210 0.35980 1.000 0.0410 . . . .
H19 H Uiso 0.31420 0.43360 0.40390 1.000 0.0370 . . . .
H20A H Uiso -0.37390 0.22970 0.28860 .5000 0.0590 . . . .
H20B H Uiso -0.40010 0.32210 0.20260 .5000 0.0590 . . . .
H20C H Uiso -0.38530 0.37860 0.35590 .5000 0.0590 . . . .
H20D H Uiso -0.39890 0.39050 0.27620 .5000 0.0590 . . . .
H20E H Uiso -0.37280 0.29820 0.36210 .5000 0.0590 . . . .
H20F H Uiso -0.38760 0.24170 0.20890 .5000 0.0590 . . . .
H22 H Uiso 0.38640 -0.22110 0.37430 1.000 0.0360 . . . .
H24 H Uiso 0.34510 -0.33610 -0.01350 1.000 0.0450 . . . .
H25 H Uiso 0.21480 -0.15880 -0.02830 1.000 0.0460 . . . .
H26 H Uiso 0.16870 -0.01180 0.15760 1.000 0.0390 . . . .
H27A H Uiso 0.47780 -0.46110 0.10940 .5000 0.0600 . . . .
H27B H Uiso 0.40140 -0.46180 0.22740 .5000 0.0600 . . . .
H27C H Uiso 0.58000 -0.37680 0.25710 .5000 0.0600 . . . .
H27D H Uiso 0.49500 -0.40540 0.28660 .5000 0.0600 . . . .
H27E H Uiso 0.57150 -0.40460 0.16850 .5000 0.0600 . . . .
H27F H Uiso 0.39280 -0.48970 0.13880 .5000 0.0600 . . . .
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C8 103.87(10) . . . yes
C11 O12 C13 116.51(10) . . . yes
C2 N3 C9 104.79(10) . . . yes
O1 C2 N3 114.82(10) . . . yes
O1 C2 C10 113.26(11) . . . yes
N3 C2 C10 131.90(11) . . . yes
C5 C4 C9 117.06(11) . . . no
C4 C5 C6 121.58(12) . . . no
C5 C6 C7 121.93(10) . . . no
C6 C7 C8 115.42(12) . . . no
O1 C8 C7 128.10(12) . . . yes
O1 C8 C9 108.03(10) . . . yes
C7 C8 C9 123.87(12) . . . no
N3 C9 C4 131.37(11) . . . yes
N3 C9 C8 108.49(11) . . . yes
C4 C9 C8 120.14(10) . . . no
C2 C10 C11 126.26(12) . . . no
O12 C11 C10 119.51(10) . . . yes
O12 C11 C21 114.42(9) . . . yes
C10 C11 C21 125.97(11) . . . no
O12 C13 O13 122.84(12) . . . yes
O12 C13 C14 111.76(13) . . . yes
O13 C13 C14 125.37(12) . . . yes
C13 C14 C15 121.58(11) . . . no
C13 C14 C19 118.05(14) . . . no
C15 C14 C19 120.37(13) . . . no
C14 C15 C16 120.73(12) . . . no
C15 C16 C17 118.33(15) . . . no
C15 C16 C20 120.24(12) . . . no
C17 C16 C20 121.40(13) . . . no
C16 C17 C18 121.09(13) . . . no
C17 C18 C19 120.24(12) . . . no
C14 C19 C18 119.24(15) . . . no
C11 C21 C22 120.25(10) . . . no
C11 C21 C26 121.00(12) . . . no
C22 C21 C26 118.75(11) . . . no
C21 C22 C23 121.46(10) . . . no
C22 C23 C24 118.70(12) . . . no
C22 C23 C27 119.55(12) . . . no
C24 C23 C27 121.75(13) . . . no
C23 C24 C25 120.62(11) . . . no
C24 C25 C26 120.37(10) . . . no
C21 C26 C25 120.11(12) . . . no
C5 C4 H4 121.00 . . . no
C9 C4 H4 121.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C5 C6 H6 119.00 . . . no
C7 C6 H6 119.00 . . . no
C6 C7 H7 122.00 . . . no
C8 C7 H7 122.00 . . . no
C2 C10 H10 117.00 . . . no
C11 C10 H10 117.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C16 C17 H17 119.00 . . . no
C18 C17 H17 119.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C14 C19 H19 120.00 . . . no
C18 C19 H19 120.00 . . . no
C16 C20 H20A 109.00 . . . no
C16 C20 H20B 109.00 . . . no
C16 C20 H20C 109.00 . . . no
C16 C20 H20D 109.00 . . . no
C16 C20 H20E 109.00 . . . no
C16 C20 H20F 109.00 . . . no
H20A C20 H20B 109.00 . . . no
H20A C20 H20C 110.00 . . . no
H20A C20 H20D 141.00 . . . no
H20A C20 H20E 56.00 . . . no
H20A C20 H20F 56.00 . . . no
H20B C20 H20C 109.00 . . . no
H20B C20 H20D 56.00 . . . no
H20B C20 H20E 141.00 . . . no
H20B C20 H20F 56.00 . . . no
H20C C20 H20D 56.00 . . . no
H20C C20 H20E 56.00 . . . no
H20C C20 H20F 141.00 . . . no
H20D C20 H20E 110.00 . . . no
H20D C20 H20F 109.00 . . . no
H20E C20 H20F 109.00 . . . no
C21 C22 H22 119.00 . . . no
C23 C22 H22 119.00 . . . no
C23 C24 H24 120.00 . . . no
C25 C24 H24 120.00 . . . no
C24 C25 H25 120.00 . . . no
C26 C25 H25 120.00 . . . no
C21 C26 H26 120.00 . . . no
C25 C26 H26 120.00 . . . no
C23 C27 H27A 110.00 . . . no
C23 C27 H27B 109.00 . . . no
C23 C27 H27C 109.00 . . . no
C23 C27 H27D 109.00 . . . no
C23 C27 H27E 109.00 . . . no
C23 C27 H27F 110.00 . . . no
H27A C27 H27B 109.00 . . . no
H27A C27 H27C 109.00 . . . no
H27A C27 H27D 141.00 . . . no
H27A C27 H27E 56.00 . . . no
H27A C27 H27F 56.00 . . . no
H27B C27 H27C 109.00 . . . no
H27B C27 H27D 56.00 . . . no
H27B C27 H27E 141.00 . . . no
H27B C27 H27F 56.00 . . . no
H27C C27 H27D 56.00 . . . no
H27C C27 H27E 56.00 . . . no
H27C C27 H27F 141.00 . . . no
H27D C27 H27E 109.00 . . . no
H27D C27 H27F 109.00 . . . no
H27E C27 H27F 110.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3853(15) . . yes
O1 C8 1.3750(16) . . yes
O12 C11 1.4003(15) . . yes
O12 C13 1.3635(17) . . yes
O13 C13 1.2031(19) . . yes
N3 C2 1.2946(17) . . yes
N3 C9 1.4014(15) . . yes
C2 C10 1.4409(17) . . no
C4 C5 1.3853(15) . . no
C4 C9 1.3907(19) . . no
C5 C6 1.397(2) . . no
C6 C7 1.387(2) . . no
C7 C8 1.3791(15) . . no
C8 C9 1.3884(18) . . no
C10 C11 1.3397(15) . . no
C11 C21 1.4716(16) . . no
C13 C14 1.481(2) . . no
C14 C15 1.392(2) . . no
C14 C19 1.3937(18) . . no
C15 C16 1.3915(19) . . no
C16 C17 1.3958(18) . . no
C16 C20 1.506(2) . . no
C17 C18 1.389(2) . . no
C18 C19 1.3849(19) . . no
C21 C22 1.4006(19) . . no
C21 C26 1.3923(15) . . no
C22 C23 1.3916(17) . . no
C23 C24 1.3894(15) . . no
C23 C27 1.512(2) . . no
C24 C25 1.3862(19) . . no
C25 C26 1.3905(17) . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C10 H10 0.9500 . . no
C15 H15 0.9500 . . no
C17 H17 0.9500 . . no
C18 H18 0.9500 . . no
C19 H19 0.9500 . . no
C20 H20A 0.9800 . . no
C20 H20B 0.9800 . . no
C20 H20C 0.9800 . . no
C20 H20D 0.9800 . . no
C20 H20E 0.9800 . . no
C20 H20F 0.9800 . . no
C22 H22 0.9500 . . no
C24 H24 0.9500 . . no
C25 H25 0.9500 . . no
C26 H26 0.9500 . . no
C27 H27A 0.9800 . . no
C27 H27B 0.9800 . . no
C27 H27C 0.9800 . . no
C27 H27D 0.9800 . . no
C27 H27E 0.9800 . . no
C27 H27F 0.9800 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15 O12 0.9500 2.3900 2.7200(17) 100.00 . yes
C15 H15 O1 0.9500 2.5800 3.4775(17) 158.00 2_556 yes
C20 H20E O13 0.9800 2.5400 3.380(2) 144.00 1_455 yes
C22 H22 O13 0.9500 2.4500 3.3101(16) 150.00 2_656 yes
C26 H26 O12 0.9500 2.4300 2.7711(16) 101.00 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 C2 N3 0.13(16) . . . . no
C8 O1 C2 C10 -178.72(13) . . . . no
C2 O1 C8 C7 -179.29(15) . . . . no
C2 O1 C8 C9 0.02(15) . . . . no
C13 O12 C11 C10 85.80(14) . . . . no
C13 O12 C11 C21 -97.75(12) . . . . no
C11 O12 C13 O13 2.02(17) . . . . no
C11 O12 C13 C14 -179.62(9) . . . . no
C9 N3 C2 O1 -0.22(16) . . . . no
C9 N3 C2 C10 178.36(16) . . . . no
C2 N3 C9 C4 -180.00(16) . . . . no
C2 N3 C9 C8 0.23(16) . . . . no
O1 C2 C10 C11 177.06(13) . . . . no
N3 C2 C10 C11 -1.5(3) . . . . no
C9 C4 C5 C6 0.2(2) . . . . no
C5 C4 C9 N3 -179.47(14) . . . . no
C5 C4 C9 C8 0.3(2) . . . . no
C4 C5 C6 C7 -0.4(3) . . . . no
C5 C6 C7 C8 0.1(2) . . . . no
C6 C7 C8 O1 179.63(15) . . . . no
C6 C7 C8 C9 0.4(2) . . . . no
O1 C8 C9 N3 -0.15(16) . . . . no
O1 C8 C9 C4 -179.97(13) . . . . no
C7 C8 C9 N3 179.19(14) . . . . no
C7 C8 C9 C4 -0.6(2) . . . . no
C2 C10 C11 O12 -1.3(2) . . . . no
C2 C10 C11 C21 -177.35(14) . . . . no
O12 C11 C21 C22 -173.89(12) . . . . no
O12 C11 C21 C26 5.44(18) . . . . no
C10 C11 C21 C22 2.3(2) . . . . no
C10 C11 C21 C26 -178.37(14) . . . . no
O12 C13 C14 C15 6.37(15) . . . . no
O12 C13 C14 C19 -173.21(10) . . . . no
O13 C13 C14 C15 -175.32(11) . . . . no
O13 C13 C14 C19 5.10(17) . . . . no
C13 C14 C15 C16 -179.82(10) . . . . no
C19 C14 C15 C16 -0.25(16) . . . . no
C13 C14 C19 C18 179.56(10) . . . . no
C15 C14 C19 C18 -0.03(16) . . . . no
C14 C15 C16 C17 0.16(16) . . . . no
C14 C15 C16 C20 -178.01(12) . . . . no
C15 C16 C17 C18 0.20(16) . . . . no
C20 C16 C17 C18 178.35(13) . . . . no
C16 C17 C18 C19 -0.48(16) . . . . no
C17 C18 C19 C14 0.39(16) . . . . no
C11 C21 C22 C23 179.10(13) . . . . no
C26 C21 C22 C23 -0.3(2) . . . . no
C11 C21 C26 C25 -178.95(13) . . . . no
C22 C21 C26 C25 0.4(2) . . . . no
C21 C22 C23 C24 -0.2(2) . . . . no
C21 C22 C23 C27 179.33(14) . . . . no
C22 C23 C24 C25 0.5(2) . . . . no
C27 C23 C24 C25 -179.03(15) . . . . no
C23 C24 C25 C26 -0.3(2) . . . . no
C24 C25 C26 C21 -0.1(2) . . . . no
