#------------------------------------------------------------------------------
#$Date: 2018-06-18 18:53:46 +0300 (Mon, 18 Jun 2018) $
#$Revision: 208483 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/11/2021167.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_2021167
loop_
_publ_author_name
'Nguyen Tien, Cong'
'Nguyen Van, Thin'
'Le Duc, Giang'
'Vu Quoc, Manh'
'Vu Quoc, Trung'
'Pham Chien, Thang'
'Nguyen Huy, Hung'
'Dang Thi Tuyet, Anh'
'Nguyen Van, Tuyen'
'Van Meervelt, Luc'
_publ_section_title
;
 Synthesis, structure and in vitro cytotoxicity testing of some
 1,3,4-oxadiazoline derivatives from 2-hydroxy-5-iodobenzoic acid
;
_journal_coeditor_code           SK3693
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618008719
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C19 H17 I N2 O4'
_chemical_formula_moiety         'C19 H17 I N2 O4'
_chemical_formula_sum            'C19 H17 I N2 O4'
_chemical_formula_weight         464.24
_chemical_name_systematic
;
2-(4-Acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl
acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 110.180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8370(10)
_cell_length_b                   20.0560(10)
_cell_length_c                   11.0150(10)
_cell_measurement_reflns_used    9773
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.10
_cell_measurement_theta_min      3.19
_cell_volume                     1832.4(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            54289
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         2.830
_exptl_absorpt_coefficient_mu    1.774
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.587
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0212P)²+1.2207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0500
_reflns_number_gt                4994
_reflns_number_total             5600
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3693sup1.cif
_cod_data_source_block           6c
_cod_database_code               2021167
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
I I1 1.02273(2) 0.44378(2) 0.71043(2) 0.02391(4) Uani d 1
O O1 0.42189(12) 0.51004(5) 0.22300(10) 0.0198(2) Uani d 1
N N1 0.44105(14) 0.63918(6) 0.32433(11) 0.0172(2) Uani d 1
C C1 0.81918(17) 0.46520(7) 0.54844(14) 0.0185(3) Uani d 1
O O2 0.57214(14) 0.56173(6) 0.12194(11) 0.0265(2) Uani d 1
N N2 0.43632(14) 0.70564(6) 0.36222(11) 0.0170(2) Uani d 1
C C2 0.75217(17) 0.52839(7) 0.53642(13) 0.0177(3) Uani d 1
H H2 0.795397 0.560319 0.603141 0.021 Uiso calc 1
O O3 0.63889(13) 0.65492(5) 0.51584(9) 0.0191(2) Uani d 1
C C3 0.62097(16) 0.54536(7) 0.42630(13) 0.0162(2) Uani d 1
O O4 0.31986(13) 0.80687(5) 0.32597(11) 0.0240(2) Uani d 1
C C4 0.55900(17) 0.49706(7) 0.33034(13) 0.0175(3) Uani d 1
C C5 0.62622(19) 0.43404(7) 0.34230(15) 0.0221(3) Uani d 1
H H5 0.582960 0.401921 0.275960 0.027 Uiso calc 1
C C6 0.75733(19) 0.41777(7) 0.45167(15) 0.0226(3) Uani d 1
H H6 0.804238 0.374628 0.460211 0.027 Uiso calc 1
C C7 0.55901(16) 0.61343(7) 0.41634(13) 0.0161(2) Uani d 1
C C8 0.58015(17) 0.72191(7) 0.47773(13) 0.0165(2) Uani d 1
C C9 0.70562(16) 0.76014(7) 0.43953(13) 0.0170(2) Uani d 1
C C10 0.82350(18) 0.72550(8) 0.40745(15) 0.0225(3) Uani d 1
H H10 0.828901 0.678281 0.414448 0.027 Uiso calc 1
C C11 0.93294(19) 0.75959(9) 0.36537(16) 0.0289(3) Uani d 1
H H11 1.012829 0.735524 0.343917 0.035 Uiso calc 1
C C12 0.92662(19) 0.82828(9) 0.35443(16) 0.0294(3) Uani d 1
H H12 1.001008 0.851359 0.324678 0.035 Uiso calc 1
C C13 0.8109(2) 0.86321(9) 0.38721(17) 0.0299(3) Uani d 1
H H13 0.806516 0.910437 0.380223 0.036 Uiso calc 1
C C14 0.70118(18) 0.82959(8) 0.43030(15) 0.0235(3) Uani d 1
H H14 0.623057 0.853966 0.453485 0.028 Uiso calc 1
C C15 0.44235(18) 0.54575(7) 0.12345(14) 0.0197(3) Uani d 1
C C16 0.2830(2) 0.55892(8) 0.02103(15) 0.0274(3) Uani d 1
H H16A 0.245772 0.518532 -0.030777 0.041 Uiso calc 1
H H16B 0.294126 0.595176 -0.034930 0.041 Uiso calc 1
H H16C 0.204476 0.571687 0.061592 0.041 Uiso calc 1
C C17 0.5379(2) 0.75217(8) 0.58752(14) 0.0236(3) Uani d 1
H H17A 0.456948 0.724354 0.605601 0.035 Uiso calc 1
H H17B 0.494300 0.797093 0.563247 0.035 Uiso calc 1
H H17C 0.634896 0.754692 0.664922 0.035 Uiso calc 1
C C18 0.31788(16) 0.74827(7) 0.29343(13) 0.0176(3) Uani d 1
C C19 0.18862(18) 0.71930(8) 0.17778(15) 0.0227(3) Uani d 1
H H19A 0.101667 0.751907 0.143604 0.034 Uiso calc 1
H H19B 0.145536 0.678758 0.203469 0.034 Uiso calc 1
H H19C 0.234431 0.708341 0.110914 0.034 Uiso calc 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'
I I -0.4742 1.8119 '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
C15 O1 C4 117.34(11)
C7 N1 N2 104.29(11)
C2 C1 I1 118.81(10)
C2 C1 C6 120.65(13)
C6 C1 I1 120.47(11)
N1 N2 C8 110.97(11)
C18 N2 N1 121.85(12)
C18 N2 C8 127.06(12)
C1 C2 H2 119.9
C1 C2 C3 120.26(13)
C3 C2 H2 119.9
C7 O3 C8 107.38(10)
C2 C3 C7 117.97(12)
C4 C3 C2 118.53(13)
C4 C3 C7 123.48(13)
O1 C4 C3 120.69(12)
C5 C4 O1 118.05(12)
C5 C4 C3 121.16(13)
C4 C5 H5 120.0
C4 C5 C6 119.91(14)
C6 C5 H5 120.0
C1 C6 H6 120.3
C5 C6 C1 119.49(14)
C5 C6 H6 120.3
N1 C7 O3 116.29(12)
N1 C7 C3 128.01(13)
O3 C7 C3 115.68(12)
N2 C8 C9 111.22(11)
N2 C8 C17 113.42(12)
O3 C8 N2 99.15(10)
O3 C8 C9 108.96(11)
O3 C8 C17 107.66(11)
C17 C8 C9 115.08(12)
C10 C9 C8 119.86(13)
C10 C9 C14 118.89(14)
C14 C9 C8 121.19(13)
C9 C10 H10 119.8
C11 C10 C9 120.41(15)
C11 C10 H10 119.8
C10 C11 H11 119.7
C12 C11 C10 120.55(15)
C12 C11 H11 119.7
C11 C12 H12 120.3
C11 C12 C13 119.49(15)
C13 C12 H12 120.3
C12 C13 H13 119.8
C12 C13 C14 120.47(16)
C14 C13 H13 119.8
C9 C14 H14 119.9
C13 C14 C9 120.17(15)
C13 C14 H14 119.9
O1 C15 C16 110.24(13)
O2 C15 O1 122.81(13)
O2 C15 C16 126.93(14)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 C17 H17A 109.5
C8 C17 H17B 109.5
C8 C17 H17C 109.5
H17A C17 H17B 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N2 C18 C19 116.25(13)
O4 C18 N2 120.54(13)
O4 C18 C19 123.21(13)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.0951(14)
O1 C4 1.3948(17)
O1 C15 1.3727(17)
N1 N2 1.4017(16)
N1 C7 1.2851(18)
C1 C2 1.386(2)
C1 C6 1.392(2)
O2 C15 1.1966(19)
N2 C8 1.4917(18)
N2 C18 1.3614(18)
C2 H2 0.9500
C2 C3 1.4004(19)
O3 C7 1.3631(16)
O3 C8 1.4493(16)
C3 C4 1.3986(19)
C3 C7 1.4610(19)
O4 C18 1.2270(18)
C4 C5 1.383(2)
C5 H5 0.9500
C5 C6 1.392(2)
C6 H6 0.9500
C8 C9 1.522(2)
C8 C17 1.5107(19)
C9 C10 1.395(2)
C9 C14 1.396(2)
C10 H10 0.9500
C10 C11 1.388(2)
C11 H11 0.9500
C11 C12 1.382(3)
C12 H12 0.9500
C12 C13 1.386(2)
C13 H13 0.9500
C13 C14 1.392(2)
C14 H14 0.9500
C15 C16 1.493(2)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.504(2)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
C5 H5 O4 2_645 0.95 2.51 3.2828(19) 139 yes
C16 H16B O4 4_575 0.98 2.55 3.529(2) 177 yes
C17 H17C <i>Cg</i>3 4_576 0.98 2.70 3.5766(17) 150 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
I1 C1 C2 C3 176.86(10)
I1 C1 C6 C5 -177.27(11)
O1 C4 C5 C6 -176.23(13)
N1 N2 C8 O3 -13.43(13)
N1 N2 C8 C9 101.12(13)
N1 N2 C8 C17 -127.29(12)
N1 N2 C18 O4 -177.27(12)
N1 N2 C18 C19 2.50(19)
C1 C2 C3 C4 0.6(2)
C1 C2 C3 C7 -177.68(13)
N2 N1 C7 O3 -0.09(16)
N2 N1 C7 C3 -178.50(13)
N2 C8 C9 C10 -88.99(15)
N2 C8 C9 C14 88.16(15)
C2 C1 C6 C5 -0.4(2)
C2 C3 C4 O1 175.70(12)
C2 C3 C4 C5 -0.8(2)
C2 C3 C7 N1 179.85(14)
C2 C3 C7 O3 1.42(18)
O3 C8 C9 C10 19.29(17)
O3 C8 C9 C14 -163.56(12)
C3 C4 C5 C6 0.3(2)
C4 O1 C15 O2 5.2(2)
C4 O1 C15 C16 -176.26(12)
C4 C3 C7 N1 1.6(2)
C4 C3 C7 O3 -176.80(12)
C4 C5 C6 C1 0.3(2)
C6 C1 C2 C3 0.0(2)
C7 N1 N2 C8 9.02(14)
C7 N1 N2 C18 -174.80(12)
C7 O3 C8 N2 12.66(13)
C7 O3 C8 C9 -103.64(12)
C7 O3 C8 C17 130.93(12)
C7 C3 C4 O1 -6.1(2)
C7 C3 C4 C5 177.43(13)
C8 N2 C18 O4 -1.7(2)
C8 N2 C18 C19 178.03(12)
C8 O3 C7 N1 -8.94(16)
C8 O3 C7 C3 169.68(11)
C8 C9 C10 C11 176.32(14)
C8 C9 C14 C13 -175.89(14)
C9 C10 C11 C12 -0.1(2)
C10 C9 C14 C13 1.3(2)
C10 C11 C12 C13 0.7(3)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C9 -0.7(3)
C14 C9 C10 C11 -0.9(2)
C15 O1 C4 C3 81.18(16)
C15 O1 C4 C5 -102.23(15)
C17 C8 C9 C10 140.28(14)
C17 C8 C9 C14 -42.57(18)
C18 N2 C8 O3 170.64(12)
C18 N2 C8 C9 -74.81(16)
C18 N2 C8 C17 56.77(18)

_cod_database_fobs_code 2021167
