#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/74/1517408.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_1517408
loop_
_publ_author_name
'Lu, Aidang'
'Wang, Jinjin'
'Liu, Tengjiao'
'Han, Jian'
'Li, Yinhui'
'Su, Min'
'Chen, Jianxin'
'Zhang, Hui'
'Wang, Lizhong'
'Wang, Qingmin'
_publ_section_title
;
 Small Changes Result in Large Differences: Discovery of (-)-Incrustoporin
 Derivatives as Novel Antiviral and Antifungal Agents.
;
_journal_issue                   35
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              8799
_journal_page_last               8807
_journal_paper_doi               10.1021/jf503060k
_journal_volume                  62
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H11 Cl O2'
_chemical_formula_weight         210.65
_chemical_melting_point          312.0(10)
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1375(12)
_cell_length_b                   7.7099(15)
_cell_length_c                   20.954(4)
_cell_measurement_reflns_used    3323
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9103
_cell_measurement_theta_min      1.9438
_cell_volume                     991.5(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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      113(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10233
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.9327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0373
_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)+(0.0390P)²+0.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2137
_reflns_number_total             2346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jf503060k_si_002.cif
_cod_data_source_block           r140419a1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '311-313' was changed to '312.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517408.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1517408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
Cl1 Cl 0.43530(8) 0.80019(7) 0.17371(2) 0.02730(15) Uani 1 1 d .
O1 O 1.1816(2) 0.69453(17) 0.48422(6) 0.0215(3) Uani 1 1 d .
O2 O 1.2031(2) 0.90842(18) 0.41284(6) 0.0256(3) Uani 1 1 d .
C1 C 1.3178(3) 0.3988(3) 0.49042(9) 0.0288(5) Uani 1 1 d .
H1A H 1.4083 0.4176 0.4525 0.043 Uiso 1 1 calc R
H1B H 1.2750 0.2765 0.4927 0.043 Uiso 1 1 calc R
H1C H 1.4008 0.4297 0.5287 0.043 Uiso 1 1 calc R
C2 C 1.1169(3) 0.5104(2) 0.48634(8) 0.0212(4) Uani 1 1 d .
H2 H 1.0221 0.4893 0.5244 0.025 Uiso 1 1 calc R
C3 C 0.9845(3) 0.4852(2) 0.42525(8) 0.0211(4) Uani 1 1 d .
H3A H 1.0023 0.3662 0.4083 0.025 Uiso 1 1 calc R
H3B H 0.8278 0.5075 0.4329 0.025 Uiso 1 1 calc R
C4 C 1.0804(3) 0.6190(2) 0.37957(8) 0.0188(4) Uani 1 1 d .
H4 H 1.2112 0.5661 0.3588 0.023 Uiso 1 1 calc R
C5 C 1.1594(3) 0.7596(2) 0.42479(8) 0.0183(4) Uani 1 1 d .
C6 C 0.9281(3) 0.6781(2) 0.32740(8) 0.0172(4) Uani 1 1 d .
C7 C 0.7372(3) 0.7675(3) 0.34191(8) 0.0201(4) Uani 1 1 d .
H7 H 0.7104 0.8018 0.3847 0.024 Uiso 1 1 calc R
C8 C 0.5856(3) 0.8073(2) 0.29515(8) 0.0200(4) Uani 1 1 d .
H8 H 0.4559 0.8685 0.3055 0.024 Uiso 1 1 calc R
C9 C 0.6277(3) 0.7555(2) 0.23258(8) 0.0185(4) Uani 1 1 d .
C10 C 0.8162(3) 0.6682(2) 0.21682(8) 0.0198(4) Uani 1 1 d .
H10 H 0.8432 0.6346 0.1739 0.024 Uiso 1 1 calc R
C11 C 0.9661(3) 0.6300(2) 0.26433(8) 0.0192(4) Uani 1 1 d .
H11 H 1.0964 0.5702 0.2537 0.023 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0238(3) 0.0341(3) 0.0240(2) 0.0078(2) -0.0063(2) 0.0003(2)
O1 0.0250(7) 0.0213(7) 0.0180(6) 0.0006(5) -0.0024(5) -0.0021(7)
O2 0.0274(8) 0.0227(7) 0.0267(7) 0.0017(6) -0.0039(6) -0.0053(7)
C1 0.0284(12) 0.0298(10) 0.0281(10) 0.0038(9) -0.0066(9) 0.0037(10)
C2 0.0232(11) 0.0202(9) 0.0201(8) 0.0023(8) 0.0021(7) -0.0020(8)
C3 0.0213(10) 0.0217(9) 0.0203(8) 0.0018(7) -0.0021(8) -0.0015(8)
C4 0.0186(10) 0.0192(9) 0.0186(8) 0.0003(7) -0.0002(8) -0.0006(8)
C5 0.0135(9) 0.0244(10) 0.0170(8) 0.0001(7) -0.0007(7) -0.0002(8)
C6 0.0184(9) 0.0170(9) 0.0161(7) 0.0015(7) -0.0017(8) -0.0013(8)
C7 0.0209(10) 0.0232(10) 0.0161(8) -0.0011(7) 0.0012(7) 0.0000(8)
C8 0.0183(10) 0.0188(9) 0.0228(8) 0.0005(7) 0.0026(7) 0.0025(9)
C9 0.0191(10) 0.0160(9) 0.0203(8) 0.0050(7) -0.0043(7) -0.0020(7)
C10 0.0226(10) 0.0218(9) 0.0151(7) 0.0012(7) 0.0015(7) -0.0007(9)
C11 0.0192(10) 0.0174(9) 0.0210(9) 0.0004(7) 0.0033(8) -0.0001(8)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C5 O1 C2 111.01(13)
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
O1 C2 C1 109.33(16)
O1 C2 C3 103.91(14)
C1 C2 C3 114.23(16)
O1 C2 H2 109.7
C1 C2 H2 109.7
C3 C2 H2 109.7
C4 C3 C2 103.56(15)
C4 C3 H3A 111.0
C2 C3 H3A 111.0
C4 C3 H3B 111.0
C2 C3 H3B 111.0
H3A C3 H3B 109.0
C6 C4 C5 115.75(15)
C6 C4 C3 114.80(16)
C5 C4 C3 102.37(13)
C6 C4 H4 107.8
C5 C4 H4 107.8
C3 C4 H4 107.8
O2 C5 O1 121.57(17)
O2 C5 C4 128.39(17)
O1 C5 C4 110.02(15)
C11 C6 C7 118.67(17)
C11 C6 C4 120.25(16)
C7 C6 C4 120.83(15)
C8 C7 C6 121.35(16)
C8 C7 H7 119.3
C6 C7 H7 119.3
C7 C8 C9 118.47(17)
C7 C8 H8 120.8
C9 C8 H8 120.8
C10 C9 C8 121.36(16)
C10 C9 Cl1 119.73(14)
C8 C9 Cl1 118.91(15)
C9 C10 C11 119.22(16)
C9 C10 H10 120.4
C11 C10 H10 120.4
C10 C11 C6 120.92(18)
C10 C11 H11 119.5
C6 C11 H11 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.7419(17)
O1 C5 1.350(2)
O1 C2 1.475(2)
O2 C5 1.204(2)
C1 C2 1.506(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.528(2)
C2 H2 1.0000
C3 C4 1.525(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C6 1.509(2)
C4 C5 1.519(2)
C4 H4 1.0000
C6 C11 1.392(2)
C6 C7 1.393(3)
C7 C8 1.386(2)
C7 H7 0.9500
C8 C9 1.395(2)
C8 H8 0.9500
C9 C10 1.379(3)
C10 C11 1.387(3)
C10 H10 0.9500
C11 H11 0.9500
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
C5 O1 C2 C1 105.08(17)
C5 O1 C2 C3 -17.26(19)
O1 C2 C3 C4 28.40(18)
C1 C2 C3 C4 -90.64(19)
C2 C3 C4 C6 -154.97(15)
C2 C3 C4 C5 -28.72(19)
C2 O1 C5 O2 179.79(18)
C2 O1 C5 C4 -1.5(2)
C6 C4 C5 O2 -36.2(3)
C3 C4 C5 O2 -161.9(2)
C6 C4 C5 O1 145.18(15)
C3 C4 C5 O1 19.5(2)
C5 C4 C6 C11 130.91(18)
C3 C4 C6 C11 -110.08(19)
C5 C4 C6 C7 -55.0(2)
C3 C4 C6 C7 64.0(2)
C11 C6 C7 C8 0.6(3)
C4 C6 C7 C8 -173.55(18)
C6 C7 C8 C9 0.1(3)
C7 C8 C9 C10 -0.7(3)
C7 C8 C9 Cl1 178.46(15)
C8 C9 C10 C11 0.5(3)
Cl1 C9 C10 C11 -178.60(14)
C9 C10 C11 C6 0.2(3)
C7 C6 C11 C10 -0.8(3)
C4 C6 C11 C10 173.43(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044055
