#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238887.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_2238887
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Hernandez, Geraldine'
'Ellena, Javier'
'De Simone, Carlos A.'
'Tenorio, Juan C.'
_publ_section_title
;
4-Formyl-2-nitrophenyl 2-chlorobenzoate
;
_journal_coeditor_code LH5661
_journal_issue 12
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o1806
_journal_paper_doi 10.1107/S1600536813031346
_journal_volume 69
_journal_year 2013
_chemical_formula_iupac 'C14 H8 Cl N O5'
_chemical_formula_moiety 'C14 H8 Cl N O5'
_chemical_formula_sum 'C14 H8 Cl N O5'
_chemical_formula_weight 305.66
_chemical_name_systematic
;
4-Formyl-2-nitrophenyl 2-chlorobenzoate
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 33
_space_group_name_Hall 'P 2c -2n'
_space_group_name_H-M_alt 'P n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_atom_sites_solution_hydrogens mixed
_audit_creation_method SHELXL-2013
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 16.2367(7)
_cell_length_b 7.1047(2)
_cell_length_c 11.4018(3)
_cell_measurement_reflns_used 4580
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 25.98
_cell_measurement_theta_min 3.08
_cell_volume 1315.28(8)
_computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection 'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material 'WinGX (Farrugia, 2012)'
_computing_structure_refinement 'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method 'CCD rotation images, thick slices'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0295
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 4581
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.980
_diffrn_reflns_theta_min 3.080
_exptl_absorpt_coefficient_mu 0.312
_exptl_absorpt_correction_type none
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.544
_exptl_crystal_description prism
_exptl_crystal_F_000 624
_exptl_crystal_size_max 0.220
_exptl_crystal_size_mid 0.190
_exptl_crystal_size_min 0.030
_refine_diff_density_max 0.198
_refine_diff_density_min -0.187
_refine_ls_abs_structure_details
;
Flack parameter determined using 664 quotients
[(I^+^)-(I^-^)]/[(I^+^)+(I^-^)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack -0.05(5)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 194
_refine_ls_number_reflns 2449
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.031
_refine_ls_R_factor_all 0.0722
_refine_ls_R_factor_gt 0.0439
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1043
_refine_ls_wR_factor_ref 0.1197
_reflns_number_gt 1762
_reflns_number_total 2449
_reflns_threshold_expression I>2\s(I)
_cod_data_source_file lh5661.cif
_cod_data_source_block I
_cod_database_code 2238887
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min 0.935
_shelx_estimated_absorpt_t_max 0.991
_shelx_hkl_checksum 92787
_shelx_hkl_file
;
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-5 7 -5 6.80 14.80 1
5 -7 5 29.90 12.20 1
-6 7 -5 3.90 16.40 1
6 -7 5 35.80 12.10 1
-7 7 -5 11.50 20.30 1
7 -7 5 45.30 14.70 1
-8 7 -5 25.20 11.90 1
8 -7 5 47.50 15.30 1
-9 7 -5 53.00 18.70 1
9 -7 5 41.10 13.90 1
8 7 -6 12.00 19.80 1
-8 -7 6 10.60 22.30 1
7 7 -6 5.10 23.30 1
-7 -7 6 38.50 11.70 1
6 7 -6 -17.00 17.00 1
-6 -7 6 -4.20 10.30 1
5 7 -6 11.70 20.60 1
-5 -7 6 10.50 11.80 1
4 7 -6 1.30 19.40 1
-4 -7 6 11.00 11.30 1
3 7 -6 52.30 19.00 1
-3 -7 6 46.00 12.40 1
2 7 -6 51.10 17.60 1
-2 -7 6 19.30 10.90 1
1 7 -6 16.90 16.10 1
-1 -7 6 22.10 9.80 1
0 7 -6 -1.80 14.90 1
0 -7 6 -3.50 10.10 1
-1 7 -6 -7.60 18.00 1
1 -7 6 23.50 8.90 1
-2 7 -6 42.40 16.00 1
2 -7 6 24.00 10.80 1
-3 7 -6 42.70 20.70 1
3 -7 6 49.10 10.80 1
-4 7 -6 9.40 17.20 1
4 -7 6 -1.50 13.70 1
-5 7 -6 23.10 17.10 1
5 -7 6 15.70 12.60 1
-6 7 -6 0.10 17.60 1
6 -7 6 10.50 14.00 1
-7 7 -6 15.80 12.00 1
7 -7 6 29.00 16.40 1
-8 7 -6 10.80 12.20 1
8 -7 6 40.10 21.90 1
6 7 -7 75.60 22.60 1
-6 -7 7 104.50 23.90 1
5 7 -7 2.70 16.10 1
-5 -7 7 -22.40 10.00 1
4 7 -7 65.70 19.40 1
-4 -7 7 87.50 12.50 1
3 7 -7 19.30 21.30 1
-3 -7 7 9.60 12.80 1
2 7 -7 38.50 19.30 1
-2 -7 7 35.70 11.90 1
1 7 -7 -14.70 18.50 1
-1 -7 7 -4.40 11.30 1
0 7 -7 28.30 17.00 1
0 -7 7 17.60 10.10 1
-1 7 -7 -2.90 16.90 1
1 -7 7 11.70 11.20 1
-2 7 -7 47.70 18.90 1
2 -7 7 41.30 11.60 1
-3 7 -7 1.90 20.20 1
3 -7 7 -8.70 11.70 1
-4 7 -7 62.30 23.00 1
4 -7 7 76.60 14.40 1
-5 7 -7 1.30 14.60 1
5 -7 7 23.10 17.10 1
-6 7 -7 65.30 16.20 1
6 -7 7 25.80 20.20 1
3 7 -8 17.40 17.50 1
2 7 -8 3.10 18.00 1
-2 -7 8 23.00 10.90 1
1 7 -8 -3.30 14.90 1
-1 -7 8 -2.70 9.30 1
0 7 -8 -6.30 17.10 1
0 -7 8 -10.80 13.50 1
-1 7 -8 15.90 20.20 1
1 -7 8 45.10 15.30 1
-2 7 -8 2.20 18.80 1
2 -7 8 60.30 21.30 1
-3 7 -8 17.60 17.60 1
3 -7 8 -7.10 17.50 1
8 8 0 23.60 19.10 1
7 8 0 -1.50 17.70 1
6 8 0 21.20 16.00 1
5 8 0 -20.40 17.40 1
4 8 0 -3.00 15.70 1
3 8 0 4.10 13.80 1
2 8 0 149.20 22.60 1
1 8 0 47.20 18.20 1
0 8 0 0.10 16.40 1
-1 8 0 17.80 14.90 1
-2 8 0 134.50 21.70 1
-3 8 0 14.50 13.70 1
-4 8 0 -18.00 15.80 1
-5 8 0 11.40 16.70 1
-6 8 0 19.00 15.60 1
-7 8 0 16.80 20.70 1
-8 8 0 2.40 17.10 1
8 8 -1 0.50 17.40 1
-8 -8 1 1.20 12.40 1
7 8 -1 -21.00 18.40 1
-7 -8 1 6.40 12.70 1
6 8 -1 8.20 18.70 1
-6 -8 1 9.70 13.10 1
5 8 -1 1.90 18.70 1
-5 -8 1 8.70 12.50 1
4 8 -1 43.00 17.10 1
-4 -8 1 54.60 16.60 1
3 8 -1 78.20 16.80 1
-3 -8 1 59.30 17.20 1
2 8 -1 12.20 16.50 1
-2 -8 1 -1.70 16.50 1
1 8 -1 9.90 14.60 1
-1 -8 1 25.90 14.50 1
0 8 -1 -2.50 14.70 1
0 -8 1 6.10 13.70 1
-1 8 -1 16.70 14.60 1
1 -8 1 -4.40 13.30 1
-2 8 -1 5.60 19.70 1
2 -8 1 31.00 17.10 1
-3 8 -1 22.30 14.60 1
3 -8 1 38.60 15.00 1
-4 8 -1 24.20 19.90 1
4 -8 1 49.00 19.50 1
-5 8 -1 5.00 21.00 1
5 -8 1 9.90 14.40 1
-6 8 -1 37.70 16.80 1
6 -8 1 45.10 20.10 1
-7 8 -1 -1.10 13.90 1
7 -8 1 -36.10 15.60 1
7 8 -2 20.20 16.50 1
-7 -8 2 8.10 12.80 1
6 8 -2 2.10 20.40 1
-6 -8 2 29.20 15.40 1
5 8 -2 45.10 19.20 1
-5 -8 2 7.40 13.30 1
4 8 -2 43.50 15.20 1
-4 -8 2 28.40 18.20 1
3 8 -2 178.90 26.30 1
-3 -8 2 225.80 23.40 1
2 8 -2 60.10 19.80 1
-2 -8 2 109.30 19.60 1
1 8 -2 18.30 17.20 1
-1 -8 2 35.00 12.50 1
0 8 -2 18.20 19.80 1
0 -8 2 19.10 15.50 1
-1 8 -2 17.00 17.40 1
1 -8 2 75.30 19.30 1
-2 8 -2 69.90 16.50 1
2 -8 2 64.10 20.30 1
-3 8 -2 195.90 26.70 1
3 -8 2 173.90 25.00 1
-4 8 -2 -7.90 20.10 1
4 -8 2 39.70 15.50 1
-5 8 -2 21.90 17.70 1
5 -8 2 36.80 19.90 1
-6 8 -2 -4.10 18.10 1
6 -8 2 0.30 13.50 1
-7 8 -2 -18.70 20.70 1
7 -8 2 6.00 18.30 1
6 8 -3 27.50 14.90 1
-6 -8 3 -1.90 13.10 1
5 8 -3 0.90 16.80 1
-5 -8 3 14.60 18.80 1
4 8 -3 70.80 18.00 1
-4 -8 3 107.60 27.20 1
3 8 -3 15.80 18.50 1
-3 -8 3 35.70 12.20 1
2 8 -3 29.50 21.50 1
-2 -8 3 17.60 25.40 1
1 8 -3 -9.60 16.10 1
-1 -8 3 17.00 17.00 1
0 8 -3 -8.20 17.60 1
0 -8 3 -10.80 15.20 1
-1 8 -3 13.20 17.50 1
1 -8 3 8.10 13.60 1
-2 8 -3 20.70 17.20 1
2 -8 3 37.30 17.50 1
-3 8 -3 2.30 16.80 1
3 -8 3 20.00 15.10 1
-4 8 -3 64.00 20.20 1
4 -8 3 64.60 18.60 1
-5 8 -3 17.40 18.60 1
5 -8 3 -7.30 11.80 1
-6 8 -3 26.60 22.20 1
6 -8 3 28.90 18.10 1
5 8 -4 19.00 18.20 1
-5 -8 4 12.40 15.50 1
4 8 -4 3.20 20.20 1
-4 -8 4 18.00 12.30 1
3 8 -4 -0.40 21.70 1
-3 -8 4 -9.90 11.90 1
2 8 -4 17.30 15.20 1
-2 -8 4 11.60 15.20 1
1 8 -4 -11.10 19.00 1
-1 -8 4 -6.20 14.20 1
0 8 -4 31.50 20.00 1
0 -8 4 19.10 15.30 1
-1 8 -4 19.30 19.20 1
1 -8 4 -11.20 14.80 1
-2 8 -4 48.70 17.70 1
2 -8 4 16.20 14.60 1
-3 8 -4 6.90 19.00 1
3 -8 4 2.90 14.70 1
-4 8 -4 -8.20 21.80 1
4 -8 4 32.90 13.00 1
-5 8 -4 -9.20 18.30 1
5 -8 4 30.70 13.80 1
3 8 -5 2.50 17.70 1
-3 -8 5 3.30 21.40 1
2 8 -5 7.80 23.00 1
-2 -8 5 -4.40 15.90 1
1 8 -5 16.00 18.40 1
-1 -8 5 -7.20 11.90 1
0 8 -5 -23.30 21.10 1
0 -8 5 -8.70 14.40 1
-1 8 -5 20.60 17.90 1
1 -8 5 -10.00 15.40 1
-2 8 -5 -14.50 21.00 1
2 -8 5 -10.70 12.50 1
-3 8 -5 -33.90 18.50 1
3 -8 5 -5.30 15.50 1
0 0 0 0.00 0.00
;
_shelx_res_checksum 21844
_shelx_res_file
;
TITL import in P c 21 n
REM transformed to space group : Pna21
CELL 0.71073 16.2367 7.1047 11.4018 90.000 90.000 90.000
ZERR 4 0.0007 0.0002 0.0003 0.000 0.000 0.000
LATT -1
SYMM -X,-Y,1/2+Z
SYMM 1/2-X,1/2+Y,1/2+Z
SYMM 1/2+X,1/2-Y,+Z
SFAC C H CL N O
UNIT 56 32 4 4 20
OMIT 0 0 2
FMAP 2
PLAN 20
SIZE 0.03 0.19 0.22
MPLA C8 C9 C10 C11 C12 C13
MPLA C1 C2 C3 C4 C5 C6
MPLA C1 C7 O1 O2 C8
MPLA C8 C9 C10 C11 C12 C13
MPLA C13 N1 O3 O4
EQIV $1 x-1/2, -y+1/2, z
HTAB C14 O4_$1
ACTA
BOND $H
HTAB
CONF
L.S. 10
TEMP 20.00
WGHT 0.071900
FVAR 1.43405
CL1 3 0.225101 0.328424 0.138417 11.00000 0.09676 0.08379 =
0.05282 -0.00487 -0.00949 0.00636
N1 4 0.317303 0.273843 0.745269 11.00000 0.05110 0.07578 =
0.04844 -0.00128 -0.00267 0.00305
O1 5 0.202775 0.176537 0.385410 11.00000 0.07922 0.08029 =
0.06177 -0.01721 0.01415 -0.01770
O2 5 0.270334 0.369204 0.510273 11.00000 0.05438 0.07515 =
0.03630 -0.00262 0.00540 -0.00505
O3 5 0.373450 0.313072 0.681339 11.00000 0.04739 0.15582 =
0.07367 0.02713 0.00051 -0.00578
O4 5 0.326799 0.192504 0.838583 11.00000 0.07567 0.14171 =
0.05841 0.02825 -0.00461 0.02362
O5 5 0.048274 0.355290 0.971976 11.00000 0.09261 0.12810 =
0.05616 0.00300 0.02699 0.00227
C1 1 0.329810 0.325000 0.325902 11.00000 0.06203 0.04962 =
0.04132 -0.00244 0.00687 0.00388
C2 1 0.409027 0.345732 0.374440 11.00000 0.06488 0.06218 =
0.05676 -0.00058 0.00723 0.00004
AFIX 43
H2 2 0.416337 0.337024 0.455157 11.00000 -1.20000
AFIX 0
C3 1 0.475687 0.378855 0.302755 11.00000 0.06708 0.07132 =
0.08108 -0.00770 0.01345 -0.00491
AFIX 43
H3 2 0.527983 0.390757 0.335188 11.00000 -1.20000
AFIX 0
C4 1 0.465403 0.394377 0.183903 11.00000 0.08707 0.07239 =
0.07662 -0.01469 0.03406 -0.02209
AFIX 43
H4 2 0.510885 0.416285 0.136241 11.00000 -1.20000
AFIX 0
C5 1 0.389126 0.378034 0.134706 11.00000 0.10470 0.06447 =
0.05085 -0.00721 0.02831 -0.00822
AFIX 43
H5 2 0.382719 0.390728 0.054038 11.00000 -1.20000
AFIX 0
C6 1 0.320509 0.342164 0.205626 11.00000 0.07268 0.05355 =
0.04991 -0.00652 0.00350 0.00409
C7 1 0.259755 0.278783 0.403755 11.00000 0.06075 0.05771 =
0.04185 -0.00112 0.00376 0.00230
C8 1 0.210066 0.358058 0.595346 11.00000 0.04873 0.05054 =
0.04304 -0.00213 0.00483 -0.00215
C9 1 0.129094 0.400272 0.570434 11.00000 0.05351 0.06657 =
0.04678 0.00462 -0.00503 0.00599
AFIX 43
H9 2 0.113469 0.427641 0.493837 11.00000 -1.20000
AFIX 0
C10 1 0.071312 0.401984 0.658763 11.00000 0.04766 0.06159 =
0.05997 -0.00353 -0.00381 0.00188
AFIX 43
H10 2 0.016610 0.428470 0.641085 11.00000 -1.20000
AFIX 0
C11 1 0.093735 0.364638 0.773924 11.00000 0.04841 0.05322 =
0.05146 -0.00630 0.01010 -0.00340
C12 1 0.174404 0.320874 0.799837 11.00000 0.05418 0.05142 =
0.04084 0.00092 0.00466 -0.00492
AFIX 43
H12 2 0.189735 0.293693 0.876581 11.00000 -1.20000
AFIX 0
C13 1 0.232571 0.317604 0.710823 11.00000 0.04418 0.05048 =
0.04081 -0.00043 -0.00136 -0.00127
C14 1 0.031853 0.374766 0.868899 11.00000 0.06103 0.08240 =
0.07573 -0.01130 0.02198 -0.01143
H14 2 -0.029180 0.423442 0.839628 11.00000 0.09791
HKLF 4
REM import in P c 21 n
REM R1 = 0.0439 for 1762 Fo > 4sig(Fo) and 0.0722 for all 2449 data
REM 194 parameters refined using 1 restraints
END
WGHT 0.0714 0.0000
REM Instructions for potential hydrogen bonds
HTAB C14 O4_$1
REM Highest difference peak 0.198, deepest hole -0.187, 1-sigma level 0.041
Q1 1 0.3596 0.1678 0.6470 11.00000 0.05 0.19
Q2 1 -0.0448 0.5623 0.8041 11.00000 0.05 0.17
Q3 1 0.2230 0.3449 0.6634 11.00000 0.05 0.15
Q4 1 0.2276 0.3791 0.6996 11.00000 0.05 0.14
Q5 1 0.3581 0.3478 0.8413 11.00000 0.05 0.13
Q6 1 0.1853 0.3768 0.9391 11.00000 0.05 0.13
Q7 1 0.2777 0.5140 0.6366 11.00000 0.05 0.13
Q8 1 0.3570 0.3592 0.5549 11.00000 0.05 0.13
Q9 1 0.2001 0.4730 0.4149 11.00000 0.05 0.13
Q10 1 0.0857 0.3879 1.0845 11.00000 0.05 0.13
Q11 1 0.2197 0.1443 0.8915 11.00000 0.05 0.12
Q12 1 0.4015 0.3464 0.8695 11.00000 0.05 0.12
Q13 1 -0.0034 0.1259 0.9738 11.00000 0.05 0.12
Q14 1 0.5957 0.2212 0.2158 11.00000 0.05 0.12
Q15 1 0.1196 0.2946 0.7638 11.00000 0.05 0.11
Q16 1 0.4595 0.3436 0.7546 11.00000 0.05 0.11
Q17 1 0.4200 0.3561 -0.0568 11.00000 0.05 0.11
Q18 1 0.1436 0.3356 0.9415 11.00000 0.05 0.11
Q19 1 0.1820 -0.0107 0.3527 11.00000 0.05 0.11
Q20 1 0.2023 0.0846 0.7202 11.00000 0.05 0.11
;
_shelxl_version_number 2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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_occupancy
Cl Cl1 0.22510(10) 0.32842(19) 0.13842(11) 0.0778(5) Uani d 1
N N1 0.3173(2) 0.2738(6) 0.7453(3) 0.0584(9) Uani d 1
O O1 0.2028(2) 0.1765(5) 0.3854(3) 0.0738(10) Uani d 1
O O2 0.27033(18) 0.3692(4) 0.5103(3) 0.0553(8) Uani d 1
O O3 0.3734(2) 0.3131(6) 0.6813(4) 0.0923(13) Uani d 1
O O4 0.3268(3) 0.1925(6) 0.8386(3) 0.0919(13) Uani d 1
O O5 0.0483(3) 0.3553(6) 0.9720(4) 0.0923(13) Uani d 1
C C1 0.3298(3) 0.3250(5) 0.3259(4) 0.0510(11) Uani d 1
C C2 0.4090(3) 0.3457(6) 0.3744(5) 0.0613(12) Uani d 1
H H2 0.4163 0.3370 0.4552 0.074 Uiso calc 1
C C3 0.4757(3) 0.3789(7) 0.3028(6) 0.0732(14) Uani d 1
H H3 0.5280 0.3908 0.3352 0.088 Uiso calc 1
C C4 0.4654(4) 0.3944(7) 0.1839(5) 0.0787(17) Uani d 1
H H4 0.5109 0.4163 0.1362 0.094 Uiso calc 1
C C5 0.3891(4) 0.3780(7) 0.1347(5) 0.0733(15) Uani d 1
H H5 0.3827 0.3907 0.0540 0.088 Uiso calc 1
C C6 0.3205(3) 0.3422(6) 0.2056(4) 0.0587(12) Uani d 1
C C7 0.2598(3) 0.2788(7) 0.4038(4) 0.0534(11) Uani d 1
C C8 0.2101(3) 0.3581(6) 0.5953(4) 0.0474(10) Uani d 1
C C9 0.1291(3) 0.4003(7) 0.5704(4) 0.0556(11) Uani d 1
H H9 0.1135 0.4276 0.4938 0.067 Uiso calc 1
C C10 0.0713(3) 0.4020(6) 0.6588(4) 0.0564(11) Uani d 1
H H10 0.0166 0.4285 0.6411 0.068 Uiso calc 1
C C11 0.0937(3) 0.3646(5) 0.7739(4) 0.0510(10) Uani d 1
C C12 0.1744(3) 0.3209(5) 0.7998(4) 0.0488(10) Uani d 1
H H12 0.1897 0.2937 0.8766 0.059 Uiso calc 1
C C13 0.2326(3) 0.3176(5) 0.7108(4) 0.0452(10) Uani d 1
C C14 0.0319(4) 0.3748(8) 0.8689(6) 0.0731(14) Uani d 1
H H14 -0.029(4) 0.423(8) 0.840(5) 0.098(18) Uiso d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0968(11) 0.0838(8) 0.0528(7) 0.0064(7) -0.0095(8) -0.0049(6)
N1 0.051(2) 0.076(2) 0.048(2) 0.003(2) -0.0027(18) -0.0013(19)
O1 0.079(2) 0.080(2) 0.062(2) -0.018(2) 0.0142(18) -0.0172(16)
O2 0.0544(18) 0.075(2) 0.0363(16) -0.0051(15) 0.0054(13) -0.0026(14)
O3 0.047(2) 0.156(4) 0.074(3) -0.006(2) 0.0005(18) 0.027(2)
O4 0.076(3) 0.142(4) 0.058(2) 0.024(2) -0.0046(18) 0.028(2)
O5 0.093(3) 0.128(3) 0.056(3) 0.002(2) 0.027(2) 0.0030(19)
C1 0.062(3) 0.050(2) 0.041(2) 0.004(2) 0.007(2) -0.0024(17)
C2 0.065(3) 0.062(3) 0.057(3) 0.000(2) 0.007(2) -0.001(2)
C3 0.067(4) 0.071(3) 0.081(4) -0.005(3) 0.013(3) -0.008(2)
C4 0.087(4) 0.072(3) 0.077(4) -0.022(3) 0.034(3) -0.015(3)
C5 0.105(5) 0.064(3) 0.051(3) -0.008(3) 0.028(3) -0.007(2)
C6 0.073(3) 0.054(3) 0.050(3) 0.004(2) 0.003(2) -0.0065(18)
C7 0.061(3) 0.058(3) 0.042(3) 0.002(2) 0.004(2) -0.0011(19)
C8 0.049(3) 0.051(2) 0.043(2) -0.0021(18) 0.0048(18) -0.0021(16)
C9 0.054(3) 0.067(3) 0.047(2) 0.006(2) -0.005(2) 0.0046(19)
C10 0.048(2) 0.062(2) 0.060(3) 0.002(2) -0.004(2) -0.004(2)
C11 0.048(3) 0.053(2) 0.051(3) -0.003(2) 0.0101(19) -0.0063(19)
C12 0.054(3) 0.051(2) 0.041(2) -0.0049(19) 0.005(2) 0.0009(16)
C13 0.044(2) 0.050(2) 0.041(2) -0.0013(18) -0.0014(19) -0.0004(16)
C14 0.061(3) 0.082(3) 0.076(4) -0.011(3) 0.022(3) -0.011(3)
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'
Cl Cl 0.1484 0.1585 '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
O3 N1 O4 122.9(4)
O3 N1 C13 120.1(4)
O4 N1 C13 116.9(4)
C8 O2 C7 120.1(3)
C6 C1 C2 118.7(5)
C6 C1 C7 122.0(4)
C2 C1 C7 119.3(4)
C3 C2 C1 120.2(5)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.4(6)
C4 C3 H3 119.8
C2 C3 H3 119.8
C5 C4 C3 120.7(5)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.0(5)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 120.1(5)
C1 C6 Cl1 122.1(4)
C5 C6 Cl1 117.8(4)
O1 C7 O2 122.1(4)
O1 C7 C1 128.7(4)
O2 C7 C1 109.1(4)
C9 C8 O2 121.3(4)
C9 C8 C13 119.3(4)
O2 C8 C13 119.3(4)
C10 C9 C8 120.1(4)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 120.8(4)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 119.7(4)
C12 C11 C14 120.0(5)
C10 C11 C14 120.3(5)
C11 C12 C13 119.6(4)
C11 C12 H12 120.2
C13 C12 H12 120.2
C12 C13 C8 120.6(4)
C12 C13 N1 116.6(4)
C8 C13 N1 122.9(4)
O5 C14 C11 123.7(6)
O5 C14 H14 122(3)
C11 C14 H14 114(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.731(5)
N1 O3 1.200(5)
N1 O4 1.221(5)
N1 C13 1.464(6)
O1 C7 1.195(6)
O2 C8 1.380(5)
O2 C7 1.385(6)
O5 C14 1.213(7)
C1 C6 1.385(7)
C1 C2 1.408(7)
C1 C7 1.480(6)
C2 C3 1.377(7)
C2 H2 0.9300
C3 C4 1.370(9)
C3 H3 0.9300
C4 C5 1.365(8)
C4 H4 0.9300
C5 C6 1.400(7)
C5 H5 0.9300
C8 C9 1.378(6)
C8 C13 1.396(6)
C9 C10 1.376(6)
C9 H9 0.9300
C10 C11 1.388(6)
C10 H10 0.9300
C11 C12 1.378(6)
C11 C14 1.479(7)
C12 C13 1.387(6)
C12 H12 0.9300
C14 H14 1.10(6)
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
C14 H14 O4 4_455 1.10(6) 2.48(6) 3.381(7) 138(4)
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
C6 C1 C2 C3 -1.2(6)
C7 C1 C2 C3 176.6(4)
C1 C2 C3 C4 0.9(7)
C2 C3 C4 C5 0.2(8)
C3 C4 C5 C6 -1.0(8)
C2 C1 C6 C5 0.5(6)
C7 C1 C6 C5 -177.2(4)
C2 C1 C6 Cl1 -177.3(3)
C7 C1 C6 Cl1 5.0(6)
C4 C5 C6 C1 0.6(7)
C4 C5 C6 Cl1 178.5(4)
C8 O2 C7 O1 -6.5(7)
C8 O2 C7 C1 175.7(4)
C6 C1 C7 O1 36.0(7)
C2 C1 C7 O1 -141.7(5)
C6 C1 C7 O2 -146.4(4)
C2 C1 C7 O2 35.9(5)
C7 O2 C8 C9 -51.7(6)
C7 O2 C8 C13 133.4(4)
O2 C8 C9 C10 -175.0(4)
C13 C8 C9 C10 -0.1(6)
C8 C9 C10 C11 1.1(6)
C9 C10 C11 C12 -1.6(6)
C9 C10 C11 C14 177.4(4)
C10 C11 C12 C13 1.0(6)
C14 C11 C12 C13 -177.9(4)
C11 C12 C13 C8 -0.1(6)
C11 C12 C13 N1 178.8(3)
C9 C8 C13 C12 -0.4(6)
O2 C8 C13 C12 174.6(4)
C9 C8 C13 N1 -179.2(4)
O2 C8 C13 N1 -4.1(6)
O3 N1 C13 C12 -161.5(4)
O4 N1 C13 C12 20.5(6)
O3 N1 C13 C8 17.3(6)
O4 N1 C13 C8 -160.7(4)
C12 C11 C14 O5 3.7(7)
C10 C11 C14 O5 -175.3(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086228