#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/08/2100803.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_2100803
loop_
_publ_author_name
'Venugopalan, P.'
'Venkatesan, K.'
_publ_section_title
;
 Solid-state photobehaviour and crystal packing of
 <i>o</i>-chlorobenzylidene-<small>DL</small>-piperitone: influence of
 molecular topology on photobehaviour
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              532
_journal_page_last               537
_journal_paper_doi               10.1107/S0108768192002167
_journal_volume                  48
_journal_year                    1992
_chemical_formula_sum            'C17 H19 Cl O'
_chemical_formula_weight         274.7
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                100.680(10)
_cell_angle_beta                 113.580(10)
_cell_angle_gamma                104.50(2)
_cell_formula_units_Z            4
_cell_length_a                   11.154(3)
_cell_length_b                   12.685(2)
_cell_length_c                   12.713(2)
_cell_volume                     1511.2(6)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    2.16
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      1.22
_exptl_crystal_F_000             584
_cod_data_source_file            li0118.cif
_cod_data_source_block           li0118a
_cod_original_cell_volume        1511.1(6)
_cod_original_formula_sum        'C17 H19 Cl1 O1'
_cod_database_code               2100803
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Cl(1) .11920(10) .72070(10) .55600(10) .0930(5)
O(1) -.1268(3) 1.1578(3) .1159(3) .125(2)
C(1) -.1392(3) .7236(2) .4156(3) .0643(14)
C(2) -.0625(3) .6705(3) .4901(3) .0696(15)
C(3) -.1270(5) .5768(3) .5139(4) .088(2)
C(4) -.2704(5) .5346(3) .4645(4) .096(2)
C(5) -.3498(5) .5851(3) .3917(4) .091(2)
C(6) -.2840(4) .6782(3) .3686(3) .0778(17)
C(7) -.0696(4) .8205(3) .3881(3) .0669(15)
C(8) -.1289(3) .8751(3) .3155(3) .0683(15)
C(9) -.0539(3) .9690(3) .2884(2) .0619(14)
C(10) .1024(3) 1.0085(3) .3428(3) .0680(16)
C(11) .1588(4) 1.0732(3) .2735(4) .0761(17)
C(12) .1021(4) 1.1674(3) .2489(3) .0752(18)
C(13) -.0565(4) 1.1172(3) .1853(3) .084(2)
C(14) -.1234(4) 1.0209(3) .2159(3) .0818(19)
C(15) .1607(4) 1.2385(3) .1838(3) .0776(18)
C(16) .1350(5) 1.1672(4) .0629(3) .090(2)
C(17) .3165(6) 1.3121(5) .2639(4) .116(3)
H(3) -.081(4) .544(4) .568(4) ?
H(4) -.313(3) .473(3) .481(3) ?
H(5) -.453(4) .557(3) .353(3) ?
H(6) -.335(3) .714(3) .320(3) ?
H(7) .022(4) .838(3) .419(3) ?
H(8) -.228(3) .855(2) .275(3) ?
H(101) .148(4) 1.055(3) .429(3) ?
H(102) .131(3) .948(3) .343(3) ?
H(111) .118(4) 1.016(3) .187(3) ?
H(112) .268(4) 1.112(2) .326(3) ?
H(12) .131(4) 1.222(3) .337(3) ?
H(14) -.228(3) .989(2) .177(3) ?
H(15) .117(4) 1.300(3) .189(3) ?
H(161) .201(4) 1.117(3) .075(3) ?
H(162) .163(4) 1.223(3) .022(3) ?
H(163) .019(5) 1.117(4) .008(4) ?
H(171) .353(4) 1.361(3) .218(3) ?
H(172) .332(5) 1.361(4) .352(5) ?
H(173) .374(6) 1.261(5) .264(5) ?
Cl(1') .43020(10) .76000(10) .46910(10) .1275(8)
O(1') -.3992(2) .3886(2) -.1559(2) .0822(11)
C(1') .2951(3) .8046(3) .2597(3) .0887(17)
C(2') .4204(4) .8347(3) .3664(3) .116(3)
C(3') .5400(5) .9202(4) .3916(5) .118(3)
C(4') .5379(5) .9801(4) .3135(6) .102(3)
C(5') .4182(5) .9543(3) .2078(5) .0800(18)
C(6') .2980(4) .8680(3) .1828(4) .0684(15)
C(7') .1692(3) .7105(3) .2332(3) .0714(16)
C(8') .0512(3) .6637(3) .1289(3) .0680(15)
C(9') -.0711(3) .5678(2) .1008(2) .0599(13)
C(10') -.0753(4) .5132(3) .1946(3) .0788(17)
C(11') -.2254(4) .4444(4) .1652(3) .086(2)
C(12') -.3064(3) .3593(3) .0368(3) .0694(15)
C(13') -.3045(3) .4224(3) -.0521(3) .0648(14)
C(14') -.1805(3) .5243(3) -.0117(3) .0653(14)
C(15') -.4535(3) .2784(3) .0019(4) .0777(18)
C(16') -.5522(5) .3415(5) .0032(6) .099(3)
C(17') -.4475(6) .1993(5) .0794(6) .118(3)
H(3') .627(6) .937(4) .469(5) ?
H(4') .619(5) 1.028(4) .318(4) ?
H(5') .415(4) .985(3) .148(3) ?
H(6') .219(4) .850(2) .110(3) ?
H(7') .176(3) .681(3) .293(3) ?
H(8') .050(3) .688(2) .061(3) ?
H(101') -.035(4) .567(3) .273(3) ?
H(102') -.0091(4) .456(3) .198(3) ?
H(111') -.279(4) .499(4) .164(4) ?
H(112') -.222(4) .402(3) .223(3) ?
H(12') -.245(3) .314(3) .033(3) ?
H(14') -.177(3) .554(2) -.074(2) ?
H(15') -.492(4) .230(3) -.087(3) ?
H(161') -.521(5) .385(4) .086(4) ?
H(162') -.559(4) .391(4) -.054(4) ?
H(163') -.630(5) .293(4) -.013(4) .116(15)
H(171') -.538(4) .148(3) .049(3) ?
H(172') -.424(5) .253(4) .166(4) ?
H(173') -.381(6) .154(4) .071(5) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) C(1) C(6) 116.4(3)
C(2) C(1) C(7) 121.3(3)
C(6) C(1) C(7) 122.3(3)
Cl(1) C(2) C(1) 120.7(3)
Cl(1) C(2) C(3) 117.4(3)
C(1) C(2) C(3) 121.9(4)
C(2) C(3) C(4) 119.5(4)
C(3) C(4) C(5) 120.5(5)
C(4) C(5) C(6) 119.4(4)
C(1) C(6) C(5) 122.3(4)
C(1) C(7) C(8) 127.7(4)
C(7) C(8) C(9) 125.2(3)
C(8) C(9) C(10) 119.7(3)
C(8) C(9) C(14) 120.6(3)
C(10) C(9) C(14) 119.7(3)
C(9) C(10) C(11) 112.8(3)
C(10) C(11) C(12) 113.1(4)
C(11) C(12) C(13) 109.3(3)
C(11) C(12) C(15) 115.0(3)
C(13) C(12) C(15) 112.7(3)
O(1) C(13) C(12) 121.9(4)
O(1) C(13) C(14) 120.7(4)
C(12) C(13) C(14) 117.4(3)
C(9) C(14) C(13) 124.4(4)
C(12) C(15) C(16) 113.2(3)
C(12) C(15) C(17) 111.8(4)
C16) C(15) C(17) 111.0(4)
C(2') C(1') C(6') 116.4(4)
C(2') C(1') C(7') 120.8(3)
C(6') C(1') C(7') 122.8(3)
Cl(1') C(2') C(1') 120.6(3)
Cl(1') C(2') C(3') 117.5(4)
C(1') C(2') C(3') 121.8(4)
C(2') C(3') C(4') 119.7(5)
C(3') C(4') C(5') 120.9(6)
C(4') C(5') C(6') 119.2(5)
C(1') C(6') C(5') 122.0(4)
C(1') C(7') C(8') 126.2(3)
C(7') C(8') C(9') 126.4(3)
C(8') C(9') C(10') 120.5(3)
C(8') C(9') C(14') 120.0(3)
C(10') C(9') C(14') 119.4(3)
C(9') C(10') C(11') 112.4(3)
C(10') C(11') C(12') 111.3(3)
C(11') C(12') C(13') 109.6(3)
C(11') C(12') C(15') 115.6(3)
C(13') C(12') C(15') 113.2(3)
O(1') C(13') C(12') 122.2(3)
O(1') C(13') C(14') 120.2(3)
C(12') C(13') C(14') 117.5(3)
C(9') C(14') C(13') 124.4(3)
C(12') C(15') C(16') 113.0(4)
C(12') C(15') C(17') 111.4(4)
C(16') C(15') C(17') 111.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl(1) C(2) 1.736(4)
O(1) C(13) 1.214(5)
C(1) C(2) 1.400(5)
C(1) C(6) 1.390(6)
C(1) C(7) 1.461(5)
C(2) C(3) 1.379(6)
C(3) C(4) 1.371(8)
C(4) C(5) 1.378(7)
C(5) C(6) 1.373(6)
C(7) C(8) 1.321(5)
C(8) C(9) 1.457(5)
C(9) C(10) 1.496(5)
C(9) C(14) 1.339(5)
C(10) C(11) 1.516(6)
C(11) C(12) 1.511(6)
C(12) C(13) 1.513(6)
C(12) C(15) 1.529(6)
C(13) C(14) 1.467(6)
C(15) C(16) 1.505(5)
C(15) C(17) 1.532(8)
Cl(1') C(2') 1.735(4)
O(1') C(13') 1.221(4)
C(1') C(2') 1.401(5)
C(1') C(6') 1.381(6)
C(1') C(7') 1.464(5)
C(2') C(3') 1.365(7)
C(3') C(4') 1.354(8)
C(4') C(5') 1.370(9)
C(5') C(6') 1.375(7)
C(7') C(8') 1.328(5)
C(8') C(9') 1.445(5)
C(9') C(10') 1.496(4)
C(9') C(14') 1.346(4)
C(10') C(11') 1.533(7)
C(11') C(12') 1.525(5)
C(12') C(13') 1.505(5)
C(12') C(15') 1.532(6)
C(13') C(14') 1.462(5)
C(15') C(16') 1.517(8)
C(15') C(17') 1.526(8)
C(3) H(3) 0.92(4)
C(4) H(4) 0.91(4)
C(5) H(5) 0.98(4)
C(6) H(6) 0.93(4)
C(7) H(7) 0.89(4)
C(8) H(8) 0.96(4)
C(10) H(101) 0.99(4)
C(10) H(102) 0.91(4)
C(11) H(111) 1.04(4)
C(11) H(112) 1.04(4)
C(12) H(12) 1.07(4)
C(14) H(14) 1.00(4)
C(15) H(15) 1.03(5)
C(16) H(161) 1.07(5)
C(16) H(162) 1.01(4)
C(16) H(163) 1.12(5)
C(17) H(171) 1.04(4)
C(17) H(172) 1.10(6)
C(17) H(173) 1.02(7)
C(3') H(3') 1.01(6)
C(4') H(4') 0.92(6)
C(5') H(5') 0.91(4)
C(6') H(6') 0.92(3)
C(7') H(7') 0.89(3)
C(8') H(8') 0.96(3)
C(10') H(101') 0.95(3)
C(10') H(102') 1.15(5)
C(11') H(111') 1.03(5)
C(11') H(112') 0.98(4)
C(12') H(12') 1.01(4)
C(14') H(14') 0.94(3)
C(15') H(15') 1.03(4)
C(16') H(161') 0.96(5)
C(16') H(162') 1.04(4)
C(16') H(163') 0.85(5)
C(17') H(171') 0.93(5)
C(17') H(172') 1.08(5)
C(17') H(173') 1.08(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139063122