#------------------------------------------------------------------------------
#$Date: 2016-02-04 22:32:03 +0100 (jue 04 de feb de 2016) $
#$Revision: 175888 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/83/7118362.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_7118362
loop_
_publ_author_name
'Ghosh, Monisankar'
'Saha, Suchandrima'
'Dutta, Samir Kumar'
_publ_section_title
;
 'Dual hit' metabolic modulator LDCA selectively kills cancer cells by
 efficient competitive inhibition of LDH-A.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2401
_journal_page_last               2404
_journal_paper_doi               10.1039/c5cc09903j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C8 H5 Cl3 F N O'
_chemical_formula_sum            'C8 H5 Cl3 F N O'
_chemical_formula_weight         256.48
_chemical_melting_point          370.15
_chemical_name_common            acetamide
_chemical_name_systematic
2,2-dichloro-N-(3-chloro-4-fluorophenyl)acetamide
_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
_audit_creation_date             2015-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-30 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.134(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1964(10)
_cell_length_b                   11.7747(12)
_cell_length_c                   9.7412(10)
_cell_measurement_reflns_used    4486
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.157
_cell_measurement_theta_min      2.24
_cell_volume                     1044.21(19)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.309
_diffrn_reflns_theta_min         2.730
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_min  0.630528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0908 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.6305.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   1.0
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0453
_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/[σ²(Fo²)+(0.0599P)²+0.6427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1787
_reflns_number_total             2321
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc09903j2.cif
_cod_data_source_block           LDCA
_cod_depositor_comments          'Adding full bibliography for 7118362.cif.'
_cod_database_code               7118362
_shelxl_version_number           2014/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C6(H6)
;
_shelx_res_file
;
TITL mg_ld_ca_0m_a.res in P2(1)/c
REM Old TITL MG_LD_CA_0m in P21/c #14
REM SHELXT solution in P2(1)/c
REM R1 0.189, Rweak 0.007, Alpha 0.017, Orientation as input
REM Formula found by SHELXT: C8 Cl3 N2 O
CELL 0.71073 9.1964 11.7747 9.7412 90 98.134 90
ZERR 4 0.001 0.0012 0.001 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl F N O
UNIT 32 20 12 4 4 4

L.S. 20
PLAN  5
TEMP 20
BOND $H
LIST 6
fmap 2
MORE -1
ACTA 52
CONF
REM <olex2.extras>
REM <HklSrc "%.\\MG_LD_CA_0m.hkl">
REM </olex2.extras>

WGHT    0.059900    0.642700
FVAR       0.59917
CL1   3    0.702949    0.266900    0.581345    11.00000    0.10541    0.07206 =
         0.10852    0.03174    0.02047   -0.00549
F1    4    0.920290    0.249228    0.387309    11.00000    0.10249    0.06721 =
         0.10697   -0.00558    0.01177    0.02452
O1    6    0.701552    0.761226    0.233290    11.00000    0.13341    0.07729 =
         0.02774    0.00498    0.02231    0.02042
N1    5    0.719391    0.687322    0.450282    11.00000    0.06436    0.05609 =
         0.02554   -0.00042    0.01137    0.00246
AFIX  43
H1    2    0.706451    0.703068    0.533910    11.00000   -1.20000
AFIX   0
C1    1    0.867457    0.355743    0.397555    11.00000    0.05962    0.06110 =
         0.06249   -0.00635   -0.00193    0.00712
CL2   3    0.505363    0.949867    0.311936    11.00000    0.06489    0.08600 =
         0.05974    0.01493    0.00886    0.01572
C2    1    0.767405    0.377217    0.487774    11.00000    0.05607    0.05992 =
         0.05383    0.00771   -0.00032   -0.00415
CL3   3    0.809521    0.972288    0.440332    11.00000    0.07232    0.08148 =
         0.08581   -0.02071    0.01229   -0.01220
C3    1    0.718439    0.487083    0.502508    11.00000    0.04991    0.06336 =
         0.03892    0.00337    0.00729   -0.00181
AFIX  43
H3    2    0.652486    0.502161    0.564292    11.00000   -1.20000
AFIX   0
C4    1    0.767333    0.575146    0.425390    11.00000    0.04749    0.05637 =
         0.03030   -0.00304    0.00231   -0.00225
C5    1    0.866724    0.551987    0.332691    11.00000    0.05538    0.06642 =
         0.04218   -0.00172    0.01409   -0.00220
AFIX  43
H5    2    0.899791    0.609999    0.280165    11.00000   -1.20000
AFIX   0
C6    1    0.915362    0.441327    0.320102    11.00000    0.05914    0.07829 =
         0.05550   -0.01201    0.01577    0.00701
AFIX  43
H6    2    0.981110    0.425225    0.258456    11.00000   -1.20000
AFIX   0
C7    1    0.692456    0.770621    0.356971    11.00000    0.06130    0.06017 =
         0.02917    0.00046    0.00925    0.00162
C8    1    0.652023    0.883849    0.419713    11.00000    0.05801    0.05952 =
         0.03498    0.00282    0.01200    0.00428
AFIX  13
H8    2    0.622296    0.869574    0.510881    11.00000   -1.20000
AFIX   0
HKLF 4

REM  mg_ld_ca_0m_a.res in P2(1)/c
REM R1 =  0.0453 for    1787 Fo > 4sig(Fo)  and  0.0596 for all    2321 data
REM    127 parameters refined using      0 restraints

END

WGHT      0.0599      0.6427

REM Highest difference peak  0.418,  deepest hole -0.473,  1-sigma level  0.070
Q1    1   0.7978  0.2765  0.6019  11.00000  0.05    0.42
Q2    1   0.5072  0.9011  0.2547  11.00000  0.05    0.37
Q3    1   0.7660  0.9955  0.3650  11.00000  0.05    0.29
Q4    1   0.5819  0.9210  0.3724  11.00000  0.05    0.28
Q5    1   0.5776  1.0044  0.3317  11.00000  0.05    0.27
;
_shelx_res_checksum              92236
_olex2_date_sample_data_collection 2015-06-18
_olex2_date_sample_submission    2015-06-18
_olex2_submission_original_sample_id MG_LD_CA
_olex2_submission_special_instructions 'No special instructions were received'
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl 0.70295(12) 0.26690(8) 0.58134(12) 0.0948(3) Uani 1 1 d .
F1 F 0.9203(3) 0.24923(16) 0.3873(2) 0.0925(6) Uani 1 1 d .
O1 O 0.7016(3) 0.76123(18) 0.23329(17) 0.0784(7) Uani 1 1 d .
N1 N 0.7194(2) 0.68732(17) 0.45028(17) 0.0482(5) Uani 1 1 d .
H1 H 0.7065 0.7031 0.5339 0.058 Uiso 1 1 calc R
C1 C 0.8675(3) 0.3557(2) 0.3976(3) 0.0621(7) Uani 1 1 d .
Cl2 Cl 0.50536(8) 0.94987(7) 0.31194(7) 0.0702(3) Uani 1 1 d .
C2 C 0.7674(3) 0.3772(2) 0.4878(3) 0.0574(6) Uani 1 1 d .
Cl3 Cl 0.80952(9) 0.97229(8) 0.44033(9) 0.0798(3) Uani 1 1 d .
C3 C 0.7184(3) 0.4871(2) 0.5025(2) 0.0506(6) Uani 1 1 d .
H3 H 0.6525 0.5022 0.5643 0.061 Uiso 1 1 calc R
C4 C 0.7673(3) 0.5751(2) 0.4254(2) 0.0450(5) Uani 1 1 d .
C5 C 0.8667(3) 0.5520(2) 0.3327(2) 0.0540(6) Uani 1 1 d .
H5 H 0.8998 0.6100 0.2802 0.065 Uiso 1 1 calc R
C6 C 0.9154(3) 0.4413(3) 0.3201(3) 0.0636(7) Uani 1 1 d .
H6 H 0.9811 0.4252 0.2585 0.076 Uiso 1 1 calc R
C7 C 0.6925(3) 0.7706(2) 0.3570(2) 0.0499(6) Uani 1 1 d .
C8 C 0.6520(3) 0.8838(2) 0.4197(2) 0.0503(6) Uani 1 1 d .
H8 H 0.6223 0.8696 0.5109 0.060 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 0.1054(7) 0.0721(5) 0.1085(7) 0.0317(5) 0.0205(6) -0.0055(5)
F1 0.1025(15) 0.0672(11) 0.1070(15) -0.0056(10) 0.0118(12) 0.0245(10)
O1 0.133(2) 0.0773(14) 0.0277(8) 0.0050(8) 0.0223(10) 0.0204(13)
N1 0.0644(12) 0.0561(11) 0.0255(8) -0.0004(7) 0.0114(8) 0.0025(9)
C1 0.0596(16) 0.0611(16) 0.0625(15) -0.0064(12) -0.0019(13) 0.0071(13)
Cl2 0.0649(5) 0.0860(5) 0.0597(4) 0.0149(3) 0.0089(3) 0.0157(4)
C2 0.0561(15) 0.0599(15) 0.0538(13) 0.0077(12) -0.0003(12) -0.0041(12)
Cl3 0.0723(5) 0.0815(6) 0.0858(5) -0.0207(4) 0.0123(4) -0.0122(4)
C3 0.0499(13) 0.0634(15) 0.0389(11) 0.0034(10) 0.0073(10) -0.0018(11)
C4 0.0475(12) 0.0564(13) 0.0303(9) -0.0030(9) 0.0023(8) -0.0022(10)
C5 0.0554(14) 0.0664(16) 0.0422(11) -0.0017(10) 0.0141(11) -0.0022(12)
C6 0.0591(16) 0.0783(19) 0.0555(14) -0.0120(13) 0.0158(12) 0.0070(14)
C7 0.0613(14) 0.0602(14) 0.0292(9) 0.0005(9) 0.0093(9) 0.0016(11)
C8 0.0580(14) 0.0595(14) 0.0350(10) 0.0028(10) 0.0120(10) 0.0043(11)
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'
F F 0.0171 0.0103 '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
C4 N1 H1 116.7
C7 N1 H1 116.7
C7 N1 C4 126.65(18)
F1 C1 C2 119.6(3)
F1 C1 C6 119.6(3)
C6 C1 C2 120.7(3)
C1 C2 Cl1 120.2(2)
C1 C2 C3 119.5(2)
C3 C2 Cl1 120.3(2)
C2 C3 H3 119.8
C2 C3 C4 120.4(2)
C4 C3 H3 119.8
C3 C4 N1 117.9(2)
C3 C4 C5 119.6(2)
C5 C4 N1 122.5(2)
C4 C5 H5 120.4
C6 C5 C4 119.2(2)
C6 C5 H5 120.4
C1 C6 C5 120.6(2)
C1 C6 H6 119.7
C5 C6 H6 119.7
O1 C7 N1 124.8(2)
O1 C7 C8 121.6(2)
N1 C7 C8 113.51(18)
Cl2 C8 Cl3 110.59(14)
Cl2 C8 H8 109.1
Cl3 C8 H8 109.1
C7 C8 Cl2 110.68(16)
C7 C8 Cl3 108.39(17)
C7 C8 H8 109.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.738(3)
F1 C1 1.354(3)
O1 C7 1.224(3)
N1 H1 0.8600
N1 C4 1.424(3)
N1 C7 1.336(3)
C1 C2 1.383(4)
C1 C6 1.369(4)
Cl2 C8 1.768(3)
C2 C3 1.384(4)
Cl3 C8 1.772(3)
C3 H3 0.9300
C3 C4 1.392(3)
C4 C5 1.400(3)
C5 H5 0.9300
C5 C6 1.389(4)
C6 H6 0.9300
C7 C8 1.534(3)
C8 H8 0.9800
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
Cl1 C2 C3 C4 -178.54(19)
F1 C1 C2 Cl1 -3.1(4)
F1 C1 C2 C3 177.2(2)
F1 C1 C6 C5 -177.6(3)
O1 C7 C8 Cl2 43.5(3)
O1 C7 C8 Cl3 -77.9(3)
N1 C4 C5 C6 176.1(2)
N1 C7 C8 Cl2 -138.1(2)
N1 C7 C8 Cl3 100.5(2)
C1 C2 C3 C4 1.1(4)
C2 C1 C6 C5 1.3(4)
C2 C3 C4 N1 -176.7(2)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 -0.4(4)
C4 N1 C7 O1 2.1(4)
C4 N1 C7 C8 -176.2(2)
C4 C5 C6 C1 -0.3(4)
C6 C1 C2 Cl1 177.9(2)
C6 C1 C2 C3 -1.8(4)
C7 N1 C4 C3 -146.6(2)
C7 N1 C4 C5 36.9(4)
