#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/01/1520143.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_1520143
loop_
_publ_author_name
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Davies, David B.'
'Kilic, A.'
'Uslu, A.'
_publ_section_title
;
 C7H14Cl4N3O2P3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              481
_journal_year                    2008
_chemical_formula_sum            'C7 H14 Cl4 N3 O2 P3'
_chemical_formula_weight         406.92
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.189(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.9483(5)
_cell_length_b                   12.1905(3)
_cell_length_c                   16.5233(4)
_cell_measurement_reflns_used    7399
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.0
_cell_volume                     3171.20(15)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41102
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  0.8177
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         7260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0399P)²+1.7946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                5579
_reflns_number_total             7260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-481.cif
_cod_data_source_block           2006src0702
_cod_depositor_comments
;
Citation :
Coles, Simon J. and Hursthouse, Michael B. and Davies, David B. and 
Kilic, A. and Uslu, A. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/481)

More at:
http://ecrystals.chem.soton.ac.uk/481/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1520143
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11462(15) 0.00981(19) 0.33034(14) 0.0213(5) Uani 1 1 d . . .
H1A H 0.1552 -0.0075 0.2926 0.026 Uiso 1 1 calc R . .
H1B H 0.0696 -0.0469 0.3228 0.026 Uiso 1 1 calc R . .
C2 C 0.16151(14) 0.00489(18) 0.41924(14) 0.0193(5) Uani 1 1 d . . .
C3 C 0.25039(14) 0.05656(18) 0.42982(14) 0.0200(5) Uani 1 1 d . . .
H3A H 0.2843 0.0285 0.4811 0.024 Uiso 1 1 calc R . .
H3B H 0.2789 0.0332 0.3837 0.024 Uiso 1 1 calc R . .
C4 C 0.18000(16) -0.11900(19) 0.43749(15) 0.0248(5) Uani 1 1 d . . .
H4A H 0.2105 -0.1484 0.3945 0.030 Uiso 1 1 calc R . .
H4B H 0.2188 -0.1248 0.4904 0.030 Uiso 1 1 calc R . .
C5 C 0.10330(18) -0.1920(2) 0.44171(18) 0.0358(6) Uani 1 1 d . . .
H5A H 0.0753 -0.1685 0.4874 0.054 Uiso 1 1 calc R . .
H5B H 0.1219 -0.2683 0.4502 0.054 Uiso 1 1 calc R . .
H5C H 0.0633 -0.1861 0.3903 0.054 Uiso 1 1 calc R . .
C6 C 0.10631(15) 0.05742(19) 0.47665(13) 0.0220(5) Uani 1 1 d . . .
H6A H 0.0989 0.1361 0.4623 0.026 Uiso 1 1 calc R . .
H6B H 0.0494 0.0229 0.4662 0.026 Uiso 1 1 calc R . .
C7 C 0.14051(17) 0.0486(2) 0.56813(14) 0.0286(6) Uani 1 1 d . . .
H7A H 0.1488 -0.0289 0.5833 0.043 Uiso 1 1 calc R . .
H7B H 0.0998 0.0815 0.5995 0.043 Uiso 1 1 calc R . .
H7C H 0.1949 0.0873 0.5803 0.043 Uiso 1 1 calc R . .
C8 C 0.27183(15) 0.50824(18) 0.59614(14) 0.0207(5) Uani 1 1 d . . .
H8A H 0.2416 0.4702 0.5470 0.025 Uiso 1 1 calc R . .
H8B H 0.2529 0.4751 0.6449 0.025 Uiso 1 1 calc R . .
C9 C 0.36787(14) 0.48899(18) 0.60124(13) 0.0181(5) Uani 1 1 d . . .
C10 C 0.41725(15) 0.48880(18) 0.68926(14) 0.0207(5) Uani 1 1 d . . .
H10A H 0.3808 0.4567 0.7263 0.025 Uiso 1 1 calc R . .
H10B H 0.4678 0.4411 0.6912 0.025 Uiso 1 1 calc R . .
C11 C 0.40754(16) 0.5720(2) 0.54872(14) 0.0235(5) Uani 1 1 d . . .
H11A H 0.4686 0.5542 0.5520 0.028 Uiso 1 1 calc R . .
H11B H 0.4038 0.6459 0.5728 0.028 Uiso 1 1 calc R . .
C12 C 0.36732(18) 0.5769(2) 0.45787(15) 0.0312(6) Uani 1 1 d . . .
H12A H 0.3708 0.5045 0.4329 0.047 Uiso 1 1 calc R . .
H12B H 0.3979 0.6306 0.4294 0.047 Uiso 1 1 calc R . .
H12C H 0.3076 0.5988 0.4534 0.047 Uiso 1 1 calc R . .
C13 C 0.37831(16) 0.37127(18) 0.56820(14) 0.0215(5) Uani 1 1 d . . .
H13A H 0.3460 0.3670 0.5119 0.026 Uiso 1 1 calc R . .
H13B H 0.4390 0.3602 0.5641 0.026 Uiso 1 1 calc R . .
C14 C 0.35005(17) 0.27675(19) 0.61765(15) 0.0277(6) Uani 1 1 d . . .
H14A H 0.3838 0.2766 0.6727 0.042 Uiso 1 1 calc R . .
H14B H 0.3583 0.2072 0.5902 0.042 Uiso 1 1 calc R . .
H14C H 0.2898 0.2856 0.6219 0.042 Uiso 1 1 calc R . .
N1 N 0.21997(12) 0.18819(15) 0.27326(11) 0.0185(4) Uani 1 1 d . . .
N2 N 0.22832(12) 0.36754(15) 0.37119(12) 0.0209(4) Uani 1 1 d . . .
N3 N 0.08095(12) 0.31883(16) 0.26915(11) 0.0208(4) Uani 1 1 d . . .
N4 N 0.29278(12) 0.64099(15) 0.74987(11) 0.0180(4) Uani 1 1 d . . .
N5 N 0.41638(12) 0.79581(15) 0.75581(11) 0.0199(4) Uani 1 1 d . . .
N6 N 0.26830(12) 0.81838(16) 0.64966(12) 0.0222(4) Uani 1 1 d . . .
O1 O 0.07603(10) 0.11754(13) 0.30844(9) 0.0215(4) Uani 1 1 d . . .
O2 O 0.24925(10) 0.17646(13) 0.43282(9) 0.0194(3) Uani 1 1 d . . .
O3 O 0.24776(10) 0.62498(13) 0.59175(9) 0.0229(4) Uani 1 1 d . . .
O4 O 0.44515(10) 0.59840(13) 0.71979(9) 0.0214(4) Uani 1 1 d . . .
P1 P 0.11939(4) 0.20062(5) 0.25582(3) 0.01760(13) Uani 1 1 d . . .
P2 P 0.26093(4) 0.24698(5) 0.35596(3) 0.01692(13) Uani 1 1 d . . .
P3 P 0.13384(4) 0.39811(5) 0.33400(4) 0.01879(13) Uani 1 1 d . . .
P4 P 0.24254(4) 0.69672(5) 0.66917(4) 0.01749(13) Uani 1 1 d . . .
P5 P 0.39059(4) 0.67184(5) 0.76906(3) 0.01662(13) Uani 1 1 d . . .
P6 P 0.35735(4) 0.86573(5) 0.68910(4) 0.01780(13) Uani 1 1 d . . .
Cl1 Cl 0.08242(4) 0.15630(5) 0.13951(3) 0.02565(14) Uani 1 1 d . . .
Cl2 Cl 0.38589(4) 0.25312(5) 0.35665(4) 0.02348(13) Uani 1 1 d . . .
Cl3 Cl 0.06916(4) 0.42147(5) 0.42797(4) 0.02872(14) Uani 1 1 d . . .
Cl4 Cl 0.13100(4) 0.54835(5) 0.28688(4) 0.02863(14) Uani 1 1 d . . .
Cl5 Cl 0.11970(4) 0.69925(5) 0.67876(4) 0.02652(14) Uani 1 1 d . . .
Cl6 Cl 0.43053(4) 0.63521(5) 0.88660(3) 0.02536(14) Uani 1 1 d . . .
Cl7 Cl 0.34327(4) 1.01429(5) 0.73445(4) 0.02678(14) Uani 1 1 d . . .
Cl8 Cl 0.42252(4) 0.90266(5) 0.59769(4) 0.02766(14) Uani 1 1 d . . .
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'
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'
P P 0.1023 0.0942 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C2 112.96(18) . .
C6 C2 C3 111.66(19) . .
C6 C2 C1 109.55(19) . .
C3 C2 C1 113.05(19) . .
C6 C2 C4 113.23(19) . .
C3 C2 C4 103.46(18) . .
C1 C2 C4 105.69(19) . .
O2 C3 C2 113.43(18) . .
C5 C4 C2 116.5(2) . .
C7 C6 C2 115.7(2) . .
O3 C8 C9 113.55(18) . .
C11 C9 C8 111.42(19) . .
C11 C9 C10 109.91(19) . .
C8 C9 C10 113.99(18) . .
C11 C9 C13 109.49(18) . .
C8 C9 C13 106.45(18) . .
C10 C9 C13 105.27(18) . .
O4 C10 C9 113.80(18) . .
C9 C11 C12 115.7(2) . .
C14 C13 C9 116.94(19) . .
P2 N1 P1 112.16(11) . .
P3 N2 P2 118.16(12) . .
P3 N3 P1 118.04(12) . .
P5 N4 P4 114.39(11) . .
P6 N5 P5 118.05(12) . .
P6 N6 P4 120.30(12) . .
C1 O1 P1 120.64(14) . .
C3 O2 P2 121.09(14) . .
C8 O3 P4 123.23(14) . .
C10 O4 P5 122.34(14) . .
O1 P1 N1 111.08(9) . .
O1 P1 N3 107.10(10) . .
N1 P1 N3 117.37(10) . .
O1 P1 Cl1 105.74(7) . .
N1 P1 Cl1 106.46(7) . .
N3 P1 Cl1 108.49(7) . .
O1 P1 P2 101.52(6) . .
N1 P1 P2 33.89(7) . .
N3 P1 P2 91.67(7) . .
Cl1 P1 P2 139.00(4) . .
O2 P2 N1 111.31(9) . .
O2 P2 N2 107.08(10) . .
N1 P2 N2 116.91(10) . .
O2 P2 Cl2 105.30(7) . .
N1 P2 Cl2 107.19(7) . .
N2 P2 Cl2 108.43(8) . .
O2 P2 P1 100.95(6) . .
N1 P2 P1 33.95(7) . .
N2 P2 P1 91.63(7) . .
Cl2 P2 P1 140.04(3) . .
N2 P3 N3 119.46(10) . .
N2 P3 Cl4 109.31(8) . .
N3 P3 Cl4 108.73(8) . .
N2 P3 Cl3 107.91(8) . .
N3 P3 Cl3 108.94(8) . .
Cl4 P3 Cl3 100.89(4) . .
O3 P4 N6 107.92(10) . .
O3 P4 N4 111.16(9) . .
N6 P4 N4 117.18(10) . .
O3 P4 Cl5 104.81(7) . .
N6 P4 Cl5 106.97(8) . .
N4 P4 Cl5 108.04(8) . .
O3 P4 P5 106.54(6) . .
N6 P4 P5 89.98(7) . .
N4 P4 P5 32.72(7) . .
Cl5 P4 P5 137.39(3) . .
O4 P5 N4 111.78(9) . .
O4 P5 N5 107.13(10) . .
N4 P5 N5 117.74(10) . .
O4 P5 Cl6 105.11(7) . .
N4 P5 Cl6 107.00(7) . .
N5 P5 Cl6 107.29(7) . .
O4 P5 P4 104.68(6) . .
N4 P5 P4 32.89(7) . .
N5 P5 P4 91.70(7) . .
Cl6 P5 P4 137.69(4) . .
N6 P6 N5 119.25(10) . .
N6 P6 Cl7 109.97(8) . .
N5 P6 Cl7 108.62(8) . .
N6 P6 Cl8 108.09(8) . .
N5 P6 Cl8 108.79(8) . .
Cl7 P6 Cl8 100.48(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.471(3) .
C1 C2 1.539(3) .
C2 C6 1.534(3) .
C2 C3 1.535(3) .
C2 C4 1.559(3) .
C3 O2 1.463(3) .
C4 C5 1.523(3) .
C6 C7 1.527(3) .
C8 O3 1.473(3) .
C8 C9 1.539(3) .
C9 C11 1.534(3) .
C9 C10 1.539(3) .
C9 C13 1.554(3) .
C10 O4 1.472(3) .
C11 C12 1.536(3) .
C13 C14 1.522(3) .
N1 P2 1.5883(19) .
N1 P1 1.5909(19) .
N2 P3 1.578(2) .
N2 P2 1.592(2) .
N3 P3 1.583(2) .
N3 P1 1.595(2) .
N4 P5 1.5866(19) .
N4 P4 1.5940(19) .
N5 P6 1.5800(19) .
N5 P5 1.5905(19) .
N6 P6 1.575(2) .
N6 P4 1.586(2) .
O1 P1 1.5659(16) .
O2 P2 1.5691(16) .
O3 P4 1.5627(16) .
O4 P5 1.5646(16) .
P1 Cl1 1.9927(8) .
P1 P2 2.6382(8) .
P2 Cl2 1.9924(8) .
P3 Cl4 1.9879(8) .
P3 Cl3 2.0169(8) .
P4 Cl5 1.9908(8) .
P4 P5 2.6733(8) .
P5 Cl6 1.9955(8) .
P6 Cl7 1.9863(8) .
P6 Cl8 2.0163(8) .
