#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/94/1519469.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_1519469
loop_
_publ_author_name
'Shaw, Robert. A.'
'Davies, David B.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C9H15Cl2F4N4O3P3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              874
_journal_year                    2002
_chemical_absolute_configuration unk
_chemical_formula_sum            'C9 H15 Cl2 F4 N4 O3 P3'
_chemical_formula_weight         467.06
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2682(2)
_cell_length_b                   13.1798(4)
_cell_length_c                   16.1482(5)
_cell_measurement_reflns_used    8005
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1759.72(9)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10491
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.8499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV Blessing (1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.5138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                3527
_reflns_number_total             3955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-874.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Shaw, Robert. A. and Davies, David B. and Coles, Simon J. and 
Hursthouse, Michael B. (2002) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/874)

More at:
http://ecrystals.chem.soton.ac.uk/874/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1519469
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9687(3) 0.24619(18) 0.89034(16) 0.0181(5) Uani 1 1 d . . .
H1A H 0.9703 0.1909 0.9318 0.022 Uiso 1 1 calc R . .
H1B H 0.9109 0.2211 0.8407 0.022 Uiso 1 1 calc R . .
C2 C 0.8775(3) 0.33786(19) 0.92624(15) 0.0168(5) Uani 1 1 d . . .
C3 C 0.7071(3) 0.35679(18) 0.89156(16) 0.0171(5) Uani 1 1 d . . .
C4 C 0.6858(3) 0.37715(18) 0.79997(15) 0.0169(5) Uani 1 1 d . . .
H4A H 0.7253 0.3182 0.7678 0.020 Uiso 1 1 calc R . .
H4B H 0.5696 0.3866 0.7874 0.020 Uiso 1 1 calc R . .
C5 C 1.3264(4) 0.5910(3) 0.94393(18) 0.0358(8) Uani 1 1 d . . .
H5A H 1.4302 0.6213 0.9260 0.043 Uiso 1 1 calc R . .
H5B H 1.3438 0.5185 0.9572 0.043 Uiso 1 1 calc R . .
C6 C 1.2569(4) 0.6478(3) 1.01810(19) 0.0322(7) Uani 1 1 d . . .
H6A H 1.2914 0.7198 1.0179 0.039 Uiso 1 1 calc R . .
H6B H 1.2912 0.6160 1.0708 0.039 Uiso 1 1 calc R . .
C7 C 1.0741(4) 0.6389(2) 1.00624(18) 0.0295(7) Uani 1 1 d . . .
H7A H 1.0159 0.6922 1.0376 0.035 Uiso 1 1 calc R . .
H7B H 1.0342 0.5715 1.0239 0.035 Uiso 1 1 calc R . .
C8 C 1.0541(4) 0.6536(2) 0.91267(17) 0.0256(6) Uani 1 1 d . . .
H8A H 0.9543 0.6205 0.8922 0.031 Uiso 1 1 calc R . .
H8B H 1.0516 0.7265 0.8978 0.031 Uiso 1 1 calc R . .
C9 C 1.4108(3) 0.5590(2) 0.66770(16) 0.0244(6) Uani 1 1 d . . .
H9A H 1.4462 0.4891 0.6777 0.037 Uiso 1 1 calc R . .
H9B H 1.5027 0.5994 0.6482 0.037 Uiso 1 1 calc R . .
H9C H 1.3255 0.5593 0.6256 0.037 Uiso 1 1 calc R . .
N1 N 1.0091(2) 0.34808(14) 0.73451(13) 0.0138(4) Uani 1 1 d . . .
N2 N 1.0447(3) 0.55300(15) 0.74302(13) 0.0166(4) Uani 1 1 d . . .
N3 N 1.2780(2) 0.42851(16) 0.80468(13) 0.0180(5) Uani 1 1 d . . .
N4 N 1.2009(3) 0.60323(17) 0.87946(14) 0.0224(5) Uani 1 1 d . . .
O1 O 1.1316(2) 0.27201(13) 0.86819(11) 0.0183(4) Uani 1 1 d . . .
O2 O 0.7741(2) 0.46654(13) 0.77621(10) 0.0181(4) Uani 1 1 d . . .
O3 O 1.3490(2) 0.60199(13) 0.74390(11) 0.0206(4) Uani 1 1 d . . .
F1 F 0.96509(19) 0.42416(11) 0.91773(9) 0.0205(3) Uani 1 1 d . . .
F2 F 0.8589(2) 0.32420(12) 1.00996(9) 0.0252(4) Uani 1 1 d . . .
F3 F 0.6432(2) 0.43524(13) 0.93523(9) 0.0267(4) Uani 1 1 d . . .
F4 F 0.61786(18) 0.27309(13) 0.90950(9) 0.0270(4) Uani 1 1 d . . .
P1 P 1.17113(7) 0.33302(5) 0.78591(4) 0.01437(14) Uani 1 1 d . . .
P2 P 0.93630(7) 0.45854(5) 0.72451(4) 0.01419(14) Uani 1 1 d . . .
P3 P 1.21218(8) 0.54254(5) 0.79253(4) 0.01566(14) Uani 1 1 d . . .
Cl1 Cl 1.31164(8) 0.23232(5) 0.72690(4) 0.02148(15) Uani 1 1 d . . .
Cl2 Cl 0.85382(8) 0.47100(5) 0.60793(4) 0.02422(16) 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'
F F 0.0171 0.0103 '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 111.6(2) . .
O1 C1 H1A 109.3 . .
C2 C1 H1A 109.3 . .
O1 C1 H1B 109.3 . .
C2 C1 H1B 109.3 . .
H1A C1 H1B 108.0 . .
F1 C2 F2 105.64(19) . .
F1 C2 C3 108.5(2) . .
F2 C2 C3 106.1(2) . .
F1 C2 C1 111.0(2) . .
F2 C2 C1 108.8(2) . .
C3 C2 C1 116.1(2) . .
F4 C3 F3 107.22(19) . .
F4 C3 C4 106.8(2) . .
F3 C3 C4 109.1(2) . .
F4 C3 C2 106.77(19) . .
F3 C3 C2 106.9(2) . .
C4 C3 C2 119.5(2) . .
O2 C4 C3 110.3(2) . .
O2 C4 H4A 109.6 . .
C3 C4 H4A 109.6 . .
O2 C4 H4B 109.6 . .
C3 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
N4 C5 C6 103.6(2) . .
N4 C5 H5A 111.0 . .
C6 C5 H5A 111.0 . .
N4 C5 H5B 111.0 . .
C6 C5 H5B 111.0 . .
H5A C5 H5B 109.0 . .
C5 C6 C7 103.7(2) . .
C5 C6 H6A 111.0 . .
C7 C6 H6A 111.0 . .
C5 C6 H6B 111.0 . .
C7 C6 H6B 111.0 . .
H6A C6 H6B 109.0 . .
C6 C7 C8 102.7(3) . .
C6 C7 H7A 111.2 . .
C8 C7 H7A 111.2 . .
C6 C7 H7B 111.2 . .
C8 C7 H7B 111.2 . .
H7A C7 H7B 109.1 . .
N4 C8 C7 102.2(2) . .
N4 C8 H8A 111.3 . .
C7 C8 H8A 111.3 . .
N4 C8 H8B 111.3 . .
C7 C8 H8B 111.3 . .
H8A C8 H8B 109.2 . .
O3 C9 H9A 109.5 . .
O3 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O3 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
P2 N1 P1 119.25(13) . .
P2 N2 P3 121.45(13) . .
P1 N3 P3 122.38(13) . .
C8 N4 C5 111.6(2) . .
C8 N4 P3 125.58(19) . .
C5 N4 P3 121.11(19) . .
C1 O1 P1 121.49(15) . .
C4 O2 P2 121.07(15) . .
C9 O3 P3 118.66(16) . .
N3 P1 O1 111.17(11) . .
N3 P1 N1 118.43(11) . .
O1 P1 N1 109.08(10) . .
N3 P1 Cl1 107.27(8) . .
O1 P1 Cl1 100.48(7) . .
N1 P1 Cl1 108.86(8) . .
N2 P2 N1 119.66(11) . .
N2 P2 O2 109.39(11) . .
N1 P2 O2 109.22(10) . .
N2 P2 Cl2 107.99(8) . .
N1 P2 Cl2 107.44(8) . .
O2 P2 Cl2 101.60(7) . .
O3 P3 N2 109.05(11) . .
O3 P3 N3 106.31(10) . .
N2 P3 N3 115.62(11) . .
O3 P3 N4 103.10(11) . .
N2 P3 N4 109.88(12) . .
N3 P3 N4 112.03(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.435(3) .
C1 C2 1.538(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 F1 1.356(3) .
C2 F2 1.372(3) .
C2 C3 1.536(3) .
C3 F4 1.359(3) .
C3 F3 1.358(3) .
C3 C4 1.513(4) .
C4 O2 1.438(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 N4 1.478(4) .
C5 C6 1.525(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.528(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.532(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 N4 1.484(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 O3 1.448(3) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
N1 P2 1.584(2) .
N1 P1 1.589(2) .
N2 P2 1.563(2) .
N2 P3 1.605(2) .
N3 P1 1.567(2) .
N3 P3 1.610(2) .
N4 P3 1.618(2) .
O1 P1 1.5871(18) .
O2 P2 1.5835(18) .
O3 P3 1.5842(18) .
P1 Cl1 2.0048(8) .
P2 Cl2 2.0089(9) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 F1 8.5(3) . . . .
O1 C1 C2 F2 -107.4(2) . . . .
O1 C1 C2 C3 133.0(2) . . . .
F1 C2 C3 F4 -173.29(18) . . . .
F2 C2 C3 F4 -60.2(2) . . . .
C1 C2 C3 F4 60.9(3) . . . .
F1 C2 C3 F3 -58.8(2) . . . .
F2 C2 C3 F3 54.3(2) . . . .
C1 C2 C3 F3 175.4(2) . . . .
F1 C2 C3 C4 65.6(3) . . . .
F2 C2 C3 C4 178.7(2) . . . .
C1 C2 C3 C4 -60.2(3) . . . .
F4 C3 C4 O2 178.67(18) . . . .
F3 C3 C4 O2 63.1(2) . . . .
C2 C3 C4 O2 -60.2(3) . . . .
N4 C5 C6 C7 28.5(3) . . . .
C5 C6 C7 C8 -40.2(3) . . . .
C6 C7 C8 N4 35.5(3) . . . .
C7 C8 N4 C5 -18.5(3) . . . .
C7 C8 N4 P3 146.6(2) . . . .
C6 C5 N4 C8 -6.2(3) . . . .
C6 C5 N4 P3 -172.0(2) . . . .
C2 C1 O1 P1 -77.3(2) . . . .
C3 C4 O2 P2 106.3(2) . . . .
P3 N3 P1 O1 -113.33(15) . . . .
P3 N3 P1 N1 14.1(2) . . . .
P3 N3 P1 Cl1 137.73(13) . . . .
C1 O1 P1 N3 127.39(18) . . . .
C1 O1 P1 N1 -5.0(2) . . . .
C1 O1 P1 Cl1 -119.32(17) . . . .
P2 N1 P1 N3 -16.12(19) . . . .
P2 N1 P1 O1 112.33(14) . . . .
P2 N1 P1 Cl1 -138.91(11) . . . .
P3 N2 P2 N1 -15.1(2) . . . .
P3 N2 P2 O2 111.94(15) . . . .
P3 N2 P2 Cl2 -138.28(12) . . . .
P1 N1 P2 N2 16.75(19) . . . .
P1 N1 P2 O2 -110.35(14) . . . .
P1 N1 P2 Cl2 140.22(11) . . . .
C4 O2 P2 N2 -153.21(17) . . . .
C4 O2 P2 N1 -20.5(2) . . . .
C4 O2 P2 Cl2 92.80(17) . . . .
C9 O3 P3 N2 -73.1(2) . . . .
C9 O3 P3 N3 52.2(2) . . . .
C9 O3 P3 N4 170.20(19) . . . .
P2 N2 P3 O3 131.88(14) . . . .
P2 N2 P3 N3 12.2(2) . . . .
P2 N2 P3 N4 -115.80(16) . . . .
P1 N3 P3 O3 -133.05(15) . . . .
P1 N3 P3 N2 -11.9(2) . . . .
P1 N3 P3 N4 115.04(16) . . . .
C8 N4 P3 O3 121.2(2) . . . .
C5 N4 P3 O3 -75.0(2) . . . .
C8 N4 P3 N2 5.0(3) . . . .
C5 N4 P3 N2 168.8(2) . . . .
C8 N4 P3 N3 -124.9(2) . . . .
C5 N4 P3 N3 38.9(3) . . . .
