#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:36:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179756 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/52/7005298.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_7005298
loop_
_publ_author_name
'Coles, Simon J.'
'Davies, David B.'
'Eaton, Robert J.'
'Hursthouse, Michael B.'
'Kiliç, Adem'
'Shaw, Robert A.'
'Uslu, Aylin'
_publ_section_title
;
 Stereogenic properties of spiranes combined with four equivalent
 conventional centres of chirality.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2040
_journal_page_last               2047
_journal_paper_doi               10.1039/b700464h
_journal_year                    2007
_chemical_formula_sum            'C13 H32 Cl4 N10 O4 P6'
_chemical_formula_weight         720.11
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.704(2)
_cell_angle_beta                 99.887(2)
_cell_angle_gamma                111.292(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0203(8)
_cell_length_b                   9.6900(9)
_cell_length_c                   19.3728(17)
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.21
_cell_volume                     1539.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68950
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13034
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7354
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+1.4697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                5002
_reflns_number_total             7354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b700464h.txt
_cod_data_source_block           2b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7005298
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
P1 P 0.22646(10) 0.23013(9) 0.52560(4) 0.02558(18) Uani 1 1 d . . .
N1 N 0.3155(4) 0.1969(3) 0.59591(15) 0.0327(6) Uani 1 1 d . . .
P2 P 0.27337(11) 0.23260(10) 0.66929(4) 0.02719(19) Uani 1 1 d . . .
N2 N 0.1222(4) 0.2773(3) 0.67018(14) 0.0325(6) Uani 1 1 d . . .
P3 P 0.03451(11) 0.31647(10) 0.60035(4) 0.02757(19) Uani 1 1 d . . .
N3 N 0.0752(3) 0.2752(3) 0.52803(14) 0.0307(6) Uani 1 1 d . . .
P4 P 0.26239(13) 0.09298(11) 0.23158(5) 0.0371(2) Uani 1 1 d . . .
N4 N 0.3957(5) 0.2167(4) 0.20220(18) 0.0540(10) Uani 1 1 d . A .
P5 P 0.4581(2) 0.18150(15) 0.13455(6) 0.0621(4) Uani 1 1 d DU . .
N5 N 0.3865(6) 0.0161(5) 0.0965(2) 0.0747(13) Uani 1 1 d . A .
P6 P 0.23024(18) -0.10273(15) 0.11653(6) 0.0600(3) Uani 1 1 d DU . .
N6 N 0.1768(4) -0.0661(4) 0.18719(17) 0.0495(9) Uani 1 1 d . A .
O1 O 0.1741(3) 0.0904(2) 0.46746(12) 0.0299(5) Uani 1 1 d . . .
O2 O 0.3581(3) 0.3558(2) 0.49526(11) 0.0284(5) Uani 1 1 d . . .
O3 O 0.1254(3) 0.1499(3) 0.24505(12) 0.0417(6) Uani 1 1 d . . .
O4 O 0.3394(3) 0.0744(3) 0.30817(12) 0.0347(5) Uani 1 1 d . . .
C1 C 0.1147(4) 0.1120(4) 0.39615(17) 0.0300(7) Uani 1 1 d . . .
H1A H 0.0156 0.1344 0.3948 0.036 Uiso 1 1 calc R . .
H1B H 0.0850 0.0187 0.3636 0.036 Uiso 1 1 calc R . .
C2 C 0.3013(4) 0.3827(4) 0.42454(16) 0.0289(7) Uani 1 1 d . . .
H2A H 0.3906 0.4627 0.4101 0.035 Uiso 1 1 calc R . .
H2B H 0.2105 0.4171 0.4247 0.035 Uiso 1 1 calc R . .
C3 C 0.1689(5) 0.2736(4) 0.30065(17) 0.0335(8) Uani 1 1 d . . .
H3A H 0.0705 0.2932 0.3054 0.040 Uiso 1 1 calc R . .
H3B H 0.2477 0.3646 0.2878 0.040 Uiso 1 1 calc R . .
C4 C 0.3898(4) 0.2011(4) 0.36340(17) 0.0319(7) Uani 1 1 d . . .
H4A H 0.4752 0.2882 0.3511 0.038 Uiso 1 1 calc R . .
H4B H 0.4359 0.1759 0.4087 0.038 Uiso 1 1 calc R . .
C5 C 0.2436(4) 0.2404(3) 0.37143(16) 0.0259(6) Uani 1 1 d . . .
Cl1 Cl 0.47286(12) 0.41056(11) 0.72545(5) 0.0465(2) Uani 1 1 d . . .
Cl2 Cl 0.10327(12) 0.54687(10) 0.61484(5) 0.0426(2) Uani 1 1 d . . .
N7 N 0.2608(3) 0.0949(3) 0.71521(15) 0.0323(6) Uani 1 1 d . . .
C6 C 0.3735(5) 0.0199(5) 0.7104(2) 0.0435(9) Uani 1 1 d . . .
H6A H 0.3880 0.0107 0.6616 0.065 Uiso 1 1 calc R . .
H6B H 0.3293 -0.0799 0.7245 0.065 Uiso 1 1 calc R . .
H6C H 0.4787 0.0785 0.7418 0.065 Uiso 1 1 calc R . .
C7 C 0.2311(5) 0.1150(5) 0.7869(2) 0.0448(9) Uani 1 1 d . . .
H7A H 0.1554 0.1665 0.7864 0.067 Uiso 1 1 calc R . .
H7B H 0.3342 0.1749 0.8196 0.067 Uiso 1 1 calc R . .
H7C H 0.1840 0.0171 0.8024 0.067 Uiso 1 1 calc R . .
N8 N -0.1614(3) 0.2493(3) 0.59533(16) 0.0333(6) Uani 1 1 d . . .
C8 C -0.2213(5) 0.2790(5) 0.6574(2) 0.0427(9) Uani 1 1 d . . .
H8A H -0.1385 0.2928 0.7001 0.064 Uiso 1 1 calc R . .
H8B H -0.3209 0.1944 0.6592 0.064 Uiso 1 1 calc R . .
H8C H -0.2447 0.3699 0.6548 0.064 Uiso 1 1 calc R . .
C9 C -0.2730(5) 0.2257(5) 0.5279(2) 0.0442(9) Uani 1 1 d . . .
H9A H -0.2226 0.2063 0.4894 0.066 Uiso 1 1 calc R . .
H9B H -0.2981 0.3151 0.5222 0.066 Uiso 1 1 calc R . .
H9C H -0.3737 0.1397 0.5268 0.066 Uiso 1 1 calc R . .
Cl3 Cl 0.4433(6) 0.3336(4) 0.07027(19) 0.0667(10) Uani 0.50 1 d PDU A 1
Cl4 Cl 0.2826(6) -0.2803(4) 0.1229(3) 0.0518(10) Uani 0.50 1 d PDU A 1
N9 N 0.6626(18) 0.249(2) 0.1445(9) 0.092(5) Uani 0.50 1 d PDU A 1
C10 C 0.7654(13) 0.3864(11) 0.1973(5) 0.064(2) Uani 0.50 1 d PDU A 1
H10A H 0.6986 0.4076 0.2281 0.096 Uiso 0.50 1 calc PR A 1
H10B H 0.8088 0.4719 0.1722 0.096 Uiso 0.50 1 calc PR A 1
H10C H 0.8557 0.3686 0.2261 0.096 Uiso 0.50 1 calc PR A 1
C11 C 0.7540(15) 0.2002(12) 0.1017(5) 0.071(3) Uani 0.50 1 d PDU A 1
H11A H 0.6826 0.1060 0.0718 0.106 Uiso 0.50 1 calc PR A 1
H11B H 0.8434 0.1847 0.1324 0.106 Uiso 0.50 1 calc PR A 1
H11C H 0.7985 0.2763 0.0718 0.106 Uiso 0.50 1 calc PR A 1
N10 N 0.0740(17) -0.146(2) 0.0437(7) 0.089(6) Uani 0.50 1 d PDU A 1
C12 C -0.0786(16) -0.243(3) 0.0578(9) 0.186(11) Uani 0.50 1 d PDU A 1
H12A H -0.0830 -0.2163 0.1069 0.279 Uiso 0.50 1 calc PR A 1
H12B H -0.0887 -0.3469 0.0503 0.279 Uiso 0.50 1 calc PR A 1
H12C H -0.1683 -0.2302 0.0258 0.279 Uiso 0.50 1 calc PR A 1
C13 C 0.1068(19) -0.1548(17) -0.0264(5) 0.112(5) Uani 0.50 1 d PDU A 1
H13A H 0.2114 -0.0756 -0.0272 0.168 Uiso 0.50 1 calc PR A 1
H13B H 0.0202 -0.1419 -0.0603 0.168 Uiso 0.50 1 calc PR A 1
H13C H 0.1110 -0.2525 -0.0395 0.168 Uiso 0.50 1 calc PR A 1
Cl5 Cl 0.6896(6) 0.2465(6) 0.1627(3) 0.0725(11) Uani 0.50 1 d PDU A 2
Cl6 Cl 0.0307(8) -0.1696(7) 0.0408(3) 0.100(2) Uani 0.50 1 d PDU A 2
N11 N 0.403(2) 0.2658(13) 0.0647(7) 0.080(4) Uani 0.50 1 d PDU A 2
C14 C 0.473(3) 0.2511(19) 0.0030(7) 0.142(7) Uani 0.50 1 d PDU A 2
H14A H 0.4657 0.1481 -0.0067 0.213 Uiso 0.50 1 calc PR A 2
H14B H 0.5870 0.3198 0.0124 0.213 Uiso 0.50 1 calc PR A 2
H14C H 0.4119 0.2755 -0.0382 0.213 Uiso 0.50 1 calc PR A 2
C15 C 0.403(3) 0.4045(17) 0.0872(5) 0.147(8) Uani 0.50 1 d PDU A 2
H15A H 0.3484 0.3971 0.1271 0.221 Uiso 0.50 1 calc PR A 2
H15B H 0.3455 0.4377 0.0483 0.221 Uiso 0.50 1 calc PR A 2
H15C H 0.5156 0.4768 0.1021 0.221 Uiso 0.50 1 calc PR A 2
N12 N 0.257(2) -0.2692(18) 0.1211(12) 0.071(5) Uani 0.50 1 d PDU A 2
C16 C 0.1392(18) -0.3922(15) 0.1482(7) 0.102(4) Uani 0.50 1 d PDU A 2
H16A H 0.0775 -0.3521 0.1750 0.153 Uiso 0.50 1 calc PR A 2
H16B H 0.1976 -0.4403 0.1792 0.153 Uiso 0.50 1 calc PR A 2
H16C H 0.0643 -0.4659 0.1084 0.153 Uiso 0.50 1 calc PR A 2
C17 C 0.3498(17) -0.3151(14) 0.0769(6) 0.090(4) Uani 0.50 1 d PDU A 2
H17A H 0.4212 -0.2275 0.0597 0.136 Uiso 0.50 1 calc PR A 2
H17B H 0.2751 -0.3874 0.0366 0.136 Uiso 0.50 1 calc PR A 2
H17C H 0.4158 -0.3615 0.1046 0.136 Uiso 0.50 1 calc PR A 2
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
_geom_angle_publ_flag
N1 P1 O1 108.28(14) . . ?
N1 P1 N3 118.40(15) . . ?
O1 P1 N3 109.20(15) . . ?
N1 P1 O2 107.98(15) . . ?
O1 P1 O2 102.37(12) . . ?
N3 P1 O2 109.42(14) . . ?
P1 N1 P2 120.60(18) . . ?
N2 P2 N1 119.23(15) . . ?
N2 P2 N7 109.68(15) . . ?
N1 P2 N7 109.57(16) . . ?
N2 P2 Cl1 106.12(12) . . ?
N1 P2 Cl1 106.43(13) . . ?
N7 P2 Cl1 104.74(12) . . ?
P2 N2 P3 120.14(17) . . ?
N3 P3 N2 118.32(15) . . ?
N3 P3 N8 110.65(16) . . ?
N2 P3 N8 109.46(15) . . ?
N3 P3 Cl2 106.49(12) . . ?
N2 P3 Cl2 105.92(12) . . ?
N8 P3 Cl2 105.03(12) . . ?
P3 N3 P1 121.18(18) . . ?
N6 P4 N4 118.21(19) . . ?
N6 P4 O3 107.70(18) . . ?
N4 P4 O3 110.00(18) . . ?
N6 P4 O4 107.90(17) . . ?
N4 P4 O4 108.99(18) . . ?
O3 P4 O4 102.95(13) . . ?
P4 N4 P5 122.4(2) . . ?
N5 P5 N4 118.2(2) . . ?
N5 P5 N9 108.7(6) . . ?
N4 P5 N9 114.7(5) . . ?
N5 P5 N11 98.6(5) . . ?
N4 P5 N11 112.7(5) . . ?
N9 P5 N11 101.5(9) . . ?
N5 P5 Cl5 109.2(3) . . ?
N4 P5 Cl5 106.5(2) . . ?
N9 P5 Cl5 10.6(8) . . ?
N11 P5 Cl5 111.6(6) . . ?
N5 P5 Cl3 114.4(2) . . ?
N4 P5 Cl3 106.9(2) . . ?
N9 P5 Cl3 90.7(7) . . ?
N11 P5 Cl3 16.6(5) . . ?
Cl5 P5 Cl3 99.9(2) . . ?
P5 N5 P6 119.5(3) . . ?
N6 P6 N5 119.4(2) . . ?
N6 P6 N12 106.8(6) . . ?
N5 P6 N12 108.7(6) . . ?
N6 P6 N10 111.7(4) . . ?
N5 P6 N10 106.5(6) . . ?
N12 P6 N10 102.4(11) . . ?
N6 P6 Cl4 108.5(2) . . ?
N5 P6 Cl4 103.6(2) . . ?
N12 P6 Cl4 5.4(8) . . ?
N10 P6 Cl4 106.1(7) . . ?
N6 P6 Cl6 105.8(2) . . ?
N5 P6 Cl6 114.4(3) . . ?
N12 P6 Cl6 99.8(8) . . ?
N10 P6 Cl6 7.9(6) . . ?
Cl4 P6 Cl6 104.0(3) . . ?
P4 N6 P6 120.4(2) . . ?
C1 O1 P1 115.3(2) . . ?
C2 O2 P1 115.0(2) . . ?
C3 O3 P4 117.9(2) . . ?
C4 O4 P4 117.3(2) . . ?
O1 C1 C5 111.1(3) . . ?
O2 C2 C5 110.8(3) . . ?
O3 C3 C5 111.4(3) . . ?
O4 C4 C5 109.8(3) . . ?
C3 C5 C1 109.4(3) . . ?
C3 C5 C2 107.4(3) . . ?
C1 C5 C2 110.2(3) . . ?
C3 C5 C4 109.6(3) . . ?
C1 C5 C4 111.0(3) . . ?
C2 C5 C4 109.2(3) . . ?
C6 N7 C7 113.8(3) . . ?
C6 N7 P2 117.8(2) . . ?
C7 N7 P2 116.2(3) . . ?
C9 N8 C8 115.3(3) . . ?
C9 N8 P3 120.5(2) . . ?
C8 N8 P3 118.1(3) . . ?
C11 N9 C10 113.5(11) . . ?
C11 N9 P5 126.7(11) . . ?
C10 N9 P5 119.5(10) . . ?
C12 N10 C13 120.7(14) . . ?
C12 N10 P6 111.7(11) . . ?
C13 N10 P6 119.9(9) . . ?
C15 N11 C14 118.1(11) . . ?
C15 N11 P5 111.8(9) . . ?
C14 N11 P5 115.3(10) . . ?
C17 N12 C16 114.9(12) . . ?
C17 N12 P6 121.7(11) . . ?
C16 N12 P6 119.4(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.573(3) . ?
P1 O1 1.575(2) . ?
P1 N3 1.583(3) . ?
P1 O2 1.588(2) . ?
N1 P2 1.582(3) . ?
P2 N2 1.576(3) . ?
P2 N7 1.632(3) . ?
P2 Cl1 2.0559(13) . ?
N2 P3 1.587(3) . ?
P3 N3 1.571(3) . ?
P3 N8 1.629(3) . ?
P3 Cl2 2.0740(12) . ?
P4 N6 1.565(3) . ?
P4 N4 1.576(4) . ?
P4 O3 1.577(3) . ?
P4 O4 1.577(2) . ?
N4 P5 1.577(3) . ?
P5 N5 1.569(5) . ?
P5 N9 1.689(15) . ?
P5 N11 1.717(12) . ?
P5 Cl5 1.915(5) . ?
P5 Cl3 2.016(3) . ?
N5 P6 1.590(5) . ?
P6 N6 1.587(3) . ?
P6 N12 1.722(14) . ?
P6 N10 1.722(14) . ?
P6 Cl4 1.949(5) . ?
P6 Cl6 1.983(6) . ?
O1 C1 1.451(4) . ?
O2 C2 1.453(4) . ?
O3 C3 1.448(4) . ?
O4 C4 1.455(4) . ?
C1 C5 1.532(5) . ?
C2 C5 1.530(4) . ?
C3 C5 1.528(4) . ?
C4 C5 1.528(5) . ?
N7 C6 1.460(5) . ?
N7 C7 1.473(5) . ?
N8 C9 1.454(5) . ?
N8 C8 1.453(5) . ?
N9 C11 1.435(13) . ?
N9 C10 1.510(13) . ?
N10 C12 1.438(14) . ?
N10 C13 1.442(12) . ?
N11 C15 1.386(11) . ?
N11 C14 1.465(12) . ?
N12 C17 1.447(13) . ?
N12 C16 1.476(13) . ?
