#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:59:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180283 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/69/7116984.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_7116984
loop_
_publ_author_name
'G. Gangadhararao'
'R. N. Prasad Tulichala'
'K. C. Kumara Swamy'
_publ_section_title
;
 Spontaneous resolution upon crystallization of allenyl-bis-phosphine
 oxides
;
_journal_name_full               Chem.Commun.
_journal_page_first              7168
_journal_paper_doi               10.1039/C5cc00232J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C40 H30 Cl N O4 P2'
_chemical_formula_weight         686.04
_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
_audit_update_record
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                106.240(3)
_cell_angle_beta                 94.143(3)
_cell_angle_gamma                110.585(3)
_cell_formula_units_Z            2
_cell_length_a                   9.9475(3)
_cell_length_b                   13.0705(5)
_cell_length_c                   14.9853(5)
_cell_measurement_reflns_used    5466
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3020
_cell_measurement_theta_min      3.8220
_cell_volume                     1719.37(12)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11875
_diffrn_reflns_theta_full        71.67
_diffrn_reflns_theta_max         71.67
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0435
_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)+(0.0716P)²+0.3938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                5708
_reflns_number_total             6554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00232j2.cif
_cod_data_source_block           compound-10
_cod_original_cell_volume        1719.36(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7116984
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 0.40128(5) 0.08209(4) 0.23673(3) 0.03387(12) Uani 1 1 d . . .
P2 P 0.28416(5) 0.41462(4) 0.28923(3) 0.03871(13) Uani 1 1 d . . .
Cl1 Cl 0.36177(10) 0.37247(8) -0.10128(5) 0.0993(3) Uani 1 1 d . . .
O1 O 0.37122(16) -0.04087(11) 0.18570(9) 0.0459(3) Uani 1 1 d . . .
C35 C 0.1641(2) 0.25903(15) 0.09449(12) 0.0378(4) Uani 1 1 d . . .
C1 C 0.49754(19) 0.13194(15) 0.35710(12) 0.0369(4) Uani 1 1 d . . .
C20 C 0.23162(18) 0.10503(14) 0.25002(11) 0.0338(3) Uani 1 1 d . . .
C7 C 0.50264(19) 0.17795(16) 0.17722(12) 0.0380(4) Uani 1 1 d . . .
O2 O 0.44118(17) 0.45717(14) 0.32479(12) 0.0627(4) Uani 1 1 d . . .
C22 C 0.20870(18) 0.27256(14) 0.19588(12) 0.0346(3) Uani 1 1 d . . .
C21 C 0.21487(18) 0.18614(15) 0.22074(12) 0.0353(3) Uani 1 1 d . . .
C36 C 0.0255(2) 0.18720(16) 0.04042(14) 0.0461(4) Uani 1 1 d . . .
C13 C 0.1192(2) 0.03104(15) 0.29024(12) 0.0383(4) Uani 1 1 d . . .
C2 C 0.4975(2) 0.22934(17) 0.42511(13) 0.0455(4) Uani 1 1 d . . .
H2 H 0.4492 0.2726 0.4085 0.055 Uiso 1 1 calc R . .
O3 O -0.11621(19) 0.18158(18) 0.15452(15) 0.0753(5) Uani 1 1 d . . .
C23 C 0.1819(2) 0.39789(16) 0.38285(14) 0.0452(4) Uani 1 1 d . . .
C34 C 0.3538(3) 0.60398(18) 0.23144(15) 0.0527(5) Uani 1 1 d . . .
H34 H 0.4492 0.6145 0.2534 0.063 Uiso 1 1 calc R . .
C19 C 0.1409(2) -0.05143(18) 0.32484(15) 0.0477(4) Uani 1 1 d . . .
H19 H 0.2279 -0.0627 0.3220 0.057 Uiso 1 1 calc R . .
C40 C 0.2679(2) 0.31594(17) 0.04911(14) 0.0465(4) Uani 1 1 d . . .
H40 H 0.3620 0.3643 0.0825 0.056 Uiso 1 1 calc R . .
N1 N -0.0905(2) 0.12570(17) 0.08329(15) 0.0591(5) Uani 1 1 d . . .
C29 C 0.2381(2) 0.51005(15) 0.23680(13) 0.0425(4) Uani 1 1 d . . .
C8 C 0.5919(2) 0.29243(18) 0.22245(15) 0.0508(5) Uani 1 1 d . . .
H8 H 0.6018 0.3244 0.2875 0.061 Uiso 1 1 calc R . .
C4 C 0.6403(2) 0.1977(2) 0.54193(15) 0.0567(5) Uani 1 1 d . . .
H4 H 0.6886 0.2198 0.6039 0.068 Uiso 1 1 calc R . .
C6 C 0.5682(2) 0.06714(19) 0.38271(15) 0.0485(4) Uani 1 1 d . . .
H6 H 0.5672 0.0011 0.3379 0.058 Uiso 1 1 calc R . .
C18 C 0.0343(2) -0.1169(2) 0.36345(16) 0.0545(5) Uani 1 1 d . . .
H18 H 0.0517 -0.1710 0.3865 0.065 Uiso 1 1 calc R . .
C12 C 0.4899(3) 0.1311(2) 0.08000(14) 0.0535(5) Uani 1 1 d . . .
H12 H 0.4299 0.0540 0.0486 0.064 Uiso 1 1 calc R . .
C39 C 0.2309(3) 0.3004(2) -0.04597(15) 0.0572(5) Uani 1 1 d . . .
C3 C 0.5687(2) 0.26206(19) 0.51714(14) 0.0516(5) Uani 1 1 d . . .
H3 H 0.5686 0.3273 0.5624 0.062 Uiso 1 1 calc R . .
C37 C -0.0094(3) 0.1706(2) -0.05498(16) 0.0610(6) Uani 1 1 d . . .
H37 H -0.1024 0.1208 -0.0893 0.073 Uiso 1 1 calc R . .
C11 C 0.5668(3) 0.1993(2) 0.02999(16) 0.0662(6) Uani 1 1 d . . .
H11 H 0.5589 0.1677 -0.0349 0.079 Uiso 1 1 calc R . .
C16 C -0.0966(3) -0.1039(2) 0.36852(18) 0.0609(6) Uani 1 1 d . . .
C28 C 0.2626(3) 0.43898(19) 0.47410(16) 0.0588(6) Uani 1 1 d . . .
H28 H 0.3643 0.4712 0.4844 0.071 Uiso 1 1 calc R . .
C5 C 0.6401(3) 0.1007(2) 0.47502(17) 0.0613(6) Uani 1 1 d . . .
H5 H 0.6885 0.0576 0.4920 0.074 Uiso 1 1 calc R . .
C24 C 0.0299(3) 0.3488(2) 0.36825(18) 0.0607(6) Uani 1 1 d . . .
H24 H -0.0248 0.3201 0.3073 0.073 Uiso 1 1 calc R . .
C10 C 0.6539(3) 0.3127(2) 0.07554(18) 0.0658(6) Uani 1 1 d . . .
H10 H 0.7049 0.3582 0.0415 0.079 Uiso 1 1 calc R . .
C30 C 0.0974(3) 0.4943(2) 0.2023(2) 0.0702(7) Uani 1 1 d . . .
H30 H 0.0186 0.4310 0.2046 0.084 Uiso 1 1 calc R . .
C38 C 0.0937(3) 0.2280(2) -0.09821(16) 0.0646(6) Uani 1 1 d . . .
H38 H 0.0716 0.2183 -0.1622 0.078 Uiso 1 1 calc R . .
C33 C 0.3290(3) 0.6825(2) 0.19368(19) 0.0685(7) Uani 1 1 d . . .
H33 H 0.4074 0.7456 0.1905 0.082 Uiso 1 1 calc R . .
O4 O -0.1573(3) 0.02191(18) 0.04329(18) 0.0991(7) Uani 1 1 d . . .
C25 C -0.0400(3) 0.3427(2) 0.4444(2) 0.0762(8) Uani 1 1 d . . .
H25 H -0.1416 0.3105 0.4346 0.091 Uiso 1 1 calc R . .
C9 C 0.6667(3) 0.3600(2) 0.17158(18) 0.0638(6) Uani 1 1 d . . .
H9 H 0.7256 0.4376 0.2024 0.077 Uiso 1 1 calc R . .
C14 C -0.0133(3) 0.0420(2) 0.2940(2) 0.0742(8) Uani 1 1 d . . .
H14 H -0.0322 0.0951 0.2703 0.089 Uiso 1 1 calc R . .
C26 C 0.0414(4) 0.3844(2) 0.5348(2) 0.0842(10) Uani 1 1 d . . .
H26 H -0.0056 0.3804 0.5859 0.101 Uiso 1 1 calc R . .
C27 C 0.1918(4) 0.4320(2) 0.54974(18) 0.0790(9) Uani 1 1 d . . .
H27 H 0.2460 0.4596 0.6108 0.095 Uiso 1 1 calc R . .
C31 C 0.0738(4) 0.5730(3) 0.1641(3) 0.0909(10) Uani 1 1 d . . .
H31 H -0.0209 0.5621 0.1403 0.109 Uiso 1 1 calc R . .
C15 C -0.1179(3) -0.0238(3) 0.3321(3) 0.0925(11) Uani 1 1 d . . .
H15 H -0.2060 -0.0141 0.3334 0.111 Uiso 1 1 calc R . .
C32 C 0.1906(4) 0.6674(3) 0.1614(2) 0.0805(8) Uani 1 1 d . . .
H32 H 0.1741 0.7211 0.1372 0.097 Uiso 1 1 calc R . .
C17 C -0.2134(4) -0.1747(3) 0.4102(3) 0.0917(10) Uani 1 1 d . . .
H17A H -0.2640 -0.2509 0.3654 0.138 Uiso 1 1 calc R . .
H17B H -0.2815 -0.1385 0.4249 0.138 Uiso 1 1 calc R . .
H17C H -0.1691 -0.1799 0.4670 0.138 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 P1 C7 112.63(8) . .
O1 P1 C1 113.39(8) . .
C7 P1 C1 108.28(8) . .
O1 P1 C20 111.33(8) . .
C7 P1 C20 107.37(8) . .
C1 P1 C20 103.27(8) . .
O2 P2 C23 111.01(10) . .
O2 P2 C29 112.06(10) . .
C23 P2 C29 108.63(9) . .
O2 P2 C22 114.22(9) . .
C23 P2 C22 105.67(8) . .
C29 P2 C22 104.82(8) . .
C40 C35 C36 117.29(17) . .
C40 C35 C22 118.77(16) . .
C36 C35 C22 123.85(17) . .
C6 C1 C2 119.51(17) . .
C6 C1 P1 118.11(14) . .
C2 C1 P1 122.32(14) . .
C21 C20 C13 123.25(16) . .
C21 C20 P1 116.89(13) . .
C13 C20 P1 119.84(12) . .
C8 C7 C12 119.15(18) . .
C8 C7 P1 123.97(14) . .
C12 C7 P1 116.88(15) . .
C21 C22 C35 121.18(15) . .
C21 C22 P2 115.97(13) . .
C35 C22 P2 122.20(12) . .
C22 C21 C20 175.30(17) . .
C37 C36 C35 122.5(2) . .
C37 C36 N1 116.90(18) . .
C35 C36 N1 120.65(18) . .
C14 C13 C19 117.12(18) . .
C14 C13 C20 120.19(17) . .
C19 C13 C20 122.69(17) . .
C3 C2 C1 120.28(19) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C28 C23 C24 119.5(2) . .
C28 C23 P2 116.73(18) . .
C24 C23 P2 123.81(17) . .
C29 C34 C33 120.6(2) . .
C29 C34 H34 119.7 . .
C33 C34 H34 119.7 . .
C18 C19 C13 120.77(19) . .
C18 C19 H19 119.6 . .
C13 C19 H19 119.6 . .
C39 C40 C35 119.77(19) . .
C39 C40 H40 120.1 . .
C35 C40 H40 120.1 . .
O3 N1 O4 124.7(2) . .
O3 N1 C36 117.82(19) . .
O4 N1 C36 117.5(2) . .
C30 C29 C34 119.1(2) . .
C30 C29 P2 124.37(16) . .
C34 C29 P2 116.53(17) . .
C7 C8 C9 120.36(19) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C5 C4 C3 120.16(19) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C5 C6 C1 120.0(2) . .
C5 C6 H6 120.0 . .
C1 C6 H6 120.0 . .
C16 C18 C19 121.7(2) . .
C16 C18 H18 119.1 . .
C19 C18 H18 119.1 . .
C11 C12 C7 120.0(2) . .
C11 C12 H12 120.0 . .
C7 C12 H12 120.0 . .
C38 C39 C40 121.9(2) . .
C38 C39 Cl1 119.00(18) . .
C40 C39 Cl1 119.09(19) . .
C2 C3 C4 119.9(2) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C38 C37 C36 119.4(2) . .
C38 C37 H37 120.3 . .
C36 C37 H37 120.3 . .
C10 C11 C12 120.3(2) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C18 C16 C15 116.9(2) . .
C18 C16 C17 122.2(2) . .
C15 C16 C17 120.9(2) . .
C27 C28 C23 120.0(3) . .
C27 C28 H28 120.0 . .
C23 C28 H28 120.0 . .
C4 C5 C6 120.2(2) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C25 C24 C23 120.1(3) . .
C25 C24 H24 119.9 . .
C23 C24 H24 119.9 . .
C11 C10 C9 120.2(2) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C29 C30 C31 119.8(2) . .
C29 C30 H30 120.1 . .
C31 C30 H30 120.1 . .
C37 C38 C39 119.2(2) . .
C37 C38 H38 120.4 . .
C39 C38 H38 120.4 . .
C32 C33 C34 119.9(2) . .
C32 C33 H33 120.0 . .
C34 C33 H33 120.0 . .
C26 C25 C24 119.9(3) . .
C26 C25 H25 120.1 . .
C24 C25 H25 120.1 . .
C10 C9 C8 120.0(2) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C15 C14 C13 121.4(2) . .
C15 C14 H14 119.3 . .
C13 C14 H14 119.3 . .
C27 C26 C25 120.3(2) . .
C27 C26 H26 119.8 . .
C25 C26 H26 119.8 . .
C26 C27 C28 120.2(3) . .
C26 C27 H27 119.9 . .
C28 C27 H27 119.9 . .
C32 C31 C30 120.1(3) . .
C32 C31 H31 120.0 . .
C30 C31 H31 120.0 . .
C14 C15 C16 122.1(2) . .
C14 C15 H15 118.9 . .
C16 C15 H15 118.9 . .
C33 C32 C31 120.5(2) . .
C33 C32 H32 119.8 . .
C31 C32 H32 119.8 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.4828(13) .
P1 C7 1.8023(18) .
P1 C1 1.8027(17) .
P1 C20 1.8300(17) .
P2 O2 1.4616(16) .
P2 C23 1.809(2) .
P2 C29 1.8115(19) .
P2 C22 1.8395(17) .
Cl1 C39 1.732(3) .
C35 C40 1.388(3) .
C35 C36 1.393(3) .
C35 C22 1.494(2) .
C1 C6 1.385(3) .
C1 C2 1.391(3) .
C20 C21 1.311(2) .
C20 C13 1.487(2) .
C7 C8 1.378(3) .
C7 C12 1.390(3) .
C22 C21 1.304(2) .
C36 C37 1.383(3) .
C36 N1 1.461(3) .
C13 C14 1.379(3) .
C13 C19 1.392(3) .
C2 C3 1.379(3) .
C2 H2 0.9300 .
O3 N1 1.214(3) .
C23 C28 1.389(3) .
C23 C24 1.392(3) .
C34 C29 1.384(3) .
C34 C33 1.385(3) .
C34 H34 0.9300 .
C19 C18 1.385(3) .
C19 H19 0.9300 .
C40 C39 1.384(3) .
C40 H40 0.9300 .
N1 O4 1.223(3) .
C29 C30 1.378(3) .
C8 C9 1.383(3) .
C8 H8 0.9300 .
C4 C5 1.378(4) .
C4 C3 1.382(3) .
C4 H4 0.9300 .
C6 C5 1.384(3) .
C6 H6 0.9300 .
C18 C16 1.376(3) .
C18 H18 0.9300 .
C12 C11 1.385(3) .
C12 H12 0.9300 .
C39 C38 1.376(4) .
C3 H3 0.9300 .
C37 C38 1.364(4) .
C37 H37 0.9300 .
C11 C10 1.364(4) .
C11 H11 0.9300 .
C16 C15 1.377(4) .
C16 C17 1.507(3) .
C28 C27 1.385(4) .
C28 H28 0.9300 .
C5 H5 0.9300 .
C24 C25 1.385(3) .
C24 H24 0.9300 .
C10 C9 1.375(3) .
C10 H10 0.9300 .
C30 C31 1.386(3) .
C30 H30 0.9300 .
C38 H38 0.9300 .
C33 C32 1.351(4) .
C33 H33 0.9300 .
C25 C26 1.381(5) .
C25 H25 0.9300 .
C9 H9 0.9300 .
C14 C15 1.371(3) .
C14 H14 0.9300 .
C26 C27 1.376(5) .
C26 H26 0.9300 .
C27 H27 0.9300 .
C31 C32 1.379(4) .
C31 H31 0.9300 .
C15 H15 0.9300 .
C32 H32 0.9300 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
