#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:09:37 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/46/7124696.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_7124696
loop_
_publ_author_name
'Blair, V. L.'
'Stevens, M. A.'
'Thompson, C. D.'
_publ_section_title
;
 The importance of the Lewis base in lithium mediated metallation and bond
 cleavage reaction of allyl amines and allyl phosphines.
;
_journal_issue                   52
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8111
_journal_page_last               8114
_journal_paper_doi               10.1039/c6cc03947b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C38 H48 Li2 O2 P2'
_chemical_formula_sum            'C38 H48 Li2 O2 P2'
_chemical_formula_weight         612.58
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-02-10 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.24(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.592(2)
_cell_length_b                   18.626(4)
_cell_length_c                   9.1190(18)
_cell_measurement_reflns_used    13140
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.21
_cell_volume                     1791.5(6)
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'ADSC Quantum 210r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_source         'MX1 beamline, Australian Synchrotron'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14517
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+1.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                4111
_reflns_number_total             4215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03947b2.cif
_cod_data_source_block           vb170
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7124696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
P1 P 0.71847(4) 0.091182(18) 0.33567(4) 0.01598(9) Uani 1 1 d .
O1 O 0.59877(12) 0.14635(6) 0.66961(14) 0.0263(3) Uani 1 1 d .
C1 C 0.65507(14) 0.05914(8) 0.16267(17) 0.0196(3) Uani 1 1 d .
H1 H 0.7081 0.0517 0.0855 0.023 Uiso 1 1 calc R
C2 C 0.52338(14) 0.04469(8) 0.14094(17) 0.0192(3) Uani 1 1 d .
H2 H 0.4796 0.0421 0.2272 0.023 Uiso 1 1 calc R
C3 C 0.45198(17) 0.03402(9) 0.0099(2) 0.0267(3) Uani 1 1 d .
H3A H 0.4907 0.0360 -0.0800 0.032 Uiso 1 1 calc R
H3B H 0.3637 0.0247 0.0088 0.032 Uiso 1 1 calc R
C4 C 0.89042(14) 0.08018(8) 0.33398(16) 0.0180(3) Uani 1 1 d .
C5 C 0.95926(15) 0.03959(9) 0.44142(18) 0.0224(3) Uani 1 1 d .
H5 H 0.9169 0.0171 0.5166 0.027 Uiso 1 1 calc R
C6 C 1.09030(16) 0.03158(10) 0.4397(2) 0.0275(3) Uani 1 1 d .
H6 H 1.1365 0.0038 0.5137 0.033 Uiso 1 1 calc R
C7 C 1.15314(15) 0.06402(10) 0.3307(2) 0.0262(3) Uani 1 1 d .
H7 H 1.2421 0.0582 0.3295 0.031 Uiso 1 1 calc R
C8 C 1.08562(16) 0.10509(10) 0.2232(2) 0.0244(3) Uani 1 1 d .
H8 H 1.1285 0.1277 0.1486 0.029 Uiso 1 1 calc R
C9 C 0.95582(15) 0.11300(9) 0.22496(18) 0.0215(3) Uani 1 1 d .
H9 H 0.9103 0.1411 0.1511 0.026 Uiso 1 1 calc R
C10 C 0.71215(17) 0.19035(7) 0.32440(19) 0.0197(3) Uani 1 1 d .
C11 C 0.62919(16) 0.22472(10) 0.2186(2) 0.0249(4) Uani 1 1 d .
H11 H 0.5781 0.1970 0.1487 0.030 Uiso 1 1 calc R
C12 C 0.62115(19) 0.29936(10) 0.2152(2) 0.0327(4) Uani 1 1 d .
H12 H 0.5649 0.3224 0.1428 0.039 Uiso 1 1 calc R
C13 C 0.69485(19) 0.34013(9) 0.3171(2) 0.0339(5) Uani 1 1 d .
H13 H 0.6889 0.3910 0.3145 0.041 Uiso 1 1 calc R
C14 C 0.77677(19) 0.30724(10) 0.4223(2) 0.0295(4) Uani 1 1 d .
H14 H 0.8275 0.3353 0.4918 0.035 Uiso 1 1 calc R
C15 C 0.78500(17) 0.23243(9) 0.42645(19) 0.0235(3) Uani 1 1 d .
H15 H 0.8410 0.2099 0.4998 0.028 Uiso 1 1 calc R
C16 C 0.6913(2) 0.17553(10) 0.7779(2) 0.0329(4) Uani 1 1 d .
H16A H 0.6533 0.1820 0.8723 0.039 Uiso 1 1 calc R
H16B H 0.7199 0.2230 0.7451 0.039 Uiso 1 1 calc R
C17 C 0.8022(2) 0.12522(11) 0.7993(2) 0.0345(4) Uani 1 1 d .
H17A H 0.7733 0.0783 0.8315 0.052 Uiso 1 1 calc R
H17B H 0.8652 0.1448 0.8742 0.052 Uiso 1 1 calc R
H17C H 0.8406 0.1198 0.7061 0.052 Uiso 1 1 calc R
C18 C 0.50283(18) 0.19916(10) 0.6233(2) 0.0340(4) Uani 1 1 d .
H18A H 0.5426 0.2406 0.5775 0.041 Uiso 1 1 calc R
H18B H 0.4620 0.2167 0.7099 0.041 Uiso 1 1 calc R
C19 C 0.40553(18) 0.16614(11) 0.5152(3) 0.0378(4) Uani 1 1 d .
H19A H 0.4458 0.1505 0.4281 0.057 Uiso 1 1 calc R
H19B H 0.3396 0.2016 0.4861 0.057 Uiso 1 1 calc R
H19C H 0.3673 0.1247 0.5604 0.057 Uiso 1 1 calc R
Li2 Li 0.6187(3) 0.05343(14) 0.5731(3) 0.0223(5) 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'
Li Li -0.0003 0.0001 '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'
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
C1 P1 C4 104.61(8) . .
C1 P1 C10 106.24(8) . .
C4 P1 C10 98.16(7) . .
C1 P1 Li2 120.34(8) . .
C4 P1 Li2 117.24(8) . .
C10 P1 Li2 107.56(8) . .
C16 O1 C18 111.14(14) . .
C16 O1 Li2 123.29(14) . .
C18 O1 Li2 124.71(14) . .
C2 C1 P1 118.66(12) . .
C2 C1 Li2 68.99(11) . 2_554
P1 C1 Li2 132.34(11) . 2_554
C3 C2 C1 127.45(16) . .
C3 C2 Li2 82.26(12) . 2_554
C1 C2 Li2 74.12(11) . 2_554
C2 C3 Li2 63.84(11) . 2_554
C5 C4 C9 118.38(14) . .
C5 C4 P1 120.80(12) . .
C9 C4 P1 120.81(12) . .
C4 C5 C6 120.51(15) . .
C7 C6 C5 120.31(16) . .
C6 C7 C8 119.78(15) . .
C9 C8 C7 119.89(15) . .
C8 C9 C4 121.14(15) . .
C15 C10 C11 118.51(14) . .
C15 C10 P1 120.59(13) . .
C11 C10 P1 120.80(13) . .
C12 C11 C10 120.32(17) . .
C13 C12 C11 120.21(18) . .
C14 C13 C12 120.28(15) . .
C13 C14 C15 119.78(17) . .
C10 C15 C14 120.89(17) . .
O1 C16 C17 109.30(15) . .
O1 C18 C19 109.66(15) . .
O1 Li2 C2 122.36(15) . 2
O1 Li2 C1 132.47(15) . 2
C2 Li2 C1 36.89(7) 2 2
O1 Li2 C3 126.28(15) . 2
C2 Li2 C3 33.90(7) 2 2
C1 Li2 C3 64.06(9) 2 2
O1 Li2 P1 101.78(11) . .
C2 Li2 P1 133.76(13) 2 .
C1 Li2 P1 118.83(12) 2 .
C3 Li2 P1 109.04(12) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.7614(17) .
P1 C4 1.8343(16) .
P1 C10 1.8508(15) .
P1 Li2 2.592(3) .
O1 C16 1.434(2) .
O1 C18 1.449(2) .
O1 Li2 1.962(3) .
C1 C2 1.417(2) .
C1 Li2 2.270(3) 2_554
C2 C3 1.369(2) .
C2 Li2 2.203(3) 2_554
C3 Li2 2.432(3) 2_554
C4 C5 1.390(2) .
C4 C9 1.403(2) .
C5 C6 1.398(2) .
C6 C7 1.384(3) .
C7 C8 1.389(3) .
C8 C9 1.384(2) .
C10 C15 1.394(2) .
C10 C11 1.399(2) .
C11 C12 1.393(3) .
C12 C13 1.384(3) .
C13 C14 1.377(3) .
C14 C15 1.396(2) .
C16 C17 1.501(3) .
C18 C19 1.492(3) .
Li2 C2 2.203(3) 2
Li2 C1 2.270(3) 2
Li2 C3 2.432(3) 2
