#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:15:32 +0100 (vie 25 de mar de 2016) $
#$Revision: 179806 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/02/7010219.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_7010219
loop_
_publ_author_name
'Henderson, Kenneth W.'
'Kennedy, Alan R.'
'McKeown, Arlene E.'
'Strachan, Diane'
_publ_section_title
;
 Lithiated α-cyanophosphonates: self-assembly of two-dimensional
 molecular sheets composed of interconnected twenty-four membered
 rings †
;
_journal_issue                   23
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              4348
_journal_paper_doi               10.1039/b007038f
_journal_year                    2000
_chemical_formula_sum            'C24 H46 Li2 N2 O8 P2'
_chemical_formula_weight         566.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.131(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.243(3)
_cell_length_b                   9.837(2)
_cell_length_c                   15.585(3)
_cell_measurement_reflns_used    18810
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     3258.8(10)
_computing_cell_refinement       'Denzo & Collect'
_computing_data_collection
;
Denzo & Collect (Otwinowski & Minor, 1997; Hooft & Nonius 1988)
;
_computing_data_reduction        'Denzo & Collect'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.446
_diffrn_measured_fraction_theta_max 0.446
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Phi & omega 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  0.0774
_diffrn_reflns_av_sigmaI/netI    0.1111
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4671
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         3.34
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav, Blessing 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0803P)²+10.2437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.2204
_reflns_number_gt                1353
_reflns_number_total             2432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b007038f.txt
_cod_data_source_block           ak61
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+10.2437P] where P=(Fo^2^+2Fc^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+10.2437P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7010219
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'
'-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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.69036(7) 0.09991(17) 0.60950(9) 0.0463(5) Uani 1 d . . .
O1 O 0.63658(17) 0.2043(4) 0.6117(2) 0.0580(11) Uani 1 d . . .
O2 O 0.64748(16) -0.0282(4) 0.5737(3) 0.0542(11) Uani 1 d . . .
O3 O 0.72081(16) 0.1569(4) 0.5442(2) 0.0482(10) Uani 1 d . . .
O4 O 0.63234(18) 0.3025(5) 0.3783(3) 0.0667(12) Uani 1 d . . .
N1 N 0.7197(2) -0.0792(6) 0.8310(3) 0.0623(14) Uani 1 d . . .
C1 C 0.7433(3) 0.0647(7) 0.7095(4) 0.0568(17) Uani 1 d . . .
H1 H 0.784(3) 0.102(8) 0.721(5) 0.10(2) Uiso 1 d . . .
C2 C 0.7303(3) -0.0138(6) 0.7752(4) 0.0515(15) Uani 1 d . . .
C3 C 0.6044(4) 0.1992(9) 0.6813(5) 0.089(3) Uani 1 d . A 1
H3 H 0.6256 0.1377 0.7324 0.106 Uiso 1 calc R A 1
C4 C 0.5332(7) 0.1489(16) 0.6259(12) 0.095(6) Uiso 0.63(3) d P A 1
H4A H 0.5142 0.2146 0.5783 0.143 Uiso 0.63(3) calc PR A 1
H4B H 0.5075 0.1425 0.6671 0.143 Uiso 0.63(3) calc PR A 1
H4C H 0.5353 0.0596 0.5991 0.143 Uiso 0.63(3) calc PR A 1
C4A C 0.5593(14) 0.101(3) 0.677(2) 0.104(11) Uiso 0.37(3) d P A 2
C5 C 0.5980(4) 0.3396(11) 0.7100(7) 0.122(4) Uani 1 d . A 1
H5A H 0.6394 0.3833 0.7285 0.184 Uiso 1 calc R A 1
H5B H 0.5803 0.3386 0.7606 0.184 Uiso 1 calc R A 1
H5C H 0.5699 0.3904 0.6599 0.184 Uiso 1 calc R A 1
C6 C 0.6743(3) -0.1592(7) 0.5625(5) 0.0702(19) Uani 1 d . . .
H6 H 0.7201 -0.1613 0.5967 0.084 Uiso 1 calc R . .
C7 C 0.6398(4) -0.2670(8) 0.5969(5) 0.086(2) Uani 1 d . . .
H7A H 0.6417 -0.2466 0.6592 0.129 Uiso 1 calc R . .
H7B H 0.6594 -0.3555 0.5943 0.129 Uiso 1 calc R . .
H7C H 0.5958 -0.2694 0.5597 0.129 Uiso 1 calc R . .
C8 C 0.6656(4) -0.1775(8) 0.4615(5) 0.096(3) Uani 1 d . . .
H8A H 0.6206 -0.1768 0.4288 0.144 Uiso 1 calc R . .
H8B H 0.6840 -0.2643 0.4514 0.144 Uiso 1 calc R . .
H8C H 0.6866 -0.1029 0.4400 0.144 Uiso 1 calc R . .
C9 C 0.5744(5) 0.2333(14) 0.3651(9) 0.085(4) Uiso 0.734(18) d P B 1
H9A H 0.5805 0.1483 0.4007 0.103 Uiso 0.734(18) calc PR B 1
H9B H 0.5552 0.2107 0.3009 0.103 Uiso 0.734(18) calc PR B 1
C10 C 0.5338(6) 0.3310(19) 0.3967(12) 0.117(5) Uiso 0.734(18) d P B 1
H10A H 0.4945 0.3463 0.3476 0.141 Uiso 0.734(18) calc PR B 1
H10B H 0.5224 0.2899 0.4477 0.141 Uiso 0.734(18) calc PR B 1
C11 C 0.5613(5) 0.4489(12) 0.4221(8) 0.086(4) Uiso 0.734(18) d P B 1
H11A H 0.5555 0.4769 0.4802 0.103 Uiso 0.734(18) calc PR B 1
H11B H 0.5428 0.5196 0.3768 0.103 Uiso 0.734(18) calc PR B 1
C12 C 0.6311(6) 0.4315(13) 0.4316(9) 0.072(4) Uiso 0.734(18) d P B 1
H12A H 0.6476 0.5101 0.4059 0.087 Uiso 0.734(18) calc PR B 1
H12B H 0.6560 0.4204 0.4953 0.087 Uiso 0.734(18) calc PR B 1
C9A C 0.5820(13) 0.183(3) 0.333(2) 0.077(10) Uiso 0.266(18) d P B 2
C10A C 0.5345(12) 0.229(3) 0.3963(18) 0.072(10) Uiso 0.266(18) d P B 2
C11A C 0.5330(13) 0.390(4) 0.359(2) 0.078(10) Uiso 0.266(18) d P B 2
C12A C 0.6151(14) 0.402(4) 0.418(2) 0.053(9) Uiso 0.266(18) d P B 2
Li1 Li 0.7130(4) 0.2096(9) 0.4225(6) 0.047(2) Uani 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
O3 P1 O2 114.1(2) . . ?
O3 P1 O1 105.6(2) . . ?
O2 P1 O1 98.3(2) . . ?
O3 P1 C1 112.0(3) . . ?
O2 P1 C1 110.2(3) . . ?
O1 P1 C1 116.0(3) . . ?
O3 P1 Li1 32.7(2) . 7_656 ?
O2 P1 Li1 145.8(2) . 7_656 ?
O1 P1 Li1 100.5(2) . 7_656 ?
C1 P1 Li1 86.7(3) . 7_656 ?
C3 O1 P1 122.0(4) . . ?
C6 O2 P1 121.6(3) . . ?
P1 O3 Li1 148.0(4) . . ?
P1 O3 Li1 122.6(3) . 7_656 ?
Li1 O3 Li1 85.5(4) . 7_656 ?
C12A O4 C9 92.8(16) . . ?
C12A O4 C12 16.0(15) . . ?
C9 O4 C12 108.5(8) . . ?
C12A O4 C9A 119.6(19) . . ?
C9 O4 C9A 27.5(11) . . ?
C12 O4 C9A 135.5(13) . . ?
C12A O4 Li1 124.6(15) . . ?
C9 O4 Li1 122.0(6) . . ?
C12 O4 Li1 111.1(6) . . ?
C9A O4 Li1 105.0(12) . . ?
C2 N1 Li1 170.3(6) . 6_556 ?
C2 C1 P1 124.0(5) . . ?
N1 C2 C1 179.5(6) . . ?
O1 C3 C5 107.8(7) . . ?
O1 C3 C4 103.1(7) . . ?
C5 C3 C4 106.1(8) . . ?
O2 C6 C7 108.3(5) . . ?
O2 C6 C8 107.1(6) . . ?
C7 C6 C8 111.1(6) . . ?
O4 C9 C10 104.8(11) . . ?
C11 C10 C9 113.2(12) . . ?
C10 C11 C12 107.4(11) . . ?
O4 C12 C11 102.8(9) . . ?
O4 C9A C10A 92(2) . . ?
C11A C10A C9A 90(2) . . ?
C10A C11A C12A 88(2) . . ?
O4 C12A C11A 97(2) . . ?
O3 Li1 O3 94.5(4) . 7_656 ?
O3 Li1 O4 106.3(4) . . ?
O3 Li1 O4 109.1(5) 7_656 . ?
O3 Li1 N1 122.5(5) . 6 ?
O3 Li1 N1 115.3(5) 7_656 6 ?
O4 Li1 N1 108.0(4) . 6 ?
O3 Li1 Li1 47.3(3) . 7_656 ?
O3 Li1 Li1 47.2(3) 7_656 7_656 ?
O4 Li1 Li1 116.6(6) . 7_656 ?
N1 Li1 Li1 135.3(6) 6 7_656 ?
O3 Li1 P1 118.1(4) . 7_656 ?
O3 Li1 P1 24.69(16) 7_656 7_656 ?
O4 Li1 P1 106.2(4) . 7_656 ?
N1 Li1 P1 94.4(3) 6 7_656 ?
Li1 Li1 P1 71.2(4) 7_656 7_656 ?
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 O3 1.488(4) . ?
P1 O2 1.580(4) . ?
P1 O1 1.585(4) . ?
P1 C1 1.689(6) . ?
P1 Li1 3.002(9) 7_656 ?
O1 C3 1.465(7) . ?
O2 C6 1.452(7) . ?
O3 Li1 1.925(9) . ?
O3 Li1 1.926(10) 7_656 ?
O4 C12A 1.27(3) . ?
O4 C9 1.419(12) . ?
O4 C12 1.522(13) . ?
O4 C9A 1.63(3) . ?
O4 Li1 1.949(9) . ?
N1 C2 1.160(7) . ?
N1 Li1 1.957(10) 6_556 ?
C1 C2 1.379(8) . ?
C3 C5 1.471(12) . ?
C3 C4 1.643(17) . ?
C6 C7 1.497(9) . ?
C6 C8 1.539(10) . ?
C9 C10 1.497(18) . ?
C10 C11 1.317(18) . ?
C11 C12 1.525(15) . ?
C9A C10A 1.70(4) . ?
C10A C11A 1.68(5) . ?
C11A C12A 1.79(4) . ?
Li1 O3 1.926(10) 7_656 ?
Li1 N1 1.957(10) 6 ?
Li1 Li1 2.615(17) 7_656 ?
Li1 P1 3.002(9) 7_656 ?
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
_geom_torsion_publ_flag
O3 P1 O1 C3 -167.0(5) . . . . ?
O2 P1 O1 C3 75.0(5) . . . . ?
C1 P1 O1 C3 -42.4(6) . . . . ?
Li1 P1 O1 C3 -133.8(5) 7_656 . . . ?
O3 P1 O2 C6 71.4(5) . . . . ?
O1 P1 O2 C6 -177.3(4) . . . . ?
C1 P1 O2 C6 -55.6(5) . . . . ?
Li1 P1 O2 C6 60.1(6) 7_656 . . . ?
O2 P1 O3 Li1 43.7(7) . . . . ?
O1 P1 O3 Li1 -63.1(7) . . . . ?
C1 P1 O3 Li1 169.8(7) . . . . ?
Li1 P1 O3 Li1 -148.1(7) 7_656 . . . ?
O2 P1 O3 Li1 -168.2(4) . . . 7_656 ?
O1 P1 O3 Li1 85.0(4) . . . 7_656 ?
C1 P1 O3 Li1 -42.1(5) . . . 7_656 ?
O3 P1 C1 C2 -166.1(5) . . . . ?
O2 P1 C1 C2 -37.9(7) . . . . ?
O1 P1 C1 C2 72.6(7) . . . . ?
Li1 P1 C1 C2 172.6(6) 7_656 . . . ?
Li1 N1 C2 C1 -97(78) 6_556 . . . ?
P1 C1 C2 N1 -143(77) . . . . ?
P1 O1 C3 C5 137.5(6) . . . . ?
P1 O1 C3 C4 -110.6(8) . . . . ?
P1 O2 C6 C7 137.3(4) . . . . ?
P1 O2 C6 C8 -102.9(5) . . . . ?
C12A O4 C9 C10 5.8(17) . . . . ?
C12 O4 C9 C10 9.2(12) . . . . ?
C9A O4 C9 C10 -162(3) . . . . ?
Li1 O4 C9 C10 140.2(9) . . . . ?
O4 C9 C10 C11 2.9(18) . . . . ?
C9 C10 C11 C12 -13.6(18) . . . . ?
C12A O4 C12 C11 -4(5) . . . . ?
C9 O4 C12 C11 -16.5(10) . . . . ?
C9A O4 C12 C11 -10.9(19) . . . . ?
Li1 O4 C12 C11 -153.2(7) . . . . ?
C10 C11 C12 O4 18.1(14) . . . . ?
C12A O4 C9A C10A -19(2) . . . . ?
C9 O4 C9A C10A -6(2) . . . . ?
C12 O4 C9A C10A -17(2) . . . . ?
Li1 O4 C9A C10A 126.7(13) . . . . ?
O4 C9A C10A C11A 54.0(17) . . . . ?
C9A C10A C11A C12A -66.0(19) . . . . ?
C9 O4 C12A C11A -30.0(18) . . . . ?
C12 O4 C12A C11A 162(7) . . . . ?
C9A O4 C12A C11A -24(3) . . . . ?
Li1 O4 C12A C11A -162.5(13) . . . . ?
C10A C11A C12A O4 57(2) . . . . ?
P1 O3 Li1 O3 153.5(6) . . . 7_656 ?
Li1 O3 Li1 O3 0.0 7_656 . . 7_656 ?
P1 O3 Li1 O4 42.1(9) . . . . ?
Li1 O3 Li1 O4 -111.4(6) 7_656 . . . ?
P1 O3 Li1 N1 -82.6(8) . . . 6 ?
Li1 O3 Li1 N1 123.9(7) 7_656 . . 6 ?
P1 O3 Li1 Li1 153.5(6) . . . 7_656 ?
P1 O3 Li1 P1 161.1(4) . . . 7_656 ?
Li1 O3 Li1 P1 7.64(17) 7_656 . . 7_656 ?
C12A O4 Li1 O3 53.2(18) . . . . ?
C9 O4 Li1 O3 -66.8(9) . . . . ?
C12 O4 Li1 O3 63.1(7) . . . . ?
C9A O4 Li1 O3 -90.5(13) . . . . ?
C12A O4 Li1 O3 -47.6(18) . . . 7_656 ?
C9 O4 Li1 O3 -167.6(7) . . . 7_656 ?
C12 O4 Li1 O3 -37.7(7) . . . 7_656 ?
C9A O4 Li1 O3 168.7(13) . . . 7_656 ?
C12A O4 Li1 N1 -173.6(17) . . . 6 ?
C9 O4 Li1 N1 66.4(9) . . . 6 ?
C12 O4 Li1 N1 -163.7(6) . . . 6 ?
C9A O4 Li1 N1 42.7(13) . . . 6 ?
C12A O4 Li1 Li1 3.3(19) . . . 7_656 ?
C9 O4 Li1 Li1 -116.6(9) . . . 7_656 ?
C12 O4 Li1 Li1 13.3(9) . . . 7_656 ?
C9A O4 Li1 Li1 -140.4(13) . . . 7_656 ?
C12A O4 Li1 P1 -73.4(17) . . . 7_656 ?
C9 O4 Li1 P1 166.7(7) . . . 7_656 ?
C12 O4 Li1 P1 -63.4(6) . . . 7_656 ?
C9A O4 Li1 P1 143.0(12) . . . 7_656 ?
