#------------------------------------------------------------------------------
#$Date: 2017-02-04 15:55:35 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/13/7041355.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_7041355
loop_
_publ_author_name
'Hanf, S.'
'García-Rodríguez, R'
'Feldmann, S.'
'Bond, A. D.'
'Hey-Hawkins, E'
'Wright, D. S.'
_publ_section_title
;
 Multidentate 2-pyridyl-phosphine ligands - towards ligand tuning and
 chirality.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              814
_journal_page_last               824
_journal_paper_doi               10.1039/c6dt04390a
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C28 H34 Cl2 Li2 N4 O2 P2'
_chemical_formula_sum            'C28 H34 Cl2 Li2 N4 O2 P2'
_chemical_formula_weight         605.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-22 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.894(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1423(14)
_cell_length_b                   8.0771(6)
_cell_length_c                   22.2684(18)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      58.20
_cell_measurement_theta_min      4.11
_cell_volume                     3327.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33730
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        59.462
_diffrn_reflns_theta_max         59.462
_diffrn_reflns_theta_min         4.108
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.5975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0719
_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)+(0.0858P)²+13.7945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.2042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1687
_reflns_number_total             2405
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt04390a2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7041350--7041357.cif.'
_cod_database_code               7041355
_cambridge_user_name             'Schirin Hanf'
_cambridge_user_crsid            sh811
_cambridge_supervisor_name       'Dominic Wright'
_cambridge_supervisor_crsid      dsw1000
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             SH185
_cambridge_data_id               DW_B2_0127
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.639
_shelx_estimated_absorpt_t_max   0.723
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30175(7) 0.89470(17) 0.30535(6) 0.0622(5) Uani 1 1 d . . . . .
P1 P 0.15425(8) 0.7274(2) 0.42557(7) 0.0661(5) Uani 1 1 d . . . . .
O1 O 0.1021(2) 0.6864(6) 0.47044(17) 0.0793(12) Uani 1 1 d D . . . .
N1 N 0.1109(2) 0.8059(5) 0.3046(2) 0.0618(12) Uani 1 1 d . . . . .
N2 N 0.2032(2) 0.5111(6) 0.3533(2) 0.0661(13) Uani 1 1 d . . . . .
Li1 Li 0.2072(5) 0.7109(12) 0.2949(5) 0.067(2) Uani 1 1 d . . . . .
C1 C 0.1217(4) 0.7718(8) 0.5321(3) 0.055(3) Uani 0.649(15) 1 d D U P A 1
H1A H 0.1719 0.7414 0.5555 0.066 Uiso 0.649(15) 1 calc R U P A 1
C2 C 0.1130(5) 0.9670(8) 0.5280(4) 0.114(3) Uani 0.649(15) 1 d D U P A 1
H2A H 0.1267 1.0141 0.5700 0.171 Uiso 0.649(15) 1 calc R U P A 1
H2B H 0.1443 1.0123 0.5035 0.171 Uiso 0.649(15) 1 calc R U P A 1
H2C H 0.0626 0.9951 0.5081 0.171 Uiso 0.649(15) 1 calc R U P A 1
C3 C 0.0666(5) 0.7057(9) 0.5660(4) 0.070(3) Uani 0.649(15) 1 d D U P A 1
H3A H 0.0166 0.7231 0.5405 0.084 Uiso 0.649(15) 1 calc R U P A 1
H3B H 0.0724 0.7629 0.6063 0.084 Uiso 0.649(15) 1 calc R U P A 1
C4 C 0.0828(5) 0.5188(8) 0.5762(4) 0.133(3) Uani 0.649(15) 1 d D U P A 1
H4A H 0.0491 0.4699 0.5978 0.199 Uiso 0.649(15) 1 calc R U P A 1
H4B H 0.0770 0.4642 0.5359 0.199 Uiso 0.649(15) 1 calc R U P A 1
H4C H 0.1325 0.5038 0.6014 0.199 Uiso 0.649(15) 1 calc R U P A 1
C1A C 0.1108(11) 0.6564(12) 0.5379(5) 0.120(10) Uani 0.351(15) 1 d D U P A 2
H1B H 0.1634 0.6720 0.5586 0.144 Uiso 0.351(15) 1 calc R U P A 2
C2A C 0.0828(5) 0.5188(8) 0.5762(4) 0.133(3) Uani 0.351(15) 1 d D U P A 2
H2D H 0.1004 0.5423 0.6207 0.199 Uiso 0.351(15) 1 calc R U P A 2
H2E H 0.0298 0.5182 0.5645 0.199 Uiso 0.351(15) 1 calc R U P A 2
H2F H 0.1007 0.4104 0.5672 0.199 Uiso 0.351(15) 1 calc R U P A 2
C3A C 0.0731(9) 0.8201(12) 0.5465(10) 0.097(8) Uani 0.351(15) 1 d D U P A 2
H3C H 0.0226 0.8184 0.5206 0.116 Uiso 0.351(15) 1 calc R U P A 2
H3D H 0.0719 0.8317 0.5905 0.116 Uiso 0.351(15) 1 calc R U P A 2
C4A C 0.1130(5) 0.9670(8) 0.5280(4) 0.114(3) Uani 0.351(15) 1 d D U P A 2
H4D H 0.0883 1.0698 0.5337 0.171 Uiso 0.351(15) 1 calc R U P A 2
H4E H 0.1627 0.9694 0.5541 0.171 Uiso 0.351(15) 1 calc R U P A 2
H4F H 0.1135 0.9562 0.4843 0.171 Uiso 0.351(15) 1 calc R U P A 2
C11 C 0.0857(3) 0.7929(7) 0.3553(3) 0.0588(14) Uani 1 1 d . . . . .
C12 C 0.0165(3) 0.8382(9) 0.3558(3) 0.0806(19) Uani 1 1 d . . . . .
H12 H 0.0008 0.8293 0.3928 0.097 Uiso 1 1 calc R U . . .
C13 C -0.0299(4) 0.8967(9) 0.3019(3) 0.092(2) Uani 1 1 d . . . . .
H13 H -0.0782 0.9267 0.3011 0.111 Uiso 1 1 calc R U . . .
C14 C -0.0052(4) 0.9106(9) 0.2501(4) 0.092(2) Uani 1 1 d . . . . .
H14 H -0.0355 0.9538 0.2127 0.111 Uiso 1 1 calc R U . . .
C15 C 0.0636(4) 0.8617(8) 0.2524(3) 0.0801(18) Uani 1 1 d . . . . .
H15 H 0.0792 0.8670 0.2153 0.096 Uiso 1 1 calc R U . . .
C21 C 0.1705(3) 0.5183(7) 0.3994(3) 0.0701(16) Uani 1 1 d . . . . .
C22 C 0.1545(6) 0.3770(10) 0.4283(5) 0.141(4) Uani 1 1 d . . . . .
H22 H 0.1308 0.3835 0.4609 0.169 Uiso 1 1 calc R U . . .
C23 C 0.1738(9) 0.2287(12) 0.4088(6) 0.190(6) Uani 1 1 d . . . . .
H23 H 0.1644 0.1301 0.4286 0.228 Uiso 1 1 calc R U . . .
C24 C 0.2062(6) 0.2188(10) 0.3616(5) 0.132(3) Uani 1 1 d . . . . .
H24 H 0.2190 0.1147 0.3477 0.159 Uiso 1 1 calc R U . . .
C25 C 0.2199(4) 0.3616(8) 0.3348(3) 0.085(2) Uani 1 1 d . . . . .
H25 H 0.2423 0.3556 0.3014 0.102 Uiso 1 1 calc R U . . .
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'
Li Li 0.0008 0.0003 '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
Li1 Cl1 Li1 78.9(4) . 7_565
O1 P1 C21 100.9(3) . .
O1 P1 C11 99.5(2) . .
C21 P1 C11 97.8(3) . .
C1A O1 P1 136.9(8) . .
C1 O1 P1 115.1(4) . .
C11 N1 C15 116.3(5) . .
C11 N1 Li1 125.8(5) . .
C15 N1 Li1 116.9(5) . .
C21 N2 C25 118.1(5) . .
C21 N2 Li1 123.1(5) . .
C25 N2 Li1 117.1(5) . .
N1 Li1 N2 92.6(4) . .
N1 Li1 Cl1 116.8(4) . .
N2 Li1 Cl1 126.0(5) . .
N1 Li1 Cl1 112.7(5) . 7_565
N2 Li1 Cl1 107.8(4) . 7_565
Cl1 Li1 Cl1 101.1(4) . 7_565
N1 Li1 Li1 131.1(6) . 7_565
N2 Li1 Li1 134.5(6) . 7_565
Cl1 Li1 Li1 51.3(3) . 7_565
Cl1 Li1 Li1 49.8(3) 7_565 7_565
O1 C1 C3 104.4(5) . .
O1 C1 C2 114.1(6) . .
C3 C1 C2 107.3(5) . .
O1 C1 H1A 110.3 . .
C3 C1 H1A 110.3 . .
C2 C1 H1A 110.3 . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 C4 105.9(6) . .
C1 C3 H3A 110.6 . .
C4 C3 H3A 110.6 . .
C1 C3 H3B 110.6 . .
C4 C3 H3B 110.6 . .
H3A C3 H3B 108.7 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O1 C1A C3A 92.9(10) . .
O1 C1A C2A 134.0(11) . .
C3A C1A C2A 107.6(8) . .
O1 C1A H1B 106.4 . .
C3A C1A H1B 106.4 . .
C2A C1A H1B 106.4 . .
C1A C2A H2D 109.5 . .
C1A C2A H2E 109.5 . .
H2D C2A H2E 109.5 . .
C1A C2A H2F 109.5 . .
H2D C2A H2F 109.5 . .
H2E C2A H2F 109.5 . .
C4A C3A C1A 110.5(9) . .
C4A C3A H3C 109.5 . .
C1A C3A H3C 109.5 . .
C4A C3A H3D 109.5 . .
C1A C3A H3D 109.5 . .
H3C C3A H3D 108.1 . .
C3A C4A H4D 109.5 . .
C3A C4A H4E 109.5 . .
H4D C4A H4E 109.5 . .
C3A C4A H4F 109.5 . .
H4D C4A H4F 109.5 . .
H4E C4A H4F 109.5 . .
N1 C11 C12 122.7(6) . .
N1 C11 P1 113.9(4) . .
C12 C11 P1 123.2(5) . .
C11 C12 C13 119.4(6) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C14 C13 C12 118.7(6) . .
C14 C13 H13 120.7 . .
C12 C13 H13 120.7 . .
C13 C14 C15 119.1(7) . .
C13 C14 H14 120.5 . .
C15 C14 H14 120.5 . .
N1 C15 C14 123.8(6) . .
N1 C15 H15 118.1 . .
C14 C15 H15 118.1 . .
N2 C21 C22 121.8(6) . .
N2 C21 P1 115.8(4) . .
C22 C21 P1 122.3(5) . .
C23 C22 C21 117.8(8) . .
C23 C22 H22 121.1 . .
C21 C22 H22 121.1 . .
C24 C23 C22 121.2(8) . .
C24 C23 H23 119.4 . .
C22 C23 H23 119.4 . .
C25 C24 C23 118.1(8) . .
C25 C24 H24 121.0 . .
C23 C24 H24 121.0 . .
N2 C25 C24 122.9(7) . .
N2 C25 H25 118.6 . .
C24 C25 H25 118.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 Li1 2.306(10) .
Cl1 Li1 2.354(10) 7_565
P1 O1 1.618(4) .
P1 C21 1.840(6) .
P1 C11 1.842(6) .
O1 C1A 1.489(9) .
O1 C1 1.495(7) .
N1 C11 1.341(6) .
N1 C15 1.354(8) .
N1 Li1 2.059(11) .
N2 C21 1.333(7) .
N2 C25 1.341(7) .
N2 Li1 2.086(11) .
Li1 Cl1 2.354(10) 7_565
Li1 Li1 2.961(19) 7_565
C1 C3 1.542(7) .
C1 C2 1.586(7) .
C1 H1A 1.0000 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 C4 1.546(8) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C1A C3A 1.542(10) .
C1A C2A 1.577(9) .
C1A H1B 1.0000 .
C2A H2D 0.9800 .
C2A H2E 0.9800 .
C2A H2F 0.9800 .
C3A C4A 1.524(9) .
C3A H3C 0.9900 .
C3A H3D 0.9900 .
C4A H4D 0.9800 .
C4A H4E 0.9800 .
C4A H4F 0.9800 .
C11 C12 1.377(8) .
C12 C13 1.379(9) .
C12 H12 0.9500 .
C13 C14 1.360(9) .
C13 H13 0.9500 .
C14 C15 1.363(9) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C21 C22 1.383(9) .
C22 C23 1.358(12) .
C22 H22 0.9500 .
C23 C24 1.352(12) .
C23 H23 0.9500 .
C24 C25 1.355(10) .
C24 H24 0.9500 .
C25 H25 0.9500 .
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
C21 P1 O1 C1A 94.1(8)
C11 P1 O1 C1A -165.9(7)
C21 P1 O1 C1 133.4(5)
C11 P1 O1 C1 -126.6(4)
P1 O1 C1 C3 -177.4(4)
P1 O1 C1 C2 65.8(7)
O1 C1 C3 C4 65.3(8)
C2 C1 C3 C4 -173.3(7)
P1 O1 C1A C3A 111.2(10)
P1 O1 C1A C2A -130.8(14)
O1 C1A C3A C4A -58.9(16)
C2A C1A C3A C4A 162.9(12)
C15 N1 C11 C12 -2.1(8)
Li1 N1 C11 C12 -170.4(6)
C15 N1 C11 P1 -176.8(4)
Li1 N1 C11 P1 14.9(7)
O1 P1 C11 N1 -167.9(4)
C21 P1 C11 N1 -65.4(4)
O1 P1 C11 C12 17.4(6)
C21 P1 C11 C12 119.9(5)
N1 C11 C12 C13 1.2(10)
P1 C11 C12 C13 175.5(5)
C11 C12 C13 C14 -1.2(11)
C12 C13 C14 C15 2.0(12)
C11 N1 C15 C14 3.0(9)
Li1 N1 C15 C14 172.4(7)
C13 C14 C15 N1 -3.1(12)
C25 N2 C21 C22 0.6(10)
Li1 N2 C21 C22 165.4(8)
C25 N2 C21 P1 176.4(5)
Li1 N2 C21 P1 -18.8(7)
O1 P1 C21 N2 169.7(4)
C11 P1 C21 N2 68.4(5)
O1 P1 C21 C22 -14.5(8)
C11 P1 C21 C22 -115.8(8)
N2 C21 C22 C23 0.7(16)
P1 C21 C22 C23 -174.8(10)
C21 C22 C23 C24 -1(2)
C22 C23 C24 C25 1(2)
C21 N2 C25 C24 -1.2(11)
Li1 N2 C25 C24 -166.9(8)
C23 C24 C25 N2 0.5(16)
