#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/10/2221059.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221059
loop_
_publ_author_name
'Berners-Price, Susan J.'
'Navarro, Maribel'
'Skelton, Brian W.'
_publ_section_title
;
 1,2-Bis(di-2-pyridylphosphinoyl)ethane
;
_journal_coeditor_code           FJ2193
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o542
_journal_paper_doi               10.1107/S1600536809004590
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H20 N4 O2 P2'
_chemical_formula_moiety         'C22 H20 N4 O2 P2'
_chemical_formula_sum            'C22 H20 N4 O2 P2'
_chemical_formula_weight         434.36
_chemical_name_systematic
;
1,2-Bis(di-2-pyridylphosphinoyl)ethane
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.627(7)
_cell_angle_beta                 92.429(5)
_cell_angle_gamma                112.559(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3760(6)
_cell_length_b                   8.8496(8)
_cell_length_c                   16.2332(11)
_cell_measurement_reflns_used    2539
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      32.6159
_cell_measurement_theta_min      3.2726
_cell_volume                     1055.67(16)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Gemini
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10983
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2219
_exptl_crystal_size_mid          0.0966
_exptl_crystal_size_min          0.0554
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)² ] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                2698
_reflns_number_total             4842
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2193.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
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 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     -p_1
_cod_database_code               2221059
_cod_database_fobs_code          2221059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.18196(9) 0.21056(9) 0.45935(4) 0.02233(18) Uani d . 1 . .
O O1 0.3253(2) 0.3074(2) 0.53572(11) 0.0272(4) Uani d . 1 . .
C C111 0.2511(3) 0.0876(3) 0.37091(16) 0.0217(6) Uani d . 1 . .
N N112 0.1239(3) -0.0366(3) 0.30732(14) 0.0267(5) Uani d . 1 . .
C C113 0.1759(4) -0.1218(4) 0.24034(17) 0.0320(7) Uani d . 1 . .
H H113 0.0879 -0.2109 0.195 0.038 Uiso calc R 1 . .
C C114 0.3487(4) -0.0891(4) 0.23254(18) 0.0320(7) Uani d . 1 . .
H H114 0.3782 -0.1528 0.1831 0.038 Uiso calc R 1 . .
C C115 0.4767(4) 0.0385(4) 0.29857(19) 0.0372(8) Uani d . 1 . .
H H115 0.5969 0.0641 0.2957 0.045 Uiso calc R 1 . .
C C116 0.4284(3) 0.1287(4) 0.36902(18) 0.0313(7) Uani d . 1 . .
H H116 0.5146 0.2172 0.4153 0.038 Uiso calc R 1 . .
C C121 0.1197(3) 0.3509(3) 0.41523(15) 0.0227(6) Uani d . 1 . .
N N122 -0.0518(3) 0.2959(3) 0.38395(15) 0.0300(6) Uani d . 1 . .
C C123 -0.0959(4) 0.4009(4) 0.35135(19) 0.0352(7) Uani d . 1 . .
H H123 -0.216 0.3661 0.3298 0.042 Uiso calc R 1 . .
C C124 0.0236(4) 0.5571(4) 0.34727(17) 0.0310(7) Uani d . 1 . .
H H124 -0.0142 0.6263 0.3228 0.037 Uiso calc R 1 . .
C C125 0.1972(4) 0.6111(4) 0.37892(17) 0.0316(7) Uani d . 1 . .
H H125 0.2816 0.7184 0.3773 0.038 Uiso calc R 1 . .
C C126 0.2464(3) 0.5055(3) 0.41316(16) 0.0256(6) Uani d . 1 . .
H H126 0.3659 0.5388 0.4351 0.031 Uiso calc R 1 . .
C C10 -0.0180(3) 0.0583(3) 0.47773(16) 0.0242(6) Uani d . 1 . .
H H10A -0.0786 0.121 0.5142 0.029 Uiso calc R 1 . .
H H10B -0.0962 -0.0124 0.4216 0.029 Uiso calc R 1 . .
P P2 0.68020(8) 0.27338(9) 0.04404(4) 0.02132(18) Uani d . 1 . .
O O2 0.7095(2) 0.3187(2) -0.03767(11) 0.0278(4) Uani d . 1 . .
C C211 0.6499(3) 0.4398(3) 0.12649(16) 0.0213(6) Uani d . 1 . .
N N212 0.6135(3) 0.4071(3) 0.20118(14) 0.0279(5) Uani d . 1 . .
C C213 0.6005(4) 0.5335(4) 0.26420(18) 0.0327(7) Uani d . 1 . .
H H213 0.5758 0.5138 0.3179 0.039 Uiso calc R 1 . .
C C214 0.6210(3) 0.6903(4) 0.2556(2) 0.0358(7) Uani d . 1 . .
H H214 0.6111 0.7759 0.3025 0.043 Uiso calc R 1 . .
C C215 0.6559(3) 0.7211(4) 0.1781(2) 0.0347(7) Uani d . 1 . .
H H215 0.6695 0.8277 0.1702 0.042 Uiso calc R 1 . .
C C216 0.6707(3) 0.5931(4) 0.11223(19) 0.0299(7) Uani d . 1 . .
H H216 0.6949 0.61 0.058 0.036 Uiso calc R 1 . .
C C221 0.8672(3) 0.2545(3) 0.09411(16) 0.0218(6) Uani d . 1 . .
N N222 0.8365(3) 0.1354(3) 0.13511(14) 0.0285(5) Uani d . 1 . .
C C223 0.9776(4) 0.1286(4) 0.17259(18) 0.0335(7) Uani d . 1 . .
H H223 0.9594 0.0457 0.2022 0.04 Uiso calc R 1 . .
C C224 1.1484(4) 0.2342(4) 0.17114(18) 0.0330(7) Uani d . 1 . .
H H224 1.2439 0.2227 0.1984 0.04 Uiso calc R 1 . .
C C225 1.1771(3) 0.3559(4) 0.12949(18) 0.0342(7) Uani d . 1 . .
H H225 1.2929 0.4316 0.1281 0.041 Uiso calc R 1 . .
C C226 1.0340(3) 0.3661(4) 0.08959(17) 0.0278(6) Uani d . 1 . .
H H226 1.0498 0.4481 0.0596 0.033 Uiso calc R 1 . .
C C20 0.4938(3) 0.0766(3) 0.03363(16) 0.0212(6) Uani d . 1 . .
H H20A 0.4874 0.0554 0.0905 0.025 Uiso calc R 1 . .
H H20B 0.3853 0.0876 0.0159 0.025 Uiso calc R 1 . .
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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 C10 . . 115.87(11) ?
O1 P1 C121 . . 112.56(12) ?
C10 P1 C121 . . 105.88(12) ?
O1 P1 C111 . . 110.98(11) ?
C10 P1 C111 . . 105.53(12) ?
C121 P1 C111 . . 105.23(11) ?
N112 C111 C116 . . 123.1(2) ?
N112 C111 P1 . . 116.64(18) ?
C116 C111 P1 . . 120.2(2) ?
C113 N112 C111 . . 116.4(2) ?
N112 C113 C114 . . 124.6(3) ?
N112 C113 H113 . . 117.7 ?
C114 C113 H113 . . 117.7 ?
C115 C114 C113 . . 118.0(3) ?
C115 C114 H114 . . 121 ?
C113 C114 H114 . . 121 ?
C114 C115 C116 . . 119.3(3) ?
C114 C115 H115 . . 120.4 ?
C116 C115 H115 . . 120.4 ?
C115 C116 C111 . . 118.7(3) ?
C115 C116 H116 . . 120.6 ?
C111 C116 H116 . . 120.6 ?
N122 C121 C126 . . 123.0(2) ?
N122 C121 P1 . . 117.2(2) ?
C126 C121 P1 . . 119.86(19) ?
C123 N122 C121 . . 116.5(2) ?
N122 C123 C124 . . 123.6(3) ?
N122 C123 H123 . . 118.2 ?
C124 C123 H123 . . 118.2 ?
C125 C124 C123 . . 119.3(3) ?
C125 C124 H124 . . 120.4 ?
C123 C124 H124 . . 120.4 ?
C124 C125 C126 . . 118.4(3) ?
C124 C125 H125 . . 120.8 ?
C126 C125 H125 . . 120.8 ?
C125 C126 C121 . . 119.3(2) ?
C125 C126 H126 . . 120.4 ?
C121 C126 H126 . . 120.4 ?
C10 C10 P1 2_556 . 111.2(2) ?
C10 C10 H10A 2_556 . 109.4 ?
P1 C10 H10A . . 109.4 ?
C10 C10 H10B 2_556 . 109.4 ?
P1 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108 ?
O2 P2 C20 . . 115.28(11) ?
O2 P2 C211 . . 111.60(12) ?
C20 P2 C211 . . 106.06(11) ?
O2 P2 C221 . . 112.89(11) ?
C20 P2 C221 . . 106.09(12) ?
C211 P2 C221 . . 104.05(11) ?
N212 C211 C216 . . 123.4(2) ?
N212 C211 P2 . . 116.2(2) ?
C216 C211 P2 . . 120.4(2) ?
C213 N212 C211 . . 116.5(2) ?
N212 C213 C214 . . 123.8(3) ?
N212 C213 H213 . . 118.1 ?
C214 C213 H213 . . 118.1 ?
C215 C214 C213 . . 119.1(3) ?
C215 C214 H214 . . 120.5 ?
C213 C214 H214 . . 120.5 ?
C214 C215 C216 . . 118.2(3) ?
C214 C215 H215 . . 120.9 ?
C216 C215 H215 . . 120.9 ?
C215 C216 C211 . . 119.0(3) ?
C215 C216 H216 . . 120.5 ?
C211 C216 H216 . . 120.5 ?
N222 C221 C226 . . 123.4(2) ?
N222 C221 P2 . . 118.23(18) ?
C226 C221 P2 . . 118.36(19) ?
C223 N222 C221 . . 116.2(2) ?
N222 C223 C224 . . 124.3(3) ?
N222 C223 H223 . . 117.8 ?
C224 C223 H223 . . 117.8 ?
C225 C224 C223 . . 118.6(2) ?
C225 C224 H224 . . 120.7 ?
C223 C224 H224 . . 120.7 ?
C224 C225 C226 . . 118.7(3) ?
C224 C225 H225 . . 120.6 ?
C226 C225 H225 . . 120.6 ?
C225 C226 C221 . . 118.8(2) ?
C225 C226 H226 . . 120.6 ?
C221 C226 H226 . . 120.6 ?
C20 C20 P2 2_655 . 111.1(2) ?
C20 C20 H20A 2_655 . 109.4 ?
P2 C20 H20A . . 109.4 ?
C20 C20 H20B 2_655 . 109.4 ?
P2 C20 H20B . . 109.4 ?
H20A C20 H20B . . 108 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.4917(18) ?
P1 C10 . 1.799(3) ?
P1 C121 . 1.809(3) ?
P1 C111 . 1.815(3) ?
C111 N112 . 1.344(3) ?
C111 C116 . 1.391(3) ?
N112 C113 . 1.339(3) ?
C113 C114 . 1.381(4) ?
C113 H113 . 0.95 ?
C114 C115 . 1.377(4) ?
C114 H114 . 0.95 ?
C115 C116 . 1.380(4) ?
C115 H115 . 0.95 ?
C116 H116 . 0.95 ?
C121 N122 . 1.352(3) ?
C121 C126 . 1.383(4) ?
N122 C123 . 1.339(3) ?
C123 C124 . 1.382(4) ?
C123 H123 . 0.95 ?
C124 C125 . 1.371(4) ?
C124 H124 . 0.95 ?
C125 C126 . 1.381(4) ?
C125 H125 . 0.95 ?
C126 H126 . 0.95 ?
C10 C10 2_556 1.516(5) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
P2 O2 . 1.4897(18) ?
P2 C20 . 1.798(2) ?
P2 C211 . 1.811(3) ?
P2 C221 . 1.819(3) ?
C211 N212 . 1.341(3) ?
C211 C216 . 1.384(4) ?
N212 C213 . 1.340(3) ?
C213 C214 . 1.378(4) ?
C213 H213 . 0.95 ?
C214 C215 . 1.378(4) ?
C214 H214 . 0.95 ?
C215 C216 . 1.382(4) ?
C215 H215 . 0.95 ?
C216 H216 . 0.95 ?
C221 N222 . 1.343(3) ?
C221 C226 . 1.386(3) ?
N222 C223 . 1.336(3) ?
C223 C224 . 1.382(4) ?
C223 H223 . 0.95 ?
C224 C225 . 1.372(4) ?
C224 H224 . 0.95 ?
C225 C226 . 1.383(4) ?
C225 H225 . 0.95 ?
C226 H226 . 0.95 ?
C20 C20 2_655 1.536(5) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
