#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/98/2239860.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_2239860
loop_
_publ_author_name
'Stöger, Berthold'
'Weil, Matthias'
'Bichler, Bernhard'
'Eder, Wolfgang'
'Kirchner, Karl'
_publ_section_title
;
 Crystal structure of
 N,N'-bis(diisopropylphosphanyl)-4-methylpyridine-2,6-diamine
;
_journal_coeditor_code           SU0004
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o889
_journal_page_last               o890
_journal_paper_doi               10.1107/S1600536814010976
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H35 N3 P2'
_chemical_formula_moiety         'C18 H35 N3 P2'
_chemical_formula_sum            'C18 H35 N3 P2'
_chemical_formula_weight         355.4
_chemical_name_systematic
;
N,N'-Bis(diisopropylphosphanyl)-4-methylpyridine-2,6-diamine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   none
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3394(12)
_cell_length_b                   10.0089(16)
_cell_length_c                   29.562(3)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    100
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.5
_cell_volume                     4242.8(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
'JANA2006 (Petříček, et al., 2014)'
_computing_structure_solution
'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            149837
_diffrn_reflns_theta_full        30.14
_diffrn_reflns_theta_max         30.14
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.1125
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.39
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    132
_refine_ls_number_parameters     216
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.0138
_refine_ls_shift/su_mean         0.0007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(σ²(F)+0.0004F²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0457
_reflns_number_gt                4614
_reflns_number_total             6241
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            su0004sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom,difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        4242.9(9)
_cod_database_code               2239860
_cod_database_fobs_code          2239860
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z+1/2
4 x+1/2,-y+1/2,-z
5 -x,-y,-z
6 x+1/2,y,-z+1/2
7 x,-y+1/2,z+1/2
8 -x+1/2,y+1/2,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_occupancy
P P1 0.781952(19) 0.61761(3) 0.277629(10) 0.01628(8) Uani d 1
P P2 0.62798(2) 0.33177(3) 0.045775(10) 0.01837(8) Uani d 1
N N1 0.70180(6) 0.42925(9) 0.16952(3) 0.0149(2) Uani d 1
N N2 0.73728(7) 0.50053(10) 0.24153(3) 0.0176(3) Uani d 1
N N3 0.66959(7) 0.33964(10) 0.10001(3) 0.0200(3) Uani d 1
C C1 0.69814(7) 0.52954(11) 0.19953(4) 0.0146(3) Uani d 1
C C2 0.65663(7) 0.65213(11) 0.19012(4) 0.0166(3) Uani d 1
C C3 0.61705(7) 0.67148(11) 0.14781(4) 0.0164(3) Uani d 1
C C4 0.62017(8) 0.56884(11) 0.11637(4) 0.0180(3) Uani d 1
C C5 0.66312(7) 0.44882(11) 0.12890(4) 0.0158(3) Uani d 1
C C6 0.57228(8) 0.80360(11) 0.13652(4) 0.0220(3) Uani d 1
C C7 0.76791(8) 0.52642(12) 0.33135(4) 0.0211(3) Uani d 1
C C8 0.66449(9) 0.50783(15) 0.34168(5) 0.0326(4) Uani d 1
C C9 0.81669(11) 0.60387(14) 0.36929(4) 0.0321(4) Uani d 1
C C10 0.90932(8) 0.60456(12) 0.26658(4) 0.0207(3) Uani d 1
C C11 0.92671(9) 0.64908(13) 0.21773(4) 0.0280(4) Uani d 1
C C12 0.95354(8) 0.46787(12) 0.27535(4) 0.0251(3) Uani d 1
C C13 0.71074(8) 0.20717(12) 0.02331(4) 0.0196(3) Uani d 1
C C14 0.80702(9) 0.27110(14) 0.01819(4) 0.0304(4) Uani d 1
C C15 0.67652(9) 0.15302(14) -0.02210(4) 0.0288(4) Uani d 1
C C16 0.51998(8) 0.23173(12) 0.05297(4) 0.0218(3) Uani d 1
C C17 0.44882(9) 0.31763(15) 0.07830(5) 0.0322(4) Uani d 1
C C18 0.53214(9) 0.09667(13) 0.07581(4) 0.0285(4) Uani d 1
H H1c2 0.655417 0.721798 0.212436 0.0199 Uiso d 1
H H1c4 0.593587 0.579767 0.086795 0.0216 Uiso d 1
H H1c6 0.531526 0.829737 0.160715 0.0264 Uiso d 1
H H2c6 0.619791 0.870155 0.132575 0.0264 Uiso d 1
H H3c6 0.536997 0.795035 0.109071 0.0264 Uiso d 1
H H1c7 0.795933 0.439591 0.328992 0.0253 Uiso d 1
H H1c8 0.634885 0.463114 0.316796 0.0392 Uiso d 1
H H2c8 0.657585 0.4551 0.368598 0.0392 Uiso d 1
H H3c8 0.635919 0.593558 0.346145 0.0392 Uiso d 1
H H1c9 0.88155 0.614221 0.362035 0.0386 Uiso d 1
H H2c9 0.788416 0.690318 0.372402 0.0386 Uiso d 1
H H3c9 0.810676 0.555582 0.397193 0.0386 Uiso d 1
H H1c10 0.939505 0.661523 0.288221 0.0248 Uiso d 1
H H1c11 0.897622 0.734181 0.212703 0.0336 Uiso d 1
H H2c11 0.992597 0.656607 0.212556 0.0336 Uiso d 1
H H3c11 0.900823 0.584359 0.197319 0.0336 Uiso d 1
H H1c12 0.950231 0.447657 0.307053 0.0302 Uiso d 1
H H2c12 0.920525 0.400794 0.258548 0.0302 Uiso d 1
H H3c12 1.017612 0.469408 0.265948 0.0302 Uiso d 1
H H1c13 0.714996 0.133665 0.044067 0.0235 Uiso d 1
H H1c14 0.823637 0.315444 0.045839 0.0365 Uiso d 1
H H2c14 0.852243 0.203124 0.011583 0.0365 Uiso d 1
H H3c14 0.805635 0.334884 -0.006051 0.0365 Uiso d 1
H H1c15 0.620148 0.103025 -0.0176 0.0345 Uiso d 1
H H2c15 0.664577 0.226133 -0.042306 0.0345 Uiso d 1
H H3c15 0.723356 0.095883 -0.034922 0.0345 Uiso d 1
H H1c16 0.498808 0.208867 0.023147 0.0262 Uiso d 1
H H1c17 0.440136 0.400466 0.062477 0.0386 Uiso d 1
H H2c17 0.390461 0.270903 0.080008 0.0386 Uiso d 1
H H3c17 0.471218 0.335423 0.108302 0.0386 Uiso d 1
H H1c18 0.569613 0.039846 0.056995 0.0343 Uiso d 1
H H2c18 0.562348 0.108617 0.104509 0.0343 Uiso d 1
H H3c18 0.472136 0.056297 0.080352 0.0343 Uiso d 1
H H1n3 0.6939(10) 0.2689(9) 0.1124(5) 0.042(4) Uiso d 1
H H1n2 0.7548(9) 0.4176(4) 0.2438(5) 0.027(4) Uiso d 1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.1023 0.0942 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 P1 C7 99.06(5)
N2 P1 C10 102.14(5)
C7 P1 C10 102.93(5)
N3 P2 C13 98.28(5)
N3 P2 C16 102.02(5)
C13 P2 C16 102.31(5)
C1 N1 C5 117.93(9)
P1 N2 C1 124.36(8)
P1 N2 H1n2 119.8(9)
C1 N2 H1n2 112.7(9)
P2 N3 C5 126.02(8)
P2 N3 H1n3 119.7(9)
C5 N3 H1n3 114.1(9)
N1 C1 N2 114.71(9)
N1 C1 C2 122.99(10)
N2 C1 C2 122.29(10)
C1 C2 C3 118.57(10)
C1 C2 H1c2 120.71
C3 C2 H1c2 120.71
C2 C3 C4 119.21(10)
C2 C3 C6 119.76(10)
C4 C3 C6 121.02(10)
C3 C4 C5 118.21(10)
C3 C4 H1c4 120.89
C5 C4 H1c4 120.89
N1 C5 N3 114.13(9)
N1 C5 C4 123.08(10)
N3 C5 C4 122.78(10)
C3 C6 H1c6 109.47
C3 C6 H2c6 109.47
C3 C6 H3c6 109.47
H1c6 C6 H2c6 109.47
H1c6 C6 H3c6 109.47
H2c6 C6 H3c6 109.47
P1 C7 C8 109.83(8)
P1 C7 C9 109.29(8)
P1 C7 H1c7 109.89
C8 C7 C9 111.03(10)
C8 C7 H1c7 108.11
C9 C7 H1c7 108.66
C7 C8 H1c8 109.47
C7 C8 H2c8 109.47
C7 C8 H3c8 109.47
H1c8 C8 H2c8 109.47
H1c8 C8 H3c8 109.47
H2c8 C8 H3c8 109.47
C7 C9 H1c9 109.47
C7 C9 H2c9 109.47
C7 C9 H3c9 109.47
H1c9 C9 H2c9 109.47
H1c9 C9 H3c9 109.47
H2c9 C9 H3c9 109.47
P1 C10 C11 107.76(8)
P1 C10 C12 116.11(8)
P1 C10 H1c10 106.5
C11 C10 C12 110.63(10)
C11 C10 H1c10 112.45
C12 C10 H1c10 103.38
C10 C11 H1c11 109.47
C10 C11 H2c11 109.47
C10 C11 H3c11 109.47
H1c11 C11 H2c11 109.47
H1c11 C11 H3c11 109.47
H2c11 C11 H3c11 109.47
C10 C12 H1c12 109.47
C10 C12 H2c12 109.47
C10 C12 H3c12 109.47
H1c12 C12 H2c12 109.47
H1c12 C12 H3c12 109.47
H2c12 C12 H3c12 109.47
P2 C13 C14 109.48(9)
P2 C13 C15 110.44(8)
P2 C13 H1c13 109.19
C14 C13 C15 110.57(10)
C14 C13 H1c13 109.06
C15 C13 H1c13 108.06
C13 C14 H1c14 109.47
C13 C14 H2c14 109.47
C13 C14 H3c14 109.47
H1c14 C14 H2c14 109.47
H1c14 C14 H3c14 109.47
H2c14 C14 H3c14 109.47
C13 C15 H1c15 109.47
C13 C15 H2c15 109.47
C13 C15 H3c15 109.47
H1c15 C15 H2c15 109.47
H1c15 C15 H3c15 109.47
H2c15 C15 H3c15 109.47
P2 C16 C17 108.02(9)
P2 C16 C18 115.76(8)
P2 C16 H1c16 106.69
C17 C16 C18 111.01(10)
C17 C16 H1c16 111.87
C18 C16 H1c16 103.42
C16 C17 H1c17 109.47
C16 C17 H2c17 109.47
C16 C17 H3c17 109.47
H1c17 C17 H2c17 109.47
H1c17 C17 H3c17 109.47
H2c17 C17 H3c17 109.47
C16 C18 H1c18 109.47
C16 C18 H2c18 109.47
C16 C18 H3c18 109.47
H1c18 C18 H2c18 109.47
H1c18 C18 H3c18 109.47
H2c18 C18 H3c18 109.47
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 N2 1.7094(10)
P1 C7 1.8426(12)
P1 C10 1.8599(12)
P2 N3 1.7125(11)
P2 C13 1.8452(12)
P2 C16 1.8564(12)
N1 C1 1.3408(14)
N1 C5 1.3372(14)
N2 C1 1.3932(14)
N2 H1n2 0.870(6)
N3 C5 1.3901(15)
N3 H1n3 0.870(11)
C1 C2 1.3918(16)
C2 C3 1.3872(16)
C2 H1c2 0.96
C3 C4 1.3861(16)
C3 C6 1.5074(16)
C4 C5 1.3998(16)
C4 H1c4 0.96
C6 H1c6 0.96
C6 H2c6 0.96
C6 H3c6 0.96
C7 C8 1.5256(17)
C7 C9 1.5324(18)
C7 H1c7 0.96
C8 H1c8 0.96
C8 H2c8 0.96
C8 H3c8 0.96
C9 H1c9 0.96
C9 H2c9 0.96
C9 H3c9 0.96
C10 C11 1.5319(18)
C10 C12 1.5300(17)
C10 H1c10 0.96
C11 H1c11 0.96
C11 H2c11 0.96
C11 H3c11 0.96
C12 H1c12 0.96
C12 H2c12 0.96
C12 H3c12 0.96
C13 C14 1.5292(18)
C13 C15 1.5286(17)
C13 H1c13 0.96
C14 H1c14 0.96
C14 H2c14 0.96
C14 H3c14 0.96
C15 H1c15 0.96
C15 H2c15 0.96
C15 H3c15 0.96
C16 C17 1.5301(18)
C16 C18 1.5212(18)
C16 H1c16 0.96
C17 H1c17 0.96
C17 H2c17 0.96
C17 H3c17 0.96
C18 H1c18 0.96
C18 H2c18 0.96
C18 H3c18 0.96
