#------------------------------------------------------------------------------
#$Date: 2022-01-07 01:06:11 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271900 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243980.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_2243980
loop_
_publ_author_name
'Purdy, Andrew P.'
'Butcher, Ray J.'
'Klug, Christopher A.'
_publ_section_title
;
 The structures of 1:1 and 1:2 adducts of phosphanetricarbonitrile with
 1,4-diazabicyclo[2.2.2]octane
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1190
_journal_page_last               1196
_journal_paper_doi               10.1107/S2056989021011464
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          '2C6 H12 N2, C3 N3 P'
_chemical_formula_moiety         '2(C6 H12 N2), C3 N3 P'
_chemical_formula_sum            'C15 H24 N7 P'
_chemical_formula_weight         333.38
_chemical_name_systematic
;
Phosphanetricarbonitrile--1,4-diazabicyclo[2.2.2]octane (1/2)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.555(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5807(2)
_cell_length_b                   12.3447(4)
_cell_length_c                   10.7719(4)
_cell_measurement_reflns_used    4473
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      35.61
_cell_measurement_theta_min      2.56
_cell_volume                     846.99(5)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick 2015a)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19743
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.294
_diffrn_reflns_theta_min         2.557
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0492
_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)+(0.0428P)²+0.3013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                3117
_reflns_number_total             4235
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yy2005sup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2243980
_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   0.950
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.80141(5) 0.750000 0.71522(4) 0.01039(8) Uani d 1 . .
N N1 1.0735(2) 0.93032(11) 0.84218(11) 0.0353(3) Uani d 1 . .
N N2 1.0131(2) 0.750000 0.50118(14) 0.0236(3) Uani d 1 . .
N N3 0.74507(18) 0.750000 0.95248(11) 0.0113(2) Uani d 1 . .
N N4 0.6178(2) 0.750000 1.16108(12) 0.0163(2) Uani d 1 . .
C C1 0.97347(17) 0.85819(10) 0.79468(10) 0.0197(2) Uani d 1 . .
C C2 0.9308(2) 0.750000 0.58324(14) 0.0144(2) Uani d 1 . .
C C3 0.9244(2) 0.750000 1.06612(15) 0.0274(4) Uani d 1 . .
H H3A 1.011990 0.814906 1.064404 0.033 Uiso calc 0.5 A .
H H3B 1.011990 0.685094 1.064404 0.033 Uiso calc 0.5 . .
C C4 0.8482(3) 0.750000 1.19066(15) 0.0228(3) Uani d 1 . .
H H4A 0.903240 0.685090 1.242177 0.027 Uiso calc 0.5 . .
H H4B 0.903240 0.814910 1.242177 0.027 Uiso calc 0.5 . .
C C5 0.6170(2) 0.65328(10) 0.95859(12) 0.0249(3) Uani d 1 . .
H H5A 0.700901 0.587287 0.955230 0.030 Uiso calc 1 A .
H H5B 0.493677 0.652299 0.883705 0.030 Uiso calc 1 . .
C C6 0.54197(19) 0.65328(10) 1.08391(11) 0.0208(2) Uani d 1 . .
H H6A 0.386635 0.651568 1.062498 0.025 Uiso calc 1 . .
H H6B 0.594804 0.587526 1.134350 0.025 Uiso calc 1 . .
N N5 0.3804(14) 0.4230(7) 0.4470(5) 0.0112(8) Uani d 0.5 A -1
C C7 0.2606(3) 0.50627(17) 0.4901(2) 0.0145(3) Uani d 0.5 A -1
H H7A 0.167(4) 0.471(2) 0.533(3) 0.017 Uiso d 0.5 B -1
H H7B 0.174(4) 0.543(3) 0.417(2) 0.017 Uiso d 0.5 C -1
C C8 0.4094(3) 0.58402(16) 0.5834(2) 0.0133(3) Uani d 0.5 A -1
H H8A 0.400(7) 0.574(3) 0.670(2) 0.016 Uiso d 0.5 D -1
H H8B 0.369(4) 0.6579(15) 0.560(2) 0.016 Uiso d 0.5 E -1
C C9 0.5267(3) 0.37247(16) 0.5606(2) 0.0146(3) Uani d 0.5 A -1
H H9A 0.441(5) 0.344(3) 0.612(3) 0.017 Uiso d 0.5 F -1
H H9B 0.603(4) 0.3139(19) 0.535(3) 0.017 Uiso d 0.5 G -1
C C10 0.6913(3) 0.45691(16) 0.6299(2) 0.0134(3) Uani d 0.5 A -1
H H10A 0.827(3) 0.441(3) 0.618(3) 0.016 Uiso d 0.5 H -1
H H10B 0.698(4) 0.457(2) 0.7198(17) 0.016 Uiso d 0.5 I -1
C C11 0.5118(3) 0.47282(18) 0.3681(2) 0.0158(4) Uani d 0.5 A -1
H H11A 0.419(4) 0.496(2) 0.288(2) 0.019 Uiso d 0.5 J -1
H H11B 0.604(7) 0.419(3) 0.351(3) 0.019 Uiso d 0.5 K -1
C C12 0.6392(3) 0.56829(16) 0.44242(19) 0.0136(3) Uani d 0.5 A -1
H H12A 0.585(5) 0.634(2) 0.400(4) 0.016 Uiso d 0.5 L -1
H H12B 0.784(3) 0.562(2) 0.439(3) 0.016 Uiso d 0.5 M -1
N N5A 0.6268(14) 0.5681(7) 0.5797(5) 0.0104(7) Uani d 0.5 A -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 0.0000 0.0000 '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'
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
C1 P1 C1 4_575 . 94.44(8) y
C1 P1 C2 4_575 . 90.54(5) ?
C1 P1 C2 . . 90.54(5) y
C1 P1 N3 4_575 . 76.69(4) ?
C1 P1 N3 . . 76.69(4) y
C2 P1 N3 . . 160.98(5) y
C1 P1 N5A 4_575 . 77.25(16) y
C1 P1 N5A . . 166.15(18) y
C2 P1 N5A . . 78.62(14) y
N3 P1 N5A . . 111.45(11) y
C1 P1 N5A 4_575 4_575 166.15(18) y
C1 P1 N5A . 4_575 77.25(16) ?
C2 P1 N5A . 4_575 78.62(14) ?
N3 P1 N5A . 4_575 111.45(11) ?
N5A P1 N5A . 4_575 108.5(3) y
C3 N3 C5 . 4_575 108.14(8) ?
C3 N3 C5 . . 108.14(8) ?
C5 N3 C5 4_575 . 108.35(13) ?
C3 N3 P1 . . 121.36(9) ?
C5 N3 P1 4_575 . 105.14(7) ?
C5 N3 P1 . . 105.14(7) ?
C6 N4 C6 4_575 . 108.77(13) ?
C6 N4 C4 4_575 . 107.95(8) ?
C6 N4 C4 . . 107.95(8) ?
N1 C1 P1 . . 176.33(13) ?
N2 C2 P1 . . 179.54(13) ?
N3 C3 C4 . . 110.79(12) ?
N3 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
N3 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
N4 C4 C3 . . 110.72(12) ?
N4 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
N4 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
N3 C5 C6 . . 110.50(9) ?
N3 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
N3 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
N4 C6 C5 . . 110.84(9) ?
N4 C6 H6A . . 109.5 ?
C5 C6 H6A . . 109.5 ?
N4 C6 H6B . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
C7 N5 C11 . . 109.4(5) ?
C7 N5 C9 . . 109.1(4) ?
C11 N5 C9 . . 107.1(5) ?
N5 C7 C8 . . 110.1(4) ?
N5 C7 H7A . . 107.3(19) ?
C8 C7 H7A . . 110.3(19) ?
N5 C7 H7B . . 110(2) ?
C8 C7 H7B . . 113(2) ?
H7A C7 H7B . . 106.6(19) ?
N5A C8 C7 . . 111.4(4) ?
N5A C8 H8A . . 108(3) ?
C7 C8 H8A . . 112(3) ?
N5A C8 H8B . . 109.4(17) ?
C7 C8 H8B . . 109.1(17) ?
H8A C8 H8B . . 107(2) ?
N5 C9 C10 . . 110.0(4) ?
N5 C9 H9A . . 106(2) ?
C10 C9 H9A . . 114(3) ?
N5 C9 H9B . . 110.8(17) ?
C10 C9 H9B . . 107.1(17) ?
H9A C9 H9B . . 109(2) ?
N5A C10 C9 . . 110.0(4) ?
N5A C10 H10A . . 109(2) ?
C9 C10 H10A . . 111(2) ?
N5A C10 H10B . . 107.9(18) ?
C9 C10 H10B . . 109.5(17) ?
H10A C10 H10B . . 109(2) ?
N5 C11 C12 . . 109.6(3) ?
N5 C11 H11A . . 107.7(18) ?
C12 C11 H11A . . 112.0(17) ?
N5 C11 H11B . . 108(3) ?
C12 C11 H11B . . 110(3) ?
H11A C11 H11B . . 109(2) ?
N5A C12 C11 . . 110.6(4) ?
N5A C12 H12A . . 111(2) ?
C11 C12 H12A . . 108(3) ?
N5A C12 H12B . . 109.8(19) ?
C11 C12 H12B . . 109.4(19) ?
H12A C12 H12B . . 107(2) ?
C8 N5A C10 . . 107.7(5) ?
C8 N5A C12 . . 108.9(5) ?
C10 N5A C12 . . 106.1(5) ?
C8 N5A P1 . . 99.0(4) ?
C10 N5A P1 . . 120.7(4) ?
C12 N5A P1 . . 113.6(4) ?
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 C1 4_575 1.8197(11) ?
P1 C1 . 1.8197(11) y
P1 C2 . 1.8315(15) y
P1 N3 . 2.6731(12) y
P1 N5A . 2.766(9) y
P1 N5A 4_575 2.766(9) ?
N1 C1 . 1.1484(16) ?
N2 C2 . 1.147(2) ?
N3 C3 . 1.4713(19) ?
N3 C5 4_575 1.4725(13) ?
N3 C5 . 1.4726(13) ?
N4 C6 4_575 1.4687(14) ?
N4 C6 . 1.4687(14) ?
N4 C4 . 1.469(2) ?
C3 C4 . 1.546(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5494(15) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
N5 C7 . 1.441(9) ?
N5 C11 . 1.489(7) ?
N5 C9 . 1.490(7) ?
C7 C8 . 1.548(3) ?
C7 H7A . 0.967(16) ?
C7 H7B . 0.962(16) ?
C8 N5A . 1.455(9) ?
C8 H8A . 0.957(17) ?
C8 H8B . 0.966(16) ?
C9 C10 . 1.553(3) ?
C9 H9A . 0.949(17) ?
C9 H9B . 0.958(16) ?
C10 N5A . 1.497(8) ?
C10 H10A . 0.952(17) ?
C10 H10B . 0.958(16) ?
C11 C12 . 1.548(3) ?
C11 H11A . 0.964(16) ?
C11 H11B . 0.955(18) ?
C12 N5A . 1.501(5) ?
C12 H12A . 0.958(16) ?
C12 H12B . 0.965(16) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8B N2 1_455 0.966(16) 2.53(2) 3.260(2) 132(2) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N3 C3 C4 4_575 . . . 58.56(8) ?
C5 N3 C3 C4 . . . . -58.56(7) ?
P1 N3 C3 C4 . . . . 180.0000(10) ?
C6 N4 C4 C3 4_575 . . . -58.71(8) ?
C6 N4 C4 C3 . . . . 58.71(8) ?
N3 C3 C4 N4 . . . . 0.0000(10) ?
C3 N3 C5 C6 . . . . 58.18(13) ?
C5 N3 C5 C6 4_575 . . . -58.81(16) ?
P1 N3 C5 C6 . . . . -170.83(9) ?
C6 N4 C6 C5 4_575 . . . 57.90(15) ?
C4 N4 C6 C5 . . . . -58.99(13) ?
N3 C5 C6 N4 . . . . 0.48(15) ?
C11 N5 C7 C8 . . . . -65.9(4) ?
C9 N5 C7 C8 . . . . 51.0(5) ?
N5 C7 C8 N5A . . . . 13.2(3) ?
C7 N5 C9 C10 . . . . -65.1(5) ?
C11 N5 C9 C10 . . . . 53.2(6) ?
N5 C9 C10 N5A . . . . 12.1(2) ?
C7 N5 C11 C12 . . . . 51.6(5) ?
C9 N5 C11 C12 . . . . -66.5(6) ?
N5 C11 C12 N5A . . . . 11.5(2) ?
C7 C8 N5A C10 . . . . -65.4(4) ?
C7 C8 N5A C12 . . . . 49.2(6) ?
C7 C8 N5A P1 . . . . 168.13(15) ?
C9 C10 N5A C8 . . . . 50.3(4) ?
C9 C10 N5A C12 . . . . -66.2(5) ?
C9 C10 N5A P1 . . . . 162.7(3) ?
C11 C12 N5A C8 . . . . -62.7(6) ?
C11 C12 N5A C10 . . . . 53.0(6) ?
C11 C12 N5A P1 . . . . -172.0(2) ?

_cod_database_fobs_code 2243980
