#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:13:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178684 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/95/4079596.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_4079596
loop_
_publ_author_name
'Marchenko, Anatoliy P.'
'Koidan, Heorgiy N.'
'Zarudnitskii, Evgeniy V.'
'Hurieva, Anastasiya N.'
'Kirilchuk, Andrey A.'
'Yurchenko, Aleksandr A.'
'Biffis, Andrea'
'Kostyuk, Aleksandr N.'
_publ_section_title
;
 Stable N-Phosphorylated 1,2,4-Triazol-5-ylidenes: Novel Ligands for Metal
 Complexes
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              8257
_journal_paper_doi               10.1021/om300872g
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C19 H30 N3 P'
_chemical_formula_sum            'C19 H30 N3 P'
_chemical_formula_weight         331.43
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.9559(6)
_cell_length_b                   11.4221(4)
_cell_length_c                   21.7288(8)
_cell_measurement_temperature    296(2)
_cell_volume                     3960.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22122
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    costr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+3.2088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1579
_reflns_number_gt                2493
_reflns_number_total             4065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300872g_si_001.cif
_cod_data_source_block           z1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4079596
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.02829(18) 0.2941(3) 0.30135(13) 0.0286(7) Uani 1 1 d .
C2 C -0.06934(17) 0.4225(3) 0.33379(13) 0.0233(6) Uani 1 1 d .
C3 C -0.0675(2) 0.3678(3) 0.21977(13) 0.0381(8) Uani 1 1 d .
H3 H -0.1219 0.4077 0.2197 0.046 Uiso 1 1 calc R
C4 C -0.0801(2) 0.2458(3) 0.19385(15) 0.0500(10) Uani 1 1 d .
H4A H -0.1191 0.2037 0.2192 0.075 Uiso 1 1 calc R
H4B H -0.0274 0.2053 0.1932 0.075 Uiso 1 1 calc R
H4C H -0.1017 0.2513 0.1527 0.075 Uiso 1 1 calc R
C5 C -0.0071(3) 0.4396(4) 0.18141(16) 0.0611(12) Uani 1 1 d .
H5A H -0.0010 0.5160 0.1993 0.092 Uiso 1 1 calc R
H5B H -0.0284 0.4469 0.1403 0.092 Uiso 1 1 calc R
H5C H 0.0465 0.4014 0.1804 0.092 Uiso 1 1 calc R
C6 C -0.14300(17) 0.5012(3) 0.33370(13) 0.0235(6) Uani 1 1 d .
C7 C -0.1474(2) 0.5985(3) 0.29580(14) 0.0330(8) Uani 1 1 d .
H7 H -0.1044 0.6138 0.2680 0.040 Uiso 1 1 calc R
C8 C -0.2156(2) 0.6729(3) 0.29921(16) 0.0422(9) Uani 1 1 d .
H8 H -0.2172 0.7395 0.2746 0.051 Uiso 1 1 calc R
C9 C -0.2813(2) 0.6495(3) 0.33876(15) 0.0391(8) Uani 1 1 d .
H9 H -0.3278 0.6987 0.3401 0.047 Uiso 1 1 calc R
C10 C -0.2770(2) 0.5527(3) 0.37604(15) 0.0348(8) Uani 1 1 d .
H10 H -0.3207 0.5363 0.4030 0.042 Uiso 1 1 calc R
C11 C -0.20789(18) 0.4793(3) 0.37385(14) 0.0284(7) Uani 1 1 d .
H11 H -0.2053 0.4146 0.3998 0.034 Uiso 1 1 calc R
C12 C 0.18714(18) 0.3945(3) 0.40983(15) 0.0321(7) Uani 1 1 d .
C13 C 0.1506(2) 0.5107(3) 0.43039(19) 0.0484(10) Uani 1 1 d .
H13A H 0.1042 0.5310 0.4043 0.073 Uiso 1 1 calc R
H13B H 0.1928 0.5704 0.4277 0.073 Uiso 1 1 calc R
H13C H 0.1316 0.5043 0.4722 0.073 Uiso 1 1 calc R
C14 C 0.2617(2) 0.3613(3) 0.44969(18) 0.0494(10) Uani 1 1 d .
H14A H 0.2844 0.2881 0.4358 0.074 Uiso 1 1 calc R
H14B H 0.2439 0.3538 0.4917 0.074 Uiso 1 1 calc R
H14C H 0.3038 0.4211 0.4468 0.074 Uiso 1 1 calc R
C15 C 0.2186(2) 0.4083(4) 0.34305(17) 0.0587(11) Uani 1 1 d .
H15A H 0.1726 0.4298 0.3169 0.088 Uiso 1 1 calc R
H15B H 0.2420 0.3356 0.3292 0.088 Uiso 1 1 calc R
H15C H 0.2607 0.4683 0.3415 0.088 Uiso 1 1 calc R
C16 C 0.0645(2) 0.2358(3) 0.48259(13) 0.0294(7) Uani 1 1 d .
C17 C -0.0148(2) 0.1651(3) 0.46897(18) 0.0540(10) Uani 1 1 d .
H17A H -0.0534 0.2124 0.4460 0.081 Uiso 1 1 calc R
H17B H -0.0404 0.1415 0.5070 0.081 Uiso 1 1 calc R
H17C H -0.0004 0.0969 0.4454 0.081 Uiso 1 1 calc R
C18 C 0.0404(2) 0.3407(3) 0.52299(15) 0.0416(9) Uani 1 1 d .
H18A H 0.0023 0.3903 0.5009 0.062 Uiso 1 1 calc R
H18B H 0.0898 0.3841 0.5335 0.062 Uiso 1 1 calc R
H18C H 0.0138 0.3132 0.5599 0.062 Uiso 1 1 calc R
C19 C 0.1249(3) 0.1586(4) 0.51931(17) 0.0607(12) Uani 1 1 d .
H19A H 0.1750 0.2019 0.5282 0.091 Uiso 1 1 calc R
H19B H 0.1388 0.0904 0.4956 0.091 Uiso 1 1 calc R
H19C H 0.0987 0.1352 0.5571 0.091 Uiso 1 1 calc R
N1 N -0.02694(15) 0.3985(2) 0.38348(11) 0.0259(6) Uani 1 1 d .
N2 N 0.03374(14) 0.3177(2) 0.36211(10) 0.0258(6) Uani 1 1 d .
N3 N -0.03747(14) 0.3619(2) 0.28383(10) 0.0263(6) Uani 1 1 d .
P1 P 0.11599(5) 0.26277(7) 0.40653(3) 0.0267(2) Uani 1 1 d .
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
N2 C1 N3 102.1(2)
N1 C2 N3 110.7(2)
N1 C2 C6 122.8(2)
N3 C2 C6 126.5(2)
N3 C3 C4 110.6(3)
N3 C3 C5 109.7(3)
C4 C3 C5 112.2(3)
C11 C6 C7 119.0(3)
C11 C6 C2 119.1(3)
C7 C6 C2 121.9(3)
C6 C7 C8 120.1(3)
C9 C8 C7 120.8(3)
C10 C9 C8 119.0(3)
C9 C10 C11 120.5(3)
C6 C11 C10 120.7(3)
C13 C12 C14 110.6(3)
C13 C12 C15 108.2(3)
C14 C12 C15 107.9(3)
C13 C12 P1 118.5(2)
C14 C12 P1 107.1(2)
C15 C12 P1 104.0(2)
C17 C16 C19 108.5(3)
C17 C16 C18 108.4(3)
C19 C16 C18 108.0(3)
C17 C16 P1 106.2(2)
C19 C16 P1 106.2(2)
C18 C16 P1 119.1(2)
C2 N1 N2 102.7(2)
C1 N2 N1 114.0(2)
C1 N2 P1 121.1(2)
N1 N2 P1 124.54(18)
C1 N3 C2 110.4(2)
C1 N3 C3 122.8(2)
C2 N3 C3 126.7(2)
N2 P1 C16 102.54(13)
N2 P1 C12 100.78(13)
C16 P1 C12 111.23(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.350(3)
C1 N3 1.359(4)
C2 N1 1.303(3)
C2 N3 1.385(3)
C2 C6 1.479(4)
C3 N3 1.474(4)
C3 C4 1.516(5)
C3 C5 1.516(5)
C6 C11 1.377(4)
C6 C7 1.385(4)
C7 C8 1.383(4)
C8 C9 1.382(5)
C9 C10 1.373(4)
C10 C11 1.386(4)
C12 C13 1.517(4)
C12 C14 1.519(4)
C12 C15 1.544(5)
C12 P1 1.886(3)
C16 C17 1.530(5)
C16 C19 1.530(4)
C16 C18 1.534(4)
C16 P1 1.872(3)
N1 N2 1.416(3)
N2 P1 1.746(2)
