#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:34:36 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179977 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/71/7027116.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7027116
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Churakov, Andrei V.'
'Easson, Morag A. M.'
'Govenlock, Linda J.'
'Howard, Judith A. K.'
'Moloney, Janet M.'
'Parker, David'
_publ_section_title
;
 Dimethylthiophosphoryl hydrazone ligands and their copper complexes:
 crystal structures and analysis of their solution complexation behaviour
 by electrospray mass spectrometry
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              323
_journal_paper_doi               10.1039/a807142j
_journal_year                    1999
_chemical_formula_sum            'C18 H24 N4 P2 S2'
_chemical_formula_weight         422.47
_chemical_melting_point_gt       523
_chemical_name_systematic
; 
 butane-2,3-bis[(dimethylthiophosphoryl)hydrazide] 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                69.43(1)
_cell_angle_beta                 87.11(1)
_cell_angle_gamma                69.74(1)
_cell_formula_units_Z            2
_cell_length_a                   9.588(1)
_cell_length_b                   11.402(1)
_cell_length_c                   11.620(1)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      1.9
_cell_volume                     1112.1(2)
_computing_cell_refinement       'Siemens SMART'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    SHELXTL-PLUS
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'Siemens SMART CCD detector'
_diffrn_measurement_method       'ω scans'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4911
_diffrn_reflns_theta_max         25.52
_diffrn_reflns_theta_min         1.88
_diffrn_standards_interval_time  '12 hours'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   'semi-empirical (equivalents)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       fragment
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0099(22)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.054
_refine_ls_goodness_of_fit_obs   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_restrained_S_obs      1.040
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_obs          0.0324
_refine_ls_shift/esd_max         -0.006
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.046P)²+0.67P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0944
_refine_ls_wR_factor_obs         0.0846
_reflns_number_observed          3319
_reflns_number_total             3567
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            807142jsup1.cif
_cod_data_source_block           L1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>523 K' was changed to
'523' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.046P)^2^+0.67P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.046P)^2^+0.67P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               7027116
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
P1 P 0.69368(5) 0.70560(5) 0.35561(4) 0.0266(2) Uani 1 d
P2 P 0.23889(5) 0.84935(5) 0.58372(4) 0.0279(2) Uani 1 d
S1 S 0.61337(7) 0.89428(5) 0.25709(5) 0.0421(2) Uani 1 d
S2 S 0.13232(6) 0.76538(5) 0.51888(5) 0.0398(2) Uani 1 d
N1 N 0.7176(2) 0.5633(2) 0.59346(14) 0.0287(4) Uani 1 d
N2 N 0.6933(2) 0.6879(2) 0.5054(2) 0.0365(4) Uani 1 d
H2N H 0.6627(25) 0.7567(25) 0.5242(21) 0.038(6) Uiso 1 d
N3 N 0.4993(2) 0.7602(2) 0.71320(14) 0.0282(4) Uani 1 d
N4 N 0.4029(2) 0.7301(2) 0.6535(2) 0.0324(4) Uani 1 d
H4N H 0.4361(25) 0.6630(24) 0.6323(21) 0.036(6) Uiso 1 d
C1 C 0.6925(2) 0.5554(2) 0.7057(2) 0.0247(4) Uani 1 d
C2 C 0.6348(2) 0.6770(2) 0.7423(2) 0.0251(4) Uani 1 d
C3 C 0.5894(4) 0.6085(3) 0.3401(3) 0.0560(7) Uani 1 d
H3A H 0.5928(33) 0.6144(30) 0.2601(30) 0.068(9) Uiso 1 d
H3B H 0.4876(42) 0.6536(36) 0.3596(32) 0.091(11) Uiso 1 d
H3C H 0.6348(32) 0.5170(32) 0.3920(28) 0.065(8) Uiso 1 d
C4 C 0.8820(3) 0.6182(3) 0.3352(3) 0.0606(8) Uani 1 d
H4A H 0.8865(35) 0.6259(32) 0.2517(33) 0.080(10) Uiso 1 d
H4B H 0.9209(35) 0.5232(35) 0.3883(31) 0.077(9) Uiso 1 d
H4C H 0.9391(48) 0.6617(42) 0.3517(39) 0.116(16) Uiso 1 d
C5 C 0.1500(2) 0.9142(2) 0.6980(2) 0.0345(5) Uani 1 d
H5A H 0.0591(29) 0.9876(26) 0.6646(23) 0.050(7) Uiso 1 d
H5B H 0.2132(28) 0.9449(24) 0.7294(23) 0.047(7) Uiso 1 d
H5C H 0.1243(27) 0.8475(27) 0.7615(25) 0.050(7) Uiso 1 d
C6 C 0.2823(3) 0.9844(2) 0.4719(2) 0.0410(5) Uani 1 d
H6A H 0.1896(29) 1.0566(26) 0.4407(23) 0.047(7) Uiso 1 d
H6B H 0.3299(27) 0.9552(24) 0.4111(23) 0.045(7) Uiso 1 d
H6C H 0.3465(30) 1.0111(26) 0.5146(24) 0.054(7) Uiso 1 d
C11 C 0.7129(2) 0.4223(2) 0.7996(2) 0.0242(4) Uani 1 d
C12 C 0.7776(2) 0.3057(2) 0.7727(2) 0.0294(4) Uani 1 d
H12 H 0.8095(23) 0.3092(20) 0.6981(21) 0.029(5) Uiso 1 d
C13 C 0.7859(2) 0.1828(2) 0.8584(2) 0.0358(5) Uani 1 d
H13 H 0.8294(26) 0.1089(25) 0.8393(21) 0.042(6) Uiso 1 d
C14 C 0.7303(3) 0.1739(2) 0.9725(2) 0.0386(5) Uani 1 d
H14 H 0.7339(26) 0.0956(26) 1.0266(23) 0.045(6) Uiso 1 d
C15 C 0.6673(2) 0.2882(2) 1.0007(2) 0.0346(4) Uani 1 d
H15 H 0.6284(26) 0.2845(23) 1.0799(23) 0.042(6) Uiso 1 d
C16 C 0.6587(2) 0.4119(2) 0.9153(2) 0.0287(4) Uani 1 d
H16 H 0.6167(24) 0.4900(23) 0.9345(20) 0.035(6) Uiso 1 d
C21 C 0.7366(2) 0.7009(2) 0.8163(2) 0.0263(4) Uani 1 d
C22 C 0.8900(2) 0.6386(2) 0.8197(2) 0.0366(5) Uani 1 d
H22 H 0.9279(26) 0.5834(24) 0.7719(22) 0.045(6) Uiso 1 d
C23 C 0.9859(3) 0.6573(2) 0.8916(2) 0.0434(5) Uani 1 d
H23 H 1.0884(32) 0.6136(26) 0.8904(24) 0.056(7) Uiso 1 d
C24 C 0.9301(3) 0.7379(2) 0.9601(2) 0.0414(5) Uani 1 d
H24 H 0.9995(27) 0.7506(23) 1.0087(22) 0.043(6) Uiso 1 d
C25 C 0.7785(3) 0.8007(2) 0.9568(2) 0.0407(5) Uani 1 d
H25 H 0.7389(27) 0.8568(24) 1.0035(23) 0.047(7) Uiso 1 d
C26 C 0.6809(2) 0.7830(2) 0.8854(2) 0.0337(4) Uani 1 d
H26 H 0.5794(27) 0.8275(23) 0.8824(20) 0.039(6) Uiso 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'
S S 0.1246 0.1234 '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 P1 C3 104.85(13)
N2 P1 C4 105.03(12)
C3 P1 C4 105.6(2)
N2 P1 S1 108.72(7)
C3 P1 S1 115.42(9)
C4 P1 S1 116.21(11)
N4 P2 C5 105.77(10)
N4 P2 C6 106.82(10)
C5 P2 C6 104.97(11)
N4 P2 S2 107.18(6)
C5 P2 S2 115.52(8)
C6 P2 S2 115.86(9)
C1 N1 N2 118.1(2)
N1 N2 P1 119.30(13)
C2 N3 N4 117.9(2)
N3 N4 P2 119.89(13)
N1 C1 C11 118.2(2)
N1 C1 C2 122.5(2)
C11 C1 C2 119.17(15)
N3 C2 C21 118.8(2)
N3 C2 C1 122.4(2)
C21 C2 C1 118.8(2)
C16 C11 C12 118.7(2)
C16 C11 C1 120.0(2)
C12 C11 C1 121.2(2)
C13 C12 C11 120.5(2)
C12 C13 C14 120.2(2)
C15 C14 C13 119.8(2)
C14 C15 C16 120.3(2)
C15 C16 C11 120.4(2)
C22 C21 C26 119.0(2)
C22 C21 C2 119.9(2)
C26 C21 C2 121.0(2)
C23 C22 C21 120.3(2)
C24 C23 C22 120.4(2)
C25 C24 C23 119.8(2)
C24 C25 C26 120.6(2)
C25 C26 C21 120.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 N2 1.680(2)
P1 C3 1.784(2)
P1 C4 1.785(3)
P1 S1 1.9346(8)
P2 N4 1.689(2)
P2 C5 1.782(2)
P2 C6 1.794(2)
P2 S2 1.9469(7)
N1 C1 1.292(2)
N1 N2 1.376(2)
N3 C2 1.291(2)
N3 N4 1.380(2)
C1 C11 1.478(3)
C1 C2 1.506(2)
C2 C21 1.483(3)
C11 C16 1.397(3)
C11 C12 1.397(3)
C12 C13 1.383(3)
C13 C14 1.387(3)
C14 C15 1.381(3)
C15 C16 1.387(3)
C21 C22 1.390(3)
C21 C26 1.394(3)
C22 C23 1.388(3)
C23 C24 1.377(3)
C24 C25 1.376(3)
C25 C26 1.390(3)
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
S1 P1 N2 N1 167.36(13)
P1 N2 N1 C1 -168.68(14)
N2 N1 C1 C2 1.4(3)
N1 C1 C2 N3 71.9(2)
C1 C2 N3 N4 4.4(3)
C2 N3 N4 P2 -165.62(14)
N3 N4 P2 S2 -177.05(13)
