#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/97/2009734.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_2009734
loop_
_publ_author_name
'Engelhardt, U.'
'Rosefid, M.'
_publ_section_title
;
 Ein Zwölfring mit Phosphor(V), Kohlenstoff und Dimethylhydrazin als
 Ringbausteinen und grossen endocyclischen Torsionswinkeln um die
 N--N-Bindungen
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              775
_journal_page_last               777
_journal_paper_doi               10.1107/S0108270193008844
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C22 H34 N8 O4 P2 S2'
_chemical_formula_weight         600.63
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_type_scat_source
' Cromer & Mann (1968); Stewart, Davidson & Simpson (1965)'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.647(5)
_cell_length_b                   11.738(2)
_cell_length_c                   11.415(3)
_cell_measurement_reflns_used    78
_cell_measurement_temperature    293
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      5
_cell_volume                     2900.5(11)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.01
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1989
_diffrn_reflns_theta_max         22
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.27
_exptl_absorpt_correction_type   keine
_exptl_crystal_colour            Farblos
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       Prismenförmig
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.1
_refine_diff_density_min         -1.2
_refine_ls_extinction_coef       1.27(7)
_refine_ls_extinction_method     isotrop
_refine_ls_goodness_of_fit_obs   1.22
_refine_ls_hydrogen_treatment    'siehe Text'
_refine_ls_number_parameters     373
_refine_ls_number_reflns         '1618 mit F~c~> F~o~'
_refine_ls_R_factor_obs          0.053
_refine_ls_shift/esd_max         '0.30 [U~22~ C(22)]'
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/σ²(Fₒ)
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.031
_reflns_number_observed          1162
_reflns_number_total             1888
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sh1063.cif
_cod_data_source_block           '_structure_1_of_1'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=1/\s^2^(F~o~)' 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^(F~o~)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2900(2)
_cod_database_code               2009734
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
S(1) .51100(10) .2047(3) .1766 .078(2)
S(2) .7754(2) .2427(3) .7577(4) .083(2)
P(3) .57460(10) .1820(2) .2922(4) .053(2)
P(9) .72300(10) .1948(2) .6322(4) .048(2)
O(1) .5801(3) .2746(5) .3939(6) .043(4)
O(2) .6880(3) .2903(5) .5592(5) .049(5)
O(6) .7345(3) .3206(6) .2898(7) .072(6)
O(12) .5527(3) .1762(6) .6602(8) .069(6)
N(1) .5383(4) .0794(7) .4890(10) .060(7)
N(2) .5686(4) .0658(7) .3820(10) .061(7)
N(4) .6437(4) .1710(6) .2316(8) .051(6)
N(5) .6925(4) .1443(7) .3097(8) .054(7)
N(7) .7757(4) .1972(7) .4228(9) .054(6)
N(8) .7558(4) .1293(7) .5164(8) .048(6)
N(10) .6700(4) .1022(6) .6781(9) .052(6)
N(11) .6300(4) .0632(7) .5933(8) .046(6)
C(1) .4740(5) .1140(10) .4850(10) .096(10)
C(2) .5505(5) -.0380(10) .3190(10) .071(9)
C(4) .6576(6) .1830(10) .1100(10) .096(11)
C(5) .7120(5) .0218(8) .2980(10) .066(8)
C(6) .7338(5) .2280(10) .3380(10) .049(8)
C(7) .8251(5) .2751(8) .4470(10) .087(10)
C(8) .7994(4) .0370(10) .5470(10) .075(10)
C(10) .6579(5) .0730(10) .8030(10) .083(10)
C(11) .6390(5) -.0601(9) .5690(10) .080(9)
C(12) .5715(5) .1127(9) .5870(10) .046(9)
C(13) .5596(4) .3878(8) .3830(10) .036(7)
C(14) .5780(5) .4560(10) .2950(10) .052(8)
C(15) .5569(7) .5680(10) .294(2) .095(13)
C(16) .5207(7) .6120(10) .380(2) .095(13)
C(17) .5031(6) .5400(10) .470(2) .072(11)
C(18) .5219(6) .4280(10) .4730(10) .059(9)
C(20) .6718(4) .3952(9) .6010(10) .040(7)
C(21) .6875(5) .4860(10) .5297(9) .043(7)
C(22) .6674(6) .5960(10) .562(2) .068(10)
C(23) .6319(6) .6120(10) .6620(10) .071(10)
C(24) .6167(5) .5180(10) .7290(10) .069(9)
C(25) .6348(5) .4090(10) .6980(10) .048(8)
H(1401) .614(4) .425(7) .243(7) ?
H(1501) .564(5) .611(8) .216(9) ?
H(1601) .496(4) .698(8) .342(9) ?
H(1701) .478(4) .567(8) .534(8) ?
H(1801) .515(5) .390(8) .532(8) ?
H(2101) .704(3) .468(6) .445(7) ?
H(2201) .686(5) .655(8) .528(8) ?
H(2301) .626(5) .672(7) .680(10) ?
H(2401) .582(4) .544(7) .814(7) ?
H(2501) .614(3) .340(6) .756(7) ?
H(11) .4720 .1882 .4424 ?
H(12) .4511 .0546 .4392 ?
H(13) .4522 .1236 .5613 ?
H(21) .5599 -.1053 .3701 ?
H(22) .5050 -.0347 .3041 ?
H(23) .5723 -.0479 .2429 ?
H(41) .6891 .2447 .1025 ?
H(42) .6759 .1091 .0832 ?
H(43) .6231 .2017 .0548 ?
H(51) .6758 -.0282 .3165 ?
H(52) .7261 .0076 .2164 ?
H(53) .7464 .0030 .3536 ?
H(71) .8110 .3270 .5113 ?
H(72) .8613 .2295 .4749 ?
H(73) .8393 .3235 .3804 ?
H(81) .8052 -.0124 .4772 ?
H(82) .8398 .0729 .5692 ?
H(83) .7852 -.0110 .6142 ?
H(101) .6161 .1040 .8221 ?
H(102) .6574 -.0115 .8083 ?
H(103) .6870 .1019 .8640 ?
H(111) .6824 -.0726 .5418 ?
H(112) .6318 -.1040 .6429 ?
H(113) .6100 -.0886 .5075 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
S(1) P(3) O(1) 117.3(3) yes
O(1) P(3) N(2) 96.4(5) yes
O(1) P(3) N(4) 106.9(4) yes
N(2) P(3) N(4) 105.0(4) yes
S(2) P(9) O(2) 117.9(3) yes
O(2) P(9) N(8) 96.4(4) yes
O(2) P(9) N(10) 107.2(4) yes
N(8) P(9) N(10) 103.8(4) yes
P(3) O(1) C(13) 123.7(7) no
S(2) P(9) N(10) 111.5(4) no
O(2) P(9) C(20) 125.0(7) no
N(2) N(1) C(1) 117.0(10) no
N(2) N(1) C(12) 119.5(9) no
C(1) N(1) C(12) 116.0(10) no
P(3) N(2) N(1) 117.9(7) no
P(3) N(2) C(2) 112.7(9) no
N(1) N(2) C(2) 113.5(8) no
P(3) N(4) N(5) 115.3(7) no
P(3) N(4) C(4) 126.2(8) no
N(5) N(4) C(4) 118.4(8) no
N(4) N(5) C(5) 111.5(8) no
N(4) N(5) C(6) 118.4(8) no
C(5) N(5) C(6) 121.8(8) no
N(8) N(7) C(6) 118.9(8) no
N(8) N(7) C(7) 116.3(10) no
C(6) N(7) C(7) 117.3(9) no
P(9) N(8) N(7) 117.9(7) no
P(9) N(8) C(8) 114.5(7) no
N(7) N(8) C(8) 113.7(8) no
P(9) N(10) N(11) 115.5(7) no
P(9) N(10) C(10) 124.8(7) no
N(11) N(10) C(10) 119.1(8) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P(3) S(1) 1.926(4) yes
P(3) O(1) 1.593(8) yes
P(3) N(2) 1.710(10) yes
P(3) N(4) 1.653(9) yes
N(1) N(2) 1.39(2) yes
N(4) N(5) 1.420(10) yes
C(6) O(6) 1.220(10) yes
C(6) N(5) 1.370(10) yes
C(6) N(7) 1.37(2) yes
P(9) S(2) 1.911(5) yes
P(9) O(2) 1.589(7) yes
P(9) N(8) 1.687(9) yes
P(9) N(10) 1.665(9) yes
N(7) N(8) 1.400(10) yes
N(10) N(11) 1.380(10) yes
C(12) O(12) 1.190(10) yes
C(12) N(1) 1.39(2) yes
C(12) N(11) 1.390(10) yes
O(1) C(13) 1.410(10) no
N(1) C(1) 1.450(10) no
N(2) C(2) 1.470(10) no
N(7) C(7) 1.430(10) no
N(8) C(8) 1.480(10) no
C(13) C(14) 1.34(2) no
C(14) C(15) 1.39(2) no
C(15) C(16) 1.35(3) no
C(16) C(17) 1.39(2) no
C(17) C(18) 1.37(2) no
C(18) C(13) 1.40(2) no
O(2) C(20) 1.370(10) no
N(4) C(4) 1.430(10) no
N(5) C(5) 1.500(10) no
N(10) C(10) 1.48(2) no
N(11) C(11) 1.490(10) no
C(20) C(21) 1.390(10) no
C(21) C(22) 1.41(2) no
C(22) C(23) 1.39(2) no
C(23) C(24) 1.38(2) no
C(24) C(25) 1.39(2) no
C(25) C(20) 1.37(2) no
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
_geom_torsion_publ_flag
C(1) N(1) N(2) C(2) -74.0(10) yes
C(12) N(1) N(2) P(3) -89.0(10) yes
C(1) N(1) N(2) P(3) 61.0(10) yes
C(12) N(1) N(2) C(2) 136.0(10) yes
C(4) N(4) N(5) C(5) -74.0(10) yes
P(3) N(4) N(5) C(6) -106.8(9) yes
C(4) N(4) N(5) C(6) 75.0(10) yes
P(3) N(4) N(5) C(5) 104.2(8) yes
C(7) N(7) N(8) C(8) -73.0(10) yes
C(6) N(7) N(8) P(9) -84.0(10) yes
C(7) N(7) N(8) P(9) 65.0(10) yes
C(6) N(7) N(8) C(8) 138.0(10) yes
C(10) N(10) N(11) C(11) -76.0(10) yes
P(9) N(10) N(11) C(12) -100.0(10) yes
C(10) N(10) N(11) C(12) 72.0(10) yes
P(9) N(10) N(11) C(11) 112.9(8) yes
C(1) N(1) C(12) O(12) -8.0(10) yes
N(2) N(1) C(12) O(12) 142.0(10) yes
C(1) N(1) C(12) N(11) 171.1(9) yes
N(2) N(1) C(12) N(11) -38.0(10) yes
C(11) N(11) C(12) O(12) 135.0(10) yes
N(10) N(11) C(12) O(12) -10(2) yes
C(11) N(11) C(12) N(1) -45.0(10) yes
N(10) N(11) C(12) N(1) 171.2(9) yes
C(7) N(7) C(6) O(6) -5(2) yes
N(8) N(7) C(6) O(6) 144.0(10) yes
C(7) N(7) C(6) N(5) 172.0(10) yes
N(8) N(7) C(6) N(5) -39.0(10) yes
C(5) N(5) C(6) O(6) 137.0(10) yes
N(4) N(5) C(6) O(6) -9(2) yes
C(5) N(5) C(6) N(7) -40.0(10) yes
N(4) N(5) C(6) N(7) 174.1(9) yes
N(1) N(2) P(3) N(4) 143.0(8) yes
N(5) N(4) P(3) N(2) -45.9(8) yes
N(7) N(8) P(9) N(10) 146.0(7) yes
N(11) N(10) P(9) N(8) -51.8(7) yes
