#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/34/4323416.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_4323416
loop_
_publ_author_name
'Musa A. Said'
'Melanie Pülm'
'Regine Herbst-Irmer'
'K. C. Kumara Swamy'
_publ_contact_author
;
      Dr. Regine Herbst-Irmer
      Institut für Anorganische Chemie
      Universität Göttingen
      Tammannstr. 4
      37077 Göttingen
      Germany
;
_publ_contact_author_email       rherbst@shelx.uni-ac.gwdg.de
_publ_contact_author_fax         '049 551 392582'
_publ_contact_author_phone       '049 551 393007'
_publ_section_title
;
 Cyclic Aminophosphites and -phosphoranes Possessing Six- and
 Higher-Membered Rings: A Comparative Study of Structure and Reactivity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2044
_journal_page_last               2051
_journal_paper_doi               10.1021/ic9611958
_journal_volume                  36
_journal_year                    1997
_chemical_formula_sum            'C17 H22 Cl4 N O4 P'
_chemical_formula_weight         477.13
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8450(10)
_cell_length_b                   17.923(4)
_cell_length_c                   12.344(2)
_cell_measurement_temperature    153(2)
_cell_volume                     2077.7(6)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4945
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.670
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.052
_refine_ls_goodness_of_fit_obs   1.054
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.289
_refine_ls_restrained_S_obs      1.054
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_obs          0.0382
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0268P)²+2.9030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1107
_refine_ls_wR_factor_obs         0.0807
_reflns_number_observed          2967
_reflns_number_total             3681
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic9611958_3.cif
_cod_data_source_block           k32
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29 (5 times).

'_geom_angle_publ_flag' value 'Y'
changed to 'y' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0268P)^2^+2.9030P] 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^)+(0.0268P)^2^+2.9030P] 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               4323416
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags
_atom_site_disorder_group
P1 P 0.76126(7) 0.11573(4) 0.35222(6) 0.0195(2) Uani 1 d . .
O3 O 0.6201(2) 0.16035(11) 0.27048(14) 0.0226(4) Uani 1 d . .
O4 O 0.7738(2) 0.06734(11) 0.22933(14) 0.0226(4) Uani 1 d . .
C21 C 0.5844(3) 0.1429(2) 0.1578(2) 0.0220(6) Uani 1 d . .
C22 C 0.4746(3) 0.1740(2) 0.0752(2) 0.0251(6) Uani 1 d . .
C23 C 0.4502(3) 0.1483(2) -0.0366(2) 0.0267(6) Uani 1 d . .
C24 C 0.5384(3) 0.0943(2) -0.0595(2) 0.0273(7) Uani 1 d . .
C25 C 0.6516(3) 0.0642(2) 0.0262(2) 0.0228(6) Uani 1 d . .
C26 C 0.6736(3) 0.0892(2) 0.1364(2) 0.0211(6) Uani 1 d . .
Cl1 Cl 0.37346(8) 0.24270(5) 0.10911(6) 0.0359(2) Uani 1 d . .
Cl2 Cl 0.31003(9) 0.18439(5) -0.14283(6) 0.0435(2) Uani 1 d . .
Cl3 Cl 0.50944(9) 0.06361(5) -0.19669(6) 0.0405(2) Uani 1 d . .
Cl4 Cl 0.76382(8) -0.00242(4) 0.00110(6) 0.0317(2) Uani 1 d . .
N1 N 0.7514(2) 0.03458(13) 0.4070(2) 0.0214(5) Uani 1 d D .
H1 H 0.7532(31) 0.0000(15) 0.3622(22) 0.026 Uiso 1 d D .
C31 C 0.7341(3) 0.0135(2) 0.5173(2) 0.0210(6) Uani 1 d . .
H31 H 0.6688(3) 0.0503(2) 0.5369(2) 0.025 Uiso 1 calc R .
C32 C 0.6650(3) -0.0629(2) 0.5058(2) 0.0249(6) Uani 1 d . .
H32A H 0.7264(3) -0.0995(2) 0.4828(2) 0.030 Uiso 1 calc R .
H32B H 0.5723(3) -0.0613(2) 0.4455(2) 0.030 Uiso 1 calc R .
C33 C 0.6416(3) -0.0881(2) 0.6166(2) 0.0287(7) Uani 1 d . .
H33A H 0.5713(3) -0.0548(2) 0.6350(2) 0.034 Uiso 1 calc R .
H33B H 0.6023(3) -0.1394(2) 0.6075(2) 0.034 Uiso 1 calc R .
C34 C 0.7795(3) -0.0867(2) 0.7134(2) 0.0323(7) Uani 1 d . .
H34A H 0.8447(3) -0.1254(2) 0.7003(2) 0.039 Uiso 1 calc R .
H34B H 0.7594(3) -0.0988(2) 0.7854(2) 0.039 Uiso 1 calc R .
C35 C 0.8517(3) -0.0111(2) 0.7243(2) 0.0329(7) Uani 1 d . .
H35A H 0.9448(3) -0.0136(2) 0.7840(2) 0.039 Uiso 1 calc R .
H35B H 0.7923(3) 0.0264(2) 0.7478(2) 0.039 Uiso 1 calc R .
C36 C 0.8746(3) 0.0133(2) 0.6126(2) 0.0265(6) Uani 1 d . .
H36A H 0.9165(3) 0.0640(2) 0.6213(2) 0.032 Uiso 1 calc R .
H36B H 0.9422(3) -0.0212(2) 0.5930(2) 0.032 Uiso 1 calc R .
O2 O 0.7431(2) 0.15836(10) 0.46300(15) 0.0217(4) Uani 1 d . .
O1 O 0.9071(2) 0.15428(11) 0.3523(2) 0.0239(4) Uani 1 d . .
C13 C 0.7566(3) 0.2380(2) 0.4715(3) 0.0297(7) Uani 1 d . .
H13A H 0.7433(3) 0.2544(2) 0.5443(3) 0.036 Uiso 1 calc R .
H13B H 0.6803(3) 0.2611(2) 0.4092(3) 0.036 Uiso 1 calc R .
C12 C 0.9005(3) 0.2656(2) 0.4656(3) 0.0324(7) Uani 1 d . .
C121 C 0.8771(5) 0.3183(2) 0.3635(4) 0.0686(13) Uani 1 d . .
H12A H 0.8217(29) 0.3616(9) 0.3737(13) 0.103 Uiso 1 calc R .
H12B H 0.8253(29) 0.2918(6) 0.2938(5) 0.103 Uiso 1 calc R .
H12C H 0.9695(5) 0.3349(14) 0.3577(16) 0.103 Uiso 1 calc R .
C122 C 0.9812(4) 0.3048(3) 0.5738(4) 0.078(2) Uani 1 d . .
H12D H 0.9230(16) 0.3455(12) 0.5889(16) 0.116 Uiso 1 calc R .
H12E H 1.0702(18) 0.3250(17) 0.5660(11) 0.116 Uiso 1 calc R .
H12F H 1.0028(32) 0.2692(5) 0.6370(6) 0.116 Uiso 1 calc R .
C11 C 0.9854(3) 0.1984(2) 0.4486(2) 0.0280(7) Uani 1 d . .
H11A H 1.0756(3) 0.2154(2) 0.4369(2) 0.034 Uiso 1 calc R .
H11B H 1.0094(3) 0.1670(2) 0.5178(2) 0.034 Uiso 1 calc R .
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 123.82(11) . . y
O1 P1 O2 97.05(10) . . y
N1 P1 O2 92.01(11) . . y
O1 P1 O3 112.45(10) . . y
N1 P1 O3 122.90(11) . . y
O2 P1 O3 90.09(9) . . y
O1 P1 O4 85.34(9) . . y
N1 P1 O4 86.95(10) . . y
O2 P1 O4 177.58(10) . . y
O3 P1 O4 88.65(9) . . y
C21 O3 P1 115.0(2) . . ?
C26 O4 P1 111.6(2) . . ?
C22 C21 O3 124.9(2) . . ?
C22 C21 C26 123.3(3) . . ?
O3 C21 C26 111.7(2) . . ?
C21 C22 C23 117.7(3) . . ?
C21 C22 Cl1 120.0(2) . . ?
C23 C22 Cl1 122.3(2) . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 Cl2 121.1(2) . . ?
C22 C23 Cl2 119.1(2) . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 Cl3 119.7(2) . . ?
C25 C24 Cl3 118.8(2) . . ?
C26 C25 C24 118.3(3) . . ?
C26 C25 Cl4 118.8(2) . . ?
C24 C25 Cl4 122.9(2) . . ?
O4 C26 C21 113.0(2) . . ?
O4 C26 C25 127.6(3) . . ?
C21 C26 C25 119.4(3) . . ?
H1 N1 C31 117.1(21) . . ?
H1 N1 P1 111.9(20) . . ?
C31 N1 P1 130.9(2) . . ?
N1 C31 C32 108.6(2) . . ?
N1 C31 C36 112.6(2) . . ?
C32 C31 C36 110.3(2) . . ?
C31 C32 C33 111.6(2) . . ?
C34 C33 C32 111.2(2) . . ?
C33 C34 C35 111.7(2) . . ?
C34 C35 C36 111.6(2) . . ?
C31 C36 C35 110.6(2) . . ?
C13 O2 P1 119.9(2) . . ?
C11 O1 P1 119.8(2) . . ?
O2 C13 C12 112.7(2) . . ?
C122 C12 C11 109.1(3) . . ?
C122 C12 C13 111.0(3) . . ?
C11 C12 C13 108.0(2) . . ?
C122 C12 C121 110.5(3) . . ?
C11 C12 C121 109.1(3) . . ?
C13 C12 C121 109.1(3) . . ?
O1 C11 C12 111.6(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.593(2) . y
P1 N1 1.619(2) . y
P1 O2 1.622(2) . y
P1 O3 1.657(2) . y
P1 O4 1.784(2) . y
O3 C21 1.365(3) . ?
O4 C26 1.327(3) . ?
C21 C22 1.362(4) . ?
C21 C26 1.381(4) . ?
C22 C23 1.405(4) . ?
C22 Cl1 1.713(3) . ?
C23 C24 1.384(4) . ?
C23 Cl2 1.719(3) . ?
C24 C25 1.394(4) . ?
C24 Cl3 1.721(3) . ?
C25 C26 1.386(4) . ?
C25 Cl4 1.717(3) . ?
N1 H1 0.83(2) . ?
N1 C31 1.471(3) . ?
C31 C32 1.517(4) . ?
C31 C36 1.523(3) . ?
C32 C33 1.522(4) . ?
C33 C34 1.516(4) . ?
C34 C35 1.517(4) . ?
C35 C36 1.527(4) . ?
O2 C13 1.435(3) . ?
O1 C11 1.442(3) . ?
C13 C12 1.523(4) . ?
C12 C122 1.508(5) . ?
C12 C11 1.517(4) . ?
C12 C121 1.536(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661138
