#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:58:33 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202018 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/21/8102171.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_8102171
loop_
_publ_author_name
'Ghadimi, Saied'
'Valmoozi, Ali A. E.'
'Pourayoubi, Mehrdad'
_publ_section_title
;
Crystal structure of N,N-dimethylphosphoramidochloridic acid 4-methylphenyl 
ester, ClP(O)[N(CH₃)₂][OC₆H₄(CH₃)]
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              339
_journal_page_last               340
_journal_volume                  222
_journal_year                    2007
_chemical_formula_moiety         'C9 H13 Cl N O2 P'
_chemical_formula_structural     ClP(O)[N(CH3)2][OC6H4(CH3)]
_chemical_formula_sum            'C9 H13 Cl N O2 P'
_chemical_formula_weight         233.62
_chemical_name_systematic
; 
N,N'-dimethylphosphoramidochloridic acid 4-methyl phenyl ester
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.111(5)
_cell_angle_beta                 97.798(5)
_cell_angle_gamma                105.440(5)
_cell_formula_units_Z            2
_cell_length_a                   6.0555(12)
_cell_length_b                   6.8582(14)
_cell_length_c                   14.370(3)
_cell_measurement_reflns_used    3831
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.90
_cell_measurement_theta_min      2.91
_cell_volume                     560.0(2)
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL, v. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL, v. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL, v. 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL, v. 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       phi/omega
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5532
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.3100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2076
_reflns_number_total             2372
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-2077.cff
_cod_data_source_block           Ghadimi_Sample1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               8102171
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.63440(8) 0.20255(6) 0.08801(3) 0.02546(13) Uani 1 2 i d . . .
P1 P 0.87282(7) 0.43169(6) 0.18602(3) 0.01660(12) Uani 1 2 i d . . .
O1 O 1.1024(2) 0.4004(2) 0.19026(9) 0.0289(3) Uani 1 2 i d . . .
O2 O 0.7617(2) 0.42070(17) 0.27927(8) 0.0182(2) Uani 1 2 i d . . .
N1 N 0.8496(2) 0.6497(2) 0.16141(10) 0.0178(3) Uani 1 2 i d . . .
C1 C 0.6834(3) 0.2342(2) 0.31267(11) 0.0165(3) Uani 1 2 i d . . .
C2 C 0.4466(3) 0.1433(2) 0.30007(11) 0.0185(3) Uani 1 2 i d . . .
H2A H 0.3399 0.2018 0.2678 0.022 Uiso 1 2 i calc R . .
C3 C 0.3673(3) -0.0367(3) 0.33583(11) 0.0202(3) Uani 1 2 i d . . .
H3A H 0.2045 -0.1007 0.3279 0.024 Uiso 1 2 i calc R . .
C4 C 0.5220(3) -0.1244(2) 0.38291(11) 0.0201(3) Uani 1 2 i d . . .
C5 C 0.7603(3) -0.0278(3) 0.39361(11) 0.0217(3) Uani 1 2 i d . . .
H5A H 0.8681 -0.0863 0.4251 0.026 Uiso 1 2 i calc R . .
C6 C 0.8435(3) 0.1529(3) 0.35901(11) 0.0201(3) Uani 1 2 i d . . .
H6A H 1.0060 0.2184 0.3671 0.024 Uiso 1 2 i calc R . .
C7 C 0.4349(4) -0.3195(3) 0.42088(13) 0.0273(4) Uani 1 2 i d . . .
H7A H 0.3166 -0.4213 0.3715 0.041 Uiso 1 2 i calc R . .
H7B H 0.3664 -0.2896 0.4772 0.041 Uiso 1 2 i calc R . .
H7C H 0.5652 -0.3745 0.4386 0.041 Uiso 1 2 i calc R . .
C8 C 1.0010(3) 0.7535(3) 0.10036(13) 0.0267(4) Uani 1 2 i d . . .
H8A H 1.0261 0.9024 0.1163 0.040 Uiso 1 2 i calc R . .
H8B H 0.9267 0.7033 0.0331 0.040 Uiso 1 2 i calc R . .
H8C H 1.1511 0.7239 0.1110 0.040 Uiso 1 2 i calc R . .
C9 C 0.6213(3) 0.6876(3) 0.15240(12) 0.0214(3) Uani 1 2 i d . . .
H9A H 0.6419 0.8344 0.1739 0.032 Uiso 1 2 i calc R . .
H9B H 0.5267 0.6073 0.1918 0.032 Uiso 1 2 i calc R . .
H9C H 0.5427 0.6463 0.0854 0.032 Uiso 1 2 i calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0396(3) 0.0171(2) 0.0176(2) 0.00311(14) 0.00306(16) 0.00585(17)
P1 0.0189(2) 0.0165(2) 0.0177(2) 0.00734(15) 0.00463(15) 0.00795(16)
O1 0.0251(7) 0.0359(7) 0.0369(7) 0.0201(6) 0.0113(5) 0.0180(6)
O2 0.0256(6) 0.0139(5) 0.0172(5) 0.0059(4) 0.0057(4) 0.0069(5)
N1 0.0191(7) 0.0151(6) 0.0219(7) 0.0083(5) 0.0055(5) 0.0063(5)
C1 0.0234(8) 0.0133(7) 0.0145(7) 0.0048(5) 0.0049(6) 0.0062(6)
C2 0.0233(8) 0.0177(8) 0.0181(7) 0.0048(6) 0.0051(6) 0.0106(7)
C3 0.0216(8) 0.0192(8) 0.0206(8) 0.0039(6) 0.0070(6) 0.0054(7)
C4 0.0310(9) 0.0161(7) 0.0152(7) 0.0040(6) 0.0073(6) 0.0083(7)
C5 0.0291(9) 0.0213(8) 0.0186(8) 0.0078(6) 0.0032(6) 0.0123(7)
C6 0.0193(8) 0.0229(8) 0.0195(8) 0.0063(6) 0.0027(6) 0.0076(7)
C7 0.0422(11) 0.0188(8) 0.0235(9) 0.0085(7) 0.0101(7) 0.0090(8)
C8 0.0258(9) 0.0280(9) 0.0313(9) 0.0178(7) 0.0103(7) 0.0075(7)
C9 0.0239(9) 0.0208(8) 0.0247(8) 0.0087(6) 0.0067(6) 0.0119(7)
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 O2 117.24(7) . . ?
O1 P1 N1 116.53(7) . . ?
O2 P1 N1 101.71(7) . . ?
O1 P1 Cl1 109.85(6) . . ?
O2 P1 Cl1 102.39(5) . . ?
N1 P1 Cl1 107.81(6) . . ?
C1 O2 P1 122.32(10) . . ?
C9 N1 C8 113.91(13) . . ?
C9 N1 P1 119.22(11) . . ?
C8 N1 P1 118.98(12) . . ?
C2 C1 C6 122.29(15) . . ?
C2 C1 O2 117.94(14) . . ?
C6 C1 O2 119.74(15) . . ?
C1 C2 C3 118.43(15) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C3 C2 121.33(16) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 118.32(15) . . ?
C3 C4 C7 121.02(16) . . ?
C5 C4 C7 120.66(15) . . ?
C6 C5 C4 121.34(15) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C1 C6 C5 118.29(16) . . ?
C1 C6 H6A 120.9 . . ?
C5 C6 H6A 120.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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
Cl1 P1 2.0380(6) . ?
P1 O1 1.4568(13) . ?
P1 O2 1.5812(12) . ?
P1 N1 1.6212(14) . ?
O2 C1 1.4155(18) . ?
N1 C9 1.466(2) . ?
N1 C8 1.471(2) . ?
C1 C2 1.378(2) . ?
C1 C6 1.383(2) . ?
C2 C3 1.396(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(3) . ?
C4 C7 1.508(2) . ?
C5 C6 1.395(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C1 -69.80(14) . . . . ?
N1 P1 O2 C1 161.90(12) . . . . ?
Cl1 P1 O2 C1 50.48(12) . . . . ?
O1 P1 N1 C9 177.63(11) . . . . ?
O2 P1 N1 C9 -53.61(13) . . . . ?
Cl1 P1 N1 C9 53.65(12) . . . . ?
O1 P1 N1 C8 30.43(16) . . . . ?
O2 P1 N1 C8 159.18(13) . . . . ?
Cl1 P1 N1 C8 -93.55(13) . . . . ?
P1 O2 C1 C2 -105.81(15) . . . . ?
P1 O2 C1 C6 76.24(17) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
O2 C1 C2 C3 -177.71(13) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C7 -179.67(15) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C7 C4 C5 C6 -179.91(15) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
O2 C1 C6 C5 178.07(14) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8761112
