#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238161.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_2238161
loop_
_publ_author_name
'Ovchynnikov, Vladimir'
_publ_section_title
;
 Methyl N-(dimethoxyphosphoryl)carbamate
;
_journal_coeditor_code           GG2115
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1188
_journal_page_last               o1189
_journal_paper_doi               10.1107/S1600536813017637
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C4 H10 N O5 P'
_chemical_formula_moiety         'C4 H10 N O5 P'
_chemical_formula_sum            'C4 H10 N O5 P'
_chemical_formula_weight         183.10
_chemical_melting_point          337
_chemical_name_systematic
;
Methyl N-(dimethoxyphosphoryl)carbamate
;
_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                99.05(3)
_cell_angle_beta                 96.70(3)
_cell_angle_gamma                100.54(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4410(10)
_cell_length_b                   7.0180(10)
_cell_length_c                   9.298(2)
_cell_measurement_reflns_used    1635
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.24
_cell_volume                     403.46(14)
_computing_cell_refinement
;
CAD-4 EXPRESS (Enraf--Nonius, 1994)
;
_computing_data_collection
;
CAD-4 EXPRESS (Enraf--Nonius, 1994)
;
_computing_data_reduction
;
XCAD4 (Harms & Wocadlo, 1996)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/Θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1417
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9244
_exptl_absorpt_correction_T_min  0.9103
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.372
_refine_ls_extinction_coef       0.38(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0766P)²+0.3565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                1322
_reflns_number_total             1417
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2115.cif
_cod_data_source_block           I
_cod_database_code               2238161
_cod_database_fobs_code          2238161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
P P1 0.12950(10) 0.49103(10) 0.73507(7) 0.0377(3) Uani d . 1 1
O O1 -0.0897(3) 0.4420(3) 0.6611(2) 0.0544(6) Uani d . 1 1
O O4 0.1726(3) 0.5989(3) 0.8985(2) 0.0502(6) Uani d . 1 1
O O3 0.2109(4) 0.2955(3) 0.7485(3) 0.0576(6) Uani d . 1 1
O O2 0.5735(3) 0.7814(3) 0.8088(2) 0.0574(6) Uani d . 1 1
O O5 0.5569(3) 0.8030(3) 0.5700(2) 0.0503(6) Uani d . 1 1
N N1 0.2820(3) 0.6223(3) 0.6387(3) 0.0420(6) Uani d . 1 1
H H1N 0.2292 0.6164 0.5484 0.050 Uiso calc R 1 1
C C3 0.1084(6) 0.7823(5) 0.9409(4) 0.0648(9) Uani d . 1 1
H H3A 0.1479 0.8264 1.0453 0.097 Uiso calc R 1 1
H H3B -0.0436 0.7643 0.9155 0.097 Uiso calc R 1 1
H H3C 0.1780 0.8790 0.8903 0.097 Uiso calc R 1 1
C C2 0.4229(6) 0.2930(5) 0.8115(5) 0.0668(9) Uani d . 1 1
H H2A 0.4385 0.1591 0.8085 0.100 Uiso calc R 1 1
H H2B 0.4501 0.3612 0.9119 0.100 Uiso calc R 1 1
H H2C 0.5229 0.3572 0.7566 0.100 Uiso calc R 1 1
C C1 0.4822(4) 0.7395(4) 0.6847(3) 0.0388(6) Uani d . 1 1
C C4 0.7664(5) 0.9297(5) 0.6001(4) 0.0560(8) Uani d . 1 1
H H4A 0.8054 0.9672 0.5105 0.084 Uiso calc R 1 1
H H4B 0.8684 0.8605 0.6400 0.084 Uiso calc R 1 1
H H4C 0.7647 1.0455 0.6700 0.084 Uiso calc R 1 1
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'
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
O1 P1 O4 117.63(12) yes
O1 P1 O3 109.28(13) yes
O4 P1 O3 101.56(12) yes
O1 P1 N1 109.55(12) yes
O4 P1 N1 108.84(12) yes
O3 P1 N1 109.57(13) yes
O1 P1 O2 149.38(10) ?
O4 P1 O2 68.54(9) ?
O3 P1 O2 97.78(10) ?
N1 P1 O2 45.52(9) ?
C3 O4 P1 121.2(2) ?
C3 O4 O2 94.46(19) ?
P1 O4 O2 81.92(10) ?
C2 O3 P1 123.2(2) ?
C1 O2 O4 87.22(16) ?
C1 O2 P1 60.15(15) ?
C1 O5 C4 116.0(2) ?
C1 N1 P1 128.4(2) ?
C1 N1 H1N 115.8 ?
P1 N1 H1N 115.8 ?
O4 C3 H3A 109.5 ?
O4 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
O4 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
O3 C2 H2A 109.5 ?
O3 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
O3 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
O2 C1 O5 125.1(2) ?
O2 C1 N1 125.7(3) ?
O5 C1 N1 109.1(2) ?
O5 C4 H4A 109.5 ?
O5 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
O5 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.451(2) yes
P1 O4 1.556(2) yes
P1 O3 1.573(2) yes
P1 N1 1.658(2) yes
P1 O2 3.126(2) yes
O4 C3 1.434(4) ?
O4 O2 2.938(3) yes
O3 C2 1.427(4) ?
O2 C1 1.198(3) yes
O5 C1 1.326(3) ?
O5 C4 1.444(3) ?
N1 C1 1.377(3) yes
N1 H1N 0.8600 ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 2_566 0.86 1.99 2.847(3) 171
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
O1 P1 O4 C3 -56.6(3)
O3 P1 O4 C3 -175.8(2)
N1 P1 O4 C3 68.7(2)
O2 P1 O4 C3 90.3(2)
O1 P1 O4 O2 -146.92(12)
O3 P1 O4 O2 93.90(11)
N1 P1 O4 O2 -21.63(11)
O1 P1 O3 C2 177.8(2)
O4 P1 O3 C2 -57.2(3)
N1 P1 O3 C2 57.8(3)
O2 P1 O3 C2 12.3(3)
C3 O4 O2 C1 -98.7(2)
P1 O4 O2 C1 22.27(18)
C3 O4 O2 P1 -120.9(2)
O1 P1 O2 C1 -45.8(3)
O4 P1 O2 C1 -154.1(2)
O3 P1 O2 C1 106.5(2)
N1 P1 O2 C1 -3.4(2)
O1 P1 O2 O4 108.3(2)
O3 P1 O2 O4 -99.42(13)
N1 P1 O2 O4 150.72(16)
O1 P1 N1 C1 161.9(2)
O4 P1 N1 C1 32.0(3)
O3 P1 N1 C1 -78.2(3)
O2 P1 N1 C1 3.27(19)
O4 O2 C1 O5 169.5(3)
P1 O2 C1 O5 -178.1(3)
O4 O2 C1 N1 -8.8(3)
P1 O2 C1 N1 3.6(2)
C4 O5 C1 O2 1.1(4)
C4 O5 C1 N1 179.7(2)
P1 N1 C1 O2 -7.5(4)
P1 N1 C1 O5 173.93(19)
