#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/63/4116330.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_4116330
loop_
_publ_author_name
'Douglas E. Berning'
'Kattesh V. Katti'
'Charles L. Barnes'
'Wynn A. Volkert'
_publ_contact_author
;
Kattesh V. Katti
Missouri University Research Reactor
University of Missouri
Columbia, MO 65211
;
_publ_section_title
;
 Chemical and Biomedical Motifs of the Reactions of
 Hydroxymethylphosphines with Amines, Amino Acids, and Model Peptides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1658
_journal_page_last               1664
_journal_paper_doi               10.1021/ja9827604
_journal_volume                  121
_journal_year                    1999
_chemical_formula_moiety         'C14 H19 N2 O4 P2 Cl '
_chemical_formula_sum            'C14 H19 Cl N2 O4 P2'
_chemical_formula_weight         376.71
_chemical_name_common            HMPB(gly)2
_chemical_name_systematic        ?
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 108.816(1)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   13.573(1)
_cell_length_b                   13.279(1)
_cell_length_c                   10.653(1)
_cell_measurement_reflns_used    3502
_cell_measurement_temperature    293
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      5.00
_cell_volume                     1817.4(3)
_computing_data_reduction        'NRCVAX DATRD2'
_computing_molecular_graphics    NRCVAX
_computing_publication_material  'NRCVAX TABLES Jan 94 Version'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    'NRCVAX SOLVER'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Siemens P -1    '
_diffrn_measurement_method       'Omega scan b/P/b        '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3502
_diffrn_reflns_theta_max         22.99
_diffrn_reflns_theta_min         0.00
_exptl_absorpt_coefficient_mu    0.40
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             785.53
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.14
_refine_ls_goodness_of_fit_obs   1.64
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1206
_refine_ls_R_factor_all          0.031
_refine_ls_R_factor_obs          0.031
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(σ²(F)+0.0009F²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.055
_refine_ls_wR_factor_obs         0.055
_reflns_number_observed          1206
_reflns_number_total             1274
_reflns_observed_criterion       'Inet > 2.0\s(Inet)'
_cod_data_source_file            ja9827604_4.cif
_cod_data_source_block           DB-IV-25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/(\s^2^(F)+0.0009F^2^)' 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)+0.0009F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C14 H19 N2 O4 P2 Cl '
_cod_database_code               4116330
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2+x,1/2+y,z
1/2-x,1/2-y,-z
-x,y,1/2-z
x,-y,1/2+z
1/2-x,1/2+y,1/2-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
Cl 0.0614(5) 0.0609(6) 0.0983(7) 0.0195(4) 0.0444(5) 0.0298(4) Cl
P1 0.0382(4) 0.0534(4) 0.0419(4) 0.00403(21) 0.0030(3) 0.01120(21) P
O1 0.1057(13) 0.0715(11) 0.0580(9) 0.0393(9) 0.0493(9) 0.0237(8) O
O2 0.1484(19) 0.0681(12) 0.1112(15) 0.0571(12) 0.0936(15) 0.0380(11) O
N 0.0366(8) 0.0447(9) 0.0328(8) 0.0035(6) 0.0108(6) 0.0014(6) n
C1 0.0507(12) 0.0457(12) 0.0666(12) 0.0036(8) 0.0237(9) 0.0063(9) C
C2 0.0839(17) 0.0574(17) 0.0915(20) 0.0130(12) 0.0375(16) 0.0208(14) C
C3 0.147(3) 0.0446(14) 0.126(3) 0.0114(16) 0.073(3) 0.0150(14) C
C4 0.0450(11) 0.0535(12) 0.0367(11) -0.0009(9) 0.0135(9) 0.0082(9) C
C5 0.0313(10) 0.0551(12) 0.0492(12) -0.0019(9) 0.0071(9) 0.0024(9) C
C6 0.0594(13) 0.0521(12) 0.0490(12) 0.0133(10) 0.0300(10) 0.0039(9) C
C7 0.0660(13) 0.0539(13) 0.0528(12) 0.0189(10) 0.0303(10) 0.0076(9) C
loop_
_atom_site_label
_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_refinement_flags
_atom_site_type_symbol
Cl 0.75000 -0.25000 0.50000 0.0691(6) Uij S Cl
P1 0.41012(3) 0.28402(4) 0.08420(5) 0.0469(4) Uij . P
O1 0.60635(13) -0.00827(12) 0.37480(15) 0.0729(11) Uij . O
O2 0.70139(19) -0.09575(15) 0.27962(22) 0.0968(15) Uij . O
N 0.57788(10) 0.14655(11) 0.20416(13) 0.0381(8) Uij . n
C1 0.46584(15) 0.39378(16) 0.18468(21) 0.0532(12) Uij . C
C2 0.43178(24) 0.48614(20) 0.1221(3) 0.0754(18) Uij . C
C3 0.4661(3) 0.57623(21) 0.1870(3) 0.099(3) Uij . C
C4 0.52049(16) 0.20240(16) 0.08135(19) 0.0450(11) Uij . C
C5 0.35164(14) 0.21135(16) 0.19071(21) 0.0466(11) Uij . C
C6 0.63418(18) 0.05687(16) 0.18000(21) 0.0505(12) Uij . C
C7 0.64504(16) -0.01778(16) 0.28964(20) 0.0549(12) Uij . C
H2O 0.705(3) -0.135(3) 0.335(3) 0.114(13) Uiso . H
H1N 0.500 0.123(3) 0.250 0.105(13) Uiso S H
H2 0.3825(24) 0.4820(23) 0.027(4) 0.097(9) Uiso . H
H3 0.440(3) 0.639(3) 0.144(3) 0.113(10) Uiso . H
H42 0.4871(18) 0.1504(21) 0.014(3) 0.077(7) Uiso . H
H41 0.5677(17) 0.2390(16) 0.0525(22) 0.055(6) Uiso . H
H52 0.2984(19) 0.1671(18) 0.1266(23) 0.065(6) Uiso . H
H51 0.3119(18) 0.2548(17) 0.235(3) 0.067(7) Uiso . H
H62 0.5966(19) 0.0283(20) 0.093(3) 0.077(8) Uiso . H
H61 0.7016(17) 0.0748(16) 0.1744(20) 0.058(6) Uiso . H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
N 0.004 0.003 'International Tables Vol. IV Table 2.2B'
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
P 0.090 0.095 'International Tables Vol. IV Table 2.2B'
Cl 0.132 0.159 'International Tables Vol. IV Table 2.2B'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 P1 C4 106.99(9)
C1 P1 C5 103.63(10)
C4 P1 C5 102.32(9)
C4 N C5a 113.62(15)
C4 N C6 113.65(14)
C5a N C6 110.65(15)
P1 C1 C1a 126.85(16)
P1 C1 C2 114.19(19)
C1a C1 C2 118.93(22)
C1 C2 C3 120.8(3)
C2 C3 C3a 120.3(3)
P1 C4 N 118.24(13)
P1 C5 Na 117.60(12)
N C6 C7 108.79(15)
O1 C7 O2 123.84(19)
O1 C7 C6 124.37(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.8221(22)
P1 C4 1.8571(20)
P1 C5 1.8519(20)
O1 C7 1.1925(23)
O2 C7 1.3118(25)
N C4 1.4869(23)
N C5a 1.4896(24)
N C6 1.4816(24)
C1 C1a 1.402(4)
C1 C2 1.401(3)
C2 C3 1.385(4)
C3 C3a 1.360(7)
C5 Na 1.4896(24)
