#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:43:02 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266047 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/72/7707230.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_7707230
loop_
_publ_author_name
'Faria, Erica N.'
'Jupp, Andrew R.'
'Goicoechea, Jose M.'
_publ_section_title
;
 Novel primary phosphinecarboxamides derived from diamines.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6991
_journal_page_last               6996
_journal_paper_doi               10.1039/d1dt01198g
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C4 H10 N2 O2 P2'
_chemical_formula_sum            'C4 H10 N2 O2 P2'
_chemical_formula_weight         180.08
_chemical_name_systematic
;
 PH2C(O)NHCH2CH2NHC(O)PH2
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2021-04-12 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.067(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1091(2)
_cell_length_b                   4.91330(10)
_cell_length_c                   12.5171(3)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      75.7343
_cell_measurement_theta_min      3.5304
_cell_volume                     436.927(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'WinGX (Farrugia, 2005)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4102
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3760
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.915
_diffrn_reflns_theta_min         7.056
_exptl_absorpt_coefficient_mu    4.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0327P)²+0.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                869
_reflns_number_total             896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01198g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7707227--7707230.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7707230
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.594
_shelx_estimated_absorpt_t_max   0.706
_shelxl_version_number           2014-1
_shelx_res_file
;
TITL p21n in P2(1)/n
CELL  1.54178   7.1091   4.9133  12.5171   90.000   92.067   90.000
ZERR     2.00   0.0002   0.0001   0.0003    0.000    0.002    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O    P
UNIT  8    20   4    4    4
MERG   2
FMAP   2
PLAN   20
SIZE     0.090   0.120   0.140
ACTA
BOND   $H
L.S.  12
TEMP  -123.00
WGHT    0.032700    0.108400
FVAR       0.31876
P1    5   -0.000841   -0.035638    0.142886    11.00000    0.03632    0.03770 =
         0.02286   -0.00284    0.00232   -0.00145
C1    1   -0.029037   -0.127519    0.285841    11.00000    0.02749    0.02022 =
         0.02646    0.00174   -0.00322   -0.00112
O1    4   -0.030259   -0.369492    0.310219    11.00000    0.06712    0.01819 =
         0.04587    0.00233   -0.00489   -0.00099
N1    3   -0.056202    0.070660    0.355473    11.00000    0.03560    0.01889 =
         0.02079    0.00358   -0.00177    0.00117
C2    1   -0.091352    0.015674    0.467208    11.00000    0.03033    0.03416 =
         0.02112    0.00422   -0.00162    0.00079
H1    2    0.168680   -0.112063    0.141788    11.00000    0.07493
H2    2    0.040696    0.204460    0.153412    11.00000    0.05722
H3    2   -0.047267    0.228493    0.336752    11.00000    0.03185
H4    2   -0.164668    0.166234    0.497577    11.00000    0.04665
H5    2   -0.164150   -0.142272    0.470349    11.00000    0.04515

HKLF    4

REM  p21n in P2(1)/n
REM R1 =  0.0238 for     869 Fo > 4sig(Fo)  and  0.0242 for all     896 data
REM     66 parameters refined using      0 restraints

END

WGHT      0.0327      0.1084

REM Highest difference peak  0.278,  deepest hole -0.254,  1-sigma level  0.053
Q1    1   0.0000  0.0000  0.5000  10.50000  0.05    0.28
Q2    1  -0.0186 -0.0807  0.2267  11.00000  0.05    0.20
Q3    1  -0.2212  0.0090  0.4839  11.00000  0.05    0.14
Q4    1   0.1205 -0.0288  0.1523  11.00000  0.05    0.13
Q5    1  -0.0572 -0.4216  0.2590  11.00000  0.05    0.12
Q6    1  -0.1527 -0.0444  0.1095  11.00000  0.05    0.11
Q7    1  -0.2757  0.1568  0.3194  11.00000  0.05    0.11
Q8    1  -0.0745  0.0393  0.4050  11.00000  0.05    0.11
Q9    1  -0.2256 -0.4075  0.2928  11.00000  0.05    0.10
Q10   1  -0.1048 -0.3350  0.3054  11.00000  0.05    0.10
Q11   1  -0.1431 -0.2376  0.4620  11.00000  0.05    0.10
Q12   1   0.2374  0.0834  0.2009  11.00000  0.05    0.10
Q13   1  -0.1233  0.2778  0.4962  11.00000  0.05    0.09
Q14   1  -0.2247  0.4297  0.4371  11.00000  0.05    0.09
Q15   1   0.3109  0.1038  0.1654  11.00000  0.05    0.09
Q16   1  -0.1978  0.4199  0.3009  11.00000  0.05    0.09
Q17   1   0.0367 -0.3593  0.3156  11.00000  0.05    0.09
Q18   1   0.1755 -0.2523  0.1548  11.00000  0.05    0.09
Q19   1  -0.1397 -0.5582  0.2435  11.00000  0.05    0.09
Q20   1   0.2356 -0.1490  0.2097  11.00000  0.05    0.09
;
_shelx_res_checksum              52581
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.00084(4) -0.03564(7) 0.14289(2) 0.03227(14) Uani 1 1 d . . . . .
C1 C -0.02904(15) -0.1275(2) 0.28584(9) 0.0248(2) Uani 1 1 d . . . . .
O1 O -0.03026(15) -0.36949(18) 0.31022(8) 0.0439(3) Uani 1 1 d . . . . .
N1 N -0.05620(15) 0.0707(2) 0.35547(8) 0.0252(2) Uani 1 1 d . . . . .
C2 C -0.09135(17) 0.0157(3) 0.46721(10) 0.0286(3) Uani 1 1 d . . . . .
H1 H 0.169(3) -0.112(4) 0.1418(17) 0.075(6) Uiso 1 1 d . . . . .
H2 H 0.041(2) 0.204(4) 0.1534(15) 0.057(5) Uiso 1 1 d . . . . .
H3 H -0.047(2) 0.228(4) 0.3368(13) 0.032(4) Uiso 1 1 d . . . . .
H4 H -0.165(2) 0.166(4) 0.4976(13) 0.047(4) Uiso 1 1 d . . . . .
H5 H -0.164(2) -0.142(4) 0.4703(13) 0.045(4) Uiso 1 1 d . . . . .
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
P1 0.0363(2) 0.0377(2) 0.02286(19) -0.00284(11) 0.00232(13) -0.00145(12)
C1 0.0275(5) 0.0202(5) 0.0265(5) 0.0017(4) -0.0032(4) -0.0011(4)
O1 0.0671(7) 0.0182(5) 0.0459(6) 0.0023(4) -0.0049(5) -0.0010(4)
N1 0.0356(5) 0.0189(5) 0.0208(5) 0.0036(4) -0.0018(4) 0.0012(4)
C2 0.0303(6) 0.0342(6) 0.0211(6) 0.0042(4) -0.0016(5) 0.0008(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C1 P1 H1 94.3(10) . . ?
C1 P1 H2 99.5(9) . . ?
H1 P1 H2 93.5(12) . . ?
O1 C1 N1 123.06(11) . . ?
O1 C1 P1 118.38(9) . . ?
N1 C1 P1 118.47(8) . . ?
C1 N1 C2 121.99(10) . . ?
C1 N1 H3 119.8(11) . . ?
C2 N1 H3 118.2(11) . . ?
N1 C2 C2 111.42(13) . 3_556 ?
N1 C2 H4 110.0(10) . . ?
C2 C2 H4 108.7(10) 3_556 . ?
N1 C2 H5 108.0(10) . . ?
C2 C2 H5 110.9(10) 3_556 . ?
H4 C2 H5 107.7(14) . . ?
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 C1 1.8633(12) . ?
P1 H1 1.26(2) . ?
P1 H2 1.22(2) . ?
C1 O1 1.2275(15) . ?
C1 N1 1.3256(15) . ?
N1 C2 1.4549(15) . ?
N1 H3 0.813(17) . ?
C2 C2 1.519(2) 3_556 ?
C2 H4 0.989(18) . ?
C2 H5 0.934(18) . ?
