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#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/06/7240640.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_7240640
loop_
_publ_author_name
'Urbanovský, Peter'
'Kotek, Jan'
'Císařová, Ivana'
'Hermann, Petr'
_publ_section_title
;
 Selective and clean synthesis of aminoalkyl-H-phosphinic acids from
 hypophosphorous acid by phospha-Mannich reaction
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              21329
_journal_page_last               21349
_journal_paper_doi               10.1039/D0RA03075A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C7 H18 N O2 P, 2(H2 O)'
_chemical_formula_sum            'C7 H22 N O4 P'
_chemical_formula_weight         215.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.384(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3640(6)
_cell_length_b                   8.5851(4)
_cell_length_c                   20.1404(11)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4702
_cell_measurement_theta_min      2.8202
_cell_volume                     2310.1(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service V6.2.9'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.820
_diffrn_source                   'I\mS micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0386P)²+1.7367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2425
_reflns_number_total             2663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra03075a3.cif
_cod_data_source_block           diprampin
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7240636--7240653.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7240640
_shelx_shelxl_version_number     2014/7
_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   0.923
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.51372(2) 0.35154(3) 0.59620(2) 0.01422(9) Uani 1 1 d . . . . .
H1 H 0.6085(10) 0.3355(16) 0.5789(7) 0.016(3) Uiso 1 1 d . . . . .
O11 O 0.44695(6) 0.35925(10) 0.53559(4) 0.02006(19) Uani 1 1 d . . . . .
O12 O 0.49424(7) 0.23103(10) 0.64827(4) 0.02268(19) Uani 1 1 d . . . . .
C2 C 0.51304(8) 0.53839(12) 0.63919(5) 0.0133(2) Uani 1 1 d . . . . .
H21 H 0.4481 0.5495 0.6613 0.016 Uiso 1 1 calc R U . . .
H22 H 0.5660 0.5363 0.6744 0.016 Uiso 1 1 calc R U . . .
N3 N 0.52890(7) 0.68082(11) 0.59674(4) 0.01232(18) Uani 1 1 d . . . . .
H31 H 0.5315(11) 0.6560(18) 0.5541(8) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.44196(8) 0.79505(13) 0.60064(6) 0.0166(2) Uani 1 1 d . . . . .
H41 H 0.4557 0.8833 0.5698 0.020 Uiso 1 1 calc R U . . .
C5 C 0.34563(9) 0.71695(15) 0.57659(6) 0.0225(3) Uani 1 1 d . . . . .
H51 H 0.2961 0.7968 0.5643 0.027 Uiso 1 1 calc R U . . .
H52 H 0.3195 0.6518 0.6122 0.027 Uiso 1 1 calc R U . . .
H53 H 0.3592 0.6520 0.5378 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43301(10) 0.86214(14) 0.66995(6) 0.0225(3) Uani 1 1 d . . . . .
H61 H 0.4951 0.9164 0.6825 0.027 Uiso 1 1 calc R U . . .
H62 H 0.4211 0.7776 0.7015 0.027 Uiso 1 1 calc R U . . .
H63 H 0.3770 0.9357 0.6706 0.027 Uiso 1 1 calc R U . . .
C7 C 0.63089(8) 0.75497(14) 0.61198(6) 0.0187(2) Uani 1 1 d . . . . .
H71 H 0.6362 0.7774 0.6607 0.022 Uiso 1 1 calc R U . . .
C8 C 0.71264(9) 0.64001(16) 0.59435(7) 0.0249(3) Uani 1 1 d . . . . .
H81 H 0.7049 0.6105 0.5475 0.030 Uiso 1 1 calc R U . . .
H82 H 0.7074 0.5470 0.6222 0.030 Uiso 1 1 calc R U . . .
H83 H 0.7783 0.6885 0.6020 0.030 Uiso 1 1 calc R U . . .
C9 C 0.64328(10) 0.90715(16) 0.57417(7) 0.0288(3) Uani 1 1 d . . . . .
H91 H 0.6275 0.8901 0.5270 0.035 Uiso 1 1 calc R U . . .
H92 H 0.7125 0.9436 0.5795 0.035 Uiso 1 1 calc R U . . .
H93 H 0.5978 0.9857 0.5918 0.035 Uiso 1 1 calc R U . . .
O1W O 0.36135(7) 0.20470(11) 0.75028(5) 0.0258(2) Uani 1 1 d . . . . .
H11W H 0.3992(13) 0.208(2) 0.7162(9) 0.035(4) Uiso 1 1 d . . . . .
H12W H 0.3996(15) 0.209(2) 0.7831(11) 0.048(5) Uiso 1 1 d . . . . .
O2W O 0.18997(7) 0.02612(13) 0.76768(5) 0.0315(2) Uani 1 1 d . . . . .
H21W H 0.2494(17) 0.060(3) 0.7624(10) 0.056(6) Uiso 1 1 d . . . . .
H22W H 0.1945(14) -0.073(3) 0.7605(9) 0.047(5) Uiso 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 P1 O12 119.38(5) . . ?
O11 P1 C2 109.81(5) . . ?
O12 P1 C2 105.77(5) . . ?
O11 P1 H1 110.2(6) . . ?
O12 P1 H1 107.1(6) . . ?
C2 P1 H1 103.4(6) . . ?
N3 C2 P1 116.18(7) . . ?
N3 C2 H21 108.2 . . ?
P1 C2 H21 108.2 . . ?
N3 C2 H22 108.2 . . ?
P1 C2 H22 108.2 . . ?
H21 C2 H22 107.4 . . ?
C2 N3 C4 111.98(8) . . ?
C2 N3 C7 111.11(8) . . ?
C4 N3 C7 113.51(8) . . ?
C2 N3 H31 111.3(10) . . ?
C4 N3 H31 104.6(10) . . ?
C7 N3 H31 103.9(10) . . ?
C6 C4 C5 112.05(10) . . ?
C6 C4 N3 111.64(9) . . ?
C5 C4 N3 109.92(9) . . ?
C6 C4 H41 107.7 . . ?
C5 C4 H41 107.7 . . ?
N3 C4 H41 107.7 . . ?
C4 C5 H51 109.5 . . ?
C4 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
C4 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
C4 C6 H61 109.5 . . ?
C4 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C4 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
C8 C7 C9 110.64(10) . . ?
C8 C7 N3 108.96(9) . . ?
C9 C7 N3 111.34(10) . . ?
C8 C7 H71 108.6 . . ?
C9 C7 H71 108.6 . . ?
N3 C7 H71 108.6 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C7 C9 H91 109.5 . . ?
C7 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
C7 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
H11W O1W H12W 105.8(17) . . ?
H21W O2W H22W 104.2(18) . . ?
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 O11 1.4960(9) . ?
P1 O12 1.5005(8) . ?
P1 C2 1.8230(11) . ?
P1 H1 1.329(13) . ?
C2 N3 1.5100(13) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5238(14) . ?
N3 C7 1.5287(14) . ?
N3 H31 0.886(16) . ?
C4 C6 1.5176(16) . ?
C4 C5 1.5203(16) . ?
C4 H41 1.0000 . ?
C5 H51 0.9800 . ?
C5 H52 0.9800 . ?
C5 H53 0.9800 . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 C8 1.5207(17) . ?
C7 C9 1.5233(17) . ?
C7 H71 1.0000 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
O1W H11W 0.863(18) . ?
O1W H12W 0.83(2) . ?
O2W H21W 0.86(2) . ?
O2W H22W 0.86(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341391
