#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/06/7240641.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_7240641
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         'C22 H24 N O2 P, C H4 O'
_chemical_formula_sum            'C23 H28 N O3 P'
_chemical_formula_weight         397.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                73.496(2)
_cell_angle_beta                 82.075(2)
_cell_angle_gamma                87.525(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7954(5)
_cell_length_b                   9.9645(5)
_cell_length_c                   11.1729(6)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5371
_cell_measurement_theta_min      2.4340
_cell_volume                     1035.62(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19211
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.099
_diffrn_source                   'I\mS micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_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    1.275
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0345
_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)+(0.0407P)²+0.5483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4190
_reflns_number_total             4763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra03075a3.cif
_cod_data_source_block           dbabnpin
_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_database_code               7240641
_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   0.958
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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_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 0.69186(3) 0.47241(3) 0.31901(3) 0.01699(9) Uani 1 1 d . . . . .
H1 H 0.6460(15) 0.5051(15) 0.2066(13) 0.019(4) Uiso 1 1 d . . . . .
O11 O 0.57845(9) 0.40951(9) 0.42181(8) 0.0225(2) Uani 1 1 d . . . . .
O12 O 0.82437(10) 0.39503(10) 0.30759(9) 0.0272(2) Uani 1 1 d . . . . .
C2 C 0.72499(12) 0.64771(12) 0.33708(10) 0.0149(2) Uani 1 1 d . . . . .
H21 H 0.6586 0.7146 0.2902 0.018 Uiso 1 1 calc R U . . .
C21 C 0.87011(12) 0.70416(13) 0.28185(11) 0.0186(2) Uani 1 1 d . . . . .
H211 H 0.8870 0.7850 0.3127 0.022 Uiso 1 1 calc R U . . .
H212 H 0.9386 0.6306 0.3119 0.022 Uiso 1 1 calc R U . . .
C22 C 0.89016(12) 0.74958(13) 0.13884(11) 0.0185(2) Uani 1 1 d . . . . .
C23 C 0.82547(17) 0.86905(15) 0.07289(13) 0.0304(3) Uani 1 1 d . . . . .
H231 H 0.7640 0.9199 0.1175 0.036 Uiso 1 1 calc R U . . .
C24 C 0.8499(2) 0.91493(17) -0.05791(14) 0.0391(4) Uani 1 1 d . . . . .
H241 H 0.8060 0.9975 -0.1022 0.047 Uiso 1 1 calc R U . . .
C25 C 0.93804(17) 0.84046(17) -0.12360(13) 0.0343(3) Uani 1 1 d . . . . .
H251 H 0.9548 0.8718 -0.2129 0.041 Uiso 1 1 calc R U . . .
C26 C 1.00140(15) 0.72082(17) -0.05931(13) 0.0316(3) Uani 1 1 d . . . . .
H261 H 1.0612 0.6690 -0.1043 0.038 Uiso 1 1 calc R U . . .
C27 C 0.97794(14) 0.67571(15) 0.07162(12) 0.0250(3) Uani 1 1 d . . . . .
H271 H 1.0225 0.5934 0.1155 0.030 Uiso 1 1 calc R U . . .
N3 N 0.69054(10) 0.64261(10) 0.47482(9) 0.0145(2) Uani 1 1 d . . . . .
H31 H 0.6047(17) 0.6054(16) 0.5014(15) 0.024(4) Uiso 1 1 d . . . . .
C4 C 0.79028(13) 0.54830(13) 0.55416(11) 0.0188(2) Uani 1 1 d . . . . .
H41 H 0.8087 0.4635 0.5250 0.023 Uiso 1 1 calc R U . . .
H42 H 0.8787 0.5981 0.5415 0.023 Uiso 1 1 calc R U . . .
C5 C 0.73669(12) 0.50475(13) 0.69259(11) 0.0179(2) Uani 1 1 d . . . . .
C6 C 0.66384(15) 0.38038(14) 0.74415(12) 0.0252(3) Uani 1 1 d . . . . .
H61 H 0.6461 0.3250 0.6915 0.030 Uiso 1 1 calc R U . . .
C7 C 0.61682(16) 0.33656(15) 0.87223(13) 0.0298(3) Uani 1 1 d . . . . .
H71 H 0.5681 0.2509 0.9071 0.036 Uiso 1 1 calc R U . . .
C8 C 0.64118(14) 0.41812(15) 0.94910(12) 0.0258(3) Uani 1 1 d . . . . .
H81 H 0.6082 0.3888 1.0365 0.031 Uiso 1 1 calc R U . . .
C9 C 0.71333(14) 0.54196(14) 0.89875(12) 0.0234(3) Uani 1 1 d . . . . .
H91 H 0.7295 0.5979 0.9515 0.028 Uiso 1 1 calc R U . . .
C10 C 0.76232(13) 0.58478(13) 0.77084(11) 0.0203(3) Uani 1 1 d . . . . .
H101 H 0.8135 0.6690 0.7368 0.024 Uiso 1 1 calc R U . . .
C11 C 0.68310(13) 0.78530(12) 0.50083(11) 0.0170(2) Uani 1 1 d . . . . .
H111 H 0.6275 0.7763 0.5837 0.020 Uiso 1 1 calc R U . . .
H112 H 0.7774 0.8130 0.5064 0.020 Uiso 1 1 calc R U . . .
C12 C 0.62192(12) 0.89977(12) 0.40328(11) 0.0164(2) Uani 1 1 d . . . . .
C13 C 0.48552(13) 0.89395(13) 0.38308(12) 0.0197(2) Uani 1 1 d . . . . .
H131 H 0.4293 0.8171 0.4317 0.024 Uiso 1 1 calc R U . . .
C14 C 0.43157(14) 1.00050(14) 0.29174(12) 0.0240(3) Uani 1 1 d . . . . .
H141 H 0.3392 0.9948 0.2766 0.029 Uiso 1 1 calc R U . . .
C15 C 0.51162(15) 1.11515(14) 0.22259(13) 0.0259(3) Uani 1 1 d . . . . .
H151 H 0.4744 1.1874 0.1599 0.031 Uiso 1 1 calc R U . . .
C16 C 0.64585(15) 1.12390(14) 0.24520(13) 0.0265(3) Uani 1 1 d . . . . .
H161 H 0.7003 1.2034 0.1998 0.032 Uiso 1 1 calc R U . . .
C17 C 0.70059(13) 1.01596(13) 0.33464(12) 0.0224(3) Uani 1 1 d . . . . .
H171 H 0.7932 1.0216 0.3491 0.027 Uiso 1 1 calc R U . . .
O1M O 0.98315(11) 0.20877(13) 0.44355(12) 0.0430(3) Uani 1 1 d . . . . .
H1M H 0.934(2) 0.266(2) 0.398(2) 0.051(6) Uiso 1 1 d . . . . .
C1M C 0.89511(15) 0.13605(17) 0.55085(14) 0.0323(3) Uani 1 1 d . . . . .
H11M H 0.8061 0.1206 0.5263 0.049 Uiso 1 1 calc R U . . .
H12M H 0.8812 0.1913 0.6115 0.049 Uiso 1 1 calc R U . . .
H13M H 0.9367 0.0456 0.5895 0.049 Uiso 1 1 calc R U . . .
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
O12 P1 O11 119.73(5) . . ?
O12 P1 C2 109.84(6) . . ?
O11 P1 C2 105.84(5) . . ?
O12 P1 H1 107.3(6) . . ?
O11 P1 H1 110.4(6) . . ?
C2 P1 H1 102.3(6) . . ?
N3 C2 C21 112.36(9) . . ?
N3 C2 P1 108.74(7) . . ?
C21 C2 P1 114.27(8) . . ?
N3 C2 H21 107.0 . . ?
C21 C2 H21 107.0 . . ?
P1 C2 H21 107.0 . . ?
C22 C21 C2 112.42(10) . . ?
C22 C21 H211 109.1 . . ?
C2 C21 H211 109.1 . . ?
C22 C21 H212 109.1 . . ?
C2 C21 H212 109.1 . . ?
H211 C21 H212 107.9 . . ?
C27 C22 C23 118.69(12) . . ?
C27 C22 C21 120.63(11) . . ?
C23 C22 C21 120.62(11) . . ?
C22 C23 C24 120.59(14) . . ?
C22 C23 H231 119.7 . . ?
C24 C23 H231 119.7 . . ?
C25 C24 C23 120.05(14) . . ?
C25 C24 H241 120.0 . . ?
C23 C24 H241 120.0 . . ?
C26 C25 C24 119.88(13) . . ?
C26 C25 H251 120.1 . . ?
C24 C25 H251 120.1 . . ?
C25 C26 C27 120.04(14) . . ?
C25 C26 H261 120.0 . . ?
C27 C26 H261 120.0 . . ?
C22 C27 C26 120.74(13) . . ?
C22 C27 H271 119.6 . . ?
C26 C27 H271 119.6 . . ?
C2 N3 C4 111.28(9) . . ?
C2 N3 C11 114.70(9) . . ?
C4 N3 C11 109.54(9) . . ?
C2 N3 H31 107.2(10) . . ?
C4 N3 H31 108.0(10) . . ?
C11 N3 H31 105.8(10) . . ?
C5 C4 N3 112.89(9) . . ?
C5 C4 H41 109.0 . . ?
N3 C4 H41 109.0 . . ?
C5 C4 H42 109.0 . . ?
N3 C4 H42 109.0 . . ?
H41 C4 H42 107.8 . . ?
C6 C5 C10 119.22(11) . . ?
C6 C5 C4 119.61(11) . . ?
C10 C5 C4 121.14(11) . . ?
C7 C6 C5 120.46(13) . . ?
C7 C6 H61 119.8 . . ?
C5 C6 H61 119.8 . . ?
C8 C7 C6 119.86(13) . . ?
C8 C7 H71 120.1 . . ?
C6 C7 H71 120.1 . . ?
C9 C8 C7 120.13(12) . . ?
C9 C8 H81 119.9 . . ?
C7 C8 H81 119.9 . . ?
C8 C9 C10 120.03(12) . . ?
C8 C9 H91 120.0 . . ?
C10 C9 H91 120.0 . . ?
C9 C10 C5 120.29(12) . . ?
C9 C10 H101 119.9 . . ?
C5 C10 H101 119.9 . . ?
C12 C11 N3 114.41(9) . . ?
C12 C11 H111 108.7 . . ?
N3 C11 H111 108.7 . . ?
C12 C11 H112 108.7 . . ?
N3 C11 H112 108.7 . . ?
H111 C11 H112 107.6 . . ?
C17 C12 C13 118.96(11) . . ?
C17 C12 C11 119.93(11) . . ?
C13 C12 C11 121.08(11) . . ?
C14 C13 C12 120.03(12) . . ?
C14 C13 H131 120.0 . . ?
C12 C13 H131 120.0 . . ?
C15 C14 C13 120.48(12) . . ?
C15 C14 H141 119.8 . . ?
C13 C14 H141 119.8 . . ?
C16 C15 C14 119.77(12) . . ?
C16 C15 H151 120.1 . . ?
C14 C15 H151 120.1 . . ?
C15 C16 C17 119.68(12) . . ?
C15 C16 H161 120.2 . . ?
C17 C16 H161 120.2 . . ?
C16 C17 C12 121.02(12) . . ?
C16 C17 H171 119.5 . . ?
C12 C17 H171 119.5 . . ?
C1M O1M H1M 106.5(14) . . ?
O1M C1M H11M 109.5 . . ?
O1M C1M H12M 109.5 . . ?
H11M C1M H12M 109.5 . . ?
O1M C1M H13M 109.5 . . ?
H11M C1M H13M 109.5 . . ?
H12M C1M H13M 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
P1 O12 1.4898(10) . ?
P1 O11 1.4985(9) . ?
P1 C2 1.8613(12) . ?
P1 H1 1.340(14) . ?
C2 N3 1.5162(14) . ?
C2 C21 1.5323(16) . ?
C2 H21 1.0000 . ?
C21 C22 1.5187(16) . ?
C21 H211 0.9900 . ?
C21 H212 0.9900 . ?
C22 C27 1.3880(18) . ?
C22 C23 1.3882(19) . ?
C23 C24 1.391(2) . ?
C23 H231 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H241 0.9500 . ?
C25 C26 1.377(2) . ?
C25 H251 0.9500 . ?
C26 C27 1.3920(19) . ?
C26 H261 0.9500 . ?
C27 H271 0.9500 . ?
N3 C4 1.5198(15) . ?
N3 C11 1.5269(15) . ?
N3 H31 0.910(17) . ?
C4 C5 1.5068(16) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.3908(18) . ?
C5 C10 1.3919(18) . ?
C6 C7 1.3896(19) . ?
C6 H61 0.9500 . ?
C7 C8 1.387(2) . ?
C7 H71 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H81 0.9500 . ?
C9 C10 1.3917(17) . ?
C9 H91 0.9500 . ?
C10 H101 0.9500 . ?
C11 C12 1.5042(16) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C17 1.3900(17) . ?
C12 C13 1.3917(17) . ?
C13 C14 1.3902(18) . ?
C13 H131 0.9500 . ?
C14 C15 1.3877(19) . ?
C14 H141 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H151 0.9500 . ?
C16 C17 1.3893(19) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?
O1M C1M 1.4077(18) . ?
O1M H1M 0.84(2) . ?
C1M H11M 0.9800 . ?
C1M H12M 0.9800 . ?
C1M H13M 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341393
