#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:45:27 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/06/7240653.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_7240653
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         'C24 H23 N2 O4 P'
_chemical_formula_sum            'C24 H23 N2 O4 P'
_chemical_formula_weight         434.41
_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                110.8480(10)
_cell_angle_beta                 92.5530(10)
_cell_angle_gamma                110.0000(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9559(5)
_cell_length_b                   10.8993(5)
_cell_length_c                   11.2372(5)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.1680
_cell_measurement_theta_min      4.7004
_cell_volume                     1051.45(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service V6.2.10'
_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      120(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17202
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.162
_diffrn_reflns_theta_min         4.700
_diffrn_source                   'I\mS micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.448
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.81
_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    1.372
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0333
_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)+(0.0369P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3629
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra03075a3.cif
_cod_data_source_block           ftmpin_dba
_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               7240653
_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   0.782
_shelx_estimated_absorpt_t_max   0.913
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 0.67957(3) 0.27047(3) 0.66347(3) 0.01442(10) Uani 1 1 d . . . . .
O11 O 0.65600(10) 0.12206(10) 0.57369(9) 0.0175(2) Uani 1 1 d . . . . .
O12 O 0.69680(11) 0.31141(11) 0.80590(9) 0.0228(2) Uani 1 1 d . . . . .
C2 C 0.52104(14) 0.29796(14) 0.60198(13) 0.0168(3) Uani 1 1 d . . . . .
H21 H 0.5011 0.3719 0.6720 0.020 Uiso 1 1 calc R U . . .
H22 H 0.5412 0.3295 0.5299 0.020 Uiso 1 1 calc R U . . .
N3 N 0.39249(12) 0.15948(12) 0.55541(11) 0.0150(2) Uani 1 1 d . . . . .
H31 H 0.4216(19) 0.0877(19) 0.5117(16) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.27208(15) 0.15146(15) 0.46340(13) 0.0194(3) Uani 1 1 d . . . . .
H41 H 0.2374 0.2280 0.5077 0.023 Uiso 1 1 calc R U . . .
H42 H 0.1895 0.0592 0.4389 0.023 Uiso 1 1 calc R U . . .
C5 C 0.32166(15) 0.16624(15) 0.34236(13) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.2983(2) 0.26525(19) 0.30314(16) 0.0335(4) Uani 1 1 d . . . . .
H61 H 0.2545 0.3256 0.3542 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3383(2) 0.2771(2) 0.18963(18) 0.0401(4) Uani 1 1 d . . . . .
H71 H 0.3194 0.3437 0.1624 0.048 Uiso 1 1 calc R U . . .
C8 C 0.40542(19) 0.19293(18) 0.11639(16) 0.0328(4) Uani 1 1 d . . . . .
H81 H 0.4338 0.2018 0.0393 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4309(2) 0.09548(19) 0.15617(16) 0.0360(4) Uani 1 1 d . . . . .
H91 H 0.4786 0.0382 0.1068 0.043 Uiso 1 1 calc R U . . .
C10 C 0.38772(19) 0.08029(17) 0.26723(15) 0.0297(4) Uani 1 1 d . . . . .
H101 H 0.4033 0.0109 0.2922 0.036 Uiso 1 1 calc R U . . .
C11 C 0.33710(15) 0.11808(14) 0.66527(13) 0.0174(3) Uani 1 1 d . . . . .
H111 H 0.2691 0.0172 0.6275 0.021 Uiso 1 1 calc R U . . .
H112 H 0.4208 0.1254 0.7222 0.021 Uiso 1 1 calc R U . . .
C12 C 0.26094(15) 0.20531(14) 0.74740(13) 0.0166(3) Uani 1 1 d . . . . .
C13 C 0.33812(16) 0.32794(15) 0.85756(14) 0.0212(3) Uani 1 1 d . . . . .
H131 H 0.4410 0.3599 0.8793 0.025 Uiso 1 1 calc R U . . .
C14 C 0.26494(18) 0.40353(16) 0.93563(14) 0.0268(3) Uani 1 1 d . . . . .
H141 H 0.3178 0.4874 1.0103 0.032 Uiso 1 1 calc R U . . .
C15 C 0.11480(19) 0.35653(17) 0.90446(15) 0.0277(3) Uani 1 1 d . . . . .
H151 H 0.0650 0.4084 0.9579 0.033 Uiso 1 1 calc R U . . .
C16 C 0.03704(17) 0.23450(17) 0.79596(15) 0.0262(3) Uani 1 1 d . . . . .
H161 H -0.0659 0.2024 0.7751 0.031 Uiso 1 1 calc R U . . .
C17 C 0.11001(15) 0.15915(16) 0.71776(14) 0.0215(3) Uani 1 1 d . . . . .
H171 H 0.0565 0.0753 0.6433 0.026 Uiso 1 1 calc R U . . .
C18 C 0.83784(15) 0.39427(15) 0.63214(14) 0.0199(3) Uani 1 1 d . . . . .
H181 H 0.8340 0.4899 0.6666 0.024 Uiso 1 1 calc R U . . .
H182 H 0.9273 0.4004 0.6801 0.024 Uiso 1 1 calc R U . . .
N19 N 0.84767(13) 0.35494(12) 0.49586(12) 0.0200(3) Uani 1 1 d . . . . .
C20 C 0.79030(16) 0.40213(15) 0.41303(15) 0.0230(3) Uani 1 1 d . . . . .
O201 O 0.73243(13) 0.48701(12) 0.44622(12) 0.0329(3) Uani 1 1 d . . . . .
C21 C 0.81562(15) 0.32719(16) 0.28255(15) 0.0229(3) Uani 1 1 d . . . . .
C22 C 0.78000(17) 0.33494(18) 0.16603(16) 0.0300(4) Uani 1 1 d . . . . .
H221 H 0.7332 0.3960 0.1604 0.036 Uiso 1 1 calc R U . . .
C23 C 0.81527(19) 0.2500(2) 0.05723(17) 0.0348(4) Uani 1 1 d . . . . .
H231 H 0.7926 0.2530 -0.0245 0.042 Uiso 1 1 calc R U . . .
C24 C 0.8834(2) 0.1606(2) 0.06632(17) 0.0358(4) Uani 1 1 d . . . . .
H241 H 0.9056 0.1030 -0.0097 0.043 Uiso 1 1 calc R U . . .
C25 C 0.91992(18) 0.15369(18) 0.18432(16) 0.0289(3) Uani 1 1 d . . . . .
H251 H 0.9669 0.0930 0.1905 0.035 Uiso 1 1 calc R U . . .
C26 C 0.88461(15) 0.23919(15) 0.29204(14) 0.0218(3) Uani 1 1 d . . . . .
C27 C 0.90834(14) 0.25703(15) 0.42982(14) 0.0194(3) Uani 1 1 d . . . . .
O271 O 0.96708(11) 0.20202(11) 0.47923(10) 0.0244(2) Uani 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 0.0181 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
O12 P1 O11 120.81(6) . . ?
O12 P1 C18 107.82(6) . . ?
O11 P1 C18 108.42(6) . . ?
O12 P1 C2 110.48(6) . . ?
O11 P1 C2 103.21(6) . . ?
C18 P1 C2 105.01(6) . . ?
N3 C2 P1 107.91(9) . . ?
N3 C2 H21 110.1 . . ?
P1 C2 H21 110.1 . . ?
N3 C2 H22 110.1 . . ?
P1 C2 H22 110.1 . . ?
H21 C2 H22 108.4 . . ?
C2 N3 C4 113.27(11) . . ?
C2 N3 C11 113.09(10) . . ?
C4 N3 C11 112.15(10) . . ?
C2 N3 H31 108.9(11) . . ?
C4 N3 H31 106.9(11) . . ?
C11 N3 H31 101.6(11) . . ?
N3 C4 C5 111.90(11) . . ?
N3 C4 H41 109.2 . . ?
C5 C4 H41 109.2 . . ?
N3 C4 H42 109.2 . . ?
C5 C4 H42 109.2 . . ?
H41 C4 H42 107.9 . . ?
C6 C5 C10 118.86(14) . . ?
C6 C5 C4 119.60(13) . . ?
C10 C5 C4 121.52(13) . . ?
C5 C6 C7 120.54(15) . . ?
C5 C6 H61 119.7 . . ?
C7 C6 H61 119.7 . . ?
C8 C7 C6 120.36(16) . . ?
C8 C7 H71 119.8 . . ?
C6 C7 H71 119.8 . . ?
C7 C8 C9 119.28(15) . . ?
C7 C8 H81 120.4 . . ?
C9 C8 H81 120.4 . . ?
C8 C9 C10 120.70(16) . . ?
C8 C9 H91 119.7 . . ?
C10 C9 H91 119.7 . . ?
C9 C10 C5 120.23(15) . . ?
C9 C10 H101 119.9 . . ?
C5 C10 H101 119.9 . . ?
C12 C11 N3 115.49(11) . . ?
C12 C11 H111 108.4 . . ?
N3 C11 H111 108.4 . . ?
C12 C11 H112 108.4 . . ?
N3 C11 H112 108.4 . . ?
H111 C11 H112 107.5 . . ?
C17 C12 C13 119.14(13) . . ?
C17 C12 C11 119.77(12) . . ?
C13 C12 C11 120.99(13) . . ?
C14 C13 C12 120.16(14) . . ?
C14 C13 H131 119.9 . . ?
C12 C13 H131 119.9 . . ?
C15 C14 C13 119.98(14) . . ?
C15 C14 H141 120.0 . . ?
C13 C14 H141 120.0 . . ?
C16 C15 C14 120.35(13) . . ?
C16 C15 H151 119.8 . . ?
C14 C15 H151 119.8 . . ?
C15 C16 C17 119.72(14) . . ?
C15 C16 H161 120.1 . . ?
C17 C16 H161 120.1 . . ?
C16 C17 C12 120.64(14) . . ?
C16 C17 H171 119.7 . . ?
C12 C17 H171 119.7 . . ?
N19 C18 P1 114.18(9) . . ?
N19 C18 H181 108.7 . . ?
P1 C18 H181 108.7 . . ?
N19 C18 H182 108.7 . . ?
P1 C18 H182 108.7 . . ?
H181 C18 H182 107.6 . . ?
C20 N19 C27 111.83(12) . . ?
C20 N19 C18 124.54(12) . . ?
C27 N19 C18 123.51(12) . . ?
O201 C20 N19 124.74(14) . . ?
O201 C20 C21 129.36(14) . . ?
N19 C20 C21 105.90(12) . . ?
C22 C21 C26 121.83(15) . . ?
C22 C21 C20 129.77(14) . . ?
C26 C21 C20 108.40(13) . . ?
C21 C22 C23 117.39(15) . . ?
C21 C22 H221 121.3 . . ?
C23 C22 H221 121.3 . . ?
C22 C23 C24 120.88(16) . . ?
C22 C23 H231 119.6 . . ?
C24 C23 H231 119.6 . . ?
C23 C24 C25 121.56(16) . . ?
C23 C24 H241 119.2 . . ?
C25 C24 H241 119.2 . . ?
C26 C25 C24 116.99(15) . . ?
C26 C25 H251 121.5 . . ?
C24 C25 H251 121.5 . . ?
C25 C26 C21 121.35(14) . . ?
C25 C26 C27 130.41(14) . . ?
C21 C26 C27 108.24(13) . . ?
O271 C27 N19 125.12(13) . . ?
O271 C27 C26 129.26(13) . . ?
N19 C27 C26 105.61(12) . . ?
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 1.4849(10) . ?
P1 O11 1.4991(9) . ?
P1 C18 1.8332(14) . ?
P1 C2 1.8526(14) . ?
C2 N3 1.4989(17) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5057(17) . ?
N3 C11 1.5228(17) . ?
N3 H31 0.912(18) . ?
C4 C5 1.5103(19) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.384(2) . ?
C5 C10 1.390(2) . ?
C6 C7 1.389(2) . ?
C6 H61 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H71 0.9500 . ?
C8 C9 1.380(2) . ?
C8 H81 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H91 0.9500 . ?
C10 H101 0.9500 . ?
C11 C12 1.5039(18) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C17 1.393(2) . ?
C12 C13 1.3944(19) . ?
C13 C14 1.390(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H141 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H151 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?
C18 N19 1.4537(18) . ?
C18 H181 0.9900 . ?
C18 H182 0.9900 . ?
N19 C20 1.3969(19) . ?
N19 C27 1.4041(18) . ?
C20 O201 1.2104(18) . ?
C20 C21 1.484(2) . ?
C21 C22 1.380(2) . ?
C21 C26 1.386(2) . ?
C22 C23 1.389(2) . ?
C22 H221 0.9500 . ?
C23 C24 1.391(3) . ?
C23 H231 0.9500 . ?
C24 C25 1.394(2) . ?
C24 H241 0.9500 . ?
C25 C26 1.384(2) . ?
C25 H251 0.9500 . ?
C26 C27 1.487(2) . ?
C27 O271 1.2074(18) . ?
