#------------------------------------------------------------------------------
#$Date: 2018-08-25 05:19:55 +0300 (Sat, 25 Aug 2018) $
#$Revision: 210138 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/26/2242618.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242618
loop_
_publ_author_name
'Rohde Jr, Laurence N.'
'Zeller, Matthias'
'Jackson, John A.'
_publ_section_title
;
 Crystal structures of chiral
 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-one derivatives for
 the absolute configuration at phosphorus
;
_journal_coeditor_code           FY2130
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1330
_journal_page_last               1335
_journal_paper_doi               10.1107/S2056989018011349
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C10 H21 Cl2 N2 O2 P'
_chemical_formula_sum            'C10 H21 Cl2 N2 O2 P'
_chemical_formula_weight         303.16
_chemical_name_systematic
(2S,4R)-2-[Bis(2-chloroethyl)amino]-4-isobutyl-1,3,2-oxazaphospholidin-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 115.409(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1044(17)
_cell_length_b                   5.3162(8)
_cell_length_c                   12.8933(17)
_cell_measurement_reflns_used    4852
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.0473
_cell_measurement_theta_min      3.0541
_cell_volume                     749.42(18)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and shelXle (Hübschle et
al.,  2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18357
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.595
_diffrn_reflns_theta_min         3.054
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.7251
_exptl_absorpt_correction_T_min  0.6161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(APEX3; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       rod
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.487
_refine_ls_abs_structure_details
;
Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0480
_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)+(0.0474P)²+0.0175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                3325
_reflns_number_total             4294
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fy2130sup1.cif
_cod_data_source_block           3b
_cod_database_code               2242618
_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   0.891
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 0.42213(6) 0.54753(18) 0.09135(7) 0.0229(2) Uani d 1
Cl Cl2 0.91388(8) 0.02057(18) 0.04717(8) 0.0286(2) Uani d 1
P P1 0.86712(6) 0.58725(13) 0.35572(7) 0.01086(18) Uani d 1
O O1 0.79674(19) 0.8438(4) 0.3538(2) 0.0143(5) Uani d 1
O O2 0.99383(17) 0.6243(4) 0.37047(19) 0.0155(5) Uani d 1
N N1 0.8406(2) 0.4528(5) 0.4568(2) 0.0135(6) Uani d 1
H H1 0.886(3) 0.329(5) 0.492(3) 0.016 Uiso d 1
N N2 0.7888(2) 0.4415(5) 0.2338(2) 0.0134(6) Uani d 1
C C1 0.7379(3) 0.8342(6) 0.4314(3) 0.0164(7) Uani d 1
H H1A 0.650845 0.786491 0.389001 0.020 Uiso calc 1
H H1B 0.742459 1.000426 0.467617 0.020 Uiso calc 1
C C2 0.8062(3) 0.6388(6) 0.5215(3) 0.0133(7) Uani d 1
H H2 0.881348 0.715273 0.582736 0.016 Uiso calc 1
C C3 0.7281(3) 0.5206(7) 0.5755(3) 0.0185(7) Uani d 1
H H3A 0.777041 0.389806 0.630753 0.022 Uiso calc 1
H H3B 0.656971 0.436364 0.514403 0.022 Uiso calc 1
C C4 0.6812(3) 0.7079(7) 0.6380(3) 0.0211(8) Uani d 1
H H4 0.633747 0.841894 0.582193 0.025 Uiso calc 1
C C5 0.5947(4) 0.5717(11) 0.6772(4) 0.0441(12) Uani d 1
H H5A 0.525838 0.501848 0.610291 0.066 Uiso calc 1
H H5B 0.564077 0.690589 0.716789 0.066 Uiso calc 1
H H5C 0.638821 0.435127 0.729761 0.066 Uiso calc 1
C C6 0.7853(3) 0.8330(8) 0.7387(3) 0.0283(9) Uani d 1
H H6A 0.838643 0.921393 0.711137 0.042 Uiso calc 1
H H6B 0.832701 0.704614 0.794716 0.042 Uiso calc 1
H H6C 0.751796 0.953468 0.775185 0.042 Uiso calc 1
C C7 0.6592(3) 0.3876(6) 0.1984(3) 0.0146(7) Uani d 1
H H7A 0.643680 0.364928 0.267210 0.018 Uiso calc 1
H H7B 0.636966 0.229454 0.153571 0.018 Uiso calc 1
C C8 0.5809(3) 0.6018(8) 0.1258(3) 0.0224(8) Uani d 1
H H8A 0.591595 0.615752 0.054077 0.027 Uiso calc 1
H H8B 0.607631 0.762141 0.168369 0.027 Uiso calc 1
C C9 0.8397(3) 0.3806(7) 0.1517(3) 0.0157(7) Uani d 1
H H9A 0.913708 0.483375 0.168799 0.019 Uiso calc 1
H H9B 0.778956 0.420611 0.072762 0.019 Uiso calc 1
C C10 0.8723(3) 0.1042(7) 0.1599(3) 0.0185(7) Uani d 1
H H10A 0.801388 0.001990 0.153912 0.022 Uiso calc 1
H H10B 0.941323 0.069086 0.235248 0.022 Uiso calc 1
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'
Cl Cl 0.1484 0.1585 '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
O2 P1 O1 113.87(12)
O2 P1 N1 120.29(13)
O1 P1 N1 95.71(12)
O2 P1 N2 109.14(13)
O1 P1 N2 107.61(13)
N1 P1 N2 109.10(14)
C1 O1 P1 111.9(2)
C2 N1 P1 111.1(2)
C2 N1 H1 119(3)
P1 N1 H1 118(2)
C7 N2 C9 117.2(3)
C7 N2 P1 119.5(2)
C9 N2 P1 123.0(2)
O1 C1 C2 106.6(2)
O1 C1 H1A 110.4
C2 C1 H1A 110.4
O1 C1 H1B 110.4
C2 C1 H1B 110.4
H1A C1 H1B 108.6
N1 C2 C1 102.7(3)
N1 C2 C3 111.4(3)
C1 C2 C3 113.1(3)
N1 C2 H2 109.8
C1 C2 H2 109.8
C3 C2 H2 109.8
C2 C3 C4 114.4(3)
C2 C3 H3A 108.7
C4 C3 H3A 108.7
C2 C3 H3B 108.7
C4 C3 H3B 108.7
H3A C3 H3B 107.6
C6 C4 C5 111.0(3)
C6 C4 C3 112.0(3)
C5 C4 C3 109.1(3)
C6 C4 H4 108.2
C5 C4 H4 108.2
C3 C4 H4 108.2
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 C8 110.3(3)
N2 C7 H7A 109.6
C8 C7 H7A 109.6
N2 C7 H7B 109.6
C8 C7 H7B 109.6
H7A C7 H7B 108.1
C7 C8 Cl1 110.5(2)
C7 C8 H8A 109.6
Cl1 C8 H8A 109.6
C7 C8 H8B 109.6
Cl1 C8 H8B 109.6
H8A C8 H8B 108.1
N2 C9 C10 109.9(3)
N2 C9 H9A 109.7
C10 C9 H9A 109.7
N2 C9 H9B 109.7
C10 C9 H9B 109.7
H9A C9 H9B 108.2
C9 C10 Cl2 109.9(2)
C9 C10 H10A 109.7
Cl2 C10 H10A 109.7
C9 C10 H10B 109.7
Cl2 C10 H10B 109.7
H10A C10 H10B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C8 1.801(3)
Cl2 C10 1.787(3)
P1 O2 1.475(2)
P1 O1 1.603(2)
P1 N1 1.634(3)
P1 N2 1.641(3)
O1 C1 1.456(4)
N1 C2 1.465(4)
N1 H1 0.85(2)
N2 C7 1.462(4)
N2 C9 1.471(4)
C1 C2 1.513(5)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.529(4)
C2 H2 1.0000
C3 C4 1.534(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C6 1.521(5)
C4 C5 1.526(5)
C4 H4 1.0000
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.520(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.513(5)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 2_746 0.85(2) 2.05(3) 2.863(3) 158(4) yes
C2 H2 O2 2_756 1.00 2.57 3.401(4) 140.7 yes
C1 H1B N1 1_565 0.99 2.71 3.481(4) 134.7 yes
C8 H8A Cl1 2_655 0.99 2.92 3.656(4) 131.6 yes
C8 H8B O1 . 0.99 2.54 3.245(4) 128.1 yes
C7 H7A N1 . 0.99 2.62 3.125(4) 111.5 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 P1 O1 C1 -130.6(2)
N1 P1 O1 C1 -3.9(2)
N2 P1 O1 C1 108.2(2)
O2 P1 N1 C2 103.6(2)
O1 P1 N1 C2 -18.4(2)
N2 P1 N1 C2 -129.3(2)
O2 P1 N2 C7 -178.7(2)
O1 P1 N2 C7 -54.7(3)
N1 P1 N2 C7 48.1(3)
O2 P1 N2 C9 -4.4(3)
O1 P1 N2 C9 119.6(3)
N1 P1 N2 C9 -137.6(3)
P1 O1 C1 C2 23.8(3)
P1 N1 C2 C1 33.0(3)
P1 N1 C2 C3 154.3(2)
O1 C1 C2 N1 -34.2(3)
O1 C1 C2 C3 -154.4(3)
N1 C2 C3 C4 -176.1(3)
C1 C2 C3 C4 -61.0(4)
C2 C3 C4 C6 -62.3(4)
C2 C3 C4 C5 174.4(3)
C9 N2 C7 C8 -83.5(4)
P1 N2 C7 C8 91.1(3)
N2 C7 C8 Cl1 -175.6(2)
C7 N2 C9 C10 -82.3(3)
P1 N2 C9 C10 103.2(3)
N2 C9 C10 Cl2 172.0(2)

_cod_database_fobs_code 2242618
