Crystal structures of chiral 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-one derivatives for the absolute configuration at phosphorus
Rohde Jr, Laurence N.; Zeller, Matthias; Jackson, John A.; Acta Crystallographica Section E 74 (2018) 1330–1335; doi:10.1107/S2056989018011349

data_2242617
_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          'C14 H21 Cl2 N2 O2 P'
_chemical_formula_sum            'C14 H21 Cl2 N2 O2 P'
_chemical_formula_weight         351.20
_chemical_name_systematic
(2<i>S</i>,4<i>S</i>,5<i>R</i>)-2-[Bis(2-chloroethyl)amino]-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6894(6)
_cell_length_b                   11.1623(6)
_cell_length_c                   14.0025(7)
_cell_measurement_reflns_used    9357
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.2097
_cell_measurement_theta_min      2.3971
_cell_volume                     1670.75(15)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and <i>shelXle</i> (H\"ubschle <i>et
al.</i>,  2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0330
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            54792
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         40.297
_diffrn_reflns_theta_min         2.333
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(APEX3; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.262
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.335
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 4150 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_extinction_coef       0.0137(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         10531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0243
_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/[\s^2^(Fo^2^)+(0.0343P)^2^+0.1289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                9765
_reflns_number_total             10531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fy2130sup1.cif
_cod_data_source_block           2b
_cod_database_code               2242617
_cod_database_fobs_code          2242617
_shelx_estimated_absorpt_t_min   0.810
_shelx_estimated_absorpt_t_max   0.882
_shelx_hkl_checksum              33865
_shelx_res_checksum              27095