Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions.
Zhang, Ying; Yuan, Jia; Huang, Guanglong; Yu, Hong; Liu, Jinpeng; Chen, Jian; Meng, Sixuan; Zhong, Jian-Ji; Dang, Li; Yu, Guang-Ao; Che, Chi-Ming; Chemical science 13 (2022) 6519–6524; doi:10.1039/d2sc00036a

data_1566851
_publ_section_title
;
 Direct visible-light-induced synthesis of P-stereogenic phosphine oxides
 under air conditions.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              6519
_journal_page_last               6524
_journal_paper_doi               10.1039/d2sc00036a
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration R
_chemical_formula_moiety         'C14 H17 N2 O P'
_chemical_formula_sum            'C14 H17 N2 O P'
_chemical_formula_weight         260.26
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-11-11 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2488(9)
_cell_length_b                   10.7508(14)
_cell_length_c                   17.638(2)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.73
_cell_measurement_theta_min      2.31
_cell_volume                     1374.5(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12443
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         2.219
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5618
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1673 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.7528.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 1363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0339
_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/[\s^2^(Fo^2^)+(0.0447P)^2^+0.1919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3299
_reflns_number_total             3496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00036a2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 1566851.cif.'
_cod_database_code               1566851
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00G,H00H), C00H(H00I,H00J,H00K), C00I(H00L,H00M,H00N)
;
_shelx_res_checksum              97472
_shelx_hkl_checksum              9312
_olex2_submission_special_instructions 'No special instructions were received'