Y(OTf)<sub>3</sub>-catalyzed phosphorylation of 2H-chromene hemiacetals with P(O)-H compounds to 2-phosphorylated 2H-chromenes.
Zheng, Shi-Lu; Zou, Yun-Xiang; Wen, Zhong; Lin, Jia-Fu; Gu, Ling-Hui; Chen, Long; Organic & biomolecular chemistry 19 (2021) 6812–6816; doi:10.1039/d1ob01221e

data_7158190
_publ_section_title
;
 Y(OTf)<sub>3</sub>-catalyzed phosphorylation of 2H-chromene hemiacetals
 with P(O)-H compounds to 2-phosphorylated 2H-chromenes.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6812
_journal_page_last               6816
_journal_paper_doi               10.1039/d1ob01221e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C30 H25 O5 P'
_chemical_formula_sum            'C30 H25 O5 P'
_chemical_formula_weight         496.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-28 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9636(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.32193(5)
_cell_length_b                   15.92387(9)
_cell_length_c                   17.03098(8)
_cell_measurement_reflns_used    18639
_cell_measurement_temperature    299.51(12)
_cell_measurement_theta_max      76.5060
_cell_measurement_theta_min      3.7850
_cell_volume                     2526.61(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.51(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -82.00  20.00   0.50    0.30    --  -46.37 101.00-164.00  204
  2  \w    -16.00  82.00   0.50    0.30    --   46.37-101.00  91.00  196
  3  \w   -175.00 -83.00   0.50    1.00    -- -102.00-101.00  91.00  184
  4  \w   -109.00 -29.00   0.50    1.00    -- -102.00 101.00-164.00  160
  5  \w     33.00 110.00   0.50    1.00    --  106.06-101.00  91.00  154
  6  \w     87.00 178.00   0.50    1.00    --  106.06 101.00-164.00  182
  7  \w    -24.00  29.00   0.50    0.30    --  -46.37  19.00-150.00  106
  8  \w    -24.00  29.00   0.50    0.30    --  -46.37  19.00   0.00  106
  9  \w   -118.00 -71.00   0.50    0.30    --  -46.37-125.00-120.00   94
 10  \w    -29.00  28.00   0.50    0.30    --   46.37 -19.00 150.00  114
 11  \w   -104.00 -29.00   0.50    1.00    -- -102.00  77.00  30.00  150
 12  \w   -175.00 -81.00   0.50    1.00    -- -102.00 -94.00  60.00  188
 13  \w    -69.00 -29.00   0.50    1.00    -- -102.00  61.00 -60.00   80
 14  \w    -69.00 -29.00   0.50    1.00    -- -102.00  61.00 -30.00   80
 15  \w    -69.00 -29.00   0.50    1.00    -- -102.00  61.00   0.00   80
 16  \w    -69.00 -29.00   0.50    1.00    -- -102.00  61.00  30.00   80
 17  \w   -104.00 -29.00   0.50    1.00    -- -102.00  77.00 -30.00  150
 18  \w     33.00  70.00   0.50    1.00    --  106.06 -61.00 -90.00   74
 19  \w     35.00  73.00   0.50    1.00    --  106.06 -61.00 120.00   76
 20  \w     33.00 107.00   0.50    1.00    --  106.06 -77.00  90.00  148
 21  \w     34.00  64.00   0.50    1.00    --  106.06 -61.00  90.00   60
 22  \w    122.00 178.00   0.50    1.00    --  106.06  61.00-180.00  112
 23  \w     33.00  73.00   0.50    1.00    --  106.06 -61.00-180.00   80
 24  \w     89.00 102.50   0.50    1.00    --  106.06  61.00-180.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0688737000
_diffrn_orient_matrix_UB_12      -0.0741956000
_diffrn_orient_matrix_UB_13      0.0428671000
_diffrn_orient_matrix_UB_21      -0.1315488000
_diffrn_orient_matrix_UB_22      0.0548886000
_diffrn_orient_matrix_UB_23      0.0167423000
_diffrn_orient_matrix_UB_31      -0.0727026000
_diffrn_orient_matrix_UB_32      -0.0290200000
_diffrn_orient_matrix_UB_33      -0.0779531000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24076
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.496
_diffrn_reflns_theta_min         3.801
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0398
_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/[\s^2^(Fo^2^)+(0.0582P)^2^+0.6245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4802
_reflns_number_total             5125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01221e2.cif
_cod_data_source_block           exp_1147
_cod_depositor_comments          'Adding full bibliography for 7158190.cif.'
_cod_original_cell_volume        2526.62(2)
_cod_database_code               7158190
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 P1'
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.851
_diffrn_oxdiff_digest_frames
;
015573789e8c84cc7c7975dfba053127bd00038fe94
;
_diffrn_oxdiff_digest_hkl
;
01f1e34d3675d1138ee5c92ad46ec0d7cbceb3
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C15(H15), C4(H4), C7(H7), C20(H20), C3(H3), C24(H24), C12(H12), C14(H14),
 C10(H10), C21(H21), C23(H23), C11(H11), C22(H22), C13(H13), C30(H30), C26(H26),
  C28(H28), C27(H27), C29(H29)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C1(H1a,H1b,H1c)
;
_shelx_res_checksum              64456
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.693
_oxdiff_exptl_absorpt_empirical_full_min 0.341