Silver(i)-promoted C5–H phosphonation of 8-aminoquinoline amides with H-phosphonates
Sun, Mengmeng; Sun, Suyan; Qiao, Huijie; Yang, Fan; Zhu, Yu; Kang, Jianxun; Wu, Yusheng; Wu, Yangjie; Organic Chemistry Frontiers 3 (2016) 1646–; doi:10.1039/C6QO00379F

data_1553505
_publ_section_title
;
 Silver(i)-promoted C5--H phosphonation of 8-aminoquinoline amides with
 H-phosphonates
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1646
_journal_paper_doi               10.1039/C6QO00379F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C22 H25 N2 O4 P'
_chemical_formula_sum            'C22 H25 N2 O4 P'
_chemical_formula_weight         412.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-18 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3031(6)
_cell_length_b                   18.1046(6)
_cell_length_c                   15.6855(6)
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4320
_cell_measurement_theta_min      3.7130
_cell_volume                     4345.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     56.00  84.00   1.00   12.50    --   18.07 178.00-150.00   28
  2  \w    -25.00   6.00   1.00   12.50    --   18.07 -99.00-180.00   31
  3  \w    -48.00  29.00   1.00   12.50    --   18.07 -57.00-120.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0443818000
_diffrn_orient_matrix_UB_12      -0.0095628000
_diffrn_orient_matrix_UB_13      0.0069549000
_diffrn_orient_matrix_UB_21      0.0037328000
_diffrn_orient_matrix_UB_22      -0.0289177000
_diffrn_orient_matrix_UB_23      -0.0302881000
_diffrn_orient_matrix_UB_31      0.0128236000
_diffrn_orient_matrix_UB_32      -0.0246474000
_diffrn_orient_matrix_UB_33      0.0328475000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11148
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4439
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0941P)^2^+0.6761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2694
_reflns_number_total             4439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00379f2.cif
_cod_data_source_block           20160340
_cod_database_code               1553505
_chemical_oxdiff_formula         C1H1N1O1P1
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17A-C19A
 1.65 with sigma of 0.02
 C17-C19
 1.55 with sigma of 0.02
 C17A-C18A
 1.55 with sigma of 0.02
 C17-C18
 1.55 with sigma of 0.02
 O4-C17
 1.4 with sigma of 0.02
 O4-C17A
 1.43 with sigma of 0.02
 O3-C20A
 1.43 with sigma of 0.02
 O3-C20
 1.43 with sigma of 0.02
 C20A-C22A
 1.55 with sigma of 0.02
 C20-C22
 1.55 with sigma of 0.02
 C20-C21
 1.55 with sigma of 0.02
 C19A-C18A
 2.4 with sigma of 0.02
 C20A-C21A
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C17A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C19) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C18)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
Uanis(C22) = Uanis(C22A)
4. Others
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19A)=
 Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19)=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=FVAR(1)
 Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=
 Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(2)
 Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C17(H17), C17A(H17A), C20(H20), C20A(H20A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), N2(H2A)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C19(H19A,H19B,H19C), C19A(H19D,
 H19E,H19F), C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F), C22(H22A,H22B,H22C),
 C22A(H22D,H22E,H22F)
;
_shelx_res_checksum              42067
_shelx_hkl_checksum              62834
_shelx_shelxl_version_number     2014/7
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.861