Three-component 3-(phosphoryl)methylindole synthesis from indoles, H-phosphine oxides and carbonyl compounds under metal-free conditions
Pan, Jiaoting; Zhao, Runmin; Guo, Jiami; Ma, Dumei; Xia, Ying; Gao, Yuxing; Xu, Pengxiang; Zhao, Yufen; Green Chemistry 21 (2019) 792–; doi:10.1039/C8GC03530J

data_7232200
_publ_section_title
;
 Three-component 3-(phosphoryl)methylindole synthesis from indoles,
 H-phosphine oxides and carbonyl compounds under metal-free conditions
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              792
_journal_paper_doi               10.1039/C8GC03530J
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C27 H20 Cl2 N O P'
_chemical_formula_sum            'C27 H20 Cl2 N O P'
_chemical_formula_weight         476.31
_chemical_name_systematic
'((5-chloro-1H-indol-3-yl)(4-chlorophenyl)methyl)diphenylphosphine oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-06 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.293(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5940(2)
_cell_length_b                   11.0586(3)
_cell_length_c                   21.6374(5)
_cell_measurement_reflns_used    3165
_cell_measurement_temperature    173
_cell_measurement_theta_max      62.1950
_cell_measurement_theta_min      4.0780
_cell_volume                     2291.86(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.862
_diffrn_measured_fraction_theta_max 0.991
_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     20.00 103.00   1.00    1.20    --   32.31  57.00 -30.00   83
  2  \w     91.00 164.00   1.00    4.79    --   94.50  64.00  90.00   73
  3  \w     67.00 117.00   1.00    4.79    --   94.50 -50.00 -60.00   50
  4  \w     79.00 121.00   1.00    4.79    --   94.50 -92.00   0.00   42
  5  \w     70.00  96.00   1.00    4.79    --   94.50 -92.00 -90.00   26
  6  \w     64.00  90.00   1.00    4.79    --   94.50 -93.00 -20.90   26
  7  \w     37.00 132.00   1.00    4.79    --   94.50 -92.00 -60.00   95
  8  \w     99.00 167.00   1.00    4.79    --   94.50  38.00-120.00   68
  9  \w     69.00 156.00   1.00    4.79    --   94.50  50.00  30.00   87
 10  \w     52.00 103.00   1.00    1.20    --   32.31  57.00-180.00   51
 11  \w     30.00  62.00   1.00    4.79    --   94.50 -50.00 -60.00   32
 12  \w     23.00  63.00   1.00    4.79    --   94.50 -92.00 -90.00   40
 13  \w     32.00  85.00   1.00    4.79    --   94.50 -50.00  30.00   53
 14  \w    -14.00  73.00   1.00    1.20    --   32.31 -99.00 120.00   87
 15  \w   -114.00 -58.00   1.00    1.20    --  -32.31 178.00 -90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0532065000
_diffrn_orient_matrix_UB_12      0.1273225000
_diffrn_orient_matrix_UB_13      -0.0180677000
_diffrn_orient_matrix_UB_21      0.1313178000
_diffrn_orient_matrix_UB_22      0.0560234000
_diffrn_orient_matrix_UB_23      0.0328130000
_diffrn_orient_matrix_UB_31      0.0760032000
_diffrn_orient_matrix_UB_32      -0.0076933000
_diffrn_orient_matrix_UB_33      -0.0607114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7551
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.043
_diffrn_reflns_theta_min         4.093
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0859P)^2^+0.2594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3186
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc03530j2.cif
_cod_data_source_block           exp_18397
_cod_depositor_comments
'Adding full bibliography for 7232200--7232201.cif.'
_cod_database_code               7232200
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C23(H23), C1(H1A), C27(H27), C11(H11), C14(H14), C4(H4),
 C12(H12), C25(H25), C26(H26), C24(H24), C17(H17), C19(H19), C7(H7), C18(H18),
 C21(H21), C20(H20), C6(H6)
;
_shelx_res_checksum              78173
_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 2.808
_oxdiff_exptl_absorpt_empirical_full_min 0.541