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_7232201
_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         'C30 H27 Cl N O P'
_chemical_formula_sum            'C30 H27 Cl N O P'
_chemical_formula_weight         483.98
_chemical_name_systematic
'(5-chloro-3-(1-phenylbutyl)-1H-indol-2-yl)diphenylphosphine oxide'
_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'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 99.4650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.60810(10)
_cell_length_b                   16.0745(2)
_cell_length_c                   18.0657(2)
_cell_measurement_reflns_used    9128
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9260
_cell_measurement_theta_min      2.7540
_cell_volume                     2465.74(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9591
_diffrn_measured_fraction_theta_max 0.9591
_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      7.00  62.00   0.50    0.05    --   46.75 -65.00  29.00  110
  2  \w     38.00 128.00   0.50    0.11    --  109.54 -65.00  29.00  180
  3  \w     95.00 174.00   0.50    0.11    --  109.54  15.00 120.00  158
  4  \w     92.00 118.00   0.50    0.11    --  109.54  65.00 165.00   52
  5  \w     49.00  74.00   0.50    0.05    --   46.75  65.00 165.00   50
  6  \w     37.00 104.00   0.50    0.11    --  109.54 -94.00 -60.00  134
  7  \w     73.00 106.00   0.50    0.11    --  109.54 -94.00-120.00   66
  8  \w     43.00  87.00   0.50    0.11    --  109.54 -94.00-180.00   88
  9  \w     38.00 108.00   0.50    0.11    --  109.54 -94.00 -90.00  140
 10  \w     39.00 104.00   0.50    0.11    --  109.54-125.00  30.00  130
 11  \w     96.00 166.00   0.50    0.11    --  109.54  45.00-150.00  140
 12  \w    -45.00 -20.00   0.50    0.11    --  -88.50  65.00 165.00   50
 13  \w    -66.00  23.00   0.50    0.05    --  -46.75  65.00 165.00  178
 14  \w    -90.00 -24.00   0.50    0.11    --  -88.50 125.00 -60.00  132
 15  \w   -112.00 -28.00   0.50    0.05    --  -46.75 -65.00  29.00  168
 16  \w   -119.00 -74.00   0.50    0.05    --  -46.75-125.00 150.00   90
 17  \w   -154.00 -80.00   0.50    0.11    --  -88.50 -65.00  29.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008014000
_diffrn_orient_matrix_UB_12      0.0089075000
_diffrn_orient_matrix_UB_13      -0.0849730000
_diffrn_orient_matrix_UB_21      -0.1209534000
_diffrn_orient_matrix_UB_22      -0.0711146000
_diffrn_orient_matrix_UB_23      -0.0151800000
_diffrn_orient_matrix_UB_31      -0.1351994000
_diffrn_orient_matrix_UB_32      0.0636354000
_diffrn_orient_matrix_UB_33      -0.0050217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16972
_diffrn_reflns_theta_full        77.7979
_diffrn_reflns_theta_max         77.80
_diffrn_reflns_theta_min         3.70
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
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    1.3036
_exptl_crystal_description       plate
_exptl_crystal_F_000             1021.2236
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.7546
_refine_diff_density_min         -0.6065
_refine_diff_density_rms         0.1263
_refine_ls_d_res_high            0.7887
_refine_ls_d_res_low             11.9358
_refine_ls_goodness_of_fit_ref   1.0309
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0309
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0858P)^2^+9.3901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4766
_reflns_number_total             5042
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8gc03530j2.cif
_cod_data_source_block           exp_2608
_cod_depositor_comments
'Adding full bibliography for 7232200--7232201.cif.'
_cod_database_code               7232201
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C24(H24), C4(H4), C26(H26), C20(H20), C7(H7), C23(H23), C6(H6),
 C22(H22), C21(H21), C30(H30), C28(H28), C27(H27), C18(H18), C29(H29), C14(H14),
  C17(H17), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_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 1.685
_oxdiff_exptl_absorpt_empirical_full_min 0.509