An efficient and green synthesis of ferrocenyl-quinoline conjugates via a TsOH-catalyzed three-component reaction in water
Mou, Rui-Qi; Zhao, Mei; Lv, Xue-Xin; Zhang, Sheng-Yan; Guo, Dian-Shun; RSC Advances 8 (2018) 9555–; doi:10.1039/C8RA01004H

data_7230266
_publ_section_title
;
 An efficient and green synthesis of ferrocenyl-quinoline conjugates via a
 TsOH-catalyzed three-component reaction in water
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              9555
_journal_paper_doi               10.1039/C8RA01004H
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C26 H21 Fe N'
_chemical_formula_sum            'C26 H21 Fe N'
_chemical_formula_weight         403.29
_chemical_name_systematic
;
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-11-05 deposited with the CCDC.
2018-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.835(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.36603(17)
_cell_length_b                   20.5582(4)
_cell_length_c                   11.3490(2)
_cell_measurement_reflns_used    3346
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.0300
_cell_measurement_theta_min      4.2950
_cell_volume                     1858.12(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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     -3.00  50.00   1.00    1.00    --    0.00  57.00  60.00   53
  2  \w     39.00 124.00   1.00    1.00    --   54.00  37.00 150.00   85
  3  \w     86.00 177.00   1.00    1.00    --  108.00  50.00 150.00   91
  4  \w    100.00 142.00   1.00    1.00    --  108.00 111.00  60.00   42
  5  \w    103.00 169.00   1.00    1.00    --  108.00  50.00 120.00   66
  6  \w     94.00 120.00   1.00    1.00    --  108.00 -63.00 -30.00   26
  7  \w     87.00 133.00   1.00    1.00    --  108.00 -91.00 -60.00   46
  8  \w     41.00 127.00   1.00    1.00    --  108.00 -50.00 -90.00   86
  9  \w     66.00  91.00   1.00    1.00    --   54.00  57.00 -60.00   25
 10  \w     89.00 177.00   1.00    1.00    --  108.00  77.00-120.00   88
 11  \w     36.00  74.00   1.00    1.00    --  108.00 -91.00 -60.00   38
 12  \w     23.00  86.00   1.00    1.00    --   54.00-125.00 -30.00   63
 13  \w    -16.00  84.00   1.00    1.00    --   54.00 -77.00   0.00  100
 14  \w    -68.00   4.00   1.00    1.00    --    0.00 -57.00 -60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0874384000
_diffrn_orient_matrix_UB_12      -0.0007889000
_diffrn_orient_matrix_UB_13      -0.1407901000
_diffrn_orient_matrix_UB_21      -0.1244996000
_diffrn_orient_matrix_UB_22      -0.0515674000
_diffrn_orient_matrix_UB_23      0.0174270000
_diffrn_orient_matrix_UB_31      -0.1192632000
_diffrn_orient_matrix_UB_32      0.0543920000
_diffrn_orient_matrix_UB_33      0.0144941000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6994
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.30
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.6844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                3136
_reflns_number_total             3490
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra01004h2.cif
_cod_data_source_block           exp_2213
_cod_original_cell_volume        1858.12(6)
_cod_database_code               7230266
_chemical_oxdiff_formula         'C1 H1 O1 N1 Fe1'
_reflns_odcompleteness_completeness 99.91
_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 Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C1(H1), C8(H8), C3(H3), C2(H2), C9(H9), C6(H6), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C26(H26), C25(H25), C24(H24), C23(H23), C20(H20), C22(H22),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 1.604
_oxdiff_exptl_absorpt_empirical_full_min 0.720