FeCl<sub>2</sub> catalyzed direct modification of dihydropyrrolo[2,1-a]isoquinolines with phenols.
Cui, Hai-Lei; Organic & biomolecular chemistry 18 (2020) 4085–4089; doi:10.1039/d0ob00917b

data_7157499
_publ_section_title
;
 FeCl<sub>2</sub> catalyzed direct modification of
 dihydropyrrolo[2,1-a]isoquinolines with phenols.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4085
_journal_page_last               4089
_journal_paper_doi               10.1039/d0ob00917b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C30 H29 N O7'
_chemical_formula_sum            'C30 H29 N O7'
_chemical_formula_weight         515.54
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-10
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-03-13 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.486(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6950(5)
_cell_length_b                   14.5145(5)
_cell_length_c                   15.6982(7)
_cell_measurement_reflns_used    4816
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      28.8290
_cell_measurement_theta_min      2.5840
_cell_volume                     2541.59(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -15.00  11.00   1.00    5.00    --  -11.59 -99.00  60.00   26
  2  \w    -55.00  24.00   1.00    5.00    --   11.74 -37.00 -90.00   79
  3  \w     -8.00  83.00   1.00    5.00    --   11.74  37.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236782000
_diffrn_orient_matrix_UB_12      -0.0429900000
_diffrn_orient_matrix_UB_13      -0.0187420000
_diffrn_orient_matrix_UB_21      0.0330756000
_diffrn_orient_matrix_UB_22      -0.0225565000
_diffrn_orient_matrix_UB_23      0.0398440000
_diffrn_orient_matrix_UB_31      -0.0489118000
_diffrn_orient_matrix_UB_32      0.0054879000
_diffrn_orient_matrix_UB_33      0.0174704000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11091
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.303
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0530P)^2^+0.5240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3690
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00917b3.cif
_cod_data_source_block           c2001078
_cod_depositor_comments          'Adding full bibliography for 7157499.cif.'
_cod_database_code               7157499
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.91
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C18(H18), C20(H20), C14(H14), C1(H1), C24(H24), C23(H23), C22(H22),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C), C30(H30A,H30B,H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_res_checksum              97823
_shelx_hkl_checksum              83024
_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 1.906
_oxdiff_exptl_absorpt_empirical_full_min 0.749