Highly Stereoselective Synthesis of Functionalized Pyrrolo[3,2-c]quinolines via N-Heterocyclic Carbene Catalyzed Cascade Sequence.
Yang, Yu-Jie; Zhang, Hai-Rui; Zhu, Shi-Ya; Zhu, Ping; Hui, Xin-Ping; Organic letters 16 (2014) 5048–5051; doi:10.1021/ol5023917

data_1517815
_publ_section_title
;
 Highly Stereoselective Synthesis of Functionalized
 Pyrrolo[3,2-c]quinolines via N-Heterocyclic Carbene Catalyzed Cascade
 Sequence.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5048
_journal_page_last               5051
_journal_paper_doi               10.1021/ol5023917
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration none
_chemical_formula_moiety         'C30 H29 Cl N2 O7 S'
_chemical_formula_sum            'C30 H29 Cl N2 O7 S'
_chemical_formula_weight         597.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-28
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90
_cell_angle_beta                 108.111(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9525(6)
_cell_length_b                   7.8235(5)
_cell_length_c                   16.0480(10)
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    294.29(10)
_cell_measurement_theta_max      26.0730
_cell_measurement_theta_min      3.7180
_cell_volume                     1426.31(16)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.29(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0210604000
_diffrn_orient_matrix_UB_12      0.0218900000
_diffrn_orient_matrix_UB_13      -0.0450849000
_diffrn_orient_matrix_UB_21      -0.0435670000
_diffrn_orient_matrix_UB_22      -0.0646096000
_diffrn_orient_matrix_UB_23      -0.0069715000
_diffrn_orient_matrix_UB_31      -0.0394489000
_diffrn_orient_matrix_UB_32      0.0597155000
_diffrn_orient_matrix_UB_33      0.0089597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5776
_diffrn_reflns_point_group_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0314P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0994
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_reflns_Friedel_fraction_full    0.477
_reflns_Friedel_fraction_max     0.469
_reflns_number_gt                3527
_reflns_number_total             4247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5023917_si_001.cif
_cod_data_source_block           yangyj0527
_cod_depositor_comments          'Adding full bibliography for 1517815.cif.'
_cod_original_cell_volume        1426.31(15)
_cod_database_code               1517815
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.78
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C5(H5), C28(H28), C15(H15), C25(H25), C16(H16), C2(H2A), C26(H26),
 C3(H3), C4(H4), C29(H29), C17(H17)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              9673
_shelx_hkl_checksum              34636