Rhodium-catalyzed pyridannulation of indoles with diazoenals: a direct approach to pyrido[1,2-a]indoles.
Dawande, Sudam Ganpat; Lad, Bapurao Sudam; Prajapati, Sunitkumar; Katukojvala, Sreenivas; Organic & biomolecular chemistry 14 (2016) 5569–5573; doi:10.1039/c6ob00360e

data_7155002
_publ_section_title
;
 Rhodium-catalyzed pyridannulation of indoles with diazoenals: a direct
 approach to pyrido[1,2-a]indoles.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5569
_journal_page_last               5573
_journal_paper_doi               10.1039/c6ob00360e
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H15 F2 N O'
_chemical_formula_sum            'C25 H15 F2 N O'
_chemical_formula_weight         383.40
_chemical_name_common            pyrido[1,2,a]indole
_chemical_name_systematic
(4-fluorophenyl)(10-(2-fluorophenyl)pyrido[1,2-a]indol-9-yl)methanone
_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_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2016-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-02-12 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.422(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3775(7)
_cell_length_b                   11.0241(8)
_cell_length_c                   9.5231(6)
_cell_volume                     922.61(11)
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9156
_diffrn_measured_fraction_theta_max 0.9156
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1243
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         22.97
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_density_diffrn    1.3800
_exptl_crystal_F_000             396.2251
_refine_diff_density_max         0.5169
_refine_diff_density_min         -0.2716
_refine_diff_density_rms         0.0527
_refine_ls_d_res_high            0.9105
_refine_ls_d_res_low             8.9246
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1402
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     262
_refine_ls_number_reflns         1237
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.1164
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1292P)^2^+0.2633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1143
_reflns_number_total             1237
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ob00360e2.cif
_cod_data_source_block           TRY2_a
_cod_depositor_comments
;
        Adding full bibliography for 7155002.cif.

2018-01-23
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_original_formula_moiety     '0.11(C25 H15 F2 N O)'
_cod_original_formula_sum        'C2.778 H1.667 F0.222 N0.111 O0.111'
_cod_original_formula_units_Z    18
_cod_original_formula_weight     42.60
_cod_database_code               7155002
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim C15 \\sim C16 \\sim C17: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C25(H25), C10(H10), C21(H21), C11(H11), C24(H24), C22(H22), C3(H3),
 C4(H4), C6(H6), C5(H5), C16(H16), C17(H17), C15(H15), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'