Divergent reactivity of α-azidochalcones with metal β-diketonates: tunable synthesis of substituted pyrroles and indoles
Rajaguru, Kandasamy; Mariappan, Arumugam; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; Organic Chemistry Frontiers 4 (2017) 124–; doi:10.1039/C6QO00541A

data_1553562
_publ_section_title
;
 Divergent reactivity of \a-azidochalcones with metal \b-diketonates:
 tunable synthesis of substituted pyrroles and indoles
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              124
_journal_paper_doi               10.1039/C6QO00541A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                86.714(4)
_cell_angle_beta                 63.827(3)
_cell_angle_gamma                90.014(4)
_cell_formula_units_Z            8
_cell_length_a                   13.451(4)
_cell_length_b                   14.313(4)
_cell_length_c                   15.248(4)
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.428
_cell_measurement_theta_min      2.240
_cell_volume                     2629.2(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23224
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.590
_diffrn_reflns_theta_max         24.590
_diffrn_reflns_theta_min         1.426
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8807.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         8719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0702P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6320
_reflns_number_total             8719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00541a2.cif
_cod_data_source_block           indole
_cod_original_cell_volume        2629.3(13)
_cod_database_code               1553562
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5340(14) 0.4660(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), N1B(H1B), C2B(H2B), C3B(H3B), C6B(H6B), C8B(H8B), C12B(H12B),
 C13B(H13B), C15B(H15B), C16B(H16B), N1D(H1D), C2D(H2D), C3D(H3D), C6D(H6D),
 C8D(H8D), C12D(H12D), C13D(H13D), C15D(H15D), C16D(H16D), N1F(H1F), C2F(H2F),
 C3F(H3F), C6F(H6F), C8F(H8F), C12F(H12F), C13F(H13F), C15F(H15F), C16F(H16F)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C), C7B(H7BA,H7BB,H7BC), C17B(H17D,H17E,
 H17F), C7D(H7DA,H7DB,H7DC), C17D(H17G,H17H,H17I), C7F(H7FA,H7FB,H7FC),
 C17F(H17J,H17K,H17L)
;
_shelx_res_checksum              1818
_shelx_hkl_checksum              9353
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'