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_1553564
_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         'C2 H6 O S, C21 H18 N2 O5'
_chemical_formula_sum            'C23 H24 N2 O6 S'
_chemical_formula_weight         456.50
_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
_audit_creation_date             2015-12-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-05-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                60.7330(10)
_cell_angle_beta                 81.883(2)
_cell_angle_gamma                87.112(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5455(4)
_cell_length_b                   12.0470(6)
_cell_length_c                   12.1501(6)
_cell_measurement_reflns_used    9788
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      2.883
_cell_volume                     1079.97(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.997
_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  0.0923
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42203
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.883
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.6908
_exptl_absorpt_correction_T_min  0.4271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1639 before and 0.1181 after correction.
The Ratio of minimum to maximum transmission is 0.6183.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.5035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4310
_reflns_number_total             4967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00541a2.cif
_cod_data_source_block           cham2
_cod_database_code               1553564
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. 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
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,H4SC), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              1227
_shelx_hkl_checksum              71552
_olex2_submission_special_instructions 'No special instructions were received'