Synthesis of Polyfunctionalized Pyrroles via a Tandem Reaction of Michael Addition and Intramolecular Cyanide-Mediated Nitrile-to-Nitrile Condensation.
Guchhait, Sankar K.; Sisodiya, Shailendra; Saini, Meenu; Shah, Yesha V.; Kumar, Gulshan; Daniel, Divine P.; Hura, Neha; Chaudhary, Vikas; The Journal of organic chemistry 83 (2018) 5807–5815; doi:10.1021/acs.joc.8b00465

data_4034780
_publ_section_title
;
 Synthesis of Polyfunctionalized Pyrroles via a Tandem Reaction of Michael
 Addition and Intramolecular Cyanide-Mediated Nitrile-to-Nitrile
 Condensation.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5807
_journal_page_last               5815
_journal_paper_doi               10.1021/acs.joc.8b00465
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C13 H10 N4'
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.186(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9373(11)
_cell_length_b                   14.8550(15)
_cell_length_c                   8.7225(11)
_cell_measurement_reflns_used    2424
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     1154.9(2)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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      298
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.105435
_diffrn_orient_matrix_UB_12      0.000766
_diffrn_orient_matrix_UB_13      0.045793
_diffrn_orient_matrix_UB_21      0.026805
_diffrn_orient_matrix_UB_22      0.001238
_diffrn_orient_matrix_UB_23      -0.061738
_diffrn_orient_matrix_UB_31      0.006008
_diffrn_orient_matrix_UB_32      0.111924
_diffrn_orient_matrix_UB_33      0.004853
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11934
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'dull dark black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0747P)^2^+0.1821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2087
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00465_si_002.cif
_cod_data_source_block           ys-104_100k
_cod_database_code               4034780
_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 Rotating group:
 N2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'