One-Pot Synthesis of 3-Substituted 2-Arylpyrrole in Aqueous Media via Addition-Annulation of Arylboronic Acid and Substituted Aliphatic Nitriles.
Yousuf, Md; Adhikari, Susanta; Organic letters 19 (2017) 2214–2217; doi:10.1021/acs.orglett.7b00490

data_1545718
_publ_section_title
;
 One-Pot Synthesis of 3-Substituted 2-Arylpyrrole in Aqueous Media via
 Addition-Annulation of Arylboronic Acid and Substituted Aliphatic
 Nitriles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2214
_journal_page_last               2217
_journal_paper_doi               10.1021/acs.orglett.7b00490
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.586(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1990(11)
_cell_length_b                   16.5906(15)
_cell_length_c                   14.4860(14)
_cell_measurement_reflns_used    78
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.865
_cell_measurement_theta_min      2.455
_cell_volume                     2931.6(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39554
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.865
_diffrn_reflns_theta_min         2.455
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1287 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.8103.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.353
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.353
_refine_ls_R_factor_all          0.2040
_refine_ls_R_factor_gt           0.1360
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3219
_refine_ls_wR_factor_ref         0.3950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2915
_reflns_number_total             5636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00490_si_002.cif
_cod_data_source_block           511rkmbg_0m_a
_cod_depositor_comments
;
Adding full bibliography for 1545718--1545719.cif.

2019-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C29 H34 N3 O8'
_cod_original_formula_weight         552.59
_cod_original_formula_moiety         'C15 H17 N O4, C14 H17 N2 O4'
_cod_original_formula_units_Z            4
_cod_database_code               1545718
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   SADABS
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2), N4(H4), N5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C01V(H01A,H01B), C01U(H01E,H01F)
2.c Aromatic/amide H refined with riding coordinates:
 C01C(H01C), C01H(H01H), C01L(H01L), C01M(H01M), C01Q(H01Q), C00S(H00S),
 C00Z(H00Z), C017(H017), C01D(H01D)
2.d Idealised Me refined as rotating group:
 C022(H02A,H02B,H02C), C025(H02D,H02E,H02F), C027(H02G,H02H,H02I), C01X(H01G,
 H01I,H01J), C01Y(H01K,H01N,H01O), C026(H02J,H02K,H02L)
;
_olex2_submission_special_instructions 'No special instructions were received'