MeOTf-Mediated Annulation of Alkylnitriles and Arylalkynes Leading to Polysubstituted NH-Pyrroles.
Liu, Yu; Yi, Xiangli; Luo, Xuewei; Xi, Chanjuan; The Journal of organic chemistry 82 (2017) 11391–11398; doi:10.1021/acs.joc.7b01845

data_4033019
_publ_section_title
;
 MeOTf-Mediated Annulation of Alkylnitriles and Arylalkynes Leading to
 Polysubstituted NH-Pyrroles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11391
_journal_page_last               11398
_journal_paper_doi               10.1021/acs.joc.7b01845
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C21 H28 Br N O'
_chemical_formula_sum            'C21 H28 Br N O'
_chemical_formula_weight         390.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   26.350(5)
_cell_length_b                   12.971(3)
_cell_length_c                   26.783(5)
_cell_measurement_reflns_used    19543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4829
_cell_measurement_theta_min      1.4858
_cell_volume                     8085(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            55530
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         0.89
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.041
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             3264
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     877
_refine_ls_number_reflns         18469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.1055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+12.9869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2035
_reflns_number_gt                12753
_reflns_number_total             18469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01845_si_002.cif
_cod_data_source_block           mx5590qaiser
_cod_depositor_comments
;
Adding full bibliography for 4033019--4033020.cif.

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        8085(3)
_cod_original_formula_moiety     '4(C21 H28 Br N O)'
_cod_original_formula_sum        'C84 H112 Br4 N4 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1561.42
_cod_database_code               4033019
_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 Secondary CH2 refined with riding coordinates:
 C19A(H19E,H19F), C6(H6A,H6B), C19B(H19A,H19B), C6B(H6BA,H6BB), C20A(H20E,
 H20F), C6C(H6CA,H6CB), C15B(H15A,H15B), C6A(H6AA,H6AB), C7C(H7CA,H7CB),
 C15(H15G,H15H), C16(H16G,H16H), C7B(H7BA,H7BB), C15A(H15E,H15F), C16C(H16C,
 H16D), C15C(H15C,H15D), C16B(H16A,H16B), C16A(H16E,H16F), C17(H17G,H17H),
 C17B(H17A,H17B), C17A(H17E,H17F), C17C(H17C,H17D), C20B(H20A,H20B), C7(H7A,
 H7B), C19C(H19C,H19D), C7A(H7AA,H7AB), C20C(H20C,H20D), C19(H19G,H19H),
 C20(H20G,H20H)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1B(H1B), N1C(H1C), N1(H1), C14C(H14C), C11C(H11C), C10A(H10A),
 C10B(H10B), C10C(H10C), C13C(H13C), C13B(H13B), C11B(H11B), C13(H13),
 C14A(H14A), C11A(H11A), C14B(H14B), C11(H11), C14(H14), C13A(H13A), C10(H10)
2.c Idealised Me refined as rotating group:
 C21A(H21G,H21H,H21I), C8B(H8BA,H8BB,H8BC), C8A(H8AA,H8AB,H8AC), C8C(H8CA,H8CB,
 H8CC), C21C(H21D,H21E,H21F), C8(H8A,H8B,H8C), C21B(H21A,H21B,H21C), C18C(H18D,
 H18E,H18F), C18B(H18A,H18B,H18C), C18(H18J,H18K,H18L), C18A(H18G,H18H,H18I),
 C21(H21J,H21K,H21L)
;