Synthesis of C3-alkenylated 2,3,4-trisubstituted pyrrole derivatives through cyclization of methylene isocyanides and ene–yne–ketones
Li, Shasha; Zeng, Gongruixue; Xing, Xiaoqi; Yang, Zhiheng; Ma, Feiyun; Li, Boxia; Cheng, Weiyan; Zhang, Jiankang; He, Ruoyu; New Journal of Chemistry 45 (2021) 1834–1837; doi:10.1039/D0NJ05253A

data_7060174
_publ_section_title
;
 Synthesis of C3-alkenylated 2,3,4-trisubstituted pyrrole derivatives
 through cyclization of methylene isocyanides and ene--yne--ketones
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1834
_journal_page_last               1837
_journal_paper_doi               10.1039/D0NJ05253A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-06 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.458(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.567(3)
_cell_length_b                   14.560(3)
_cell_length_c                   18.343(5)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.30
_cell_volume                     3250.0(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26636
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.075
_diffrn_reflns_theta_min         2.293
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0432 after correction.
The Ratio of minimum to maximum transmission is 0.9268.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         7119
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0453P)^2^+1.7426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5830
_reflns_number_total             7119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05253a2.cif
_cod_data_source_block           200506_zjk_1_d_0m
_cod_depositor_comments
'Adding full bibliography for 7060174--7060175.cif.'
_cod_database_code               7060174
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.963
_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. Restrained distances
 C2-C8 \\sim C2-C8A
 with sigma of 0.02
 C10-C9 \\sim C10-C9A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C2-C9 \\sim C2-C9A
 with sigma of 0.04
 C10-C8 \\sim C10-C8A
 with sigma of 0.04
 C27-C26 \\sim C27A-C26
 with sigma of 0.02
 C28-C27 \\sim C28-C27A
 with sigma of 0.02
3. Rigid bond restraints
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C28, C33, C32, C31, C30, C29
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C8 \\sim C9 \\sim C8A \\sim C9A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C27 \\sim C27A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
5. Others
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=FVAR(1)
 Sof(H26A)=Sof(C27A)=Sof(H27A)=1-FVAR(2)
 Sof(H26)=Sof(C27)=Sof(H27)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B), C24(H24A,H24B), C35(H35A,H35B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C8(H8),
 C9(H9), C8A(H8A), C9A(H9A), N2(H2), C22(H22), C26(H26), C26(H26A), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33), C27(H27), C27A(H27A)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              96643
_shelx_hkl_checksum              40205
_olex2_submission_special_instructions 'No special instructions were received'