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_7060175
_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_absolute_configuration unk
_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           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-11
_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                 102.492(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.8475(15)
_cell_length_b                   13.2526(18)
_cell_length_c                   29.650(4)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.45
_cell_volume                     4928.8(11)
_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 0.995
_diffrn_measured_fraction_theta_max 0.991
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            34556
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         2.236
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1348 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.8669.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 4831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1266
_refine_ls_number_reflns         18954
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0726P)^2^+3.1497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                13233
_reflns_number_total             18954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05253a2.cif
_cod_data_source_block           200506_zjk_1_e_0m
_cod_depositor_comments
'Adding full bibliography for 7060174--7060175.cif.'
_cod_database_code               7060175
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O6, C24, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C43 \\sim C43A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
C41 \\sim O10 \\sim C42: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
O6 \\sim C24 \\sim C25: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43D)=Sof(H43E)=Sof(H43F)=1-FVAR(1)
 Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=FVAR(1)
5.a Riding coordinates:
 N2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B), C24(H24A,H24B), C35(H35A,H35B), C42(H42A,H42B),
 C42(H42C,H42D), C53(H53A,H53B), C60(H60A,H60B), C71(H71A,H71B), C78(H78A,H78B),
  C89(H89A,H89B), C96(H96A,H96B), C107(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), N3(H3), C40(H40), C44(H44), C45(H45), C47(H47), C48(H48), C49(H49),
 C50(H50), C51(H51), N4(H4), C58(H58), C62(H62), C63(H63), C65(H65), C66(H66),
 C67(H67), C68(H68), C69(H69), N5(H5), C76(H76), C80(H80), C81(H81), C83(H83),
 C84(H84), C85(H85), C86(H86), C87(H87), N6(H6), C94(H94), C98(H98), C99(H99),
 C101(H101), C102(H102), C103(H103), C104(H104), C105(H105)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C36(H36A,H36B,
 H36C), C54(H54A,H54B,H54C), C43(H43A,H43B,H43C), C43A(H43D,H43E,H43F),
 C61(H61A,H61B,H61C), C72(H72A,H72B,H72C), C79(H79A,H79B,H79C), C90(H90A,H90B,
 H90C), C97(H97A,H97B,H97C), C108(H10C,H10D,H10E)
;
_shelx_res_checksum              41855
_shelx_hkl_checksum              92725
_olex2_submission_special_instructions 'No special instructions were received'