Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles.
Miao, Maozhong; Luo, Yi; Xu, Huaping; Jin, Mengchao; Chen, Zhengkai; Xu, Jianfeng; Ren, Hongjun; The Journal of organic chemistry 82 (2017) 12224–12237; doi:10.1021/acs.joc.7b02087

data_4037528
_publ_section_title
;
 Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the
 Application for the Synthesis of Pyrroles.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12224
_journal_page_last               12237
_journal_paper_doi               10.1021/acs.joc.7b02087
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H18 N O2 S'
_chemical_formula_sum            'C18 H18 N O2 S'
_chemical_formula_weight         312.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                108.463(10)
_cell_angle_beta                 90.621(8)
_cell_angle_gamma                108.390(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1086(8)
_cell_length_b                   9.7037(10)
_cell_length_c                   11.3963(12)
_cell_measurement_reflns_used    1681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2392
_cell_measurement_theta_min      3.4531
_cell_volume                     800.98(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -74.00   12.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 86

  2 omega  -38.00   63.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000  150.0000 101

  3 omega  -22.00   69.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0351054000
_diffrn_orient_matrix_UB_12      0.0553847000
_diffrn_orient_matrix_UB_13      -0.0076455000
_diffrn_orient_matrix_UB_21      -0.0803514000
_diffrn_orient_matrix_UB_22      -0.0595238000
_diffrn_orient_matrix_UB_23      -0.0286157000
_diffrn_orient_matrix_UB_31      -0.0306517000
_diffrn_orient_matrix_UB_32      0.0092258000
_diffrn_orient_matrix_UB_33      0.0591141000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.460
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0817
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1557P)^2^+0.3197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2263
_refine_ls_wR_factor_ref         0.2667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1963
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02087_si_001.cif
_cod_data_source_block           170426_xhp_3_105_cmpd_5j
_cod_original_cell_volume        800.97(15)
_cod_database_code               4037528
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.918
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C3(H3A,H3B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              42334
_shelx_hkl_checksum              50866
_olex2_submission_special_instructions 'No special instructions were received'