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_4037529
_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_absolute_configuration unk
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_Int_Tables_number      5
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-07-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.07 svn.r3419 for OlexSys, GUI svn.r5356)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.790(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5394(7)
_cell_length_b                   5.6134(2)
_cell_length_c                   19.1987(10)
_cell_measurement_reflns_used    1208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2180
_cell_measurement_theta_min      4.7800
_cell_volume                     1389.37(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.6674
_diffrn_measured_fraction_theta_max 0.6674
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     24.00  82.00   1.00    2.95    --   36.71  57.00  30.00   58
  2  \w     13.00 104.00   1.00    2.95    --   36.71  77.00 -90.00   91
  3  \w     70.00 103.00   1.00    2.95    --   36.71  77.00-150.00   33
  4  \w     94.00 169.00   1.00   11.81    --  108.00  45.00 -30.00   75
  5  \w    102.00 161.00   1.00   11.81    --  108.00  45.00  90.00   59
  6  \w     61.00  96.00   1.00    2.95    --   36.71 178.00  90.00   35
  7  \w     28.00  55.00   1.00    2.95    --   36.71  77.00-150.00   27
  8  \w     54.00 134.00   1.00   11.81    --  108.00 -15.00 -60.00   80
  9  \w     91.00 121.00   1.00   11.81    --  108.00-130.00   3.00   30
 10  \w     59.00  87.00   1.00   11.81    --  108.00-130.00   3.00   28
 11  \w     41.00 109.00   1.00   11.81    --  108.00 -95.00   0.00   68
 12  \w     44.00 124.00   1.00   11.81    --  108.00 -61.00   0.00   80
 13  \w     10.00  70.00   1.00    2.95    --   36.71 -99.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0986414000
_diffrn_orient_matrix_UB_12      0.0422377000
_diffrn_orient_matrix_UB_13      -0.0648876000
_diffrn_orient_matrix_UB_21      0.0609209000
_diffrn_orient_matrix_UB_22      -0.0575432000
_diffrn_orient_matrix_UB_23      -0.0537845000
_diffrn_orient_matrix_UB_31      -0.0289967000
_diffrn_orient_matrix_UB_32      -0.2649916000
_diffrn_orient_matrix_UB_33      0.0013113000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2434
_diffrn_reflns_theta_full        72.2334
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_min         3.54
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2636
_exptl_crystal_F_000             561.7372
_refine_diff_density_max         0.1110
_refine_diff_density_min         -0.1256
_refine_diff_density_rms         0.0290
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_d_res_high            0.8095
_refine_ls_d_res_low             12.4841
_refine_ls_goodness_of_fit_ref   1.0305
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0305
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.0781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.282
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              4
_reflns_limit_k_min              -6
_reflns_limit_l_max              23
_reflns_limit_l_min              -23
_reflns_number_gt                1707
_reflns_number_total             1822
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo7b02087_si_001.cif
_cod_data_source_block           20170706-1_cmpd_6a_prime
_cod_original_sg_symbol_Hall     ' C 2y (x,y,-x+z)'
_cod_database_code               4037529
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C17(H17a,H17b)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C6(H6), C3(H3), C5(H5), C4(H4), C15(H15), C14(H14),
 C12(H12), C13(H13)
;
_olex2_date_sample_data_collection 2017-07-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.576