Development of a Gold-Multifaceted Catalysis Approach to the Synthesis of Highly Substituted Pyrroles: Mechanistic Insights via Huisgen Cycloaddition Studies
Simbarashe Ngwerume; William Lewis; Jason E. Camp; Journal of Organic Chemistry 78 (2013) 920–934; doi:10.1021/jo302349k

data_4027896
_publ_contact_author_address
;
  School of Chemistry
  The University of Nottingham
  University Park
  Nottingham  NG7 2RD
  England UK
;
_publ_contact_author_email       jason.camp@nottingham.ac.uk
_publ_contact_author_fax         '0115 951 3563'
_publ_contact_author_name        'Jason E. Camp'
_publ_contact_author_phone       '0115 84 68464'
_publ_section_title
;
 Development of a Gold-Multifaceted Catalysis Approach to the Synthesis of
 Highly Substituted Pyrroles: Mechanistic Insights via Huisgen
 Cycloaddition Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              920
_journal_page_last               934
_journal_paper_doi               10.1021/jo302349k
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H14 N2 O7'
_chemical_formula_sum            'C14 H14 N2 O7'
_chemical_formula_weight         322.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL-97 created file'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5363(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.86962(17)
_cell_length_b                   12.1226(3)
_cell_length_c                   15.5340(3)
_cell_measurement_reflns_used    4311
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.87
_cell_measurement_theta_min      3.65
_cell_volume                     1469.15(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6017
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         75.12
_diffrn_reflns_theta_min         4.64
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.9287
_exptl_crystal_size_mid          0.5835
_exptl_crystal_size_min          0.4397
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.6198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                2545
_reflns_number_total             2918
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo302349k_si_002_3.cif
_cod_data_source_block           5b
_cod_original_cell_volume        1469.14(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027896
_nottingham_internal_coll_name   SNJCCA
_nottingham_internal_coll_number 9570
_nottingham_internal_coll_client SN/JC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time 1.5s
_nottingham_internal_coll_frame_width '1 degree'
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   6/7/2010
_nottingham_internal_process_user WL
_nottingham_internal_process_date 06/07/2010
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 6/7/2010
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 14/7/2010
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 14/7/2010
_nottingham_internal_archive_date 14/7/2010