Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.
Xu, Xinfang; Ratnikov, Maxim O.; Zavalij, Peter Y.; Doyle, Michael P.; Organic letters 13 (2011) 6122–6125; doi:10.1021/ol2026125

data_1502585
_publ_section_title
;
 Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade
 process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6122
_journal_page_last               6125
_journal_paper_doi               10.1021/ol2026125
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_chemical_name_common            organic
_chemical_name_systematic
;
organic
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                90.9745(9)
_cell_angle_beta                 97.1725(9)
_cell_angle_gamma                90.8725(9)
_cell_formula_units_Z            2
_cell_length_a                   5.9348(4)
_cell_length_b                   8.4805(5)
_cell_length_c                   15.4624(9)
_cell_measurement_reflns_used    9643
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.4
_cell_volume                     771.90(8)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker Smart Apex2, CCD'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      610,610,610,1200
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.1096110
_diffrn_orient_matrix_UB_12      -0.0853977
_diffrn_orient_matrix_UB_13      -0.0089152
_diffrn_orient_matrix_UB_21      -0.0532551
_diffrn_orient_matrix_UB_22      -0.0016108
_diffrn_orient_matrix_UB_23      -0.0639767
_diffrn_orient_matrix_UB_31      0.1183201
_diffrn_orient_matrix_UB_32      0.0813484
_diffrn_orient_matrix_UB_33      -0.0088239
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11993
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.40
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_id                'Doyle/Xu R4(C4HNO) or R4(C4HN) 150K'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+0.459P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                4151
_reflns_number_total             4469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2026125_si_003.cif
_cod_data_source_block           2136
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502585
_diffrn_measurement_frame_width-ccd -0.30
_diffrn_measurement_total_frames-ccd 3030
_diffrn_measurement_frame_time-ccd 20
_diffrn_measurement_total_time-ccd 21.9
_diffrn_detector_distance-ccd    5.0000
_diffrn_measurement_frame_size-ccd 512