Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and Aromatic Compounds
Matthew R. Smith; Alexander J. Blake; Christopher J. Hayes; Malcolm F. G. Stevens; Christopher J. Moody; Journal of Organic Chemistry 74 (2009) 9372–9380; doi:10.1021/jo902165w

data_4025116
_publ_section_title
;
Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and
Aromatic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9372
_journal_page_last               9380
_journal_paper_doi               10.1021/jo902165w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C17 H15 N3 O2, H2 O'
_chemical_formula_sum            'C17 H17 N3 O3'
_chemical_formula_weight         311.34
_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
'water H atoms from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.200(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.273(2)
_cell_length_b                   22.469(5)
_cell_length_c                   9.528(2)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      2.4
_cell_volume                     1509.4(10)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.137
_diffrn_reflns_av_sigmaI/netI    0.081
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13082
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             656
_exptl_crystal_size_max          1.08
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.30
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    'rigid rotor; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3474
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0526
_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^)+(0.052P)^2^+0.242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.130
_refine_ls_wR_factor_ref         0.136
_reflns_number_gt                2965
_reflns_number_total             3474
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo902165w_si_001.cif
_cod_data_source_block           pyimet
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025116