Synthesis of substituted imidazo[1,5-a]pyrazines via mono-, di-, and directed remote metalation strategies.
Board, Johnathan; Wang, Jian-Xin; Crew, Andrew P.; Jin, Meizhong; Foreman, Kenneth; Mulvihill, Mark J.; Snieckus, Victor; Organic letters 11 (2009) 5118–5121; doi:10.1021/ol901889e

data_1504184
_publ_section_title
;
 Synthesis of substituted imidazo[1,5-a]pyrazines via mono-, di-, and
 directed remote metalation strategies.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5118
_journal_page_last               5121
_journal_paper_doi               10.1021/ol901889e
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C15 H11 N3 O2'
_chemical_formula_weight         265.27
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 111.391(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.1116(4)
_cell_length_b                   4.16500(10)
_cell_length_c                   16.2443(5)
_cell_measurement_reflns_used    2414
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.29
_cell_volume                     1203.97(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       23
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_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
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_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5381
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prsim
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.173
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_refine_ls_extinction_coef       0.0048(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_number_parameters     183
_refine_ls_number_reflns         2349
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_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.3793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                1973
_reflns_number_total             2349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901889e_si_002.cif
_cod_data_source_block           vs19
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1203.97(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504184