Synthesis of substituted pyridines and pyridazines via ring closing metathesis.
Donohoe, Timothy J; Fishlock, Lisa P; Basutto, José A; Bower, John F; Procopiou, Panayiotis A; Thompson, Amber L; Chemical communications (Cambridge, England) 34 (2009) 3008–3010; doi:10.1039/b904363b

data_7104472
_publ_section_title
;
 Synthesis of substituted pyridines and pyridazines via ring closing
 metathesis.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3008
_journal_page_last               3010
_journal_paper_doi               10.1039/b904363b
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C7 H8 Br1 N1 O1'
_chemical_formula_sum            'C7 H8 Br N O'
_chemical_formula_weight         202.05
_chemical_melting_point          ?
_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
_audit_creation_date             08-06-13
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                77.0394(11)
_cell_angle_beta                 80.0903(12)
_cell_angle_gamma                89.1157(11)
_cell_formula_units_Z            4
_cell_length_a                   7.8535(2)
_cell_length_b                   9.0195(2)
_cell_length_c                   11.4762(3)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     780.16(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10712
_diffrn_reflns_theta_full        26.955
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         5.121
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.198
_exptl_absorpt_correction_T_max  0.44
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.99
_refine_diff_density_min         -1.06
_refine_ls_extinction_coef       62(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001486
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.46P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0781
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0781
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3163
_reflns_number_total             3555
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.68
_oxford_diffrn_Wilson_scale      1.54
_oxford_refine_ls_r_factor_ref   0.0390
_oxford_refine_ls_scale          0.860(3)
_oxford_reflns_number_all        3555
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 5880
_cod_data_source_file            b904363b.txt
_cod_data_source_block           Compound-9
_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C7 H8 Br1 N1 O1'
_cod_database_code               7104472