Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers.
Sankaranarayanan, Jagadis; Bort, Lauren N.; Mandel, Sarah M.; Chen, Ping; Krause, Jeanette A.; Brooks, Elwood E.; Tsang, Pearl; Gudmundsdottir, Anna D.; Organic letters 10 (2008) 937–940; doi:10.1021/ol703098q

data_1504560
_publ_section_title
;
 Orbital-Overlap control in the solid-state reactivity of
 beta-azido-propiophenones: selective formation of cis-azo-dimers.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              937
_journal_page_last               940
_journal_paper_doi               10.1021/ol703098q
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C9 H8 Br N3 O'
_chemical_formula_sum            'C9 H8 Br N3 O'
_chemical_formula_weight         254.09
_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
_cell_angle_alpha                94.508(2)
_cell_angle_beta                 95.291(2)
_cell_angle_gamma                95.818(2)
_cell_formula_units_Z            2
_cell_length_a                   3.9521(3)
_cell_length_b                   8.8020(6)
_cell_length_c                   13.9895(9)
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.65
_cell_volume                     480.17(6)
_computing_cell_refinement       'SAINT v5.A06 (Bruker)'
_computing_data_collection       'SMART v5.054 (Bruker)'
_computing_data_reduction        'SAINT v5.A06 (Bruker)'
_computing_molecular_graphics    'SHELXTL v5.03,6.14 (Sheldrick)'
_computing_publication_material  'SHELXTL v5.03,6.14 (Sheldrick)'
_computing_structure_refinement  'SHELXTL v5.03,6.14 (Sheldrick)'
_computing_structure_solution    'SHELXTL v5.03,6.14 (Sheldrick)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5050
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.248
_exptl_absorpt_correction_T_max  0.9198
_exptl_absorpt_correction_T_min  0.2951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0454
_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^)+(0.0478P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                1945
_reflns_number_total             2316
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol703098q_si.cif
_cod_data_source_block           00150b
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504560