Synthesis of α-diazo-β-keto esters, phosphonates and sulfones via acylbenzotriazole-mediated acylation of a diazomethyl anion.
Pramanik, Mukund M. D.; Rastogi, Namrata; Organic & biomolecular chemistry 13 (2015) 11567–11571; doi:10.1039/c5ob01975c

data_7154756
_publ_section_title
;
 Synthesis of \a-diazo-\b-keto esters, phosphonates and sulfones via
 acylbenzotriazole-mediated acylation of a diazomethyl anion.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11567
_journal_page_last               11571
_journal_paper_doi               10.1039/c5ob01975c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 Cl N3 O4 P'
_chemical_formula_sum            'C10 H11 Cl N3 O4 P'
_chemical_formula_weight         303.64
_chemical_melting_point          374.0(10)
_chemical_name_systematic
'Dimethyl 5-chloro-2-(2-diazoacetyl)phenylphosphoramidate '
_chemical_properties_physical
'Air-sensitive, Moisture-sensitive, Heat-sensitive, Light-sensitive, Photo-sensitive'
_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
_audit_update_record
;
2015-08-08 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                106.549(5)
_cell_angle_beta                 97.092(5)
_cell_angle_gamma                94.090(5)
_cell_formula_units_Z            2
_cell_length_a                   5.927(5)
_cell_length_b                   8.999(5)
_cell_length_c                   13.598(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.43
_cell_volume                     685.6(7)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8330
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0666P)^2^+0.1861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                1509
_reflns_number_total             2555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01975c2.cif
_cod_data_source_block           6augb_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '373-375' was changed to '374.0(10)'
- the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154756.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154756