Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant.
Stress, Cedric J.; Schmidt, Pascal J.; Gillingham, Dennis G.; Organic & biomolecular chemistry 14 (2016) 5529–5533; doi:10.1039/c6ob00168h

data_7154974
_publ_section_title
;
 Comparison of boron-assisted oxime and hydrazone formations leads to the
 discovery of a fluorogenic variant.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5529
_journal_page_last               5533
_journal_paper_doi               10.1039/c6ob00168h
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        'Pascal Schmidt'
_chemical_formula_moiety         'C14 H14 B1 N1 O3'
_chemical_formula_sum            'C14 H14 B N O3'
_chemical_formula_weight         255.08
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2015-01-19
_audit_creation_method           CRYSTALS_ver_14.61
_audit_update_record
;
2016-01-19 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.102(4)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.5248(15)
_cell_length_b                   15.2275(12)
_cell_length_c                   18.9615(16)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    123
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_cell_volume                     5335.1(8)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17258
_diffrn_reflns_theta_full        68.196
_diffrn_reflns_theta_max         68.196
_diffrn_reflns_theta_min         3.761
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.03
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8971
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         4673
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.0007962
_refine_ls_shift/su_mean         0.0000700
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 4.03 6.01 2.70 0.655 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0884
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0884
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4487
_reflns_number_total             4673
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0402
_oxford_refine_ls_scale          0.071969(15)
_oxford_reflns_number_all        4673
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ps655_123k_0m in C2/c'
_cod_data_source_file            c6ob00168h2.cif
_cod_data_source_block           PS655_123K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154974.cif.
;
_cod_original_cell_volume        5335.1(5)
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_original_formula_sum        'C14 H14 B1 N1 O3'
_cod_database_code               7154974