Water-soluble and UV traceable isatoic anhydride-based reagents for bioconjugation
Fessler, Adam B.; Garmon, Corey B.; Heavey, Thomas; Fowler, Anthony John; Ogle, Craig; Organic & Biomolecular Chemistry  (2017) –; doi:10.1039/C7OB02377D

data_7155957
_publ_section_title
;
 Water-soluble and UV traceable isatoic anhydride-based reagents for
 bioconjugation
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02377D
_journal_year                    2017
_chemical_formula_moiety         'Br, C15 H17 N2 O3'
_chemical_formula_sum            'C15 H17 Br N2 O3'
_chemical_formula_weight         353.21
_chemical_name_systematic
'N-(2-(2,4-dioxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)ethyl)-N,N-dimethylethynaminium bromide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2017-09-21 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1025(4)
_cell_length_b                   17.9372(15)
_cell_length_c                   11.9529(9)
_cell_measurement_reflns_used    1098
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.1400
_cell_measurement_theta_min      4.4220
_cell_volume                     1522.79(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.4419
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega   20.00  112.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       40.8425   57.0000  -60.0000 92

  2 omega   40.00   69.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       40.8425  -57.0000  150.0000 29

  3 omega   20.00   77.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 57

  4 omega   56.00   86.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   90.0000 30

  5 omega   64.00  131.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   30.0000 67

  6 omega   63.00   96.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -90.0000 33

  7 omega   26.00   53.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -90.0000 27

  8 omega   19.00   69.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 50

  9 omega   70.00  107.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -30.0000 37

 10 omega   26.00   51.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 25

 11 omega   21.00   56.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 35

 12 omega   82.00  133.00   1.0000    5.2200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -134.7012 51
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1097312000
_diffrn_orient_matrix_UB_12      0.0115511000
_diffrn_orient_matrix_UB_13      -0.1097753000
_diffrn_orient_matrix_UB_21      -0.1861448000
_diffrn_orient_matrix_UB_22      -0.0150000000
_diffrn_orient_matrix_UB_23      0.0620845000
_diffrn_orient_matrix_UB_31      -0.0184018000
_diffrn_orient_matrix_UB_32      0.0838090000
_diffrn_orient_matrix_UB_33      0.0264597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4592
_diffrn_reflns_point_group_measured_fraction_full 0.760
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.023
_diffrn_reflns_theta_min         4.445
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0441P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.475
_reflns_Friedel_fraction_full    0.517
_reflns_Friedel_fraction_max     0.525
_reflns_number_gt                1693
_reflns_number_total             2099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02377d2.cif
_cod_data_source_block           131029_th_cg_briqyne_x5_cu1
_cod_database_code               7155957
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C15 H17 O3 N2 Br1'
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C6(H6a,H6b), C1(H1a,H1b)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C28(H28), C30(H30)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C10(H10a,H10b,H10c)
2.d :
 C3(H3)
;
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a cryoloop with oil'
_olex2_submission_special_instructions 'No special instructions were received'