One-step protecting-group-free synthesis of azepinomycin in water.
Coggins, Adam J.; Tocher, Derek A.; Powner, Matthew W.; Organic & biomolecular chemistry 13 (2015) 3378–3381; doi:10.1039/c5ob00210a

data_7154331
_publ_section_title
;
 One-step protecting-group-free synthesis of azepinomycin in water.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3378
_journal_page_last               3381
_journal_paper_doi               10.1039/c5ob00210a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C6 H8 N4 O2'
_chemical_formula_sum            'C6 H8 N4 O2'
_chemical_formula_weight         168.16
_chemical_name_systematic        azepinomycin
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2014-11-14 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8750(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.68948(7)
_cell_length_b                   14.04389(15)
_cell_length_c                   7.22458(9)
_cell_measurement_reflns_used    8155
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.3580
_cell_measurement_theta_min      6.1050
_cell_volume                     677.171(13)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150
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_diffrn_measured_fraction_theta_full 0.9936
_diffrn_measured_fraction_theta_max 0.9875
_diffrn_measurement_details
;
  1 omega  -37.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -44.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   30.0000 36

  3 omega  -50.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega -119.00  -75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   30.0000 44

  5 omega -100.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -37.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   90.0000 28

  7 omega  -50.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000 -180.0000 69

  8 omega -106.00  -71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   90.0000 35

  9 omega  -54.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000 -150.0000 46

 10 omega   20.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651   38.0000  120.0000 31

 11 omega  -96.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  125.0000    0.0000 93

 12 omega  -56.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 26

 13 omega  -68.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000    0.0000 39

 14 omega  -56.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 26

 15 omega  -62.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 33

 16 omega  -69.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 40

 17 omega  -55.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000  -90.0000 67

 18 omega  -68.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 40

 19 omega -100.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 65

 20 omega   74.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000   90.0000 88

 21 omega   80.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000   30.0000 92

 22 omega   33.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -45.0000  150.0000 44

 23 omega   74.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000   60.0000 58

 24 omega   76.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -180.0000 102

 25 omega   80.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  -30.0000 28

 26 omega  117.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  -60.0000 58

 27 omega   24.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -95.0000   30.0000 83

 28 omega   74.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -120.0000 96

 29 omega   78.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  150.0000 62

 30 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  120.0000 26

 31 omega   83.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  -60.0000 32

 32 omega   34.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -45.0000  -90.0000 55

 33 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   45.0000  -30.0000 26

 34 omega   32.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180 -125.0000  -30.0000 84

 35 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000    0.0000 26

 36 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  -90.0000 26

 37 omega   74.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -150.0000 53

 38 omega   81.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  150.0000 56

 39 omega  134.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000    0.0000 35

 40 omega   80.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000    0.0000 58

 41 omega   78.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000 -150.0000 25

 42 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000   60.0000 26

 43 omega   30.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -95.0000  150.0000 80

 44 omega  108.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   70.0000  118.1129 25

 45 omega  107.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000 -150.0000 67

 46 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   70.0000  118.1129 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1776708000
_diffrn_orient_matrix_UB_12      0.0234663000
_diffrn_orient_matrix_UB_13      -0.1171613000
_diffrn_orient_matrix_UB_21      0.0870981000
_diffrn_orient_matrix_UB_22      -0.1000904000
_diffrn_orient_matrix_UB_23      0.0392542000
_diffrn_orient_matrix_UB_31      -0.1188257000
_diffrn_orient_matrix_UB_32      -0.0382924000
_diffrn_orient_matrix_UB_33      -0.1743843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9206
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.672
_diffrn_reflns_theta_min         6.303
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83086
_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            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.4643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1294
_reflns_number_total             1328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00210a2.cif
_cod_data_source_block           xstr0044
_cod_depositor_comments          'Adding full bibliography for 7154331.cif.'
_cod_database_code               7154331
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C6 H8 N4 O2'
_chemical_oxdiff_usercomment     'AC (powner) DAT 27-9-13'
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), N4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              69423