Solid-phase synthesis of coralmycin A/<i>epi</i>-coralmycin A and desmethoxycoralmycin A.
Hawkins, Paige M. E.; Liu, Dennis Y.; Linington, Roger G.; Payne, Richard J.; Organic & biomolecular chemistry 19 (2021) 6291–6300; doi:10.1039/d1ob01062j

data_7158151
_publ_section_title
;
 Solid-phase synthesis of coralmycin A/<i>epi</i>-coralmycin A and
 desmethoxycoralmycin A.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6291
_journal_page_last               6300
_journal_paper_doi               10.1039/d1ob01062j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C14 H11 N O7 S'
_chemical_formula_sum            'C14 H11 N O7 S'
_chemical_formula_weight         337.30
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-01-07
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8819(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.61747(19)
_cell_length_b                   13.02984(15)
_cell_length_c                   10.52228(16)
_cell_measurement_reflns_used    16594
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5790
_cell_measurement_theta_min      5.4040
_cell_volume                     1424.50(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -112.00 -12.00   1.00    1.00    --  -40.33 -57.00   0.00  100
  2  \w    -92.00 -14.00   1.00    1.00    --  -40.33 -38.00-180.00   78
  3  \w   -102.00 -24.00   1.00    1.00    --  -40.33 -57.00 -60.00   78
  4  \w   -112.00 -12.00   1.00    1.00    --  -40.33 -57.00  90.00  100
  5  \w   -101.00 -11.00   1.00    1.00    --  -40.33 -57.00 150.00   90
  6  \w    -32.00  71.00   1.00    1.00    --   40.33 -62.00  96.80  103
  7  \w      9.00  43.00   1.00    1.00    --   40.33  65.00  50.36   34
  8  \w    -30.00  71.00   1.00    1.00    --   40.33 -64.00-141.50  101
  9  \w     75.00 102.00   1.00    1.00    --   40.33  65.00-116.78   27
 10  \w    -33.00   4.00   1.00    1.00    --   40.33 -63.00  -3.91   37
 11  \w      8.00  71.00   1.00    1.00    --   40.33 -63.00  -3.91   63
 12  \w     86.00 111.00   1.00    1.00    --   40.33  65.00 -40.58   25
 13  \w     10.00  42.00   1.00    1.00    --   40.33  63.00 135.40   32
 14  \w      9.00  49.00   1.00    1.00    --   40.33  65.00 -40.58   40
 15  \w    -25.00  70.00   1.00    1.00    --   40.33 -62.00 -60.79   95
 16  \w     10.00  45.00   1.00    1.00    --   40.33  65.00-116.78   35
 17  \w     82.00 108.00   1.00    4.00    --  113.00  63.00-110.63   26
 18  \w     83.00 116.00   1.00    4.00    --  113.00  59.00 115.10   33
 19  \w     83.00 144.00   1.00    4.00    --  113.00  61.00  98.47   61
 20  \w    133.00 173.00   1.00    4.00    --  113.00  64.00 -43.80   40
 21  \w    129.00 177.00   1.00    4.00    --  113.00  61.00 -30.00   48
 22  \w     39.00 107.00   1.00    4.00    --  113.00 -65.00 -85.51   68
 23  \w     82.00 108.00   1.00    4.00    --  113.00  64.00 -43.80   26
 24  \w    113.00 141.00   1.00    4.00    --  113.00 -65.00 -85.51   28
 25  \w     83.00 151.00   1.00    4.00    --  113.00  61.00-180.00   68
 26  \w     83.00 109.00   1.00    4.00    --  113.00  61.00   0.00   26
 27  \w    122.00 178.00   1.00    4.00    --  113.00  61.00   0.00   56
 28  \w     83.00 109.00   1.00    4.00    --  113.00  61.00-150.00   26
 29  \w    126.00 164.00   1.00    4.00    --  113.00  61.00-150.00   38
 30  \w     83.00 109.00   1.00    4.00    --  113.00  61.00 150.00   26
 31  \w    128.00 170.00   1.00    4.00    --  113.00  51.00  67.68   42
 32  \w     77.00 109.00   1.00    4.00    --  113.00 -35.00-119.15   32
 33  \w     36.00  74.00   1.00    4.00    --  113.00 -35.00-119.15   38
 34  \w    128.00 169.00   1.00    4.00    --  113.00  43.00 -76.80   41
 35  \w    105.00 142.00   1.00    4.00    --  113.00 -31.00 -49.64   37
 36  \w     85.00 111.00   1.00    4.00    --  113.00  45.00  30.00   26
 37  \w     35.00  98.00   1.00    4.00    --  113.00 -31.00 -49.64   63
 38  \w     87.00 115.00   1.00    4.00    --  113.00  43.00 -76.80   28
 39  \w     84.00 122.00   1.00    4.00    --  113.00  51.00  67.68   38
 40  \w    116.00 148.00   1.00    4.00    --  113.00  45.00  30.00   32
 41  \w     86.00 152.00   1.00    4.00    --  113.00  45.00  90.00   66
 42  \w     87.00 119.00   1.00    4.00    --  113.00  45.00 -60.00   32
 43  \w    133.00 177.00   1.00    4.00    --  113.00  45.00 -60.00   44
 44  \w     85.00 123.00   1.00    4.00    --  113.00  45.00-180.00   38
 45  \w    131.00 178.00   1.00    4.00    --  113.00  45.00-180.00   47
 46  \w     84.00 115.00   1.00    4.00    --  113.00  61.00 -30.00   31
 47  \w     86.00 160.00   1.00    4.00    --  113.00  45.00   0.00   74
 48  \w     40.00  69.00   1.00    4.00    --  113.00 -65.00-140.56   29
 49  \w     72.00 110.00   1.00    4.00    --  113.00 -65.00-140.56   38
 50  \w    119.00 144.00   1.00    4.00    --  113.00 -65.00-140.56   25
 51  \w     41.00 103.00   1.00    4.00    --  113.00 -65.00 179.63   62
 52  \w     83.00 109.00   1.00    4.00    --  113.00  61.00-120.00   26
 53  \w     85.00 134.00   1.00    4.00    --  113.00  45.00-150.00   49
 54  \w     83.00 110.00   1.00    4.00    --  113.00  61.00  30.00   27
 55  \w    135.00 178.00   1.00    4.00    --  113.00  61.00  30.00   43
 56  \w     54.00 113.00   1.00    4.00    --  113.00 -65.00 -24.15   59
 57  \w     46.00 107.00   1.00    4.00    --  113.00 -65.00 138.66   61
 58  \w    119.00 144.00   1.00    4.00    --  113.00 -65.00 138.66   25
 59  \w     83.00 109.00   1.00    4.00    --  113.00  61.00 -90.00   26
 60  \w    153.00 178.00   1.00    4.00    --  113.00  61.00 -90.00   25
 61  \w     85.00 174.00   1.00    4.00    --  113.00  45.00 150.00   89
 62  \w     83.00 109.00   1.00    4.00    --  113.00  61.00  90.00   26
 63  \w    108.00 140.00   1.00    4.00    --  113.00 -40.00  15.22   32
 64  \w    127.00 167.00   1.00    4.00    --  113.00  61.00 120.00   40
 65  \w     83.00 120.00   1.00    4.00    --  113.00  61.00 120.00   37
 66  \w     39.00  87.00   1.00    4.00    --  113.00 -40.00  15.22   48
 67  \w    135.00 177.00   1.00    4.00    --  113.00  60.00  39.31   42
 68  \w     85.00 135.00   1.00    4.00    --  113.00  45.00 -30.00   50
 69  \w     83.00 119.00   1.00    4.00    --  113.00  61.00 -60.00   36
 70  \w    111.00 136.00   1.00    4.00    --  113.00 -65.00  95.89   25
 71  \w     64.00 114.00   1.00    4.00    --  113.00 -65.00  24.29   50
 72  \w    125.00 150.00   1.00    4.00    --  113.00  61.00  60.00   25
 73  \w     84.00 109.00   1.00    4.00    --  113.00  61.00  60.00   25
 74  \w     38.00 107.00   1.00    4.00    --  113.00 -65.00  95.89   69
 75  \w     85.00 157.00   1.00    4.00    --  113.00  45.00-120.00   72
 76  \w    119.00 144.00   1.00    4.00    --  113.00 -65.00 179.63   25
 77  \w    140.00 175.00   1.00    4.00    --  113.00  61.00  90.00   35
 78  \w    134.00 160.00   1.00    4.00    --  113.00  61.00 150.00   26
 79  \w    129.00 174.00   1.00    4.00    --  113.00  63.00-110.63   45
 80  \w     83.00 124.00   1.00    4.00    --  113.00  60.00  39.31   41
 81  \w     86.00 112.00   1.00    4.00    --  113.00  43.00 105.64   26
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0268449000
_diffrn_orient_matrix_UB_12      -0.0181175000
_diffrn_orient_matrix_UB_13      0.1366788000
_diffrn_orient_matrix_UB_21      0.0714710000
_diffrn_orient_matrix_UB_22      -0.1034045000
_diffrn_orient_matrix_UB_23      0.0078836000
_diffrn_orient_matrix_UB_31      0.1271336000
_diffrn_orient_matrix_UB_32      0.0543478000
_diffrn_orient_matrix_UB_33      0.0603438000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.467
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'crystallised from a mixture of ethyl acetate and petroleum benzine'
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0585P)^2^+0.5851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2843
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01062j2.cif
_cod_data_source_block           rjp18pt2_s1634
_cod_depositor_comments          'Adding full bibliography for 7158151.cif.'
_cod_database_code               7158151
_sydney_internal_submission_code rjp18_s1634
_sydney_internal_submission_date 2018-04-24
_sydney_internal_submission_number s1634
_sydney_internal_client_code     PMH
_sydney_internal_client_email    phaw1541@chem.usyd.edu.au
_sydney_internal_client_name     'Paige Hawkins'
_sydney_internal_supervisor_code rjp
_sydney_internal_supervisor_name 'Richard Payne'
_sydney_internal_collection_date 2018-05-24
_sydney_internal_collection_user petert
_sydney_internal_process_date    2020-01-07
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2020-01-07
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2020-01-07
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2020-01-07
_sydney_internal_check_user      wlew0588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H11NO7S
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              78522
_olex2_date_sample_data_collection 2019-05-24
_olex2_date_sample_submission    2019-04-24
_olex2_exptl_crystal_mounting_method 'in paratone on a nylon loop'
_olex2_submission_original_sample_id PH-7-38
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.860