Synthesis of norbornane bisether antibiotics via silver-mediated alkylation
Hickey, Shane M.; Ashton, Trent D.; White, Jonathan M.; Li, Jian; Nation, Roger L.; Yu, Heidi Y.; Elliott, Alysha G.; Butler, Mark S.; Huang, Johnny X.; Cooper, Matthew A.; Pfeffer, Frederick M.; RSC Adv. 5 (2015) 28582–; doi:10.1039/C5RA03321G

data_7219981
_publ_section_title
;
 Synthesis of norbornane bisether antibiotics via silver-mediated
 alkylation
;
_journal_issue                   36
_journal_name_full               'RSC Adv.'
_journal_page_first              28582
_journal_paper_doi               10.1039/C5RA03321G
_journal_volume                  5
_journal_year                    2015
_chemical_formula_sum            'C24 H25 Br2 O6'
_chemical_formula_weight         569.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-02-20 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.4380(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.39290(10)
_cell_length_b                   5.46580(10)
_cell_length_c                   33.5433(4)
_cell_measurement_reflns_used    13284
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      76.6510
_cell_measurement_theta_min      3.6880
_cell_volume                     2434.81(6)
_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_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16695
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.571
_diffrn_reflns_theta_min         4.522
_exptl_absorpt_coefficient_mu    4.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68385
_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_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.5408
_exptl_crystal_size_mid          0.4941
_exptl_crystal_size_min          0.3769
_refine_diff_density_max         1.692
_refine_diff_density_min         -1.387
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.15(2)
_refine_ls_extinction_coef       0.00154(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         8602
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0791P)^2^+3.1059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                8569
_reflns_number_total             8602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_depositor_comments
;

2017-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H50 Br4 O12'
_cod_original_formula_weight         1138.52
_cod_original_formula_units_Z            2
_cod_data_source_file            c5ra03321g2.cif
_cod_data_source_block           shelx
_cod_database_code               7219981
_publcif_datablock.id            {b66b3370-9dbd-4c65-a91d-3b0d3f7994d8}
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              90089
_shelx_fab_checksum              9416