Studies towards the synthesis of halomon: asymmetric hexafunctionalisation of myrcene
D. Christopher Braddock; Alison X. Gao; Andrew J. P. White; Mariko Whyte; Chem.Commun. 50 (2014) 13725–; doi:10.1039/C4cc06234E

data_7115908
_publ_section_title
;
 Studies towards the synthesis of halomon: asymmetric
 hexafunctionalisation of myrcene
;
_journal_name_full               Chem.Commun.
_journal_page_first              13725
_journal_paper_doi               10.1039/C4cc06234E
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H20 Br2 O4'
_chemical_formula_sum            'C10 H20 Br2 O4'
_chemical_formula_weight         364.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2172(3)
_cell_length_b                   12.8186(6)
_cell_length_c                   21.7125(15)
_cell_measurement_reflns_used    1036
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.3810
_cell_measurement_theta_min      3.6800
_cell_volume                     1452.07(15)
_computing_cell_refinement       CrysAlisPro,
_computing_data_collection       CrysAlisPro,
_computing_data_reduction        CrysAlisPro,
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4605
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.136
_diffrn_reflns_theta_min         2.458
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.580
_exptl_absorpt_correction_T_max  0.638
_exptl_absorpt_correction_T_min  0.252
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       'platy needles'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.014(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0167P)^2^+1.4062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.767
_reflns_number_gt                2040
_reflns_number_total             2874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc06234e2.cif
_cod_data_source_block           (3R,6S,7S)-3
_cod_database_code               7115908
_shelxl_version_number           2013-4