Forwards and backwards – synthesis of Laurencia natural products using a biomimetic and retrobiomimetic strategy incorporating structural reassignment of laurefurenynes C–F
Chan, Hau Sun Sam; Thompson, Amber L.; Christensen, Kirsten E.; Burton, Jonathan W.; Chemical Science  (2020) –; doi:10.1039/D0SC04120C

data_1559305
_publ_section_title
;
 Forwards and backwards -- synthesis of Laurencia natural products using a
 biomimetic and retrobiomimetic strategy incorporating structural
 reassignment of laurefurenynes C--F
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04120C
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H21 Br O3'
_chemical_formula_sum            'C13 H21 Br O3'
_chemical_formula_weight         305.21
_chemical_melting_point          ?
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2019-11-20
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '
_audit_update_record
;
2020-05-21 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6615(2)
_cell_length_b                   9.1823(2)
_cell_length_c                   22.2795(6)
_cell_measurement_reflns_used    14742
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.89
_cell_measurement_theta_min      3.97
_cell_volume                     1362.79(6)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_av_unetI/netI     0.031
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23624
_diffrn_reflns_theta_full        77.356
_diffrn_reflns_theta_max         77.356
_diffrn_reflns_theta_min         3.968
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.078
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.46
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1181 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   -0.034(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0686
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.0009912
_refine_ls_shift/su_mean         0.0000251
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 3.03P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0923
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0923
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2824
_reflns_number_total             2891
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0331
_oxford_refine_ls_scale          6.76(16)
_oxford_reflns_number_all        2886
_oxford_structure_analysis_title 7242
_cod_data_source_file            d0sc04120c2.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1559305
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  -0.047(9)
_oxford_bijvoet_difference       -0.034(5)
_oxford_refined_flack_x          -0.02(3)