Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes <i>via</i> directed bridgehead functionalization.
McNamee, Ryan E.; Haugland, Marius M.; Nugent, Jeremy; Chan, Rachel; Christensen, Kirsten E.; Anderson, Edward A.; Chemical science 12 (2021) 7480–7485; doi:10.1039/d1sc01836a

data_1562169
_publ_section_title
;
 Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes <i>via</i> directed
 bridgehead functionalization.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              7480
_journal_page_last               7485
_journal_paper_doi               10.1039/d1sc01836a
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 O2 S'
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.35
_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             2019-11-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '
_audit_update_record
;
2021-03-31 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   6.19930(10)
_cell_length_b                   22.8971(3)
_cell_length_c                   27.5542(3)
_cell_measurement_reflns_used    10878
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.13
_cell_measurement_theta_min      3.82
_cell_volume                     3911.21(9)
_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 0.996
_diffrn_measured_fraction_theta_max 0.992
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_av_unetI/netI     0.049
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            22609
_diffrn_reflns_theta_full        74.767
_diffrn_reflns_theta_max         76.292
_diffrn_reflns_theta_min         3.744
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.156
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.83
_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    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 3403 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.028(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         8095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.0010746
_refine_ls_shift/su_mean         0.0000786
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.05P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0824
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0824
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                7636
_reflns_number_total             8095
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.78
_oxford_diffrn_Wilson_scale      0.24
_oxford_refine_ls_r_factor_ref   0.0342
_oxford_refine_ls_scale          2.106(11)
_oxford_reflns_number_all        8095
_oxford_structure_analysis_title '7246 Cassie 150K'
_cod_data_source_file            d1sc01836a2.cif
_cod_data_source_block           11-150K
_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 

 Adding full bibliography for 1562166--1562170.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1562169
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  0.033(6)
_oxford_bijvoet_difference       0.028(6)
_oxford_refined_flack_x          0.017(9)