Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes.
Caputo, Dimitri F. J.; Arroniz, Carlos; Dürr, Alexander B; Mousseau, James J.; Stepan, Antonia F.; Mansfield, Steven J.; Anderson, Edward A.; Chemical science 9 (2018) 5295–5300; doi:10.1039/c8sc01355a

data_1549434
_publ_section_title
;
 Synthesis and applications of highly functionalized 1-halo-3-substituted
 bicyclo[1.1.1]pentanes.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              5295
_journal_page_last               5300
_journal_paper_doi               10.1039/c8sc01355a
_journal_volume                  9
_journal_year                    2018
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C8 H12 Br1 N1 O2'
_chemical_formula_sum            'C8 H12 Br N O2'
_chemical_formula_weight         234.09
_chemical_melting_point          352.5(5)
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2017-10-30
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_audit_update_record
;
2018-02-21 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                72.797(4)
_cell_angle_beta                 86.293(4)
_cell_angle_gamma                89.879(3)
_cell_formula_units_Z            4
_cell_length_a                   7.0213(3)
_cell_length_b                   11.7894(5)
_cell_length_c                   12.2156(5)
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      6
_cell_volume                     963.76(7)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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 0.987
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16923
_diffrn_reflns_theta_full        74.196
_diffrn_reflns_theta_max         76.491
_diffrn_reflns_theta_min         3.797
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.523
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3998
_refine_ls_number_restraints     948
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.0010829
_refine_ls_shift/su_mean         0.0000531
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.45P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0875
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0875
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3545
_reflns_number_total             3999
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.29
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0378
_oxford_refine_ls_scale          5.71(9)
_oxford_reflns_number_all        3998
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 070eaa17
_cod_data_source_file            c8sc01355a2.cif
_cod_data_source_block           6b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '352-353' was changed to '352.5(5)' -
the average value was taken and precision was estimated.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549433--1549437.cif.
;
_cod_original_formula_sum        'C8 H12 Br1 N1 O2'
_cod_database_code               1549434