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_1549436
_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         'C12 H12 I1 N1 O2'
_chemical_formula_sum            'C12 H12 I N O2'
_chemical_formula_weight         329.14
_chemical_temperature_decomposition 349
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2017-09-18
_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                90
_cell_angle_beta                 99.0055(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8692(2)
_cell_length_b                   8.45340(10)
_cell_length_c                   11.4743(2)
_cell_measurement_reflns_used    15554
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1232.88(3)
_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 0.998
_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  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26750
_diffrn_reflns_theta_full        76.128
_diffrn_reflns_theta_max         76.128
_diffrn_reflns_theta_min         6.288
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    20.300
_exptl_absorpt_correction_T_max  0.07
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.86
_refine_diff_density_min         -0.99
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.0012215
_refine_ls_shift/su_mean         0.0000258
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.54P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0760
_refine_ls_wR_factor_gt          0.0756
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_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2525
_reflns_number_total             2580
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.12
_oxford_diffrn_Wilson_scale      0.06
_oxford_refine_ls_r_factor_ref   0.0278
_oxford_refine_ls_scale          4.29(6)
_oxford_reflns_number_all        2575
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 052eaa17-c
_cod_data_source_file            c8sc01355a2.cif
_cod_data_source_block           5r
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '349
(decomposition)'. The value '349 (decomposition)' was changed to
'349'.

'_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_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C12 H12 I1 N1 O2'
_cod_database_code               1549436