# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1411982'
_audit_update_record             
;
2015-07-10 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        
'3-fluorobicyclo[1.1.1]pentane-1-carboxylic acid'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 F O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         130.12

_chemical_melting_point          397.15

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3910(6)
_cell_length_b                   5.4434(6)
_cell_length_c                   11.1433(12)
_cell_angle_alpha                84.283(8)
_cell_angle_beta                 78.772(9)
_cell_angle_gamma                68.545(7)
_cell_volume                     298.37(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1048
_cell_measurement_theta_min      5.0672
_cell_measurement_theta_max      27.0315
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.260
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             136

_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            5361
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0852
_diffrn_reflns_theta_min         5.07
_diffrn_reflns_theta_max         31.20
_diffrn_reflns_theta_full        31.20
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             1889
_reflns_number_gt                1303
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1499
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         1889
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.0197P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7548(3) 0.3029(3) 0.36778(14) 0.0150(3) Uani d . . . 1 . .
C C2 0.9612(3) 0.1380(3) 0.27122(14) 0.0158(3) Uani d . . . 1 . .
C C3 1.2082(3) -0.1085(3) 0.30061(15) 0.0205(4) Uani d . . . 1 . .
H H3A 1.3478 -0.0726 0.3345 0.025 Uiso calc U . R 1 . .
H H3B 1.1667 -0.2633 0.3402 0.025 Uiso calc U . R 1 . .
C C4 1.1614(4) 0.2195(3) 0.16956(16) 0.0225(4) Uani d . . . 1 . .
H H4A 1.0828 0.3329 0.1013 0.027 Uiso calc U . R 1 . .
H H4B 1.2982 0.2714 0.1975 0.027 Uiso calc U . R 1 . .
C C5 0.9220(3) -0.0292(3) 0.17662(16) 0.0214(4) Uani d . . . 1 . .
H H5A 0.8649 -0.1793 0.2101 0.026 Uiso calc U . R 1 . .
H H5B 0.8294 0.0698 0.1088 0.026 Uiso calc U . R 1 . .
C C6 1.2256(3) -0.0782(3) 0.16146(15) 0.0204(4) Uani d . . . 1 . .
F F1 1.4246(2) -0.24192(19) 0.07889(10) 0.0289(3) Uani d . . . 1 . .
O O1 0.8057(3) 0.4871(2) 0.40701(11) 0.0258(3) Uani d . . . 1 . .
H H1O 0.6947 0.5656 0.4685 0.039 Uiso d U . R 1 . .
O O2 0.5469(2) 0.2456(2) 0.40885(11) 0.0252(3) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.2611(19) ?
C1 O1 . 1.2674(19) ?
C1 C2 . 1.482(2) ?
C2 C5 . 1.550(2) ?
C2 C4 . 1.555(2) ?
C2 C3 . 1.567(2) ?
C2 C6 . 1.815(2) ?
C3 C6 . 1.531(2) ?
C4 C6 . 1.536(2) ?
C5 C6 . 1.537(2) ?
C6 F1 . 1.3678(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 124.32(14) ?
O2 C1 C2 . . 118.51(14) ?
O1 C1 C2 . . 117.11(14) ?
C1 C2 C5 . . 128.26(15) ?
C1 C2 C4 . . 128.34(13) ?
C5 C2 C4 . . 88.81(12) ?
C1 C2 C3 . . 122.76(13) ?
C5 C2 C3 . . 88.11(12) ?
C4 C2 C3 . . 87.69(12) ?
C1 C2 C6 . . 175.97(13) ?
C5 C2 C6 . . 53.64(10) ?
C4 C2 C6 . . 53.57(9) ?
C3 C2 C6 . . 53.21(9) ?
C6 C3 C2 . . 71.71(11) ?
C6 C4 C2 . . 71.90(11) ?
C6 C5 C2 . . 72.03(11) ?
F1 C6 C3 . . 124.84(14) ?
F1 C6 C4 . . 125.68(14) ?
C3 C6 C4 . . 89.69(12) ?
F1 C6 C5 . . 125.53(14) ?
C3 C6 C5 . . 89.93(13) ?
C4 C6 C5 . . 89.99(13) ?
F1 C6 C2 . . 179.79(16) ?
C3 C6 C2 . . 55.08(9) ?
C4 C6 C2 . . 54.53(9) ?
C5 C6 C2 . . 54.33(9) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1421038'
_audit_update_record             
;
2015-08-28 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        
'tert-butyl (3-fluorobicyclo[1.1.1]pentan-1-yl)carbamate'
_chemical_name_common            ?
_chemical_formula_moiety         C10H16FNO2
_chemical_formula_sum            'C10 H16 F N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         201.24

_chemical_melting_point          410

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.9983(6)
_cell_length_b                   11.2142(3)
_cell_length_c                   20.2881(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4322.4(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6339
_cell_measurement_theta_min      2.9843
_cell_measurement_theta_max      22.8506
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            57841
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             5157
_reflns_number_gt                3546
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1183
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.018
_refine_ls_number_reflns         5157
_refine_ls_number_parameters     293
_refine_ls_number_restraints     75
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+1.8872P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.49056(8) 0.15747(13) 0.58742(7) 0.0216(3) Uani d . . . 1.0 . .
C C2 0.54786(19) 0.0610(3) 0.58429(16) 0.0362(8) Uani d U P D 0.715(6) A 1
H H2A 0.5353 -0.0134 0.5608 0.043 Uiso calc U P R 0.715(6) A 1
H H2B 0.5962 0.0889 0.5748 0.043 Uiso calc U P R 0.715(6) A 1
C C3 0.5252(2) 0.2073(3) 0.65030(14) 0.0388(8) Uani d U P D 0.715(6) A 1
H H3A 0.494 0.2517 0.6808 0.047 Uiso calc U P R 0.715(6) A 1
H H3B 0.5721 0.2445 0.6448 0.047 Uiso calc U P R 0.715(6) A 1
C C4 0.44647(15) 0.0735(3) 0.63200(16) 0.0346(7) Uani d U P D 0.715(6) A 1
H H4A 0.4121 0.1122 0.6618 0.042 Uiso calc U P R 0.715(6) A 1
H H4B 0.4283 -0.0002 0.6111 0.042 Uiso calc U P R 0.715(6) A 1
C C2A 0.5167(6) 0.0247(7) 0.5864(4) 0.0369(18) Uani d U P D 0.285(6) A 2
H H2A1 0.4803 -0.037 0.5788 0.044 Uiso calc U P R 0.285(6) A 2
H H2A2 0.5612 0.0091 0.5624 0.044 Uiso calc U P R 0.285(6) A 2
C C3A 0.5600(5) 0.1829(7) 0.6301(4) 0.0386(18) Uani d U P D 0.285(6) A 2
H H3A1 0.6057 0.1715 0.6075 0.046 Uiso calc U P R 0.285(6) A 2
H H3A2 0.5589 0.2536 0.6593 0.046 Uiso calc U P R 0.285(6) A 2
C C4A 0.4553(4) 0.1295(9) 0.6536(4) 0.0400(18) Uani d U P D 0.285(6) A 2
H H4A1 0.449 0.1979 0.6839 0.048 Uiso calc U P R 0.285(6) A 2
H H4A2 0.4137 0.0766 0.6518 0.048 Uiso calc U P R 0.285(6) A 2
C C5 0.52369(9) 0.07027(14) 0.65589(7) 0.0298(4) Uani d . . . 1.0 . .
C C6 0.50086(7) 0.26211(13) 0.48336(7) 0.0204(3) Uani d . . . 1.0 . .
C C7 0.49099(8) 0.36797(13) 0.37788(7) 0.0236(3) Uani d . . . 1.0 . .
C C8 0.53643(10) 0.28219(16) 0.33904(8) 0.0373(4) Uani d . . . 1.0 . .
H H8A 0.5789 0.2633 0.3644 0.056 Uiso calc U . R 1.0 . .
H H8B 0.5498 0.319 0.297 0.056 Uiso calc U . R 1.0 . .
H H8C 0.51 0.2088 0.3305 0.056 Uiso calc U . R 1.0 . .
C C9 0.52889(11) 0.47969(16) 0.39917(10) 0.0462(5) Uani d . . . 1.0 . .
H H9A 0.4965 0.5309 0.4238 0.069 Uiso calc U . R 1.0 . .
H H9B 0.546 0.5224 0.3602 0.069 Uiso calc U . R 1.0 . .
H H9C 0.5689 0.4583 0.4273 0.069 Uiso calc U . R 1.0 . .
C C10 0.42662(9) 0.39943(18) 0.33695(8) 0.0386(4) Uani d . . . 1.0 . .
H H10A 0.4023 0.3261 0.3238 0.058 Uiso calc U . R 1.0 . .
H H10B 0.4413 0.4434 0.2975 0.058 Uiso calc U . R 1.0 . .
H H10C 0.3947 0.4491 0.3632 0.058 Uiso calc U . R 1.0 . .
C C11 0.73941(8) 0.34702(13) 0.50909(7) 0.0206(3) Uani d . . . 1.0 . .
C C12 0.76601(9) 0.43917(14) 0.57811(7) 0.0270(4) Uani d . . . 1.0 . .
C C13 0.77742(10) 0.30443(15) 0.57282(8) 0.0345(4) Uani d . . . 1.0 . .
H H13A 0.7495 0.254 0.6032 0.041 Uiso calc U . R 1.0 . .
H H13B 0.8267 0.2773 0.5676 0.041 Uiso calc U . R 1.0 . .
C C14 0.69122(9) 0.42325(17) 0.55336(9) 0.0373(4) Uani d . . . 1.0 . .
H H14A 0.6693 0.4937 0.5324 0.045 Uiso calc U . R 1.0 . .
H H14B 0.6588 0.3791 0.5827 0.045 Uiso calc U . R 1.0 . .
C C15 0.79162(10) 0.45351(16) 0.50708(8) 0.0345(4) Uani d . . . 1.0 . .
H H15A 0.8416 0.4337 0.4986 0.041 Uiso calc U . R 1.0 . .
H H15B 0.7755 0.5257 0.4834 0.041 Uiso calc U . R 1.0 . .
C C16 0.75681(8) 0.23075(13) 0.40969(7) 0.0201(3) Uani d . . . 1.0 . .
C C17 0.75007(8) 0.12270(13) 0.30383(7) 0.0244(3) Uani d . . . 1.0 . .
C C18 0.80551(10) 0.19578(17) 0.26938(9) 0.0421(5) Uani d . . . 1.0 . .
H H18A 0.786 0.2739 0.2577 0.063 Uiso calc U . R 1.0 . .
H H18B 0.8207 0.1544 0.2293 0.063 Uiso calc U . R 1.0 . .
H H18C 0.846 0.2066 0.2988 0.063 Uiso calc U . R 1.0 . .
C C19 0.77753(12) 0.00484(16) 0.32854(10) 0.0474(5) Uani d . . . 1.0 . .
H H19A 0.8162 0.0188 0.3596 0.071 Uiso calc U . R 1.0 . .
H H19B 0.7947 -0.0425 0.2912 0.071 Uiso calc U . R 1.0 . .
H H19C 0.7396 -0.0385 0.3508 0.071 Uiso calc U . R 1.0 . .
C C20 0.68718(10) 0.10443(19) 0.25861(9) 0.0418(5) Uani d . . . 1.0 . .
H H20A 0.6496 0.0634 0.2828 0.063 Uiso calc U . R 1.0 . .
H H20B 0.7013 0.0561 0.2206 0.063 Uiso calc U . R 1.0 . .
H H20C 0.67 0.182 0.2433 0.063 Uiso calc U . R 1.0 . .
F F1 0.54865(6) 0.00425(9) 0.70777(5) 0.0447(3) Uani d . . . 1.0 . .
F F2 0.78592(5) 0.50982(9) 0.63011(5) 0.0398(3) Uani d . . . 1.0 . .
N N1 0.46107(7) 0.22190(11) 0.53372(6) 0.0225(3) Uani d . . . 1.0 . .
H H1N 0.4195(10) 0.2424(16) 0.5362(8) 0.034 Uiso d U . . 1.0 . .
N N2 0.71389(7) 0.27926(11) 0.45523(6) 0.0229(3) Uani d . . . 1.0 . .
H H2N 0.6700(10) 0.2708(16) 0.4511(9) 0.034 Uiso d U . . 1.0 . .
O O1 0.56437(5) 0.25274(11) 0.48110(5) 0.0342(3) Uani d . . . 1.0 . .
O O2 0.45978(5) 0.31064(10) 0.43664(5) 0.0250(2) Uani d . . . 1.0 . .
O O3 0.82057(5) 0.22826(10) 0.41361(5) 0.0297(3) Uani d . . . 1.0 . .
O O4 0.71797(5) 0.18722(9) 0.35971(5) 0.0245(2) Uani d . . . 1.0 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.4223(18) ?
C1 C4A . 1.532(7) ?
C1 C2 . 1.536(3) ?
C1 C3 . 1.540(3) ?
C1 C4 . 1.552(3) ?
C1 C2A . 1.570(8) ?
C1 C3A . 1.604(7) ?
C1 C5 . 1.812(2) ?
C2 C5 . 1.527(3) ?
C3 C5 . 1.542(3) ?
C4 C5 . 1.546(3) ?
C2A C5 . 1.506(8) ?
C3A C5 . 1.531(7) ?
C4A C5 . 1.460(8) ?
C5 F1 . 1.3714(17) ?
C6 O1 . 1.2121(17) ?
C6 O2 . 1.3431(17) ?
C6 N1 . 1.3485(18) ?
C7 O2 . 1.4785(17) ?
C7 C9 . 1.508(2) ?
C7 C8 . 1.514(2) ?
C7 C10 . 1.520(2) ?
C11 N2 . 1.4166(18) ?
C11 C14 . 1.541(2) ?
C11 C15 . 1.553(2) ?
C11 C13 . 1.556(2) ?
C11 C12 . 1.812(2) ?
C12 F2 . 1.3724(17) ?
C12 C14 . 1.518(2) ?
C12 C15 . 1.530(2) ?
C12 C13 . 1.530(2) ?
C16 O3 . 1.2143(17) ?
C16 O4 . 1.3456(17) ?
C16 N2 . 1.3469(19) ?
C17 O4 . 1.4767(17) ?
C17 C18 . 1.507(2) ?
C17 C19 . 1.507(2) ?
C17 C20 . 1.520(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C4A . . 127.1(3) ?
N1 C1 C2 . . 127.25(16) ?
N1 C1 C3 . . 128.18(15) ?
C2 C1 C3 . . 89.29(19) ?
N1 C1 C4 . . 122.84(15) ?
C2 C1 C4 . . 88.80(18) ?
C3 C1 C4 . . 88.17(17) ?
N1 C1 C2A . . 126.6(3) ?
C4A C1 C2A . . 87.5(4) ?
N1 C1 C3A . . 130.4(3) ?
C4A C1 C3A . . 85.6(4) ?
C2A C1 C3A . . 85.2(4) ?
N1 C1 C5 . . 176.77(13) ?
C4A C1 C5 . . 50.9(3) ?
C2 C1 C5 . . 53.51(13) ?
C3 C1 C5 . . 54.03(12) ?
C4 C1 C5 . . 54.04(13) ?
C2A C1 C5 . . 52.3(3) ?
C3A C1 C5 . . 52.8(3) ?
C5 C2 C1 . . 72.52(15) ?
C1 C3 C5 . . 72.01(14) ?
C5 C4 C1 . . 71.60(14) ?
C5 C2A C1 . . 72.1(4) ?
C5 C3A C1 . . 70.5(3) ?
C5 C4A C1 . . 74.5(3) ?
F1 C5 C4A . . 125.3(3) ?
F1 C5 C2A . . 124.5(3) ?
C4A C5 C2A . . 92.6(4) ?
F1 C5 C2 . . 126.11(17) ?
F1 C5 C3A . . 123.5(3) ?
C4A C5 C3A . . 90.8(4) ?
C2A C5 C3A . . 90.0(4) ?
F1 C5 C3 . . 126.06(16) ?
C2 C5 C3 . . 89.57(19) ?
F1 C5 C4 . . 125.55(16) ?
C2 C5 C4 . . 89.36(18) ?
C3 C5 C4 . . 88.33(18) ?
F1 C5 C1 . . 179.90(17) ?
C4A C5 C1 . . 54.6(3) ?
C2A C5 C1 . . 55.6(3) ?
C2 C5 C1 . . 53.97(13) ?
C3A C5 C1 . . 56.6(3) ?
C3 C5 C1 . . 53.95(12) ?
C4 C5 C1 . . 54.36(12) ?
O1 C6 O2 . . 125.93(13) ?
O1 C6 N1 . . 123.90(13) ?
O2 C6 N1 . . 110.15(12) ?
O2 C7 C9 . . 108.76(12) ?
O2 C7 C8 . . 111.85(12) ?
C9 C7 C8 . . 113.87(15) ?
O2 C7 C10 . . 102.64(12) ?
C9 C7 C10 . . 110.36(14) ?
C8 C7 C10 . . 108.78(13) ?
N2 C11 C14 . . 122.94(13) ?
N2 C11 C15 . . 127.65(13) ?
C14 C11 C15 . . 88.18(12) ?
N2 C11 C13 . . 129.43(13) ?
C14 C11 C13 . . 87.80(12) ?
C15 C11 C13 . . 87.79(12) ?
N2 C11 C12 . . 175.88(13) ?
C14 C11 C12 . . 53.07(9) ?
C15 C11 C12 . . 53.39(9) ?
C13 C11 C12 . . 53.38(9) ?
F2 C12 C14 . . 125.47(14) ?
F2 C12 C15 . . 125.16(13) ?
C14 C12 C15 . . 89.90(13) ?
F2 C12 C13 . . 125.80(14) ?
C14 C12 C13 . . 89.61(13) ?
C15 C12 C13 . . 89.58(12) ?
F2 C12 C11 . . 179.49(15) ?
C14 C12 C11 . . 54.27(9) ?
C15 C12 C11 . . 54.59(9) ?
C13 C12 C11 . . 54.70(9) ?
C12 C13 C11 . . 71.91(11) ?
C12 C14 C11 . . 72.66(11) ?
C12 C15 C11 . . 72.02(10) ?
O3 C16 O4 . . 126.01(13) ?
O3 C16 N2 . . 124.63(13) ?
O4 C16 N2 . . 109.35(12) ?
O4 C17 C18 . . 112.23(12) ?
O4 C17 C19 . . 108.51(13) ?
C18 C17 C19 . . 112.92(16) ?
O4 C17 C20 . . 101.82(12) ?
C18 C17 C20 . . 110.04(14) ?
C19 C17 C20 . . 110.77(15) ?
C6 N1 C1 . . 121.96(12) ?
C16 N2 C11 . . 122.58(12) ?
C6 O2 C7 . . 120.81(11) ?
C16 O4 C17 . . 121.99(11) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1421039'
_audit_update_record             
;
2015-08-28 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_chemical_name_systematic        
1,3-bis(3-fluorobicyclo[1.1.1]pentan-1-yl)urea
_chemical_name_common            ?
_chemical_formula_moiety         C11H14F2N2O
_chemical_formula_sum            'C11 H14 F2 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         228.24

_chemical_melting_point          '508 (decomposition)'

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   20.8723(11)
_cell_length_b                   5.5406(3)
_cell_length_c                   9.5443(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1103.75(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2017
_cell_measurement_theta_min      3.8049
_cell_measurement_theta_max      23.7337
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14511
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             1382
_reflns_number_gt                971
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1129
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         1382
_refine_ls_number_parameters     105
_refine_ls_number_restraints     72
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.5997P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.75 0.25 0.6872(2) 0.0222(4) Uani d T P S 1.0 . .
C C2 0.64915(7) 0.4664(3) 0.70028(14) 0.0235(3) Uani d . . . 1.0 . .
C C3 0.6489(3) 0.7225(11) 0.6387(9) 0.0423(15) Uani d U P . 0.531(13) A 1
H H3A 0.6546 0.8565 0.7062 0.051 Uiso calc U P R 0.531(13) A 1
H H3B 0.6731 0.7456 0.5505 0.051 Uiso calc U P R 0.531(13) A 1
C C4 0.5869(5) 0.5317(19) 0.7768(11) 0.050(2) Uani d U P . 0.531(13) A 1
H H4A 0.5902 0.6577 0.8501 0.06 Uiso calc U P R 0.531(13) A 1
H H4B 0.5589 0.3953 0.8036 0.06 Uiso calc U P R 0.531(13) A 1
C C5 0.6063(4) 0.3852(16) 0.5742(7) 0.0374(15) Uani d U P . 0.531(13) A 1
H H5A 0.627 0.3851 0.4808 0.045 Uiso calc U P R 0.531(13) A 1
H H5B 0.5785 0.2431 0.5904 0.045 Uiso calc U P R 0.531(13) A 1
C C3A 0.6510(4) 0.6636(18) 0.5836(9) 0.0430(18) Uani d U P . 0.469(13) A 2
H H3A1 0.6696 0.8214 0.6102 0.052 Uiso calc U P R 0.469(13) A 2
H H3A2 0.6638 0.6092 0.4889 0.052 Uiso calc U P R 0.469(13) A 2
C C4A 0.5975(6) 0.6202(17) 0.7752(12) 0.0412(19) Uani d U P . 0.469(13) A 2
H H4A1 0.5677 0.5316 0.8374 0.049 Uiso calc U P R 0.469(13) A 2
H H4A2 0.6122 0.7756 0.8152 0.049 Uiso calc U P R 0.469(13) A 2
C C5A 0.5943(5) 0.3474(19) 0.6204(11) 0.0434(18) Uani d U P . 0.469(13) A 2
H H5A1 0.565 0.2446 0.6761 0.052 Uiso calc U P R 0.469(13) A 2
H H5A2 0.605 0.2781 0.5278 0.052 Uiso calc U P R 0.469(13) A 2
C C6 0.58120(7) 0.6216(3) 0.62436(17) 0.0303(4) Uani d . . . 1.0 . .
F F1 0.52963(5) 0.7399(2) 0.56933(11) 0.0467(3) Uani d . . . 1.0 . .
N N1 0.70169(6) 0.3467(3) 0.76403(13) 0.0274(3) Uani d . . . 1.0 . .
H H1N 0.7050(9) 0.344(3) 0.851(2) 0.041 Uiso d U . . 1.0 . .
O O1 0.75 0.25 0.55787(14) 0.0279(4) Uani d T P S 1.0 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.235(2) ?
C1 N1 . 1.3568(16) ?
C1 N1 2_655 1.3569(16) ?
C2 N1 . 1.4186(19) ?
C2 C5A . 1.525(10) ?
C2 C4 . 1.533(10) ?
C2 C3 . 1.536(6) ?
C2 C4A . 1.549(11) ?
C2 C3A . 1.561(7) ?
C2 C5 . 1.566(8) ?
C2 C6 . 1.810(2) ?
C3 C6 . 1.526(7) ?
C4 C6 . 1.543(11) ?
C5 C6 . 1.490(9) ?
C3A C6 . 1.526(7) ?
C4A C6 . 1.480(12) ?
C5A C6 . 1.544(10) ?
C6 F1 . 1.3654(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 122.70(9) ?
O1 C1 N1 . 2_655 122.69(9) ?
N1 C1 N1 . 2_655 114.61(17) ?
N1 C2 C5A . . 126.3(4) ?
N1 C2 C4 . . 124.1(4) ?
N1 C2 C3 . . 126.8(3) ?
C4 C2 C3 . . 87.8(4) ?
N1 C2 C4A . . 126.7(5) ?
C5A C2 C4A . . 86.9(5) ?
N1 C2 C3A . . 127.9(3) ?
C5A C2 C3A . . 88.0(4) ?
C4A C2 C3A . . 87.8(4) ?
N1 C2 C5 . . 129.6(3) ?
C4 C2 C5 . . 87.1(5) ?
C3 C2 C5 . . 88.2(4) ?
N1 C2 C6 . . 178.20(12) ?
C5A C2 C6 . . 54.3(4) ?
C4 C2 C6 . . 54.2(4) ?
C3 C2 C6 . . 53.5(3) ?
C4A C2 C6 . . 51.6(4) ?
C3A C2 C6 . . 53.2(3) ?
C5 C2 C6 . . 51.8(3) ?
C6 C3 C2 . . 72.5(3) ?
C2 C4 C6 . . 72.1(5) ?
C6 C5 C2 . . 72.6(4) ?
C6 C3A C2 . . 71.8(3) ?
C6 C4A C2 . . 73.4(5) ?
C2 C5A C6 . . 72.3(4) ?
F1 C6 C4A . . 123.9(4) ?
F1 C6 C5 . . 125.1(3) ?
F1 C6 C3A . . 125.5(3) ?
C4A C6 C3A . . 91.7(5) ?
F1 C6 C3 . . 126.1(3) ?
C5 C6 C3 . . 91.5(4) ?
F1 C6 C4 . . 125.4(4) ?
C5 C6 C4 . . 89.6(4) ?
C3 C6 C4 . . 87.8(4) ?
F1 C6 C5A . . 127.1(4) ?
C4A C6 C5A . . 88.7(4) ?
C3A C6 C5A . . 88.6(4) ?
F1 C6 C2 . . 179.02(14) ?
C4A C6 C2 . . 55.1(4) ?
C5 C6 C2 . . 55.6(3) ?
C3A C6 C2 . . 55.0(3) ?
C3 C6 C2 . . 54.0(2) ?
C4 C6 C2 . . 53.7(4) ?
C5A C6 C2 . . 53.4(4) ?
C1 N1 C2 . . 121.83(12) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether and dichloromethane'
