# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_FF010815cn_0t
_database_code_depnum_ccdc_archive 'CCDC 1054201'
#Added by publCIF



_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;


_refine_ls_number_constraints    ?
#Added by publCIF




_diffrn_standards_number         ?
#Added by publCIF




_diffrn_radiation_monochromator  Triumph
#Added by publCIF




_symmetry_space_group_name_hall  ?
#Added by publCIF




_cell_special_details            ?

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H4 F4 I N'
_chemical_formula_weight         401.09

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4665(9)
_cell_length_b                   9.3784(11)
_cell_length_c                   10.5061(13)
_cell_angle_alpha                85.468(3)
_cell_angle_beta                 75.250(3)
_cell_angle_gamma                67.203(2)
_cell_volume                     655.70(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    2.480
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.612237
_exptl_absorpt_correction_T_max  0.748124
_exptl_absorpt_process_details   'TWINABS 2008/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14322
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         41.240
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7687
_reflns_number_gt                6677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7696
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I01 I 0.77440(4) -0.54884(2) 0.75861(2) 0.01281(4) Uani 1 1 d . . . . .
F01 F 0.4785(3) -0.2833(2) 0.97527(18) 0.0190(4) Uani 1 1 d . . . . .
F02 F 0.3209(3) 0.0244(2) 0.96225(19) 0.0203(4) Uani 1 1 d . . . . .
F03 F 0.6866(3) -0.0057(2) 0.51914(19) 0.0207(4) Uani 1 1 d . . . . .
F04 F 0.8295(3) -0.3140(2) 0.52749(18) 0.0177(4) Uani 1 1 d . . . . .
N01 N -0.0563(8) 1.1087(3) 0.7687(5) 0.0310(7) Uani 1 1 d . . . . .
C01 C 0.6574(7) -0.3095(2) 0.7513(3) 0.0105(3) Uani 1 1 d . . . . .
C02 C 0.5285(5) -0.2173(4) 0.8611(3) 0.0140(5) Uani 1 1 d . . . . .
C03 C 0.4490(5) -0.0572(4) 0.8552(3) 0.0139(5) Uani 1 1 d . . . . .
C04 C 0.4987(8) 0.0191(3) 0.7413(4) 0.0147(5) Uani 1 1 d . . . . .
C05 C 0.6309(5) -0.0729(3) 0.6317(3) 0.0132(5) Uani 1 1 d . . . . .
C06 C 0.7060(5) -0.2318(3) 0.6365(3) 0.0116(5) Uani 1 1 d . . . . .
C07 C 0.4186(6) 0.1841(3) 0.7354(3) 0.0161(5) Uani 1 1 d . . . . .
C08 C 0.3486(7) 0.3227(3) 0.7364(4) 0.0162(5) Uani 1 1 d . . . . .
C09 C 0.2630(6) 0.4884(3) 0.7417(3) 0.0136(4) Uani 1 1 d . . . . .
C10 C 0.1862(5) 0.5651(5) 0.8646(3) 0.0174(6) Uani 1 1 d . . . . .
H01 H 0.1902 0.5075 0.9431 0.021 Uiso 1 1 calc R U . . .
C11 C 0.1036(5) 0.7267(4) 0.8714(3) 0.0172(6) Uani 1 1 d . . . . .
H02 H 0.0517 0.7796 0.9543 0.021 Uiso 1 1 calc R U . . .
C12 C 0.0981(8) 0.8092(3) 0.7559(4) 0.0162(5) Uani 1 1 d . . . . .
C13 C 0.1745(6) 0.7340(4) 0.6321(3) 0.0174(6) Uani 1 1 d . . . . .
H03 H 0.1708 0.7921 0.5538 0.021 Uiso 1 1 calc R U . . .
C14 C 0.2558(5) 0.5732(4) 0.6259(3) 0.0151(6) Uani 1 1 d . . . . .
H04 H 0.3065 0.5206 0.5429 0.018 Uiso 1 1 calc R U . . .
C15 C 0.0131(8) 0.9764(3) 0.7615(4) 0.0213(6) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I01 C01 2.073(2) . ?
F01 C02 1.340(3) . ?
F02 C03 1.337(3) . ?
F03 C05 1.343(3) . ?
F04 C06 1.344(3) . ?
N01 C15 1.144(3) . ?
C01 C02 1.397(4) . ?
C01 C06 1.400(4) . ?
C02 C03 1.387(4) . ?
C03 C04 1.388(5) . ?
C04 C05 1.401(5) . ?
C04 C07 1.429(3) . ?
C05 C06 1.375(4) . ?
C07 C08 1.198(3) . ?
C08 C09 1.432(3) . ?
C09 C14 1.401(4) . ?
C09 C10 1.401(4) . ?
C10 C11 1.397(5) . ?
C10 H01 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H02 0.9500 . ?
C12 C13 1.403(5) . ?
C12 C15 1.446(3) . ?
C13 C14 1.391(5) . ?
C13 H03 0.9500 . ?
C14 H04 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C02 C01 C06 116.5(2) . . ?
C02 C01 I01 121.8(2) . . ?
C06 C01 I01 121.7(2) . . ?
F01 C02 C03 118.5(3) . . ?
F01 C02 C01 120.0(3) . . ?
C03 C02 C01 121.5(3) . . ?
F02 C03 C02 118.7(3) . . ?
F02 C03 C04 119.7(3) . . ?
C02 C03 C04 121.6(3) . . ?
C03 C04 C05 117.0(2) . . ?
C03 C04 C07 121.7(4) . . ?
C05 C04 C07 121.3(3) . . ?
F03 C05 C06 118.8(3) . . ?
F03 C05 C04 119.7(3) . . ?
C06 C05 C04 121.4(3) . . ?
F04 C06 C05 118.7(3) . . ?
F04 C06 C01 119.4(3) . . ?
C05 C06 C01 121.9(3) . . ?
C08 C07 C04 177.1(4) . . ?
C07 C08 C09 178.3(4) . . ?
C14 C09 C10 120.2(2) . . ?
C14 C09 C08 120.7(3) . . ?
C10 C09 C08 119.1(3) . . ?
C11 C10 C09 119.8(3) . . ?
C11 C10 H01 120.1 . . ?
C09 C10 H01 120.1 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H02 120.3 . . ?
C10 C11 H02 120.3 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 C15 120.0(4) . . ?
C13 C12 C15 118.5(4) . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H03 120.6 . . ?
C12 C13 H03 120.6 . . ?
C13 C14 C09 120.2(3) . . ?
C13 C14 H04 119.9 . . ?
C09 C14 H04 119.9 . . ?
N01 C15 C12 178.5(6) . . ?

_refine_diff_density_max         3.231
_refine_diff_density_min         -2.182
_refine_diff_density_rms         0.240

####################################################################### 
# 
# 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_FF022615OF_Fddd_d
_database_code_depnum_ccdc_archive 'CCDC 1054202'
#Added by publCIF



_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  Triumph
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8 I N'
_chemical_formula_weight         329.12

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   18.421(3)
_cell_length_b                   7.6185(14)
_cell_length_c                   17.387(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2440.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.599
_shelx_estimated_absorpt_T_min   0.595
_shelx_estimated_absorpt_T_max   0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10033
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_max         28.937
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1610
_reflns_number_gt                1385
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+24.2007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1610
_refine_ls_number_parameters     83
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_restrained_S_all      1.255
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.5000 0.5000 -0.07364(2) 0.0198(2) Uani 1 2 d S T P . .
C004 C 0.5000 0.5000 0.2888(12) 0.024(3) Uani 1 2 d S T P . .
C006 C 0.5000 0.5000 0.0467(7) 0.019(2) Uani 1 2 d S T P . .
C007 C 0.5643(6) 0.4630(13) 0.5615(6) 0.021(2) Uani 1 1 d . . . . .
H007 H 0.6080 0.4390 0.5885 0.025 Uiso 1 1 calc R U . . .
C00C C 0.5000 0.5000 0.6850(16) 0.030(3) Uani 1 2 d S T P . .
N00E N 0.5000 0.5000 0.7446(10) 0.035(3) Uani 1 2 d S T P . .
C00G C 0.5000 0.5000 0.3593(9) 0.021(3) Uani 1 2 d S TU P . .
C00H C 0.5640(5) 0.4614(13) 0.4811(6) 0.023(2) Uani 1 1 d . . . . .
H00H H 0.6070 0.4343 0.4533 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5652(5) 0.5200(12) 0.1660(5) 0.0211(18) Uani 1 1 d . . . . .
H2 H 0.6095 0.5351 0.1932 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5656(5) 0.5179(15) 0.0868(5) 0.022(2) Uani 1 1 d . . . . .
H4 H 0.6100 0.5285 0.0595 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5000 0.5000 0.4421(5) 0.014(3) Uani 1 2 d S TU P . .
C6 C 0.5000 0.5000 0.2071(14) 0.021(3) Uani 1 2 d S T P . .
C3 C 0.5000 0.5000 0.6026(18) 0.023(3) Uani 1 2 d S T P . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I001 C006 2.092(13) . ?
C004 C00G 1.22(3) . ?
C004 C6 1.42(3) . ?
C006 C4 1.402(11) . ?
C006 C4 1.402(11) 2_665 ?
C007 C00H 1.398(13) . ?
C007 C3 1.413(19) . ?
C007 H007 0.9500 . ?
C00C N00E 1.04(3) . ?
C00C C3 1.43(4) . ?
C00G C1 1.440(17) . ?
C00H C1 1.391(11) . ?
C00H H00H 0.9500 . ?
C2 C4 1.377(13) . ?
C2 C6 1.406(16) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C1 C00H 1.391(11) 2_665 ?
C6 C2 1.406(16) 2_665 ?
C3 C007 1.413(19) 2_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00G C004 C6 180.0 . . ?
C4 C006 C4 120.2(12) . 2_665 ?
C4 C006 I001 119.9(6) . . ?
C4 C006 I001 119.9(6) 2_665 . ?
C00H C007 C3 120.3(14) . . ?
C00H C007 H007 119.8 . . ?
C3 C007 H007 119.8 . . ?
N00E C00C C3 180.000(11) . . ?
C004 C00G C1 180.0 . . ?
C1 C00H C007 119.3(9) . . ?
C1 C00H H00H 120.4 . . ?
C007 C00H H00H 120.4 . . ?
C4 C2 C6 120.7(12) . . ?
C4 C2 H2 119.7 . . ?
C6 C2 H2 119.7 . . ?
C2 C4 C006 119.7(9) . . ?
C2 C4 H4 120.2 . . ?
C006 C4 H4 120.2 . . ?
C00H C1 C00H 121.7(11) . 2_665 ?
C00H C1 C00G 119.2(5) . . ?
C00H C1 C00G 119.2(5) 2_665 . ?
C2 C6 C2 119.0(19) 2_665 . ?
C2 C6 C004 120.5(10) 2_665 . ?
C2 C6 C004 120.5(10) . . ?
C007 C3 C007 119(2) . 2_665 ?
C007 C3 C00C 120.4(12) . . ?
C007 C3 C00C 120.4(12) 2_665 . ?

_refine_diff_density_max         3.484
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.197

####################################################################### 
# 
# 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_RP-4_a
_database_code_depnum_ccdc_archive 'CCDC 1054203'
#Added by publCIF



_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;


_diffrn_standards_number         ?
#Added by publCIF




_diffrn_radiation_monochromator  Triumph
#Added by publCIF




_cell_special_details            ?
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H4 Br F4 N'
_chemical_formula_weight         354.10

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2997(14)
_cell_length_b                   9.7019(11)
_cell_length_c                   19.917(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.415(3)
_cell_angle_gamma                90
_cell_volume                     2509.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    3.315
_shelx_estimated_absorpt_T_min   0.192
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72556
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         34.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11025
_reflns_number_gt                8677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11025
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.78495(2) 0.47606(2) 0.12705(2) 0.01532(3) Uani 1 1 d . . . . .
Br02 Br 0.53552(2) 0.01079(2) 0.39209(2) 0.01711(3) Uani 1 1 d . . . . .
F1 F 0.98848(5) 0.35148(7) 0.20316(4) 0.01705(14) Uani 1 1 d . . . . .
F2 F 1.02322(5) 0.16523(7) 0.30354(4) 0.01664(14) Uani 1 1 d . . . . .
F3 F 0.66662(5) 0.13484(8) 0.29372(4) 0.02037(15) Uani 1 1 d . . . . .
F4 F 0.63157(5) 0.32516(8) 0.19555(4) 0.02094(15) Uani 1 1 d . . . . .
F05 F 0.73963(5) 0.14658(7) 0.45951(3) 0.01654(14) Uani 1 1 d . . . . .
F06 F 0.77542(5) 0.34979(7) 0.55252(4) 0.01772(14) Uani 1 1 d . . . . .
F07 F 0.42045(5) 0.37320(8) 0.54994(4) 0.01966(15) Uani 1 1 d . . . . .
F08 F 0.38418(5) 0.17551(8) 0.45455(4) 0.02000(15) Uani 1 1 d . . . . .
N01 N 0.98271(9) -0.52737(11) 0.65219(6) 0.0231(2) Uani 1 1 d . . . . .
N02 N 0.73265(9) 1.06674(12) 0.88929(6) 0.0261(2) Uani 1 1 d . . . . .
C01 C 0.80949(8) 0.34369(11) 0.19656(5) 0.01195(19) Uani 1 1 d . . . . .
C02 C 0.90864(8) 0.29995(11) 0.22523(6) 0.01162(19) Uani 1 1 d . . . . .
C03 C 0.92631(8) 0.20215(11) 0.27684(5) 0.01129(19) Uani 1 1 d . . . . .
C04 C 0.84628(8) 0.14231(11) 0.30187(5) 0.01157(19) Uani 1 1 d . . . . .
C05 C 0.74719(9) 0.18764(11) 0.27232(6) 0.0130(2) Uani 1 1 d . . . . .
C06 C 0.72901(8) 0.28613(11) 0.22117(6) 0.0132(2) Uani 1 1 d . . . . .
C07 C 0.86492(9) 0.04025(11) 0.35432(6) 0.0133(2) Uani 1 1 d . . . . .
C08 C 0.88074(9) -0.04711(12) 0.39816(6) 0.0136(2) Uani 1 1 d . . . . .
C09 C 0.90134(9) -0.15065(11) 0.45034(5) 0.01236(19) Uani 1 1 d . . . . .
C10 C 1.00202(9) -0.19739(12) 0.47480(6) 0.0158(2) Uani 1 1 d . . . . .
H01 H 1.0566 -0.1610 0.4563 0.019 Uiso 1 1 calc R U . . .
C11 C 1.02255(9) -0.29689(12) 0.52610(6) 0.0156(2) Uani 1 1 d . . . . .
H00S H 1.0909 -0.3286 0.5428 0.019 Uiso 1 1 calc R U . . .
C12 C 0.94187(9) -0.34974(11) 0.55285(6) 0.0135(2) Uani 1 1 d . . . . .
C13 C 0.84099(9) -0.30482(12) 0.52831(6) 0.0169(2) Uani 1 1 d . . . . .
H00Z H 0.7864 -0.3423 0.5465 0.020 Uiso 1 1 calc R U . . .
C14 C 0.82085(9) -0.20537(12) 0.47729(6) 0.0162(2) Uani 1 1 d . . . . .
H016 H 0.7523 -0.1742 0.4605 0.019 Uiso 1 1 calc R U . . .
C15 C 0.96441(9) -0.44975(13) 0.60772(6) 0.0168(2) Uani 1 1 d . . . . .
C16 C 0.56104(9) 0.15719(11) 0.45435(5) 0.01259(19) Uani 1 1 d . . . . .
C17 C 0.66019(8) 0.20399(11) 0.48000(5) 0.01204(19) Uani 1 1 d . . . . .
C18 C 0.67843(8) 0.30821(11) 0.52833(6) 0.01238(19) Uani 1 1 d . . . . .
C19 C 0.59917(8) 0.36787(11) 0.55384(5) 0.01211(19) Uani 1 1 d . . . . .
C20 C 0.49968(9) 0.32035(11) 0.52690(6) 0.0134(2) Uani 1 1 d . . . . .
C21 C 0.48093(9) 0.21803(12) 0.47781(6) 0.0134(2) Uani 1 1 d . . . . .
C22 C 0.61896(9) 0.47009(12) 0.60623(6) 0.0151(2) Uani 1 1 d . . . . .
C23 C 0.63567(9) 0.55516(12) 0.65137(6) 0.0153(2) Uani 1 1 d . . . . .
C24 C 0.65641(9) 0.65809(11) 0.70398(6) 0.0134(2) Uani 1 1 d . . . . .
C25 C 0.75756(9) 0.70251(12) 0.72924(6) 0.0158(2) Uani 1 1 d . . . . .
H015 H 0.8125 0.6619 0.7126 0.019 Uiso 1 1 calc R U . . .
C26 C 0.77783(9) 0.80596(12) 0.77853(6) 0.0159(2) Uani 1 1 d . . . . .
H00X H 0.8463 0.8369 0.7956 0.019 Uiso 1 1 calc R U . . .
C27 C 0.69627(9) 0.86386(11) 0.80271(6) 0.0145(2) Uani 1 1 d . . . . .
C28 C 0.59516(9) 0.81812(12) 0.77870(6) 0.0183(2) Uani 1 1 d . . . . .
H011 H 0.5404 0.8574 0.7960 0.022 Uiso 1 1 calc R U . . .
C29 C 0.57552(9) 0.71524(12) 0.72957(6) 0.0179(2) Uani 1 1 d . . . . .
H013 H 0.5071 0.6833 0.7132 0.022 Uiso 1 1 calc R U . . .
C30 C 0.71667(10) 0.97579(12) 0.85126(7) 0.0181(2) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C01 1.8649(11) . ?
Br02 C16 1.8680(11) . ?
F1 C02 1.3310(12) . ?
F2 C03 1.3333(12) . ?
F3 C05 1.3374(13) . ?
F4 C06 1.3412(12) . ?
F05 C17 1.3337(12) . ?
F06 C18 1.3385(12) . ?
F07 C20 1.3385(12) . ?
F08 C21 1.3358(13) . ?
N01 C15 1.1481(16) . ?
N02 C30 1.1524(16) . ?
C01 C02 1.3861(15) . ?
C01 C06 1.3869(15) . ?
C02 C03 1.3812(15) . ?
C03 C04 1.3952(15) . ?
C04 C05 1.3939(15) . ?
C04 C07 1.4219(15) . ?
C05 C06 1.3796(15) . ?
C07 C08 1.2026(16) . ?
C08 C09 1.4289(15) . ?
C09 C10 1.3984(16) . ?
C09 C14 1.4010(15) . ?
C10 C11 1.3894(16) . ?
C11 C12 1.3943(16) . ?
C12 C13 1.3953(16) . ?
C12 C15 1.4438(16) . ?
C13 C14 1.3849(15) . ?
C16 C21 1.3842(15) . ?
C16 C17 1.3843(15) . ?
C17 C18 1.3811(15) . ?
C18 C19 1.3910(15) . ?
C19 C20 1.3949(15) . ?
C19 C22 1.4225(16) . ?
C20 C21 1.3780(16) . ?
C22 C23 1.2054(16) . ?
C23 C24 1.4307(16) . ?
C24 C25 1.3991(16) . ?
C24 C29 1.4001(16) . ?
C25 C26 1.3892(15) . ?
C26 C27 1.3960(16) . ?
C27 C28 1.3991(16) . ?
C27 C30 1.4406(16) . ?
C28 C29 1.3828(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C02 C01 C06 117.99(10) . . ?
C02 C01 Br01 121.05(8) . . ?
C06 C01 Br01 120.96(8) . . ?
F1 C02 C03 118.93(9) . . ?
F1 C02 C01 120.31(9) . . ?
C03 C02 C01 120.76(10) . . ?
F2 C03 C02 118.46(9) . . ?
F2 C03 C04 119.47(9) . . ?
C02 C03 C04 122.07(10) . . ?
C05 C04 C03 116.27(10) . . ?
C05 C04 C07 121.97(10) . . ?
C03 C04 C07 121.76(10) . . ?
F3 C05 C06 118.39(10) . . ?
F3 C05 C04 119.62(10) . . ?
C06 C05 C04 122.00(10) . . ?
F4 C06 C05 118.56(10) . . ?
F4 C06 C01 120.52(10) . . ?
C05 C06 C01 120.92(10) . . ?
C08 C07 C04 179.31(13) . . ?
C07 C08 C09 179.04(13) . . ?
C10 C09 C14 119.80(10) . . ?
C10 C09 C08 120.05(10) . . ?
C14 C09 C08 120.14(10) . . ?
C11 C10 C09 120.23(11) . . ?
C10 C11 C12 119.40(10) . . ?
C11 C12 C13 120.81(10) . . ?
C11 C12 C15 119.00(10) . . ?
C13 C12 C15 120.17(10) . . ?
C14 C13 C12 119.63(11) . . ?
C13 C14 C09 120.12(11) . . ?
N01 C15 C12 178.76(14) . . ?
C21 C16 C17 118.47(10) . . ?
C21 C16 Br02 120.34(8) . . ?
C17 C16 Br02 121.14(8) . . ?
F05 C17 C18 119.15(9) . . ?
F05 C17 C16 120.30(10) . . ?
C18 C17 C16 120.54(10) . . ?
F06 C18 C17 118.87(10) . . ?
F06 C18 C19 119.38(10) . . ?
C17 C18 C19 121.72(10) . . ?
C18 C19 C20 116.92(10) . . ?
C18 C19 C22 121.52(10) . . ?
C20 C19 C22 121.55(10) . . ?
F07 C20 C21 118.92(10) . . ?
F07 C20 C19 119.54(10) . . ?
C21 C20 C19 121.53(10) . . ?
F08 C21 C20 118.84(10) . . ?
F08 C21 C16 120.35(10) . . ?
C20 C21 C16 120.78(10) . . ?
C23 C22 C19 178.99(13) . . ?
C22 C23 C24 178.75(13) . . ?
C25 C24 C29 120.12(10) . . ?
C25 C24 C23 119.82(10) . . ?
C29 C24 C23 120.05(10) . . ?
C26 C25 C24 120.14(11) . . ?
C25 C26 C27 119.17(11) . . ?
C26 C27 C28 121.03(10) . . ?
C26 C27 C30 119.13(11) . . ?
C28 C27 C30 119.80(11) . . ?
C29 C28 C27 119.49(11) . . ?
C28 C29 C24 120.03(11) . . ?
N02 C30 C27 178.96(15) . . ?

_refine_diff_density_max         1.233
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_FF0930_P1bar_a
_database_code_depnum_ccdc_archive 'CCDC 1054204'
#Added by publCIF



_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;
# publcif _publ_body_element loop end


_diffrn_standards_number         ?
#Added by publCIF




_diffrn_radiation_monochromator  Triumph
#Added by publCIF




_cell_special_details            'calculated from global refinement'

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H6 Br F2 N'
_chemical_formula_weight         318.12

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7972(9)
_cell_length_b                   8.6736(14)
_cell_length_c                   12.715(2)
_cell_angle_alpha                73.612(3)
_cell_angle_beta                 85.418(3)
_cell_angle_gamma                86.061(3)
_cell_volume                     610.70(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    3.373
_shelx_estimated_absorpt_T_min   0.552
_shelx_estimated_absorpt_T_max   0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5520
_exptl_absorpt_correction_T_max  0.5520
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9756
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         28.879
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3194
_reflns_number_gt                2811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+0.5325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.15271(4) 0.01237(3) 0.85230(2) 0.02200(7) Uani 1 1 d . . . . .
F002 F 0.62456(19) 0.00447(14) 0.61989(10) 0.0204(3) Uani 1 1 d . . . . .
F1 F -0.2148(2) 0.30511(15) 0.65945(10) 0.0214(3) Uani 1 1 d . . . . .
N1 N 1.3722(3) 0.7130(2) -0.04729(15) 0.0248(4) Uani 1 1 d . . . . .
C14 C 1.0881(3) 0.5657(2) 0.11054(16) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.0549(3) 0.0911(2) 0.73003(15) 0.0155(4) Uani 1 1 d . . . . .
C5 C 0.4144(3) 0.0780(2) 0.62955(16) 0.0152(4) Uani 1 1 d . . . . .
C3 C 0.2696(3) 0.0141(2) 0.72090(16) 0.0162(4) Uani 1 1 d . . . . .
H3 H 0.3159 -0.0799 0.7758 0.019 Uiso 1 1 calc R U . . .
C2 C -0.0077(3) 0.2281(2) 0.64926(16) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.6389(3) 0.3430(2) 0.37861(17) 0.0177(4) Uani 1 1 d . . . . .
C11 C 1.0100(3) 0.3461(2) 0.27004(16) 0.0175(4) Uani 1 1 d . . . . .
H11 H 1.0568 0.2465 0.3194 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1379(3) 0.2896(2) 0.55833(16) 0.0166(4) Uani 1 1 d . . . . .
H4 H 0.0896 0.3824 0.5030 0.020 Uiso 1 1 calc R U . . .
C10 C 0.7208(3) 0.5630(2) 0.21273(16) 0.0170(4) Uani 1 1 d . . . . .
H10 H 0.5718 0.6112 0.2233 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3565(3) 0.2157(2) 0.54737(16) 0.0151(4) Uani 1 1 d . . . . .
C9 C 0.7908(3) 0.4176(2) 0.28646(16) 0.0159(4) Uani 1 1 d . . . . .
C12 C 0.8680(3) 0.6367(2) 0.12464(16) 0.0173(4) Uani 1 1 d . . . . .
H12 H 0.8201 0.7348 0.0740 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5136(3) 0.2821(2) 0.45568(16) 0.0172(4) Uani 1 1 d . . . . .
C13 C 1.1585(3) 0.4197(2) 0.18232(16) 0.0173(4) Uani 1 1 d . . . . .
H13 H 1.3070 0.3712 0.1712 0.021 Uiso 1 1 calc R U . . .
C15 C 1.2460(3) 0.6470(2) 0.02149(17) 0.0182(4) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.8832(18) . ?
F002 C5 1.349(2) . ?
F1 C2 1.349(2) . ?
N1 C15 1.140(3) . ?
C14 C13 1.393(3) . ?
C14 C12 1.399(3) . ?
C14 C15 1.446(3) . ?
C1 C2 1.382(3) . ?
C1 C3 1.384(3) . ?
C5 C3 1.381(3) . ?
C5 C6 1.389(3) . ?
C2 C4 1.375(3) . ?
C8 C7 1.189(3) . ?
C8 C9 1.433(3) . ?
C11 C13 1.383(3) . ?
C11 C9 1.402(3) . ?
C4 C6 1.395(3) . ?
C10 C12 1.382(3) . ?
C10 C9 1.399(3) . ?
C6 C7 1.430(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C14 C12 120.92(17) . . ?
C13 C14 C15 119.66(18) . . ?
C12 C14 C15 119.41(18) . . ?
C2 C1 C3 119.85(17) . . ?
C2 C1 Br1 119.46(15) . . ?
C3 C1 Br1 120.68(15) . . ?
F002 C5 C3 118.55(17) . . ?
F002 C5 C6 118.01(16) . . ?
C3 C5 C6 123.44(18) . . ?
C5 C3 C1 117.95(18) . . ?
F1 C2 C4 118.70(17) . . ?
F1 C2 C1 119.80(17) . . ?
C4 C2 C1 121.50(18) . . ?
C7 C8 C9 179.3(2) . . ?
C13 C11 C9 120.34(18) . . ?
C2 C4 C6 120.00(18) . . ?
C12 C10 C9 120.15(18) . . ?
C5 C6 C4 117.24(17) . . ?
C5 C6 C7 122.09(17) . . ?
C4 C6 C7 120.66(18) . . ?
C10 C9 C11 119.75(18) . . ?
C10 C9 C8 119.90(18) . . ?
C11 C9 C8 120.35(18) . . ?
C10 C12 C14 119.50(18) . . ?
C8 C7 C6 177.4(2) . . ?
C11 C13 C14 119.32(18) . . ?
N1 C15 C14 178.5(2) . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.088

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_FF022715MC_Fdd_f
_database_code_depnum_ccdc_archive 'CCDC 1054205'
#Added by publCIF



_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  Triumph
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8 Br N'
_chemical_formula_weight         282.13

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   17.893(4)
_cell_length_b                   7.5409(14)
_cell_length_c                   17.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2316.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    3.522
_shelx_estimated_absorpt_T_min   0.376
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3760
_exptl_absorpt_correction_T_max  0.7960
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14475
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         32.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2029
_reflns_number_gt                1783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+7.4239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2029
_refine_ls_number_parameters     83
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_restrained_S_all      1.297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.2500 0.2500 0.91468(2) 0.01614(13) Uani 1 2 d S T P . .
C002 C 0.2500 0.2500 0.1580(6) 0.024(2) Uani 1 2 d S T P . .
C003 C 0.2500 0.2500 0.5595(4) 0.0158(15) Uani 1 2 d S T P . .
C004 C 0.2500 0.2500 0.4041(5) 0.0126(17) Uani 1 2 d S T P . .
C005 C 0.2500 0.2500 0.4883(3) 0.0175(11) Uani 1 2 d S T P . .
C006 C 0.1831(2) 0.2260(5) 0.6835(2) 0.0145(7) Uani 1 1 d . . . . .
H006 H 0.1376 0.2083 0.6559 0.017 Uiso 1 1 calc R U . . .
C007 C 0.1827(2) 0.2278(7) 0.7644(2) 0.0157(9) Uani 1 1 d . . . . .
H007 H 0.1373 0.2141 0.7923 0.019 Uiso 1 1 calc R U . . .
C008 C 0.1842(2) 0.2878(5) 0.3644(2) 0.0153(8) Uani 1 1 d . . . . .
H008 H 0.1397 0.3142 0.3923 0.018 Uiso 1 1 calc R U . . .
C009 C 0.2500 0.2500 0.8038(3) 0.0136(9) Uani 1 2 d S T P . .
N00A N 0.2500 0.2500 0.0944(4) 0.0302(14) Uani 1 2 d S T P . .
C00B C 0.2500 0.2500 0.2428(5) 0.0153(16) Uani 1 2 d S T P . .
C00C C 0.1839(2) 0.2868(5) 0.2832(2) 0.0146(8) Uani 1 1 d . . . . .
H00C H 0.1391 0.3109 0.2554 0.018 Uiso 1 1 calc R U . . .
C00E C 0.2500 0.2500 0.6423(4) 0.0152(16) Uani 1 2 d S T P . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C009 1.903(6) . ?
C002 N00A 1.092(13) . ?
C002 C00B 1.454(12) . ?
C003 C005 1.221(10) . ?
C003 C00E 1.421(10) . ?
C004 C008 1.391(6) . ?
C004 C008 1.391(6) 14 ?
C004 C005 1.445(10) . ?
C006 C007 1.389(5) . ?
C006 C00E 1.403(5) . ?
C006 H006 0.9500 . ?
C007 C009 1.391(5) . ?
C007 H007 0.9500 . ?
C008 C00C 1.394(6) . ?
C008 H008 0.9500 . ?
C009 C007 1.391(5) 14 ?
C00B C00C 1.399(6) 14 ?
C00B C00C 1.399(6) . ?
C00C H00C 0.9500 . ?
C00E C006 1.403(5) 14 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N00A C002 C00B 180.0 . . ?
C005 C003 C00E 180.0 . . ?
C008 C004 C008 121.2(7) . 14 ?
C008 C004 C005 119.4(4) . . ?
C008 C004 C005 119.4(4) 14 . ?
C003 C005 C004 180.0 . . ?
C007 C006 C00E 120.5(4) . . ?
C007 C006 H006 119.8 . . ?
C00E C006 H006 119.8 . . ?
C006 C007 C009 118.9(4) . . ?
C006 C007 H007 120.5 . . ?
C009 C007 H007 120.5 . . ?
C004 C008 C00C 119.5(5) . . ?
C004 C008 H008 120.2 . . ?
C00C C008 H008 120.2 . . ?
C007 C009 C007 121.8(6) 14 . ?
C007 C009 Br01 119.1(3) 14 . ?
C007 C009 Br01 119.1(3) . . ?
C00C C00B C00C 120.5(6) 14 . ?
C00C C00B C002 119.7(3) 14 . ?
C00C C00B C002 119.7(3) . . ?
C008 C00C C00B 119.6(4) . . ?
C008 C00C H00C 120.2 . . ?
C00B C00C H00C 120.2 . . ?
C006 C00E C006 119.4(6) . 14 ?
C006 C00E C003 120.3(3) . . ?
C006 C00E C003 120.3(3) 14 . ?

_refine_diff_density_max         0.900
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_FF1128_P-1_a
_database_code_depnum_ccdc_archive 'CCDC 1054206'
#Added by publCIF



_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;


_cell_special_details            ?
#Added by publCIF




_diffrn_radiation_monochromator  Triumph
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 N'
_chemical_formula_weight         203.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.404(3)
_cell_length_b                   9.480(3)
_cell_length_c                   13.047(4)
_cell_angle_alpha                94.412(6)
_cell_angle_beta                 102.356(6)
_cell_angle_gamma                103.038(6)
_cell_volume                     1097.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9310
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15077
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4487
_reflns_number_gt                2527
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1090P)²+0.1842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4487
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.2104
_refine_ls_wR_factor_gt          0.1753
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.2629(3) 0.3262(2) 0.51660(18) 0.0401(6) Uani 1 1 d . . . . .
C002 C 0.8771(3) 0.3545(3) 0.12242(19) 0.0244(6) Uani 1 1 d . . . . .
N003 N 1.2020(3) 0.6749(3) 0.48918(19) 0.0444(7) Uani 1 1 d . . . . .
C004 C 0.6192(3) 0.6429(2) 0.87383(19) 0.0258(6) Uani 1 1 d . . . . .
C005 C 0.8812(3) 0.8801(2) 1.14780(19) 0.0250(6) Uani 1 1 d . . . . .
C006 C 1.0320(3) 0.9472(3) 1.1563(2) 0.0269(6) Uani 1 1 d . . . . .
H006 H 1.0717 0.9473 1.0952 0.032 Uiso 1 1 calc R U . . .
C007 C 0.4339(3) 0.4835(2) 0.68719(18) 0.0248(6) Uani 1 1 d . . . . .
C008 C 0.7886(3) 0.8019(3) 1.0498(2) 0.0259(6) Uani 1 1 d . . . . .
C009 C 1.0450(3) 0.5180(3) 0.31351(19) 0.0263(6) Uani 1 1 d . . . . .
C00A C 0.7847(3) 0.2731(3) 0.0258(2) 0.0269(6) Uani 1 1 d . . . . .
C00B C 0.6100(3) 0.1288(2) -0.15395(19) 0.0249(6) Uani 1 1 d . . . . .
C00C C 0.7128(3) 0.7290(3) 0.9691(2) 0.0273(6) Uani 1 1 d . . . . .
C00D C 0.6021(3) 0.1972(3) -0.24516(19) 0.0267(6) Uani 1 1 d . . . . .
H00D H 0.6524 0.2972 -0.2402 0.032 Uiso 1 1 calc R U . . .
C00E C 0.9823(3) 0.3700(3) 0.30934(19) 0.0270(6) Uani 1 1 d . . . . .
H00E H 0.9961 0.3245 0.3718 0.032 Uiso 1 1 calc R U . . .
C00F C 0.6736(3) 0.6322(2) 0.78247(19) 0.0264(6) Uani 1 1 d . . . . .
H00F H 0.7748 0.6795 0.7846 0.032 Uiso 1 1 calc R U . . .
C00G C 0.3379(3) 0.3971(3) 0.5921(2) 0.0283(6) Uani 1 1 d . . . . .
C00H C 0.3792(3) 0.4916(3) 0.77790(19) 0.0263(6) Uani 1 1 d . . . . .
H00H H 0.2787 0.4421 0.7761 0.032 Uiso 1 1 calc R U . . .
C00I C 1.0253(3) 0.5845(3) 0.2220(2) 0.0275(6) Uani 1 1 d . . . . .
H00I H 1.0685 0.6860 0.2250 0.033 Uiso 1 1 calc R U . . .
C00J C 0.9438(3) 0.5044(3) 0.1275(2) 0.0270(6) Uani 1 1 d . . . . .
H00J H 0.9322 0.5501 0.0650 0.032 Uiso 1 1 calc R U . . .
C00K C 0.4708(3) 0.5713(3) 0.86992(19) 0.0262(6) Uani 1 1 d . . . . .
H00K H 0.4330 0.5779 0.9316 0.031 Uiso 1 1 calc R U . . .
C00L C 0.5819(3) 0.5540(3) 0.68999(19) 0.0283(6) Uani 1 1 d . . . . .
H00L H 0.6191 0.5480 0.6280 0.034 Uiso 1 1 calc R U . . .
C00M C 0.9002(3) 0.2895(3) 0.21496(19) 0.0262(6) Uani 1 1 d . . . . .
H00M H 0.8583 0.1879 0.2125 0.031 Uiso 1 1 calc R U . . .
C00N C 0.5319(3) -0.0172(3) -0.1622(2) 0.0286(6) Uani 1 1 d . . . . .
H00N H 0.5336 -0.0648 -0.1006 0.034 Uiso 1 1 calc R U . . .
C00O C 1.1312(3) 0.6046(3) 0.4112(2) 0.0309(6) Uani 1 1 d . . . . .
C00P C 0.4474(3) -0.0235(3) -0.3497(2) 0.0315(6) Uani 1 1 d . . . . .
H00P H 0.3925 -0.0759 -0.4167 0.038 Uiso 1 1 calc R U . . .
C00Q C 0.8247(3) 0.8832(3) 1.23789(19) 0.0279(6) Uani 1 1 d . . . . .
H00Q H 0.7219 0.8386 1.2330 0.034 Uiso 1 1 calc R U . . .
C00R C 0.5224(3) 0.1216(3) -0.3419(2) 0.0307(6) Uani 1 1 d . . . . .
H00R H 0.5188 0.1691 -0.4036 0.037 Uiso 1 1 calc R U . . .
C00S C 0.4525(3) -0.0921(3) -0.2597(2) 0.0313(6) Uani 1 1 d . . . . .
H00S H 0.4007 -0.1918 -0.2652 0.038 Uiso 1 1 calc R U . . .
C00T C 1.1233(3) 1.0132(3) 1.2529(2) 0.0287(6) Uani 1 1 d . . . . .
H00T H 1.2262 1.0583 1.2583 0.034 Uiso 1 1 calc R U . . .
C00U C 0.9167(3) 0.9505(3) 1.3340(2) 0.0328(6) Uani 1 1 d . . . . .
H00U H 0.8769 0.9528 1.3949 0.039 Uiso 1 1 calc R U . . .
C00V C 0.7013(3) 0.2065(3) -0.0552(2) 0.0272(6) Uani 1 1 d . . . . .
C00W C 1.0663(3) 1.0145(3) 1.3424(2) 0.0312(6) Uani 1 1 d . . . . .
H00W H 1.1300 1.0592 1.4091 0.037 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C00G 1.143(3) . ?
C002 C00M 1.396(3) . ?
C002 C00J 1.407(3) . ?
C002 C00A 1.421(3) . ?
N003 C00O 1.152(3) . ?
C004 C00K 1.395(3) . ?
C004 C00F 1.400(3) . ?
C004 C00C 1.428(3) . ?
C005 C00Q 1.391(3) . ?
C005 C006 1.393(3) . ?
C005 C008 1.424(3) . ?
C006 C00T 1.375(3) . ?
C006 H006 0.9500 . ?
C007 C00H 1.391(3) . ?
C007 C00L 1.392(3) . ?
C007 C00G 1.433(3) . ?
C008 C00C 1.200(3) . ?
C009 C00E 1.385(3) . ?
C009 C00I 1.390(3) . ?
C009 C00O 1.433(4) . ?
C00A C00V 1.204(3) . ?
C00B C00D 1.394(3) . ?
C00B C00N 1.397(3) . ?
C00B C00V 1.427(3) . ?
C00D C00R 1.372(3) . ?
C00D H00D 0.9500 . ?
C00E C00M 1.370(3) . ?
C00E H00E 0.9500 . ?
C00F C00L 1.370(3) . ?
C00F H00F 0.9500 . ?
C00H C00K 1.371(3) . ?
C00H H00H 0.9500 . ?
C00I C00J 1.368(3) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N C00S 1.377(4) . ?
C00N H00N 0.9500 . ?
C00P C00R 1.382(4) . ?
C00P C00S 1.383(4) . ?
C00P H00P 0.9500 . ?
C00Q C00U 1.375(4) . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00T C00W 1.385(4) . ?
C00T H00T 0.9500 . ?
C00U C00W 1.378(4) . ?
C00U H00U 0.9500 . ?
C00W H00W 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00M C002 C00J 118.4(2) . . ?
C00M C002 C00A 121.1(2) . . ?
C00J C002 C00A 120.5(2) . . ?
C00K C004 C00F 119.1(2) . . ?
C00K C004 C00C 120.3(2) . . ?
C00F C004 C00C 120.5(2) . . ?
C00Q C005 C006 119.0(2) . . ?
C00Q C005 C008 120.4(2) . . ?
C006 C005 C008 120.6(2) . . ?
C00T C006 C005 120.2(2) . . ?
C00T C006 H006 119.9 . . ?
C005 C006 H006 119.9 . . ?
C00H C007 C00L 120.3(2) . . ?
C00H C007 C00G 119.1(2) . . ?
C00L C007 C00G 120.5(2) . . ?
C00C C008 C005 176.3(3) . . ?
C00E C009 C00I 120.0(2) . . ?
C00E C009 C00O 121.0(2) . . ?
C00I C009 C00O 119.0(2) . . ?
C00V C00A C002 177.2(3) . . ?
C00D C00B C00N 118.9(2) . . ?
C00D C00B C00V 119.9(2) . . ?
C00N C00B C00V 121.2(2) . . ?
C008 C00C C004 178.5(3) . . ?
C00R C00D C00B 120.8(2) . . ?
C00R C00D H00D 119.6 . . ?
C00B C00D H00D 119.6 . . ?
C00M C00E C009 119.9(2) . . ?
C00M C00E H00E 120.0 . . ?
C009 C00E H00E 120.0 . . ?
C00L C00F C004 120.5(2) . . ?
C00L C00F H00F 119.8 . . ?
C004 C00F H00F 119.8 . . ?
N001 C00G C007 178.6(3) . . ?
C00K C00H C007 119.7(2) . . ?
C00K C00H H00H 120.1 . . ?
C007 C00H H00H 120.1 . . ?
C00J C00I C009 120.2(2) . . ?
C00J C00I H00I 119.9 . . ?
C009 C00I H00I 119.9 . . ?
C00I C00J C002 120.4(2) . . ?
C00I C00J H00J 119.8 . . ?
C002 C00J H00J 119.8 . . ?
C00H C00K C004 120.6(2) . . ?
C00H C00K H00K 119.7 . . ?
C004 C00K H00K 119.7 . . ?
C00F C00L C007 119.8(2) . . ?
C00F C00L H00L 120.1 . . ?
C007 C00L H00L 120.1 . . ?
C00E C00M C002 121.0(2) . . ?
C00E C00M H00M 119.5 . . ?
C002 C00M H00M 119.5 . . ?
C00S C00N C00B 119.9(2) . . ?
C00S C00N H00N 120.1 . . ?
C00B C00N H00N 120.1 . . ?
N003 C00O C009 179.1(3) . . ?
C00R C00P C00S 119.8(2) . . ?
C00R C00P H00P 120.1 . . ?
C00S C00P H00P 120.1 . . ?
C00U C00Q C005 120.4(3) . . ?
C00U C00Q H00Q 119.8 . . ?
C005 C00Q H00Q 119.8 . . ?
C00D C00R C00P 120.0(2) . . ?
C00D C00R H00R 120.0 . . ?
C00P C00R H00R 120.0 . . ?
C00N C00S C00P 120.6(2) . . ?
C00N C00S H00S 119.7 . . ?
C00P C00S H00S 119.7 . . ?
C006 C00T C00W 120.4(3) . . ?
C006 C00T H00T 119.8 . . ?
C00W C00T H00T 119.8 . . ?
C00Q C00U C00W 120.4(2) . . ?
C00Q C00U H00U 119.8 . . ?
C00W C00U H00U 119.8 . . ?
C00A C00V C00B 176.6(3) . . ?
C00U C00W C00T 119.6(2) . . ?
C00U C00W H00W 120.2 . . ?
C00T C00W H00W 120.2 . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/6

