# 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_pb_p-1
_database_code_depnum_ccdc_archive 'CCDC 1410851'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;

_audit_creation_date             2015-07-02T12:22:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
1-[4-(6-bromobenzo[1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta-[c]quinolin-8-yl]ethanone
_chemical_formula_sum            'C16 H10 B Br F2 N2 O2'
_chemical_formula_weight         390.98

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.70700(10)
_cell_length_b                   9.4550(2)
_cell_length_c                   12.9340(3)
_cell_angle_alpha                110.6160(10)
_cell_angle_beta                 95.0070(10)
_cell_angle_gamma                95.5940(10)
_cell_volume                     757.49(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1236
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      36.02

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_correction_T_min  0.6358
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_type   multi-scan

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_number            23026
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             3628
_reflns_number_gt                3126
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0332P)²+0.1852P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3628
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.92985(3) 0.07007(2) 0.29878(2) 0.04091(8) Uani 1 d . .
O2 O 0.4891(2) -0.29021(16) -0.15369(11) 0.0489(3) Uani 1 d . .
F2 F 0.6156(2) -0.53464(14) 0.40165(11) 0.0644(4) Uani 1 d . .
O1 O 0.6812(2) -0.06068(15) -0.12781(10) 0.0424(3) Uani 1 d . .
C5 C 0.7969(2) 0.0031(2) 0.07094(14) 0.0336(4) Uani 1 d . .
H1D H 0.87 0.0971 0.0818 0.04 Uiso 1 calc . .
F1 F 0.8265(2) -0.32594(17) 0.51077(11) 0.0746(4) Uani 1 d . .
N2 N 0.5551(2) -0.29297(18) 0.39119(12) 0.0413(4) Uani 1 d . .
C1 C 0.6758(3) -0.1917(2) 0.14285(14) 0.0326(4) Uani 1 d . .
C2 C 0.5658(3) -0.2790(2) 0.03825(15) 0.0389(4) Uani 1 d . .
H2 H 0.4857 -0.3705 0.0269 0.047 Uiso 1 calc . .
N1 N 0.8448(3) -0.41894(18) 0.31383(14) 0.0426(4) Uani 1 d . .
C4 C 0.6943(2) -0.0880(2) -0.03024(14) 0.0324(4) Uani 1 d . .
C6 C 0.7862(2) -0.0529(2) 0.15771(13) 0.0312(3) Uani 1 d . .
C15 C 0.3883(3) -0.1395(3) 0.32404(18) 0.0496(5) Uani 1 d . .
H7 H 0.3492 -0.0837 0.281 0.059 Uiso 1 calc . .
C8 C 0.6829(3) -0.2585(2) 0.23195(14) 0.0344(4) Uani 1 d . .
C9 C 0.8271(3) -0.3554(2) 0.23227(16) 0.0399(4) Uani 1 d . .
C16 C 0.5490(3) -0.2278(2) 0.30946(15) 0.0376(4) Uani 1 d . .
C13 C 0.4066(3) -0.2460(3) 0.45182(18) 0.0547(5) Uani 1 d . .
H11 H 0.3776 -0.2731 0.5119 0.066 Uiso 1 calc . .
B1 B 0.7116(4) -0.3958(3) 0.40834(18) 0.0425(5) Uani 1 d . .
C7 C 0.5767(3) -0.1994(2) -0.21100(15) 0.0438(4) Uani 1 d . .
H13A H 0.4721 -0.1769 -0.2572 0.053 Uiso 1 calc . .
H13B H 0.6702 -0.2538 -0.2583 0.053 Uiso 1 calc . .
C3 C 0.5803(3) -0.2250(2) -0.04614(14) 0.0354(4) Uani 1 d . .
C14 C 0.3005(4) -0.1507(3) 0.4129(2) 0.0618(6) Uani 1 d . .
H15 H 0.1914 -0.104 0.4418 0.074 Uiso 1 calc . .
C12 C 0.9929(4) -0.5063(3) 0.2926(2) 0.0625(6) Uani 1 d . .
H16 H 1.036 -0.5619 0.335 0.075 Uiso 1 calc . .
C10 C 0.9710(4) -0.4074(3) 0.1606(2) 0.0567(6) Uani 1 d . .
H1C H 0.9932 -0.3823 0.0988 0.068 Uiso 1 calc . .
C11 C 1.0728(4) -0.5019(3) 0.1983(2) 0.0739(8) Uani 1 d . .
H1B H 1.1764 -0.5536 0.1666 0.089 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.8947(17) . ?
O2 C3 1.365(2) . ?
O2 C7 1.434(2) . ?
F2 B1 1.375(3) . ?
O1 C4 1.3717(19) . ?
O1 C7 1.437(2) . ?
C5 C4 1.365(2) . ?
C5 C6 1.403(2) . ?
C5 H1D 0.93 . ?
F1 B1 1.375(3) . ?
N2 C13 1.335(3) . ?
N2 C16 1.398(2) . ?
N2 B1 1.552(3) . ?
C1 C6 1.385(2) . ?
C1 C2 1.406(3) . ?
C1 C8 1.495(2) . ?
C2 C3 1.365(2) . ?
C2 H2 0.93 . ?
N1 C12 1.339(3) . ?
N1 C9 1.388(2) . ?
N1 B1 1.543(3) . ?
C4 C3 1.377(2) . ?
C15 C14 1.368(3) . ?
C15 C16 1.412(3) . ?
C15 H7 0.93 . ?
C8 C16 1.378(2) . ?
C8 C9 1.396(3) . ?
C9 C10 1.400(3) . ?
C13 C14 1.398(3) . ?
C13 H11 0.93 . ?
C7 H13A 0.97 . ?
C7 H13B 0.97 . ?
C14 H15 0.93 . ?
C12 C11 1.386(4) . ?
C12 H16 0.93 . ?
C10 C11 1.368(3) . ?
C10 H1C 0.93 . ?
C11 H1B 0.93 . ?

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
C3 O2 C7 105.39(14) . . ?
C4 O1 C7 105.19(14) . . ?
C4 C5 C6 116.32(16) . . ?
C4 C5 H1D 121.8 . . ?
C6 C5 H1D 121.8 . . ?
C13 N2 C16 107.04(16) . . ?
C13 N2 B1 127.54(16) . . ?
C16 N2 B1 125.39(16) . . ?
C6 C1 C2 119.36(15) . . ?
C6 C1 C8 122.00(15) . . ?
C2 C1 C8 118.45(15) . . ?
C3 C2 C1 117.81(16) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C12 N1 C9 107.29(18) . . ?
C12 N1 B1 127.14(17) . . ?
C9 N1 B1 125.54(16) . . ?
C5 C4 O1 127.90(16) . . ?
C5 C4 C3 122.20(15) . . ?
O1 C4 C3 109.87(15) . . ?
C1 C6 C5 122.33(16) . . ?
C1 C6 Br1 120.38(12) . . ?
C5 C6 Br1 117.29(13) . . ?
C14 C15 C16 107.66(18) . . ?
C14 C15 H7 126.2 . . ?
C16 C15 H7 126.2 . . ?
C16 C8 C9 121.26(16) . . ?
C16 C8 C1 121.10(16) . . ?
C9 C8 C1 117.62(16) . . ?
N1 C9 C8 120.69(17) . . ?
N1 C9 C10 107.94(17) . . ?
C8 C9 C10 131.36(18) . . ?
C8 C16 N2 120.51(16) . . ?
C8 C16 C15 131.81(17) . . ?
N2 C16 C15 107.66(16) . . ?
N2 C13 C14 110.96(18) . . ?
N2 C13 H11 124.5 . . ?
C14 C13 H11 124.5 . . ?
F2 B1 F1 109.32(16) . . ?
F2 B1 N1 109.72(17) . . ?
F1 B1 N1 110.76(19) . . ?
F2 B1 N2 110.50(18) . . ?
F1 B1 N2 110.03(17) . . ?
N1 B1 N2 106.47(14) . . ?
O2 C7 O1 107.32(14) . . ?
O2 C7 H13A 110.2 . . ?
O1 C7 H13A 110.2 . . ?
O2 C7 H13B 110.2 . . ?
O1 C7 H13B 110.2 . . ?
H13A C7 H13B 108.5 . . ?
O2 C3 C2 127.97(17) . . ?
O2 C3 C4 110.13(15) . . ?
C2 C3 C4 121.90(16) . . ?
C15 C14 C13 106.68(19) . . ?
C15 C14 H15 126.7 . . ?
C13 C14 H15 126.7 . . ?
N1 C12 C11 110.2(2) . . ?
N1 C12 H16 124.9 . . ?
C11 C12 H16 124.9 . . ?
C11 C10 C9 107.3(2) . . ?
C11 C10 H1C 126.3 . . ?
C9 C10 H1C 126.3 . . ?
C10 C11 C12 107.3(2) . . ?
C10 C11 H1B 126.4 . . ?
C12 C11 H1B 126.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.8(3) . . . . ?
C8 C1 C2 C3 -172.25(16) . . . . ?
C6 C5 C4 O1 -179.66(15) . . . . ?
C6 C5 C4 C3 2.2(2) . . . . ?
C7 O1 C4 C5 173.17(17) . . . . ?
C7 O1 C4 C3 -8.50(18) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
C8 C1 C6 C5 173.24(16) . . . . ?
C2 C1 C6 Br1 178.19(13) . . . . ?
C8 C1 C6 Br1 -6.9(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 Br1 179.29(12) . . . . ?
C6 C1 C8 C16 90.4(2) . . . . ?
C2 C1 C8 C16 -94.7(2) . . . . ?
C6 C1 C8 C9 -91.0(2) . . . . ?
C2 C1 C8 C9 83.9(2) . . . . ?
C12 N1 C9 C8 179.7(2) . . . . ?
B1 N1 C9 C8 1.6(3) . . . . ?
C12 N1 C9 C10 -0.1(2) . . . . ?
B1 N1 C9 C10 -178.26(19) . . . . ?
C16 C8 C9 N1 -2.6(3) . . . . ?
C1 C8 C9 N1 178.74(16) . . . . ?
C16 C8 C9 C10 177.1(2) . . . . ?
C1 C8 C9 C10 -1.5(3) . . . . ?
C9 C8 C16 N2 0.4(3) . . . . ?
C1 C8 C16 N2 178.93(16) . . . . ?
C9 C8 C16 C15 -177.7(2) . . . . ?
C1 C8 C16 C15 0.9(3) . . . . ?
C13 N2 C16 C8 -178.62(19) . . . . ?
B1 N2 C16 C8 3.2(3) . . . . ?
C13 N2 C16 C15 -0.2(2) . . . . ?
B1 N2 C16 C15 -178.38(18) . . . . ?
C14 C15 C16 C8 178.5(2) . . . . ?
C14 C15 C16 N2 0.3(3) . . . . ?
C16 N2 C13 C14 0.0(3) . . . . ?
B1 N2 C13 C14 178.1(2) . . . . ?
C12 N1 B1 F2 -56.7(3) . . . . ?
C9 N1 B1 F2 121.0(2) . . . . ?
C12 N1 B1 F1 64.1(3) . . . . ?
C9 N1 B1 F1 -118.2(2) . . . . ?
C12 N1 B1 N2 -176.3(2) . . . . ?
C9 N1 B1 N2 1.4(3) . . . . ?
C13 N2 B1 F2 59.3(3) . . . . ?
C16 N2 B1 F2 -122.86(19) . . . . ?
C13 N2 B1 F1 -61.5(3) . . . . ?
C16 N2 B1 F1 116.3(2) . . . . ?
C13 N2 B1 N1 178.4(2) . . . . ?
C16 N2 B1 N1 -3.8(3) . . . . ?
C3 O2 C7 O1 -14.15(19) . . . . ?
C4 O1 C7 O2 13.91(18) . . . . ?
C7 O2 C3 C2 -171.89(19) . . . . ?
C7 O2 C3 C4 9.09(19) . . . . ?
C1 C2 C3 O2 179.50(17) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C5 C4 C3 O2 178.08(16) . . . . ?
O1 C4 C3 O2 -0.4(2) . . . . ?
C5 C4 C3 C2 -1.0(3) . . . . ?
O1 C4 C3 C2 -179.46(16) . . . . ?
C16 C15 C14 C13 -0.3(3) . . . . ?
N2 C13 C14 C15 0.2(3) . . . . ?
C9 N1 C12 C11 -0.2(3) . . . . ?
B1 N1 C12 C11 177.9(2) . . . . ?
N1 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -179.4(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
N1 C12 C11 C10 0.4(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_common            BODIPY1
_exptl_crystal_preparation       Luminescent
