# 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/. 
# 
# Audit and citation data items have may 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_2-(2,4,5-trichlorophenyl)isoindolin-1-one
_database_code_depnum_ccdc_archive 'CCDC 1021394'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;

_audit_creation_date             2014-08-26T11:05:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14  H8  Cl3  N1  O1'
_chemical_formula_sum            'C14 H8 Cl3 N O'
_chemical_formula_weight         312.56
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.2868(5)
_cell_length_b                   8.7137(5)
_cell_length_c                   24.2013(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1325.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_number            7221
_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       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.484
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_number_total             3773
_reflns_number_gt                2844
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   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)+(0.0410P)²+0.1022P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3773
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(2)
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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'

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
Cl1 Cl 0.17887(10) 0.17268(7) 0.30705(2) 0.04785(16) Uani 1 d . .
Cl2 Cl 0.66385(14) 0.36550(11) 0.47449(3) 0.0725(2) Uani 1 d . .
Cl3 Cl 0.98470(11) 0.51578(10) 0.38932(3) 0.0677(2) Uani 1 d . .
O1 O 0.1824(3) 0.4725(2) 0.23430(7) 0.0489(4) Uani 1 d . .
N1 N 0.4982(3) 0.3373(2) 0.23340(7) 0.0374(4) Uani 1 d . .
C9 C 0.5383(3) 0.3405(3) 0.29108(9) 0.0349(5) Uani 1 d . .
C1 C 0.3256(4) 0.4082(2) 0.20956(9) 0.0364(5) Uani 1 d . .
C2 C 0.3566(4) 0.3921(2) 0.14923(8) 0.0366(5) Uani 1 d . .
C10 C 0.7194(4) 0.4142(3) 0.31067(9) 0.0402(5) Uani 1 d . .
H10 H 0.8166 0.4593 0.2854 0.048 Uiso 1 calc . .
C14 C 0.4008(4) 0.2726(3) 0.32897(9) 0.0361(5) Uani 1 d . .
C13 C 0.4397(4) 0.2813(3) 0.38510(10) 0.0438(5) Uani 1 d . .
H13 H 0.3434 0.2357 0.4105 0.053 Uiso 1 calc . .
C7 C 0.5479(4) 0.3195(3) 0.13922(9) 0.0390(5) Uani 1 d . .
C12 C 0.6184(4) 0.3562(3) 0.40417(9) 0.0428(6) Uani 1 d . .
C8 C 0.6540(4) 0.2794(3) 0.19340(8) 0.0398(5) Uani 1 d . .
H8A H 0.6746 0.1672 0.1972 0.048 Uiso 1 calc . .
H8B H 0.7929 0.3317 0.1974 0.048 Uiso 1 calc . .
C11 C 0.7587(4) 0.4222(3) 0.36703(10) 0.0417(5) Uani 1 d . .
C3 C 0.2282(4) 0.4445(3) 0.10654(10) 0.0483(6) Uani 1 d . .
H3 H 0.0969 0.4945 0.1138 0.058 Uiso 1 calc . .
C6 C 0.6173(5) 0.2975(3) 0.08546(10) 0.0554(7) Uani 1 d . .
H6 H 0.7492 0.2485 0.078 0.067 Uiso 1 calc . .
C4 C 0.2984(5) 0.4211(3) 0.05294(10) 0.0569(7) Uani 1 d . .
H4 H 0.2139 0.4553 0.0228 0.068 Uiso 1 calc . .
C5 C 0.4885(5) 0.3493(3) 0.04286(10) 0.0601(7) Uani 1 d . .
H5 H 0.5331 0.3345 0.0057 0.072 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
Cl1 C14 1.728(2) . ?
Cl2 C12 1.728(2) . ?
Cl3 C11 1.725(2) . ?
O1 C1 1.218(3) . ?
N1 C1 1.375(3) . ?
N1 C9 1.419(3) . ?
N1 C8 1.467(3) . ?
C9 C10 1.391(3) . ?
C9 C14 1.392(3) . ?
C1 C2 1.480(3) . ?
C2 C7 1.380(3) . ?
C2 C3 1.388(3) . ?
C10 C11 1.388(3) . ?
C14 C13 1.382(3) . ?
C13 C12 1.379(4) . ?
C7 C6 1.386(3) . ?
C7 C8 1.512(3) . ?
C12 C11 1.385(3) . ?
C3 C4 1.385(4) . ?
C6 C5 1.386(4) . ?
C4 C5 1.371(4) . ?

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
C1 N1 C9 122.99(18) . . ?
C1 N1 C8 113.87(17) . . ?
C9 N1 C8 122.48(18) . . ?
C10 C9 C14 118.67(19) . . ?
C10 C9 N1 119.35(19) . . ?
C14 C9 N1 121.98(19) . . ?
O1 C1 N1 125.7(2) . . ?
O1 C1 C2 128.8(2) . . ?
N1 C1 C2 105.52(19) . . ?
C7 C2 C3 121.8(2) . . ?
C7 C2 C1 109.3(2) . . ?
C3 C2 C1 128.8(2) . . ?
C11 C10 C9 120.3(2) . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 Cl1 118.15(19) . . ?
C9 C14 Cl1 120.86(17) . . ?
C12 C13 C14 119.9(2) . . ?
C2 C7 C6 120.2(2) . . ?
C2 C7 C8 109.75(19) . . ?
C6 C7 C8 130.1(2) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 Cl2 119.13(19) . . ?
C11 C12 Cl2 120.97(19) . . ?
N1 C8 C7 101.43(18) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 Cl3 121.21(18) . . ?
C10 C11 Cl3 118.54(18) . . ?
C4 C3 C2 117.6(2) . . ?
C7 C6 C5 118.0(3) . . ?
C5 C4 C3 120.8(2) . . ?
C4 C5 C6 121.7(2) . . ?

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
C1 N1 C9 C10 -115.5(2) . . . . ?
C8 N1 C9 C10 54.6(3) . . . . ?
C1 N1 C9 C14 64.1(3) . . . . ?
C8 N1 C9 C14 -125.8(2) . . . . ?
C9 N1 C1 O1 -4.8(4) . . . . ?
C8 N1 C1 O1 -175.7(2) . . . . ?
C9 N1 C1 C2 173.86(19) . . . . ?
C8 N1 C1 C2 3.0(2) . . . . ?
O1 C1 C2 C7 176.0(2) . . . . ?
N1 C1 C2 C7 -2.6(2) . . . . ?
O1 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
C14 C9 C10 C11 -1.3(3) . . . . ?
N1 C9 C10 C11 178.2(2) . . . . ?
C10 C9 C14 C13 1.6(3) . . . . ?
N1 C9 C14 C13 -177.9(2) . . . . ?
C10 C9 C14 Cl1 -177.39(17) . . . . ?
N1 C9 C14 Cl1 3.1(3) . . . . ?
C9 C14 C13 C12 -0.9(4) . . . . ?
Cl1 C14 C13 C12 178.15(19) . . . . ?
C3 C2 C7 C6 0.2(4) . . . . ?
C1 C2 C7 C6 -177.0(2) . . . . ?
C3 C2 C7 C8 178.6(2) . . . . ?
C1 C2 C7 C8 1.4(3) . . . . ?
C14 C13 C12 C11 -0.2(4) . . . . ?
C14 C13 C12 Cl2 -179.9(2) . . . . ?
C1 N1 C8 C7 -2.2(2) . . . . ?
C9 N1 C8 C7 -173.07(19) . . . . ?
C2 C7 C8 N1 0.4(2) . . . . ?
C6 C7 C8 N1 178.5(3) . . . . ?
C13 C12 C11 C10 0.5(4) . . . . ?
Cl2 C12 C11 C10 -179.77(19) . . . . ?
C13 C12 C11 Cl3 -179.58(19) . . . . ?
Cl2 C12 C11 Cl3 0.2(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 Cl3 -179.67(17) . . . . ?
C7 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 176.8(2) . . . . ?
C2 C7 C6 C5 -0.5(4) . . . . ?
C8 C7 C6 C5 -178.5(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C7 C6 C5 C4 0.4(5) . . . . ?



# END of CIF
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_2-(4-bromo-2-methylphenyl)isoindolin-1-one
_database_code_depnum_ccdc_archive 'CCDC 1019580'
_audit_update_record             
;
2014-08-15 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;


_diffrn_measurement_device_type  'Bruker APEX-II CCD'
#Added by publCIF




_cell_special_details            ?
#Added by publCIF




_diffrn_measurement_method       ?
#Added by publCIF




_diffrn_radiation_monochromator  graphite
#Added by publCIF




_diffrn_radiation_source         'fine-focus sealed tube'
#Added by publCIF




_diffrn_reflns_av_R_equivalents  0.0691
#Added by publCIF



_audit_creation_date             2014-08-14T23:35:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C15  H12  N1  O1  Br1'
_chemical_formula_sum            'C15 H12 Br N O'
_chemical_formula_weight         302.17

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.335(3)
_cell_length_b                   8.635(2)
_cell_length_c                   13.184(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.87(2)
_cell_angle_gamma                90
_cell_volume                     1285.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_colour            white
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    3.183
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_number            3273
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.476
_diffrn_reflns_theta_max         28.051
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_number_total             3070
_reflns_number_gt                2105
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   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)+(0.1000P)²+0.0640P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3070
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.057
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.992
_refine_diff_density_min         -1.324
_refine_diff_density_rms         0.127

#----------------------------------------------------------------------------#
#                   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'
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'
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 0.39043(4) 0.87238(6) 1.02135(4) 0.0540(2) Uani 1 d . .
O1 O 0.1048(2) 0.1794(4) 0.9517(2) 0.0400(7) Uani 1 d . .
N1 N 0.0640(3) 0.3771(4) 0.8351(2) 0.0305(7) Uani 1 d . .
C4 C -0.1615(4) -0.0444(5) 0.7287(4) 0.0442(11) Uani 1 d . .
H4 H -0.1914 -0.1447 0.7284 0.053 Uiso 1 calc . .
C3 C -0.0791(4) 0.0019(5) 0.8058(3) 0.0398(10) Uani 1 d . .
H3 H -0.0538 -0.0648 0.8586 0.048 Uiso 1 calc . .
C2 C -0.0357(3) 0.1509(4) 0.8017(3) 0.0293(9) Uani 1 d . .
C1 C 0.0526(3) 0.2295(5) 0.8734(3) 0.0294(8) Uani 1 d . .
C9 C 0.1422(3) 0.4930(5) 0.8779(3) 0.0311(9) Uani 1 d . .
C14 C 0.2644(3) 0.4726(5) 0.8755(3) 0.0324(9) Uani 1 d . .
C13 C 0.3365(4) 0.5898(5) 0.9173(3) 0.0388(10) Uani 1 d . .
H13 H 0.4182 0.5813 0.9167 0.047 Uiso 1 calc . .
C12 C 0.2888(4) 0.7188(5) 0.9597(3) 0.0363(10) Uani 1 d . .
C15 C 0.3163(4) 0.3303(6) 0.8300(4) 0.0449(11) Uani 1 d . .
H15A H 0.3987 0.3475 0.822 0.067 Uiso 1 calc . .
H15C H 0.2752 0.3093 0.7648 0.067 Uiso 1 calc . .
H15B H 0.3081 0.2434 0.8743 0.067 Uiso 1 calc . .
C8 C -0.0114(3) 0.4053(5) 0.7417(3) 0.0312(9) Uani 1 d . .
H8A H 0.0352 0.431 0.6856 0.037 Uiso 1 calc . .
H8B H -0.0675 0.488 0.7506 0.037 Uiso 1 calc . .
C7 C -0.0729(3) 0.2528(4) 0.7246(3) 0.0289(8) Uani 1 d . .
C5 C -0.2001(4) 0.0580(6) 0.6515(3) 0.0416(11) Uani 1 d . .
H5 H -0.2564 0.0247 0.6008 0.05 Uiso 1 calc . .
C6 C -0.1572(3) 0.2083(5) 0.6476(3) 0.0365(9) Uani 1 d . .
H6 H -0.1837 0.2761 0.5958 0.044 Uiso 1 calc . .
C10 C 0.0958(4) 0.6234(5) 0.9186(3) 0.0329(9) Uani 1 d . .
H10 H 0.0141 0.6337 0.9183 0.039 Uiso 1 calc . .
C11 C 0.1686(4) 0.7399(5) 0.9599(3) 0.0365(10) Uani 1 d . .
H11 H 0.1374 0.829 0.9869 0.044 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 C12 1.894(4) . ?
O1 C1 1.225(5) . ?
N1 C1 1.381(5) . ?
N1 C9 1.422(5) . ?
N1 C8 1.458(5) . ?
C4 C3 1.380(6) . ?
C4 C5 1.390(7) . ?
C4 H4 0.93 . ?
C3 C2 1.380(5) . ?
C3 H3 0.93 . ?
C2 C7 1.384(6) . ?
C2 C1 1.481(6) . ?
C9 C10 1.371(5) . ?
C9 C14 1.399(5) . ?
C14 C13 1.386(6) . ?
C14 C15 1.509(6) . ?
C13 C12 1.377(6) . ?
C13 H13 0.93 . ?
C12 C11 1.375(6) . ?
C15 H15A 0.96 . ?
C15 H15C 0.96 . ?
C15 H15B 0.96 . ?
C8 C7 1.498(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C7 C6 1.388(5) . ?
C5 C6 1.389(7) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C10 C11 1.383(6) . ?
C10 H10 0.93 . ?
C11 H11 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
C1 N1 C9 125.4(3) . . ?
C1 N1 C8 113.4(3) . . ?
C9 N1 C8 121.2(3) . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C2 C3 C4 117.6(4) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C3 C2 C7 122.3(4) . . ?
C3 C2 C1 128.8(4) . . ?
C7 C2 C1 108.9(3) . . ?
O1 C1 N1 125.5(4) . . ?
O1 C1 C2 128.9(4) . . ?
N1 C1 C2 105.6(3) . . ?
C10 C9 C14 121.7(4) . . ?
C10 C9 N1 119.1(3) . . ?
C14 C9 N1 119.2(4) . . ?
C13 C14 C9 116.8(4) . . ?
C13 C14 C15 121.1(4) . . ?
C9 C14 C15 122.1(4) . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C11 C12 C13 122.1(4) . . ?
C11 C12 Br1 118.2(3) . . ?
C13 C12 Br1 119.7(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
N1 C8 C7 102.2(3) . . ?
N1 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
N1 C8 H8B 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C2 C7 C6 120.6(4) . . ?
C2 C7 C8 109.9(3) . . ?
C6 C7 C8 129.5(4) . . ?
C6 C5 C4 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C7 C6 C5 117.0(4) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 117.4(4) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?

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
C5 C4 C3 C2 -1.3(6) . . . . ?
C4 C3 C2 C7 0.7(6) . . . . ?
C4 C3 C2 C1 -179.8(4) . . . . ?
C9 N1 C1 O1 3.0(6) . . . . ?
C8 N1 C1 O1 -178.6(4) . . . . ?
C9 N1 C1 C2 -178.2(3) . . . . ?
C8 N1 C1 C2 0.3(4) . . . . ?
C3 C2 C1 O1 -0.7(6) . . . . ?
C7 C2 C1 O1 178.8(4) . . . . ?
C3 C2 C1 N1 -179.5(4) . . . . ?
C7 C2 C1 N1 0.1(4) . . . . ?
C1 N1 C9 C10 -113.3(4) . . . . ?
C8 N1 C9 C10 68.3(5) . . . . ?
C1 N1 C9 C14 68.0(5) . . . . ?
C8 N1 C9 C14 -110.3(4) . . . . ?
C10 C9 C14 C13 0.7(6) . . . . ?
N1 C9 C14 C13 179.3(3) . . . . ?
C10 C9 C14 C15 -179.4(4) . . . . ?
N1 C9 C14 C15 -0.8(6) . . . . ?
C9 C14 C13 C12 0.6(6) . . . . ?
C15 C14 C13 C12 -179.3(4) . . . . ?
C14 C13 C12 C11 -2.0(6) . . . . ?
C14 C13 C12 Br1 177.3(3) . . . . ?
C1 N1 C8 C7 -0.5(4) . . . . ?
C9 N1 C8 C7 178.1(3) . . . . ?
C3 C2 C7 C6 0.3(6) . . . . ?
C1 C2 C7 C6 -179.3(3) . . . . ?
C3 C2 C7 C8 179.3(3) . . . . ?
C1 C2 C7 C8 -0.3(4) . . . . ?
N1 C8 C7 C2 0.5(4) . . . . ?
N1 C8 C7 C6 179.3(3) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C2 C7 C6 C5 -0.8(5) . . . . ?
C8 C7 C6 C5 -179.5(4) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C14 C9 C10 C11 -0.6(6) . . . . ?
N1 C9 C10 C11 -179.2(4) . . . . ?
C13 C12 C11 C10 2.1(6) . . . . ?
Br1 C12 C11 C10 -177.2(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575
C8 H8A Br1 0.97 2.97 3.846(4) 151.3 2_546
C8 H8A Br1 0.97 3.11 3.579(4) 111.5 4_575



# END of CIF

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_2-([1,1'-biphenyl]-4-yl)isoindolin-1-one
_database_code_depnum_ccdc_archive 'CCDC 1020238'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;

_audit_creation_date             2014-08-20T00:48:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20  H15  N1  O1'
_chemical_formula_sum            'C20 H15 N O'
_chemical_formula_weight         285.33

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4297(13)
_cell_length_b                   5.9995(6)
_cell_length_c                   21.003(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.386(8)
_cell_angle_gamma                90
_cell_volume                     1431.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_number            16331
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.793
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_number_total             3428
_reflns_number_gt                1706
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   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)+(0.0807P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.015(3)
_refine_ls_number_reflns         3428
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.065
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
#                   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'
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'

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
O1 O 0.91981(13) 0.1134(2) 0.09625(7) 0.0533(5) Uani 1 d . .
N1 N 0.95802(15) 0.4546(3) 0.14700(8) 0.0407(5) Uani 1 d . .
C1 C 1.2078(2) 0.3676(4) -0.00903(11) 0.0555(6) Uani 1 d . .
H1 H 1.2404 0.3034 -0.0433 0.067 Uiso 1 calc . .
C2 C 1.1198(2) 0.2588(4) 0.01797(10) 0.0486(6) Uani 1 d . .
H15 H 1.0927 0.1203 0.0029 0.058 Uiso 1 calc . .
C3 C 1.07253(18) 0.3622(3) 0.06837(9) 0.0399(5) Uani 1 d . .
C4 C 0.97516(19) 0.2880(3) 0.10356(10) 0.0419(5) Uani 1 d . .
C5 C 0.87037(18) 0.4611(3) 0.18917(10) 0.0395(5) Uani 1 d . .
C6 C 0.7856(2) 0.2968(4) 0.19062(11) 0.0568(7) Uani 1 d . .
H7 H 0.7857 0.1759 0.1629 0.068 Uiso 1 calc . .
C7 C 0.7014(2) 0.3094(4) 0.23243(12) 0.0581(7) Uani 1 d . .
H8 H 0.6453 0.1968 0.2316 0.07 Uiso 1 calc . .
C8 C 0.69635(19) 0.4820(3) 0.27558(10) 0.0428(5) Uani 1 d . .
C9 C 0.60616(19) 0.4910(3) 0.32147(10) 0.0439(6) Uani 1 d . .
C10 C 0.5245(2) 0.3212(4) 0.32448(12) 0.0596(7) Uani 1 d . .
H10 H 0.5248 0.2019 0.2962 0.071 Uiso 1 calc . .
C11 C 0.4431(2) 0.3245(4) 0.36809(12) 0.0660(8) Uani 1 d . .
H11 H 0.3893 0.2083 0.3687 0.079 Uiso 1 calc . .
C12 C 0.4404(2) 0.4971(4) 0.41062(12) 0.0630(7) Uani 1 d . .
H2 H 0.3862 0.4983 0.4405 0.076 Uiso 1 calc . .
C13 C 1.2485(2) 0.5731(4) 0.01464(12) 0.0589(7) Uani 1 d . .
H3 H 1.3092 0.643 -0.0037 0.071 Uiso 1 calc . .
C14 C 1.04099(19) 0.6403(3) 0.14341(10) 0.0461(6) Uani 1 d . .
H6 H 1.0906 0.6592 0.1836 0.055 Uiso 1 calc . .
H5 H 0.9997 0.7787 0.1325 0.055 Uiso 1 calc . .
C15 C 1.11155(19) 0.5682(3) 0.09125(10) 0.0427(5) Uani 1 d . .
C16 C 1.2010(2) 0.6759(4) 0.06452(11) 0.0518(6) Uani 1 d . .
H4 H 1.2285 0.814 0.0798 0.062 Uiso 1 calc . .
C17 C 0.8653(2) 0.6366(4) 0.23154(11) 0.0592(7) Uani 1 d . .
H14 H 0.9201 0.7511 0.2318 0.071 Uiso 1 calc . .
C18 C 0.7808(2) 0.6451(4) 0.27326(12) 0.0597(7) Uani 1 d . .
H13 H 0.7806 0.7658 0.301 0.072 Uiso 1 calc . .
C19 C 0.6006(2) 0.6650(4) 0.36433(11) 0.0580(7) Uani 1 d . .
H9 H 0.6532 0.783 0.3635 0.07 Uiso 1 calc . .
C20 C 0.5197(2) 0.6686(4) 0.40817(12) 0.0660(8) Uani 1 d . .
H12 H 0.5186 0.7879 0.4364 0.079 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
O1 C4 1.224(2) . ?
N1 C4 1.382(2) . ?
N1 C5 1.410(3) . ?
N1 C14 1.470(2) . ?
C1 C2 1.374(3) . ?
C1 C13 1.390(3) . ?
C1 H1 0.93 . ?
C2 C3 1.387(3) . ?
C2 H15 0.93 . ?
C3 C15 1.382(3) . ?
C3 C4 1.472(3) . ?
C5 C17 1.384(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.376(3) . ?
C6 H7 0.93 . ?
C7 C8 1.381(3) . ?
C7 H8 0.93 . ?
C8 C18 1.379(3) . ?
C8 C9 1.488(3) . ?
C9 C19 1.384(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.93 . ?
C11 C12 1.370(3) . ?
C11 H11 0.93 . ?
C12 C20 1.376(3) . ?
C12 H2 0.93 . ?
C13 C16 1.378(3) . ?
C13 H3 0.93 . ?
C14 C15 1.495(3) . ?
C14 H6 0.97 . ?
C14 H5 0.97 . ?
C15 C16 1.381(3) . ?
C16 H4 0.93 . ?
C17 C18 1.375(3) . ?
C17 H14 0.93 . ?
C18 H13 0.93 . ?
C19 C20 1.376(3) . ?
C19 H9 0.93 . ?
C20 H12 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
C4 N1 C5 126.69(17) . . ?
C4 N1 C14 111.99(17) . . ?
C5 N1 C14 121.27(16) . . ?
C2 C1 C13 120.3(2) . . ?
C2 C1 H1 119.8 . . ?
C13 C1 H1 119.8 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H15 121.1 . . ?
C3 C2 H15 121.1 . . ?
C15 C3 C2 121.8(2) . . ?
C15 C3 C4 109.20(18) . . ?
C2 C3 C4 128.9(2) . . ?
O1 C4 N1 126.3(2) . . ?
O1 C4 C3 127.23(19) . . ?
N1 C4 C3 106.45(18) . . ?
C17 C5 C6 116.6(2) . . ?
C17 C5 N1 120.57(19) . . ?
C6 C5 N1 122.82(19) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H7 119.5 . . ?
C5 C6 H7 119.5 . . ?
C6 C7 C8 122.9(2) . . ?
C6 C7 H8 118.6 . . ?
C8 C7 H8 118.6 . . ?
C18 C8 C7 115.4(2) . . ?
C18 C8 C9 122.3(2) . . ?
C7 C8 C9 122.3(2) . . ?
C19 C9 C10 116.4(2) . . ?
C19 C9 C8 122.2(2) . . ?
C10 C9 C8 121.4(2) . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C20 118.6(2) . . ?
C11 C12 H2 120.7 . . ?
C20 C12 H2 120.7 . . ?
C16 C13 C1 121.7(2) . . ?
C16 C13 H3 119.2 . . ?
C1 C13 H3 119.2 . . ?
N1 C14 C15 102.83(16) . . ?
N1 C14 H6 111.2 . . ?
C15 C14 H6 111.2 . . ?
N1 C14 H5 111.2 . . ?
C15 C14 H5 111.2 . . ?
H6 C14 H5 109.1 . . ?
C16 C15 C3 120.2(2) . . ?
C16 C15 C14 130.3(2) . . ?
C3 C15 C14 109.52(19) . . ?
C13 C16 C15 118.1(2) . . ?
C13 C16 H4 120.9 . . ?
C15 C16 H4 120.9 . . ?
C18 C17 C5 121.4(2) . . ?
C18 C17 H14 119.3 . . ?
C5 C17 H14 119.3 . . ?
C17 C18 C8 122.7(2) . . ?
C17 C18 H13 118.7 . . ?
C8 C18 H13 118.7 . . ?
C20 C19 C9 122.0(2) . . ?
C20 C19 H9 119 . . ?
C9 C19 H9 119 . . ?
C12 C20 C19 120.5(2) . . ?
C12 C20 H12 119.7 . . ?
C19 C20 H12 119.7 . . ?

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
C13 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C15 0.1(3) . . . . ?
C1 C2 C3 C4 177.0(2) . . . . ?
C5 N1 C4 O1 -3.2(3) . . . . ?
C14 N1 C4 O1 179.4(2) . . . . ?
C5 N1 C4 C3 176.94(17) . . . . ?
C14 N1 C4 C3 -0.6(2) . . . . ?
C15 C3 C4 O1 -179.6(2) . . . . ?
C2 C3 C4 O1 3.1(4) . . . . ?
C15 C3 C4 N1 0.3(2) . . . . ?
C2 C3 C4 N1 -176.98(19) . . . . ?
C4 N1 C5 C17 178.3(2) . . . . ?
C14 N1 C5 C17 -4.4(3) . . . . ?
C4 N1 C5 C6 -2.0(3) . . . . ?
C14 N1 C5 C6 175.30(19) . . . . ?
C17 C5 C6 C7 -0.1(3) . . . . ?
N1 C5 C6 C7 -179.9(2) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C6 C7 C8 C18 1.2(4) . . . . ?
C6 C7 C8 C9 -178.7(2) . . . . ?
C18 C8 C9 C19 0.6(3) . . . . ?
C7 C8 C9 C19 -179.5(2) . . . . ?
C18 C8 C9 C10 -177.8(2) . . . . ?
C7 C8 C9 C10 2.1(3) . . . . ?
C19 C9 C10 C11 -0.6(4) . . . . ?
C8 C9 C10 C11 177.9(2) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C20 1.0(4) . . . . ?
C2 C1 C13 C16 -1.3(4) . . . . ?
C4 N1 C14 C15 0.6(2) . . . . ?
C5 N1 C14 C15 -177.04(17) . . . . ?
C2 C3 C15 C16 -0.9(3) . . . . ?
C4 C3 C15 C16 -178.36(18) . . . . ?
C2 C3 C15 C14 177.60(18) . . . . ?
C4 C3 C15 C14 0.1(2) . . . . ?
N1 C14 C15 C16 177.8(2) . . . . ?
N1 C14 C15 C3 -0.4(2) . . . . ?
C1 C13 C16 C15 0.5(3) . . . . ?
C3 C15 C16 C13 0.6(3) . . . . ?
C14 C15 C16 C13 -177.6(2) . . . . ?
C6 C5 C17 C18 0.6(4) . . . . ?
N1 C5 C17 C18 -179.7(2) . . . . ?
C5 C17 C18 C8 -0.2(4) . . . . ?
C7 C8 C18 C17 -0.7(4) . . . . ?
C9 C8 C18 C17 179.2(2) . . . . ?
C10 C9 C19 C20 0.8(4) . . . . ?
C8 C9 C19 C20 -177.7(2) . . . . ?
C11 C12 C20 C19 -0.7(4) . . . . ?
C9 C19 C20 C12 -0.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565
C6 H7 O1 0.93 2.22 2.858(3) 125.1 .
C14 H5 O1 0.97 2.3 3.264(3) 172.1 1_565



# END of CIF
