# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_sg365
_database_code_depnum_ccdc_archive 'CCDC 906867'
_audit_update_record             
;
2012-10-19 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;
#TrackingRef '14799_web_deposit_cif_file_0_SamuelGuieu_1350656402.(3-bromo-4-(dimethylamino)phenyl)(4-(dimethylamino)phenyl)methanone.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(3-bromo-4-(dimethylamino)phenyl)(4-(dimethylamino)phenyl)methanone
;
_chemical_name_common            
(3-bromo-4-(dimethylamino)phenyl)(4-(dimethylamino)phenyl)methanone
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Br N2 O'
_chemical_formula_sum            'C17 H19 Br N2 O'
_chemical_formula_weight         347.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6422(3)
_cell_length_b                   9.6691(4)
_cell_length_c                   10.1342(4)
_cell_angle_alpha                66.683(2)
_cell_angle_beta                 71.5110(10)
_cell_angle_gamma                67.1620(10)
_cell_volume                     784.58(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5503
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.84

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    2.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_T_max  0.8178
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13329
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         31.15
_reflns_number_total             4843
_reflns_number_gt                3855
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.3514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4843
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.15896(3) 0.08128(3) 1.07974(2) 0.03996(9) Uani 1 1 d . . .
C8 C 0.6919(2) 0.5727(2) 0.6398(2) 0.0208(3) Uani 1 1 d . . .
C13 C 0.6091(2) 0.5925(2) 0.5386(2) 0.0231(4) Uani 1 1 d . . .
H13 H 0.6433 0.5170 0.4883 0.028 Uiso 1 1 calc R . .
C1 C 0.8183(2) 0.4252(2) 0.6777(2) 0.0229(4) Uani 1 1 d . . .
O1 O 0.82525(17) 0.30540(17) 0.65652(18) 0.0332(3) Uani 1 1 d . . .
N2 N 0.28609(19) 0.9457(2) 0.5699(2) 0.0276(4) Uani 1 1 d . . .
C9 C 0.6409(2) 0.6881(2) 0.7090(2) 0.0216(3) Uani 1 1 d . . .
H9 H 0.6983 0.6806 0.7737 0.026 Uiso 1 1 calc R . .
C12 C 0.4795(2) 0.7185(2) 0.5104(2) 0.0237(4) Uani 1 1 d . . .
H12 H 0.4284 0.7309 0.4384 0.028 Uiso 1 1 calc R . .
C4 C 1.1077(2) 0.2660(2) 0.9187(2) 0.0242(4) Uani 1 1 d . . .
N1 N 1.29369(19) 0.3697(2) 0.93780(18) 0.0265(3) Uani 1 1 d . . .
C11 C 0.4219(2) 0.8294(2) 0.5873(2) 0.0218(4) Uani 1 1 d . . .
C3 C 0.9945(2) 0.2794(2) 0.8544(2) 0.0233(4) Uani 1 1 d . . .
H3 H 0.9551 0.1933 0.8837 0.028 Uiso 1 1 calc R . .
C5 C 1.1755(2) 0.3868(2) 0.8742(2) 0.0220(4) Uani 1 1 d . . .
C6 C 1.1152(2) 0.5259(2) 0.7666(2) 0.0251(4) Uani 1 1 d . . .
H6 H 1.1561 0.6113 0.7349 0.030 Uiso 1 1 calc R . .
C7 C 0.9976(2) 0.5424(2) 0.7052(2) 0.0250(4) Uani 1 1 d . . .
H7 H 0.9578 0.6391 0.6343 0.030 Uiso 1 1 calc R . .
C10 C 0.5089(2) 0.8126(2) 0.6853(2) 0.0222(4) Uani 1 1 d . . .
H10 H 0.4758 0.8882 0.7353 0.027 Uiso 1 1 calc R . .
C2 C 0.9376(2) 0.4184(2) 0.7467(2) 0.0223(4) Uani 1 1 d . . .
C16 C 1.3237(3) 0.5154(3) 0.9141(2) 0.0356(5) Uani 1 1 d . . .
H16A H 1.4075 0.4909 0.9625 0.053 Uiso 1 1 calc R . .
H16C H 1.2311 0.5869 0.9550 0.053 Uiso 1 1 calc R . .
H16B H 1.3527 0.5662 0.8088 0.053 Uiso 1 1 calc R . .
C15 C 1.4384(2) 0.2464(3) 0.9114(3) 0.0394(5) Uani 1 1 d . . .
H15C H 1.5129 0.2442 0.9599 0.059 Uiso 1 1 calc R . .
H15B H 1.4790 0.2695 0.8059 0.059 Uiso 1 1 calc R . .
H15A H 1.4198 0.1435 0.9510 0.059 Uiso 1 1 calc R . .
C17 C 0.2223(2) 1.0532(2) 0.6559(3) 0.0325(5) Uani 1 1 d . . .
H17B H 0.1249 1.1283 0.6288 0.049 Uiso 1 1 calc R . .
H17A H 0.2943 1.1108 0.6368 0.049 Uiso 1 1 calc R . .
H17C H 0.2044 0.9931 0.7602 0.049 Uiso 1 1 calc R . .
C18 C 0.2101(3) 0.9720(3) 0.4556(3) 0.0388(5) Uani 1 1 d . . .
H18A H 0.1145 1.0593 0.4584 0.058 Uiso 1 1 calc R . .
H18B H 0.1869 0.8760 0.4711 0.058 Uiso 1 1 calc R . .
H18C H 0.2774 0.9987 0.3600 0.058 Uiso 1 1 calc R . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.9015(18) . ?
C8 C9 1.398(3) . ?
C8 C13 1.404(3) . ?
C8 C1 1.477(2) . ?
C13 C12 1.377(3) . ?
C13 H13 0.9500 . ?
C1 O1 1.233(2) . ?
C1 C2 1.494(3) . ?
N2 C11 1.363(2) . ?
N2 C17 1.449(3) . ?
N2 C18 1.451(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9500 . ?
C12 C11 1.411(3) . ?
C12 H12 0.9500 . ?
C4 C3 1.382(3) . ?
C4 C5 1.408(3) . ?
N1 C5 1.406(2) . ?
N1 C16 1.460(3) . ?
N1 C15 1.471(3) . ?
C11 C10 1.418(3) . ?
C3 C2 1.395(3) . ?
C3 H3 0.9500 . ?
C5 C6 1.403(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C2 1.390(3) . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C9 C8 C13 117.70(16) . . ?
C9 C8 C1 123.38(16) . . ?
C13 C8 C1 118.66(17) . . ?
C12 C13 C8 121.74(18) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
O1 C1 C8 120.93(17) . . ?
O1 C1 C2 119.05(16) . . ?
C8 C1 C2 120.00(16) . . ?
C11 N2 C17 120.81(17) . . ?
C11 N2 C18 120.09(18) . . ?
C17 N2 C18 118.89(17) . . ?
C10 C9 C8 121.32(17) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C13 C12 C11 120.64(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C3 C4 C5 122.10(17) . . ?
C3 C4 Br1 116.58(14) . . ?
C5 C4 Br1 121.20(14) . . ?
C5 N1 C16 115.81(17) . . ?
C5 N1 C15 115.84(17) . . ?
C16 N1 C15 110.38(18) . . ?
N2 C11 C12 120.87(17) . . ?
N2 C11 C10 121.67(18) . . ?
C12 C11 C10 117.45(16) . . ?
C4 C3 C2 120.40(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C6 C5 N1 122.26(17) . . ?
C6 C5 C4 116.26(17) . . ?
N1 C5 C4 121.45(17) . . ?
C7 C6 C5 121.90(18) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 120.54(17) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C9 C10 C11 120.93(17) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C7 C2 C3 118.70(17) . . ?
C7 C2 C1 123.00(17) . . ?
C3 C2 C1 118.27(17) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
N1 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        31.15
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_sg112
_database_code_depnum_ccdc_archive 'CCDC 906868'
_audit_update_record             
;
2012-10-19 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;
#TrackingRef '14800_web_deposit_cif_file_1_SamuelGuieu_1350656402.bis(3-bromo-4-(dimethylamino)phenyl)methanone.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis(3-bromo-4-(dimethylamino)phenyl)methanone
;
_chemical_name_common            bis(3-bromo-4-(dimethylamino)phenyl)methanone
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 Br2 N2 O1'
_chemical_formula_sum            'C17 H18 Br2 N2 O1'
_chemical_formula_weight         426.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   18.632(6)
_cell_length_b                   8.288(2)
_cell_length_c                   14.009(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.796(8)
_cell_angle_gamma                90.00
_cell_volume                     1709.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5604
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    4.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2526
_exptl_absorpt_correction_T_max  0.4504
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5582
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         28.00
_reflns_number_total             2051
_reflns_number_gt                1702
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0332P)²+2.9188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2051
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.08276(2) 0.80691(3) 0.45357(3) 0.05083(12) Uani 1 1 d . . .
C8 C 0.1854(2) 0.2917(4) 0.5885(3) 0.0548(7) Uani 1 1 d . . .
H8B H 0.2129 0.2536 0.5530 0.082 Uiso 1 1 calc R . .
H8C H 0.1275 0.2406 0.5497 0.082 Uiso 1 1 calc R . .
H8A H 0.2240 0.2663 0.6731 0.082 Uiso 1 1 calc R . .
C4 C 0.09294(16) 0.6949(3) 0.5802(2) 0.0339(5) Uani 1 1 d . . .
C2 C 0.04589(16) 0.6913(3) 0.7078(2) 0.0341(5) Uani 1 1 d . . .
O1 O 0.0000 0.9276(3) 0.7500 0.0557(7) Uani 1 2 d S . .
C3 C 0.05295(16) 0.7696(3) 0.6255(2) 0.0336(5) Uani 1 1 d . . .
H3 H 0.0304 0.8738 0.6007 0.040 Uiso 1 1 calc R . .
C6 C 0.12688(18) 0.4669(3) 0.7042(2) 0.0423(6) Uani 1 1 d . . .
H6 H 0.1532 0.3657 0.7337 0.051 Uiso 1 1 calc R . .
C5 C 0.13270(15) 0.5412(3) 0.6194(2) 0.0343(5) Uani 1 1 d . . .
N1 N 0.17310(14) 0.4659(3) 0.5728(2) 0.0421(5) Uani 1 1 d . . .
C1 C 0.0000 0.7802(4) 0.7500 0.0379(7) Uani 1 2 d S . .
C7 C 0.08326(17) 0.5383(3) 0.7466(2) 0.0414(6) Uani 1 1 d . . .
H7 H 0.0793 0.4830 0.8010 0.050 Uiso 1 1 calc R . .
C9 C 0.2525(2) 0.5451(4) 0.5947(3) 0.0640(9) Uani 1 1 d . . .
H9B H 0.2734 0.4828 0.5582 0.096 Uiso 1 1 calc R . .
H9A H 0.3001 0.5530 0.6801 0.096 Uiso 1 1 calc R . .
H9C H 0.2359 0.6513 0.5600 0.096 Uiso 1 1 calc R . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.905(2) . ?
C8 N1 1.457(4) . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8A 0.9600 . ?
C4 C3 1.387(3) . ?
C4 C5 1.405(3) . ?
C2 C7 1.387(3) . ?
C2 C3 1.397(3) . ?
C2 C1 1.498(3) . ?
O1 C1 1.221(4) . ?
C3 H3 0.9300 . ?
C6 C7 1.398(4) . ?
C6 C5 1.401(3) . ?
C6 H6 0.9300 . ?
C5 N1 1.409(3) . ?
N1 C9 1.469(4) . ?
C1 C2 1.498(3) 2_556 ?
C7 H7 0.9300 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9C 0.9600 . ?

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
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 Br1 115.74(17) . . ?
C5 C4 Br1 122.26(17) . . ?
C7 C2 C3 118.0(2) . . ?
C7 C2 C1 124.4(2) . . ?
C3 C2 C1 117.6(2) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C7 C6 C5 122.8(2) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C5 C4 115.7(2) . . ?
C6 C5 N1 122.7(2) . . ?
C4 C5 N1 121.6(2) . . ?
C5 N1 C8 116.7(2) . . ?
C5 N1 C9 117.5(2) . . ?
C8 N1 C9 111.5(2) . . ?
O1 C1 C2 119.45(15) . 2_556 ?
O1 C1 C2 119.45(15) . . ?
C2 C1 C2 121.1(3) 2_556 . ?
C2 C7 C6 120.2(2) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?

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 -3.6(4) . . . . ?
Br1 C4 C3 C2 172.08(18) . . . . ?
C7 C2 C3 C4 2.4(4) . . . . ?
C1 C2 C3 C4 -178.8(2) . . . . ?
C7 C6 C5 C4 1.0(4) . . . . ?
C7 C6 C5 N1 -177.1(2) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
Br1 C4 C5 C6 -173.59(18) . . . . ?
C3 C4 C5 N1 179.9(2) . . . . ?
Br1 C4 C5 N1 4.5(3) . . . . ?
C6 C5 N1 C8 17.2(4) . . . . ?
C4 C5 N1 C8 -160.7(2) . . . . ?
C6 C5 N1 C9 -119.0(3) . . . . ?
C4 C5 N1 C9 63.0(3) . . . . ?
C7 C2 C1 O1 152.34(19) . . . . ?
C3 C2 C1 O1 -26.4(2) . . . . ?
C7 C2 C1 C2 -27.66(19) . . . 2_556 ?
C3 C2 C1 C2 153.6(2) . . . 2_556 ?
C3 C2 C7 C6 0.4(4) . . . . ?
C1 C2 C7 C6 -178.3(2) . . . . ?
C5 C6 C7 C2 -2.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.068


####################################################################### 
# 
# 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_sg680
_database_code_depnum_ccdc_archive 'CCDC 1531068'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '3,3?-Dibromo-4,4?-dimethoxybenzophenone '
_chemical_name_common            ?
_chemical_melting_point          112-114?C
_chemical_formula_moiety         'C15 H12 Br2 O3'
_chemical_formula_sum            'C15 H12 Br2 O3'
_chemical_formula_weight         400.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2012(7)
_cell_length_b                   10.0238(10)
_cell_length_c                   10.6964(10)
_cell_angle_alpha                84.210(3)
_cell_angle_beta                 81.717(3)
_cell_angle_gamma                70.242(3)
_cell_volume                     717.94(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      33.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    5.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2109
_exptl_absorpt_correction_T_max  0.5505
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(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  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  5
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            64169
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         33.34
_reflns_number_total             5527
_reflns_number_gt                4962
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0343P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5527
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.00848(2) 0.334642(13) 0.564437(12) 0.02805(4) Uani 1 1 d . . .
Br1 Br 0.59437(2) -0.429499(15) 1.291341(14) 0.03041(4) Uani 1 1 d . . .
C9 C 0.24609(17) -0.02140(12) 0.79825(11) 0.01807(19) Uani 1 1 d . . .
O3 O 0.19551(15) 0.07976(10) 0.41568(8) 0.02379(17) Uani 1 1 d . . .
C12 C 0.21784(17) 0.03995(12) 0.53831(11) 0.01815(18) Uani 1 1 d . . .
C7 C 0.18675(18) -0.27451(13) 0.96837(11) 0.0202(2) Uani 1 1 d . . .
H7 H 0.1065 -0.2444 0.9010 0.024 Uiso 1 1 calc R . .
C6 C 0.19641(18) -0.40146(13) 1.03753(12) 0.0212(2) Uani 1 1 d . . .
H6 H 0.1215 -0.4567 1.0175 0.025 Uiso 1 1 calc R . .
O1 O 0.26899(16) 0.04915(10) 0.99747(9) 0.02701(19) Uani 1 1 d . . .
O2 O 0.33005(14) -0.56878(9) 1.20916(9) 0.02414(17) Uani 1 1 d . . .
C10 C 0.15696(17) 0.11864(12) 0.75209(11) 0.01861(19) Uani 1 1 d . . .
H10 H 0.1074 0.1934 0.8086 0.022 Uiso 1 1 calc R . .
C2 C 0.29362(17) -0.19132(12) 0.99703(10) 0.01812(18) Uani 1 1 d . . .
C8 C 0.1998(2) -0.64510(14) 1.19404(15) 0.0289(3) Uani 1 1 d . . .
H8C H 0.0622 -0.5806 1.2020 0.043 Uiso 1 1 calc R . .
H8A H 0.2139 -0.7225 1.2595 0.043 Uiso 1 1 calc R . .
H8B H 0.2341 -0.6845 1.1103 0.043 Uiso 1 1 calc R . .
C3 C 0.41587(17) -0.23902(12) 1.09427(11) 0.01865(19) Uani 1 1 d . . .
H3 H 0.4912 -0.1839 1.1140 0.022 Uiso 1 1 calc R . .
C11 C 0.14146(17) 0.14742(11) 0.62463(11) 0.01823(19) Uani 1 1 d . . .
C14 C 0.32007(18) -0.12916(12) 0.71320(11) 0.0204(2) Uani 1 1 d . . .
H14 H 0.3791 -0.2244 0.7439 0.024 Uiso 1 1 calc R . .
C5 C 0.31484(17) -0.44841(12) 1.13588(11) 0.01841(19) Uani 1 1 d . . .
C13 C 0.30860(18) -0.09909(12) 0.58434(11) 0.0208(2) Uani 1 1 d . . .
H13 H 0.3626 -0.1733 0.5274 0.025 Uiso 1 1 calc R . .
C1 C 0.26958(17) -0.04694(12) 0.93534(11) 0.01907(19) Uani 1 1 d . . .
C4 C 0.42693(17) -0.36601(12) 1.16149(11) 0.01880(19) Uani 1 1 d . . .
C15 C 0.2788(2) -0.02743(14) 0.32557(12) 0.0250(2) Uani 1 1 d . . .
H15C H 0.4222 -0.0696 0.3297 0.038 Uiso 1 1 calc R . .
H15A H 0.2550 0.0152 0.2403 0.038 Uiso 1 1 calc R . .
H15B H 0.2164 -0.1013 0.3450 0.038 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br2 C11 1.8901(11) . ?
Br1 C4 1.8903(11) . ?
C9 C14 1.3956(16) . ?
C9 C10 1.4031(15) . ?
C9 C1 1.4869(16) . ?
O3 C12 1.3481(14) . ?
O3 C15 1.4317(15) . ?
C12 C13 1.3966(16) . ?
C12 C11 1.4033(16) . ?
C7 C2 1.3910(16) . ?
C7 C6 1.3915(16) . ?
C7 H7 0.9500 . ?
C6 C5 1.3938(17) . ?
C6 H6 0.9500 . ?
O1 C1 1.2226(15) . ?
O2 C5 1.3516(14) . ?
O2 C8 1.4298(16) . ?
C10 C11 1.3773(16) . ?
C10 H10 0.9500 . ?
C2 C3 1.4015(16) . ?
C2 C1 1.4936(15) . ?
C8 H8C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C3 C4 1.3809(16) . ?
C3 H3 0.9500 . ?
C14 C13 1.3891(16) . ?
C14 H14 0.9500 . ?
C5 C4 1.4032(16) . ?
C13 H13 0.9500 . ?
C15 H15C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?

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
C14 C9 C10 119.04(10) . . ?
C14 C9 C1 122.71(10) . . ?
C10 C9 C1 118.12(10) . . ?
C12 O3 C15 117.48(10) . . ?
O3 C12 C13 124.78(11) . . ?
O3 C12 C11 116.65(10) . . ?
C13 C12 C11 118.57(11) . . ?
C2 C7 C6 120.56(11) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C6 C5 120.69(11) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 O2 C8 117.71(10) . . ?
C11 C10 C9 119.81(10) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C7 C2 C3 119.11(10) . . ?
C7 C2 C1 122.21(10) . . ?
C3 C2 C1 118.47(10) . . ?
O2 C8 H8C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C3 C2 120.07(11) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C10 C11 C12 121.47(10) . . ?
C10 C11 Br2 119.54(8) . . ?
C12 C11 Br2 118.97(8) . . ?
C13 C14 C9 120.93(10) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
O2 C5 C6 124.55(11) . . ?
O2 C5 C4 117.12(10) . . ?
C6 C5 C4 118.33(10) . . ?
C12 C13 C14 120.14(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O1 C1 C9 120.52(10) . . ?
O1 C1 C2 120.05(10) . . ?
C9 C1 C2 119.42(10) . . ?
C3 C4 C5 121.20(10) . . ?
C3 C4 Br1 119.50(9) . . ?
C5 C4 Br1 119.31(8) . . ?
O3 C15 H15C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?

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
C15 O3 C12 C13 -2.92(17) . . . . ?
C15 O3 C12 C11 177.78(10) . . . . ?
C2 C7 C6 C5 -0.67(19) . . . . ?
C14 C9 C10 C11 0.84(17) . . . . ?
C1 C9 C10 C11 176.81(10) . . . . ?
C6 C7 C2 C3 1.81(18) . . . . ?
C6 C7 C2 C1 -172.83(11) . . . . ?
C7 C2 C3 C4 -0.95(17) . . . . ?
C1 C2 C3 C4 173.89(11) . . . . ?
C9 C10 C11 C12 -1.72(17) . . . . ?
C9 C10 C11 Br2 176.60(8) . . . . ?
O3 C12 C11 C10 -179.71(11) . . . . ?
C13 C12 C11 C10 0.95(17) . . . . ?
O3 C12 C11 Br2 1.96(14) . . . . ?
C13 C12 C11 Br2 -177.38(9) . . . . ?
C10 C9 C14 C13 0.79(18) . . . . ?
C1 C9 C14 C13 -174.99(11) . . . . ?
C8 O2 C5 C6 -7.16(18) . . . . ?
C8 O2 C5 C4 172.91(11) . . . . ?
C7 C6 C5 O2 178.75(11) . . . . ?
C7 C6 C5 C4 -1.31(18) . . . . ?
O3 C12 C13 C14 -178.59(11) . . . . ?
C11 C12 C13 C14 0.70(18) . . . . ?
C9 C14 C13 C12 -1.56(18) . . . . ?
C14 C9 C1 O1 154.15(12) . . . . ?
C10 C9 C1 O1 -21.66(17) . . . . ?
C14 C9 C1 C2 -25.96(17) . . . . ?
C10 C9 C1 C2 158.22(11) . . . . ?
C7 C2 C1 O1 140.29(13) . . . . ?
C3 C2 C1 O1 -34.38(17) . . . . ?
C7 C2 C1 C9 -39.60(16) . . . . ?
C3 C2 C1 C9 145.73(11) . . . . ?
C2 C3 C4 C5 -1.07(18) . . . . ?
C2 C3 C4 Br1 179.45(9) . . . . ?
O2 C5 C4 C3 -177.87(11) . . . . ?
C6 C5 C4 C3 2.19(17) . . . . ?
O2 C5 C4 Br1 1.61(15) . . . . ?
C6 C5 C4 Br1 -178.33(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        33.34
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.073
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1531067'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 (3-bromo-4-(dimethylamino)phenyl)(3-bromo-4-(methylamino)phenyl)methanone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br2 N2 O'
_chemical_formula_sum            'C16 H16 Br2 N2 O'
_chemical_formula_weight         412.13

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8321(10)
_cell_length_b                   9.9164(8)
_cell_length_c                   13.5148(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.805(3)
_cell_angle_gamma                90
_cell_volume                     1580.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.42

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   0.2987
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.130
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14859
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3219
_reflns_number_gt                2610
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.1116P)²+7.2523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3219
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
N01 N 0.6951(4) 0.5173(5) 1.6164(4) 0.0375(11) Uani 1 1 d . . . . .
O01 O 0.6150(6) 0.1405(6) 1.2421(4) 0.0666(17) Uani 1 1 d . . . . .
N02 N 0.2941(4) 0.4481(6) 0.9145(4) 0.0386(12) Uani 1 1 d . . . . .
C04 C 0.6645(5) 0.5259(6) 1.4344(5) 0.0379(13) Uani 1 1 d . . . . .
H04 H 0.6900 0.6146 1.4351 0.045 Uiso 1 1 calc R U . . .
C09 C 0.4984(5) 0.2427(6) 1.0699(4) 0.0359(12) Uani 1 1 d . . . . .
H09 H 0.5412 0.1649 1.0641 0.043 Uiso 1 1 calc R U . . .
C03 C 0.6601(5) 0.4573(6) 1.5243(4) 0.0324(12) Uani 1 1 d . . . . .
C05 C 0.6319(5) 0.4654(7) 1.3444(5) 0.0411(14) Uani 1 1 d . . . . .
H05 H 0.6350 0.5144 1.2860 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7911(6) 0.4496(7) 1.6745(5) 0.0454(15) Uani 1 1 d . . . . .
H16A H 0.7806 0.3537 1.6713 0.068 Uiso 1 1 calc R U . . .
H16B H 0.7939 0.4785 1.7424 0.068 Uiso 1 1 calc R U . . .
H16C H 0.8609 0.4728 1.6472 0.068 Uiso 1 1 calc R U . . .
C01 C 0.5874(5) 0.2628(6) 1.4298(4) 0.0360(13) Uani 1 1 d . . . . .
H01 H 0.5640 0.1733 1.4291 0.043 Uiso 1 1 calc R U . . .
C07 C 0.5742(6) 0.2543(7) 1.2458(5) 0.0453(15) Uani 1 1 d . . . . .
C14 C 0.2215(6) 0.5628(7) 0.9178(5) 0.0472(16) Uani 1 1 d . . . . .
H14A H 0.1709 0.5504 0.9690 0.071 Uiso 1 1 calc R U . . .
H14B H 0.1783 0.5731 0.8550 0.071 Uiso 1 1 calc R U . . .
H14C H 0.2666 0.6422 0.9318 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7124(7) 0.6630(7) 1.6176(6) 0.0490(17) Uani 1 1 d . . . . .
H15C H 0.7837 0.6836 1.5921 0.074 Uiso 1 1 calc R U . . .
H15A H 0.7127 0.6957 1.6845 0.074 Uiso 1 1 calc R U . . .
H15B H 0.6522 0.7057 1.5770 0.074 Uiso 1 1 calc R U . . .
H02 H 0.286(10) 0.396(13) 0.858(9) 0.11(4) Uiso 1 1 d . . . . .
Br2 Br 0.42151(5) 0.17853(7) 0.86765(4) 0.0383(3) Uani 1 1 d . . . . .
Br1 Br 0.58228(6) 0.23162(8) 1.63539(4) 0.0447(3) Uani 1 1 d . . . . .
C11 C 0.3623(5) 0.4054(6) 0.9943(4) 0.0309(11) Uani 1 1 d . . . . .
C02 C 0.6151(5) 0.3271(6) 1.5188(4) 0.0353(13) Uani 1 1 d . . . . .
C10 C 0.4293(5) 0.2850(6) 0.9904(4) 0.0325(12) Uani 1 1 d . . . . .
C08 C 0.5070(5) 0.3130(7) 1.1603(5) 0.0382(13) Uani 1 1 d . . . . .
C12 C 0.3707(5) 0.4737(6) 1.0846(5) 0.0368(13) Uani 1 1 d . . . . .
H12 H 0.3283 0.5518 1.0903 0.044 Uiso 1 1 calc R U . . .
C06 C 0.5947(5) 0.3327(6) 1.3399(5) 0.0371(13) Uani 1 1 d . . . . .
C13 C 0.4397(5) 0.4301(7) 1.1665(4) 0.0367(13) Uani 1 1 d . . . . .
H13 H 0.4416 0.4781 1.2257 0.044 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
N01 C03 1.410(8) . ?
N01 C15 1.459(9) . ?
N01 C16 1.486(8) . ?
O01 C07 1.230(9) . ?
N02 C11 1.359(8) . ?
N02 C14 1.428(9) . ?
N02 H02 0.92(12) . ?
C04 C05 1.381(9) . ?
C04 C03 1.397(8) . ?
C04 H04 0.9300 . ?
C09 C10 1.362(8) . ?
C09 C08 1.403(9) . ?
C09 H09 0.9300 . ?
C03 C02 1.396(9) . ?
C05 C06 1.388(9) . ?
C05 H05 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C01 C02 1.376(9) . ?
C01 C06 1.408(9) . ?
C01 H01 0.9300 . ?
C07 C08 1.467(9) . ?
C07 C06 1.493(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
Br2 C10 1.962(6) . ?
Br1 C02 1.906(6) . ?
C11 C12 1.392(8) . ?
C11 C10 1.436(9) . ?
C08 C13 1.414(9) . ?
C12 C13 1.388(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
C03 N01 C15 117.3(5) . . ?
C03 N01 C16 115.5(5) . . ?
C15 N01 C16 110.0(5) . . ?
C11 N02 C14 122.8(5) . . ?
C11 N02 H02 120(7) . . ?
C14 N02 H02 117(7) . . ?
C05 C04 C03 121.8(6) . . ?
C05 C04 H04 119.1 . . ?
C03 C04 H04 119.1 . . ?
C10 C09 C08 122.0(6) . . ?
C10 C09 H09 119.0 . . ?
C08 C09 H09 119.0 . . ?
C02 C03 C04 116.4(6) . . ?
C02 C03 N01 121.3(5) . . ?
C04 C03 N01 122.2(6) . . ?
C04 C05 C06 121.0(6) . . ?
C04 C05 H05 119.5 . . ?
C06 C05 H05 119.5 . . ?
N01 C16 H16A 109.5 . . ?
N01 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N01 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C02 C01 C06 120.0(6) . . ?
C02 C01 H01 120.0 . . ?
C06 C01 H01 120.0 . . ?
O01 C07 C08 121.4(6) . . ?
O01 C07 C06 118.4(6) . . ?
C08 C07 C06 120.2(6) . . ?
N02 C14 H14A 109.5 . . ?
N02 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N02 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N01 C15 H15C 109.5 . . ?
N01 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
N01 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N02 C11 C12 122.6(6) . . ?
N02 C11 C10 121.5(5) . . ?
C12 C11 C10 115.9(5) . . ?
C01 C02 C03 122.5(6) . . ?
C01 C02 Br1 116.2(5) . . ?
C03 C02 Br1 121.2(5) . . ?
C09 C10 C11 121.6(5) . . ?
C09 C10 Br2 118.9(5) . . ?
C11 C10 Br2 119.5(4) . . ?
C09 C08 C13 117.3(5) . . ?
C09 C08 C07 118.9(6) . . ?
C13 C08 C07 123.4(6) . . ?
C13 C12 C11 122.8(6) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C05 C06 C01 118.1(6) . . ?
C05 C06 C07 124.0(6) . . ?
C01 C06 C07 117.5(6) . . ?
C12 C13 C08 120.3(6) . . ?
C12 C13 H13 119.8 . . ?
C08 C13 H13 119.8 . . ?

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
C05 C04 C03 C02 -3.5(9) . . . . ?
C05 C04 C03 N01 178.8(6) . . . . ?
C15 N01 C03 C02 -164.2(6) . . . . ?
C16 N01 C03 C02 63.7(8) . . . . ?
C15 N01 C03 C04 13.4(9) . . . . ?
C16 N01 C03 C04 -118.8(7) . . . . ?
C03 C04 C05 C06 -0.8(10) . . . . ?
C14 N02 C11 C12 -2.9(9) . . . . ?
C14 N02 C11 C10 176.2(6) . . . . ?
C06 C01 C02 C03 -5.7(9) . . . . ?
C06 C01 C02 Br1 171.6(5) . . . . ?
C04 C03 C02 C01 6.8(9) . . . . ?
N01 C03 C02 C01 -175.5(6) . . . . ?
C04 C03 C02 Br1 -170.4(4) . . . . ?
N01 C03 C02 Br1 7.3(8) . . . . ?
C08 C09 C10 C11 0.9(9) . . . . ?
C08 C09 C10 Br2 -179.2(5) . . . . ?
N02 C11 C10 C09 179.4(6) . . . . ?
C12 C11 C10 C09 -1.4(8) . . . . ?
N02 C11 C10 Br2 -0.5(7) . . . . ?
C12 C11 C10 Br2 178.7(4) . . . . ?
C10 C09 C08 C13 0.6(9) . . . . ?
C10 C09 C08 C07 173.9(6) . . . . ?
O01 C07 C08 C09 -6.1(11) . . . . ?
C06 C07 C08 C09 173.8(6) . . . . ?
O01 C07 C08 C13 166.7(7) . . . . ?
C06 C07 C08 C13 -13.3(10) . . . . ?
N02 C11 C12 C13 179.6(6) . . . . ?
C10 C11 C12 C13 0.4(9) . . . . ?
C04 C05 C06 C01 2.1(10) . . . . ?
C04 C05 C06 C07 -170.7(6) . . . . ?
C02 C01 C06 C05 1.1(9) . . . . ?
C02 C01 C06 C07 174.4(6) . . . . ?
O01 C07 C06 C05 131.3(8) . . . . ?
C08 C07 C06 C05 -48.6(10) . . . . ?
O01 C07 C06 C01 -41.5(10) . . . . ?
C08 C07 C06 C01 138.5(7) . . . . ?
C11 C12 C13 C08 1.1(10) . . . . ?
C09 C08 C13 C12 -1.6(9) . . . . ?
C07 C08 C13 C12 -174.6(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
C16 H16A Br1 0.96 2.65 3.292(7) 124.8 .
N02 H02 O01 0.92(12) 2.48(11) 3.140(7) 129(9) 4_565
N02 H02 Br2 0.92(12) 2.68(12) 3.159(5) 113(8) .

_refine_diff_density_max         2.146
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.186

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1531066'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 (4-(dimethylamino)-3-iodophenyl)(3-iodo-4-(methylamino)phenyl)methanone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 I2 N2 O'
_chemical_formula_sum            'C16 H16 I2 N2 O'
_chemical_formula_weight         506.11

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'
O O 0.0106 0.0060 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2967(5)
_cell_length_b                   9.6212(5)
_cell_length_c                   14.0625(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.740(2)
_cell_angle_gamma                90
_cell_volume                     1652.22(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   0.5919
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.807
_shelx_estimated_absorpt_T_min   0.488
_shelx_estimated_absorpt_T_max   0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71380
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4125
_reflns_number_gt                3517
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0185P)²+1.7164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4125
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0504
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
N01 N 0.69384(18) 0.4542(2) 0.07488(16) 0.0263(5) Uani 1 1 d . . . . .
N02 N 0.31315(16) 0.5019(2) -0.61430(14) 0.0237(4) Uani 1 1 d . . . . .
C15 C 0.3001(2) 0.6520(3) -0.6187(2) 0.0332(6) Uani 1 1 d . . . . .
H15A H 0.2326 0.6781 -0.5924 0.050 Uiso 1 1 calc R U . . .
H15B H 0.2960 0.6827 -0.6855 0.050 Uiso 1 1 calc R U . . .
H15C H 0.3628 0.6963 -0.5812 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7626(2) 0.5757(3) 0.0744(2) 0.0336(6) Uani 1 1 d . . . . .
H14A H 0.8148 0.5631 0.0276 0.050 Uiso 1 1 calc R U . . .
H14B H 0.8026 0.5890 0.1382 0.050 Uiso 1 1 calc R U . . .
H14C H 0.7170 0.6575 0.0571 0.050 Uiso 1 1 calc R U . . .
C16 C 0.2192(2) 0.4340(3) -0.66995(19) 0.0323(6) Uani 1 1 d . . . . .
H16A H 0.2219 0.3338 -0.6574 0.048 Uiso 1 1 calc R U . . .
H16B H 0.2220 0.4506 -0.7384 0.048 Uiso 1 1 calc R U . . .
H16C H 0.1510 0.4722 -0.6512 0.048 Uiso 1 1 calc R U . . .
H03 H 0.708(2) 0.401(3) 0.121(2) 0.024(7) Uiso 1 1 d . . . . .
I1 I 0.57419(2) 0.16708(2) 0.12561(2) 0.02860(5) Uani 1 1 d . . . . .
I2 I 0.42589(2) 0.19553(2) -0.63493(2) 0.03351(6) Uani 1 1 d . . . . .
C10 C 0.3416(2) 0.5174(3) -0.43862(17) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.3166 0.6109 -0.4418 0.031 Uiso 1 1 calc R U . . .
C02 C 0.56536(19) 0.2856(2) -0.00038(16) 0.0204(5) Uani 1 1 d . . . . .
C09 C 0.3730(2) 0.4584(3) -0.34971(17) 0.0266(5) Uani 1 1 d . . . . .
H09 H 0.3717 0.5125 -0.2933 0.032 Uiso 1 1 calc R U . . .
C12 C 0.38712(19) 0.3074(2) -0.51483(16) 0.0212(5) Uani 1 1 d . . . . .
C06 C 0.4939(2) 0.3084(2) -0.16689(17) 0.0236(5) Uani 1 1 d . . . . .
C01 C 0.4998(2) 0.2378(2) -0.07950(17) 0.0230(5) Uani 1 1 d . . . . .
H01 H 0.4579 0.1557 -0.0748 0.028 Uiso 1 1 calc R U . . .
C11 C 0.34571(18) 0.4438(2) -0.52375(16) 0.0207(5) Uani 1 1 d . . . . .
C04 C 0.62117(19) 0.4783(2) -0.09172(17) 0.0224(5) Uani 1 1 d . . . . .
H04 H 0.6617 0.5615 -0.0965 0.027 Uiso 1 1 calc R U . . .
C07 C 0.4291(3) 0.2442(3) -0.25053(18) 0.0356(6) Uani 1 1 d . . . . .
C08 C 0.4061(2) 0.3209(3) -0.34282(18) 0.0261(5) Uani 1 1 d . . . . .
C13 C 0.4132(2) 0.2463(3) -0.42650(17) 0.0246(5) Uani 1 1 d . . . . .
H13 H 0.4362 0.1520 -0.4227 0.029 Uiso 1 1 calc R U . . .
C03 C 0.62905(18) 0.4078(2) -0.00345(16) 0.0196(5) Uani 1 1 d . . . . .
C05 C 0.5561(2) 0.4297(2) -0.17151(17) 0.0240(5) Uani 1 1 d . . . . .
H05 H 0.5535 0.4791 -0.2302 0.029 Uiso 1 1 calc R U . . .
O01 O 0.3954(3) 0.1241(2) -0.24709(15) 0.0709(9) 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
N01 C03 1.357(3) . ?
N01 C14 1.443(3) . ?
N01 H03 0.83(3) . ?
N02 C11 1.405(3) . ?
N02 C15 1.453(3) . ?
N02 C16 1.471(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
I1 C02 2.099(2) . ?
I2 C12 2.104(2) . ?
C10 C09 1.386(3) . ?
C10 C11 1.397(3) . ?
C10 H10 0.9500 . ?
C02 C01 1.375(3) . ?
C02 C03 1.416(3) . ?
C09 C08 1.385(4) . ?
C09 H09 0.9500 . ?
C12 C13 1.378(3) . ?
C12 C11 1.408(3) . ?
C06 C01 1.399(3) . ?
C06 C05 1.401(3) . ?
C06 C07 1.476(3) . ?
C01 H01 0.9500 . ?
C04 C05 1.381(3) . ?
C04 C03 1.408(3) . ?
C04 H04 0.9500 . ?
C07 O01 1.230(3) . ?
C07 C08 1.491(3) . ?
C08 C13 1.390(3) . ?
C13 H13 0.9500 . ?
C05 H05 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
C03 N01 C14 123.5(2) . . ?
C03 N01 H03 118.5(19) . . ?
C14 N01 H03 116.1(19) . . ?
C11 N02 C15 116.9(2) . . ?
C11 N02 C16 115.3(2) . . ?
C15 N02 C16 110.1(2) . . ?
N02 C15 H15A 109.5 . . ?
N02 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N02 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N01 C14 H14A 109.5 . . ?
N01 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N01 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N02 C16 H16A 109.5 . . ?
N02 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N02 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C09 C10 C11 122.1(2) . . ?
C09 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C01 C02 C03 121.8(2) . . ?
C01 C02 I1 117.96(17) . . ?
C03 C02 I1 120.18(17) . . ?
C08 C09 C10 120.2(2) . . ?
C08 C09 H09 119.9 . . ?
C10 C09 H09 119.9 . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 I2 117.03(18) . . ?
C11 C12 I2 121.27(17) . . ?
C01 C06 C05 118.2(2) . . ?
C01 C06 C07 117.7(2) . . ?
C05 C06 C07 123.9(2) . . ?
C02 C01 C06 120.9(2) . . ?
C02 C01 H01 119.5 . . ?
C06 C01 H01 119.5 . . ?
C10 C11 N02 122.7(2) . . ?
C10 C11 C12 116.4(2) . . ?
N02 C11 C12 120.9(2) . . ?
C05 C04 C03 121.8(2) . . ?
C05 C04 H04 119.1 . . ?
C03 C04 H04 119.1 . . ?
O01 C07 C06 120.9(2) . . ?
O01 C07 C08 118.0(2) . . ?
C06 C07 C08 121.0(2) . . ?
C09 C08 C13 118.8(2) . . ?
C09 C08 C07 123.9(2) . . ?
C13 C08 C07 117.2(2) . . ?
C12 C13 C08 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C08 C13 H13 119.6 . . ?
N01 C03 C04 122.0(2) . . ?
N01 C03 C02 121.5(2) . . ?
C04 C03 C02 116.5(2) . . ?
C04 C05 C06 120.8(2) . . ?
C04 C05 H05 119.6 . . ?
C06 C05 H05 119.6 . . ?

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
C11 C10 C09 C08 -2.3(4) . . . . ?
C03 C02 C01 C06 0.3(4) . . . . ?
I1 C02 C01 C06 -177.18(18) . . . . ?
C05 C06 C01 C02 -0.4(4) . . . . ?
C07 C06 C01 C02 174.9(2) . . . . ?
C09 C10 C11 N02 179.3(2) . . . . ?
C09 C10 C11 C12 -2.2(4) . . . . ?
C15 N02 C11 C10 14.7(3) . . . . ?
C16 N02 C11 C10 -117.0(3) . . . . ?
C15 N02 C11 C12 -163.7(2) . . . . ?
C16 N02 C11 C12 64.6(3) . . . . ?
C13 C12 C11 C10 5.4(3) . . . . ?
I2 C12 C11 C10 -168.67(17) . . . . ?
C13 C12 C11 N02 -176.1(2) . . . . ?
I2 C12 C11 N02 9.8(3) . . . . ?
C01 C06 C07 O01 -10.6(4) . . . . ?
C05 C06 C07 O01 164.3(3) . . . . ?
C01 C06 C07 C08 171.7(2) . . . . ?
C05 C06 C07 C08 -13.3(4) . . . . ?
C10 C09 C08 C13 3.6(4) . . . . ?
C10 C09 C08 C07 -172.8(2) . . . . ?
O01 C07 C08 C09 137.5(3) . . . . ?
C06 C07 C08 C09 -44.7(4) . . . . ?
O01 C07 C08 C13 -38.9(4) . . . . ?
C06 C07 C08 C13 138.8(3) . . . . ?
C11 C12 C13 C08 -4.3(4) . . . . ?
I2 C12 C13 C08 170.05(19) . . . . ?
C09 C08 C13 C12 -0.3(4) . . . . ?
C07 C08 C13 C12 176.3(2) . . . . ?
C14 N01 C03 C04 -2.1(4) . . . . ?
C14 N01 C03 C02 178.1(2) . . . . ?
C05 C04 C03 N01 179.2(2) . . . . ?
C05 C04 C03 C02 -1.0(3) . . . . ?
C01 C02 C03 N01 -179.8(2) . . . . ?
I1 C02 C03 N01 -2.4(3) . . . . ?
C01 C02 C03 C04 0.4(3) . . . . ?
I1 C02 C03 C04 177.79(16) . . . . ?
C03 C04 C05 C06 0.9(4) . . . . ?
C01 C06 C05 C04 -0.2(4) . . . . ?
C07 C06 C05 C04 -175.2(3) . . . . ?

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
C16 H16A I2 0.98 2.82 3.417(3) 119.7 .
N01 H03 I1 0.83(3) 2.79(3) 3.249(2) 117(2) .
C01 H01 I1 0.95 3.20 4.035(2) 147.7 3_655

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.113

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_pv109_3
_database_code_depnum_ccdc_archive 'CCDC 1531065'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (3-iodo-4-(dimethylamino)phenyl)(4-(dimethylamino)phenyl)methanone
;
_chemical_name_common            
(3-iodo-4-(dimethylamino)phenyl)(4-(dimethylamino)phenyl)methanone
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 I N2 O'
_chemical_formula_sum            'C17 H19 I N2 O'
_chemical_formula_weight         394.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5382(5)
_cell_length_b                   9.6556(5)
_cell_length_c                   10.2314(5)
_cell_angle_alpha                72.585(2)
_cell_angle_beta                 68.506(2)
_cell_angle_gamma                67.819(2)
_cell_volume                     797.58(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      33.87

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    2.008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6663
_exptl_absorpt_correction_T_max  0.8244
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  2
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50383
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         33.87
_reflns_number_total             6372
_reflns_number_gt                5094
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.2496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6372
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N01 N 0.11825(18) 0.70537(16) 0.56332(15) 0.0238(3) Uani 1 1 d . . .
C15 C -0.0288(2) 0.6788(2) 0.5808(2) 0.0316(4) Uani 1 1 d . . .
H15A H -0.0665 0.6260 0.6786 0.047 Uiso 1 1 calc R . .
H15B H -0.0102 0.6160 0.5130 0.047 Uiso 1 1 calc R . .
H15C H -0.1085 0.7765 0.5624 0.047 Uiso 1 1 calc R . .
C14 C 0.2370(3) 0.5600(2) 0.5953(2) 0.0366(4) Uani 1 1 d . . .
H14A H 0.3312 0.5794 0.5939 0.055 Uiso 1 1 calc R . .
H14B H 0.2656 0.4986 0.5233 0.055 Uiso 1 1 calc R . .
H14C H 0.1933 0.5048 0.6902 0.055 Uiso 1 1 calc R . .
I01 I 0.419674(14) 0.841917(14) 0.405100(13) 0.03200(5) Uani 1 1 d . . .
C12 C -0.31321(19) 1.47987(17) 0.80928(17) 0.0190(3) Uani 1 1 d . . .
H12 H -0.3902 1.5101 0.7599 0.023 Uiso 1 1 calc R . .
C08 C -0.07225(18) 1.30121(17) 0.85801(16) 0.0185(3) Uani 1 1 d . . .
C10 C -0.21465(19) 1.51758(19) 0.97776(17) 0.0217(3) Uani 1 1 d . . .
H10 H -0.2250 1.5718 1.0461 0.026 Uiso 1 1 calc R . .
C09 C -0.08971(19) 1.38842(19) 0.95373(17) 0.0211(3) Uani 1 1 d . . .
H09 H -0.0128 1.3572 1.0034 0.025 Uiso 1 1 calc R . .
C01 C 0.07336(19) 1.17498(18) 0.82390(17) 0.0209(3) Uani 1 1 d . . .
O01 O 0.19431(15) 1.16706(16) 0.84666(15) 0.0307(3) Uani 1 1 d . . .
C04 C 0.22297(18) 0.89109(18) 0.58332(17) 0.0208(3) Uani 1 1 d . . .
C13 C -0.19000(18) 1.34871(18) 0.78899(17) 0.0190(3) Uani 1 1 d . . .
H13 H -0.1843 1.2891 0.7272 0.023 Uiso 1 1 calc R . .
C11 C -0.32832(18) 1.57084(17) 0.90161(16) 0.0186(3) Uani 1 1 d . . .
C05 C 0.10339(19) 0.82150(17) 0.62874(17) 0.0196(3) Uani 1 1 d . . .
C02 C 0.07700(18) 1.05621(17) 0.75614(17) 0.0195(3) Uani 1 1 d . . .
C03 C 0.21173(18) 1.00269(18) 0.64872(17) 0.0206(3) Uani 1 1 d . . .
H03 H 0.2973 1.0433 0.6198 0.025 Uiso 1 1 calc R . .
C06 C -0.0314(2) 0.87693(18) 0.73671(18) 0.0224(3) Uani 1 1 d . . .
H06 H -0.1155 0.8337 0.7688 0.027 Uiso 1 1 calc R . .
C07 C -0.04576(19) 0.99351(18) 0.79819(18) 0.0225(3) Uani 1 1 d . . .
H07 H -0.1401 1.0307 0.8695 0.027 Uiso 1 1 calc R . .
N02 N -0.44357(17) 1.70573(16) 0.91509(17) 0.0255(3) Uani 1 1 d . . .
C16 C -0.5550(2) 1.7634(2) 0.8319(2) 0.0298(4) Uani 1 1 d . . .
H16A H -0.4972 1.7676 0.7302 0.045 Uiso 1 1 calc R . .
H16B H -0.6225 1.8659 0.8483 0.045 Uiso 1 1 calc R . .
H16C H -0.6206 1.6959 0.8611 0.045 Uiso 1 1 calc R . .
C17 C -0.4603(2) 1.7935(2) 1.0148(2) 0.0361(4) Uani 1 1 d . . .
H17C H -0.4825 1.7342 1.1122 0.054 Uiso 1 1 calc R . .
H17A H -0.5476 1.8880 1.0084 0.054 Uiso 1 1 calc R . .
H17B H -0.3621 1.8181 0.9916 0.054 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N01 C05 1.409(2) . ?
N01 C15 1.458(2) . ?
N01 C14 1.469(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
I01 C04 2.0998(16) . ?
C12 C13 1.372(2) . ?
C12 C11 1.409(2) . ?
C12 H12 0.9500 . ?
C08 C09 1.401(2) . ?
C08 C13 1.403(2) . ?
C08 C01 1.469(2) . ?
C10 C09 1.372(2) . ?
C10 C11 1.416(2) . ?
C10 H10 0.9500 . ?
C09 H09 0.9500 . ?
C01 O01 1.229(2) . ?
C01 C02 1.492(2) . ?
C04 C03 1.383(2) . ?
C04 C05 1.404(2) . ?
C13 H13 0.9500 . ?
C11 N02 1.356(2) . ?
C05 C06 1.398(2) . ?
C02 C03 1.389(2) . ?
C02 C07 1.390(2) . ?
C03 H03 0.9500 . ?
C06 C07 1.388(2) . ?
C06 H06 0.9500 . ?
C07 H07 0.9500 . ?
N02 C17 1.443(2) . ?
N02 C16 1.447(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?

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
C05 N01 C15 115.81(15) . . ?
C05 N01 C14 114.91(15) . . ?
C15 N01 C14 109.94(15) . . ?
N01 C15 H15A 109.5 . . ?
N01 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N01 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N01 C14 H14A 109.5 . . ?
N01 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N01 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C12 C11 121.63(14) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C09 C08 C13 117.49(14) . . ?
C09 C08 C01 119.28(14) . . ?
C13 C08 C01 122.95(14) . . ?
C09 C10 C11 120.62(14) . . ?
C09 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C09 C08 121.93(15) . . ?
C10 C09 H09 119.0 . . ?
C08 C09 H09 119.0 . . ?
O01 C01 C08 121.27(15) . . ?
O01 C01 C02 118.98(15) . . ?
C08 C01 C02 119.72(14) . . ?
C03 C04 C05 121.35(15) . . ?
C03 C04 I01 116.64(12) . . ?
C05 C04 I01 121.89(11) . . ?
C12 C13 C08 121.05(14) . . ?
C12 C13 H13 119.5 . . ?
C08 C13 H13 119.5 . . ?
N02 C11 C12 122.05(15) . . ?
N02 C11 C10 120.83(14) . . ?
C12 C11 C10 117.10(14) . . ?
C06 C05 C04 116.90(14) . . ?
C06 C05 N01 122.36(15) . . ?
C04 C05 N01 120.70(15) . . ?
C03 C02 C07 118.56(15) . . ?
C03 C02 C01 118.23(14) . . ?
C07 C02 C01 123.19(15) . . ?
C04 C03 C02 120.88(15) . . ?
C04 C03 H03 119.6 . . ?
C02 C03 H03 119.6 . . ?
C07 C06 C05 121.73(15) . . ?
C07 C06 H06 119.1 . . ?
C05 C06 H06 119.1 . . ?
C06 C07 C02 120.44(15) . . ?
C06 C07 H07 119.8 . . ?
C02 C07 H07 119.8 . . ?
C11 N02 C17 120.86(15) . . ?
C11 N02 C16 120.73(14) . . ?
C17 N02 C16 118.40(15) . . ?
N02 C16 H16A 109.5 . . ?
N02 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N02 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N02 C17 H17C 109.5 . . ?
N02 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
N02 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?

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
C11 C10 C09 C08 -2.4(3) . . . . ?
C13 C08 C09 C10 -1.4(2) . . . . ?
C01 C08 C09 C10 172.70(15) . . . . ?
C09 C08 C01 O01 -18.7(2) . . . . ?
C13 C08 C01 O01 155.15(17) . . . . ?
C09 C08 C01 C02 163.26(15) . . . . ?
C13 C08 C01 C02 -22.9(2) . . . . ?
C11 C12 C13 C08 -1.1(2) . . . . ?
C09 C08 C13 C12 3.2(2) . . . . ?
C01 C08 C13 C12 -170.73(15) . . . . ?
C13 C12 C11 N02 175.51(15) . . . . ?
C13 C12 C11 C10 -2.8(2) . . . . ?
C09 C10 C11 N02 -173.82(16) . . . . ?
C09 C10 C11 C12 4.5(2) . . . . ?
C03 C04 C05 C06 3.9(2) . . . . ?
I01 C04 C05 C06 -171.97(12) . . . . ?
C03 C04 C05 N01 -178.46(15) . . . . ?
I01 C04 C05 N01 5.7(2) . . . . ?
C15 N01 C05 C06 18.3(2) . . . . ?
C14 N01 C05 C06 -111.65(19) . . . . ?
C15 N01 C05 C04 -159.19(15) . . . . ?
C14 N01 C05 C04 70.9(2) . . . . ?
O01 C01 C02 C03 -38.5(2) . . . . ?
C08 C01 C02 C03 139.58(16) . . . . ?
O01 C01 C02 C07 139.49(18) . . . . ?
C08 C01 C02 C07 -42.4(2) . . . . ?
C05 C04 C03 C02 -3.9(2) . . . . ?
I01 C04 C03 C02 172.16(12) . . . . ?
C07 C02 C03 C04 1.0(2) . . . . ?
C01 C02 C03 C04 179.07(15) . . . . ?
C04 C05 C06 C07 -1.1(2) . . . . ?
N01 C05 C06 C07 -178.67(15) . . . . ?
C05 C06 C07 C02 -1.8(3) . . . . ?
C03 C02 C07 C06 1.8(2) . . . . ?
C01 C02 C07 C06 -176.17(15) . . . . ?
C12 C11 N02 C17 177.41(17) . . . . ?
C10 C11 N02 C17 -4.4(2) . . . . ?
C12 C11 N02 C16 -1.2(2) . . . . ?
C10 C11 N02 C16 176.99(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        33.87
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.270
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.113
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
