# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1819612'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Br N O2'
_chemical_formula_sum            'C14 H10 Br N O2'
_chemical_formula_weight         304.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   3.87870(10)
_cell_length_b                   13.3741(4)
_cell_length_c                   26.3417(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.45(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5072
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      66.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1258
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    4.053
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6591
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.355
_diffrn_reflns_theta_max         66.568
_diffrn_reflns_theta_full        66.568
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2395
_reflns_number_gt                2255
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.977

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1375P)²+2.0362P] 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_abs_structure_details 
;
 Flack x determined using 841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     167
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.1433(3) 0.48047(9) 0.08288(3) 0.0495(5) Uani 1 1 d . U . . .
O1 O 0.209(2) 0.3544(5) 0.3128(3) 0.0527(19) Uani 1 1 d . U . . .
C1 C 0.024(2) 0.5041(7) 0.1499(3) 0.0398(19) Uani 1 1 d . U . . .
O2 O 0.520(2) 0.7139(5) 0.2987(2) 0.0411(16) Uani 1 1 d . U . . .
C2 C 0.183(3) 0.5927(7) 0.1614(3) 0.0385(18) Uani 1 1 d . U . . .
H2 H 0.2080 0.6427 0.1361 0.046 Uiso 1 1 calc R U . . .
C3 C 0.309(2) 0.6095(7) 0.2102(3) 0.0341(17) Uani 1 1 d . U . . .
H3 H 0.4158 0.6715 0.2182 0.041 Uiso 1 1 calc R U . . .
N1 N 0.409(2) 0.5467(5) 0.2967(3) 0.0329(14) Uani 1 1 d . U . . .
C4 C 0.279(2) 0.5359(6) 0.2473(3) 0.0293(15) Uani 1 1 d . U . . .
C5 C 0.123(2) 0.4434(7) 0.2348(3) 0.0333(15) Uani 1 1 d . U . . .
C6 C -0.007(2) 0.4273(8) 0.1855(3) 0.0378(16) Uani 1 1 d . U . . .
H6 H -0.1142 0.3657 0.1767 0.045 Uiso 1 1 calc R U . . .
C7 C 0.088(3) 0.3586(7) 0.2697(4) 0.0403(19) Uani 1 1 d . U . . .
H7 H -0.0379 0.3022 0.2581 0.048 Uiso 1 1 calc R U . . .
C8 C 0.530(2) 0.6311(6) 0.3190(3) 0.0302(16) Uani 1 1 d . U . . .
C9 C 0.683(2) 0.6175(6) 0.3712(3) 0.0284(15) Uani 1 1 d . U . . .
C14 C 0.752(3) 0.5250(8) 0.3934(3) 0.0404(18) Uani 1 1 d . U . . .
H14 H 0.6963 0.4648 0.3761 0.048 Uiso 1 1 calc R U . . .
C13 C 0.902(3) 0.5218(9) 0.4407(4) 0.049(2) Uani 1 1 d . U . . .
H13 H 0.9494 0.4587 0.4558 0.058 Uiso 1 1 calc R U . . .
C12 C 0.985(3) 0.6081(9) 0.4668(3) 0.044(2) Uani 1 1 d . U . . .
H12 H 1.0901 0.6045 0.4993 0.053 Uiso 1 1 calc R U . . .
C11 C 0.913(3) 0.6997(8) 0.4450(3) 0.0407(19) Uani 1 1 d . U . . .
H11 H 0.9693 0.7592 0.4628 0.049 Uiso 1 1 calc R U . . .
C10 C 0.763(2) 0.7060(7) 0.3978(3) 0.0351(18) Uani 1 1 d . U . . .
H10 H 0.7125 0.7694 0.3833 0.042 Uiso 1 1 calc R U . . .
H1A H 0.41(2) 0.481(6) 0.317(3) 0.012(17) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.908(9) . ?
O1 C7 1.229(13) . ?
C1 C2 1.371(13) . ?
C1 C6 1.396(14) . ?
O2 C8 1.230(11) . ?
C2 C3 1.393(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(13) . ?
C3 H3 0.9500 . ?
N1 C8 1.356(11) . ?
N1 C4 1.404(11) . ?
N1 H1A 1.03(7) . ?
C4 C5 1.416(12) . ?
C5 C6 1.411(12) . ?
C5 C7 1.467(13) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.509(12) . ?
C9 C14 1.395(13) . ?
C9 C10 1.411(12) . ?
C14 C13 1.374(15) . ?
C14 H14 0.9500 . ?
C13 C12 1.381(17) . ?
C13 H13 0.9500 . ?
C12 C11 1.381(16) . ?
C12 H12 0.9500 . ?
C11 C10 1.376(14) . ?
C11 H11 0.9500 . ?
C10 H10 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
C2 C1 C6 121.9(8) . . ?
C2 C1 Br1 120.1(7) . . ?
C6 C1 Br1 118.0(7) . . ?
C1 C2 C3 120.1(9) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.3(8) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C8 N1 C4 127.6(8) . . ?
C8 N1 H1A 119(4) . . ?
C4 N1 H1A 113(4) . . ?
C3 C4 N1 123.3(8) . . ?
C3 C4 C5 119.4(7) . . ?
N1 C4 C5 117.3(8) . . ?
C6 C5 C4 120.0(8) . . ?
C6 C5 C7 115.2(8) . . ?
C4 C5 C7 124.7(7) . . ?
C1 C6 C5 118.3(8) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C5 125.4(9) . . ?
O1 C7 H7 117.3 . . ?
C5 C7 H7 117.3 . . ?
O2 C8 N1 123.4(8) . . ?
O2 C8 C9 121.1(8) . . ?
N1 C8 C9 115.4(7) . . ?
C14 C9 C10 119.5(8) . . ?
C14 C9 C8 124.5(8) . . ?
C10 C9 C8 116.0(8) . . ?
C13 C14 C9 119.3(9) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
C14 C13 C12 121.5(10) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C11 C12 C13 119.2(8) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C10 C11 C12 121.1(9) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C10 C9 119.4(9) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?

_refine_diff_density_max         2.609
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.237

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1819622'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C18 H13 N O2'
_chemical_formula_sum            ' C18 H12 N O2'
_chemical_formula_weight         275.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.6111(3)
_cell_length_b                   8.5608(2)
_cell_length_c                   26.6519(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2649.21(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      4.98
_cell_measurement_theta_max      66.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             22
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.727
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24111
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         6.644
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_full        66.593
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2320
_reflns_number_gt                2208
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0526P)²+0.3761P] 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         2320
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O1 O 0.54898(7) 0.72716(9) 0.39721(3) 0.0474(2) Uani 1 1 d . . . . .
N1 N 0.37652(8) 0.52616(11) 0.40104(3) 0.0413(2) Uani 1 1 d . . . . .
C1 C 0.43850(11) 0.49682(15) 0.29705(4) 0.0529(3) Uani 1 1 d . . . . .
H1 H 0.4842 0.5639 0.3173 0.064 Uiso 1 1 calc R U . . .
O2 O 0.21597(8) 0.37930(11) 0.38611(3) 0.0600(3) Uani 1 1 d . . . . .
C2 C 0.46751(13) 0.47392(16) 0.24714(5) 0.0606(3) Uani 1 1 d . . . . .
H2 H 0.5324 0.5260 0.2334 0.073 Uiso 1 1 calc R U . . .
C3 C 0.40258(15) 0.37586(17) 0.21740(5) 0.0675(4) Uani 1 1 d . . . . .
H3 H 0.4225 0.3603 0.1832 0.081 Uiso 1 1 calc R U . . .
C4 C 0.30874(16) 0.30076(18) 0.23763(5) 0.0736(4) Uani 1 1 d . . . . .
H4 H 0.2644 0.2321 0.2174 0.088 Uiso 1 1 calc R U . . .
C5 C 0.27825(12) 0.32427(16) 0.28734(5) 0.0612(3) Uani 1 1 d . . . . .
H5 H 0.2126 0.2729 0.3007 0.073 Uiso 1 1 calc R U . . .
C6 C 0.34315(10) 0.42255(13) 0.31773(4) 0.0466(3) Uani 1 1 d . . . . .
C7 C 0.30487(10) 0.43959(13) 0.37135(4) 0.0447(3) Uani 1 1 d . . . . .
C8 C 0.36706(8) 0.56091(12) 0.45173(4) 0.0381(2) Uani 1 1 d . . . . .
C9 C 0.28687(9) 0.48220(12) 0.48303(4) 0.0405(3) Uani 1 1 d . . . . .
H9 H 0.2374 0.4049 0.4692 0.049 Uiso 1 1 calc R U . . .
C10 C 0.28085(9) 0.51734(12) 0.53273(4) 0.0414(3) Uani 1 1 d . . . . .
H10 H 0.2269 0.4631 0.5531 0.050 Uiso 1 1 calc R U . . .
C11 C 0.35209(9) 0.63197(12) 0.55528(4) 0.0395(3) Uani 1 1 d . . . . .
C12 C 0.34281(10) 0.66652(13) 0.60703(4) 0.0455(3) Uani 1 1 d . . . . .
H12 H 0.2871 0.6136 0.6268 0.055 Uiso 1 1 calc R U . . .
C13 C 0.41290(11) 0.77487(14) 0.62886(4) 0.0491(3) Uani 1 1 d . . . . .
H13 H 0.4056 0.7980 0.6636 0.059 Uiso 1 1 calc R U . . .
C14 C 0.49587(10) 0.85196(13) 0.59970(4) 0.0469(3) Uani 1 1 d . . . . .
H14 H 0.5451 0.9267 0.6150 0.056 Uiso 1 1 calc R U . . .
C15 C 0.50712(9) 0.82124(12) 0.54948(4) 0.0426(3) Uani 1 1 d . . . . .
H15 H 0.5642 0.8749 0.5306 0.051 Uiso 1 1 calc R U . . .
C16 C 0.43500(9) 0.71050(11) 0.52506(4) 0.0379(3) Uani 1 1 d . . . . .
C17 C 0.44186(8) 0.67298(12) 0.47230(4) 0.0377(2) Uani 1 1 d . . . . .
C18 C 0.52749(9) 0.75211(13) 0.44138(4) 0.0430(3) Uani 1 1 d . . . . .
H18 H 0.5713 0.8317 0.4573 0.052 Uiso 1 1 calc R U . . .
H1A H 0.4347(12) 0.5793(17) 0.3867(5) 0.055(4) Uiso 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
O1 C18 1.2220(14) . ?
N1 C7 1.3666(14) . ?
N1 C8 1.3877(14) . ?
N1 H1A 0.900(15) . ?
C1 C2 1.3862(17) . ?
C1 C6 1.3906(18) . ?
C1 H1 0.9500 . ?
O2 C7 1.2192(14) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3899(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.5036(16) . ?
C8 C17 1.4054(15) . ?
C8 C9 1.4202(14) . ?
C9 C10 1.3601(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4172(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.4147(15) . ?
C11 C16 1.4240(15) . ?
C12 C13 1.3642(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4027(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3702(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4226(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.4444(15) . ?
C17 C18 1.4584(15) . ?
C18 H18 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
C7 N1 C8 129.18(10) . . ?
C7 N1 H1A 119.1(8) . . ?
C8 N1 H1A 111.3(9) . . ?
C2 C1 C6 120.60(12) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.33(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.49(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.62(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.43(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.52(12) . . ?
C5 C6 C7 116.89(11) . . ?
C1 C6 C7 124.59(10) . . ?
O2 C7 N1 123.93(11) . . ?
O2 C7 C6 121.05(10) . . ?
N1 C7 C6 115.02(10) . . ?
N1 C8 C17 118.51(9) . . ?
N1 C8 C9 121.47(9) . . ?
C17 C8 C9 119.98(10) . . ?
C10 C9 C8 120.06(10) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 122.42(10) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 120.92(10) . . ?
C12 C11 C16 120.28(10) . . ?
C10 C11 C16 118.79(10) . . ?
C13 C12 C11 120.83(11) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.56(11) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 121.09(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.24(10) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 116.99(10) . . ?
C15 C16 C17 124.14(9) . . ?
C11 C16 C17 118.87(9) . . ?
C8 C17 C16 119.84(9) . . ?
C8 C17 C18 121.18(10) . . ?
C16 C17 C18 118.98(9) . . ?
O1 C18 C17 127.05(10) . . ?
O1 C18 H18 116.5 . . ?
C17 C18 H18 116.5 . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028

