# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_20161123-mdl-mxp-3-135
_database_code_depnum_ccdc_archive 'CCDC 1572350'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.
2017-10-31 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         ?
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40

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'

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

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

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

_cell_length_a                   9.2362(9)
_cell_length_b                   9.2949(8)
_cell_length_c                   10.8564(9)
_cell_angle_alpha                89.518(7)
_cell_angle_beta                 83.330(8)
_cell_angle_gamma                80.219(8)
_cell_volume                     912.19(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3236
_cell_measurement_theta_min      3.4330
_cell_measurement_theta_max      27.8310

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12054
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.316
_diffrn_reflns_theta_max         28.577
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4243
_reflns_number_gt                3183
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4243
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.33005(14) 0.40812(15) 0.05963(10) 0.0431(3) Uani 1 1 d . . . . .
O2 O 0.57526(14) 0.47662(16) 0.34369(13) 0.0540(4) Uani 1 1 d . . . . .
N1 N 0.11779(16) 0.63092(15) 0.36363(13) 0.0378(3) Uani 1 1 d . . . . .
H1 H 0.0241 0.6339 0.3809 0.045 Uiso 1 1 d R U . . .
C1 C 0.18912(19) 0.38701(18) 0.10138(15) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.1112(2) 0.33328(19) 0.01476(16) 0.0445(4) Uani 1 1 d . . . . .
H2 H 0.1561 0.3120 -0.0657 0.053 Uiso 1 1 calc R U . . .
C3 C -0.0312(2) 0.3116(2) 0.04752(19) 0.0496(5) Uani 1 1 d . . . . .
H3 H -0.0828 0.2758 -0.0108 0.060 Uiso 1 1 calc R U . . .
C4 C -0.0982(2) 0.3427(2) 0.1666(2) 0.0490(5) Uani 1 1 d . . . . .
H4 H -0.1950 0.3283 0.1889 0.059 Uiso 1 1 calc R U . . .
C5 C -0.0207(2) 0.3954(2) 0.25291(17) 0.0434(4) Uani 1 1 d . . . . .
H5 H -0.0662 0.4151 0.3334 0.052 Uiso 1 1 calc R U . . .
C6 C 0.12365(18) 0.41958(18) 0.22225(14) 0.0344(4) Uani 1 1 d . . . . .
C7 C 0.20125(17) 0.48658(17) 0.31901(14) 0.0327(4) Uani 1 1 d . . . . .
C8 C 0.15735(19) 0.73534(18) 0.27818(15) 0.0364(4) Uani 1 1 d . . . . .
C9 C 0.0838(2) 0.8758(2) 0.26065(19) 0.0463(5) Uani 1 1 d . . . . .
H9 H -0.0071 0.9110 0.3057 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1499(2) 0.9615(2) 0.1741(2) 0.0553(5) Uani 1 1 d . . . . .
H10 H 0.1017 1.0556 0.1605 0.066 Uiso 1 1 calc R U . . .
C11 C 0.2854(2) 0.9115(2) 0.1073(2) 0.0544(5) Uani 1 1 d . . . . .
H11 H 0.3276 0.9722 0.0504 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3589(2) 0.7712(2) 0.12490(17) 0.0441(4) Uani 1 1 d . . . . .
H12 H 0.4505 0.7368 0.0808 0.053 Uiso 1 1 calc R U . . .
C13 C 0.29237(18) 0.68345(18) 0.20970(15) 0.0343(4) Uani 1 1 d . . . . .
C14 C 0.34755(17) 0.53079(18) 0.25310(14) 0.0331(4) Uani 1 1 d . . . . .
C15 C 0.4533(2) 0.5453(2) 0.34708(16) 0.0403(4) Uani 1 1 d . . . . .
H15 H 0.4211 0.6123 0.4118 0.048 Uiso 1 1 calc R U . . .
C16 C 0.42137(19) 0.4195(2) 0.15491(15) 0.0391(4) Uani 1 1 d . . . . .
H16A H 0.5136 0.4470 0.1185 0.047 Uiso 1 1 calc R U . . .
H16B H 0.4445 0.3250 0.1932 0.047 Uiso 1 1 calc R U . . .
C17 C 0.23019(19) 0.38715(19) 0.42730(14) 0.0364(4) Uani 1 1 d . . . . .
H17 H 0.2449 0.4305 0.5007 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2365(2) 0.2442(2) 0.42728(16) 0.0409(4) Uani 1 1 d . . . . .
H18 H 0.2152 0.2021 0.3555 0.049 Uiso 1 1 calc R U . . .
C19 C 0.2738(2) 0.1448(2) 0.52916(16) 0.0409(4) Uani 1 1 d . . . . .
C20 C 0.2820(3) -0.0036(2) 0.5115(2) 0.0614(6) Uani 1 1 d . . . . .
H20 H 0.2660 -0.0386 0.4351 0.074 Uiso 1 1 calc R U . . .
C21 C 0.3135(3) -0.1008(2) 0.6055(2) 0.0764(8) Uani 1 1 d . . . . .
H21 H 0.3172 -0.2001 0.5921 0.092 Uiso 1 1 calc R U . . .
C22 C 0.3391(3) -0.0523(3) 0.7177(2) 0.0651(6) Uani 1 1 d . . . . .
H22 H 0.3606 -0.1181 0.7808 0.078 Uiso 1 1 calc R U . . .
C23 C 0.3331(2) 0.0944(3) 0.73708(19) 0.0568(5) Uani 1 1 d . . . . .
H23 H 0.3518 0.1278 0.8132 0.068 Uiso 1 1 calc R U . . .
C24 C 0.2994(2) 0.1930(2) 0.64415(18) 0.0481(5) Uani 1 1 d . . . . .
H24 H 0.2938 0.2923 0.6588 0.058 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
O1 C1 1.374(2) . ?
O1 C16 1.424(2) . ?
O2 C15 1.194(2) . ?
N1 C8 1.401(2) . ?
N1 C7 1.484(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.371(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.392(2) . ?
C6 C7 1.531(2) . ?
C7 C17 1.509(2) . ?
C7 C14 1.570(2) . ?
C8 C9 1.388(2) . ?
C8 C13 1.388(2) . ?
C9 C10 1.382(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.384(2) . ?
C13 C14 1.515(2) . ?
C14 C16 1.510(2) . ?
C14 C15 1.514(2) . ?
C17 C18 1.320(2) . ?
C18 C19 1.469(2) . ?
C19 C20 1.383(3) . ?
C19 C24 1.389(3) . ?
C20 C21 1.380(3) . ?
C21 C22 1.363(4) . ?
C22 C23 1.372(3) . ?
C23 C24 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C16 114.62(12) . . ?
C8 N1 C7 107.48(13) . . ?
O1 C1 C2 116.28(15) . . ?
O1 C1 C6 123.09(15) . . ?
C2 C1 C6 120.62(17) . . ?
C3 C2 C1 120.32(17) . . ?
C2 C3 C4 120.11(17) . . ?
C3 C4 C5 119.62(18) . . ?
C4 C5 C6 121.62(17) . . ?
C5 C6 C1 117.71(15) . . ?
C5 C6 C7 119.53(14) . . ?
C1 C6 C7 122.70(15) . . ?
N1 C7 C17 110.25(13) . . ?
N1 C7 C6 111.55(13) . . ?
C17 C7 C6 112.80(14) . . ?
N1 C7 C14 101.11(12) . . ?
C17 C7 C14 111.83(12) . . ?
C6 C7 C14 108.70(12) . . ?
C9 C8 C13 120.56(17) . . ?
C9 C8 N1 128.77(17) . . ?
C13 C8 N1 110.61(14) . . ?
C10 C9 C8 117.87(18) . . ?
C11 C10 C9 121.86(18) . . ?
C10 C11 C12 120.24(18) . . ?
C13 C12 C11 118.37(18) . . ?
C12 C13 C8 121.08(16) . . ?
C12 C13 C14 130.51(16) . . ?
C8 C13 C14 108.25(14) . . ?
C16 C14 C15 109.62(14) . . ?
C16 C14 C13 117.09(14) . . ?
C15 C14 C13 106.86(13) . . ?
C16 C14 C7 110.95(13) . . ?
C15 C14 C7 110.34(13) . . ?
C13 C14 C7 101.64(12) . . ?
O2 C15 C14 124.36(17) . . ?
O1 C16 C14 112.00(13) . . ?
C18 C17 C7 125.91(15) . . ?
C17 C18 C19 126.56(17) . . ?
C20 C19 C24 117.92(17) . . ?
C20 C19 C18 119.05(17) . . ?
C24 C19 C18 123.02(17) . . ?
C21 C20 C19 121.1(2) . . ?
C22 C21 C20 120.5(2) . . ?
C21 C22 C23 119.52(19) . . ?
C22 C23 C24 120.5(2) . . ?
C23 C24 C19 120.52(19) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1573973'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_audit_creation_date             2017-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H17 Br2 N O2'
_chemical_formula_sum            'C24 H17 Br2 N O2'
_chemical_formula_weight         511.21
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8958(12)
_cell_length_b                   18.729(2)
_cell_length_c                   13.2336(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.186(2)
_cell_angle_gamma                90.00
_cell_volume                     2094.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.216
_cell_measurement_theta_min      2.718
_exptl_absorpt_coefficient_mu    3.890
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            light
_exptl_crystal_colour_modifier   light
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18359
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.95
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2740
_reflns_number_total             4305
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.284
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     281
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0844P)²+3.4632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1810
_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 > 2sigma(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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), N1(H1), C8(H8), C1(H1A), C14(H14), C18(H18), C11(H11), C3(H3),
 C13(H13), C22(H22), C23(H23), C24(H24), C20(H20), C21(H21), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br2 Br 0.88482(9) 0.19952(4) 0.39965(5) 0.0695(3) Uani 1 d . . . U
Br1 Br 0.70300(15) -0.07094(4) 0.20730(8) 0.1125(5) Uani 1 d . . . U
O2 O 0.6751(5) 0.1617(3) -0.1509(3) 0.0681(12) Uani 1 d . . . U
C17 C 0.9305(7) 0.2879(3) -0.0002(4) 0.0472(11) Uani 1 d . . . U
H17 H 0.9578 0.2880 -0.0626 0.057 Uiso 1 calc . . R .
N1 N 0.9328(5) 0.2274(2) 0.1684(3) 0.0387(9) Uani 1 d . . . U
H1 H 0.9325 0.2655 0.2045 0.046 Uiso 1 calc . . R .
C6 C 0.8624(6) 0.1135(3) 0.1067(4) 0.0408(10) Uani 1 d . . . U
C8 C 0.7245(7) 0.1744(3) -0.0581(4) 0.0497(12) Uani 1 d . . . U
H8 H 0.6581 0.1987 -0.0278 0.060 Uiso 1 calc . . R .
C15 C 1.1567(6) 0.2128(3) 0.0964(4) 0.0434(10) Uani 1 d . . . U
O1 O 1.1327(5) 0.0944(2) 0.0205(3) 0.0592(10) Uani 1 d . . . U
C5 C 0.8905(6) 0.1597(3) 0.1928(4) 0.0383(9) Uani 1 d . . . U
C4 C 0.8620(7) 0.1365(3) 0.2845(4) 0.0491(11) Uani 1 d . . . U
C16 C 0.9787(6) 0.2231(3) 0.0695(4) 0.0391(9) Uani 1 d . . . U
C1 C 0.8061(7) 0.0455(3) 0.1087(4) 0.0503(12) Uani 1 d . . . U
H1A H 0.7860 0.0154 0.0500 0.060 Uiso 1 calc . . R .
C7 C 0.8870(6) 0.1541(3) 0.0141(4) 0.0413(9) Uani 1 d . . . U
C2 C 0.7805(9) 0.0235(3) 0.2021(5) 0.0614(13) Uani 1 d . . . U
C14 C 1.2557(7) 0.2676(4) 0.1465(5) 0.0558(12) Uani 1 d . . . U
H14 H 1.2127 0.3099 0.1619 0.067 Uiso 1 calc . . R .
C19 C 0.8130(10) 0.4080(4) -0.0507(5) 0.0733(14) Uani 1 d . . . U
C9 C 0.9806(7) 0.1141(3) -0.0467(4) 0.0503(11) Uani 1 d . . . U
H9A H 0.9229 0.0716 -0.0785 0.060 Uiso 1 calc . . R .
H9B H 0.9917 0.1442 -0.1036 0.060 Uiso 1 calc . . R .
C18 C 0.8548(8) 0.3441(3) 0.0169(5) 0.0571(13) Uani 1 d . . . U
H18 H 0.8243 0.3436 0.0779 0.069 Uiso 1 calc . . R .
C10 C 1.2222(7) 0.1508(3) 0.0707(5) 0.0534(11) Uani 1 d . . . U
C11 C 1.3874(8) 0.1442(4) 0.0980(5) 0.0679(14) Uani 1 d . . . U
H11 H 1.4328 0.1029 0.0812 0.082 Uiso 1 calc . . R .
C3 C 0.8056(8) 0.0682(3) 0.2883(5) 0.0605(13) Uani 1 d . . . U
H3 H 0.7844 0.0524 0.3492 0.073 Uiso 1 calc . . R .
C13 C 1.4193(8) 0.2602(4) 0.1743(5) 0.0679(14) Uani 1 d . . . U
H13 H 1.4852 0.2969 0.2097 0.081 Uiso 1 calc . . R .
C22 C 0.7263(13) 0.5301(4) -0.1746(7) 0.102(2) Uani 1 d . . . U
H22 H 0.7050 0.5729 -0.2122 0.122 Uiso 1 calc . . R .
C23 C 0.7996(13) 0.4780(5) -0.2060(7) 0.108(2) Uani 1 d . . . U
H23 H 0.8236 0.4825 -0.2692 0.129 Uiso 1 calc . . R .
C24 C 0.8424(13) 0.4155(4) -0.1453(7) 0.0981(18) Uani 1 d . . . U
H24 H 0.8916 0.3786 -0.1700 0.118 Uiso 1 calc . . R .
C20 C 0.7247(12) 0.4591(4) -0.0269(7) 0.0949(18) Uani 1 d . . . U
H20 H 0.6901 0.4533 0.0321 0.114 Uiso 1 calc . . R .
C21 C 0.6830(13) 0.5207(4) -0.0879(7) 0.106(2) Uani 1 d . . . U
H21 H 0.6240 0.5558 -0.0679 0.127 Uiso 1 calc . . R .
C12 C 1.4810(9) 0.2001(5) 0.1501(6) 0.0737(15) Uani 1 d . . . U
H12 H 1.5905 0.1957 0.1689 0.088 Uiso 1 calc . . R .


_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
Br2 C4 1.888(5) . ?
Br1 C2 1.908(6) . ?
O2 C8 1.192(6) . ?
C17 C16 1.503(7) . ?
C17 C18 1.306(8) . ?
N1 C5 1.389(7) . ?
N1 C16 1.490(6) . ?
C6 C5 1.389(7) . ?
C6 C1 1.373(8) . ?
C6 C7 1.514(7) . ?
C8 C7 1.511(8) . ?
C15 C16 1.523(8) . ?
C15 C14 1.379(8) . ?
C15 C10 1.388(8) . ?
O1 C9 1.417(7) . ?
O1 C10 1.366(8) . ?
C5 C4 1.385(7) . ?
C4 C3 1.381(8) . ?
C16 C7 1.581(7) . ?
C1 C2 1.387(8) . ?
C7 C9 1.523(7) . ?
C2 C3 1.376(8) . ?
C14 C13 1.392(9) . ?
C19 C18 1.471(8) . ?
C19 C24 1.365(10) . ?
C19 C20 1.336(11) . ?
C10 C11 1.405(9) . ?
C11 C12 1.380(10) . ?
C13 C12 1.335(10) . ?
C22 C23 1.312(12) . ?
C22 C21 1.331(13) . ?
C23 C24 1.403(11) . ?
C20 C21 1.390(11) . ?

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
C18 C17 C16 127.4(5) . . ?
C5 N1 C16 108.9(4) . . ?
C5 C6 C7 108.5(4) . . ?
C1 C6 C5 122.3(5) . . ?
C1 C6 C7 128.9(5) . . ?
O2 C8 C7 125.0(6) . . ?
C14 C15 C16 118.7(5) . . ?
C14 C15 C10 119.0(5) . . ?
C10 C15 C16 122.3(5) . . ?
C10 O1 C9 113.6(4) . . ?
C6 C5 N1 111.7(4) . . ?
C4 C5 N1 128.8(5) . . ?
C4 C5 C6 119.3(5) . . ?
C5 C4 Br2 120.6(4) . . ?
C3 C4 Br2 119.9(4) . . ?
C3 C4 C5 119.4(5) . . ?
C17 C16 C15 108.8(4) . . ?
C17 C16 C7 111.6(4) . . ?
N1 C16 C17 113.1(4) . . ?
N1 C16 C15 110.6(4) . . ?
N1 C16 C7 102.0(4) . . ?
C15 C16 C7 110.7(4) . . ?
C6 C1 C2 117.0(5) . . ?
C6 C7 C16 102.7(4) . . ?
C6 C7 C9 114.9(4) . . ?
C8 C7 C6 106.7(4) . . ?
C8 C7 C16 109.9(4) . . ?
C8 C7 C9 111.2(4) . . ?
C9 C7 C16 111.0(4) . . ?
C1 C2 Br1 117.9(5) . . ?
C3 C2 Br1 120.1(5) . . ?
C3 C2 C1 122.0(6) . . ?
C15 C14 C13 120.7(6) . . ?
C24 C19 C18 123.8(6) . . ?
C20 C19 C18 119.7(7) . . ?
C20 C19 C24 116.0(7) . . ?
O1 C9 C7 111.7(4) . . ?
C17 C18 C19 126.7(6) . . ?
C15 C10 C11 119.8(6) . . ?
O1 C10 C15 122.8(5) . . ?
O1 C10 C11 117.4(6) . . ?
C12 C11 C10 118.7(7) . . ?
C2 C3 C4 119.9(5) . . ?
C12 C13 C14 119.7(7) . . ?
C23 C22 C21 118.6(8) . . ?
C22 C23 C24 120.9(9) . . ?
C19 C24 C23 121.0(8) . . ?
C19 C20 C21 121.8(9) . . ?
C22 C21 C20 121.0(9) . . ?
C13 C12 C11 122.0(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zzzz
_database_code_depnum_ccdc_archive 'CCDC 1572351'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.
2017-10-31 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         ?
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.45

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'

_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                   9.272(3)
_cell_length_b                   9.723(3)
_cell_length_c                   21.851(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1969.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5286
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23643
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         26.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4081
_reflns_number_gt                2956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4081
_refine_ls_number_parameters     254
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1675
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.006
_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
N1 N 0.41981(15) 0.75999(15) 0.02344(6) 0.0343(3) Uani 1 1 d . . . . .
C2 C 0.14123(19) 0.71540(19) 0.14283(8) 0.0387(4) Uani 1 1 d . . . . .
C3 C 0.22513(18) 0.76570(17) 0.09083(8) 0.0344(4) Uani 1 1 d . . . . .
C4 C 0.38187(18) 0.72202(17) 0.08648(7) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.56080(18) 0.75935(17) 0.00078(8) 0.0337(4) Uani 1 1 d . . . . .
C6 C 0.30804(18) 0.84874(17) -0.00415(7) 0.0344(4) Uani 1 1 d . . . . .
H6 H 0.3438 0.9432 -0.0076 0.041 Uiso 1 1 calc R U . . .
C7 C 0.1974(2) 0.6061(2) 0.17807(8) 0.0427(4) Uani 1 1 d . . . . .
C8 C 0.25287(17) 0.79936(18) -0.06565(7) 0.0341(4) Uani 1 1 d . . . . .
C9 C 0.19008(19) 0.84194(18) 0.04254(8) 0.0374(4) Uani 1 1 d . . . . .
H9 H 0.1018 0.8863 0.0382 0.045 Uiso 1 1 calc R U . . .
N10 N 0.32669(19) 0.54556(18) 0.16230(7) 0.0520(4) Uani 1 1 d . . . . .
C11 C 0.67722(19) 0.7060(2) 0.03374(9) 0.0427(4) Uani 1 1 d . . . . .
H11 H 0.6624 0.6714 0.0729 0.051 Uiso 1 1 calc R U . . .
C12 C 0.5903(2) 0.81198(19) -0.05785(8) 0.0413(4) Uani 1 1 d . . . . .
H12 H 0.5156 0.8491 -0.0810 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2346(2) 0.6608(2) -0.07765(8) 0.0467(5) Uani 1 1 d . . . . .
H13 H 0.2620 0.5959 -0.0486 0.056 Uiso 1 1 calc R U . . .
O14 O 0.5377(2) 0.7793(2) 0.17205(8) 0.0818(5) Uani 1 1 d . U . . .
C15 C 0.4669(2) 0.8135(2) 0.13107(8) 0.0505(5) Uani 1 1 d . U . . .
H15 H 0.4608 0.9078 0.1244 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3903(2) 0.56894(18) 0.10231(8) 0.0417(4) Uani 1 1 d . . . . .
H16A H 0.3389 0.5158 0.0717 0.050 Uiso 1 1 calc R U . . .
H16B H 0.4902 0.5393 0.1024 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8143(2) 0.7040(2) 0.00873(10) 0.0537(5) Uani 1 1 d . . . . .
H17 H 0.8899 0.6673 0.0314 0.064 Uiso 1 1 calc R U . . .
C18 C 0.2115(2) 0.8947(2) -0.10940(9) 0.0477(5) Uani 1 1 d . . . . .
H18 H 0.2240 0.9882 -0.1021 0.057 Uiso 1 1 calc R U . . .
C19 C 0.7284(2) 0.8094(2) -0.08165(10) 0.0535(5) Uani 1 1 d . . . . .
H19 H 0.7453 0.8450 -0.1205 0.064 Uiso 1 1 calc R U . . .
C20 C 0.1170(2) 0.5627(2) 0.22947(9) 0.0566(6) Uani 1 1 d . . . . .
H20 H 0.1535 0.4934 0.2544 0.068 Uiso 1 1 calc R U . . .
C21 C 0.0067(2) 0.7712(2) 0.15809(9) 0.0491(5) Uani 1 1 d . . . . .
H21 H -0.0310 0.8419 0.1343 0.059 Uiso 1 1 calc R U . . .
C22 C -0.0712(2) 0.7238(3) 0.20750(10) 0.0600(6) Uani 1 1 d . . . . .
H22 H -0.1612 0.7608 0.2166 0.072 Uiso 1 1 calc R U . . .
C23 C 0.1339(2) 0.7131(3) -0.17572(9) 0.0616(6) Uani 1 1 d . . . . .
H23 H 0.0941 0.6839 -0.2126 0.074 Uiso 1 1 calc R U . . .
C24 C 0.1756(2) 0.6183(2) -0.13270(10) 0.0593(6) Uani 1 1 d . . . . .
H24 H 0.1641 0.5250 -0.1406 0.071 Uiso 1 1 calc R U . . .
C25 C 0.8415(2) 0.7548(3) -0.04864(11) 0.0600(6) Uani 1 1 d . . . . .
H25 H 0.9341 0.7525 -0.0649 0.072 Uiso 1 1 calc R U . . .
C26 C -0.0136(3) 0.6207(3) 0.24332(10) 0.0621(6) Uani 1 1 d . . . . .
H26 H -0.0642 0.5901 0.2774 0.074 Uiso 1 1 calc R U . . .
C27 C 0.3918(3) 0.4422(3) 0.20039(11) 0.0736(7) Uani 1 1 d . . . . .
H27A H 0.4081 0.4791 0.2405 0.110 Uiso 1 1 calc R U . . .
H27B H 0.4822 0.4142 0.1829 0.110 Uiso 1 1 calc R U . . .
H27C H 0.3287 0.3641 0.2032 0.110 Uiso 1 1 calc R U . . .
C28 C 0.1512(2) 0.8506(3) -0.16436(9) 0.0613(6) Uani 1 1 d . . . . .
H28 H 0.1226 0.9147 -0.1935 0.074 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
N1 C5 1.398(2) . ?
N1 C4 1.469(2) . ?
N1 C6 1.477(2) . ?
C2 C21 1.401(3) . ?
C2 C7 1.412(3) . ?
C2 C3 1.461(3) . ?
C3 C9 1.330(2) . ?
C3 C4 1.517(2) . ?
C4 C16 1.530(2) . ?
C4 C15 1.537(2) . ?
C5 C11 1.398(2) . ?
C5 C12 1.406(3) . ?
C6 C9 1.497(2) . ?
C6 C8 1.516(2) . ?
C7 N10 1.379(3) . ?
C7 C20 1.412(3) . ?
C8 C13 1.383(3) . ?
C8 C18 1.386(2) . ?
N10 C27 1.438(3) . ?
N10 C16 1.455(2) . ?
C11 C17 1.383(3) . ?
C12 C19 1.383(3) . ?
C13 C24 1.385(3) . ?
O14 C15 1.159(2) . ?
C17 C25 1.371(3) . ?
C18 C28 1.392(3) . ?
C19 C25 1.379(3) . ?
C20 C26 1.369(3) . ?
C21 C22 1.378(3) . ?
C22 C26 1.380(4) . ?
C23 C28 1.369(4) . ?
C23 C24 1.371(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 123.71(13) . . ?
C5 N1 C6 120.94(14) . . ?
C4 N1 C6 111.19(13) . . ?
C21 C2 C7 119.36(17) . . ?
C21 C2 C3 121.99(17) . . ?
C7 C2 C3 118.65(16) . . ?
C9 C3 C2 132.33(17) . . ?
C9 C3 C4 109.90(15) . . ?
C2 C3 C4 117.71(15) . . ?
N1 C4 C3 102.58(13) . . ?
N1 C4 C16 116.38(14) . . ?
C3 C4 C16 107.87(14) . . ?
N1 C4 C15 109.03(14) . . ?
C3 C4 C15 106.84(14) . . ?
C16 C4 C15 113.19(15) . . ?
C11 C5 N1 122.78(16) . . ?
C11 C5 C12 117.02(16) . . ?
N1 C5 C12 120.19(15) . . ?
N1 C6 C9 102.04(13) . . ?
N1 C6 C8 114.42(14) . . ?
C9 C6 C8 110.10(14) . . ?
N10 C7 C2 120.37(16) . . ?
N10 C7 C20 122.01(19) . . ?
C2 C7 C20 117.62(18) . . ?
C13 C8 C18 119.13(17) . . ?
C13 C8 C6 121.20(15) . . ?
C18 C8 C6 119.55(16) . . ?
C3 C9 C6 112.75(15) . . ?
C7 N10 C27 121.25(17) . . ?
C7 N10 C16 120.70(15) . . ?
C27 N10 C16 117.41(17) . . ?
C17 C11 C5 120.74(19) . . ?
C19 C12 C5 121.08(18) . . ?
C8 C13 C24 120.26(18) . . ?
O14 C15 C4 127.9(2) . . ?
N10 C16 C4 109.57(15) . . ?
C25 C17 C11 121.69(19) . . ?
C8 C18 C28 120.0(2) . . ?
C25 C19 C12 121.0(2) . . ?
C26 C20 C7 121.3(2) . . ?
C22 C21 C2 121.6(2) . . ?
C21 C22 C26 118.9(2) . . ?
C28 C23 C24 119.90(19) . . ?
C23 C24 C13 120.4(2) . . ?
C17 C25 C19 118.5(2) . . ?
C20 C26 C22 121.1(2) . . ?
C23 C28 C18 120.3(2) . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.049

