# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_structure1_120K
_database_code_depnum_ccdc_archive 'CCDC 1412010'
_audit_update_record             
;
2015-07-09 deposited with the CCDC.
2015-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_compound_source        'synthesis as described'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2'
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   5.6780(10)
_cell_length_b                   5.6456(7)
_cell_length_c                   32.491(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.09(2)
_cell_angle_gamma                90.00
_cell_volume                     1040.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    825
_cell_measurement_theta_min      2.5130
_cell_measurement_theta_max      27.6090

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34c (release 10-06-2014 CrysAlis171 .NET)
(compiled Jun 10 2014,17:39:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2283
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4203
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0859
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         28.35
_diffrn_measured_fraction_theta_max 0.870
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_reflns_number_total             2332
_reflns_number_gt                1635
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Version 1.171.37.34c'
_computing_cell_refinement       'CrysAlisPro, Version 1.171.37.34c'
_computing_data_reduction        'CrysAlisPro, Version 1.171.37.34c'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1173P)²+1.4378P] 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         2332
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_ref         0.2598
_refine_ls_wR_factor_gt          0.2314
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.142

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
N1 N 1.2566(5) -0.7129(5) 0.22529(8) 0.0270(7) Uani 1 1 d . . .
C1 C 1.0431(6) -0.7817(5) 0.21107(10) 0.0250(8) Uani 1 1 d . . .
H1 H 0.9890 -0.9328 0.2193 0.030 Uiso 1 1 calc R . .
C2 C 1.3286(6) -0.4982(6) 0.21276(10) 0.0246(7) Uani 1 1 d . . .
H2 H 1.4797 -0.4439 0.2226 0.029 Uiso 1 1 calc R . .
C3 C 0.8959(6) -0.6486(5) 0.18531(10) 0.0214(7) Uani 1 1 d . . .
H3 H 0.7445 -0.7065 0.1765 0.026 Uiso 1 1 calc R . .
C4 C 1.1963(6) -0.3539(5) 0.18661(9) 0.0221(7) Uani 1 1 d . . .
H4 H 1.2570 -0.2055 0.1783 0.027 Uiso 1 1 calc R . .
C5 C 0.9722(6) -0.4268(5) 0.17231(9) 0.0206(7) Uani 1 1 d . . .
C6 C 0.8239(6) -0.2802(6) 0.14594(10) 0.0231(7) Uani 1 1 d . . .
C7 C 0.6986(6) -0.1611(6) 0.12391(10) 0.0252(7) Uani 1 1 d . A .
C8 C 0.5475(6) -0.0185(6) 0.09651(10) 0.0253(8) Uani 1 1 d . . .
C9A C 0.3596(12) 0.1732(10) 0.10971(17) 0.0351(16) Uani 0.656(7) 1 d P A 1
H9A1 H 0.4240 0.3192 0.1229 0.042 Uiso 0.656(7) 1 calc PR A 1
H9A2 H 0.2182 0.1115 0.1227 0.042 Uiso 0.656(7) 1 calc PR A 1
C10A C 0.6232(11) 0.1653(10) 0.06465(19) 0.0342(16) Uani 0.656(7) 1 d P A 1
H10A H 0.6968 0.3118 0.0761 0.041 Uiso 0.656(7) 1 calc PR A 1
H10B H 0.7054 0.1014 0.0409 0.041 Uiso 0.656(7) 1 calc PR A 1
C11A C 0.3584(11) -0.1056(9) 0.06487(18) 0.0344(16) Uani 0.656(7) 1 d P A 1
H11A H 0.2166 -0.1772 0.0762 0.041 Uiso 0.656(7) 1 calc PR A 1
H11B H 0.4161 -0.1954 0.0412 0.041 Uiso 0.656(7) 1 calc PR A 1
C9B C 0.551(2) -0.0350(18) 0.0462(3) 0.028(3) Uani 0.344(7) 1 d P A 2
H9B1 H 0.4871 -0.1818 0.0332 0.034 Uiso 0.344(7) 1 calc PR A 2
H9B2 H 0.6932 0.0264 0.0335 0.034 Uiso 0.344(7) 1 calc PR A 2
C10B C 0.2799(17) -0.018(2) 0.0909(3) 0.027(3) Uani 0.344(7) 1 d P A 2
H10C H 0.2076 -0.1635 0.0789 0.033 Uiso 0.344(7) 1 calc PR A 2
H10D H 0.1947 0.0444 0.1144 0.033 Uiso 0.344(7) 1 calc PR A 2
C11B C 0.547(2) 0.2514(16) 0.0903(3) 0.027(3) Uani 0.344(7) 1 d P A 2
H11C H 0.4948 0.3466 0.1137 0.033 Uiso 0.344(7) 1 calc PR A 2
H11D H 0.6886 0.3182 0.0780 0.033 Uiso 0.344(7) 1 calc PR A 2
C12 C 0.3551(6) 0.1646(6) 0.06027(11) 0.0292(8) Uani 1 1 d . A .
C13 C 0.2028(6) 0.3055(6) 0.03299(11) 0.0311(8) Uani 1 1 d . . .
C14 C 0.0751(7) 0.4290(6) 0.01189(12) 0.0338(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0282(16) 0.0191(14) 0.0331(14) 0.0025(11) -0.0030(12) 0.0051(13)
C1 0.035(2) 0.0097(14) 0.0311(16) 0.0016(12) 0.0037(14) 0.0056(14)
C2 0.0155(16) 0.0227(17) 0.0351(17) -0.0044(13) -0.0032(13) 0.0042(14)
C3 0.0168(16) 0.0133(14) 0.0339(17) -0.0013(12) -0.0004(12) 0.0019(13)
C4 0.0211(17) 0.0128(14) 0.0322(16) 0.0007(12) 0.0008(13) 0.0000(13)
C5 0.0209(17) 0.0125(14) 0.0283(15) 0.0004(12) 0.0010(12) 0.0050(13)
C6 0.0230(17) 0.0128(14) 0.0328(16) 0.0015(12) -0.0032(13) 0.0000(13)
C7 0.0240(18) 0.0173(15) 0.0340(17) 0.0044(13) -0.0005(13) -0.0004(14)
C8 0.0285(19) 0.0149(15) 0.0318(17) 0.0045(13) -0.0033(14) 0.0006(14)
C9A 0.045(4) 0.026(3) 0.034(3) 0.003(2) -0.006(2) 0.012(3)
C10A 0.030(3) 0.025(3) 0.047(3) 0.015(3) -0.004(3) 0.001(3)
C11A 0.041(4) 0.016(3) 0.045(3) 0.005(2) -0.010(3) 0.006(2)
C9B 0.042(7) 0.020(5) 0.023(5) 0.002(4) 0.001(4) 0.004(5)
C10B 0.012(5) 0.032(6) 0.038(6) 0.010(5) 0.000(4) 0.002(4)
C11B 0.038(6) 0.010(4) 0.033(5) 0.005(4) -0.008(4) 0.010(4)
C12 0.029(2) 0.0176(16) 0.0396(19) 0.0087(14) -0.0068(15) 0.0007(15)
C13 0.0242(18) 0.0212(17) 0.047(2) 0.0091(15) -0.0088(15) -0.0054(16)
C14 0.0270(19) 0.0222(18) 0.051(2) 0.0137(16) -0.0113(16) -0.0034(16)

_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
N1 C1 1.332(4) . ?
N1 C2 1.349(4) . ?
C1 C3 1.374(4) . ?
C2 C4 1.372(4) . ?
C3 C5 1.398(4) . ?
C4 C5 1.393(5) . ?
C5 C6 1.432(4) . ?
C6 C7 1.190(5) . ?
C7 C8 1.447(5) . ?
C8 C10B 1.521(10) . ?
C8 C11A 1.527(7) . ?
C8 C11B 1.537(9) . ?
C8 C10A 1.543(6) . ?
C8 C9A 1.595(7) . ?
C8 C9B 1.638(9) . ?
C9A C12 1.606(6) . ?
C10A C12 1.521(7) . ?
C11A C12 1.533(6) . ?
C9B C12 1.664(11) . ?
C10B C12 1.508(10) . ?
C11B C12 1.507(11) . ?
C12 C13 1.443(5) . ?
C13 C14 1.195(5) . ?
C14 C14 1.377(7) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.3(3) . . ?
N1 C1 C3 124.3(3) . . ?
N1 C2 C4 123.8(3) . . ?
C1 C3 C5 119.1(3) . . ?
C2 C4 C5 119.4(3) . . ?
C4 C5 C3 117.1(3) . . ?
C4 C5 C6 121.8(3) . . ?
C3 C5 C6 121.1(3) . . ?
C7 C6 C5 179.1(4) . . ?
C6 C7 C8 179.0(4) . . ?
C7 C8 C10B 129.2(5) . . ?
C7 C8 C11A 127.4(3) . . ?
C7 C8 C11B 128.9(5) . . ?
C10B C8 C11B 89.3(6) . . ?
C7 C8 C10A 127.6(3) . . ?
C11A C8 C10A 88.6(4) . . ?
C7 C8 C9A 126.5(3) . . ?
C11A C8 C9A 86.7(4) . . ?
C10A C8 C9A 86.5(4) . . ?
C7 C8 C9B 123.0(4) . . ?
C10B C8 C9B 86.9(6) . . ?
C11B C8 C9B 85.7(5) . . ?
C7 C8 C12 179.0(3) . . ?
C10B C8 C12 51.5(4) . . ?
C11A C8 C12 52.4(2) . . ?
C11B C8 C12 51.3(4) . . ?
C10A C8 C12 51.8(3) . . ?
C9A C8 C12 54.4(2) . . ?
C9B C8 C12 56.1(4) . . ?
C8 C9A C12 71.7(3) . . ?
C12 C10A C8 75.4(3) . . ?
C8 C11A C12 75.5(3) . . ?
C8 C9B C12 69.1(4) . . ?
C12 C10B C8 76.4(5) . . ?
C12 C11B C8 76.0(5) . . ?
C13 C12 C11B 127.4(4) . . ?
C13 C12 C10B 126.8(5) . . ?
C11B C12 C10B 90.9(6) . . ?
C13 C12 C10A 128.3(3) . . ?
C13 C12 C11A 127.7(4) . . ?
C10A C12 C11A 89.2(4) . . ?
C13 C12 C9A 125.1(4) . . ?
C10A C12 C9A 86.8(4) . . ?
C11A C12 C9A 86.2(4) . . ?
C13 C12 C9B 126.3(4) . . ?
C11B C12 C9B 85.8(6) . . ?
C10B C12 C9B 86.3(6) . . ?
C13 C12 C8 178.7(3) . . ?
C11B C12 C8 52.7(4) . . ?
C10B C12 C8 52.1(4) . . ?
C10A C12 C8 52.8(2) . . ?
C11A C12 C8 52.1(3) . . ?
C9A C12 C8 53.9(2) . . ?
C9B C12 C8 54.8(3) . . ?
C14 C13 C12 177.0(4) . . ?
C13 C14 C14 178.9(6) . 3_565 ?

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
C2 H2 N1 0.95 2.56 3.418(4) 150.9 2_855
####################################################################### 
# 
# 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_structure1_293K
_database_code_depnum_ccdc_archive 'CCDC 1412011'
_audit_update_record             
;
2015-07-09 deposited with the CCDC.
2015-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_compound_source        'synthesis as described'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2'
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   5.7123(19)
_cell_length_b                   5.7076(17)
_cell_length_c                   33.016(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.68(5)
_cell_angle_gamma                90.00
_cell_volume                     1074.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    601
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.08

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3587
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       'combined φ and ω-scans'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7162
_diffrn_reflns_av_R_equivalents  0.1652
_diffrn_reflns_av_sigmaI/netI    0.2546
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.08
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_reflns_number_total             2400
_reflns_number_gt                790
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0374P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2400
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2607
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1598
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_restrained_S_all      0.861
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.092

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
N1 N 1.2548(5) -0.6858(6) 0.22511(9) 0.0650(9) Uani 1 1 d . . .
C1 C 1.0424(6) -0.7560(6) 0.21087(10) 0.0613(11) Uani 1 1 d . . .
H1 H 0.9909 -0.9028 0.2187 0.074 Uiso 1 1 calc R . .
C2 C 1.3245(6) -0.4768(7) 0.21269(11) 0.0636(11) Uani 1 1 d . . .
H2 H 1.4728 -0.4252 0.2219 0.076 Uiso 1 1 calc R . .
C3 C 0.8955(5) -0.6250(6) 0.18542(10) 0.0510(9) Uani 1 1 d . . .
H3 H 0.7478 -0.6812 0.1768 0.061 Uiso 1 1 calc R . .
C4 C 1.1915(5) -0.3320(6) 0.18704(10) 0.0584(10) Uani 1 1 d . . .
H4 H 1.2482 -0.1869 0.1794 0.070 Uiso 1 1 calc R . .
C5 C 0.9697(5) -0.4087(6) 0.17282(9) 0.0504(9) Uani 1 1 d . . .
C6 C 0.8214(6) -0.2617(6) 0.14620(11) 0.0593(10) Uani 1 1 d . . .
C7 C 0.6948(5) -0.1450(6) 0.12460(10) 0.0577(10) Uani 1 1 d . A .
C8 C 0.5452(5) -0.0062(6) 0.09673(10) 0.0528(10) Uani 1 1 d . . .
C9A C 0.3591(16) 0.1794(18) 0.1077(2) 0.075(4) Uani 0.62(2) 1 d P A 1
H9A1 H 0.2217 0.1195 0.1201 0.090 Uiso 0.62(2) 1 calc PR A 1
H9A2 H 0.4199 0.3222 0.1203 0.090 Uiso 0.62(2) 1 calc PR A 1
C10A C 0.6177(12) 0.1712(19) 0.0650(3) 0.084(5) Uani 0.62(2) 1 d P A 1
H10A H 0.6906 0.3139 0.0756 0.101 Uiso 0.62(2) 1 calc PR A 1
H10B H 0.6960 0.1068 0.0423 0.101 Uiso 0.62(2) 1 calc PR A 1
C11A C 0.3642(19) -0.0944(13) 0.0646(3) 0.087(6) Uani 0.62(2) 1 d P A 1
H11A H 0.2272 -0.1699 0.0746 0.104 Uiso 0.62(2) 1 calc PR A 1
H11B H 0.4259 -0.1771 0.0419 0.104 Uiso 0.62(2) 1 calc PR A 1
C9B C 0.547(2) -0.013(3) 0.0486(4) 0.073(6) Uani 0.38(2) 1 d P A 2
H9B1 H 0.6852 0.0515 0.0370 0.087 Uiso 0.38(2) 1 calc PR A 2
H9B2 H 0.4907 -0.1557 0.0355 0.087 Uiso 0.38(2) 1 calc PR A 2
C10B C 0.279(2) -0.008(3) 0.0930(6) 0.091(9) Uani 0.38(2) 1 d P A 2
H10C H 0.2016 0.0571 0.1159 0.109 Uiso 0.38(2) 1 calc PR A 2
H10D H 0.2057 -0.1508 0.0826 0.109 Uiso 0.38(2) 1 calc PR A 2
C11B C 0.544(4) 0.263(2) 0.0924(6) 0.085(9) Uani 0.38(2) 1 d P A 2
H11C H 0.6815 0.3320 0.0816 0.102 Uiso 0.38(2) 1 calc PR A 2
H11D H 0.4878 0.3499 0.1151 0.102 Uiso 0.38(2) 1 calc PR A 2
C12 C 0.3517(5) 0.1718(6) 0.06064(10) 0.0542(10) Uani 1 1 d . A .
C13 C 0.2023(6) 0.3110(6) 0.03306(11) 0.0598(10) Uani 1 1 d . . .
C14 C 0.0726(6) 0.4306(6) 0.01219(11) 0.0632(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0542(18) 0.069(2) 0.070(2) 0.0002(18) -0.0093(15) 0.0213(16)
C1 0.073(3) 0.053(2) 0.058(2) 0.0068(19) 0.004(2) 0.0116(19)
C2 0.049(2) 0.066(3) 0.074(3) -0.004(2) -0.0088(18) 0.000(2)
C3 0.0458(19) 0.046(2) 0.060(2) 0.0007(19) -0.0025(16) 0.0052(16)
C4 0.051(2) 0.057(2) 0.066(2) 0.008(2) -0.0048(17) 0.0021(17)
C5 0.0430(19) 0.056(2) 0.051(2) 0.0013(19) -0.0039(15) 0.0108(17)
C6 0.056(2) 0.048(2) 0.072(3) 0.002(2) -0.0071(19) 0.0035(18)
C7 0.054(2) 0.053(2) 0.065(2) 0.008(2) -0.0057(18) 0.0000(17)
C8 0.0449(19) 0.055(2) 0.056(2) 0.016(2) -0.0142(16) 0.0037(16)
C9A 0.072(7) 0.075(8) 0.077(6) 0.009(5) -0.008(4) 0.032(6)
C10A 0.059(4) 0.089(11) 0.101(9) 0.035(9) -0.014(5) 0.001(5)
C11A 0.109(11) 0.051(5) 0.092(9) 0.009(5) -0.057(9) 0.004(5)
C9B 0.053(8) 0.069(11) 0.095(10) 0.006(7) -0.008(6) -0.011(8)
C10B 0.072(9) 0.092(19) 0.107(16) 0.049(17) -0.015(8) -0.001(8)
C11B 0.112(19) 0.048(8) 0.088(15) 0.013(8) -0.056(15) 0.002(8)
C12 0.0438(19) 0.054(2) 0.063(3) 0.012(2) -0.0095(16) 0.0067(17)
C13 0.053(2) 0.053(2) 0.072(3) 0.013(2) -0.0118(19) -0.0112(18)
C14 0.054(2) 0.058(2) 0.074(3) 0.015(2) -0.0190(18) -0.0018(17)

_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
N1 C1 1.334(4) . ?
N1 C2 1.331(4) . ?
C1 C3 1.371(4) . ?
C2 C4 1.376(4) . ?
C3 C5 1.378(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.449(5) . ?
C6 C7 1.187(4) . ?
C7 C8 1.450(5) . ?
C8 C10B 1.520(12) . ?
C8 C11B 1.542(12) . ?
C8 C11A 1.520(7) . ?
C8 C10A 1.533(8) . ?
C8 C9A 1.560(7) . ?
C8 C9B 1.589(13) . ?
C9A C12 1.552(8) . ?
C10A C12 1.517(7) . ?
C11A C12 1.527(8) . ?
C9B C12 1.605(13) . ?
C10B C12 1.557(14) . ?
C11B C12 1.558(12) . ?
C12 C13 1.445(5) . ?
C13 C14 1.193(4) . ?
C14 C14 1.370(7) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.3(3) . . ?
N1 C1 C3 124.0(3) . . ?
N1 C2 C4 124.3(3) . . ?
C5 C3 C1 119.0(3) . . ?
C2 C4 C5 118.2(3) . . ?
C3 C5 C4 118.1(3) . . ?
C3 C5 C6 121.5(3) . . ?
C4 C5 C6 120.4(3) . . ?
C7 C6 C5 178.2(4) . . ?
C6 C7 C8 177.5(4) . . ?
C7 C8 C10B 126.5(6) . . ?
C7 C8 C11B 127.0(5) . . ?
C10B C8 C11B 89.9(10) . . ?
C7 C8 C11A 127.5(4) . . ?
C10B C8 C11A 46.3(7) . . ?
C11B C8 C11A 105.4(5) . . ?
C7 C8 C10A 128.3(3) . . ?
C11A C8 C10A 86.7(6) . . ?
C7 C8 C9A 127.3(4) . . ?
C11A C8 C9A 86.8(5) . . ?
C10A C8 C9A 85.9(5) . . ?
C7 C8 C9B 125.4(5) . . ?
C10B C8 C9B 89.5(8) . . ?
C11B C8 C9B 86.1(9) . . ?
C9A C8 C9B 107.3(5) . . ?
C7 C8 C12 179.8(3) . . ?
C10B C8 C12 53.4(5) . . ?
C11B C8 C12 53.2(4) . . ?
C11A C8 C12 52.2(3) . . ?
C10A C8 C12 51.7(3) . . ?
C9A C8 C12 52.8(3) . . ?
C9B C8 C12 54.5(4) . . ?
C12 C9A C8 74.0(4) . . ?
C12 C10A C8 75.7(4) . . ?
C12 C10A C11A 46.7(3) . . ?
C8 C10A C11A 46.4(3) . . ?
C8 C11A C12 75.8(4) . . ?
C8 C11A C10A 46.9(4) . . ?
C12 C11A C10A 46.3(3) . . ?
C12 C9B C8 71.8(6) . . ?
C12 C9B C11B 46.5(6) . . ?
C8 C9B C11B 46.0(6) . . ?
C8 C10B C12 74.9(6) . . ?
C8 C11B C12 74.3(6) . . ?
C8 C11B C9B 47.9(6) . . ?
C12 C11B C9B 48.4(5) . . ?
C13 C12 C10A 127.5(4) . . ?
C13 C12 C11B 127.1(5) . . ?
C13 C12 C10B 128.4(5) . . ?
C11B C12 C10B 88.0(9) . . ?
C13 C12 C9A 126.3(4) . . ?
C10A C12 C9A 86.7(5) . . ?
C13 C12 C11A 128.5(4) . . ?
C10A C12 C11A 87.0(5) . . ?
C11B C12 C11A 104.3(5) . . ?
C10B C12 C11A 45.6(6) . . ?
C9A C12 C11A 86.8(5) . . ?
C13 C12 C9B 126.7(5) . . ?
C11B C12 C9B 85.1(9) . . ?
C10B C12 C9B 87.7(8) . . ?
C13 C12 C8 179.5(3) . . ?
C10A C12 C8 52.5(3) . . ?
C11B C12 C8 52.5(4) . . ?
C10B C12 C8 51.6(4) . . ?
C9A C12 C8 53.2(3) . . ?
C11A C12 C8 51.9(3) . . ?
C9B C12 C8 53.7(4) . . ?
C14 C13 C12 176.2(4) . . ?
C13 C14 C14 178.9(5) . 3_565 ?

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
C2 H2 N1 0.93 2.64 3.481(4) 150.0 2_855
