# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_scd0381_05112016_Monoclinic_100K
_database_code_depnum_ccdc_archive 'CCDC 1497526'
#Added by publCIF



_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2017-08-10 downloaded from the CCDC.
;
_publcif_datablock.id            {4a4983a4-0a80-4720-bfd2-e5377475b215}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2ybc'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'butoxyphenyl N-substituted naphthalene diimide '
_chemical_name_common            BNDI
_chemical_melting_point          635
_chemical_formula_moiety         'C34 H30 N2 O6'
_chemical_formula_sum            'C34 H30 N2 O6'
_chemical_formula_weight         562.60

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.026(2)
_cell_length_b                   33.756(5)
_cell_length_c                   7.9533(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.997(10)
_cell_angle_gamma                90
_cell_volume                     1328.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7185
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.53

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.840
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16317
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4061
_reflns_number_gt                3266
_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    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0783P)²+0.4261P] 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         4061
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.67779(19) 0.60970(3) 0.79878(11) 0.0147(2) Uani 1 1 d . . . . .
O2 O -0.06737(18) 0.53784(3) 0.58139(11) 0.0146(2) Uani 1 1 d . . . . .
O3 O 0.10927(19) 0.67389(3) 0.11841(11) 0.0143(2) Uani 1 1 d . . . . .
N1 N 0.3241(2) 0.57126(3) 0.67603(12) 0.0112(2) Uani 1 1 d . . . . .
C1 C 0.5495(2) 0.57933(3) 0.80167(15) 0.0111(2) Uani 1 1 d . . . . .
C2 C 0.1436(2) 0.53964(3) 0.68085(14) 0.0108(2) Uani 1 1 d . . . . .
C3 C 0.2281(2) 0.50886(3) 0.81278(14) 0.0102(2) Uani 1 1 d . . . . .
C4 C 0.4620(2) 0.51462(3) 0.93653(14) 0.0098(2) Uani 1 1 d . . . . .
C5 C 0.0766(2) 0.47482(4) 0.81341(14) 0.0115(2) Uani 1 1 d . . . . .
H5 H -0.0799 0.4710 0.7290 0.014 Uiso 1 1 calc R U . . .
C6 C 0.1535(2) 0.44565(3) 0.93893(15) 0.0119(2) Uani 1 1 d . . . . .
H6 H 0.0492 0.4222 0.9383 0.014 Uiso 1 1 calc R U . . .
C7 C 0.3789(2) 0.45097(3) 1.06267(14) 0.0101(2) Uani 1 1 d . . . . .
C8 C 0.2705(2) 0.59806(3) 0.53116(15) 0.0111(2) Uani 1 1 d . . . . .
C9 C 0.4228(2) 0.59426(4) 0.40310(15) 0.0127(2) Uani 1 1 d . . . . .
H9 H 0.5592 0.5745 0.4112 0.015 Uiso 1 1 calc R U . . .
C10 C 0.3760(3) 0.61941(4) 0.26201(15) 0.0124(2) Uani 1 1 d . . . . .
H10 H 0.4811 0.6170 0.1741 0.015 Uiso 1 1 calc R U . . .
C11 C 0.1740(2) 0.64807(3) 0.25072(15) 0.0111(2) Uani 1 1 d . . . . .
C12 C 0.0216(3) 0.65157(3) 0.38130(15) 0.0129(2) Uani 1 1 d . . . . .
H12 H -0.1157 0.6712 0.3737 0.015 Uiso 1 1 calc R U . . .
C13 C 0.0696(3) 0.62665(3) 0.52167(15) 0.0127(2) Uani 1 1 d . . . . .
H13 H -0.0337 0.6291 0.6105 0.015 Uiso 1 1 calc R U . . .
C14 C 0.2537(3) 0.67025(4) -0.02198(15) 0.0161(3) Uani 1 1 d . . . . .
H14A H 0.2266 0.6435 -0.0733 0.019 Uiso 1 1 calc R U . . .
H14B H 0.4495 0.6743 0.0180 0.019 Uiso 1 1 calc R U . . .
C15 C 0.1438(3) 0.70155(4) -0.15208(15) 0.0168(3) Uani 1 1 d . . . . .
H15A H -0.0530 0.6973 -0.1871 0.020 Uiso 1 1 calc R U . . .
H15B H 0.2286 0.6980 -0.2545 0.020 Uiso 1 1 calc R U . . .
C16 C 0.1918(3) 0.74411(4) -0.08836(16) 0.0168(3) Uani 1 1 d . . . . .
H16A H 0.0864 0.7622 -0.1725 0.020 Uiso 1 1 calc R U . . .
H16B H 0.1230 0.7470 0.0203 0.020 Uiso 1 1 calc R U . . .
C17 C 0.4865(3) 0.75662(5) -0.0599(2) 0.0258(3) Uani 1 1 d . . . . .
H17A H 0.5930 0.7387 0.0227 0.039 Uiso 1 1 calc R U . . .
H17B H 0.5031 0.7838 -0.0156 0.039 Uiso 1 1 calc R U . . .
H17C H 0.5537 0.7554 -0.1683 0.039 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 1.2135(15) . ?
O2 C2 1.2095(15) . ?
O3 C11 1.3616(13) . ?
O3 C14 1.4387(15) . ?
N1 C1 1.4010(16) . ?
N1 C2 1.4055(15) . ?
N1 C8 1.4527(14) . ?
C1 C7 1.4848(16) 3_667 ?
C2 C3 1.4852(15) . ?
C3 C5 1.3790(17) . ?
C3 C4 1.4096(17) . ?
C4 C7 1.4095(16) 3_667 ?
C4 C4 1.416(2) 3_667 ?
C5 C6 1.4076(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3775(17) . ?
C6 H6 0.9500 . ?
C7 C4 1.4095(16) 3_667 ?
C7 C1 1.4848(16) 3_667 ?
C8 C9 1.3821(16) . ?
C8 C13 1.3892(17) . ?
C9 C10 1.3940(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3939(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3984(17) . ?
C12 C13 1.3852(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.5142(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5286(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C11 O3 C14 117.39(9) . . ?
C1 N1 C2 125.01(10) . . ?
C1 N1 C8 117.42(10) . . ?
C2 N1 C8 117.56(10) . . ?
O1 C1 N1 121.14(11) . . ?
O1 C1 C7 122.22(11) . 3_667 ?
N1 C1 C7 116.64(10) . 3_667 ?
O2 C2 N1 121.13(10) . . ?
O2 C2 C3 122.52(11) . . ?
N1 C2 C3 116.35(10) . . ?
C5 C3 C4 120.42(10) . . ?
C5 C3 C2 119.69(11) . . ?
C4 C3 C2 119.89(10) . . ?
C7 C4 C3 121.35(10) 3_667 . ?
C7 C4 C4 119.26(13) 3_667 3_667 ?
C3 C4 C4 119.39(13) . 3_667 ?
C3 C5 C6 120.12(11) . . ?
C3 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.39(11) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C4 120.40(11) . 3_667 ?
C6 C7 C1 119.66(10) . 3_667 ?
C4 C7 C1 119.92(11) 3_667 3_667 ?
C9 C8 C13 120.96(11) . . ?
C9 C8 N1 118.46(10) . . ?
C13 C8 N1 120.58(10) . . ?
C8 C9 C10 119.95(11) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.58(11) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
O3 C11 C10 124.60(11) . . ?
O3 C11 C12 115.57(10) . . ?
C10 C11 C12 119.83(11) . . ?
C13 C12 C11 120.41(11) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 119.27(11) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
O3 C14 C15 107.31(10) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 114.29(11) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 113.84(12) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C2 N1 C1 O1 -171.30(11) . . . . ?
C8 N1 C1 O1 7.58(17) . . . . ?
C2 N1 C1 C7 8.49(17) . . . 3_667 ?
C8 N1 C1 C7 -172.63(10) . . . 3_667 ?
C1 N1 C2 O2 169.00(11) . . . . ?
C8 N1 C2 O2 -9.89(16) . . . . ?
C1 N1 C2 C3 -11.50(16) . . . . ?
C8 N1 C2 C3 169.62(10) . . . . ?
O2 C2 C3 C5 6.65(18) . . . . ?
N1 C2 C3 C5 -172.85(10) . . . . ?
O2 C2 C3 C4 -173.29(11) . . . . ?
N1 C2 C3 C4 7.21(16) . . . . ?
C5 C3 C4 C7 179.45(11) . . . 3_667 ?
C2 C3 C4 C7 -0.61(17) . . . 3_667 ?
C5 C3 C4 C4 -1.0(2) . . . 3_667 ?
C2 C3 C4 C4 178.90(12) . . . 3_667 ?
C4 C3 C5 C6 0.57(18) . . . . ?
C2 C3 C5 C6 -179.37(10) . . . . ?
C3 C5 C6 C7 0.48(18) . . . . ?
C5 C6 C7 C4 -1.04(18) . . . 3_667 ?
C5 C6 C7 C1 177.45(10) . . . 3_667 ?
C1 N1 C8 C9 78.29(14) . . . . ?
C2 N1 C8 C9 -102.73(13) . . . . ?
C1 N1 C8 C13 -102.04(14) . . . . ?
C2 N1 C8 C13 76.93(15) . . . . ?
C13 C8 C9 C10 0.13(19) . . . . ?
N1 C8 C9 C10 179.79(11) . . . . ?
C8 C9 C10 C11 -0.45(18) . . . . ?
C14 O3 C11 C10 2.29(17) . . . . ?
C14 O3 C11 C12 -177.52(11) . . . . ?
C9 C10 C11 O3 -179.35(11) . . . . ?
C9 C10 C11 C12 0.46(18) . . . . ?
O3 C11 C12 C13 179.67(11) . . . . ?
C10 C11 C12 C13 -0.15(18) . . . . ?
C11 C12 C13 C8 -0.17(18) . . . . ?
C9 C8 C13 C12 0.18(18) . . . . ?
N1 C8 C13 C12 -179.48(11) . . . . ?
C11 O3 C14 C15 179.31(10) . . . . ?
O3 C14 C15 C16 63.50(15) . . . . ?
C14 C15 C16 C17 68.56(15) . . . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_scd0497_Triclinic_100K
_database_code_depnum_ccdc_archive 'CCDC 1497523'
#Added by publCIF



_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2017-08-10 downloaded from the CCDC.
;
_publcif_datablock.id            {dc48d5fa-6034-47e2-beca-65b2ac4106b6}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'butoxyphenyl N-substituted naphthalene diimide '
_chemical_name_common            BNDI
_chemical_melting_point          635
_chemical_formula_moiety         'C34 H30 N2 O6'
_chemical_formula_sum            'C34 H30 N2 O6'
_chemical_formula_weight         562.60

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                   4.1636(8)
_cell_length_b                   8.1371(18)
_cell_length_c                   20.104(5)
_cell_angle_alpha                100.182(11)
_cell_angle_beta                 93.124(14)
_cell_angle_gamma                94.102(14)
_cell_volume                     667.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6075
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      30.44

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14793
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         30.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3710
_reflns_number_gt                2854
_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    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0555P)²+0.2578P] 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         3710
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.6252(2) 1.01365(11) 0.70924(4) 0.0149(2) Uani 1 1 d . . . . .
O2 O -0.0723(2) 0.63226(11) 0.57043(4) 0.0154(2) Uani 1 1 d . . . . .
O3 O 0.1453(2) 0.41476(11) 0.83759(4) 0.0147(2) Uani 1 1 d . . . . .
N1 N 0.3144(3) 0.80567(12) 0.63843(5) 0.0115(2) Uani 1 1 d . . . . .
C1 C 0.5169(3) 0.95419(14) 0.65216(6) 0.0110(2) Uani 1 1 d . . . . .
C2 C 0.1415(3) 0.74407(14) 0.57577(6) 0.0114(2) Uani 1 1 d . . . . .
C3 C 0.2342(3) 0.82118(14) 0.51740(6) 0.0107(2) Uani 1 1 d . . . . .
C4 C 0.1014(3) 0.75410(15) 0.45315(6) 0.0123(2) Uani 1 1 d . . . . .
H4 H -0.0499 0.6586 0.4465 0.015 Uiso 1 1 calc R U . . .
C5 C 0.1888(3) 0.82643(15) 0.39758(6) 0.0120(2) Uani 1 1 d . . . . .
H5 H 0.0990 0.7784 0.3534 0.014 Uiso 1 1 calc R U . . .
C6 C 0.4038(3) 0.96659(14) 0.40676(6) 0.0106(2) Uani 1 1 d . . . . .
C7 C 0.5420(3) 1.03681(14) 0.47210(6) 0.0100(2) Uani 1 1 d . . . . .
C8 C 0.2784(3) 0.70653(15) 0.69140(6) 0.0114(2) Uani 1 1 d . . . . .
C9 C 0.1262(3) 0.76481(15) 0.74961(6) 0.0135(2) Uani 1 1 d . . . . .
H9 H 0.0472 0.8728 0.7562 0.016 Uiso 1 1 calc R U . . .
C10 C 0.0904(3) 0.66481(15) 0.79792(6) 0.0141(3) Uani 1 1 d . . . . .
H10 H -0.0115 0.7047 0.8381 0.017 Uiso 1 1 calc R U . . .
C11 C 0.2029(3) 0.50563(15) 0.78809(6) 0.0120(2) Uani 1 1 d . . . . .
C12 C 0.3613(3) 0.44887(15) 0.73016(6) 0.0121(2) Uani 1 1 d . . . . .
H12 H 0.4429 0.3415 0.7236 0.015 Uiso 1 1 calc R U . . .
C13 C 0.3987(3) 0.55103(15) 0.68201(6) 0.0125(2) Uani 1 1 d . . . . .
H13 H 0.5075 0.5136 0.6425 0.015 Uiso 1 1 calc R U . . .
C14 C 0.2785(3) 0.25521(15) 0.83178(6) 0.0142(3) Uani 1 1 d . . . . .
H14A H 0.5149 0.2689 0.8284 0.017 Uiso 1 1 calc R U . . .
H14B H 0.1820 0.1785 0.7906 0.017 Uiso 1 1 calc R U . . .
C15 C 0.2025(3) 0.18434(16) 0.89444(6) 0.0156(3) Uani 1 1 d . . . . .
H15A H 0.2988 0.0759 0.8924 0.019 Uiso 1 1 calc R U . . .
H15B H -0.0343 0.1627 0.8950 0.019 Uiso 1 1 calc R U . . .
C16 C 0.3296(3) 0.30131(17) 0.95968(6) 0.0184(3) Uani 1 1 d . . . . .
H16A H 0.2278 0.4083 0.9622 0.022 Uiso 1 1 calc R U . . .
H16B H 0.5651 0.3260 0.9582 0.022 Uiso 1 1 calc R U . . .
C17 C 0.2660(4) 0.2306(2) 1.02350(7) 0.0277(3) Uani 1 1 d . . . . .
H17A H 0.0327 0.2120 1.0269 0.042 Uiso 1 1 calc R U . . .
H17B H 0.3601 0.3102 1.0633 0.042 Uiso 1 1 calc R U . . .
H17C H 0.3643 0.1240 1.0213 0.042 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 1.2127(15) . ?
O2 C2 1.2128(15) . ?
O3 C11 1.3620(14) . ?
O3 C14 1.4364(15) . ?
N1 C1 1.3995(16) . ?
N1 C2 1.4081(16) . ?
N1 C8 1.4529(15) . ?
C1 C6 1.4864(16) 2_676 ?
C2 C3 1.4815(16) . ?
C3 C4 1.3789(17) . ?
C3 C7 1.4094(16) 2_676 ?
C4 C5 1.4047(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3777(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4100(16) . ?
C6 C1 1.4864(16) 2_676 ?
C7 C3 1.4094(16) 2_676 ?
C7 C7 1.411(2) 2_676 ?
C8 C13 1.3799(17) . ?
C8 C9 1.3869(17) . ?
C9 C10 1.3803(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3938(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3935(17) . ?
C12 C13 1.3910(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.5146(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5221(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5247(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C11 O3 C14 117.36(9) . . ?
C1 N1 C2 124.13(10) . . ?
C1 N1 C8 118.84(10) . . ?
C2 N1 C8 117.03(10) . . ?
O1 C1 N1 121.44(10) . . ?
O1 C1 C6 121.87(11) . 2_676 ?
N1 C1 C6 116.68(10) . 2_676 ?
O2 C2 N1 120.85(10) . . ?
O2 C2 C3 122.11(11) . . ?
N1 C2 C3 117.04(10) . . ?
C4 C3 C7 120.30(10) . 2_676 ?
C4 C3 C2 120.00(11) . . ?
C7 C3 C2 119.70(10) 2_676 . ?
C3 C4 C5 120.27(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.44(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.04(10) . . ?
C5 C6 C1 119.75(10) . 2_676 ?
C7 C6 C1 120.19(10) . 2_676 ?
C3 C7 C6 121.06(10) 2_676 . ?
C3 C7 C7 119.27(13) 2_676 2_676 ?
C6 C7 C7 119.67(13) . 2_676 ?
C13 C8 C9 120.58(11) . . ?
C13 C8 N1 117.98(10) . . ?
C9 C8 N1 121.44(11) . . ?
C10 C9 C8 119.52(11) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.40(11) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
O3 C11 C12 124.34(11) . . ?
O3 C11 C10 115.77(10) . . ?
C12 C11 C10 119.89(11) . . ?
C13 C12 C11 119.31(11) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C13 C12 120.27(11) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O3 C14 C15 107.57(10) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 112.64(11) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 113.74(12) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C2 N1 C1 O1 169.74(11) . . . . ?
C8 N1 C1 O1 -10.59(17) . . . . ?
C2 N1 C1 C6 -11.22(17) . . . 2_676 ?
C8 N1 C1 C6 168.44(10) . . . 2_676 ?
C1 N1 C2 O2 -166.71(11) . . . . ?
C8 N1 C2 O2 13.62(17) . . . . ?
C1 N1 C2 C3 13.62(17) . . . . ?
C8 N1 C2 C3 -166.05(10) . . . . ?
O2 C2 C3 C4 -7.22(18) . . . . ?
N1 C2 C3 C4 172.45(11) . . . . ?
O2 C2 C3 C7 172.72(11) . . . 2_676 ?
N1 C2 C3 C7 -7.62(16) . . . 2_676 ?
C7 C3 C4 C5 0.20(18) 2_676 . . . ?
C2 C3 C4 C5 -179.87(11) . . . . ?
C3 C4 C5 C6 -1.06(18) . . . . ?
C4 C5 C6 C7 1.07(18) . . . . ?
C4 C5 C6 C1 -177.42(11) . . . 2_676 ?
C5 C6 C7 C3 179.15(11) . . . 2_676 ?
C1 C6 C7 C3 -2.37(17) 2_676 . . 2_676 ?
C5 C6 C7 C7 -0.2(2) . . . 2_676 ?
C1 C6 C7 C7 178.24(13) 2_676 . . 2_676 ?
C1 N1 C8 C13 -113.09(13) . . . . ?
C2 N1 C8 C13 66.60(15) . . . . ?
C1 N1 C8 C9 67.34(15) . . . . ?
C2 N1 C8 C9 -112.97(13) . . . . ?
C13 C8 C9 C10 -1.10(18) . . . . ?
N1 C8 C9 C10 178.46(11) . . . . ?
C8 C9 C10 C11 -0.71(19) . . . . ?
C14 O3 C11 C12 4.89(17) . . . . ?
C14 O3 C11 C10 -175.48(11) . . . . ?
C9 C10 C11 O3 -177.69(11) . . . . ?
C9 C10 C11 C12 1.96(19) . . . . ?
O3 C11 C12 C13 178.21(11) . . . . ?
C10 C11 C12 C13 -1.41(18) . . . . ?
C9 C8 C13 C12 1.65(19) . . . . ?
N1 C8 C13 C12 -177.93(11) . . . . ?
C11 C12 C13 C8 -0.38(18) . . . . ?
C11 O3 C14 C15 176.17(10) . . . . ?
O3 C14 C15 C16 -56.78(14) . . . . ?
C14 C15 C16 C17 -178.12(11) . . . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
