# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1454173'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_chemical_name_systematic        
'naphthalene bridged phenoxyl-imidazolyl radical complex'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H20 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         436.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.6295(14)
_cell_length_b                   11.7772(10)
_cell_length_c                   23.646(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.3750(10)
_cell_angle_gamma                90
_cell_volume                     4281.4(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.4352
_cell_measurement_theta_max      26.3763
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22198
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             8756
_reflns_number_gt                7251
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0932
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_number_reflns         8756
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+1.8513P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N2 0.06321(6) 0.46518(9) 0.19550(4) 0.0164(2) Uani d . . . 1 . .
N N4 0.68505(6) 0.97330(9) 0.05483(4) 0.0147(2) Uani d . . . 1 . .
C C3 0.65912(7) 0.86220(10) 0.05277(5) 0.0146(2) Uani d . . . 1 . .
C C4 0.09340(8) 0.35590(11) 0.19959(5) 0.0165(2) Uani d . . . 1 . .
N N3 0.58144(6) 0.85007(9) 0.06644(4) 0.0158(2) Uani d . . . 1 . .
N N1 0.16922(7) 0.34651(9) 0.18310(4) 0.0179(2) Uani d . . . 1 . .
O O1 0.90328(6) 1.32075(9) 0.07271(5) 0.0340(3) Uani d . . . 1 . .
C C8 0.83694(8) 0.72220(11) -0.01046(5) 0.0182(3) Uani d . . . 1 . .
C C9 -0.06238(8) 0.41064(11) 0.24029(5) 0.0180(3) Uani d . . . 1 . .
C C10 0.81249(7) 0.92281(11) 0.01102(5) 0.0157(2) Uani d . . . 1 . .
C C11 0.04439(8) 0.26593(11) 0.22113(5) 0.0178(3) Uani d . . . 1 . .
C C12 -0.07997(8) 0.21072(11) 0.26550(5) 0.0210(3) Uani d . . . 1 . .
C C13 0.61845(7) 1.03666(11) 0.07136(5) 0.0155(2) Uani d . . . 1 . .
C C14 0.76853(7) 1.01607(10) 0.04171(5) 0.0145(2) Uani d . . . 1 . .
C C15 0.16317(8) 0.72970(11) 0.20453(5) 0.0182(3) Uani d . . . 1 . .
H H15 0.2001 0.7013 0.2379 0.022 Uiso calc U . R 1 . .
C C16 -0.03288(8) 0.29668(11) 0.24144(5) 0.0173(3) Uani d . . . 1 . .
C C17 0.92629(8) 0.86867(12) -0.04106(5) 0.0211(3) Uani d . . . 1 . .
H H17 0.9717 0.8909 -0.0606 0.025 Uiso calc U . R 1 . .
C C18 0.62547(7) 1.16014(10) 0.08332(5) 0.0156(2) Uani d . . . 1 . .
C C19 0.71258(8) 0.77326(11) 0.03464(5) 0.0159(2) Uani d . . . 1 . .
C C20 0.11707(8) 0.65408(11) 0.16480(5) 0.0173(3) Uani d . . . 1 . .
C C21 0.47154(7) 0.97599(11) 0.09709(5) 0.0155(2) Uani d . . . 1 . .
C C22 0.67202(8) 1.19860(11) 0.13569(5) 0.0190(3) Uani d . . . 1 . .
H H22 0.6979 1.1453 0.1638 0.023 Uiso calc U . R 1 . .
C C23 0.81298(8) 0.60689(11) -0.00690(5) 0.0217(3) Uani d . . . 1 . .
H H23 0.8468 0.5496 -0.0206 0.026 Uiso calc U . R 1 . .
O O2 -0.12702(6) 0.83006(8) 0.19291(5) 0.0326(2) Uani d . . . 1 . .
C C25 0.12540(8) 0.53015(11) 0.17461(5) 0.0172(3) Uani d . . . 1 . .
C C26 0.10081(8) 0.88729(11) 0.14707(6) 0.0231(3) Uani d . . . 1 . .
H H26 0.0944 0.9669 0.1414 0.028 Uiso calc U . R 1 . .
C C27 0.87381(8) 1.13898(12) 0.10657(5) 0.0218(3) Uani d . . . 1 . .
H H27 0.9141 1.1485 0.1415 0.026 Uiso calc U . R 1 . .
C C28 0.27109(8) 0.47557(11) 0.14511(5) 0.0183(3) Uani d . . . 1 . .
C C29 -0.08170(8) 0.54410(12) 0.15944(5) 0.0198(3) Uani d . . . 1 . .
H H29 -0.0956 0.4923 0.1283 0.024 Uiso calc U . R 1 . .
C C30 0.69003(8) 0.66059(11) 0.03551(5) 0.0195(3) Uani d . . . 1 . .
H H30 0.639 0.6391 0.0494 0.023 Uiso calc U . R 1 . .
C C31 0.78796(7) 0.80703(10) 0.01280(5) 0.0155(2) Uani d . . . 1 . .
C C32 0.43828(8) 0.88899(11) 0.12715(5) 0.0168(2) Uani d . . . 1 . .
H H32 0.4693 0.8196 0.1342 0.02 Uiso calc U . R 1 . .
C C33 0.55529(7) 0.95828(10) 0.07794(5) 0.0152(2) Uani d . . . 1 . .
C C34 0.36035(8) 0.90297(11) 0.14688(5) 0.0189(3) Uani d . . . 1 . .
H H34 0.3384 0.8432 0.1672 0.023 Uiso calc U . R 1 . .
C C35 0.58660(8) 1.23948(11) 0.04276(5) 0.0175(3) Uani d . . . 1 . .
H H35 0.5538 1.2144 0.0072 0.021 Uiso calc U . R 1 . .
C C36 -0.01805(8) 0.50724(11) 0.21227(5) 0.0164(2) Uani d . . . 1 . .
C C37 -0.17855(8) 0.35354(12) 0.28949(6) 0.0247(3) Uani d . . . 1 . .
H H37 -0.2268 0.3741 0.3067 0.03 Uiso calc U . R 1 . .
C C38 -0.11901(8) 0.64597(12) 0.15478(5) 0.0232(3) Uani d . . . 1 . .
H H38 -0.1618 0.6623 0.1219 0.028 Uiso calc U . R 1 . .
C C39 0.90642(8) 0.75633(11) -0.03768(5) 0.0210(3) Uani d . . . 1 . .
H H39 0.9393 0.7009 -0.0536 0.025 Uiso calc U . R 1 . .
C C40 0.00404(8) 0.60116(11) 0.25593(5) 0.0178(3) Uani d . . . 1 . .
H H40 0.0469 0.5868 0.2891 0.021 Uiso calc U . R 1 . .
C C41 -0.05031(9) 0.09724(12) 0.26598(6) 0.0252(3) Uani d . . . 1 . .
H H41 -0.0824 0.039 0.2805 0.03 Uiso calc U . R 1 . .
C C42 0.74197(8) 0.57676(11) 0.01591(5) 0.0224(3) Uani d . . . 1 . .
H H42 0.7275 0.4988 0.0186 0.027 Uiso calc U . R 1 . .
C C43 0.83064(7) 1.04157(11) 0.09719(5) 0.0176(3) Uani d . . . 1 . .
H H43 0.8391 0.9855 0.1265 0.021 Uiso calc U . R 1 . .
C C44 -0.03332(8) 0.70275(11) 0.25043(5) 0.0207(3) Uani d . . . 1 . .
H H44 -0.019 0.7565 0.2806 0.025 Uiso calc U . R 1 . .
C C45 -0.15326(9) 0.24291(12) 0.28941(5) 0.0246(3) Uani d . . . 1 . .
H H45 -0.1851 0.1866 0.3056 0.029 Uiso calc U . R 1 . .
C C46 0.15535(8) 0.84547(11) 0.19566(5) 0.0208(3) Uani d . . . 1 . .
H H46 0.1872 0.8965 0.2227 0.025 Uiso calc U . R 1 . .
C C47 0.64318(9) 1.39169(11) 0.10649(6) 0.0235(3) Uani d . . . 1 . .
H H47 0.6497 1.4707 0.1142 0.028 Uiso calc U . R 1 . .
C C48 -0.09614(8) 0.73402(12) 0.19891(6) 0.0226(3) Uani d . . . 1 . .
C C49 0.18989(8) 0.45459(11) 0.16728(5) 0.0169(2) Uani d . . . 1 . .
C C50 0.75129(8) 1.11836(11) 0.00288(5) 0.0173(3) Uani d . . . 1 . .
H H50 0.7066 1.1136 -0.0301 0.021 Uiso calc U . R 1 . .
C C51 0.06483(8) 0.69671(11) 0.11545(5) 0.0197(3) Uani d . . . 1 . .
H H51 0.0351 0.6459 0.0874 0.024 Uiso calc U . R 1 . .
C C52 0.59572(8) 1.35458(11) 0.05433(5) 0.0200(3) Uani d . . . 1 . .
H H52 0.5695 1.4083 0.0266 0.024 Uiso calc U . R 1 . .
C C53 0.05591(8) 0.81305(12) 0.10700(6) 0.0232(3) Uani d . . . 1 . .
H H53 0.019 0.8417 0.0737 0.028 Uiso calc U . R 1 . .
C C54 0.68088(9) 1.31382(12) 0.14713(6) 0.0239(3) Uani d . . . 1 . .
H H54 0.7129 1.3392 0.1829 0.029 Uiso calc U . R 1 . .
C C55 0.31445(8) 1.00423(11) 0.13695(5) 0.0197(3) Uani d . . . 1 . .
H H55 0.2617 1.0143 0.151 0.024 Uiso calc U . R 1 . .
C C56 0.79560(8) 1.21464(11) 0.01259(6) 0.0208(3) Uani d . . . 1 . .
H H56 0.7845 1.2739 -0.015 0.025 Uiso calc U . R 1 . .
C C57 0.86124(8) 1.23248(11) 0.06467(6) 0.0228(3) Uani d . . . 1 . .
C C58 -0.13381(8) 0.43735(12) 0.26431(5) 0.0218(3) Uani d . . . 1 . .
H H58 -0.1531 0.5139 0.2638 0.026 Uiso calc U . R 1 . .
C C59 0.34613(8) 1.09060(11) 0.10640(5) 0.0185(3) Uani d . . . 1 . .
H H59 0.3144 1.1595 0.0991 0.022 Uiso calc U . R 1 . .
C C60 0.07240(8) 0.15494(11) 0.22402(5) 0.0215(3) Uani d . . . 1 . .
H H60 0.1247 0.1354 0.2112 0.026 Uiso calc U . R 1 . .
C C61 0.42390(8) 1.07685(11) 0.08648(5) 0.0169(3) Uani d . . . 1 . .
H H61 0.4449 1.1363 0.0655 0.02 Uiso calc U . R 1 . .
C C62 0.42407(8) 0.50700(12) 0.10076(5) 0.0235(3) Uani d . . . 1 . .
H H62 0.4759 0.5177 0.0858 0.028 Uiso calc U . R 1 . .
C C63 0.28931(8) 0.58009(11) 0.12158(5) 0.0205(3) Uani d . . . 1 . .
H H63 0.2494 0.6412 0.1206 0.025 Uiso calc U . R 1 . .
C C64 0.36518(8) 0.59519(12) 0.09973(5) 0.0226(3) Uani d . . . 1 . .
H H64 0.3768 0.6665 0.084 0.027 Uiso calc U . R 1 . .
C C65 0.02369(9) 0.07015(12) 0.24599(6) 0.0259(3) Uani d . . . 1 . .
H H65 0.0426 -0.0066 0.2469 0.031 Uiso calc U . R 1 . .
C C66 0.88030(8) 0.95212(11) -0.01597(5) 0.0187(3) Uani d . . . 1 . .
H H66 0.8963 1.0297 -0.0177 0.022 Uiso calc U . R 1 . .
C C67 0.33151(8) 0.38763(11) 0.14614(5) 0.0213(3) Uani d . . . 1 . .
H H67 0.3207 0.3164 0.1623 0.026 Uiso calc U . R 1 . .
C C68 0.40677(8) 0.40286(12) 0.12389(5) 0.0236(3) Uani d . . . 1 . .
H H68 0.4467 0.3419 0.1244 0.028 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N2 C4 . 1.3681(16) ?
N2 C25 . 1.3953(16) ?
N2 C36 . 1.4824(15) ?
N4 C3 . 1.3681(16) ?
N4 C13 . 1.3927(15) ?
N4 C14 . 1.4825(14) ?
C3 N3 . 1.3190(15) ?
C3 C19 . 1.4519(17) ?
C4 N1 . 1.3172(15) ?
C4 C11 . 1.4524(17) ?
N3 C33 . 1.3803(16) ?
N1 C49 . 1.3813(16) ?
O1 C57 . 1.2262(16) ?
C8 C23 . 1.4153(19) ?
C8 C39 . 1.4166(18) ?
C8 C31 . 1.4277(17) ?
C9 C58 . 1.3772(17) ?
C9 C16 . 1.4178(18) ?
C9 C36 . 1.5423(17) ?
C10 C66 . 1.3759(17) ?
C10 C31 . 1.4192(17) ?
C10 C14 . 1.5444(16) ?
C11 C60 . 1.3764(18) ?
C11 C16 . 1.4244(17) ?
C12 C41 . 1.4139(19) ?
C12 C45 . 1.4174(18) ?
C12 C16 . 1.4287(18) ?
C13 C33 . 1.3807(17) ?
C13 C18 . 1.4818(17) ?
C14 C50 . 1.5093(17) ?
C14 C43 . 1.5148(16) ?
C15 C46 . 1.3815(18) ?
C15 C20 . 1.3967(17) ?
C15 H15 . 0.95 ?
C17 C39 . 1.3646(19) ?
C17 C66 . 1.4099(18) ?
C17 H17 . 0.95 ?
C18 C35 . 1.3973(17) ?
C18 C22 . 1.3942(17) ?
C19 C30 . 1.3740(18) ?
C19 C31 . 1.4255(16) ?
C20 C51 . 1.3919(17) ?
C20 C25 . 1.4800(18) ?
C21 C32 . 1.3994(17) ?
C21 C61 . 1.4003(17) ?
C21 C33 . 1.4749(16) ?
C22 C54 . 1.3857(19) ?
C22 H22 . 0.95 ?
C23 C42 . 1.3654(18) ?
C23 H23 . 0.95 ?
O2 C48 . 1.2278(16) ?
C25 C49 . 1.3788(17) ?
C26 C53 . 1.3841(19) ?
C26 C46 . 1.3916(18) ?
C26 H26 . 0.95 ?
C27 C43 . 1.3292(18) ?
C27 C57 . 1.4706(19) ?
C27 H27 . 0.95 ?
C28 C67 . 1.3988(18) ?
C28 C63 . 1.4010(18) ?
C28 C49 . 1.4785(17) ?
C29 C38 . 1.3298(19) ?
C29 C36 . 1.5137(16) ?
C29 H29 . 0.95 ?
C30 C42 . 1.4085(18) ?
C30 H30 . 0.95 ?
C32 C34 . 1.3903(17) ?
C32 H32 . 0.95 ?
C34 C55 . 1.3896(18) ?
C34 H34 . 0.95 ?
C35 C52 . 1.3852(18) ?
C35 H35 . 0.95 ?
C36 C40 . 1.5099(17) ?
C37 C45 . 1.362(2) ?
C37 C58 . 1.4028(19) ?
C37 H37 . 0.95 ?
C38 C48 . 1.4690(19) ?
C38 H38 . 0.95 ?
C39 H39 . 0.95 ?
C40 C44 . 1.3274(18) ?
C40 H40 . 0.95 ?
C41 C65 . 1.3639(19) ?
C41 H41 . 0.95 ?
C42 H42 . 0.95 ?
C43 H43 . 0.95 ?
C44 C48 . 1.4671(18) ?
C44 H44 . 0.95 ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C47 C54 . 1.3812(19) ?
C47 C52 . 1.3902(18) ?
C47 H47 . 0.95 ?
C50 C56 . 1.3269(18) ?
C50 H50 . 0.95 ?
C51 C53 . 1.3880(19) ?
C51 H51 . 0.95 ?
C52 H52 . 0.95 ?
C53 H53 . 0.95 ?
C54 H54 . 0.95 ?
C55 C59 . 1.3894(18) ?
C55 H55 . 0.95 ?
C56 C57 . 1.4691(19) ?
C56 H56 . 0.95 ?
C58 H58 . 0.95 ?
C59 C61 . 1.3901(17) ?
C59 H59 . 0.95 ?
C60 C65 . 1.4103(19) ?
C60 H60 . 0.95 ?
C61 H61 . 0.95 ?
C62 C64 . 1.3851(19) ?
C62 C68 . 1.389(2) ?
C62 H62 . 0.95 ?
C63 C64 . 1.3875(18) ?
C63 H63 . 0.95 ?
C64 H64 . 0.95 ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?
C67 C68 . 1.3841(18) ?
C67 H67 . 0.95 ?
C68 H68 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N2 C25 . . 106.71(10) ?
C4 N2 C36 . . 126.63(10) ?
C25 N2 C36 . . 126.62(10) ?
C3 N4 C13 . . 106.91(10) ?
C3 N4 C14 . . 125.72(10) ?
C13 N4 C14 . . 127.37(10) ?
N3 C3 N4 . . 112.00(11) ?
N3 C3 C19 . . 126.74(11) ?
N4 C3 C19 . . 121.19(10) ?
N1 C4 N2 . . 112.03(11) ?
N1 C4 C11 . . 127.02(11) ?
N2 C4 C11 . . 120.94(11) ?
C3 N3 C33 . . 105.47(10) ?
C4 N1 C49 . . 105.65(10) ?
C23 C8 C39 . . 122.14(12) ?
C23 C8 C31 . . 118.85(11) ?
C39 C8 C31 . . 118.99(12) ?
C58 C9 C16 . . 119.56(12) ?
C58 C9 C36 . . 117.96(11) ?
C16 C9 C36 . . 122.47(11) ?
C66 C10 C31 . . 119.32(11) ?
C66 C10 C14 . . 118.99(11) ?
C31 C10 C14 . . 121.59(10) ?
C60 C11 C16 . . 120.40(12) ?
C60 C11 C4 . . 121.82(11) ?
C16 C11 C4 . . 117.74(11) ?
C41 C12 C45 . . 122.48(12) ?
C41 C12 C16 . . 118.78(12) ?
C45 C12 C16 . . 118.73(12) ?
C33 C13 N4 . . 105.02(10) ?
C33 C13 C18 . . 131.64(11) ?
N4 C13 C18 . . 123.10(10) ?
N4 C14 C50 . . 109.34(9) ?
N4 C14 C43 . . 109.70(9) ?
C50 C14 C43 . . 112.64(10) ?
N4 C14 C10 . . 109.84(9) ?
C50 C14 C10 . . 109.12(9) ?
C43 C14 C10 . . 106.14(9) ?
C46 C15 C20 . . 120.42(12) ?
C46 C15 H15 . . 119.8 ?
C20 C15 H15 . . 119.8 ?
C9 C16 C11 . . 121.78(11) ?
C9 C16 C12 . . 119.30(11) ?
C11 C16 C12 . . 118.88(12) ?
C39 C17 C66 . . 120.83(12) ?
C39 C17 H17 . . 119.6 ?
C66 C17 H17 . . 119.6 ?
C35 C18 C22 . . 119.03(11) ?
C35 C18 C13 . . 121.15(11) ?
C22 C18 C13 . . 119.82(11) ?
C30 C19 C31 . . 120.38(11) ?
C30 C19 C3 . . 121.97(11) ?
C31 C19 C3 . . 117.57(11) ?
C51 C20 C15 . . 119.18(12) ?
C51 C20 C25 . . 120.60(11) ?
C15 C20 C25 . . 120.21(11) ?
C32 C21 C61 . . 118.55(11) ?
C32 C21 C33 . . 118.93(11) ?
C61 C21 C33 . . 122.52(11) ?
C54 C22 C18 . . 120.62(12) ?
C54 C22 H22 . . 119.7 ?
C18 C22 H22 . . 119.7 ?
C42 C23 C8 . . 121.03(12) ?
C42 C23 H23 . . 119.5 ?
C8 C23 H23 . . 119.5 ?
C49 C25 N2 . . 105.20(11) ?
C49 C25 C20 . . 131.49(11) ?
N2 C25 C20 . . 123.31(11) ?
C53 C26 C46 . . 120.09(12) ?
C53 C26 H26 . . 120.0 ?
C46 C26 H26 . . 120.0 ?
C43 C27 C57 . . 122.12(12) ?
C43 C27 H27 . . 118.9 ?
C57 C27 H27 . . 118.9 ?
C67 C28 C63 . . 118.20(11) ?
C67 C28 C49 . . 119.33(12) ?
C63 C28 C49 . . 122.44(11) ?
C38 C29 C36 . . 122.71(12) ?
C38 C29 H29 . . 118.6 ?
C36 C29 H29 . . 118.6 ?
C19 C30 C42 . . 120.49(12) ?
C19 C30 H30 . . 119.8 ?
C42 C30 H30 . . 119.8 ?
C10 C31 C19 . . 121.62(11) ?
C10 C31 C8 . . 119.63(11) ?
C19 C31 C8 . . 118.68(11) ?
C34 C32 C21 . . 120.77(12) ?
C34 C32 H32 . . 119.6 ?
C21 C32 H32 . . 119.6 ?
C13 C33 N3 . . 110.60(10) ?
C13 C33 C21 . . 129.21(11) ?
N3 C33 C21 . . 120.12(10) ?
C32 C34 C55 . . 120.12(12) ?
C32 C34 H34 . . 119.9 ?
C55 C34 H34 . . 119.9 ?
C52 C35 C18 . . 120.15(11) ?
C52 C35 H35 . . 119.9 ?
C18 C35 H35 . . 119.9 ?
N2 C36 C40 . . 109.05(9) ?
N2 C36 C29 . . 110.02(9) ?
C40 C36 C29 . . 112.93(10) ?
N2 C36 C9 . . 109.95(10) ?
C40 C36 C9 . . 108.17(9) ?
C29 C36 C9 . . 106.66(10) ?
C45 C37 C58 . . 120.37(12) ?
C45 C37 H37 . . 119.8 ?
C58 C37 H37 . . 119.8 ?
C29 C38 C48 . . 122.07(12) ?
C29 C38 H38 . . 119.0 ?
C48 C38 H38 . . 119.0 ?
C17 C39 C8 . . 120.19(12) ?
C17 C39 H39 . . 119.9 ?
C8 C39 H39 . . 119.9 ?
C44 C40 C36 . . 123.43(11) ?
C44 C40 H40 . . 118.3 ?
C36 C40 H40 . . 118.3 ?
C65 C41 C12 . . 121.04(12) ?
C65 C41 H41 . . 119.5 ?
C12 C41 H41 . . 119.5 ?
C23 C42 C30 . . 120.37(12) ?
C23 C42 H42 . . 119.8 ?
C30 C42 H42 . . 119.8 ?
C27 C43 C14 . . 122.86(12) ?
C27 C43 H43 . . 118.6 ?
C14 C43 H43 . . 118.6 ?
C40 C44 C48 . . 121.63(12) ?
C40 C44 H44 . . 119.2 ?
C48 C44 H44 . . 119.2 ?
C37 C45 C12 . . 120.81(12) ?
C37 C45 H45 . . 119.6 ?
C12 C45 H45 . . 119.6 ?
C15 C46 C26 . . 119.93(12) ?
C15 C46 H46 . . 120.0 ?
C26 C46 H46 . . 120.0 ?
C54 C47 C52 . . 120.07(12) ?
C54 C47 H47 . . 120.0 ?
C52 C47 H47 . . 120.0 ?
O2 C48 C44 . . 121.17(13) ?
O2 C48 C38 . . 121.86(12) ?
C44 C48 C38 . . 116.97(11) ?
C25 C49 N1 . . 110.40(11) ?
C25 C49 C28 . . 129.08(12) ?
N1 C49 C28 . . 120.51(11) ?
C56 C50 C14 . . 123.12(11) ?
C56 C50 H50 . . 118.4 ?
C14 C50 H50 . . 118.4 ?
C53 C51 C20 . . 120.36(12) ?
C53 C51 H51 . . 119.8 ?
C20 C51 H51 . . 119.8 ?
C35 C52 C47 . . 120.17(12) ?
C35 C52 H52 . . 119.9 ?
C47 C52 H52 . . 119.9 ?
C26 C53 C51 . . 119.97(12) ?
C26 C53 H53 . . 120.0 ?
C51 C53 H53 . . 120.0 ?
C47 C54 C22 . . 119.96(12) ?
C47 C54 H54 . . 120.0 ?
C22 C54 H54 . . 120.0 ?
C59 C55 C34 . . 119.65(11) ?
C59 C55 H55 . . 120.2 ?
C34 C55 H55 . . 120.2 ?
C50 C56 C57 . . 122.09(12) ?
C50 C56 H56 . . 119.0 ?
C57 C56 H56 . . 119.0 ?
O1 C57 C27 . . 121.84(13) ?
O1 C57 C56 . . 121.67(13) ?
C27 C57 C56 . . 116.49(11) ?
C9 C58 C37 . . 121.16(13) ?
C9 C58 H58 . . 119.4 ?
C37 C58 H58 . . 119.4 ?
C61 C59 C55 . . 120.40(12) ?
C61 C59 H59 . . 119.8 ?
C55 C59 H59 . . 119.8 ?
C11 C60 C65 . . 120.19(12) ?
C11 C60 H60 . . 119.9 ?
C65 C60 H60 . . 119.9 ?
C59 C61 C21 . . 120.48(11) ?
C59 C61 H61 . . 119.8 ?
C21 C61 H61 . . 119.8 ?
C64 C62 C68 . . 119.55(12) ?
C64 C62 H62 . . 120.2 ?
C68 C62 H62 . . 120.2 ?
C64 C63 C28 . . 120.59(12) ?
C64 C63 H63 . . 119.7 ?
C28 C63 H63 . . 119.7 ?
C62 C64 C63 . . 120.47(13) ?
C62 C64 H64 . . 119.8 ?
C63 C64 H64 . . 119.8 ?
C41 C65 C60 . . 120.65(13) ?
C41 C65 H65 . . 119.7 ?
C60 C65 H65 . . 119.7 ?
C10 C66 C17 . . 120.92(12) ?
C10 C66 H66 . . 119.5 ?
C17 C66 H66 . . 119.5 ?
C68 C67 C28 . . 120.98(13) ?
C68 C67 H67 . . 119.5 ?
C28 C67 H67 . . 119.5 ?
C67 C68 C62 . . 120.20(12) ?
C67 C68 H68 . . 119.9 ?
C62 C68 H68 . . 119.9 ?


_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       'photochromic compound'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and hexane'
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1454174'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_chemical_name_systematic        
'naphthalene bridged naphthoxyl-imidazolyl radical complex'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H22 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         486.54
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.417(3)
_cell_length_b                   7.846(3)
_cell_length_c                   15.614(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.024(4)
_cell_angle_gamma                90
_cell_volume                     1206.5(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3312
_cell_measurement_theta_min      2.7598
_cell_measurement_theta_max      26.2911
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6504
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_full        26.55
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4678
_reflns_number_gt                4319
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0728
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         4678
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+0.2858P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
;
_refine_ls_abs_structure_Flack   0.8(8)

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'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6168(2) 0.2695(3) 0.47715(15) 0.0253(5) Uani d . . . 1 . .
H H1 0.5831 0.3699 0.4433 0.03 Uiso calc U . R 1 . .
C C2 0.7425(2) 0.0070(3) 0.49674(14) 0.0181(4) Uani d . . . 1 . .
C C3 0.8352(2) -0.2929(3) 0.59637(15) 0.0247(5) Uani d . . . 1 . .
H H3 0.8646 -0.3958 0.6289 0.03 Uiso calc U . R 1 . .
C C4 0.8245(2) -0.1122(3) 0.46932(14) 0.0169(4) Uani d . . . 1 . .
C C24 0.7046(2) 0.1886(3) 0.35205(14) 0.0169(4) Uani d . . . 1 . .
C C5 0.6370(2) 0.0971(3) 0.60799(15) 0.0263(5) Uani d . . . 1 . .
H H5 0.6174 0.0782 0.6625 0.032 Uiso calc U . R 1 . .
C C6 0.6894(2) 0.1541(3) 0.44529(14) 0.0188(4) Uani d . . . 1 . .
C C7 0.5916(3) 0.2415(3) 0.55912(16) 0.0302(6) Uani d . . . 1 . .
H H7 0.5426 0.3238 0.5806 0.036 Uiso calc U . R 1 . .
C C8 0.8701(2) -0.2584(3) 0.51824(15) 0.0207(5) Uani d . . . 1 . .
H H8 0.9252 -0.3363 0.4993 0.025 Uiso calc U . R 1 . .
C C9 0.7593(2) -0.1793(3) 0.62573(15) 0.0246(5) Uani d . . . 1 . .
H H9 0.7371 -0.2041 0.6788 0.03 Uiso calc U . R 1 . .
C C10 0.7131(2) -0.0251(3) 0.57829(15) 0.0220(5) Uani d . . . 1 . .
C C12 0.9781(2) -0.1725(3) 0.20622(14) 0.0174(4) Uani d . . . 1 . .
C C13 1.0394(2) -0.1757(3) 0.06933(15) 0.0242(5) Uani d . . . 1 . .
H H13 1.0376 -0.1227 0.0143 0.029 Uiso calc U . R 1 . .
C C14 1.0439(2) -0.3296(3) 0.22933(15) 0.0218(5) Uani d . . . 1 . .
H H14 1.0463 -0.3837 0.2842 0.026 Uiso calc U . R 1 . .
C C15 1.1037(2) -0.3309(3) 0.09320(15) 0.0222(5) Uani d . . . 1 . .
H H15 1.146 -0.3847 0.0549 0.027 Uiso calc U . R 1 . .
C C16 0.9775(2) -0.0966(3) 0.12510(16) 0.0242(5) Uani d . . . 1 . .
H H16 0.9341 0.0105 0.1079 0.029 Uiso calc U . R 1 . .
C C17 1.1056(2) -0.4072(3) 0.17345(16) 0.0267(5) Uani d . . . 1 . .
H H17 1.1498 -0.5138 0.1903 0.032 Uiso calc U . R 1 . .
C C18 0.6029(2) 0.1779(4) 0.02305(16) 0.0302(6) Uani d . . . 1 . .
H H18 0.5288 0.1331 -0.0249 0.036 Uiso calc U . R 1 . .
C C19 0.8203(2) 0.3083(3) 0.16204(15) 0.0220(5) Uani d . . . 1 . .
H H19 0.8959 0.3522 0.2092 0.026 Uiso calc U . R 1 . .
C C20 0.6551(2) 0.3376(4) 0.01444(17) 0.0328(6) Uani d . . . 1 . .
H H20 0.6162 0.4023 -0.0393 0.039 Uiso calc U . R 1 . .
C C21 0.6589(2) 0.0843(3) 0.10137(15) 0.0227(5) Uani d . . . 1 . .
H H21 0.6233 -0.0249 0.1072 0.027 Uiso calc U . R 1 . .
C C22 0.7672(2) 0.1495(3) 0.17163(14) 0.0187(4) Uani d . . . 1 . .
C C23 0.7632(2) 0.4026(3) 0.08373(17) 0.0288(5) Uani d . . . 1 . .
H H23 0.7985 0.5119 0.0778 0.035 Uiso calc U . R 1 . .
C C25 0.5061(2) 0.3283(3) 0.23127(14) 0.0181(4) Uani d . . . 1 . .
C C26 0.5784(2) 0.4944(3) 0.24748(15) 0.0219(5) Uani d . . . 1 . .
C C27 0.3649(2) 0.0210(3) 0.20099(15) 0.0233(5) Uani d . . . 1 . .
H H27 0.316 -0.0833 0.1915 0.028 Uiso calc U . R 1 . .
C C28 0.7161(2) 0.4965(3) 0.31182(15) 0.0230(5) Uani d . . . 1 . .
H H28 0.7659 0.6002 0.3214 0.028 Uiso calc U . R 1 . .
C C29 0.5644(2) 0.1836(3) 0.28010(14) 0.0161(4) Uani d . . . 1 . .
C C30 0.4932(2) 0.0299(3) 0.26422(14) 0.0189(4) Uani d . . . 1 . .
H H30 0.5332 -0.0692 0.2971 0.023 Uiso calc U . R 1 . .
C C31 0.7744(2) 0.3590(3) 0.35747(15) 0.0205(5) Uani d . . . 1 . .
H H31 0.866 0.3682 0.396 0.025 Uiso calc U . R 1 . .
C C32 0.3070(2) 0.1656(3) 0.15092(15) 0.0254(5) Uani d . . . 1 . .
H H32 0.2191 0.1595 0.1069 0.03 Uiso calc U . R 1 . .
C C33 0.3779(2) 0.3172(3) 0.16575(15) 0.0227(5) Uani d . . . 1 . .
H H33 0.339 0.4149 0.131 0.027 Uiso calc U . R 1 . .
C C34 0.9115(2) -0.0966(3) 0.26669(14) 0.0165(4) Uani d . . . 1 . .
C C35 0.8268(2) 0.0432(3) 0.25307(13) 0.0166(4) Uani d . . . 1 . .
C C36 0.8533(2) -0.0767(3) 0.38636(14) 0.0156(4) Uani d . . . 1 . .
N N1 0.92764(16) -0.1695(2) 0.35011(12) 0.0170(4) Uani d . . . 1 . .
N N2 0.79124(17) 0.0560(2) 0.33136(11) 0.0156(4) Uani d . . . 1 . .
O O1 0.52517(18) 0.6247(2) 0.20868(12) 0.0333(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.373(3) ?
C1 C7 . 1.405(3) ?
C1 H1 . 0.95 ?
C2 C6 . 1.412(3) ?
C2 C10 . 1.425(3) ?
C2 C4 . 1.424(3) ?
C3 C9 . 1.365(3) ?
C3 C8 . 1.408(3) ?
C3 H3 . 0.95 ?
C4 C8 . 1.374(3) ?
C4 C36 . 1.449(3) ?
C24 N2 . 1.481(3) ?
C24 C31 . 1.512(3) ?
C24 C29 . 1.525(3) ?
C24 C6 . 1.539(3) ?
C5 C7 . 1.362(4) ?
C5 C10 . 1.414(3) ?
C5 H5 . 0.95 ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 C10 . 1.419(3) ?
C9 H9 . 0.95 ?
C12 C16 . 1.398(3) ?
C12 C14 . 1.399(3) ?
C12 C34 . 1.468(3) ?
C13 C15 . 1.381(3) ?
C13 C16 . 1.388(3) ?
C13 H13 . 0.95 ?
C14 C17 . 1.382(3) ?
C14 H14 . 0.95 ?
C15 C17 . 1.383(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C21 . 1.382(3) ?
C18 C20 . 1.390(4) ?
C18 H18 . 0.95 ?
C19 C23 . 1.386(3) ?
C19 C22 . 1.391(3) ?
C19 H19 . 0.95 ?
C20 C23 . 1.380(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.390(3) ?
C21 H21 . 0.95 ?
C22 C35 . 1.478(3) ?
C23 H23 . 0.95 ?
C25 C29 . 1.392(3) ?
C25 C33 . 1.396(3) ?
C25 C26 . 1.485(3) ?
C26 O1 . 1.225(3) ?
C26 C28 . 1.459(3) ?
C27 C30 . 1.380(3) ?
C27 C32 . 1.398(3) ?
C27 H27 . 0.95 ?
C28 C31 . 1.326(3) ?
C28 H28 . 0.95 ?
C29 C30 . 1.395(3) ?
C30 H30 . 0.95 ?
C31 H31 . 0.95 ?
C32 C33 . 1.379(3) ?
C32 H32 . 0.95 ?
C33 H33 . 0.95 ?
C34 N1 . 1.381(3) ?
C34 C35 . 1.380(3) ?
C35 N2 . 1.392(2) ?
C36 N1 . 1.318(3) ?
C36 N2 . 1.370(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C7 . . 121.0(2) ?
C6 C1 H1 . . 119.5 ?
C7 C1 H1 . . 119.5 ?
C6 C2 C10 . . 119.61(19) ?
C6 C2 C4 . . 121.88(19) ?
C10 C2 C4 . . 118.51(19) ?
C9 C3 C8 . . 120.4(2) ?
C9 C3 H3 . . 119.8 ?
C8 C3 H3 . . 119.8 ?
C8 C4 C2 . . 120.90(19) ?
C8 C4 C36 . . 121.53(19) ?
C2 C4 C36 . . 117.53(19) ?
N2 C24 C31 . . 108.48(16) ?
N2 C24 C29 . . 109.06(16) ?
C31 C24 C29 . . 113.07(18) ?
N2 C24 C6 . . 109.95(17) ?
C31 C24 C6 . . 107.37(17) ?
C29 C24 C6 . . 108.87(16) ?
C7 C5 C10 . . 120.6(2) ?
C7 C5 H5 . . 119.7 ?
C10 C5 H5 . . 119.7 ?
C1 C6 C2 . . 119.5(2) ?
C1 C6 C24 . . 117.8(2) ?
C2 C6 C24 . . 122.67(19) ?
C5 C7 C1 . . 120.5(2) ?
C5 C7 H7 . . 119.8 ?
C1 C7 H7 . . 119.8 ?
C4 C8 C3 . . 120.1(2) ?
C4 C8 H8 . . 119.9 ?
C3 C8 H8 . . 119.9 ?
C3 C9 C10 . . 121.1(2) ?
C3 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C5 C10 C9 . . 122.5(2) ?
C5 C10 C2 . . 118.6(2) ?
C9 C10 C2 . . 118.8(2) ?
C16 C12 C14 . . 117.8(2) ?
C16 C12 C34 . . 123.1(2) ?
C14 C12 C34 . . 119.09(19) ?
C15 C13 C16 . . 120.6(2) ?
C15 C13 H13 . . 119.7 ?
C16 C13 H13 . . 119.7 ?
C17 C14 C12 . . 121.0(2) ?
C17 C14 H14 . . 119.5 ?
C12 C14 H14 . . 119.5 ?
C13 C15 C17 . . 119.3(2) ?
C13 C15 H15 . . 120.4 ?
C17 C15 H15 . . 120.4 ?
C13 C16 C12 . . 120.8(2) ?
C13 C16 H16 . . 119.6 ?
C12 C16 H16 . . 119.6 ?
C15 C17 C14 . . 120.6(2) ?
C15 C17 H17 . . 119.7 ?
C14 C17 H17 . . 119.7 ?
C21 C18 C20 . . 119.9(2) ?
C21 C18 H18 . . 120.0 ?
C20 C18 H18 . . 120.0 ?
C23 C19 C22 . . 120.1(2) ?
C23 C19 H19 . . 120.0 ?
C22 C19 H19 . . 120.0 ?
C23 C20 C18 . . 120.1(2) ?
C23 C20 H20 . . 119.9 ?
C18 C20 H20 . . 119.9 ?
C18 C21 C22 . . 120.2(2) ?
C18 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C21 C22 C19 . . 119.6(2) ?
C21 C22 C35 . . 118.4(2) ?
C19 C22 C35 . . 121.9(2) ?
C20 C23 C19 . . 120.1(2) ?
C20 C23 H23 . . 120.0 ?
C19 C23 H23 . . 120.0 ?
C29 C25 C33 . . 119.5(2) ?
C29 C25 C26 . . 121.06(18) ?
C33 C25 C26 . . 119.4(2) ?
O1 C26 C28 . . 121.1(2) ?
O1 C26 C25 . . 121.7(2) ?
C28 C26 C25 . . 117.22(19) ?
C30 C27 C32 . . 120.0(2) ?
C30 C27 H27 . . 120.0 ?
C32 C27 H27 . . 120.0 ?
C31 C28 C26 . . 122.4(2) ?
C31 C28 H28 . . 118.8 ?
C26 C28 H28 . . 118.8 ?
C25 C29 C30 . . 119.72(19) ?
C25 C29 C24 . . 121.63(19) ?
C30 C29 C24 . . 118.64(19) ?
C27 C30 C29 . . 120.4(2) ?
C27 C30 H30 . . 119.8 ?
C29 C30 H30 . . 119.8 ?
C28 C31 C24 . . 124.2(2) ?
C28 C31 H31 . . 117.9 ?
C24 C31 H31 . . 117.9 ?
C33 C32 C27 . . 119.7(2) ?
C33 C32 H32 . . 120.1 ?
C27 C32 H32 . . 120.1 ?
C32 C33 C25 . . 120.6(2) ?
C32 C33 H33 . . 119.7 ?
C25 C33 H33 . . 119.7 ?
N1 C34 C35 . . 110.46(18) ?
N1 C34 C12 . . 120.04(19) ?
C35 C34 C12 . . 129.48(19) ?
C34 C35 N2 . . 105.17(17) ?
C34 C35 C22 . . 130.51(18) ?
N2 C35 C22 . . 123.89(18) ?
N1 C36 N2 . . 111.94(18) ?
N1 C36 C4 . . 126.87(19) ?
N2 C36 C4 . . 120.91(18) ?
C36 N1 C34 . . 105.57(18) ?
C36 N2 C35 . . 106.83(17) ?
C36 N2 C24 . . 126.42(16) ?
C35 N2 C24 . . 126.75(17) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       'photochromic compound'
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1454175'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_chemical_name_systematic        'by-product 1'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H20 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         468.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.4123(13)
_cell_length_b                   10.6141(13)
_cell_length_c                   22.372(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.1402(17)
_cell_angle_gamma                90
_cell_volume                     2425.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4504
_cell_measurement_theta_min      2.6696
_cell_measurement_theta_max      25.2922
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          600.000
_exptl_crystal_size_mid          200.000
_exptl_crystal_size_min          50.000
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.10
_exptl_absorpt_correction_T_max  0.10

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11645
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_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       -26
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             4436
_reflns_number_gt                3603
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0800
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_number_reflns         4436
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+0.9079P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N3 0.86251(10) 0.18461(9) 0.13742(5) 0.0177(2) Uani d . . . 1 . .
O O2 0.87894(10) 0.24510(9) 0.23680(4) 0.0305(2) Uani d . . . 1 . .
O O3 0.83902(9) -0.02781(9) 0.12758(4) 0.0291(2) Uani d . . . 1 . .
N N4 0.64659(10) 0.22549(10) 0.09890(5) 0.0195(2) Uani d . . . 1 . .
C C5 0.78640(12) 0.17893(11) 0.02494(6) 0.0182(3) Uani d . . . 1 . .
O O1 0.15599(10) 0.33347(12) 0.07244(5) 0.0456(3) Uani d . . . 1 . .
C C7 0.90948(13) 0.15334(12) 0.01490(6) 0.0217(3) Uani d . . . 1 . .
C C8 0.68028(13) 0.19403(13) -0.02504(6) 0.0228(3) Uani d . . . 1 . .
C C9 0.55405(13) 0.22341(15) -0.01535(6) 0.0297(3) Uani d . . . 1 . .
C C10 0.90043(12) 0.05999(12) 0.15358(6) 0.0209(3) Uani d . . . 1 . .
C C11 0.93158(14) 0.14054(13) -0.04499(6) 0.0256(3) Uani d . . . 1 . .
C C12 0.90440(12) 0.44792(12) 0.11094(6) 0.0215(3) Uani d . . . 1 . .
C C13 0.70287(14) 0.18043(14) -0.08555(6) 0.0294(3) Uani d . . . 1 . .
C C14 0.75599(12) 0.19698(11) 0.08568(5) 0.0172(3) Uani d . . . 1 . .
C C15 0.86911(12) 0.27741(12) 0.18421(6) 0.0200(3) Uani d . . . 1 . .
C C16 1.02251(13) 0.04220(12) 0.19993(6) 0.0229(3) Uani d . . . 1 . .
C C17 0.86843(12) 0.41082(12) 0.16510(6) 0.0205(3) Uani d . . . 1 . .
C C18 0.83159(14) 0.15379(14) -0.09368(6) 0.0281(3) Uani d . . . 1 . .
C C19 1.02804(15) -0.05958(14) 0.23947(6) 0.0297(3) Uani d . . . 1 . .
C C20 0.48500(13) 0.37580(14) 0.05555(6) 0.0254(3) Uani d . . . 1 . .
C C21 0.83911(14) 0.50147(14) 0.20568(7) 0.0294(3) Uani d . . . 1 . .
C C39 0.91098(14) 0.57502(13) 0.09748(7) 0.0291(3) Uani d . . . 1 . .
C C23 0.36419(14) 0.40495(15) 0.06160(6) 0.0291(3) Uani d . . . 1 . .
C C24 0.26782(13) 0.30659(15) 0.06686(6) 0.0305(3) Uani d . . . 1 . .
C C25 0.53087(12) 0.24272(13) 0.04977(6) 0.0228(3) Uani d . . . 1 . .
C C26 0.43244(13) 0.14600(14) 0.06132(6) 0.0259(3) Uani d . . . 1 . .
C C27 0.88127(15) 0.66435(14) 0.13774(8) 0.0355(4) Uani d . . . 1 . .
C C28 0.31177(14) 0.17551(15) 0.06753(6) 0.0295(3) Uani d . . . 1 . .
C C29 1.13101(14) 0.11920(15) 0.20226(7) 0.0310(3) Uani d . . . 1 . .
C C31 0.84503(15) 0.62759(15) 0.19157(8) 0.0381(4) Uani d . . . 1 . .
C C32 0.59585(17) 0.1945(2) -0.13442(7) 0.0499(5) Uani d . . . 1 . .
C C33 1.24988(17) -0.00731(17) 0.28349(8) 0.0457(4) Uani d . . . 1 . .
C C34 1.24521(16) 0.09295(18) 0.24376(8) 0.0440(4) Uani d . . . 1 . .
C C35 0.47410(18) 0.2203(3) -0.12392(8) 0.0673(7) Uani d . . . 1 . .
C C36 0.45307(17) 0.2355(2) -0.06424(7) 0.0548(6) Uani d . . . 1 . .
H H6 0.9819(14) 0.1452(13) 0.0492(6) 0.024(4) Uiso d . . . 1 . .
H H16 0.9275(13) 0.3847(13) 0.0832(6) 0.022(4) Uiso d . . . 1 . .
H H12 0.5505(14) 0.4404(14) 0.0545(6) 0.030(4) Uiso d . . . 1 . .
H H17 0.9375(14) 0.5990(14) 0.0584(7) 0.033(4) Uiso d . . . 1 . .
H H7 1.0205(15) 0.1235(13) -0.0515(6) 0.028(4) Uiso d . . . 1 . .
H H14 0.2491(15) 0.1099(15) 0.0730(7) 0.037(4) Uiso d . . . 1 . .
H H1 1.1269(14) 0.1884(14) 0.1749(7) 0.031(4) Uiso d . . . 1 . .
H H8 0.8443(14) 0.1450(14) -0.1358(7) 0.033(4) Uiso d . . . 1 . .
H H20 0.8161(15) 0.4753(14) 0.2443(7) 0.035(4) Uiso d . . . 1 . .
H H13 0.4635(15) 0.0580(15) 0.0625(7) 0.034(4) Uiso d . . . 1 . .
H H5 0.9508(15) -0.1145(15) 0.2373(7) 0.036(4) Uiso d . . . 1 . .
H H15 0.3375(15) 0.4926(15) 0.0650(7) 0.033(4) Uiso d . . . 1 . .
H H18 0.8849(16) 0.7551(17) 0.1277(7) 0.045(5) Uiso d . . . 1 . .
H H2 1.3211(18) 0.1476(17) 0.2458(8) 0.054(5) Uiso d . . . 1 . .
H H19 0.8229(16) 0.6905(16) 0.2202(8) 0.047(5) Uiso d . . . 1 . .
H H9 0.6112(17) 0.1844(16) -0.1746(8) 0.051(5) Uiso d . . . 1 . .
H H3 1.3300(18) -0.0245(17) 0.3133(8) 0.058(5) Uiso d . . . 1 . .
H H4 1.1436(16) -0.1568(17) 0.3092(8) 0.051(5) Uiso d . . . 1 . .
H H10 0.402(2) 0.230(2) -0.1569(10) 0.078(7) Uiso d . . . 1 . .
H H11 0.366(2) 0.2556(19) -0.0576(9) 0.063(6) Uiso d . . . 1 . .
C C38 1.14180(17) -0.08289(16) 0.28162(7) 0.0393(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N3 C10 . 1.4075(16) ?
N3 C15 . 1.4293(16) ?
N3 C14 . 1.4461(15) ?
O2 C15 . 1.2107(15) ?
O3 C10 . 1.2132(15) ?
N4 C14 . 1.2675(16) ?
N4 C25 . 1.4769(15) ?
C5 C7 . 1.3703(18) ?
C5 C8 . 1.4211(17) ?
C5 C14 . 1.4662(17) ?
O1 C24 . 1.2284(17) ?
C7 C11 . 1.4092(19) ?
C7 H6 . 0.970(14) ?
C8 C9 . 1.4078(19) ?
C8 C13 . 1.4256(18) ?
C9 C36 . 1.369(2) ?
C9 C25 . 1.5358(18) ?
C10 C16 . 1.4891(17) ?
C11 C18 . 1.361(2) ?
C11 H7 . 0.982(15) ?
C12 C39 . 1.3869(19) ?
C12 C17 . 1.3923(19) ?
C12 H16 . 0.976(14) ?
C13 C32 . 1.410(2) ?
C13 C18 . 1.415(2) ?
C15 C17 . 1.4788(18) ?
C16 C29 . 1.387(2) ?
C16 C19 . 1.3904(19) ?
C17 C21 . 1.3966(19) ?
C18 H8 . 0.981(15) ?
C19 C38 . 1.386(2) ?
C19 H5 . 0.986(16) ?
C20 C23 . 1.328(2) ?
C20 C25 . 1.505(2) ?
C20 H12 . 0.971(15) ?
C21 C31 . 1.380(2) ?
C21 H20 . 0.980(16) ?
C39 C27 . 1.383(2) ?
C39 H17 . 1.000(16) ?
C23 C24 . 1.468(2) ?
C23 H15 . 0.978(16) ?
C24 C28 . 1.464(2) ?
C25 C26 . 1.5078(19) ?
C26 C28 . 1.328(2) ?
C26 H13 . 0.987(16) ?
C27 C31 . 1.386(2) ?
C27 H18 . 0.992(18) ?
C28 H14 . 0.978(16) ?
C29 C34 . 1.388(2) ?
C29 H1 . 0.952(15) ?
C31 H19 . 0.982(18) ?
C32 C35 . 1.361(2) ?
C32 H9 . 0.949(18) ?
C33 C38 . 1.376(2) ?
C33 C34 . 1.381(3) ?
C33 H3 . 0.979(19) ?
C34 H2 . 0.974(19) ?
C35 C36 . 1.403(2) ?
C35 H10 . 0.95(2) ?
C36 H11 . 0.97(2) ?
C38 H4 . 0.996(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N3 C15 . . 119.22(10) ?
C10 N3 C14 . . 115.13(10) ?
C15 N3 C14 . . 116.40(10) ?
C14 N4 C25 . . 119.79(10) ?
C7 C5 C8 . . 120.19(12) ?
C7 C5 C14 . . 123.65(11) ?
C8 C5 C14 . . 116.12(11) ?
C5 C7 C11 . . 120.31(12) ?
C5 C7 H6 . . 119.7(8) ?
C11 C7 H6 . . 119.9(8) ?
C9 C8 C13 . . 119.93(12) ?
C9 C8 C5 . . 120.73(12) ?
C13 C8 C5 . . 119.34(12) ?
C36 C9 C8 . . 119.57(13) ?
C36 C9 C25 . . 120.55(13) ?
C8 C9 C25 . . 119.88(11) ?
O3 C10 N3 . . 120.21(11) ?
O3 C10 C16 . . 122.43(12) ?
N3 C10 C16 . . 117.22(11) ?
C18 C11 C7 . . 120.72(13) ?
C18 C11 H7 . . 119.9(8) ?
C7 C11 H7 . . 119.4(8) ?
C39 C12 C17 . . 119.80(13) ?
C39 C12 H16 . . 120.2(8) ?
C17 C12 H16 . . 120.0(8) ?
C32 C13 C18 . . 123.20(13) ?
C32 C13 C8 . . 118.35(13) ?
C18 C13 C8 . . 118.44(12) ?
N4 C14 N3 . . 114.83(11) ?
N4 C14 C5 . . 127.74(11) ?
N3 C14 C5 . . 117.41(10) ?
O2 C15 N3 . . 119.97(12) ?
O2 C15 C17 . . 123.16(12) ?
N3 C15 C17 . . 116.82(11) ?
C29 C16 C19 . . 120.04(13) ?
C29 C16 C10 . . 122.07(12) ?
C19 C16 C10 . . 117.80(12) ?
C12 C17 C21 . . 120.01(13) ?
C12 C17 C15 . . 122.37(12) ?
C21 C17 C15 . . 117.46(12) ?
C11 C18 C13 . . 120.99(13) ?
C11 C18 H8 . . 122.3(9) ?
C13 C18 H8 . . 116.7(9) ?
C38 C19 C16 . . 119.76(15) ?
C38 C19 H5 . . 120.6(9) ?
C16 C19 H5 . . 119.6(9) ?
C23 C20 C25 . . 123.39(14) ?
C23 C20 H12 . . 121.4(9) ?
C25 C20 H12 . . 115.2(9) ?
C31 C21 C17 . . 119.65(14) ?
C31 C21 H20 . . 120.4(9) ?
C17 C21 H20 . . 119.9(9) ?
C27 C39 C12 . . 119.91(14) ?
C27 C39 H17 . . 121.9(9) ?
C12 C39 H17 . . 118.1(9) ?
C20 C23 C24 . . 121.21(14) ?
C20 C23 H15 . . 121.2(9) ?
C24 C23 H15 . . 117.5(9) ?
O1 C24 C28 . . 121.35(14) ?
O1 C24 C23 . . 121.26(14) ?
C28 C24 C23 . . 117.35(12) ?
N4 C25 C20 . . 106.21(10) ?
N4 C25 C26 . . 105.78(10) ?
C20 C25 C26 . . 112.76(11) ?
N4 C25 C9 . . 115.73(10) ?
C20 C25 C9 . . 108.51(11) ?
C26 C25 C9 . . 107.96(11) ?
C28 C26 C25 . . 123.06(14) ?
C28 C26 H13 . . 122.1(9) ?
C25 C26 H13 . . 114.8(9) ?
C39 C27 C31 . . 120.37(14) ?
C39 C27 H18 . . 119.7(10) ?
C31 C27 H18 . . 119.9(10) ?
C26 C28 C24 . . 121.56(14) ?
C26 C28 H14 . . 120.8(9) ?
C24 C28 H14 . . 117.6(9) ?
C16 C29 C34 . . 119.54(15) ?
C16 C29 H1 . . 119.7(9) ?
C34 C29 H1 . . 120.8(9) ?
C21 C31 C27 . . 120.25(14) ?
C21 C31 H19 . . 119.0(10) ?
C27 C31 H19 . . 120.8(10) ?
C35 C32 C13 . . 120.69(14) ?
C35 C32 H9 . . 121.3(11) ?
C13 C32 H9 . . 118.1(11) ?
C38 C33 C34 . . 120.18(15) ?
C38 C33 H3 . . 119.7(11) ?
C34 C33 H3 . . 120.1(11) ?
C33 C34 C29 . . 120.27(17) ?
C33 C34 H2 . . 120.1(11) ?
C29 C34 H2 . . 119.6(11) ?
C32 C35 C36 . . 120.61(15) ?
C32 C35 H10 . . 120.6(13) ?
C36 C35 H10 . . 118.8(13) ?
C9 C36 C35 . . 120.83(16) ?
C9 C36 H11 . . 119.6(11) ?
C35 C36 H11 . . 119.5(11) ?
C33 C38 C19 . . 120.19(15) ?
C33 C38 H4 . . 121.5(10) ?
C19 C38 H4 . . 118.3(10) ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1454176'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_chemical_name_systematic        'by-product 2'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H19.46 Cl0.08 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         438.91

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.6018(16)
_cell_length_b                   11.8059(12)
_cell_length_c                   23.666(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.4922(12)
_cell_angle_gamma                90
_cell_volume                     4286.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7054
_cell_measurement_theta_min      2.4347
_cell_measurement_theta_max      26.4575
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1831

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22553
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
;

_reflns_number_total             8842
_reflns_number_gt                6884
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1098
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         8842
_refine_ls_number_parameters     636
_refine_ls_number_restraints     12
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.2925P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.65850(9) 0.36299(12) 0.05254(6) 0.0156(3) Uani d . . . 1.0 . .
C C4 0.09374(9) 0.85689(12) 0.19942(6) 0.0178(3) Uani d . . . 1.0 . .
C C7 -0.06234(9) 0.91168(12) 0.24010(6) 0.0193(3) Uani d . . . 1.0 . .
C C9 -0.08034(10) 0.71217(13) 0.26504(6) 0.0227(3) Uani d . . . 1.0 . .
C C10 0.83626(9) 0.22303(12) -0.01095(6) 0.0190(3) Uani d . . . 1.0 . .
C C11 0.04462(9) 0.76737(12) 0.22076(6) 0.0191(3) Uani d . . . 1.0 . .
C C12 0.11763(9) 1.15463(12) 0.16481(6) 0.0185(3) Uani d . . . 1.0 . .
C C13 0.81216(9) 0.42310(12) 0.01071(6) 0.0165(3) Uani d . . . 1.0 . .
C C14 0.68892(10) 0.16173(12) 0.03465(6) 0.0208(3) Uani d . . . 1.0 . .
H H14 0.6378 0.1403 0.0485 0.025 Uiso calc U . R 1.0 . .
C C15 0.71191(9) 0.27438(12) 0.03416(6) 0.0167(3) Uani d . . . 1.0 . .
C C16 0.61825(9) 0.53712(12) 0.07142(6) 0.0161(3) Uani d . . . 1.0 . .
C C17 0.76828(9) 0.51638(11) 0.04141(6) 0.0151(3) Uani d . . . 1.0 . .
C C18 0.67261(10) 0.69896(12) 0.13534(6) 0.0204(3) Uani d . . . 1.0 . .
H H18 0.6984 0.6459 0.1635 0.025 Uiso calc U . R 1.0 . .
C C19 0.10049(10) 1.38719(13) 0.14709(7) 0.0243(3) Uani d . . . 1.0 . .
H H19 0.0938 1.4666 0.1414 0.029 Uiso calc U . R 1.0 . .
C C20 0.92628(10) 0.36905(13) -0.04115(6) 0.0221(3) Uani d . . . 1.0 . .
H H20 0.9719 0.3912 -0.0605 0.027 Uiso calc U . R 1.0 . .
C C21 0.47133(9) 0.47676(12) 0.09747(6) 0.0161(3) Uani d . . . 1.0 . .
C C22 0.62559(9) 0.66045(12) 0.08317(6) 0.0163(3) Uani d . . . 1.0 . .
C C23 0.87385(10) 0.63933(13) 0.10604(6) 0.0234(3) Uani d . . . 1.0 . .
H H23 0.9143 0.649 0.1409 0.028 Uiso calc U . R 1.0 . .
C C24 -0.08169(9) 1.04353(13) 0.15866(6) 0.0219(3) Uani d . . . 1.0 . .
H H24 -0.0951 0.9914 0.1277 0.026 Uiso calc U . R 1.0 . .
C C25 0.55509(9) 0.45906(12) 0.07814(6) 0.0158(3) Uani d . . . 1.0 . .
C C26 0.27232(9) 0.97636(12) 0.14549(6) 0.0195(3) Uani d . . . 1.0 . .
C C27 0.90605(10) 0.25693(13) -0.03788(6) 0.0221(3) Uani d . . . 1.0 . .
H H27 0.9389 0.2015 -0.0537 0.027 Uiso calc U . R 1.0 . .
C C28 0.16357(9) 1.23009(12) 0.20459(6) 0.0197(3) Uani d . . . 1.0 . .
H H28 0.2008 1.2019 0.2379 0.024 Uiso calc U . R 1.0 . .
C C29 0.74066(10) 0.07801(13) 0.01481(6) 0.0243(3) Uani d . . . 1.0 . .
H H29 0.7258 0.0003 0.017 0.029 Uiso calc U . R 1.0 . .
C C31 0.12628(9) 1.03088(12) 0.17474(6) 0.0188(3) Uani d . . . 1.0 . .
C C33 0.78729(9) 0.30761(12) 0.01242(6) 0.0167(3) Uani d . . . 1.0 . .
C C34 -0.03277(9) 0.79809(12) 0.24100(6) 0.0186(3) Uani d . . . 1.0 . .
C C35 0.58657(9) 0.73947(12) 0.04256(6) 0.0182(3) Uani d . . . 1.0 . .
H H35 0.5533 0.7144 0.0071 0.022 Uiso calc U . R 1.0 . .
C C36 0.19083(9) 0.95531(12) 0.16739(6) 0.0182(3) Uani d . . . 1.0 . .
C C37 -0.05101(11) 0.59827(14) 0.26548(7) 0.0275(4) Uani d . . . 1.0 A 1
C C38 0.64448(10) 0.89158(13) 0.10580(7) 0.0253(3) Uani d . . . 1.0 . .
H H38 0.6515 0.9704 0.1133 0.03 Uiso calc U . R 1.0 . .
C C39 -0.01801(9) 1.00805(12) 0.21178(6) 0.0183(3) Uani d . . . 1.0 . .
C C40 0.00365(10) 1.10265(12) 0.25491(6) 0.0204(3) Uani d . . . 1.0 . .
H H40 0.0469 1.0893 0.2881 0.024 Uiso calc U . R 1.0 . .
C C41 -0.03439(10) 1.20340(13) 0.24899(7) 0.0236(3) Uani d . . . 1.0 . .
H H41 -0.0204 1.2575 0.279 0.028 Uiso calc U . R 1.0 . .
C C42 0.05586(10) 1.31302(13) 0.10708(7) 0.0237(3) Uani d . . . 1.0 . .
H H42 0.0186 1.3415 0.0739 0.028 Uiso calc U . R 1.0 . .
C C43 0.15528(10) 1.34587(13) 0.19579(6) 0.0221(3) Uani d . . . 1.0 . .
H H43 0.1869 1.3969 0.2229 0.027 Uiso calc U . R 1.0 . .
C C44 -0.15331(10) 0.74448(14) 0.28902(6) 0.0262(4) Uani d . . . 1.0 . .
H H44 -0.1853 0.6884 0.3052 0.031 Uiso calc U . R 1.0 . .
C C45 0.83067(9) 0.54206(13) 0.09676(6) 0.0189(3) Uani d . . . 1.0 . .
H H45 0.8393 0.4862 0.1262 0.023 Uiso calc U . R 1.0 . .
C C46 0.06531(10) 1.19699(13) 0.11533(6) 0.0214(3) Uani d . . . 1.0 . .
H H46 0.036 1.1463 0.0871 0.026 Uiso calc U . R 1.0 . .
C C47 -0.17835(10) 0.85520(14) 0.28923(6) 0.0272(4) Uani d . . . 1.0 . .
H H47 -0.2265 0.8759 0.3065 0.033 Uiso calc U . R 1.0 . .
C C48 0.43819(9) 0.38986(12) 0.12760(6) 0.0180(3) Uani d . . . 1.0 . .
H H48 0.4692 0.3205 0.1345 0.022 Uiso calc U . R 1.0 . .
C C49 0.75082(9) 0.61836(12) 0.00249(6) 0.0182(3) Uani d . . . 1.0 . .
H H49 0.7059 0.6136 -0.0304 0.022 Uiso calc U . R 1.0 . .
C C50 0.59628(10) 0.85447(12) 0.05389(6) 0.0212(3) Uani d . . . 1.0 . .
H H50 0.5699 0.908 0.0261 0.025 Uiso calc U . R 1.0 . .
C C51 0.36038(9) 0.40393(13) 0.14753(6) 0.0202(3) Uani d . . . 1.0 . .
H H51 0.3386 0.3444 0.1679 0.024 Uiso calc U . R 1.0 . .
C C52 -0.11974(10) 1.14490(14) 0.15356(7) 0.0265(4) Uani d . . . 1.0 . .
H H52 -0.1627 1.1605 0.1205 0.032 Uiso calc U . R 1.0 . .
C C53 0.79536(10) 0.71432(12) 0.01208(7) 0.0224(3) Uani d . . . 1.0 . .
H H53 0.7843 0.7732 -0.0157 0.027 Uiso calc U . R 1.0 . .
C C54 -0.09745(10) 1.23349(13) 0.19740(7) 0.0269(4) Uani d . . . 1.0 . .
C C55 -0.13349(10) 0.93852(14) 0.26408(6) 0.0242(3) Uani d . . . 1.0 . .
H H55 -0.1527 1.015 0.2636 0.029 Uiso calc U . R 1.0 . .
C C56 0.34608(9) 0.59116(12) 0.10717(6) 0.0193(3) Uani d . . . 1.0 . .
H H56 0.3144 0.6599 0.0999 0.023 Uiso calc U . R 1.0 . .
C C57 0.07245(10) 0.65673(12) 0.22360(6) 0.0224(3) Uani d . . . 1.0 . .
H H57 0.125 0.6373 0.211 0.027 Uiso calc U . R 1.0 . .
C C58 0.68219(10) 0.81409(13) 0.14651(7) 0.0264(3) Uani d . . . 1.0 . .
H H58 0.7147 0.8395 0.1821 0.032 Uiso calc U . R 1.0 . .
C C59 0.86091(10) 0.73254(13) 0.06397(7) 0.0250(3) Uani d . . . 1.0 . .
C C60 0.31436(9) 0.50512(13) 0.13767(6) 0.0207(3) Uani d . . . 1.0 . .
H H60 0.2616 0.5153 0.1517 0.025 Uiso calc U . R 1.0 . .
C C61 0.42572(10) 1.00786(14) 0.10147(6) 0.0255(3) Uani d . . . 1.0 . .
H H61 0.4777 1.0183 0.0865 0.031 Uiso calc U . R 1.0 . .
C C62 0.88017(9) 0.45218(13) -0.01610(6) 0.0200(3) Uani d . . . 1.0 . .
H H62 0.8963 0.5295 -0.0178 0.024 Uiso calc U . R 1.0 . .
C C63 0.36688(10) 1.09578(13) 0.10020(6) 0.0233(3) Uani d . . . 1.0 . .
H H63 0.3786 1.1669 0.0844 0.028 Uiso calc U . R 1.0 . .
C C64 0.02346(11) 0.57170(13) 0.24517(7) 0.0277(4) Uani d . . . 1.0 . .
H H64 0.0423 0.4951 0.2456 0.033 Uiso calc U . R 1.0 A 1
C C65 0.33301(10) 0.88867(13) 0.14682(6) 0.0224(3) Uani d . . . 1.0 . .
H H65 0.3222 0.8177 0.1631 0.027 Uiso calc U . R 1.0 . .
C C66 0.42368(9) 0.57756(12) 0.08716(6) 0.0177(3) Uani d . . . 1.0 . .
H H66 0.4447 0.637 0.0663 0.021 Uiso calc U . R 1.0 . .
C C67 0.29078(10) 1.08063(13) 0.12194(6) 0.0218(3) Uani d . . . 1.0 . .
H H67 0.2508 1.1416 0.1208 0.026 Uiso calc U . R 1.0 . .
C C68 0.40833(10) 0.90354(14) 0.12490(6) 0.0251(3) Uani d . . . 1.0 . .
H H68 0.4484 0.8428 0.1257 0.03 Uiso calc U . R 1.0 . .
Cl Cl6 0.8906(7) 0.0115(9) -0.0189(4) 0.085(3) Uani d U P . 0.0835(16) B 2
Cl Cl5 -0.1149(4) 0.5125(5) 0.2829(2) 0.0426(19) Uani d U P . 0.0835(16) A 1
C C30 0.81172(11) 0.10835(14) -0.00742(7) 0.0240(3) Uani d . . . 1.0 . .
N N1 0.58105(8) 0.35103(10) 0.06647(5) 0.0166(2) Uani d . . . 1.0 . .
N N2 0.68470(7) 0.47389(9) 0.05458(5) 0.0152(2) Uani d . . . 1.0 . .
N N3 0.16993(8) 0.84754(10) 0.18301(5) 0.0180(3) Uani d . . . 1.0 . .
N N4 0.06372(8) 0.96633(10) 0.19542(5) 0.0177(3) Uani d . . . 1.0 . .
O O1 -0.12869(8) 1.32911(10) 0.19100(6) 0.0395(3) Uani d . . . 1.0 . .
O O2 0.90293(8) 0.82080(10) 0.07197(6) 0.0378(3) Uani d . . . 1.0 . .
H H2 0.8368(16) 0.0639(19) -0.0214(9) 0.037(6) Uiso d . P . 0.9165(16) . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 N1 . 1.3168(18) ?
C3 N2 . 1.3698(17) ?
C3 C15 . 1.4525(19) ?
C4 N3 . 1.3206(18) ?
C4 N4 . 1.3717(18) ?
C4 C11 . 1.449(2) ?
C7 C55 . 1.373(2) ?
C7 C34 . 1.417(2) ?
C7 C39 . 1.546(2) ?
C9 C44 . 1.414(2) ?
C9 C37 . 1.420(2) ?
C9 C34 . 1.434(2) ?
C10 C30 . 1.414(2) ?
C10 C27 . 1.416(2) ?
C10 C33 . 1.428(2) ?
C11 C57 . 1.374(2) ?
C11 C34 . 1.425(2) ?
C12 C46 . 1.393(2) ?
C12 C28 . 1.396(2) ?
C12 C31 . 1.482(2) ?
C13 C62 . 1.375(2) ?
C13 C33 . 1.420(2) ?
C13 C17 . 1.5460(19) ?
C14 C15 . 1.378(2) ?
C14 C29 . 1.410(2) ?
C14 H14 . 0.95 ?
C15 C33 . 1.422(2) ?
C16 C25 . 1.3794(19) ?
C16 N2 . 1.3934(18) ?
C16 C22 . 1.4829(19) ?
C17 N2 . 1.4823(17) ?
C17 C49 . 1.5103(19) ?
C17 C45 . 1.5137(19) ?
C18 C58 . 1.388(2) ?
C18 C22 . 1.393(2) ?
C18 H18 . 0.95 ?
C19 C42 . 1.381(2) ?
C19 C43 . 1.392(2) ?
C19 H19 . 0.95 ?
C20 C27 . 1.366(2) ?
C20 C62 . 1.410(2) ?
C20 H20 . 0.95 ?
C21 C66 . 1.401(2) ?
C21 C48 . 1.4009(19) ?
C21 C25 . 1.4760(19) ?
C22 C35 . 1.3970(19) ?
C23 C45 . 1.329(2) ?
C23 C59 . 1.473(2) ?
C23 H23 . 0.95 ?
C24 C52 . 1.332(2) ?
C24 C39 . 1.5126(19) ?
C24 H24 . 0.95 ?
C25 N1 . 1.3811(18) ?
C26 C65 . 1.399(2) ?
C26 C67 . 1.403(2) ?
C26 C36 . 1.479(2) ?
C27 H27 . 0.95 ?
C28 C43 . 1.385(2) ?
C28 H28 . 0.95 ?
C29 C30 . 1.359(2) ?
C29 H29 . 0.95 ?
C31 C36 . 1.380(2) ?
C31 N4 . 1.3953(18) ?
C35 C50 . 1.387(2) ?
C35 H35 . 0.95 ?
C36 N3 . 1.3805(18) ?
C37 C64 . 1.372(2) ?
C37 Cl5 . 1.530(6) ?
C38 C58 . 1.380(2) ?
C38 C50 . 1.389(2) ?
C38 H38 . 0.95 ?
C39 N4 . 1.4828(18) ?
C39 C40 . 1.5092(19) ?
C40 C41 . 1.325(2) ?
C40 H40 . 0.95 ?
C41 C54 . 1.465(2) ?
C41 H41 . 0.95 ?
C42 C46 . 1.388(2) ?
C42 H42 . 0.95 ?
C43 H43 . 0.95 ?
C44 C47 . 1.365(2) ?
C44 H44 . 0.95 ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C47 C55 . 1.401(2) ?
C47 H47 . 0.95 ?
C48 C51 . 1.390(2) ?
C48 H48 . 0.95 ?
C49 C53 . 1.327(2) ?
C49 H49 . 0.95 ?
C50 H50 . 0.95 ?
C51 C60 . 1.391(2) ?
C51 H51 . 0.95 ?
C52 C54 . 1.470(2) ?
C52 H52 . 0.95 ?
C53 C59 . 1.464(2) ?
C53 H53 . 0.95 ?
C54 O1 . 1.2281(19) ?
C55 H55 . 0.95 ?
C56 C66 . 1.387(2) ?
C56 C60 . 1.388(2) ?
C56 H56 . 0.95 ?
C57 C64 . 1.412(2) ?
C57 H57 . 0.95 ?
C58 H58 . 0.95 ?
C59 O2 . 1.2273(18) ?
C60 H60 . 0.95 ?
C61 C63 . 1.382(2) ?
C61 C68 . 1.397(2) ?
C61 H61 . 0.95 ?
C62 H62 . 0.95 ?
C63 C67 . 1.389(2) ?
C63 H63 . 0.95 ?
C64 H64 . 0.95 ?
C65 C68 . 1.379(2) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?
C67 H67 . 0.95 ?
C68 H68 . 0.95 ?
Cl6 C30 . 1.738(11) ?
Cl6 H2 . 1.04(2) ?
C30 H2 . 0.76(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C3 N2 . . 112.04(12) ?
N1 C3 C15 . . 126.90(13) ?
N2 C3 C15 . . 121.01(12) ?
N3 C4 N4 . . 111.88(12) ?
N3 C4 C11 . . 127.08(13) ?
N4 C4 C11 . . 121.03(13) ?
C55 C7 C34 . . 119.85(14) ?
C55 C7 C39 . . 117.94(13) ?
C34 C7 C39 . . 122.20(13) ?
C44 C9 C37 . . 122.31(14) ?
C44 C9 C34 . . 118.76(14) ?
C37 C9 C34 . . 118.90(14) ?
C30 C10 C27 . . 122.41(14) ?
C30 C10 C33 . . 118.49(14) ?
C27 C10 C33 . . 119.08(13) ?
C57 C11 C34 . . 120.34(14) ?
C57 C11 C4 . . 121.86(14) ?
C34 C11 C4 . . 117.76(13) ?
C46 C12 C28 . . 119.24(13) ?
C46 C12 C31 . . 120.65(13) ?
C28 C12 C31 . . 120.10(13) ?
C62 C13 C33 . . 119.37(13) ?
C62 C13 C17 . . 118.94(12) ?
C33 C13 C17 . . 121.58(12) ?
C15 C14 C29 . . 120.53(14) ?
C15 C14 H14 . . 119.7 ?
C29 C14 H14 . . 119.7 ?
C14 C15 C33 . . 120.21(13) ?
C14 C15 C3 . . 121.88(13) ?
C33 C15 C3 . . 117.83(13) ?
C25 C16 N2 . . 105.03(12) ?
C25 C16 C22 . . 131.82(13) ?
N2 C16 C22 . . 122.93(12) ?
N2 C17 C49 . . 109.28(11) ?
N2 C17 C45 . . 109.72(11) ?
C49 C17 C45 . . 112.60(12) ?
N2 C17 C13 . . 109.85(11) ?
C49 C17 C13 . . 109.11(11) ?
C45 C17 C13 . . 106.22(11) ?
C58 C18 C22 . . 120.65(14) ?
C58 C18 H18 . . 119.7 ?
C22 C18 H18 . . 119.7 ?
C42 C19 C43 . . 120.15(14) ?
C42 C19 H19 . . 119.9 ?
C43 C19 H19 . . 119.9 ?
C27 C20 C62 . . 120.64(14) ?
C27 C20 H20 . . 119.7 ?
C62 C20 H20 . . 119.7 ?
C66 C21 C48 . . 118.52(13) ?
C66 C21 C25 . . 122.55(12) ?
C48 C21 C25 . . 118.92(13) ?
C18 C22 C35 . . 119.02(13) ?
C18 C22 C16 . . 119.80(12) ?
C35 C22 C16 . . 121.18(12) ?
C45 C23 C59 . . 122.05(14) ?
C45 C23 H23 . . 119.0 ?
C59 C23 H23 . . 119.0 ?
C52 C24 C39 . . 122.60(14) ?
C52 C24 H24 . . 118.7 ?
C39 C24 H24 . . 118.7 ?
C16 C25 N1 . . 110.63(12) ?
C16 C25 C21 . . 129.23(13) ?
N1 C25 C21 . . 120.08(12) ?
C65 C26 C67 . . 118.10(14) ?
C65 C26 C36 . . 119.29(13) ?
C67 C26 C36 . . 122.59(13) ?
C20 C27 C10 . . 120.26(14) ?
C20 C27 H27 . . 119.9 ?
C10 C27 H27 . . 119.9 ?
C43 C28 C12 . . 120.40(14) ?
C43 C28 H28 . . 119.8 ?
C12 C28 H28 . . 119.8 ?
C30 C29 C14 . . 120.08(14) ?
C30 C29 H29 . . 120.0 ?
C14 C29 H29 . . 120.0 ?
C36 C31 N4 . . 105.33(12) ?
C36 C31 C12 . . 131.68(13) ?
N4 C31 C12 . . 123.00(13) ?
C13 C33 C15 . . 121.57(13) ?
C13 C33 C10 . . 119.47(13) ?
C15 C33 C10 . . 118.88(13) ?
C7 C34 C11 . . 121.96(13) ?
C7 C34 C9 . . 118.99(13) ?
C11 C34 C9 . . 119.00(13) ?
C50 C35 C22 . . 120.14(13) ?
C50 C35 H35 . . 119.9 ?
C22 C35 H35 . . 119.9 ?
C31 C36 N3 . . 110.41(13) ?
C31 C36 C26 . . 129.00(13) ?
N3 C36 C26 . . 120.59(13) ?
C64 C37 C9 . . 120.42(15) ?
C64 C37 Cl5 . . 125.3(2) ?
C9 C37 Cl5 . . 113.8(2) ?
C58 C38 C50 . . 120.10(14) ?
C58 C38 H38 . . 119.9 ?
C50 C38 H38 . . 119.9 ?
N4 C39 C40 . . 108.97(11) ?
N4 C39 C24 . . 109.93(11) ?
C40 C39 C24 . . 112.92(12) ?
N4 C39 C7 . . 110.04(11) ?
C40 C39 C7 . . 108.32(11) ?
C24 C39 C7 . . 106.62(11) ?
C41 C40 C39 . . 123.50(14) ?
C41 C40 H40 . . 118.3 ?
C39 C40 H40 . . 118.3 ?
C40 C41 C54 . . 121.70(14) ?
C40 C41 H41 . . 119.2 ?
C54 C41 H41 . . 119.2 ?
C19 C42 C46 . . 120.13(14) ?
C19 C42 H42 . . 119.9 ?
C46 C42 H42 . . 119.9 ?
C28 C43 C19 . . 119.78(14) ?
C28 C43 H43 . . 120.1 ?
C19 C43 H43 . . 120.1 ?
C47 C44 C9 . . 120.79(15) ?
C47 C44 H44 . . 119.6 ?
C9 C44 H44 . . 119.6 ?
C23 C45 C17 . . 122.87(13) ?
C23 C45 H45 . . 118.6 ?
C17 C45 H45 . . 118.6 ?
C42 C46 C12 . . 120.25(14) ?
C42 C46 H46 . . 119.9 ?
C12 C46 H46 . . 119.9 ?
C44 C47 C55 . . 120.36(15) ?
C44 C47 H47 . . 119.8 ?
C55 C47 H47 . . 119.8 ?
C51 C48 C21 . . 120.74(13) ?
C51 C48 H48 . . 119.6 ?
C21 C48 H48 . . 119.6 ?
C53 C49 C17 . . 123.08(13) ?
C53 C49 H49 . . 118.5 ?
C17 C49 H49 . . 118.5 ?
C35 C50 C38 . . 120.15(14) ?
C35 C50 H50 . . 119.9 ?
C38 C50 H50 . . 119.9 ?
C48 C51 C60 . . 120.10(13) ?
C48 C51 H51 . . 119.9 ?
C60 C51 H51 . . 119.9 ?
C24 C52 C54 . . 122.09(14) ?
C24 C52 H52 . . 119.0 ?
C54 C52 H52 . . 119.0 ?
C49 C53 C59 . . 122.21(14) ?
C49 C53 H53 . . 118.9 ?
C59 C53 H53 . . 118.9 ?
O1 C54 C41 . . 121.12(16) ?
O1 C54 C52 . . 121.97(15) ?
C41 C54 C52 . . 116.90(13) ?
C7 C55 C47 . . 121.18(15) ?
C7 C55 H55 . . 119.4 ?
C47 C55 H55 . . 119.4 ?
C66 C56 C60 . . 120.57(14) ?
C66 C56 H56 . . 119.7 ?
C60 C56 H56 . . 119.7 ?
C11 C57 C64 . . 120.42(14) ?
C11 C57 H57 . . 119.8 ?
C64 C57 H57 . . 119.8 ?
C38 C58 C18 . . 119.92(14) ?
C38 C58 H58 . . 120.0 ?
C18 C58 H58 . . 120.0 ?
O2 C59 C53 . . 121.74(15) ?
O2 C59 C23 . . 121.76(15) ?
C53 C59 C23 . . 116.50(13) ?
C56 C60 C51 . . 119.57(13) ?
C56 C60 H60 . . 120.2 ?
C51 C60 H60 . . 120.2 ?
C63 C61 C68 . . 119.62(14) ?
C63 C61 H61 . . 120.2 ?
C68 C61 H61 . . 120.2 ?
C13 C62 C20 . . 121.06(14) ?
C13 C62 H62 . . 119.5 ?
C20 C62 H62 . . 119.5 ?
C61 C63 C67 . . 120.29(14) ?
C61 C63 H63 . . 119.9 ?
C67 C63 H63 . . 119.9 ?
C37 C64 C57 . . 120.84(15) ?
C37 C64 H64 . . 119.6 ?
C57 C64 H64 . . 119.6 ?
C68 C65 C26 . . 121.11(14) ?
C68 C65 H65 . . 119.4 ?
C26 C65 H65 . . 119.4 ?
C56 C66 C21 . . 120.48(13) ?
C56 C66 H66 . . 119.8 ?
C21 C66 H66 . . 119.8 ?
C63 C67 C26 . . 120.76(14) ?
C63 C67 H67 . . 119.6 ?
C26 C67 H67 . . 119.6 ?
C65 C68 C61 . . 120.11(14) ?
C65 C68 H68 . . 119.9 ?
C61 C68 H68 . . 119.9 ?
C30 Cl6 H2 . . 13.0(13) ?
C29 C30 C10 . . 121.61(15) ?
C29 C30 Cl6 . . 122.6(3) ?
C10 C30 Cl6 . . 114.4(3) ?
C29 C30 H2 . . 120.3(16) ?
C10 C30 H2 . . 117.8(16) ?
Cl6 C30 H2 . . 17.8(17) ?
C3 N1 C25 . . 105.48(11) ?
C3 N2 C16 . . 106.82(11) ?
C3 N2 C17 . . 125.76(11) ?
C16 N2 C17 . . 127.42(11) ?
C4 N3 C36 . . 105.72(12) ?
C4 N4 C31 . . 106.67(12) ?
C4 N4 C39 . . 126.43(12) ?
C31 N4 C39 . . 126.88(12) ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
