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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1057706'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_audit_creation_date             2014-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        EH-ICor-2CN
_chemical_formula_moiety         'C32 H23 N3 O2'
_chemical_formula_sum            'C32 H23 N3 O2'
_chemical_formula_weight         481.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.040(3)
_cell_length_b                   21.8380(18)
_cell_length_c                   7.2037(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.946(9)
_cell_angle_gamma                90
_cell_volume                     5169.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12299
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.813
_diffrn_reflns_theta_min         2.995
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3242
_reflns_number_total             5844
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.462
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1949
_refine_ls_R_factor_gt           0.1191
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1981P)²+4.3275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3431
_refine_ls_wR_factor_ref         0.3910
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C1A)
Uanis(C6) = Uanis(C2A)
3. Others
 Sof(H49A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(H49)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(2)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C49(H49), C49(H49A)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C18(H18A,H18B), C52(H52A,H52B), C5(H5A,H5B),
 C1A(H1AA,H1AB)
4.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C32(H32), C46(H46), C55(H55), C8(H8), C66(H66)
4.d Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C6(H6A,H6B,H6C), C2A(H2AA,H2AB,H2AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O4 O 0.29319(11) 0.64789(15) 0.6434(5) 0.0264(9) Uani 1 1 d . . . . .
O5 O 0.36868(11) 0.47667(16) 0.8027(5) 0.0284(9) Uani 1 1 d . . . . .
C10 C 0.4087(2) 0.7255(3) 0.2805(10) 0.0543(18) Uani 1 1 d . . . . .
H10A H 0.3873 0.7553 0.3055 0.065 Uiso 1 1 calc R . . . .
H10B H 0.3960 0.6938 0.1951 0.065 Uiso 1 1 calc R . . . .
N13 N 0.34080(12) 0.57251(18) 0.7318(5) 0.0220(9) Uani 1 1 d . . . . .
N22 N 0.10708(16) 0.6414(2) 0.4699(8) 0.0487(14) Uani 1 1 d . . . . .
C24 C 0.15775(16) 0.3098(2) 0.5935(7) 0.0278(12) Uani 1 1 d . . . . .
H24 H 0.1354 0.2851 0.6208 0.033 Uiso 1 1 calc R . . . .
C26 C 0.14969(16) 0.3687(2) 0.5026(7) 0.0261(12) Uani 1 1 d . . . . .
C32 C 0.11589(16) 0.4697(2) 0.4607(7) 0.0293(12) Uani 1 1 d . . . . .
H32 H 0.0917 0.4933 0.4567 0.035 Uiso 1 1 calc R . . . .
N36 N 0.29809(15) 0.2253(2) 0.8782(7) 0.0356(12) Uani 1 1 d . . . . .
C41 C 0.22336(15) 0.3753(2) 0.4933(6) 0.0212(11) Uani 1 1 d . . . . .
C44 C 0.13378(17) 0.6083(2) 0.4641(7) 0.0290(12) Uani 1 1 d . . . . .
C46 C 0.11414(17) 0.4081(2) 0.4961(7) 0.0312(13) Uani 1 1 d . . . . .
H46 H 0.0887 0.3905 0.5171 0.037 Uiso 1 1 calc R . . . .
C49 C 0.40755(19) 0.6273(4) 0.7373(9) 0.0502(19) Uani 1 1 d . . . . .
H49 H 0.4225 0.6579 0.8217 0.060 Uiso 0.501(10) 1 calc R . P A 1
H49A H 0.4144 0.5868 0.6834 0.060 Uiso 0.499(10) 1 calc R . P A 2
C55 C 0.19657(16) 0.2888(2) 0.6411(7) 0.0258(12) Uani 1 1 d . . . . .
H55 H 0.2005 0.2502 0.7012 0.031 Uiso 1 1 calc R . . . .
C58 C 0.4423(3) 0.7584(4) 0.1870(14) 0.091(3) Uani 1 1 d . . . . .
H58A H 0.4317 0.7708 0.0605 0.136 Uiso 1 1 calc GR . . . .
H58B H 0.4654 0.7306 0.1806 0.136 Uiso 1 1 calc GR . . . .
H58C H 0.4512 0.7946 0.2601 0.136 Uiso 1 1 calc GR . . . .
C62 C 0.27333(16) 0.3217(2) 0.6879(6) 0.0221(11) Uani 1 1 d . . . . .
C64 C 0.23135(14) 0.3242(2) 0.6017(6) 0.0198(10) Uani 1 1 d . . . . .
C68 C 0.30404(14) 0.5949(2) 0.6484(6) 0.0179(10) Uani 1 1 d . . . . .
C4 C 0.15365(16) 0.4995(2) 0.4294(6) 0.0225(11) Uani 1 1 d . . . . .
C8 C 0.30005(14) 0.3707(2) 0.6834(6) 0.0191(10) Uani 1 1 d . . . . .
H8 H 0.3271 0.3666 0.7410 0.023 Uiso 1 1 calc R . . . .
C13 C 0.3946(2) 0.6647(3) 0.5622(8) 0.0491(17) Uani 1 1 d . . . . .
H13A H 0.3791 0.6372 0.4717 0.059 Uiso 1 1 calc R . . . .
H13B H 0.3754 0.6966 0.5969 0.059 Uiso 1 1 calc R . . . .
C18 C 0.4259(2) 0.6956(5) 0.4635(11) 0.081(3) Uani 1 1 d . . . . .
H18A H 0.4468 0.6653 0.4369 0.097 Uiso 1 1 calc R . . . .
H18B H 0.4394 0.7274 0.5462 0.097 Uiso 1 1 calc R . . . .
C22 C 0.28704(16) 0.2679(2) 0.7954(7) 0.0260(12) Uani 1 1 d . . . . .
C1 C 0.16551(15) 0.5639(2) 0.4518(6) 0.0199(10) Uani 1 1 d . . . . .
C25 C 0.18358(16) 0.3968(2) 0.4464(6) 0.0224(11) Uani 1 1 d . . . . .
C27 C 0.30306(15) 0.4891(2) 0.6216(6) 0.0197(10) Uani 1 1 d . . . . .
C30 C 0.23857(15) 0.5376(2) 0.4861(6) 0.0182(10) Uani 1 1 d . . . . .
C34 C 0.25002(15) 0.4257(2) 0.4909(6) 0.0196(10) Uani 1 1 d . . . . .
C43 C 0.27984(15) 0.5405(2) 0.5723(6) 0.0193(10) Uani 1 1 d . . . . .
C48 C 0.22655(15) 0.4787(2) 0.4403(6) 0.0181(10) Uani 1 1 d . . . . .
C2 C 0.18579(16) 0.4605(2) 0.4113(6) 0.0221(11) Uani 1 1 d . . . . .
C52 C 0.37107(16) 0.6111(3) 0.8414(7) 0.0297(12) Uani 1 1 d . . . . .
H52A H 0.3808 0.5893 0.9580 0.036 Uiso 1 1 calc R . . . .
H52B H 0.3577 0.6494 0.8763 0.036 Uiso 1 1 calc R . . . .
C3 C 0.34168(15) 0.5090(2) 0.7278(6) 0.0211(11) Uani 1 1 d . . . . .
C66 C 0.20569(16) 0.5824(2) 0.4800(6) 0.0212(11) Uani 1 1 d . . . . .
H66 H 0.2120 0.6246 0.4954 0.025 Uiso 1 1 calc R . . . .
C70 C 0.28762(14) 0.4272(2) 0.5937(6) 0.0181(10) Uani 1 1 d . . . . .
C5 C 0.4368(4) 0.5812(7) 0.724(2) 0.050(2) Uani 0.501(10) 1 d . . P A 1
H5A H 0.4574 0.5973 0.6467 0.060 Uiso 0.501(10) 1 calc R . P A 1
H5B H 0.4231 0.5465 0.6550 0.060 Uiso 0.501(10) 1 calc R . P A 1
C6 C 0.4592(6) 0.5557(11) 0.902(3) 0.085(6) Uani 0.497(17) 1 d . . P A 1
H6A H 0.4829 0.5322 0.8718 0.127 Uiso 0.497(17) 1 calc GR . P A 1
H6B H 0.4410 0.5288 0.9643 0.127 Uiso 0.497(17) 1 calc GR . P A 1
H6C H 0.4683 0.5895 0.9861 0.127 Uiso 0.497(17) 1 calc GR . P A 1
C1A C 0.4472(4) 0.6423(7) 0.867(2) 0.050(2) Uani 0.499(10) 1 d . . P A 2
H1AA H 0.4694 0.6494 0.7870 0.060 Uiso 0.499(10) 1 calc R . P A 2
H1AB H 0.4428 0.6813 0.9325 0.060 Uiso 0.499(10) 1 calc R . P A 2
C2A C 0.4619(6) 0.5935(11) 1.016(3) 0.085(6) Uani 0.503(17) 1 d . . P A 2
H2AA H 0.4721 0.5576 0.9538 0.127 Uiso 0.503(17) 1 calc GR . P A 2
H2AB H 0.4392 0.5815 1.0849 0.127 Uiso 0.503(17) 1 calc GR . P A 2
H2AC H 0.4838 0.6108 1.1024 0.127 Uiso 0.503(17) 1 calc GR . P A 2


_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
O4 C68 1.211(6) . ?
O5 C3 1.219(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C58 1.534(10) . ?
C10 C18 1.527(9) . ?
N13 C68 1.387(6) . ?
N13 C52 1.473(6) . ?
N13 C3 1.387(6) . ?
N22 C44 1.145(7) . ?
C24 H24 0.9500 . ?
C24 C26 1.455(7) . ?
C24 C55 1.372(7) . ?
C26 C46 1.453(8) . ?
C26 C25 1.374(7) . ?
C32 H32 0.9500 . ?
C32 C46 1.371(7) . ?
C32 C4 1.445(8) . ?
N36 C22 1.145(6) . ?
C41 C64 1.373(6) . ?
C41 C25 1.403(7) . ?
C41 C34 1.411(7) . ?
C44 C1 1.438(7) . ?
C46 H46 0.9500 . ?
C49 H49 1.0000 . ?
C49 H49A 1.0000 . ?
C49 C13 1.526(9) . ?
C49 C52 1.526(8) . ?
C49 C5 1.404(15) . ?
C49 C1A 1.563(13) . ?
C55 H55 0.9500 . ?
C55 C64 1.437(7) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C62 C64 1.461(7) . ?
C62 C8 1.389(7) . ?
C62 C22 1.453(7) . ?
C68 C43 1.502(6) . ?
C4 C1 1.465(7) . ?
C4 C2 1.377(7) . ?
C8 H8 0.9500 . ?
C8 C70 1.434(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C18 1.477(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C1 C66 1.382(7) . ?
C25 C2 1.418(7) . ?
C27 C43 1.385(7) . ?
C27 C3 1.483(7) . ?
C27 C70 1.452(6) . ?
C30 C43 1.440(7) . ?
C30 C48 1.376(6) . ?
C30 C66 1.458(7) . ?
C34 C48 1.419(6) . ?
C34 C70 1.379(7) . ?
C48 C2 1.399(7) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C66 H66 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.52(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.55(2) . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 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
H10A C10 H10B 108.0 . . ?
C58 C10 H10A 109.5 . . ?
C58 C10 H10B 109.5 . . ?
C18 C10 H10A 109.5 . . ?
C18 C10 H10B 109.5 . . ?
C18 C10 C58 110.9(6) . . ?
C68 N13 C52 123.1(4) . . ?
C68 N13 C3 111.3(4) . . ?
C3 N13 C52 124.6(4) . . ?
C26 C24 H24 119.0 . . ?
C55 C24 H24 119.0 . . ?
C55 C24 C26 122.1(5) . . ?
C46 C26 C24 130.4(5) . . ?
C25 C26 C24 114.2(5) . . ?
C25 C26 C46 114.0(5) . . ?
C46 C32 H32 119.2 . . ?
C46 C32 C4 121.6(5) . . ?
C4 C32 H32 119.2 . . ?
C64 C41 C25 121.9(5) . . ?
C64 C41 C34 123.9(4) . . ?
C25 C41 C34 107.9(4) . . ?
N22 C44 C1 176.4(6) . . ?
C26 C46 H46 118.7 . . ?
C32 C46 C26 122.5(5) . . ?
C32 C46 H46 118.7 . . ?
C13 C49 H49 102.8 . . ?
C13 C49 H49A 102.0 . . ?
C13 C49 C1A 121.8(7) . . ?
C52 C49 H49 102.8 . . ?
C52 C49 H49A 102.0 . . ?
C52 C49 C13 111.3(5) . . ?
C52 C49 C1A 114.3(7) . . ?
C5 C49 H49 102.8 . . ?
C5 C49 C13 117.7(8) . . ?
C5 C49 C52 116.7(7) . . ?
C1A C49 H49A 102.0 . . ?
C24 C55 H55 119.4 . . ?
C24 C55 C64 121.1(5) . . ?
C64 C55 H55 119.4 . . ?
C10 C58 H58A 109.5 . . ?
C10 C58 H58B 109.5 . . ?
C10 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C8 C62 C64 122.7(4) . . ?
C8 C62 C22 118.1(4) . . ?
C22 C62 C64 119.1(4) . . ?
C41 C64 C55 116.1(4) . . ?
C41 C64 C62 112.9(4) . . ?
C55 C64 C62 129.8(4) . . ?
O4 C68 N13 126.3(4) . . ?
O4 C68 C43 126.8(4) . . ?
N13 C68 C43 106.8(4) . . ?
C32 C4 C1 129.8(5) . . ?
C2 C4 C32 115.0(5) . . ?
C2 C4 C1 113.8(4) . . ?
C62 C8 H8 119.3 . . ?
C62 C8 C70 121.4(4) . . ?
C70 C8 H8 119.3 . . ?
C49 C13 H13A 107.4 . . ?
C49 C13 H13B 107.4 . . ?
H13A C13 H13B 107.0 . . ?
C18 C13 C49 119.5(6) . . ?
C18 C13 H13A 107.4 . . ?
C18 C13 H13B 107.4 . . ?
C10 C18 H18A 108.9 . . ?
C10 C18 H18B 108.9 . . ?
C13 C18 C10 113.2(6) . . ?
C13 C18 H18A 108.9 . . ?
C13 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
N36 C22 C62 179.1(6) . . ?
C44 C1 C4 117.8(4) . . ?
C66 C1 C44 119.3(4) . . ?
C66 C1 C4 122.6(4) . . ?
C26 C25 C41 123.5(4) . . ?
C26 C25 C2 123.3(5) . . ?
C41 C25 C2 107.8(4) . . ?
C43 C27 C3 108.6(4) . . ?
C43 C27 C70 122.8(4) . . ?
C70 C27 C3 128.0(4) . . ?
C43 C30 C66 130.7(4) . . ?
C48 C30 C43 112.5(4) . . ?
C48 C30 C66 115.1(4) . . ?
C41 C34 C48 108.3(4) . . ?
C70 C34 C41 122.7(4) . . ?
C70 C34 C48 123.8(4) . . ?
C27 C43 C68 106.7(4) . . ?
C27 C43 C30 123.3(4) . . ?
C30 C43 C68 129.6(4) . . ?
C30 C48 C34 124.3(4) . . ?
C30 C48 C2 123.4(4) . . ?
C2 C48 C34 107.3(4) . . ?
C4 C2 C25 122.4(5) . . ?
C4 C2 C48 123.4(4) . . ?
C48 C2 C25 108.6(4) . . ?
N13 C52 C49 113.4(4) . . ?
N13 C52 H52A 108.9 . . ?
N13 C52 H52B 108.9 . . ?
C49 C52 H52A 108.9 . . ?
C49 C52 H52B 108.9 . . ?
H52A C52 H52B 107.7 . . ?
O5 C3 N13 125.9(4) . . ?
O5 C3 C27 127.6(4) . . ?
N13 C3 C27 106.5(4) . . ?
C1 C66 C30 120.6(4) . . ?
C1 C66 H66 119.7 . . ?
C30 C66 H66 119.7 . . ?
C8 C70 C27 131.3(4) . . ?
C34 C70 C8 114.9(4) . . ?
C34 C70 C27 112.4(4) . . ?
C49 C5 H5A 107.6 . . ?
C49 C5 H5B 107.6 . . ?
C49 C5 C6 119.0(15) . . ?
H5A C5 H5B 107.0 . . ?
C6 C5 H5A 107.6 . . ?
C6 C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C49 C1A H1AA 108.1 . . ?
C49 C1A H1AB 108.1 . . ?
H1AA C1A H1AB 107.3 . . ?
C2A C1A C49 116.8(12) . . ?
C2A C1A H1AA 108.1 . . ?
C2A C1A H1AB 108.1 . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 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
O4 C68 C43 C27 -175.6(5) . . . . ?
O4 C68 C43 C30 -3.4(8) . . . . ?
N13 C68 C43 C27 2.3(5) . . . . ?
N13 C68 C43 C30 174.5(4) . . . . ?
C24 C26 C46 C32 157.3(5) . . . . ?
C24 C26 C25 C41 -8.2(7) . . . . ?
C24 C26 C25 C2 -159.1(4) . . . . ?
C24 C55 C64 C41 -8.3(7) . . . . ?
C24 C55 C64 C62 158.0(5) . . . . ?
C26 C24 C55 C64 -0.4(7) . . . . ?
C26 C25 C2 C4 -0.6(7) . . . . ?
C26 C25 C2 C48 153.6(4) . . . . ?
C32 C4 C1 C44 -16.5(7) . . . . ?
C32 C4 C1 C66 156.9(5) . . . . ?
C32 C4 C2 C25 -8.4(6) . . . . ?
C32 C4 C2 C48 -158.7(4) . . . . ?
C41 C25 C2 C4 -155.4(4) . . . . ?
C41 C25 C2 C48 -1.3(5) . . . . ?
C41 C34 C48 C30 155.6(4) . . . . ?
C41 C34 C48 C2 -0.2(5) . . . . ?
C41 C34 C70 C8 8.1(6) . . . . ?
C41 C34 C70 C27 -159.8(4) . . . . ?
C44 C1 C66 C30 174.1(4) . . . . ?
C46 C26 C25 C41 159.8(4) . . . . ?
C46 C26 C25 C2 8.8(7) . . . . ?
C46 C32 C4 C1 -157.0(5) . . . . ?
C46 C32 C4 C2 8.9(7) . . . . ?
C49 C13 C18 C10 173.9(7) . . . . ?
C55 C24 C26 C46 -156.9(5) . . . . ?
C55 C24 C26 C25 8.5(7) . . . . ?
C58 C10 C18 C13 178.4(8) . . . . ?
C62 C8 C70 C27 155.8(5) . . . . ?
C62 C8 C70 C34 -9.2(6) . . . . ?
C64 C41 C25 C26 -0.5(7) . . . . ?
C64 C41 C25 C2 154.3(4) . . . . ?
C64 C41 C34 C48 -153.0(4) . . . . ?
C64 C41 C34 C70 2.4(7) . . . . ?
C64 C62 C8 C70 0.4(7) . . . . ?
C68 N13 C52 C49 -104.3(6) . . . . ?
C68 N13 C3 O5 -174.1(5) . . . . ?
C68 N13 C3 C27 3.9(5) . . . . ?
C4 C32 C46 C26 -0.6(8) . . . . ?
C4 C1 C66 C30 0.8(7) . . . . ?
C8 C62 C64 C41 9.5(6) . . . . ?
C8 C62 C64 C55 -157.1(5) . . . . ?
C13 C49 C52 N13 62.4(7) . . . . ?
C13 C49 C5 C6 162.6(12) . . . . ?
C13 C49 C1A C2A -167.6(14) . . . . ?
C22 C62 C64 C41 -175.5(4) . . . . ?
C22 C62 C64 C55 17.9(7) . . . . ?
C22 C62 C8 C70 -174.7(4) . . . . ?
C1 C4 C2 C25 159.8(4) . . . . ?
C1 C4 C2 C48 9.4(6) . . . . ?
C25 C26 C46 C32 -8.1(7) . . . . ?
C25 C41 C64 C55 8.9(6) . . . . ?
C25 C41 C64 C62 -159.7(4) . . . . ?
C25 C41 C34 C48 -0.6(5) . . . . ?
C25 C41 C34 C70 154.8(4) . . . . ?
C30 C48 C2 C4 -1.3(7) . . . . ?
C30 C48 C2 C25 -155.2(4) . . . . ?
C34 C41 C64 C55 157.7(4) . . . . ?
C34 C41 C64 C62 -10.9(7) . . . . ?
C34 C41 C25 C26 -153.6(5) . . . . ?
C34 C41 C25 C2 1.1(5) . . . . ?
C34 C48 C2 C4 154.8(4) . . . . ?
C34 C48 C2 C25 0.9(5) . . . . ?
C43 C27 C3 O5 175.7(5) . . . . ?
C43 C27 C3 N13 -2.3(5) . . . . ?
C43 C27 C70 C8 -156.9(5) . . . . ?
C43 C27 C70 C34 8.4(6) . . . . ?
C43 C30 C48 C34 7.0(6) . . . . ?
C43 C30 C48 C2 159.1(4) . . . . ?
C43 C30 C66 C1 -156.0(5) . . . . ?
C48 C30 C43 C68 -177.7(4) . . . . ?
C48 C30 C43 C27 -6.6(6) . . . . ?
C48 C30 C66 C1 7.4(6) . . . . ?
C48 C34 C70 C8 159.7(4) . . . . ?
C48 C34 C70 C27 -8.2(6) . . . . ?
C2 C4 C1 C44 177.5(4) . . . . ?
C2 C4 C1 C66 -9.1(6) . . . . ?
C52 N13 C68 O4 5.1(7) . . . . ?
C52 N13 C68 C43 -172.8(4) . . . . ?
C52 N13 C3 O5 -5.4(8) . . . . ?
C52 N13 C3 C27 172.6(4) . . . . ?
C52 C49 C13 C18 167.6(7) . . . . ?
C52 C49 C5 C6 -61.2(15) . . . . ?
C52 C49 C1A C2A 54.1(17) . . . . ?
C3 N13 C68 O4 174.0(4) . . . . ?
C3 N13 C68 C43 -3.9(5) . . . . ?
C3 N13 C52 C49 88.3(6) . . . . ?
C3 C27 C43 C68 0.0(5) . . . . ?
C3 C27 C43 C30 -172.8(4) . . . . ?
C3 C27 C70 C8 13.1(8) . . . . ?
C3 C27 C70 C34 178.5(4) . . . . ?
C66 C30 C43 C68 -14.0(8) . . . . ?
C66 C30 C43 C27 157.1(5) . . . . ?
C66 C30 C48 C34 -159.5(4) . . . . ?
C66 C30 C48 C2 -7.4(6) . . . . ?
C70 C27 C43 C68 171.8(4) . . . . ?
C70 C27 C43 C30 -1.1(7) . . . . ?
C70 C27 C3 O5 4.5(8) . . . . ?
C70 C27 C3 N13 -173.5(4) . . . . ?
C70 C34 C48 C30 0.6(7) . . . . ?
C70 C34 C48 C2 -155.3(4) . . . . ?
C5 C49 C13 C18 -53.9(11) . . . . ?
C5 C49 C52 N13 -76.5(9) . . . . ?
C5 C49 C1A C2A -56.9(16) . . . . ?
C1A C49 C13 C18 28.1(13) . . . . ?
C1A C49 C52 N13 -155.0(8) . . . . ?
C1A C49 C5 C6 46.5(14) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.073 332.5 0.0 ?
2 0.500 0.000 -0.281 332.5 0.0 ?

_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# 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_cr140911a
_database_code_depnum_ccdc_archive 'CCDC 1057707'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_audit_creation_date             2014-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        C6-ICor-2CN
_chemical_formula_moiety         'C30 H19 N3 O2'
_chemical_formula_sum            'C30 H19 N3 O2'
_chemical_formula_weight         453.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   7.2119(4)
_cell_length_b                   21.7175(15)
_cell_length_c                   31.966(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.488(6)
_cell_angle_gamma                90
_cell_volume                     4983.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2820
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.0800
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.867
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10586
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.146
_diffrn_reflns_theta_min         4.071
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.867
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -26.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  -38.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega   39.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  178.0000   60.0000 73

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066   57.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3066  178.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega   25.00   73.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -50.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega   94.00  144.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   38.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   71.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  8 omega  141.00  166.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   24.00   50.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -64.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   90.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -64.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   19.00   45.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   62.00   89.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000 -112.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   94.00  119.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   79.00  141.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
 15 omega   19.00   72.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00   68.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 17 omega   33.00   59.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  107.00  132.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   31.00   70.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 20 omega   24.00   67.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -38.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 21 omega   24.00   85.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -75.0000  -76.0000 61

#__ type_ start__ end____ width___ exp.time_
 22 omega   19.00   72.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 23 omega  118.00  165.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000   25.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 24 omega   50.00   82.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.5000 -112.0000  -90.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.0239352000
_diffrn_orient_matrix_UB_12      -0.0425053000
_diffrn_orient_matrix_UB_13      -0.0387905000
_diffrn_orient_matrix_UB_21      -0.2028061000
_diffrn_orient_matrix_UB_22      -0.0128770000
_diffrn_orient_matrix_UB_23      0.0086526000
_diffrn_orient_matrix_UB_31      -0.0654231000
_diffrn_orient_matrix_UB_32      0.0552927000
_diffrn_orient_matrix_UB_33      -0.0277239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3070
_reflns_number_total             3918
_reflns_odcompleteness_completeness 77.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1229P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2105
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C1(H1A,H1B), C31(H31A,H31B), C41(H41A,H41B), C55(H55A,H55B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C26(H26), C60(H60), C64(H64), C67(H67), C80(H80)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O3 O -0.0386(3) 0.52090(9) 0.12650(5) 0.0490(5) Uani 1 1 d . . . . .
O6 O 0.1079(2) 0.34980(9) 0.20557(6) 0.0453(5) Uani 1 1 d . . . . .
N13 N 0.2735(4) 0.35552(13) 0.39725(8) 0.0646(7) Uani 1 1 d . . . . .
N17 N 0.0224(3) 0.42547(10) 0.15661(6) 0.0399(5) Uani 1 1 d . . . . .
N2 N -0.1213(3) 0.77377(12) 0.19936(8) 0.0534(6) Uani 1 1 d . . . . .
C8 C 0.6077(6) 0.2632(3) 0.04376(14) 0.1134(19) Uani 1 1 d . . . . .
H8A H 0.5349 0.2379 0.0238 0.170 Uiso 1 1 calc GR . . . .
H8B H 0.7168 0.2410 0.0547 0.170 Uiso 1 1 calc GR . . . .
H8C H 0.6442 0.3001 0.0302 0.170 Uiso 1 1 calc GR . . . .
C11 C 0.1806(3) 0.45754(11) 0.21908(7) 0.0361(6) Uani 1 1 d . . . . .
C13 C 0.1050(3) 0.40304(12) 0.19464(7) 0.0369(6) Uani 1 1 d . . . . .
C19 C 0.3036(3) 0.60213(12) 0.31866(7) 0.0382(6) Uani 1 1 d . . . . .
C22 C -0.0392(3) 0.73105(12) 0.21071(8) 0.0438(6) Uani 1 1 d . . . . .
C24 C 0.0371(4) 0.37115(15) 0.08832(8) 0.0559(8) Uani 1 1 d . . . . .
H24A H -0.0414 0.3498 0.0667 0.067 Uiso 1 1 calc R . . . .
H24B H 0.0794 0.4089 0.0761 0.067 Uiso 1 1 calc R . . . .
C36 C 0.3359(3) 0.53812(12) 0.31699(8) 0.0369(6) Uani 1 1 d . . . . .
C40 C 0.2804(4) 0.38959(13) 0.37025(8) 0.0456(6) Uani 1 1 d . . . . .
C43 C 0.0670(3) 0.67713(12) 0.22532(8) 0.0402(6) Uani 1 1 d . . . . .
C48 C 0.3093(3) 0.51982(11) 0.27446(7) 0.0346(5) Uani 1 1 d . . . . .
C4 C 0.1336(3) 0.50950(12) 0.19528(7) 0.0358(6) Uani 1 1 d . . . . .
C10 C 0.2603(3) 0.57309(11) 0.24976(7) 0.0356(6) Uani 1 1 d . . . . .
C1 C -0.0793(4) 0.38754(14) 0.12394(9) 0.0484(7) Uani 1 1 d . . . . .
H1A H -0.1896 0.4097 0.1125 0.058 Uiso 1 1 calc R . . . .
H1B H -0.1199 0.3499 0.1366 0.058 Uiso 1 1 calc R . . . .
C15 C 0.0733(3) 0.62807(12) 0.19770(8) 0.0383(6) Uani 1 1 d . . . . .
H15 H 0.0198 0.6322 0.1702 0.046 Uiso 1 1 calc R . . . .
C17 C 0.0308(3) 0.48911(12) 0.15512(7) 0.0385(6) Uani 1 1 d . . . . .
C26 C 0.1541(3) 0.68953(13) 0.34512(8) 0.0455(6) Uani 1 1 d . . . . .
H26 H 0.1263 0.7142 0.3675 0.055 Uiso 1 1 calc R . . . .
C30 C 0.2926(3) 0.43482(12) 0.33735(7) 0.0387(6) Uani 1 1 d . . . . .
C31 C 0.3174(5) 0.31351(19) 0.06618(10) 0.0716(10) Uani 1 1 d . . . . .
H31A H 0.2407 0.2880 0.0465 0.086 Uiso 1 1 calc R . . . .
H31B H 0.3481 0.3505 0.0513 0.086 Uiso 1 1 calc R . . . .
C34 C 0.1613(3) 0.57097(12) 0.21093(8) 0.0376(6) Uani 1 1 d . . . . .
C38 C 0.3145(3) 0.49883(13) 0.34989(7) 0.0390(6) Uani 1 1 d . . . . .
C41 C 0.4936(4) 0.27966(18) 0.07907(10) 0.0639(8) Uani 1 1 d . . . . .
H41A H 0.4629 0.2421 0.0933 0.077 Uiso 1 1 calc R . . . .
H41B H 0.5694 0.3047 0.0992 0.077 Uiso 1 1 calc R . . . .
C44 C 0.2575(3) 0.62354(12) 0.27764(8) 0.0384(6) Uani 1 1 d . . . . .
C45 C 0.2443(3) 0.63070(13) 0.35398(8) 0.0427(6) Uani 1 1 d . . . . .
C49 C 0.2628(3) 0.46027(11) 0.26204(7) 0.0341(5) Uani 1 1 d . . . . .
C55 C 0.2040(4) 0.33154(16) 0.10134(9) 0.0536(7) Uani 1 1 d . . . . .
H55A H 0.2840 0.3535 0.1225 0.064 Uiso 1 1 calc R . . . .
H55B H 0.1618 0.2944 0.1143 0.064 Uiso 1 1 calc R . . . .
C60 C 0.2671(3) 0.41587(12) 0.29571(8) 0.0374(6) Uani 1 1 d . . . . .
H60 H 0.2526 0.3742 0.2895 0.045 Uiso 1 1 calc R . . . .
C64 C 0.2479(4) 0.59157(14) 0.39042(8) 0.0483(7) Uani 1 1 d . . . . .
H64 H 0.2264 0.6091 0.4161 0.058 Uiso 1 1 calc R . . . .
C66 C 0.1488(3) 0.67493(12) 0.26866(8) 0.0400(6) Uani 1 1 d . . . . .
C67 C 0.2818(4) 0.52936(14) 0.38887(8) 0.0459(6) Uani 1 1 d . . . . .
H67 H 0.2838 0.5063 0.4134 0.055 Uiso 1 1 calc R . . . .
C80 C 0.1082(3) 0.71016(13) 0.30478(8) 0.0428(6) Uani 1 1 d . . . . .
H80 H 0.0492 0.7481 0.3007 0.051 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C17 1.215(3) . ?
O6 C13 1.208(3) . ?
N13 C40 1.141(4) . ?
N17 C13 1.390(3) . ?
N17 C1 1.470(3) . ?
N17 C17 1.385(4) . ?
N2 C22 1.141(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C41 1.502(5) . ?
C11 C13 1.492(3) . ?
C11 C4 1.385(4) . ?
C11 C49 1.444(4) . ?
C19 C36 1.412(4) . ?
C19 C44 1.401(4) . ?
C19 C45 1.391(4) . ?
C22 C43 1.452(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C1 1.520(4) . ?
C24 C55 1.506(4) . ?
C36 C48 1.412(3) . ?
C36 C38 1.374(4) . ?
C40 C30 1.448(4) . ?
C43 C15 1.387(4) . ?
C43 C66 1.453(4) . ?
C48 C10 1.426(3) . ?
C48 C49 1.385(3) . ?
C4 C17 1.487(4) . ?
C4 C34 1.433(4) . ?
C10 C34 1.372(3) . ?
C10 C44 1.414(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C34 1.438(4) . ?
C26 H26 0.9300 . ?
C26 C45 1.449(4) . ?
C26 C80 1.375(4) . ?
C30 C38 1.451(4) . ?
C30 C60 1.389(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C41 1.492(5) . ?
C31 C55 1.504(4) . ?
C38 C67 1.451(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C44 C66 1.378(4) . ?
C45 C64 1.440(4) . ?
C49 C60 1.443(3) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C60 H60 0.9300 . ?
C64 H64 0.9300 . ?
C64 C67 1.375(4) . ?
C66 C80 1.438(4) . ?
C67 H67 0.9300 . ?
C80 H80 0.9300 . ?

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
C13 N17 C1 124.6(2) . . ?
C17 N17 C13 111.3(2) . . ?
C17 N17 C1 123.7(2) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C41 C8 H8A 109.5 . . ?
C41 C8 H8B 109.5 . . ?
C41 C8 H8C 109.5 . . ?
C4 C11 C13 107.5(2) . . ?
C4 C11 C49 123.1(2) . . ?
C49 C11 C13 128.8(2) . . ?
O6 C13 N17 125.6(2) . . ?
O6 C13 C11 127.8(2) . . ?
N17 C13 C11 106.5(2) . . ?
C44 C19 C36 108.5(2) . . ?
C45 C19 C36 122.3(2) . . ?
C45 C19 C44 123.2(2) . . ?
N2 C22 C43 179.3(3) . . ?
H24A C24 H24B 107.6 . . ?
C1 C24 H24A 108.7 . . ?
C1 C24 H24B 108.7 . . ?
C55 C24 H24A 108.7 . . ?
C55 C24 H24B 108.7 . . ?
C55 C24 C1 114.3(2) . . ?
C19 C36 C48 107.8(2) . . ?
C38 C36 C19 123.5(2) . . ?
C38 C36 C48 123.2(2) . . ?
N13 C40 C30 177.4(3) . . ?
C22 C43 C66 119.1(2) . . ?
C15 C43 C22 117.6(2) . . ?
C15 C43 C66 123.1(2) . . ?
C36 C48 C10 108.0(2) . . ?
C49 C48 C36 123.1(2) . . ?
C49 C48 C10 124.0(2) . . ?
C11 C4 C17 107.9(2) . . ?
C11 C4 C34 123.3(2) . . ?
C34 C4 C17 128.3(2) . . ?
C34 C10 C48 123.6(2) . . ?
C34 C10 C44 124.0(2) . . ?
C44 C10 C48 107.3(2) . . ?
N17 C1 C24 112.9(2) . . ?
N17 C1 H1A 109.0 . . ?
N17 C1 H1B 109.0 . . ?
C24 C1 H1A 109.0 . . ?
C24 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C43 C15 H15 119.5 . . ?
C43 C15 C34 121.0(2) . . ?
C34 C15 H15 119.5 . . ?
O3 C17 N17 125.2(2) . . ?
O3 C17 C4 128.0(2) . . ?
N17 C17 C4 106.7(2) . . ?
C45 C26 H26 118.9 . . ?
C80 C26 H26 118.9 . . ?
C80 C26 C45 122.2(2) . . ?
C40 C30 C38 117.5(2) . . ?
C60 C30 C40 118.9(2) . . ?
C60 C30 C38 123.3(2) . . ?
H31A C31 H31B 107.4 . . ?
C41 C31 H31A 108.4 . . ?
C41 C31 H31B 108.4 . . ?
C41 C31 C55 115.6(3) . . ?
C55 C31 H31A 108.4 . . ?
C55 C31 H31B 108.4 . . ?
C4 C34 C15 131.1(2) . . ?
C10 C34 C4 113.0(2) . . ?
C10 C34 C15 114.5(2) . . ?
C36 C38 C30 113.6(2) . . ?
C36 C38 C67 114.4(2) . . ?
C67 C38 C30 130.8(2) . . ?
C8 C41 H41A 108.5 . . ?
C8 C41 H41B 108.5 . . ?
C31 C41 C8 115.0(3) . . ?
C31 C41 H41A 108.5 . . ?
C31 C41 H41B 108.5 . . ?
H41A C41 H41B 107.5 . . ?
C19 C44 C10 108.4(2) . . ?
C66 C44 C19 122.9(2) . . ?
C66 C44 C10 122.6(2) . . ?
C19 C45 C26 113.7(2) . . ?
C19 C45 C64 114.2(2) . . ?
C64 C45 C26 130.6(2) . . ?
C48 C49 C11 112.2(2) . . ?
C48 C49 C60 115.0(2) . . ?
C60 C49 C11 131.3(2) . . ?
C24 C55 H55A 108.6 . . ?
C24 C55 H55B 108.6 . . ?
C31 C55 C24 114.8(2) . . ?
C31 C55 H55A 108.6 . . ?
C31 C55 H55B 108.6 . . ?
H55A C55 H55B 107.5 . . ?
C30 C60 C49 120.5(2) . . ?
C30 C60 H60 119.7 . . ?
C49 C60 H60 119.7 . . ?
C45 C64 H64 118.6 . . ?
C67 C64 C45 122.7(2) . . ?
C67 C64 H64 118.6 . . ?
C44 C66 C43 113.3(2) . . ?
C44 C66 C80 114.7(2) . . ?
C80 C66 C43 130.7(2) . . ?
C38 C67 H67 119.2 . . ?
C64 C67 C38 121.6(2) . . ?
C64 C67 H67 119.2 . . ?
C26 C80 C66 122.0(2) . . ?
C26 C80 H80 119.0 . . ?
C66 C80 H80 119.0 . . ?

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
C11 C4 C17 O3 177.6(2) . . . . ?
C11 C4 C17 N17 -0.5(2) . . . . ?
C11 C4 C34 C10 7.9(3) . . . . ?
C11 C4 C34 C15 -157.4(2) . . . . ?
C11 C49 C60 C30 -156.4(2) . . . . ?
C13 N17 C1 C24 -99.9(3) . . . . ?
C13 N17 C17 O3 -176.2(2) . . . . ?
C13 N17 C17 C4 2.0(2) . . . . ?
C13 C11 C4 C17 -1.0(2) . . . . ?
C13 C11 C4 C34 171.45(19) . . . . ?
C13 C11 C49 C48 -177.2(2) . . . . ?
C13 C11 C49 C60 -12.5(4) . . . . ?
C19 C36 C48 C10 0.1(2) . . . . ?
C19 C36 C48 C49 -155.8(2) . . . . ?
C19 C36 C38 C30 160.2(2) . . . . ?
C19 C36 C38 C67 -8.5(3) . . . . ?
C19 C44 C66 C43 -160.4(2) . . . . ?
C19 C44 C66 C80 8.6(3) . . . . ?
C19 C45 C64 C67 -8.6(4) . . . . ?
C22 C43 C15 C34 -174.4(2) . . . . ?
C22 C43 C66 C44 -175.4(2) . . . . ?
C22 C43 C66 C80 17.9(4) . . . . ?
C36 C19 C44 C10 0.0(3) . . . . ?
C36 C19 C44 C66 153.1(2) . . . . ?
C36 C19 C45 C26 -158.3(2) . . . . ?
C36 C19 C45 C64 9.4(3) . . . . ?
C36 C48 C10 C34 -155.5(2) . . . . ?
C36 C48 C10 C44 0.0(2) . . . . ?
C36 C48 C49 C11 159.6(2) . . . . ?
C36 C48 C49 C60 -7.8(3) . . . . ?
C36 C38 C67 C64 9.2(3) . . . . ?
C40 C30 C38 C36 176.4(2) . . . . ?
C40 C30 C38 C67 -17.3(4) . . . . ?
C40 C30 C60 C49 174.8(2) . . . . ?
C43 C15 C34 C4 155.4(2) . . . . ?
C43 C15 C34 C10 -9.7(3) . . . . ?
C43 C66 C80 C26 158.5(2) . . . . ?
C48 C36 C38 C30 9.7(3) . . . . ?
C48 C36 C38 C67 -159.0(2) . . . . ?
C48 C10 C34 C4 -7.8(3) . . . . ?
C48 C10 C34 C15 160.0(2) . . . . ?
C48 C10 C44 C19 0.0(2) . . . . ?
C48 C10 C44 C66 -153.2(2) . . . . ?
C48 C49 C60 C30 8.0(3) . . . . ?
C4 C11 C13 O6 -175.6(2) . . . . ?
C4 C11 C13 N17 2.2(2) . . . . ?
C4 C11 C49 C48 -7.5(3) . . . . ?
C4 C11 C49 C60 157.3(2) . . . . ?
C10 C48 C49 C11 7.6(3) . . . . ?
C10 C48 C49 C60 -159.8(2) . . . . ?
C10 C44 C66 C43 -11.0(3) . . . . ?
C10 C44 C66 C80 157.9(2) . . . . ?
C1 N17 C13 O6 1.6(4) . . . . ?
C1 N17 C13 C11 -176.24(19) . . . . ?
C1 N17 C17 O3 -2.4(4) . . . . ?
C1 N17 C17 C4 175.7(2) . . . . ?
C1 C24 C55 C31 178.4(3) . . . . ?
C15 C43 C66 C44 9.6(3) . . . . ?
C15 C43 C66 C80 -157.1(3) . . . . ?
C17 N17 C13 O6 175.3(2) . . . . ?
C17 N17 C13 C11 -2.6(2) . . . . ?
C17 N17 C1 C24 87.2(3) . . . . ?
C17 C4 C34 C10 178.7(2) . . . . ?
C17 C4 C34 C15 13.5(4) . . . . ?
C26 C45 C64 C67 156.5(3) . . . . ?
C30 C38 C67 C64 -157.1(3) . . . . ?
C34 C4 C17 O3 5.6(4) . . . . ?
C34 C4 C17 N17 -172.5(2) . . . . ?
C34 C10 C44 C19 155.3(2) . . . . ?
C34 C10 C44 C66 2.1(3) . . . . ?
C38 C36 C48 C10 154.5(2) . . . . ?
C38 C36 C48 C49 -1.3(3) . . . . ?
C38 C30 C60 C49 0.6(3) . . . . ?
C41 C31 C55 C24 174.1(3) . . . . ?
C44 C19 C36 C48 -0.1(3) . . . . ?
C44 C19 C36 C38 -154.4(2) . . . . ?
C44 C19 C45 C26 -8.6(3) . . . . ?
C44 C19 C45 C64 159.0(2) . . . . ?
C44 C10 C34 C4 -159.3(2) . . . . ?
C44 C10 C34 C15 8.6(3) . . . . ?
C44 C66 C80 C26 -8.1(3) . . . . ?
C45 C19 C36 C48 153.4(2) . . . . ?
C45 C19 C36 C38 -0.9(4) . . . . ?
C45 C19 C44 C10 -153.2(2) . . . . ?
C45 C19 C44 C66 -0.1(4) . . . . ?
C45 C26 C80 C66 -0.7(4) . . . . ?
C45 C64 C67 C38 -0.7(4) . . . . ?
C49 C11 C13 O6 -4.6(4) . . . . ?
C49 C11 C13 N17 173.2(2) . . . . ?
C49 C11 C4 C17 -172.66(19) . . . . ?
C49 C11 C4 C34 -0.2(3) . . . . ?
C49 C48 C10 C34 0.1(3) . . . . ?
C49 C48 C10 C44 155.5(2) . . . . ?
C55 C24 C1 N17 64.0(4) . . . . ?
C55 C31 C41 C8 -178.7(4) . . . . ?
C60 C30 C38 C36 -9.3(3) . . . . ?
C60 C30 C38 C67 157.0(2) . . . . ?
C66 C43 C15 C34 0.7(3) . . . . ?
C80 C26 C45 C19 8.9(3) . . . . ?
C80 C26 C45 C64 -156.2(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.899 0.000 0.000 280.5 33.1 ?
2 -0.367 0.000 0.500 193.3 32.3 ?
3 -0.001 0.500 0.500 280.5 33.1 ?
4 0.351 0.500 0.000 193.3 32.3 ?

_olex2_submission_special_instructions 'No special instructions were received'
