# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

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

data_141215_cm_a
_database_code_depnum_ccdc_archive 'CCDC 1500090'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_audit_creation_date             2014-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.7512(9)
_cell_length_b                   8.8377(10)
_cell_length_c                   11.1832(10)
_cell_angle_alpha                90.101(8)
_cell_angle_beta                 91.344(8)
_cell_angle_gamma                106.984(9)
_cell_volume                     826.93(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4049
_cell_measurement_theta_min      2.8762
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5128
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0566845000
_diffrn_orient_matrix_UB_12      0.0320902000
_diffrn_orient_matrix_UB_13      0.0465871000
_diffrn_orient_matrix_UB_21      -0.0510198000
_diffrn_orient_matrix_UB_22      -0.0421381000
_diffrn_orient_matrix_UB_23      -0.0224459000
_diffrn_orient_matrix_UB_31      0.0370204000
_diffrn_orient_matrix_UB_32      -0.0650962000
_diffrn_orient_matrix_UB_33      0.0367584000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1798
_reflns_number_total             3021
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.47551(15) 0.32624(17) 0.15376(11) 0.0575(4) Uani 1 d . . .
N1 N 0.46105(16) 0.53295(19) 0.31248(12) 0.0439(4) Uani 1 d . . .
H1 H 0.4202 0.4404 0.2815 0.053 Uiso 1 calc . . R
N2 N 0.59489(19) 0.8280(2) 0.41460(14) 0.0547(5) Uani 1 d . . .
C1 C 0.3889(2) 0.5758(2) 0.40911(15) 0.0417(5) Uani 1 d . . .
C2 C 0.2518(2) 0.4743(3) 0.45705(16) 0.0514(5) Uani 1 d . . .
H2 H 0.2062 0.3742 0.4238 0.062 Uiso 1 calc . . R
C3 C 0.1846(2) 0.5234(3) 0.55398(18) 0.0579(6) Uani 1 d . . .
H3 H 0.0936 0.4555 0.5869 0.070 Uiso 1 calc . . R
C4 C 0.2504(3) 0.6724(3) 0.60324(19) 0.0649(6) Uani 1 d . . .
H4 H 0.2024 0.7043 0.6681 0.078 Uiso 1 calc . . R
C5 C 0.3857(3) 0.7734(3) 0.55730(18) 0.0643(6) Uani 1 d . . .
H5 H 0.4298 0.8734 0.5910 0.077 Uiso 1 calc . . R
C6 C 0.4575(2) 0.7254(2) 0.45922(16) 0.0474(5) Uani 1 d . . .
C7 C 0.6582(2) 0.7837(2) 0.32091(16) 0.0455(5) Uani 1 d . . .
C8 C 0.5926(2) 0.6293(2) 0.26424(15) 0.0405(5) Uani 1 d . . .
C9 C 0.6619(2) 0.5778(2) 0.16639(15) 0.0442(5) Uani 1 d . . .
H9 H 0.7533 0.6467 0.1348 0.053 Uiso 1 calc . . R
C10 C 0.6006(2) 0.4286(2) 0.11417(15) 0.0432(5) Uani 1 d . . .
C11 C 0.6774(2) 0.3781(2) 0.00905(15) 0.0442(5) Uani 1 d . . .
C12 C 0.6219(2) 0.2237(3) -0.03154(18) 0.0596(6) Uani 1 d . . .
H12 H 0.5387 0.1526 0.0076 0.072 Uiso 1 calc . . R
C13 C 0.6878(3) 0.1730(3) -0.1292(2) 0.0721(7) Uani 1 d . . .
H13 H 0.6492 0.0687 -0.1557 0.087 Uiso 1 calc . . R
C14 C 0.8101(3) 0.2772(3) -0.18657(19) 0.0717(7) Uani 1 d . . .
H14 H 0.8551 0.2436 -0.2523 0.086 Uiso 1 calc . . R
C15 C 0.8666(3) 0.4305(3) -0.14783(19) 0.0687(7) Uani 1 d . . .
H15 H 0.9501 0.5009 -0.1872 0.082 Uiso 1 calc . . R
C16 C 0.8006(2) 0.4814(3) -0.05073(17) 0.0570(6) Uani 1 d . . .
H16 H 0.8394 0.5862 -0.0252 0.068 Uiso 1 calc . . R
C17 C 0.8070(2) 0.8984(2) 0.27722(16) 0.0489(5) Uani 1 d . . .
C18 C 0.9433(2) 0.9373(3) 0.34850(18) 0.0571(6) Uani 1 d . . .
H18 H 0.9423 0.8894 0.4226 0.068 Uiso 1 calc . . R
C19 C 1.0812(3) 1.0461(3) 0.3118(2) 0.0653(6) Uani 1 d . . .
H19 H 1.1729 1.0698 0.3603 0.078 Uiso 1 calc . . R
C20 C 1.0833(3) 1.1196(3) 0.2038(2) 0.0721(7) Uani 1 d . . .
H20 H 1.1759 1.1940 0.1792 0.087 Uiso 1 calc . . R
C21 C 0.9481(3) 1.0826(3) 0.1323(2) 0.0828(8) Uani 1 d . . .
H21 H 0.9486 1.1326 0.0592 0.099 Uiso 1 calc . . R
C22 C 0.8117(3) 0.9716(3) 0.16847(19) 0.0742(7) Uani 1 d . . .
H22 H 0.7211 0.9457 0.1185 0.089 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.288(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.371(2) . ?
N1 C8 1.341(2) . ?
N2 C6 1.382(2) . ?
N2 C7 1.308(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(3) . ?
C7 C8 1.454(3) . ?
C7 C17 1.491(3) . ?
C8 C9 1.401(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(3) . ?
C10 C11 1.498(2) . ?
C11 C12 1.380(3) . ?
C11 C16 1.380(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.366(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 C22 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(3) . ?
C22 H22 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
C1 N1 H1 118.6 . . ?
C8 N1 H1 118.6 . . ?
C8 N1 C1 122.79(17) . . ?
C7 N2 C6 118.52(18) . . ?
N1 C1 C2 121.78(19) . . ?
N1 C1 C6 117.93(17) . . ?
C2 C1 C6 120.29(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
N2 C6 C1 121.60(17) . . ?
N2 C6 C5 119.1(2) . . ?
C1 C6 C5 119.33(19) . . ?
N2 C7 C8 122.63(18) . . ?
N2 C7 C17 116.22(18) . . ?
C8 C7 C17 121.11(16) . . ?
N1 C8 C7 116.49(16) . . ?
N1 C8 C9 120.08(18) . . ?
C9 C8 C7 123.40(17) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 C8 123.18(18) . . ?
C10 C9 H9 118.4 . . ?
O1 C10 C9 121.97(17) . . ?
O1 C10 C11 116.34(18) . . ?
C9 C10 C11 121.69(17) . . ?
C12 C11 C10 119.32(18) . . ?
C12 C11 C16 118.32(18) . . ?
C16 C11 C10 122.35(19) . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C7 119.71(17) . . ?
C22 C17 C7 121.98(17) . . ?
C22 C17 C18 118.28(19) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.94(19) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 121.0(2) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?

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
O1 C10 C11 C12 -6.3(2) . . . . ?
O1 C10 C11 C16 172.48(15) . . . . ?
N1 C1 C2 C3 179.99(15) . . . . ?
N1 C1 C6 N2 -0.7(2) . . . . ?
N1 C1 C6 C5 179.34(14) . . . . ?
N1 C8 C9 C10 0.3(2) . . . . ?
N2 C7 C8 N1 0.5(2) . . . . ?
N2 C7 C8 C9 -177.77(15) . . . . ?
N2 C7 C17 C18 64.6(2) . . . . ?
N2 C7 C17 C22 -113.3(2) . . . . ?
C1 N1 C8 C7 0.8(2) . . . . ?
C1 N1 C8 C9 179.19(14) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 N2 179.10(14) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 N2 -179.36(16) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 N2 C7 C8 -1.9(3) . . . . ?
C6 N2 C7 C17 -179.51(14) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C7 N2 C6 C1 2.0(3) . . . . ?
C7 N2 C6 C5 -178.05(16) . . . . ?
C7 C8 C9 C10 178.50(14) . . . . ?
C7 C17 C18 C19 -178.23(19) . . . . ?
C7 C17 C22 C21 176.9(2) . . . . ?
C8 N1 C1 C2 179.49(14) . . . . ?
C8 N1 C1 C6 -0.8(2) . . . . ?
C8 C7 C17 C18 -113.1(2) . . . . ?
C8 C7 C17 C22 69.1(3) . . . . ?
C8 C9 C10 O1 -0.8(3) . . . . ?
C8 C9 C10 C11 179.59(14) . . . . ?
C9 C10 C11 C12 173.35(15) . . . . ?
C9 C10 C11 C16 -7.8(2) . . . . ?
C10 C11 C12 C13 179.04(16) . . . . ?
C10 C11 C16 C15 -179.25(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C17 C7 C8 N1 178.06(14) . . . . ?
C17 C7 C8 C9 -0.2(3) . . . . ?
C17 C18 C19 C20 1.2(3) . . . . ?
C18 C17 C22 C21 -0.9(3) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C17 1.3(4) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?

####################################################################### 
# 
# 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_141212_cm_c
_database_code_depnum_ccdc_archive 'CCDC 1500092'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_audit_creation_date             2014-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8856(12)
_cell_length_b                   5.8214(6)
_cell_length_c                   26.159(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.577(13)
_cell_angle_gamma                90.00
_cell_volume                     1649.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1214
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6140
_cell_measurement_theta_min      3.1234
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            6398
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.13
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0502910000
_diffrn_orient_matrix_UB_12      0.0650347000
_diffrn_orient_matrix_UB_13      0.0074854000
_diffrn_orient_matrix_UB_21      -0.0074288000
_diffrn_orient_matrix_UB_22      0.0521032000
_diffrn_orient_matrix_UB_23      -0.0246296000
_diffrn_orient_matrix_UB_31      -0.0412319000
_diffrn_orient_matrix_UB_32      -0.0888730000
_diffrn_orient_matrix_UB_33      -0.0089579000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1907
_reflns_number_total             2992
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.4401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1653
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.18335(16) 0.7724(3) 0.20196(7) 0.0571(5) Uani 1 d . . .
N1 N 0.08101(18) 0.4304(4) 0.15219(8) 0.0462(5) Uani 1 d . . .
H1 H 0.0823 0.5222 0.1780 0.055 Uiso 1 calc . . R
N2 N 0.07300(19) 0.1428(3) 0.06771(8) 0.0481(6) Uani 1 d . . .
C1 C 0.0039(2) 0.2435(4) 0.15028(10) 0.0448(6) Uani 1 d . . .
C2 C -0.0691(2) 0.1982(5) 0.18968(11) 0.0559(7) Uani 1 d . . .
H2 H -0.0686 0.2969 0.2176 0.067 Uiso 1 calc . . R
C3 C -0.1419(3) 0.0063(5) 0.18682(12) 0.0650(8) Uani 1 d . . .
H3 H -0.1907 -0.0256 0.2132 0.078 Uiso 1 calc . . R
C4 C -0.1441(3) -0.1411(5) 0.14517(13) 0.0659(8) Uani 1 d . . .
H4 H -0.1939 -0.2712 0.1440 0.079 Uiso 1 calc . . R
C5 C -0.0735(2) -0.0968(5) 0.10582(12) 0.0576(7) Uani 1 d . . .
H5 H -0.0757 -0.1956 0.0778 0.069 Uiso 1 calc . . R
C6 C 0.0021(2) 0.0981(4) 0.10794(10) 0.0448(6) Uani 1 d . . .
C7 C 0.1439(2) 0.3240(4) 0.07101(9) 0.0419(6) Uani 1 d . . .
C8 C 0.1543(2) 0.4745(4) 0.11507(9) 0.0399(6) Uani 1 d . . .
C9 C 0.2389(2) 0.6558(4) 0.12150(9) 0.0447(6) Uani 1 d . . .
H9 H 0.2885 0.6860 0.0953 0.054 Uiso 1 calc . . R
C10 C 0.2523(2) 0.7936(4) 0.16539(9) 0.0426(6) Uani 1 d . . .
C11 C 0.3491(2) 0.9762(4) 0.17136(9) 0.0428(6) Uani 1 d . . .
C12 C 0.3372(2) 1.1543(4) 0.20568(10) 0.0505(7) Uani 1 d . . .
H12 H 0.2684 1.1597 0.2241 0.061 Uiso 1 calc . . R
C13 C 0.4261(3) 1.3240(5) 0.21284(11) 0.0612(8) Uani 1 d . . .
H13 H 0.4169 1.4431 0.2359 0.073 Uiso 1 calc . . R
C14 C 0.5271(3) 1.3162(5) 0.18606(12) 0.0651(8) Uani 1 d . . .
H14 H 0.5868 1.4306 0.1906 0.078 Uiso 1 calc . . R
C15 C 0.5413(3) 1.1397(5) 0.15227(11) 0.0630(8) Uani 1 d . . .
H15 H 0.6110 1.1339 0.1344 0.076 Uiso 1 calc . . R
C16 C 0.4522(2) 0.9707(5) 0.14479(10) 0.0522(7) Uani 1 d . . .
H16 H 0.4620 0.8525 0.1216 0.063 Uiso 1 calc . . R
C17 C 0.2188(2) 0.3688(4) 0.02765(9) 0.0431(6) Uani 1 d . . .
C18 C 0.3035(3) 0.2090(5) 0.01447(10) 0.0571(7) Uani 1 d . . .
H18 H 0.3125 0.0719 0.0327 0.069 Uiso 1 calc . . R
C19 C 0.3748(3) 0.2485(5) -0.02508(11) 0.0665(9) Uani 1 d . . .
H19 H 0.4326 0.1399 -0.0331 0.080 Uiso 1 calc . . R
C20 C 0.3609(3) 0.4489(5) -0.05274(11) 0.0642(8) Uani 1 d . . .
H20 H 0.4101 0.4776 -0.0792 0.077 Uiso 1 calc . . R
C21 C 0.2740(3) 0.6066(5) -0.04121(11) 0.0629(8) Uani 1 d . . .
H21 H 0.2623 0.7395 -0.0608 0.075 Uiso 1 calc . . R
C22 C 0.2043(3) 0.5697(4) -0.00107(10) 0.0556(7) Uani 1 d . . .
H22 H 0.1471 0.6794 0.0070 0.067 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.278(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.372(3) . ?
N1 C8 1.340(3) . ?
N2 C6 1.389(3) . ?
N2 C7 1.305(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(4) . ?
C7 C8 1.443(3) . ?
C7 C17 1.482(3) . ?
C8 C9 1.400(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.396(3) . ?
C10 C11 1.495(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.361(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 C22 1.391(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(4) . ?
C22 H22 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
C1 N1 H1 119.0 . . ?
C8 N1 H1 119.0 . . ?
C8 N1 C1 122.0(2) . . ?
C7 N2 C6 118.1(2) . . ?
N1 C1 C2 121.1(2) . . ?
N1 C1 C6 118.2(2) . . ?
C2 C1 C6 120.7(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
N2 C6 C1 121.5(2) . . ?
N2 C6 C5 119.3(2) . . ?
C1 C6 C5 119.2(2) . . ?
N2 C7 C8 122.9(2) . . ?
N2 C7 C17 117.2(2) . . ?
C8 C7 C17 119.9(2) . . ?
N1 C8 C7 117.2(2) . . ?
N1 C8 C9 119.2(2) . . ?
C9 C8 C7 123.5(2) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 C8 123.1(2) . . ?
C10 C9 H9 118.4 . . ?
O1 C10 C9 122.5(2) . . ?
O1 C10 C11 116.7(2) . . ?
C9 C10 C11 120.7(2) . . ?
C12 C11 C10 119.3(2) . . ?
C16 C11 C10 122.1(2) . . ?
C16 C11 C12 118.5(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.5(3) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C7 120.2(2) . . ?
C18 C17 C22 118.4(2) . . ?
C22 C17 C7 121.3(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.2(2) . . ?
C21 C22 H22 119.9 . . ?

####################################################################### 
# 
# 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_141211_cm_b
_database_code_depnum_ccdc_archive 'CCDC 1500091'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_audit_creation_date             2014-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.2692(8)
_cell_length_b                   9.9355(10)
_cell_length_c                   10.8222(9)
_cell_angle_alpha                79.332(8)
_cell_angle_beta                 65.483(8)
_cell_angle_gamma                69.001(9)
_cell_volume                     845.80(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1675
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4692
_cell_measurement_theta_min      3.8364
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5305
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.84
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0098785000
_diffrn_orient_matrix_UB_12      -0.0124558000
_diffrn_orient_matrix_UB_13      0.0693118000
_diffrn_orient_matrix_UB_21      0.0367025000
_diffrn_orient_matrix_UB_22      0.0538762000
_diffrn_orient_matrix_UB_23      -0.0067273000
_diffrn_orient_matrix_UB_31      -0.0800474000
_diffrn_orient_matrix_UB_32      0.0529194000
_diffrn_orient_matrix_UB_33      0.0186927000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2122
_reflns_number_total             3075
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0639P)²+0.1096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1468
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.44573(16) 0.70219(17) 0.27601(13) 0.0647(4) Uani 1 d . . .
N1 N 0.16969(17) 0.78212(16) 0.47915(14) 0.0439(4) Uani 1 d . . .
H1 H 0.2222 0.7630 0.3945 0.053 Uiso 1 calc . . R
N2 N 0.00114(17) 0.84603(17) 0.75041(14) 0.0458(4) Uani 1 d . . .
C1 C -0.0016(2) 0.82885(19) 0.53129(18) 0.0420(4) Uani 1 d . . .
C2 C -0.0913(2) 0.8454(2) 0.4499(2) 0.0515(5) Uani 1 d . . .
H2 H -0.0357 0.8266 0.3579 0.062 Uiso 1 calc . . R
C3 C -0.2624(3) 0.8898(2) 0.5074(2) 0.0597(6) Uani 1 d . . .
H3 H -0.3227 0.9007 0.4537 0.072 Uiso 1 calc . . R
C4 C -0.3472(2) 0.9188(2) 0.6441(2) 0.0614(6) Uani 1 d . . .
H4 H -0.4633 0.9481 0.6814 0.074 Uiso 1 calc . . R
C5 C -0.2608(2) 0.9046(2) 0.7244(2) 0.0560(5) Uani 1 d . . .
H5 H -0.3183 0.9248 0.8160 0.067 Uiso 1 calc . . R
C6 C -0.0854(2) 0.8595(2) 0.66897(18) 0.0437(4) Uani 1 d . . .
C7 C 0.1643(2) 0.80087(19) 0.69772(16) 0.0405(4) Uani 1 d . . .
C8 C 0.2580(2) 0.76522(19) 0.55565(17) 0.0398(4) Uani 1 d . . .
C9 C 0.4349(2) 0.7196(2) 0.49381(17) 0.0440(4) Uani 1 d . . .
H9 H 0.4958 0.7093 0.5469 0.053 Uiso 1 calc . . R
C10 C 0.5204(2) 0.6898(2) 0.35738(18) 0.0489(5) Uani 1 d . . .
C11 C 0.7065(2) 0.6447(2) 0.29542(18) 0.0511(5) Uani 1 d . . .
C12 C 0.7845(3) 0.6812(3) 0.1597(2) 0.0781(7) Uani 1 d . . .
H12 H 0.7204 0.7327 0.1090 0.094 Uiso 1 calc . . R
C13 C 0.9559(3) 0.6421(4) 0.0994(3) 0.1024(10) Uani 1 d . . .
H13 H 1.0070 0.6688 0.0088 0.123 Uiso 1 calc . . R
C14 C 1.0510(3) 0.5642(3) 0.1721(3) 0.0941(9) Uani 1 d . . .
H14 H 1.1669 0.5374 0.1305 0.113 Uiso 1 calc . . R
C15 C 0.9772(3) 0.5252(3) 0.3059(3) 0.0733(7) Uani 1 d . . .
H15 H 1.0428 0.4714 0.3549 0.088 Uiso 1 calc . . R
C16 C 0.8042(2) 0.5662(2) 0.3682(2) 0.0562(5) Uani 1 d . . .
H16 H 0.7540 0.5407 0.4594 0.067 Uiso 1 calc . . R
C17 C 0.2492(2) 0.7938(2) 0.79000(16) 0.0432(5) Uani 1 d . . .
C18 C 0.1960(2) 0.9112(2) 0.86828(18) 0.0547(5) Uani 1 d . . .
H18 H 0.1128 0.9939 0.8581 0.066 Uiso 1 calc . . R
C19 C 0.2641(3) 0.9074(3) 0.9604(2) 0.0744(7) Uani 1 d . . .
H19 H 0.2270 0.9869 1.0121 0.089 Uiso 1 calc . . R
C20 C 0.3870(3) 0.7859(4) 0.9759(2) 0.0850(9) Uani 1 d . . .
H20 H 0.4333 0.7828 1.0383 0.102 Uiso 1 calc . . R
C21 C 0.4416(3) 0.6688(3) 0.8991(2) 0.0768(8) Uani 1 d . . .
H21 H 0.5257 0.5871 0.9095 0.092 Uiso 1 calc . . R
C22 C 0.3733(2) 0.6707(2) 0.80670(19) 0.0570(5) Uani 1 d . . .
H22 H 0.4101 0.5903 0.7561 0.068 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.294(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.371(2) . ?
N1 C8 1.340(2) . ?
N2 C6 1.380(2) . ?
N2 C7 1.307(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(2) . ?
C7 C8 1.455(2) . ?
C7 C17 1.486(2) . ?
C8 C9 1.418(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 C11 1.491(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 C22 1.391(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(3) . ?
C22 H22 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
C1 N1 H1 118.9 . . ?
C8 N1 H1 118.9 . . ?
C8 N1 C1 122.19(14) . . ?
C7 N2 C6 118.98(14) . . ?
N1 C1 C2 121.29(16) . . ?
N1 C1 C6 118.30(16) . . ?
C2 C1 C6 120.41(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.06(18) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.20(18) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.25(18) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.16(18) . . ?
C6 C5 H5 119.9 . . ?
N2 C6 C1 121.21(15) . . ?
N2 C6 C5 119.88(16) . . ?
C1 C6 C5 118.91(17) . . ?
N2 C7 C8 122.16(16) . . ?
N2 C7 C17 116.05(14) . . ?
C8 C7 C17 121.74(14) . . ?
N1 C8 C7 117.15(15) . . ?
N1 C8 C9 118.95(15) . . ?
C9 C8 C7 123.86(16) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.50(17) . . ?
C10 C9 H9 118.8 . . ?
O1 C10 C9 122.86(16) . . ?
O1 C10 C11 116.19(15) . . ?
C9 C10 C11 120.93(18) . . ?
C12 C11 C10 119.0(2) . . ?
C16 C11 C10 122.26(17) . . ?
C16 C11 C12 118.72(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C7 118.82(16) . . ?
C18 C17 C22 118.77(18) . . ?
C22 C17 C7 122.30(17) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?

