# 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_nj1501
_database_code_depnum_ccdc_archive 'CCDC 1452788'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_audit_creation_date             2015-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18'
_chemical_formula_sum            'C18 H18'
_chemical_formula_weight         234.32
_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'

_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           14
_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                   10.230(4)
_cell_length_b                   4.7903(17)
_cell_length_c                   14.674(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.855(8)
_cell_angle_gamma                90
_cell_volume                     680.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1175 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.6664.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11902
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.775
_diffrn_reflns_theta_min         2.928
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_source         'ImuS micro-focus tube'
_diffrn_radiation_monochromator  'Quazar focussing montel optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 83.33
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1353
_reflns_number_total             1766
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1766
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Same fragment restrains
{C1, C2, C3, C4, C5, C6, C7, C8, C9} sigma for 1-2: 0.02, 1-3: 0.04
as
{C11, C12, C13, C14, C15, C16, C17, C18, C19}
4. Others
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(H19)=1-FVAR(1)
 Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(C7)=Sof(C8)=Sof(C9)=
 Sof(H1)=Sof(H2)=Sof(H3)=Sof(H4)=Sof(H5)=Sof(H6)=Sof(H7)=Sof(H8)=Sof(H9)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.97339(15) -0.0093(3) 1.18850(9) 0.0228(3) Uani 0.951(2) 1 d D . P A 1
C2 C 0.89409(13) 0.2145(3) 1.14136(9) 0.0220(3) Uani 0.951(2) 1 d D . P A 1
C3 C 0.76449(16) 0.2941(3) 1.14290(10) 0.0228(3) Uani 0.951(2) 1 d D . P A 1
C4 C 0.68484(13) 0.5063(3) 1.08433(10) 0.0231(3) Uani 0.951(2) 1 d D . P A 1
C5 C 0.72539(12) 0.6488(3) 1.01545(9) 0.0214(3) Uani 0.951(2) 1 d D . P A 1
C6 C 0.65710(14) 0.8635(3) 0.95515(12) 0.0223(3) Uani 0.951(2) 1 d D . P A 1
C7 C 0.71251(14) 1.0100(3) 0.89317(9) 0.0223(3) Uani 0.951(2) 1 d D . P A 1
C8 C 0.84193(13) 0.9583(3) 0.88519(9) 0.0211(3) Uani 0.951(2) 1 d D . P A 1
C9 C 0.9000(2) 1.0877(4) 0.82260(13) 0.0236(3) Uani 0.951(2) 1 d D . P A 1
H1 H 0.9386(14) -0.126(3) 1.2323(10) 0.032(4) Uiso 0.951(2) 1 d . . P A 1
H2 H 0.9330(14) 0.330(3) 1.1017(9) 0.026(4) Uiso 0.951(2) 1 d . . P A 1
H3 H 0.7234(14) 0.188(3) 1.1852(10) 0.025(3) Uiso 0.951(2) 1 d . . P A 1
H4 H 0.5961(15) 0.555(3) 1.0930(10) 0.031(4) Uiso 0.951(2) 1 d . . P A 1
H5 H 0.8143(14) 0.592(3) 1.0090(10) 0.028(4) Uiso 0.951(2) 1 d . . P A 1
H6 H 0.5659(15) 0.920(3) 0.9573(10) 0.031(4) Uiso 0.951(2) 1 d . . P A 1
H7 H 0.6573(14) 1.156(3) 0.8535(10) 0.028(4) Uiso 0.951(2) 1 d . . P A 1
H8 H 0.8968(14) 0.807(3) 0.9274(10) 0.032(4) Uiso 0.951(2) 1 d . . P A 1
H9 H 0.8486(14) 1.246(3) 0.7839(10) 0.028(4) Uiso 0.951(2) 1 d . . P A 1
C11 C 1.029(2) 0.061(6) 1.1493(18) 0.025(6) Uani 0.049(2) 1 d D U P A 2
H11 H 1.0215 0.2081 1.1044 0.030 Uiso 0.049(2) 1 calc R . P A 2
C12 C 0.922(2) 0.070(5) 1.1846(18) 0.017(6) Uani 0.049(2) 1 d D U P A 2
H12 H 0.9287 -0.0666 1.2328 0.020 Uiso 0.049(2) 1 calc R . P A 2
C13 C 0.807(3) 0.231(7) 1.166(3) 0.050(14) Uani 0.049(2) 1 d D U P A 2
H13 H 0.7458 0.2030 1.2025 0.060 Uiso 0.049(2) 1 calc R . P A 2
C14 C 0.778(2) 0.431(5) 1.0979(16) 0.026(6) Uani 0.049(2) 1 d D U P A 2
H14 H 0.8522 0.4564 1.0735 0.031 Uiso 0.049(2) 1 calc R . P A 2
C15 C 0.672(3) 0.603(5) 1.0547(18) 0.023(7) Uani 0.049(2) 1 d D U P A 2
H15 H 0.5933 0.5808 1.0746 0.027 Uiso 0.049(2) 1 calc R . P A 2
C16 C 0.661(3) 0.803(6) 0.987(2) 0.024(9) Uani 0.049(2) 1 d D U P A 2
H16 H 0.5787 0.9117 0.9688 0.029 Uiso 0.049(2) 1 calc R . P A 2
C17 C 0.755(2) 0.861(4) 0.9438(15) 0.021(6) Uani 0.049(2) 1 d D U P A 2
H17 H 0.8308 0.7344 0.9612 0.026 Uiso 0.049(2) 1 calc R . P A 2
C18 C 0.768(2) 1.058(5) 0.8812(15) 0.014(5) Uani 0.049(2) 1 d D U P A 2
H18 H 0.6980 1.1978 0.8626 0.017 Uiso 0.049(2) 1 calc R . P A 2
C19 C 0.874(3) 1.072(9) 0.842(3) 0.025(11) Uani 0.049(2) 1 d D U P A 2
H19 H 0.8644 1.2248 0.7994 0.030 Uiso 0.049(2) 1 calc R . 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
C1 C2 1.3870(19) . ?
C1 C9 1.408(3) 3_767 ?
C1 H1 1.000(15) . ?
C2 C3 1.387(2) . ?
C2 H2 0.975(15) . ?
C3 C4 1.408(2) . ?
C3 H3 0.995(14) . ?
C4 C5 1.3895(19) . ?
C4 H4 0.985(15) . ?
C5 C6 1.389(2) . ?
C5 H5 0.982(14) . ?
C6 C7 1.405(2) . ?
C6 H6 0.983(15) . ?
C7 C8 1.3885(18) . ?
C7 H7 0.969(15) . ?
C8 C9 1.390(2) . ?
C8 H8 0.999(15) . ?
C9 C1 1.408(3) 3_767 ?
C9 H9 0.990(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.353(18) . ?
C11 C19 1.16(4) 3_767 ?
C12 H12 0.9500 . ?
C12 C13 1.360(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.348(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.341(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.356(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.349(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.350(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(19) . ?
C19 C11 1.16(4) 3_767 ?
C19 H19 0.9500 . ?

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
C2 C1 C9 124.06(14) . 3_767 ?
C2 C1 H1 118.7(9) . . ?
C9 C1 H1 117.2(8) 3_767 . ?
C1 C2 H2 116.7(8) . . ?
C3 C2 C1 127.77(14) . . ?
C3 C2 H2 115.5(8) . . ?
C2 C3 C4 123.79(13) . . ?
C2 C3 H3 117.9(8) . . ?
C4 C3 H3 118.2(8) . . ?
C3 C4 H4 117.9(9) . . ?
C5 C4 C3 123.27(12) . . ?
C5 C4 H4 118.9(9) . . ?
C4 C5 H5 116.0(8) . . ?
C6 C5 C4 128.33(13) . . ?
C6 C5 H5 115.7(8) . . ?
C5 C6 C7 123.85(13) . . ?
C5 C6 H6 118.2(9) . . ?
C7 C6 H6 118.0(9) . . ?
C6 C7 H7 118.2(8) . . ?
C8 C7 C6 124.11(12) . . ?
C8 C7 H7 117.7(8) . . ?
C7 C8 C9 126.80(14) . . ?
C7 C8 H8 115.9(8) . . ?
C9 C8 H8 117.2(8) . . ?
C1 C9 H9 118.4(8) 3_767 . ?
C8 C9 C1 124.28(15) . 3_767 ?
C8 C9 H9 117.3(8) . . ?
C12 C11 H11 110.5 . . ?
C19 C11 H11 110.5 3_767 . ?
C19 C11 C12 139(3) 3_767 . ?
C11 C12 H12 112.9 . . ?
C11 C12 C13 134(2) . . ?
C13 C12 H12 112.9 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 111.3 . . ?
C15 C14 C13 137(2) . . ?
C15 C14 H14 111.3 . . ?
C14 C15 H15 114.8 . . ?
C14 C15 C16 130(2) . . ?
C16 C15 H15 114.8 . . ?
C15 C16 H16 117.1 . . ?
C17 C16 C15 126(2) . . ?
C17 C16 H16 117.1 . . ?
C16 C17 H17 112.6 . . ?
C16 C17 C18 135(2) . . ?
C18 C17 H17 112.6 . . ?
C17 C18 H18 117.6 . . ?
C17 C18 C19 125(3) . . ?
C19 C18 H18 117.6 . . ?
C11 C19 C18 134(4) 3_767 . ?
C11 C19 H19 112.9 3_767 . ?
C18 C19 H19 112.9 . . ?

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
C1 C2 C3 C4 -172.68(13) . . . . ?
C2 C3 C4 C5 3.2(2) . . . . ?
C3 C4 C5 C6 -178.78(13) . . . . ?
C4 C5 C6 C7 174.53(13) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 177.14(14) . . . . ?
C7 C8 C9 C1 -173.97(14) . . . 3_767 ?
C9 C1 C2 C3 175.12(14) 3_767 . . . ?
C11 C12 C13 C14 2(6) . . . . ?
C12 C13 C14 C15 172(3) . . . . ?
C13 C14 C15 C16 178(4) . . . . ?
C14 C15 C16 C17 4(6) . . . . ?
C15 C16 C17 C18 -175(3) . . . . ?
C16 C17 C18 C19 -177(3) . . . . ?
C17 C18 C19 C11 0(7) . . . 3_767 ?
C19 C11 C12 C13 -176(5) 3_767 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


#===END OF ALL DATA

####################################################################### 
# 
# 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_dl09_2
_database_code_depnum_ccdc_archive 'CCDC 1452902'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_audit_creation_date             2015-04-24
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H6, C6 H6'
_chemical_formula_sum            'C24 H12'
_chemical_formula_weight         300.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H6 N'
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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z+1/2'
'-x+1/2, y, -z'
'y+3/4, x+1/4, -z+1/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1'
'-x+1, y+1/2, -z+1/2'
'y+5/4, x+3/4, -z+3/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z-1/2'
'x-1/2, -y, z'
'-y-3/4, -x-1/4, z-1/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-y-1/4, -x+1/4, z+1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   21.6492(2)
_cell_length_b                   21.6492(2)
_cell_length_c                   14.6312(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6857.48(17)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4676
_cell_measurement_temperature    173.1(6)
_cell_measurement_theta_max      61.2620
_cell_measurement_theta_min      5.4880
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.2806
_exptl_crystal_size_mid          0.1921
_exptl_crystal_size_min          0.1659
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9384
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         61.548
_diffrn_reflns_theta_min         4.084
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.1(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9828
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   91.00  144.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -       82.5931   15.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega   59.00   96.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -       82.5931  -45.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  169.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -       82.5931    0.0000   30.0000 149

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00   67.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -       82.5931   15.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00  106.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ frames
    -       82.5931  -94.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
  7 omega  -76.00  -46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega  -88.00  -48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega  -83.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0676168000
_diffrn_orient_matrix_UB_12      -0.0062056000
_diffrn_orient_matrix_UB_13      -0.0315012000
_diffrn_orient_matrix_UB_21      0.0150331000
_diffrn_orient_matrix_UB_22      0.0372597000
_diffrn_orient_matrix_UB_23      -0.0869205000
_diffrn_orient_matrix_UB_31      0.0162074000
_diffrn_orient_matrix_UB_32      -0.0603601000
_diffrn_orient_matrix_UB_33      -0.0503376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1132
_reflns_number_total             1342
_reflns_odcompleteness_completeness 98.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.05
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+0.8363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.28125(6) 0.38207(5) -0.00135(7) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.33731(6) 0.37916(5) -0.00290(7) 0.0385(4) Uani 1 1 d . . . . .
C3 C 0.40195(6) 0.37565(6) -0.00223(8) 0.0447(4) Uani 1 1 d . . . . .
H3 H 0.4243 0.4123 -0.0048 0.054 Uiso 1 1 calc R . . . .
C4 C 0.43357(6) 0.32218(6) 0.00191(8) 0.0460(4) Uani 1 1 d . . . . .
H4 H 0.4765 0.3240 0.0025 0.055 Uiso 1 1 calc R . . . .
C5 C 0.40528(6) 0.26371(6) 0.00539(7) 0.0406(4) Uani 1 1 d . . . . .
C6 C 0.37912(5) 0.21424(6) 0.00799(8) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.34715(6) 0.16025(6) 0.00934(8) 0.0381(4) Uani 1 1 d . . . . .
C8 C 0.31657(6) 0.11338(6) 0.00816(8) 0.0419(4) Uani 1 1 d . . . . .
C9 C 0.28093(7) 0.05932(6) 0.00422(9) 0.0532(4) Uani 1 1 d . . . . .
H9 H 0.3011 0.0215 0.0076 0.064 Uiso 1 1 calc R . . . .
C11 C 0.24917(4) 0.24856(5) 0.15530(8) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.2486 0.2476 0.0918 0.041 Uiso 1 1 calc R . . . .
C12 C 0.21178(5) 0.20886(5) 0.20486(8) 0.0357(3) Uani 1 1 d . . . . .
H12 H 0.1861 0.1812 0.1746 0.043 Uiso 1 1 calc R . . . .
C13 C 0.21261(5) 0.21041(5) 0.29934(7) 0.0355(3) Uani 1 1 d . . . . .
H13 H 0.1874 0.1838 0.3325 0.043 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
C1 C1 1.354(3) 6 ?
C1 C2 1.2156(19) . ?
C2 C3 1.401(2) . ?
C3 C4 1.3461(19) . ?
C4 C5 1.4072(19) . ?
C5 C6 1.2121(19) . ?
C6 C7 1.3585(19) . ?
C7 C8 1.2117(19) . ?
C8 C9 1.4030(19) . ?
C9 C9 1.345(3) 6 ?
C11 C12 1.3857(16) . ?
C11 C13 1.3835(16) 25 ?
C12 C13 1.3829(17) . ?
C13 C11 1.3834(16) 25 ?

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
C2 C1 C1 176.97(8) . 6 ?
C1 C2 C3 178.52(11) . . ?
C4 C3 C2 123.69(12) . . ?
C3 C4 C5 123.64(13) . . ?
C6 C5 C4 177.92(14) . . ?
C5 C6 C7 177.08(13) . . ?
C8 C7 C6 177.02(13) . . ?
C7 C8 C9 178.44(14) . . ?
C9 C9 C8 123.47(8) 6 . ?
C13 C11 C12 119.78(12) 25 . ?
C13 C12 C11 120.03(10) . . ?
C12 C13 C11 120.19(10) . 25 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9 -2 -7 0.1301 9.1212 -1.5035 -7.1634 -0.3818 0.7037 0.5992
-1 -14 -1 0.0777 -1.4281 -13.8165 -1.4061 0.2266 -0.4140 0.8816
-9 2 7 0.1012 -8.8949 2.4842 7.1688 0.3602 -0.6643 -0.6550
2 14 1 0.0838 1.9095 13.8281 1.0444 -0.2478 0.4532 -0.8563
9 5 -6 0.1289 9.3508 5.3466 -6.1047 -0.4731 0.8704 0.1361
0 -9 -8 0.0997 -0.3262 -8.6010 -7.5098 0.3120 0.3274 0.8919
7 -6 7 0.0450 7.4717 -6.4831 6.7397 -0.6773 -0.7150 0.1732
-4 13 3 0.1180 -4.3798 12.5214 3.1326 0.1198 0.1284 -0.9845
-7 6 -7 0.1375 -7.3896 6.0448 -6.9636 0.6815 0.7194 -0.1341
-5 -2 -9 0.1180 -4.7234 -1.5888 -8.8798 0.6090 0.6416 0.4663
13 -3 -2 0.1291 12.9982 -3.0009 -1.9994 -0.7973 0.2574 0.4924
-13 3 2 0.1291 -12.9982 3.0009 1.9994 0.7973 -0.2574 -0.4924
14 2 -1 0.1347 13.9994 1.9994 -0.9995 -0.9275 0.3718 0.1565
-14 -2 1 0.1347 -13.9994 -1.9994 0.9995 0.9275 -0.3718 -0.1565
1 1 -9 0.0960 1.0029 0.9999 -8.9996 0.2095 0.8346 0.4089
-1 -1 9 0.0960 -1.0029 -0.9999 8.9996 -0.2095 -0.8346 -0.4089

_olex2_date_sample_data_collection 2015-04-21
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C11(H11), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2014/6
