# 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_ia114a
_audit_block_doi                 10.5517/cc14glhp
_database_code_depnum_ccdc_archive 'CCDC 1056712'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-05-10 downloaded from the CCDC.
;
_audit_creation_date             2014-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H11 N3 O2, 0.5(H2 O)'
_chemical_formula_sum            'C13 H12 N3 O2.50'
_chemical_formula_weight         250.26
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   23.2307(11)
_cell_length_b                   11.1515(5)
_cell_length_c                   9.2568(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2398.04(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4401
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.157
_cell_measurement_theta_min      3.805
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0832 before and 0.0730 after correction. The Ratio of minimum to maximum transmission is 0.7622. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.116
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11703
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.164
_diffrn_reflns_theta_min         3.805
_diffrn_ambient_temperature      172.99
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1798
_reflns_number_total             2305
_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       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT (BRUKER, V8.27BA, 20112)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0837
_refine_ls_restrained_S_all      1.108
_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)+(0.1318P)²+2.4340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2561
_refine_ls_wR_factor_ref         0.2690
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O4(0.25) H4A(0.25) H4B(0.25) O5(0.25) H5A(0.25) H5B(0.25)
3.a Everything fixed:
 H4A, H4B, H5A, H5B
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.47821(11) 0.1055(3) 0.4327(3) 0.0606(8) Uani 1 1 d . . . . .
O2 O 0.44042(12) 0.2791(3) 0.3614(3) 0.0659(8) Uani 1 1 d . . . . .
N1 N 0.36845(12) 0.2706(3) 0.1531(3) 0.0503(8) Uani 1 1 d . . . . .
H1 H 0.3911 0.3141 0.2084 0.060 Uiso 1 1 calc R . . . .
N2 N 0.36866(11) 0.1531(3) 0.1654(3) 0.0461(7) Uani 1 1 d . . . . .
N3 N 0.43648(11) -0.0921(3) 0.3403(3) 0.0467(7) Uani 1 1 d . . . . .
H3 H 0.4585 -0.0516 0.4005 0.056 Uiso 1 1 calc R . . . .
C1 C 0.44416(15) 0.1678(4) 0.3587(4) 0.0494(9) Uani 1 1 d . . . . .
C2 C 0.40365(13) 0.1007(3) 0.2573(3) 0.0468(8) Uani 1 1 d . . . . .
C3 C 0.40156(13) -0.0297(3) 0.2525(3) 0.0456(8) Uani 1 1 d . . . . .
C4 C 0.36535(15) -0.0968(4) 0.1606(4) 0.0525(9) Uani 1 1 d . . . . .
H4 H 0.3392 -0.0567 0.0982 0.063 Uiso 1 1 calc R . . . .
C5 C 0.36775(16) -0.2190(4) 0.1610(4) 0.0569(10) Uani 1 1 d . . . . .
H5 H 0.3430 -0.2635 0.0993 0.068 Uiso 1 1 calc R . . . .
C6 C 0.40608(16) -0.2793(4) 0.2513(4) 0.0582(10) Uani 1 1 d . . . . .
H6 H 0.4088 -0.3643 0.2504 0.070 Uiso 1 1 calc R . . . .
C7 C 0.43992(15) -0.2108(4) 0.3421(4) 0.0528(9) Uani 1 1 d . . . . .
H7 H 0.4659 -0.2491 0.4064 0.063 Uiso 1 1 calc R . . . .
C8 C 0.33233(14) 0.3270(3) 0.0527(3) 0.0461(8) Uani 1 1 d . . . . .
C9 C 0.28648(14) 0.2684(4) -0.0112(4) 0.0524(9) Uani 1 1 d . . . . .
H9 H 0.2780 0.1879 0.0146 0.063 Uiso 1 1 calc R . . . .
C10 C 0.25313(16) 0.3267(4) -0.1121(4) 0.0590(10) Uani 1 1 d . . . . .
H10 H 0.2218 0.2858 -0.1561 0.071 Uiso 1 1 calc R . . . .
C11 C 0.26473(17) 0.4440(4) -0.1500(4) 0.0611(11) Uani 1 1 d . . . . .
H11 H 0.2416 0.4836 -0.2199 0.073 Uiso 1 1 calc R . . . .
C12 C 0.31038(17) 0.5036(4) -0.0853(4) 0.0582(10) Uani 1 1 d . . . . .
H12 H 0.3184 0.5845 -0.1103 0.070 Uiso 1 1 calc R . . . .
C13 C 0.34437(16) 0.4448(3) 0.0164(4) 0.0521(9) Uani 1 1 d . . . . .
H13 H 0.3757 0.4854 0.0607 0.062 Uiso 1 1 calc R . . . .
O4 O 0.4927(9) 0.4813(16) 0.077(2) 0.107(5) Uiso 0.25 1 d . . P A 1
H4A H 0.4828 0.4420 0.1829 0.161 Uiso 0.25 1 d . . P B 1
H4B H 0.5021 0.4152 0.0352 0.161 Uiso 0.25 1 d . . P C 1
O5 O 0.4878(4) 0.4763(9) 0.1583(12) 0.051(2) Uiso 0.25 1 d . . P D 2
H5A H 0.5000 0.4833 0.2500 0.077 Uiso 0.5 2 d S T P E 2
H5B H 0.4754 0.4174 0.1291 0.077 Uiso 0.25 1 d . . P F 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
O1 C1 1.256(4) . ?
O2 C1 1.245(5) . ?
N1 H1 0.8800 . ?
N1 N2 1.315(4) . ?
N1 C8 1.402(4) . ?
N2 C2 1.314(4) . ?
N3 H3 0.8800 . ?
N3 C3 1.342(4) . ?
N3 C7 1.326(5) . ?
C1 C2 1.525(5) . ?
C2 C3 1.456(5) . ?
C3 C4 1.411(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(5) . ?
C8 C13 1.385(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(5) . ?
C13 H13 0.9500 . ?
O4 O4 1.53(4) 5_665 ?
O4 H4A 1.0958 . ?
O4 H4B 0.8625 . ?
O5 O5 1.79(2) 3_655 ?
O5 H5A 0.8980 . ?
O5 H5B 0.7658 . ?

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
N2 N1 H1 119.8 . . ?
N2 N1 C8 120.4(3) . . ?
C8 N1 H1 119.8 . . ?
C2 N2 N1 120.1(3) . . ?
C3 N3 H3 117.9 . . ?
C7 N3 H3 117.9 . . ?
C7 N3 C3 124.1(3) . . ?
O1 C1 C2 116.9(4) . . ?
O2 C1 O1 125.8(4) . . ?
O2 C1 C2 117.2(3) . . ?
N2 C2 C1 124.2(3) . . ?
N2 C2 C3 113.8(3) . . ?
C3 C2 C1 121.9(3) . . ?
N3 C3 C2 118.6(3) . . ?
N3 C3 C4 116.8(3) . . ?
C4 C3 C2 124.6(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 121.3 . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 H6 121.3 . . ?
N3 C7 C6 120.7(3) . . ?
N3 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 N1 122.2(3) . . ?
C9 C8 C13 120.0(3) . . ?
C13 C8 N1 117.7(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.7(4) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O4 O4 H4A 172.3 5_665 . ?
O4 O4 H4B 75.7 5_665 . ?
H4A O4 H4B 96.6 . . ?
O5 O5 H5A 5.0 3_655 . ?
O5 O5 H5B 117.0 3_655 . ?
H5A O5 H5B 121.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 1.86 2.553(4) 134.0 .
N3 H3 O1 0.88 1.84 2.554(4) 137.5 .
O4 H4A O5 1.10 1.67 2.49(3) 127.5 3_655

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 C1 C2 N2 -174.7(3) . . . . ?
O1 C1 C2 C3 3.9(4) . . . . ?
O2 C1 C2 N2 5.6(5) . . . . ?
O2 C1 C2 C3 -175.8(3) . . . . ?
N1 N2 C2 C1 2.3(4) . . . . ?
N1 N2 C2 C3 -176.4(3) . . . . ?
N1 C8 C9 C10 -178.3(3) . . . . ?
N1 C8 C13 C12 178.6(3) . . . . ?
N2 N1 C8 C9 16.1(5) . . . . ?
N2 N1 C8 C13 -163.0(3) . . . . ?
N2 C2 C3 N3 178.8(3) . . . . ?
N2 C2 C3 C4 -0.8(4) . . . . ?
N3 C3 C4 C5 -1.5(5) . . . . ?
C1 C2 C3 N3 0.0(4) . . . . ?
C1 C2 C3 C4 -179.6(3) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C3 N3 C7 C6 -0.7(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C5 C6 C7 N3 -1.3(5) . . . . ?
C7 N3 C3 C2 -177.5(3) . . . . ?
C7 N3 C3 C4 2.1(4) . . . . ?
C8 N1 N2 C2 178.3(3) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C8 C13 C12 -0.5(5) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C8 -0.1(5) . . . . ?
C13 C8 C9 C10 0.7(5) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
####################################################################### 
# 
# 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_p1barsb
_database_code_depnum_ccdc_archive 'CCDC 1056713'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-05-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_p1barsb             
;
PROBLEM: Hirshfeld Test Diff for N1 -- C2 .. 9.4 su
RESPONSE: N1, C2, C3, C4 and C5 all show thermal values that are reasonable. 
C3 is the carbon of an aryl ring that bears a substitutent, so its location is 
more defined than atoms C4 and C5 of the ring which can freely rotate. 
C2 bears a disordered phenyl ring, which likely contributes to the slightly 
larger thermal value for this atom relative to N1.
;
_vrf_PLAT332_p1barsb             
;
PROBLEM: Large Phenyl C-C Range C9 -C13A 0.29 Ang.
RESPONSE: This bond is within a disordered phenyl ring.
;
# end Validation Reply Form


_audit_creation_date             2014-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0320(2)
_cell_length_b                   9.7091(4)
_cell_length_c                   12.6168(6)
_cell_angle_alpha                89.600(4)
_cell_angle_beta                 89.102(4)
_cell_angle_gamma                79.669(4)
_cell_volume                     606.34(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2697
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.180
_cell_measurement_theta_min      3.503
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0805 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8442.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8490
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.396
_diffrn_reflns_theta_min         3.503
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1585
_reflns_number_total             2310
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.037
_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)+(0.0764P)²+0.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C11A(0.5) H11A(0.5) C11B(0.5) H11B(0.5) C12A(0.5) H12A(0.5)
 C12B(0.5) H12B(0.5) C13A(0.5) H13A(0.5) C13B(0.5) H13B(0.5) C14A(0.5)
 H14A(0.5) C14B(0.5) H14B(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B), C13A(H13A), C13B(H13B),
 C14A(H14A), C14B(H14B)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.2755(3) 0.41166(18) 0.95362(14) 0.0538(5) Uani 1 1 d . . . . .
O2 O 0.3815(4) 0.6090(2) 0.88728(14) 0.0556(5) Uani 1 1 d . . . . .
H2 H 0.505(8) 0.603(4) 0.954(3) 0.112(13) Uiso 1 1 d . . . . .
N1 N -0.0725(4) 0.4071(2) 0.77548(16) 0.0506(5) Uani 1 1 d . . . . .
N2 N -0.0823(4) 0.3076(2) 0.84365(17) 0.0553(6) Uani 1 1 d . . . . .
H2A H 0.043(8) 0.300(4) 0.900(3) 0.105(13) Uiso 1 1 d . . . . .
C1 C 0.2534(5) 0.5031(3) 0.8836(2) 0.0480(6) Uani 1 1 d . . . . .
C2 C 0.0813(4) 0.5006(3) 0.7901(2) 0.0469(6) Uani 1 1 d . . . . .
C3 C -0.2406(5) 0.2034(3) 0.8214(2) 0.0521(6) Uani 1 1 d . . . . .
C4 C -0.3989(6) 0.2114(3) 0.7330(2) 0.0575(7) Uani 1 1 d . . . . .
H4 H -0.409(7) 0.291(4) 0.688(3) 0.092(11) Uiso 1 1 d . . . . .
C5 C -0.5516(6) 0.1067(4) 0.7154(3) 0.0685(8) Uani 1 1 d . . . . .
H5 H -0.659(7) 0.106(3) 0.658(3) 0.072(9) Uiso 1 1 d . . . . .
C6 C -0.5392(7) -0.0050(3) 0.7857(3) 0.0653(8) Uani 1 1 d . . . . .
H6 H -0.624(6) -0.071(3) 0.777(2) 0.069(10) Uiso 1 1 d . . . . .
C7 C -0.3769(8) -0.0087(3) 0.8718(3) 0.0725(9) Uani 1 1 d . . . . .
H7 H -0.368(7) -0.081(3) 0.921(3) 0.077(10) Uiso 1 1 d . . . . .
C8 C -0.2318(7) 0.0950(3) 0.8907(3) 0.0674(8) Uani 1 1 d . . . . .
H8 H -0.118(9) 0.088(4) 0.957(3) 0.123(15) Uiso 1 1 d . . . . .
C9 C 0.0761(5) 0.6040(3) 0.70357(18) 0.0467(6) Uani 1 1 d . . . . .
C10 C 0.0595(6) 0.7909(3) 0.5342(2) 0.0628(8) Uani 1 1 d . . . . .
H10 H 0.055(6) 0.860(3) 0.473(3) 0.080(10) Uiso 1 1 d . . . . .
C11A C 0.0328(9) 0.7323(5) 0.7201(4) 0.0434(10) Uani 0.5 1 d . . P A 1
H11A H 0.0034 0.7665 0.7904 0.052 Uiso 0.5 1 calc R . P A 1
C11B C 0.3162(10) 0.6456(6) 0.6542(4) 0.0508(12) Uani 0.5 1 d . . P A 2
H11B H 0.4885 0.6053 0.6808 0.061 Uiso 0.5 1 calc R . P A 2
C12A C 0.0274(10) 0.8252(5) 0.6362(4) 0.0520(12) Uani 0.5 1 d . . P A 1
H12A H -0.0017 0.9220 0.6528 0.062 Uiso 0.5 1 calc R . P A 1
C12B C 0.3053(11) 0.7402(6) 0.5713(4) 0.0576(13) Uani 0.5 1 d . . P A 2
H12B H 0.4634 0.7675 0.5423 0.069 Uiso 0.5 1 calc R . P A 2
C13A C 0.1012(10) 0.5417(5) 0.5984(4) 0.0502(12) Uani 0.5 1 d . . P A 1
H13A H 0.1192 0.4436 0.5882 0.060 Uiso 0.5 1 calc R . P A 1
C13B C -0.1677(10) 0.6847(5) 0.6645(4) 0.0479(11) Uani 0.5 1 d . . P A 2
H13B H -0.3331 0.6733 0.6978 0.057 Uiso 0.5 1 calc R . P A 2
C14A C 0.0972(11) 0.6330(6) 0.5156(4) 0.0563(13) Uani 0.5 1 d . . P A 1
H14A H 0.1182 0.5981 0.4453 0.068 Uiso 0.5 1 calc R . P A 1
C14B C -0.1781(11) 0.7780(5) 0.5814(4) 0.0531(12) Uani 0.5 1 d . . P A 2
H14B H -0.3446 0.8310 0.5582 0.064 Uiso 0.5 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
O1 C1 1.239(3) . ?
O2 C1 1.310(3) . ?
N1 N2 1.296(3) . ?
N1 C2 1.309(3) . ?
N2 C3 1.427(3) . ?
C1 C2 1.477(3) . ?
C2 C9 1.476(4) . ?
C3 C4 1.375(4) . ?
C3 C8 1.358(4) . ?
C4 C5 1.400(4) . ?
C5 C6 1.389(5) . ?
C6 C7 1.366(5) . ?
C7 C8 1.370(5) . ?
C9 C11A 1.244(5) . ?
C9 C11B 1.470(6) . ?
C9 C13A 1.456(5) . ?
C9 C13B 1.425(5) . ?
C10 C12A 1.332(6) . ?
C10 C12B 1.337(6) . ?
C10 C14A 1.530(6) . ?
C10 C14B 1.353(6) . ?
C11A C12A 1.383(7) . ?
C11B C12B 1.382(7) . ?
C13A C14A 1.364(7) . ?
C13B C14B 1.377(7) . ?

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
N2 N1 C2 121.4(2) . . ?
N1 N2 C3 119.4(2) . . ?
O1 C1 O2 122.3(2) . . ?
O1 C1 C2 122.6(2) . . ?
O2 C1 C2 115.1(2) . . ?
N1 C2 C1 123.9(2) . . ?
N1 C2 C9 114.6(2) . . ?
C9 C2 C1 121.5(2) . . ?
C4 C3 N2 121.6(3) . . ?
C8 C3 N2 118.1(3) . . ?
C8 C3 C4 120.3(3) . . ?
C3 C4 C5 119.2(3) . . ?
C6 C5 C4 120.2(3) . . ?
C7 C6 C5 118.3(3) . . ?
C6 C7 C8 121.7(3) . . ?
C3 C8 C7 120.2(3) . . ?
C11A C9 C2 122.3(3) . . ?
C11A C9 C13A 124.0(4) . . ?
C11B C9 C2 124.9(3) . . ?
C13A C9 C2 113.5(3) . . ?
C13B C9 C2 123.0(3) . . ?
C13B C9 C11B 111.9(3) . . ?
C12A C10 C14A 113.0(4) . . ?
C12B C10 C14B 125.9(4) . . ?
C9 C11A C12A 120.1(4) . . ?
C12B C11B C9 123.6(4) . . ?
C10 C12A C11A 125.8(5) . . ?
C10 C12B C11B 116.2(4) . . ?
C14A C13A C9 115.8(4) . . ?
C14B C13B C9 124.0(4) . . ?
C13A C14A C10 121.0(4) . . ?
C10 C14B C13B 117.0(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 C1 C2 N1 3.7(4) . . . . ?
O1 C1 C2 C9 -174.8(2) . . . . ?
O2 C1 C2 N1 -176.4(2) . . . . ?
O2 C1 C2 C9 5.1(3) . . . . ?
N1 N2 C3 C4 -4.8(4) . . . . ?
N1 N2 C3 C8 175.4(2) . . . . ?
N1 C2 C9 C11A 128.5(3) . . . . ?
N1 C2 C9 C11B -132.7(3) . . . . ?
N1 C2 C9 C13A -46.2(3) . . . . ?
N1 C2 C9 C13B 53.0(4) . . . . ?
N2 N1 C2 C1 -0.5(4) . . . . ?
N2 N1 C2 C9 178.1(2) . . . . ?
N2 C3 C4 C5 -179.6(2) . . . . ?
N2 C3 C8 C7 -178.9(3) . . . . ?
C1 C2 C9 C11A -52.8(4) . . . . ?
C1 C2 C9 C11B 45.9(4) . . . . ?
C1 C2 C9 C13A 132.5(3) . . . . ?
C1 C2 C9 C13B -128.3(3) . . . . ?
C2 N1 N2 C3 -176.4(2) . . . . ?
C2 C9 C11A C12A -179.4(3) . . . . ?
C2 C9 C11B C12B 178.2(4) . . . . ?
C2 C9 C13A C14A 180.0(4) . . . . ?
C2 C9 C13B C14B -177.6(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C3 C8 C7 1.2(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C3 -1.9(5) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C9 C11A C12A C10 1.6(7) . . . . ?
C9 C11B C12B C10 -2.0(7) . . . . ?
C9 C13A C14A C10 -1.9(7) . . . . ?
C9 C13B C14B C10 0.9(7) . . . . ?
C11A C9 C13A C14A 5.4(6) . . . . ?
C11B C9 C13B C14B 7.5(6) . . . . ?
C12A C10 C14A C13A -1.2(6) . . . . ?
C12B C10 C14B C13B -12.1(7) . . . . ?
C13A C9 C11A C12A -5.3(6) . . . . ?
C13B C9 C11B C12B -7.0(6) . . . . ?
C14A C10 C12A C11A 1.6(6) . . . . ?
C14B C10 C12B C11B 12.4(7) . . . . ?

_olex2_submission_original_sample_id '1PhdEHZH (IA1014b)'
_olex2_submission_special_instructions 'No special instructions were received'
