# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_pmal_ab_3_532_0m
_database_code_depnum_ccdc_archive 'CCDC 1550265'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_audit_creation_date             2016-08-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl N2 O3'
_chemical_formula_sum            'C16 H13 Cl N2 O3'
_chemical_formula_weight         316.73
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   10.4606(4)
_cell_length_b                   12.8372(4)
_cell_length_c                   11.2997(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.445(2)
_cell_angle_gamma                90
_cell_volume                     1455.30(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5395
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.8826.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15342
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.084
_diffrn_reflns_theta_min         2.344
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             4271
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.015
_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)+(0.0760P)²+0.3980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C14(H14), C13(H13), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.053
;
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
Cl1 Cl 0.17720(6) 1.07716(4) 0.58146(6) 0.0638(2) Uani 1 1 d . . . . .
O1 O 0.28479(15) 0.27588(12) 0.32968(12) 0.0560(4) Uani 1 1 d . . . . .
N1 N 0.37923(14) 0.30454(11) 0.53223(12) 0.0365(3) Uani 1 1 d . . . . .
O2 O 0.07613(15) 0.30901(12) 0.43669(16) 0.0645(4) Uani 1 1 d . . . . .
N2 N 0.09897(16) 0.39206(13) 0.39512(16) 0.0508(4) Uani 1 1 d . . . . .
O3 O 0.02956(18) 0.43072(12) 0.30025(17) 0.0861(7) Uani 1 1 d . . . . .
C4 C 0.33153(16) 0.40685(12) 0.53399(14) 0.0323(3) Uani 1 1 d . . . . .
C3 C 0.42386(16) 0.46738(13) 0.62033(13) 0.0341(3) Uani 1 1 d . . . . .
C7 C 0.28531(16) 0.62000(13) 0.56157(14) 0.0345(3) Uani 1 1 d . . . . .
C9 C 0.26050(16) 0.73310(13) 0.56980(14) 0.0351(4) Uani 1 1 d . . . . .
C5 C 0.21283(16) 0.45282(14) 0.46794(15) 0.0369(4) Uani 1 1 d . . . . .
C6 C 0.19048(17) 0.55828(13) 0.48040(16) 0.0391(4) Uani 1 1 d . . . . .
H6 H 0.1111 0.5881 0.4339 0.047 Uiso 1 1 calc R . . . .
C8 C 0.40187(17) 0.57226(13) 0.63321(14) 0.0356(4) Uani 1 1 d . . . . .
H8 H 0.4651 0.6116 0.6901 0.043 Uiso 1 1 calc R . . . .
C15 C 0.35640(18) 0.24476(14) 0.42801(16) 0.0400(4) Uani 1 1 d . . . . .
C14 C 0.29710(19) 0.78664(14) 0.68128(15) 0.0411(4) Uani 1 1 d . . . . .
H14 H 0.3384 0.7509 0.7535 0.049 Uiso 1 1 calc R . . . .
C13 C 0.27309(19) 0.89247(14) 0.68650(16) 0.0434(4) Uani 1 1 d . . . . .
H13 H 0.2975 0.9275 0.7616 0.052 Uiso 1 1 calc R . . . .
C12 C 0.21256(19) 0.94508(14) 0.57895(18) 0.0421(4) Uani 1 1 d . . . . .
C10 C 0.20183(19) 0.78907(14) 0.46306(16) 0.0437(4) Uani 1 1 d . . . . .
H10 H 0.1784 0.7549 0.3874 0.052 Uiso 1 1 calc R . . . .
C2 C 0.53910(18) 0.40001(15) 0.68671(16) 0.0444(4) Uani 1 1 d . . . . .
H2A H 0.5578 0.4075 0.7754 0.053 Uiso 1 1 calc R . . . .
H2B H 0.6186 0.4175 0.6629 0.053 Uiso 1 1 calc R . . . .
C11 C 0.1778(2) 0.89413(15) 0.46727(18) 0.0488(5) Uani 1 1 d . . . . .
H11 H 0.1383 0.9305 0.3950 0.059 Uiso 1 1 calc R . . . .
C1 C 0.4920(2) 0.28962(15) 0.64563(16) 0.0474(5) Uani 1 1 d . . . . .
H1A H 0.5629 0.2495 0.6278 0.057 Uiso 1 1 calc R . . . .
H1B H 0.4625 0.2540 0.7089 0.057 Uiso 1 1 calc R . . . .
C16 C 0.4227(2) 0.13961(16) 0.4415(2) 0.0552(5) Uani 1 1 d . . . . .
H16A H 0.3787 0.0965 0.3725 0.083 Uiso 1 1 calc GR . . . .
H16B H 0.4169 0.1074 0.5165 0.083 Uiso 1 1 calc GR . . . .
H16C H 0.5146 0.1478 0.4440 0.083 Uiso 1 1 calc GR . . . .


_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
Cl1 C12 1.7374(18) . ?
O1 C15 1.218(2) . ?
N1 C4 1.407(2) . ?
N1 C15 1.369(2) . ?
N1 C1 1.488(2) . ?
O2 N2 1.216(2) . ?
N2 O3 1.217(2) . ?
N2 C5 1.466(2) . ?
C4 C3 1.398(2) . ?
C4 C5 1.386(2) . ?
C3 C8 1.381(2) . ?
C3 C2 1.501(2) . ?
C7 C9 1.482(2) . ?
C7 C6 1.392(2) . ?
C7 C8 1.400(2) . ?
C9 C14 1.390(2) . ?
C9 C10 1.389(2) . ?
C5 C6 1.388(2) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C15 C16 1.505(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(3) . ?
C12 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.529(3) . ?
C11 H11 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C4 N1 C1 107.80(13) . . ?
C15 N1 C4 124.01(14) . . ?
C15 N1 C1 124.86(15) . . ?
O2 N2 O3 124.36(17) . . ?
O2 N2 C5 117.84(16) . . ?
O3 N2 C5 117.69(17) . . ?
C3 C4 N1 110.54(13) . . ?
C5 C4 N1 131.06(15) . . ?
C5 C4 C3 118.39(15) . . ?
C4 C3 C2 109.09(15) . . ?
C8 C3 C4 120.85(14) . . ?
C8 C3 C2 130.06(15) . . ?
C6 C7 C9 119.61(14) . . ?
C6 C7 C8 118.26(15) . . ?
C8 C7 C9 122.13(14) . . ?
C14 C9 C7 122.20(15) . . ?
C10 C9 C7 119.63(14) . . ?
C10 C9 C14 118.14(16) . . ?
C4 C5 N2 122.49(15) . . ?
C4 C5 C6 120.77(15) . . ?
C6 C5 N2 116.26(15) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.86(15) . . ?
C5 C6 H6 119.6 . . ?
C3 C8 C7 120.66(14) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
O1 C15 N1 120.88(16) . . ?
O1 C15 C16 122.20(17) . . ?
N1 C15 C16 116.92(16) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.10(16) . . ?
C13 C14 H14 119.4 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 C14 119.11(16) . . ?
C12 C13 H13 120.4 . . ?
C13 C12 Cl1 120.71(14) . . ?
C11 C12 Cl1 118.47(15) . . ?
C11 C12 C13 120.81(17) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.17(16) . . ?
C11 C10 H10 119.4 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C3 C2 C1 103.77(14) . . ?
H2A C2 H2B 109.0 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.64(17) . . ?
C10 C11 H11 120.2 . . ?
N1 C1 C2 104.54(14) . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C12 C11 C10 -178.47(16) . . . . ?
N1 C4 C3 C8 176.25(15) . . . . ?
N1 C4 C3 C2 -3.24(19) . . . . ?
N1 C4 C5 N2 11.9(3) . . . . ?
N1 C4 C5 C6 -176.31(18) . . . . ?
O2 N2 C5 C4 38.0(3) . . . . ?
O2 N2 C5 C6 -134.16(19) . . . . ?
N2 C5 C6 C7 170.77(16) . . . . ?
O3 N2 C5 C4 -145.8(2) . . . . ?
O3 N2 C5 C6 42.0(3) . . . . ?
C4 N1 C15 O1 -4.5(3) . . . . ?
C4 N1 C15 C16 176.00(16) . . . . ?
C4 N1 C1 C2 -20.89(19) . . . . ?
C4 C3 C8 C7 1.2(3) . . . . ?
C4 C3 C2 C1 -9.77(19) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C3 C4 C5 N2 -166.96(16) . . . . ?
C3 C4 C5 C6 4.8(3) . . . . ?
C3 C2 C1 N1 18.20(19) . . . . ?
C7 C9 C14 C13 179.84(17) . . . . ?
C7 C9 C10 C11 -179.76(18) . . . . ?
C9 C7 C6 C5 177.98(16) . . . . ?
C9 C7 C8 C3 -177.83(16) . . . . ?
C9 C14 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C5 C4 C3 C8 -4.7(2) . . . . ?
C5 C4 C3 C2 175.85(15) . . . . ?
C6 C7 C9 C14 141.68(18) . . . . ?
C6 C7 C9 C10 -40.0(2) . . . . ?
C6 C7 C8 C3 2.2(2) . . . . ?
C8 C3 C2 C1 170.80(18) . . . . ?
C8 C7 C9 C14 -38.3(2) . . . . ?
C8 C7 C9 C10 140.07(18) . . . . ?
C8 C7 C6 C5 -2.0(3) . . . . ?
C15 N1 C4 C3 -144.69(16) . . . . ?
C15 N1 C4 C5 36.4(3) . . . . ?
C15 N1 C1 C2 139.08(17) . . . . ?
C14 C9 C10 C11 -1.3(3) . . . . ?
C14 C13 C12 Cl1 178.59(15) . . . . ?
C14 C13 C12 C11 -0.9(3) . . . . ?
C13 C12 C11 C10 1.1(3) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C2 C3 C8 C7 -179.46(17) . . . . ?
C1 N1 C4 C3 15.49(19) . . . . ?
C1 N1 C4 C5 -163.45(18) . . . . ?
C1 N1 C15 O1 -161.33(18) . . . . ?
C1 N1 C15 C16 19.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_try1
_database_code_depnum_ccdc_archive 'CCDC 1550269'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_audit_creation_date             2016-09-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N2 O3'
_chemical_formula_sum            'C15 H12 N2 O3'
_chemical_formula_weight         268.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1122(4)
_cell_length_b                   7.8149(3)
_cell_length_c                   10.1296(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.368(2)
_cell_angle_gamma                90
_cell_volume                     627.27(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2601
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.059
_cell_measurement_theta_min      2.571
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0625 before and 0.0434 after correction.
The Ratio of minimum to maximum transmission is 0.9406.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11174
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.738
_diffrn_reflns_theta_min         2.058
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                2501
_reflns_number_total             3064
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.034
_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)+(0.0462P)²+0.0572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0999
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.041
;
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 0.2641(4) 0.0648(4) -1.1498(2) 0.0916(9) Uani 1 1 d . . . . .
O2 O 0.4688(3) -0.0889(4) -1.0399(2) 0.0872(8) Uani 1 1 d . . . . .
O3 O 0.1272(2) -0.2322(3) -0.47983(19) 0.0665(6) Uani 1 1 d . . . . .
N1 N 0.3293(3) -0.0229(4) -1.0520(2) 0.0612(7) Uani 1 1 d . . . . .
N2 N -0.0534(2) -0.1269(3) -0.66386(18) 0.0384(4) Uani 1 1 d . . . . .
C1 C 0.2339(3) -0.0530(4) -0.9475(2) 0.0463(6) Uani 1 1 d . . . . .
C2 C 0.0792(3) 0.0264(3) -0.9585(2) 0.0469(6) Uani 1 1 d . . . . .
H2 H 0.0355 0.0978 -1.0310 0.056 Uiso 1 1 calc R . . . .
C3 C -0.0075(3) -0.0042(3) -0.8580(2) 0.0405(5) Uani 1 1 d . . . . .
C4 C 0.0604(3) -0.1112(3) -0.7498(2) 0.0358(5) Uani 1 1 d . . . . .
C5 C -0.0160(3) -0.1913(3) -0.5352(2) 0.0434(5) Uani 1 1 d . . . . .
C6 C -0.1605(3) -0.2091(3) -0.4653(2) 0.0407(5) Uani 1 1 d . . . . .
C7 C -0.2977(3) -0.3129(3) -0.5174(3) 0.0486(6) Uani 1 1 d . . . . .
H7 H -0.3036 -0.3693 -0.5991 0.058 Uiso 1 1 calc R . . . .
C8 C -0.4261(3) -0.3326(4) -0.4477(3) 0.0545(7) Uani 1 1 d . . . . .
H8 H -0.5174 -0.4035 -0.4819 0.065 Uiso 1 1 calc R . . . .
C9 C -0.4180(3) -0.2469(4) -0.3276(3) 0.0551(7) Uani 1 1 d . . . . .
H9 H -0.5057 -0.2576 -0.2821 0.066 Uiso 1 1 calc R . . . .
C10 C -0.1726(3) 0.0677(4) -0.8386(3) 0.0486(6) Uani 1 1 d . . . . .
H10A H -0.2585 0.0602 -0.9213 0.058 Uiso 1 1 calc R . . . .
H10B H -0.1603 0.1862 -0.8097 0.058 Uiso 1 1 calc R . . . .
C11 C -0.2163(3) -0.0459(3) -0.7285(2) 0.0440(6) Uani 1 1 d . . . . .
H11A H -0.2605 0.0216 -0.6635 0.053 Uiso 1 1 calc R . . . .
H11B H -0.2991 -0.1317 -0.7670 0.053 Uiso 1 1 calc R . . . .
C12 C -0.2811(4) -0.1458(4) -0.2746(3) 0.0559(7) Uani 1 1 d . . . . .
H12 H -0.2759 -0.0890 -0.1931 0.067 Uiso 1 1 calc R . . . .
C13 C -0.1506(3) -0.1283(4) -0.3430(2) 0.0482(6) Uani 1 1 d . . . . .
H13 H -0.0567 -0.0622 -0.3061 0.058 Uiso 1 1 calc R . . . .
C14 C 0.2166(3) -0.1884(3) -0.7389(2) 0.0440(5) Uani 1 1 d . . . . .
H14 H 0.2619 -0.2578 -0.6655 0.053 Uiso 1 1 calc R . . . .
C15 C 0.3030(3) -0.1592(3) -0.8406(3) 0.0465(6) Uani 1 1 d . . . . .
H15 H 0.4072 -0.2108 -0.8371 0.056 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
O1 N1 1.227(4) . ?
O2 N1 1.226(4) . ?
O3 C5 1.220(3) . ?
N1 C1 1.458(3) . ?
N2 C4 1.403(3) . ?
N2 C5 1.369(3) . ?
N2 C11 1.485(3) . ?
C1 C2 1.383(4) . ?
C1 C15 1.385(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 C4 1.395(3) . ?
C3 C10 1.503(4) . ?
C4 C14 1.387(3) . ?
C5 C6 1.500(3) . ?
C6 C7 1.387(4) . ?
C6 C13 1.378(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(4) . ?
C9 H9 0.9300 . ?
C9 C12 1.375(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.390(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 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
O1 N1 C1 118.2(3) . . ?
O2 N1 O1 123.0(2) . . ?
O2 N1 C1 118.8(3) . . ?
C4 N2 C11 109.32(17) . . ?
C5 N2 C4 125.57(19) . . ?
C5 N2 C11 124.81(18) . . ?
C2 C1 N1 118.9(2) . . ?
C2 C1 C15 122.7(2) . . ?
C15 C1 N1 118.4(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 C10 130.0(2) . . ?
C4 C3 C10 109.5(2) . . ?
C3 C4 N2 109.80(19) . . ?
C14 C4 N2 128.6(2) . . ?
C14 C4 C3 121.6(2) . . ?
O3 C5 N2 121.9(2) . . ?
O3 C5 C6 121.5(2) . . ?
N2 C5 C6 116.58(19) . . ?
C7 C6 C5 121.3(2) . . ?
C13 C6 C5 118.8(2) . . ?
C13 C6 C7 119.9(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.8 . . ?
C12 C9 C8 120.4(2) . . ?
C12 C9 H9 119.8 . . ?
C3 C10 H10A 111.1 . . ?
C3 C10 H10B 111.1 . . ?
C3 C10 C11 103.4(2) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
N2 C11 C10 104.23(19) . . ?
N2 C11 H11A 110.9 . . ?
N2 C11 H11B 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C9 C12 H12 120.0 . . ?
C9 C12 C13 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C6 C13 C12 119.9(2) . . ?
C6 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C4 C14 H14 121.0 . . ?
C15 C14 C4 118.0(2) . . ?
C15 C14 H14 121.0 . . ?
C1 C15 H15 120.1 . . ?
C14 C15 C1 119.8(2) . . ?
C14 C15 H15 120.1 . . ?

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 N1 C1 C2 -3.9(4) . . . . ?
O1 N1 C1 C15 176.6(3) . . . . ?
O2 N1 C1 C2 177.7(3) . . . . ?
O2 N1 C1 C15 -1.8(4) . . . . ?
O3 C5 C6 C7 -119.5(3) . . . . ?
O3 C5 C6 C13 56.6(4) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
N1 C1 C15 C14 179.1(2) . . . . ?
N2 C4 C14 C15 177.0(2) . . . . ?
N2 C5 C6 C7 60.6(3) . . . . ?
N2 C5 C6 C13 -123.3(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C10 177.2(3) . . . . ?
C2 C1 C15 C14 -0.3(4) . . . . ?
C2 C3 C4 N2 -178.0(2) . . . . ?
C2 C3 C4 C14 0.6(3) . . . . ?
C2 C3 C10 C11 167.9(2) . . . . ?
C3 C4 C14 C15 -1.2(3) . . . . ?
C3 C10 C11 N2 18.9(3) . . . . ?
C4 N2 C5 O3 4.7(4) . . . . ?
C4 N2 C5 C6 -175.4(2) . . . . ?
C4 N2 C11 C10 -17.4(3) . . . . ?
C4 C3 C10 C11 -14.9(3) . . . . ?
C4 C14 C15 C1 1.1(4) . . . . ?
C5 N2 C4 C3 -165.6(2) . . . . ?
C5 N2 C4 C14 16.0(4) . . . . ?
C5 N2 C11 C10 156.7(2) . . . . ?
C5 C6 C7 C8 177.3(2) . . . . ?
C5 C6 C13 C12 -178.6(2) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C7 C6 C13 C12 -2.5(4) . . . . ?
C7 C8 C9 C12 -1.8(4) . . . . ?
C8 C9 C12 C13 0.6(4) . . . . ?
C9 C12 C13 C6 1.6(4) . . . . ?
C10 C3 C4 N2 4.5(3) . . . . ?
C10 C3 C4 C14 -177.0(2) . . . . ?
C11 N2 C4 C3 8.4(3) . . . . ?
C11 N2 C4 C14 -169.9(2) . . . . ?
C11 N2 C5 O3 -168.4(3) . . . . ?
C11 N2 C5 C6 11.5(4) . . . . ?
C13 C6 C7 C8 1.2(4) . . . . ?
C15 C1 C2 C3 -0.4(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
