# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_pere59
_database_code_depnum_ccdc_archive 'CCDC 1440140'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H32 N2 O4'
_chemical_formula_sum            'C26 H32 N2 O4'
_chemical_formula_weight         436.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.9402(9)
_cell_length_b                   4.8707(2)
_cell_length_c                   17.3118(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.785(2)
_cell_angle_gamma                90
_cell_volume                     2323.63(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    105
_cell_measurement_theta_max      60.644
_cell_measurement_theta_min      2.791
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1385 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.8445.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2663
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.707
_diffrn_reflns_theta_min         2.790
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2423
_reflns_number_total             2663
_reflns_special_details          
;
 _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       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.213
_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)+(0.0382P)²+6.4023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1521
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.892(3) 0.108(3)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
O1 O 0.55843(5) -0.0880(3) 0.67120(8) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.59099(5) 0.6249(3) 0.46616(9) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.56403(6) 0.2107(3) 0.56900(10) 0.0156(4) Uani 1 1 d . . . . .
C4 C 0.55117(7) 0.4588(4) 0.43645(12) 0.0158(4) Uani 1 1 d . . . . .
C1 C 0.54198(7) -0.0042(4) 0.60107(11) 0.0148(4) Uani 1 1 d . . . . .
C7 C 0.52851(8) 0.5168(4) 0.35615(12) 0.0192(4) Uani 1 1 d . . . . .
H7 H 0.5002 0.4313 0.3215 0.023 Uiso 1 1 calc R . . . .
C3 C 0.53870(7) 0.2607(4) 0.48770(11) 0.0150(4) Uani 1 1 d . . . . .
C8 C 0.61021(7) 0.3305(4) 0.61758(12) 0.0178(4) Uani 1 1 d . . . . .
H8A H 0.6138 0.3051 0.6759 0.021 Uiso 1 1 calc R . . . .
H8B H 0.6100 0.5301 0.6068 0.021 Uiso 1 1 calc R . . . .
C2 C 0.50040(7) -0.0823(4) 0.53395(11) 0.0157(4) Uani 1 1 d . . . . .
C5 C 0.59266(8) 0.7890(4) 0.40284(13) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.6166 0.9258 0.4061 0.026 Uiso 1 1 calc R . . . .
C10 C 0.70123(7) 0.3369(5) 0.64343(13) 0.0213(4) Uani 1 1 d . . . . .
H10A H 0.7004 0.5301 0.6253 0.026 Uiso 1 1 calc R . . . .
H10B H 0.7050 0.3379 0.7022 0.026 Uiso 1 1 calc R . . . .
C6 C 0.55594(8) 0.7308(4) 0.33529(13) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.5496 0.8162 0.2838 0.025 Uiso 1 1 calc R . . . .
C9 C 0.65330(7) 0.1991(4) 0.59839(13) 0.0200(4) Uani 1 1 d . . . . .
H9A H 0.6550 0.0023 0.6134 0.024 Uiso 1 1 calc R . . . .
H9B H 0.6482 0.2109 0.5393 0.024 Uiso 1 1 calc R . . . .
C11 C 0.74484(8) 0.1937(5) 0.62961(13) 0.0220(4) Uani 1 1 d . . . . .
H11A H 0.7406 0.1897 0.5707 0.026 Uiso 1 1 calc R . . . .
H11B H 0.7458 0.0013 0.6485 0.026 Uiso 1 1 calc R . . . .
C12 C 0.79326(8) 0.3312(5) 0.67312(15) 0.0254(5) Uani 1 1 d . . . . .
H12A H 0.7933 0.5193 0.6515 0.030 Uiso 1 1 calc R . . . .
H12B H 0.7966 0.3467 0.7316 0.030 Uiso 1 1 calc R . . . .
C13 C 0.83680(8) 0.1739(5) 0.66327(15) 0.0275(5) Uani 1 1 d . . . . .
H13A H 0.8349 0.1686 0.6058 0.041 Uiso 1 1 calc GR . . . .
H13B H 0.8366 -0.0138 0.6835 0.041 Uiso 1 1 calc GR . . . .
H13C H 0.8668 0.2662 0.6942 0.041 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
O1 C1 1.230(2) . ?
O2 C4 1.373(2) . ?
O2 C5 1.369(2) . ?
N1 C1 1.424(3) . ?
N1 C3 1.395(2) . ?
N1 C8 1.465(2) . ?
C4 C7 1.373(3) . ?
C4 C3 1.430(3) . ?
C1 C2 1.445(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.422(3) . ?
C3 C2 1.384(3) 5_656 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(3) . ?
C2 C3 1.384(3) 5_656 ?
C2 C2 1.417(4) 5_656 ?
C5 H5 0.9500 . ?
C5 C6 1.348(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.524(3) . ?
C10 C11 1.524(3) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.528(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C4 105.95(16) . . ?
C1 N1 C8 120.50(16) . . ?
C3 N1 C1 111.20(16) . . ?
C3 N1 C8 127.99(17) . . ?
O2 C4 C3 120.49(17) . . ?
C7 C4 O2 110.16(17) . . ?
C7 C4 C3 129.36(18) . . ?
O1 C1 N1 122.96(18) . . ?
O1 C1 C2 133.01(19) . . ?
N1 C1 C2 104.02(16) . . ?
C4 C7 H7 127.0 . . ?
C4 C7 C6 106.07(18) . . ?
C6 C7 H7 127.0 . . ?
N1 C3 C4 126.10(18) . . ?
C2 C3 N1 107.32(17) 5_656 . ?
C2 C3 C4 126.58(18) 5_656 . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.77(16) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C3 C2 C1 142.54(18) 5_656 . ?
C3 C2 C2 109.0(2) 5_656 5_656 ?
C2 C2 C1 108.5(2) 5_656 . ?
O2 C5 H5 124.4 . . ?
C6 C5 O2 111.14(18) . . ?
C6 C5 H5 124.4 . . ?
H10A C10 H10B 107.8 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C11 C10 C9 112.72(18) . . ?
C7 C6 H6 126.7 . . ?
C5 C6 C7 106.68(18) . . ?
C5 C6 H6 126.7 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 C8 112.37(17) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C10 C11 C12 113.62(18) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.9(2) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C1 C2 C3 0.9(4) . . . 5_656 ?
O1 C1 C2 C2 -178.7(2) . . . 5_656 ?
O2 C4 C7 C6 0.0(2) . . . . ?
O2 C4 C3 N1 -0.9(3) . . . . ?
O2 C4 C3 C2 179.52(18) . . . 5_656 ?
O2 C5 C6 C7 0.4(2) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . 5_656 ?
N1 C1 C2 C2 0.7(3) . . . 5_656 ?
N1 C8 C9 C10 175.41(17) . . . . ?
C4 O2 C5 C6 -0.4(2) . . . . ?
C4 C7 C6 C5 -0.2(2) . . . . ?
C1 N1 C3 C4 -178.91(18) . . . . ?
C1 N1 C3 C2 0.7(2) . . . 5_656 ?
C1 N1 C8 C9 95.9(2) . . . . ?
C7 C4 C3 N1 179.1(2) . . . . ?
C7 C4 C3 C2 -0.5(3) . . . 5_656 ?
C3 N1 C1 O1 178.59(18) . . . . ?
C3 N1 C1 C2 -0.9(2) . . . . ?
C3 N1 C8 C9 -77.2(2) . . . . ?
C3 C4 C7 C6 -180.0(2) . . . . ?
C8 N1 C1 O1 4.4(3) . . . . ?
C8 N1 C1 C2 -175.02(16) . . . . ?
C8 N1 C3 C4 -5.3(3) . . . . ?
C8 N1 C3 C2 174.35(18) . . . 5_656 ?
C5 O2 C4 C7 0.2(2) . . . . ?
C5 O2 C4 C3 -179.80(18) . . . . ?
C10 C11 C12 C13 176.11(19) . . . . ?
C9 C10 C11 C12 179.05(18) . . . . ?
C11 C10 C9 C8 175.68(18) . . . . ?

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

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.892(3)
2 0.108(3)

_vrf_PLAT931_pere59              
;
PROBLEM:Found Twin Law (     )[ 0 0 -1]Estimated BASF       0.11 Check 
RESPONSE: The structure solved without difficulties by SHELXT indicated twinning: 
the R1 factor was 6.97%. TWINROTMAT give the twin law: -1 0 -1 0 -1 0 0 0 1. 
Using the HKLF5 reflection file obtained by TWINROTMAT and refining the BASF parameter,
the R1 decreases to 5.28% while the twin fraction refines to 0.108(3).
;

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylforamide'
_chemical_properties_physical    'Oxygen-sensitive, Photo-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_pere60
_database_code_depnum_ccdc_archive 'CCDC 1440141'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H64 N2 O4'
_chemical_formula_sum            'C42 H64 N2 O4'
_chemical_formula_weight         660.95
_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 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.8248(10)
_cell_length_b                   4.6921(3)
_cell_length_c                   21.4035(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.903(3)
_cell_angle_gamma                90
_cell_volume                     1856.40(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    105
_cell_measurement_theta_max      60.612
_cell_measurement_theta_min      3.660
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1190 before and 0.0757 after correction.
The Ratio of minimum to maximum transmission is 0.7665.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.594
_diffrn_reflns_theta_min         3.659
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3087
_reflns_number_total             4222
_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       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.013
_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)+(0.0572P)²+0.4714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1234
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
O1 O 0.85584(5) 1.0591(2) 1.03450(4) 0.0321(2) Uani 1 1 d . . . . .
O2 O 0.92971(5) 0.3759(2) 0.86248(4) 0.0347(3) Uani 1 1 d . . . . .
N1 N 0.90280(6) 0.7710(2) 0.96353(5) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.90761(7) 0.9865(3) 1.01122(6) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.98236(7) 1.0787(3) 1.02066(6) 0.0272(3) Uani 1 1 d . . . . .
C3 C 0.96883(7) 0.7354(3) 0.94414(6) 0.0273(3) Uani 1 1 d . . . . .
C4 C 0.98384(7) 0.5405(3) 0.89683(6) 0.0287(3) Uani 1 1 d . . . . .
C5 C 0.96173(8) 0.2150(3) 0.82227(6) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.9371 0.0799 0.7929 0.044 Uiso 1 1 calc R . . . .
C6 C 1.03283(8) 0.2734(3) 0.82983(6) 0.0359(3) Uani 1 1 d . . . . .
H6 H 1.0664 0.1898 0.8073 0.043 Uiso 1 1 calc R . . . .
C7 C 1.04783(8) 0.4847(3) 0.87811(6) 0.0324(3) Uani 1 1 d . . . . .
H7 H 1.0934 0.5701 0.8942 0.039 Uiso 1 1 calc R . . . .
C8 C 0.83398(7) 0.6282(3) 0.93952(6) 0.0299(3) Uani 1 1 d . . . . .
H8A H 0.8061 0.6138 0.9743 0.036 Uiso 1 1 calc R . . . .
H8B H 0.8437 0.4321 0.9262 0.036 Uiso 1 1 calc R . . . .
C9 C 0.78860(7) 0.7837(3) 0.88351(6) 0.0316(3) Uani 1 1 d . . . . .
H9A H 0.7716 0.9664 0.8986 0.038 Uiso 1 1 calc R . . . .
H9B H 0.8193 0.8282 0.8520 0.038 Uiso 1 1 calc R . . . .
C10 C 0.72345(7) 0.6118(3) 0.85122(6) 0.0304(3) Uani 1 1 d . . . . .
H10A H 0.6933 0.5642 0.8830 0.036 Uiso 1 1 calc R . . . .
H10B H 0.7405 0.4307 0.8354 0.036 Uiso 1 1 calc R . . . .
C11 C 0.67712(7) 0.7701(3) 0.79575(6) 0.0310(3) Uani 1 1 d . . . . .
H11A H 0.6532 0.9326 0.8129 0.037 Uiso 1 1 calc R . . . .
H11B H 0.7092 0.8489 0.7683 0.037 Uiso 1 1 calc R . . . .
C12 C 0.61936(7) 0.5881(3) 0.75494(6) 0.0312(3) Uani 1 1 d . . . . .
H12A H 0.5863 0.5137 0.7819 0.037 Uiso 1 1 calc R . . . .
H12B H 0.6429 0.4227 0.7386 0.037 Uiso 1 1 calc R . . . .
C13 C 0.57510(7) 0.7482(3) 0.69885(6) 0.0311(3) Uani 1 1 d . . . . .
H13A H 0.5487 0.9049 0.7154 0.037 Uiso 1 1 calc R . . . .
H13B H 0.6086 0.8351 0.6738 0.037 Uiso 1 1 calc R . . . .
C14 C 0.52091(7) 0.5631(3) 0.65496(6) 0.0329(3) Uani 1 1 d . . . . .
H14A H 0.5473 0.4056 0.6386 0.039 Uiso 1 1 calc R . . . .
H14B H 0.4872 0.4773 0.6800 0.039 Uiso 1 1 calc R . . . .
C15 C 0.47716(7) 0.7231(3) 0.59879(6) 0.0321(3) Uani 1 1 d . . . . .
H15A H 0.5109 0.8112 0.5741 0.039 Uiso 1 1 calc R . . . .
H15B H 0.4502 0.8788 0.6151 0.039 Uiso 1 1 calc R . . . .
C16 C 0.42374(7) 0.5368(3) 0.55448(6) 0.0335(3) Uani 1 1 d . . . . .
H16A H 0.4507 0.3816 0.5380 0.040 Uiso 1 1 calc R . . . .
H16B H 0.3902 0.4481 0.5792 0.040 Uiso 1 1 calc R . . . .
C17 C 0.37969(7) 0.6965(3) 0.49841(6) 0.0330(3) Uani 1 1 d . . . . .
H17A H 0.4132 0.7902 0.4744 0.040 Uiso 1 1 calc R . . . .
H17B H 0.3514 0.8477 0.5148 0.040 Uiso 1 1 calc R . . . .
C18 C 0.32802(7) 0.5068(3) 0.45320(6) 0.0326(3) Uani 1 1 d . . . . .
H18A H 0.3562 0.3535 0.4374 0.039 Uiso 1 1 calc R . . . .
H18B H 0.2939 0.4157 0.4771 0.039 Uiso 1 1 calc R . . . .
C19 C 0.28490(7) 0.6651(3) 0.39655(6) 0.0327(3) Uani 1 1 d . . . . .
H19A H 0.3189 0.7660 0.3741 0.039 Uiso 1 1 calc R . . . .
H19B H 0.2543 0.8103 0.4122 0.039 Uiso 1 1 calc R . . . .
C20 C 0.23687(7) 0.4713(3) 0.34962(6) 0.0338(3) Uani 1 1 d . . . . .
H20A H 0.2023 0.3726 0.3718 0.041 Uiso 1 1 calc R . . . .
H20B H 0.2673 0.3244 0.3344 0.041 Uiso 1 1 calc R . . . .
C21 C 0.19465(8) 0.6311(4) 0.29250(6) 0.0382(4) Uani 1 1 d . . . . .
H21A H 0.1679 0.4945 0.2622 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.2283 0.7388 0.2718 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.1606 0.7628 0.3068 0.057 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
O1 C1 1.2237(16) . ?
O2 C4 1.3756(17) . ?
O2 C5 1.3675(16) . ?
N1 C1 1.4274(18) . ?
N1 C3 1.3931(16) . ?
N1 C8 1.4629(17) . ?
C1 C2 1.4493(18) . ?
C2 C2 1.411(2) 3_777 ?
C2 C3 1.3825(19) 3_777 ?
C3 C2 1.3824(19) 3_777 ?
C3 C4 1.4314(18) . ?
C4 C7 1.3648(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.346(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.421(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5206(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5206(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5266(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5216(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5237(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5218(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5208(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5213(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5207(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5228(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5194(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.520(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.523(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C4 106.04(11) . . ?
C1 N1 C8 120.53(11) . . ?
C3 N1 C1 111.02(11) . . ?
C3 N1 C8 128.40(11) . . ?
O1 C1 N1 122.72(12) . . ?
O1 C1 C2 133.41(13) . . ?
N1 C1 C2 103.86(11) . . ?
C2 C2 C1 108.43(15) 3_777 . ?
C3 C2 C1 142.37(12) 3_777 . ?
C3 C2 C2 109.20(14) 3_777 3_777 ?
N1 C3 C4 126.44(12) . . ?
C2 C3 N1 107.48(11) 3_777 . ?
C2 C3 C4 126.08(12) 3_777 . ?
O2 C4 C3 120.76(11) . . ?
C7 C4 O2 109.93(12) . . ?
C7 C4 C3 129.31(13) . . ?
O2 C5 H5 124.5 . . ?
C6 C5 O2 111.02(13) . . ?
C6 C5 H5 124.5 . . ?
C5 C6 H6 126.7 . . ?
C5 C6 C7 106.60(12) . . ?
C7 C6 H6 126.7 . . ?
C4 C7 C6 106.40(13) . . ?
C4 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
N1 C8 C9 112.65(11) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 112.83(12) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 112.85(12) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.49(12) . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C11 C12 C13 113.60(12) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.05(12) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.93(12) . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C14 C15 C16 113.85(12) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.98(12) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C16 C17 C18 113.64(13) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.70(12) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C18 C19 C20 113.35(13) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C19 C20 C21 113.02(13) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C1 C2 C2 -178.84(15) . . . 3_777 ?
O1 C1 C2 C3 1.6(3) . . . 3_777 ?
O2 C4 C7 C6 -0.28(15) . . . . ?
O2 C5 C6 C7 0.21(17) . . . . ?
N1 C1 C2 C2 0.38(17) . . . 3_777 ?
N1 C1 C2 C3 -179.21(17) . . . 3_777 ?
N1 C3 C4 O2 4.0(2) . . . . ?
N1 C3 C4 C7 -176.16(14) . . . . ?
N1 C8 C9 C10 170.12(11) . . . . ?
C1 N1 C3 C2 1.09(15) . . . 3_777 ?
C1 N1 C3 C4 -179.40(12) . . . . ?
C1 N1 C8 C9 88.43(14) . . . . ?
C2 C3 C4 O2 -176.61(12) 3_777 . . . ?
C2 C3 C4 C7 3.3(2) 3_777 . . . ?
C3 N1 C1 O1 178.43(12) . . . . ?
C3 N1 C1 C2 -0.90(14) . . . . ?
C3 N1 C8 C9 -88.69(16) . . . . ?
C3 C4 C7 C6 179.83(13) . . . . ?
C4 O2 C5 C6 -0.38(15) . . . . ?
C5 O2 C4 C3 -179.70(12) . . . . ?
C5 O2 C4 C7 0.41(15) . . . . ?
C5 C6 C7 C4 0.05(16) . . . . ?
C8 N1 C1 O1 0.84(19) . . . . ?
C8 N1 C1 C2 -178.49(11) . . . . ?
C8 N1 C3 C2 178.44(12) . . . 3_777 ?
C8 N1 C3 C4 -2.1(2) . . . . ?
C8 C9 C10 C11 178.95(11) . . . . ?
C9 C10 C11 C12 169.71(11) . . . . ?
C10 C11 C12 C13 -178.46(11) . . . . ?
C11 C12 C13 C14 175.76(11) . . . . ?
C12 C13 C14 C15 -179.63(11) . . . . ?
C13 C14 C15 C16 179.21(11) . . . . ?
C14 C15 C16 C17 179.76(11) . . . . ?
C15 C16 C17 C18 178.23(11) . . . . ?
C16 C17 C18 C19 -179.01(11) . . . . ?
C17 C18 C19 C20 176.50(11) . . . . ?
C18 C19 C20 C21 -179.18(11) . . . . ?

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

_vrf_PLAT910_pere60              
;
PROBLEM:Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
RESPONSE: the reflection 1 0 0 affected by beamstop was omitted in last cycles.
;

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate'
_chemical_properties_physical    'Oxygen-sensitive, Photo-sensitive'
