# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 2077531'
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_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           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                   8.6130(2)
_cell_length_b                   8.1005(2)
_cell_length_c                   22.9376(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.1990(10)
_cell_angle_gamma                90
_cell_volume                     1600.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.82
_cell_measurement_theta_min      3.35
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.3012
_exptl_absorpt_correction_T_min  0.2235
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0885 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.7420.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14265
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.323
_diffrn_reflns_theta_min         1.776
_diffrn_ambient_temperature      193.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2611
_reflns_number_total             2906
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.136
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.030
_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)+(0.0500P)²+0.3594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0988
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.26808(11) 1.16896(11) 0.48287(4) 0.0487(3) Uani 1 1 d . . . . .
O2 O 0.18800(11) 0.94998(11) 0.53290(4) 0.0492(3) Uani 1 1 d . . . . .
N1 N 0.57183(11) 0.53004(12) 0.35648(4) 0.0345(2) Uani 1 1 d . . . . .
C1 C 0.72346(13) 0.47517(14) 0.36646(5) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.82412(14) 0.51111(17) 0.41287(6) 0.0448(3) Uani 1 1 d . . . . .
H2 H 0.7937 0.5805 0.4440 0.054 Uiso 1 1 calc R . . . .
C3 C 0.97083(16) 0.4412(2) 0.41167(8) 0.0608(4) Uani 1 1 d . U . . .
H3 H 1.0426 0.4628 0.4428 0.073 Uiso 1 1 calc R . . . .
C4 C 1.01527(18) 0.3404(2) 0.36601(9) 0.0704(5) Uani 1 1 d . U . . .
H4 H 1.1171 0.2953 0.3663 0.084 Uiso 1 1 calc R . . . .
C5 C 0.91506(18) 0.30437(19) 0.32031(8) 0.0613(4) Uani 1 1 d . . . . .
H5 H 0.9468 0.2344 0.2895 0.074 Uiso 1 1 calc R . . . .
C6 C 0.76537(15) 0.37236(15) 0.31983(6) 0.0436(3) Uani 1 1 d . . . . .
C7 C 0.63363(16) 0.36482(14) 0.28022(6) 0.0426(3) Uani 1 1 d . . . . .
C8 C 0.6019(2) 0.28142(18) 0.22820(6) 0.0583(4) Uani 1 1 d . . . . .
H8 H 0.6783 0.2126 0.2114 0.070 Uiso 1 1 calc R . . . .
C9 C 0.4587(2) 0.3000(2) 0.20145(7) 0.0668(5) Uani 1 1 d . . . . .
H9 H 0.4366 0.2433 0.1660 0.080 Uiso 1 1 calc R . . . .
C10 C 0.3453(2) 0.4006(2) 0.22542(6) 0.0592(4) Uani 1 1 d . . . . .
H10 H 0.2477 0.4120 0.2058 0.071 Uiso 1 1 calc R . . . .
C11 C 0.37224(16) 0.48436(17) 0.27733(6) 0.0448(3) Uani 1 1 d . . . . .
H11 H 0.2949 0.5523 0.2939 0.054 Uiso 1 1 calc R . . . .
C12 C 0.51689(14) 0.46464(14) 0.30400(5) 0.0363(3) Uani 1 1 d . . . . .
C13 C 0.49376(12) 0.65218(14) 0.38998(5) 0.0314(3) Uani 1 1 d . . . . .
C14 C 0.50763(13) 0.81679(14) 0.37482(5) 0.0333(3) Uani 1 1 d . . . . .
H14 H 0.5679 0.8452 0.3421 0.040 Uiso 1 1 calc R . . . .
C15 C 0.43592(13) 0.94237(14) 0.40602(5) 0.0324(3) Uani 1 1 d . . . . .
C16 C 0.34660(12) 0.89621(14) 0.45377(5) 0.0319(3) Uani 1 1 d . . . . .
C17 C 0.33249(15) 0.72963(16) 0.46826(5) 0.0409(3) Uani 1 1 d . . . . .
H17 H 0.2712 0.6995 0.5005 0.049 Uiso 1 1 calc R . . . .
C18 C 0.40527(15) 0.60740(15) 0.43692(5) 0.0406(3) Uani 1 1 d . . . . .
H18 H 0.3946 0.4946 0.4475 0.049 Uiso 1 1 calc R . . . .
C19 C 0.45956(17) 1.11780(16) 0.38627(6) 0.0499(4) Uani 1 1 d . . . . .
H19A H 0.5308 1.1194 0.3535 0.075 Uiso 1 1 calc GR . . . .
H19B H 0.5037 1.1830 0.4186 0.075 Uiso 1 1 calc GR . . . .
H19C H 0.3595 1.1652 0.3739 0.075 Uiso 1 1 calc GR . . . .
C20 C 0.26608(13) 1.02190(15) 0.49006(5) 0.0354(3) Uani 1 1 d . . . . .
C21 C 0.10461(17) 1.05811(19) 0.57128(7) 0.0547(4) Uani 1 1 d . . . . .
H21A H 0.0407 1.1347 0.5480 0.082 Uiso 1 1 calc GR . . . .
H21B H 0.1788 1.1208 0.5955 0.082 Uiso 1 1 calc GR . . . .
H21C H 0.0377 0.9923 0.5963 0.082 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 C20 1.2029(15) . ?
O2 C20 1.3359(15) . ?
O2 C21 1.4437(15) . ?
N1 C1 1.3939(15) . ?
N1 C12 1.3893(15) . ?
N1 C13 1.4293(14) . ?
C1 C2 1.3896(19) . ?
C1 C6 1.4086(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3853(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(2) . ?
C6 C7 1.440(2) . ?
C7 C8 1.393(2) . ?
C7 C12 1.4090(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3856(18) . ?
C13 C14 1.3839(16) . ?
C13 C18 1.3807(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3953(16) . ?
C15 C16 1.4023(16) . ?
C15 C19 1.5067(17) . ?
C16 C17 1.3956(17) . ?
C16 C20 1.4949(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3816(17) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C20 O2 C21 116.64(10) . . ?
C1 N1 C13 125.60(10) . . ?
C12 N1 C1 108.76(10) . . ?
C12 N1 C13 125.05(10) . . ?
N1 C1 C6 108.54(11) . . ?
C2 C1 N1 128.78(11) . . ?
C2 C1 C6 122.68(12) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.00(14) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.42(16) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.42(14) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.02(15) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 107.05(11) . . ?
C5 C6 C1 118.46(14) . . ?
C5 C6 C7 134.49(14) . . ?
C8 C7 C6 134.32(13) . . ?
C8 C7 C12 118.76(14) . . ?
C12 C7 C6 106.90(11) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.15(14) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.17(14) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.30(16) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.10(14) . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C7 108.74(11) . . ?
C11 C12 N1 128.71(11) . . ?
C11 C12 C7 122.52(12) . . ?
C14 C13 N1 119.20(10) . . ?
C18 C13 N1 120.73(10) . . ?
C18 C13 C14 120.07(10) . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.15(10) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C16 117.53(10) . . ?
C14 C15 C19 117.99(10) . . ?
C16 C15 C19 124.48(11) . . ?
C15 C16 C20 121.46(10) . . ?
C17 C16 C15 119.71(11) . . ?
C17 C16 C20 118.83(10) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.76(11) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 118.77(11) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 O2 122.79(11) . . ?
O1 C20 C16 126.16(11) . . ?
O2 C20 C16 111.05(10) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_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_ww_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2077532'
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_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      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                   7.9261(4)
_cell_length_b                   9.7507(6)
_cell_length_c                   11.1901(5)
_cell_angle_alpha                72.299(2)
_cell_angle_beta                 77.213(2)
_cell_angle_gamma                86.046(2)
_cell_volume                     803.45(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2266
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1274 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.8626.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8006
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         2.635
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3281
_reflns_number_total             3910
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.291
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.024
_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)+(0.0403P)²+0.2758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1074
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.80358(11) 0.71834(9) 0.01397(8) 0.0287(2) Uani 1 1 d . . . . .
O2 O 1.05341(12) 0.80238(10) 0.09960(10) 0.0327(2) Uani 1 1 d . . . . .
O3 O 1.25909(13) 0.63387(12) 0.12624(12) 0.0493(3) Uani 1 1 d . . . . .
N1 N 0.56320(13) 0.26376(11) 0.30088(10) 0.0260(2) Uani 1 1 d . . . . .
C1 C 0.55788(16) 0.12309(13) 0.29588(11) 0.0242(2) Uani 1 1 d . . . . .
C2 C 0.67975(17) 0.04958(14) 0.22853(12) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.7840 0.0923 0.1795 0.036 Uiso 1 1 calc R . . . .
C3 C 0.64052(19) -0.08947(15) 0.23697(13) 0.0347(3) Uani 1 1 d . . . . .
H3 H 0.7198 -0.1412 0.1928 0.042 Uiso 1 1 calc R . . . .
C4 C 0.4844(2) -0.15349(15) 0.31043(14) 0.0356(3) Uani 1 1 d . . . . .
H4 H 0.4612 -0.2471 0.3144 0.043 Uiso 1 1 calc R . . . .
C5 C 0.36358(18) -0.07995(14) 0.37757(13) 0.0301(3) Uani 1 1 d . . . . .
H5 H 0.2598 -0.1236 0.4266 0.036 Uiso 1 1 calc R . . . .
C6 C 0.39945(16) 0.06043(13) 0.37072(11) 0.0244(2) Uani 1 1 d . . . . .
C7 C 0.30645(15) 0.16693(13) 0.42592(11) 0.0241(2) Uani 1 1 d . . . . .
C8 C 0.14896(16) 0.16740(15) 0.51167(12) 0.0303(3) Uani 1 1 d . . . . .
H8 H 0.0773 0.0871 0.5422 0.036 Uiso 1 1 calc R . . . .
C9 C 0.10113(18) 0.28858(16) 0.55043(13) 0.0346(3) Uani 1 1 d . . . . .
H9 H -0.0041 0.2900 0.6068 0.042 Uiso 1 1 calc R . . . .
C10 C 0.20825(18) 0.40872(15) 0.50624(13) 0.0349(3) Uani 1 1 d . . . . .
H10 H 0.1738 0.4885 0.5347 0.042 Uiso 1 1 calc R . . . .
C11 C 0.36493(17) 0.41220(14) 0.42090(13) 0.0306(3) Uani 1 1 d . . . . .
H11 H 0.4361 0.4927 0.3914 0.037 Uiso 1 1 calc R . . . .
C12 C 0.41151(15) 0.29039(13) 0.38116(11) 0.0247(2) Uani 1 1 d . . . . .
C13 C 0.70517(15) 0.36038(13) 0.24392(11) 0.0249(2) Uani 1 1 d . . . . .
C14 C 0.68050(15) 0.49194(13) 0.15629(12) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.5748 0.5131 0.1316 0.030 Uiso 1 1 calc R . . . .
C15 C 0.81435(15) 0.59194(13) 0.10556(11) 0.0236(2) Uani 1 1 d . . . . .
C16 C 0.97098(15) 0.56078(13) 0.14850(11) 0.0241(2) Uani 1 1 d . . . . .
C17 C 0.99451(16) 0.42509(14) 0.23048(12) 0.0278(3) Uani 1 1 d . . . . .
H17 H 1.1008 0.4017 0.2538 0.033 Uiso 1 1 calc R . . . .
C18 C 0.86355(16) 0.32412(14) 0.27808(12) 0.0283(3) Uani 1 1 d . . . . .
H18 H 0.8815 0.2333 0.3322 0.034 Uiso 1 1 calc R . . . .
C19 C 1.11150(16) 0.66713(14) 0.12073(12) 0.0277(3) Uani 1 1 d . . . . .
C20 C 1.17240(19) 0.90870(16) 0.09771(15) 0.0379(3) Uani 1 1 d . . . . .
H20A H 1.2801 0.9013 0.0405 0.057 Uiso 1 1 calc GR . . . .
H20B H 1.1919 0.8925 0.1826 0.057 Uiso 1 1 calc GR . . . .
H20C H 1.1244 1.0031 0.0688 0.057 Uiso 1 1 calc GR . . . .
C21 C 0.65496(18) 0.74138(16) -0.04225(14) 0.0377(3) Uani 1 1 d . . . . .
H21A H 0.6675 0.8304 -0.1105 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.5534 0.7457 0.0218 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.6441 0.6635 -0.0758 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 C15 1.3538(14) . ?
O1 C21 1.4281(15) . ?
O2 C19 1.3349(16) . ?
O2 C20 1.4413(16) . ?
O3 C19 1.2021(15) . ?
N1 C1 1.3935(15) . ?
N1 C12 1.3931(15) . ?
N1 C13 1.4225(15) . ?
C1 C2 1.3876(17) . ?
C1 C6 1.4074(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3825(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3930(17) . ?
C6 C7 1.4444(17) . ?
C7 C8 1.3966(18) . ?
C7 C12 1.4072(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3844(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.3902(17) . ?
C13 C14 1.3895(17) . ?
C13 C18 1.3842(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3921(17) . ?
C15 C16 1.4099(16) . ?
C16 C17 1.3894(17) . ?
C16 C19 1.4908(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.3812(18) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C15 O1 C21 117.55(10) . . ?
C19 O2 C20 116.57(10) . . ?
C1 N1 C13 126.22(10) . . ?
C12 N1 C1 108.48(10) . . ?
C12 N1 C13 125.06(10) . . ?
N1 C1 C6 108.85(11) . . ?
C2 C1 N1 129.00(12) . . ?
C2 C1 C6 122.13(12) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.56(12) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.23(13) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.00(13) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.05(13) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.90(11) . . ?
C5 C6 C1 119.03(12) . . ?
C5 C6 C7 134.08(12) . . ?
C8 C7 C6 134.13(12) . . ?
C8 C7 C12 118.98(12) . . ?
C12 C7 C6 106.84(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.12(12) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.89(12) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.55(13) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.28(13) . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C7 108.91(11) . . ?
C11 C12 N1 128.84(12) . . ?
C11 C12 C7 122.18(12) . . ?
C14 C13 N1 118.87(11) . . ?
C18 C13 N1 120.05(11) . . ?
C18 C13 C14 121.06(11) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.86(11) . . ?
C15 C14 H14 120.1 . . ?
O1 C15 C14 123.17(11) . . ?
O1 C15 C16 117.51(10) . . ?
C14 C15 C16 119.31(11) . . ?
C15 C16 C19 124.71(11) . . ?
C17 C16 C15 119.05(11) . . ?
C17 C16 C19 116.06(11) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.48(11) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 120.6 . . ?
C17 C18 C13 118.86(11) . . ?
C17 C18 H18 120.6 . . ?
O2 C19 C16 112.79(10) . . ?
O3 C19 O2 123.41(12) . . ?
O3 C19 C16 123.58(12) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
