# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_111a
_database_code_depnum_ccdc_archive 'CCDC 1912663'
loop_
_audit_author_name
_audit_author_address
'chaoqun ma'
;Nanjing Tech University (NanjingTech)
China
;
_audit_update_record             
;
2019-04-28 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N4 O3'
_chemical_formula_sum            'C20 H20 N4 O3'
_chemical_formula_weight         364.40
_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/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                   13.0085(17)
_cell_length_b                   10.9842(14)
_cell_length_c                   12.9585(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.979(4)
_cell_angle_gamma                90
_cell_volume                     1817.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    146
_cell_measurement_temperature    287.82
_cell_measurement_theta_max      0.991
_cell_measurement_theta_min      0.989
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.376
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      287.82
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_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                2638
_reflns_number_total             4533
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.213
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.044
_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)+(0.0650P)²+0.4920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1618
_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:
 C00G(H00B,H00C), C00J(H00D,H00E), C00K(H00F,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00Q(H00J,H00K,H00Q), C00R(H00R,H00S,H00T)
;
_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
O001 O 0.55950(12) 0.58189(14) 0.74014(13) 0.0570(5) Uani 1 1 d . . . . .
O002 O 0.69825(13) 0.26374(14) 0.92670(13) 0.0582(4) Uani 1 1 d . . . . .
O003 O 0.89896(12) 0.47534(15) 0.74045(13) 0.0602(5) Uani 1 1 d . . . . .
N004 N 0.73002(13) 0.53628(15) 0.73331(14) 0.0444(4) Uani 1 1 d . . . . .
N005 N 0.80627(14) 0.36952(15) 0.83768(14) 0.0460(4) Uani 1 1 d . . . . .
N006 N 0.62823(14) 0.42189(16) 0.83293(15) 0.0482(5) Uani 1 1 d . . . . .
N007 N 0.65156(13) 0.81907(15) 0.50491(14) 0.0438(4) Uani 1 1 d . . . . .
C008 C 0.79461(16) 0.93597(17) 0.56803(15) 0.0381(5) Uani 1 1 d . . . . .
C009 C 0.68745(16) 0.91815(17) 0.56820(16) 0.0398(5) Uani 1 1 d . . . . .
C00A C 0.84674(18) 1.03195(18) 0.62432(16) 0.0446(5) Uani 1 1 d . . . . .
H00A H 0.9175 1.0449 0.6249 0.053 Uiso 1 1 calc R . . . .
C00B C 0.64291(16) 0.51186(19) 0.76918(17) 0.0438(5) Uani 1 1 d . . . . .
C00C C 0.73476(16) 0.77292(18) 0.46435(16) 0.0428(5) Uani 1 1 d . . . . .
C00D C 0.71326(17) 0.35559(18) 0.86365(16) 0.0439(5) Uani 1 1 d . . . . .
C00E C 0.80778(16) 0.46217(19) 0.77098(17) 0.0435(5) Uani 1 1 d . . . . .
C00F C 0.82486(16) 0.84180(18) 0.50202(16) 0.0411(5) Uani 1 1 d . . . . .
C00G C 0.54471(16) 0.65383(19) 0.55942(18) 0.0494(6) Uani 1 1 d . . . . .
H00B H 0.4758 0.6169 0.5424 0.059 Uiso 1 1 calc R . . . .
H00C H 0.5955 0.5946 0.5451 0.059 Uiso 1 1 calc R . . . .
C00H C 0.63290(17) 0.99377(19) 0.62538(17) 0.0481(5) Uani 1 1 d . . . . .
H00H H 0.5625 0.9808 0.6265 0.058 Uiso 1 1 calc R . . . .
C00I C 0.73685(19) 0.6751(2) 0.39642(17) 0.0531(6) Uani 1 1 d . . . . .
H00I H 0.6774 0.6286 0.3724 0.064 Uiso 1 1 calc R . . . .
C00J C 0.56840(17) 0.68669(19) 0.67429(17) 0.0484(5) Uani 1 1 d . . . . .
H00D H 0.6388 0.7194 0.6921 0.058 Uiso 1 1 calc R . . . .
H00E H 0.5201 0.7494 0.6878 0.058 Uiso 1 1 calc R . . . .
C00K C 0.54798(17) 0.7655(2) 0.49055(18) 0.0501(5) Uani 1 1 d . . . . .
H00F H 0.5258 0.7426 0.4174 0.060 Uiso 1 1 calc R . . . .
H00G H 0.4990 0.8257 0.5071 0.060 Uiso 1 1 calc R . . . .
C00L C 0.79252(19) 1.10836(19) 0.67961(17) 0.0509(6) Uani 1 1 d . . . . .
H00L H 0.8267 1.1737 0.7169 0.061 Uiso 1 1 calc R . . . .
C00M C 0.91883(19) 0.8121(2) 0.47221(18) 0.0531(6) Uani 1 1 d . . . . .
H00M H 0.9794 0.8561 0.4978 0.064 Uiso 1 1 calc R . . . .
C00N C 0.68729(19) 1.0882(2) 0.67991(18) 0.0525(6) Uani 1 1 d . . . . .
H00N H 0.6525 1.1403 0.7183 0.063 Uiso 1 1 calc R . . . .
C00O C 0.8306(2) 0.6501(2) 0.36625(19) 0.0630(7) Uani 1 1 d . . . . .
H00O H 0.8336 0.5870 0.3191 0.076 Uiso 1 1 calc R . . . .
C00P C 0.9205(2) 0.7163(2) 0.4039(2) 0.0638(7) Uani 1 1 d . . . . .
H00P H 0.9828 0.6957 0.3830 0.077 Uiso 1 1 calc R . . . .
C00Q C 0.9088(2) 0.5749(3) 0.6700(2) 0.0678(7) Uani 1 1 d . . . . .
H00J H 0.8583 0.5654 0.6061 0.102 Uiso 1 1 calc GR . . . .
H00K H 0.9780 0.5749 0.6543 0.102 Uiso 1 1 calc GR . . . .
H00Q H 0.8967 0.6506 0.7027 0.102 Uiso 1 1 calc GR . . . .
C00R C 0.7844(2) 0.1847(2) 0.9664(2) 0.0662(7) Uani 1 1 d . . . . .
H00R H 0.8025 0.1385 0.9095 0.099 Uiso 1 1 calc GR . . . .
H00S H 0.7650 0.1303 1.0174 0.099 Uiso 1 1 calc GR . . . .
H00T H 0.8436 0.2325 0.9989 0.099 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
O001 C00B 1.325(2) . ?
O001 C00J 1.451(2) . ?
O002 C00D 1.336(2) . ?
O002 C00R 1.433(3) . ?
O003 C00E 1.328(3) . ?
O003 C00Q 1.447(3) . ?
N004 C00B 1.331(3) . ?
N004 C00E 1.318(3) . ?
N005 C00D 1.325(3) . ?
N005 C00E 1.338(3) . ?
N006 C00B 1.325(3) . ?
N006 C00D 1.321(3) . ?
N007 C009 1.389(3) . ?
N007 C00C 1.386(3) . ?
N007 C00K 1.450(3) . ?
C008 C009 1.408(3) . ?
C008 C00A 1.384(3) . ?
C008 C00F 1.444(3) . ?
C009 C00H 1.394(3) . ?
C00A H00A 0.9300 . ?
C00A C00L 1.381(3) . ?
C00C C00F 1.402(3) . ?
C00C C00I 1.393(3) . ?
C00F C00M 1.389(3) . ?
C00G H00B 0.9700 . ?
C00G H00C 0.9700 . ?
C00G C00J 1.505(3) . ?
C00G C00K 1.522(3) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.373(3) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.377(3) . ?
C00J H00D 0.9700 . ?
C00J H00E 0.9700 . ?
C00K H00F 0.9700 . ?
C00K H00G 0.9700 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.387(3) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.378(3) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00P 1.384(4) . ?
C00P H00P 0.9300 . ?
C00Q H00J 0.9600 . ?
C00Q H00K 0.9600 . ?
C00Q H00Q 0.9600 . ?
C00R H00R 0.9600 . ?
C00R H00S 0.9600 . ?
C00R H00T 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
C00B O001 C00J 118.37(16) . . ?
C00D O002 C00R 118.77(19) . . ?
C00E O003 C00Q 117.54(17) . . ?
C00E N004 C00B 113.00(18) . . ?
C00D N005 C00E 112.24(18) . . ?
C00D N006 C00B 112.79(18) . . ?
C009 N007 C00K 126.42(18) . . ?
C00C N007 C009 108.15(16) . . ?
C00C N007 C00K 125.21(18) . . ?
C009 C008 C00F 106.43(17) . . ?
C00A C008 C009 119.40(18) . . ?
C00A C008 C00F 134.16(19) . . ?
N007 C009 C008 109.24(17) . . ?
N007 C009 C00H 129.26(19) . . ?
C00H C009 C008 121.50(19) . . ?
C008 C00A H00A 120.4 . . ?
C00L C00A C008 119.3(2) . . ?
C00L C00A H00A 120.4 . . ?
O001 C00B N004 119.30(19) . . ?
O001 C00B N006 113.74(18) . . ?
N006 C00B N004 126.96(19) . . ?
N007 C00C C00F 109.39(17) . . ?
N007 C00C C00I 129.2(2) . . ?
C00I C00C C00F 121.4(2) . . ?
N005 C00D O002 119.31(19) . . ?
N006 C00D O002 112.91(19) . . ?
N006 C00D N005 127.77(19) . . ?
O003 C00E N005 113.53(18) . . ?
N004 C00E O003 119.25(19) . . ?
N004 C00E N005 127.20(19) . . ?
C00C C00F C008 106.78(17) . . ?
C00M C00F C008 133.3(2) . . ?
C00M C00F C00C 119.87(19) . . ?
H00B C00G H00C 108.0 . . ?
C00J C00G H00B 109.4 . . ?
C00J C00G H00C 109.4 . . ?
C00J C00G C00K 111.30(18) . . ?
C00K C00G H00B 109.4 . . ?
C00K C00G H00C 109.4 . . ?
C009 C00H H00H 121.3 . . ?
C00N C00H C009 117.3(2) . . ?
C00N C00H H00H 121.3 . . ?
C00C C00I H00I 121.4 . . ?
C00O C00I C00C 117.3(2) . . ?
C00O C00I H00I 121.4 . . ?
O001 C00J C00G 111.54(18) . . ?
O001 C00J H00D 109.3 . . ?
O001 C00J H00E 109.3 . . ?
C00G C00J H00D 109.3 . . ?
C00G C00J H00E 109.3 . . ?
H00D C00J H00E 108.0 . . ?
N007 C00K C00G 112.40(17) . . ?
N007 C00K H00F 109.1 . . ?
N007 C00K H00G 109.1 . . ?
C00G C00K H00F 109.1 . . ?
C00G C00K H00G 109.1 . . ?
H00F C00K H00G 107.9 . . ?
C00A C00L H00L 119.8 . . ?
C00A C00L C00N 120.4(2) . . ?
C00N C00L H00L 119.8 . . ?
C00F C00M H00M 120.7 . . ?
C00P C00M C00F 118.7(2) . . ?
C00P C00M H00M 120.7 . . ?
C00H C00N C00L 122.1(2) . . ?
C00H C00N H00N 119.0 . . ?
C00L C00N H00N 119.0 . . ?
C00I C00O H00O 119.0 . . ?
C00I C00O C00P 122.0(2) . . ?
C00P C00O H00O 119.0 . . ?
C00M C00P C00O 120.8(2) . . ?
C00M C00P H00P 119.6 . . ?
C00O C00P H00P 119.6 . . ?
O003 C00Q H00J 109.5 . . ?
O003 C00Q H00K 109.5 . . ?
O003 C00Q H00Q 109.5 . . ?
H00J C00Q H00K 109.5 . . ?
H00J C00Q H00Q 109.5 . . ?
H00K C00Q H00Q 109.5 . . ?
O002 C00R H00R 109.5 . . ?
O002 C00R H00S 109.5 . . ?
O002 C00R H00T 109.5 . . ?
H00R C00R H00S 109.5 . . ?
H00R C00R H00T 109.5 . . ?
H00S C00R H00T 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_111a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1912664'
loop_
_audit_author_name
_audit_author_address
'chaoqun ma'
;Nanjing Tech University (NanjingTech)
China
;
_audit_update_record             
;
2019-04-28 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N4 O3'
_chemical_formula_sum            'C20 H20 N4 O3'
_chemical_formula_weight         364.40
_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/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                   12.9566(14)
_cell_length_b                   10.8698(12)
_cell_length_c                   12.9109(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.360(3)
_cell_angle_gamma                90
_cell_volume                     1782.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    123
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      0.991
_cell_measurement_theta_min      0.989
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18715
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.175
_diffrn_reflns_theta_min         2.466
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_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                4163
_reflns_number_total             5729
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.385
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.040
_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)+(0.0750P)²+0.4410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1502
_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:
 C00H(H00A,H00B), C00J(H00C,H00E), C00N(H00G,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00P(H00J,H00N,H00P), C00R(H00R,H00S,H00T)
;
_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
O001 O 0.55804(8) 0.58660(9) 0.74383(8) 0.0255(2) Uani 1 1 d . . . . .
O002 O 0.69854(8) 0.26413(9) 0.93226(8) 0.0257(2) Uani 1 1 d . . . . .
O003 O 0.89871(8) 0.47421(10) 0.74127(9) 0.0274(2) Uani 1 1 d . . . . .
N004 N 0.72918(9) 0.53816(10) 0.73549(9) 0.0207(2) Uani 1 1 d . . . . .
N005 N 0.62764(9) 0.42461(11) 0.83795(10) 0.0221(2) Uani 1 1 d . . . . .
N006 N 0.65138(9) 0.82116(10) 0.50610(9) 0.0200(2) Uani 1 1 d . . . . .
N007 N 0.80661(9) 0.36915(10) 0.84097(9) 0.0213(2) Uani 1 1 d . . . . .
C008 C 0.68859(10) 0.92085(11) 0.56987(10) 0.0183(3) Uani 1 1 d . . . . .
C009 C 0.79678(10) 0.93766(12) 0.57000(10) 0.0177(2) Uani 1 1 d . . . . .
C00A C 0.73403(10) 0.77323(12) 0.46530(10) 0.0194(3) Uani 1 1 d . . . . .
C00B C 0.71347(11) 0.35578(12) 0.86825(11) 0.0201(3) Uani 1 1 d . . . . .
C00C C 0.64218(10) 0.51503(12) 0.77285(11) 0.0198(3) Uani 1 1 d . . . . .
C00D C 0.85092(11) 1.03493(12) 0.62667(11) 0.0206(3) Uani 1 1 d . . . . .
H00D H 0.9235 1.0476 0.6268 0.025 Uiso 1 1 calc R . . . .
C00E C 0.80767(11) 0.46220(12) 0.77305(11) 0.0201(3) Uani 1 1 d . . . . .
C00F C 0.73489(12) 0.67422(13) 0.39661(11) 0.0238(3) Uani 1 1 d . . . . .
H00F H 0.6733 0.6269 0.3721 0.029 Uiso 1 1 calc R . . . .
C00G C 0.82623(11) 0.84255(12) 0.50330(10) 0.0194(3) Uani 1 1 d . . . . .
C00H C 0.54241(11) 0.65542(12) 0.56076(11) 0.0218(3) Uani 1 1 d . . . . .
H00A H 0.4714 0.6180 0.5434 0.026 Uiso 1 1 calc R . . . .
H00B H 0.5941 0.5935 0.5469 0.026 Uiso 1 1 calc R . . . .
C00I C 0.63448(11) 0.99742(13) 0.62805(11) 0.0220(3) Uani 1 1 d . . . . .
H00I H 0.5624 0.9841 0.6297 0.026 Uiso 1 1 calc R . . . .
C00J C 0.56704(11) 0.69125(12) 0.67624(11) 0.0222(3) Uani 1 1 d . . . . .
H00C H 0.6394 0.7247 0.6942 0.027 Uiso 1 1 calc R . . . .
H00E H 0.5178 0.7566 0.6890 0.027 Uiso 1 1 calc R . . . .
C00K C 0.79757(11) 1.11277(12) 0.68264(11) 0.0226(3) Uani 1 1 d . . . . .
H00K H 0.8336 1.1798 0.7210 0.027 Uiso 1 1 calc R . . . .
C00L C 0.69030(12) 1.09330(13) 0.68308(11) 0.0240(3) Uani 1 1 d . . . . .
H00L H 0.6552 1.1476 0.7223 0.029 Uiso 1 1 calc R . . . .
C00M C 0.92040(11) 0.81177(13) 0.47303(11) 0.0242(3) Uani 1 1 d . . . . .
H00M H 0.9831 0.8565 0.4993 0.029 Uiso 1 1 calc R . . . .
C00N C 0.54651(10) 0.76804(13) 0.49094(11) 0.0225(3) Uani 1 1 d . . . . .
H00G H 0.5236 0.7441 0.4159 0.027 Uiso 1 1 calc R . . . .
H00H H 0.4967 0.8309 0.5072 0.027 Uiso 1 1 calc R . . . .
C00O C 0.82867(13) 0.64744(14) 0.36555(12) 0.0274(3) Uani 1 1 d . . . . .
H00O H 0.8306 0.5820 0.3172 0.033 Uiso 1 1 calc R . . . .
C00P C 0.90773(12) 0.57566(15) 0.67060(13) 0.0296(3) Uani 1 1 d . . . . .
H00J H 0.8556 0.5658 0.6050 0.044 Uiso 1 1 calc GR . . . .
H00N H 0.9786 0.5763 0.6545 0.044 Uiso 1 1 calc GR . . . .
H00P H 0.8952 0.6534 0.7045 0.044 Uiso 1 1 calc GR . . . .
C00Q C 0.92069(12) 0.71419(14) 0.40356(12) 0.0281(3) Uani 1 1 d . . . . .
H00Q H 0.9841 0.6925 0.3816 0.034 Uiso 1 1 calc R . . . .
C00R C 0.78567(13) 0.18304(13) 0.97023(13) 0.0295(3) Uani 1 1 d . . . . .
H00R H 0.8030 0.1366 0.9108 0.044 Uiso 1 1 calc GR . . . .
H00S H 0.7664 0.1257 1.0219 0.044 Uiso 1 1 calc GR . . . .
H00T H 0.8469 0.2316 1.0038 0.044 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
O001 C00C 1.3316(16) . ?
O001 C00J 1.4523(16) . ?
O002 C00B 1.3326(16) . ?
O002 C00R 1.4399(17) . ?
O003 C00E 1.3295(17) . ?
O003 C00P 1.4506(18) . ?
N004 C00C 1.3343(17) . ?
N004 C00E 1.3254(17) . ?
N005 C00B 1.3335(18) . ?
N005 C00C 1.3306(17) . ?
N006 C008 1.3886(17) . ?
N006 C00A 1.3849(17) . ?
N006 C00N 1.4537(17) . ?
N007 C00B 1.3300(18) . ?
N007 C00E 1.3405(18) . ?
C008 C009 1.4132(18) . ?
C008 C00I 1.3985(18) . ?
C009 C00D 1.3939(19) . ?
C009 C00G 1.4441(18) . ?
C00A C00F 1.3960(18) . ?
C00A C00G 1.4159(19) . ?
C00D H00D 0.9500 . ?
C00D C00K 1.3830(19) . ?
C00F H00F 0.9500 . ?
C00F C00O 1.383(2) . ?
C00G C00M 1.3933(19) . ?
C00H H00A 0.9900 . ?
C00H H00B 0.9900 . ?
C00H C00J 1.513(2) . ?
C00H C00N 1.5273(19) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.383(2) . ?
C00J H00C 0.9900 . ?
C00J H00E 0.9900 . ?
C00K H00K 0.9500 . ?
C00K C00L 1.407(2) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00Q 1.390(2) . ?
C00N H00G 0.9900 . ?
C00N H00H 0.9900 . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.399(2) . ?
C00P H00J 0.9800 . ?
C00P H00N 0.9800 . ?
C00P H00P 0.9800 . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9800 . ?
C00R H00S 0.9800 . ?
C00R H00T 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
C00C O001 C00J 117.94(10) . . ?
C00B O002 C00R 117.96(11) . . ?
C00E O003 C00P 117.07(11) . . ?
C00E N004 C00C 113.10(12) . . ?
C00C N005 C00B 112.71(12) . . ?
C008 N006 C00N 126.58(12) . . ?
C00A N006 C008 108.36(11) . . ?
C00A N006 C00N 124.86(12) . . ?
C00B N007 C00E 112.48(12) . . ?
N006 C008 C009 109.27(11) . . ?
N006 C008 C00I 129.10(12) . . ?
C00I C008 C009 121.63(12) . . ?
C008 C009 C00G 106.58(11) . . ?
C00D C009 C008 119.68(12) . . ?
C00D C009 C00G 133.72(12) . . ?
N006 C00A C00F 129.44(13) . . ?
N006 C00A C00G 109.31(11) . . ?
C00F C00A C00G 121.24(12) . . ?
O002 C00B N005 112.76(12) . . ?
N007 C00B O002 119.74(12) . . ?
N007 C00B N005 127.50(12) . . ?
O001 C00C N004 119.42(12) . . ?
N005 C00C O001 113.53(11) . . ?
N005 C00C N004 127.04(12) . . ?
C009 C00D H00D 120.4 . . ?
C00K C00D C009 119.12(13) . . ?
C00K C00D H00D 120.4 . . ?
O003 C00E N007 113.58(12) . . ?
N004 C00E O003 119.30(12) . . ?
N004 C00E N007 127.11(12) . . ?
C00A C00F H00F 121.2 . . ?
C00O C00F C00A 117.63(13) . . ?
C00O C00F H00F 121.2 . . ?
C00A C00G C009 106.47(11) . . ?
C00M C00G C009 133.48(13) . . ?
C00M C00G C00A 120.04(12) . . ?
H00A C00H H00B 108.1 . . ?
C00J C00H H00A 109.6 . . ?
C00J C00H H00B 109.6 . . ?
C00J C00H C00N 110.49(11) . . ?
C00N C00H H00A 109.6 . . ?
C00N C00H H00B 109.6 . . ?
C008 C00I H00I 121.4 . . ?
C00L C00I C008 117.24(13) . . ?
C00L C00I H00I 121.4 . . ?
O001 C00J C00H 111.35(11) . . ?
O001 C00J H00C 109.4 . . ?
O001 C00J H00E 109.4 . . ?
C00H C00J H00C 109.4 . . ?
C00H C00J H00E 109.4 . . ?
H00C C00J H00E 108.0 . . ?
C00D C00K H00K 119.8 . . ?
C00D C00K C00L 120.39(13) . . ?
C00L C00K H00K 119.8 . . ?
C00I C00L C00K 121.90(13) . . ?
C00I C00L H00L 119.0 . . ?
C00K C00L H00L 119.0 . . ?
C00G C00M H00M 120.7 . . ?
C00Q C00M C00G 118.57(13) . . ?
C00Q C00M H00M 120.7 . . ?
N006 C00N C00H 112.28(11) . . ?
N006 C00N H00G 109.1 . . ?
N006 C00N H00H 109.1 . . ?
C00H C00N H00G 109.1 . . ?
C00H C00N H00H 109.1 . . ?
H00G C00N H00H 107.9 . . ?
C00F C00O H00O 119.1 . . ?
C00F C00O C00Q 121.70(13) . . ?
C00Q C00O H00O 119.1 . . ?
O003 C00P H00J 109.5 . . ?
O003 C00P H00N 109.5 . . ?
O003 C00P H00P 109.5 . . ?
H00J C00P H00N 109.5 . . ?
H00J C00P H00P 109.5 . . ?
H00N C00P H00P 109.5 . . ?
C00M C00Q C00O 120.77(13) . . ?
C00M C00Q H00Q 119.6 . . ?
C00O C00Q H00Q 119.6 . . ?
O002 C00R H00R 109.5 . . ?
O002 C00R H00S 109.5 . . ?
O002 C00R H00T 109.5 . . ?
H00R C00R H00S 109.5 . . ?
H00R C00R H00T 109.5 . . ?
H00S C00R H00T 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
