# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_exp_5701
_database_code_depnum_ccdc_archive 'CCDC 1880922'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           80
_space_group_name_H-M_alt        'I 41'
_space_group_name_Hall           'I 4bw'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'

_cell_length_a                   27.330(4)
_cell_length_b                   27.330(4)
_cell_length_c                   5.9874(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4472.3(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    978
_cell_measurement_theta_min      4.3000
_cell_measurement_theta_max      19.5420

_exptl_crystal_description       strip
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9595
_diffrn_reflns_av_unetI/netI     0.1542
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.483
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3875
_reflns_number_gt                2201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.970

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0182P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 553 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3875
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 -1.21596(16) -0.79541(15) -1.8930(8) 0.0408(12) Uani 1 1 d . . . . .
H001 H -1.2082 -0.7690 -1.8383 0.061 Uiso 1 1 calc R U . . .
O002 O -1.22100(15) -1.20166(15) -1.3856(8) 0.0402(12) Uani 1 1 d . . . . .
H002 H -1.2086 -1.2240 -1.3137 0.060 Uiso 1 1 calc R U . . .
N003 N -1.19339(19) -1.09934(17) -1.3758(8) 0.0324(13) Uani 1 1 d . . . . .
N004 N -1.17858(19) -0.89383(17) -1.8878(8) 0.0320(13) Uani 1 1 d . . . . .
C005 C -1.2158(3) -1.0592(2) -1.0599(10) 0.0295(16) Uani 1 1 d . . . . .
C006 C -1.2325(2) -1.0854(2) -1.2455(10) 0.0296(17) Uani 1 1 d . . . . .
C007 C -1.1631(2) -1.0584(2) -1.0757(10) 0.0290(16) Uani 1 1 d . . . . .
C008 C -1.2491(3) -1.0407(2) -0.9088(11) 0.0366(17) Uani 1 1 d . . . . .
H008 H -1.2383 -1.0234 -0.7842 0.044 Uiso 1 1 calc R U . . .
C009 C -1.1835(2) -0.8649(2) -2.0883(9) 0.0310(16) Uani 1 1 d . . . . .
H00A H -1.2150 -0.8717 -2.1556 0.037 Uiso 1 1 calc R U . . .
H00B H -1.1584 -0.8748 -2.1938 0.037 Uiso 1 1 calc R U . . .
C00A C -1.1514(3) -1.0837(2) -1.2723(10) 0.0323(17) Uani 1 1 d . . . . .
C00B C -1.2162(3) -0.9117(2) -1.7550(10) 0.0319(18) Uani 1 1 d . . . . .
C00C C -1.1945(2) -1.1284(2) -1.5774(9) 0.0353(17) Uani 1 1 d . . . . .
H00E H -1.1698 -1.1162 -1.6795 0.042 Uiso 1 1 calc R U . . .
H00F H -1.2261 -1.1244 -1.6485 0.042 Uiso 1 1 calc R U . . .
C00D C -1.1960(3) -0.9361(2) -1.5719(11) 0.0355(18) Uani 1 1 d . . . . .
C00E C -1.1266(3) -1.0384(2) -0.9444(11) 0.0382(19) Uani 1 1 d . . . . .
H00G H -1.1344 -1.0214 -0.8148 0.046 Uiso 1 1 calc R U . . .
C00F C -1.1855(2) -1.1821(2) -1.5378(11) 0.0387(19) Uani 1 1 d . . . . .
H00H H -1.1874 -1.1995 -1.6787 0.046 Uiso 1 1 calc R U . . .
H00J H -1.1530 -1.1867 -1.4770 0.046 Uiso 1 1 calc R U . . .
C00G C -1.3148(2) -1.0743(2) -1.1286(11) 0.0405(18) Uani 1 1 d . . . . .
H00K H -1.3482 -1.0790 -1.1500 0.049 Uiso 1 1 calc R U . . .
C00H C -1.1441(3) -0.9327(2) -1.5947(11) 0.0353(18) Uani 1 1 d . . . . .
C00I C -1.2660(3) -0.9087(2) -1.7844(10) 0.0383(18) Uani 1 1 d . . . . .
H00I H -1.2790 -0.8923 -1.9070 0.046 Uiso 1 1 calc R U . . .
C00J C -1.1342(3) -0.9067(2) -1.7901(11) 0.0354(18) Uani 1 1 d . . . . .
C00K C -1.1792(2) -0.8107(2) -2.0470(10) 0.0341(18) Uani 1 1 d . . . . .
H00C H -1.1470 -0.8033 -1.9870 0.041 Uiso 1 1 calc R U . . .
H00D H -1.1829 -0.7931 -2.1867 0.041 Uiso 1 1 calc R U . . .
C00L C -1.2964(3) -0.9304(2) -1.6301(12) 0.045(2) Uani 1 1 d . . . . .
H00L H -1.3302 -0.9286 -1.6480 0.054 Uiso 1 1 calc R U . . .
C00M C -1.2818(3) -1.0933(2) -1.2791(10) 0.0391(19) Uani 1 1 d . . . . .
H00M H -1.2927 -1.1112 -1.4016 0.047 Uiso 1 1 calc R U . . .
C00N C -1.0785(3) -1.0441(2) -1.0083(11) 0.044(2) Uani 1 1 d . . . . .
H00N H -1.0538 -1.0306 -0.9213 0.052 Uiso 1 1 calc R U . . .
C00O C -1.1027(3) -1.0895(2) -1.3380(11) 0.0392(18) Uani 1 1 d . . . . .
H00O H -1.0947 -1.1060 -1.4687 0.047 Uiso 1 1 calc R U . . .
C00P C -1.2981(3) -1.0479(2) -0.9435(11) 0.0382(18) Uani 1 1 d . . . . .
H00P H -1.3206 -1.0350 -0.8428 0.046 Uiso 1 1 calc R U . . .
C00Q C -1.2271(3) -0.9575(2) -1.4161(11) 0.047(2) Uani 1 1 d . . . . .
H00Q H -1.2144 -0.9733 -1.2915 0.056 Uiso 1 1 calc R U . . .
C00R C -1.2768(3) -0.9548(3) -1.4480(12) 0.051(2) Uani 1 1 d . . . . .
H00R H -1.2977 -0.9697 -1.3457 0.061 Uiso 1 1 calc R U . . .
C00S C -1.0667(2) -1.0697(2) -1.2014(12) 0.0439(19) Uani 1 1 d . . . . .
H00S H -1.0340 -1.0737 -1.2400 0.053 Uiso 1 1 calc R U . . .
C00T C -1.0873(3) -0.8975(2) -1.8630(12) 0.0467(19) Uani 1 1 d . . . . .
H00T H -1.0814 -0.8798 -1.9927 0.056 Uiso 1 1 calc R U . . .
C00U C -1.1053(3) -0.9508(3) -1.4701(12) 0.056(2) Uani 1 1 d . . . . .
H00U H -1.1110 -0.9683 -1.3395 0.068 Uiso 1 1 calc R U . . .
C00V C -1.0582(3) -0.9426(3) -1.5418(14) 0.065(3) Uani 1 1 d . . . . .
H00V H -1.0320 -0.9550 -1.4602 0.078 Uiso 1 1 calc R U . . .
C00W C -1.0494(3) -0.9158(3) -1.7361(15) 0.062(3) Uani 1 1 d . . . . .
H00W H -1.0173 -0.9101 -1.7807 0.074 Uiso 1 1 calc R U . . .


_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 C00K 1.427(7) . ?
O002 C00F 1.434(7) . ?
N003 C00A 1.373(8) . ?
N003 C006 1.376(7) . ?
N003 C00C 1.445(7) . ?
N004 C00B 1.388(8) . ?
N004 C00J 1.391(8) . ?
N004 C009 1.443(7) . ?
C005 C008 1.380(8) . ?
C005 C006 1.398(8) . ?
C005 C007 1.443(8) . ?
C006 C00M 1.382(8) . ?
C007 C00E 1.381(8) . ?
C007 C00A 1.401(8) . ?
C008 C00P 1.371(8) . ?
C009 C00K 1.508(7) . ?
C00A C00O 1.396(8) . ?
C00B C00I 1.376(8) . ?
C00B C00D 1.397(8) . ?
C00C C00F 1.506(8) . ?
C00D C00Q 1.391(9) . ?
C00D C00H 1.427(8) . ?
C00E C00N 1.377(9) . ?
C00G C00M 1.376(8) . ?
C00G C00P 1.398(8) . ?
C00H C00U 1.389(9) . ?
C00H C00J 1.396(8) . ?
C00I C00L 1.376(8) . ?
C00J C00T 1.378(8) . ?
C00L C00R 1.386(10) . ?
C00N C00S 1.390(9) . ?
C00O C00S 1.389(8) . ?
C00Q C00R 1.373(10) . ?
C00T C00W 1.378(9) . ?
C00U C00V 1.375(10) . ?
C00V C00W 1.396(11) . ?

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
C00A N003 C006 107.8(5) . . ?
C00A N003 C00C 124.4(5) . . ?
C006 N003 C00C 127.6(5) . . ?
C00B N004 C00J 108.4(5) . . ?
C00B N004 C009 126.9(5) . . ?
C00J N004 C009 124.7(6) . . ?
C008 C005 C006 119.6(7) . . ?
C008 C005 C007 134.1(6) . . ?
C006 C005 C007 106.4(6) . . ?
N003 C006 C00M 129.2(6) . . ?
N003 C006 C005 109.8(6) . . ?
C00M C006 C005 121.0(6) . . ?
C00E C007 C00A 120.6(7) . . ?
C00E C007 C005 133.5(6) . . ?
C00A C007 C005 105.9(6) . . ?
C00P C008 C005 119.5(7) . . ?
N004 C009 C00K 113.2(5) . . ?
N003 C00A C00O 129.3(6) . . ?
N003 C00A C007 110.0(6) . . ?
C00O C00A C007 120.6(7) . . ?
C00I C00B N004 129.7(6) . . ?
C00I C00B C00D 121.3(7) . . ?
N004 C00B C00D 109.0(6) . . ?
N003 C00C C00F 113.6(5) . . ?
C00Q C00D C00B 119.0(7) . . ?
C00Q C00D C00H 134.4(7) . . ?
C00B C00D C00H 106.6(6) . . ?
C00N C00E C007 119.0(6) . . ?
O002 C00F C00C 110.8(5) . . ?
C00M C00G C00P 120.1(7) . . ?
C00U C00H C00J 118.9(7) . . ?
C00U C00H C00D 133.2(7) . . ?
C00J C00H C00D 107.8(6) . . ?
C00B C00I C00L 119.1(7) . . ?
C00T C00J N004 129.2(6) . . ?
C00T C00J C00H 122.6(7) . . ?
N004 C00J C00H 108.2(6) . . ?
O001 C00K C009 109.8(5) . . ?
C00I C00L C00R 120.1(7) . . ?
C00G C00M C006 119.0(6) . . ?
C00E C00N C00S 120.7(7) . . ?
C00S C00O C00A 117.7(6) . . ?
C008 C00P C00G 120.8(7) . . ?
C00R C00Q C00D 119.3(7) . . ?
C00Q C00R C00L 121.2(7) . . ?
C00O C00S C00N 121.4(7) . . ?
C00W C00T C00J 117.4(7) . . ?
C00V C00U C00H 119.3(8) . . ?
C00U C00V C00W 120.6(8) . . ?
C00T C00W C00V 121.3(8) . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_linzhh-1103
_database_code_depnum_ccdc_archive 'CCDC 1880923'
_audit_update_record             
;
2018-11-23 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C14 H13 N O)'
_chemical_formula_sum            'C56 H52 N4 O4'
_chemical_formula_weight         845.01
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           80
_space_group_name_H-M_alt        'I 41'
_space_group_name_Hall           'I 4bw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'

_cell_length_a                   27.4577(12)
_cell_length_b                   27.4577(12)
_cell_length_c                   5.9843(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4511.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2596
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.2120
_cell_measurement_theta_min      3.4800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       strip
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7636
_diffrn_reflns_point_group_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.318
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5148
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  64.00   1.00  125.24    --   10.21  57.00  90.00   82
  2  ω     10.00  71.00   1.00  125.24    --   10.21  77.00 -60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0017312000
_diffrn_orient_matrix_UB_12      0.0247278000
_diffrn_orient_matrix_UB_13      0.0328091000
_diffrn_orient_matrix_UB_21      0.0250220000
_diffrn_orient_matrix_UB_22      0.0033692000
_diffrn_orient_matrix_UB_23      -0.0252273000
_diffrn_orient_matrix_UB_31      -0.0062201000
_diffrn_orient_matrix_UB_32      0.0065791000
_diffrn_orient_matrix_UB_33      -0.1110605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_full    0.599
_reflns_Friedel_fraction_max     0.599
_reflns_number_gt                2701
_reflns_number_total             3244
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         -0.234
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.066
_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)+(0.0451P)²+0.2296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1100
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00F,H00G), C00I(H00A,H00B), C00J(H00C,H00D), C00N(H00N,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00D(H00H), C00E(H00E), C00G(H00I), C00H(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_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 0.78532(9) 0.29477(9) 0.8889(4) 0.0277(6) Uani 1 1 d . . . . .
H001 H 0.7586 0.2927 0.9497 0.042 Uiso 1 1 calc GR . . . .
O002 O 0.77934(9) 0.70130(8) 0.3811(5) 0.0279(7) Uani 1 1 d . . . . .
H002 H 0.7887 0.7279 0.3359 0.042 Uiso 1 1 calc GR . . . .
N003 N 0.80593(10) 0.59880(10) 0.3785(5) 0.0227(7) Uani 1 1 d . . . . .
N004 N 0.82188(10) 0.39398(10) 0.8927(5) 0.0234(7) Uani 1 1 d . . . . .
C005 C 0.76615(13) 0.58522(12) 0.2476(6) 0.0214(8) Uani 1 1 d . . . . .
C006 C 0.74944(13) 0.54038(12) -0.0941(7) 0.0241(9) Uani 1 1 d . . . . .
H006 H 0.7601 0.5230 -0.2180 0.029 Uiso 1 1 calc R . . . .
C007 C 0.83581(13) 0.55767(12) 0.0757(6) 0.0212(8) Uani 1 1 d . . . . .
C008 C 0.78299(13) 0.55906(12) 0.0584(6) 0.0204(8) Uani 1 1 d . . . . .
C009 C 0.78410(13) 0.41169(12) 0.7586(6) 0.0235(9) Uani 1 1 d . . . . .
C00A C 0.80432(13) 0.62850(13) 0.5807(6) 0.0240(9) Uani 1 1 d . . . . .
H00F H 0.8284 0.6164 0.6856 0.029 Uiso 1 1 calc R . . . .
H00G H 0.7725 0.6251 0.6496 0.029 Uiso 1 1 calc R . . . .
C00B C 0.84824(13) 0.58284(12) 0.2740(6) 0.0216(9) Uani 1 1 d . . . . .
C00C C 0.80421(14) 0.43618(12) 0.5720(7) 0.0256(9) Uani 1 1 d . . . . .
C00D C 0.89692(13) 0.58869(13) 0.3397(7) 0.0264(9) Uani 1 1 d . . . . .
H00H H 0.9051 0.6053 0.4699 0.032 Uiso 1 1 calc R . . . .
C00E C 0.73367(13) 0.40876(13) 0.7881(7) 0.0264(9) Uani 1 1 d . . . . .
H00E H 0.7205 0.3924 0.9101 0.032 Uiso 1 1 calc R . . . .
C00F C 0.86598(13) 0.40641(12) 0.7931(7) 0.0241(9) Uani 1 1 d . . . . .
C00G C 0.68386(13) 0.57437(13) 0.1268(7) 0.0287(9) Uani 1 1 d . . . . .
H00I H 0.6506 0.5792 0.1470 0.034 Uiso 1 1 calc R . . . .
C00H C 0.87257(13) 0.53763(12) -0.0584(7) 0.0268(9) Uani 1 1 d . . . . .
H00J H 0.8649 0.5208 -0.1886 0.032 Uiso 1 1 calc R . . . .
C00I C 0.82081(13) 0.31043(13) 1.0484(7) 0.0246(9) Uani 1 1 d . . . . .
H00A H 0.8532 0.3032 0.9923 0.029 Uiso 1 1 calc R . . . .
H00B H 0.8163 0.2926 1.1868 0.029 Uiso 1 1 calc R . . . .
C00J C 0.81671(13) 0.36457(13) 1.0941(6) 0.0244(9) Uani 1 1 d . . . . .
H00C H 0.7853 0.3712 1.1615 0.029 Uiso 1 1 calc R . . . .
H00D H 0.8417 0.3739 1.2004 0.029 Uiso 1 1 calc R . . . .
C00K C 0.70026(14) 0.54791(12) -0.0601(7) 0.0263(9) Uani 1 1 d . . . . .
H00K H 0.6778 0.5354 -0.1615 0.032 Uiso 1 1 calc R . . . .
C00L C 0.92056(14) 0.54342(13) 0.0070(7) 0.0289(10) Uani 1 1 d . . . . .
H00L H 0.9453 0.5303 -0.0804 0.035 Uiso 1 1 calc R . . . .
C00M C 0.71641(13) 0.59333(13) 0.2817(7) 0.0263(9) Uani 1 1 d . . . . .
H00M H 0.7054 0.6109 0.4046 0.032 Uiso 1 1 calc R . . . .
C00N C 0.81397(13) 0.68216(13) 0.5363(7) 0.0261(9) Uani 1 1 d . . . . .
H00N H 0.8120 0.7002 0.6755 0.031 Uiso 1 1 calc R . . . .
H00O H 0.8466 0.6861 0.4766 0.031 Uiso 1 1 calc R . . . .
C00O C 0.85683(14) 0.43257(13) 0.5947(7) 0.0268(9) Uani 1 1 d . . . . .
C00P C 0.93247(13) 0.56868(13) 0.2026(7) 0.0297(10) Uani 1 1 d . . . . .
H00P H 0.9651 0.5722 0.2417 0.036 Uiso 1 1 calc R . . . .
C00Q C 0.77349(16) 0.45756(12) 0.4154(7) 0.0309(10) Uani 1 1 d . . . . .
H00Q H 0.7865 0.4735 0.2918 0.037 Uiso 1 1 calc R . . . .
C00R C 0.72322(16) 0.45498(13) 0.4443(7) 0.0322(10) Uani 1 1 d . . . . .
H00R H 0.7025 0.4692 0.3403 0.039 Uiso 1 1 calc R . . . .
C00S C 0.70393(15) 0.43074(13) 0.6314(7) 0.0315(10) Uani 1 1 d . . . . .
H00S H 0.6703 0.4295 0.6502 0.038 Uiso 1 1 calc R . . . .
C00T C 0.91352(13) 0.39714(13) 0.8677(7) 0.0302(10) Uani 1 1 d . . . . .
H00T H 0.9193 0.3794 0.9974 0.036 Uiso 1 1 calc R . . . .
C00U C 0.94311(16) 0.44243(15) 0.5455(8) 0.0443(13) Uani 1 1 d . . . . .
H00U H 0.9694 0.4547 0.4657 0.053 Uiso 1 1 calc R . . . .
C00V C 0.95138(15) 0.41541(15) 0.7414(9) 0.0419(12) Uani 1 1 d . . . . .
H00V H 0.9832 0.4097 0.7871 0.050 Uiso 1 1 calc R . . . .
C00W C 0.89635(16) 0.45090(14) 0.4704(8) 0.0379(11) Uani 1 1 d . . . . .
H00W H 0.8910 0.4684 0.3398 0.046 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H001 0.8200 . ?
O001 C00I 1.430(4) . ?
O002 H002 0.8200 . ?
O002 C00N 1.429(5) . ?
N003 C005 1.395(4) . ?
N003 C00A 1.460(5) . ?
N003 C00B 1.390(5) . ?
N004 C009 1.399(5) . ?
N004 C00F 1.392(5) . ?
N004 C00J 1.457(5) . ?
C005 C008 1.418(5) . ?
C005 C00M 1.399(5) . ?
C006 H006 0.9300 . ?
C006 C008 1.395(5) . ?
C006 C00K 1.381(5) . ?
C007 C008 1.455(5) . ?
C007 C00B 1.415(5) . ?
C007 C00H 1.402(5) . ?
C009 C00C 1.416(5) . ?
C009 C00E 1.398(5) . ?
C00A H00F 0.9700 . ?
C00A H00G 0.9700 . ?
C00A C00N 1.520(5) . ?
C00B C00D 1.402(5) . ?
C00C C00O 1.455(5) . ?
C00C C00Q 1.391(6) . ?
C00D H00H 0.9300 . ?
C00D C00P 1.389(5) . ?
C00E H00E 0.9300 . ?
C00E C00S 1.382(5) . ?
C00F C00O 1.410(5) . ?
C00F C00T 1.403(5) . ?
C00G H00I 0.9300 . ?
C00G C00K 1.408(6) . ?
C00G C00M 1.389(5) . ?
C00H H00J 0.9300 . ?
C00H C00L 1.384(5) . ?
C00I H00A 0.9700 . ?
C00I H00B 0.9700 . ?
C00I C00J 1.516(5) . ?
C00J H00C 0.9700 . ?
C00J H00D 0.9700 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00P 1.399(6) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9700 . ?
C00N H00O 0.9700 . ?
C00O C00W 1.409(5) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.393(6) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.406(6) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00T C00V 1.380(6) . ?
C00U H00U 0.9300 . ?
C00U C00V 1.406(7) . ?
C00U C00W 1.380(6) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I O001 H001 109.5 . . ?
C00N O002 H002 109.5 . . ?
C005 N003 C00A 126.2(3) . . ?
C00B N003 C005 108.5(3) . . ?
C00B N003 C00A 125.0(3) . . ?
C009 N004 C00J 126.5(3) . . ?
C00F N004 C009 108.3(3) . . ?
C00F N004 C00J 125.1(3) . . ?
N003 C005 C008 109.2(3) . . ?
N003 C005 C00M 129.8(3) . . ?
C00M C005 C008 121.0(3) . . ?
C008 C006 H006 120.2 . . ?
C00K C006 H006 120.2 . . ?
C00K C006 C008 119.6(4) . . ?
C00B C007 C008 106.7(3) . . ?
C00H C007 C008 133.4(4) . . ?
C00H C007 C00B 119.9(3) . . ?
C005 C008 C007 106.4(3) . . ?
C006 C008 C005 119.6(3) . . ?
C006 C008 C007 134.1(4) . . ?
N004 C009 C00C 109.2(3) . . ?
C00E C009 N004 129.9(4) . . ?
C00E C009 C00C 120.9(4) . . ?
N003 C00A H00F 109.0 . . ?
N003 C00A H00G 109.0 . . ?
N003 C00A C00N 113.0(3) . . ?
H00F C00A H00G 107.8 . . ?
C00N C00A H00F 109.0 . . ?
C00N C00A H00G 109.0 . . ?
N003 C00B C007 109.2(3) . . ?
N003 C00B C00D 129.4(3) . . ?
C00D C00B C007 121.4(3) . . ?
C009 C00C C00O 106.3(3) . . ?
C00Q C00C C009 119.7(4) . . ?
C00Q C00C C00O 134.0(4) . . ?
C00B C00D H00H 121.3 . . ?
C00P C00D C00B 117.3(4) . . ?
C00P C00D H00H 121.3 . . ?
C009 C00E H00E 120.8 . . ?
C00S C00E C009 118.3(4) . . ?
C00S C00E H00E 120.8 . . ?
N004 C00F C00O 109.3(3) . . ?
N004 C00F C00T 128.9(4) . . ?
C00T C00F C00O 121.8(4) . . ?
C00K C00G H00I 119.4 . . ?
C00M C00G H00I 119.4 . . ?
C00M C00G C00K 121.2(3) . . ?
C007 C00H H00J 120.7 . . ?
C00L C00H C007 118.6(4) . . ?
C00L C00H H00J 120.7 . . ?
O001 C00I H00A 109.4 . . ?
O001 C00I H00B 109.4 . . ?
O001 C00I C00J 111.4(3) . . ?
H00A C00I H00B 108.0 . . ?
C00J C00I H00A 109.4 . . ?
C00J C00I H00B 109.4 . . ?
N004 C00J C00I 112.8(3) . . ?
N004 C00J H00C 109.0 . . ?
N004 C00J H00D 109.0 . . ?
C00I C00J H00C 109.0 . . ?
C00I C00J H00D 109.0 . . ?
H00C C00J H00D 107.8 . . ?
C006 C00K C00G 120.5(4) . . ?
C006 C00K H00K 119.8 . . ?
C00G C00K H00K 119.8 . . ?
C00H C00L H00L 119.5 . . ?
C00H C00L C00P 121.1(4) . . ?
C00P C00L H00L 119.5 . . ?
C005 C00M H00M 120.9 . . ?
C00G C00M C005 118.1(4) . . ?
C00G C00M H00M 120.9 . . ?
O002 C00N C00A 110.7(3) . . ?
O002 C00N H00N 109.5 . . ?
O002 C00N H00O 109.5 . . ?
C00A C00N H00N 109.5 . . ?
C00A C00N H00O 109.5 . . ?
H00N C00N H00O 108.1 . . ?
C00F C00O C00C 106.9(3) . . ?
C00W C00O C00C 133.7(4) . . ?
C00W C00O C00F 119.3(4) . . ?
C00D C00P C00L 121.8(4) . . ?
C00D C00P H00P 119.1 . . ?
C00L C00P H00P 119.1 . . ?
C00C C00Q H00Q 120.1 . . ?
C00C C00Q C00R 119.7(4) . . ?
C00R C00Q H00Q 120.1 . . ?
C00Q C00R H00R 120.1 . . ?
C00Q C00R C00S 119.8(4) . . ?
C00S C00R H00R 120.1 . . ?
C00E C00S C00R 121.6(4) . . ?
C00E C00S H00S 119.2 . . ?
C00R C00S H00S 119.2 . . ?
C00F C00T H00T 121.3 . . ?
C00V C00T C00F 117.4(4) . . ?
C00V C00T H00T 121.3 . . ?
C00V C00U H00U 119.6 . . ?
C00W C00U H00U 119.6 . . ?
C00W C00U C00V 120.7(4) . . ?
C00T C00V C00U 121.8(4) . . ?
C00T C00V H00V 119.1 . . ?
C00U C00V H00V 119.1 . . ?
C00O C00W H00W 120.5 . . ?
C00U C00W C00O 119.0(4) . . ?
C00U C00W H00W 120.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.785
