# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_shelx
_audit_block_doi                 10.5517/ccyb019
_database_code_depnum_ccdc_archive 'CCDC 873550'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5RA09036A 2015
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2,4-dinitrophenol-1-methylpiperidine (1:1)
;
_chemical_name_common            MP(DNP)
_chemical_melting_point          416.2
_chemical_formula_moiety         'C6 H3 N2 O5,C6 H14 N'
_chemical_formula_sum            'C12 H17 N3 O5'
_chemical_formula_weight         283.29

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5357(6)
_cell_length_b                   17.1542(11)
_cell_length_c                   10.8286(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.802(9)
_cell_angle_gamma                90
_cell_volume                     1365.00(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1204
_cell_measurement_theta_min      0.974
_cell_measurement_theta_max      0.979

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            6011
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         29.112
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3110
_reflns_number_gt                1917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    Wingx
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_refine_special_details          'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.2939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3110
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_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
O16 O 0.2670(2) 0.51460(8) 0.20443(14) 0.0595(5) Uani 1 1 d . . . . .
C11 C 0.2669(3) 0.39144(12) 0.52846(19) 0.0456(5) Uani 1 1 d . . . . .
C8 C 0.2734(3) 0.47937(11) 0.30735(19) 0.0408(5) Uani 1 1 d . . . . .
C9 C 0.2554(3) 0.51391(10) 0.42502(19) 0.0405(5) Uani 1 1 d . . . . .
C13 C 0.2936(3) 0.39618(11) 0.3139(2) 0.0460(5) Uani 1 1 d . . . . .
H13 H 0.3094 0.3699 0.2420 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2911(3) 0.35414(11) 0.4186(2) 0.0474(5) Uani 1 1 d . . . . .
H12 H 0.3054 0.3003 0.4178 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2495(3) 0.47067(12) 0.5312(2) 0.0465(5) Uani 1 1 d . . . . .
H10 H 0.2337 0.4953 0.6045 0.056 Uiso 1 1 calc R U . . .
O17 O 0.2966(3) 0.63959(9) 0.36103(19) 0.0864(6) Uani 1 1 d . . . . .
N15 N 0.2606(3) 0.34693(14) 0.6395(2) 0.0678(6) Uani 1 1 d . . . . .
N14 N 0.2426(3) 0.59723(11) 0.4366(2) 0.0577(5) Uani 1 1 d . . . . .
O20 O 0.2802(3) 0.27643(12) 0.63755(19) 0.0980(7) Uani 1 1 d . . . . .
O19 O 0.2347(3) 0.38140(13) 0.73345(18) 0.0985(7) Uani 1 1 d . . . . .
O18 O 0.1852(3) 0.62353(10) 0.5250(2) 0.0990(7) Uani 1 1 d . . . . .
N1 N 0.1839(2) 0.64838(10) 0.07121(18) 0.0494(5) Uani 1 1 d . . . . .
C2 C 0.3581(3) 0.68366(12) 0.0544(2) 0.0554(6) Uani 1 1 d . . . . .
H2A H 0.4293 0.7005 0.1359 0.066 Uiso 1 1 calc R U . . .
H2B H 0.3320 0.7291 0.0000 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4667(3) 0.62539(14) -0.0037(3) 0.0609(6) Uani 1 1 d . . . . .
H3A H 0.5757 0.6505 -0.0181 0.073 Uiso 1 1 calc R U . . .
H3B H 0.5042 0.5829 0.0554 0.073 Uiso 1 1 calc R U . . .
C5 C 0.1858(4) 0.55772(16) -0.1071(3) 0.0691(7) Uani 1 1 d . . . . .
H5A H 0.1136 0.5396 -0.1875 0.083 Uiso 1 1 calc R U . . .
H5B H 0.2140 0.5130 -0.0512 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3595(4) 0.59281(16) -0.1274(2) 0.0671(7) Uani 1 1 d . . . . .
H4A H 0.3323 0.6341 -0.1900 0.081 Uiso 1 1 calc R U . . .
H4B H 0.4307 0.5533 -0.1586 0.081 Uiso 1 1 calc R U . . .
C6 C 0.0768(3) 0.61536(15) -0.0504(2) 0.0614(6) Uani 1 1 d . . . . .
H6A H 0.0379 0.6574 -0.1101 0.074 Uiso 1 1 calc R U . . .
H6B H -0.0313 0.5899 -0.0350 0.074 Uiso 1 1 calc R U . . .
C7 C 0.0726(4) 0.70616(15) 0.1226(3) 0.0724(8) Uani 1 1 d . . . . .
H7A H -0.0384 0.6821 0.1325 0.109 Uiso 1 1 calc R U . . .
H7B H 0.1395 0.7244 0.2033 0.109 Uiso 1 1 calc R U . . .
H7C H 0.0447 0.7493 0.0651 0.109 Uiso 1 1 calc R U . . .
H1 H 0.212(3) 0.6088(14) 0.128(2) 0.062(7) Uiso 1 1 d . . . . .


_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
O16 C8 1.259(2) . ?
C11 C10 1.366(3) . ?
C11 C12 1.398(3) . ?
C11 N15 1.434(3) . ?
C8 C13 1.435(3) . ?
C8 C9 1.439(3) . ?
C9 C10 1.377(3) . ?
C9 N14 1.440(3) . ?
C13 C12 1.347(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
O17 N14 1.229(2) . ?
N15 O20 1.219(3) . ?
N15 O19 1.229(3) . ?
N14 O18 1.221(2) . ?
N1 C7 1.484(3) . ?
N1 C2 1.493(3) . ?
N1 C6 1.495(3) . ?
N1 H1 0.91(2) . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.510(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.501(3) . ?
C5 C4 1.501(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C10 C11 C12 120.32(19) . . ?
C10 C11 N15 119.4(2) . . ?
C12 C11 N15 120.31(19) . . ?
O16 C8 C13 120.25(18) . . ?
O16 C8 C9 126.41(17) . . ?
C13 C8 C9 113.30(17) . . ?
C10 C9 C8 122.98(17) . . ?
C10 C9 N14 116.54(19) . . ?
C8 C9 N14 120.48(18) . . ?
C12 C13 C8 123.55(19) . . ?
C12 C13 H13 118.2 . . ?
C8 C13 H13 118.2 . . ?
C13 C12 C11 119.99(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C10 C9 119.78(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
O20 N15 O19 122.3(2) . . ?
O20 N15 C11 119.1(2) . . ?
O19 N15 C11 118.6(2) . . ?
O18 N14 O17 122.0(2) . . ?
O18 N14 C9 118.5(2) . . ?
O17 N14 C9 119.37(19) . . ?
C7 N1 C2 111.12(18) . . ?
C7 N1 C6 110.08(19) . . ?
C2 N1 C6 111.34(17) . . ?
C7 N1 H1 108.1(14) . . ?
C2 N1 H1 107.8(14) . . ?
C6 N1 H1 108.3(15) . . ?
N1 C2 C3 110.72(17) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 112.4(2) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C6 C5 C4 111.7(2) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C5 C4 C3 109.30(19) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C6 C5 111.9(2) . . ?
N1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A O19 0.96 2.54 3.413(3) 151.9 3_566
C7 H7B O17 0.96 2.35 2.982(3) 122.5 .
C7 H7C O18 0.96 2.50 3.282(3) 138.1 4_575
N1 H1 O16 0.91(2) 1.82(2) 2.709(2) 165(2) .
N1 H1 O17 0.91(2) 2.52(2) 3.068(3) 119.5(17) .
C7 H7A O19 0.96 2.54 3.413(3) 151.9 3_566
C7 H7B O17 0.96 2.35 2.982(3) 122.5 .
C7 H7C O18 0.96 2.50 3.282(3) 138.1 4_575
N1 H1 O16 0.91(2) 1.82(2) 2.709(2) 165(2) .
N1 H1 O17 0.91(2) 2.52(2) 3.068(3) 119.5(17) .

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/cc10gy1g
_database_code_depnum_ccdc_archive 'CCDC 937875'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5RA09036A 2015
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(naphthalen-1-ylmethylene)malononitrile
_chemical_name_common            2-(naphthalen-1-ylmethylene)malononitrile
_chemical_melting_point          439.5K
_chemical_formula_moiety         C14H8N2
_chemical_formula_sum            'C14 H8 N2'
_chemical_formula_weight         204.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8269(4)
_cell_length_b                   15.7916(15)
_cell_length_c                   17.2303(16)
_cell_angle_alpha                90.000
_cell_angle_beta                 91.290
_cell_angle_gamma                90.000
_cell_volume                     1041.02(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    940
_cell_measurement_theta_min      0.96559
_cell_measurement_theta_max      1.0000

_exptl_crystal_description       rectangualr
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.32
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_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  0.972
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            4249
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.501
_diffrn_reflns_theta_max         29.002
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2767
_reflns_number_gt                1558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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)+(0.0486P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2372
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003

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
C9 C 0.4938(3) 0.08696(9) 0.23109(9) 0.0354(4) Uani 1 1 d . . . . .
C1 C 0.3709(4) 0.13975(9) 0.29248(8) 0.0358(4) Uani 1 1 d . . . . .
N16 N 0.6779(4) 0.28231(10) 0.45655(9) 0.0667(5) Uani 1 1 d . . . . .
C8 C 0.5678(4) -0.00005(10) 0.24022(10) 0.0439(4) Uani 1 1 d . . . . .
H8 H 0.5375 -0.0257 0.2882 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2984(4) 0.10329(10) 0.36780(9) 0.0407(4) Uani 1 1 d . . . . .
C4 C 0.4886(4) 0.21186(10) 0.14740(10) 0.0490(4) Uani 1 1 d . . . . .
H4 H 0.5290 0.2366 0.0994 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3681(4) 0.26050(10) 0.20609(10) 0.0496(4) Uani 1 1 d . . . . .
H3 H 0.3251 0.3178 0.1980 0.059 Uiso 1 1 calc R U . . .
C6 C 0.7369(4) -0.00998(11) 0.10683(11) 0.0551(5) Uani 1 1 d . . . . .
H6 H 0.8142 -0.0428 0.0658 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2532(5) 0.10119(10) 0.50847(10) 0.0491(4) Uani 1 1 d . . . . .
C2 C 0.3086(4) 0.22435(9) 0.27873(9) 0.0427(4) Uani 1 1 d . . . . .
H2 H 0.2253 0.2581 0.3185 0.051 Uiso 1 1 calc R U . . .
C14 C 0.5301(4) 0.22057(10) 0.44665(9) 0.0454(4) Uani 1 1 d . . . . .
C12 C 0.3549(4) 0.14064(9) 0.43726(9) 0.0406(4) Uani 1 1 d . . . . .
N15 N 0.1708(5) 0.07159(10) 0.56556(9) 0.0710(5) Uani 1 1 d . . . . .
C10 C 0.5536(4) 0.12459(10) 0.15771(9) 0.0399(4) Uani 1 1 d . . . . .
C5 C 0.6762(4) 0.07381(11) 0.09640(10) 0.0520(5) Uani 1 1 d . . . . .
H5 H 0.7155 0.0983 0.0483 0.062 Uiso 1 1 calc R U . . .
C7 C 0.6833(4) -0.04709(11) 0.17938(11) 0.0521(5) Uani 1 1 d . . . . .
H7 H 0.7270 -0.1046 0.1863 0.062 Uiso 1 1 calc R U . . .
H1 H 0.207(4) 0.0453(10) 0.3689(9) 0.045(4) Uiso 1 1 d . . . . .


_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
C9 C8 1.411(2) . ?
C9 C10 1.420(2) . ?
C9 C1 1.434(2) . ?
C1 C2 1.377(2) . ?
C1 C11 1.452(2) . ?
N16 C14 1.138(2) . ?
C8 C7 1.366(2) . ?
C8 H8 0.9300 . ?
C11 C12 1.347(2) . ?
C11 H1 0.981(15) . ?
C4 C3 1.359(2) . ?
C4 C10 1.411(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.399(2) . ?
C3 H3 0.9300 . ?
C6 C5 1.355(2) . ?
C6 C7 1.400(2) . ?
C6 H6 0.9300 . ?
C13 N15 1.140(2) . ?
C13 C12 1.438(2) . ?
C2 H2 0.9300 . ?
C14 C12 1.437(2) . ?
C10 C5 1.415(2) . ?
C5 H5 0.9300 . ?
C7 H7 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
C8 C9 C10 118.07(14) . . ?
C8 C9 C1 123.50(14) . . ?
C10 C9 C1 118.40(14) . . ?
C2 C1 C9 119.70(14) . . ?
C2 C1 C11 120.17(14) . . ?
C9 C1 C11 120.07(13) . . ?
C7 C8 C9 120.75(16) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C12 C11 C1 126.16(14) . . ?
C12 C11 H1 116.2(9) . . ?
C1 C11 H1 117.6(9) . . ?
C3 C4 C10 121.35(15) . . ?
C3 C4 H4 119.3 . . ?
C10 C4 H4 119.3 . . ?
C4 C3 C2 120.01(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C6 C7 119.94(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N15 C13 C12 178.51(18) . . ?
C1 C2 C3 121.25(15) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
N16 C14 C12 177.01(18) . . ?
C11 C12 C14 123.35(14) . . ?
C11 C12 C13 121.82(14) . . ?
C14 C12 C13 114.79(14) . . ?
C4 C10 C5 121.33(15) . . ?
C4 C10 C9 119.29(14) . . ?
C5 C10 C9 119.38(15) . . ?
C6 C5 C10 120.89(16) . . ?
C6 C5 H5 119.6 . . ?
C10 C5 H5 119.6 . . ?
C8 C7 C6 120.94(16) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/cc10s1jc
_database_code_depnum_ccdc_archive 'CCDC 946632'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5RA09036A 2015
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
  ethyl 2-amino-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
;
_chemical_name_common            1H-Chromene
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N2 O5'
_chemical_formula_sum            'C17 H18 N2 O5'
_chemical_formula_weight         330.33

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.271(5)
_cell_length_b                   8.507(5)
_cell_length_c                   21.337(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.690(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1679.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2141
_cell_measurement_theta_min      0.966
_cell_measurement_theta_max      0.971

_exptl_crystal_description       rectangular
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            7434
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         29.022
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4477
_reflns_number_gt                2141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    
;
 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_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1271P)²+0.7021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.001(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.2815
_refine_ls_wR_factor_gt          0.2360
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_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
O1 O -0.0500(2) 0.1781(3) 0.97891(11) 0.0439(6) Uani 1 1 d . . . . .
C2 C -0.0596(3) 0.3670(4) 0.89493(15) 0.0374(8) Uani 1 1 d . . . . .
C6 C -0.2703(3) 0.2036(4) 0.91569(15) 0.0359(7) Uani 1 1 d . . . . .
C5 C -0.1945(3) 0.1486(4) 0.96792(15) 0.0387(8) Uani 1 1 d . . . . .
C13 C -0.1588(4) 0.1757(4) 0.81135(15) 0.0400(8) Uani 1 1 d . . . . .
C8 C 0.1247(4) 0.5679(5) 0.89874(19) 0.0581(11) Uani 1 1 d . . . . .
H4 H 0.1625 0.6595 0.8826 0.070 Uiso 1 1 calc R U . . .
O5 O -0.0506(4) 0.1712(4) 0.71455(14) 0.0882(12) Uani 1 1 d . . . . .
N3 N -0.2422(3) 0.0620(4) 1.01432(14) 0.0537(9) Uani 1 1 d . . . . .
H1A H -0.3315 0.0341 1.0134 0.064 Uiso 1 1 calc R U . . .
H1B H -0.1837 0.0340 1.0452 0.064 Uiso 1 1 calc R U . . .
C1 C -0.1935(3) 0.2893(4) 0.86570(15) 0.0350(7) Uani 1 1 d . . . . .
C10 C 0.1343(4) 0.3657(5) 0.97586(17) 0.0502(9) Uani 1 1 d . . . . .
H6 H 0.1796 0.3185 1.0112 0.060 Uiso 1 1 calc R U . . .
C9 C 0.1924(4) 0.4986(5) 0.95003(19) 0.0571(11) Uani 1 1 d . . . . .
H5 H 0.2781 0.5408 0.9678 0.069 Uiso 1 1 calc R U . . .
C3 C 0.0076(3) 0.3044(4) 0.94826(15) 0.0384(8) Uani 1 1 d . . . . .
C14 C -0.0462(4) 0.0621(4) 0.83223(16) 0.0459(9) Uani 1 1 d . . . . .
C7 C 0.0001(4) 0.5033(4) 0.87047(17) 0.0475(9) Uani 1 1 d . . . . .
H3 H -0.0443 0.5506 0.8350 0.057 Uiso 1 1 calc R U . . .
N2 N 0.0423(4) -0.0199(4) 0.85206(16) 0.0689(11) Uani 1 1 d . . . . .
C16 C -0.1236(4) 0.2593(5) 0.75144(16) 0.0496(9) Uani 1 1 d . . . . .
C18 C -0.0098(8) 0.2396(9) 0.6545(2) 0.121(3) Uani 1 1 d . . . . .
H18A H -0.0284 0.3518 0.6550 0.146 Uiso 1 1 calc R U . . .
H18B H 0.0932 0.2250 0.6512 0.146 Uiso 1 1 calc R U . . .
C23 C -0.0784(10) 0.1788(11) 0.6052(3) 0.165(4) Uani 1 1 d . . . . .
H9A H -0.0593 0.0680 0.6038 0.247 Uiso 1 1 calc R U . . .
H9B H -0.0462 0.2278 0.5680 0.247 Uiso 1 1 calc R U . . .
H9C H -0.1804 0.1957 0.6073 0.247 Uiso 1 1 calc R U . . .
C12 C -0.4228(3) 0.1730(4) 0.90714(16) 0.0425(8) Uani 1 1 d . . . . .
O2 O -0.4810(2) 0.2268(3) 0.85192(11) 0.0506(7) Uani 1 1 d . . . . .
C20 C -0.6358(4) 0.2034(5) 0.8388(2) 0.0586(11) Uani 1 1 d . . . . .
H10A H -0.6589(8) 0.091(3) 0.8396(2) 0.070 Uiso 1 1 calc R U . . .
H10B H -0.6896(17) 0.2565(17) 0.8705(10) 0.070 Uiso 1 1 calc R U . . .
C22 C -0.6745(5) 0.2679(9) 0.7772(2) 0.109(2) Uani 1 1 d . . . . .
H11A H -0.7762 0.2539 0.7674 0.164 Uiso 1 1 calc R U . . .
H11B H -0.6516 0.3780 0.7770 0.164 Uiso 1 1 calc R U . . .
H11C H -0.6212 0.2147 0.7465 0.164 Uiso 1 1 calc R U . . .
O3 O -0.4960(3) 0.1037(4) 0.94413(13) 0.0653(9) Uani 1 1 d . . . . .
O4 O -0.1581(5) 0.3912(4) 0.73974(16) 0.1023(14) Uani 1 1 d . . . . .
H2 H -0.258(3) 0.366(4) 0.8435(14) 0.034(8) Uiso 1 1 d . . . . .
H7 H -0.252(4) 0.124(5) 0.7980(17) 0.056(11) Uiso 1 1 d . . . . .


_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 C5 1.368(4) . ?
O1 C3 1.383(4) . ?
C2 C3 1.369(4) . ?
C2 C7 1.400(5) . ?
C2 C1 1.506(4) . ?
C6 C5 1.361(4) . ?
C6 C12 1.437(4) . ?
C6 C1 1.508(4) . ?
C5 N3 1.332(4) . ?
C13 C14 1.471(5) . ?
C13 C16 1.517(5) . ?
C13 C1 1.559(4) . ?
C13 H7 0.99(4) . ?
C8 C9 1.360(6) . ?
C8 C7 1.382(5) . ?
C8 H4 0.9300 . ?
O5 C16 1.307(5) . ?
O5 C18 1.478(6) . ?
N3 H1A 0.8600 . ?
N3 H1B 0.8600 . ?
C1 H2 0.99(3) . ?
C10 C3 1.382(5) . ?
C10 C9 1.382(6) . ?
C10 H6 0.9300 . ?
C9 H5 0.9300 . ?
C14 N2 1.137(5) . ?
C7 H3 0.9300 . ?
C16 O4 1.189(5) . ?
C18 C23 1.302(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C23 H9A 0.9600 . ?
C23 H9B 0.9600 . ?
C23 H9C 0.9600 . ?
C12 O3 1.225(4) . ?
C12 O2 1.344(4) . ?
O2 C20 1.458(4) . ?
C20 C22 1.447(6) . ?
C20 H10A 0.98(3) . ?
C20 H10B 0.98(3) . ?
C22 H11A 0.9600 . ?
C22 H11B 0.9600 . ?
C22 H11C 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
C5 O1 C3 117.7(2) . . ?
C3 C2 C7 117.5(3) . . ?
C3 C2 C1 119.5(3) . . ?
C7 C2 C1 123.0(3) . . ?
C5 C6 C12 119.6(3) . . ?
C5 C6 C1 120.2(3) . . ?
C12 C6 C1 120.2(3) . . ?
N3 C5 C6 128.3(3) . . ?
N3 C5 O1 110.0(3) . . ?
C6 C5 O1 121.7(3) . . ?
C14 C13 C16 112.1(3) . . ?
C14 C13 C1 111.0(3) . . ?
C16 C13 C1 113.7(3) . . ?
C14 C13 H7 112(2) . . ?
C16 C13 H7 101(2) . . ?
C1 C13 H7 106(2) . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H4 119.7 . . ?
C7 C8 H4 119.7 . . ?
C16 O5 C18 117.9(4) . . ?
C5 N3 H1A 120.0 . . ?
C5 N3 H1B 120.0 . . ?
H1A N3 H1B 120.0 . . ?
C2 C1 C6 109.5(3) . . ?
C2 C1 C13 112.1(3) . . ?
C6 C1 C13 110.9(3) . . ?
C2 C1 H2 111.6(18) . . ?
C6 C1 H2 111.0(18) . . ?
C13 C1 H2 101.7(18) . . ?
C3 C10 C9 118.8(4) . . ?
C3 C10 H6 120.6 . . ?
C9 C10 H6 120.6 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H5 119.9 . . ?
C10 C9 H5 119.9 . . ?
C2 C3 C10 122.4(3) . . ?
C2 C3 O1 121.7(3) . . ?
C10 C3 O1 115.8(3) . . ?
N2 C14 C13 175.3(4) . . ?
C8 C7 C2 120.4(4) . . ?
C8 C7 H3 119.8 . . ?
C2 C7 H3 119.8 . . ?
O4 C16 O5 123.9(4) . . ?
O4 C16 C13 123.4(4) . . ?
O5 C16 C13 112.7(3) . . ?
C23 C18 O5 114.0(6) . . ?
C23 C18 H18A 108.8 . . ?
O5 C18 H18A 108.8 . . ?
C23 C18 H18B 108.8 . . ?
O5 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C23 H9A 109.5 . . ?
C18 C23 H9B 109.5 . . ?
H9A C23 H9B 109.5 . . ?
C18 C23 H9C 109.5 . . ?
H9A C23 H9C 109.5 . . ?
H9B C23 H9C 109.5 . . ?
O3 C12 O2 121.4(3) . . ?
O3 C12 C6 125.9(3) . . ?
O2 C12 C6 112.7(3) . . ?
C12 O2 C20 117.2(3) . . ?
C22 C20 O2 107.8(3) . . ?
C22 C20 H10A 110.1 . . ?
O2 C20 H10A 110.1 . . ?
C22 C20 H10B 110.1 . . ?
O2 C20 H10B 110.1 . . ?
H10A C20 H10B 108.5 . . ?
C20 C22 H11A 109.5 . . ?
C20 C22 H11B 109.5 . . ?
H11A C22 H11B 109.5 . . ?
C20 C22 H11C 109.5 . . ?
H11A C22 H11C 109.5 . . ?
H11B C22 H11C 109.5 . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.067

