# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 2098423'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C11 H8 N2 O'
_chemical_formula_sum            'C13 H14 N2 O2 S'
_chemical_formula_weight         262.32
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6003(5)
_cell_length_b                   9.7756(7)
_cell_length_c                   9.7883(7)
_cell_angle_alpha                96.092(2)
_cell_angle_beta                 103.963(2)
_cell_angle_gamma                111.340(3)
_cell_volume                     642.06(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2640
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.467
_cell_measurement_theta_min      2.195
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.247
_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            ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6838
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_min         2.195
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_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                1981
_reflns_number_total             2640
_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    ?
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.030
_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)+(0.0368P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E),
 C00G(H00G), C00H(H00H)
2.b Idealised Me refined as rotating group:
 C00F(H00D,H00F,H00I), C00I(H00J,H00K,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S001 S 0.32134(8) 0.52833(6) 0.67175(6) 0.04403(19) Uani 1 1 d . . . . .
O002 O 0.2650(2) 0.45525(18) 0.51533(16) 0.0537(4) Uani 1 1 d . . . . .
N003 N 0.2746(3) 0.16625(19) 0.41383(17) 0.0395(4) Uani 1 1 d . . . . .
H003 H 0.3245 0.2611 0.4503 0.047 Uiso 1 1 calc R . . . .
O004 O 0.2420(3) -0.06004(18) 0.47083(17) 0.0700(6) Uani 1 1 d . . . . .
N005 N 0.6030(3) 0.2962(2) 0.9509(2) 0.0542(5) Uani 1 1 d . . . . .
C006 C 0.0309(3) -0.0521(2) 0.0326(2) 0.0341(4) Uani 1 1 d . . . . .
C007 C 0.1175(3) 0.2264(2) 0.1992(2) 0.0396(5) Uani 1 1 d . . . . .
H007 H 0.1482 0.3199 0.2549 0.047 Uiso 1 1 calc R . . . .
C008 C 0.1755(3) 0.1209(2) 0.2641(2) 0.0353(5) Uani 1 1 d . . . . .
C009 C 0.4067(3) 0.1566(2) 0.6603(2) 0.0378(5) Uani 1 1 d . . . . .
C00A C 0.0172(3) 0.1928(2) 0.0561(2) 0.0406(5) Uani 1 1 d . . . . .
H00A H -0.0204 0.2637 0.0158 0.049 Uiso 1 1 calc R . . . .
C00B C 0.5606(3) 0.2975(2) 0.7002(2) 0.0437(5) Uani 1 1 d . . . . .
H00B H 0.6011 0.3488 0.6310 0.052 Uiso 1 1 calc R . . . .
C00C C 0.1347(3) -0.0159(2) 0.1813(2) 0.0384(5) Uani 1 1 d . . . . .
H00C H 0.1755 -0.0847 0.2231 0.046 Uiso 1 1 calc R . . . .
C00D C 0.2990(3) 0.0757(2) 0.5059(2) 0.0421(5) Uani 1 1 d . . . . .
C00E C 0.3544(3) 0.0867(3) 0.7688(2) 0.0463(5) Uani 1 1 d . . . . .
H00E H 0.2533 -0.0089 0.7466 0.056 Uiso 1 1 calc R . . . .
C00F C 0.2570(4) 0.6852(3) 0.6747(3) 0.0569(6) Uani 1 1 d . . . . .
H00D H 0.3409 0.7590 0.6351 0.085 Uiso 1 1 calc GR . . . .
H00F H 0.2739 0.7281 0.7723 0.085 Uiso 1 1 calc GR . . . .
H00I H 0.1212 0.6535 0.6183 0.085 Uiso 1 1 calc GR . . . .
C00G C 0.6527(4) 0.3603(3) 0.8454(2) 0.0523(6) Uani 1 1 d . . . . .
H00G H 0.7574 0.4544 0.8710 0.063 Uiso 1 1 calc R . . . .
C00H C 0.4541(4) 0.1609(3) 0.9102(2) 0.0535(6) Uani 1 1 d . . . . .
H00H H 0.4150 0.1133 0.9818 0.064 Uiso 1 1 calc R . . . .
C00I C 0.1362(5) 0.4127(3) 0.7396(3) 0.0766(9) Uani 1 1 d . . . . .
H00J H 0.0079 0.3999 0.6810 0.115 Uiso 1 1 calc GR . . . .
H00K H 0.1577 0.4593 0.8370 0.115 Uiso 1 1 calc GR . . . .
H00L H 0.1428 0.3163 0.7375 0.115 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
S001 O002 1.5056(15) . ?
S001 C00F 1.771(2) . ?
S001 C00I 1.775(3) . ?
N003 H003 0.8600 . ?
N003 C008 1.413(2) . ?
N003 C00D 1.356(3) . ?
O004 C00D 1.216(3) . ?
N005 C00G 1.325(3) . ?
N005 C00H 1.331(3) . ?
C006 C006 1.416(4) 2 ?
C006 C00A 1.416(3) 2 ?
C006 C00C 1.414(3) . ?
C007 H007 0.9300 . ?
C007 C008 1.412(3) . ?
C007 C00A 1.363(3) . ?
C008 C00C 1.374(3) . ?
C009 C00B 1.382(3) . ?
C009 C00D 1.502(3) . ?
C009 C00E 1.383(3) . ?
C00A C006 1.416(3) 2 ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00G 1.382(3) . ?
C00C H00C 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00H 1.377(3) . ?
C00F H00D 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00I 0.9600 . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00J 0.9600 . ?
C00I H00K 0.9600 . ?
C00I H00L 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
O002 S001 C00F 106.24(10) . . ?
O002 S001 C00I 105.92(12) . . ?
C00F S001 C00I 98.38(14) . . ?
C008 N003 H003 116.6 . . ?
C00D N003 H003 116.6 . . ?
C00D N003 C008 126.75(18) . . ?
C00G N005 C00H 115.8(2) . . ?
C006 C006 C00A 117.6(2) 2 2 ?
C00C C006 C006 120.5(2) . 2 ?
C00C C006 C00A 121.87(19) . 2 ?
C008 C007 H007 119.6 . . ?
C00A C007 H007 119.6 . . ?
C00A C007 C008 120.84(19) . . ?
C007 C008 N003 116.04(17) . . ?
C00C C008 N003 124.31(19) . . ?
C00C C008 C007 119.65(18) . . ?
C00B C009 C00D 123.10(19) . . ?
C00B C009 C00E 117.73(19) . . ?
C00E C009 C00D 119.15(19) . . ?
C006 C00A H00A 119.4 2 . ?
C007 C00A C006 121.29(19) . 2 ?
C007 C00A H00A 119.4 . . ?
C009 C00B H00B 120.8 . . ?
C00G C00B C009 118.4(2) . . ?
C00G C00B H00B 120.8 . . ?
C006 C00C H00C 120.0 . . ?
C008 C00C C006 120.08(19) . . ?
C008 C00C H00C 120.0 . . ?
N003 C00D C009 114.48(18) . . ?
O004 C00D N003 124.7(2) . . ?
O004 C00D C009 120.81(19) . . ?
C009 C00E H00E 120.5 . . ?
C00H C00E C009 119.0(2) . . ?
C00H C00E H00E 120.5 . . ?
S001 C00F H00D 109.5 . . ?
S001 C00F H00F 109.5 . . ?
S001 C00F H00I 109.5 . . ?
H00D C00F H00F 109.5 . . ?
H00D C00F H00I 109.5 . . ?
H00F C00F H00I 109.5 . . ?
N005 C00G C00B 124.8(2) . . ?
N005 C00G H00G 117.6 . . ?
C00B C00G H00G 117.6 . . ?
N005 C00H C00E 124.2(2) . . ?
N005 C00H H00H 117.9 . . ?
C00E C00H H00H 117.9 . . ?
S001 C00I H00J 109.5 . . ?
S001 C00I H00K 109.5 . . ?
S001 C00I H00L 109.5 . . ?
H00J C00I H00K 109.5 . . ?
H00J C00I H00L 109.5 . . ?
H00K C00I H00L 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_5
_database_code_depnum_ccdc_archive 'CCDC 2098427'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, 0.5(C26 H18 N4 O2)'
_chemical_formula_sum            'C15 H15 N2 O2 S'
_chemical_formula_weight         287.35
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1303(5)
_cell_length_b                   9.5438(5)
_cell_length_c                   18.2326(9)
_cell_angle_alpha                86.920(2)
_cell_angle_beta                 78.265(2)
_cell_angle_gamma                66.827(2)
_cell_volume                     1429.43(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5819
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.470
_cell_measurement_theta_min      2.322
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.229
_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            ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15101
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.470
_diffrn_reflns_theta_min         2.322
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_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                4604
_reflns_number_total             5819
_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    ?
_refine_diff_density_max         1.101
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.733
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      0.733
_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)+(0.1714P)²+1.4295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011)
2.b Idealised Me refined as rotating group:
 C010(H01G,H01H,H01I), C012(H01A,H01B,H01C), C013(H01D,H01E,H01F), C014(H01J,
 H01K,H01L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S001 S 0.31726(8) 0.74499(9) 0.35669(4) 0.0489(2) Uani 1 1 d . . . . .
S002 S 1.28654(9) 0.14483(8) 0.05298(5) 0.0550(2) Uani 1 1 d . . . . .
O003 O 1.1212(2) 0.8008(2) 0.11604(12) 0.0538(5) Uani 1 1 d . . . . .
O004 O 0.2036(2) 0.7586(3) 0.43052(10) 0.0579(6) Uani 1 1 d . . . . .
N005 N 0.2594(2) 0.8803(2) 0.55356(10) 0.0354(4) Uani 1 1 d . . . . .
H005 H 0.2158 0.8552 0.5216 0.043 Uiso 1 1 calc R . . . .
N006 N 1.1760(2) 0.5632(2) 0.07479(11) 0.0361(4) Uani 1 1 d . . . . .
H006 H 1.1386 0.4938 0.0736 0.043 Uiso 1 1 calc R . . . .
O007 O 1.1364(2) 0.2862(2) 0.07037(14) 0.0583(6) Uani 1 1 d . . . . .
O008 O 0.2663(3) 0.8944(3) 0.67620(10) 0.0597(6) Uani 1 1 d . . . . .
C009 C 0.3809(3) 0.9419(3) 0.52713(12) 0.0314(5) Uani 1 1 d . . . . .
C00A C 0.3388(3) 1.0985(3) 0.53146(12) 0.0320(5) Uani 1 1 d . . . . .
C00B C 1.4680(3) 0.4351(2) 0.07005(12) 0.0313(5) Uani 1 1 d . . . . .
C00C C 0.0849(3) 0.7944(3) 0.64629(12) 0.0344(5) Uani 1 1 d . . . . .
C00D C 1.3400(3) 0.5331(2) 0.03726(12) 0.0313(5) Uani 1 1 d . . . . .
N00E N 0.5935(3) 0.7505(3) 0.21795(15) 0.0583(7) Uani 1 1 d . . . . .
C00F C 0.9097(3) 0.7095(2) 0.14822(12) 0.0320(5) Uani 1 1 d . . . . .
C00G C 1.3676(3) 0.5997(2) -0.03175(12) 0.0308(5) Uani 1 1 d . . . . .
C00H C 1.0789(3) 0.6956(3) 0.11161(13) 0.0349(5) Uani 1 1 d . . . . .
C00I C 0.5400(3) 0.8411(3) 0.49639(12) 0.0328(5) Uani 1 1 d . . . . .
C00J C 0.2124(3) 0.8611(3) 0.62687(13) 0.0358(5) Uani 1 1 d . . . . .
N00K N -0.1525(3) 0.6743(3) 0.69198(15) 0.0612(7) Uani 1 1 d . . . . .
C00L C 1.2386(3) 0.6983(3) -0.06644(14) 0.0387(5) Uani 1 1 d . . . . .
H00L H 1.1315 0.7205 -0.0425 0.046 Uiso 1 1 calc R . . . .
C00M C 0.8323(3) 0.6267(3) 0.12412(14) 0.0397(5) Uani 1 1 d . . . . .
H00M H 0.8847 0.5559 0.0845 0.048 Uiso 1 1 calc R . . . .
C00N C 0.1769(3) 1.2029(3) 0.56035(14) 0.0416(6) Uani 1 1 d . . . . .
H00N H 0.0970 1.1657 0.5792 0.050 Uiso 1 1 calc R . . . .
C00O C 1.5585(3) 0.6317(3) -0.14132(14) 0.0408(5) Uani 1 1 d . . . . .
H00O H 1.6643 0.6100 -0.1672 0.049 Uiso 1 1 calc R . . . .
C00P C -0.0416(3) 0.8276(3) 0.60919(15) 0.0468(6) Uani 1 1 d . . . . .
H00P H -0.0496 0.8898 0.5679 0.056 Uiso 1 1 calc R . . . .
C00Q C 0.5869(3) 0.6799(3) 0.49340(16) 0.0455(6) Uani 1 1 d . . . . .
H00Q H 0.5092 0.6391 0.5103 0.055 Uiso 1 1 calc R . . . .
C00R C 0.8260(3) 0.8141(3) 0.20683(15) 0.0437(6) Uani 1 1 d . . . . .
H00R H 0.8736 0.8732 0.2236 0.052 Uiso 1 1 calc R . . . .
C00S C 1.2692(3) 0.7601(3) -0.13357(15) 0.0462(6) Uani 1 1 d . . . . .
H00S H 1.1835 0.8252 -0.1549 0.055 Uiso 1 1 calc R . . . .
C00T C 0.0911(3) 0.6985(3) 0.70634(15) 0.0491(6) Uani 1 1 d . . . . .
H00T H 0.1742 0.6732 0.7331 0.059 Uiso 1 1 calc R . . . .
C00U C 1.4326(4) 0.7255(3) -0.17144(15) 0.0479(6) Uani 1 1 d . . . . .
H00U H 1.4527 0.7681 -0.2175 0.057 Uiso 1 1 calc R . . . .
C00V C 0.6698(3) 0.8294(4) 0.24030(17) 0.0573(8) Uani 1 1 d . . . . .
H00V H 0.6152 0.8983 0.2805 0.069 Uiso 1 1 calc R . . . .
C00W C 0.6755(3) 0.6520(3) 0.16043(17) 0.0512(7) Uani 1 1 d . . . . .
H00W H 0.6238 0.5969 0.1437 0.061 Uiso 1 1 calc R . . . .
C00X C -0.1571(4) 0.7658(4) 0.63500(17) 0.0568(7) Uani 1 1 d . . . . .
H00X H -0.2433 0.7907 0.6103 0.068 Uiso 1 1 calc R . . . .
C00Y C 0.1377(4) 1.3558(3) 0.56077(18) 0.0570(7) Uani 1 1 d . . . . .
H00Y H 0.0311 1.4221 0.5791 0.068 Uiso 1 1 calc R . . . .
C00Z C 0.7426(4) 0.5854(3) 0.46631(19) 0.0579(8) Uani 1 1 d . . . . .
H00Z H 0.7709 0.4805 0.4655 0.069 Uiso 1 1 calc R . . . .
C010 C 1.2397(5) 0.0219(4) 0.0007(2) 0.0671(9) Uani 1 1 d . . . . .
H01G H 1.1404 0.0143 0.0263 0.101 Uiso 1 1 calc GR . . . .
H01H H 1.3263 -0.0774 -0.0045 0.101 Uiso 1 1 calc GR . . . .
H01I H 1.2271 0.0623 -0.0480 0.101 Uiso 1 1 calc GR . . . .
C011 C -0.0278(4) 0.6416(4) 0.72563(18) 0.0632(9) Uani 1 1 d . . . . .
H011 H -0.0202 0.5753 0.7653 0.076 Uiso 1 1 calc R . . . .
C012 C 0.1992(4) 0.7687(5) 0.28739(18) 0.0744(11) Uani 1 1 d . . . . .
H01A H 0.1459 0.6987 0.2955 0.112 Uiso 1 1 calc GR . . . .
H01B H 0.2686 0.7490 0.2387 0.112 Uiso 1 1 calc GR . . . .
H01C H 0.1192 0.8713 0.2905 0.112 Uiso 1 1 calc GR . . . .
C013 C 0.4351(5) 0.5475(4) 0.3390(2) 0.0756(10) Uani 1 1 d . . . . .
H01D H 0.5107 0.5116 0.3722 0.113 Uiso 1 1 calc GR . . . .
H01E H 0.4936 0.5310 0.2880 0.113 Uiso 1 1 calc GR . . . .
H01F H 0.3648 0.4929 0.3472 0.113 Uiso 1 1 calc GR . . . .
C014 C 1.2968(6) 0.0400(5) 0.1372(3) 0.0949(15) Uani 1 1 d . . . . .
H01J H 1.3243 0.0900 0.1734 0.142 Uiso 1 1 calc GR . . . .
H01K H 1.3784 -0.0614 0.1266 0.142 Uiso 1 1 calc GR . . . .
H01L H 1.1933 0.0348 0.1569 0.142 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
S001 O004 1.4999(19) . ?
S001 C012 1.772(3) . ?
S001 C013 1.773(4) . ?
S002 O007 1.488(2) . ?
S002 C010 1.774(3) . ?
S002 C014 1.785(4) . ?
O003 C00H 1.222(3) . ?
N005 H005 0.8600 . ?
N005 C009 1.440(3) . ?
N005 C00J 1.344(3) . ?
N006 H006 0.8600 . ?
N006 C00D 1.435(3) . ?
N006 C00H 1.342(3) . ?
O008 C00J 1.219(3) . ?
C009 C00A 1.391(3) . ?
C009 C00I 1.406(3) . ?
C00A C00I 1.434(3) 2_676 ?
C00A C00N 1.426(3) . ?
C00B C00D 1.401(3) . ?
C00B C00G 1.435(3) 2_865 ?
C00B C00O 1.434(3) 2_865 ?
C00C C00J 1.509(3) . ?
C00C C00P 1.378(4) . ?
C00C C00T 1.384(3) . ?
C00D C00G 1.400(3) . ?
N00E C00V 1.333(4) . ?
N00E C00W 1.333(4) . ?
C00F C00H 1.509(3) . ?
C00F C00M 1.386(3) . ?
C00F C00R 1.380(3) . ?
C00G C00B 1.435(3) 2_865 ?
C00G C00L 1.428(3) . ?
C00I C00A 1.434(3) 2_676 ?
C00I C00Q 1.426(3) . ?
N00K C00X 1.317(4) . ?
N00K C011 1.325(4) . ?
C00L H00L 0.9300 . ?
C00L C00S 1.356(4) . ?
C00M H00M 0.9300 . ?
C00M C00W 1.380(3) . ?
C00N H00N 0.9300 . ?
C00N C00Y 1.359(4) . ?
C00O C00B 1.434(3) 2_865 ?
C00O H00O 0.9300 . ?
C00O C00U 1.349(4) . ?
C00P H00P 0.9300 . ?
C00P C00X 1.393(4) . ?
C00Q H00Q 0.9300 . ?
C00Q C00Z 1.354(4) . ?
C00R H00R 0.9300 . ?
C00R C00V 1.385(4) . ?
C00S H00S 0.9300 . ?
C00S C00U 1.424(4) . ?
C00T H00T 0.9300 . ?
C00T C011 1.373(4) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C00Z 1.410(4) 2_676 ?
C00Z C00Y 1.410(4) 2_676 ?
C00Z H00Z 0.9300 . ?
C010 H01G 0.9600 . ?
C010 H01H 0.9600 . ?
C010 H01I 0.9600 . ?
C011 H011 0.9300 . ?
C012 H01A 0.9600 . ?
C012 H01B 0.9600 . ?
C012 H01C 0.9600 . ?
C013 H01D 0.9600 . ?
C013 H01E 0.9600 . ?
C013 H01F 0.9600 . ?
C014 H01J 0.9600 . ?
C014 H01K 0.9600 . ?
C014 H01L 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
O004 S001 C012 105.76(14) . . ?
O004 S001 C013 106.33(16) . . ?
C012 S001 C013 96.7(2) . . ?
O007 S002 C010 106.37(15) . . ?
O007 S002 C014 106.0(2) . . ?
C010 S002 C014 97.27(18) . . ?
C009 N005 H005 119.2 . . ?
C00J N005 H005 119.2 . . ?
C00J N005 C009 121.70(19) . . ?
C00D N006 H006 118.7 . . ?
C00H N006 H006 118.7 . . ?
C00H N006 C00D 122.50(18) . . ?
C00A C009 N005 119.8(2) . . ?
C00A C009 C00I 121.5(2) . . ?
C00I C009 N005 118.6(2) . . ?
C009 C00A C00I 119.4(2) . 2_676 ?
C009 C00A C00N 122.3(2) . . ?
C00N C00A C00I 118.3(2) . 2_676 ?
C00D C00B C00G 119.3(2) . 2_865 ?
C00D C00B C00O 122.5(2) . 2_865 ?
C00O C00B C00G 118.2(2) 2_865 2_865 ?
C00P C00C C00J 123.7(2) . . ?
C00P C00C C00T 117.7(2) . . ?
C00T C00C C00J 118.6(2) . . ?
C00B C00D N006 118.9(2) . . ?
C00G C00D N006 119.2(2) . . ?
C00G C00D C00B 121.95(19) . . ?
C00W N00E C00V 116.7(2) . . ?
C00M C00F C00H 123.3(2) . . ?
C00R C00F C00H 118.2(2) . . ?
C00R C00F C00M 118.5(2) . . ?
C00D C00G C00B 118.8(2) . 2_865 ?
C00D C00G C00L 122.7(2) . . ?
C00L C00G C00B 118.5(2) . 2_865 ?
O003 C00H N006 123.4(2) . . ?
O003 C00H C00F 120.5(2) . . ?
N006 C00H C00F 116.10(19) . . ?
C009 C00I C00A 119.1(2) . 2_676 ?
C009 C00I C00Q 122.4(2) . . ?
C00Q C00I C00A 118.5(2) . 2_676 ?
N005 C00J C00C 115.86(19) . . ?
O008 C00J N005 123.9(2) . . ?
O008 C00J C00C 120.3(2) . . ?
C00X N00K C011 115.9(2) . . ?
C00G C00L H00L 119.4 . . ?
C00S C00L C00G 121.3(2) . . ?
C00S C00L H00L 119.4 . . ?
C00F C00M H00M 120.9 . . ?
C00W C00M C00F 118.3(2) . . ?
C00W C00M H00M 120.9 . . ?
C00A C00N H00N 119.5 . . ?
C00Y C00N C00A 121.0(2) . . ?
C00Y C00N H00N 119.5 . . ?
C00B C00O H00O 119.5 2_865 . ?
C00U C00O C00B 121.1(2) . 2_865 ?
C00U C00O H00O 119.5 . . ?
C00C C00P H00P 120.8 . . ?
C00C C00P C00X 118.4(2) . . ?
C00X C00P H00P 120.8 . . ?
C00I C00Q H00Q 119.5 . . ?
C00Z C00Q C00I 121.0(3) . . ?
C00Z C00Q H00Q 119.5 . . ?
C00F C00R H00R 120.6 . . ?
C00F C00R C00V 118.8(2) . . ?
C00V C00R H00R 120.6 . . ?
C00L C00S H00S 120.0 . . ?
C00L C00S C00U 120.0(2) . . ?
C00U C00S H00S 120.0 . . ?
C00C C00T H00T 120.7 . . ?
C011 C00T C00C 118.7(3) . . ?
C011 C00T H00T 120.7 . . ?
C00O C00U C00S 120.9(2) . . ?
C00O C00U H00U 119.6 . . ?
C00S C00U H00U 119.6 . . ?
N00E C00V C00R 123.6(2) . . ?
N00E C00V H00V 118.2 . . ?
C00R C00V H00V 118.2 . . ?
N00E C00W C00M 124.1(2) . . ?
N00E C00W H00W 117.9 . . ?
C00M C00W H00W 117.9 . . ?
N00K C00X C00P 124.5(3) . . ?
N00K C00X H00X 117.8 . . ?
C00P C00X H00X 117.8 . . ?
C00N C00Y H00Y 119.8 . . ?
C00N C00Y C00Z 120.5(3) . 2_676 ?
C00Z C00Y H00Y 119.8 2_676 . ?
C00Q C00Z C00Y 120.7(3) . 2_676 ?
C00Q C00Z H00Z 119.7 . . ?
C00Y C00Z H00Z 119.7 2_676 . ?
S002 C010 H01G 109.5 . . ?
S002 C010 H01H 109.5 . . ?
S002 C010 H01I 109.5 . . ?
H01G C010 H01H 109.5 . . ?
H01G C010 H01I 109.5 . . ?
H01H C010 H01I 109.5 . . ?
N00K C011 C00T 124.8(3) . . ?
N00K C011 H011 117.6 . . ?
C00T C011 H011 117.6 . . ?
S001 C012 H01A 109.5 . . ?
S001 C012 H01B 109.5 . . ?
S001 C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?
S001 C013 H01D 109.5 . . ?
S001 C013 H01E 109.5 . . ?
S001 C013 H01F 109.5 . . ?
H01D C013 H01E 109.5 . . ?
H01D C013 H01F 109.5 . . ?
H01E C013 H01F 109.5 . . ?
S002 C014 H01J 109.5 . . ?
S002 C014 H01K 109.5 . . ?
S002 C014 H01L 109.5 . . ?
H01J C014 H01K 109.5 . . ?
H01J C014 H01L 109.5 . . ?
H01K C014 H01L 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_2
_database_code_depnum_ccdc_archive 'CCDC 2098424'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H22 N4 O2'
_chemical_formula_sum            'C27 H22 N4 O2'
_chemical_formula_weight         434.48
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1477(9)
_cell_length_b                   10.3739(8)
_cell_length_c                   25.486(3)
_cell_angle_alpha                89.281(5)
_cell_angle_beta                 79.975(6)
_cell_angle_gamma                67.010(5)
_cell_volume                     2188.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7702
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.955
_cell_measurement_theta_min      1.763
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.684
_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            ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1801
_diffrn_reflns_av_unetI/netI     0.1808
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24434
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.955
_diffrn_reflns_theta_min         1.763
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2477
_reflns_number_total             7702
_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    ?
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         7702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2545
_refine_ls_R_factor_gt           0.0931
_refine_ls_restrained_S_all      0.938
_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)+(0.1330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2999
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C01R(0.5) H01R(0.5) C01U(0.5) H01U(0.5) C01V(0.5) H01V(0.5)
 C01W(0.5) H01W(0.5) C1(0.5) H1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C5(0.5)
 H5(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N001(H001), N002(H002), N004(H004), C00A(H00A), N00H(H00H), C00O(H00O),
 C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00X(H00X), C00Z(H00Z),
 C010(H010), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C01A(H01J), C01B(H01D), C01C(H01E), C01F(H01K), C01H(H01L), C01I(H01I),
 C01N(H01N), C01O(H01O), C01P(H01P), C01Q(H01Q), C01R(H01R), C01U(H01U),
 C01V(H01V), C01W(H01W), C1(H1), C2(H2), C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C00K(H00B,H00C,H00D), C00M(H00E,H00F,H00G), C013(H01A,H01B,H01C), C01K(H01F,
 H01G,H01H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N001 N 0.7637(6) 0.0284(5) 0.5054(2) 0.0569(15) Uani 1 1 d . . . . .
H001 H 0.7801 0.0604 0.5347 0.068 Uiso 1 1 calc R . . . .
N002 N 0.8364(6) 0.6823(5) 0.2370(2) 0.0593(15) Uani 1 1 d . . . . .
H002 H 0.8533 0.6620 0.2025 0.071 Uiso 1 1 calc R . . . .
O003 O 0.6979(6) -0.1402(5) 0.4723(2) 0.0897(17) Uani 1 1 d . . . . .
N004 N 0.7021(6) 0.5412(5) 0.7566(2) 0.0726(18) Uani 1 1 d . . . . .
H004 H 0.7219 0.5763 0.7259 0.087 Uiso 1 1 calc R . . . .
O005 O 0.7895(8) 0.8592(5) 0.2962(2) 0.110(2) Uani 1 1 d . . . . .
N006 N 0.7447(7) 0.2079(5) 0.6025(2) 0.0650(16) Uani 1 1 d . . . . .
N007 N 0.6912(7) -0.2730(5) 0.6605(2) 0.0705(17) Uani 1 1 d . . . . .
N008 N 0.8215(10) 1.5751(7) 1.1171(3) 0.0752(19) Uani 1 1 d . . . . .
N009 N 0.8029(8) 1.0885(7) 0.1227(3) 0.0799(19) Uani 1 1 d . . . . .
C00A C 0.7715(7) 0.2388(6) 0.4650(3) 0.0504(17) Uani 1 1 d . . . . .
H00A H 0.7548 0.2812 0.4995 0.060 Uiso 1 1 calc R . . . .
C00B C 0.7851(7) 0.3120(6) 0.4193(3) 0.0465(16) Uani 1 1 d . . . . .
C00C C 0.8032(7) 0.4734(6) 0.3553(3) 0.0488(16) Uani 1 1 d . . . . .
C00D C 0.8124(7) 0.2492(6) 0.3690(3) 0.0503(17) Uani 1 1 d . . . . .
O00E O 0.6467(8) 0.3646(6) 0.7940(2) 0.120(2) Uani 1 1 d . . . . .
C00F C 0.8184(8) 0.8108(6) 0.2518(3) 0.0580(19) Uani 1 1 d . . . . .
C00G C 0.8206(7) 0.3508(6) 0.3294(3) 0.0530(17) Uani 1 1 d . . . . .
N00H N 0.7348(7) 1.2062(6) 1.0133(2) 0.086(2) Uani 1 1 d . . . . .
H00H H 0.7392 1.1894 1.0470 0.103 Uiso 1 1 calc R . . . .
C00I C 0.7117(8) -0.1413(6) 0.5639(3) 0.0584(19) Uani 1 1 d . . . . .
C00J C 0.7768(7) 0.4628(5) 0.4153(3) 0.0492(16) Uani 1 1 d . . . . .
C00K C 0.9030(7) 0.4867(6) 0.4420(2) 0.0554(17) Uani 1 1 d . . . . .
H00B H 0.8905 0.4620 0.4792 0.083 Uiso 1 1 calc GR . . . .
H00C H 0.8874 0.5856 0.4407 0.083 Uiso 1 1 calc GR . . . .
H00D H 1.0116 0.4278 0.4230 0.083 Uiso 1 1 calc GR . . . .
C00L C 0.7831(7) 0.1007(6) 0.4584(3) 0.0536(18) Uani 1 1 d . . . . .
C00M C 0.6061(7) 0.5677(5) 0.4427(2) 0.0574(18) Uani 1 1 d . . . . .
H00E H 0.5238 0.5527 0.4266 0.086 Uiso 1 1 calc GR . . . .
H00F H 0.5979 0.6640 0.4379 0.086 Uiso 1 1 calc GR . . . .
H00G H 0.5893 0.5523 0.4809 0.086 Uiso 1 1 calc GR . . . .
C00N C 0.7230(8) -0.0836(6) 0.5099(3) 0.066(2) Uani 1 1 d . . . . .
C00O C 0.8085(7) 0.5865(6) 0.3273(3) 0.0554(18) Uani 1 1 d . . . . .
H00O H 0.7973 0.6706 0.3452 0.066 Uiso 1 1 calc R . . . .
C00P C 0.6940(8) 0.9772(6) 0.8422(3) 0.0558(18) Uani 1 1 d . . . . .
C00Q C 0.8100(7) 0.0385(6) 0.4079(3) 0.0586(18) Uani 1 1 d . . . . .
H00Q H 0.8179 -0.0551 0.4041 0.070 Uiso 1 1 calc R . . . .
O00R O 0.7492(9) 1.3579(5) 0.9543(2) 0.131(3) Uani 1 1 d . . . . .
C00S C 0.6973(7) 0.7526(6) 0.7967(3) 0.0628(19) Uani 1 1 d . . . . .
H00S H 0.6983 0.7899 0.7625 0.075 Uiso 1 1 calc R . . . .
C00T C 0.8257(8) 0.1130(6) 0.3626(3) 0.0610(19) Uani 1 1 d . . . . .
H00T H 0.8452 0.0704 0.3279 0.073 Uiso 1 1 calc R . . . .
C00U C 0.7082(8) 1.1101(7) 0.9274(3) 0.068(2) Uani 1 1 d . . . . .
H00U H 0.7080 1.1904 0.9090 0.081 Uiso 1 1 calc R . . . .
C00V C 0.6944(8) 0.8315(6) 0.8404(3) 0.0603(19) Uani 1 1 d . . . . .
C00W C 0.8185(8) 0.9062(7) 0.2063(3) 0.0625(19) Uani 1 1 d . . . . .
C00X C 0.7943(8) -0.1285(6) 0.6021(3) 0.0558(18) Uani 1 1 d . . . . .
H00X H 0.8599 -0.0759 0.5965 0.067 Uiso 1 1 calc R . . . .
C00Y C 0.7003(8) 0.9959(6) 0.9009(3) 0.0627(19) Uani 1 1 d . . . . .
C00Z C 0.7792(8) -0.1957(6) 0.6498(3) 0.0638(19) Uani 1 1 d . . . . .
H00Z H 0.8356 -0.1853 0.6763 0.077 Uiso 1 1 calc R . . . .
C010 C 0.7266(8) 1.0499(7) 0.2149(3) 0.065(2) Uani 1 1 d . . . . .
H010 H 0.6681 1.0890 0.2495 0.078 Uiso 1 1 calc R . . . .
C011 C 0.8311(7) 0.5730(6) 0.2715(3) 0.0557(17) Uani 1 1 d . . . . .
C012 C 0.7460(10) 1.3238(7) 0.9978(3) 0.072(2) Uani 1 1 d . . . . .
C013 C 0.5392(8) 1.0851(5) 0.8276(3) 0.0639(19) Uani 1 1 d . . . . .
H01A H 0.5360 1.0668 0.7903 0.096 Uiso 1 1 calc GR . . . .
H01B H 0.5368 1.1795 0.8324 0.096 Uiso 1 1 calc GR . . . .
H01C H 0.4453 1.0783 0.8508 0.096 Uiso 1 1 calc GR . . . .
C014 C 0.6179(8) -0.2210(6) 0.5737(3) 0.066(2) Uani 1 1 d . . . . .
H014 H 0.5602 -0.2331 0.5479 0.079 Uiso 1 1 calc R . . . .
C015 C 0.6118(8) -0.2819(7) 0.6225(3) 0.074(2) Uani 1 1 d . . . . .
H015 H 0.5458 -0.3339 0.6293 0.089 Uiso 1 1 calc R . . . .
C016 C 0.8441(9) 0.3373(6) 0.2743(3) 0.074(2) Uani 1 1 d . . . . .
H016 H 0.8558 0.2528 0.2566 0.088 Uiso 1 1 calc R . . . .
C017 C 0.6091(8) 0.2803(6) 0.6937(3) 0.069(2) Uani 1 1 d . . . . .
H017 H 0.5295 0.2769 0.7225 0.083 Uiso 1 1 calc R . . . .
C018 C 0.9084(9) 0.8566(7) 0.1555(3) 0.070(2) Uani 1 1 d . . . . .
H018 H 0.9760 0.7600 0.1481 0.084 Uiso 1 1 calc R . . . .
C019 C 0.6989(8) 0.6183(7) 0.8027(3) 0.070(2) Uani 1 1 d . . . . .
C01A C 0.7218(9) 1.1351(8) 0.1725(4) 0.075(2) Uani 1 1 d . . . . .
H01J H 0.6571 1.2325 0.1790 0.089 Uiso 1 1 calc R . . . .
C01B C 0.8159(8) 0.3560(6) 0.6560(3) 0.068(2) Uani 1 1 d . . . . .
H01D H 0.8822 0.4065 0.6576 0.081 Uiso 1 1 calc R . . . .
C01C C 0.6332(9) 0.2100(6) 0.6457(3) 0.074(2) Uani 1 1 d . . . . .
H01E H 0.5677 0.1596 0.6424 0.089 Uiso 1 1 calc R . . . .
C01D C 0.7004(9) 0.3563(6) 0.7004(3) 0.070(2) Uani 1 1 d . . . . .
C01E C 0.7729(9) 1.4076(7) 1.0405(3) 0.064(2) Uani 1 1 d . . . . .
C01F C 0.8499(8) 0.4497(7) 0.2457(3) 0.071(2) Uani 1 1 d . . . . .
H01K H 0.8672 0.4421 0.2079 0.086 Uiso 1 1 calc R . . . .
C01G C 0.6796(10) 0.4249(8) 0.7540(4) 0.083(2) Uani 1 1 d . . . . .
C01H C 0.8977(10) 0.9508(9) 0.1157(3) 0.080(2) Uani 1 1 d . . . . .
H01L H 0.9613 0.9158 0.0813 0.096 Uiso 1 1 calc R . . . .
C01I C 0.8297(9) 0.2806(7) 0.6105(3) 0.078(2) Uani 1 1 d . . . . .
H01I H 0.9098 0.2806 0.5813 0.094 Uiso 1 1 calc R . . . .
C01J C 0.7164(9) 1.1021(7) 0.9818(3) 0.078(2) Uani 1 1 d . . . . .
C01K C 0.8404(8) 0.9880(7) 0.8049(3) 0.083(2) Uani 1 1 d . . . . .
H01F H 0.9405 0.9192 0.8140 0.125 Uiso 1 1 calc GR . . . .
H01G H 0.8378 1.0826 0.8093 0.125 Uiso 1 1 calc GR . . . .
H01H H 0.8358 0.9690 0.7678 0.125 Uiso 1 1 calc GR . . . .
C01L C 0.6942(10) 0.7769(7) 0.8898(3) 0.090(3) Uani 1 1 d . . . . .
C01M C 0.6967(10) 0.8796(7) 0.9276(3) 0.090(3) Uani 1 1 d . . . . .
C01N C 0.6968(11) 0.5635(8) 0.8527(4) 0.104(3) Uani 1 1 d . . . . .
H01N H 0.6973 0.4722 0.8569 0.125 Uiso 1 1 calc R . . . .
C01O C 0.6939(13) 0.6438(8) 0.8968(4) 0.130(4) Uani 1 1 d . . . . .
H01O H 0.6917 0.6078 0.9312 0.156 Uiso 1 1 calc R . . . .
C01P C 0.7089(13) 0.9871(9) 1.0089(4) 0.128(4) Uani 1 1 d . . . . .
H01P H 0.7095 0.9856 1.0462 0.153 Uiso 1 1 calc R . . . .
C01Q C 0.7007(13) 0.8745(9) 0.9827(4) 0.137(4) Uani 1 1 d . . . . .
H01Q H 0.6979 0.7955 1.0015 0.164 Uiso 1 1 calc R . . . .
C01R C 0.6690(17) 1.4497(13) 1.0922(6) 0.060(4) Uani 0.5 1 d . . P A 1
H01R H 0.5821 1.4202 1.1011 0.072 Uiso 0.5 1 calc R . P A 1
C01U C 0.9034(17) 1.3410(13) 1.0688(5) 0.063(4) Uani 0.5 1 d . . P A -1
H01U H 0.9720 1.2445 1.0619 0.075 Uiso 0.5 1 calc R . P A -1
C01V C 0.9247(19) 1.4233(15) 1.1062(6) 0.079(5) Uani 0.5 1 d . . P A -1
H01V H 1.0090 1.3813 1.1259 0.095 Uiso 0.5 1 calc R . P A -1
C01W C 0.6939(19) 1.5329(13) 1.1292(7) 0.070(4) Uani 0.5 1 d . . P A 1
H01W H 0.6234 1.5607 1.1629 0.084 Uiso 0.5 1 calc R . P A 1
C1 C 0.898(2) 1.5548(14) 1.0686(7) 0.072(4) Uani 0.5 1 d . . P A 1
H1 H 0.9729 1.5975 1.0595 0.086 Uiso 0.5 1 calc R . P A 1
C2 C 0.8809(19) 1.4785(13) 1.0294(6) 0.072(4) Uani 0.5 1 d . . P A 1
H2 H 0.9407 1.4716 0.9944 0.086 Uiso 0.5 1 calc R . P A 1
C3 C 0.680(2) 1.5380(16) 1.0509(7) 0.087(5) Uani 0.5 1 d . . P A -1
H3 H 0.5893 1.5837 1.0341 0.104 Uiso 0.5 1 calc R . P A -1
C5 C 0.721(2) 1.6067(17) 1.0884(8) 0.084(5) Uani 0.5 1 d . . P A -1
H5 H 0.6529 1.7038 1.0929 0.101 Uiso 0.5 1 calc R . P A -1


_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
N001 C00L 1.427(7) . ?
N001 C00N 1.349(7) . ?
N002 C00F 1.329(7) . ?
N002 C011 1.436(7) . ?
O003 C00N 1.230(7) . ?
N004 C019 1.419(8) . ?
N004 C01G 1.305(8) . ?
O005 C00F 1.187(7) . ?
N006 C01C 1.357(8) . ?
N006 C01I 1.316(8) . ?
N007 C00Z 1.337(7) . ?
N007 C015 1.330(8) . ?
N008 C01V 1.486(15) . ?
N008 C01W 1.385(17) . ?
N008 C1 1.285(16) . ?
N008 C5 1.218(18) . ?
N009 C01A 1.342(8) . ?
N009 C01H 1.346(8) . ?
C00A C00B 1.396(8) . ?
C00A C00L 1.404(7) . ?
C00B C00D 1.383(7) . ?
C00B C00J 1.539(7) . ?
C00C C00G 1.379(7) . ?
C00C C00J 1.517(8) . ?
C00C C00O 1.378(8) . ?
C00D C00G 1.464(8) . ?
C00D C00T 1.379(7) . ?
O00E C01G 1.243(8) . ?
C00F C00W 1.514(9) . ?
C00G C016 1.385(8) . ?
N00H C012 1.314(8) . ?
N00H C01J 1.430(8) . ?
C00I C00N 1.496(9) . ?
C00I C00X 1.369(8) . ?
C00I C014 1.398(8) . ?
C00J C00K 1.535(7) . ?
C00J C00M 1.556(7) . ?
C00L C00Q 1.386(8) . ?
C00O C011 1.403(8) . ?
C00P C00V 1.511(7) . ?
C00P C00Y 1.525(9) . ?
C00P C013 1.527(8) . ?
C00P C01K 1.543(8) . ?
C00Q C00T 1.400(8) . ?
O00R C012 1.158(7) . ?
C00S C00V 1.379(8) . ?
C00S C019 1.395(8) . ?
C00U C00Y 1.402(8) . ?
C00U C01J 1.403(9) . ?
C00V C01L 1.375(9) . ?
C00W C010 1.394(8) . ?
C00W C018 1.392(9) . ?
C00X C00Z 1.406(8) . ?
C00Y C01M 1.387(9) . ?
C010 C01A 1.384(9) . ?
C011 C01F 1.380(8) . ?
C012 C01E 1.512(9) . ?
C014 C015 1.390(9) . ?
C016 C01F 1.381(8) . ?
C017 C01C 1.373(8) . ?
C017 C01D 1.384(8) . ?
C018 C01H 1.388(9) . ?
C019 C01N 1.389(9) . ?
C01B C01D 1.406(9) . ?
C01B C01I 1.366(9) . ?
C01D C01G 1.496(10) . ?
C01E C01R 1.444(15) . ?
C01E C01U 1.437(14) . ?
C01E C2 1.436(15) . ?
C01E C3 1.287(15) . ?
C01J C01P 1.390(9) . ?
C01L C01M 1.456(9) . ?
C01L C01O 1.391(9) . ?
C01M C01Q 1.411(10) . ?
C01N C01O 1.397(10) . ?
C01P C01Q 1.386(10) . ?
C01R C01U 1.98(2) . ?
C01R C01W 1.391(17) . ?
C01R C3 1.403(19) . ?
C01R C5 1.86(2) . ?
C01U C01V 1.375(16) . ?
C01U C2 1.700(17) . ?
C01V C01W 1.95(2) . ?
C01V C1 1.621(19) . ?
C01W C3 2.02(2) . ?
C01W C5 1.33(2) . ?
C1 C2 1.347(17) . ?
C1 C5 1.48(2) . ?
C2 C3 1.69(2) . ?
C2 C5 1.98(2) . ?
C3 C5 1.38(2) . ?

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
C00N N001 C00L 127.2(6) . . ?
C00F N002 C011 126.9(6) . . ?
C01G N004 C019 128.3(7) . . ?
C01I N006 C01C 113.9(6) . . ?
C015 N007 C00Z 115.4(6) . . ?
C01W N008 C01V 85.5(8) . . ?
C1 N008 C01V 71.2(9) . . ?
C1 N008 C01W 117.9(11) . . ?
C5 N008 C01V 107.9(10) . . ?
C5 N008 C01W 61.0(10) . . ?
C5 N008 C1 72.7(11) . . ?
C01A N009 C01H 116.1(7) . . ?
C00B C00A C00L 118.2(6) . . ?
C00A C00B C00J 128.6(5) . . ?
C00D C00B C00A 120.8(5) . . ?
C00D C00B C00J 110.6(6) . . ?
C00G C00C C00J 110.9(6) . . ?
C00O C00C C00G 121.4(6) . . ?
C00O C00C C00J 127.6(5) . . ?
C00B C00D C00G 108.4(5) . . ?
C00T C00D C00B 121.0(6) . . ?
C00T C00D C00G 130.6(6) . . ?
N002 C00F C00W 114.6(6) . . ?
O005 C00F N002 126.6(7) . . ?
O005 C00F C00W 118.5(6) . . ?
C00C C00G C00D 109.2(6) . . ?
C00C C00G C016 121.0(6) . . ?
C016 C00G C00D 129.8(5) . . ?
C012 N00H C01J 127.8(6) . . ?
C00X C00I C00N 124.4(6) . . ?
C00X C00I C014 118.8(7) . . ?
C014 C00I C00N 116.6(7) . . ?
C00B C00J C00M 109.4(5) . . ?
C00C C00J C00B 100.8(5) . . ?
C00C C00J C00K 113.9(5) . . ?
C00C C00J C00M 111.5(5) . . ?
C00K C00J C00B 112.7(5) . . ?
C00K C00J C00M 108.3(5) . . ?
C00A C00L N001 117.7(6) . . ?
C00Q C00L N001 121.6(5) . . ?
C00Q C00L C00A 120.7(6) . . ?
N001 C00N C00I 116.9(6) . . ?
O003 C00N N001 123.6(7) . . ?
O003 C00N C00I 119.5(6) . . ?
C00C C00O C011 117.5(6) . . ?
C00V C00P C00Y 100.7(5) . . ?
C00V C00P C013 110.9(5) . . ?
C00V C00P C01K 112.8(5) . . ?
C00Y C00P C013 111.6(5) . . ?
C00Y C00P C01K 112.0(5) . . ?
C013 C00P C01K 108.8(6) . . ?
C00L C00Q C00T 120.2(6) . . ?
C00V C00S C019 120.2(7) . . ?
C00D C00T C00Q 119.1(6) . . ?
C00Y C00U C01J 117.9(6) . . ?
C00S C00V C00P 128.4(7) . . ?
C01L C00V C00P 111.9(6) . . ?
C01L C00V C00S 119.7(6) . . ?
C010 C00W C00F 119.7(7) . . ?
C018 C00W C00F 122.7(6) . . ?
C018 C00W C010 117.6(7) . . ?
C00I C00X C00Z 118.0(6) . . ?
C00U C00Y C00P 128.3(6) . . ?
C01M C00Y C00P 110.1(6) . . ?
C01M C00Y C00U 121.6(7) . . ?
N007 C00Z C00X 124.8(7) . . ?
C01A C010 C00W 119.2(7) . . ?
C00O C011 N002 124.0(6) . . ?
C01F C011 N002 115.1(6) . . ?
C01F C011 C00O 120.9(6) . . ?
N00H C012 C01E 114.5(7) . . ?
O00R C012 N00H 124.4(7) . . ?
O00R C012 C01E 120.8(7) . . ?
C015 C014 C00I 117.9(7) . . ?
N007 C015 C014 125.1(7) . . ?
C01F C016 C00G 118.3(6) . . ?
C01C C017 C01D 120.2(7) . . ?
C01H C018 C00W 118.9(7) . . ?
C00S C019 N004 118.1(7) . . ?
C01N C019 N004 121.7(6) . . ?
C01N C019 C00S 120.1(7) . . ?
N009 C01A C010 124.0(7) . . ?
C01I C01B C01D 117.9(7) . . ?
N006 C01C C017 124.1(7) . . ?
C017 C01D C01B 116.4(7) . . ?
C017 C01D C01G 119.4(8) . . ?
C01B C01D C01G 124.1(7) . . ?
C01R C01E C012 123.2(8) . . ?
C01U C01E C012 119.6(8) . . ?
C01U C01E C01R 86.7(9) . . ?
C2 C01E C012 122.4(8) . . ?
C2 C01E C01R 113.0(9) . . ?
C2 C01E C01U 72.5(8) . . ?
C3 C01E C012 119.7(9) . . ?
C3 C01E C01R 61.5(9) . . ?
C3 C01E C01U 120.7(10) . . ?
C3 C01E C2 76.3(10) . . ?
C011 C01F C016 120.9(6) . . ?
N004 C01G C01D 118.9(7) . . ?
O00E C01G N004 123.5(8) . . ?
O00E C01G C01D 117.6(7) . . ?
N009 C01H C018 124.1(8) . . ?
N006 C01I C01B 127.5(8) . . ?
C00U C01J N00H 124.3(7) . . ?
C01P C01J N00H 115.2(7) . . ?
C01P C01J C00U 120.5(7) . . ?
C00V C01L C01M 108.1(6) . . ?
C00V C01L C01O 121.0(7) . . ?
C01O C01L C01M 130.9(8) . . ?
C00Y C01M C01L 109.2(7) . . ?
C00Y C01M C01Q 119.9(7) . . ?
C01Q C01M C01L 130.9(7) . . ?
C019 C01N C01O 119.4(7) . . ?
C01L C01O C01N 119.4(8) . . ?
C01Q C01P C01J 121.4(8) . . ?
C01P C01Q C01M 118.6(7) . . ?
C01E C01R C01U 46.5(6) . . ?
C01E C01R C5 84.9(10) . . ?
C01W C01R C01E 121.1(13) . . ?
C01W C01R C01U 92.4(11) . . ?
C01W C01R C3 92.7(12) . . ?
C01W C01R C5 45.4(9) . . ?
C3 C01R C01E 53.8(9) . . ?
C3 C01R C01U 87.2(11) . . ?
C3 C01R C5 47.6(9) . . ?
C5 C01R C01U 85.4(9) . . ?
C01E C01U C01R 46.8(6) . . ?
C01E C01U C2 53.7(7) . . ?
C01V C01U C01E 117.0(12) . . ?
C01V C01U C01R 86.4(10) . . ?
C01V C01U C2 85.1(10) . . ?
C2 C01U C01R 81.2(9) . . ?
N008 C01V C01W 45.1(6) . . ?
N008 C01V C1 48.6(7) . . ?
C01U C01V N008 122.7(13) . . ?
C01U C01V C01W 94.1(11) . . ?
C01U C01V C1 94.0(12) . . ?
C1 C01V C01W 79.1(10) . . ?
N008 C01W C01R 120.1(15) . . ?
N008 C01W C01V 49.4(7) . . ?
N008 C01W C3 88.4(11) . . ?
C01R C01W C01V 87.1(10) . . ?
C01R C01W C3 43.9(8) . . ?
C01V C01W C3 86.5(10) . . ?
C5 C01W N008 53.2(10) . . ?
C5 C01W C01R 86.4(15) . . ?
C5 C01W C01V 81.5(13) . . ?
C5 C01W C3 42.9(11) . . ?
N008 C1 C01V 60.2(9) . . ?
N008 C1 C2 126.0(15) . . ?
N008 C1 C5 51.5(9) . . ?
C2 C1 C01V 89.2(11) . . ?
C2 C1 C5 88.8(14) . . ?
C5 C1 C01V 89.7(13) . . ?
C01E C2 C01U 53.8(7) . . ?
C01E C2 C3 47.9(7) . . ?
C01E C2 C5 80.7(10) . . ?
C01U C2 C5 89.7(10) . . ?
C1 C2 C01E 120.2(13) . . ?
C1 C2 C01U 91.6(11) . . ?
C1 C2 C3 91.8(12) . . ?
C1 C2 C5 48.5(10) . . ?
C3 C2 C01U 88.8(11) . . ?
C3 C2 C5 43.4(8) . . ?
C01E C3 C01R 64.8(10) . . ?
C01E C3 C01W 93.8(11) . . ?
C01E C3 C2 55.9(8) . . ?
C01E C3 C5 114.9(14) . . ?
C01R C3 C01W 43.4(8) . . ?
C01R C3 C2 101.7(12) . . ?
C2 C3 C01W 94.6(10) . . ?
C5 C3 C01R 83.9(14) . . ?
C5 C3 C01W 40.8(10) . . ?
C5 C3 C2 79.8(12) . . ?
N008 C5 C01R 100.6(13) . . ?
N008 C5 C01W 65.7(13) . . ?
N008 C5 C1 55.7(11) . . ?
N008 C5 C2 91.0(12) . . ?
N008 C5 C3 136.6(16) . . ?
C01R C5 C2 77.2(8) . . ?
C01W C5 C01R 48.2(10) . . ?
C01W C5 C1 108.6(17) . . ?
C01W C5 C2 109.7(12) . . ?
C01W C5 C3 96.3(17) . . ?
C1 C5 C01R 106.6(11) . . ?
C1 C5 C2 42.8(8) . . ?
C3 C5 C01R 48.5(10) . . ?
C3 C5 C1 99.5(14) . . ?
C3 C5 C2 56.8(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_2                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.881 Why?  
RESPONSE: The crystal was poorly diffracting at high angles
;
# end Validation Reply Form
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2098426'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 N4 O3, 2(H2 O)'
_chemical_formula_sum            'C25 H20 N4 O5'
_chemical_formula_weight         456.45
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.5492(10)
_cell_length_b                   7.4023(5)
_cell_length_c                   21.4841(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.382(2)
_cell_angle_gamma                90
_cell_volume                     2119.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2197
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.548
_cell_measurement_theta_min      1.927
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_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            ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11535
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.548
_diffrn_reflns_theta_min         1.927
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?\~A^1^
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1660
_reflns_number_total             2197
_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    ?
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0733
_refine_ls_restrained_S_all      1.124
_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)+(0.0456P)²+5.8115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1582
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O004(H00C,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.26962(17) 0.9477(3) 0.61628(11) 0.0378(6) Uani 1 1 d . . . . .
O002 O 0.0000 1.0068(4) 0.7500 0.0374(8) Uani 1 2 d S T P . .
N003 N 0.28478(18) 0.6478(3) 0.64030(12) 0.0279(6) Uani 1 1 d . . . . .
H003 H 0.3226 0.5528 0.6370 0.033 Uiso 1 1 calc R . . . .
O004 O 0.6530(2) 0.6959(3) 0.40118(15) 0.0622(9) Uani 1 1 d . . . . .
H00C H 0.6764 0.8048 0.3990 0.093 Uiso 1 1 d G . . . .
H00F H 0.6216 0.6994 0.4331 0.093 Uiso 1 1 d G . . . .
N5 N 0.5304(2) 0.7325(4) 0.49468(13) 0.0349(7) Uani 1 1 d . . . . .
C006 C 0.0707(2) 0.7207(4) 0.72385(13) 0.0213(6) Uani 1 1 d . . . . .
C007 C 0.0449(2) 0.5412(4) 0.73468(13) 0.0212(6) Uani 1 1 d . . . . .
C008 C 0.2050(2) 0.6230(4) 0.67468(13) 0.0236(6) Uani 1 1 d . . . . .
C009 C 0.3084(2) 0.7978(4) 0.61272(14) 0.0256(7) Uani 1 1 d . . . . .
C00A C 0.1496(2) 0.7653(4) 0.69408(13) 0.0246(7) Uani 1 1 d . . . . .
H00A H 0.1657 0.8877 0.6871 0.030 Uiso 1 1 calc R . . . .
C00B C 0.1814(2) 0.4444(4) 0.68725(14) 0.0268(7) Uani 1 1 d . . . . .
H00B H 0.2208 0.3493 0.6748 0.032 Uiso 1 1 calc R . . . .
C00C C 0.0000 0.8418(5) 0.7500 0.0250(9) Uani 1 2 d S T P . .
C00D C 0.1021(2) 0.4023(4) 0.71726(14) 0.0261(7) Uani 1 1 d . . . . .
H00D H 0.0874 0.2802 0.7257 0.031 Uiso 1 1 calc R . . . .
C00E C 0.4743(2) 0.6725(4) 0.59194(15) 0.0299(7) Uani 1 1 d . . . . .
H00E H 0.4853 0.6145 0.6320 0.036 Uiso 1 1 calc R . . . .
C00F C 0.3879(2) 0.7735(4) 0.57175(15) 0.0280(7) Uani 1 1 d . . . . .
C00G C 0.3744(2) 0.8536(5) 0.51276(15) 0.0330(7) Uani 1 1 d . . . . .
H00G H 0.3168 0.9254 0.4979 0.040 Uiso 1 1 calc R . . . .
C00H C 0.5441(2) 0.6585(4) 0.55237(17) 0.0355(8) Uani 1 1 d . . . . .
H00H H 0.6043 0.5934 0.5668 0.043 Uiso 1 1 calc R . . . .
C00I C 0.4467(2) 0.8268(5) 0.47593(16) 0.0361(8) Uani 1 1 d . . . . .
H00I H 0.4361 0.8786 0.4348 0.043 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 C009 1.236(4) . ?
O002 C00C 1.221(5) . ?
N003 H003 0.8800 . ?
N003 C008 1.426(3) . ?
N003 C009 1.324(4) . ?
O004 H00C 0.8701 . ?
O004 H00F 0.8701 . ?
N5 C00H 1.337(4) . ?
N5 C00I 1.331(4) . ?
C006 C007 1.404(4) . ?
C006 C00A 1.382(4) . ?
C006 C00C 1.493(3) . ?
C007 C007 1.484(5) 2_556 ?
C007 C00D 1.380(4) . ?
C008 C00A 1.400(4) . ?
C008 C00B 1.399(4) . ?
C009 C00F 1.519(4) . ?
C00A H00A 0.9500 . ?
C00B H00B 0.9500 . ?
C00B C00D 1.384(4) . ?
C00C C006 1.493(4) 2_556 ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00E C00F 1.392(4) . ?
C00E C00H 1.384(4) . ?
C00F C00G 1.381(4) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.380(4) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?

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
C008 N003 H003 116.4 . . ?
C009 N003 H003 116.4 . . ?
C009 N003 C008 127.3(2) . . ?
H00C O004 H00F 104.5 . . ?
C00I N5 C00H 117.6(3) . . ?
C007 C006 C00C 108.1(2) . . ?
C00A C006 C007 122.6(2) . . ?
C00A C006 C00C 129.3(3) . . ?
C006 C007 C007 108.77(15) . 2_556 ?
C00D C007 C006 119.4(2) . . ?
C00D C007 C007 131.78(16) . 2_556 ?
C00A C008 N003 123.7(3) . . ?
C00B C008 N003 116.3(2) . . ?
C00B C008 C00A 120.0(2) . . ?
O001 C009 N003 125.8(3) . . ?
O001 C009 C00F 119.7(3) . . ?
N003 C009 C00F 114.4(3) . . ?
C006 C00A C008 117.4(3) . . ?
C006 C00A H00A 121.3 . . ?
C008 C00A H00A 121.3 . . ?
C008 C00B H00B 119.1 . . ?
C00D C00B C008 121.8(3) . . ?
C00D C00B H00B 119.1 . . ?
O002 C00C C006 126.89(16) . . ?
O002 C00C C006 126.89(16) . 2_556 ?
C006 C00C C006 106.2(3) . 2_556 ?
C007 C00D C00B 118.7(3) . . ?
C007 C00D H00D 120.7 . . ?
C00B C00D H00D 120.7 . . ?
C00F C00E H00E 120.7 . . ?
C00H C00E H00E 120.7 . . ?
C00H C00E C00F 118.6(3) . . ?
C00E C00F C009 121.9(3) . . ?
C00G C00F C009 119.4(3) . . ?
C00G C00F C00E 118.8(3) . . ?
C00F C00G H00G 120.8 . . ?
C00I C00G C00F 118.3(3) . . ?
C00I C00G H00G 120.8 . . ?
N5 C00H C00E 122.9(3) . . ?
N5 C00H H00H 118.6 . . ?
C00E C00H H00H 118.6 . . ?
N5 C00I C00G 123.8(3) . . ?
N5 C00I H00I 118.1 . . ?
C00G C00I H00I 118.1 . . ?

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
N003 H003 O004 0.88 2.07 2.872(3) 151.7 5_666

_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_1
_database_code_depnum_ccdc_archive 'CCDC 2098425'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 N4 O2'
_chemical_formula_sum            'C25 H18 N4 O2'
_chemical_formula_weight         406.43
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7678(2)
_cell_length_b                   5.82960(10)
_cell_length_c                   42.6250(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.468(2)
_cell_angle_gamma                90
_cell_volume                     1929.56(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3947
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.435
_cell_measurement_theta_min      4.150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_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            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1363
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            34359
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.435
_diffrn_reflns_theta_min         4.150
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2426
_reflns_number_total             3947
_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    ?
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.011
_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)+(0.0898P)²+0.0303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1713
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00C,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F),
 C00I(H00I), C00K(H00K), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6090(3) 0.4292(4) 0.37740(4) 0.0496(5) Uani 1 1 d . . . . .
O002 O 0.4630(3) 0.3264(3) 0.13195(4) 0.0519(6) Uani 1 1 d . . . . .
N003 N 0.5874(3) 0.6766(4) 0.14087(4) 0.0341(5) Uani 1 1 d . . . . .
H003 H 0.6393 0.7900 0.1313 0.041 Uiso 1 1 calc R . . . .
N004 N 0.3790(3) 0.6488(4) 0.36449(5) 0.0370(5) Uani 1 1 d . . . . .
H004 H 0.2821 0.7087 0.3709 0.044 Uiso 1 1 calc R . . . .
N005 N 0.6864(3) 0.5249(4) 0.02610(5) 0.0469(6) Uani 1 1 d . . . . .
N006 N 0.2987(3) 0.4724(4) 0.47923(5) 0.0497(6) Uani 1 1 d . . . . .
C007 C 0.5475(3) 0.7880(4) 0.23782(5) 0.0280(5) Uani 1 1 d . . . . .
C008 C 0.5207(3) 0.7828(4) 0.27180(5) 0.0273(5) Uani 1 1 d . . . . .
C009 C 0.4766(3) 0.5888(4) 0.22439(5) 0.0285(5) Uani 1 1 d . . . . .
C00A C 0.6242(3) 0.9490(4) 0.21857(5) 0.0314(5) Uani 1 1 d . . . . .
H00A H 0.6710 1.0861 0.2273 0.038 Uiso 1 1 calc R . . . .
C00B C 0.4833(3) 0.5453(4) 0.19243(5) 0.0315(6) Uani 1 1 d . . . . .
H00B H 0.4341 0.4099 0.1836 0.038 Uiso 1 1 calc R . . . .
C00C C 0.4311(3) 0.5809(4) 0.27892(5) 0.0300(5) Uani 1 1 d . . . . .
C00D C 0.6318(3) 0.9082(4) 0.18675(5) 0.0329(6) Uani 1 1 d . . . . .
H00D H 0.6836 1.0186 0.1736 0.039 Uiso 1 1 calc R . . . .
C00E C 0.5642(3) 0.7061(4) 0.17362(5) 0.0303(6) Uani 1 1 d . . . . .
C00F C 0.3849(3) 0.5338(4) 0.30937(5) 0.0333(6) Uani 1 1 d . . . . .
H00F H 0.3241 0.3974 0.3142 0.040 Uiso 1 1 calc R . . . .
C00G C 0.4739(3) 0.5229(4) 0.38447(6) 0.0343(6) Uani 1 1 d . . . . .
C00H C 0.4084(3) 0.5071(4) 0.41732(6) 0.0341(6) Uani 1 1 d . . . . .
C00I C 0.5648(3) 0.9391(4) 0.29532(5) 0.0329(6) Uani 1 1 d . . . . .
H00I H 0.6255 1.0757 0.2906 0.039 Uiso 1 1 calc R . . . .
C00J C 0.5929(3) 0.5151(5) 0.08907(5) 0.0349(6) Uani 1 1 d . . . . .
C00K C 0.5185(3) 0.8916(4) 0.32595(5) 0.0354(6) Uani 1 1 d . . . . .
H00K H 0.5476 0.9963 0.3423 0.042 Uiso 1 1 calc R . . . .
C00L C 0.4293(3) 0.6903(4) 0.33268(6) 0.0341(6) Uani 1 1 d . . . . .
C00M C 0.3968(3) 0.4442(4) 0.24943(5) 0.0333(6) Uani 1 1 d . . . . .
H00C H 0.4519 0.2913 0.2508 0.040 Uiso 1 1 calc R . . . .
H00E H 0.2716 0.4245 0.2453 0.040 Uiso 1 1 calc R . . . .
C00N C 0.5402(3) 0.4975(5) 0.12266(6) 0.0370(6) Uani 1 1 d . . . . .
C00O C 0.3116(4) 0.6795(5) 0.43072(6) 0.0399(7) Uani 1 1 d . . . . .
H00O H 0.2804 0.8120 0.4189 0.048 Uiso 1 1 calc R . . . .
C00P C 0.6746(4) 0.3294(5) 0.07553(6) 0.0410(7) Uani 1 1 d . . . . .
H00P H 0.6994 0.1953 0.0875 0.049 Uiso 1 1 calc R . . . .
C00Q C 0.2609(4) 0.6562(5) 0.46159(6) 0.0460(7) Uani 1 1 d . . . . .
H00Q H 0.1963 0.7767 0.4706 0.055 Uiso 1 1 calc R . . . .
C00R C 0.4502(4) 0.3185(5) 0.43564(6) 0.0438(7) Uani 1 1 d . . . . .
H00R H 0.5181 0.1979 0.4275 0.053 Uiso 1 1 calc R . . . .
C00S C 0.5576(4) 0.7049(5) 0.07057(6) 0.0433(7) Uani 1 1 d . . . . .
H00S H 0.5020 0.8356 0.0790 0.052 Uiso 1 1 calc R . . . .
C00T C 0.7193(4) 0.3424(5) 0.04426(6) 0.0453(7) Uani 1 1 d . . . . .
H00T H 0.7763 0.2150 0.0353 0.054 Uiso 1 1 calc R . . . .
C00U C 0.6054(4) 0.6996(5) 0.03945(6) 0.0476(8) Uani 1 1 d . . . . .
H00U H 0.5785 0.8295 0.0268 0.057 Uiso 1 1 calc R . . . .
C00V C 0.3918(4) 0.3078(5) 0.46603(7) 0.0525(8) Uani 1 1 d . . . . .
H00V H 0.4197 0.1757 0.4782 0.063 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 C00G 1.228(3) . ?
O002 C00N 1.234(3) . ?
N003 C00E 1.422(3) . ?
N003 C00N 1.347(3) . ?
N004 C00G 1.332(3) . ?
N004 C00L 1.441(3) . ?
N005 C00T 1.336(4) . ?
N005 C00U 1.333(4) . ?
N006 C00Q 1.338(4) . ?
N006 C00V 1.335(4) . ?
C007 C008 1.469(3) . ?
C007 C009 1.401(3) . ?
C007 C00A 1.391(3) . ?
C008 C00C 1.404(3) . ?
C008 C00I 1.391(3) . ?
C009 C00B 1.388(3) . ?
C009 C00M 1.506(3) . ?
C00A C00D 1.380(3) . ?
C00B C00E 1.394(3) . ?
C00C C00F 1.383(3) . ?
C00C C00M 1.506(3) . ?
C00D C00E 1.401(3) . ?
C00F C00L 1.386(3) . ?
C00G C00H 1.505(3) . ?
C00H C00O 1.386(3) . ?
C00H C00R 1.382(4) . ?
C00I C00K 1.391(3) . ?
C00J C00N 1.503(3) . ?
C00J C00P 1.388(4) . ?
C00J C00S 1.382(4) . ?
C00K C00L 1.396(3) . ?
C00O C00Q 1.390(3) . ?
C00P C00T 1.388(4) . ?
C00R C00V 1.385(4) . ?
C00S C00U 1.387(4) . ?

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
C00N N003 C00E 128.3(2) . . ?
C00G N004 C00L 122.3(2) . . ?
C00U N005 C00T 116.5(2) . . ?
C00V N006 C00Q 116.9(2) . . ?
C009 C007 C008 108.8(2) . . ?
C00A C007 C008 132.0(2) . . ?
C00A C007 C009 119.2(2) . . ?
C00C C008 C007 108.3(2) . . ?
C00I C008 C007 131.2(2) . . ?
C00I C008 C00C 120.5(2) . . ?
C007 C009 C00M 109.8(2) . . ?
C00B C009 C007 121.9(2) . . ?
C00B C009 C00M 128.3(2) . . ?
C00D C00A C007 119.6(2) . . ?
C009 C00B C00E 118.1(2) . . ?
C008 C00C C00M 109.9(2) . . ?
C00F C00C C008 120.7(2) . . ?
C00F C00C C00M 129.3(2) . . ?
C00A C00D C00E 120.8(2) . . ?
C00B C00E N003 123.6(2) . . ?
C00B C00E C00D 120.4(2) . . ?
C00D C00E N003 116.0(2) . . ?
C00C C00F C00L 118.4(2) . . ?
O001 C00G N004 123.4(2) . . ?
O001 C00G C00H 120.8(2) . . ?
N004 C00G C00H 115.7(2) . . ?
C00O C00H C00G 122.6(2) . . ?
C00R C00H C00G 119.6(2) . . ?
C00R C00H C00O 117.8(2) . . ?
C00K C00I C008 118.7(2) . . ?
C00P C00J C00N 118.8(2) . . ?
C00S C00J C00N 122.9(2) . . ?
C00S C00J C00P 118.3(2) . . ?
C00I C00K C00L 120.1(2) . . ?
C00F C00L N004 119.7(2) . . ?
C00F C00L C00K 121.4(2) . . ?
C00K C00L N004 118.9(2) . . ?
C009 C00M C00C 103.2(2) . . ?
O002 C00N N003 124.7(2) . . ?
O002 C00N C00J 120.5(2) . . ?
N003 C00N C00J 114.8(2) . . ?
C00H C00O C00Q 119.3(3) . . ?
C00T C00P C00J 119.0(3) . . ?
N006 C00Q C00O 123.2(3) . . ?
C00H C00R C00V 119.1(3) . . ?
C00J C00S C00U 118.3(3) . . ?
N005 C00T C00P 123.4(3) . . ?
N005 C00U C00S 124.5(3) . . ?
N006 C00V C00R 123.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
