# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_DCPV
_database_code_depnum_ccdc_archive 'CCDC 2226858'
loop_
_audit_author_name
_audit_author_address
'Sanjay Mandal'
;IISER Mohali
India
;
_audit_update_record             
;
2023-02-23 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2018.7-2'
_chemical_formula_moiety         'C16 H12 N4'
_chemical_formula_sum            'C16 H12 N4'
_chemical_formula_weight         260.301
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   18.742(2)
_cell_length_b                   5.2346(5)
_cell_length_c                   14.0627(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.787(3)
_cell_angle_gamma                90
_cell_volume                     1327.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9700
_cell_measurement_temperature    102.(2)
_cell_measurement_theta_max      66.6954
_cell_measurement_theta_min      4.5877
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6181
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9962
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19721
_diffrn_reflns_point_group_measured_fraction_full 0.9962
_diffrn_reflns_point_group_measured_fraction_max 0.9962
_diffrn_reflns_theta_full        66.6993
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_min         2.45
_diffrn_ambient_temperature      102.00
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -22
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2237
_reflns_number_total             2344
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.3808
_refine_diff_density_min         -0.3022
_refine_diff_density_rms         0.0920
_refine_ls_d_res_high            0.8393
_refine_ls_d_res_low             18.0350
_refine_ls_goodness_of_fit_ref   1.1234
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.1234
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0535
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-01-05_17-21-55
;
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_refinement_flags_posn
N1 N 0.45104(3) 0.80029(8) 0.92150(3) 0.02087(12) Uani 1.000000 .
H1a H 0.4342(4) 0.9709(15) 0.9409(6) 0.039(2) Uani 1.000000 .
H1b H 0.5047(5) 0.7870(15) 0.9202(6) 0.0353(19) Uani 1.000000 .
N4 N 0.17400(3) -0.22225(9) 0.44882(4) 0.03367(13) Uani 1.000000 .
N3 N 0.37193(2) 0.25088(8) 0.50302(3) 0.02304(12) Uani 1.000000 .
N2 N 0.49743(2) 0.38745(8) 0.82861(3) 0.01837(11) Uani 1.000000 .
H2a H 0.5226(4) 0.3845(15) 0.9027(6) 0.0359(19) Uani 1.000000 .
H2b H 0.5062(4) 0.2206(15) 0.7978(6) 0.041(2) Uani 1.000000 .
C1 C 0.39946(2) 0.66692(8) 0.85058(3) 0.01566(12) Uani 1.000000 .
C2 C 0.42171(2) 0.45073(8) 0.80504(3) 0.01442(12) Uani 1.000000 .
C3 C 0.36896(2) 0.31434(8) 0.73551(3) 0.01523(12) Uani 1.000000 .
H3 H 0.3869(4) 0.1448(13) 0.7052(5) 0.0345(17) Uani 1.000000 .
C4 C 0.29357(2) 0.38419(8) 0.70954(3) 0.01557(12) Uani 1.000000 .
C7 C 0.23847(2) 0.24034(8) 0.63626(3) 0.01569(12) Uani 1.000000 .
C8 C 0.16337(3) 0.21403(8) 0.64922(3) 0.01629(12) Uani 1.000000 .
C9 C 0.15437(3) 0.15141(8) 0.74214(3) 0.01902(12) Uani 1.000000 .
H9 H 0.2030(4) 0.1234(15) 0.8044(5) 0.0410(19) Uani 1.000000 .
C10 C 0.08385(3) 0.11881(9) 0.75426(4) 0.02275(13) Uani 1.000000 .
H10 H 0.0786(4) 0.0659(17) 0.8267(6) 0.048(2) Uani 1.000000 .
C11 C 0.02157(3) 0.15497(9) 0.67472(4) 0.02367(13) Uani 1.000000 .
H11 H -0.0330(4) 0.1303(15) 0.6850(6) 0.0446(19) Uani 1.000000 .
C5 C 0.27178(3) 0.59361(8) 0.75782(3) 0.01751(12) Uani 1.000000 .
H5 H 0.2139(4) 0.6479(13) 0.7406(5) 0.0342(17) Uani 1.000000 .
C6 C 0.32430(3) 0.73307(8) 0.82646(3) 0.01775(12) Uani 1.000000 .
H6 H 0.3086(4) 0.8955(13) 0.8626(6) 0.0367(18) Uani 1.000000 .
C14 C 0.25490(2) 0.12744(8) 0.55594(3) 0.01756(12) Uani 1.000000 .
C16 C 0.20859(3) -0.06183(9) 0.49621(3) 0.02268(13) Uani 1.000000 .
C15 C 0.32009(3) 0.19258(8) 0.52749(3) 0.01870(12) Uani 1.000000 .
C12 C 0.02998(3) 0.22720(9) 0.58314(4) 0.02328(13) Uani 1.000000 .
H12 H -0.0178(4) 0.2603(17) 0.5230(6) 0.049(2) Uani 1.000000 .
C13 C 0.10050(3) 0.25455(9) 0.56999(4) 0.02067(13) Uani 1.000000 .
H13 H 0.1080(4) 0.3122(17) 0.4990(5) 0.045(2) Uani 1.000000 .


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
N1 H1a 1.009(7) . ?
N1 H1b 1.013(8) . ?
N1 C1 1.3755(6) . ?
N4 C16 1.1552(7) . ?
N3 C15 1.1563(7) . ?
N2 H2a 1.021(8) . ?
N2 H2b 1.008(7) . ?
N2 C2 1.4063(6) . ?
C1 C2 1.4177(6) . ?
C1 C6 1.3998(7) . ?
C2 C3 1.3846(6) . ?
C3 H3 1.077(6) . ?
C3 C4 1.4082(6) . ?
C4 C7 1.4547(6) . ?
C4 C5 1.4072(6) . ?
C7 C8 1.4742(7) . ?
C7 C14 1.3816(6) . ?
C8 C9 1.4012(7) . ?
C8 C13 1.4002(6) . ?
C9 H9 1.088(7) . ?
C9 C10 1.3883(7) . ?
C10 H10 1.086(8) . ?
C10 C11 1.3926(8) . ?
C11 H11 1.078(7) . ?
C11 C12 1.3918(7) . ?
C5 H5 1.083(7) . ?
C5 C6 1.3843(6) . ?
C6 H6 1.072(7) . ?
C14 C16 1.4296(6) . ?
C14 C15 1.4267(6) . ?
C12 H12 1.065(7) . ?
C12 C13 1.3909(7) . ?
C13 H13 1.087(8) . ?

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
H1b N1 H1a 116.7(6) . . ?
C1 N1 H1a 115.8(5) . . ?
C1 N1 H1b 117.2(4) . . ?
H2b N2 H2a 110.0(6) . . ?
C2 N2 H2a 113.6(4) . . ?
C2 N2 H2b 112.0(4) . . ?
C2 C1 N1 119.84(4) . . ?
C6 C1 N1 120.84(4) . . ?
C6 C1 C2 119.22(4) . . ?
C1 C2 N2 118.91(4) . . ?
C3 C2 N2 121.73(4) . . ?
C3 C2 C1 119.30(4) . . ?
H3 C3 C2 117.7(4) . . ?
C4 C3 C2 121.50(4) . . ?
C4 C3 H3 120.7(4) . . ?
C7 C4 C3 121.21(4) . . ?
C5 C4 C3 118.65(4) . . ?
C5 C4 C7 120.12(4) . . ?
C8 C7 C4 118.58(4) . . ?
C14 C7 C4 121.84(4) . . ?
C14 C7 C8 119.58(4) . . ?
C9 C8 C7 119.90(4) . . ?
C13 C8 C7 120.84(4) . . ?
C13 C8 C9 119.26(4) . . ?
H9 C9 C8 119.7(4) . . ?
C10 C9 C8 120.23(5) . . ?
C10 C9 H9 120.1(4) . . ?
H10 C10 C9 118.6(4) . . ?
C11 C10 C9 120.18(5) . . ?
C11 C10 H10 121.2(4) . . ?
H11 C11 C10 119.6(4) . . ?
C12 C11 C10 119.93(5) . . ?
C12 C11 H11 120.5(4) . . ?
H5 C5 C4 120.0(4) . . ?
C6 C5 C4 120.17(4) . . ?
C6 C5 H5 119.8(3) . . ?
C5 C6 C1 121.08(4) . . ?
H6 C6 C1 118.0(4) . . ?
H6 C6 C5 120.9(4) . . ?
C16 C14 C7 122.82(4) . . ?
C15 C14 C7 121.69(4) . . ?
C15 C14 C16 115.49(4) . . ?
C14 C16 N4 176.81(6) . . ?
C14 C15 N3 178.16(5) . . ?
H12 C12 C11 119.8(5) . . ?
C13 C12 C11 120.13(5) . . ?
C13 C12 H12 120.1(5) . . ?
C12 C13 C8 120.20(5) . . ?
H13 C13 C8 118.8(4) . . ?
H13 C13 C12 121.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -4.38(5) . . . . ?
N1 C1 C2 C3 178.42(4) . . . . ?
N1 C1 C6 C5 -177.55(4) . . . . ?
N2 C2 C1 C6 179.13(4) . . . . ?
N2 C2 C3 C4 -177.64(4) . . . . ?
C1 C2 C3 C4 -0.53(5) . . . . ?
C1 C6 C5 C4 -1.17(5) . . . . ?
C2 C3 C4 C7 179.86(4) . . . . ?
C2 C3 C4 C5 -1.72(5) . . . . ?
C3 C4 C7 C8 145.68(4) . . . . ?
C3 C4 C7 C14 -33.87(5) . . . . ?
C3 C4 C5 C6 2.57(5) . . . . ?
C4 C7 C8 C9 -45.28(4) . . . . ?
C4 C7 C8 C13 133.77(4) . . . . ?
C4 C7 C14 C16 164.96(4) . . . . ?
C4 C7 C14 C15 -14.73(5) . . . . ?
C7 C8 C9 C10 -178.08(4) . . . . ?
C7 C8 C13 C12 179.53(4) . . . . ?
C8 C9 C10 C11 -1.75(5) . . . . ?
C8 C13 C12 C11 -1.14(5) . . . . ?
C9 C10 C11 C12 -0.84(5) . . . . ?
C10 C11 C12 C13 2.28(6) . . . . ?


_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_bidcpv
_database_code_depnum_ccdc_archive 'CCDC 2226859'
loop_
_audit_author_name
_audit_author_address
'Sanjay Mandal'
;IISER Mohali
India
;
_audit_update_record             
;
2023-02-23 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2018.7-2'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 N4, 1.25(C H4 O)'
_chemical_formula_sum            'C24.25 H19 N4 O1.25'
_chemical_formula_weight         386.43
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9540(15)
_cell_length_b                   27.051(4)
_cell_length_c                   7.6877(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.868(6)
_cell_angle_gamma                90
_cell_volume                     2059.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9418
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.74
_cell_measurement_theta_min      4.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1484 before and 0.1160 after correction.
The Ratio of minimum to maximum transmission is 0.7643.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             810
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            29626
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.734
_diffrn_reflns_theta_max         66.734
_diffrn_reflns_theta_min         4.465
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3253
_reflns_number_total             3638
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 v2018.7-2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.071
_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)+(0.0896P)²+0.4761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1483
_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, All O(H) groups
2. Rigid bond restraints
 O1A, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C24) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C25, O1B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1A, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: H1(0.5) H2(0.5) O1A(0.5) H1A(0.5) C24(0.5) H24A(0.5) H24B(0.5)
 H24C(0.5) O1C(0.5) H1C(0.5) C26(0.5) H26A(0.5) H26B(0.5) H26C(0.5) C25(0.25)
 H25A(0.25) H25B(0.25) H25C(0.25) O1B(0.25) H1B(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
6.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
6.c Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1C(H1C), O1B(H1B)
;
_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
N1 N 0.41487(13) 0.47856(5) 0.73467(18) 0.0371(3) Uani 1 1 d . . . . .
H1 H 0.490938 0.489503 0.699776 0.045 Uiso 0.5 1 calc R . P . .
N2 N 0.22314(14) 0.47669(5) 0.86029(18) 0.0386(3) Uani 1 1 d . . . . .
H2 H 0.156126 0.486107 0.918923 0.046 Uiso 0.5 1 calc R . P . .
N3 N 0.07372(16) 0.17218(5) 0.6251(2) 0.0502(4) Uani 1 1 d . . . . .
N4 N 0.43472(15) 0.24453(5) 0.8063(2) 0.0501(4) Uani 1 1 d . . . . .
C1 C 0.33015(15) 0.50372(5) 0.82716(19) 0.0338(3) Uani 1 1 d . . . . .
C2 C 0.23876(15) 0.43099(5) 0.7840(2) 0.0340(3) Uani 1 1 d . . . . .
C3 C 0.35977(15) 0.43249(5) 0.7052(2) 0.0330(3) Uani 1 1 d . . . . .
C4 C 0.40244(16) 0.39244(6) 0.6115(2) 0.0382(4) Uani 1 1 d . . . . .
H4 H 0.483248 0.393871 0.555784 0.046 Uiso 1 1 calc R . . . .
C5 C 0.32352(15) 0.35089(5) 0.6027(2) 0.0362(4) Uani 1 1 d . . . . .
H5 H 0.350618 0.323010 0.539757 0.043 Uiso 1 1 calc R . . . .
C6 C 0.20240(15) 0.34829(5) 0.6849(2) 0.0339(3) Uani 1 1 d . . . . .
C7 C 0.15812(15) 0.38899(6) 0.7743(2) 0.0373(4) Uani 1 1 d . . . . .
H7 H 0.075747 0.388051 0.826625 0.045 Uiso 1 1 calc R . . . .
C8 C 0.12218(15) 0.30253(5) 0.67282(19) 0.0333(3) Uani 1 1 d . . . . .
C9 C 0.18444(15) 0.25745(5) 0.6918(2) 0.0347(3) Uani 1 1 d . . . . .
C10 C 0.11838(15) 0.21078(6) 0.6549(2) 0.0378(4) Uani 1 1 d . . . . .
C11 C 0.32486(16) 0.25188(6) 0.7534(2) 0.0385(4) Uani 1 1 d . . . . .
C12 C -0.02593(15) 0.30589(5) 0.6363(2) 0.0328(3) Uani 1 1 d . . . . .
C13 C -0.11115(15) 0.27363(6) 0.7152(2) 0.0364(4) Uani 1 1 d . . . . .
H13 H -0.073950 0.250077 0.798229 0.044 Uiso 1 1 calc R . . . .
C14 C -0.24934(16) 0.27588(6) 0.6728(2) 0.0429(4) Uani 1 1 d . . . . .
H14 H -0.306960 0.253793 0.726148 0.052 Uiso 1 1 calc R . . . .
C15 C -0.30358(17) 0.31029(6) 0.5526(3) 0.0473(4) Uani 1 1 d . . . . .
H15 H -0.398481 0.311455 0.522320 0.057 Uiso 1 1 calc R . . . .
C16 C -0.22049(18) 0.34309(6) 0.4760(2) 0.0456(4) Uani 1 1 d . . . . .
H16 H -0.258560 0.366896 0.394482 0.055 Uiso 1 1 calc R . . . .
C17 C -0.08181(16) 0.34121(6) 0.5181(2) 0.0390(4) Uani 1 1 d . . . . .
H17 H -0.024917 0.363964 0.466548 0.047 Uiso 1 1 calc R . . . .
C18 C 0.35384(16) 0.55529(5) 0.88079(19) 0.0353(3) Uani 1 1 d . . . . .
C19 C 0.25371(18) 0.58280(6) 0.9506(2) 0.0452(4) Uani 1 1 d . . . . .
H19 H 0.168987 0.568001 0.964858 0.054 Uiso 1 1 calc R . . . .
C20 C 0.2771(2) 0.63157(7) 0.9992(3) 0.0525(5) Uani 1 1 d . . . . .
H20 H 0.208329 0.650121 1.046266 0.063 Uiso 1 1 calc R . . . .
C21 C 0.3999(2) 0.65330(6) 0.9794(2) 0.0495(4) Uani 1 1 d . . . . .
H21 H 0.416023 0.686696 1.013661 0.059 Uiso 1 1 calc R . . . .
C22 C 0.49951(19) 0.62644(6) 0.9096(3) 0.0498(4) Uani 1 1 d . . . . .
H22 H 0.583999 0.641474 0.895754 0.060 Uiso 1 1 calc R . . . .
C23 C 0.47688(17) 0.57769(6) 0.8598(2) 0.0420(4) Uani 1 1 d . . . . .
H23 H 0.545634 0.559510 0.811136 0.050 Uiso 1 1 calc R . . . .
O1A O 0.0432(2) 0.48840(10) 1.1018(3) 0.0491(6) Uani 0.5 1 d . U P A -1
H1A H -0.028597 0.504399 1.106796 0.074 Uiso 0.5 1 calc GR . P A -1
C24 C 0.1017(5) 0.47530(18) 1.2822(6) 0.0543(11) Uani 0.5 1 d . U P A -1
H24A H 0.145629 0.442914 1.280629 0.081 Uiso 0.5 1 calc GR . P A -1
H24B H 0.029479 0.474076 1.359748 0.081 Uiso 0.5 1 calc GR . P A -1
H24C H 0.168307 0.500307 1.324824 0.081 Uiso 0.5 1 calc GR . P A -1
O1C O 0.3394(3) 0.51321(12) 1.3780(4) 0.0622(8) Uani 0.5 1 d . . P B -2
H1C H 0.365720 0.502618 1.478445 0.093 Uiso 0.5 1 calc GR . P B -2
C26 C 0.1977(6) 0.5157(3) 1.3578(8) 0.0598(16) Uani 0.5 1 d . . P B -2
H26A H 0.168675 0.542827 1.278213 0.090 Uiso 0.5 1 calc GR . P B -2
H26B H 0.164722 0.521573 1.471893 0.090 Uiso 0.5 1 calc GR . P B -2
H26C H 0.160807 0.484450 1.309370 0.090 Uiso 0.5 1 calc GR . P B -2
C25 C 0.1357(12) 0.4622(4) 1.3083(14) 0.057(3) Uiso 0.25 1 d . U P C -3
H25A H 0.182292 0.456075 1.204192 0.086 Uiso 0.25 1 calc GR . P C -3
H25B H 0.038553 0.456717 1.280312 0.086 Uiso 0.25 1 calc GR . P C -3
H25C H 0.170469 0.439703 1.402085 0.086 Uiso 0.25 1 calc GR . P C -3
O1B O 0.1608(11) 0.5172(5) 1.3700(17) 0.078(4) Uiso 0.25 1 d . U P C -3
H1B H 0.086390 0.530993 1.380690 0.118 Uiso 0.25 1 calc GR . P C -3


_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
N1 H1 0.8800 . ?
N1 C1 1.343(2) . ?
N1 C3 1.371(2) . ?
N2 H2 0.8800 . ?
N2 C1 1.338(2) . ?
N2 C2 1.384(2) . ?
N3 C10 1.149(2) . ?
N4 C11 1.145(2) . ?
C1 C18 1.467(2) . ?
C2 C3 1.403(2) . ?
C2 C7 1.389(2) . ?
C3 C4 1.391(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.369(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.419(2) . ?
C6 C7 1.393(2) . ?
C6 C8 1.471(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(2) . ?
C8 C12 1.475(2) . ?
C9 C10 1.438(2) . ?
C9 C11 1.437(2) . ?
C12 C13 1.398(2) . ?
C12 C17 1.394(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(2) . ?
C18 C23 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?
O1A H1A 0.8400 . ?
O1A C24 1.490(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1C H1C 0.8400 . ?
O1C C26 1.405(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 O1B 1.574(16) . ?
O1B H1B 0.8400 . ?

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
C1 N1 H1 126.7 . . ?
C1 N1 C3 106.62(12) . . ?
C3 N1 H1 126.7 . . ?
C1 N2 H2 126.8 . . ?
C1 N2 C2 106.34(12) . . ?
C2 N2 H2 126.8 . . ?
N1 C1 C18 122.64(14) . . ?
N2 C1 N1 112.29(13) . . ?
N2 C1 C18 125.06(14) . . ?
N2 C2 C3 107.20(13) . . ?
N2 C2 C7 131.64(14) . . ?
C7 C2 C3 121.15(14) . . ?
N1 C3 C2 107.55(13) . . ?
N1 C3 C4 130.94(14) . . ?
C4 C3 C2 121.47(14) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.45(14) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.89(14) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C8 119.63(13) . . ?
C7 C6 C5 120.42(14) . . ?
C7 C6 C8 119.94(13) . . ?
C2 C7 C6 117.58(14) . . ?
C2 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C6 C8 C12 119.05(13) . . ?
C9 C8 C6 120.40(13) . . ?
C9 C8 C12 120.53(13) . . ?
C8 C9 C10 124.62(14) . . ?
C8 C9 C11 122.88(13) . . ?
C11 C9 C10 112.50(13) . . ?
N3 C10 C9 175.58(16) . . ?
N4 C11 C9 175.63(16) . . ?
C13 C12 C8 121.19(13) . . ?
C17 C12 C8 119.39(14) . . ?
C17 C12 C13 119.41(14) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.24(15) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.92(16) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.42(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.07(16) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 119.91(15) . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C1 121.00(14) . . ?
C23 C18 C1 120.00(14) . . ?
C23 C18 C19 118.99(15) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.35(16) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.21(17) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.88(16) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.37(17) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.20(16) . . ?
C22 C23 H23 119.9 . . ?
C24 O1A H1A 109.5 . . ?
O1A C24 H24A 109.5 . . ?
O1A C24 H24B 109.5 . . ?
O1A C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 O1C H1C 109.5 . . ?
O1C C26 H26A 109.5 . . ?
O1C C26 H26B 109.5 . . ?
O1C C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1B C25 H25A 109.5 . . ?
O1B C25 H25B 109.5 . . ?
O1B C25 H25C 109.5 . . ?
C25 O1B H1B 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
_geom_hbond_publ_flag
N2 H2 O1A 0.88 1.89 2.727(3) 158.5 . yes
N2 H2 O1A 0.88 2.09 2.857(3) 145.0 3_567 yes
O1A H1A N2 0.84 2.04 2.857(3) 163.0 3_567 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C18 C19 169.15(15) . . . . ?
N1 C1 C18 C23 -9.8(2) . . . . ?
N1 C3 C4 C5 -178.82(15) . . . . ?
N2 C1 C18 C19 -9.6(2) . . . . ?
N2 C1 C18 C23 171.43(15) . . . . ?
N2 C2 C3 N1 0.01(17) . . . . ?
N2 C2 C3 C4 -177.78(14) . . . . ?
N2 C2 C7 C6 179.37(16) . . . . ?
C1 N1 C3 C2 -0.13(17) . . . . ?
C1 N1 C3 C4 177.37(16) . . . . ?
C1 N2 C2 C3 0.11(17) . . . . ?
C1 N2 C2 C7 -178.77(17) . . . . ?
C1 C18 C19 C20 -179.42(16) . . . . ?
C1 C18 C23 C22 179.75(15) . . . . ?
C2 N2 C1 N1 -0.20(18) . . . . ?
C2 N2 C1 C18 178.64(14) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C3 N1 C1 N2 0.21(18) . . . . ?
C3 N1 C1 C18 -178.67(13) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C4 C5 C6 C8 -179.34(14) . . . . ?
C5 C6 C7 C2 -2.0(2) . . . . ?
C5 C6 C8 C9 42.3(2) . . . . ?
C5 C6 C8 C12 -136.39(15) . . . . ?
C6 C8 C9 C10 -169.53(14) . . . . ?
C6 C8 C9 C11 11.1(2) . . . . ?
C6 C8 C12 C13 -142.88(15) . . . . ?
C6 C8 C12 C17 38.5(2) . . . . ?
C7 C2 C3 N1 179.04(14) . . . . ?
C7 C2 C3 C4 1.3(2) . . . . ?
C7 C6 C8 C9 -138.72(16) . . . . ?
C7 C6 C8 C12 42.6(2) . . . . ?
C8 C6 C7 C2 179.00(14) . . . . ?
C8 C12 C13 C14 -176.90(14) . . . . ?
C8 C12 C17 C16 176.73(14) . . . . ?
C9 C8 C12 C13 38.4(2) . . . . ?
C9 C8 C12 C17 -140.19(15) . . . . ?
C12 C8 C9 C10 9.1(2) . . . . ?
C12 C8 C9 C11 -170.22(14) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C12 C17 C16 -1.9(2) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C12 0.7(2) . . . . ?
C17 C12 C13 C14 1.7(2) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C18 C23 C22 0.7(2) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C18 -0.4(3) . . . . ?
C23 C18 C19 C20 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


# 
_vrf_PLAT375_bidcpv              
;
PROBLEM:  Strange C-O-H Geometry (C-O > 1.45 Ang)
RESPONSE: This is due to modeling of disordered methanol.
;
_vrf_PLAT042_bidcpv              
;
PROBLEM: Calc. and Reported MoietyFormula Strings Differ
RESPONSE: For representing it differently by the software used.
;
# end 
