# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_PMDI-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2266873'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2022-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'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/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.5200(7)
_cell_length_b                   9.3992(5)
_cell_length_c                   15.1096(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.583(2)
_cell_angle_gamma                90
_cell_volume                     1903.99(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3795
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.96
_cell_measurement_theta_min      2.61
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0772 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.8821.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             752.442
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.9986
_diffrn_reflns_Laue_measured_fraction_max 0.9986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34521
_diffrn_reflns_point_group_measured_fraction_full 0.9986
_diffrn_reflns_point_group_measured_fraction_max 0.9986
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.61
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2805
_reflns_number_total             3602
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.3424
_refine_diff_density_min         -0.3314
_refine_diff_density_rms         0.0706
_refine_ls_d_res_high            0.8202
_refine_ls_d_res_low             7.7951
_refine_ls_goodness_of_fit_ref   1.0789
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.0789
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0769P)²+0.9690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1730
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C8(H8), C16(H16), C11(H11), C4(H4), C2(H2a), C19(H19),
 C22(H22), C20(H20), C5(H5), C21(H21), C6(H6), C14(H14), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     dual
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
O1 O 0.75689(15) 0.6372(2) 0.91149(15) 0.0591(6) Uani 1.000000 .
H1 H 0.7017(11) 0.600(4) 0.8887(14) 0.0886(9) Uiso 1.000000 GR
N2 N 0.28706(17) 0.5902(2) 0.52234(15) 0.0454(6) Uani 1.000000 .
H2 H 0.26373(17) 0.6680(2) 0.49202(15) 0.0545(7) Uiso 1.000000 R
N3 N 0.21159(18) 0.4330(3) 0.88570(16) 0.0502(6) Uani 1.000000 .
H3 H 0.21060(18) 0.4609(3) 0.93953(16) 0.0603(7) Uiso 1.000000 R
C9 C 0.32425(16) 0.4197(2) 0.63456(16) 0.0334(5) Uani 1.000000 .
C7 C 0.33809(17) 0.3325(2) 0.72302(17) 0.0338(5) Uani 1.000000 .
H7 H 0.31995(17) 0.2347(2) 0.70062(17) 0.0406(6) Uiso 1.000000 R
N1 N 0.60636(17) 0.4442(3) 0.86129(19) 0.0617(7) Uani 1.000000 .
C10 C 0.36146(16) 0.3781(3) 0.56345(17) 0.0342(5) Uani 1.000000 .
C15 C 0.33702(18) 0.4870(3) 0.49419(18) 0.0403(6) Uani 1.000000 .
C17 C 0.27079(18) 0.3736(2) 0.77366(17) 0.0353(5) Uani 1.000000 .
C18 C 0.16358(18) 0.3601(2) 0.73353(17) 0.0362(6) Uani 1.000000 .
C8 C 0.28048(18) 0.5488(3) 0.60704(18) 0.0399(6) Uani 1.000000 .
H8 H 0.25040(18) 0.6016(3) 0.64064(18) 0.0478(7) Uiso 1.000000 R
C3 C 0.44715(18) 0.3275(2) 0.79066(17) 0.0348(5) Uani 1.000000 .
C23 C 0.1293(2) 0.3967(3) 0.80555(19) 0.0419(6) Uani 1.000000 .
C16 C 0.2954(2) 0.4171(3) 0.86536(19) 0.0439(6) Uani 1.000000 .
H16 H 0.3602(2) 0.4339(3) 0.90862(19) 0.0527(8) Uiso 1.000000 R
C11 C 0.4155(2) 0.2605(3) 0.5531(2) 0.0485(7) Uani 1.000000 .
H11 H 0.4337(2) 0.1879(3) 0.5984(2) 0.0582(8) Uiso 1.000000 R
C4 C 0.4896(2) 0.2051(3) 0.83993(19) 0.0441(6) Uani 1.000000 .
H4 H 0.4506(2) 0.1243(3) 0.83411(19) 0.0529(8) Uiso 1.000000 R
C2 C 0.50901(19) 0.4442(3) 0.8047(2) 0.0477(7) Uani 1.000000 .
H2a H 0.48144(19) 0.5280(3) 0.7729(2) 0.0572(8) Uiso 1.000000 R
C19 C 0.0939(2) 0.3184(3) 0.6439(2) 0.0465(7) Uani 1.000000 .
H19 H 0.1145(2) 0.2936(3) 0.5948(2) 0.0559(8) Uiso 1.000000 R
C22 C 0.0287(2) 0.3931(3) 0.7908(2) 0.0549(8) Uani 1.000000 .
H22 H 0.0071(2) 0.4181(3) 0.8393(2) 0.0659(9) Uiso 1.000000 R
C20 C -0.0057(2) 0.3146(3) 0.6295(2) 0.0566(8) Uani 1.000000 .
H20 H -0.0525(2) 0.2870(3) 0.5702(2) 0.0680(9) Uiso 1.000000 R
C5 C 0.5897(2) 0.2024(3) 0.8978(2) 0.0549(8) Uani 1.000000 .
H5 H 0.6191(2) 0.1202(3) 0.9308(2) 0.0659(9) Uiso 1.000000 R
C21 C -0.0375(2) 0.3515(3) 0.7024(3) 0.0606(9) Uani 1.000000 .
H21 H -0.1051(2) 0.3477(3) 0.6909(3) 0.0727(10) Uiso 1.000000 R
C6 C 0.6445(2) 0.3224(3) 0.9054(2) 0.0600(8) Uani 1.000000 .
H6 H 0.7122(2) 0.3194(3) 0.9435(2) 0.0721(10) Uiso 1.000000 R
C14 C 0.3631(2) 0.4788(4) 0.4147(2) 0.0582(8) Uani 1.000000 .
H14 H 0.3457(2) 0.5505(4) 0.3687(2) 0.0698(10) Uiso 1.000000 R
C13 C 0.4150(3) 0.3618(4) 0.4066(2) 0.0675(9) Uani 1.000000 .
H13 H 0.4333(3) 0.3538(4) 0.3542(2) 0.0810(11) Uiso 1.000000 R
C12 C 0.4410(2) 0.2547(4) 0.4746(2) 0.0646(9) Uani 1.000000 .
H12 H 0.4767(2) 0.1768(4) 0.4670(2) 0.0775(11) Uiso 1.000000 R
C1 C 0.8080(3) 0.6142(5) 0.8497(3) 0.0969(14) Uani 1.000000 .
H1a H 0.7733(14) 0.662(3) 0.7898(9) 0.145(2) Uiso 1.000000 GR
H1b H 0.8745(9) 0.651(3) 0.8788(11) 0.145(2) Uiso 1.000000 GR
H1c H 0.811(2) 0.5140(6) 0.8387(19) 0.145(2) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.414(4) . ?
N2 H2 0.8600 . ?
N2 C15 1.373(3) . ?
N2 C8 1.376(3) . ?
N3 H3 0.8600 . ?
N3 C23 1.378(4) . ?
N3 C16 1.373(3) . ?
C9 C7 1.514(3) . ?
C9 C10 1.430(3) . ?
C9 C8 1.359(3) . ?
C7 H7 0.9800 . ?
C7 C17 1.505(3) . ?
C7 C3 1.520(3) . ?
N1 C2 1.342(3) . ?
N1 C6 1.333(4) . ?
C10 C15 1.408(3) . ?
C10 C11 1.399(4) . ?
C15 C14 1.393(4) . ?
C17 C18 1.443(3) . ?
C17 C16 1.354(4) . ?
C18 C23 1.402(4) . ?
C18 C19 1.400(4) . ?
C8 H8 0.9300 . ?
C3 C4 1.381(3) . ?
C3 C2 1.381(4) . ?
C23 C22 1.392(4) . ?
C16 H16 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.373(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C2 H2a 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.369(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(4) . ?
C21 H21 0.9300 . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.366(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.384(5) . ?
C12 H12 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 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
C1 O1 H1 109.5 . . ?
C15 N2 H2 125.62(14) . . ?
C8 N2 H2 125.62(14) . . ?
C8 N2 C15 108.8(2) . . ?
C23 N3 H3 125.66(14) . . ?
C16 N3 H3 125.66(15) . . ?
C16 N3 C23 108.7(2) . . ?
C10 C9 C7 123.7(2) . . ?
C8 C9 C7 129.9(2) . . ?
C8 C9 C10 106.3(2) . . ?
H7 C7 C9 105.99(12) . . ?
C17 C7 C9 114.72(19) . . ?
C17 C7 H7 105.99(13) . . ?
C3 C7 C9 111.17(19) . . ?
C3 C7 H7 105.99(12) . . ?
C3 C7 C17 112.23(19) . . ?
C6 N1 C2 116.9(2) . . ?
C15 C10 C9 107.5(2) . . ?
C11 C10 C9 133.6(2) . . ?
C11 C10 C15 118.9(2) . . ?
C10 C15 N2 107.2(2) . . ?
C14 C15 N2 131.1(3) . . ?
C14 C15 C10 121.8(3) . . ?
C18 C17 C7 124.8(2) . . ?
C16 C17 C7 129.0(2) . . ?
C16 C17 C18 106.0(2) . . ?
C23 C18 C17 107.4(2) . . ?
C19 C18 C17 133.9(2) . . ?
C19 C18 C23 118.7(2) . . ?
C9 C8 N2 110.2(2) . . ?
H8 C8 N2 124.88(14) . . ?
H8 C8 C9 124.88(15) . . ?
C4 C3 C7 121.5(2) . . ?
C2 C3 C7 121.8(2) . . ?
C2 C3 C4 116.7(2) . . ?
C18 C23 N3 107.3(2) . . ?
C22 C23 N3 130.5(3) . . ?
C22 C23 C18 122.2(3) . . ?
C17 C16 N3 110.7(2) . . ?
H16 C16 N3 124.65(15) . . ?
H16 C16 C17 124.65(15) . . ?
H11 C11 C10 120.77(16) . . ?
C12 C11 C10 118.5(3) . . ?
C12 C11 H11 120.77(19) . . ?
H4 C4 C3 119.98(15) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 119.98(16) . . ?
C3 C2 N1 124.2(2) . . ?
H2a C2 N1 117.91(16) . . ?
H2a C2 C3 117.91(15) . . ?
H19 C19 C18 120.52(15) . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.52(18) . . ?
H22 C22 C23 121.19(18) . . ?
C21 C22 C23 117.6(3) . . ?
C21 C22 H22 121.19(17) . . ?
H20 C20 C19 119.47(18) . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.47(18) . . ?
H5 C5 C4 120.71(16) . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.71(17) . . ?
C20 C21 C22 121.4(3) . . ?
H21 C21 C22 119.28(17) . . ?
H21 C21 C20 119.28(18) . . ?
C5 C6 N1 123.6(3) . . ?
H6 C6 N1 118.20(16) . . ?
H6 C6 C5 118.20(17) . . ?
H14 C14 C15 121.18(18) . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 H14 121.18(19) . . ?
H13 C13 C14 119.29(19) . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 H13 119.29(18) . . ?
C13 C12 C11 121.8(3) . . ?
H12 C12 C11 119.12(19) . . ?
H12 C12 C13 119.12(18) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?

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
N2 C15 C10 C9 0.0(2) . . . . ?
N2 C15 C10 C11 -178.4(2) . . . . ?
N2 C15 C14 C13 178.9(3) . . . . ?
N2 C8 C9 C7 178.26(18) . . . . ?
N2 C8 C9 C10 0.6(2) . . . . ?
N3 C23 C18 C17 0.8(2) . . . . ?
N3 C23 C18 C19 179.9(2) . . . . ?
N3 C23 C22 C21 -179.7(3) . . . . ?
N3 C16 C17 C7 -174.95(19) . . . . ?
N3 C16 C17 C18 -0.5(2) . . . . ?
C9 C7 C17 C18 64.8(2) . . . . ?
C9 C7 C17 C16 -121.7(2) . . . . ?
C9 C7 C3 C4 -141.1(2) . . . . ?
C9 C7 C3 C2 37.8(3) . . . . ?
C9 C10 C15 C14 -180.0(2) . . . . ?
C9 C10 C11 C12 -179.1(3) . . . . ?
C7 C17 C18 C23 174.6(2) . . . . ?
C7 C17 C18 C19 -4.3(3) . . . . ?
C7 C3 C4 C5 177.4(3) . . . . ?
C7 C3 C2 N1 -177.9(3) . . . . ?
N1 C2 C3 C4 1.1(4) . . . . ?
N1 C6 C5 C4 1.3(4) . . . . ?
C10 C15 C14 C13 -1.0(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C15 C14 C13 C12 0.1(4) . . . . ?
C17 C18 C23 C22 -179.1(2) . . . . ?
C17 C18 C19 C20 178.7(3) . . . . ?
C18 C23 C22 C21 0.2(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C23 C22 C21 C20 -0.3(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Photo-sensitive
####################################################################### 
# 
# 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_80MIr-PMDI-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2303200'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.4831(18)
_cell_length_b                   9.3913(9)
_cell_length_c                   15.0356(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.580(4)
_cell_angle_gamma                90
_cell_volume                     1888.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5846
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.12
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             752.442
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21421
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9987
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2049
_reflns_number_total             3720
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.5611
_refine_diff_density_min         -0.5150
_refine_diff_density_rms         0.1106
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             7.7787
_refine_ls_goodness_of_fit_ref   1.6190
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1776
_refine_ls_R_factor_gt           0.1189
_refine_ls_restrained_S_all      1.6190
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3019
_refine_ls_wR_factor_ref         0.4517
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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
O1 O 0.7562(3) 0.6366(4) 0.9104(3) 0.0838(12) Uani 1.000000 .
N2 N 0.2868(3) 0.5902(4) 0.5222(3) 0.0707(12) Uani 1.000000 .
N3 N 0.2110(3) 0.4328(5) 0.8862(3) 0.0753(13) Uani 1.000000 .
N1 N 0.6063(3) 0.4441(5) 0.8611(4) 0.0839(14) Uani 1.000000 .
C9 C 0.3240(3) 0.4200(5) 0.6349(3) 0.0586(12) Uani 1.000000 .
C17 C 0.2702(4) 0.3742(5) 0.7728(3) 0.0610(12) Uani 1.000000 .
C18 C 0.1639(4) 0.3615(5) 0.7337(3) 0.0628(13) Uani 1.000000 .
C7 C 0.3378(3) 0.3334(5) 0.7230(3) 0.0596(12) Uani 1.000000 .
C11 C 0.3367(4) 0.4878(5) 0.4940(3) 0.0634(12) Uani 1.000000 .
C3 C 0.4468(4) 0.3280(5) 0.7908(3) 0.0607(12) Uani 1.000000 .
C10 C 0.3622(3) 0.3791(5) 0.5634(3) 0.0605(13) Uani 1.000000 .
C19 C 0.1297(4) 0.3967(5) 0.8061(4) 0.0669(14) Uani 1.000000 .
C8 C 0.2804(4) 0.5493(5) 0.6073(4) 0.0661(13) Uani 1.000000 .
C23 C 0.0939(4) 0.3190(5) 0.6440(4) 0.0709(14) Uani 1.000000 .
C4 C 0.4893(4) 0.2049(5) 0.8397(4) 0.0675(14) Uani 1.000000 .
C15 C 0.4148(4) 0.2612(6) 0.5526(4) 0.0708(14) Uani 1.000000 .
C16 C 0.2958(4) 0.4170(5) 0.8662(4) 0.0708(14) Uani 1.000000 .
C2 C 0.5086(4) 0.4450(6) 0.8049(4) 0.0727(14) Uani 1.000000 .
C5 C 0.5899(4) 0.2019(6) 0.8967(4) 0.0805(16) Uani 1.000000 .
C12 C 0.3637(4) 0.4795(6) 0.4154(4) 0.0791(15) Uani 1.000000 .
C22 C -0.0055(4) 0.3152(6) 0.6294(5) 0.0811(16) Uani 1.000000 .
C6 C 0.6451(4) 0.3226(6) 0.9050(4) 0.0839(17) Uani 1.000000 .
C21 C -0.0377(5) 0.3516(6) 0.7017(5) 0.0837(17) Uani 1.000000 .
C20 C 0.0290(4) 0.3926(6) 0.7909(5) 0.0810(17) Uani 1.000000 .
C14 C 0.4413(5) 0.2541(7) 0.4750(5) 0.0899(18) Uani 1.000000 .
C13 C 0.4149(5) 0.3609(8) 0.4062(5) 0.097(2) Uani 1.000000 .
C1 C 0.8073(6) 0.6155(8) 0.8485(5) 0.113(2) Uani 1.000000 .
H12 H 0.3476(4) 0.5523(6) 0.3700(4) 0.0949(18) Uiso 1.000000 R
H13 H 0.4321(5) 0.3522(8) 0.3529(5) 0.116(2) Uiso 1.000000 R
H14 H 0.4778(5) 0.1763(7) 0.4681(5) 0.108(2) Uiso 1.000000 R
H15 H 0.4317(4) 0.1881(6) 0.5977(4) 0.0850(17) Uiso 1.000000 R
H23 H 0.1145(4) 0.2935(5) 0.5947(4) 0.0850(17) Uiso 1.000000 R
H22 H -0.0521(4) 0.2876(6) 0.5697(5) 0.097(2) Uiso 1.000000 R
H21 H -0.1057(5) 0.3484(6) 0.6898(5) 0.100(2) Uiso 1.000000 R
H20 H 0.0073(4) 0.4168(6) 0.8397(5) 0.097(2) Uiso 1.000000 R
H2a H 0.4808(4) 0.5293(6) 0.7735(4) 0.0873(17) Uiso 1.000000 R
H6 H 0.7130(4) 0.3198(6) 0.9432(4) 0.101(2) Uiso 1.000000 R
H5 H 0.6197(4) 0.1191(6) 0.9289(4) 0.0966(19) Uiso 1.000000 R
H4 H 0.4502(4) 0.1243(5) 0.8342(4) 0.0810(16) Uiso 1.000000 R
H7 H 0.3196(3) 0.2356(5) 0.7003(3) 0.0715(15) Uiso 1.000000 R
H8 H 0.2504(4) 0.6024(5) 0.6412(4) 0.0793(16) Uiso 1.000000 R
H16 H 0.3608(4) 0.4331(5) 0.9098(4) 0.0850(17) Uiso 1.000000 R
H1a H 0.7685(19) 0.654(5) 0.7862(12) 0.169(4) Uiso 1.000000 GR
H1b H 0.8709(18) 0.663(5) 0.874(2) 0.169(4) Uiso 1.000000 GR
H1c H 0.817(4) 0.5154(9) 0.843(3) 0.169(4) Uiso 1.000000 GR
H1 H 0.704(3) 0.590(6) 0.891(3) 0.1258(18) Uiso 1.000000 GR
H2 H 0.2633(3) 0.6678(4) 0.4916(3) 0.0849(15) Uiso 1.000000 R
H3 H 0.2096(3) 0.4607(5) 0.9402(3) 0.0903(15) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.407(7) . ?
O1 H1 0.8200 . ?
N2 C11 1.364(6) . ?
N2 C8 1.373(6) . ?
N2 H2 0.8600 . ?
N3 C19 1.365(6) . ?
N3 C16 1.379(7) . ?
N3 H3 0.8600 . ?
N1 C2 1.341(6) . ?
N1 C6 1.330(7) . ?
C9 C7 1.501(7) . ?
C9 C10 1.437(7) . ?
C9 C8 1.358(6) . ?
C17 C18 1.426(7) . ?
C17 C7 1.492(7) . ?
C17 C16 1.369(7) . ?
C18 C19 1.398(7) . ?
C18 C23 1.398(7) . ?
C7 C3 1.516(6) . ?
C7 H7 0.9800 . ?
C11 C10 1.404(7) . ?
C11 C12 1.382(7) . ?
C3 C4 1.382(7) . ?
C3 C2 1.381(7) . ?
C10 C15 1.388(7) . ?
C19 C20 1.388(7) . ?
C8 H8 0.9300 . ?
C23 C22 1.371(8) . ?
C23 H23 0.9300 . ?
C4 C5 1.378(7) . ?
C4 H4 0.9300 . ?
C15 C14 1.364(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C2 H2a 0.9300 . ?
C5 C6 1.365(8) . ?
C5 H5 0.9300 . ?
C12 C13 1.375(9) . ?
C12 H12 0.9300 . ?
C22 C21 1.380(9) . ?
C22 H22 0.9300 . ?
C6 H6 0.9300 . ?
C21 C20 1.373(8) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C14 C13 1.384(9) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 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
H1 O1 C1 109.5 . . ?
C8 N2 C11 109.0(4) . . ?
H2 N2 C11 125.5(3) . . ?
H2 N2 C8 125.5(3) . . ?
C16 N3 C19 108.6(4) . . ?
H3 N3 C19 125.7(3) . . ?
H3 N3 C16 125.7(3) . . ?
C6 N1 C2 117.5(5) . . ?
C10 C9 C7 123.8(4) . . ?
C8 C9 C7 130.0(4) . . ?
C8 C9 C10 106.1(4) . . ?
C7 C17 C18 125.7(4) . . ?
C16 C17 C18 105.8(4) . . ?
C16 C17 C7 128.2(5) . . ?
C19 C18 C17 107.9(4) . . ?
C23 C18 C17 133.6(5) . . ?
C23 C18 C19 118.4(5) . . ?
C17 C7 C9 114.4(4) . . ?
C3 C7 C9 111.2(4) . . ?
C3 C7 C17 112.7(4) . . ?
H7 C7 C9 105.9(2) . . ?
H7 C7 C17 105.9(3) . . ?
H7 C7 C3 105.9(2) . . ?
C10 C11 N2 107.5(4) . . ?
C12 C11 N2 131.5(5) . . ?
C12 C11 C10 121.0(5) . . ?
C4 C3 C7 121.5(4) . . ?
C2 C3 C7 121.6(4) . . ?
C2 C3 C4 117.0(5) . . ?
C11 C10 C9 107.1(4) . . ?
C15 C10 C9 133.3(5) . . ?
C15 C10 C11 119.5(5) . . ?
C18 C19 N3 107.6(4) . . ?
C20 C19 N3 130.4(5) . . ?
C20 C19 C18 122.0(5) . . ?
C9 C8 N2 110.1(4) . . ?
H8 C8 N2 124.9(3) . . ?
H8 C8 C9 124.9(3) . . ?
C22 C23 C18 119.3(5) . . ?
H23 C23 C18 120.4(3) . . ?
H23 C23 C22 120.4(4) . . ?
C5 C4 C3 119.8(5) . . ?
H4 C4 C3 120.1(3) . . ?
H4 C4 C5 120.1(3) . . ?
C14 C15 C10 119.1(5) . . ?
H15 C15 C10 120.4(3) . . ?
H15 C15 C14 120.4(4) . . ?
C17 C16 N3 110.0(5) . . ?
H16 C16 N3 125.0(3) . . ?
H16 C16 C17 125.0(3) . . ?
C3 C2 N1 123.8(5) . . ?
H2a C2 N1 118.1(3) . . ?
H2a C2 C3 118.1(3) . . ?
C6 C5 C4 118.8(5) . . ?
H5 C5 C4 120.6(3) . . ?
H5 C5 C6 120.6(3) . . ?
C13 C12 C11 118.2(6) . . ?
H12 C12 C11 120.9(3) . . ?
H12 C12 C13 120.9(4) . . ?
C21 C22 C23 121.3(6) . . ?
H22 C22 C23 119.3(4) . . ?
H22 C22 C21 119.3(4) . . ?
C5 C6 N1 123.1(5) . . ?
H6 C6 N1 118.5(3) . . ?
H6 C6 C5 118.5(3) . . ?
C20 C21 C22 121.0(6) . . ?
H21 C21 C22 119.5(4) . . ?
H21 C21 C20 119.5(3) . . ?
C21 C20 C19 118.0(6) . . ?
H20 C20 C19 121.0(4) . . ?
H20 C20 C21 121.0(3) . . ?
C13 C14 C15 121.1(6) . . ?
H14 C14 C15 119.5(4) . . ?
H14 C14 C13 119.5(4) . . ?
C14 C13 C12 121.1(6) . . ?
H13 C13 C12 119.4(4) . . ?
H13 C13 C14 119.4(4) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?

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
N2 C11 C10 C9 0.7(4) . . . . ?
N2 C11 C10 C15 -179.4(4) . . . . ?
N2 C11 C12 C13 179.7(6) . . . . ?
N2 C8 C9 C7 178.4(3) . . . . ?
N2 C8 C9 C10 1.3(4) . . . . ?
N3 C19 C18 C17 1.2(4) . . . . ?
N3 C19 C18 C23 179.3(4) . . . . ?
N3 C19 C20 C21 -180.0(6) . . . . ?
N3 C16 C17 C18 -0.7(4) . . . . ?
N3 C16 C17 C7 -174.7(4) . . . . ?
N1 C2 C3 C7 -177.4(5) . . . . ?
N1 C2 C3 C4 1.3(7) . . . . ?
N1 C6 C5 C4 0.4(7) . . . . ?
C9 C7 C17 C18 64.7(5) . . . . ?
C9 C7 C17 C16 -122.4(4) . . . . ?
C9 C7 C3 C4 -140.7(4) . . . . ?
C9 C7 C3 C2 37.9(5) . . . . ?
C9 C10 C11 C12 179.8(4) . . . . ?
C9 C10 C15 C14 -179.6(6) . . . . ?
C17 C18 C19 C20 -179.1(4) . . . . ?
C17 C18 C23 C22 178.5(6) . . . . ?
C17 C7 C3 C4 89.3(4) . . . . ?
C17 C7 C3 C2 -92.1(5) . . . . ?
C18 C19 C20 C21 0.4(6) . . . . ?
C18 C23 C22 C21 -0.4(6) . . . . ?
C7 C3 C4 C5 176.5(5) . . . . ?
C11 C10 C15 C14 0.5(6) . . . . ?
C11 C12 C13 C14 -1.7(7) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
C10 C15 C14 C13 -1.3(6) . . . . ?
C19 C20 C21 C22 0.2(6) . . . . ?
C23 C22 C21 C20 -0.2(6) . . . . ?
C15 C14 C13 C12 2.0(8) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_25MIr-PMDI-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2303198'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.4915(18)
_cell_length_b                   9.3952(9)
_cell_length_c                   15.0402(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.575(4)
_cell_angle_gamma                90
_cell_volume                     1890.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             752.442
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21320
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9989
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2056
_reflns_number_total             3727
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.5526
_refine_diff_density_min         -0.4247
_refine_diff_density_rms         0.1042
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             7.7818
_refine_ls_goodness_of_fit_ref   1.6254
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1787
_refine_ls_R_factor_gt           0.1197
_refine_ls_restrained_S_all      1.6254
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3027
_refine_ls_wR_factor_ref         0.4518
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C8(H8), C15(H15), C4(H4), C23(H23), C16(H16), C5(H5), C2(H2a),
  C12(H12), C22(H22), C13(H13), C6(H6), C20(H20), C21(H21), C14(H14)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     dual
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
O1 O 0.7566(3) 0.6366(4) 0.9104(3) 0.0853(12) Uani 1.000000 .
H1 H 0.703(2) 0.595(7) 0.889(3) 0.1279(18) Uiso 1.000000 GR
N2 N 0.2866(3) 0.5902(4) 0.5221(3) 0.0710(12) Uani 1.000000 .
H2 H 0.2627(3) 0.6677(4) 0.4914(3) 0.0852(15) Uiso 1.000000 R
N3 N 0.2114(3) 0.4330(5) 0.8862(3) 0.0755(13) Uani 1.000000 .
H3 H 0.2100(3) 0.4609(5) 0.9401(3) 0.0906(15) Uiso 1.000000 R
N1 N 0.6059(3) 0.4439(5) 0.8608(3) 0.0841(14) Uani 1.000000 .
C9 C 0.3244(3) 0.4203(5) 0.6348(3) 0.0585(12) Uani 1.000000 .
C7 C 0.3377(3) 0.3334(5) 0.7231(3) 0.0602(12) Uani 1.000000 .
H7 H 0.3195(3) 0.2356(5) 0.7004(3) 0.0723(15) Uiso 1.000000 R
C11 C 0.3368(3) 0.4873(5) 0.4939(3) 0.0632(12) Uani 1.000000 .
C10 C 0.3622(3) 0.3798(5) 0.5633(3) 0.0602(12) Uani 1.000000 .
C18 C 0.1637(4) 0.3619(5) 0.7334(3) 0.0618(13) Uani 1.000000 .
C3 C 0.4469(3) 0.3281(5) 0.7905(3) 0.0603(12) Uani 1.000000 .
C17 C 0.2703(4) 0.3741(5) 0.7728(4) 0.0614(12) Uani 1.000000 .
C8 C 0.2806(4) 0.5490(5) 0.6075(4) 0.0669(13) Uani 1.000000 .
H8 H 0.2508(4) 0.6019(5) 0.6415(4) 0.0803(16) Uiso 1.000000 R
C15 C 0.4151(4) 0.2612(6) 0.5527(4) 0.0696(14) Uani 1.000000 .
H15 H 0.4324(4) 0.1882(6) 0.5980(4) 0.0835(16) Uiso 1.000000 R
C4 C 0.4895(4) 0.2055(5) 0.8400(4) 0.0704(14) Uani 1.000000 .
H4 H 0.4502(4) 0.1254(5) 0.8352(4) 0.0845(17) Uiso 1.000000 R
C23 C 0.0939(4) 0.3191(5) 0.6440(4) 0.0705(14) Uani 1.000000 .
H23 H 0.1146(4) 0.2931(5) 0.5950(4) 0.0846(17) Uiso 1.000000 R
C19 C 0.1299(4) 0.3970(5) 0.8056(4) 0.0670(14) Uani 1.000000 .
C16 C 0.2962(4) 0.4171(5) 0.8664(4) 0.0699(14) Uani 1.000000 .
H16 H 0.3611(4) 0.4331(5) 0.9100(4) 0.0838(17) Uiso 1.000000 R
C5 C 0.5899(4) 0.2021(6) 0.8963(4) 0.0808(16) Uani 1.000000 .
H5 H 0.6195(4) 0.1191(6) 0.9283(4) 0.0970(19) Uiso 1.000000 R
C2 C 0.5090(4) 0.4449(5) 0.8047(4) 0.0741(15) Uani 1.000000 .
H2a H 0.4815(4) 0.5292(5) 0.7732(4) 0.0889(18) Uiso 1.000000 R
C12 C 0.3633(4) 0.4799(6) 0.4151(4) 0.0797(15) Uani 1.000000 .
H12 H 0.3470(4) 0.5524(6) 0.3695(4) 0.0957(18) Uiso 1.000000 R
C22 C -0.0057(4) 0.3157(6) 0.6293(5) 0.0809(16) Uani 1.000000 .
H22 H -0.0524(4) 0.2890(6) 0.5694(5) 0.097(2) Uiso 1.000000 R
C13 C 0.4149(5) 0.3607(8) 0.4064(5) 0.0943(19) Uani 1.000000 .
H13 H 0.4325(5) 0.3518(8) 0.3533(5) 0.113(2) Uiso 1.000000 R
C6 C 0.6452(4) 0.3223(6) 0.9046(5) 0.0850(17) Uani 1.000000 .
H6 H 0.7132(4) 0.3193(6) 0.9424(5) 0.102(2) Uiso 1.000000 R
C20 C 0.0285(4) 0.3921(6) 0.7907(5) 0.0811(17) Uani 1.000000 .
H20 H 0.0069(4) 0.4158(6) 0.8396(5) 0.097(2) Uiso 1.000000 R
C21 C -0.0377(5) 0.3513(6) 0.7019(5) 0.0847(17) Uani 1.000000 .
H21 H -0.1056(5) 0.3475(6) 0.6901(5) 0.102(2) Uiso 1.000000 R
C14 C 0.4410(5) 0.2544(7) 0.4749(4) 0.0901(18) Uani 1.000000 .
H14 H 0.4771(5) 0.1764(7) 0.4678(4) 0.108(2) Uiso 1.000000 R
C1 C 0.8073(5) 0.6147(8) 0.8483(5) 0.114(2) Uani 1.000000 .
H1a H 0.769(2) 0.654(5) 0.7861(13) 0.171(4) Uiso 1.000000 GR
H1b H 0.8713(18) 0.661(5) 0.874(2) 0.171(4) Uiso 1.000000 GR
H1c H 0.817(4) 0.5145(9) 0.842(3) 0.171(4) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.408(7) . ?
N2 H2 0.8600 . ?
N2 C11 1.372(6) . ?
N2 C8 1.376(6) . ?
N3 H3 0.8600 . ?
N3 C19 1.371(6) . ?
N3 C16 1.378(7) . ?
N1 C2 1.333(6) . ?
N1 C6 1.332(7) . ?
C9 C7 1.507(7) . ?
C9 C10 1.433(7) . ?
C9 C8 1.354(6) . ?
C7 H7 0.9800 . ?
C7 C3 1.517(6) . ?
C7 C17 1.489(7) . ?
C11 C10 1.396(7) . ?
C11 C12 1.381(7) . ?
C10 C15 1.397(7) . ?
C18 C17 1.431(7) . ?
C18 C23 1.396(7) . ?
C18 C19 1.392(7) . ?
C3 C4 1.382(7) . ?
C3 C2 1.382(7) . ?
C17 C16 1.372(7) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.360(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(7) . ?
C23 H23 0.9300 . ?
C23 C22 1.374(8) . ?
C19 C20 1.399(7) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.363(8) . ?
C2 H2a 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.381(9) . ?
C22 H22 0.9300 . ?
C22 C21 1.381(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(9) . ?
C6 H6 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.367(8) . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 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
C1 O1 H1 109.5 . . ?
C11 N2 H2 125.6(3) . . ?
C8 N2 H2 125.6(3) . . ?
C8 N2 C11 108.7(4) . . ?
C19 N3 H3 125.7(3) . . ?
C16 N3 H3 125.7(3) . . ?
C16 N3 C19 108.7(4) . . ?
C6 N1 C2 117.8(5) . . ?
C10 C9 C7 124.1(4) . . ?
C8 C9 C7 129.7(4) . . ?
C8 C9 C10 106.2(4) . . ?
H7 C7 C9 105.9(2) . . ?
C3 C7 C9 110.7(4) . . ?
C3 C7 H7 105.9(2) . . ?
C17 C7 C9 114.6(4) . . ?
C17 C7 H7 105.9(2) . . ?
C17 C7 C3 113.0(4) . . ?
C10 C11 N2 107.3(4) . . ?
C12 C11 N2 131.0(5) . . ?
C12 C11 C10 121.7(5) . . ?
C11 C10 C9 107.6(4) . . ?
C15 C10 C9 133.0(5) . . ?
C15 C10 C11 119.3(4) . . ?
C23 C18 C17 133.6(5) . . ?
C19 C18 C17 107.9(4) . . ?
C19 C18 C23 118.5(5) . . ?
C4 C3 C7 121.5(4) . . ?
C2 C3 C7 121.8(4) . . ?
C2 C3 C4 116.7(5) . . ?
C18 C17 C7 125.7(4) . . ?
C16 C17 C7 128.1(5) . . ?
C16 C17 C18 105.9(4) . . ?
C9 C8 N2 110.2(4) . . ?
H8 C8 N2 124.9(3) . . ?
H8 C8 C9 124.9(3) . . ?
H15 C15 C10 120.6(3) . . ?
C14 C15 C10 118.7(5) . . ?
C14 C15 H15 120.6(4) . . ?
H4 C4 C3 120.0(3) . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0(3) . . ?
H23 C23 C18 120.3(3) . . ?
C22 C23 C18 119.3(5) . . ?
C22 C23 H23 120.3(4) . . ?
C18 C19 N3 107.8(4) . . ?
C20 C19 N3 130.3(5) . . ?
C20 C19 C18 122.0(5) . . ?
C17 C16 N3 109.8(5) . . ?
H16 C16 N3 125.1(3) . . ?
H16 C16 C17 125.1(3) . . ?
H5 C5 C4 120.5(3) . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 H5 120.5(3) . . ?
C3 C2 N1 123.9(5) . . ?
H2a C2 N1 118.1(3) . . ?
H2a C2 C3 118.1(3) . . ?
H12 C12 C11 121.3(3) . . ?
C13 C12 C11 117.5(6) . . ?
C13 C12 H12 121.3(4) . . ?
H22 C22 C23 119.4(4) . . ?
C21 C22 C23 121.2(6) . . ?
C21 C22 H22 119.4(4) . . ?
H13 C13 C12 119.4(4) . . ?
C14 C13 C12 121.3(6) . . ?
C14 C13 H13 119.4(4) . . ?
C5 C6 N1 122.7(5) . . ?
H6 C6 N1 118.6(3) . . ?
H6 C6 C5 118.6(3) . . ?
H20 C20 C19 121.1(4) . . ?
C21 C20 C19 117.8(5) . . ?
C21 C20 H20 121.1(3) . . ?
C20 C21 C22 121.1(5) . . ?
H21 C21 C22 119.4(4) . . ?
H21 C21 C20 119.4(3) . . ?
C13 C14 C15 121.5(6) . . ?
H14 C14 C15 119.3(4) . . ?
H14 C14 C13 119.3(4) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?

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
N2 C11 C10 C9 0.6(4) . . . . ?
N2 C11 C10 C15 -179.5(4) . . . . ?
N2 C11 C12 C13 179.7(6) . . . . ?
N2 C8 C9 C7 178.9(3) . . . . ?
N2 C8 C9 C10 1.4(4) . . . . ?
N3 C19 C18 C17 1.4(4) . . . . ?
N3 C19 C18 C23 179.0(4) . . . . ?
N3 C19 C20 C21 -179.7(6) . . . . ?
N3 C16 C17 C7 -174.8(4) . . . . ?
N3 C16 C17 C18 -0.5(4) . . . . ?
N1 C2 C3 C7 -177.9(5) . . . . ?
N1 C2 C3 C4 1.5(7) . . . . ?
N1 C6 C5 C4 0.5(7) . . . . ?
C9 C7 C3 C4 -141.2(4) . . . . ?
C9 C7 C3 C2 38.2(5) . . . . ?
C9 C7 C17 C18 64.6(5) . . . . ?
C9 C7 C17 C16 -122.1(4) . . . . ?
C9 C10 C11 C12 179.7(4) . . . . ?
C9 C10 C15 C14 -179.8(6) . . . . ?
C7 C3 C4 C5 176.5(5) . . . . ?
C7 C17 C18 C23 -3.2(6) . . . . ?
C7 C17 C18 C19 174.0(5) . . . . ?
C11 C10 C15 C14 0.4(6) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C10 C15 C14 C13 -0.9(6) . . . . ?
C18 C23 C22 C21 -1.2(6) . . . . ?
C18 C19 C20 C21 -0.0(6) . . . . ?
C3 C4 C5 C6 2.0(6) . . . . ?
C15 C14 C13 C12 1.4(8) . . . . ?
C23 C22 C21 C20 0.4(6) . . . . ?
C19 C20 C21 C22 0.2(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_PMDI-MeOH_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2303197'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.5114(18)
_cell_length_b                   9.3994(11)
_cell_length_c                   15.0586(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.506(4)
_cell_angle_gamma                90
_cell_volume                     1897.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7318
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             752.442
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.9991
_diffrn_reflns_Laue_measured_fraction_max 0.9992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21149
_diffrn_reflns_point_group_measured_fraction_full 0.9991
_diffrn_reflns_point_group_measured_fraction_max 0.9992
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2222
_reflns_number_total             3592
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.5477
_refine_diff_density_min         -0.4368
_refine_diff_density_rms         0.1043
_refine_ls_d_res_high            0.8201
_refine_ls_d_res_low             7.7883
_refine_ls_goodness_of_fit_ref   1.5726
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.1083
_refine_ls_restrained_S_all      1.5726
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2779
_refine_ls_wR_factor_ref         0.4118
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C16(H16), C8(H8), C15(H15), C4(H4), C23(H23), C2(H2a), C5(H5),
  C20(H20), C22(H22), C6(H6), C21(H21), C12(H12), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     dual
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
O1 O 0.7563(3) 0.3637(4) 0.9103(2) 0.0799(11) Uani 1.000000 .
N2 N 0.2866(3) 0.4101(4) 0.5219(2) 0.0667(10) Uani 1.000000 .
H2 H 0.2627(3) 0.3327(4) 0.4913(2) 0.0801(13) Uiso 1.000000 R
N3 N 0.2110(3) 0.5675(4) 0.8860(3) 0.0709(11) Uani 1.000000 .
H3 H 0.2096(3) 0.5399(4) 0.9400(3) 0.0851(13) Uiso 1.000000 R
N1 N 0.6062(3) 0.5557(4) 0.8607(3) 0.0795(12) Uani 1.000000 .
C7 C 0.3381(3) 0.6666(4) 0.7229(3) 0.0562(10) Uani 1.000000 .
H7 H 0.3200(3) 0.7643(4) 0.7002(3) 0.0674(13) Uiso 1.000000 R
C9 C 0.3239(3) 0.5795(4) 0.6348(3) 0.0547(10) Uani 1.000000 .
C18 C 0.1637(3) 0.6389(5) 0.7334(3) 0.0592(11) Uani 1.000000 .
C17 C 0.2700(3) 0.6256(4) 0.7733(3) 0.0565(10) Uani 1.000000 .
C11 C 0.3368(3) 0.5123(5) 0.4939(3) 0.0595(11) Uani 1.000000 .
C3 C 0.4467(3) 0.6719(5) 0.7907(3) 0.0575(11) Uani 1.000000 .
C10 C 0.3620(3) 0.6213(5) 0.5633(3) 0.0563(11) Uani 1.000000 .
C19 C 0.1298(3) 0.6028(5) 0.8063(3) 0.0637(12) Uani 1.000000 .
C16 C 0.2958(3) 0.5830(5) 0.8664(3) 0.0666(12) Uani 1.000000 .
H16 H 0.3607(3) 0.5670(5) 0.9099(3) 0.0799(14) Uiso 1.000000 R
C8 C 0.2805(3) 0.4514(5) 0.6070(3) 0.0625(11) Uani 1.000000 .
H8 H 0.2506(3) 0.3984(5) 0.6408(3) 0.0750(14) Uiso 1.000000 R
C15 C 0.4147(3) 0.7389(5) 0.5527(3) 0.0689(12) Uani 1.000000 .
H15 H 0.4316(3) 0.8121(5) 0.5977(3) 0.0827(15) Uiso 1.000000 R
C4 C 0.4894(3) 0.7945(5) 0.8399(3) 0.0650(12) Uani 1.000000 .
H4 H 0.4502(3) 0.8749(5) 0.8348(3) 0.0780(14) Uiso 1.000000 R
C23 C 0.0937(3) 0.6809(5) 0.6440(3) 0.0669(12) Uani 1.000000 .
H23 H 0.1143(3) 0.7067(5) 0.5949(3) 0.0802(15) Uiso 1.000000 R
C2 C 0.5087(3) 0.5551(5) 0.8047(3) 0.0696(12) Uani 1.000000 .
H2a H 0.4811(3) 0.4709(5) 0.7733(3) 0.0836(15) Uiso 1.000000 R
C5 C 0.5901(4) 0.7979(6) 0.8967(3) 0.0764(14) Uani 1.000000 .
H5 H 0.6199(4) 0.8807(6) 0.9287(3) 0.0917(16) Uiso 1.000000 R
C20 C 0.0285(4) 0.6078(6) 0.7909(4) 0.0755(14) Uani 1.000000 .
H20 H 0.0067(4) 0.5841(6) 0.8395(4) 0.0906(16) Uiso 1.000000 R
C22 C -0.0055(3) 0.6838(5) 0.6291(4) 0.0778(14) Uani 1.000000 .
H22 H -0.0521(3) 0.7098(5) 0.5691(4) 0.0934(17) Uiso 1.000000 R
C6 C 0.6448(4) 0.6774(6) 0.9048(4) 0.0803(15) Uani 1.000000 .
H6 H 0.7125(4) 0.6801(6) 0.9430(4) 0.0964(18) Uiso 1.000000 R
C21 C -0.0376(4) 0.6487(6) 0.7022(4) 0.0800(15) Uani 1.000000 .
H21 H -0.1053(4) 0.6531(6) 0.6906(4) 0.0960(18) Uiso 1.000000 R
C12 C 0.3631(4) 0.5199(6) 0.4148(3) 0.0761(13) Uani 1.000000 .
H12 H 0.3463(4) 0.4480(6) 0.3689(3) 0.0913(16) Uiso 1.000000 R
C14 C 0.4414(4) 0.7452(6) 0.4747(4) 0.0836(15) Uani 1.000000 .
H14 H 0.4777(4) 0.8228(6) 0.4674(4) 0.1004(18) Uiso 1.000000 R
C13 C 0.4154(4) 0.6389(7) 0.4071(4) 0.0906(17) Uani 1.000000 .
H13 H 0.4336(4) 0.6473(7) 0.3544(4) 0.109(2) Uiso 1.000000 R
C1 C 0.8073(5) 0.3853(8) 0.8485(5) 0.109(2) Uani 1.000000 .
H1a H 0.772(2) 0.338(4) 0.7884(14) 0.164(3) Uiso 1.000000 GR
H1b H 0.811(3) 0.4853(8) 0.837(3) 0.164(3) Uiso 1.000000 GR
H1c H 0.8735(13) 0.347(5) 0.8775(16) 0.164(3) Uiso 1.000000 GR
H1 H 0.695(4) 0.426(6) 0.885(4) 0.095(16) Uiso 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
O1 C1 1.407(6) . ?
O1 H1 1.01(6) . ?
N2 H2 0.8600 . ?
N2 C11 1.366(5) . ?
N2 C8 1.374(5) . ?
N3 H3 0.8600 . ?
N3 C19 1.363(5) . ?
N3 C16 1.379(6) . ?
N1 C2 1.341(5) . ?
N1 C6 1.334(6) . ?
C7 H7 0.9800 . ?
C7 C9 1.504(6) . ?
C7 C17 1.507(6) . ?
C7 C3 1.516(5) . ?
C9 C10 1.441(6) . ?
C9 C8 1.349(6) . ?
C18 C17 1.431(6) . ?
C18 C19 1.405(6) . ?
C18 C23 1.398(6) . ?
C17 C16 1.366(6) . ?
C11 C10 1.408(6) . ?
C11 C12 1.386(6) . ?
C3 C4 1.381(6) . ?
C3 C2 1.384(6) . ?
C10 C15 1.388(6) . ?
C19 C20 1.399(6) . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.373(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(6) . ?
C23 H23 0.9300 . ?
C23 C22 1.369(6) . ?
C2 H2a 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.362(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.368(7) . ?
C22 H22 0.9300 . ?
C22 C21 1.389(7) . ?
C6 H6 0.9300 . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.382(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.372(8) . ?
C13 H13 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 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
H1 O1 C1 106(3) . . ?
C11 N2 H2 125.6(2) . . ?
C8 N2 H2 125.6(2) . . ?
C8 N2 C11 108.7(4) . . ?
C19 N3 H3 125.5(2) . . ?
C16 N3 H3 125.5(2) . . ?
C16 N3 C19 109.0(3) . . ?
C6 N1 C2 117.2(4) . . ?
C9 C7 H7 106.0(2) . . ?
C17 C7 H7 106.0(2) . . ?
C17 C7 C9 114.2(3) . . ?
C3 C7 H7 106.0(2) . . ?
C3 C7 C9 111.6(3) . . ?
C3 C7 C17 112.5(3) . . ?
C10 C9 C7 123.3(4) . . ?
C8 C9 C7 130.5(4) . . ?
C8 C9 C10 106.1(4) . . ?
C19 C18 C17 107.2(4) . . ?
C23 C18 C17 134.3(4) . . ?
C23 C18 C19 118.5(4) . . ?
C18 C17 C7 125.1(4) . . ?
C16 C17 C7 128.1(4) . . ?
C16 C17 C18 106.5(4) . . ?
C10 C11 N2 107.5(4) . . ?
C12 C11 N2 131.0(4) . . ?
C12 C11 C10 121.4(4) . . ?
C4 C3 C7 121.7(4) . . ?
C2 C3 C7 121.6(4) . . ?
C2 C3 C4 116.7(4) . . ?
C11 C10 C9 106.9(4) . . ?
C15 C10 C9 133.5(4) . . ?
C15 C10 C11 119.6(4) . . ?
C18 C19 N3 107.7(4) . . ?
C20 C19 N3 130.8(4) . . ?
C20 C19 C18 121.5(4) . . ?
C17 C16 N3 109.6(4) . . ?
H16 C16 N3 125.2(2) . . ?
H16 C16 C17 125.2(3) . . ?
C9 C8 N2 110.7(4) . . ?
H8 C8 N2 124.7(2) . . ?
H8 C8 C9 124.7(2) . . ?
H15 C15 C10 120.6(3) . . ?
C14 C15 C10 118.7(5) . . ?
C14 C15 H15 120.6(3) . . ?
H4 C4 C3 120.0(3) . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0(3) . . ?
H23 C23 C18 120.2(3) . . ?
C22 C23 C18 119.7(4) . . ?
C22 C23 H23 120.2(3) . . ?
C3 C2 N1 124.1(4) . . ?
H2a C2 N1 118.0(3) . . ?
H2a C2 C3 118.0(3) . . ?
H5 C5 C4 120.7(3) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 H5 120.7(3) . . ?
H20 C20 C19 120.9(3) . . ?
C21 C20 C19 118.1(5) . . ?
C21 C20 H20 120.9(3) . . ?
H22 C22 C23 119.5(3) . . ?
C21 C22 C23 121.0(5) . . ?
C21 C22 H22 119.5(3) . . ?
C5 C6 N1 123.4(5) . . ?
H6 C6 N1 118.3(3) . . ?
H6 C6 C5 118.3(3) . . ?
C22 C21 C20 121.1(4) . . ?
H21 C21 C20 119.4(3) . . ?
H21 C21 C22 119.4(3) . . ?
H12 C12 C11 121.5(3) . . ?
C13 C12 C11 117.1(5) . . ?
C13 C12 H12 121.5(3) . . ?
H14 C14 C15 119.4(3) . . ?
C13 C14 C15 121.1(5) . . ?
C13 C14 H14 119.4(3) . . ?
C14 C13 C12 122.1(5) . . ?
H13 C13 C12 119.0(3) . . ?
H13 C13 C14 119.0(3) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?

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
N2 C11 C10 C9 -0.1(3) . . . . ?
N2 C11 C10 C15 179.5(3) . . . . ?
N2 C11 C12 C13 -179.5(5) . . . . ?
N2 C8 C9 C7 -178.5(3) . . . . ?
N2 C8 C9 C10 -1.2(4) . . . . ?
N3 C19 C18 C17 -0.8(4) . . . . ?
N3 C19 C18 C23 -179.3(4) . . . . ?
N3 C19 C20 C21 179.5(5) . . . . ?
N3 C16 C17 C7 174.8(3) . . . . ?
N3 C16 C17 C18 0.8(4) . . . . ?
N1 C2 C3 C7 177.2(4) . . . . ?
N1 C2 C3 C4 -1.4(6) . . . . ?
N1 C6 C5 C4 -0.1(6) . . . . ?
C7 C9 C10 C11 178.3(4) . . . . ?
C7 C9 C10 C15 -1.2(5) . . . . ?
C7 C17 C18 C19 -174.3(4) . . . . ?
C7 C17 C18 C23 4.0(6) . . . . ?
C7 C3 C4 C5 -176.1(4) . . . . ?
C9 C10 C11 C12 -179.9(3) . . . . ?
C9 C10 C15 C14 179.1(5) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C18 C23 C22 C21 1.4(5) . . . . ?
C11 C10 C15 C14 -0.3(5) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C10 C15 C14 C13 1.1(5) . . . . ?
C19 C20 C21 C22 0.3(6) . . . . ?
C15 C14 C13 C12 -1.2(7) . . . . ?
C23 C22 C21 C20 -1.1(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_40MIr-PMDI-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2303199'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.4807(19)
_cell_length_b                   9.3916(10)
_cell_length_c                   15.0389(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.567(4)
_cell_angle_gamma                90
_cell_volume                     1888.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5748
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             752.442
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21276
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2036
_reflns_number_total             3720
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.4400
_refine_diff_density_min         -0.4421
_refine_diff_density_rms         0.0999
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             7.7796
_refine_ls_goodness_of_fit_ref   1.5304
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1730
_refine_ls_R_factor_gt           0.1119
_refine_ls_restrained_S_all      1.5304
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2865
_refine_ls_wR_factor_ref         0.4333
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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
O1 O 0.7565(3) 0.3631(4) 0.9103(3) 0.0839(12) Uani 1.000000 .
N2 N 0.2868(3) 0.4098(4) 0.5220(3) 0.0690(12) Uani 1.000000 .
N3 N 0.2114(3) 0.5675(4) 0.8861(3) 0.0736(12) Uani 1.000000 .
N1 N 0.6060(3) 0.5555(5) 0.8608(3) 0.0833(14) Uani 1.000000 .
C9 C 0.3243(3) 0.5799(5) 0.6347(3) 0.0566(11) Uani 1.000000 .
C7 C 0.3378(3) 0.6668(5) 0.7233(3) 0.0591(12) Uani 1.000000 .
C11 C 0.3368(3) 0.5124(5) 0.4938(3) 0.0628(12) Uani 1.000000 .
C8 C 0.2805(4) 0.4513(5) 0.6074(3) 0.0643(13) Uani 1.000000 .
C18 C 0.1637(4) 0.6385(5) 0.7334(3) 0.0605(12) Uani 1.000000 .
C3 C 0.4472(3) 0.6716(5) 0.7909(3) 0.0595(12) Uani 1.000000 .
C10 C 0.3620(3) 0.6212(5) 0.5635(3) 0.0599(12) Uani 1.000000 .
C17 C 0.2704(3) 0.6261(5) 0.7730(3) 0.0597(12) Uani 1.000000 .
C4 C 0.4896(4) 0.7948(5) 0.8401(4) 0.0691(13) Uani 1.000000 .
C19 C 0.1298(4) 0.6034(5) 0.8058(4) 0.0656(13) Uani 1.000000 .
C15 C 0.4146(4) 0.7392(6) 0.5524(4) 0.0691(13) Uani 1.000000 .
C23 C 0.0940(4) 0.6808(5) 0.6444(4) 0.0707(14) Uani 1.000000 .
C2 C 0.5088(4) 0.5557(5) 0.8047(4) 0.0714(14) Uani 1.000000 .
C16 C 0.2960(4) 0.5830(5) 0.8662(4) 0.0702(14) Uani 1.000000 .
C5 C 0.5894(4) 0.7977(6) 0.8964(4) 0.0794(15) Uani 1.000000 .
C22 C -0.0054(4) 0.6844(6) 0.6289(5) 0.0797(16) Uani 1.000000 .
C6 C 0.6448(4) 0.6775(6) 0.9048(4) 0.0846(17) Uani 1.000000 .
C20 C 0.0290(4) 0.6075(6) 0.7910(5) 0.0792(16) Uani 1.000000 .
C12 C 0.3632(4) 0.5201(6) 0.4146(4) 0.0789(15) Uani 1.000000 .
C21 C -0.0376(4) 0.6489(6) 0.7019(5) 0.0839(17) Uani 1.000000 .
C14 C 0.4408(5) 0.7457(7) 0.4749(4) 0.0884(17) Uani 1.000000 .
C13 C 0.4149(5) 0.6390(7) 0.4064(4) 0.0918(18) Uani 1.000000 .
C1 C 0.8075(5) 0.3850(8) 0.8483(5) 0.114(2) Uani 1.000000 .
H12 H 0.3466(4) 0.4479(6) 0.3688(4) 0.0947(18) Uiso 1.000000 R
H13 H 0.4329(5) 0.6477(7) 0.3536(4) 0.110(2) Uiso 1.000000 R
H14 H 0.4770(5) 0.8236(7) 0.4677(4) 0.106(2) Uiso 1.000000 R
H15 H 0.4315(4) 0.8126(6) 0.5973(4) 0.0829(16) Uiso 1.000000 R
H23 H 0.1150(4) 0.7068(5) 0.5955(4) 0.0848(17) Uiso 1.000000 R
H22 H -0.0519(4) 0.7109(6) 0.5688(5) 0.0957(19) Uiso 1.000000 R
H21 H -0.1054(4) 0.6531(6) 0.6903(5) 0.101(2) Uiso 1.000000 R
H20 H 0.0074(4) 0.5831(6) 0.8399(5) 0.0950(19) Uiso 1.000000 R
H2a H 0.4810(4) 0.4718(5) 0.7728(4) 0.0857(17) Uiso 1.000000 R
H6 H 0.7127(4) 0.6805(6) 0.9431(4) 0.101(2) Uiso 1.000000 R
H5 H 0.6192(4) 0.8806(6) 0.9285(4) 0.0953(19) Uiso 1.000000 R
H4 H 0.4504(4) 0.8753(5) 0.8349(4) 0.0829(16) Uiso 1.000000 R
H7 H 0.3198(3) 0.7647(5) 0.7007(3) 0.0709(14) Uiso 1.000000 R
H8 H 0.2506(4) 0.3984(5) 0.6413(3) 0.0771(15) Uiso 1.000000 R
H16 H 0.3610(4) 0.5666(5) 0.9098(4) 0.0843(16) Uiso 1.000000 R
H1a H 0.7678(19) 0.349(5) 0.7854(12) 0.172(4) Uiso 1.000000 GR
H1b H 0.819(4) 0.4850(10) 0.844(3) 0.172(4) Uiso 1.000000 GR
H1c H 0.8704(18) 0.336(5) 0.873(2) 0.172(4) Uiso 1.000000 GR
H1 H 0.705(3) 0.411(6) 0.892(3) 0.1258(18) Uiso 1.000000 GR
H2 H 0.2632(3) 0.3321(4) 0.4915(3) 0.0828(14) Uiso 1.000000 R
H3 H 0.2100(3) 0.5398(4) 0.9401(3) 0.0884(15) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.409(7) . ?
O1 H1 0.8200 . ?
N2 C11 1.366(6) . ?
N2 C8 1.378(6) . ?
N2 H2 0.8600 . ?
N3 C19 1.369(6) . ?
N3 C16 1.376(6) . ?
N3 H3 0.8600 . ?
N1 C2 1.335(6) . ?
N1 C6 1.334(7) . ?
C9 C7 1.510(6) . ?
C9 C8 1.353(6) . ?
C9 C10 1.430(7) . ?
C7 C3 1.519(6) . ?
C7 C17 1.490(7) . ?
C7 H7 0.9800 . ?
C11 C10 1.408(7) . ?
C11 C12 1.385(7) . ?
C8 H8 0.9300 . ?
C18 C17 1.431(7) . ?
C18 C19 1.394(7) . ?
C18 C23 1.390(7) . ?
C3 C4 1.384(6) . ?
C3 C2 1.372(7) . ?
C10 C15 1.390(7) . ?
C17 C16 1.367(7) . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C19 C20 1.390(7) . ?
C15 C14 1.359(7) . ?
C15 H15 0.9300 . ?
C23 C22 1.367(7) . ?
C23 H23 0.9300 . ?
C2 H2a 0.9300 . ?
C16 H16 0.9300 . ?
C5 C6 1.363(8) . ?
C5 H5 0.9300 . ?
C22 C21 1.390(9) . ?
C22 H22 0.9300 . ?
C6 H6 0.9300 . ?
C20 C21 1.373(8) . ?
C20 H20 0.9300 . ?
C12 C13 1.376(8) . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C14 C13 1.381(9) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 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
H1 O1 C1 109.5 . . ?
C8 N2 C11 108.8(4) . . ?
H2 N2 C11 125.6(3) . . ?
H2 N2 C8 125.6(3) . . ?
C16 N3 C19 108.8(4) . . ?
H3 N3 C19 125.6(3) . . ?
H3 N3 C16 125.6(3) . . ?
C6 N1 C2 117.0(4) . . ?
C8 C9 C7 129.6(4) . . ?
C10 C9 C7 123.8(4) . . ?
C10 C9 C8 106.5(4) . . ?
C3 C7 C9 110.9(4) . . ?
C17 C7 C9 114.6(4) . . ?
C17 C7 C3 112.8(4) . . ?
H7 C7 C9 105.9(2) . . ?
H7 C7 C3 105.9(2) . . ?
H7 C7 C17 105.9(2) . . ?
C10 C11 N2 107.3(4) . . ?
C12 C11 N2 131.1(5) . . ?
C12 C11 C10 121.6(5) . . ?
C9 C8 N2 110.1(4) . . ?
H8 C8 N2 124.9(3) . . ?
H8 C8 C9 124.9(3) . . ?
C19 C18 C17 107.7(4) . . ?
C23 C18 C17 133.8(4) . . ?
C23 C18 C19 118.4(5) . . ?
C4 C3 C7 121.2(4) . . ?
C2 C3 C7 121.9(4) . . ?
C2 C3 C4 116.9(5) . . ?
C11 C10 C9 107.2(4) . . ?
C15 C10 C9 133.7(5) . . ?
C15 C10 C11 119.1(4) . . ?
C18 C17 C7 125.6(4) . . ?
C16 C17 C7 128.2(4) . . ?
C16 C17 C18 106.0(4) . . ?
C5 C4 C3 119.7(5) . . ?
H4 C4 C3 120.2(3) . . ?
H4 C4 C5 120.2(3) . . ?
C18 C19 N3 107.6(4) . . ?
C20 C19 N3 130.2(5) . . ?
C20 C19 C18 122.2(5) . . ?
C14 C15 C10 119.0(5) . . ?
H15 C15 C10 120.5(3) . . ?
H15 C15 C14 120.5(4) . . ?
C22 C23 C18 120.0(5) . . ?
H23 C23 C18 120.0(3) . . ?
H23 C23 C22 120.0(3) . . ?
C3 C2 N1 124.3(5) . . ?
H2a C2 N1 117.8(3) . . ?
H2a C2 C3 117.8(3) . . ?
C17 C16 N3 109.9(5) . . ?
H16 C16 N3 125.1(3) . . ?
H16 C16 C17 125.1(3) . . ?
C6 C5 C4 119.1(5) . . ?
H5 C5 C4 120.5(3) . . ?
H5 C5 C6 120.5(3) . . ?
C21 C22 C23 120.6(5) . . ?
H22 C22 C23 119.7(4) . . ?
H22 C22 C21 119.7(3) . . ?
C5 C6 N1 123.0(5) . . ?
H6 C6 N1 118.5(3) . . ?
H6 C6 C5 118.5(3) . . ?
C21 C20 C19 117.7(5) . . ?
H20 C20 C19 121.2(3) . . ?
H20 C20 C21 121.2(3) . . ?
C13 C12 C11 117.3(5) . . ?
H12 C12 C11 121.4(3) . . ?
H12 C12 C13 121.4(4) . . ?
C20 C21 C22 121.1(5) . . ?
H21 C21 C22 119.4(3) . . ?
H21 C21 C20 119.4(3) . . ?
C13 C14 C15 121.4(6) . . ?
H14 C14 C15 119.3(4) . . ?
H14 C14 C13 119.3(3) . . ?
C14 C13 C12 121.6(5) . . ?
H13 C13 C12 119.2(4) . . ?
H13 C13 C14 119.2(3) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?

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
N2 C11 C10 C9 -0.4(4) . . . . ?
N2 C11 C10 C15 179.5(4) . . . . ?
N2 C11 C12 C13 -179.5(6) . . . . ?
N2 C8 C9 C7 -178.6(3) . . . . ?
N2 C8 C9 C10 -1.1(4) . . . . ?
N3 C19 C18 C17 -1.4(4) . . . . ?
N3 C19 C18 C23 -179.1(4) . . . . ?
N3 C19 C20 C21 179.7(6) . . . . ?
N3 C16 C17 C7 174.7(3) . . . . ?
N3 C16 C17 C18 0.3(4) . . . . ?
N1 C2 C3 C7 177.7(5) . . . . ?
N1 C2 C3 C4 -1.0(7) . . . . ?
N1 C6 C5 C4 -0.2(7) . . . . ?
C9 C7 C3 C4 140.9(4) . . . . ?
C9 C7 C3 C2 -37.8(5) . . . . ?
C9 C7 C17 C18 -64.4(4) . . . . ?
C9 C7 C17 C16 122.1(4) . . . . ?
C9 C10 C11 C12 -179.8(4) . . . . ?
C9 C10 C15 C14 179.4(6) . . . . ?
C7 C3 C4 C5 -176.5(5) . . . . ?
C7 C17 C18 C19 -174.0(5) . . . . ?
C7 C17 C18 C23 3.3(6) . . . . ?
C11 C10 C15 C14 -0.5(5) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C18 C23 C22 C21 1.4(6) . . . . ?
C3 C4 C5 C6 -1.7(6) . . . . ?
C10 C15 C14 C13 1.1(6) . . . . ?
C19 C20 C21 C22 0.4(6) . . . . ?
C15 C14 C13 C12 -1.3(7) . . . . ?
C23 C22 C21 C20 -0.9(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_80MIr+2Weeks-PMDI-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2303201'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.4804(19)
_cell_length_b                   9.3873(10)
_cell_length_c                   15.0373(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.596(4)
_cell_angle_gamma                90
_cell_volume                     1887.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5602
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.13
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             752.442
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.9971
_diffrn_reflns_Laue_measured_fraction_max 0.9971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16290
_diffrn_reflns_point_group_measured_fraction_full 0.9971
_diffrn_reflns_point_group_measured_fraction_max 0.9971
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.73
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -17
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2145
_reflns_number_total             3448
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.5626
_refine_diff_density_min         -0.4913
_refine_diff_density_rms         0.1107
_refine_ls_d_res_high            0.8301
_refine_ls_d_res_low             7.4554
_refine_ls_goodness_of_fit_ref   1.5692
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.1228
_refine_ls_restrained_S_all      1.5692
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3134
_refine_ls_wR_factor_ref         0.4094
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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
O1 O 0.7567(3) 0.6368(4) 0.9105(3) 0.0835(11) Uani 1.000000 .
N2 N 0.2871(3) 0.5902(4) 0.5221(3) 0.0708(11) Uani 1.000000 .
N3 N 0.2112(3) 0.4326(4) 0.8863(3) 0.0741(12) Uani 1.000000 .
N1 N 0.6060(3) 0.4443(4) 0.8610(3) 0.0820(13) Uani 1.000000 .
C9 C 0.3240(3) 0.4196(4) 0.6350(3) 0.0553(10) Uani 1.000000 .
C7 C 0.3380(3) 0.3333(4) 0.7234(3) 0.0582(11) Uani 1.000000 .
C18 C 0.1635(3) 0.3622(4) 0.7332(3) 0.0606(11) Uani 1.000000 .
C17 C 0.2700(3) 0.3741(4) 0.7727(3) 0.0597(11) Uani 1.000000 .
C11 C 0.3366(3) 0.4872(5) 0.4938(3) 0.0633(11) Uani 1.000000 .
C10 C 0.3617(3) 0.3785(5) 0.5631(3) 0.0593(11) Uani 1.000000 .
C3 C 0.4470(3) 0.3285(4) 0.7907(3) 0.0601(11) Uani 1.000000 .
C15 C 0.4145(3) 0.2600(5) 0.5526(3) 0.0695(13) Uani 1.000000 .
C8 C 0.2803(3) 0.5491(5) 0.6073(3) 0.0651(12) Uani 1.000000 .
C19 C 0.1296(4) 0.3972(4) 0.8056(3) 0.0659(12) Uani 1.000000 .
C16 C 0.2959(4) 0.4171(5) 0.8661(3) 0.0694(13) Uani 1.000000 .
C23 C 0.0937(4) 0.3197(5) 0.6443(3) 0.0693(13) Uani 1.000000 .
C4 C 0.4892(4) 0.2046(5) 0.8398(3) 0.0682(12) Uani 1.000000 .
C22 C -0.0053(4) 0.3149(5) 0.6296(4) 0.0797(15) Uani 1.000000 .
C2 C 0.5081(4) 0.4443(5) 0.8048(4) 0.0737(13) Uani 1.000000 .
C5 C 0.5898(4) 0.2017(5) 0.8968(4) 0.0808(15) Uani 1.000000 .
C12 C 0.3634(4) 0.4797(6) 0.4153(3) 0.0776(14) Uani 1.000000 .
C6 C 0.6451(4) 0.3221(6) 0.9050(4) 0.0837(16) Uani 1.000000 .
C21 C -0.0380(4) 0.3516(6) 0.7019(5) 0.0835(16) Uani 1.000000 .
C20 C 0.0292(4) 0.3922(5) 0.7910(4) 0.0782(15) Uani 1.000000 .
C13 C 0.4147(5) 0.3616(7) 0.4063(4) 0.0932(17) Uani 1.000000 .
C14 C 0.4414(4) 0.2537(7) 0.4761(4) 0.0899(17) Uani 1.000000 .
C1 C 0.8069(5) 0.6155(7) 0.8489(5) 0.115(2) Uani 1.000000 .
H12 H 0.3472(4) 0.5526(6) 0.3699(3) 0.0932(17) Uiso 1.000000 R
H13 H 0.4321(5) 0.3529(7) 0.3531(4) 0.112(2) Uiso 1.000000 R
H14 H 0.4783(4) 0.1762(7) 0.4695(4) 0.108(2) Uiso 1.000000 R
H15 H 0.4310(3) 0.1866(5) 0.5975(3) 0.0834(15) Uiso 1.000000 R
H23 H 0.1143(4) 0.2946(5) 0.5950(3) 0.0831(15) Uiso 1.000000 R
H22 H -0.0518(4) 0.2865(5) 0.5699(4) 0.0957(18) Uiso 1.000000 R
H21 H -0.1059(4) 0.3487(6) 0.6900(5) 0.1002(19) Uiso 1.000000 R
H20 H 0.0079(4) 0.4158(5) 0.8401(4) 0.0939(18) Uiso 1.000000 R
H2a H 0.4801(4) 0.5285(5) 0.7734(4) 0.0884(16) Uiso 1.000000 R
H6 H 0.7131(4) 0.3190(6) 0.9430(4) 0.1004(19) Uiso 1.000000 R
H5 H 0.6195(4) 0.1189(5) 0.9291(4) 0.0970(18) Uiso 1.000000 R
H4 H 0.4499(4) 0.1241(5) 0.8344(3) 0.0819(15) Uiso 1.000000 R
H7 H 0.3200(3) 0.2353(4) 0.7009(3) 0.0699(13) Uiso 1.000000 R
H8 H 0.2502(3) 0.6021(5) 0.6411(3) 0.0781(14) Uiso 1.000000 R
H16 H 0.3610(4) 0.4334(5) 0.9095(3) 0.0833(15) Uiso 1.000000 R
H1a H 0.7673(18) 0.652(5) 0.7862(11) 0.172(3) Uiso 1.000000 GR
H1b H 0.8701(17) 0.664(5) 0.874(2) 0.172(3) Uiso 1.000000 GR
H1c H 0.818(3) 0.5155(9) 0.844(3) 0.172(3) Uiso 1.000000 GR
H1 H 0.703(2) 0.594(6) 0.890(3) 0.1252(17) Uiso 1.000000 GR
H2 H 0.2640(3) 0.6682(4) 0.4917(3) 0.0849(13) Uiso 1.000000 R
H3 H 0.2098(3) 0.4599(4) 0.9404(3) 0.0890(14) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.395(7) . ?
O1 H1 0.8200 . ?
N2 C11 1.366(5) . ?
N2 C8 1.378(6) . ?
N2 H2 0.8600 . ?
N3 C19 1.370(6) . ?
N3 C16 1.381(6) . ?
N3 H3 0.8600 . ?
N1 C2 1.344(6) . ?
N1 C6 1.337(6) . ?
C9 C7 1.502(6) . ?
C9 C10 1.437(6) . ?
C9 C8 1.360(6) . ?
C7 C17 1.492(6) . ?
C7 C3 1.513(6) . ?
C7 H7 0.9800 . ?
C18 C17 1.428(6) . ?
C18 C19 1.395(6) . ?
C18 C23 1.389(6) . ?
C17 C16 1.368(6) . ?
C11 C10 1.404(6) . ?
C11 C12 1.379(6) . ?
C10 C15 1.393(6) . ?
C3 C4 1.388(6) . ?
C3 C2 1.366(6) . ?
C15 C14 1.349(7) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C19 C20 1.385(7) . ?
C16 H16 0.9300 . ?
C23 C22 1.365(7) . ?
C23 H23 0.9300 . ?
C4 C5 1.377(7) . ?
C4 H4 0.9300 . ?
C22 C21 1.385(8) . ?
C22 H22 0.9300 . ?
C2 H2a 0.9300 . ?
C5 C6 1.362(7) . ?
C5 H5 0.9300 . ?
C12 C13 1.370(8) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C21 C20 1.374(7) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C13 C14 1.402(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 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
H1 O1 C1 109.5 . . ?
C8 N2 C11 109.0(4) . . ?
H2 N2 C11 125.5(2) . . ?
H2 N2 C8 125.5(2) . . ?
C16 N3 C19 108.4(4) . . ?
H3 N3 C19 125.8(2) . . ?
H3 N3 C16 125.8(3) . . ?
C6 N1 C2 117.1(4) . . ?
C10 C9 C7 124.0(4) . . ?
C8 C9 C7 129.9(4) . . ?
C8 C9 C10 106.1(4) . . ?
C17 C7 C9 114.2(3) . . ?
C3 C7 C9 111.1(3) . . ?
C3 C7 C17 113.2(4) . . ?
H7 C7 C9 105.9(2) . . ?
H7 C7 C17 105.9(2) . . ?
H7 C7 C3 105.9(2) . . ?
C19 C18 C17 107.7(4) . . ?
C23 C18 C17 133.9(4) . . ?
C23 C18 C19 118.3(4) . . ?
C18 C17 C7 125.9(4) . . ?
C16 C17 C7 127.8(4) . . ?
C16 C17 C18 106.1(4) . . ?
C10 C11 N2 107.5(4) . . ?
C12 C11 N2 131.1(5) . . ?
C12 C11 C10 121.4(4) . . ?
C11 C10 C9 107.4(4) . . ?
C15 C10 C9 133.1(4) . . ?
C15 C10 C11 119.5(4) . . ?
C4 C3 C7 120.9(4) . . ?
C2 C3 C7 121.8(4) . . ?
C2 C3 C4 117.2(4) . . ?
C14 C15 C10 118.9(5) . . ?
H15 C15 C10 120.5(3) . . ?
H15 C15 C14 120.5(3) . . ?
C9 C8 N2 110.1(4) . . ?
H8 C8 N2 124.9(2) . . ?
H8 C8 C9 124.9(3) . . ?
C18 C19 N3 107.9(4) . . ?
C20 C19 N3 130.1(5) . . ?
C20 C19 C18 122.1(5) . . ?
C17 C16 N3 109.9(4) . . ?
H16 C16 N3 125.0(3) . . ?
H16 C16 C17 125.0(3) . . ?
C22 C23 C18 119.8(5) . . ?
H23 C23 C18 120.1(3) . . ?
H23 C23 C22 120.1(3) . . ?
C5 C4 C3 119.4(4) . . ?
H4 C4 C3 120.3(3) . . ?
H4 C4 C5 120.3(3) . . ?
C21 C22 C23 121.3(5) . . ?
H22 C22 C23 119.4(3) . . ?
H22 C22 C21 119.4(3) . . ?
C3 C2 N1 124.2(4) . . ?
H2a C2 N1 117.9(3) . . ?
H2a C2 C3 117.9(3) . . ?
C6 C5 C4 119.0(4) . . ?
H5 C5 C4 120.5(3) . . ?
H5 C5 C6 120.5(3) . . ?
C13 C12 C11 117.9(5) . . ?
H12 C12 C11 121.1(3) . . ?
H12 C12 C13 121.1(3) . . ?
C5 C6 N1 123.0(5) . . ?
H6 C6 N1 118.5(3) . . ?
H6 C6 C5 118.5(3) . . ?
C20 C21 C22 120.5(5) . . ?
H21 C21 C22 119.8(3) . . ?
H21 C21 C20 119.8(3) . . ?
C21 C20 C19 118.1(5) . . ?
H20 C20 C19 120.9(3) . . ?
H20 C20 C21 120.9(3) . . ?
C14 C13 C12 121.0(5) . . ?
H13 C13 C12 119.5(3) . . ?
H13 C13 C14 119.5(3) . . ?
C13 C14 C15 121.3(5) . . ?
H14 C14 C15 119.4(3) . . ?
H14 C14 C13 119.4(3) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?

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
N2 C11 C10 C9 0.6(4) . . . . ?
N2 C11 C10 C15 -179.0(3) . . . . ?
N2 C11 C12 C13 179.1(6) . . . . ?
N2 C8 C9 C7 178.0(3) . . . . ?
N2 C8 C9 C10 0.9(4) . . . . ?
N3 C19 C18 C17 1.3(4) . . . . ?
N3 C19 C18 C23 178.8(3) . . . . ?
N3 C19 C20 C21 -179.5(5) . . . . ?
N3 C16 C17 C7 -174.5(3) . . . . ?
N3 C16 C17 C18 -0.2(4) . . . . ?
N1 C2 C3 C7 -177.6(5) . . . . ?
N1 C2 C3 C4 1.6(6) . . . . ?
N1 C6 C5 C4 0.7(7) . . . . ?
C9 C7 C17 C18 64.0(4) . . . . ?
C9 C7 C17 C16 -122.6(4) . . . . ?
C9 C7 C3 C4 -140.8(4) . . . . ?
C9 C7 C3 C2 38.3(4) . . . . ?
C9 C10 C11 C12 179.4(4) . . . . ?
C9 C10 C15 C14 -178.8(6) . . . . ?
C7 C17 C18 C19 173.8(4) . . . . ?
C7 C17 C18 C23 -3.2(6) . . . . ?
C7 C3 C4 C5 176.8(4) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C18 C23 C22 C21 -0.1(5) . . . . ?
C11 C10 C15 C14 0.8(5) . . . . ?
C11 C12 C13 C14 -1.7(6) . . . . ?
C10 C15 C14 C13 -1.8(6) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C15 C14 C13 C12 2.3(7) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C23 C22 C21 C20 -0.8(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_PMDI-MeOH'
_database_code_depnum_ccdc_archive 'CCDC 2266874'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2022-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C H4 O, C22 H17 N3'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.443
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'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/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.5277(5)
_cell_length_b                   9.4021(4)
_cell_length_c                   15.0821(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.559(1)
_cell_angle_gamma                90
_cell_volume                     1902.45(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7904
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.61
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0785 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       needle
_exptl_crystal_F_000             752.442
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            69093
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9989
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.61
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -19
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -10
_reflns_number_gt                3596
_reflns_number_total             4533
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.2700
_refine_diff_density_min         -0.3204
_refine_diff_density_rms         0.0738
_refine_ls_d_res_high            0.7602
_refine_ls_d_res_low             7.7928
_refine_ls_goodness_of_fit_ref   1.0891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0746
_refine_ls_restrained_S_all      1.0891
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+1.2009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1672
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C2(H2a), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22)
1.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     dual
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
O1 O 0.75663(13) 0.3629(2) 0.91090(13) 0.0568(5) Uani 1.000000 .
H1 H 0.7031(11) 0.405(3) 0.8899(13) 0.0852(7) Uiso 1.000000 GR
C1 C 0.8079(3) 0.3862(4) 0.8496(3) 0.0845(11) Uani 1.000000 .
H1a H 0.7714(10) 0.344(2) 0.7881(7) 0.1267(16) Uiso 1.000000 GR
H1b H 0.8143(17) 0.4866(4) 0.8418(15) 0.1267(16) Uiso 1.000000 GR
H1c H 0.8730(8) 0.344(3) 0.8770(10) 0.1267(16) Uiso 1.000000 GR
N1 N 0.60600(15) 0.5556(2) 0.86089(16) 0.0571(6) Uani 1.000000 .
N2 N 0.28690(14) 0.4097(2) 0.52194(13) 0.0430(5) Uani 1.000000 .
H2 H 0.26349(14) 0.3321(2) 0.49145(13) 0.0516(5) Uiso 1.000000 R
N3 N 0.21127(15) 0.5668(2) 0.88578(14) 0.0476(5) Uani 1.000000 .
H3 H 0.21014(15) 0.5388(2) 0.93964(14) 0.0572(6) Uiso 1.000000 R
C2 C 0.50889(16) 0.5554(2) 0.80463(17) 0.0447(5) Uani 1.000000 .
H2a H 0.48127(16) 0.4715(2) 0.77285(17) 0.0536(7) Uiso 1.000000 R
C3 C 0.44726(15) 0.6720(2) 0.79090(14) 0.0322(4) Uani 1.000000 .
C4 C 0.48952(17) 0.7947(2) 0.83992(16) 0.0415(5) Uani 1.000000 .
H4 H 0.45048(17) 0.8752(2) 0.83422(16) 0.0498(6) Uiso 1.000000 R
C5 C 0.58961(19) 0.7977(3) 0.89730(18) 0.0527(6) Uani 1.000000 .
H5 H 0.61909(19) 0.8798(3) 0.93033(18) 0.0632(8) Uiso 1.000000 R
C6 C 0.64451(18) 0.6772(3) 0.90455(19) 0.0570(7) Uani 1.000000 .
H6 H 0.71239(18) 0.6803(3) 0.94197(19) 0.0684(8) Uiso 1.000000 R
C7 C 0.33813(14) 0.6669(2) 0.72306(14) 0.0317(4) Uani 1.000000 .
H7 H 0.32005(14) 0.7647(2) 0.70064(14) 0.0381(5) Uiso 1.000000 R
C8 C 0.28035(16) 0.4508(2) 0.60696(15) 0.0377(5) Uani 1.000000 .
H8 H 0.25036(16) 0.3979(2) 0.64064(15) 0.0453(6) Uiso 1.000000 R
C9 C 0.32415(14) 0.5801(2) 0.63453(14) 0.0307(4) Uani 1.000000 .
C10 C 0.36145(14) 0.6212(2) 0.56325(14) 0.0322(4) Uani 1.000000 .
C11 C 0.41526(17) 0.7391(3) 0.55306(17) 0.0452(5) Uani 1.000000 .
H11 H 0.43332(17) 0.8116(3) 0.59850(17) 0.0542(7) Uiso 1.000000 R
C12 C 0.4408(2) 0.7455(3) 0.4745(2) 0.0613(7) Uani 1.000000 .
H12 H 0.4763(2) 0.8236(3) 0.4667(2) 0.0736(9) Uiso 1.000000 R
C13 C 0.4148(2) 0.6377(4) 0.4062(2) 0.0642(8) Uani 1.000000 .
H13 H 0.4330(2) 0.6456(4) 0.3536(2) 0.0771(9) Uiso 1.000000 R
C14 C 0.3631(2) 0.5205(3) 0.41445(17) 0.0538(6) Uani 1.000000 .
H14 H 0.3461(2) 0.4486(3) 0.36864(17) 0.0646(8) Uiso 1.000000 R
C15 C 0.33681(16) 0.5126(2) 0.49389(15) 0.0379(5) Uani 1.000000 .
C16 C 0.29542(17) 0.5828(2) 0.86563(16) 0.0418(5) Uani 1.000000 .
H16 H 0.36015(17) 0.5662(2) 0.90905(16) 0.0501(6) Uiso 1.000000 R
C17 C 0.27072(15) 0.6260(2) 0.77370(14) 0.0334(4) Uani 1.000000 .
C18 C 0.16367(15) 0.6396(2) 0.73360(15) 0.0343(4) Uani 1.000000 .
C19 C 0.09407(17) 0.6814(3) 0.64392(17) 0.0441(5) Uani 1.000000 .
H19 H 0.11465(17) 0.7065(3) 0.59477(17) 0.0529(6) Uiso 1.000000 R
C20 C -0.00554(19) 0.6847(3) 0.6295(2) 0.0552(7) Uani 1.000000 .
H20 H -0.05221(19) 0.7118(3) 0.5700(2) 0.0662(8) Uiso 1.000000 R
C21 C -0.03752(19) 0.6483(3) 0.7024(2) 0.0579(7) Uani 1.000000 .
H21 H -0.10512(19) 0.6524(3) 0.6908(2) 0.0695(9) Uiso 1.000000 R
C22 C 0.0286(2) 0.6066(3) 0.7908(2) 0.0521(6) Uani 1.000000 .
H22 H 0.0071(2) 0.5817(3) 0.8394(2) 0.0625(8) Uiso 1.000000 R
C23 C 0.12947(17) 0.6028(2) 0.80572(16) 0.0401(5) 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
O1 H1 0.8200 . ?
O1 C1 1.410(4) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
N1 C2 1.339(3) . ?
N1 C6 1.330(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.377(3) . ?
N2 C15 1.370(3) . ?
N3 H3 0.8600 . ?
N3 C16 1.376(3) . ?
N3 C23 1.373(3) . ?
C2 H2a 0.9300 . ?
C2 C3 1.380(3) . ?
C3 C4 1.381(3) . ?
C3 C7 1.523(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C9 1.511(3) . ?
C7 C17 1.505(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.361(3) . ?
C9 C10 1.430(3) . ?
C10 C11 1.399(3) . ?
C10 C15 1.406(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.354(3) . ?
C17 C18 1.442(3) . ?
C18 C19 1.399(3) . ?
C18 C23 1.401(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.395(3) . ?

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 O1 H1 109.5 . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C6 N1 C2 117.1(2) . . ?
C8 N2 H2 125.58(12) . . ?
C15 N2 H2 125.58(12) . . ?
C15 N2 C8 108.84(18) . . ?
C16 N3 H3 125.63(13) . . ?
C23 N3 H3 125.63(12) . . ?
C23 N3 C16 108.75(18) . . ?
H2a C2 N1 118.01(13) . . ?
C3 C2 N1 124.0(2) . . ?
C3 C2 H2a 118.01(12) . . ?
C4 C3 C2 117.00(19) . . ?
C7 C3 C2 121.63(18) . . ?
C7 C3 C4 121.36(18) . . ?
H4 C4 C3 120.05(13) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.05(14) . . ?
H5 C5 C4 120.76(14) . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.76(14) . . ?
C5 C6 N1 123.5(2) . . ?
H6 C6 N1 118.27(14) . . ?
H6 C6 C5 118.27(14) . . ?
H7 C7 C3 105.95(10) . . ?
C9 C7 C3 111.29(16) . . ?
C9 C7 H7 105.95(10) . . ?
C17 C7 C3 112.30(16) . . ?
C17 C7 H7 105.95(11) . . ?
C17 C7 C9 114.66(16) . . ?
H8 C8 N2 124.94(12) . . ?
C9 C8 N2 110.13(19) . . ?
C9 C8 H8 124.94(13) . . ?
C8 C9 C7 129.89(19) . . ?
C10 C9 C7 123.83(18) . . ?
C10 C9 C8 106.23(18) . . ?
C11 C10 C9 133.3(2) . . ?
C15 C10 C9 107.51(18) . . ?
C15 C10 C11 119.2(2) . . ?
H11 C11 C10 120.75(13) . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.75(16) . . ?
H12 C12 C11 119.29(16) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.29(15) . . ?
H13 C13 C12 119.21(15) . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.21(16) . . ?
H14 C14 C13 121.19(16) . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 H14 121.19(15) . . ?
C10 C15 N2 107.29(18) . . ?
C14 C15 N2 131.0(2) . . ?
C14 C15 C10 121.7(2) . . ?
H16 C16 N3 124.76(13) . . ?
C17 C16 N3 110.5(2) . . ?
C17 C16 H16 124.76(13) . . ?
C16 C17 C7 128.90(19) . . ?
C18 C17 C7 124.86(18) . . ?
C18 C17 C16 105.99(19) . . ?
C19 C18 C17 133.9(2) . . ?
C23 C18 C17 107.40(19) . . ?
C23 C18 C19 118.7(2) . . ?
H19 C19 C18 120.52(13) . . ?
C20 C19 C18 119.0(2) . . ?
C20 C19 H19 120.52(16) . . ?
H20 C20 C19 119.37(16) . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.37(15) . . ?
H21 C21 C20 119.40(15) . . ?
C22 C21 C20 121.2(2) . . ?
C22 C21 H21 119.40(15) . . ?
H22 C22 C21 121.12(15) . . ?
C23 C22 C21 117.8(2) . . ?
C23 C22 H22 121.12(15) . . ?
C18 C23 N3 107.37(19) . . ?
C22 C23 N3 130.5(2) . . ?
C22 C23 C18 122.1(2) . . ?

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 C2 C3 C4 -1.0(3) . . . . ?
N1 C2 C3 C7 177.7(2) . . . . ?
N1 C6 C5 C4 -1.7(3) . . . . ?
N2 C8 C9 C7 -178.23(15) . . . . ?
N2 C8 C9 C10 -0.83(19) . . . . ?
N2 C15 C10 C9 -0.15(19) . . . . ?
N2 C15 C10 C11 178.59(17) . . . . ?
N2 C15 C14 C13 -179.1(3) . . . . ?
N3 C16 C17 C7 175.06(16) . . . . ?
N3 C16 C17 C18 0.7(2) . . . . ?
N3 C23 C18 C17 -0.7(2) . . . . ?
N3 C23 C18 C19 -179.77(18) . . . . ?
N3 C23 C22 C21 179.5(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C7 C9 -37.7(2) . . . . ?
C2 C3 C7 C17 92.4(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C7 C9 C8 110.01(18) . . . . ?
C3 C7 C9 C10 -66.99(18) . . . . ?
C3 C7 C17 C16 -6.4(2) . . . . ?
C3 C7 C17 C18 166.99(16) . . . . ?
C7 C9 C10 C11 -0.3(3) . . . . ?
C7 C9 C10 C15 178.2(2) . . . . ?
C7 C17 C18 C19 4.2(3) . . . . ?
C7 C17 C18 C23 -174.7(2) . . . . ?
C8 C9 C10 C11 -177.90(17) . . . . ?
C8 C9 C10 C15 0.59(18) . . . . ?
C9 C10 C11 C12 179.3(3) . . . . ?
C9 C10 C15 C14 -179.87(17) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C10 C15 C14 C13 0.5(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C16 C17 C18 C19 178.92(18) . . . . ?
C16 C17 C18 C23 0.0(2) . . . . ?
C17 C18 C19 C20 -178.9(3) . . . . ?
C17 C18 C23 C22 179.10(17) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C18 C23 C22 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
