# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_NCR_FA
_database_code_depnum_ccdc_archive 'CCDC 2026185'
loop_
_audit_author_name
_audit_author_address
'MMK Chaitanya'
;University of Hyderabad
India
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_audit_creation_date             2020-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Nicorandil-Fumaric acid salt'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N3 O4, C4 H3 O4'
_chemical_formula_sum            'C12 H13 N3 O8'
_chemical_formula_weight         327.25
_chemical_absolute_configuration ?
_chemical_melting_point          382.55
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   29.813(6)
_cell_length_b                   4.787(2)
_cell_length_c                   9.861(2)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1407.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      3.42
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7162
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         3.427
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                2245
_reflns_number_total             2353
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C11(H11), C3(H3), C10(H10), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.61998(6) 0.2158(3) 0.08875(18) 0.0427(4) Uani 1 1 d . . . . .
O8 O 0.79107(6) 0.3753(5) 0.9084(2) 0.0634(6) Uani 1 1 d . . . . .
O5 O 0.63823(6) 0.0422(4) 0.7610(2) 0.0575(6) Uani 1 1 d . . . . .
O6 O 0.68325(6) -0.1733(5) 0.6209(2) 0.0636(6) Uani 1 1 d . . . . .
O1 O 0.55027(6) 0.0174(4) 0.3248(2) 0.0588(5) Uani 1 1 d . . . . .
O4 O 0.59164(8) -0.1792(4) 0.0067(2) 0.0673(6) Uani 1 1 d . . . . .
O7 O 0.74398(6) 0.6300(4) 1.0289(2) 0.0589(5) Uani 1 1 d . . . . .
N1 N 0.58265(6) 0.6715(5) 0.6654(2) 0.0404(5) Uani 1 1 d . . . . .
N3 N 0.58791(7) 0.0675(5) 0.0148(2) 0.0454(5) Uani 1 1 d . . . . .
O3 O 0.55951(7) 0.2126(5) -0.0320(3) 0.0676(6) Uani 1 1 d . . . . .
N2 N 0.62289(7) 0.0716(5) 0.3760(2) 0.0424(5) Uani 1 1 d . . . . .
C1 C 0.59604(8) 0.5019(5) 0.5660(3) 0.0374(5) Uani 1 1 d . . . . .
H1A H 0.625424 0.512618 0.534758 0.045 Uiso 1 1 calc R U . . .
C2 C 0.56712(7) 0.3117(5) 0.5091(2) 0.0350(5) Uani 1 1 d . . . . .
C11 C 0.71305(7) 0.3220(5) 0.8727(3) 0.0397(6) Uani 1 1 d . . . . .
H11 H 0.684931 0.389636 0.897005 0.048 Uiso 1 1 calc R U . . .
C6 C 0.57947(8) 0.1215(5) 0.3948(3) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.52393(8) 0.2995(5) 0.5601(3) 0.0447(6) Uani 1 1 d . . . . .
H3 H 0.503494 0.173542 0.523496 0.054 Uiso 1 1 calc R U . . .
C12 C 0.75344(8) 0.4433(5) 0.9376(3) 0.0403(6) Uani 1 1 d . . . . .
C10 C 0.71572(8) 0.1236(5) 0.7829(3) 0.0424(6) Uani 1 1 d . . . . .
H10 H 0.744150 0.061765 0.758229 0.051 Uiso 1 1 calc R U . . .
C9 C 0.67669(7) -0.0102(5) 0.7173(3) 0.0391(5) Uani 1 1 d . . . . .
C8 C 0.65459(8) 0.0432(6) 0.1478(3) 0.0471(6) Uani 1 1 d . . . . .
H8A H 0.679861 0.160424 0.172345 0.056 Uiso 1 1 calc R U . . .
H8B H 0.664864 -0.089751 0.080434 0.056 Uiso 1 1 calc R U . . .
C5 C 0.54121(8) 0.6599(6) 0.7149(3) 0.0458(6) Uani 1 1 d . . . . .
H5 H 0.532765 0.780387 0.784342 0.055 Uiso 1 1 calc R U . . .
C7 C 0.63925(9) -0.1127(6) 0.2708(3) 0.0463(6) Uani 1 1 d . . . . .
H7A H 0.615551 -0.241114 0.245114 0.056 Uiso 1 1 calc R U . . .
H7B H 0.664029 -0.222024 0.306111 0.056 Uiso 1 1 calc R U . . .
C4 C 0.51098(8) 0.4724(6) 0.6647(3) 0.0500(7) Uani 1 1 d . . . . .
H4 H 0.482154 0.461639 0.700352 0.060 Uiso 1 1 calc R U . . .
H7 H 0.7723(12) 0.713(8) 1.066(4) 0.097(13) Uiso 1 1 d . . . . .
H2 H 0.6405(10) 0.136(6) 0.425(3) 0.048(8) Uiso 1 1 d . . . . .
H1 H 0.6058(10) 0.827(7) 0.699(4) 0.075(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N3 1.396(3) . ?
O2 C8 1.444(3) . ?
O8 C12 1.203(3) . ?
O5 C9 1.250(3) . ?
O6 C9 1.246(3) . ?
O1 C6 1.218(3) . ?
O4 N3 1.189(3) . ?
O7 C12 1.300(3) . ?
O7 H7 1.00(4) . ?
N1 C1 1.333(3) . ?
N1 C5 1.330(3) . ?
N1 H1 1.07(4) . ?
N3 O3 1.189(3) . ?
N2 C6 1.329(3) . ?
N2 C7 1.447(3) . ?
N2 H2 0.78(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.374(3) . ?
C2 C6 1.495(4) . ?
C2 C3 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.482(3) . ?
C11 C10 1.301(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.477(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.495(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O2 C8 114.14(19) . . ?
C12 O7 H7 110(2) . . ?
C1 N1 H1 117.3(19) . . ?
C5 N1 C1 121.5(2) . . ?
C5 N1 H1 121.1(19) . . ?
O4 N3 O2 118.4(2) . . ?
O3 N3 O2 113.2(2) . . ?
O3 N3 O4 128.4(2) . . ?
C6 N2 C7 122.5(2) . . ?
C6 N2 H2 120(2) . . ?
C7 N2 H2 117(2) . . ?
N1 C1 H1A 119.5 . . ?
N1 C1 C2 121.0(2) . . ?
C2 C1 H1A 119.5 . . ?
C1 C2 C6 123.8(2) . . ?
C1 C2 C3 117.6(2) . . ?
C3 C2 C6 118.5(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.0(2) . . ?
O1 C6 N2 122.9(3) . . ?
O1 C6 C2 120.0(2) . . ?
N2 C6 C2 117.0(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
O8 C12 O7 123.7(2) . . ?
O8 C12 C11 123.2(2) . . ?
O7 C12 C11 113.1(2) . . ?
C11 C10 H10 117.8 . . ?
C11 C10 C9 124.5(2) . . ?
C9 C10 H10 117.8 . . ?
O5 C9 C10 119.0(2) . . ?
O6 C9 O5 122.2(2) . . ?
O6 C9 C10 118.8(2) . . ?
O2 C8 H8A 108.9 . . ?
O2 C8 H8B 108.9 . . ?
O2 C8 C7 113.22(19) . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
N1 C5 H5 119.7 . . ?
N1 C5 C4 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
N2 C7 C8 112.3(2) . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?

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
O2 C8 C7 N2 -58.0(3) . . . . ?
N1 C1 C2 C6 178.1(2) . . . . ?
N1 C1 C2 C3 -1.0(3) . . . . ?
N1 C5 C4 C3 -1.2(4) . . . . ?
N3 O2 C8 C7 -76.1(3) . . . . ?
C1 N1 C5 C4 -0.1(4) . . . . ?
C1 C2 C6 O1 -159.3(2) . . . . ?
C1 C2 C6 N2 21.5(3) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C11 C10 C9 O5 -9.3(4) . . . . ?
C11 C10 C9 O6 171.2(3) . . . . ?
C6 N2 C7 C8 98.6(3) . . . . ?
C6 C2 C3 C4 -179.5(2) . . . . ?
C3 C2 C6 O1 19.8(3) . . . . ?
C3 C2 C6 N2 -159.3(2) . . . . ?
C12 C11 C10 C9 178.4(2) . . . . ?
C10 C11 C12 O8 2.8(4) . . . . ?
C10 C11 C12 O7 -177.1(2) . . . . ?
C8 O2 N3 O4 -0.1(3) . . . . ?
C8 O2 N3 O3 179.4(2) . . . . ?
C5 N1 C1 C2 1.3(4) . . . . ?
C7 N2 C6 O1 -0.3(4) . . . . ?
C7 N2 C6 C2 178.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NCR_SBA
_database_code_depnum_ccdc_archive 'CCDC 2026186'
loop_
_audit_author_name
_audit_author_address
'MMK Chaitanya'
;University of Hyderabad
India
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Nicorandil-Subaric acid cocrystal'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N3 O4, C4 H7 O2'
_chemical_formula_sum            'C12 H16 N3 O6'
_chemical_formula_weight         298.28
_chemical_melting_point          357.67
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.835(2)
_cell_length_b                   23.752(5)
_cell_length_c                   8.939(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.16(3)
_cell_angle_gamma                90
_cell_volume                     1423.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    298
_cell_measurement_theta_max      3.42
_cell_measurement_theta_min      24.92
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13448
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         2.887
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1411
_reflns_number_total             2491
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+0.1582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1635
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5)
2.d Tetrahedral OH refined with riding coordinates:
 O9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0318(3) 0.24845(9) -0.0048(2) 0.0590(7) Uani 1 1 d . . . . .
O2 O 0.6969(3) 0.30866(9) 0.2339(3) 0.0584(7) Uani 1 1 d . . . . .
O3 O 0.9969(4) 0.30315(14) 0.3603(4) 0.0968(10) Uani 1 1 d . . . . .
O4 O 0.8173(4) 0.37070(12) 0.4174(4) 0.0875(9) Uani 1 1 d . . . . .
N1 N 0.1013(4) 0.10529(11) 0.3736(3) 0.0502(7) Uani 1 1 d . . . . .
N2 N 0.3013(3) 0.25538(10) 0.1805(3) 0.0427(7) Uani 1 1 d . . . . .
H2 H 0.369333 0.246246 0.276092 0.051 Uiso 1 1 d R U . . .
N3 N 0.8494(4) 0.33065(15) 0.3482(4) 0.0621(8) Uani 1 1 d . . . . .
C1 C 0.1713(4) 0.14990(13) 0.3075(3) 0.0436(8) Uani 1 1 d . . . . .
H1 H 0.305289 0.159191 0.338206 0.052 Uiso 1 1 calc R U . . .
C2 C 0.0562(4) 0.18259(12) 0.1972(3) 0.0367(7) Uani 1 1 d . . . . .
C3 C -0.1427(5) 0.16814(14) 0.1536(4) 0.0526(9) Uani 1 1 d . . . . .
H3 H -0.226177 0.189128 0.079605 0.063 Uiso 1 1 calc R U . . .
C4 C -0.2165(5) 0.12275(15) 0.2197(4) 0.0613(10) Uani 1 1 d . . . . .
H4 H -0.349889 0.112589 0.191243 0.074 Uiso 1 1 calc R U . . .
C5 C -0.0906(5) 0.09276(14) 0.3282(4) 0.0569(9) Uani 1 1 d . . . . .
H5 H -0.141671 0.062022 0.372443 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1288(4) 0.23131(12) 0.1172(3) 0.0386(7) Uani 1 1 d . . . . .
C7 C 0.3652(5) 0.30585(13) 0.1098(4) 0.0516(9) Uani 1 1 d . . . . .
H7A H 0.249750 0.329182 0.071829 0.062 Uiso 1 1 calc R U . . .
H7B H 0.423716 0.294950 0.023510 0.062 Uiso 1 1 calc R U . . .
C8 C 0.5131(5) 0.33912(14) 0.2187(4) 0.0546(9) Uani 1 1 d . . . . .
H8A H 0.527060 0.376658 0.179321 0.066 Uiso 1 1 calc R U . . .
H8B H 0.472370 0.342245 0.316433 0.066 Uiso 1 1 calc R U . . .
O9 O 0.2952(4) 0.03854(10) 0.5953(3) 0.0742(8) Uani 1 1 d . . . . .
H9 H 0.248071 0.059796 0.525302 0.111 Uiso 1 1 calc R U . . .
O10 O 0.5629(4) 0.08596(14) 0.5830(4) 0.1098(13) Uani 1 1 d . . . . .
C9 C 0.4830(5) 0.05008(14) 0.6422(4) 0.0524(9) Uani 1 1 d . . . . .
C10 C 0.5832(5) 0.01320(14) 0.7704(4) 0.0533(9) Uani 1 1 d . . . . .
H10A H 0.581033 -0.025309 0.734020 0.064 Uiso 1 1 calc R U . . .
H10B H 0.506687 0.014414 0.851125 0.064 Uiso 1 1 calc R U . . .
C11 C 0.7955(5) 0.02913(14) 0.8363(4) 0.0535(9) Uani 1 1 d . . . . .
H11A H 0.798366 0.067893 0.870826 0.064 Uiso 1 1 calc R U . . .
H11B H 0.873046 0.027028 0.756337 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8936(4) -0.00770(14) 0.9683(4) 0.0516(9) Uani 1 1 d . . . . .
H12A H 0.817669 -0.005045 1.049144 0.062 Uiso 1 1 calc R U . . .
H12B H 0.888736 -0.046555 0.934390 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.231(3) . ?
O2 N3 1.411(4) . ?
O2 C8 1.433(4) . ?
O3 N3 1.189(4) . ?
O4 N3 1.178(4) . ?
N1 C1 1.345(4) . ?
N1 C5 1.329(4) . ?
N2 H2 0.9163 . ?
N2 C6 1.333(4) . ?
N2 C7 1.461(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(4) . ?
C2 C3 1.383(4) . ?
C2 C6 1.495(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(5) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.488(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O9 H9 0.8200 . ?
O9 C9 1.300(4) . ?
O10 C9 1.190(4) . ?
C9 C10 1.499(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.505(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.517(5) . ?
C12 C12 1.500(6) 3_757 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
N3 O2 C8 113.1(3) . . ?
C5 N1 C1 117.2(3) . . ?
C6 N2 H2 122.8 . . ?
C6 N2 C7 118.8(2) . . ?
C7 N2 H2 117.2 . . ?
O3 N3 O2 110.9(3) . . ?
O4 N3 O2 119.5(3) . . ?
O4 N3 O3 129.5(3) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(3) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 117.2(3) . . ?
C1 C2 C6 125.6(3) . . ?
C3 C2 C6 117.2(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.3(3) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 N2 121.0(3) . . ?
O1 C6 C2 120.5(3) . . ?
N2 C6 C2 118.5(2) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 112.0(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C8 C7 105.4(3) . . ?
O2 C8 H8A 110.7 . . ?
O2 C8 H8B 110.7 . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C9 O9 H9 109.5 . . ?
O9 C9 C10 113.5(3) . . ?
O10 C9 O9 121.1(3) . . ?
O10 C9 C10 125.3(3) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.6(3) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C10 C11 C12 114.0(3) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C12 C12 C11 113.8(3) 3_757 . ?
C12 C12 H12A 108.8 3_757 . ?
C12 C12 H12B 108.8 3_757 . ?
H12A C12 H12B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.2(4) . . . . ?
N1 C1 C2 C6 -177.9(3) . . . . ?
N2 C7 C8 O2 75.4(3) . . . . ?
N3 O2 C8 C7 -172.6(2) . . . . ?
C1 N1 C5 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C6 O1 160.7(3) . . . . ?
C1 C2 C6 N2 -18.8(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C2 C6 O1 -17.3(4) . . . . ?
C3 C2 C6 N2 163.1(3) . . . . ?
C3 C4 C5 N1 0.1(5) . . . . ?
C5 N1 C1 C2 0.0(4) . . . . ?
C6 N2 C7 C8 158.9(3) . . . . ?
C6 C2 C3 C4 178.0(3) . . . . ?
C7 N2 C6 O1 5.4(4) . . . . ?
C7 N2 C6 C2 -175.0(3) . . . . ?
C8 O2 N3 O3 177.8(3) . . . . ?
C8 O2 N3 O4 -1.1(4) . . . . ?
O9 C9 C10 C11 -174.6(3) . . . . ?
O10 C9 C10 C11 7.2(6) . . . . ?
C9 C10 C11 C12 178.7(3) . . . . ?
C10 C11 C12 C12 178.9(3) . . . 3_757 ?

_olex2_submission_special_instructions 'No special instructions were received'
