# 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_NAA-2-AP
_database_code_depnum_ccdc_archive 'CCDC 1978640'
loop_
_audit_author_name
_audit_author_address
'Yasser Azim'
;Aligarh Muslim University
India
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        '1-Naphthalene acetic acid + 2-aminopyrimidine'
_chemical_name_common            '1-Naphthalene acetic acid + 2-aminopyrimidine'
_chemical_melting_point          369.95
_chemical_formula_moiety         'C12 H10 O2, C4 H5 N3 '
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.3833(6)
_cell_length_b                   6.9029(4)
_cell_length_c                   20.2517(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.255(3)
_cell_angle_gamma                90
_cell_volume                     1451.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9471
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      78.67

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.710
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22025
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.367
_diffrn_reflns_theta_max         78.809
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3096
_reflns_number_gt                2278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)²+0.8773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0068(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3096
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0820
_refine_ls_wR_factor_ref         0.2078
_refine_ls_wR_factor_gt          0.1882
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.4984(2) 0.3043(4) 0.56598(12) 0.0743(8) Uani 1 1 d . . . . .
O1 O 0.5877(2) 0.5787(4) 0.59906(11) 0.0767(8) Uani 1 1 d . . . . .
N1 N 0.8123(3) 0.5298(4) 0.51171(15) 0.0597(8) Uani 1 1 d . . . . .
N3 N 0.6995(2) 0.2556(4) 0.48400(12) 0.0561(7) Uani 1 1 d . . . . .
N2 N 0.9208(3) 0.2903(4) 0.45828(13) 0.0577(7) Uani 1 1 d . . . . .
C5 C 0.5713(3) 0.6935(4) 0.80985(13) 0.0516(7) Uani 1 1 d . . . . .
C10 C 0.5359(3) 0.5549(4) 0.76091(13) 0.0492(7) Uani 1 1 d . . . . .
C13 C 0.8110(3) 0.3548(4) 0.48405(13) 0.0460(6) Uani 1 1 d . . . . .
C9 C 0.6071(3) 0.3760(5) 0.76185(16) 0.0604(9) Uani 1 1 d . . . . .
H9 H 0.586327 0.280015 0.731190 0.072 Uiso 1 1 calc R U . . .
C1 C 0.4378(3) 0.5969(5) 0.71417(15) 0.0593(8) Uani 1 1 d . . . . .
C12 C 0.5094(3) 0.4531(5) 0.60549(14) 0.0607(9) Uani 1 1 d . . . . .
C2 C 0.3770(3) 0.7671(6) 0.71878(19) 0.0744(11) Uani 1 1 d . . . . .
H2 H 0.311529 0.794769 0.688138 0.089 Uiso 1 1 calc R U . . .
C16 C 0.7007(4) 0.0814(5) 0.45591(17) 0.0683(10) Uani 1 1 d . . . . .
H16 H 0.625287 0.008702 0.455430 0.082 Uiso 1 1 calc R U . . .
C7 C 0.7386(4) 0.4813(7) 0.8515(2) 0.0820(12) Uani 1 1 d . . . . .
H7 H 0.806549 0.457644 0.881095 0.098 Uiso 1 1 calc R U . . .
C6 C 0.6756(4) 0.6499(6) 0.85357(16) 0.0714(10) Uani 1 1 d . . . . .
H6 H 0.701105 0.741824 0.884781 0.086 Uiso 1 1 calc R U . . .
C3 C 0.4068(4) 0.9070(6) 0.7677(2) 0.0919(16) Uani 1 1 d . . . . .
H3 H 0.360564 1.022252 0.769637 0.110 Uiso 1 1 calc R U . . .
C4 C 0.5063(4) 0.8696(5) 0.8129(2) 0.0759(11) Uani 1 1 d . . . . .
H4 H 0.529257 0.960944 0.844840 0.091 Uiso 1 1 calc R U . . .
C8 C 0.7037(4) 0.3447(6) 0.80654(18) 0.0743(11) Uani 1 1 d . . . . .
H8 H 0.747135 0.226910 0.806360 0.089 Uiso 1 1 calc R U . . .
C11 C 0.4081(3) 0.4555(6) 0.65863(16) 0.0748(11) Uani 1 1 d . . . . .
H11A H 0.325492 0.488796 0.638459 0.090 Uiso 1 1 calc R U . . .
H11B H 0.400852 0.326313 0.677044 0.090 Uiso 1 1 calc R U . . .
C14 C 0.9154(4) 0.1164(5) 0.43051(17) 0.0703(10) Uani 1 1 d . . . . .
H14 H 0.989759 0.067940 0.411758 0.084 Uiso 1 1 calc R U . . .
C15 C 0.8070(4) 0.0046(5) 0.42786(19) 0.0723(10) Uani 1 1 d . . . . .
H15 H 0.805916 -0.116988 0.408043 0.087 Uiso 1 1 calc R U . . .
H1A H 0.743(4) 0.573(5) 0.5352(17) 0.069(10) Uiso 1 1 d . . . . .
H1B H 0.882(4) 0.589(5) 0.5165(16) 0.059(10) Uiso 1 1 d . . . . .
H2A H 0.567(4) 0.302(6) 0.535(2) 0.097(13) 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 C12 1.306(4) . ?
O1 C12 1.198(4) . ?
N1 C13 1.331(4) . ?
N3 C16 1.330(4) . ?
N3 C13 1.345(3) . ?
N2 C14 1.326(4) . ?
N2 C13 1.340(4) . ?
C5 C4 1.392(5) . ?
C5 C6 1.416(5) . ?
C5 C10 1.420(4) . ?
C10 C1 1.406(4) . ?
C10 C9 1.439(4) . ?
C9 C8 1.354(5) . ?
C1 C2 1.338(5) . ?
C1 C11 1.516(5) . ?
C12 C11 1.521(4) . ?
C2 C3 1.414(6) . ?
C16 C15 1.360(5) . ?
C7 C6 1.336(6) . ?
C7 C8 1.355(6) . ?
C3 C4 1.390(6) . ?
C14 C15 1.365(5) . ?

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
C16 N3 C13 116.3(3) . . ?
C14 N2 C13 115.9(3) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 C10 120.1(3) . . ?
C6 C5 C10 118.4(3) . . ?
C1 C10 C5 120.2(3) . . ?
C1 C10 C9 123.4(3) . . ?
C5 C10 C9 116.4(3) . . ?
N1 C13 N2 117.7(3) . . ?
N1 C13 N3 117.6(3) . . ?
N2 C13 N3 124.8(3) . . ?
C8 C9 C10 121.2(3) . . ?
C2 C1 C10 118.1(4) . . ?
C2 C1 C11 121.9(4) . . ?
C10 C1 C11 119.9(3) . . ?
O1 C12 O2 123.6(3) . . ?
O1 C12 C11 123.4(3) . . ?
O2 C12 C11 112.9(3) . . ?
C1 C2 C3 123.6(4) . . ?
N3 C16 C15 123.1(3) . . ?
C6 C7 C8 120.2(4) . . ?
C7 C6 C5 122.3(4) . . ?
C4 C3 C2 118.9(3) . . ?
C3 C4 C5 119.1(4) . . ?
C9 C8 C7 121.5(4) . . ?
C1 C11 C12 113.6(3) . . ?
N2 C14 C15 123.8(3) . . ?
C16 C15 C14 116.0(3) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_naatap
_database_code_depnum_ccdc_archive 'CCDC 1978642'
loop_
_audit_author_name
_audit_author_address
'Yasser Azim'
;Aligarh Muslim University
India
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_audit_creation_date             2020-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'1-Naphthalene acetic acid + 2,4,6-triaminopyrimidine'
_chemical_name_systematic        
'1-Naphthalene acetic acid + 2,4,6-triaminopyrimidine'
_chemical_formula_moiety         'C12 H9 O2, C4 H8 N5'
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.34
_chemical_melting_point          485.05
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7424(9)
_cell_length_b                   11.8549(8)
_cell_length_c                   12.7190(7)
_cell_angle_alpha                104.860(5)
_cell_angle_beta                 93.046(6)
_cell_angle_gamma                112.269(7)
_cell_volume                     1561.16(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6580
_cell_measurement_theta_min      3.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 6 0.0558
-1 7 -3 0.0985
1 -7 3 0.0985
6 1 -4 0.0793
-7 2 3 0.0475
-1 1 -8 0.0366
0 4 5 0.0638
1 0 8 0.0476
5 1 -7 0.0633
4 -7 0 0.0997
-5 2 6 0.0459
5 -7 3 0.0959
7 0 0 0.0714
2 -4 -6 0.0748
-5 1 -5 0.0328

_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9245
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.797
_diffrn_reflns_theta_max         66.797
_diffrn_reflns_theta_min         3.647
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  59.00   1.00    1.00    --   25.57 -57.00 -90.00  104
  2  ω     13.00 109.00   1.00    1.50    --   66.78-111.00-150.00   96
  3  ω     69.00 153.00   1.00    5.00    --  108.00 -43.00 -30.00   84
  4  ω    120.00 175.00   1.00    5.00    --  108.00  21.00-120.00   55
  5  ω    137.00 178.00   1.00    5.00    --  108.00 104.00 -60.00   41
  6  ω    140.00 177.00   1.00    5.00    --  108.00 138.00-150.00   37
  7  ω    103.00 178.00   1.00    5.00    --  108.00 138.00 -90.00   75
  8  ω    135.00 178.00   1.00    5.00    --  108.00  32.00   0.00   43
  9  ω    140.00 166.00   1.00    5.00    --  108.00  21.00  90.00   26
 10  ω    140.00 166.00   1.00    5.00    --  108.00 -32.00 150.00   26
 11  ω     85.00 138.00   1.00    5.00    --  108.00 -65.00   0.00   53
 12  ω     79.00 113.00   1.00    5.00    --  108.00-123.00   6.00   34
 13  ω     43.00  69.00   1.00    5.00    --  108.00 -65.00   0.00   26
 14  ω     31.00 117.00   1.00    5.00    --  108.00 -77.00 -30.00   86
 15  ω     41.00 120.00   1.00    5.00    --  108.00 -65.00-150.00   79
 16  ω     43.00 132.00   1.00    5.00    --  108.00  32.00   0.00   89
 17  ω    100.00 149.00   1.00    1.50    --   66.78 111.00  90.00   49
 18  ω     53.00 133.00   1.00    5.00    --  108.00 -32.00 150.00   80
 19  ω     68.00 116.00   1.00    5.00    --  108.00-111.00 144.11   48
 20  ω     29.00  56.00   1.00    5.00    --  108.00 -43.00 -30.00   27
 21  ω     27.00 101.00   1.00    5.00    --  108.00  21.00-120.00   74
 22  ω     32.00 139.00   1.00    1.50    --   66.78  61.00  30.00  107
 23  ω     71.00 126.00   1.00    1.50    --   66.78 178.00-180.00   55
 24  ω     34.00 142.00   1.00    1.50    --   66.78  61.00  90.00  108
 25  ω     32.00 132.00   1.00    1.50    --   66.78  61.00 150.00  100
 26  ω     28.00 122.00   1.00    5.00    --  108.00  21.00  90.00   94
 27  ω     23.00 118.00   1.00    5.00    --  108.00 -89.00-150.00   95
 28  ω    -13.00  86.00   1.00    1.50    --   66.78 -45.00-180.00   99
 29  ω    -48.00  59.00   1.00    1.00    --   25.57 -77.00-180.00  107
 30  ω    -46.00  55.00   1.00    1.00    --   25.57 -77.00  60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4015
_reflns_number_total             5445
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.049
_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)+(0.0856P)²+0.9406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1849
_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:
 C11(H11A,H11B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C14(H14), C18(H18), C25(H25), C1(H1), C24(H24), C3(H3), C23(H23),
 C8(H8), C2(H2), C21(H21), C19(H19), C5(H5), C20(H20), C7(H7), C6(H6)
;
_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
O3 O 0.2637(2) -0.13513(18) 0.48435(16) 0.0341(5) Uani 1 1 d . . . . .
O1 O 0.4584(2) 0.45501(18) 0.67407(18) 0.0374(5) Uani 1 1 d . . . . .
O2 O 0.46257(19) 0.64481(18) 0.76230(17) 0.0345(5) Uani 1 1 d . . . . .
O4 O 0.3018(2) 0.04113(19) 0.43631(18) 0.0465(6) Uani 1 1 d . . . . .
N2 N 0.6780(2) 0.5493(2) 0.60557(19) 0.0279(5) Uani 1 1 d . . . . .
N7 N 0.4623(2) -0.0010(2) 0.85494(19) 0.0295(5) Uani 1 1 d . . . . .
N6 N 0.4157(2) 0.0189(2) 0.6795(2) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.8492(2) 0.5102(2) 0.54392(18) 0.0284(5) Uani 1 1 d . . . . .
N9 N 0.4282(2) 0.2051(2) 0.6480(2) 0.0315(5) Uani 1 1 d . . . . .
N5 N 0.6799(3) 0.3504(2) 0.5732(2) 0.0349(6) Uani 1 1 d . . . . .
N10 N 0.3932(3) -0.1743(2) 0.6983(2) 0.0372(6) Uani 1 1 d . . . . .
N3 N 0.6618(3) 0.7417(2) 0.6369(2) 0.0324(5) Uani 1 1 d . . . . .
N8 N 0.5312(3) 0.1733(3) 1.0072(2) 0.0370(6) Uani 1 1 d . . . . .
N4 N 1.0153(3) 0.6705(3) 0.5138(2) 0.0394(6) Uani 1 1 d . . . . .
C29 C 0.4443(2) 0.1475(2) 0.7217(2) 0.0276(5) Uani 1 1 d . . . . .
C13 C 0.7289(3) 0.6738(2) 0.6043(2) 0.0265(5) Uani 1 1 d . . . . .
C32 C 0.4258(3) -0.0503(2) 0.7472(2) 0.0285(6) Uani 1 1 d . . . . .
C16 C 0.7387(3) 0.4723(2) 0.5744(2) 0.0271(6) Uani 1 1 d . . . . .
C12 C 0.4070(3) 0.5268(3) 0.7206(2) 0.0289(6) Uani 1 1 d . . . . .
C15 C 0.9025(3) 0.6349(3) 0.5438(2) 0.0287(6) Uani 1 1 d . . . . .
C31 C 0.4940(2) 0.1275(3) 0.8984(2) 0.0290(6) Uani 1 1 d . . . . .
C30 C 0.4884(3) 0.2046(2) 0.8331(2) 0.0298(6) Uani 1 1 d . . . . .
H30 H 0.513735 0.292126 0.864070 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8435(3) 0.7181(2) 0.5711(2) 0.0290(6) Uani 1 1 d . . . . .
H14 H 0.880297 0.801132 0.566947 0.035 Uiso 1 1 calc R U . . .
C28 C 0.2571(3) -0.0762(3) 0.4153(2) 0.0337(6) Uani 1 1 d . . . . .
C10 C 0.2229(3) 0.5167(3) 0.8219(2) 0.0340(6) Uani 1 1 d . . . . .
C9 C 0.2426(3) 0.4838(3) 0.9195(3) 0.0385(7) Uani 1 1 d . . . . .
C11 C 0.2668(3) 0.4638(3) 0.7194(2) 0.0393(7) Uani 1 1 d . . . . .
H11A H 0.223580 0.472507 0.656806 0.047 Uiso 1 1 calc R U . . .
H11B H 0.243144 0.373213 0.708145 0.047 Uiso 1 1 calc R U . . .
C22 C 0.0449(3) 0.0321(3) 0.1800(3) 0.0414(7) Uani 1 1 d . . . . .
C17 C 0.0661(3) -0.0448(3) 0.2421(3) 0.0406(7) Uani 1 1 d . . . . .
C4 C 0.1994(3) 0.5323(3) 1.0159(3) 0.0485(8) Uani 1 1 d . . . . .
C18 C -0.0159(3) -0.0761(3) 0.3207(3) 0.0485(8) Uani 1 1 d . . . . .
H18 H -0.006474 -0.126943 0.362395 0.058 Uiso 1 1 calc R U . . .
C27 C 0.1923(4) -0.1589(3) 0.2985(3) 0.0458(8) Uani 1 1 d . . . . .
H27A H 0.244948 -0.198766 0.264153 0.055 Uiso 1 1 calc R U . . .
H27B H 0.114895 -0.226396 0.302135 0.055 Uiso 1 1 calc R U . . .
C26 C 0.1636(3) -0.0862(3) 0.2269(3) 0.0414(7) Uani 1 1 d . . . . .
C25 C 0.2335(3) -0.0534(4) 0.1491(3) 0.0495(8) Uani 1 1 d . . . . .
H25 H 0.295824 -0.083230 0.136906 0.059 Uiso 1 1 calc R U . . .
C1 C 0.1630(3) 0.5960(3) 0.8246(3) 0.0497(8) Uani 1 1 d . . . . .
H1 H 0.149289 0.618557 0.761760 0.060 Uiso 1 1 calc R U . . .
C24 C 0.2178(4) 0.0225(4) 0.0859(3) 0.0551(9) Uani 1 1 d . . . . .
H24 H 0.269396 0.043522 0.034635 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1393(4) 0.6129(4) 1.0142(4) 0.0608(11) Uani 1 1 d . . . . .
H3 H 0.111180 0.644905 1.077400 0.073 Uiso 1 1 calc R U . . .
C23 C 0.1242(4) 0.0648(4) 0.1017(3) 0.0585(10) Uani 1 1 d . . . . .
H23 H 0.112498 0.115500 0.060879 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3025(4) 0.4018(5) 0.9241(3) 0.0616(11) Uani 1 1 d . . . . .
H8 H 0.333539 0.370994 0.862468 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1211(4) 0.6452(4) 0.9233(4) 0.0634(11) Uani 1 1 d . . . . .
H2 H 0.081114 0.699635 0.924016 0.076 Uiso 1 1 calc R U . . .
C21 C -0.0510(4) 0.0738(4) 0.1978(3) 0.0629(11) Uani 1 1 d . . . . .
H21 H -0.064758 0.123683 0.157101 0.075 Uiso 1 1 calc R U . . .
C19 C -0.1067(3) -0.0315(4) 0.3339(4) 0.0650(12) Uani 1 1 d . . . . .
H19 H -0.158523 -0.051602 0.385226 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2187(4) 0.4946(5) 1.1116(3) 0.0695(13) Uani 1 1 d . . . . .
H5 H 0.192551 0.526890 1.175937 0.083 Uiso 1 1 calc R U . . .
C20 C -0.1233(4) 0.0428(5) 0.2726(4) 0.0739(13) Uani 1 1 d . . . . .
H20 H -0.186073 0.072178 0.283369 0.089 Uiso 1 1 calc R U . . .
C7 C 0.3164(5) 0.3664(6) 1.0154(4) 0.0863(17) Uani 1 1 d . . . . .
H7 H 0.354606 0.310447 1.014769 0.104 Uiso 1 1 calc R U . . .
C6 C 0.2742(5) 0.4130(6) 1.1099(4) 0.0832(16) Uani 1 1 d . . . . .
H6 H 0.284102 0.388059 1.172214 0.100 Uiso 1 1 calc R U . . .
H3A H 0.599(3) 0.712(3) 0.674(3) 0.025(7) Uiso 1 1 d . . . . .
H4A H 1.060(4) 0.747(4) 0.516(3) 0.043(10) Uiso 1 1 d . . . . .
H10A H 0.377(3) -0.203(3) 0.622(3) 0.029(8) Uiso 1 1 d . . . . .
H10B H 0.401(3) -0.218(3) 0.728(3) 0.026(8) Uiso 1 1 d . . . . .
H5A H 0.719(3) 0.299(4) 0.560(3) 0.043(10) Uiso 1 1 d . . . . .
H9A H 0.427(3) 0.276(4) 0.667(3) 0.043(10) Uiso 1 1 d . . . . .
H3B H 0.684(3) 0.817(4) 0.632(3) 0.042(10) Uiso 1 1 d . . . . .
H2A H 0.606(4) 0.517(4) 0.630(3) 0.041(9) Uiso 1 1 d . . . . .
H8A H 0.532(4) 0.118(4) 1.048(3) 0.050(10) Uiso 1 1 d . . . . .
H6A H 0.375(3) -0.025(3) 0.612(3) 0.038(9) Uiso 1 1 d . . . . .
H9B H 0.389(3) 0.158(4) 0.578(3) 0.041(9) Uiso 1 1 d . . . . .
H8B H 0.551(3) 0.250(3) 1.039(2) 0.022(7) Uiso 1 1 d . . . . .
H4B H 1.051(4) 0.619(4) 0.502(3) 0.044(10) Uiso 1 1 d . . . . .
H5B H 0.613(4) 0.323(3) 0.599(3) 0.038(9) 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
O3 C28 1.271(3) . ?
O1 C12 1.267(3) . ?
O2 C12 1.247(3) . ?
O4 C28 1.234(3) . ?
N2 C13 1.372(3) . ?
N2 C16 1.356(3) . ?
N2 H2A 0.89(4) . ?
N7 C32 1.319(4) . ?
N7 C31 1.372(3) . ?
N6 C29 1.377(3) . ?
N6 C32 1.361(4) . ?
N6 H6A 0.88(4) . ?
N1 C16 1.317(4) . ?
N1 C15 1.370(3) . ?
N9 C29 1.337(4) . ?
N9 H9A 0.82(4) . ?
N9 H9B 0.91(4) . ?
N5 C16 1.340(4) . ?
N5 H5A 0.89(4) . ?
N5 H5B 0.85(4) . ?
N10 C32 1.332(4) . ?
N10 H10A 0.92(3) . ?
N10 H10B 0.75(4) . ?
N3 C13 1.336(4) . ?
N3 H3A 0.90(3) . ?
N3 H3B 0.85(4) . ?
N8 C31 1.331(4) . ?
N8 H8A 0.94(4) . ?
N8 H8B 0.83(3) . ?
N4 C15 1.338(4) . ?
N4 H4A 0.85(4) . ?
N4 H4B 0.85(4) . ?
C29 C30 1.377(4) . ?
C13 C14 1.380(4) . ?
C12 C11 1.526(4) . ?
C15 C14 1.393(4) . ?
C31 C30 1.400(4) . ?
C30 H30 0.9300 . ?
C14 H14 0.9300 . ?
C28 C27 1.521(4) . ?
C10 C9 1.425(4) . ?
C10 C11 1.503(4) . ?
C10 C1 1.366(4) . ?
C9 C4 1.420(4) . ?
C9 C8 1.409(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C22 C17 1.428(5) . ?
C22 C23 1.425(5) . ?
C22 C21 1.399(5) . ?
C17 C18 1.444(5) . ?
C17 C26 1.410(4) . ?
C4 C3 1.390(6) . ?
C4 C5 1.435(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.359(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C26 1.508(5) . ?
C26 C25 1.358(5) . ?
C25 H25 0.9300 . ?
C25 C24 1.404(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.437(6) . ?
C24 H24 0.9300 . ?
C24 C23 1.375(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.339(7) . ?
C23 H23 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.353(5) . ?
C2 H2 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.338(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(7) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.388(7) . ?
C6 H6 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
C13 N2 H2A 122(2) . . ?
C16 N2 C13 120.6(2) . . ?
C16 N2 H2A 117(2) . . ?
C32 N7 C31 116.9(2) . . ?
C29 N6 H6A 122(2) . . ?
C32 N6 C29 120.6(2) . . ?
C32 N6 H6A 116(2) . . ?
C16 N1 C15 116.5(2) . . ?
C29 N9 H9A 122(3) . . ?
C29 N9 H9B 120(2) . . ?
H9A N9 H9B 114(3) . . ?
C16 N5 H5A 120(2) . . ?
C16 N5 H5B 124(2) . . ?
H5A N5 H5B 115(3) . . ?
C32 N10 H10A 118(2) . . ?
C32 N10 H10B 123(3) . . ?
H10A N10 H10B 118(3) . . ?
C13 N3 H3A 119(2) . . ?
C13 N3 H3B 121(2) . . ?
H3A N3 H3B 119(3) . . ?
C31 N8 H8A 120(2) . . ?
C31 N8 H8B 120(2) . . ?
H8A N8 H8B 120(3) . . ?
C15 N4 H4A 124(3) . . ?
C15 N4 H4B 120(3) . . ?
H4A N4 H4B 116(4) . . ?
N9 C29 N6 115.4(2) . . ?
N9 C29 C30 126.5(2) . . ?
C30 C29 N6 118.1(2) . . ?
N2 C13 C14 118.1(2) . . ?
N3 C13 N2 115.9(3) . . ?
N3 C13 C14 126.0(3) . . ?
N7 C32 N6 123.4(2) . . ?
N7 C32 N10 120.8(3) . . ?
N10 C32 N6 115.8(3) . . ?
N1 C16 N2 123.8(2) . . ?
N1 C16 N5 119.5(3) . . ?
N5 C16 N2 116.8(3) . . ?
O1 C12 C11 116.9(3) . . ?
O2 C12 O1 124.2(3) . . ?
O2 C12 C11 118.8(3) . . ?
N1 C15 C14 122.9(3) . . ?
N4 C15 N1 114.8(3) . . ?
N4 C15 C14 122.3(3) . . ?
N7 C31 C30 122.4(2) . . ?
N8 C31 N7 114.9(3) . . ?
N8 C31 C30 122.7(3) . . ?
C29 C30 C31 118.4(2) . . ?
C29 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C13 C14 C15 118.1(2) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
O3 C28 C27 116.3(2) . . ?
O4 C28 O3 124.5(3) . . ?
O4 C28 C27 119.2(3) . . ?
C9 C10 C11 120.0(3) . . ?
C1 C10 C9 118.3(3) . . ?
C1 C10 C11 121.7(3) . . ?
C4 C9 C10 120.0(3) . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 C4 117.7(3) . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 C12 115.1(2) . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C23 C22 C17 118.2(3) . . ?
C21 C22 C17 119.7(3) . . ?
C21 C22 C23 122.1(4) . . ?
C22 C17 C18 116.7(3) . . ?
C26 C17 C22 120.8(3) . . ?
C26 C17 C18 122.5(3) . . ?
C9 C4 C5 118.3(4) . . ?
C3 C4 C9 119.3(4) . . ?
C3 C4 C5 122.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C26 C27 C28 113.8(3) . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C17 C26 C27 120.8(3) . . ?
C25 C26 C17 117.6(3) . . ?
C25 C26 C27 121.6(3) . . ?
C26 C25 H25 117.8 . . ?
C26 C25 C24 124.4(4) . . ?
C24 C25 H25 117.8 . . ?
C10 C1 H1 119.6 . . ?
C10 C1 C2 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
C25 C24 H24 120.9 . . ?
C23 C24 C25 118.2(3) . . ?
C23 C24 H24 120.9 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(4) . . ?
C24 C23 H23 119.6 . . ?
C9 C8 H8 118.9 . . ?
C7 C8 C9 122.1(4) . . ?
C7 C8 H8 118.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.9(4) . . ?
C20 C21 H21 119.6 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N10 H10B O2 0.75(4) 2.13(4) 2.841(3) 158(3) 1_545 yes
N5 H5A O3 0.89(4) 1.97(4) 2.805(3) 157(3) 2_656 yes
N9 H9A O1 0.82(4) 1.99(4) 2.775(3) 161(4) . yes
N3 H3B O4 0.85(4) 2.04(4) 2.849(3) 158(3) 2_666 yes
N2 H2A O1 0.89(4) 1.79(4) 2.686(3) 177(4) . yes
N6 H6A O3 0.88(4) 1.86(4) 2.724(3) 169(3) . yes
N9 H9B O4 0.91(4) 1.91(4) 2.817(3) 173(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C28 C27 C26 168.0(3) . . . . ?
O1 C12 C11 C10 143.7(3) . . . . ?
O2 C12 C11 C10 -39.4(4) . . . . ?
O4 C28 C27 C26 -13.7(5) . . . . ?
N2 C13 C14 C15 -1.9(4) . . . . ?
N7 C31 C30 C29 2.7(4) . . . . ?
N6 C29 C30 C31 -4.1(4) . . . . ?
N1 C15 C14 C13 3.0(4) . . . . ?
N9 C29 C30 C31 177.4(3) . . . . ?
N3 C13 C14 C15 177.5(3) . . . . ?
N8 C31 C30 C29 -177.6(3) . . . . ?
N4 C15 C14 C13 -178.0(3) . . . . ?
C29 N6 C32 N7 0.2(4) . . . . ?
C29 N6 C32 N10 178.5(3) . . . . ?
C13 N2 C16 N1 1.7(4) . . . . ?
C13 N2 C16 N5 -177.0(3) . . . . ?
C32 N7 C31 N8 -179.5(3) . . . . ?
C32 N7 C31 C30 0.2(4) . . . . ?
C32 N6 C29 N9 -178.5(2) . . . . ?
C32 N6 C29 C30 2.9(4) . . . . ?
C16 N2 C13 N3 -179.8(2) . . . . ?
C16 N2 C13 C14 -0.3(4) . . . . ?
C16 N1 C15 N4 179.2(3) . . . . ?
C16 N1 C15 C14 -1.7(4) . . . . ?
C15 N1 C16 N2 -0.6(4) . . . . ?
C15 N1 C16 N5 178.1(3) . . . . ?
C31 N7 C32 N6 -1.7(4) . . . . ?
C31 N7 C32 N10 -179.9(3) . . . . ?
C28 C27 C26 C17 -73.8(4) . . . . ?
C28 C27 C26 C25 103.2(4) . . . . ?
C10 C9 C4 C3 -0.7(5) . . . . ?
C10 C9 C4 C5 178.6(3) . . . . ?
C10 C9 C8 C7 -177.1(4) . . . . ?
C10 C1 C2 C3 -0.5(6) . . . . ?
C9 C10 C11 C12 -76.3(4) . . . . ?
C9 C10 C1 C2 0.0(5) . . . . ?
C9 C4 C3 C2 0.2(6) . . . . ?
C9 C4 C5 C6 -1.3(6) . . . . ?
C9 C8 C7 C6 -1.6(9) . . . . ?
C11 C10 C9 C4 -179.1(3) . . . . ?
C11 C10 C9 C8 -0.2(5) . . . . ?
C11 C10 C1 C2 179.7(3) . . . . ?
C22 C17 C18 C19 -0.8(5) . . . . ?
C22 C17 C26 C27 175.3(3) . . . . ?
C22 C17 C26 C25 -1.9(5) . . . . ?
C22 C21 C20 C19 -0.5(7) . . . . ?
C17 C22 C23 C24 0.6(5) . . . . ?
C17 C22 C21 C20 0.2(6) . . . . ?
C17 C18 C19 C20 0.6(6) . . . . ?
C17 C26 C25 C24 2.4(5) . . . . ?
C4 C9 C8 C7 1.8(7) . . . . ?
C4 C3 C2 C1 0.4(6) . . . . ?
C4 C5 C6 C7 1.5(8) . . . . ?
C18 C17 C26 C27 -4.1(5) . . . . ?
C18 C17 C26 C25 178.7(3) . . . . ?
C18 C19 C20 C21 0.1(7) . . . . ?
C27 C26 C25 C24 -174.8(3) . . . . ?
C26 C17 C18 C19 178.6(3) . . . . ?
C26 C25 C24 C23 -1.3(6) . . . . ?
C25 C24 C23 C22 -0.2(6) . . . . ?
C1 C10 C9 C4 0.6(4) . . . . ?
C1 C10 C9 C8 179.5(4) . . . . ?
C1 C10 C11 C12 104.0(4) . . . . ?
C3 C4 C5 C6 178.0(4) . . . . ?
C23 C22 C17 C18 180.0(3) . . . . ?
C23 C22 C17 C26 0.5(5) . . . . ?
C23 C22 C21 C20 -179.3(4) . . . . ?
C8 C9 C4 C3 -179.6(4) . . . . ?
C8 C9 C4 C5 -0.3(5) . . . . ?
C8 C7 C6 C5 -0.1(9) . . . . ?
C21 C22 C17 C18 0.5(4) . . . . ?
C21 C22 C17 C26 -178.9(3) . . . . ?
C21 C22 C23 C24 -180.0(4) . . . . ?
C5 C4 C3 C2 -179.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_naadmp
_database_code_depnum_ccdc_archive 'CCDC 1978641'
loop_
_audit_author_name
_audit_author_address
'Yasser Azim'
;Aligarh Muslim University
India
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_audit_creation_date             2020-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'1-Naphthalene acetic acid + 2-amino-4,6-dimethylpyrimidine'
_chemical_name_systematic        
'1-Naphthalene acetic acid + 2-amino-4,6-dimethylpyrimidine'
_chemical_formula_moiety         '2(C12 H10 O2), C6 H9 N3'
_chemical_formula_sum            'C30 H29 N3 O4'
_chemical_formula_weight         495.56
_chemical_melting_point          375.05
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4504(3)
_cell_length_b                   12.4728(5)
_cell_length_c                   28.0306(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.076(4)
_cell_angle_gamma                90
_cell_volume                     2594.59(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8050
_cell_measurement_theta_min      3.8720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 18 0.0795
4 3 -4 0.1070
-4 -3 4 0.1070
0 -5 14 0.0784
0 5 -14 0.0499
-3 1 15 0.0916
0 -7 9 0.0763
-4 5 -4 0.0950
0 8 -5 0.0448
-4 4 4 0.0794
0 5 14 0.0641
0 -3 -17 0.0626
2 0 15 0.0948
1 -8 -2 0.0727
0 -7 -7 0.0628
4 1 -13 0.1043
0 0 -18 0.0534

_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8354
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.912
_diffrn_reflns_theta_max         66.912
_diffrn_reflns_theta_min         3.882
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  99.00   1.00    1.00    --   25.69  57.00  60.00  105
  2  ω     49.00 145.00   1.00    5.00    --   66.85  50.00 -30.00   96
  3  ω    129.00 178.00   1.00   12.50    --  108.00  43.00 -90.00   49
  4  ω    153.00 178.00   1.00   12.50    --  108.00 104.00-150.00   25
  5  ω    127.00 162.00   1.00   12.50    --  108.00 138.00 -60.00   35
  6  ω    111.00 149.00   1.00    5.00    --   66.85 111.00-150.00   38
  7  ω    112.00 137.00   1.00    5.00    --   66.85 111.00-180.00   25
  8  ω    103.00 156.00   1.00   12.50    --  108.00 104.00-180.00   53
  9  ω    106.00 149.00   1.00   12.50    --  108.00 104.00-150.00   43
 10  ω    103.00 178.00   1.00   12.50    --  108.00 104.00 -30.00   75
 11  ω     89.00 124.00   1.00   12.50    --  108.00 138.00 -60.00   35
 12  ω     74.00 172.00   1.00   12.50    --  108.00  65.00   0.00   98
 13  ω     69.00 120.00   1.00   12.50    --  108.00  43.00 -90.00   51
 14  ω     57.00 116.00   1.00    1.00    --   25.69 178.00-180.00   59
 15  ω     58.00 111.00   1.00    1.00    --   25.69 178.00   0.00   53
 16  ω     25.00 132.00   1.00    5.00    --   66.85  77.00-150.00  107
 17  ω     24.00  72.00   1.00   12.50    --  108.00-104.00  60.00   48
 18  ω     84.00 111.00   1.00   12.50    --  108.00-104.00  60.00   27
 19  ω     72.00 100.00   1.00   12.50    --  108.00-104.00   0.00   28
 20  ω     56.00 111.00   1.00    5.00    --   66.85-111.00  30.00   55
 21  ω     44.00  93.00   1.00   12.50    --  108.00-104.00  30.00   49
 22  ω     24.00  59.00   1.00   12.50    --  108.00-104.00   0.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3470
_reflns_number_total             4534
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.061
_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)+(0.0786P)²+0.6302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1681
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C3(H3), C30(H30), C28(H28), C24(H24), C29(H29), C26(H26), C25(H25),
 C17(H17), C16(H16), C14(H14), C10(H10), C12(H12), C15(H15), C11(H11)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O4 O 0.5755(3) 0.74543(14) 0.43553(6) 0.0799(6) Uani 1 1 d . . . . .
N1 N 0.6878(2) 0.92776(13) 0.47720(6) 0.0522(4) Uani 1 1 d . . . . .
N3 N 0.8118(2) 1.03699(13) 0.54171(6) 0.0546(4) Uani 1 1 d . . . . .
O3 O 0.6097(3) 0.66140(14) 0.50491(6) 0.0828(6) Uani 1 1 d . . . . .
O1 O 0.9278(3) 1.07314(16) 0.63344(7) 0.0898(6) Uani 1 1 d . . . . .
H1 H 0.894002 1.053618 0.606179 0.135 Uiso 1 1 calc R U . . .
N2 N 0.7449(3) 0.85911(15) 0.55284(7) 0.0679(5) Uani 1 1 d . . . . .
H2A H 0.705114 0.798262 0.542027 0.081 Uiso 1 1 calc R U . . .
H2B H 0.782369 0.865838 0.582592 0.081 Uiso 1 1 calc R U . . .
O2 O 0.8643(4) 0.90662(18) 0.65103(7) 0.1054(8) Uani 1 1 d . . . . .
C22 C 0.6180(3) 0.40696(16) 0.38699(7) 0.0493(5) Uani 1 1 d . . . . .
C1 C 0.7483(3) 0.94275(16) 0.52355(7) 0.0514(5) Uani 1 1 d . . . . .
C21 C 0.6578(3) 0.49067(16) 0.42109(7) 0.0506(5) Uani 1 1 d . . . . .
C27 C 0.7602(3) 0.34080(17) 0.37358(8) 0.0557(5) Uani 1 1 d . . . . .
C2 C 0.8130(3) 1.12049(17) 0.51182(8) 0.0581(5) Uani 1 1 d . . . . .
C19 C 0.5686(3) 0.66037(17) 0.46210(8) 0.0580(5) Uani 1 1 d . . . . .
C20 C 0.5063(3) 0.56186(17) 0.43480(8) 0.0589(5) Uani 1 1 d . . . . .
H20A H 0.434252 0.583525 0.405883 0.071 Uiso 1 1 calc R U . . .
H20B H 0.429329 0.520610 0.454097 0.071 Uiso 1 1 calc R U . . .
C23 C 0.4423(3) 0.38619(17) 0.36543(8) 0.0585(5) Uani 1 1 d . . . . .
H23 H 0.346829 0.428279 0.373706 0.070 Uiso 1 1 calc R U . . .
C4 C 0.6892(3) 1.01162(18) 0.44774(8) 0.0576(5) Uani 1 1 d . . . . .
C3 C 0.7502(3) 1.11042(18) 0.46430(9) 0.0654(6) Uani 1 1 d . . . . .
H3 H 0.748963 1.169082 0.443791 0.078 Uiso 1 1 calc R U . . .
C30 C 0.8317(3) 0.5026(2) 0.44088(8) 0.0620(6) Uani 1 1 d . . . . .
H30 H 0.858319 0.556638 0.463246 0.074 Uiso 1 1 calc R U . . .
C28 C 0.9374(3) 0.3569(2) 0.39549(9) 0.0661(6) Uani 1 1 d . . . . .
H28 H 1.030857 0.313195 0.387200 0.079 Uiso 1 1 calc R U . . .
C24 C 0.4101(4) 0.30603(19) 0.33287(9) 0.0696(6) Uani 1 1 d . . . . .
H24 H 0.293042 0.293153 0.319766 0.084 Uiso 1 1 calc R U . . .
C29 C 0.9706(3) 0.4350(2) 0.42814(9) 0.0704(7) Uani 1 1 d . . . . .
H29 H 1.086997 0.444370 0.442474 0.085 Uiso 1 1 calc R U . . .
C26 C 0.7212(4) 0.25980(19) 0.33893(9) 0.0702(6) Uani 1 1 d . . . . .
H26 H 0.814301 0.217121 0.329627 0.084 Uiso 1 1 calc R U . . .
C7 C 0.9194(4) 0.9930(2) 0.66279(9) 0.0702(6) Uani 1 1 d . . . . .
C18 C 0.7887(4) 0.9330(2) 0.77016(8) 0.0722(7) Uani 1 1 d . . . . .
C25 C 0.5511(4) 0.2429(2) 0.31896(10) 0.0751(7) Uani 1 1 d . . . . .
H25 H 0.528537 0.189529 0.296063 0.090 Uiso 1 1 calc R U . . .
C5 C 0.6206(4) 0.9928(2) 0.39651(9) 0.0772(7) Uani 1 1 d . . . . .
H5A H 0.696947 0.941960 0.382418 0.116 Uiso 1 1 calc R U . . .
H5B H 0.620960 1.059190 0.379191 0.116 Uiso 1 1 calc R U . . .
H5C H 0.499958 0.965212 0.395130 0.116 Uiso 1 1 calc R U . . .
C6 C 0.8866(4) 1.2241(2) 0.53240(11) 0.0774(7) Uani 1 1 d . . . . .
H6A H 0.820341 1.244847 0.558770 0.116 Uiso 1 1 calc R U . . .
H6B H 0.875154 1.278709 0.508192 0.116 Uiso 1 1 calc R U . . .
H6C H 1.011368 1.215047 0.543408 0.116 Uiso 1 1 calc R U . . .
C9 C 0.9534(5) 0.9333(3) 0.74994(9) 0.0851(9) Uani 1 1 d . . . . .
C13 C 0.7514(5) 0.8560(2) 0.80455(9) 0.0832(8) Uani 1 1 d . . . . .
C17 C 0.6521(5) 1.0129(3) 0.75861(11) 0.0890(9) Uani 1 1 d . . . . .
H17 H 0.668947 1.064524 0.735493 0.107 Uiso 1 1 calc R U . . .
C8 C 0.9946(5) 1.0184(3) 0.71327(10) 0.0970(10) Uani 1 1 d . . . . .
H8A H 0.945625 1.086431 0.722699 0.116 Uiso 1 1 calc R U . . .
H8B H 1.124249 1.026441 0.713761 0.116 Uiso 1 1 calc R U . . .
C16 C 0.4989(5) 1.0129(3) 0.78136(15) 0.1033(11) Uani 1 1 d . . . . .
H16 H 0.412106 1.065294 0.773862 0.124 Uiso 1 1 calc R U . . .
C14 C 0.5919(6) 0.8583(3) 0.82672(12) 0.1060(12) Uani 1 1 d . . . . .
H14 H 0.569446 0.806199 0.849180 0.127 Uiso 1 1 calc R U . . .
C10 C 1.0747(5) 0.8552(3) 0.76413(12) 0.1047(11) Uani 1 1 d . . . . .
H10 H 1.184318 0.853550 0.750625 0.126 Uiso 1 1 calc R U . . .
C12 C 0.8835(7) 0.7760(3) 0.81820(12) 0.1089(12) Uani 1 1 d . . . . .
H12 H 0.860563 0.723898 0.840599 0.131 Uiso 1 1 calc R U . . .
C15 C 0.4695(6) 0.9363(4) 0.81560(15) 0.1119(12) Uani 1 1 d . . . . .
H15 H 0.364302 0.938527 0.831106 0.134 Uiso 1 1 calc R U . . .
C11 C 1.0407(7) 0.7768(4) 0.79844(15) 0.1184(14) Uani 1 1 d . . . . .
H11 H 1.127751 0.725499 0.807384 0.142 Uiso 1 1 calc R U . . .
H4 H 0.608(4) 0.805(3) 0.4526(11) 0.088(9) 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
O4 C19 1.300(3) . ?
O4 H4 0.90(3) . ?
N1 C1 1.350(3) . ?
N1 C4 1.333(3) . ?
N3 C1 1.350(3) . ?
N3 C2 1.337(3) . ?
O3 C19 1.212(3) . ?
O1 H1 0.8200 . ?
O1 C7 1.300(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.329(3) . ?
O2 C7 1.189(3) . ?
C22 C21 1.429(3) . ?
C22 C27 1.419(3) . ?
C22 C23 1.416(3) . ?
C21 C20 1.512(3) . ?
C21 C30 1.372(3) . ?
C27 C28 1.420(3) . ?
C27 C26 1.414(3) . ?
C2 C3 1.378(3) . ?
C2 C6 1.499(3) . ?
C19 C20 1.499(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C24 1.361(3) . ?
C4 C3 1.380(3) . ?
C4 C5 1.499(3) . ?
C3 H3 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.405(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.345(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.396(4) . ?
C29 H29 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.355(4) . ?
C7 C8 1.509(4) . ?
C18 C9 1.396(4) . ?
C18 C13 1.406(4) . ?
C18 C17 1.441(4) . ?
C25 H25 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 C8 1.527(5) . ?
C9 C10 1.364(5) . ?
C13 C14 1.389(5) . ?
C13 C12 1.430(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.355(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C15 1.386(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.351(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.410(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.339(6) . ?
C15 H15 0.9300 . ?
C11 H11 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
C19 O4 H4 113(2) . . ?
C4 N1 C1 117.86(18) . . ?
C2 N3 C1 117.62(18) . . ?
C7 O1 H1 109.5 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C27 C22 C21 119.10(18) . . ?
C23 C22 C21 123.3(2) . . ?
C23 C22 C27 117.63(19) . . ?
N1 C1 N3 124.02(18) . . ?
N2 C1 N1 117.56(18) . . ?
N2 C1 N3 118.43(18) . . ?
C22 C21 C20 118.92(17) . . ?
C30 C21 C22 118.8(2) . . ?
C30 C21 C20 122.2(2) . . ?
C22 C27 C28 119.4(2) . . ?
C26 C27 C22 119.0(2) . . ?
C26 C27 C28 121.6(2) . . ?
N3 C2 C3 120.9(2) . . ?
N3 C2 C6 116.9(2) . . ?
C3 C2 C6 122.1(2) . . ?
O4 C19 C20 113.74(19) . . ?
O3 C19 O4 122.6(2) . . ?
O3 C19 C20 123.6(2) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 C21 113.99(18) . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.6 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.3 . . ?
N1 C4 C3 120.8(2) . . ?
N1 C4 C5 116.7(2) . . ?
C3 C4 C5 122.4(2) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C21 C30 H30 119.2 . . ?
C21 C30 C29 121.5(2) . . ?
C29 C30 H30 119.2 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.3(2) . . ?
C29 C28 H28 119.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C30 C29 H29 119.6 . . ?
C28 C29 C30 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C27 C26 H26 119.3 . . ?
C25 C26 C27 121.5(2) . . ?
C25 C26 H26 119.3 . . ?
O1 C7 C8 113.4(2) . . ?
O2 C7 O1 123.8(2) . . ?
O2 C7 C8 122.7(3) . . ?
C9 C18 C13 120.9(3) . . ?
C9 C18 C17 122.4(3) . . ?
C13 C18 C17 116.6(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(2) . . ?
C26 C25 H25 120.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C18 C9 C8 120.7(3) . . ?
C10 C9 C18 117.6(3) . . ?
C10 C9 C8 121.7(3) . . ?
C18 C13 C12 119.1(3) . . ?
C14 C13 C18 121.4(3) . . ?
C14 C13 C12 119.4(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C7 C8 C9 113.9(2) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C17 C16 H16 119.5 . . ?
C17 C16 C15 121.1(4) . . ?
C15 C16 H16 119.5 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(4) . . ?
C11 C10 H10 118.7 . . ?
C13 C12 H12 120.3 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N3 0.82 1.87 2.677(3) 169.1 . yes
N2 H2A O3 0.86 2.09 2.943(2) 170.8 . yes
N2 H2B O2 0.86 2.03 2.878(3) 171.0 . yes
O4 H4 N1 0.90(3) 1.76(3) 2.658(2) 170(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C19 C20 C21 97.0(2) . . . . ?
N1 C4 C3 C2 1.2(4) . . . . ?
N3 C2 C3 C4 -1.3(4) . . . . ?
O3 C19 C20 C21 -82.7(3) . . . . ?
O1 C7 C8 C9 168.9(3) . . . . ?
O2 C7 C8 C9 -13.8(5) . . . . ?
C22 C21 C20 C19 -167.34(19) . . . . ?
C22 C21 C30 C29 0.4(3) . . . . ?
C22 C27 C28 C29 -0.9(3) . . . . ?
C22 C27 C26 C25 -1.1(4) . . . . ?
C22 C23 C24 C25 -1.4(4) . . . . ?
C1 N1 C4 C3 -0.1(3) . . . . ?
C1 N1 C4 C5 -179.8(2) . . . . ?
C1 N3 C2 C3 0.4(3) . . . . ?
C1 N3 C2 C6 -179.1(2) . . . . ?
C21 C22 C27 C28 2.1(3) . . . . ?
C21 C22 C27 C26 -178.4(2) . . . . ?
C21 C22 C23 C24 179.6(2) . . . . ?
C21 C30 C29 C28 0.8(4) . . . . ?
C27 C22 C21 C20 179.22(19) . . . . ?
C27 C22 C21 C30 -1.8(3) . . . . ?
C27 C22 C23 C24 -0.2(3) . . . . ?
C27 C28 C29 C30 -0.6(4) . . . . ?
C27 C26 C25 C24 -0.4(4) . . . . ?
C2 N3 C1 N1 0.6(3) . . . . ?
C2 N3 C1 N2 -179.5(2) . . . . ?
C20 C21 C30 C29 179.3(2) . . . . ?
C23 C22 C21 C20 -0.6(3) . . . . ?
C23 C22 C21 C30 178.3(2) . . . . ?
C23 C22 C27 C28 -178.1(2) . . . . ?
C23 C22 C27 C26 1.4(3) . . . . ?
C23 C24 C25 C26 1.7(4) . . . . ?
C4 N1 C1 N3 -0.8(3) . . . . ?
C4 N1 C1 N2 179.3(2) . . . . ?
C30 C21 C20 C19 13.8(3) . . . . ?
C28 C27 C26 C25 178.4(2) . . . . ?
C26 C27 C28 C29 179.6(2) . . . . ?
C18 C9 C8 C7 -83.2(4) . . . . ?
C18 C9 C10 C11 -1.0(5) . . . . ?
C18 C13 C14 C15 -0.5(5) . . . . ?
C18 C13 C12 C11 0.8(5) . . . . ?
C18 C17 C16 C15 -0.7(5) . . . . ?
C5 C4 C3 C2 -179.2(2) . . . . ?
C6 C2 C3 C4 178.2(2) . . . . ?
C9 C18 C13 C14 176.6(3) . . . . ?
C9 C18 C13 C12 -1.0(4) . . . . ?
C9 C18 C17 C16 -176.0(3) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C13 C18 C9 C8 -178.9(2) . . . . ?
C13 C18 C9 C10 1.1(4) . . . . ?
C13 C18 C17 C16 1.6(4) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C13 C12 C11 C10 -0.6(6) . . . . ?
C17 C18 C9 C8 -1.3(4) . . . . ?
C17 C18 C9 C10 178.7(3) . . . . ?
C17 C18 C13 C14 -1.1(4) . . . . ?
C17 C18 C13 C12 -178.7(3) . . . . ?
C17 C16 C15 C14 -1.0(5) . . . . ?
C8 C9 C10 C11 179.0(3) . . . . ?
C14 C13 C12 C11 -176.9(3) . . . . ?
C10 C9 C8 C7 96.8(4) . . . . ?
C12 C13 C14 C15 177.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
