# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_sb1455_hy
_database_code_depnum_ccdc_archive 'CCDC 2158276'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-03-14 deposited with the CCDC.	2022-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
tris(4-azidophenyl)methanol
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N9 O'
_chemical_formula_sum            'C19 H13 N9 O'
_chemical_formula_weight         383.38

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.422(3)
_cell_length_b                   17.540(6)
_cell_length_c                   10.109(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1847.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.9

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7479
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 4+1 runs, 732 frames, 12 sec./frame
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38376
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4217
_reflns_number_gt                3742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.997

_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       'APEX3 (Bruker AXS Inc., 2019)'
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2019)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0496P)²+0.2804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The absolute structure cannot be determined reliably.
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4217
_refine_ls_number_parameters     265
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.18858(15) 0.58830(9) 0.42572(17) 0.0363(4) Uani 1 1 d D . . . .
H1 H 0.239(3) 0.5689(17) 0.370(3) 0.054 Uiso 1 1 d D U . . .
C1 C 0.2536(2) 0.64751(12) 0.4983(2) 0.0304(4) Uani 1 1 d . . . . .
C11 C 0.3806(2) 0.61380(12) 0.5505(2) 0.0308(5) Uani 1 1 d . . . . .
C12 C 0.4853(2) 0.60647(13) 0.4658(2) 0.0381(5) Uani 1 1 d . . . . .
H12 H 0.4813 0.6279 0.3818 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5956(2) 0.56794(14) 0.5041(3) 0.0401(5) Uani 1 1 d . . . . .
H13 H 0.6644 0.5633 0.4460 0.048 Uiso 1 1 calc R U . . .
C14 C 0.6024(2) 0.53639(13) 0.6298(3) 0.0360(5) Uani 1 1 d . . . . .
C15 C 0.5009(2) 0.54493(15) 0.7170(3) 0.0424(6) Uani 1 1 d . . . . .
H15 H 0.5063 0.5250 0.8021 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3912(2) 0.58332(14) 0.6772(3) 0.0387(5) Uani 1 1 d . . . . .
H16 H 0.3234 0.5888 0.7362 0.046 Uiso 1 1 calc R U . . .
N17 N 0.7105(2) 0.49413(14) 0.6782(2) 0.0489(5) Uani 1 1 d . . . . .
N18 N 0.7941(2) 0.47824(15) 0.5950(3) 0.0538(6) Uani 1 1 d . . . . .
N19 N 0.8763(3) 0.4604(2) 0.5305(4) 0.0904(11) Uani 1 1 d . . . . .
C21 C 0.2756(2) 0.71634(12) 0.4078(2) 0.0319(5) Uani 1 1 d . . . . .
C22 C 0.2002(2) 0.72676(14) 0.2955(2) 0.0367(5) Uani 1 1 d . . . . .
H22 H 0.1393 0.6901 0.2734 0.044 Uiso 1 1 calc R U . . .
C23 C 0.2139(2) 0.79062(15) 0.2157(3) 0.0420(6) Uani 1 1 d . . . . .
H23 H 0.1627 0.7965 0.1411 0.050 Uiso 1 1 calc R U . . .
C24 C 0.3041(2) 0.84551(13) 0.2477(2) 0.0374(5) Uani 1 1 d . . . . .
C25 C 0.3807(2) 0.83649(14) 0.3586(3) 0.0379(5) Uani 1 1 d . . . . .
H25 H 0.4411 0.8735 0.3804 0.046 Uiso 1 1 calc R U . . .
C26 C 0.3670(2) 0.77209(13) 0.4369(2) 0.0351(5) Uani 1 1 d . . . . .
H26 H 0.4197 0.7659 0.5103 0.042 Uiso 1 1 calc R U . . .
N27 N 0.3227(3) 0.91398(13) 0.1723(3) 0.0538(6) Uani 1 1 d . . . . .
N28 N 0.2574(3) 0.91835(13) 0.0696(3) 0.0515(6) Uani 1 1 d . . . . .
N29 N 0.2031(3) 0.92810(16) -0.0249(3) 0.0739(8) Uani 1 1 d . . . . .
C31 C 0.1623(2) 0.66855(13) 0.6123(2) 0.0313(5) Uani 1 1 d . . . . .
C32 C 0.1699(2) 0.73847(14) 0.6769(3) 0.0401(5) Uani 1 1 d . . . . .
H32 H 0.2301 0.7741 0.6489 0.048 Uiso 1 1 calc R U . . .
C33 C 0.0895(3) 0.75620(15) 0.7823(3) 0.0450(6) Uani 1 1 d . . . . .
H33 H 0.0965 0.8031 0.8245 0.054 Uiso 1 1 calc R U . . .
C34 C -0.0010(3) 0.70388(15) 0.8240(3) 0.0418(5) Uani 1 1 d . . . . .
C35 C -0.0091(3) 0.63342(16) 0.7626(3) 0.0463(6) Uani 1 1 d . . . . .
H35 H -0.0690 0.5978 0.7914 0.056 Uiso 1 1 calc R U . . .
C36 C 0.0724(2) 0.61607(14) 0.6581(2) 0.0390(5) Uani 1 1 d . . . . .
H36 H 0.0667 0.5685 0.6179 0.047 Uiso 1 1 calc R U . . .
N37 N -0.0882(3) 0.71772(16) 0.9315(3) 0.0607(7) Uani 1 1 d . . . . .
N38 N -0.0909(3) 0.78322(17) 0.9753(3) 0.0646(7) Uani 1 1 d . . . . .
N39 N -0.1027(4) 0.8398(2) 1.0249(5) 0.1104(15) Uani 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
O1 C1 1.441(3) . ?
O1 H1 0.84(2) . ?
C1 C21 1.532(3) . ?
C1 C31 1.540(3) . ?
C1 C11 1.543(3) . ?
C11 C16 1.392(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 N17 1.435(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N17 N18 1.243(3) . ?
N18 N19 1.121(4) . ?
C21 C22 1.394(3) . ?
C21 C26 1.396(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(4) . ?
C24 N27 1.436(3) . ?
C25 C26 1.387(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N27 N28 1.244(4) . ?
N28 N29 1.123(4) . ?
C31 C32 1.391(3) . ?
C31 C36 1.393(3) . ?
C32 C33 1.391(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.382(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.386(4) . ?
C34 N37 1.437(3) . ?
C35 C36 1.390(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N37 N38 1.231(4) . ?
N38 N39 1.119(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 110(2) . . ?
O1 C1 C21 109.56(18) . . ?
O1 C1 C31 105.26(17) . . ?
C21 C1 C31 110.53(18) . . ?
O1 C1 C11 107.55(17) . . ?
C21 C1 C11 112.20(17) . . ?
C31 C1 C11 111.46(18) . . ?
C16 C11 C12 117.9(2) . . ?
C16 C11 C1 122.0(2) . . ?
C12 C11 C1 119.82(19) . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 N17 116.0(2) . . ?
C13 C14 N17 124.0(2) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N18 N17 C14 115.8(2) . . ?
N19 N18 N17 172.7(3) . . ?
C22 C21 C26 117.7(2) . . ?
C22 C21 C1 120.4(2) . . ?
C26 C21 C1 121.9(2) . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 N27 123.3(2) . . ?
C25 C24 N27 116.6(2) . . ?
C24 C25 C26 119.7(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C21 121.4(2) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
N28 N27 C24 114.9(2) . . ?
N29 N28 N27 174.2(3) . . ?
C32 C31 C36 117.7(2) . . ?
C32 C31 C1 121.8(2) . . ?
C36 C31 C1 120.4(2) . . ?
C33 C32 C31 121.5(2) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C34 C33 C32 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 119.8(2) . . ?
C33 C34 N37 123.4(2) . . ?
C35 C34 N37 116.8(2) . . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 121.3(2) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
N38 N37 C34 116.3(2) . . ?
N39 N38 N37 172.4(3) . . ?

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
O1 C1 C11 C16 -94.9(2) . . . . ?
C21 C1 C11 C16 144.6(2) . . . . ?
C31 C1 C11 C16 20.0(3) . . . . ?
O1 C1 C11 C12 78.8(2) . . . . ?
C21 C1 C11 C12 -41.7(3) . . . . ?
C31 C1 C11 C12 -166.3(2) . . . . ?
C16 C11 C12 C13 2.1(4) . . . . ?
C1 C11 C12 C13 -171.9(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 -1.5(4) . . . . ?
C12 C13 C14 N17 178.6(2) . . . . ?
C13 C14 C15 C16 1.7(4) . . . . ?
N17 C14 C15 C16 -178.4(2) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C12 C11 C16 C15 -1.8(4) . . . . ?
C1 C11 C16 C15 172.0(2) . . . . ?
C15 C14 N17 N18 171.2(2) . . . . ?
C13 C14 N17 N18 -8.9(4) . . . . ?
O1 C1 C21 C22 21.8(3) . . . . ?
C31 C1 C21 C22 -93.8(2) . . . . ?
C11 C1 C21 C22 141.2(2) . . . . ?
O1 C1 C21 C26 -160.9(2) . . . . ?
C31 C1 C21 C26 83.5(2) . . . . ?
C11 C1 C21 C26 -41.5(3) . . . . ?
C26 C21 C22 C23 -0.7(4) . . . . ?
C1 C21 C22 C23 176.7(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C22 C23 C24 N27 -178.7(2) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
N27 C24 C25 C26 179.3(2) . . . . ?
C24 C25 C26 C21 -1.1(3) . . . . ?
C22 C21 C26 C25 1.3(3) . . . . ?
C1 C21 C26 C25 -176.0(2) . . . . ?
C23 C24 N27 N28 -4.7(4) . . . . ?
C25 C24 N27 N28 176.3(2) . . . . ?
O1 C1 C31 C32 -158.4(2) . . . . ?
C21 C1 C31 C32 -40.2(3) . . . . ?
C11 C1 C31 C32 85.3(3) . . . . ?
O1 C1 C31 C36 24.5(3) . . . . ?
C21 C1 C31 C36 142.7(2) . . . . ?
C11 C1 C31 C36 -91.8(2) . . . . ?
C36 C31 C32 C33 -0.9(4) . . . . ?
C1 C31 C32 C33 -178.2(2) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 C35 1.4(4) . . . . ?
C32 C33 C34 N37 -179.7(3) . . . . ?
C33 C34 C35 C36 -1.0(4) . . . . ?
N37 C34 C35 C36 -179.9(3) . . . . ?
C34 C35 C36 C31 -0.5(4) . . . . ?
C32 C31 C36 C35 1.4(4) . . . . ?
C1 C31 C36 C35 178.7(2) . . . . ?
C33 C34 N37 N38 9.3(4) . . . . ?
C35 C34 N37 N38 -171.8(3) . . . . ?

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
O1 H1 N17 0.84(2) 2.29(3) 3.075(3) 155(3) 2_664

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034

