# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_TY_11_038
_database_code_depnum_ccdc_archive 'CCDC 1879115'
_audit_update_record             
;
2018-11-15 deposited with the CCDC.
2018-12-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H20 N8 O3'
_chemical_formula_moiety         'C16 H20 N8 O3'
_chemical_formula_weight         372.39
_chemical_melting_point          358-359

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.5247(4)
_cell_length_b                   7.64772(17)
_cell_length_c                   17.7480(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.938(7)
_cell_angle_gamma                90.0000
_cell_volume                     1818.14(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18562
_cell_measurement_theta_min      2.04
_cell_measurement_theta_max      25.36
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784.00
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            24512
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3334
_reflns_number_gt                2850
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0783
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3334
_refine_ls_number_parameters     245
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0335P)²+0.7498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.60204(7) 0.78992(13) 0.81181(5) 0.0244(2) Uani 1 1 d . . . . .
O2 O 0.70708(9) 0.33560(15) 0.43119(6) 0.0357(3) Uani 1 1 d . . . . .
O3 O 0.49224(8) 0.13554(13) 0.58474(6) 0.0279(2) Uani 1 1 d . . . . .
H3 H 0.458110 0.165552 0.618687 0.034 Uiso 1 1 calc R U . . .
N1 N 0.69626(8) 0.74985(14) 0.71838(6) 0.0181(2) Uani 1 1 d . . . . .
N2 N 0.43050(9) 0.84486(16) 0.71430(8) 0.0296(3) Uani 1 1 d . . . . .
N3 N 0.36972(9) 0.74503(15) 0.73751(7) 0.0243(3) Uani 1 1 d . . . . .
N4 N 0.30770(11) 0.67125(18) 0.76001(8) 0.0352(3) Uani 1 1 d . . . . .
N5 N 1.03965(10) -0.03114(17) 0.84030(8) 0.0345(3) Uani 1 1 d . . . . .
N6 N 1.09242(10) -0.14461(18) 0.87231(8) 0.0366(3) Uani 1 1 d . . . . .
N7 N 1.14300(11) -0.2567(2) 0.89629(11) 0.0505(4) Uani 1 1 d . . . . .
N8 N 0.54907(9) 0.27540(15) 0.56670(6) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.70589(10) 0.72446(18) 0.63936(7) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.68281(10) 0.56357(18) 0.60567(7) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.661310 0.470019 0.634666 0.023 Uiso 1 1 calc R U . . .
C3 C 0.69131(10) 0.53963(18) 0.52874(7) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.72536(11) 0.67730(19) 0.48784(8) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.732002 0.661773 0.435670 0.030 Uiso 1 1 calc R U . . .
C5 C 0.74957(11) 0.8364(2) 0.52257(8) 0.0276(3) Uani 1 1 d . . . . .
H5 H 0.773027 0.929251 0.494205 0.033 Uiso 1 1 calc R U . . .
C6 C 0.73979(11) 0.86106(19) 0.59850(8) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.756167 0.970511 0.622307 0.029 Uiso 1 1 calc R U . . .
C7 C 0.60754(10) 0.76723(17) 0.74374(7) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.51466(10) 0.75959(19) 0.68472(8) 0.0251(3) Uani 1 1 d . . . . .
H8A H 0.527836 0.819170 0.637589 0.030 Uiso 1 1 calc R U . . .
H8B H 0.497632 0.636143 0.672124 0.030 Uiso 1 1 calc R U . . .
C9 C 0.78794(10) 0.75117(18) 0.77380(7) 0.0202(3) Uani 1 1 d . . . . .
H9A H 0.780673 0.837527 0.814232 0.024 Uiso 1 1 calc R U . . .
H9B H 0.844910 0.787866 0.747977 0.024 Uiso 1 1 calc R U . . .
C10 C 0.80978(10) 0.57236(18) 0.80963(8) 0.0220(3) Uani 1 1 d . . . . .
H10A H 0.754530 0.538438 0.837860 0.026 Uiso 1 1 calc R U . . .
H10B H 0.813482 0.484771 0.769042 0.026 Uiso 1 1 calc R U . . .
C11 C 0.90731(11) 0.57203(19) 0.86359(8) 0.0249(3) Uani 1 1 d . . . . .
H11A H 0.903514 0.662331 0.903058 0.030 Uiso 1 1 calc R U . . .
H11B H 0.962043 0.605340 0.834729 0.030 Uiso 1 1 calc R U . . .
C12 C 0.93333(11) 0.39747(19) 0.90278(8) 0.0273(3) Uani 1 1 d . . . . .
H12A H 0.989537 0.415282 0.944086 0.033 Uiso 1 1 calc R U . . .
H12B H 0.875246 0.356562 0.926316 0.033 Uiso 1 1 calc R U . . .
C13 C 0.96188(11) 0.25655(19) 0.84967(8) 0.0278(3) Uani 1 1 d . . . . .
H13A H 0.902729 0.224837 0.812917 0.033 Uiso 1 1 calc R U . . .
H13B H 1.013689 0.302381 0.820594 0.033 Uiso 1 1 calc R U . . .
C14 C 1.00099(12) 0.0958(2) 0.89313(9) 0.0310(4) Uani 1 1 d . . . . .
H14A H 1.055222 0.128946 0.933937 0.037 Uiso 1 1 calc R U . . .
H14B H 0.946806 0.040828 0.917066 0.037 Uiso 1 1 calc R U . . .
C15 C 0.66899(11) 0.36928(19) 0.48812(8) 0.0242(3) Uani 1 1 d . . . . .
C16 C 0.60222(10) 0.23728(19) 0.51504(8) 0.0235(3) Uani 1 1 d . . . . .
H16 H 0.598867 0.123159 0.493694 0.028 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C7 1.2327(16) . ?
O2 C15 1.2233(17) . ?
O3 N8 1.3803(15) . ?
O3 H3 0.8400 . ?
N1 C7 1.3451(17) . ?
N1 C1 1.4394(16) . ?
N1 C9 1.4725(17) . ?
N2 N3 1.2336(18) . ?
N2 C8 1.4703(18) . ?
N3 N4 1.1287(17) . ?
N5 N6 1.2137(19) . ?
N5 C14 1.4935(19) . ?
N6 N7 1.142(2) . ?
N8 C16 1.2745(18) . ?
C1 C2 1.3847(19) . ?
C1 C6 1.3855(19) . ?
C2 C3 1.3980(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C3 C15 1.499(2) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5217(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5198(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5192(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.516(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.508(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.477(2) . ?
C16 H16 0.9500 . ?

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
N8 O3 H3 109.5 . . ?
C7 N1 C1 122.98(11) . . ?
C7 N1 C9 118.92(11) . . ?
C1 N1 C9 118.08(10) . . ?
N3 N2 C8 115.42(12) . . ?
N4 N3 N2 171.72(14) . . ?
N6 N5 C14 113.90(13) . . ?
N7 N6 N5 174.05(18) . . ?
C16 N8 O3 112.15(11) . . ?
C2 C1 C6 121.01(12) . . ?
C2 C1 N1 119.69(12) . . ?
C6 C1 N1 119.30(12) . . ?
C1 C2 C3 119.61(12) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.19(13) . . ?
C4 C3 C15 117.73(12) . . ?
C2 C3 C15 123.03(12) . . ?
C5 C4 C3 120.52(13) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.33(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.32(13) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 N1 121.28(12) . . ?
O1 C7 C8 121.61(12) . . ?
N1 C7 C8 117.10(11) . . ?
N2 C8 C7 110.08(11) . . ?
N2 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C10 111.74(11) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 111.53(11) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 114.51(12) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 113.67(12) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 111.28(12) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N5 C14 C13 109.71(12) . . ?
N5 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
N5 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O2 C15 C16 117.98(13) . . ?
O2 C15 C3 120.02(13) . . ?
C16 C15 C3 121.99(12) . . ?
N8 C16 C15 120.47(13) . . ?
N8 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?

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
C7 N1 C1 C2 -74.43(17) . . . . ?
C9 N1 C1 C2 103.61(14) . . . . ?
C7 N1 C1 C6 106.63(15) . . . . ?
C9 N1 C1 C6 -75.34(16) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
N1 C1 C2 C3 179.41(12) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C1 C2 C3 C15 179.26(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C15 C3 C4 C5 -178.42(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
N1 C1 C6 C5 179.66(12) . . . . ?
C1 N1 C7 O1 -179.54(12) . . . . ?
C9 N1 C7 O1 2.44(19) . . . . ?
C1 N1 C7 C8 -0.18(18) . . . . ?
C9 N1 C7 C8 -178.20(11) . . . . ?
N3 N2 C8 C7 -101.65(14) . . . . ?
O1 C7 C8 N2 20.97(18) . . . . ?
N1 C7 C8 N2 -158.39(12) . . . . ?
C7 N1 C9 C10 82.98(14) . . . . ?
C1 N1 C9 C10 -95.14(13) . . . . ?
N1 C9 C10 C11 176.96(11) . . . . ?
C9 C10 C11 C12 179.02(11) . . . . ?
C10 C11 C12 C13 70.09(17) . . . . ?
C11 C12 C13 C14 171.78(13) . . . . ?
N6 N5 C14 C13 164.11(14) . . . . ?
C12 C13 C14 N5 -173.22(13) . . . . ?
C4 C3 C15 O2 21.8(2) . . . . ?
C2 C3 C15 O2 -155.85(14) . . . . ?
C4 C3 C15 C16 -158.72(13) . . . . ?
C2 C3 C15 C16 23.6(2) . . . . ?
O3 N8 C16 C15 -179.55(11) . . . . ?
O2 C15 C16 N8 -169.40(14) . . . . ?
C3 C15 C16 N8 11.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O1 . . 2_646 2.6528(15) 0.840 1.834 164.3 no


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
2-Azido-N-(6-azidohexyl)-N-(3-(2-(hydroxyimino)acetyl)phenyl)acetamide
_chemical_name_common            'trialkyl diazido oxime'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
