# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2244996'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.7087(2)
_cell_length_b                   11.2855(2)
_cell_length_c                   12.0893(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.9689(6)
_cell_angle_gamma                90
_cell_volume                     1024.90(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'

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4
_chemical_name_systematic        
' 1-(4-(p-tolyl)-2H-1,2,3-triazol-2-yl)ethan-1-one'
_chemical_formula_moiety         'C11 H11 N3 O'

# Given Formula = C11 H11 N3 O1 
# Dc =      1.30 Fooo =    424.00 Mu =      7.10 M =    201.23
# Found Formula = C11 H11 N3 O1 
# Dc =      1.30 FOOO =    424.00 Mu =      7.10 M =    201.23

_chemical_formula_sum            'C11 H11 N3 O'
_chemical_compound_source        ?
_chemical_formula_weight         201.23


_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      3.9170
_cell_measurement_theta_max      70.0476
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.088
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_max          0.333

_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.710

# Sheldrick geometric approximatio 0.91 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19496
_reflns_number_total             1876
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1876 
# Theoretical number of reflections is about 3752 


_diffrn_reflns_theta_min         5.428
_diffrn_reflns_theta_max         68.224
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        68.224
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.28
_oxford_diffrn_Wilson_scale      14.58

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.22


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_number_parameters     137
_oxford_refine_ls_R_factor_ref   0.0379
_refine_ls_wR_factor_ref         0.0404
_refine_ls_goodness_of_fit_ref   1.0701
_refine_ls_shift/su_max          0.0003834
_refine_ls_shift/su_mean         0.0000595


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1876
_refine_ls_R_factor_all          0.0396
_refine_ls_wR_factor_all         0.0429

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1807
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_gt          0.0404


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.174 0.140 0.453E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.96590(12) 0.62823(8) 0.88273(7) 0.0439 1.0000 Uani . . . . . .
C2 C 0.95292(15) 0.55611(10) 0.80822(9) 0.0323 1.0000 Uani . . . . . .
N3 N 0.85967(12) 0.58602(8) 0.69655(7) 0.0290 1.0000 Uani . . . . . .
N4 N 0.83767(11) 0.50844(8) 0.60964(7) 0.0285 1.0000 Uani . . . . . .
C5 C 0.73779(13) 0.56669(10) 0.52319(9) 0.0276 1.0000 Uani . . . . . .
C6 C 0.70169(16) 0.68050(10) 0.56256(10) 0.0346 1.0000 Uani . . . . . .
N7 N 0.77897(13) 0.69156(8) 0.67084(8) 0.0354 1.0000 Uani . . . . . .
C8 C 0.67903(13) 0.51374(10) 0.41010(9) 0.0278 1.0000 Uani . . . . . .
C9 C 0.74739(14) 0.40445(10) 0.38542(10) 0.0313 1.0000 Uani . . . . . .
C10 C 0.68765(15) 0.35273(10) 0.28054(10) 0.0347 1.0000 Uani . . . . . .
C11 C 0.55778(15) 0.40646(11) 0.19688(10) 0.0356 1.0000 Uani . . . . . .
C12 C 0.49340(14) 0.51631(11) 0.22098(10) 0.0343 1.0000 Uani . . . . . .
C13 C 0.55256(14) 0.56980(10) 0.32594(9) 0.0308 1.0000 Uani . . . . . .
C14 C 0.4856(2) 0.34520(14) 0.08564(12) 0.0535 1.0000 Uani . . . . . .
C15 C 1.02715(17) 0.43374(11) 0.82093(10) 0.0385 1.0000 Uani . . . . . .
H61 H 0.6335 0.7440 0.5204 0.0423 1.0000 Uiso R . . . . .
H91 H 0.8344 0.3659 0.4422 0.0368 1.0000 Uiso R . . . . .
H101 H 0.7366 0.2777 0.2658 0.0416 1.0000 Uiso R . . . . .
H121 H 0.4056 0.5544 0.1639 0.0406 1.0000 Uiso R . . . . .
H131 H 0.5068 0.6451 0.3408 0.0373 1.0000 Uiso R . . . . .
H141 H 0.4355 0.3993 0.0249 0.0820 1.0000 Uiso R . . . . .
H143 H 0.5708 0.2996 0.0614 0.0833 1.0000 Uiso R . . . . .
H142 H 0.3852 0.2925 0.0929 0.0828 1.0000 Uiso R . . . . .
H152 H 0.9349 0.3750 0.7909 0.0578 1.0000 Uiso R . . . . .
H151 H 1.1183 0.4269 0.7751 0.0580 1.0000 Uiso R . . . . .
H153 H 1.0785 0.4197 0.9006 0.0579 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0582(6) 0.0395(5) 0.0323(4) -0.0066(4) 0.0062(4) -0.0059(4)
C2 0.0333(6) 0.0338(6) 0.0299(6) -0.0006(5) 0.0076(4) -0.0074(5)
N3 0.0314(5) 0.0267(5) 0.0293(5) -0.0017(4) 0.0077(4) -0.0021(4)
N4 0.0293(4) 0.0276(5) 0.0292(5) -0.0027(4) 0.0076(4) -0.0029(4)
C5 0.0253(5) 0.0280(5) 0.0308(5) 0.0012(4) 0.0088(4) -0.0027(4)
C6 0.0400(6) 0.0286(6) 0.0343(6) 0.0009(5) 0.0067(5) 0.0029(5)
N7 0.0422(5) 0.0270(5) 0.0368(5) -0.0009(4) 0.0085(4) 0.0024(4)
C8 0.0266(5) 0.0282(5) 0.0301(5) 0.0001(4) 0.0095(4) -0.0047(4)
C9 0.0302(5) 0.0285(6) 0.0357(6) 0.0030(5) 0.0086(4) -0.0012(4)
C10 0.0365(6) 0.0274(6) 0.0429(6) -0.0039(5) 0.0146(5) -0.0040(5)
C11 0.0351(6) 0.0388(6) 0.0344(6) -0.0057(5) 0.0114(5) -0.0088(5)
C12 0.0303(5) 0.0402(7) 0.0313(6) 0.0015(5) 0.0049(4) -0.0012(5)
C13 0.0292(5) 0.0293(6) 0.0348(6) 0.0002(4) 0.0091(4) -0.0001(4)
C14 0.0596(8) 0.0579(9) 0.0409(7) -0.0158(6) 0.0069(6) -0.0041(7)
C15 0.0435(7) 0.0359(7) 0.0339(6) 0.0043(5) 0.0041(5) -0.0017(5)

_refine_ls_extinction_coef       24(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.2859(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2014(14) yes
C2 . N3 . 1.4204(14) yes
C2 . C15 . 1.4896(17) yes
N3 . N4 . 1.3488(12) yes
N3 . N7 . 1.3474(13) yes
N4 . C5 . 1.3252(14) yes
C5 . C6 . 1.4188(16) yes
C5 . C8 . 1.4674(15) yes
C6 . N7 . 1.3169(15) yes
C6 . H61 . 0.964 no
C8 . C9 . 1.3995(16) yes
C8 . C13 . 1.3931(15) yes
C9 . C10 . 1.3779(16) yes
C9 . H91 . 0.951 no
C10 . C11 . 1.3922(18) yes
C10 . H101 . 0.960 no
C11 . C12 . 1.3903(17) yes
C11 . C14 . 1.5035(17) yes
C12 . C13 . 1.3867(16) yes
C12 . H121 . 0.953 no
C13 . H131 . 0.952 no
C14 . H141 . 0.966 no
C14 . H143 . 0.932 no
C14 . H142 . 0.995 no
C15 . H152 . 0.980 no
C15 . H151 . 0.990 no
C15 . H153 . 0.969 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 119.39(11) yes
O1 . C2 . C15 . 125.83(11) yes
N3 . C2 . C15 . 114.78(10) yes
C2 . N3 . N4 . 122.30(9) yes
C2 . N3 . N7 . 122.56(9) yes
N4 . N3 . N7 . 115.05(9) yes
N3 . N4 . C5 . 103.98(9) yes
N4 . C5 . C6 . 107.91(10) yes
N4 . C5 . C8 . 122.41(10) yes
C6 . C5 . C8 . 129.67(10) yes
C5 . C6 . N7 . 109.89(10) yes
C5 . C6 . H61 . 128.3 no
N7 . C6 . H61 . 121.8 no
N3 . N7 . C6 . 103.18(9) yes
C5 . C8 . C9 . 120.35(10) yes
C5 . C8 . C13 . 120.97(10) yes
C9 . C8 . C13 . 118.67(10) yes
C8 . C9 . C10 . 120.36(10) yes
C8 . C9 . H91 . 119.2 no
C10 . C9 . H91 . 120.5 no
C9 . C10 . C11 . 121.42(11) yes
C9 . C10 . H101 . 118.7 no
C11 . C10 . H101 . 119.9 no
C10 . C11 . C12 . 117.94(11) yes
C10 . C11 . C14 . 120.73(12) yes
C12 . C11 . C14 . 121.30(12) yes
C11 . C12 . C13 . 121.36(11) yes
C11 . C12 . H121 . 118.6 no
C13 . C12 . H121 . 120.0 no
C8 . C13 . C12 . 120.21(11) yes
C8 . C13 . H131 . 119.7 no
C12 . C13 . H131 . 120.1 no
C11 . C14 . H141 . 113.2 no
C11 . C14 . H143 . 112.9 no
H141 . C14 . H143 . 107.4 no
C11 . C14 . H142 . 109.6 no
H141 . C14 . H142 . 105.0 no
H143 . C14 . H142 . 108.3 no
C2 . C15 . H152 . 111.0 no
C2 . C15 . H151 . 108.6 no
H152 . C15 . H151 . 106.7 no
C2 . C15 . H153 . 108.4 no
H152 . C15 . H153 . 111.0 no
H151 . C15 . H153 . 111.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . O1 4_464 167.37(3) 0.964 2.356 3.3039(17) yes


_iucr_refine_instructions_details 
;
#
# Punched on 21/02/23 at 14:33:15
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 143,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) H   ( 153,X'S) 
END                                                                             
#
# Punched on 21/02/23 at 14:33:15
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2244997'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.1806(6)
_cell_length_b                   9.0341(6)
_cell_length_c                   11.2117(8)
_cell_angle_alpha                93.215(2)
_cell_angle_beta                 106.075(2)
_cell_angle_gamma                113.5933(19)
_cell_volume                     716.42(9)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2
_chemical_name_systematic        
(4-methoxyphenyl)(4-(p-tolyl)-1H-1,2,3-triazol-1-yl)methanone
_chemical_formula_moiety         'C17 H15 N3 O2'

# Given Formula = C17 H15 N3 O2 
# Dc =      1.36 Fooo =    308.00 Mu =      7.44 M =    293.33
# Found Formula = C17 H15 N3 O2 
# Dc =      1.36 FOOO =    308.00 Mu =      7.44 M =    293.33

_chemical_formula_sum            'C17 H15 N3 O2'
_chemical_compound_source        ?
_chemical_formula_weight         293.33


_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      4.1794
_cell_measurement_theta_max      68.4213
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.156
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_max          0.323

_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.744

# Sheldrick geometric approximatio 0.87 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20666
_reflns_number_total             2602
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2602 
# Theoretical number of reflections is about 5267 


_diffrn_reflns_theta_min         4.179
_diffrn_reflns_theta_max         68.415
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        68.415
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.51
_oxford_diffrn_Wilson_scale      5.95

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.23


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_number_parameters     244
_oxford_refine_ls_R_factor_ref   0.0436
_refine_ls_wR_factor_ref         0.0471
_refine_ls_goodness_of_fit_ref   1.0128
_refine_ls_shift/su_max          0.0002223
_refine_ls_shift/su_mean         0.0000250


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2602
_refine_ls_R_factor_all          0.0445
_refine_ls_wR_factor_all         0.0478

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2489
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_gt          0.0471


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refxyz #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.553 0.754 0.454 0.200 0.521E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O -0.05626(13) 0.07193(11) -0.27252(8) 0.0462 1.0000 Uani . . . . . .
C2 C -0.14009(17) 0.04172(15) -0.19705(11) 0.0346 1.0000 Uani . . . . . .
N3 N -0.05839(14) 0.15959(12) -0.08145(9) 0.0335 1.0000 Uani . . . . . .
N4 N -0.10846(15) 0.13102(13) 0.02453(9) 0.0400 1.0000 Uani . . . . . .
N5 N 0.00156(15) 0.26167(14) 0.11089(10) 0.0412 1.0000 Uani . . . . . .
C6 C 0.12483(16) 0.37631(15) 0.06343(11) 0.0345 1.0000 Uani . . . . . .
C7 C 0.08730(17) 0.31099(15) -0.05871(11) 0.0356 1.0000 Uani . . . . . .
C8 C 0.26890(17) 0.53478(15) 0.14264(11) 0.0351 1.0000 Uani . . . . . .
C9 C 0.42525(18) 0.63012(16) 0.10902(12) 0.0405 1.0000 Uani . . . . . .
C10 C 0.5653(2) 0.77607(17) 0.18723(13) 0.0455 1.0000 Uani . . . . . .
C11 C 0.55385(19) 0.83088(16) 0.30157(12) 0.0443 1.0000 Uani . . . . . .
C12 C 0.3955(2) 0.73763(18) 0.33294(12) 0.0462 1.0000 Uani . . . . . .
C13 C 0.2548(2) 0.59199(17) 0.25578(12) 0.0418 1.0000 Uani . . . . . .
C14 C 0.7085(3) 0.9863(2) 0.38850(17) 0.0579 1.0000 Uani . . . . . .
C15 C -0.31894(16) -0.10593(14) -0.21920(11) 0.0323 1.0000 Uani . . . . . .
C16 C -0.36278(18) -0.23224(16) -0.31603(12) 0.0386 1.0000 Uani . . . . . .
C17 C -0.53221(18) -0.37192(15) -0.35264(12) 0.0380 1.0000 Uani . . . . . .
C18 C -0.66264(17) -0.38553(14) -0.29211(11) 0.0353 1.0000 Uani . . . . . .
O19 O -0.83533(13) -0.51581(11) -0.32181(9) 0.0463 1.0000 Uani . . . . . .
C20 C -0.8915(2) -0.63999(17) -0.42845(14) 0.0476 1.0000 Uani . . . . . .
C21 C -0.62078(19) -0.26104(16) -0.19459(13) 0.0417 1.0000 Uani . . . . . .
C22 C -0.45132(18) -0.12296(15) -0.15774(12) 0.0381 1.0000 Uani . . . . . .
H71 H 0.136(2) 0.3508(18) -0.1198(14) 0.0435 1.0000 Uiso . . . . . .
H91 H 0.438(2) 0.5935(19) 0.0306(15) 0.0501 1.0000 Uiso . . . . . .
H101 H 0.674(2) 0.839(2) 0.1632(15) 0.0553 1.0000 Uiso . . . . . .
H121 H 0.382(2) 0.775(2) 0.4098(16) 0.0574 1.0000 Uiso . . . . . .
H131 H 0.146(2) 0.5281(19) 0.2782(15) 0.0496 1.0000 Uiso . . . . . .
H142 H 0.662(3) 1.067(3) 0.402(2) 0.0881 1.0000 Uiso . . . . . .
H141 H 0.809(3) 1.037(3) 0.351(2) 0.0888 1.0000 Uiso . . . . . .
H143 H 0.755(3) 0.965(3) 0.468(2) 0.0879 1.0000 Uiso . . . . . .
H161 H -0.273(2) -0.2224(18) -0.3574(14) 0.0477 1.0000 Uiso . . . . . .
H171 H -0.557(2) -0.4593(19) -0.4165(15) 0.0469 1.0000 Uiso . . . . . .
H201 H -1.016(3) -0.717(2) -0.4297(18) 0.0718 1.0000 Uiso . . . . . .
H203 H -0.897(3) -0.597(2) -0.5060(18) 0.0693 1.0000 Uiso . . . . . .
H202 H -0.805(3) -0.696(2) -0.4146(17) 0.0704 1.0000 Uiso . . . . . .
H211 H -0.709(2) -0.2673(19) -0.1571(15) 0.0504 1.0000 Uiso . . . . . .
H221 H -0.426(2) -0.0337(19) -0.0902(15) 0.0461 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0453(5) 0.0432(5) 0.0392(5) 0.0004(4) 0.0215(4) 0.0042(4)
C2 0.0365(6) 0.0360(6) 0.0317(6) 0.0060(5) 0.0128(5) 0.0150(5)
N3 0.0339(5) 0.0338(5) 0.0309(5) 0.0044(4) 0.0109(4) 0.0128(4)
N4 0.0373(6) 0.0463(6) 0.0326(5) 0.0046(4) 0.0135(4) 0.0133(5)
N5 0.0358(5) 0.0482(6) 0.0338(5) 0.0010(5) 0.0105(4) 0.0141(5)
C6 0.0318(6) 0.0389(6) 0.0334(6) 0.0037(5) 0.0076(5) 0.0184(5)
C7 0.0375(6) 0.0336(6) 0.0326(6) 0.0048(5) 0.0112(5) 0.0128(5)
C8 0.0350(6) 0.0376(6) 0.0317(6) 0.0017(5) 0.0042(5) 0.0199(5)
C9 0.0404(7) 0.0401(7) 0.0373(6) -0.0025(5) 0.0106(5) 0.0164(6)
C10 0.0402(7) 0.0413(7) 0.0482(7) -0.0015(6) 0.0103(6) 0.0151(6)
C11 0.0461(7) 0.0399(7) 0.0404(7) -0.0030(5) -0.0008(6) 0.0236(6)
C12 0.0549(8) 0.0513(8) 0.0326(6) -0.0028(6) 0.0059(6) 0.0303(7)
C13 0.0436(7) 0.0479(7) 0.0355(6) 0.0030(5) 0.0108(5) 0.0234(6)
C14 0.0604(10) 0.0432(8) 0.0510(9) -0.0095(7) -0.0033(7) 0.0204(7)
C15 0.0332(6) 0.0322(6) 0.0317(6) 0.0070(5) 0.0109(5) 0.0142(5)
C16 0.0378(7) 0.0403(7) 0.0399(6) 0.0047(5) 0.0196(5) 0.0151(5)
C17 0.0417(7) 0.0319(6) 0.0392(6) 0.0008(5) 0.0164(5) 0.0134(5)
C18 0.0350(6) 0.0311(6) 0.0387(6) 0.0097(5) 0.0140(5) 0.0117(5)
O19 0.0403(5) 0.0374(5) 0.0503(5) 0.0007(4) 0.0201(4) 0.0037(4)
C20 0.0459(8) 0.0350(7) 0.0476(8) 0.0019(6) 0.0130(6) 0.0060(6)
C21 0.0380(7) 0.0444(7) 0.0436(7) 0.0040(6) 0.0218(6) 0.0135(6)
C22 0.0388(7) 0.0375(6) 0.0370(6) 0.0014(5) 0.0148(5) 0.0147(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4765(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2075(15) yes
C2 . N3 . 1.4340(15) yes
C2 . C15 . 1.4768(17) yes
N3 . N4 . 1.3658(14) yes
N3 . C7 . 1.3579(16) yes
N4 . N5 . 1.2960(15) yes
N5 . C6 . 1.3769(17) yes
C6 . C7 . 1.3598(17) yes
C6 . C8 . 1.4678(17) yes
C7 . H71 . 0.906(16) no
C8 . C9 . 1.3934(19) yes
C8 . C13 . 1.3945(18) yes
C9 . C10 . 1.3873(19) yes
C9 . H91 . 0.970(16) no
C10 . C11 . 1.389(2) yes
C10 . H101 . 0.962(17) no
C11 . C12 . 1.387(2) yes
C11 . C14 . 1.5045(19) yes
C12 . C13 . 1.383(2) yes
C12 . H121 . 0.958(17) no
C13 . H131 . 0.955(16) no
C14 . H142 . 0.97(2) no
C14 . H141 . 0.98(2) no
C14 . H143 . 0.93(2) no
C15 . C16 . 1.3882(17) yes
C15 . C22 . 1.4012(17) yes
C16 . C17 . 1.3815(18) yes
C16 . H161 . 0.950(16) no
C17 . C18 . 1.3855(18) yes
C17 . H171 . 0.952(16) no
C18 . O19 . 1.3626(15) yes
C18 . C21 . 1.3871(18) yes
O19 . C20 . 1.4255(17) yes
C20 . H201 . 0.97(2) no
C20 . H203 . 0.971(19) no
C20 . H202 . 1.007(19) no
C21 . C22 . 1.3745(18) yes
C21 . H211 . 0.917(17) no
C22 . H221 . 0.989(15) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 116.47(11) yes
O1 . C2 . C15 . 123.59(11) yes
N3 . C2 . C15 . 119.94(10) yes
C2 . N3 . N4 . 124.52(10) yes
C2 . N3 . C7 . 125.12(10) yes
N4 . N3 . C7 . 110.24(10) yes
N3 . N4 . N5 . 106.84(10) yes
N4 . N5 . C6 . 109.87(10) yes
N5 . C6 . C7 . 107.80(11) yes
N5 . C6 . C8 . 121.27(11) yes
C7 . C6 . C8 . 130.90(12) yes
C6 . C7 . N3 . 105.25(11) yes
C6 . C7 . H71 . 133.0(9) no
N3 . C7 . H71 . 121.7(9) no
C6 . C8 . C9 . 121.30(11) yes
C6 . C8 . C13 . 120.53(12) yes
C9 . C8 . C13 . 118.15(12) yes
C8 . C9 . C10 . 120.97(12) yes
C8 . C9 . H91 . 119.9(9) no
C10 . C9 . H91 . 119.1(9) no
C9 . C10 . C11 . 120.89(14) yes
C9 . C10 . H101 . 119.6(10) no
C11 . C10 . H101 . 119.4(10) no
C10 . C11 . C12 . 117.84(12) yes
C10 . C11 . C14 . 121.01(15) yes
C12 . C11 . C14 . 121.15(14) yes
C11 . C12 . C13 . 121.82(13) yes
C11 . C12 . H121 . 119.4(10) no
C13 . C12 . H121 . 118.8(10) no
C8 . C13 . C12 . 120.28(14) yes
C8 . C13 . H131 . 118.3(9) no
C12 . C13 . H131 . 121.4(9) no
C11 . C14 . H142 . 111.4(13) no
C11 . C14 . H141 . 110.4(13) no
H142 . C14 . H141 . 106.6(18) no
C11 . C14 . H143 . 110.6(13) no
H142 . C14 . H143 . 105.7(18) no
H141 . C14 . H143 . 111.9(18) no
C2 . C15 . C16 . 115.89(11) yes
C2 . C15 . C22 . 125.60(11) yes
C16 . C15 . C22 . 118.34(11) yes
C15 . C16 . C17 . 121.71(11) yes
C15 . C16 . H161 . 118.9(9) no
C17 . C16 . H161 . 119.4(9) no
C16 . C17 . C18 . 119.16(11) yes
C16 . C17 . H171 . 120.3(9) no
C18 . C17 . H171 . 120.5(9) no
C17 . C18 . O19 . 124.29(11) yes
C17 . C18 . C21 . 119.93(11) yes
O19 . C18 . C21 . 115.77(11) yes
C18 . O19 . C20 . 117.83(11) yes
O19 . C20 . H201 . 102.1(11) no
O19 . C20 . H203 . 112.1(11) no
H201 . C20 . H203 . 111.6(15) no
O19 . C20 . H202 . 110.9(10) no
H201 . C20 . H202 . 109.8(15) no
H203 . C20 . H202 . 110.2(15) no
C18 . C21 . C22 . 120.69(12) yes
C18 . C21 . H211 . 120.1(10) no
C22 . C21 . H211 . 119.1(10) no
C15 . C22 . C21 . 120.16(12) yes
C15 . C22 . H221 . 120.3(9) no
C21 . C22 . H221 . 119.5(9) no


_iucr_refine_instructions_details 
;
#
# Punched on 21/02/23 at 15:47:54
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL C    (   22 ) 
CONT H    (   71 ,X'S)  UNTIL H    (  221 ) 
END                                                                             
#
# Punched on 21/02/23 at 15:47:54
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

