# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1455633'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2015-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            5a
_chemical_name_systematic        
3-(4-phenyl-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_chemical_formula_moiety         'C17 H11 N3 O2'
_chemical_formula_sum            'C17 H11 N3 O2'
_chemical_formula_weight         289.29
_chemical_melting_point          477

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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9013(6)
_cell_length_b                   7.3232(3)
_cell_length_c                   15.7261(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.248(5)
_cell_angle_gamma                90.00
_cell_volume                     1365.14(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5011
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3250
_cell_measurement_theta_min      3.0190
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.3754
_exptl_crystal_size_mid          0.3031
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14623
_diffrn_reflns_theta_full        74.50
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         3.78
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -124.00  -99.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega -118.00    3.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -19.0000    0.0000 121

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   25.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   37.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega   64.00  107.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   84.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  107.00  137.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   84.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00  109.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   90.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega  129.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  100.0000   12.0000 49

#__ type_ start__ end____ width___ exp.time_
 11 omega  102.00  135.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   46.00   92.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   80.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  107.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  125.00  152.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00   88.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 17 omega   49.00   86.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 18 omega  153.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   54.00   80.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega -123.00    5.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -19.0000  150.0000 128

#__ type_ start__ end____ width___ exp.time_
 21 omega -120.00   -8.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
 22 omega -115.00  -12.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 23 omega   57.00  131.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
 24 omega   57.00  131.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 25 omega   54.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   15.0000  -30.0000 124

#__ type_ start__ end____ width___ exp.time_
 26 omega   81.00  162.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 81

#__ type_ start__ end____ width___ exp.time_
 27 omega   84.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
 28 omega   85.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
 29 omega   37.00  116.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 30 omega   85.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
 31 omega   84.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   60.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0046270000
_diffrn_orient_matrix_UB_12      -0.1323761000
_diffrn_orient_matrix_UB_13      -0.0775758000
_diffrn_orient_matrix_UB_21      0.1119954000
_diffrn_orient_matrix_UB_22      -0.0868258000
_diffrn_orient_matrix_UB_23      0.0651243000
_diffrn_orient_matrix_UB_31      -0.0657152000
_diffrn_orient_matrix_UB_32      -0.1385722000
_diffrn_orient_matrix_UB_33      0.0332935000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2325
_reflns_number_total             2786
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.2207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C2 C 0.53723(13) 0.8258(2) 0.15150(11) 0.0518(4) Uani 1 d . . .
C3 C 0.44147(12) 0.8481(2) 0.17853(9) 0.0436(3) Uani 1 d . . .
C4 C 0.41585(12) 0.7222(2) 0.22881(10) 0.0471(3) Uani 1 d . . .
H4 H 0.3546 0.7405 0.2449 0.056 Uiso 1 calc . . R
C5 C 0.46087(14) 0.4212(2) 0.31041(12) 0.0576(4) Uani 1 d . . .
H5 H 0.4000 0.4315 0.3277 0.069 Uiso 1 calc . . R
C6 C 0.52974(16) 0.2703(3) 0.33637(13) 0.0645(4) Uani 1 d . . .
H6 H 0.5154 0.1792 0.3715 0.077 Uiso 1 calc . . R
C7 C 0.61995(15) 0.2527(3) 0.31073(12) 0.0637(5) Uani 1 d . . .
H7 H 0.6659 0.1501 0.3289 0.076 Uiso 1 calc . . R
C8 C 0.64252(14) 0.3853(3) 0.25867(12) 0.0592(4) Uani 1 d . . .
H8 H 0.7033 0.3736 0.2413 0.071 Uiso 1 calc . . R
C9 C 0.38070(13) 1.1463(2) 0.09206(10) 0.0490(3) Uani 1 d . . .
H9 H 0.4297 1.1569 0.0620 0.059 Uiso 1 calc . . R
C10 C 0.29775(13) 1.2649(2) 0.08857(10) 0.0480(3) Uani 1 d . . .
C11 C 0.26584(13) 1.4428(2) 0.04211(10) 0.0498(4) Uani 1 d . . .
C12 C 0.17441(16) 1.5383(2) 0.04400(13) 0.0635(4) Uani 1 d . . .
H12 H 0.1310 1.4878 0.0732 0.076 Uiso 1 calc . . R
C13 C 0.14680(18) 1.7089(3) 0.00274(14) 0.0743(5) Uani 1 d . . .
H13 H 0.0848 1.7715 0.0042 0.089 Uiso 1 calc . . R
C14 C 0.21019(19) 1.7854(3) -0.03997(12) 0.0720(5) Uani 1 d . . .
H14 H 0.1916 1.9002 -0.0671 0.086 Uiso 1 calc . . R
C15 C 0.30170(19) 1.6923(3) -0.04274(12) 0.0689(5) Uani 1 d . . .
H15 H 0.3449 1.7443 -0.0717 0.083 Uiso 1 calc . . R
C16 C 0.32937(16) 1.5210(2) -0.00228(11) 0.0588(4) Uani 1 d . . .
H16 H 0.3907 1.4581 -0.0048 0.071 Uiso 1 calc . . R
C17 C 0.48233(12) 0.5590(2) 0.25807(10) 0.0470(3) Uani 1 d . . .
C18 C 0.57295(12) 0.5366(2) 0.23261(10) 0.0485(3) Uani 1 d . . .
N1 N 0.37659(10) 1.01007(17) 0.14841(8) 0.0459(3) Uani 1 d . . .
N2 N 0.29346(13) 1.0425(2) 0.17878(11) 0.0616(4) Uani 1 d . . .
N3 N 0.24632(13) 1.1962(2) 0.14218(11) 0.0626(4) Uani 1 d . . .
O1 O 0.59823(9) 0.66801(17) 0.18094(8) 0.0569(3) Uani 1 d . . .
O2 O 0.56772(11) 0.9291(2) 0.10702(11) 0.0761(4) Uani 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
C2 C3 1.4657(19) . ?
C2 O1 1.371(2) . ?
C2 O2 1.197(2) . ?
C3 C4 1.338(2) . ?
C3 N1 1.4207(19) . ?
C4 C17 1.437(2) . ?
C5 C6 1.375(2) . ?
C5 C17 1.397(2) . ?
C6 C7 1.380(3) . ?
C7 C8 1.373(3) . ?
C8 C18 1.382(2) . ?
C9 C10 1.363(2) . ?
C9 N1 1.3491(19) . ?
C10 C11 1.471(2) . ?
C10 N3 1.359(2) . ?
C11 C12 1.382(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.367(3) . ?
C14 C15 1.379(3) . ?
C15 C16 1.388(3) . ?
C17 C18 1.387(2) . ?
C18 O1 1.3789(19) . ?
N1 N2 1.3562(17) . ?
N2 N3 1.300(2) . ?

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
O1 C2 C3 115.67(13) . . ?
O2 C2 C3 127.42(16) . . ?
O2 C2 O1 116.90(14) . . ?
C4 C3 C2 121.83(14) . . ?
C4 C3 N1 121.44(12) . . ?
N1 C3 C2 116.72(13) . . ?
C3 C4 C17 120.46(13) . . ?
C6 C5 C17 120.02(16) . . ?
C5 C6 C7 120.57(17) . . ?
C8 C7 C6 120.68(16) . . ?
C7 C8 C18 118.55(15) . . ?
N1 C9 C10 105.32(13) . . ?
C9 C10 C11 130.26(14) . . ?
N3 C10 C9 107.85(14) . . ?
N3 C10 C11 121.81(14) . . ?
C12 C11 C10 120.77(14) . . ?
C12 C11 C16 118.63(16) . . ?
C16 C11 C10 120.57(15) . . ?
C11 C12 C13 120.62(18) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 119.90(18) . . ?
C14 C15 C16 120.07(18) . . ?
C15 C16 C11 120.38(18) . . ?
C5 C17 C4 123.88(14) . . ?
C18 C17 C4 118.07(14) . . ?
C18 C17 C5 118.05(15) . . ?
C8 C18 C17 122.13(15) . . ?
O1 C18 C8 117.20(14) . . ?
O1 C18 C17 120.67(14) . . ?
C9 N1 C3 131.72(12) . . ?
C9 N1 N2 110.08(12) . . ?
N2 N1 C3 118.20(12) . . ?
N3 N2 N1 107.00(12) . . ?
N2 N3 C10 109.75(13) . . ?
C2 O1 C18 123.30(11) . . ?

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
C2 C3 C4 C17 -0.1(2) . . . . ?
C2 C3 N1 C9 5.8(2) . . . . ?
C2 C3 N1 N2 -174.45(13) . . . . ?
C3 C2 O1 C18 0.1(2) . . . . ?
C3 C4 C17 C5 -179.83(15) . . . . ?
C3 C4 C17 C18 0.0(2) . . . . ?
C3 N1 N2 N3 -179.77(14) . . . . ?
C4 C3 N1 C9 -173.92(15) . . . . ?
C4 C3 N1 N2 5.8(2) . . . . ?
C4 C17 C18 C8 179.08(14) . . . . ?
C4 C17 C18 O1 0.2(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C17 C18 C8 -1.1(2) . . . . ?
C5 C17 C18 O1 179.99(14) . . . . ?
C6 C5 C17 C4 -179.23(15) . . . . ?
C6 C5 C17 C18 1.0(2) . . . . ?
C6 C7 C8 C18 0.0(3) . . . . ?
C7 C8 C18 C17 0.6(2) . . . . ?
C7 C8 C18 O1 179.55(15) . . . . ?
C8 C18 O1 C2 -179.15(14) . . . . ?
C9 C10 C11 C12 177.02(17) . . . . ?
C9 C10 C11 C16 -5.0(2) . . . . ?
C9 C10 N3 N2 0.4(2) . . . . ?
C9 N1 N2 N3 -0.01(19) . . . . ?
C10 C9 N1 C3 179.94(14) . . . . ?
C10 C9 N1 N2 0.22(17) . . . . ?
C10 C11 C12 C13 177.82(16) . . . . ?
C10 C11 C16 C15 -177.32(15) . . . . ?
C11 C10 N3 N2 -176.84(14) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C11 C16 C15 0.7(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
C17 C5 C6 C7 -0.4(3) . . . . ?
C17 C18 O1 C2 -0.2(2) . . . . ?
N1 C3 C4 C17 179.66(13) . . . . ?
N1 C9 C10 C11 176.53(14) . . . . ?
N1 C9 C10 N3 -0.34(18) . . . . ?
N1 N2 N3 C10 -0.2(2) . . . . ?
N3 C10 C11 C12 -6.5(2) . . . . ?
N3 C10 C11 C16 171.52(15) . . . . ?
O1 C2 C3 C4 0.1(2) . . . . ?
O1 C2 C3 N1 -179.68(12) . . . . ?
O2 C2 C3 C4 -179.88(17) . . . . ?
O2 C2 C3 N1 0.4(2) . . . . ?
O2 C2 O1 C18 -179.97(15) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7 -1 -8 0.1498 7.0017 -0.9984 -7.9993 0.7203 0.3499 -0.5881
0 -5 1 0.1583 -0.0029 -5.0017 0.9986 0.5847 0.4990 0.7265
-8 -1 7 0.1207 -8.0027 -1.0018 6.9992 -0.3733 -0.3535 0.8977
-2 5 1 0.1604 -1.9977 5.0013 1.0012 -0.7305 -0.5928 -0.5284
8 -1 -7 0.1381 8.0016 -0.9988 -6.9996 0.6382 0.5270 -0.6205
-8 -1 6 0.1158 -8.0025 -1.0015 5.9994 -0.2958 -0.4186 0.8644
6 -2 4 0.0964 5.9988 -2.0024 3.9979 -0.0728 1.1061 0.0164
-4 1 -6 0.0964 -3.9987 1.0026 -5.9979 0.3511 -0.9255 -0.0758
5 0 5 0.0775 4.9995 -0.0021 4.9983 -0.4106 0.8856 -0.1618
3 0 7 0.1041 2.9990 -0.0025 6.9981 -0.5564 0.7918 0.0363
-2 -2 9 0.1364 -2.0030 -2.0033 8.9978 -0.4236 0.5356 0.7088
-6 -2 -2 0.1038 -6.0013 -1.9994 -1.9993 0.4475 -0.6287 0.6049
6 3 -6 0.1273 6.0033 3.0022 -5.9987 0.0402 0.0210 -1.0103
-4 0 10 0.1476 -4.0023 -0.0028 9.9982 -0.7567 0.2031 0.5963
-6 0 9 0.1393 -6.0023 -0.0023 8.9987 -0.6700 -0.0860 0.6944
2 4 1 0.1555 2.0021 4.0006 1.0005 -0.6165 -0.0580 -0.6526
-3 4 -1 0.1501 -2.9980 4.0017 -0.9985 -0.4384 -0.7482 -0.3908
-8 -1 4 0.1105 -8.0021 -1.0008 3.9998 -0.1408 -0.5488 0.7977
4 -4 3 0.1318 3.9977 -4.0025 2.9979 0.2788 0.9905 0.3917
8 -1 -2 0.1191 8.0006 -1.0004 -2.0007 0.2506 0.8526 -0.4537
-3 4 -3 0.1398 -2.9976 4.0024 -2.9980 -0.2834 -0.8785 -0.4574
-5 2 -4 0.1080 -4.9987 2.0023 -3.9980 0.0682 -0.9941 -0.0821
-8 -1 2 0.0983 -8.0017 -1.0002 2.0003 0.0143 -0.6790 0.7310
3 -3 6 0.1261 2.9976 -3.0031 5.9976 -0.0816 0.9870 0.4188
-5 0 -5 0.0824 -4.9995 0.0021 -4.9983 0.4106 -0.8856 0.1618
-6 -1 -3 0.0862 -6.0006 -0.9988 -2.9988 0.3926 -0.7806 0.4329
-1 -1 -8 0.1311 -0.9991 -0.9976 -7.9983 0.7572 -0.5462 -0.0624
4 3 4 0.1359 4.0012 2.9992 3.9993 -0.7258 0.4482 -0.5454
-3 -4 -2 0.1364 -3.0020 -4.0002 -2.0001 0.6986 -0.1191 0.6850

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

data_5b
_database_code_depnum_ccdc_archive 'CCDC 1455634'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2015-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_common            5b
_chemical_formula_moiety         'C18 H13 N3 O3'
_chemical_formula_sum            'C18 H13 N3 O3'
_chemical_formula_weight         319.31
_chemical_melting_point          487

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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.0621(5)
_cell_length_b                   6.4884(3)
_cell_length_c                   17.3730(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.527(4)
_cell_angle_gamma                90.00
_cell_volume                     1474.55(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9591
_cell_measurement_theta_min      3.3758
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4504
_exptl_crystal_size_mid          0.2365
_exptl_crystal_size_min          0.1107
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13711
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.48
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -108.00  -81.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -99.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   28.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504   38.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega -108.00  -81.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -99.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega -120.00  -23.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   83.00  159.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   45.0000 -120.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00   85.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -45.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00   90.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -45.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00   99.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -45.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega   45.00   70.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   26.00  107.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -94.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00   91.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -30.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   73.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -61.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
 13 omega -120.00   -8.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 14 omega -120.00   -8.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 15 omega   18.00   99.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -       41.5504 -125.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
 16 omega   23.00  109.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -94.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
 17 omega   76.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   30.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
 18 omega   73.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   77.0000   60.0000 105

#__ type_ start__ end____ width___ exp.time_
 19 omega   73.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   77.0000  -90.0000 105

#__ type_ start__ end____ width___ exp.time_
 20 omega   77.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   61.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 21 omega   46.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   15.0000   30.0000 132

#__ type_ start__ end____ width___ exp.time_
 22 omega -116.00  -12.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -57.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 23 omega -120.00  -84.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504 -159.0000  108.0000 36

#__ type_ start__ end____ width___ exp.time_
 24 omega   72.00  119.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -       41.5504  159.0000  140.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1088854000
_diffrn_orient_matrix_UB_12      -0.0716900000
_diffrn_orient_matrix_UB_13      -0.0529401000
_diffrn_orient_matrix_UB_21      0.0265112000
_diffrn_orient_matrix_UB_22      0.0142021000
_diffrn_orient_matrix_UB_23      -0.0783831000
_diffrn_orient_matrix_UB_31      0.0362592000
_diffrn_orient_matrix_UB_32      -0.2258284000
_diffrn_orient_matrix_UB_33      0.0119079000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2144
_reflns_number_total             2638
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.80470(8) 0.09648(18) 0.16123(6) 0.0533(3) Uani 1 d . . .
O2 O 0.69945(10) 0.3588(2) 0.13277(9) 0.0781(4) Uani 1 d . . .
O3 O 1.14977(8) -0.29740(18) 0.15840(7) 0.0603(3) Uani 1 d . . .
N1 N 0.78831(9) 0.54417(19) 0.02718(7) 0.0451(3) Uani 1 d . . .
N2 N 0.84601(10) 0.6456(2) -0.00823(8) 0.0550(3) Uani 1 d . . .
N3 N 0.79256(10) 0.8025(2) -0.04766(9) 0.0556(3) Uani 1 d . . .
C2 C 0.77142(12) 0.2797(3) 0.12273(10) 0.0519(4) Uani 1 d . . .
C3 C 0.82649(10) 0.3602(2) 0.07217(8) 0.0448(3) Uani 1 d . . .
C4 C 0.91055(10) 0.2658(2) 0.06968(9) 0.0460(3) Uani 1 d . . .
H4 H 0.9452 0.3218 0.0381 0.055 Uiso 1 calc . . R
C5 C 1.03457(11) -0.0249(2) 0.11712(9) 0.0472(3) Uani 1 d . . .
H5 H 1.0734 0.0277 0.0884 0.057 Uiso 1 calc . . R
C6 C 1.06375(10) -0.2061(2) 0.16139(9) 0.0467(3) Uani 1 d . . .
C7 C 1.00587(11) -0.2854(2) 0.20537(9) 0.0487(4) Uani 1 d . . .
H7 H 1.0259 -0.4068 0.2354 0.058 Uiso 1 calc . . R
C8 C 0.91929(11) -0.1835(2) 0.20409(9) 0.0500(4) Uani 1 d . . .
H8 H 0.8805 -0.2358 0.2330 0.060 Uiso 1 calc . . R
C9 C 0.69717(11) 0.6408(3) 0.00918(9) 0.0510(4) Uani 1 d . . .
H9 H 0.6441 0.6032 0.0261 0.061 Uiso 1 calc . . R
C10 C 0.69996(10) 0.8045(2) -0.03892(8) 0.0453(3) Uani 1 d . . .
C11 C 0.62215(11) 0.9626(2) -0.07750(8) 0.0459(3) Uani 1 d . . .
C12 C 0.64775(12) 1.1472(2) -0.10561(9) 0.0512(4) Uani 1 d . . .
H12 H 0.7150 1.1713 -0.1003 0.061 Uiso 1 calc . . R
C13 C 0.57384(13) 1.2954(3) -0.14140(10) 0.0587(4) Uani 1 d . . .
H13 H 0.5917 1.4182 -0.1602 0.070 Uiso 1 calc . . R
C14 C 0.47349(13) 1.2615(3) -0.14935(10) 0.0611(4) Uani 1 d . . .
H14 H 0.4242 1.3624 -0.1722 0.073 Uiso 1 calc . . R
C15 C 0.44726(13) 1.0775(3) -0.12325(11) 0.0626(5) Uani 1 d . . .
H15 H 0.3797 1.0531 -0.1295 0.075 Uiso 1 calc . . R
C16 C 0.52055(11) 0.9285(3) -0.08776(10) 0.0553(4) Uani 1 d . . .
H16 H 0.5018 0.8044 -0.0706 0.066 Uiso 1 calc . . R
C17 C 1.18865(13) -0.4737(3) 0.20838(12) 0.0646(5) Uani 1 d . . .
H17A H 1.1391 -0.5826 0.1915 0.097 Uiso 1 calc . . GR
H17B H 1.2026 -0.4398 0.2653 0.097 Uiso 1 calc . . GR
H17C H 1.2506 -0.5178 0.2022 0.097 Uiso 1 calc . . GR
C18 C 0.94703(10) 0.0794(2) 0.11539(8) 0.0435(3) Uani 1 d . . .
C19 C 0.89094(10) -0.0036(2) 0.15963(8) 0.0441(3) Uani 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 C2 1.3603(19) . ?
O1 C19 1.3849(17) . ?
O2 C2 1.2031(19) . ?
O3 C6 1.3650(18) . ?
O3 C17 1.419(2) . ?
N1 N2 1.3551(17) . ?
N1 C3 1.4201(19) . ?
N1 C9 1.3562(19) . ?
N2 N3 1.3011(19) . ?
N3 C10 1.3654(19) . ?
C2 C3 1.464(2) . ?
C3 C4 1.346(2) . ?
C4 C18 1.434(2) . ?
C5 C6 1.382(2) . ?
C5 C18 1.395(2) . ?
C6 C7 1.402(2) . ?
C7 C8 1.378(2) . ?
C8 C19 1.375(2) . ?
C9 C10 1.361(2) . ?
C10 C11 1.470(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.385(2) . ?
C13 C14 1.384(2) . ?
C14 C15 1.374(3) . ?
C15 C16 1.382(2) . ?
C18 C19 1.396(2) . ?

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
C2 O1 C19 123.09(12) . . ?
C6 O3 C17 118.32(12) . . ?
N2 N1 C3 119.33(12) . . ?
N2 N1 C9 110.09(12) . . ?
C9 N1 C3 130.53(12) . . ?
N3 N2 N1 107.02(12) . . ?
N2 N3 C10 109.80(13) . . ?
O1 C2 C3 116.38(13) . . ?
O2 C2 O1 117.23(14) . . ?
O2 C2 C3 126.39(15) . . ?
N1 C3 C2 116.98(13) . . ?
C4 C3 N1 121.59(13) . . ?
C4 C3 C2 121.42(14) . . ?
C3 C4 C18 120.37(13) . . ?
C6 C5 C18 120.27(13) . . ?
O3 C6 C5 115.74(13) . . ?
O3 C6 C7 124.14(14) . . ?
C5 C6 C7 120.13(14) . . ?
C8 C7 C6 120.07(14) . . ?
C19 C8 C7 119.23(14) . . ?
N1 C9 C10 105.34(13) . . ?
N3 C10 C11 122.43(13) . . ?
C9 C10 N3 107.74(13) . . ?
C9 C10 C11 129.83(14) . . ?
C12 C11 C10 121.08(14) . . ?
C12 C11 C16 118.59(14) . . ?
C16 C11 C10 120.32(14) . . ?
C13 C12 C11 120.51(15) . . ?
C14 C13 C12 120.28(16) . . ?
C15 C14 C13 119.49(16) . . ?
C14 C15 C16 120.54(16) . . ?
C15 C16 C11 120.56(16) . . ?
C5 C18 C4 123.67(13) . . ?
C5 C18 C19 118.24(13) . . ?
C19 C18 C4 118.09(13) . . ?
O1 C19 C18 120.39(13) . . ?
C8 C19 O1 117.54(13) . . ?
C8 C19 C18 122.07(13) . . ?

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 C2 C3 N1 175.87(12) . . . . ?
O1 C2 C3 C4 -5.3(2) . . . . ?
O2 C2 C3 N1 -3.4(2) . . . . ?
O2 C2 C3 C4 175.45(17) . . . . ?
O3 C6 C7 C8 -179.29(13) . . . . ?
N1 N2 N3 C10 -0.36(17) . . . . ?
N1 C3 C4 C18 -179.64(12) . . . . ?
N1 C9 C10 N3 -0.59(16) . . . . ?
N1 C9 C10 C11 179.28(14) . . . . ?
N2 N1 C3 C2 168.04(13) . . . . ?
N2 N1 C3 C4 -10.8(2) . . . . ?
N2 N1 C9 C10 0.38(17) . . . . ?
N2 N3 C10 C9 0.61(17) . . . . ?
N2 N3 C10 C11 -179.27(13) . . . . ?
N3 C10 C11 C12 -17.7(2) . . . . ?
N3 C10 C11 C16 161.31(14) . . . . ?
C2 O1 C19 C8 177.13(13) . . . . ?
C2 O1 C19 C18 -1.7(2) . . . . ?
C2 C3 C4 C18 1.6(2) . . . . ?
C3 N1 N2 N3 177.72(12) . . . . ?
C3 N1 C9 C10 -177.02(13) . . . . ?
C3 C4 C18 C5 -178.73(14) . . . . ?
C3 C4 C18 C19 2.2(2) . . . . ?
C4 C18 C19 O1 -2.3(2) . . . . ?
C4 C18 C19 C8 178.94(13) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C5 C18 C19 O1 178.64(12) . . . . ?
C5 C18 C19 C8 -0.2(2) . . . . ?
C6 C5 C18 C4 -178.72(13) . . . . ?
C6 C5 C18 C19 0.3(2) . . . . ?
C6 C7 C8 C19 -0.3(2) . . . . ?
C7 C8 C19 O1 -178.69(13) . . . . ?
C7 C8 C19 C18 0.1(2) . . . . ?
C9 N1 N2 N3 -0.02(17) . . . . ?
C9 N1 C3 C2 -14.8(2) . . . . ?
C9 N1 C3 C4 166.39(15) . . . . ?
C9 C10 C11 C12 162.49(15) . . . . ?
C9 C10 C11 C16 -18.5(2) . . . . ?
C10 C11 C12 C13 -179.62(14) . . . . ?
C10 C11 C16 C15 179.35(15) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C11 C16 C15 -1.7(2) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C16 C11 C12 C13 1.4(2) . . . . ?
C17 O3 C6 C5 174.51(14) . . . . ?
C17 O3 C6 C7 -5.7(2) . . . . ?
C18 C5 C6 O3 179.29(13) . . . . ?
C18 C5 C6 C7 -0.5(2) . . . . ?
C19 O1 C2 O2 -175.32(15) . . . . ?
C19 O1 C2 C3 5.3(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6 0 5 0.0755 6.0000 0.0000 4.9999 -0.9180 -0.2328 0.2771
-3 4 0 0.1936 -3.0000 4.0000 0.0001 0.0399 -0.0227 -1.0121
0 0 10 0.0554 -0.0000 -0.0000 10.0000 -0.5294 -0.7838 0.1191
0 -1 -10 0.0519 0.0000 -1.0000 -10.0000 0.6011 0.7696 0.1067
2 0 -11 0.0519 2.0000 0.0000 -11.0000 0.3646 0.9152 -0.0585
-2 0 11 0.0589 -2.0000 -0.0000 11.0000 -0.3646 -0.9152 0.0585
5 0 -11 0.0726 5.0000 0.0000 -11.0000 0.0379 0.9948 0.0503
3 -4 0 0.2351 3.0000 -4.0000 -0.0001 -0.0399 0.0227 1.0121
-7 0 10 0.0796 -7.0000 -0.0000 10.0000 0.2328 -0.9694 -0.1347
9 0 -7 0.0855 9.0000 0.0000 -7.0001 -0.6094 0.7873 0.2430
9 0 -4 0.0897 9.0000 0.0000 -4.0001 -0.7682 0.5521 0.2787
-5 -1 -6 0.0727 -5.0000 -1.0000 -6.0000 0.9338 0.3235 -0.0269
-1 4 2 0.1946 -1.0000 4.0000 2.0001 -0.2838 -0.1265 -0.9158
3 0 8 0.0637 3.0000 -0.0000 8.0000 -0.7502 -0.5475 0.2040
-3 -1 -8 0.0622 -3.0000 -1.0000 -8.0000 0.8219 0.5333 0.0218
1 0 10 0.0523 1.0000 -0.0000 10.0000 -0.6383 -0.7573 0.1553
0 -1 -10 0.0519 0.0000 -1.0000 -10.0000 0.6011 0.7696 0.1067
-5 0 11 0.0691 -5.0000 -0.0000 11.0000 -0.0379 -0.9948 -0.0503
0 -4 5 0.2149 0.0000 -4.0000 4.9999 0.0221 -0.4487 0.9629
-8 -1 8 0.0899 -8.0000 -1.0000 8.0000 0.5193 -0.8534 0.0310

_olex2_submission_special_instructions 'No special instructions were received'

_chemical_name_systematic        
'6-methoxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one '
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
####################################################################### 
# 
# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 1455635'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2015-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            5c
_chemical_name_systematic        
7-methoxy-3-(4-phenyl-1,2,3-triazol-1-yl)-chromen-2-one
_chemical_formula_moiety         'C18 H13 N3 O3'
_chemical_formula_sum            'C18 H13 N3 O3'
_chemical_formula_weight         319.31
_chemical_melting_point          512

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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.17677(17)
_cell_length_b                   9.5698(3)
_cell_length_c                   30.6216(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.127(3)
_cell_angle_gamma                90.00
_cell_volume                     1515.96(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8136
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1060
_cell_measurement_theta_min      4.6160
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.1865
_exptl_crystal_size_mid          0.0547
_exptl_crystal_size_min          0.0547
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            53243
_diffrn_reflns_theta_full        77.68
_diffrn_reflns_theta_max         77.68
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000  -90.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega -114.00  -89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00  -41.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega  -52.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega  -37.00   -9.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega  -71.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000   79.0000 63

#__ type_ start__ end____ width___ exp.time_
  7 omega   80.00  128.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega  -60.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega -135.00  -94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -78.0000  -21.4535 41

#__ type_ start__ end____ width___ exp.time_
 11 omega -140.00  -93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -99.3781 47

#__ type_ start__ end____ width___ exp.time_
 12 omega  -54.00   13.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
 13 omega  -77.00  -30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 14 omega  -93.00  -66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega  -64.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega -138.00 -102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 17 omega  -58.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 18 omega -136.00 -108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 19 omega  -69.00  -30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -99.3781 39

#__ type_ start__ end____ width___ exp.time_
 20 omega -135.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   79.0000 107

#__ type_ start__ end____ width___ exp.time_
 21 omega  -63.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -78.0000  -21.4535 35

#__ type_ start__ end____ width___ exp.time_
 22 omega -140.00  -95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 23 omega  -62.00  -30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   50.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   52.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 27 omega   86.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
 28 omega   84.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 29 omega   53.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -61.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 30 omega  113.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
 31 omega   86.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
 32 omega   38.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
 33 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   85.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
 35 omega  131.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 36 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 40 omega   49.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 41 omega   42.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
 42 omega   92.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 43 omega   85.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 44 omega   85.00  160.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 45 omega   85.00  154.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
 46 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 47 omega   87.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 48 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega  126.00  153.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 50 omega   85.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
 51 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   82.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 53 omega  133.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 54 omega   81.00  167.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -154.0000 86

#__ type_ start__ end____ width___ exp.time_
 55 omega   81.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 56 omega  113.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
 57 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 59 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 60 omega   57.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 61 omega -120.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 62 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
 63 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 64 omega -115.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 65 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 66 omega   57.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
 67 omega   15.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004   37.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
 68 omega  -55.00   13.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
 69 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
 70 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
 71 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 72 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
 73 omega -141.00  -27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000  -29.7275 114

#__ type_ start__ end____ width___ exp.time_
 74 omega   87.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
 75 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -154.0000 97

#__ type_ start__ end____ width___ exp.time_
 76 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 93

#__ type_ start__ end____ width___ exp.time_
 77 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
 78 omega   37.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 79 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -90.0000 78

#__ type_ start__ end____ width___ exp.time_
 80 omega   84.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 81 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 82 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
 83 omega   40.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 84 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
 85 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 86 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
 87 omega  100.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
 88 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 89 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
 90 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
 91 omega   87.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 92 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
 93 omega   87.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000   30.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0635508000
_diffrn_orient_matrix_UB_12      0.1129458000
_diffrn_orient_matrix_UB_13      -0.0338129000
_diffrn_orient_matrix_UB_21      -0.1550153000
_diffrn_orient_matrix_UB_22      0.1079451000
_diffrn_orient_matrix_UB_23      0.0256248000
_diffrn_orient_matrix_UB_31      0.2461869000
_diffrn_orient_matrix_UB_32      0.0387955000
_diffrn_orient_matrix_UB_33      0.0271083000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2272
_reflns_number_total             3210
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.3292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C2 C 0.9158(3) 0.85414(18) 0.52896(6) 0.0480(4) Uani 1 d . . .
C3 C 1.1019(3) 0.74097(17) 0.52438(5) 0.0448(4) Uani 1 d . . .
C4 C 1.1064(3) 0.66353(17) 0.48765(5) 0.0467(4) Uani 1 d . . .
H4 H 1.2269 0.5920 0.4854 0.056 Uiso 1 calc . . R
C5 C 0.9173(4) 0.61495(19) 0.41287(6) 0.0532(4) Uani 1 d . . .
H5 H 1.0324 0.5418 0.4090 0.064 Uiso 1 calc . . R
C6 C 0.7395(4) 0.6477(2) 0.38027(6) 0.0559(5) Uani 1 d . . .
H6 H 0.7337 0.5963 0.3545 0.067 Uiso 1 calc . . R
C7 C 0.5665(3) 0.75827(19) 0.38559(6) 0.0504(4) Uani 1 d . . .
C8 C 0.5698(3) 0.83449(18) 0.42394(6) 0.0489(4) Uani 1 d . . .
H8 H 0.4541 0.9074 0.4278 0.059 Uiso 1 calc . . R
C9 C 1.2620(4) 0.75024(19) 0.60298(6) 0.0525(4) Uani 1 d . . .
H9 H 1.1295 0.7984 0.6161 0.063 Uiso 1 calc . . R
C10 C 1.4807(3) 0.69737(18) 0.62277(6) 0.0494(4) Uani 1 d . . .
C11 C 1.5691(4) 0.6985(2) 0.66898(6) 0.0547(4) Uani 1 d . . .
C12 C 1.7691(5) 0.6137(3) 0.68374(7) 0.0784(7) Uani 1 d . . .
H12 H 1.8487 0.5544 0.6643 0.094 Uiso 1 calc . . R
C13 C 1.8523(5) 0.6155(3) 0.72702(8) 0.0944(9) Uani 1 d . . .
H13 H 1.9894 0.5589 0.7364 0.113 Uiso 1 calc . . R
C14 C 1.7347(5) 0.7001(3) 0.75623(8) 0.0943(8) Uani 1 d . . .
H14 H 1.7903 0.7007 0.7855 0.113 Uiso 1 calc . . R
C15 C 1.5367(6) 0.7831(3) 0.74230(8) 0.1005(9) Uani 1 d . . .
H15 H 1.4561 0.8406 0.7621 0.121 Uiso 1 calc . . R
C16 C 1.4529(5) 0.7832(3) 0.69895(7) 0.0822(7) Uani 1 d . . .
H16 H 1.3167 0.8409 0.6899 0.099 Uiso 1 calc . . R
C17 C 0.2399(4) 0.9032(2) 0.35243(7) 0.0704(6) Uani 1 d . . .
H17A H 0.1491 0.9148 0.3248 0.106 Uiso 1 calc . . GR
H17B H 0.3428 0.9847 0.3587 0.106 Uiso 1 calc . . GR
H17C H 0.1176 0.8907 0.3749 0.106 Uiso 1 calc . . GR
C18 C 0.9275(3) 0.69076(17) 0.45222(5) 0.0453(4) Uani 1 d . . .
C19 C 0.7508(3) 0.79887(17) 0.45637(5) 0.0453(4) Uani 1 d . . .
N1 N 1.2784(3) 0.71768(15) 0.56009(4) 0.0467(3) Uani 1 d . . .
N2 N 1.5007(3) 0.64680(17) 0.55348(5) 0.0549(4) Uani 1 d . . .
N3 N 1.6215(3) 0.63528(17) 0.59151(5) 0.0559(4) Uani 1 d . . .
O1 O 0.7491(2) 0.87713(13) 0.49407(4) 0.0516(3) Uani 1 d . . .
O2 O 0.8974(3) 0.92919(14) 0.56022(4) 0.0624(4) Uani 1 d . . .
O3 O 0.4034(3) 0.78374(15) 0.35078(4) 0.0637(4) Uani 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
C2 C3 1.460(2) . ?
C2 O1 1.366(2) . ?
C2 O2 1.203(2) . ?
C3 C4 1.348(2) . ?
C3 N1 1.416(2) . ?
C4 H4 0.9300 . ?
C4 C18 1.424(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(3) . ?
C5 C18 1.406(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.400(3) . ?
C7 C8 1.382(2) . ?
C7 O3 1.357(2) . ?
C8 H8 0.9300 . ?
C8 C19 1.382(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(2) . ?
C9 N1 1.356(2) . ?
C10 C11 1.471(2) . ?
C10 N3 1.361(2) . ?
C11 C12 1.379(3) . ?
C11 C16 1.379(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.353(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 O3 1.425(2) . ?
C18 C19 1.390(2) . ?
C19 O1 1.3764(19) . ?
N1 N2 1.3575(19) . ?
N2 N3 1.306(2) . ?

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
O1 C2 C3 116.38(14) . . ?
O2 C2 C3 126.27(17) . . ?
O2 C2 O1 117.35(15) . . ?
C4 C3 C2 121.34(16) . . ?
C4 C3 N1 121.82(15) . . ?
N1 C3 C2 116.84(15) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C18 120.27(15) . . ?
C18 C4 H4 119.9 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C18 120.66(16) . . ?
C18 C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.25(16) . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.68(17) . . ?
O3 C7 C6 115.24(16) . . ?
O3 C7 C8 124.08(17) . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C19 117.84(16) . . ?
C19 C8 H8 121.1 . . ?
C10 C9 H9 127.3 . . ?
N1 C9 H9 127.3 . . ?
N1 C9 C10 105.36(15) . . ?
C9 C10 C11 130.47(17) . . ?
N3 C10 C9 107.91(16) . . ?
N3 C10 C11 121.61(16) . . ?
C12 C11 C10 120.92(18) . . ?
C12 C11 C16 117.96(19) . . ?
C16 C11 C10 121.12(18) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.7(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
C5 C18 C4 124.13(15) . . ?
C19 C18 C4 118.58(15) . . ?
C19 C18 C5 117.29(16) . . ?
C8 C19 C18 123.28(16) . . ?
O1 C19 C8 116.31(15) . . ?
O1 C19 C18 120.41(15) . . ?
C9 N1 C3 130.57(14) . . ?
C9 N1 N2 110.07(14) . . ?
N2 N1 C3 119.31(13) . . ?
N3 N2 N1 106.86(14) . . ?
N2 N3 C10 109.80(14) . . ?
C2 O1 C19 123.02(13) . . ?
C7 O3 C17 117.99(15) . . ?

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
C2 C3 C4 C18 -0.1(3) . . . . ?
C2 C3 N1 C9 23.3(3) . . . . ?
C2 C3 N1 N2 -159.81(15) . . . . ?
C3 C2 O1 C19 0.5(2) . . . . ?
C3 C4 C18 C5 -179.64(17) . . . . ?
C3 C4 C18 C19 0.4(2) . . . . ?
C3 N1 N2 N3 -177.56(15) . . . . ?
C4 C3 N1 C9 -157.33(18) . . . . ?
C4 C3 N1 N2 19.6(2) . . . . ?
C4 C18 C19 C8 179.69(16) . . . . ?
C4 C18 C19 O1 -0.3(2) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 O3 178.37(17) . . . . ?
C5 C18 C19 C8 -0.3(3) . . . . ?
C5 C18 C19 O1 179.76(15) . . . . ?
C6 C5 C18 C4 -179.90(17) . . . . ?
C6 C5 C18 C19 0.1(3) . . . . ?
C6 C7 C8 C19 0.7(3) . . . . ?
C6 C7 O3 C17 -173.98(18) . . . . ?
C7 C8 C19 C18 -0.1(3) . . . . ?
C7 C8 C19 O1 179.84(15) . . . . ?
C8 C7 O3 C17 5.3(3) . . . . ?
C8 C19 O1 C2 179.86(15) . . . . ?
C9 C10 C11 C12 165.9(2) . . . . ?
C9 C10 C11 C16 -13.3(3) . . . . ?
C9 C10 N3 N2 -0.2(2) . . . . ?
C9 N1 N2 N3 -0.1(2) . . . . ?
C10 C9 N1 C3 177.08(17) . . . . ?
C10 C9 N1 N2 0.0(2) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C10 C11 C16 C15 179.7(2) . . . . ?
C11 C10 N3 N2 179.15(17) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C16 C11 C12 C13 -1.1(4) . . . . ?
C18 C5 C6 C7 0.5(3) . . . . ?
C18 C19 O1 C2 -0.2(2) . . . . ?
N1 C3 C4 C18 -179.43(15) . . . . ?
N1 C9 C10 C11 -179.12(18) . . . . ?
N1 C9 C10 N3 0.1(2) . . . . ?
N1 N2 N3 C10 0.1(2) . . . . ?
N3 C10 C11 C12 -13.2(3) . . . . ?
N3 C10 C11 C16 167.6(2) . . . . ?
O1 C2 C3 C4 -0.3(3) . . . . ?
O1 C2 C3 N1 179.04(14) . . . . ?
O2 C2 C3 C4 -179.66(18) . . . . ?
O2 C2 C3 N1 -0.3(3) . . . . ?
O2 C2 O1 C19 179.85(16) . . . . ?
O3 C7 C8 C19 -178.53(16) . . . . ?

_olex2_date_sample_data_collection 1383586274.5
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
####################################################################### 
# 
# 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_5f
_database_code_depnum_ccdc_archive 'CCDC 1455636'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2015-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            5f
_chemical_formula_moiety         'C21 H20 N4 O2'
_chemical_formula_sum            'C21 H20 N4 O2'
_chemical_formula_weight         360.41
_chemical_melting_point          529

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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.7803(4)
_cell_length_b                   19.8443(6)
_cell_length_c                   7.6437(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.403(3)
_cell_angle_gamma                90.00
_cell_volume                     1767.69(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4661
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0220
_cell_measurement_theta_min      3.7630
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.5018
_exptl_crystal_size_mid          0.3403
_exptl_crystal_size_min          0.2714
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18529
_diffrn_reflns_theta_full        74.45
_diffrn_reflns_theta_max         74.45
_diffrn_reflns_theta_min         3.79
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -71.00    8.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   57.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega -114.00  -85.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega -121.00  -85.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00  129.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       41.4254 -178.0000  120.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega   88.00  114.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   48.00   81.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00   95.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega  122.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00  103.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  120.0000 68

#__ type_ start__ end____ width___ exp.time_
 10 omega  110.00  171.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
 11 omega  110.00  175.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
 12 omega   63.00   89.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   59.00   99.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -105.0000   88.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega   66.00   93.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   95.00  177.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   90.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 17 omega   89.00  117.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega -120.00   -8.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 19 omega -124.00  -79.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 20 omega -115.00  -12.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 21 omega -115.00  -12.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 22 omega -115.00  -12.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 23 omega   84.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 24 omega   31.00   71.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 25 omega   37.00   90.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 26 omega   87.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
 27 omega   84.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
 28 omega   37.00  116.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
 29 omega   54.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   15.0000 -150.0000 124
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0862983000
_diffrn_orient_matrix_UB_12      -0.0561935000
_diffrn_orient_matrix_UB_13      0.0645425000
_diffrn_orient_matrix_UB_21      0.0681023000
_diffrn_orient_matrix_UB_22      0.0497220000
_diffrn_orient_matrix_UB_23      0.1301747000
_diffrn_orient_matrix_UB_31      -0.0734677000
_diffrn_orient_matrix_UB_32      -0.0198897000
_diffrn_orient_matrix_UB_33      0.1427942000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2831
_reflns_number_total             3616
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0773P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1410
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C2 C 0.85655(13) 0.00916(9) 0.2668(2) 0.0413(4) Uani 1 d . . .
C3 C 0.73708(13) -0.00626(8) 0.1987(2) 0.0389(3) Uani 1 d . . .
C4 C 0.65074(13) 0.01421(8) 0.2838(2) 0.0410(3) Uani 1 d . . .
H4 H 0.5752 0.0060 0.2340 0.049 Uiso 1 calc . . R
C5 C 0.59039(14) 0.06940(8) 0.5507(2) 0.0444(4) Uani 1 d . . .
H5 H 0.5132 0.0631 0.5071 0.053 Uiso 1 calc . . R
C6 C 0.61938(14) 0.09902(9) 0.7119(2) 0.0449(4) Uani 1 d . . .
H6 H 0.5617 0.1123 0.7756 0.054 Uiso 1 calc . . R
C7 C 0.73601(14) 0.11003(8) 0.7846(2) 0.0425(4) Uani 1 d . . .
C8 C 0.82037(14) 0.09042(9) 0.6815(2) 0.0443(4) Uani 1 d . . .
H8 H 0.8976 0.0976 0.7230 0.053 Uiso 1 calc . . R
C9 C 0.78099(14) -0.05781(8) -0.0860(2) 0.0418(4) Uani 1 d . . .
H9 H 0.8553 -0.0429 -0.0906 0.050 Uiso 1 calc . . R
C10 C 0.71439(14) -0.09806(8) -0.2059(2) 0.0408(3) Uani 1 d . . .
C11 C 0.74051(13) -0.12899(8) -0.3703(2) 0.0393(3) Uani 1 d . . .
C12 C 0.66065(15) -0.17017(9) -0.4702(2) 0.0478(4) Uani 1 d . . .
H12 H 0.5899 -0.1779 -0.4334 0.057 Uiso 1 calc . . R
C13 C 0.68513(17) -0.19986(11) -0.6239(3) 0.0578(5) Uani 1 d . . .
H13 H 0.6309 -0.2276 -0.6890 0.069 Uiso 1 calc . . R
C14 C 0.78911(19) -0.18886(11) -0.6816(3) 0.0596(5) Uani 1 d . . .
H14 H 0.8053 -0.2088 -0.7853 0.071 Uiso 1 calc . . R
C15 C 0.86907(18) -0.14770(11) -0.5826(3) 0.0581(5) Uani 1 d . . .
H15 H 0.9395 -0.1400 -0.6204 0.070 Uiso 1 calc . . R
C16 C 0.84560(15) -0.11781(9) -0.4280(3) 0.0496(4) Uani 1 d . . .
H16 H 0.9001 -0.0903 -0.3629 0.060 Uiso 1 calc . . R
C17 C 0.67777(18) 0.16159(10) 1.0508(2) 0.0539(4) Uani 1 d . . .
H17A H 0.7108 0.1641 1.1745 0.065 Uiso 1 calc . . R
H17B H 0.6161 0.1288 1.0408 0.065 Uiso 1 calc . . R
C18 C 0.6270(2) 0.22950(13) 0.9947(3) 0.0745(7) Uani 1 d . . .
H18A H 0.5948 0.2280 0.8719 0.112 Uiso 1 calc . . GR
H18B H 0.6860 0.2632 1.0123 0.112 Uiso 1 calc . . GR
H18C H 0.5680 0.2404 1.0642 0.112 Uiso 1 calc . . GR
C19 C 0.88593(19) 0.15153(12) 1.0189(3) 0.0632(5) Uani 1 d . . .
H19A H 0.9329 0.1137 0.9927 0.076 Uiso 1 calc . . R
H19B H 0.8936 0.1559 1.1465 0.076 Uiso 1 calc . . R
C20 C 0.9304(3) 0.21461(15) 0.9437(4) 0.0911(9) Uani 1 d . . .
H20A H 0.9222 0.2110 0.8172 0.137 Uiso 1 calc . . GR
H20B H 1.0100 0.2204 0.9905 0.137 Uiso 1 calc . . GR
H20C H 0.8875 0.2527 0.9753 0.137 Uiso 1 calc . . GR
C21 C 0.67390(13) 0.04810(8) 0.4484(2) 0.0397(3) Uani 1 d . . .
C22 C 0.78813(13) 0.06064(8) 0.5195(2) 0.0392(3) Uani 1 d . . .
N1 N 0.71499(11) -0.04458(7) 0.04030(18) 0.0404(3) Uani 1 d . . .
N2 N 0.61173(13) -0.07578(10) 0.0016(2) 0.0560(4) Uani 1 d . . .
N3 N 0.61198(13) -0.10770(9) -0.1474(2) 0.0553(4) Uani 1 d . . .
N4 N 0.76604(13) 0.13705(8) 0.9498(2) 0.0516(4) Uani 1 d . . .
O1 O 0.87500(9) 0.04332(6) 0.42442(16) 0.0459(3) Uani 1 d . . .
O2 O 0.93957(10) -0.00356(7) 0.19744(17) 0.0531(3) Uani 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
C2 C3 1.460(2) . ?
C2 O1 1.372(2) . ?
C2 O2 1.206(2) . ?
C3 C4 1.348(2) . ?
C3 N1 1.421(2) . ?
C4 C21 1.417(2) . ?
C5 C6 1.362(2) . ?
C5 C21 1.408(2) . ?
C6 C7 1.422(2) . ?
C7 C8 1.410(2) . ?
C7 N4 1.370(2) . ?
C8 C22 1.375(2) . ?
C9 C10 1.373(2) . ?
C9 N1 1.351(2) . ?
C10 C11 1.470(2) . ?
C10 N3 1.360(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.382(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.386(3) . ?
C17 C18 1.511(3) . ?
C17 N4 1.466(2) . ?
C19 C20 1.503(4) . ?
C19 N4 1.462(3) . ?
C21 C22 1.398(2) . ?
C22 O1 1.3823(19) . ?
N1 N2 1.359(2) . ?
N2 N3 1.304(2) . ?

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
O1 C2 C3 115.96(14) . . ?
O2 C2 C3 126.94(16) . . ?
O2 C2 O1 117.08(14) . . ?
C4 C3 C2 121.39(15) . . ?
C4 C3 N1 121.02(14) . . ?
N1 C3 C2 117.58(14) . . ?
C3 C4 C21 120.69(15) . . ?
C6 C5 C21 121.91(15) . . ?
C5 C6 C7 121.32(15) . . ?
C8 C7 C6 117.32(16) . . ?
N4 C7 C6 121.66(15) . . ?
N4 C7 C8 121.00(16) . . ?
C22 C8 C7 119.83(15) . . ?
N1 C9 C10 104.95(14) . . ?
C9 C10 C11 130.02(15) . . ?
N3 C10 C9 108.05(15) . . ?
N3 C10 C11 121.92(15) . . ?
C12 C11 C10 120.41(15) . . ?
C12 C11 C16 118.83(16) . . ?
C16 C11 C10 120.75(15) . . ?
C13 C12 C11 120.67(17) . . ?
C14 C13 C12 120.67(18) . . ?
C13 C14 C15 118.92(18) . . ?
C14 C15 C16 120.91(18) . . ?
C15 C16 C11 119.99(17) . . ?
N4 C17 C18 115.38(18) . . ?
N4 C19 C20 113.4(2) . . ?
C5 C21 C4 125.17(15) . . ?
C22 C21 C4 118.63(15) . . ?
C22 C21 C5 116.19(15) . . ?
C8 C22 C21 123.39(15) . . ?
C8 C22 O1 116.88(14) . . ?
O1 C22 C21 119.73(15) . . ?
C9 N1 C3 131.30(14) . . ?
C9 N1 N2 110.27(14) . . ?
N2 N1 C3 118.42(13) . . ?
N3 N2 N1 107.17(14) . . ?
N2 N3 C10 109.55(15) . . ?
C7 N4 C17 120.52(16) . . ?
C7 N4 C19 121.01(16) . . ?
C19 N4 C17 117.83(16) . . ?
C2 O1 C22 123.37(12) . . ?

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
C2 C3 C4 C21 -3.7(3) . . . . ?
C2 C3 N1 C9 -17.4(3) . . . . ?
C2 C3 N1 N2 161.37(16) . . . . ?
C3 C2 O1 C22 2.3(2) . . . . ?
C3 C4 C21 C5 -177.65(16) . . . . ?
C3 C4 C21 C22 0.8(2) . . . . ?
C3 N1 N2 N3 -179.58(15) . . . . ?
C4 C3 N1 C9 163.49(17) . . . . ?
C4 C3 N1 N2 -17.7(2) . . . . ?
C4 C21 C22 C8 -177.04(16) . . . . ?
C4 C21 C22 O1 3.6(2) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
C5 C6 C7 N4 -177.07(17) . . . . ?
C5 C21 C22 C8 1.6(2) . . . . ?
C5 C21 C22 O1 -177.82(14) . . . . ?
C6 C5 C21 C4 176.91(16) . . . . ?
C6 C5 C21 C22 -1.6(2) . . . . ?
C6 C7 C8 C22 -1.4(3) . . . . ?
C6 C7 N4 C17 -5.9(3) . . . . ?
C6 C7 N4 C19 -176.59(18) . . . . ?
C7 C8 C22 C21 -0.1(3) . . . . ?
C7 C8 C22 O1 179.31(15) . . . . ?
C8 C7 N4 C17 175.72(17) . . . . ?
C8 C7 N4 C19 5.0(3) . . . . ?
C8 C22 O1 C2 175.33(15) . . . . ?
C9 C10 C11 C12 177.98(18) . . . . ?
C9 C10 C11 C16 -1.7(3) . . . . ?
C9 C10 N3 N2 0.0(2) . . . . ?
C9 N1 N2 N3 -0.6(2) . . . . ?
C10 C9 N1 C3 179.36(16) . . . . ?
C10 C9 N1 N2 0.53(19) . . . . ?
C10 C11 C12 C13 -179.40(17) . . . . ?
C10 C11 C16 C15 179.58(17) . . . . ?
C11 C10 N3 N2 179.02(16) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C18 C17 N4 C7 -77.5(2) . . . . ?
C18 C17 N4 C19 93.5(2) . . . . ?
C20 C19 N4 C7 77.2(3) . . . . ?
C20 C19 N4 C17 -93.7(2) . . . . ?
C21 C5 C6 C7 0.2(3) . . . . ?
C21 C22 O1 C2 -5.3(2) . . . . ?
N1 C3 C4 C21 175.34(14) . . . . ?
N1 C9 C10 C11 -179.25(16) . . . . ?
N1 C9 C10 N3 -0.3(2) . . . . ?
N1 N2 N3 C10 0.4(2) . . . . ?
N3 C10 C11 C12 -0.9(3) . . . . ?
N3 C10 C11 C16 179.42(17) . . . . ?
N4 C7 C8 C22 177.06(16) . . . . ?
O1 C2 C3 C4 2.2(2) . . . . ?
O1 C2 C3 N1 -176.90(14) . . . . ?
O2 C2 C3 C4 -175.94(18) . . . . ?
O2 C2 C3 N1 4.9(3) . . . . ?
O2 C2 O1 C22 -179.32(16) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7 -4 -1 0.1373 -7.0000 -4.0000 -1.0000 -0.4439 -0.8058 0.4510
-5 -6 -2 0.1643 -5.0000 -6.0000 -2.0000 -0.2234 -0.8992 0.2011
2 4 4 0.1722 2.0000 4.0001 4.0000 0.2060 0.8558 0.3447
7 6 -1 0.1716 7.0000 6.0000 -1.0000 0.2024 0.6449 -0.7764
-5 -9 0 0.1259 -5.0000 -9.0000 0.0000 0.0743 -0.7880 0.5463
4 9 2 0.1522 4.0000 9.0001 2.0000 -0.0315 0.9803 -0.1873
-3 -11 0 0.1186 -3.0000 -11.0000 0.0000 0.3592 -0.7513 0.4392
-1 -13 0 0.1300 -1.0000 -13.0000 -0.0000 0.6442 -0.7145 0.3320
-3 10 3 0.1186 -3.0000 10.0001 3.0000 -0.6272 0.6834 0.4499
5 3 -4 0.1507 5.0000 2.9999 -4.0000 0.0047 -0.0310 -0.9982
1 -13 0 0.1265 1.0000 -13.0001 -0.0000 0.8168 -0.5783 0.1851
-7 0 -1 0.1516 -7.0000 0.0000 -1.0000 -0.6686 -0.6069 0.3715
1 11 3 0.1361 1.0000 11.0001 3.0000 -0.3382 1.0056 0.1361
5 3 -4 0.1507 5.0000 2.9999 -4.0000 0.0047 -0.0310 -0.9982
-4 9 2 0.1116 -4.0000 9.0001 2.0000 -0.7219 0.4354 0.4004
-7 6 1 0.1167 -7.0000 6.0001 1.0000 -0.8767 -0.0482 0.5377
6 -7 0 0.1316 6.0000 -7.0001 -0.0000 0.9111 0.0606 -0.3016
-7 3 1 0.1154 -7.0000 3.0001 1.0000 -0.7081 -0.1974 0.5974
-3 -5 4 0.2287 -3.0000 -4.9999 4.0000 0.2802 0.0678 0.8910
7 0 1 0.1373 7.0000 -0.0000 1.0000 0.6686 0.6069 -0.3715

_olex2_submission_special_instructions 'No special instructions were received'

_chemical_name_systematic        
7-(diethylamino)-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_5h
_database_code_depnum_ccdc_archive 'CCDC 1455637'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2015-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            5h
_chemical_name_systematic        
3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_chemical_formula_moiety         'C17 H10 F N3 O2'
_chemical_formula_sum            'C17 H10 F N3 O2'
_chemical_formula_weight         307.28
_chemical_melting_point          516

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.8032(3)
_cell_length_b                   7.5652(4)
_cell_length_c                   15.7517(7)
_cell_angle_alpha                79.805(4)
_cell_angle_beta                 89.756(4)
_cell_angle_gamma                84.314(4)
_cell_volume                     677.21(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1130
_cell_measurement_theta_min      5.6630
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.6567
_exptl_crystal_size_mid          0.5217
_exptl_crystal_size_min          0.3536
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11484
_diffrn_reflns_theta_full        74.50
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         2.85
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -120.00   -4.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -19.0000   90.0000 116

#__ type_ start__ end____ width___ exp.time_
  2 omega -122.00  -90.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -77.00  -21.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -37.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  130.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  120.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00   88.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00  101.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega   85.00  129.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   80.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega   46.00   75.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   80.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 11 omega   81.00  113.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega  122.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   49.00   88.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   87.00  125.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega   78.00  125.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00  116.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 17 omega   48.00  107.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00  104.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -77.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
 19 omega   50.00   85.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 20 omega   85.00  118.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega  128.00  173.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 22 omega   50.00  108.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 23 omega  103.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
 24 omega  130.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 25 omega   62.00   99.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 26 omega   90.00  173.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
 27 omega -115.00  -12.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 28 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 29 omega -124.00  -79.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 30 omega -124.00  -79.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
 31 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
 32 omega -115.00  -12.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 33 omega   57.00  131.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
 34 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
 36 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 37 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 38 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 39 omega   87.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 40 omega   31.00  109.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
 41 omega   31.00  109.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
 42 omega   54.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   15.0000 -180.0000 124

#__ type_ start__ end____ width___ exp.time_
 43 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
 44 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 45 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
 46 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
 47 omega   84.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
 48 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 49 omega -120.00  -27.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
 50 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 51 omega   57.00  131.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
 52 omega   -4.00   83.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  -99.0000  -90.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1371517000
_diffrn_orient_matrix_UB_12      0.1095506000
_diffrn_orient_matrix_UB_13      -0.0787636000
_diffrn_orient_matrix_UB_21      0.2179213000
_diffrn_orient_matrix_UB_22      -0.0130188000
_diffrn_orient_matrix_UB_23      -0.0556326000
_diffrn_orient_matrix_UB_31      -0.0698932000
_diffrn_orient_matrix_UB_32      -0.1762663000
_diffrn_orient_matrix_UB_33      -0.0240390000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2296
_reflns_number_total             2775
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0871P)²+0.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1492
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C2 C 0.3169(3) 0.7280(2) 0.12306(10) 0.0434(4) Uani 1 d . . .
C3 C 0.5319(2) 0.67485(19) 0.08098(9) 0.0390(3) Uani 1 d . . .
C4 C 0.7101(3) 0.5743(2) 0.12554(10) 0.0414(3) Uani 1 d . . .
H4 H 0.8451 0.5437 0.0972 0.050 Uiso 1 calc . . R
C5 C 0.8722(3) 0.4105(2) 0.26745(11) 0.0484(4) Uani 1 d . . .
H5 H 1.0108 0.3767 0.2421 0.058 Uiso 1 calc . . R
C6 C 0.8441(3) 0.3586(2) 0.35494(11) 0.0534(4) Uani 1 d . . .
H6 H 0.9641 0.2908 0.3885 0.064 Uiso 1 calc . . R
C7 C 0.6371(3) 0.4073(2) 0.39291(11) 0.0538(4) Uani 1 d . . .
H7 H 0.6196 0.3716 0.4520 0.065 Uiso 1 calc . . R
C8 C 0.4562(3) 0.5080(2) 0.34434(11) 0.0502(4) Uani 1 d . . .
H8 H 0.3166 0.5389 0.3698 0.060 Uiso 1 calc . . R
C9 C 0.3960(3) 0.8450(2) -0.06630(10) 0.0434(4) Uani 1 d . . .
H9 H 0.2534 0.9026 -0.0545 0.052 Uiso 1 calc . . R
C10 C 0.5015(3) 0.85320(19) -0.14433(10) 0.0414(3) Uani 1 d . . .
C11 C 0.4244(3) 0.95076(18) -0.23016(9) 0.0402(3) Uani 1 d . . .
C12 C 0.5719(3) 0.9537(2) -0.30006(11) 0.0469(4) Uani 1 d . . .
H12 H 0.7209 0.8953 -0.2919 0.056 Uiso 1 calc . . R
C13 C 0.5006(3) 1.0420(2) -0.38162(11) 0.0537(4) Uani 1 d . . .
H13 H 0.5990 1.0428 -0.4284 0.064 Uiso 1 calc . . R
C14 C 0.2796(3) 1.1287(2) -0.39148(11) 0.0520(4) Uani 1 d . . .
C15 C 0.1305(3) 1.1311(2) -0.32417(12) 0.0533(4) Uani 1 d . . .
H15 H -0.0171 1.1920 -0.3328 0.064 Uiso 1 calc . . R
C16 C 0.2032(3) 1.0414(2) -0.24316(11) 0.0487(4) Uani 1 d . . .
H16 H 0.1034 1.0416 -0.1968 0.058 Uiso 1 calc . . R
C17 C 0.6933(3) 0.51372(19) 0.21677(10) 0.0409(3) Uani 1 d . . .
C18 C 0.4878(3) 0.56159(19) 0.25691(10) 0.0420(4) Uani 1 d . . .
N1 N 0.5444(2) 0.73455(16) -0.00981(8) 0.0412(3) Uani 1 d . . .
N2 N 0.7335(2) 0.6747(2) -0.05140(9) 0.0539(4) Uani 1 d . . .
N3 N 0.7068(2) 0.7470(2) -0.13232(9) 0.0537(4) Uani 1 d . . .
O1 O 0.30789(18) 0.66544(15) 0.20997(7) 0.0471(3) Uani 1 d . . .
O2 O 0.1505(2) 0.81976(18) 0.08928(8) 0.0597(4) Uani 1 d . . .
F1 F 0.2089(2) 1.21598(18) -0.47135(7) 0.0781(4) Uani 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
C2 C3 1.465(2) . ?
C2 O1 1.3695(19) . ?
C2 O2 1.1992(19) . ?
C3 C4 1.342(2) . ?
C3 N1 1.4252(19) . ?
C4 C17 1.435(2) . ?
C5 C6 1.378(2) . ?
C5 C17 1.397(2) . ?
C6 C7 1.386(3) . ?
C7 C8 1.382(2) . ?
C8 C18 1.382(2) . ?
C9 C10 1.365(2) . ?
C9 N1 1.3537(19) . ?
C10 C11 1.469(2) . ?
C10 N3 1.364(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.378(3) . ?
C14 C15 1.367(3) . ?
C14 F1 1.3579(19) . ?
C15 C16 1.381(2) . ?
C17 C18 1.393(2) . ?
C18 O1 1.3757(19) . ?
N1 N2 1.3562(18) . ?
N2 N3 1.298(2) . ?

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
O1 C2 C3 115.81(13) . . ?
O2 C2 C3 126.73(15) . . ?
O2 C2 O1 117.46(14) . . ?
C4 C3 C2 121.78(14) . . ?
C4 C3 N1 121.13(13) . . ?
N1 C3 C2 117.09(13) . . ?
C3 C4 C17 120.33(14) . . ?
C6 C5 C17 120.23(16) . . ?
C5 C6 C7 120.08(16) . . ?
C8 C7 C6 121.02(16) . . ?
C18 C8 C7 118.35(16) . . ?
N1 C9 C10 104.88(13) . . ?
C9 C10 C11 130.37(14) . . ?
N3 C10 C9 108.05(14) . . ?
N3 C10 C11 121.57(14) . . ?
C12 C11 C10 120.35(14) . . ?
C12 C11 C16 118.77(15) . . ?
C16 C11 C10 120.88(14) . . ?
C13 C12 C11 121.11(15) . . ?
C14 C13 C12 118.04(16) . . ?
C15 C14 C13 122.63(16) . . ?
F1 C14 C13 118.32(16) . . ?
F1 C14 C15 119.05(16) . . ?
C14 C15 C16 118.75(16) . . ?
C15 C16 C11 120.68(15) . . ?
C5 C17 C4 123.52(15) . . ?
C18 C17 C4 118.13(14) . . ?
C18 C17 C5 118.35(15) . . ?
C8 C18 C17 121.96(15) . . ?
O1 C18 C8 117.54(14) . . ?
O1 C18 C17 120.50(14) . . ?
C9 N1 C3 131.46(13) . . ?
C9 N1 N2 110.35(13) . . ?
N2 N1 C3 118.19(12) . . ?
N3 N2 N1 107.07(13) . . ?
N2 N3 C10 109.65(13) . . ?
C2 O1 C18 123.44(12) . . ?

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
C2 C3 C4 C17 0.7(2) . . . . ?
C2 C3 N1 C9 5.0(2) . . . . ?
C2 C3 N1 N2 -174.56(13) . . . . ?
C3 C2 O1 C18 1.1(2) . . . . ?
C3 C4 C17 C5 -179.28(14) . . . . ?
C3 C4 C17 C18 0.3(2) . . . . ?
C3 N1 N2 N3 -179.67(13) . . . . ?
C4 C3 N1 C9 -174.97(15) . . . . ?
C4 C3 N1 N2 5.4(2) . . . . ?
C4 C17 C18 C8 179.52(14) . . . . ?
C4 C17 C18 O1 -0.6(2) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C5 C17 C18 C8 -0.9(2) . . . . ?
C5 C17 C18 O1 179.02(13) . . . . ?
C6 C5 C17 C4 179.42(15) . . . . ?
C6 C5 C17 C18 -0.2(2) . . . . ?
C6 C7 C8 C18 -1.0(3) . . . . ?
C7 C8 C18 C17 1.4(2) . . . . ?
C7 C8 C18 O1 -178.45(14) . . . . ?
C8 C18 O1 C2 179.74(13) . . . . ?
C9 C10 C11 C12 173.66(16) . . . . ?
C9 C10 C11 C16 -6.5(3) . . . . ?
C9 C10 N3 N2 -0.2(2) . . . . ?
C9 N1 N2 N3 0.64(19) . . . . ?
C10 C9 N1 C3 179.61(14) . . . . ?
C10 C9 N1 N2 -0.76(18) . . . . ?
C10 C11 C12 C13 178.77(15) . . . . ?
C10 C11 C16 C15 -179.22(15) . . . . ?
C11 C10 N3 N2 -179.32(14) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C11 C16 C15 0.7(2) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 F1 179.87(15) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C17 C5 C6 C7 0.6(3) . . . . ?
C17 C18 O1 C2 -0.2(2) . . . . ?
N1 C3 C4 C17 -179.29(12) . . . . ?
N1 C9 C10 C11 179.59(15) . . . . ?
N1 C9 C10 N3 0.59(17) . . . . ?
N1 N2 N3 C10 -0.3(2) . . . . ?
N3 C10 C11 C12 -7.5(2) . . . . ?
N3 C10 C11 C16 172.41(14) . . . . ?
O1 C2 C3 C4 -1.4(2) . . . . ?
O1 C2 C3 N1 178.62(12) . . . . ?
O2 C2 C3 C4 178.60(16) . . . . ?
O2 C2 C3 N1 -1.4(2) . . . . ?
O2 C2 O1 C18 -178.88(14) . . . . ?
F1 C14 C15 C16 179.70(15) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -4 4 0.2025 -0.0004 -3.9992 3.9971 -0.7529 -0.1704 0.6089
-1 2 -8 0.2789 -1.0000 1.9995 -7.9966 0.9860 0.2009 -0.0903
-2 -2 6 0.1564 -2.0015 -1.9994 5.9966 -0.4168 -0.7437 0.3482
2 1 -8 0.1755 2.0016 0.9995 -7.9962 0.4648 0.8680 -0.1239
-4 -1 3 0.1564 -4.0023 -0.9995 2.9975 0.2033 -1.0259 0.3839
3 -1 -5 0.1767 3.0018 -1.0001 -4.9977 -0.1276 0.9452 0.0866
-4 -1 0 0.1742 -4.0021 -0.9996 -0.0014 0.4395 -0.8591 0.4560
3 -3 0 0.1898 3.0015 -2.9996 -0.0003 -0.7402 0.6932 0.3190
-2 4 2 0.3063 -2.0010 3.9994 2.0001 0.5550 -0.5994 -0.6132
-3 -1 -6 0.1951 -3.0013 -0.9998 -5.9989 0.7746 -0.3073 0.5302
2 -3 5 0.2433 2.0006 -2.9994 4.9976 -0.9966 0.1970 0.2687
-2 -1 -9 0.2089 -2.0006 -0.9999 -8.9976 0.8735 0.0776 0.5324
0 -2 9 0.2287 -0.0006 -1.9994 8.9960 -0.9275 -0.4746 0.1362
-1 -1 9 0.1927 -1.0011 -0.9996 8.9961 -0.6808 -0.7056 0.0299
1 -1 -9 0.1672 1.0010 -1.0001 -8.9968 0.4618 0.7317 0.3226
-2 0 8 0.1791 -2.0015 0.0003 7.9966 -0.3553 -0.8810 -0.0524
2 -2 -8 0.1544 2.0015 -1.9999 -7.9973 0.1363 0.9071 0.4049
-3 0 7 0.1836 -3.0020 0.0003 6.9967 -0.1393 -1.0434 0.0416
2 -4 -4 0.1617 2.0011 -3.9995 -3.9994 -0.3976 0.7107 0.6612
-4 1 2 0.2239 -4.0022 1.0001 1.9986 0.5010 -0.9964 0.0554
2 -4 -2 0.1742 2.0010 -3.9994 -2.0001 -0.5550 0.5994 0.6132
1 5 4 0.2194 1.0005 4.9991 4.0005 0.0953 -0.0696 -1.0473

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_5j
_database_code_depnum_ccdc_archive 'CCDC 1455638'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2015-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18 H12 Cl N3 O3'
_chemical_formula_sum            'C18 H12 Cl N3 O3'
_chemical_formula_weight         353.77

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_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.8823(4)
_cell_length_b                   7.5418(4)
_cell_length_c                   18.0542(8)
_cell_angle_alpha                78.784(4)
_cell_angle_beta                 83.537(4)
_cell_angle_gamma                83.826(5)
_cell_volume                     777.63(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6665
_cell_measurement_theta_max      76.0410
_cell_measurement_theta_min      4.9930
_exptl_absorpt_coefficient_mu    2.391
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.5107
_exptl_crystal_F_000             365.8788
_exptl_crystal_size_max          0.4171
_exptl_crystal_size_mid          0.3177
_exptl_crystal_size_min          0.1315
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_cell_measurement_temperature    293(2)
_diffrn_reflns_number            19292
_diffrn_reflns_theta_full        74.4970
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         5.02
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   35.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   37.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega -115.00  -12.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -57.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   34.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   37.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00  122.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
  5 omega   67.00  100.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   86.00  131.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   76.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00   88.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega  144.00  173.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega  135.00  172.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  110.0000  -67.0000 37

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   90.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  116.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   64.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   85.00  113.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   91.00  164.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   60.0000 73

#__ type_ start__ end____ width___ exp.time_
 16 omega   88.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   87.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
 18 omega  132.00  169.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 19 omega   56.00  102.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 20 omega  107.00  164.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 21 omega   57.00  114.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 22 omega  109.00  161.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 23 omega  101.00  150.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 24 omega   61.00   88.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega  115.00  144.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -77.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 26 omega  110.00  164.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 27 omega   64.00  143.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -61.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 28 omega -115.00  -11.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -57.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
 29 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 30 omega  -70.00   33.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   57.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 31 omega -117.00  -14.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -37.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 32 omega  -49.00   35.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   37.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 33 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
 34 omega   53.00  129.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754 -178.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
 36 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 93

#__ type_ start__ end____ width___ exp.time_
 37 omega   87.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
 38 omega   84.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 39 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 40 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
 41 omega   37.00  116.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 42 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 43 omega   84.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
 44 omega   31.00  109.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 45 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
 46 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
 47 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 97

#__ type_ start__ end____ width___ exp.time_
 48 omega   84.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
 49 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 50 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 51 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
 52 omega -117.00  -14.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -37.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 53 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
 54 omega    7.00  119.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754   77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 55 omega   57.00  131.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
 56 omega   81.00  144.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
 57 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
 58 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
 59 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 60 omega   87.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 61 omega   31.00  109.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000   60.0000 78
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2285328000
_diffrn_orient_matrix_UB_12      -0.0294380000
_diffrn_orient_matrix_UB_13      0.0366547000
_diffrn_orient_matrix_UB_21      -0.1312877000
_diffrn_orient_matrix_UB_22      0.0224342000
_diffrn_orient_matrix_UB_23      0.0768760000
_diffrn_orient_matrix_UB_31      -0.0233878000
_diffrn_orient_matrix_UB_32      -0.2057542000
_diffrn_orient_matrix_UB_33      0.0195297000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2694
_reflns_number_total             3194
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_refine_diff_density_max         0.2428
_refine_diff_density_min         -0.3143
_refine_diff_density_rms         0.0427
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             8.8155
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.0481
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.2177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1187

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_refinement_flags_posn
C2 C 0.7816(3) -0.2722(2) 0.60541(10) 0.0463(4) Uani 1.000000 .
C3 C 1.0088(3) -0.3241(2) 0.56897(9) 0.0420(3) Uani 1.000000 .
C4 C 1.1721(3) -0.4244(2) 0.60888(9) 0.0439(4) Uani 1.000000 .
H4 H 1.3146(3) -0.4546(2) 0.58443(9) 0.0527(4) Uiso 1.000000 R
C5 C 1.2896(3) -0.5881(2) 0.73434(10) 0.0481(4) Uani 1.000000 .
H5 H 1.4349(3) -0.6216(2) 0.71257(10) 0.0577(5) Uiso 1.000000 R
C6 C 1.2341(3) -0.6404(2) 0.81148(10) 0.0492(4) Uani 1.000000 .
C7 C 1.0149(3) -0.5944(3) 0.84410(10) 0.0533(4) Uani 1.000000 .
H7 H 0.9779(3) -0.6313(3) 0.89588(10) 0.0640(5) Uiso 1.000000 R
C8 C 0.8524(3) -0.4940(3) 0.79976(10) 0.0532(4) Uani 1.000000 .
H8 H 0.7057(3) -0.4638(3) 0.82128(10) 0.0639(5) Uiso 1.000000 R
C9 C 0.9155(3) -0.1519(2) 0.43949(9) 0.0468(4) Uani 1.000000 .
H9 H 0.7709(3) -0.0940(2) 0.44986(9) 0.0561(4) Uiso 1.000000 R
C10 C 1.0418(3) -0.1432(2) 0.37076(9) 0.0441(4) Uani 1.000000 .
C11 C 0.9845(3) -0.0442(2) 0.29565(9) 0.0428(3) Uani 1.000000 .
C12 C 1.1465(3) -0.0383(3) 0.23290(10) 0.0533(4) Uani 1.000000 .
H12 H 1.2930(3) -0.0960(3) 0.23872(10) 0.0639(5) Uiso 1.000000 R
C13 C 1.0919(4) 0.0525(3) 0.16194(11) 0.0611(5) Uani 1.000000 .
H13 H 1.2001(4) 0.0554(3) 0.12009(11) 0.0734(6) Uiso 1.000000 R
C14 C 0.8748(3) 0.1382(3) 0.15435(10) 0.0539(4) Uani 1.000000 .
C15 C 0.7125(3) 0.1352(3) 0.21525(11) 0.0566(4) Uani 1.000000 .
H15 H 0.5667(3) 0.1939(3) 0.20902(11) 0.0679(5) Uiso 1.000000 R
C16 C 0.7673(3) 0.0445(3) 0.28581(10) 0.0533(4) Uani 1.000000 .
H16 H 0.6578(3) 0.0425(3) 0.32727(10) 0.0640(5) Uiso 1.000000 R
C17 C 1.3649(4) -0.7789(3) 0.93126(12) 0.0754(6) Uani 1.000000 .
H17a H 1.246(2) -0.860(2) 0.94555(12) 0.1131(10) Uiso 1.000000 GR
H17b H 1.5035(10) -0.835(2) 0.95235(13) 0.1131(10) Uiso 1.000000 GR
H17c H 1.318(3) -0.6688(5) 0.95017(14) 0.1131(10) Uiso 1.000000 GR
C18 C 1.1274(3) -0.4853(2) 0.68923(9) 0.0426(3) Uani 1.000000 .
C19 C 0.9105(3) -0.4393(2) 0.72331(9) 0.0450(4) Uani 1.000000 .
N1 N 1.0473(2) -0.26343(18) 0.48924(8) 0.0438(3) Uani 1.000000 .
N2 N 1.2466(3) -0.3233(2) 0.45219(8) 0.0563(4) Uani 1.000000 .
N3 N 1.2420(3) -0.2502(2) 0.38084(8) 0.0555(4) Uani 1.000000 .
O1 O 0.74525(19) -0.33530(17) 0.68129(7) 0.0504(3) Uani 1.000000 .
O2 O 0.6266(2) -0.1805(2) 0.57467(7) 0.0629(4) Uani 1.000000 .
O3 O 1.4045(2) -0.7388(2) 0.85156(7) 0.0648(4) Uani 1.000000 .
Cl1 Cl 0.80316(12) 0.25359(8) 0.06504(3) 0.0811(2) Uani 1.000000 .


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
C2 C3 1.471(2) . ?
C2 O1 1.361(2) . ?
C2 O2 1.203(2) . ?
C3 C4 1.342(2) . ?
C3 N1 1.423(2) . ?
C4 C18 1.437(2) . ?
C5 C6 1.383(2) . ?
C5 C18 1.395(2) . ?
C6 C7 1.394(2) . ?
C6 O3 1.369(2) . ?
C7 C8 1.381(2) . ?
C8 C19 1.376(2) . ?
C9 C10 1.366(2) . ?
C9 N1 1.356(2) . ?
C10 C11 1.471(2) . ?
C10 N3 1.363(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.390(2) . ?
C12 C13 1.385(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.371(3) . ?
C14 Cl1 1.7502(18) . ?
C15 C16 1.379(3) . ?
C17 O3 1.410(2) . ?
C18 C19 1.392(2) . ?
C19 O1 1.381(2) . ?
N1 N2 1.3610(19) . ?
N2 N3 1.301(2) . ?

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
O1 C2 C3 116.13(14) . . ?
O2 C2 C3 126.38(16) . . ?
O2 C2 O1 117.49(15) . . ?
C4 C3 C2 121.66(15) . . ?
N1 C3 C2 116.82(14) . . ?
N1 C3 C4 121.52(14) . . ?
C18 C4 C3 120.27(14) . . ?
C18 C5 C6 119.94(15) . . ?
C7 C6 C5 120.26(16) . . ?
O3 C6 C5 116.04(15) . . ?
O3 C6 C7 123.70(16) . . ?
C8 C7 C6 120.20(16) . . ?
C19 C8 C7 119.17(16) . . ?
N1 C9 C10 104.83(14) . . ?
C11 C10 C9 129.35(15) . . ?
N3 C10 C9 108.40(15) . . ?
N3 C10 C11 122.23(14) . . ?
C12 C11 C10 120.64(15) . . ?
C16 C11 C10 120.68(15) . . ?
C16 C11 C12 118.68(16) . . ?
C13 C12 C11 120.75(17) . . ?
C14 C13 C12 118.92(18) . . ?
C15 C14 C13 121.51(17) . . ?
Cl1 C14 C13 119.47(15) . . ?
Cl1 C14 C15 119.02(15) . . ?
C16 C15 C14 119.42(17) . . ?
C15 C16 C11 120.73(16) . . ?
C5 C18 C4 123.36(15) . . ?
C19 C18 C4 117.96(15) . . ?
C19 C18 C5 118.68(15) . . ?
C18 C19 C8 121.73(16) . . ?
O1 C19 C8 117.41(14) . . ?
O1 C19 C18 120.86(14) . . ?
C9 N1 C3 131.24(13) . . ?
N2 N1 C3 118.63(13) . . ?
N2 N1 C9 110.12(13) . . ?
N3 N2 N1 107.28(13) . . ?
N2 N3 C10 109.37(14) . . ?
C19 O1 C2 123.10(13) . . ?
C17 O3 C6 118.18(16) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 4 0.1519
3.9941 -0.0268 4.0251 1.0611
-0.2155 -0.0093 -3 2
-1 0.1970 -2.9925 2.0146
-1.0018 -0.7799 0.3611 -0.3641
4 0 -3 0.1429
4.0024 0.0032 -2.9699 0.8057
-0.7537 -0.1523 -4 -1
3 0.1418 -4.0051 -1.0047
2.9606 -0.7772 0.7309 0.3582
-3 2 6 0.1762
-3.0008 1.9845 5.9933 -0.5245
0.8992 -0.2211 -3 0
6 0.1247 -3.0062 -0.0185
5.9748 -0.4675 0.8536 0.1908
-1 1 11 0.0822
-1.0100 0.9567 10.9944 0.1440
0.9993 0.0415 0 -5
-6 0.1685 -0.0066 -4.9819
-6.0421 -0.0763 -0.5754 0.9072
-1 0 -11 0.0993
-0.9867 0.0496 -10.9992 -0.6301
-0.7149 -0.2019 1 0
11 0.0964 0.9867 -0.0496
10.9992 0.6301 0.7149 0.2019
-3 0 -8 0.1441
-2.9897 0.0416 -8.0153 -0.9783
-0.2227 -0.0952 4 0
1 0.1480 3.9977 -0.0139
1.0273 0.9517 -0.4462 -0.0706
3 -1 -6 0.1402
3.0035 -0.9830 -5.9840 0.4960
-0.8764 0.0151 1 0
-11 0.0841 1.0127 0.0448
-10.9852 -0.1725 -0.9765 -0.2474
0 -5 -5 0.1744
-0.0077 -4.9861 -5.0428 -0.0398
-0.4985 0.9276 1 5
0 0.1870 1.0134 5.0052
0.0533 0.0862 -0.0167 -1.0525
0 0 -11 0.0680
0.0130 0.0472 -10.9922 -0.4013
-0.8457 -0.2247 0 0
-12 0.0672 0.0142 0.0515
-11.9915 -0.4378 -0.9226 -0.2451
0 0 11 0.0642
-0.0130 -0.0472 10.9922 0.4013
0.8457 0.2247 2 0
10 0.1223 1.9876 -0.0477
10.0069 0.8224 0.5073 0.1588


_chemical_name_systematic        
'3-(4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl)-6-methoxy-2H-chromen-2-one '
_chemical_name_common            5j
_chemical_melting_point          521
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
####################################################################### 
# 
# 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_5k
_database_code_depnum_ccdc_archive 'CCDC 1455639'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2015-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            5k
_chemical_name_systematic        
7-methoxy-3-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_chemical_formula_moiety         'C19 H15 N3 O4'
_chemical_formula_sum            'C19 H15 N3 O4'
_chemical_formula_weight         349.34
_chemical_melting_point          505

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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.2786(3)
_cell_length_b                   5.9228(3)
_cell_length_c                   36.7067(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.466(5)
_cell_angle_gamma                90.00
_cell_volume                     1582.36(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3057
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2070
_cell_measurement_theta_min      4.7970
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.1872
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.1185
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            9333
_diffrn_reflns_theta_full        74.44
_diffrn_reflns_theta_max         74.44
_diffrn_reflns_theta_min         4.82
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -124.00  -79.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega -106.00  -80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   -8.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   37.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega -115.00  -65.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254 -147.0000   51.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   63.00  101.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega  152.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  125.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  9 omega  102.00  128.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega   44.00   70.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   87.00  164.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 13 omega -115.00  -12.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 14 omega -116.00  -10.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -66.0000   94.0000 106

#__ type_ start__ end____ width___ exp.time_
 15 omega -115.00  -12.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 16 omega   84.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 18 omega   85.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1375685000
_diffrn_orient_matrix_UB_12      -0.1878557000
_diffrn_orient_matrix_UB_13      0.0101853000
_diffrn_orient_matrix_UB_21      -0.0202023000
_diffrn_orient_matrix_UB_22      0.0604436000
_diffrn_orient_matrix_UB_23      0.0405843000
_diffrn_orient_matrix_UB_31      -0.1597072000
_diffrn_orient_matrix_UB_32      -0.1693449000
_diffrn_orient_matrix_UB_33      0.0031780000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2446
_reflns_number_total             3129
_reflns_odcompleteness_completeness 96.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.2233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.78129(16) 0.18111(19) 0.06514(3) 0.0523(3) Uani 1 d . . .
O2 O 1.05127(17) 0.0533(2) 0.08285(4) 0.0619(4) Uani 1 d . . .
O3 O 0.19564(17) 0.4304(2) 0.02184(4) 0.0604(3) Uani 1 d . . .
O4 O 2.05776(17) 0.2272(2) 0.22498(4) 0.0591(3) Uani 1 d . . .
N1 N 1.11634(18) 0.4318(2) 0.12927(4) 0.0459(3) Uani 1 d . . .
N2 N 1.1479(2) 0.6369(3) 0.14482(4) 0.0575(4) Uani 1 d . . .
N3 N 1.3019(2) 0.6220(3) 0.16280(4) 0.0578(4) Uani 1 d . . .
C2 C 0.9401(2) 0.2024(3) 0.08540(4) 0.0465(4) Uani 1 d . . .
C3 C 0.9550(2) 0.4048(3) 0.10786(4) 0.0426(4) Uani 1 d . . .
C4 C 0.8219(2) 0.5621(3) 0.10761(4) 0.0471(4) Uani 1 d . . .
H4 H 0.8351 0.6905 0.1220 0.057 Uiso 1 calc . . R
C5 C 0.5150(2) 0.6902(3) 0.08383(5) 0.0507(4) Uani 1 d . . .
H5 H 0.5215 0.8225 0.0974 0.061 Uiso 1 calc . . R
C6 C 0.3639(2) 0.6510(3) 0.06257(5) 0.0513(4) Uani 1 d . . .
H6 H 0.2689 0.7560 0.0618 0.062 Uiso 1 calc . . R
C7 C 0.3513(2) 0.4531(3) 0.04190(4) 0.0477(4) Uani 1 d . . .
C8 C 0.4926(2) 0.2961(3) 0.04292(5) 0.0498(4) Uani 1 d . . .
H8 H 0.4859 0.1640 0.0293 0.060 Uiso 1 calc . . R
C9 C 1.2540(2) 0.2871(3) 0.13811(4) 0.0468(4) Uani 1 d . . .
H9 H 1.2656 0.1369 0.1311 0.056 Uiso 1 calc . . R
C10 C 1.3722(2) 0.4091(3) 0.15951(4) 0.0463(4) Uani 1 d . . .
C11 C 1.5488(2) 0.3504(3) 0.17667(4) 0.0454(4) Uani 1 d . . .
C12 C 1.6391(2) 0.5080(3) 0.19848(5) 0.0520(4) Uani 1 d . . .
H12 H 1.5852 0.6480 0.2025 0.062 Uiso 1 calc . . R
C13 C 1.8068(2) 0.4597(3) 0.21409(5) 0.0538(4) Uani 1 d . . .
H13 H 1.8641 0.5671 0.2288 0.065 Uiso 1 calc . . R
C14 C 1.8917(2) 0.2544(3) 0.20836(4) 0.0463(4) Uani 1 d . . .
C15 C 1.8037(3) 0.0941(3) 0.18692(5) 0.0535(4) Uani 1 d . . .
H15 H 1.8583 -0.0454 0.1828 0.064 Uiso 1 calc . . R
C16 C 1.6331(3) 0.1437(3) 0.17158(5) 0.0543(4) Uani 1 d . . .
H16 H 1.5740 0.0347 0.1575 0.065 Uiso 1 calc . . R
C17 C 2.1468(3) 0.0144(3) 0.22274(6) 0.0658(5) Uani 1 d . . .
H17A H 2.1703 -0.0209 0.1977 0.099 Uiso 1 calc . . GR
H17B H 2.0695 -0.0999 0.2330 0.099 Uiso 1 calc . . GR
H17C H 2.2610 0.0201 0.2360 0.099 Uiso 1 calc . . GR
C18 C 0.1775(3) 0.2354(3) -0.00093(5) 0.0628(5) Uani 1 d . . .
H18A H 0.2800 0.2275 -0.0172 0.094 Uiso 1 calc . . GR
H18B H 0.0655 0.2457 -0.0149 0.094 Uiso 1 calc . . GR
H18C H 0.1747 0.1021 0.0139 0.094 Uiso 1 calc . . GR
C19 C 0.6610(2) 0.5353(3) 0.08569(4) 0.0441(4) Uani 1 d . . .
C20 C 0.6438(2) 0.3416(3) 0.06480(4) 0.0443(4) Uani 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 C2 1.3749(19) . ?
O1 C20 1.3798(18) . ?
O2 C2 1.2019(19) . ?
O3 C7 1.353(2) . ?
O3 C18 1.431(2) . ?
O4 C14 1.3594(19) . ?
O4 C17 1.420(2) . ?
N1 N2 1.3607(19) . ?
N1 C3 1.417(2) . ?
N1 C9 1.356(2) . ?
N2 N3 1.299(2) . ?
N3 C10 1.367(2) . ?
C2 C3 1.458(2) . ?
C3 C4 1.344(2) . ?
C4 C19 1.424(2) . ?
C5 C6 1.363(2) . ?
C5 C19 1.405(2) . ?
C6 C7 1.399(2) . ?
C7 C8 1.387(2) . ?
C8 C20 1.384(2) . ?
C9 C10 1.367(2) . ?
C10 C11 1.469(2) . ?
C11 C12 1.391(2) . ?
C11 C16 1.383(2) . ?
C12 C13 1.375(2) . ?
C13 C14 1.380(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.390(2) . ?
C19 C20 1.385(2) . ?

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
C2 O1 C20 123.23(13) . . ?
C7 O3 C18 118.11(13) . . ?
C14 O4 C17 118.95(14) . . ?
N2 N1 C3 118.02(13) . . ?
C9 N1 N2 110.00(14) . . ?
C9 N1 C3 131.97(14) . . ?
N3 N2 N1 107.12(13) . . ?
N2 N3 C10 109.88(14) . . ?
O1 C2 C3 116.06(14) . . ?
O2 C2 O1 117.02(15) . . ?
O2 C2 C3 126.93(16) . . ?
N1 C3 C2 117.65(13) . . ?
C4 C3 N1 121.29(15) . . ?
C4 C3 C2 121.05(15) . . ?
C3 C4 C19 121.06(15) . . ?
C6 C5 C19 121.55(16) . . ?
C5 C6 C7 120.13(15) . . ?
O3 C7 C6 115.42(14) . . ?
O3 C7 C8 124.44(16) . . ?
C8 C7 C6 120.15(16) . . ?
C20 C8 C7 118.12(15) . . ?
N1 C9 C10 105.30(15) . . ?
N3 C10 C11 120.51(15) . . ?
C9 C10 N3 107.69(15) . . ?
C9 C10 C11 131.77(16) . . ?
C12 C11 C10 119.72(15) . . ?
C16 C11 C10 122.63(15) . . ?
C16 C11 C12 117.65(16) . . ?
C13 C12 C11 120.92(16) . . ?
C12 C13 C14 121.11(16) . . ?
O4 C14 C13 115.68(15) . . ?
O4 C14 C15 125.35(16) . . ?
C13 C14 C15 118.97(16) . . ?
C14 C15 C16 119.48(16) . . ?
C11 C16 C15 121.85(16) . . ?
C5 C19 C4 124.97(15) . . ?
C20 C19 C4 118.35(14) . . ?
C20 C19 C5 116.67(15) . . ?
O1 C20 C8 116.39(14) . . ?
O1 C20 C19 120.23(14) . . ?
C8 C20 C19 123.38(15) . . ?

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 C2 C3 N1 179.66(13) . . . . ?
O1 C2 C3 C4 -1.7(2) . . . . ?
O2 C2 C3 N1 -0.2(3) . . . . ?
O2 C2 C3 C4 178.41(17) . . . . ?
O3 C7 C8 C20 -179.82(15) . . . . ?
O4 C14 C15 C16 179.76(17) . . . . ?
N1 N2 N3 C10 -0.3(2) . . . . ?
N1 C3 C4 C19 179.21(14) . . . . ?
N1 C9 C10 N3 0.02(18) . . . . ?
N1 C9 C10 C11 -177.94(16) . . . . ?
N2 N1 C3 C2 167.80(14) . . . . ?
N2 N1 C3 C4 -10.8(2) . . . . ?
N2 N1 C9 C10 -0.23(18) . . . . ?
N2 N3 C10 C9 0.2(2) . . . . ?
N2 N3 C10 C11 178.44(15) . . . . ?
N3 C10 C11 C12 4.4(2) . . . . ?
N3 C10 C11 C16 -174.37(17) . . . . ?
C2 O1 C20 C8 179.78(15) . . . . ?
C2 O1 C20 C19 -0.4(2) . . . . ?
C2 C3 C4 C19 0.7(2) . . . . ?
C3 N1 N2 N3 -179.82(14) . . . . ?
C3 N1 C9 C10 179.98(15) . . . . ?
C3 C4 C19 C5 179.73(16) . . . . ?
C3 C4 C19 C20 0.6(2) . . . . ?
C4 C19 C20 O1 -0.8(2) . . . . ?
C4 C19 C20 C8 179.04(15) . . . . ?
C5 C6 C7 O3 179.82(16) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C19 C20 O1 -179.97(14) . . . . ?
C5 C19 C20 C8 -0.1(2) . . . . ?
C6 C5 C19 C4 -178.99(16) . . . . ?
C6 C5 C19 C20 0.1(2) . . . . ?
C6 C7 C8 C20 0.1(3) . . . . ?
C7 C8 C20 O1 179.88(15) . . . . ?
C7 C8 C20 C19 0.1(3) . . . . ?
C9 N1 N2 N3 0.36(19) . . . . ?
C9 N1 C3 C2 -12.4(2) . . . . ?
C9 N1 C3 C4 168.98(17) . . . . ?
C9 C10 C11 C12 -177.86(18) . . . . ?
C9 C10 C11 C16 3.4(3) . . . . ?
C10 C11 C12 C13 -178.29(16) . . . . ?
C10 C11 C16 C15 177.51(16) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
C12 C13 C14 O4 179.46(16) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 0.9(3) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
C17 O4 C14 C13 175.09(16) . . . . ?
C17 O4 C14 C15 -4.4(3) . . . . ?
C18 O3 C7 C6 177.78(16) . . . . ?
C18 O3 C7 C8 -2.4(3) . . . . ?
C19 C5 C6 C7 0.0(3) . . . . ?
C20 O1 C2 O2 -178.53(15) . . . . ?
C20 O1 C2 C3 1.6(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 2 3 0.1021 -3.9994 1.9972 3.0017 -0.8948 0.3233 0.3101
-1 4 1 0.0722 -1.0013 4.0010 1.0006 -0.8792 0.3027 -0.5145
0 3 -10 0.0670 -0.0017 3.0018 -9.9998 -0.6660 -0.2244 -0.5399
-4 0 -11 0.0918 -3.9992 -0.0033 -10.9984 -0.6616 -0.3658 0.6043
-1 3 -17 0.0687 -1.0017 3.0011 -16.9995 -0.8747 -0.4883 -0.4023
0 -2 21 0.0611 0.0018 -2.0017 20.9999 0.5902 0.7312 0.4054
1 1 -22 0.0616 0.9983 1.0022 -22.0003 -0.2750 -0.8525 -0.3991
-1 0 -23 0.0552 -1.0007 -0.0001 -22.9996 -0.3719 -0.9132 0.0868
-2 -2 18 0.0612 -1.9977 -2.0035 18.0007 0.2849 0.6498 0.7155
4 2 7 0.0796 3.9982 2.0045 6.9985 0.2448 0.3244 -0.9557
2 -3 -2 0.0764 2.0005 -2.9996 -2.0009 0.8183 -0.3029 0.1821
0 -3 16 0.0567 0.0019 -3.0020 15.9998 0.7272 0.4678 0.5589
4 -1 -15 0.0830 3.9984 -0.9963 -15.0016 0.5844 -0.7498 -0.5175
-1 1 23 0.0712 -0.9990 0.9988 23.0004 -0.0908 1.0140 0.0635
1 -2 -20 0.0687 0.9996 -1.9994 -20.0005 0.3094 -0.9527 0.1154
-1 -4 0 0.0756 -0.9980 -4.0029 0.0002 0.6147 -0.2218 0.8373
4 2 -2 0.0826 3.9978 2.0048 -2.0015 0.1530 -0.0408 -0.9843
-1 -2 18 0.0529 -0.9980 -2.0025 18.0003 0.4222 0.6297 0.5557
1 0 24 0.0629 1.0007 0.0001 23.9996 0.3821 0.9538 -0.0836
1 0 -23 0.0659 0.9986 0.0017 -23.0004 -0.0972 -0.9535 -0.2329
0 2 -20 0.0581 -0.0017 2.0017 -19.9999 -0.5800 -0.6907 -0.4023
1 3 17 0.0845 0.9992 3.0018 16.9997 -0.2533 0.8512 -0.6139
-2 2 16 0.0826 -1.9994 1.9986 16.0009 -0.4875 0.8106 0.0317
-4 -1 10 0.0776 -3.9978 -1.0045 10.0015 -0.2594 0.4260 0.8404

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_5l
_database_code_depnum_ccdc_archive 'CCDC 1455640'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2014-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            5l
_chemical_name_systematic        
3-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_chemical_formula_moiety         'C16 H10 N4 O2'
_chemical_formula_sum            'C16 H10 N4 O2'
_chemical_formula_weight         290.28
_chemical_absolute_configuration unk
_chemical_melting_point          508

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.3822(2)
_cell_length_b                   7.6039(3)
_cell_length_c                   23.2450(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1304.82(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.1710
_cell_measurement_theta_min      3.7490
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.1589
_exptl_crystal_size_mid          0.1589
_exptl_crystal_size_min          0.1254
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            47344
_diffrn_reflns_theta_full        78.42
_diffrn_reflns_theta_max         78.42
_diffrn_reflns_theta_min         3.80
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -56.00  -16.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -37.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00  -82.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -37.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   -9.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega -120.00  -93.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -57.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega -119.00  -43.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  7 omega  -42.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega -119.00  -53.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00  114.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega   13.00   38.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254   57.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   57.00  127.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   45.00  120.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254 -166.0000   57.0000 75

#__ type_ start__ end____ width___ exp.time_
 13 omega  -84.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 14 omega -137.00 -102.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000 -147.8753 35

#__ type_ start__ end____ width___ exp.time_
 15 omega -139.00  -80.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 16 omega -117.00  -89.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega  -67.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega -131.00 -104.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega  -56.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega  -53.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega -139.00  -86.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000   -7.9207 53

#__ type_ start__ end____ width___ exp.time_
 22 omega  -60.00  -27.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000   -7.9207 33

#__ type_ start__ end____ width___ exp.time_
 23 omega  -93.00  -27.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000 -147.8753 66

#__ type_ start__ end____ width___ exp.time_
 24 omega  -92.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 25 omega  131.00  166.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 26 omega   86.00  113.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   32.00  102.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 28 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 29 omega   54.00  144.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -61.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 30 omega   82.00  109.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   33.00   90.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
 32 omega  125.00  153.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 33 omega   86.00  114.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 34 omega   85.00  174.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  153.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 36 omega   87.00  139.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 37 omega  119.00  172.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 38 omega   81.00  107.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   81.00  111.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 40 omega   86.00  113.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 42 omega   69.00  107.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 43 omega   85.00  125.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 44 omega   86.00  142.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
 45 omega   85.00  112.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 46 omega  120.00  173.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 47 omega  115.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 48 omega   81.00  114.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 49 omega   85.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 50 omega   87.00  177.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
 51 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 52 omega   58.00  139.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000  150.0000 81

#__ type_ start__ end____ width___ exp.time_
 53 omega  115.00  152.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 54 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 55 omega   38.00  110.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 56 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
 57 omega   85.00  128.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
 58 omega   88.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -116.0000 -113.0000 30

#__ type_ start__ end____ width___ exp.time_
 59 omega   38.00   80.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 60 omega   85.00  148.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 63

#__ type_ start__ end____ width___ exp.time_
 61 omega   81.00  111.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 62 omega   79.00  115.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 63 omega   38.00   77.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 64 omega  124.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 65 omega   81.00  176.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
 66 omega  -71.00   33.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   57.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
 67 omega -130.00  -32.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  178.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 68 omega -115.00  -12.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 69 omega -124.00  -79.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 70 omega -120.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 71 omega -120.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
 72 omega -118.00  -15.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -37.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 73 omega -124.00  -79.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 74 omega -120.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
 75 omega   68.00  122.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254  165.0000  122.0000 54

#__ type_ start__ end____ width___ exp.time_
 76 omega -136.00  -31.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -61.0000  -30.0000 105

#__ type_ start__ end____ width___ exp.time_
 77 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
 78 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 79 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 80 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
 81 omega -141.00  -27.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000 -147.8753 114

#__ type_ start__ end____ width___ exp.time_
 82 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 83 omega   40.00   98.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 84 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 85 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
 86 omega  100.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 87 omega   38.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -116.0000   24.0000 80

#__ type_ start__ end____ width___ exp.time_
 88 omega   32.00  176.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -15.0000  120.0000 144

#__ type_ start__ end____ width___ exp.time_
 89 omega   40.00   98.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 90 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 91 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
 92 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 93 omega   37.00  116.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 94 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
 95 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 96 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
 97 omega   38.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -116.0000 -113.0000 80

#__ type_ start__ end____ width___ exp.time_
 98 omega   31.00   82.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -60.0000 51
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0459494000
_diffrn_orient_matrix_UB_12      0.1834257000
_diffrn_orient_matrix_UB_13      -0.0241485000
_diffrn_orient_matrix_UB_21      -0.0515064000
_diffrn_orient_matrix_UB_22      0.0625824000
_diffrn_orient_matrix_UB_23      0.0608830000
_diffrn_orient_matrix_UB_31      0.1968475000
_diffrn_orient_matrix_UB_32      0.0590635000
_diffrn_orient_matrix_UB_33      0.0102907000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2270
_reflns_number_total             2795
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.4951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1371
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.7697(3) 0.7067(3) 0.21807(8) 0.0574(5) Uani 1 d . . .
O2 O 1.0263(3) 0.8485(4) 0.23189(9) 0.0702(7) Uani 1 d . . .
N1 N 1.1143(3) 0.8441(3) 0.11210(9) 0.0491(6) Uani 1 d . . .
N2 N 1.1382(3) 0.8347(4) 0.05424(10) 0.0598(7) Uani 1 d . . .
N3 N 1.2936(3) 0.9106(4) 0.04318(10) 0.0593(7) Uani 1 d . . .
N4 N 1.6087(3) 1.0993(4) 0.14607(10) 0.0559(6) Uani 1 d . . .
C2 C 0.9257(4) 0.7802(4) 0.19745(12) 0.0533(7) Uani 1 d . . .
C3 C 0.9526(3) 0.7700(4) 0.13538(11) 0.0464(6) Uani 1 d . . .
C4 C 0.8284(4) 0.6966(4) 0.10084(11) 0.0480(6) Uani 1 d . . .
H4 H 0.8486 0.6920 0.0614 0.058 Uiso 1 calc . . R
C5 C 0.5277(4) 0.5490(4) 0.09072(13) 0.0537(7) Uani 1 d . . .
H5 H 0.5401 0.5439 0.0509 0.064 Uiso 1 calc . . R
C6 C 0.3753(4) 0.4820(4) 0.11648(13) 0.0584(7) Uani 1 d . . .
H6 H 0.2847 0.4316 0.0941 0.070 Uiso 1 calc . . R
C7 C 0.3558(4) 0.4891(4) 0.17567(14) 0.0612(8) Uani 1 d . . .
H7 H 0.2525 0.4419 0.1926 0.073 Uiso 1 calc . . R
C8 C 0.4858(4) 0.5643(4) 0.20973(13) 0.0593(8) Uani 1 d . . .
H8 H 0.4714 0.5703 0.2494 0.071 Uiso 1 calc . . R
C9 C 1.2559(4) 0.9253(4) 0.13736(11) 0.0504(6) Uani 1 d . . .
H9 H 1.2727 0.9476 0.1763 0.060 Uiso 1 calc . . R
C10 C 1.3695(4) 0.9676(4) 0.09294(11) 0.0489(6) Uani 1 d . . .
C11 C 1.5486(4) 1.0519(4) 0.09442(12) 0.0493(6) Uani 1 d . . .
C12 C 1.6466(4) 1.0785(4) 0.04390(13) 0.0571(7) Uani 1 d . . .
H12 H 1.6014 1.0415 0.0086 0.069 Uiso 1 calc . . R
C13 C 1.8123(4) 1.1613(5) 0.04783(15) 0.0655(8) Uani 1 d . . .
H13 H 1.8812 1.1818 0.0150 0.079 Uiso 1 calc . . R
C14 C 1.8744(4) 1.2129(4) 0.10098(16) 0.0655(8) Uani 1 d . . .
H14 H 1.9850 1.2704 0.1046 0.079 Uiso 1 calc . . R
C15 C 1.7708(4) 1.1784(5) 0.14828(14) 0.0631(8) Uani 1 d . . .
H15 H 1.8153 1.2117 0.1841 0.076 Uiso 1 calc . . R
C16 C 0.6647(4) 0.6251(4) 0.12428(12) 0.0471(6) Uani 1 d . . .
C17 C 0.6398(4) 0.6315(4) 0.18330(12) 0.0493(6) Uani 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 C2 1.367(3) . ?
O1 C17 1.378(3) . ?
O2 C2 1.209(3) . ?
N1 N2 1.358(3) . ?
N1 C3 1.427(3) . ?
N1 C9 1.348(3) . ?
N2 N3 1.309(3) . ?
N3 C10 1.356(3) . ?
N4 C11 1.330(4) . ?
N4 C15 1.340(4) . ?
C2 C3 1.459(4) . ?
C3 C4 1.340(4) . ?
C4 C16 1.433(4) . ?
C5 C6 1.373(4) . ?
C5 C16 1.402(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.370(4) . ?
C8 C17 1.389(4) . ?
C9 C10 1.368(4) . ?
C10 C11 1.469(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.379(4) . ?
C13 C14 1.375(5) . ?
C14 C15 1.364(5) . ?
C16 C17 1.385(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
C2 O1 C17 123.4(2) . . ?
N2 N1 C3 117.6(2) . . ?
C9 N1 N2 110.8(2) . . ?
C9 N1 C3 131.6(2) . . ?
N3 N2 N1 106.6(2) . . ?
N2 N3 C10 109.6(2) . . ?
C11 N4 C15 117.0(3) . . ?
O1 C2 C3 116.1(2) . . ?
O2 C2 O1 117.4(3) . . ?
O2 C2 C3 126.4(3) . . ?
N1 C3 C2 117.9(2) . . ?
C4 C3 N1 120.6(2) . . ?
C4 C3 C2 121.4(3) . . ?
C3 C4 C16 120.5(2) . . ?
C6 C5 C16 120.1(3) . . ?
C5 C6 C7 120.3(3) . . ?
C8 C7 C6 121.2(3) . . ?
C7 C8 C17 118.1(3) . . ?
N1 C9 C10 104.7(2) . . ?
N3 C10 C9 108.4(2) . . ?
N3 C10 C11 122.1(2) . . ?
C9 C10 C11 129.5(2) . . ?
N4 C11 C10 116.1(2) . . ?
N4 C11 C12 123.2(3) . . ?
C12 C11 C10 120.7(3) . . ?
C13 C12 C11 118.1(3) . . ?
C14 C13 C12 119.0(3) . . ?
C15 C14 C13 118.8(3) . . ?
N4 C15 C14 123.8(3) . . ?
C5 C16 C4 123.6(3) . . ?
C17 C16 C4 118.4(3) . . ?
C17 C16 C5 118.0(3) . . ?
O1 C17 C8 117.5(2) . . ?
O1 C17 C16 120.2(2) . . ?
C16 C17 C8 122.2(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 C2 C3 N1 -179.6(2) . . . . ?
O1 C2 C3 C4 1.7(4) . . . . ?
O2 C2 C3 N1 1.2(5) . . . . ?
O2 C2 C3 C4 -177.4(3) . . . . ?
N1 N2 N3 C10 0.3(3) . . . . ?
N1 C3 C4 C16 -178.9(2) . . . . ?
N1 C9 C10 N3 -0.2(3) . . . . ?
N1 C9 C10 C11 -177.4(3) . . . . ?
N2 N1 C3 C2 -179.8(3) . . . . ?
N2 N1 C3 C4 -1.1(4) . . . . ?
N2 N1 C9 C10 0.4(3) . . . . ?
N2 N3 C10 C9 -0.1(3) . . . . ?
N2 N3 C10 C11 177.4(3) . . . . ?
N3 C10 C11 N4 -179.0(3) . . . . ?
N3 C10 C11 C12 0.9(4) . . . . ?
N4 C11 C12 C13 -1.3(5) . . . . ?
C2 O1 C17 C8 -178.8(3) . . . . ?
C2 O1 C17 C16 1.0(4) . . . . ?
C2 C3 C4 C16 -0.2(4) . . . . ?
C3 N1 N2 N3 179.8(2) . . . . ?
C3 N1 C9 C10 -179.9(3) . . . . ?
C3 C4 C16 C5 178.9(3) . . . . ?
C3 C4 C16 C17 -1.0(4) . . . . ?
C4 C16 C17 O1 0.6(4) . . . . ?
C4 C16 C17 C8 -179.6(3) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C5 C16 C17 O1 -179.3(3) . . . . ?
C5 C16 C17 C8 0.5(4) . . . . ?
C6 C5 C16 C4 179.5(3) . . . . ?
C6 C5 C16 C17 -0.6(4) . . . . ?
C6 C7 C8 C17 -0.9(5) . . . . ?
C7 C8 C17 O1 -180.0(3) . . . . ?
C7 C8 C17 C16 0.3(5) . . . . ?
C9 N1 N2 N3 -0.4(3) . . . . ?
C9 N1 C3 C2 0.6(5) . . . . ?
C9 N1 C3 C4 179.2(3) . . . . ?
C9 C10 C11 N4 -2.1(4) . . . . ?
C9 C10 C11 C12 177.8(3) . . . . ?
C10 C11 C12 C13 178.8(3) . . . . ?
C11 N4 C15 C14 0.4(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 N4 -1.3(5) . . . . ?
C15 N4 C11 C10 -179.2(3) . . . . ?
C15 N4 C11 C12 0.9(4) . . . . ?
C16 C5 C6 C7 0.0(5) . . . . ?
C17 O1 C2 O2 177.1(3) . . . . ?
C17 O1 C2 C3 -2.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
