# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_y1
_database_code_depnum_ccdc_archive 'CCDC 1416490'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1.HOAc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N3 O3'
_chemical_formula_weight         339.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   6.4775(13)
_cell_length_b                   7.7267(15)
_cell_length_c                   35.195(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1761.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle-like
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14895
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3945
_reflns_number_gt                2522
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXS-97 (Sheldrick, 1990)'
_computing_cell_refinement       'SHELXS-97 (Sheldrick, 1990)'
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.8840P)²+0.0965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(4)
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.4256
_refine_ls_wR_factor_gt          0.2972
_refine_ls_goodness_of_fit_ref   0.457
_refine_ls_restrained_S_all      0.457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.7583(7) 1.4139(6) 0.47378(10) 0.0566(11) Uani 1 1 d . . .
H1A H -0.7788 1.4015 0.4966 0.085 Uiso 1 1 calc R . .
N1 N -0.5998(8) 1.3530(6) 0.40406(12) 0.0446(10) Uani 1 1 d . . .
H1 H -0.5797 1.3267 0.4307 0.067 Uiso 1 1 d . . .
N2 N -0.4644(7) 1.3229(6) 0.37586(11) 0.0436(11) Uani 1 1 d . . .
N3 N -0.1197(8) 1.4133(7) 0.20298(13) 0.0532(12) Uani 1 1 d . . .
C1 C -0.9218(8) 1.4947(7) 0.45786(14) 0.0430(11) Uani 1 1 d . . .
C2 C -1.0912(9) 1.5521(8) 0.47963(16) 0.0526(14) Uani 1 1 d . . .
H2B H -1.0910 1.5361 0.5058 0.063 Uiso 1 1 calc R . .
C3 C -1.2555(10) 1.6309(9) 0.4626(2) 0.0605(15) Uani 1 1 d . . .
H3A H -1.3671 1.6673 0.4771 0.073 Uiso 1 1 calc R . .
C4 C -1.2566(9) 1.6567(9) 0.4235(2) 0.0585(15) Uani 1 1 d . . .
H4A H -1.3686 1.7108 0.4120 0.070 Uiso 1 1 calc R . .
C5 C -1.0923(9) 1.6024(8) 0.40184(16) 0.0491(13) Uani 1 1 d . . .
H5A H -1.0945 1.6209 0.3757 0.059 Uiso 1 1 calc R . .
C6 C -0.9214(8) 1.5198(7) 0.41830(14) 0.0412(11) Uani 1 1 d . . .
C7 C -0.7529(8) 1.4659(6) 0.39380(14) 0.0410(11) Uani 1 1 d . . .
C8 C -0.7091(8) 1.5092(7) 0.35612(14) 0.0440(12) Uani 1 1 d . . .
H8A H -0.7852 1.5834 0.3407 0.053 Uiso 1 1 calc R . .
C9 C -0.5290(7) 1.4199(6) 0.34574(13) 0.0372(10) Uani 1 1 d . . .
C10 C -0.4177(8) 1.4198(6) 0.30967(13) 0.0377(10) Uani 1 1 d . . .
C11 C -0.5032(8) 1.5020(7) 0.27790(15) 0.0434(11) Uani 1 1 d . . .
H11A H -0.6305 1.5567 0.2802 0.052 Uiso 1 1 calc R . .
C12 C -0.4049(9) 1.5040(8) 0.24367(14) 0.0476(12) Uani 1 1 d . . .
H12A H -0.4645 1.5631 0.2234 0.057 Uiso 1 1 calc R . .
C13 C -0.2143(8) 1.4182(6) 0.23827(13) 0.0390(10) Uani 1 1 d . . .
C14 C -0.1288(9) 1.3373(8) 0.26966(14) 0.0487(13) Uani 1 1 d . . .
H14A H -0.0031 1.2803 0.2672 0.058 Uiso 1 1 calc R . .
C15 C -0.2269(10) 1.3393(7) 0.30483(15) 0.0486(13) Uani 1 1 d . . .
H15A H -0.1640 1.2860 0.3255 0.058 Uiso 1 1 calc R . .
C16 C -0.2159(11) 1.4962(11) 0.17105(16) 0.0644(17) Uani 1 1 d . . .
H16A H -0.3403 1.4356 0.1645 0.097 Uiso 1 1 calc R . .
H16B H -0.1231 1.4947 0.1498 0.097 Uiso 1 1 calc R . .
H16C H -0.2485 1.6138 0.1775 0.097 Uiso 1 1 calc R . .
C17 C 0.0846(11) 1.3511(9) 0.19916(16) 0.0558(15) Uani 1 1 d . . .
H17A H 0.1731 1.4112 0.2166 0.084 Uiso 1 1 calc R . .
H17B H 0.1318 1.3706 0.1737 0.084 Uiso 1 1 calc R . .
H17C H 0.0877 1.2294 0.2046 0.084 Uiso 1 1 calc R . .
O2 O -0.1574(7) 1.1282(6) 0.39404(11) 0.0592(12) Uani 1 1 d . . .
H2 H -0.2683 1.1706 0.3877 0.089 Uiso 1 1 calc R . .
O3 O -0.3016(7) 1.1390(6) 0.45083(11) 0.0562(11) Uani 1 1 d . . .
C18 C -0.1565(9) 1.1024(7) 0.43011(15) 0.0470(12) Uani 1 1 d . . .
C19 C 0.0396(10) 1.0218(9) 0.44469(19) 0.0580(15) Uani 1 1 d . . .
H19A H 0.1329 1.0031 0.4239 0.087 Uiso 1 1 calc R . .
H19B H 0.0085 0.9130 0.4566 0.087 Uiso 1 1 calc R . .
H19C H 0.1026 1.0977 0.4629 0.087 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.351(7) . ?
O1 H1A 0.8200 . ?
N1 N2 1.345(6) . ?
N1 C7 1.370(7) . ?
N1 H1 0.9684 . ?
N2 C9 1.364(6) . ?
N3 C13 1.386(7) . ?
N3 C17 1.414(9) . ?
N3 C16 1.436(8) . ?
C1 C6 1.406(7) . ?
C1 C2 1.410(8) . ?
C2 C3 1.366(10) . ?
C2 H2B 0.9300 . ?
C3 C4 1.388(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.403(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.452(7) . ?
C7 C8 1.397(7) . ?
C8 C9 1.404(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.460(6) . ?
C10 C15 1.394(8) . ?
C10 C11 1.400(6) . ?
C11 C12 1.363(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.415(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(7) . ?
C14 C15 1.392(8) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O2 C18 1.285(7) . ?
O2 H2 0.8200 . ?
O3 C18 1.223(8) . ?
C18 C19 1.505(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
N2 N1 C7 112.8(4) . . ?
N2 N1 H1 126.2 . . ?
C7 N1 H1 119.1 . . ?
N1 N2 C9 106.2(4) . . ?
C13 N3 C17 120.6(5) . . ?
C13 N3 C16 119.8(5) . . ?
C17 N3 C16 118.9(5) . . ?
O1 C1 C6 118.2(5) . . ?
O1 C1 C2 122.0(5) . . ?
C6 C1 C2 119.8(5) . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2B 119.7 . . ?
C1 C2 H2B 119.7 . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C1 118.1(5) . . ?
C5 C6 C7 118.6(4) . . ?
C1 C6 C7 123.4(5) . . ?
N1 C7 C8 104.8(5) . . ?
N1 C7 C6 124.8(5) . . ?
C8 C7 C6 130.4(5) . . ?
C7 C8 C9 107.4(5) . . ?
C7 C8 H8A 126.3 . . ?
C9 C8 H8A 126.3 . . ?
N2 C9 C8 108.8(4) . . ?
N2 C9 C10 121.6(4) . . ?
C8 C9 C10 129.5(4) . . ?
C15 C10 C11 117.1(5) . . ?
C15 C10 C9 123.0(4) . . ?
C11 C10 C9 119.9(5) . . ?
C12 C11 C10 121.8(5) . . ?
C12 C11 H11A 119.1 . . ?
C10 C11 H11A 119.1 . . ?
C11 C12 C13 121.4(4) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C14 C13 N3 121.7(5) . . ?
C14 C13 C12 117.0(4) . . ?
N3 C13 C12 121.3(4) . . ?
C13 C14 C15 121.5(5) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C14 C15 C10 121.2(5) . . ?
C14 C15 H15A 119.4 . . ?
C10 C15 H15A 119.4 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 O2 H2 109.5 . . ?
O3 C18 O2 123.3(5) . . ?
O3 C18 C19 122.8(5) . . ?
O2 C18 C19 113.9(6) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O3 0.82 1.88 2.699(5) 174.5 4_476
N1 H1 O1 0.97 2.02 2.701(6) 125.4 .
N1 H1 O3 0.97 2.42 3.029(6) 120.6 .
O2 H2 N2 0.82 1.78 2.574(6) 162.2 .
O2 H2 N1 0.82 2.63 3.369(6) 150.4 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 1416489'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N3 O2'
_chemical_formula_weight         309.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.516(4)
_cell_length_b                   10.555(5)
_cell_length_c                   35.019(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3148(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       flaky
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12735
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_av_sigmaI/netI    0.3211
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         23.29
_reflns_number_total             8856
_reflns_number_gt                2430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8856
_refine_ls_number_parameters     848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3359
_refine_ls_R_factor_gt           0.1245
_refine_ls_wR_factor_ref         0.3418
_refine_ls_wR_factor_gt          0.2309
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N14 N 0.5022(12) 0.9679(9) 0.1873(3) 0.080(3) Uani 1 1 d . . .
H14 H 0.5745 1.0078 0.1996 0.096 Uiso 1 1 calc R . .
O1 O 0.8748(11) 0.6227(8) 0.4914(3) 0.090(3) Uani 1 1 d . . .
O2 O 0.3738(12) 0.3779(8) 1.0081(3) 0.085(3) Uani 1 1 d . . .
O4 O 0.5047(11) 0.4623(9) 0.5770(3) 0.095(3) Uani 1 1 d . . .
H4 H 0.4623 0.4748 0.5977 0.143 Uiso 1 1 calc R . .
N7 N 0.6755(12) 0.6433(10) 0.8663(3) 0.078(3) Uani 1 1 d . . .
N10 N 0.5124(12) 0.5250(11) 0.6501(3) 0.087(4) Uani 1 1 d . . .
N12 N 0.1807(13) 0.3590(11) 0.6340(4) 0.078(3) Uani 1 1 d . . .
C15 C 0.6256(14) 0.5409(12) 0.5730(4) 0.069(4) Uani 1 1 d . . .
O16 O 0.0046(11) 0.5328(9) 0.9219(3) 0.096(3) Uani 1 1 d . . .
H16 H 0.0211 0.5995 0.9332 0.143 Uiso 1 1 calc R . .
C17 C 0.6315(16) 0.5990(11) 0.6421(4) 0.066(4) Uani 1 1 d . . .
N22 N 0.4974(13) 0.5316(10) 0.6876(3) 0.082(3) Uani 1 1 d . . .
H22 H 0.4241 0.4925 0.6997 0.099 Uiso 1 1 calc R . .
C24 C 0.1305(19) 0.3991(13) 0.8570(5) 0.068(4) Uani 1 1 d . . .
C25 C 0.2302(13) 0.2780(11) 0.6981(4) 0.067(4) Uani 1 1 d . . .
H25 H 0.2919 0.2131 0.6882 0.080 Uiso 1 1 calc R . .
N29 N -0.0024(13) 0.4666(10) 0.8124(4) 0.089(4) Uani 1 1 d . . .
H29 H -0.0757 0.5059 0.8004 0.107 Uiso 1 1 calc R . .
N30 N 0.0117(15) 0.4748(12) 0.8511(4) 0.089(4) Uani 1 1 d . . .
C31 C 0.6046(13) 0.6036(11) 0.7055(4) 0.062(4) Uani 1 1 d . . .
C32 C 0.6562(15) 0.6338(11) 0.8276(4) 0.070(4) Uani 1 1 d . . .
C33 C 0.0698(11) 0.4635(12) 0.6893(4) 0.060(3) Uani 1 1 d . . .
H33 H 0.0226 0.5247 0.6740 0.072 Uiso 1 1 calc R . .
C39 C 0.8867(13) 0.6959(11) 0.5575(4) 0.068(4) Uani 1 1 d . . .
H39 H 0.9739 0.7466 0.5528 0.082 Uiso 1 1 calc R . .
C42 C 0.1260(16) 0.4536(12) 0.9273(5) 0.073(4) Uani 1 1 d . . .
C45 C 0.5711(12) 0.5357(12) 0.8097(5) 0.076(4) Uani 1 1 d . . .
H45 H 0.5241 0.4742 0.8249 0.091 Uiso 1 1 calc R . .
C47 C 0.319(2) 0.3113(12) 0.9058(4) 0.083(4) Uani 1 1 d . . .
H47 H 0.3603 0.2603 0.8866 0.099 Uiso 1 1 calc R . .
C48 C 0.2123(13) 0.2886(11) 0.7371(4) 0.070(4) Uani 1 1 d . . .
H48 H 0.2645 0.2334 0.7535 0.084 Uiso 1 1 calc R . .
C49 C 0.7312(12) 0.7217(11) 0.8019(4) 0.071(4) Uani 1 1 d . . .
H49 H 0.7942 0.7863 0.8115 0.085 Uiso 1 1 calc R . .
C50 C 0.1009(14) 0.3961(12) 0.7941(5) 0.071(4) Uani 1 1 d . . .
C51 C 0.1535(16) 0.3673(13) 0.6717(5) 0.073(4) Uani 1 1 d . . .
C53 C 0.5550(12) 0.5271(12) 0.7713(4) 0.065(4) Uani 1 1 d . . .
H53 H 0.5003 0.4586 0.7612 0.078 Uiso 1 1 calc R . .
C54 C 0.196(2) 0.4553(14) 0.9641(5) 0.082(5) Uani 1 1 d . . .
H54 H 0.1600 0.5101 0.9829 0.099 Uiso 1 1 calc R . .
C55 C 0.7097(14) 0.7098(12) 0.7635(4) 0.075(4) Uani 1 1 d . . .
H55 H 0.7601 0.7675 0.7476 0.090 Uiso 1 1 calc R . .
C58 C 0.8173(17) 0.6232(12) 0.5285(4) 0.075(4) Uani 1 1 d . . .
C63 C 0.6957(17) 0.5459(11) 0.5361(4) 0.085(4) Uani 1 1 d . . .
H63 H 0.6563 0.4945 0.5168 0.102 Uiso 1 1 calc R . .
C65 C 0.3864(14) 0.3026(12) 0.9422(5) 0.076(4) Uani 1 1 d . . .
H65 H 0.4726 0.2507 0.9469 0.091 Uiso 1 1 calc R . .
C69 C 0.6972(15) 0.6113(11) 0.6030(4) 0.065(4) Uani 1 1 d . . .
C71 C 0.8191(15) 0.6890(11) 0.5937(4) 0.079(4) Uani 1 1 d . . .
H71 H 0.8599 0.7408 0.6128 0.094 Uiso 1 1 calc R . .
C72 C 0.318(2) 0.3751(13) 0.9712(5) 0.082(5) Uani 1 1 d . . .
C74 C 0.0535(12) 0.4727(11) 0.7278(4) 0.058(3) Uani 1 1 d . . .
H74 H -0.0006 0.5415 0.7379 0.070 Uiso 1 1 calc R . .
C75 C 0.1165(15) 0.4605(13) 0.6088(4) 0.087(4) Uani 1 1 d . . .
H75A H 0.0056 0.4686 0.6130 0.131 Uiso 1 1 calc R . .
H75B H 0.1354 0.4388 0.5825 0.131 Uiso 1 1 calc R . .
H75C H 0.1673 0.5394 0.6145 0.131 Uiso 1 1 calc R . .
C76 C 0.1963(18) 0.3903(12) 0.8967(5) 0.072(4) Uani 1 1 d . . .
C77 C 0.6182(14) 0.5397(12) 0.8909(4) 0.090(5) Uani 1 1 d . . .
H77A H 0.5076 0.5500 0.8952 0.134 Uiso 1 1 calc R . .
H77B H 0.6727 0.5419 0.9149 0.134 Uiso 1 1 calc R . .
H77C H 0.6369 0.4599 0.8786 0.134 Uiso 1 1 calc R . .
C78 C 0.1134(13) 0.3849(12) 0.7520(4) 0.060(4) Uani 1 1 d . . .
C79 C 0.6167(13) 0.6162(11) 0.7466(4) 0.060(3) Uani 1 1 d . . .
C81 C 1.0135(16) 0.6938(12) 0.4833(3) 0.096(5) Uani 1 1 d . . .
H81A H 0.9876 0.7821 0.4816 0.143 Uiso 1 1 calc R . .
H81B H 1.0573 0.6658 0.4595 0.143 Uiso 1 1 calc R . .
H81C H 1.0888 0.6812 0.5033 0.143 Uiso 1 1 calc R . .
C86 C 0.2673(14) 0.2547(12) 0.6176(4) 0.083(4) Uani 1 1 d . . .
H86A H 0.3766 0.2635 0.6237 0.124 Uiso 1 1 calc R . .
H86B H 0.2542 0.2549 0.5904 0.124 Uiso 1 1 calc R . .
H86C H 0.2286 0.1763 0.6278 0.124 Uiso 1 1 calc R . .
C87 C 0.7659(13) 0.7433(12) 0.8835(4) 0.085(4) Uani 1 1 d . . .
H87A H 0.8752 0.7310 0.8779 0.128 Uiso 1 1 calc R . .
H87B H 0.7505 0.7423 0.9106 0.128 Uiso 1 1 calc R . .
H87C H 0.7323 0.8235 0.8734 0.128 Uiso 1 1 calc R . .
C88 C 0.6995(15) 0.6482(11) 0.6758(4) 0.070(4) Uani 1 1 d . . .
H88 H 0.7882 0.6991 0.6778 0.084 Uiso 1 1 calc R . .
C89 C 0.5123(18) 0.3050(13) 1.0169(4) 0.099(5) Uani 1 1 d . . .
H89A H 0.4900 0.2164 1.0138 0.149 Uiso 1 1 calc R . .
H89B H 0.5435 0.3210 1.0428 0.149 Uiso 1 1 calc R . .
H89C H 0.5958 0.3289 0.9999 0.149 Uiso 1 1 calc R . .
C92 C 0.2002(16) 0.3497(12) 0.8235(4) 0.074(4) Uani 1 1 d . . .
H92 H 0.2892 0.2992 0.8212 0.088 Uiso 1 1 calc R . .
O3 O 0.3758(11) 0.8753(8) 0.4920(3) 0.083(3) Uani 1 1 d . . .
O5 O 0.1255(11) 0.8767(8) -0.0087(3) 0.092(3) Uani 1 1 d . . .
O6 O 0.4977(10) 1.0363(9) 0.0766(2) 0.095(3) Uani 1 1 d . . .
H6 H 0.5206 1.0469 0.0992 0.142 Uiso 1 1 calc R . .
N8 N 0.3224(12) 0.8582(10) 0.3665(3) 0.074(3) Uani 1 1 d . . .
N9 N 0.1771(13) 0.8582(10) 0.8654(4) 0.077(3) Uani 1 1 d . . .
O11 O 0.0034(12) 1.0362(9) 0.5767(3) 0.086(3) Uani 1 1 d . . .
C13 C 0.3669(16) 0.8980(11) 0.1420(4) 0.072(4) Uani 1 1 d . . .
N18 N -0.0055(14) 0.9687(11) 0.6882(4) 0.090(4) Uani 1 1 d . . .
H18 H -0.0784 1.0074 0.7005 0.108 Uiso 1 1 calc R . .
C19 C 0.1278(18) 0.9033(12) 0.6420(4) 0.063(4) Uani 1 1 d . . .
N20 N 0.0102(13) 0.9755(10) 0.6502(4) 0.081(3) Uani 1 1 d . . .
C21 C 0.2689(11) 0.7800(10) 0.3027(4) 0.057(3) Uani 1 1 d . . .
H21 H 0.2029 0.7176 0.3124 0.069 Uiso 1 1 calc R . .
C23 C 0.1296(18) 0.9577(13) 0.5727(5) 0.070(4) Uani 1 1 d . . .
C26 C 0.2906(13) 0.7880(10) 0.2637(4) 0.069(4) Uani 1 1 d . . .
H26 H 0.2405 0.7289 0.2482 0.082 Uiso 1 1 calc R . .
C27 C 0.1035(14) 0.8956(12) 0.7053(5) 0.065(4) Uani 1 1 d . . .
C28 C 0.3744(16) 0.9584(11) 0.0742(5) 0.080(4) Uani 1 1 d . . .
C34 C 0.0709(12) 0.9650(12) 0.8112(5) 0.066(4) Uani 1 1 d . . .
H34 H 0.0265 1.0265 0.8268 0.079 Uiso 1 1 calc R . .
C35 C 0.3961(13) 0.8943(11) 0.2052(4) 0.059(3) Uani 1 1 d . . .
C36 C 0.3860(12) 0.8823(10) 0.2459(4) 0.054(3) Uani 1 1 d . . .
N37 N 0.4879(12) 0.9750(10) 0.1492(3) 0.081(3) Uani 1 1 d . . .
C38 C 0.3019(16) 0.8893(10) 0.1025(4) 0.069(4) Uani 1 1 d . . .
C40 C 0.3443(15) 0.8644(12) 0.3286(4) 0.076(4) Uani 1 1 d . . .
C41 C 0.2293(13) 0.7788(12) 0.8023(4) 0.068(4) Uani 1 1 d . . .
H41 H 0.2917 0.7152 0.8126 0.081 Uiso 1 1 calc R . .
C43 C 0.2119(14) 0.7875(12) 0.7635(5) 0.076(4) Uani 1 1 d . . .
H43 H 0.2632 0.7303 0.7476 0.091 Uiso 1 1 calc R . .
C44 C 0.3056(16) 0.9536(11) 0.0367(5) 0.086(5) Uani 1 1 d . . .
H44 H 0.3463 1.0053 0.0176 0.104 Uiso 1 1 calc R . .
C46 C 0.1831(17) 0.8762(11) 0.0283(4) 0.071(4) Uani 1 1 d . . .
C52 C 0.3840(13) 0.8029(11) 0.5585(5) 0.069(4) Uani 1 1 d . . .
H52 H 0.4691 0.7500 0.5538 0.083 Uiso 1 1 calc R . .
C56 C 0.3207(17) 0.8108(13) 0.5947(4) 0.077(4) Uani 1 1 d . . .
H56 H 0.3638 0.7622 0.6142 0.092 Uiso 1 1 calc R . .
C57 C 0.1141(14) 0.8037(11) 0.0572(4) 0.072(4) Uani 1 1 d . . .
H57 H 0.0265 0.7535 0.0524 0.087 Uiso 1 1 calc R . .
C59 C 0.1182(14) 0.9590(13) 0.8907(4) 0.086(4) Uani 1 1 d . . .
H59A H 0.1906 1.0288 0.8906 0.129 Uiso 1 1 calc R . .
H59B H 0.1082 0.9267 0.9162 0.129 Uiso 1 1 calc R . .
H59C H 0.0175 0.9873 0.8818 0.129 Uiso 1 1 calc R . .
C60 C 0.4278(12) 0.9643(12) 0.3103(4) 0.074(4) Uani 1 1 d . . .
H60 H 0.4704 1.0285 0.3253 0.089 Uiso 1 1 calc R . .
C61 C 0.1950(17) 0.8889(12) 0.6026(4) 0.068(4) Uani 1 1 d . . .
C62 C 0.1823(16) 0.8096(11) 0.0935(4) 0.082(4) Uani 1 1 d . . .
H62 H 0.1437 0.7563 0.1124 0.099 Uiso 1 1 calc R . .
C64 C 0.1536(17) 0.8650(14) 0.8263(4) 0.073(4) Uani 1 1 d . . .
C66 C 0.1144(14) 0.8848(12) 0.7472(4) 0.059(4) Uani 1 1 d . . .
C67 C 0.3811(15) 0.9594(12) 0.3911(4) 0.089(4) Uani 1 1 d . . .
H67A H 0.4926 0.9507 0.3941 0.133 Uiso 1 1 calc R . .
H67B H 0.3312 0.9542 0.4156 0.133 Uiso 1 1 calc R . .
H67C H 0.3581 1.0400 0.3797 0.133 Uiso 1 1 calc R . .
C68 C 0.192(2) 0.9516(13) 0.5356(5) 0.082(4) Uani 1 1 d . . .
H68 H 0.1488 0.9987 0.5158 0.099 Uiso 1 1 calc R . .
C70 C 0.4477(12) 0.9695(11) 0.2719(4) 0.065(4) Uani 1 1 d . . .
H70 H 0.5069 1.0361 0.2621 0.078 Uiso 1 1 calc R . .
C73 C 0.0560(12) 0.9710(12) 0.7719(5) 0.069(4) Uani 1 1 d . . .
H73 H 0.0017 1.0395 0.7617 0.082 Uiso 1 1 calc R . .
C80 C 0.321(2) 0.8734(15) 0.5293(5) 0.089(5) Uani 1 1 d . . .
C82 C 0.5154(18) 0.8059(13) 0.4837(4) 0.108(5) Uani 1 1 d . . .
H82A H 0.5982 0.8331 0.5004 0.162 Uiso 1 1 calc R . .
H82B H 0.5455 0.8208 0.4576 0.162 Uiso 1 1 calc R . .
H82C H 0.4965 0.7171 0.4874 0.162 Uiso 1 1 calc R . .
C83 C 0.2989(15) 0.8499(11) 0.1753(4) 0.076(4) Uani 1 1 d . . .
H83 H 0.2095 0.7998 0.1773 0.091 Uiso 1 1 calc R . .
C84 C 0.2327(14) 0.7558(12) 0.3820(3) 0.083(4) Uani 1 1 d . . .
H84A H 0.1235 0.7688 0.3764 0.124 Uiso 1 1 calc R . .
H84B H 0.2474 0.7524 0.4091 0.124 Uiso 1 1 calc R . .
H84C H 0.2669 0.6776 0.3708 0.124 Uiso 1 1 calc R . .
C85 C 0.2662(13) 0.7555(13) 0.8830(4) 0.086(4) Uani 1 1 d . . .
H85A H 0.2346 0.6761 0.8720 0.129 Uiso 1 1 calc R . .
H85B H 0.2464 0.7543 0.9100 0.129 Uiso 1 1 calc R . .
H85C H 0.3763 0.7684 0.8785 0.129 Uiso 1 1 calc R . .
C90 C -0.0127(16) 0.8078(12) -0.0170(4) 0.099(5) Uani 1 1 d . . .
H90A H 0.0124 0.7195 -0.0195 0.148 Uiso 1 1 calc R . .
H90B H -0.0575 0.8383 -0.0404 0.148 Uiso 1 1 calc R . .
H90C H -0.0868 0.8188 0.0034 0.148 Uiso 1 1 calc R . .
C91 C 0.1987(16) 0.8499(12) 0.6758(5) 0.082(4) Uani 1 1 d . . .
H91 H 0.2865 0.7978 0.6776 0.098 Uiso 1 1 calc R . .
H11 H -0.007(12) 1.051(10) 0.603(3) 0.06(4) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N14 N37 1.343(12) . ?
N14 C35 1.346(12) . ?
O1 C58 1.388(14) . ?
O1 C81 1.428(12) . ?
O2 C72 1.375(15) . ?
O2 C89 1.442(14) . ?
O4 C15 1.330(12) . ?
N7 C32 1.367(14) . ?
N7 C87 1.438(13) . ?
N7 C77 1.476(14) . ?
N10 C17 1.311(14) . ?
N10 N22 1.321(12) . ?
N12 C51 1.343(15) . ?
N12 C86 1.444(14) . ?
N12 C75 1.492(15) . ?
C15 C63 1.425(16) . ?
C15 C69 1.424(15) . ?
O16 C42 1.344(14) . ?
C17 C88 1.414(15) . ?
C17 C69 1.482(15) . ?
N22 C31 1.343(13) . ?
C24 N30 1.306(16) . ?
C24 C92 1.415(16) . ?
C24 C76 1.503(18) . ?
C25 C48 1.382(15) . ?
C25 C51 1.473(17) . ?
N29 C50 1.318(15) . ?
N29 N30 1.362(14) . ?
C31 C88 1.399(15) . ?
C31 C79 1.447(15) . ?
C32 C45 1.412(15) . ?
C32 C49 1.442(15) . ?
C33 C74 1.360(14) . ?
C33 C51 1.385(16) . ?
C39 C71 1.393(14) . ?
C39 C58 1.404(15) . ?
C42 C76 1.398(16) . ?
C42 C54 1.419(16) . ?
C45 C53 1.355(15) . ?
C47 C76 1.377(17) . ?
C47 C65 1.399(15) . ?
C48 C78 1.419(15) . ?
C49 C55 1.363(15) . ?
C50 C92 1.418(16) . ?
C50 C78 1.485(17) . ?
C53 C79 1.382(15) . ?
C54 C72 1.364(18) . ?
C55 C79 1.399(15) . ?
C58 C63 1.345(16) . ?
C65 C72 1.397(17) . ?
C69 C71 1.363(15) . ?
C74 C78 1.355(15) . ?
O3 C80 1.386(15) . ?
O3 C82 1.426(14) . ?
O5 C46 1.385(13) . ?
O5 C90 1.414(12) . ?
O6 C28 1.336(12) . ?
N8 C40 1.342(14) . ?
N8 C84 1.429(13) . ?
N8 C67 1.461(14) . ?
N9 C64 1.387(15) . ?
N9 C85 1.459(14) . ?
N9 C59 1.472(15) . ?
O11 C23 1.364(15) . ?
C13 N37 1.337(14) . ?
C13 C83 1.394(15) . ?
C13 C38 1.494(16) . ?
N18 N20 1.337(14) . ?
N18 C27 1.348(15) . ?
C19 N20 1.290(15) . ?
C19 C91 1.444(16) . ?
C19 C61 1.501(16) . ?
C21 C26 1.382(14) . ?
C21 C40 1.424(15) . ?
C23 C61 1.391(16) . ?
C23 C68 1.406(17) . ?
C26 C36 1.428(14) . ?
C27 C91 1.399(17) . ?
C27 C66 1.475(16) . ?
C28 C38 1.378(15) . ?
C28 C44 1.438(16) . ?
C34 C64 1.375(16) . ?
C34 C73 1.382(16) . ?
C35 C83 1.415(15) . ?
C35 C36 1.433(15) . ?
C36 C70 1.398(14) . ?
C38 C62 1.358(15) . ?
C40 C60 1.424(15) . ?
C41 C43 1.369(15) . ?
C41 C64 1.397(16) . ?
C43 C66 1.438(16) . ?
C44 C46 1.357(16) . ?
C46 C57 1.397(15) . ?
C52 C80 1.373(17) . ?
C52 C56 1.380(15) . ?
C56 C61 1.380(16) . ?
C57 C62 1.400(15) . ?
C60 C70 1.358(15) . ?
C66 C73 1.350(15) . ?
C68 C80 1.389(19) . ?

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
N37 N14 C35 115.7(10) . . ?
C58 O1 C81 118.5(9) . . ?
C72 O2 C89 117.9(12) . . ?
C32 N7 C87 122.2(11) . . ?
C32 N7 C77 118.9(10) . . ?
C87 N7 C77 118.5(11) . . ?
C17 N10 N22 104.9(11) . . ?
C51 N12 C86 121.9(13) . . ?
C51 N12 C75 118.1(13) . . ?
C86 N12 C75 120.0(12) . . ?
O4 C15 C63 116.3(12) . . ?
O4 C15 C69 125.4(12) . . ?
C63 C15 C69 118.1(11) . . ?
N10 C17 C88 110.8(12) . . ?
N10 C17 C69 122.8(13) . . ?
C88 C17 C69 125.7(12) . . ?
N10 N22 C31 115.4(10) . . ?
N30 C24 C92 114.9(16) . . ?
N30 C24 C76 118.2(14) . . ?
C92 C24 C76 126.0(16) . . ?
C48 C25 C51 121.4(13) . . ?
C50 N29 N30 117.4(14) . . ?
C24 N30 N29 100.7(13) . . ?
N22 C31 C88 103.6(12) . . ?
N22 C31 C79 124.3(11) . . ?
C88 C31 C79 131.9(11) . . ?
N7 C32 C45 123.8(12) . . ?
N7 C32 C49 121.1(12) . . ?
C45 C32 C49 115.0(13) . . ?
C74 C33 C51 123.2(13) . . ?
C71 C39 C58 117.1(12) . . ?
O16 C42 C76 121.1(17) . . ?
O16 C42 C54 116.5(15) . . ?
C76 C42 C54 121.4(14) . . ?
C53 C45 C32 122.9(12) . . ?
C76 C47 C65 124.2(15) . . ?
C25 C48 C78 119.1(13) . . ?
C55 C49 C32 119.8(12) . . ?
N29 C50 C92 104.0(14) . . ?
N29 C50 C78 125.2(15) . . ?
C92 C50 C78 130.5(12) . . ?
N12 C51 C33 125.0(15) . . ?
N12 C51 C25 119.9(14) . . ?
C33 C51 C25 114.7(13) . . ?
C45 C53 C79 122.6(12) . . ?
C72 C54 C42 118.7(15) . . ?
C49 C55 C79 124.1(12) . . ?
C63 C58 O1 117.0(12) . . ?
C63 C58 C39 120.9(14) . . ?
O1 C58 C39 122.1(12) . . ?
C58 C63 C15 121.6(13) . . ?
C72 C65 C47 117.2(14) . . ?
C71 C69 C15 117.6(12) . . ?
C71 C69 C17 124.1(12) . . ?
C15 C69 C17 118.3(12) . . ?
C69 C71 C39 124.4(12) . . ?
C54 C72 O2 114.8(15) . . ?
C54 C72 C65 121.5(17) . . ?
O2 C72 C65 123.6(17) . . ?
C78 C74 C33 122.2(13) . . ?
C47 C76 C42 115.9(16) . . ?
C47 C76 C24 122.4(14) . . ?
C42 C76 C24 121.4(15) . . ?
C74 C78 C48 119.0(13) . . ?
C74 C78 C50 122.7(13) . . ?
C48 C78 C50 117.7(13) . . ?
C53 C79 C55 115.4(13) . . ?
C53 C79 C31 122.2(11) . . ?
C55 C79 C31 121.8(12) . . ?
C31 C88 C17 105.2(11) . . ?
C24 C92 C50 102.9(14) . . ?
C80 O3 C82 117.9(12) . . ?
C46 O5 C90 119.0(9) . . ?
C40 N8 C84 119.1(11) . . ?
C40 N8 C67 120.0(10) . . ?
C84 N8 C67 120.8(11) . . ?
C64 N9 C85 122.0(13) . . ?
C64 N9 C59 120.5(12) . . ?
C85 N9 C59 117.4(13) . . ?
N37 C13 C83 112.6(13) . . ?
N37 C13 C38 119.8(11) . . ?
C83 C13 C38 126.7(12) . . ?
N20 N18 C27 113.9(13) . . ?
N20 C19 C91 111.9(12) . . ?
N20 C19 C61 124.1(15) . . ?
C91 C19 C61 123.7(15) . . ?
C19 N20 N18 105.5(12) . . ?
C26 C21 C40 122.1(11) . . ?
O11 C23 C61 123.7(15) . . ?
O11 C23 C68 115.0(16) . . ?
C61 C23 C68 121.3(15) . . ?
C21 C26 C36 123.4(11) . . ?
N18 C27 C91 105.5(14) . . ?
N18 C27 C66 122.1(14) . . ?
C91 C27 C66 132.2(14) . . ?
O6 C28 C38 129.2(15) . . ?
O6 C28 C44 113.6(12) . . ?
C38 C28 C44 117.1(12) . . ?
C64 C34 C73 117.6(14) . . ?
N14 C35 C83 103.9(11) . . ?
N14 C35 C36 123.6(12) . . ?
C83 C35 C36 132.2(10) . . ?
C70 C36 C26 112.8(12) . . ?
C70 C36 C35 124.6(11) . . ?
C26 C36 C35 122.0(11) . . ?
C13 N37 N14 102.8(10) . . ?
C62 C38 C28 119.8(14) . . ?
C62 C38 C13 122.1(11) . . ?
C28 C38 C13 117.9(13) . . ?
N8 C40 C21 122.4(11) . . ?
N8 C40 C60 123.4(12) . . ?
C21 C40 C60 113.7(13) . . ?
C43 C41 C64 120.2(14) . . ?
C41 C43 C66 120.2(13) . . ?
C46 C44 C28 122.1(12) . . ?
C44 C46 O5 118.2(12) . . ?
C44 C46 C57 119.8(14) . . ?
O5 C46 C57 122.0(13) . . ?
C80 C52 C56 119.8(14) . . ?
C61 C56 C52 121.7(14) . . ?
C46 C57 C62 117.3(12) . . ?
C70 C60 C40 122.5(13) . . ?
C56 C61 C23 118.1(14) . . ?
C56 C61 C19 122.8(14) . . ?
C23 C61 C19 119.1(15) . . ?
C38 C62 C57 123.3(12) . . ?
C34 C64 N9 119.6(15) . . ?
C34 C64 C41 120.4(14) . . ?
N9 C64 C41 119.6(15) . . ?
C73 C66 C43 116.1(14) . . ?
C73 C66 C27 124.2(14) . . ?
C43 C66 C27 119.0(13) . . ?
C80 C68 C23 118.3(15) . . ?
C60 C70 C36 124.9(12) . . ?
C66 C73 C34 125.0(13) . . ?
C52 C80 O3 125.1(17) . . ?
C52 C80 C68 120.8(15) . . ?
O3 C80 C68 114.1(17) . . ?
C13 C83 C35 104.7(11) . . ?
C27 C91 C19 103.2(13) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        23.29
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_y1
_database_code_depnum_ccdc_archive 'CCDC 1416583'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 F N3 O'
_chemical_formula_weight         297.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.2423(18)
_cell_length_b                   7.698(4)
_cell_length_c                   30.617(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.29(2)
_cell_angle_gamma                90.00
_cell_volume                     1467.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       flaky
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3863
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2080
_reflns_number_gt                1293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0924P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2080
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.0844(4) 0.2092(3) 0.55628(7) 0.1092(9) Uani 1 1 d . . .
O1 O -0.3972(4) 0.4675(4) 0.42923(9) 0.0900(9) Uani 1 1 d . . .
H1 H -0.3786 0.4821 0.4033 0.135 Uiso 1 1 calc R . .
N1 N -0.1859(4) 0.4687(4) 0.35802(9) 0.0704(9) Uani 1 1 d . . .
N2 N -0.1194(4) 0.4842(3) 0.31729(9) 0.0660(8) Uani 1 1 d . . .
H2A H -0.2059 0.5409 0.2947 0.099 Uiso 1 1 d . . .
N3 N 0.4925(4) 0.4016(3) 0.15430(8) 0.0609(8) Uani 1 1 d . . .
C1 C -0.2262(5) 0.3809(4) 0.44892(11) 0.0597(9) Uani 1 1 d . . .
C2 C -0.2406(6) 0.3365(5) 0.49232(12) 0.0708(10) Uani 1 1 d . . .
H2 H -0.371(6) 0.365(4) 0.5072(11) 0.092(11) Uiso 1 1 d . . .
C3 C -0.0713(7) 0.2517(5) 0.51340(11) 0.0726(10) Uani 1 1 d . . .
C4 C 0.1128(7) 0.2082(5) 0.49434(12) 0.0734(11) Uani 1 1 d . . .
H4 H 0.244(6) 0.146(5) 0.5119(13) 0.104(13) Uiso 1 1 d . . .
C5 C 0.1208(6) 0.2537(4) 0.45061(11) 0.0640(9) Uani 1 1 d . . .
H5 H 0.243(5) 0.234(4) 0.4354(10) 0.071(9) Uiso 1 1 d . . .
C6 C -0.0465(5) 0.3391(4) 0.42663(10) 0.0494(8) Uani 1 1 d . . .
C7 C -0.0282(5) 0.3816(3) 0.38077(10) 0.0490(8) Uani 1 1 d . . .
C8 C 0.1346(5) 0.3411(4) 0.35337(10) 0.0498(8) Uani 1 1 d . . .
H8 H 0.271(4) 0.294(4) 0.3614(9) 0.053(8) Uiso 1 1 d . . .
C9 C 0.0729(5) 0.4083(3) 0.31257(10) 0.0469(8) Uani 1 1 d . . .
C10 C 0.1786(4) 0.4075(3) 0.27177(9) 0.0422(7) Uani 1 1 d . . .
C11 C 0.0934(5) 0.4912(4) 0.23392(11) 0.0532(9) Uani 1 1 d . . .
H11 H -0.037(4) 0.539(4) 0.2343(9) 0.055(8) Uiso 1 1 d . . .
C12 C 0.1948(5) 0.4892(4) 0.19590(13) 0.0554(9) Uani 1 1 d . . .
H12 H 0.128(5) 0.530(4) 0.1713(11) 0.068(11) Uiso 1 1 d . . .
C13 C 0.3883(4) 0.4017(3) 0.19222(9) 0.0459(8) Uani 1 1 d . . .
C14 C 0.4743(5) 0.3158(3) 0.23049(10) 0.0501(8) Uani 1 1 d . . .
H14 H 0.604(4) 0.251(4) 0.2278(9) 0.056(8) Uiso 1 1 d . . .
C15 C 0.3709(5) 0.3211(3) 0.26825(11) 0.0476(8) Uani 1 1 d . . .
H3 H 0.433(4) 0.269(4) 0.2948(9) 0.049(8) Uiso 1 1 d . . .
C16 C 0.6718(6) 0.2891(5) 0.14909(11) 0.0875(13) Uani 1 1 d . . .
H16A H 0.7788 0.3071 0.1728 0.131 Uiso 1 1 calc R . .
H16B H 0.7319 0.3144 0.1218 0.131 Uiso 1 1 calc R . .
H16C H 0.6246 0.1704 0.1491 0.131 Uiso 1 1 calc R . .
C17 C 0.3844(6) 0.4666(5) 0.11428(12) 0.0853(12) Uani 1 1 d . . .
H17A H 0.2585 0.3981 0.1068 0.128 Uiso 1 1 calc R . .
H17B H 0.4794 0.4596 0.0911 0.128 Uiso 1 1 calc R . .
H17C H 0.3436 0.5855 0.1183 0.128 Uiso 1 1 calc R . .


_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
F1 C3 1.361(4) . ?
O1 C1 1.361(4) . ?
O1 H1 0.8200 . ?
N1 C7 1.342(4) . ?
N1 N2 1.349(4) . ?
N2 C9 1.352(4) . ?
N2 H2A 0.9515 . ?
N3 C13 1.373(3) . ?
N3 C16 1.434(4) . ?
N3 C17 1.443(4) . ?
C1 C2 1.381(5) . ?
C1 C6 1.394(4) . ?
C2 C3 1.363(5) . ?
C2 H2 0.99(3) . ?
C3 C4 1.369(5) . ?
C4 C5 1.389(5) . ?
C4 H4 1.06(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.94(3) . ?
C6 C7 1.455(4) . ?
C7 C8 1.400(4) . ?
C8 C9 1.380(4) . ?
C8 H8 0.94(3) . ?
C9 C10 1.456(4) . ?
C10 C15 1.384(4) . ?
C10 C11 1.396(4) . ?
C11 C12 1.366(4) . ?
C11 H11 0.89(3) . ?
C12 C13 1.394(4) . ?
C12 H12 0.89(3) . ?
C13 C14 1.416(4) . ?
C14 C15 1.366(4) . ?
C14 H14 0.96(3) . ?
C15 H3 0.96(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C7 N1 N2 105.0(2) . . ?
N1 N2 C9 113.4(3) . . ?
N1 N2 H2A 121.1 . . ?
C9 N2 H2A 125.5 . . ?
C13 N3 C16 121.2(3) . . ?
C13 N3 C17 119.8(3) . . ?
C16 N3 C17 115.7(3) . . ?
O1 C1 C2 116.2(3) . . ?
O1 C1 C6 122.0(3) . . ?
C2 C1 C6 121.8(4) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 122(2) . . ?
C1 C2 H2 120(2) . . ?
F1 C3 C2 118.1(3) . . ?
F1 C3 C4 117.7(4) . . ?
C2 C3 C4 124.1(3) . . ?
C3 C4 C5 116.2(4) . . ?
C3 C4 H4 122(2) . . ?
C5 C4 H4 121(2) . . ?
C4 C5 C6 123.2(3) . . ?
C4 C5 H5 121.8(19) . . ?
C6 C5 H5 115.0(19) . . ?
C1 C6 C5 116.7(3) . . ?
C1 C6 C7 123.0(3) . . ?
C5 C6 C7 120.3(3) . . ?
N1 C7 C8 109.7(3) . . ?
N1 C7 C6 120.4(3) . . ?
C8 C7 C6 129.9(3) . . ?
C9 C8 C7 107.1(3) . . ?
C9 C8 H8 124.6(17) . . ?
C7 C8 H8 127.7(17) . . ?
N2 C9 C8 104.8(3) . . ?
N2 C9 C10 123.8(3) . . ?
C8 C9 C10 131.4(3) . . ?
C15 C10 C11 115.8(3) . . ?
C15 C10 C9 121.4(3) . . ?
C11 C10 C9 122.8(2) . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.8(18) . . ?
C10 C11 H11 117.9(18) . . ?
C11 C12 C13 122.3(3) . . ?
C11 C12 H12 119.8(19) . . ?
C13 C12 H12 117.2(19) . . ?
N3 C13 C12 122.5(3) . . ?
N3 C13 C14 121.7(2) . . ?
C12 C13 C14 115.8(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 123.0(16) . . ?
C13 C14 H14 116.2(16) . . ?
C14 C15 C10 123.2(3) . . ?
C14 C15 H3 121.0(15) . . ?
C10 C15 H3 115.7(15) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.804
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.804
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 1416488'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.2675(10)
_cell_length_b                   9.2336(11)
_cell_length_c                   20.109(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.166(2)
_cell_angle_gamma                90.00
_cell_volume                     1515.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       slab-like
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8535
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2669
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.3003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2669
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.15680(18) 0.41961(16) 0.40050(8) 0.0366(4) Uani 1 1 d . . .
H1 H 1.040(4) 0.422(3) 0.3820(14) 0.084(10) Uiso 1 1 d . . .
N1 N 0.8740(2) 0.5052(2) 0.33553(9) 0.0339(5) Uani 1 1 d . . .
N2 N 0.7202(2) 0.5088(2) 0.29990(9) 0.0344(5) Uani 1 1 d . . .
H2A H 0.653(3) 0.437(3) 0.3056(12) 0.055(8) Uiso 1 1 d . . .
N3 N 0.0999(2) 0.6797(2) 0.07468(9) 0.0358(5) Uani 1 1 d . . .
C1 C 1.2156(2) 0.5521(2) 0.38543(10) 0.0263(5) Uani 1 1 d . . .
C2 C 1.3768(2) 0.5832(2) 0.41242(10) 0.0300(5) Uani 1 1 d . . .
H2 H 1.439(2) 0.508(2) 0.4408(10) 0.029(5) Uiso 1 1 d . . .
C3 C 1.4468(3) 0.7154(2) 0.40166(11) 0.0337(5) Uani 1 1 d . . .
C4 C 1.3514(3) 0.8165(3) 0.36182(11) 0.0350(6) Uani 1 1 d . . .
H4 H 1.398(2) 0.908(2) 0.3526(10) 0.037(6) Uiso 1 1 d . . .
C5 C 1.1926(3) 0.7848(2) 0.33341(11) 0.0319(5) Uani 1 1 d . . .
H5 H 1.127(2) 0.855(2) 0.3061(11) 0.037(6) Uiso 1 1 d . . .
C6 C 1.1194(2) 0.6530(2) 0.34429(10) 0.0261(5) Uani 1 1 d . . .
C7 C 0.9486(2) 0.6216(2) 0.31467(10) 0.0265(5) Uani 1 1 d . . .
C8 C 0.8408(2) 0.6978(2) 0.26566(10) 0.0285(5) Uani 1 1 d . . .
H8 H 0.864(2) 0.786(2) 0.2426(10) 0.026(5) Uiso 1 1 d . . .
C9 C 0.6946(2) 0.6230(2) 0.25713(10) 0.0273(5) Uani 1 1 d . . .
C10 C 0.5390(2) 0.6438(2) 0.21223(10) 0.0272(5) Uani 1 1 d . . .
C11 C 0.5321(3) 0.7217(2) 0.15252(11) 0.0287(5) Uani 1 1 d . . .
H11 H 0.632(2) 0.761(2) 0.1398(10) 0.029(5) Uiso 1 1 d . . .
C12 C 0.3888(2) 0.7341(2) 0.10720(11) 0.0299(5) Uani 1 1 d . . .
H12 H 0.392(2) 0.785(2) 0.0660(11) 0.036(6) Uiso 1 1 d . . .
C13 C 0.2426(2) 0.6682(2) 0.11952(10) 0.0277(5) Uani 1 1 d . . .
C14 C 0.2501(3) 0.5916(2) 0.18035(10) 0.0308(5) Uani 1 1 d . . .
H14 H 0.151(3) 0.544(2) 0.1937(10) 0.036(6) Uiso 1 1 d . . .
C15 C 0.3939(2) 0.5803(2) 0.22487(11) 0.0313(5) Uani 1 1 d . . .
H15 H 0.393(3) 0.528(2) 0.2668(11) 0.044(7) Uiso 1 1 d . . .
C16 C 1.6214(3) 0.7491(3) 0.43238(13) 0.0470(7) Uani 1 1 d . . .
H16A H 1.6749 0.6619 0.4501 0.071 Uiso 1 1 calc R . .
H16B H 1.6219 0.8182 0.4681 0.071 Uiso 1 1 calc R . .
H16C H 1.6783 0.7887 0.3985 0.071 Uiso 1 1 calc R . .
C17 C 0.0963(3) 0.7620(3) 0.01301(12) 0.0371(6) Uani 1 1 d . . .
H17A H 0.131(3) 0.863(3) 0.0251(11) 0.042(7) Uiso 1 1 d . . .
H17B H -0.023(3) 0.764(2) -0.0104(11) 0.045(6) Uiso 1 1 d . . .
H17C H 0.168(3) 0.718(2) -0.0163(12) 0.045(7) Uiso 1 1 d . . .
C18 C -0.0407(3) 0.5920(3) 0.08354(13) 0.0377(6) Uani 1 1 d . . .
H18A H -0.086(3) 0.617(3) 0.1267(13) 0.058(8) Uiso 1 1 d . . .
H18B H -0.130(3) 0.606(2) 0.0450(12) 0.049(7) Uiso 1 1 d . . .
H18C H -0.011(3) 0.487(3) 0.0851(13) 0.066(8) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.368(2) . ?
O1 H1 0.98(3) . ?
N1 C7 1.339(3) . ?
N1 N2 1.357(2) . ?
N2 C9 1.356(3) . ?
N2 H2A 0.88(3) . ?
N3 C13 1.371(3) . ?
N3 C18 1.450(3) . ?
N3 C17 1.451(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.99(2) . ?
C3 C4 1.390(3) . ?
C3 C16 1.509(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.392(3) . ?
C5 H5 0.96(2) . ?
C6 C7 1.472(3) . ?
C7 C8 1.407(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.97(2) . ?
C9 C10 1.461(3) . ?
C10 C11 1.393(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.97(2) . ?
C12 C13 1.410(3) . ?
C12 H12 0.96(2) . ?
C13 C14 1.406(3) . ?
C14 C15 1.373(3) . ?
C14 H14 1.00(2) . ?
C15 H15 0.97(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.99(2) . ?
C17 H17B 1.02(2) . ?
C17 H17C 0.99(2) . ?
C18 H18A 1.03(3) . ?
C18 H18B 0.99(2) . ?
C18 H18C 1.00(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 104.9(17) . . ?
C7 N1 N2 104.75(17) . . ?
C9 N2 N1 113.10(18) . . ?
C9 N2 H2A 129.1(16) . . ?
N1 N2 H2A 117.7(16) . . ?
C13 N3 C18 119.93(19) . . ?
C13 N3 C17 120.07(18) . . ?
C18 N3 C17 119.33(19) . . ?
O1 C1 C2 116.84(18) . . ?
O1 C1 C6 122.40(18) . . ?
C2 C1 C6 120.77(19) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 121.0(12) . . ?
C1 C2 H2 117.6(12) . . ?
C2 C3 C4 118.0(2) . . ?
C2 C3 C16 121.0(2) . . ?
C4 C3 C16 121.0(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.5(13) . . ?
C3 C4 H4 119.7(13) . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 H5 120.6(13) . . ?
C6 C5 H5 117.4(13) . . ?
C5 C6 C1 116.95(19) . . ?
C5 C6 C7 121.42(18) . . ?
C1 C6 C7 121.62(18) . . ?
N1 C7 C8 110.43(18) . . ?
N1 C7 C6 119.41(18) . . ?
C8 C7 C6 130.15(19) . . ?
C9 C8 C7 106.33(19) . . ?
C9 C8 H8 126.6(11) . . ?
C7 C8 H8 127.1(11) . . ?
N2 C9 C8 105.39(18) . . ?
N2 C9 C10 121.85(19) . . ?
C8 C9 C10 132.7(2) . . ?
C11 C10 C15 117.12(19) . . ?
C11 C10 C9 120.79(18) . . ?
C15 C10 C9 121.98(19) . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 118.0(12) . . ?
C10 C11 H11 120.0(12) . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 H12 118.1(13) . . ?
C13 C12 H12 120.7(13) . . ?
N3 C13 C14 121.67(19) . . ?
N3 C13 C12 121.56(19) . . ?
C14 C13 C12 116.76(19) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 116.8(12) . . ?
C13 C14 H14 122.0(12) . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 H15 118.5(13) . . ?
C10 C15 H15 119.5(13) . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 108.4(13) . . ?
N3 C17 H17B 106.9(13) . . ?
H17A C17 H17B 108.6(18) . . ?
N3 C17 H17C 111.2(13) . . ?
H17A C17 H17C 110.5(19) . . ?
H17B C17 H17C 111.1(18) . . ?
N3 C18 H18A 112.7(14) . . ?
N3 C18 H18B 110.1(13) . . ?
H18A C18 H18B 107.6(19) . . ?
N3 C18 H18C 110.2(15) . . ?
H18A C18 H18C 108(2) . . ?
H18B C18 H18C 108(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1554802'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-(5-phenyl-1H-pyrazol-3-yl)phenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C15H12N2O
_chemical_formula_sum            'C2.50 H2 N0.33 O0.17'
_chemical_formula_weight         39.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   18.2533(11)
_cell_length_b                   6.3201(3)
_cell_length_c                   20.6576(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2383.1(2)
_cell_formula_units_Z            48
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2843
_cell_measurement_theta_min      2.4397
_cell_measurement_theta_max      21.5408

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15179
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.74
_reflns_number_total             4486
_reflns_number_gt                3385
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0615P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(14)
_refine_ls_number_reflns         4486
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.47188(12) -0.0722(4) -0.28832(11) 0.0478(5) Uani 1 1 d . . .
N4 N -0.61282(12) 0.0036(3) -0.40281(10) 0.0637(6) Uani 1 1 d . . .
H4 H -0.6466 0.0796 -0.4202 0.076 Uiso 1 1 calc R . .
C6 C -0.52556(13) -0.0918(3) -0.34055(11) 0.0487(5) Uani 1 1 d . . .
O7 O -0.51238(11) 0.2801(3) -0.25894(9) 0.0687(5) Uani 1 1 d . . .
H7 H -0.5389 0.2585 -0.2903 0.103 Uiso 1 1 calc R . .
N9 N -0.57110(13) 0.0697(3) -0.35303(11) 0.0637(6) Uani 1 1 d . . .
C10 C -0.59621(13) -0.1936(4) -0.42261(12) 0.0496(6) Uani 1 1 d . . .
C14 C -0.46711(14) 0.1106(4) -0.25000(12) 0.0532(6) Uani 1 1 d . . .
C16 C -0.41548(14) 0.1256(5) -0.20107(13) 0.0625(7) Uani 1 1 d . . .
H16 H -0.4128 0.2477 -0.1761 0.075 Uiso 1 1 calc R . .
C17 C -0.53966(13) -0.2590(4) -0.38341(11) 0.0505(6) Uani 1 1 d . . .
H17 H -0.5155 -0.3886 -0.3850 0.061 Uiso 1 1 calc R . .
C19 C -0.37159(15) -0.2220(4) -0.22658(12) 0.0658(7) Uani 1 1 d . . .
H19 H -0.3395 -0.3335 -0.2187 0.079 Uiso 1 1 calc R . .
C22 C -0.36831(15) -0.0391(5) -0.18937(14) 0.0666(7) Uani 1 1 d . . .
H22 H -0.3339 -0.0282 -0.1563 0.080 Uiso 1 1 calc R . .
C23 C -0.42297(14) -0.2359(4) -0.27526(11) 0.0568(6) Uani 1 1 d . . .
H23 H -0.4251 -0.3583 -0.3002 0.068 Uiso 1 1 calc R . .
C25 C -0.63546(13) -0.2952(4) -0.47608(11) 0.0517(6) Uani 1 1 d . . .
C31 C -0.69560(16) -0.2017(5) -0.50506(13) 0.0701(7) Uani 1 1 d . . .
H31 H -0.7125 -0.0720 -0.4899 0.084 Uiso 1 1 calc R . .
C32 C -0.70666(17) -0.4853(6) -0.57964(16) 0.0842(10) Uani 1 1 d . . .
H32 H -0.7297 -0.5477 -0.6149 0.101 Uiso 1 1 calc R . .
C33 C -0.73104(18) -0.2988(6) -0.55638(13) 0.0791(9) Uani 1 1 d . . .
H33 H -0.7719 -0.2349 -0.5749 0.095 Uiso 1 1 calc R . .
C35 C -0.61281(17) -0.4888(5) -0.49970(17) 0.0799(9) Uani 1 1 d . . .
H35 H -0.5732 -0.5568 -0.4805 0.096 Uiso 1 1 calc R . .
C36 C -0.64778(19) -0.5826(6) -0.55108(17) 0.0992(12) Uani 1 1 d . . .
H36 H -0.6315 -0.7125 -0.5666 0.119 Uiso 1 1 calc R . .
N2 N -0.12619(12) -0.5797(3) -0.23035(9) 0.0591(6) Uani 1 1 d . . .
H2 H -0.0908 -0.5110 -0.2126 0.071 Uiso 1 1 calc R . .
O3 O -0.22676(11) -0.2746(3) -0.36965(9) 0.0715(6) Uani 1 1 d . . .
H3 H -0.1956 -0.3114 -0.3434 0.107 Uiso 1 1 calc R . .
N5 N -0.16802(11) -0.5021(3) -0.27901(10) 0.0601(6) Uani 1 1 d . . .
C8 C -0.27060(13) -0.6237(3) -0.34432(11) 0.0475(5) Uani 1 1 d . . .
C11 C -0.21619(13) -0.6542(4) -0.29269(11) 0.0482(5) Uani 1 1 d . . .
C12 C -0.37188(16) -0.7578(4) -0.40751(12) 0.0653(7) Uani 1 1 d . . .
H12 H -0.4046 -0.8662 -0.4169 0.078 Uiso 1 1 calc R . .
C13 C -0.32112(14) -0.7832(4) -0.35918(11) 0.0586(6) Uani 1 1 d . . .
H13 H -0.3202 -0.9089 -0.3358 0.070 Uiso 1 1 calc R . .
C15 C -0.37435(15) -0.5721(4) -0.44194(13) 0.0637(7) Uani 1 1 d . . .
H15 H -0.4090 -0.5549 -0.4745 0.076 Uiso 1 1 calc R . .
C18 C -0.11162(12) -0.8940(4) -0.15972(11) 0.0469(5) Uani 1 1 d . . .
C20 C -0.20397(13) -0.8298(4) -0.25220(11) 0.0508(5) Uani 1 1 d . . .
H20 H -0.2299 -0.9565 -0.2522 0.061 Uiso 1 1 calc R . .
C21 C -0.14635(13) -0.7772(3) -0.21283(11) 0.0478(5) Uani 1 1 d . . .
C24 C -0.27418(13) -0.4374(4) -0.38029(12) 0.0530(6) Uani 1 1 d . . .
C26 C -0.32609(15) -0.4123(4) -0.42851(13) 0.0627(7) Uani 1 1 d . . .
H26 H -0.3282 -0.2866 -0.4518 0.075 Uiso 1 1 calc R . .
C27 C -0.05398(16) -1.1191(5) -0.05563(13) 0.0699(8) Uani 1 1 d . . .
H27 H -0.0353 -1.1932 -0.0204 0.084 Uiso 1 1 calc R . .
C28 C -0.13707(14) -1.0947(4) -0.14426(13) 0.0599(7) Uani 1 1 d . . .
H28 H -0.1741 -1.1552 -0.1690 0.072 Uiso 1 1 calc R . .
C29 C -0.05559(14) -0.8101(4) -0.12191(12) 0.0617(7) Uani 1 1 d . . .
H29 H -0.0371 -0.6766 -0.1314 0.074 Uiso 1 1 calc R . .
C30 C -0.02729(16) -0.9229(5) -0.07059(13) 0.0704(8) Uani 1 1 d . . .
H30 H 0.0103 -0.8651 -0.0459 0.084 Uiso 1 1 calc R . .
C34 C -0.10831(17) -1.2058(4) -0.09274(14) 0.0713(8) Uani 1 1 d . . .
H34 H -0.1259 -1.3403 -0.0832 0.086 Uiso 1 1 calc R . .


_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
C1 C23 1.393(3) . ?
C1 C14 1.403(3) . ?
C1 C6 1.463(3) . ?
N4 N9 1.346(3) . ?
N4 C10 1.347(3) . ?
C6 N9 1.342(3) . ?
C6 C17 1.403(3) . ?
O7 C14 1.365(3) . ?
C10 C17 1.375(3) . ?
C10 C25 1.465(3) . ?
C14 C16 1.385(4) . ?
C16 C22 1.372(4) . ?
C19 C23 1.378(3) . ?
C19 C22 1.390(4) . ?
C25 C35 1.381(4) . ?
C25 C31 1.383(3) . ?
C31 C33 1.385(4) . ?
C32 C33 1.348(4) . ?
C32 C36 1.372(5) . ?
C35 C36 1.373(4) . ?
N2 C21 1.351(3) . ?
N2 N5 1.354(3) . ?
O3 C24 1.362(3) . ?
N5 C11 1.333(3) . ?
C8 C24 1.394(3) . ?
C8 C13 1.400(3) . ?
C8 C11 1.470(3) . ?
C11 C20 1.407(3) . ?
C12 C13 1.372(4) . ?
C12 C15 1.373(4) . ?
C15 C26 1.369(4) . ?
C18 C28 1.388(3) . ?
C18 C29 1.392(3) . ?
C18 C21 1.466(3) . ?
C20 C21 1.370(3) . ?
C24 C26 1.384(3) . ?
C27 C30 1.368(4) . ?
C27 C34 1.368(4) . ?
C28 C34 1.379(4) . ?
C29 C30 1.378(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
C23 C1 C14 117.6(2) . . ?
C23 C1 C6 120.6(2) . . ?
C14 C1 C6 121.8(2) . . ?
N9 N4 C10 113.1(2) . . ?
N9 C6 C17 109.8(2) . . ?
N9 C6 C1 119.5(2) . . ?
C17 C6 C1 130.7(2) . . ?
C6 N9 N4 105.14(19) . . ?
N4 C10 C17 105.6(2) . . ?
N4 C10 C25 121.6(2) . . ?
C17 C10 C25 132.8(2) . . ?
O7 C14 C16 117.2(2) . . ?
O7 C14 C1 122.1(2) . . ?
C16 C14 C1 120.7(2) . . ?
C22 C16 C14 120.3(3) . . ?
C10 C17 C6 106.4(2) . . ?
C23 C19 C22 119.1(3) . . ?
C16 C22 C19 120.4(3) . . ?
C19 C23 C1 122.0(2) . . ?
C35 C25 C31 117.6(2) . . ?
C35 C25 C10 120.6(2) . . ?
C31 C25 C10 121.8(2) . . ?
C25 C31 C33 120.9(3) . . ?
C33 C32 C36 119.8(3) . . ?
C32 C33 C31 120.4(3) . . ?
C36 C35 C25 121.1(3) . . ?
C32 C36 C35 120.2(3) . . ?
C21 N2 N5 112.3(2) . . ?
C11 N5 N2 105.54(19) . . ?
C24 C8 C13 117.4(2) . . ?
C24 C8 C11 122.0(2) . . ?
C13 C8 C11 120.6(2) . . ?
N5 C11 C20 109.8(2) . . ?
N5 C11 C8 120.3(2) . . ?
C20 C11 C8 129.9(2) . . ?
C13 C12 C15 120.0(3) . . ?
C12 C13 C8 121.3(2) . . ?
C26 C15 C12 120.3(2) . . ?
C28 C18 C29 117.7(2) . . ?
C28 C18 C21 119.2(2) . . ?
C29 C18 C21 123.1(2) . . ?
C21 C20 C11 106.5(2) . . ?
N2 C21 C20 105.9(2) . . ?
N2 C21 C18 123.2(2) . . ?
C20 C21 C18 130.8(2) . . ?
O3 C24 C26 117.7(2) . . ?
O3 C24 C8 121.5(2) . . ?
C26 C24 C8 120.8(2) . . ?
C15 C26 C24 120.1(2) . . ?
C30 C27 C34 119.6(3) . . ?
C34 C28 C18 121.0(3) . . ?
C30 C29 C18 120.7(2) . . ?
C27 C30 C29 120.6(3) . . ?
C27 C34 C28 120.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.74
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/ hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 1416487'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N3 O'
_chemical_formula_weight         279.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.9445(11)
_cell_length_b                   7.7091(14)
_cell_length_c                   15.328(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.942(3)
_cell_angle_gamma                90.00
_cell_volume                     700.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       slab-like
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Omega scan'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4099
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1910
_reflns_number_gt                1570
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXS-97 (Sheldrick, 1990)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_number_reflns         1910
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0251(5) 1.0626(4) 0.16165(18) 0.0470(9) Uani 1 1 d . . .
H1 H 0.0803 1.1253 0.2152 0.071 Uiso 1 1 d . . .
N1 N 0.3060(6) 1.0907(5) 0.3000(2) 0.0343(9) Uani 1 1 d . . .
N2 N 0.3963(6) 1.1100(5) 0.3830(2) 0.0352(9) Uani 1 1 d . . .
H2A H 0.3298 1.1820 0.4267 0.042 Uiso 1 1 d . . .
N3 N 1.0763(5) 0.9957(5) 0.7326(2) 0.0344(9) Uani 1 1 d . . .
C1 C 0.1836(7) 0.9619(6) 0.1267(2) 0.0327(10) Uani 1 1 d . . .
C2 C 0.1280(8) 0.8923(6) 0.0446(3) 0.0370(12) Uani 1 1 d . . .
H2 H -0.014(9) 0.908(7) 0.016(3) 0.064(16) Uiso 1 1 d . . .
C3 C 0.2794(8) 0.7868(6) 0.0055(3) 0.0431(13) Uani 1 1 d . . .
H3 H 0.246(6) 0.747(6) -0.048(2) 0.032(12) Uiso 1 1 d . . .
C4 C 0.4884(9) 0.7511(7) 0.0475(3) 0.0454(13) Uani 1 1 d . . .
H4 H 0.599(8) 0.674(7) 0.021(3) 0.061(16) Uiso 1 1 d . . .
C5 C 0.5411(8) 0.8212(6) 0.1294(3) 0.0393(12) Uani 1 1 d . . .
H5 H 0.683(7) 0.797(5) 0.154(2) 0.027(11) Uiso 1 1 d . . .
C6 C 0.3918(7) 0.9251(6) 0.1710(2) 0.0282(9) Uani 1 1 d . . .
C7 C 0.4459(6) 0.9833(5) 0.2618(2) 0.0278(9) Uani 1 1 d . . .
C8 C 0.6252(7) 0.9333(6) 0.3208(2) 0.0284(10) Uani 1 1 d . . .
H8 H 0.744(7) 0.856(7) 0.310(3) 0.054(14) Uiso 1 1 d . . .
C9 C 0.5904(6) 1.0168(5) 0.3991(2) 0.0268(9) Uani 1 1 d . . .
C10 C 0.7163(6) 1.0123(6) 0.4846(2) 0.0267(9) Uani 1 1 d . . .
C11 C 0.9196(7) 0.9265(6) 0.4966(3) 0.0318(10) Uani 1 1 d . . .
H11 H 0.992(6) 0.878(5) 0.449(2) 0.019(9) Uiso 1 1 d . . .
C12 C 1.0401(7) 0.9194(6) 0.5777(3) 0.0324(10) Uani 1 1 d . . .
H12 H 1.182(7) 0.856(6) 0.589(2) 0.038(12) Uiso 1 1 d . . .
C13 C 0.9587(6) 1.0002(5) 0.6514(2) 0.0285(9) Uani 1 1 d . . .
C14 C 0.7536(7) 1.0890(6) 0.6386(3) 0.0299(10) Uani 1 1 d . . .
H14 H 0.697(6) 1.153(5) 0.690(2) 0.016(9) Uiso 1 1 d . . .
C15 C 0.6364(7) 1.0951(6) 0.5580(3) 0.0299(10) Uani 1 1 d . . .
H15 H 0.496(7) 1.160(6) 0.553(3) 0.046(14) Uiso 1 1 d . . .
C16 C 0.9543(7) 1.0250(7) 0.8109(2) 0.0422(12) Uani 1 1 d . . .
H16A H 0.8895 1.1391 0.8087 0.063 Uiso 1 1 calc R . .
H16B H 1.0567 1.0148 0.8619 0.063 Uiso 1 1 calc R . .
H16C H 0.8367 0.9402 0.8135 0.063 Uiso 1 1 calc R . .
C17 C 1.2772(6) 0.8876(6) 0.7451(3) 0.0390(12) Uani 1 1 d . . .
H17A H 1.2353 0.7677 0.7392 0.058 Uiso 1 1 calc R . .
H17B H 1.3479 0.9073 0.8025 0.058 Uiso 1 1 calc R . .
H17C H 1.3805 0.9165 0.7019 0.058 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.359(5) . ?
O1 H1 0.9891 . ?
N1 C7 1.336(5) . ?
N1 N2 1.354(4) . ?
N2 C9 1.367(5) . ?
N2 H2A 0.9745 . ?
N3 C13 1.385(5) . ?
N3 C17 1.458(5) . ?
N3 C16 1.462(5) . ?
C1 C2 1.386(6) . ?
C1 C6 1.399(5) . ?
C2 C3 1.381(7) . ?
C2 H2 0.93(5) . ?
C3 C4 1.387(6) . ?
C3 H3 0.89(4) . ?
C4 C5 1.384(6) . ?
C4 H4 1.00(5) . ?
C5 C6 1.383(6) . ?
C5 H5 0.92(4) . ?
C6 C7 1.477(5) . ?
C7 C8 1.404(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.95(5) . ?
C9 C10 1.465(5) . ?
C10 C11 1.379(6) . ?
C10 C15 1.404(5) . ?
C11 C12 1.392(6) . ?
C11 H11 0.95(3) . ?
C12 C13 1.405(5) . ?
C12 H12 0.98(4) . ?
C13 C14 1.400(5) . ?
C14 C15 1.377(5) . ?
C14 H14 1.01(4) . ?
C15 H15 0.97(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 114.0 . . ?
C7 N1 N2 105.1(3) . . ?
N1 N2 C9 112.8(3) . . ?
N1 N2 H2A 123.7 . . ?
C9 N2 H2A 123.5 . . ?
C13 N3 C17 119.4(3) . . ?
C13 N3 C16 119.1(3) . . ?
C17 N3 C16 115.3(3) . . ?
O1 C1 C2 116.7(4) . . ?
O1 C1 C6 122.6(4) . . ?
C2 C1 C6 120.7(4) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 118(3) . . ?
C1 C2 H2 122(3) . . ?
C2 C3 C4 120.3(5) . . ?
C2 C3 H3 120(3) . . ?
C4 C3 H3 120(3) . . ?
C5 C4 C3 118.9(5) . . ?
C5 C4 H4 119(3) . . ?
C3 C4 H4 122(3) . . ?
C6 C5 C4 122.2(5) . . ?
C6 C5 H5 122(2) . . ?
C4 C5 H5 116(2) . . ?
C5 C6 C1 117.9(4) . . ?
C5 C6 C7 120.4(4) . . ?
C1 C6 C7 121.6(4) . . ?
N1 C7 C8 110.8(3) . . ?
N1 C7 C6 120.0(4) . . ?
C8 C7 C6 129.1(4) . . ?
C9 C8 C7 106.1(4) . . ?
C9 C8 H8 127(3) . . ?
C7 C8 H8 127(3) . . ?
N2 C9 C8 105.1(3) . . ?
N2 C9 C10 123.1(3) . . ?
C8 C9 C10 131.7(4) . . ?
C11 C10 C15 116.9(4) . . ?
C11 C10 C9 121.3(3) . . ?
C15 C10 C9 121.8(4) . . ?
C10 C11 C12 122.0(4) . . ?
C10 C11 H11 122(2) . . ?
C12 C11 H11 116(2) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 124(2) . . ?
C13 C12 H12 115(2) . . ?
N3 C13 C14 121.2(3) . . ?
N3 C13 C12 122.1(4) . . ?
C14 C13 C12 116.7(3) . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 121(2) . . ?
C13 C14 H14 118(2) . . ?
C14 C15 C10 121.7(4) . . ?
C14 C15 H15 118(2) . . ?
C10 C15 H15 121(2) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.058
