# 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_pn100216o
_database_code_depnum_ccdc_archive 'CCDC 1494536'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.5413(3)
_cell_length_b                   3.77083(7)
_cell_length_c                   18.5858(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.6727(17)
_cell_angle_gamma                90
_cell_volume                     1296.78(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    7590
_cell_measurement_theta_min      2.998
_cell_measurement_theta_max      32.951

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Agilent SuperNova dual radiation CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            17616
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         33.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4512
_reflns_number_gt                3791
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Rigaku, 2015)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku, 2015)'
_computing_data_reduction        'CrysAlis PRO (Rigaku, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.5804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4512
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.004
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42868(6) -0.2120(3) 0.65211(6) 0.0222(2) Uani 1 1 d . . . . .
C2 C 0.36194(6) -0.0386(3) 0.64899(6) 0.0236(2) Uani 1 1 d . . . . .
H2 H 0.3385 0.0179 0.6035 0.028 Uiso 1 1 calc R U . . .
C3 C 0.32978(6) 0.0515(3) 0.71141(7) 0.0248(2) Uani 1 1 d . . . . .
H3 H 0.2845 0.1698 0.7086 0.030 Uiso 1 1 calc R U . . .
C4 C 0.36361(6) -0.0305(3) 0.77903(6) 0.0240(2) Uani 1 1 d . . . . .
C5 C 0.43081(6) -0.2032(3) 0.78226(6) 0.0255(2) Uani 1 1 d . . . . .
H5 H 0.4544 -0.2602 0.8277 0.031 Uiso 1 1 calc R U . . .
C6 C 0.46266(6) -0.2900(3) 0.71974(7) 0.0248(2) Uani 1 1 d . . . . .
H6 H 0.5084 -0.4047 0.7225 0.030 Uiso 1 1 calc R U . . .
C7 C 0.46202(6) -0.3224(3) 0.58655(6) 0.0240(2) Uani 1 1 d . . . . .
C11 C 0.15469(6) 0.2284(3) 0.42876(6) 0.0221(2) Uani 1 1 d . . . . .
C12 C 0.22147(6) 0.3171(4) 0.46337(7) 0.0254(2) Uani 1 1 d . . . . .
H12 H 0.2230 0.4338 0.5087 0.030 Uiso 1 1 calc R U . . .
C13 C 0.28505(6) 0.2375(4) 0.43254(7) 0.0273(2) Uani 1 1 d . . . . .
H13 H 0.3299 0.2983 0.4569 0.033 Uiso 1 1 calc R U . . .
C14 C 0.28401(6) 0.0673(4) 0.36549(7) 0.0261(2) Uani 1 1 d . . . . .
C15 C 0.21703(7) -0.0242(3) 0.33089(7) 0.0263(2) Uani 1 1 d . . . . .
H15 H 0.2155 -0.1416 0.2856 0.032 Uiso 1 1 calc R U . . .
C16 C 0.15338(6) 0.0550(3) 0.36221(6) 0.0235(2) Uani 1 1 d . . . . .
H16 H 0.1084 -0.0088 0.3383 0.028 Uiso 1 1 calc R U . . .
C17 C 0.08793(6) 0.3298(3) 0.46134(6) 0.0234(2) Uani 1 1 d . . . . .
N8 N 0.32990(7) 0.0473(4) 0.84083(6) 0.0327(3) Uani 1 1 d . . . . .
H8A H 0.3549(11) 0.030(6) 0.8810(12) 0.049 Uiso 1 1 d . U . . .
H8B H 0.2956(11) 0.201(6) 0.8374(11) 0.049 Uiso 1 1 d . U . . .
N18 N 0.34715(7) 0.0025(4) 0.33266(8) 0.0381(3) Uani 1 1 d . . . . .
H18A H 0.3437(11) -0.185(6) 0.2998(12) 0.057 Uiso 1 1 d . U . . .
H18B H 0.3875(12) 0.032(6) 0.3581(12) 0.057 Uiso 1 1 d . U . . .
O9 O 0.52144(5) -0.4752(3) 0.58803(5) 0.0325(2) Uani 1 1 d . . . . .
O10 O 0.42453(5) -0.2541(3) 0.52590(5) 0.0333(2) Uani 1 1 d . . . . .
H10 H 0.4464 -0.3348 0.4912 0.050 Uiso 1 1 calc R U . . .
O19 O 0.08696(5) 0.4976(3) 0.51831(5) 0.0309(2) Uani 1 1 d . . . . .
O20 O 0.02773(5) 0.2340(3) 0.42466(5) 0.0322(2) Uani 1 1 d . . . . .
H20 H -0.0080 0.3128 0.4452 0.048 Uiso 1 1 calc R U . . .


_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 C2 1.3977(16) . ?
C1 C6 1.4007(16) . ?
C1 C7 1.4616(17) . ?
C2 C3 1.3804(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4028(17) . ?
C3 H3 0.9500 . ?
C4 N8 1.3740(17) . ?
C4 C5 1.4037(17) . ?
C5 C6 1.3763(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O9 1.2420(15) . ?
C7 O10 1.3112(14) . ?
C11 C16 1.3979(16) . ?
C11 C12 1.3989(16) . ?
C11 C17 1.4633(16) . ?
C12 C13 1.3765(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4006(18) . ?
C13 H13 0.9500 . ?
C14 N18 1.3761(17) . ?
C14 C15 1.4045(17) . ?
C15 C16 1.3816(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O19 1.2347(15) . ?
C17 O20 1.3204(14) . ?
N8 H8A 0.86(2) . ?
N8 H8B 0.86(2) . ?
N18 H18A 0.93(2) . ?
N18 H18B 0.87(2) . ?
O10 H10 0.8400 . ?
O20 H20 0.8400 . ?

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 C1 C6 118.79(11) . . ?
C2 C1 C7 121.28(11) . . ?
C6 C1 C7 119.90(11) . . ?
C3 C2 C1 120.62(11) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.42(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N8 C4 C3 120.04(12) . . ?
N8 C4 C5 120.89(11) . . ?
C3 C4 C5 119.03(11) . . ?
C6 C5 C4 120.14(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 121.00(11) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O9 C7 O10 122.06(11) . . ?
O9 C7 C1 122.37(11) . . ?
O10 C7 C1 115.56(11) . . ?
C16 C11 C12 118.90(11) . . ?
C16 C11 C17 121.42(10) . . ?
C12 C11 C17 119.64(11) . . ?
C13 C12 C11 120.85(11) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.46(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
N18 C14 C13 120.81(12) . . ?
N18 C14 C15 120.38(13) . . ?
C13 C14 C15 118.77(11) . . ?
C16 C15 C14 120.54(12) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.47(11) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
O19 C17 O20 121.65(11) . . ?
O19 C17 C11 123.22(11) . . ?
O20 C17 C11 115.11(10) . . ?
C4 N8 H8A 117.6(14) . . ?
C4 N8 H8B 117.2(13) . . ?
H8A N8 H8B 118.2(19) . . ?
C14 N18 H18A 113.6(13) . . ?
C14 N18 H18B 117.7(15) . . ?
H18A N18 H18B 118(2) . . ?
C7 O10 H10 109.5 . . ?
C17 O20 H20 109.5 . . ?

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
C6 C1 C2 C3 -0.55(18) . . . . ?
C7 C1 C2 C3 177.41(12) . . . . ?
C1 C2 C3 C4 -0.13(19) . . . . ?
C2 C3 C4 N8 -177.38(12) . . . . ?
C2 C3 C4 C5 0.43(19) . . . . ?
N8 C4 C5 C6 177.75(13) . . . . ?
C3 C4 C5 C6 -0.04(19) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C2 C1 C6 C5 0.95(19) . . . . ?
C7 C1 C6 C5 -177.04(12) . . . . ?
C2 C1 C7 O9 179.62(12) . . . . ?
C6 C1 C7 O9 -2.44(19) . . . . ?
C2 C1 C7 O10 -1.33(18) . . . . ?
C6 C1 C7 O10 176.62(11) . . . . ?
C16 C11 C12 C13 0.35(19) . . . . ?
C17 C11 C12 C13 -177.41(12) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 N18 176.77(13) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
N18 C14 C15 C16 -177.05(13) . . . . ?
C13 C14 C15 C16 0.55(19) . . . . ?
C14 C15 C16 C11 0.17(19) . . . . ?
C12 C11 C16 C15 -0.62(18) . . . . ?
C17 C11 C16 C15 177.10(12) . . . . ?
C16 C11 C17 O19 -176.50(12) . . . . ?
C12 C11 C17 O19 1.21(19) . . . . ?
C16 C11 C17 O20 2.34(18) . . . . ?
C12 C11 C17 O20 -179.96(11) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.049


_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_pn070216o
_database_code_depnum_ccdc_archive 'CCDC 1494537'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.49441(10)
_cell_length_b                   11.06430(14)
_cell_length_c                   13.80360(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.9142(11)
_cell_angle_gamma                90
_cell_volume                     1143.12(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    13370
_cell_measurement_theta_min      2.953
_cell_measurement_theta_max      37.401

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            28870
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.360
_diffrn_reflns_theta_max         37.825
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5891
_reflns_number_gt                4768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+0.1423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5891
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74022(11) 0.39061(7) 0.80827(5) 0.02409(13) Uani 1 1 d . . . . .
H1 H 0.6545 0.3911 0.8567 0.029 Uiso 1 1 calc R U . . .
C2 C 0.90103(11) 0.44957(7) 0.82584(5) 0.02661(14) Uani 1 1 d . . . . .
H2 H 0.9248 0.4907 0.8855 0.032 Uiso 1 1 calc R U . . .
C3 C 1.02765(11) 0.44855(7) 0.75598(6) 0.02665(14) Uani 1 1 d . . . . .
H3 H 1.1386 0.4888 0.7678 0.032 Uiso 1 1 calc R U . . .
C4 C 0.99222(10) 0.38867(7) 0.66866(5) 0.02336(13) Uani 1 1 d . . . . .
H4 H 1.0788 0.3886 0.6207 0.028 Uiso 1 1 calc R U . . .
C6 C 0.68993(11) 0.36166(7) 0.40975(5) 0.02497(13) Uani 1 1 d . . . . .
H6 H 0.8106 0.3710 0.3931 0.030 Uiso 1 1 calc R U . . .
C7 C 0.55207(12) 0.39719(7) 0.34488(6) 0.02925(16) Uani 1 1 d . . . . .
H7 H 0.5781 0.4296 0.2835 0.035 Uiso 1 1 calc R U . . .
C8 C 0.37629(12) 0.38510(7) 0.37029(6) 0.02829(16) Uani 1 1 d . . . . .
H8 H 0.2816 0.4088 0.3260 0.034 Uiso 1 1 calc R U . . .
C9 C 0.33866(10) 0.33854(7) 0.45998(6) 0.02578(14) Uani 1 1 d . . . . .
H9 H 0.2177 0.3312 0.4767 0.031 Uiso 1 1 calc R U . . .
C10 C 0.42863(10) 0.25813(7) 0.62198(5) 0.02437(13) Uani 1 1 d . . . . .
H10 H 0.3188 0.2158 0.6251 0.029 Uiso 1 1 calc R U . . .
C11 C 0.52624(10) 0.27196(7) 0.70568(5) 0.02409(13) Uani 1 1 d . . . . .
H11 H 0.4757 0.2402 0.7621 0.029 Uiso 1 1 calc R U . . .
C12 C 0.83078(9) 0.32893(6) 0.65119(4) 0.01843(11) Uani 1 1 d . . . . .
C13 C 0.65153(9) 0.31233(6) 0.49919(5) 0.01973(11) Uani 1 1 d . . . . .
C14 C 0.47511(9) 0.30191(6) 0.52681(5) 0.02075(12) Uani 1 1 d . . . . .
C15 C 0.70052(9) 0.32987(6) 0.72038(5) 0.01969(11) Uani 1 1 d . . . . .
C16 C 0.88142(9) 0.16058(6) 0.54142(5) 0.01819(11) Uani 1 1 d . . . . .
N5 N 0.79466(8) 0.26689(5) 0.56145(4) 0.02005(11) Uani 1 1 d . . . . .
N18 N 0.81968(9) 0.10040(6) 0.46143(5) 0.02729(14) Uani 1 1 d . . . . .
H18B H 0.8702 0.0321 0.4450 0.033 Uiso 1 1 calc R U . . .
H18A H 0.7289 0.1295 0.4258 0.033 Uiso 1 1 calc R U . . .
O17 O 1.00836(7) 0.12351(5) 0.59381(4) 0.02388(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3811(12) . ?
C1 C15 1.4054(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.3869(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.3892(10) . ?
C3 H3 0.9500 . ?
C4 C12 1.3890(10) . ?
C4 H4 0.9500 . ?
C6 C7 1.3891(11) . ?
C6 C13 1.3932(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.3868(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.3832(12) . ?
C8 H8 0.9500 . ?
C9 C14 1.4018(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.3444(10) . ?
C10 C14 1.4588(10) . ?
C10 H10 0.9500 . ?
C11 C15 1.4597(10) . ?
C11 H11 0.9500 . ?
C12 C15 1.4000(9) . ?
C12 N5 1.4300(8) . ?
C13 C14 1.3993(10) . ?
C13 N5 1.4313(8) . ?
C16 O17 1.2355(8) . ?
C16 N18 1.3508(9) . ?
C16 N5 1.3788(8) . ?
N18 H18B 0.8800 . ?
N18 H18A 0.8800 . ?

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 C1 C15 121.47(7) . . ?
C2 C1 H1 119.3 . . ?
C15 C1 H1 119.3 . . ?
C1 C2 C3 119.73(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.99(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C12 C4 C3 120.26(7) . . ?
C12 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C7 C6 C13 120.11(7) . . ?
C7 C6 H6 119.9 . . ?
C13 C6 H6 119.9 . . ?
C8 C7 C6 119.65(7) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.12(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C14 121.44(7) . . ?
C8 C9 H9 119.3 . . ?
C14 C9 H9 119.3 . . ?
C11 C10 C14 126.28(7) . . ?
C11 C10 H10 116.9 . . ?
C14 C10 H10 116.9 . . ?
C10 C11 C15 127.83(7) . . ?
C10 C11 H11 116.1 . . ?
C15 C11 H11 116.1 . . ?
C4 C12 C15 120.63(6) . . ?
C4 C12 N5 120.24(6) . . ?
C15 C12 N5 119.12(6) . . ?
C6 C13 C14 120.96(6) . . ?
C6 C13 N5 119.17(6) . . ?
C14 C13 N5 119.81(6) . . ?
C13 C14 C9 117.68(7) . . ?
C13 C14 C10 123.02(6) . . ?
C9 C14 C10 119.28(7) . . ?
C12 C15 C1 117.91(7) . . ?
C12 C15 C11 123.50(6) . . ?
C1 C15 C11 118.59(6) . . ?
O17 C16 N18 122.44(6) . . ?
O17 C16 N5 121.52(6) . . ?
N18 C16 N5 116.04(6) . . ?
C16 N5 C12 120.85(5) . . ?
C16 N5 C13 121.73(5) . . ?
C12 N5 C13 117.04(5) . . ?
C16 N18 H18B 120.0 . . ?
C16 N18 H18A 120.0 . . ?
H18B N18 H18A 120.0 . . ?

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
C15 C1 C2 C3 -0.52(11) . . . . ?
C1 C2 C3 C4 0.19(12) . . . . ?
C2 C3 C4 C12 -0.47(12) . . . . ?
C13 C6 C7 C8 1.03(12) . . . . ?
C6 C7 C8 C9 0.38(12) . . . . ?
C7 C8 C9 C14 -0.42(12) . . . . ?
C14 C10 C11 C15 -1.85(13) . . . . ?
C3 C4 C12 C15 1.10(11) . . . . ?
C3 C4 C12 N5 -179.75(6) . . . . ?
C7 C6 C13 C14 -2.44(11) . . . . ?
C7 C6 C13 N5 174.73(7) . . . . ?
C6 C13 C14 C9 2.35(10) . . . . ?
N5 C13 C14 C9 -174.80(6) . . . . ?
C6 C13 C14 C10 -175.97(7) . . . . ?
N5 C13 C14 C10 6.87(10) . . . . ?
C8 C9 C14 C13 -0.93(11) . . . . ?
C8 C9 C14 C10 177.46(7) . . . . ?
C11 C10 C14 C13 31.24(11) . . . . ?
C11 C10 C14 C9 -147.06(8) . . . . ?
C4 C12 C15 C1 -1.39(10) . . . . ?
N5 C12 C15 C1 179.44(6) . . . . ?
C4 C12 C15 C11 178.21(7) . . . . ?
N5 C12 C15 C11 -0.95(10) . . . . ?
C2 C1 C15 C12 1.12(10) . . . . ?
C2 C1 C15 C11 -178.51(7) . . . . ?
C10 C11 C15 C12 -32.12(12) . . . . ?
C10 C11 C15 C1 147.48(8) . . . . ?
O17 C16 N5 C12 -9.41(11) . . . . ?
N18 C16 N5 C12 170.82(7) . . . . ?
O17 C16 N5 C13 177.83(7) . . . . ?
N18 C16 N5 C13 -1.94(10) . . . . ?
C4 C12 N5 C16 71.70(9) . . . . ?
C15 C12 N5 C16 -109.13(8) . . . . ?
C4 C12 N5 C13 -115.21(7) . . . . ?
C15 C12 N5 C13 63.96(8) . . . . ?
C6 C13 N5 C16 -72.72(9) . . . . ?
C14 C13 N5 C16 104.49(8) . . . . ?
C6 C13 N5 C12 114.26(7) . . . . ?
C14 C13 N5 C12 -68.54(8) . . . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropanol'
####################################################################### 
# 
# 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_pn040216o
_database_code_depnum_ccdc_archive 'CCDC 1494538'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12.33 N2 O1.17'
_chemical_formula_weight         239.27

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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   35.2832(9)
_cell_length_b                   35.2832(9)
_cell_length_c                   5.20165(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5608.0(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    3545
_cell_measurement_theta_min      4.303
_cell_measurement_theta_max      73.840

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             2262
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_reflns_number            5908
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_av_R_equivalents  0.0086
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         74.211
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2482
_reflns_number_gt                2277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1062P)²+3.5824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2482
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.009
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23976(5) -0.02148(5) 0.2886(3) 0.0405(4) Uani 1 1 d . . . . .
H1 H 0.2238 -0.0468 0.3925 0.049 Uiso 1 1 calc R U . . .
C2 C 0.26572(5) -0.02227(5) 0.0914(3) 0.0413(4) Uani 1 1 d . . . . .
H2 H 0.2673 -0.0480 0.0598 0.050 Uiso 1 1 calc R U . . .
C3 C 0.28931(5) 0.01446(5) -0.0589(3) 0.0393(4) Uani 1 1 d . . . . .
H3 H 0.3069 0.0140 -0.1954 0.047 Uiso 1 1 calc R U . . .
C4 C 0.28732(5) 0.05211(5) -0.0108(3) 0.0363(4) Uani 1 1 d . . . . .
H4 H 0.3037 0.0774 -0.1138 0.044 Uiso 1 1 calc R U . . .
C6 C 0.21842(7) 0.11760(6) -0.0050(3) 0.0488(4) Uani 1 1 d . . . . .
H6 H 0.2438 0.1357 -0.1041 0.059 Uiso 1 1 calc R U . . .
C7 C 0.17995(8) 0.11778(7) -0.0520(4) 0.0607(6) Uani 1 1 d . . . . .
H7 H 0.1789 0.1362 -0.1818 0.073 Uiso 1 1 calc R U . . .
C8 C 0.14297(8) 0.09098(7) 0.0910(4) 0.0626(6) Uani 1 1 d . . . . .
H8 H 0.1164 0.0907 0.0573 0.075 Uiso 1 1 calc R U . . .
C9 C 0.14457(6) 0.06464(7) 0.2826(4) 0.0546(5) Uani 1 1 d . . . . .
H9 H 0.1191 0.0468 0.3815 0.065 Uiso 1 1 calc R U . . .
C10 C 0.18334(5) 0.03479(5) 0.5339(3) 0.0411(4) Uani 1 1 d . . . . .
H10 H 0.1650 0.0301 0.6781 0.049 Uiso 1 1 calc R U . . .
C11 C 0.20643(5) 0.01417(5) 0.5371(3) 0.0388(4) Uani 1 1 d . . . . .
H11 H 0.2030 -0.0033 0.6839 0.047 Uiso 1 1 calc R U . . .
C12 C 0.26145(4) 0.05274(4) 0.1877(3) 0.0294(3) Uani 1 1 d . . . . .
C13 C 0.22010(5) 0.09110(5) 0.1865(3) 0.0347(3) Uani 1 1 d . . . . .
C14 C 0.18315(5) 0.06379(5) 0.3333(3) 0.0385(4) Uani 1 1 d . . . . .
C15 C 0.23645(5) 0.01569(5) 0.3382(3) 0.0322(3) Uani 1 1 d . . . . .
C16 C 0.29220(5) 0.12351(4) 0.3942(3) 0.0319(3) Uani 1 1 d . . . . .
N5 N 0.26039(4) 0.09216(4) 0.2393(2) 0.0325(3) Uani 1 1 d . . . . .
N18 N 0.28820(5) 0.15837(4) 0.4501(3) 0.0461(4) Uani 1 1 d . . . . .
H18A H 0.3077 0.1793 0.5491 0.055 Uiso 1 1 calc R U . . .
H18B H 0.2661 0.1604 0.3878 0.055 Uiso 1 1 calc R U . . .
O17 O 0.32263(4) 0.11915(4) 0.4769(2) 0.0410(3) Uani 1 1 d . . . . .
O21 O 0.0250(5) 0.0104(10) 0.640(5) 0.176(11) Uani 0.1667 1 d . . P . .


_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 C2 1.385(2) . ?
C1 C15 1.398(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C12 1.386(2) . ?
C4 H4 0.9500 . ?
C6 C7 1.382(3) . ?
C6 C13 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C14 1.401(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.336(2) . ?
C10 C14 1.464(2) . ?
C10 H10 0.9500 . ?
C11 C15 1.462(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.3954(19) . ?
C12 N5 1.4352(17) . ?
C13 C14 1.398(2) . ?
C13 N5 1.4296(18) . ?
C16 O17 1.2356(19) . ?
C16 N18 1.3382(19) . ?
C16 N5 1.3752(18) . ?
N18 H18A 0.8800 . ?
N18 H18B 0.8800 . ?
O21 O21 1.33(3) 2 ?
O21 O21 1.33(3) 3 ?
O21 O21 1.65(5) 12_556 ?
O21 O21 1.65(5) 11_556 ?

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 C1 C15 121.47(14) . . ?
C2 C1 H1 119.3 . . ?
C15 C1 H1 119.3 . . ?
C3 C2 C1 119.67(14) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.10(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C12 C4 C3 119.92(14) . . ?
C12 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C7 C6 C13 120.19(19) . . ?
C7 C6 H6 119.9 . . ?
C13 C6 H6 119.9 . . ?
C6 C7 C8 119.63(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.32(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C14 121.1(2) . . ?
C8 C9 H9 119.5 . . ?
C14 C9 H9 119.5 . . ?
C11 C10 C14 127.35(14) . . ?
C11 C10 H10 116.3 . . ?
C14 C10 H10 116.3 . . ?
C10 C11 C15 126.77(14) . . ?
C10 C11 H11 116.6 . . ?
C15 C11 H11 116.6 . . ?
C4 C12 C15 121.05(13) . . ?
C4 C12 N5 119.45(12) . . ?
C15 C12 N5 119.50(13) . . ?
C6 C13 C14 121.13(15) . . ?
C6 C13 N5 119.80(15) . . ?
C14 C13 N5 119.05(13) . . ?
C13 C14 C9 117.62(16) . . ?
C13 C14 C10 122.85(14) . . ?
C9 C14 C10 119.53(16) . . ?
C12 C15 C1 117.74(13) . . ?
C12 C15 C11 122.58(13) . . ?
C1 C15 C11 119.66(13) . . ?
O17 C16 N18 122.44(13) . . ?
O17 C16 N5 120.96(13) . . ?
N18 C16 N5 116.60(13) . . ?
C16 N5 C13 122.32(12) . . ?
C16 N5 C12 118.86(12) . . ?
C13 N5 C12 116.49(11) . . ?
C16 N18 H18A 120.0 . . ?
C16 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
O21 O21 O21 60.001(14) 2 3 ?
O21 O21 O21 66.2(9) 2 12_556 ?
O21 O21 O21 90.000(9) 3 12_556 ?
O21 O21 O21 90.000(6) 2 11_556 ?
O21 O21 O21 66.2(9) 3 11_556 ?
O21 O21 O21 47.6(18) 12_556 11_556 ?

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
C15 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C12 -0.3(2) . . . . ?
C13 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 C14 -1.2(3) . . . . ?
C14 C10 C11 C15 -0.7(3) . . . . ?
C3 C4 C12 C15 -1.3(2) . . . . ?
C3 C4 C12 N5 178.64(13) . . . . ?
C7 C6 C13 C14 0.7(2) . . . . ?
C7 C6 C13 N5 -178.02(14) . . . . ?
C6 C13 C14 C9 -0.9(2) . . . . ?
N5 C13 C14 C9 177.85(13) . . . . ?
C6 C13 C14 C10 178.89(14) . . . . ?
N5 C13 C14 C10 -2.3(2) . . . . ?
C8 C9 C14 C13 1.2(2) . . . . ?
C8 C9 C14 C10 -178.67(16) . . . . ?
C11 C10 C14 C13 -33.1(2) . . . . ?
C11 C10 C14 C9 146.67(18) . . . . ?
C4 C12 C15 C1 2.5(2) . . . . ?
N5 C12 C15 C1 -177.45(12) . . . . ?
C4 C12 C15 C11 -175.55(13) . . . . ?
N5 C12 C15 C11 4.5(2) . . . . ?
C2 C1 C15 C12 -2.2(2) . . . . ?
C2 C1 C15 C11 175.94(14) . . . . ?
C10 C11 C15 C12 32.8(2) . . . . ?
C10 C11 C15 C1 -145.26(17) . . . . ?
O17 C16 N5 C13 165.96(13) . . . . ?
N18 C16 N5 C13 -13.8(2) . . . . ?
O17 C16 N5 C12 3.9(2) . . . . ?
N18 C16 N5 C12 -175.81(13) . . . . ?
C6 C13 N5 C16 82.62(18) . . . . ?
C14 C13 N5 C16 -96.17(16) . . . . ?
C6 C13 N5 C12 -114.95(15) . . . . ?
C14 C13 N5 C12 66.26(17) . . . . ?
C4 C12 N5 C16 -84.96(16) . . . . ?
C15 C12 N5 C16 94.99(16) . . . . ?
C4 C12 N5 C13 111.98(15) . . . . ?
C15 C12 N5 C13 -68.07(17) . . . . ?

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.083


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropanol'
