# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_vbchem152_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1566643'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        vbchem152_0m_a
_chemical_name_common            vbchem152_0m_a
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O'
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.5942(6)
_cell_length_b                   9.7522(7)
_cell_length_c                   10.4775(6)
_cell_angle_alpha                101.242(3)
_cell_angle_beta                 98.692(3)
_cell_angle_gamma                100.998(3)
_cell_volume                     925.62(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3230
_cell_measurement_theta_min      2.205
_cell_measurement_theta_max      28.631

_exptl_crystal_description       vbchem152_0m_a
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  char
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28082
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         28.631
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4749
_reflns_number_gt                3230
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.6685P] 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         4665
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.2730
_refine_ls_wR_factor_gt          0.2333
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6690(2) 0.3650(2) 0.57513(18) 0.0511(5) Uani 1 1 d . . . . .
N2 N 0.5503(2) 0.4237(3) 0.2528(2) 0.0461(6) Uani 1 1 d . . . . .
N1 N 0.5549(2) 0.2427(3) 0.3546(2) 0.0460(6) Uani 1 1 d . . . . .
C17 C 0.8264(3) 0.3385(3) 0.7582(2) 0.0386(5) Uani 1 1 d . . . . .
C15 C 0.8062(3) 0.3445(3) 0.6172(2) 0.0398(6) Uani 1 1 d . . . . .
C9 C 0.6911(3) 0.6294(3) 0.4321(3) 0.0427(6) Uani 1 1 d . . . . .
C8 C 0.6239(3) 0.4759(3) 0.3818(2) 0.0406(6) Uani 1 1 d . . . . .
C18 C 0.7392(3) 0.3931(3) 0.8399(3) 0.0442(6) Uani 1 1 d . . . . .
H14 H 0.6662 0.4342 0.8060 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5091(3) 0.2823(3) 0.2388(3) 0.0430(6) Uani 1 1 d . . . . .
C7 C 0.6264(3) 0.3676(3) 0.4455(2) 0.0424(6) Uani 1 1 d . . . . .
C19 C 0.7611(3) 0.3863(3) 0.9722(3) 0.0505(7) Uani 1 1 d . . . . .
H15 H 0.7023 0.4243 1.0258 0.061 Uiso 1 1 calc R U . . .
C20 C 0.8663(3) 0.3256(4) 1.0269(3) 0.0526(7) Uani 1 1 d . . . . .
C22 C 0.9326(3) 0.2784(4) 0.8120(3) 0.0536(7) Uani 1 1 d . . . . .
H17 H 0.9925 0.2417 0.7589 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7483(3) 0.6879(3) 0.5667(3) 0.0536(7) Uani 1 1 d . . . . .
H11 H 0.7425 0.6298 0.6273 0.064 Uiso 1 1 calc R U . . .
C4 C 0.4275(3) 0.1753(4) 0.1278(3) 0.0578(8) Uani 1 1 d . . . . .
C16 C 0.8988(3) 0.3340(4) 0.5389(3) 0.0574(8) Uani 1 1 d . . . . .
H13 H 0.8739 0.3403 0.4512 0.069 Uiso 1 1 calc R U . . .
H12 H 0.9898 0.3203 0.5706 0.069 Uiso 1 1 calc R U . . .
C21 C 0.9522(3) 0.2717(4) 0.9452(3) 0.0599(8) Uani 1 1 d . . . . .
H16 H 1.0246 0.2300 0.9792 0.072 Uiso 1 1 calc R U . . .
C14 C 0.7028(3) 0.7205(4) 0.3455(3) 0.0588(8) Uani 1 1 d . . . . .
H7 H 0.6653 0.6840 0.2554 0.071 Uiso 1 1 calc R U . . .
C1 C 0.5297(4) 0.1040(4) 0.3660(4) 0.0612(8) Uani 1 1 d . . . . .
H1 H 0.5631 0.0810 0.4454 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8135(4) 0.8322(4) 0.6097(4) 0.0664(9) Uani 1 1 d . . . . .
H10 H 0.8510 0.8711 0.6995 0.080 Uiso 1 1 calc R U . . .
C2 C 0.4556(4) 0.0011(4) 0.2599(4) 0.0715(10) Uani 1 1 d . . . . .
H2 H 0.4395 -0.0945 0.2655 0.086 Uiso 1 1 calc R U . . .
C12 C 0.8233(4) 0.9179(4) 0.5219(4) 0.0714(10) Uani 1 1 d . . . . .
H9 H 0.8679 1.0149 0.5519 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7684(4) 0.8628(4) 0.3905(5) 0.0738(10) Uani 1 1 d . . . . .
H8 H 0.7755 0.9220 0.3311 0.089 Uiso 1 1 calc R U . . .
C3 C 0.4021(4) 0.0353(4) 0.1410(4) 0.0737(11) Uani 1 1 d . . . . .
H3 H 0.3485 -0.0377 0.0698 0.088 Uiso 1 1 calc R U . . .
C23 C 0.8841(4) 0.3174(5) 1.1700(3) 0.0740(11) Uani 1 1 d . . . . .
H18 H 0.8302 0.2263 1.1764 0.111 Uiso 1 1 calc R U . . .
H19 H 0.8489 0.3930 1.2190 0.111 Uiso 1 1 calc R U . . .
H20 H 0.9847 0.3279 1.2059 0.111 Uiso 1 1 calc R U . . .
C6 C 0.3745(4) 0.2195(5) 0.0033(4) 0.0827(12) Uani 1 1 d . . . . .
H5 H 0.4555 0.2554 -0.0340 0.124 Uiso 1 1 calc R U . . .
H4 H 0.3225 0.2933 0.0237 0.124 Uiso 1 1 calc R U . . .
H6 H 0.3114 0.1381 -0.0595 0.124 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
O1 C7 1.365(3) . ?
O1 C15 1.387(3) . ?
N2 C5 1.332(4) . ?
N2 C8 1.375(3) . ?
N1 C1 1.360(4) . ?
N1 C7 1.375(4) . ?
N1 C5 1.378(4) . ?
C17 C22 1.372(4) . ?
C17 C18 1.387(3) . ?
C17 C15 1.475(3) . ?
C15 C16 1.303(4) . ?
C9 C14 1.390(4) . ?
C9 C10 1.396(4) . ?
C9 C8 1.469(4) . ?
C8 C7 1.357(4) . ?
C18 C19 1.387(4) . ?
C18 H14 0.9300 . ?
C5 C4 1.413(4) . ?
C19 C20 1.373(4) . ?
C19 H15 0.9300 . ?
C20 C21 1.375(4) . ?
C20 C23 1.502(4) . ?
C22 C21 1.395(4) . ?
C22 H17 0.9300 . ?
C10 C11 1.380(5) . ?
C10 H11 0.9300 . ?
C4 C3 1.378(5) . ?
C4 C6 1.499(5) . ?
C16 H13 0.9300 . ?
C16 H12 0.9300 . ?
C21 H16 0.9300 . ?
C14 C13 1.365(5) . ?
C14 H7 0.9300 . ?
C1 C2 1.343(5) . ?
C1 H1 0.9300 . ?
C11 C12 1.360(6) . ?
C11 H10 0.9300 . ?
C2 C3 1.400(6) . ?
C2 H2 0.9300 . ?
C12 C13 1.358(6) . ?
C12 H9 0.9300 . ?
C13 H8 0.9300 . ?
C3 H3 0.9300 . ?
C23 H18 0.9600 . ?
C23 H19 0.9600 . ?
C23 H20 0.9600 . ?
C6 H5 0.9600 . ?
C6 H4 0.9600 . ?
C6 H6 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
C7 O1 C15 119.15(19) . . ?
C5 N2 C8 105.2(2) . . ?
C1 N1 C7 130.7(3) . . ?
C1 N1 C5 123.0(3) . . ?
C7 N1 C5 106.2(2) . . ?
C22 C17 C18 118.3(2) . . ?
C22 C17 C15 120.6(2) . . ?
C18 C17 C15 121.2(2) . . ?
C16 C15 O1 122.4(2) . . ?
C16 C15 C17 127.7(2) . . ?
O1 C15 C17 109.9(2) . . ?
C14 C9 C10 117.9(3) . . ?
C14 C9 C8 120.5(3) . . ?
C10 C9 C8 121.6(3) . . ?
C7 C8 N2 110.6(2) . . ?
C7 C8 C9 128.6(2) . . ?
N2 C8 C9 120.7(2) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H14 120.0 . . ?
C17 C18 H14 120.0 . . ?
N2 C5 N1 111.2(2) . . ?
N2 C5 C4 129.8(3) . . ?
N1 C5 C4 119.0(3) . . ?
C8 C7 O1 133.0(3) . . ?
C8 C7 N1 106.7(2) . . ?
O1 C7 N1 119.8(2) . . ?
C20 C19 C18 122.4(3) . . ?
C20 C19 H15 118.8 . . ?
C18 C19 H15 118.8 . . ?
C19 C20 C21 117.3(3) . . ?
C19 C20 C23 120.7(3) . . ?
C21 C20 C23 122.1(3) . . ?
C17 C22 C21 121.0(3) . . ?
C17 C22 H17 119.5 . . ?
C21 C22 H17 119.5 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H11 120.1 . . ?
C9 C10 H11 120.1 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C6 124.0(3) . . ?
C5 C4 C6 118.7(3) . . ?
C15 C16 H13 120.0 . . ?
C15 C16 H12 120.0 . . ?
H13 C16 H12 120.0 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H16 119.4 . . ?
C22 C21 H16 119.4 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H7 119.5 . . ?
C9 C14 H7 119.5 . . ?
C2 C1 N1 118.4(3) . . ?
C2 C1 H1 120.8 . . ?
N1 C1 H1 120.8 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H10 119.7 . . ?
C10 C11 H10 119.7 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H9 119.8 . . ?
C11 C12 H9 119.8 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H8 119.9 . . ?
C14 C13 H8 119.9 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C20 C23 H18 109.5 . . ?
C20 C23 H19 109.5 . . ?
H18 C23 H19 109.5 . . ?
C20 C23 H20 109.5 . . ?
H18 C23 H20 109.5 . . ?
H19 C23 H20 109.5 . . ?
C4 C6 H5 109.5 . . ?
C4 C6 H4 109.5 . . ?
H5 C6 H4 109.5 . . ?
C4 C6 H6 109.5 . . ?
H5 C6 H6 109.5 . . ?
H4 C6 H6 109.5 . . ?

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_vbchem162_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1566644'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            vbchem162_0m_a
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.2376(4)
_cell_length_b                   8.7359(4)
_cell_length_c                   11.8649(6)
_cell_angle_alpha                98.745(2)
_cell_angle_beta                 102.654(2)
_cell_angle_gamma                102.432(2)
_cell_volume                     795.58(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2996
_cell_measurement_theta_min      2.441
_cell_measurement_theta_max      28.614

_exptl_crystal_description       vbchem162_0m_a
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  char
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24863
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         28.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4065
_reflns_number_gt                2996
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.2595P] 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         4065
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.1789
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.013
_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
O1 O 0.25832(17) 0.18653(16) 0.29532(12) 0.0471(4) Uani 1 1 d . . . . .
O2 O -0.23908(18) 0.05316(19) 0.06709(13) 0.0535(4) Uani 1 1 d . . . . .
O3 O -0.0130(2) -0.04063(19) 0.13373(17) 0.0652(5) Uani 1 1 d . . . . .
N2 N 0.63043(18) 0.33339(18) 0.54386(13) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.3694(2) 0.16099(17) 0.48925(15) 0.0394(4) Uani 1 1 d . . . . .
C8 C 0.6375(2) 0.4346(2) 0.36053(15) 0.0352(4) Uani 1 1 d . . . . .
C17 C -0.0792(2) 0.0687(2) 0.13343(17) 0.0427(4) Uani 1 1 d . . . . .
C7 C 0.5495(2) 0.3380(2) 0.42976(15) 0.0347(4) Uani 1 1 d . . . . .
C14 C 0.3884(2) 0.2344(2) 0.39743(16) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.5217(2) 0.2261(2) 0.57817(16) 0.0374(4) Uani 1 1 d . . . . .
C9 C 0.8059(2) 0.5263(2) 0.40899(18) 0.0453(5) Uani 1 1 d . . . . .
H9 H 0.8604 0.5268 0.4865 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0047(3) 0.2322(3) 0.20236(19) 0.0488(5) Uani 1 1 d . . . . .
H16 H -0.0703 0.3057 0.1918 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1487(2) 0.2840(2) 0.27861(17) 0.0437(4) Uani 1 1 d . . . . .
H15 H 0.1831 0.3889 0.3219 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5389(3) 0.1701(3) 0.68456(19) 0.0479(5) Uani 1 1 d . . . . .
C5 C 0.2367(3) 0.0418(2) 0.4984(2) 0.0516(5) Uani 1 1 d . . . . .
H5 H 0.1370 0.0008 0.4370 0.062 Uiso 1 1 calc R U . . .
C10 C 0.8944(3) 0.6162(3) 0.3455(2) 0.0530(5) Uani 1 1 d . . . . .
H10 H 1.0070 0.6767 0.3803 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5615(3) 0.4367(3) 0.2445(2) 0.0569(6) Uani 1 1 d . . . . .
H13 H 0.4491 0.3762 0.2088 0.068 Uiso 1 1 calc R U . . .
C18 C -0.3230(3) -0.1014(3) -0.0074(2) 0.0629(6) Uani 1 1 d . . . . .
H18A H -0.2603 -0.1236 -0.0647 0.094 Uiso 1 1 calc R U . . .
H18B H -0.4382 -0.1027 -0.0473 0.094 Uiso 1 1 calc R U . . .
H18C H -0.3266 -0.1816 0.0397 0.094 Uiso 1 1 calc R U . . .
C3 C 0.4058(3) 0.0504(3) 0.6918(2) 0.0582(6) Uani 1 1 d . . . . .
H3 H 0.4153 0.0102 0.7605 0.070 Uiso 1 1 calc R U . . .
C4 C 0.2553(3) -0.0138(3) 0.5990(2) 0.0608(6) Uani 1 1 d . . . . .
H4 H 0.1680 -0.0954 0.6072 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8166(3) 0.6169(3) 0.2307(2) 0.0585(6) Uani 1 1 d . . . . .
H11 H 0.8759 0.6772 0.1872 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6508(3) 0.5275(4) 0.1815(2) 0.0707(8) Uani 1 1 d . . . . .
H12 H 0.5973 0.5280 0.1039 0.085 Uiso 1 1 calc R U . . .
C1 C 0.7001(3) 0.2420(4) 0.7814(2) 0.0673(7) Uani 1 1 d . . . . .
H1A H 0.6855 0.2072 0.8523 0.101 Uiso 1 1 calc R U . . .
H1B H 0.7242 0.3568 0.7950 0.101 Uiso 1 1 calc R U . . .
H1C H 0.7942 0.2083 0.7591 0.101 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
O1 C14 1.369(2) . ?
O1 C15 1.372(2) . ?
O2 C17 1.345(2) . ?
O2 C18 1.432(3) . ?
O3 C17 1.197(3) . ?
N2 C6 1.327(2) . ?
N2 C7 1.383(2) . ?
N1 C14 1.366(2) . ?
N1 C5 1.374(2) . ?
N1 C6 1.393(2) . ?
C8 C13 1.386(3) . ?
C8 C9 1.389(2) . ?
C8 C7 1.456(2) . ?
C17 C16 1.461(3) . ?
C7 C14 1.372(2) . ?
C6 C2 1.412(3) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C16 C15 1.322(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C2 C3 1.370(3) . ?
C2 C1 1.494(3) . ?
C5 C4 1.346(4) . ?
C5 H5 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C13 C12 1.379(3) . ?
C13 H13 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 C4 1.407(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C14 O1 C15 116.03(14) . . ?
C17 O2 C18 115.59(17) . . ?
C6 N2 C7 106.48(15) . . ?
C14 N1 C5 130.49(18) . . ?
C14 N1 C6 106.06(14) . . ?
C5 N1 C6 123.39(18) . . ?
C13 C8 C9 117.17(18) . . ?
C13 C8 C7 122.63(17) . . ?
C9 C8 C7 120.18(16) . . ?
O3 C17 O2 122.53(19) . . ?
O3 C17 C16 126.83(17) . . ?
O2 C17 C16 110.64(17) . . ?
C14 C7 N2 108.93(16) . . ?
C14 C7 C8 129.47(17) . . ?
N2 C7 C8 121.51(15) . . ?
N1 C14 O1 118.11(16) . . ?
N1 C14 C7 107.77(16) . . ?
O1 C14 C7 133.94(18) . . ?
N2 C6 N1 110.73(16) . . ?
N2 C6 C2 130.86(18) . . ?
N1 C6 C2 118.40(17) . . ?
C10 C9 C8 121.83(19) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C15 C16 C17 125.14(18) . . ?
C15 C16 H16 117.4 . . ?
C17 C16 H16 117.4 . . ?
C16 C15 O1 121.53(18) . . ?
C16 C15 H15 119.2 . . ?
O1 C15 H15 119.2 . . ?
C3 C2 C6 117.4(2) . . ?
C3 C2 C1 123.9(2) . . ?
C6 C2 C1 118.7(2) . . ?
C4 C5 N1 118.0(2) . . ?
C4 C5 H5 121.0 . . ?
N1 C5 H5 121.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.076

