# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1911210'
loop_
_audit_author_name
_audit_author_address
'Dilip K Maiti'
;Department of Chemistry, University of Calcutta
India
;
_audit_update_record             
;
2019-04-19 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38

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'

_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                   9.2441(16)
_cell_length_b                   9.5954(16)
_cell_length_c                   10.6672(18)
_cell_angle_alpha                73.867(4)
_cell_angle_beta                 70.650(4)
_cell_angle_gamma                78.883(4)
_cell_volume                     852.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    890
_cell_measurement_theta_min      2.223
_cell_measurement_theta_max      27.176

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   0.639
_exptl_transmission_factor_max   0.755
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABAS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21150
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_max         27.176
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3744
_reflns_number_gt                3048
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0632P)²+0.3097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.33398(13) 0.10971(13) 0.58355(12) 0.0493(3) Uani 1 1 d . . . . .
O2 O 0.11380(15) 0.20293(14) 0.89328(13) 0.0608(4) Uani 1 1 d . . . . .
N1 N 0.56649(15) 0.04249(13) 0.62386(13) 0.0392(3) Uani 1 1 d . . . . .
C1 C 0.0879(2) 0.6569(2) 0.5331(2) 0.0602(5) Uani 1 1 d . . . . .
H1 H 0.060879 0.744874 0.477584 0.072 Uiso 1 1 calc R U . . .
C2 C -0.0250(2) 0.5812(2) 0.6345(2) 0.0630(5) Uani 1 1 d . . . . .
H3 H -0.128263 0.618154 0.647527 0.076 Uiso 1 1 calc R U . . .
C3 C 0.01464(19) 0.45089(19) 0.71664(19) 0.0506(4) Uani 1 1 d . . . . .
H4 H -0.061892 0.400110 0.785205 0.061 Uiso 1 1 calc R U . . .
C4 C 0.16895(17) 0.39475(15) 0.69746(14) 0.0374(3) Uani 1 1 d . . . . .
C5 C 0.20978(18) 0.25827(16) 0.79128(15) 0.0387(3) Uani 1 1 d . . . . .
C6 C 0.37387(17) 0.18701(14) 0.76129(14) 0.0356(3) Uani 1 1 d . . . . .
C7 C 0.46875(18) 0.18473(15) 0.83645(14) 0.0373(3) Uani 1 1 d . . . . .
C8 C 0.4119(2) 0.26339(18) 0.95266(16) 0.0478(4) Uani 1 1 d . . . . .
H10 H 0.315386 0.229214 1.014409 0.057 Uiso 1 1 calc R U . . .
H9 H 0.486563 0.239611 1.003500 0.057 Uiso 1 1 calc R U . . .
C9 C 0.38781(19) 0.42715(17) 0.90164(15) 0.0414(3) Uani 1 1 d . . . . .
C10 C 0.2450(2) 0.5045(2) 0.94434(18) 0.0539(4) Uani 1 1 d . . . . .
H8 H 0.163942 0.455522 1.008037 0.065 Uiso 1 1 calc R U . . .
C11 C 0.2207(2) 0.6532(2) 0.8940(2) 0.0652(5) Uani 1 1 d . . . . .
H5 H 0.124312 0.703888 0.924352 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3389(3) 0.7259(2) 0.7993(2) 0.0667(5) Uani 1 1 d . . . . .
H2 H 0.322340 0.825727 0.763572 0.080 Uiso 1 1 calc R U . . .
C13 C 0.4825(3) 0.6512(2) 0.7568(2) 0.0638(5) Uani 1 1 d . . . . .
H6 H 0.563161 0.700791 0.693281 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5069(2) 0.50316(19) 0.80824(19) 0.0522(4) Uani 1 1 d . . . . .
H7 H 0.604550 0.453675 0.779909 0.063 Uiso 1 1 calc R U . . .
C15 C 0.62356(18) 0.10979(15) 0.80228(15) 0.0382(3) Uani 1 1 d . . . . .
C16 C 0.7349(2) 0.10479(19) 0.86803(18) 0.0512(4) Uani 1 1 d . . . . .
H11 H 0.709915 0.152269 0.938741 0.061 Uiso 1 1 calc R U . . .
C17 C 0.8796(2) 0.0309(2) 0.8294(2) 0.0582(5) Uani 1 1 d . . . . .
H12 H 0.951257 0.029145 0.874024 0.070 Uiso 1 1 calc R U . . .
C18 C 0.9194(2) -0.0408(2) 0.7244(2) 0.0586(5) Uani 1 1 d . . . . .
H13 H 1.017120 -0.091304 0.699562 0.070 Uiso 1 1 calc R U . . .
C19 C 0.8154(2) -0.03769(18) 0.65691(19) 0.0492(4) Uani 1 1 d . . . . .
H14 H 0.842320 -0.085733 0.586380 0.059 Uiso 1 1 calc R U . . .
C20 C 0.66867(17) 0.03806(15) 0.69471(15) 0.0378(3) Uani 1 1 d . . . . .
C21 C 0.42123(17) 0.11264(15) 0.65033(15) 0.0367(3) Uani 1 1 d . . . . .
C22 C 0.28114(19) 0.47120(17) 0.59501(16) 0.0455(4) Uani 1 1 d . . . . .
H15 H 0.384455 0.434003 0.580569 0.055 Uiso 1 1 calc R U . . .
C23 C 0.2407(2) 0.60260(19) 0.51390(19) 0.0562(5) Uani 1 1 d . . . . .
H16 H 0.316861 0.654530 0.446100 0.067 Uiso 1 1 calc R U . . .
H1A H 0.602(2) -0.008(2) 0.5533(19) 0.050(5) 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 C21 1.2488(18) . ?
O2 C5 1.2141(18) . ?
N1 C21 1.3571(19) . ?
N1 C20 1.3802(19) . ?
N1 H1A 0.94(2) . ?
C1 C23 1.375(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C3 H4 0.9300 . ?
C4 C22 1.380(2) . ?
C4 C5 1.480(2) . ?
C5 C6 1.507(2) . ?
C6 C7 1.364(2) . ?
C6 C21 1.4517(19) . ?
C7 C15 1.450(2) . ?
C7 C8 1.523(2) . ?
C8 C9 1.512(2) . ?
C8 H10 0.9700 . ?
C8 H9 0.9700 . ?
C9 C10 1.383(2) . ?
C9 C14 1.384(2) . ?
C10 C11 1.381(3) . ?
C10 H8 0.9300 . ?
C11 C12 1.368(3) . ?
C11 H5 0.9300 . ?
C12 C13 1.377(3) . ?
C12 H2 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H6 0.9300 . ?
C14 H7 0.9300 . ?
C15 C20 1.406(2) . ?
C15 C16 1.412(2) . ?
C16 C17 1.376(3) . ?
C16 H11 0.9300 . ?
C17 C18 1.387(3) . ?
C17 H12 0.9300 . ?
C18 C19 1.371(3) . ?
C18 H13 0.9300 . ?
C19 C20 1.396(2) . ?
C19 H14 0.9300 . ?
C22 C23 1.380(2) . ?
C22 H15 0.9300 . ?
C23 H16 0.9300 . ?

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
C21 N1 C20 124.46(12) . . ?
C21 N1 H1A 119.1(11) . . ?
C20 N1 H1A 116.4(11) . . ?
C23 C1 C2 120.07(16) . . ?
C23 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.08(17) . . ?
C3 C2 H3 120.0 . . ?
C1 C2 H3 120.0 . . ?
C2 C3 C4 120.24(16) . . ?
C2 C3 H4 119.9 . . ?
C4 C3 H4 119.9 . . ?
C22 C4 C3 119.18(14) . . ?
C22 C4 C5 121.35(13) . . ?
C3 C4 C5 119.41(14) . . ?
O2 C5 C4 121.29(14) . . ?
O2 C5 C6 119.03(14) . . ?
C4 C5 C6 119.68(12) . . ?
C7 C6 C21 122.06(13) . . ?
C7 C6 C5 123.23(13) . . ?
C21 C6 C5 114.62(12) . . ?
C6 C7 C15 119.29(13) . . ?
C6 C7 C8 119.65(14) . . ?
C15 C7 C8 121.05(14) . . ?
C9 C8 C7 112.14(12) . . ?
C9 C8 H10 109.2 . . ?
C7 C8 H10 109.2 . . ?
C9 C8 H9 109.2 . . ?
C7 C8 H9 109.2 . . ?
H10 C8 H9 107.9 . . ?
C10 C9 C14 118.22(16) . . ?
C10 C9 C8 120.84(15) . . ?
C14 C9 C8 120.91(15) . . ?
C11 C10 C9 121.10(17) . . ?
C11 C10 H8 119.5 . . ?
C9 C10 H8 119.5 . . ?
C12 C11 C10 119.83(18) . . ?
C12 C11 H5 120.1 . . ?
C10 C11 H5 120.1 . . ?
C11 C12 C13 119.92(18) . . ?
C11 C12 H2 120.0 . . ?
C13 C12 H2 120.0 . . ?
C14 C13 C12 120.17(19) . . ?
C14 C13 H6 119.9 . . ?
C12 C13 H6 119.9 . . ?
C13 C14 C9 120.73(17) . . ?
C13 C14 H7 119.6 . . ?
C9 C14 H7 119.6 . . ?
C20 C15 C16 116.84(15) . . ?
C20 C15 C7 118.32(13) . . ?
C16 C15 C7 124.82(14) . . ?
C17 C16 C15 121.22(17) . . ?
C17 C16 H11 119.4 . . ?
C15 C16 H11 119.4 . . ?
C16 C17 C18 120.41(16) . . ?
C16 C17 H12 119.8 . . ?
C18 C17 H12 119.8 . . ?
C19 C18 C17 120.33(17) . . ?
C19 C18 H13 119.8 . . ?
C17 C18 H13 119.8 . . ?
C18 C19 C20 119.61(17) . . ?
C18 C19 H14 120.2 . . ?
C20 C19 H14 120.2 . . ?
N1 C20 C19 118.82(14) . . ?
N1 C20 C15 119.61(13) . . ?
C19 C20 C15 121.57(14) . . ?
O1 C21 N1 120.95(13) . . ?
O1 C21 C6 122.81(13) . . ?
N1 C21 C6 116.23(13) . . ?
C23 C22 C4 120.29(15) . . ?
C23 C22 H15 119.9 . . ?
C4 C22 H15 119.9 . . ?
C1 C23 C22 120.13(17) . . ?
C1 C23 H16 119.9 . . ?
C22 C23 H16 119.9 . . ?

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
C23 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C22 -0.2(3) . . . . ?
C2 C3 C4 C5 176.92(17) . . . . ?
C22 C4 C5 O2 168.80(16) . . . . ?
C3 C4 C5 O2 -8.2(2) . . . . ?
C22 C4 C5 C6 -10.4(2) . . . . ?
C3 C4 C5 C6 172.57(14) . . . . ?
O2 C5 C6 C7 -69.9(2) . . . . ?
C4 C5 C6 C7 109.28(16) . . . . ?
O2 C5 C6 C21 106.55(16) . . . . ?
C4 C5 C6 C21 -74.24(17) . . . . ?
C21 C6 C7 C15 2.0(2) . . . . ?
C5 C6 C7 C15 178.22(12) . . . . ?
C21 C6 C7 C8 -179.31(13) . . . . ?
C5 C6 C7 C8 -3.1(2) . . . . ?
C6 C7 C8 C9 -67.03(19) . . . . ?
C15 C7 C8 C9 111.65(16) . . . . ?
C7 C8 C9 C10 121.46(17) . . . . ?
C7 C8 C9 C14 -56.8(2) . . . . ?
C14 C9 C10 C11 0.9(3) . . . . ?
C8 C9 C10 C11 -177.41(17) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C10 C9 C14 C13 -1.6(3) . . . . ?
C8 C9 C14 C13 176.70(16) . . . . ?
C6 C7 C15 C20 -1.9(2) . . . . ?
C8 C7 C15 C20 179.42(13) . . . . ?
C6 C7 C15 C16 177.14(14) . . . . ?
C8 C7 C15 C16 -1.5(2) . . . . ?
C20 C15 C16 C17 -1.0(2) . . . . ?
C7 C15 C16 C17 179.94(15) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C21 N1 C20 C19 -179.78(14) . . . . ?
C21 N1 C20 C15 0.0(2) . . . . ?
C18 C19 C20 N1 178.71(15) . . . . ?
C18 C19 C20 C15 -1.0(2) . . . . ?
C16 C15 C20 N1 -178.18(13) . . . . ?
C7 C15 C20 N1 0.9(2) . . . . ?
C16 C15 C20 C19 1.6(2) . . . . ?
C7 C15 C20 C19 -179.32(13) . . . . ?
C20 N1 C21 O1 -178.63(14) . . . . ?
C20 N1 C21 C6 0.0(2) . . . . ?
C7 C6 C21 O1 177.58(14) . . . . ?
C5 C6 C21 O1 1.1(2) . . . . ?
C7 C6 C21 N1 -1.1(2) . . . . ?
C5 C6 C21 N1 -177.59(12) . . . . ?
C3 C4 C22 C23 0.9(2) . . . . ?
C5 C4 C22 C23 -176.19(16) . . . . ?
C2 C1 C23 C22 0.8(3) . . . . ?
C4 C22 C23 C1 -1.2(3) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_ajarul_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1911211'
loop_
_audit_author_name
_audit_author_address
'Dilip K. Maiti'
;Department of Chemistry, University of Calcutta
India
;
_audit_update_record             
;
2019-04-19 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.41

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.893(9)
_cell_length_b                   10.210(11)
_cell_length_c                   11.258(10)
_cell_angle_alpha                80.88(4)
_cell_angle_beta                 85.50(3)
_cell_angle_gamma                69.03(3)
_cell_volume                     942.2(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5090
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.09

_exptl_crystal_description       crystalline
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             438
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30258
_diffrn_reflns_av_R_equivalents  0.1795
_diffrn_reflns_av_sigmaI/netI    0.1363
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.42
_reflns_number_total             4725
_reflns_number_gt                2257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.2081P] 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         4725
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_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
O2 O 0.0507(2) 0.81542(19) 0.01530(18) 0.0524(5) Uani 1 1 d . . .
O1 O 0.2080(2) 0.4688(2) 0.1280(2) 0.0591(6) Uani 1 1 d . . .
O3 O 0.7936(2) 0.1316(2) 0.43598(18) 0.0589(6) Uani 1 1 d . . .
N1 N 0.2101(3) 0.9281(2) 0.0587(2) 0.0420(6) Uani 1 1 d . . .
C18 C 0.5261(3) 0.4973(2) 0.2169(2) 0.0324(6) Uani 1 1 d . . .
C8 C 0.2743(3) 0.6726(3) 0.1289(2) 0.0351(6) Uani 1 1 d . . .
C10 C 0.4356(3) 0.6287(2) 0.1396(2) 0.0334(6) Uani 1 1 d . . .
C3 C 0.0517(3) 0.6180(3) 0.2656(2) 0.0387(6) Uani 1 1 d . . .
C13 C 0.3309(3) 0.9518(3) 0.1170(2) 0.0379(6) Uani 1 1 d . . .
C11 C 0.5270(3) 0.7180(3) 0.0737(2) 0.0427(7) Uani 1 1 d . . .
H6 H 0.6418 0.6656 0.0793 0.051 Uiso 1 1 calc R . .
H7 H 0.4998 0.7400 -0.0107 0.051 Uiso 1 1 calc R . .
C21 C 0.6992(3) 0.2526(3) 0.3678(2) 0.0391(6) Uani 1 1 d . . .
C7 C 0.1790(3) 0.5775(3) 0.1709(2) 0.0397(6) Uani 1 1 d . . .
C9 C 0.1749(3) 0.8095(3) 0.0626(2) 0.0395(6) Uani 1 1 d . . .
C12 C 0.4864(3) 0.8525(3) 0.1264(2) 0.0391(6) Uani 1 1 d . . .
C22 C 0.7580(3) 0.2827(3) 0.2536(2) 0.0420(7) Uani 1 1 d . . .
H14 H 0.8549 0.2209 0.2264 0.050 Uiso 1 1 calc R . .
C19 C 0.4707(3) 0.4639(3) 0.3320(2) 0.0393(6) Uani 1 1 d . . .
H12 H 0.3730 0.5245 0.3593 0.047 Uiso 1 1 calc R . .
C23 C 0.6737(3) 0.4039(3) 0.1799(2) 0.0388(6) Uani 1 1 d . . .
H15 H 0.7158 0.4241 0.1038 0.047 Uiso 1 1 calc R . .
C20 C 0.5555(3) 0.3439(3) 0.4076(2) 0.0409(6) Uani 1 1 d . . .
H13 H 0.5158 0.3248 0.4848 0.049 Uiso 1 1 calc R . .
C14 C 0.2939(3) 1.0813(3) 0.1576(2) 0.0472(7) Uani 1 1 d . . .
H8 H 0.1910 1.1488 0.1478 0.057 Uiso 1 1 calc R . .
C17 C 0.6000(3) 0.8844(3) 0.1830(3) 0.0495(7) Uani 1 1 d . . .
H11 H 0.7038 0.8183 0.1922 0.059 Uiso 1 1 calc R . .
C4 C 0.0353(3) 0.7291(3) 0.3267(3) 0.0530(8) Uani 1 1 d . . .
H3 H 0.1000 0.7836 0.3051 0.064 Uiso 1 1 calc R . .
C2 C -0.0467(3) 0.5401(3) 0.2976(3) 0.0513(8) Uani 1 1 d . . .
H2 H -0.0373 0.4652 0.2566 0.062 Uiso 1 1 calc R . .
C15 C 0.4096(4) 1.1100(3) 0.2123(2) 0.0544(8) Uani 1 1 d . . .
H9 H 0.3847 1.1964 0.2404 0.065 Uiso 1 1 calc R . .
C16 C 0.5622(4) 1.0106(3) 0.2253(3) 0.0573(8) Uani 1 1 d . . .
H10 H 0.6399 1.0295 0.2632 0.069 Uiso 1 1 calc R . .
C5 C -0.0762(4) 0.7600(4) 0.4197(3) 0.0675(9) Uani 1 1 d . . .
H4 H -0.0862 0.8347 0.4610 0.081 Uiso 1 1 calc R . .
C1 C -0.1598(4) 0.5723(4) 0.3903(3) 0.0658(9) Uani 1 1 d . . .
H1 H -0.2270 0.5199 0.4107 0.079 Uiso 1 1 calc R . .
C6 C -0.1726(4) 0.6802(4) 0.4512(3) 0.0686(10) Uani 1 1 d . . .
H5 H -0.2469 0.7004 0.5147 0.082 Uiso 1 1 calc R . .
C24 C 0.7286(5) 0.0898(4) 0.5488(3) 0.0769(11) Uani 1 1 d . . .
H17 H 0.6998 0.1653 0.5969 0.115 Uiso 1 1 calc R . .
H16 H 0.8074 0.0070 0.5896 0.115 Uiso 1 1 calc R . .
H18 H 0.6345 0.0690 0.5360 0.115 Uiso 1 1 calc R . .
H1A H 0.124(4) 1.011(3) 0.028(3) 0.064(9) 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
O2 C9 1.241(3) . ?
O1 C7 1.215(3) . ?
O3 C21 1.370(3) . ?
O3 C24 1.421(4) . ?
N1 C9 1.348(4) . ?
N1 C13 1.412(3) . ?
N1 H1A 0.96(3) . ?
C18 C19 1.385(4) . ?
C18 C23 1.397(4) . ?
C18 C10 1.474(3) . ?
C8 C10 1.350(4) . ?
C8 C9 1.477(4) . ?
C8 C7 1.506(4) . ?
C10 C11 1.505(3) . ?
C3 C2 1.374(4) . ?
C3 C4 1.376(4) . ?
C3 C7 1.484(4) . ?
C13 C14 1.386(4) . ?
C13 C12 1.392(4) . ?
C11 C12 1.496(4) . ?
C11 H6 0.9700 . ?
C11 H7 0.9700 . ?
C21 C20 1.376(4) . ?
C21 C22 1.381(4) . ?
C12 C17 1.391(4) . ?
C22 C23 1.375(4) . ?
C22 H14 0.9300 . ?
C19 C20 1.380(4) . ?
C19 H12 0.9300 . ?
C23 H15 0.9300 . ?
C20 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 H8 0.9300 . ?
C17 C16 1.364(4) . ?
C17 H11 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H3 0.9300 . ?
C2 C1 1.384(4) . ?
C2 H2 0.9300 . ?
C15 C16 1.375(4) . ?
C15 H9 0.9300 . ?
C16 H10 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H4 0.9300 . ?
C1 C6 1.355(5) . ?
C1 H1 0.9300 . ?
C6 H5 0.9300 . ?
C24 H17 0.9600 . ?
C24 H16 0.9600 . ?
C24 H18 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
C21 O3 C24 117.3(2) . . ?
C9 N1 C13 130.3(2) . . ?
C9 N1 H1A 112.1(17) . . ?
C13 N1 H1A 115.6(18) . . ?
C19 C18 C23 117.0(2) . . ?
C19 C18 C10 121.1(2) . . ?
C23 C18 C10 121.9(2) . . ?
C10 C8 C9 124.8(2) . . ?
C10 C8 C7 122.5(2) . . ?
C9 C8 C7 112.2(2) . . ?
C8 C10 C18 122.2(2) . . ?
C8 C10 C11 119.5(2) . . ?
C18 C10 C11 118.3(2) . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 C7 120.1(3) . . ?
C4 C3 C7 121.0(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 N1 118.2(2) . . ?
C12 C13 N1 121.2(2) . . ?
C12 C11 C10 110.4(2) . . ?
C12 C11 H6 109.6 . . ?
C10 C11 H6 109.6 . . ?
C12 C11 H7 109.6 . . ?
C10 C11 H7 109.6 . . ?
H6 C11 H7 108.1 . . ?
O3 C21 C20 124.1(3) . . ?
O3 C21 C22 116.0(2) . . ?
C20 C21 C22 119.8(2) . . ?
O1 C7 C3 121.2(2) . . ?
O1 C7 C8 119.8(2) . . ?
C3 C7 C8 119.0(2) . . ?
O2 C9 N1 119.9(2) . . ?
O2 C9 C8 118.1(2) . . ?
N1 C9 C8 122.0(2) . . ?
C17 C12 C13 118.0(3) . . ?
C17 C12 C11 122.4(3) . . ?
C13 C12 C11 119.6(2) . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H14 119.9 . . ?
C21 C22 H14 119.9 . . ?
C20 C19 C18 122.3(2) . . ?
C20 C19 H12 118.9 . . ?
C18 C19 H12 118.9 . . ?
C22 C23 C18 121.3(2) . . ?
C22 C23 H15 119.3 . . ?
C18 C23 H15 119.3 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H13 120.3 . . ?
C19 C20 H13 120.3 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H8 120.0 . . ?
C13 C14 H8 120.0 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H11 119.3 . . ?
C12 C17 H11 119.3 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H3 119.8 . . ?
C5 C4 H3 119.8 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H9 120.1 . . ?
C14 C15 H9 120.1 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H10 119.8 . . ?
C15 C16 H10 119.8 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H4 120.0 . . ?
C4 C5 H4 120.0 . . ?
C6 C1 C2 119.9(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H5 119.9 . . ?
C5 C6 H5 119.9 . . ?
O3 C24 H17 109.5 . . ?
O3 C24 H16 109.5 . . ?
H17 C24 H16 109.5 . . ?
O3 C24 H18 109.5 . . ?
H17 C24 H18 109.5 . . ?
H16 C24 H18 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.42
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.069
