# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_170328LT
_database_code_depnum_ccdc_archive 'CCDC 1580618'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl N O'
_chemical_formula_weight         371.84

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0623(5)
_cell_length_b                   18.5108(9)
_cell_length_c                   9.7609(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.868(2)
_cell_angle_gamma                90
_cell_volume                     1974.87(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3092
_cell_measurement_theta_min      2.3812
_cell_measurement_theta_max      22.0739

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9026
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14743
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4036
_reflns_number_gt                2577
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0504P)²+0.4467P] 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         4036
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl -0.32795(6) 0.85204(4) 0.03568(9) 0.1019(3) Uani 1 1 d . . . . .
O1 O 0.14219(14) 0.73799(8) 0.09212(15) 0.0707(4) Uani 1 1 d . . . . .
N1 N 0.19934(14) 0.86869(8) 0.24960(15) 0.0474(4) Uani 1 1 d . . . . .
C1 C 0.3612(3) 0.53649(15) 0.3488(4) 0.0937(9) Uani 1 1 d . . . . .
H1 H 0.3911 0.4907 0.3822 0.112 Uiso 1 1 calc R U . . .
C2 C 0.3543(2) 0.59215(15) 0.4410(3) 0.0799(7) Uani 1 1 d . . . . .
H15 H 0.3783 0.5847 0.5377 0.096 Uiso 1 1 calc R U . . .
C3 C 0.3122(2) 0.65870(12) 0.3914(2) 0.0645(6) Uani 1 1 d . . . . .
H16 H 0.3079 0.6975 0.4541 0.077 Uiso 1 1 calc R U . . .
C4 C 0.27625(18) 0.66922(11) 0.25063(19) 0.0516(5) Uani 1 1 d . . . . .
C5 C 0.22369(18) 0.73890(11) 0.1926(2) 0.0526(5) Uani 1 1 d . . . . .
C6 C 0.27218(18) 0.80687(10) 0.25624(19) 0.0503(5) Uani 1 1 d . . . . .
C7 C 0.27003(18) 0.92673(11) 0.30066(18) 0.0498(5) Uani 1 1 d . . . . .
C8 C 0.22502(19) 0.99980(11) 0.32246(19) 0.0527(5) Uani 1 1 d . . . . .
C9 C 0.1091(2) 1.01459(12) 0.3542(2) 0.0640(6) Uani 1 1 d . . . . .
H7 H 0.0531 0.9760 0.3582 0.077 Uiso 1 1 calc R U . . .
C10 C 0.0739(3) 1.08439(14) 0.3801(3) 0.0793(7) Uani 1 1 d . . . . .
H8 H -0.0061 1.0932 0.4001 0.095 Uiso 1 1 calc R U . . .
C11 C 0.1532(3) 1.14060(14) 0.3770(3) 0.0889(8) Uani 1 1 d . . . . .
H2 H 0.1291 1.1884 0.3955 0.107 Uiso 1 1 calc R U . . .
C12 C 0.3253(3) 0.54652(15) 0.2096(3) 0.0992(10) Uani 1 1 d . . . . .
H18 H 0.3304 0.5078 0.1469 0.119 Uiso 1 1 calc R U . . .
C13 C 0.2823(2) 0.61216(13) 0.1610(2) 0.0739(7) Uani 1 1 d . . . . .
H17 H 0.2562 0.6187 0.0644 0.089 Uiso 1 1 calc R U . . .
C14 C 0.38790(18) 0.90128(12) 0.3351(2) 0.0588(5) Uani 1 1 d . . . . .
H3 H 0.4568 0.9299 0.3711 0.071 Uiso 1 1 calc R U . . .
C15 C 0.39077(18) 0.82741(12) 0.3090(2) 0.0588(5) Uani 1 1 d . . . . .
C16 C 0.5053(2) 0.78238(15) 0.3302(3) 0.0911(8) Uani 1 1 d . . . . .
H4 H 0.5129 0.7580 0.4203 0.137 Uiso 1 1 calc R U . . .
H6 H 0.5765 0.8136 0.3279 0.137 Uiso 1 1 calc R U . . .
H5 H 0.5010 0.7462 0.2563 0.137 Uiso 1 1 calc R U . . .
C17 C 0.2681(3) 1.12731(14) 0.3468(3) 0.0892(8) Uani 1 1 d . . . . .
H10 H 0.3239 1.1662 0.3452 0.107 Uiso 1 1 calc R U . . .
C18 C 0.3038(2) 1.05792(13) 0.3186(2) 0.0713(6) Uani 1 1 d . . . . .
H9 H 0.3834 1.0499 0.2963 0.086 Uiso 1 1 calc R U . . .
C19 C 0.07044(17) 0.86819(10) 0.20118(19) 0.0476(5) Uani 1 1 d . . . . .
C20 C -0.00629(19) 0.83365(11) 0.2784(2) 0.0563(5) Uani 1 1 d . . . . .
H14 H 0.0256 0.8125 0.3652 0.068 Uiso 1 1 calc R U . . .
C21 C -0.1298(2) 0.82995(12) 0.2289(2) 0.0644(6) Uani 1 1 d . . . . .
H13 H -0.1840 0.8066 0.2813 0.077 Uiso 1 1 calc R U . . .
C22 C -0.17354(19) 0.86061(12) 0.1019(3) 0.0638(6) Uani 1 1 d . . . . .
C23 C -0.0974(2) 0.89620(12) 0.0260(2) 0.0683(6) Uani 1 1 d . . . . .
H12 H -0.1295 0.9180 -0.0600 0.082 Uiso 1 1 calc R U . . .
C24 C 0.02564(19) 0.89994(12) 0.0756(2) 0.0603(6) Uani 1 1 d . . . . .
H11 H 0.0794 0.9242 0.0239 0.072 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
Cl1 C22 1.738(2) . ?
O1 C5 1.226(2) . ?
N1 C7 1.376(2) . ?
N1 C6 1.395(2) . ?
N1 C19 1.431(2) . ?
C1 C12 1.368(4) . ?
C1 C2 1.378(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H15 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H16 0.9500 . ?
C4 C13 1.380(3) . ?
C4 C5 1.490(3) . ?
C5 C6 1.468(3) . ?
C6 C15 1.387(3) . ?
C7 C14 1.378(3) . ?
C7 C8 1.468(3) . ?
C8 C18 1.389(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.384(3) . ?
C9 H7 0.9500 . ?
C10 C11 1.364(4) . ?
C10 H8 0.9500 . ?
C11 C17 1.371(4) . ?
C11 H2 0.9500 . ?
C12 C13 1.363(3) . ?
C12 H18 0.9500 . ?
C13 H17 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H3 0.9500 . ?
C15 C16 1.504(3) . ?
C16 H4 0.9800 . ?
C16 H6 0.9800 . ?
C16 H5 0.9800 . ?
C17 C18 1.384(4) . ?
C17 H10 0.9500 . ?
C18 H9 0.9500 . ?
C19 C20 1.377(3) . ?
C19 C24 1.381(3) . ?
C20 C21 1.379(3) . ?
C20 H14 0.9500 . ?
C21 C22 1.381(3) . ?
C21 H13 0.9500 . ?
C22 C23 1.373(3) . ?
C23 C24 1.375(3) . ?
C23 H12 0.9500 . ?
C24 H11 0.9500 . ?

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 N1 C6 109.37(16) . . ?
C7 N1 C19 127.32(16) . . ?
C6 N1 C19 123.28(16) . . ?
C12 C1 C2 120.7(2) . . ?
C12 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H15 120.4 . . ?
C3 C2 H15 120.4 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H16 119.8 . . ?
C4 C3 H16 119.8 . . ?
C13 C4 C3 119.1(2) . . ?
C13 C4 C5 118.42(18) . . ?
C3 C4 C5 122.32(18) . . ?
O1 C5 C6 121.74(18) . . ?
O1 C5 C4 119.21(18) . . ?
C6 C5 C4 119.05(17) . . ?
C15 C6 N1 107.39(18) . . ?
C15 C6 C5 130.96(19) . . ?
N1 C6 C5 120.85(17) . . ?
N1 C7 C14 106.55(18) . . ?
N1 C7 C8 125.81(17) . . ?
C14 C7 C8 127.50(19) . . ?
C18 C8 C9 117.2(2) . . ?
C18 C8 C7 118.8(2) . . ?
C9 C8 C7 123.93(19) . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H7 119.4 . . ?
C8 C9 H7 119.4 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H8 119.7 . . ?
C9 C10 H8 119.7 . . ?
C10 C11 C17 119.2(3) . . ?
C10 C11 H2 120.4 . . ?
C17 C11 H2 120.4 . . ?
C13 C12 C1 119.9(3) . . ?
C13 C12 H18 120.0 . . ?
C1 C12 H18 120.0 . . ?
C12 C13 C4 120.7(2) . . ?
C12 C13 H17 119.7 . . ?
C4 C13 H17 119.7 . . ?
C7 C14 C15 109.79(18) . . ?
C7 C14 H3 125.1 . . ?
C15 C14 H3 125.1 . . ?
C6 C15 C14 106.87(18) . . ?
C6 C15 C16 128.9(2) . . ?
C14 C15 C16 124.2(2) . . ?
C15 C16 H4 109.5 . . ?
C15 C16 H6 109.5 . . ?
H4 C16 H6 109.5 . . ?
C15 C16 H5 109.5 . . ?
H4 C16 H5 109.5 . . ?
H6 C16 H5 109.5 . . ?
C11 C17 C18 120.8(3) . . ?
C11 C17 H10 119.6 . . ?
C18 C17 H10 119.6 . . ?
C17 C18 C8 120.9(2) . . ?
C17 C18 H9 119.5 . . ?
C8 C18 H9 119.5 . . ?
C20 C19 C24 121.12(19) . . ?
C20 C19 N1 119.28(17) . . ?
C24 C19 N1 119.56(17) . . ?
C19 C20 C21 119.47(19) . . ?
C19 C20 H14 120.3 . . ?
C21 C20 H14 120.3 . . ?
C20 C21 C22 119.1(2) . . ?
C20 C21 H13 120.5 . . ?
C22 C21 H13 120.5 . . ?
C23 C22 C21 121.5(2) . . ?
C23 C22 Cl1 119.49(18) . . ?
C21 C22 Cl1 119.01(19) . . ?
C22 C23 C24 119.4(2) . . ?
C22 C23 H12 120.3 . . ?
C24 C23 H12 120.3 . . ?
C23 C24 C19 119.5(2) . . ?
C23 C24 H11 120.3 . . ?
C19 C24 H11 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C13 0.4(3) . . . . ?
C2 C3 C4 C5 176.5(2) . . . . ?
C13 C4 C5 O1 32.3(3) . . . . ?
C3 C4 C5 O1 -143.8(2) . . . . ?
C13 C4 C5 C6 -146.8(2) . . . . ?
C3 C4 C5 C6 37.1(3) . . . . ?
C7 N1 C6 C15 -1.5(2) . . . . ?
C19 N1 C6 C15 -179.37(16) . . . . ?
C7 N1 C6 C5 -172.33(17) . . . . ?
C19 N1 C6 C5 9.9(3) . . . . ?
O1 C5 C6 C15 -140.2(2) . . . . ?
C4 C5 C6 C15 38.9(3) . . . . ?
O1 C5 C6 N1 28.1(3) . . . . ?
C4 C5 C6 N1 -152.75(17) . . . . ?
C6 N1 C7 C14 1.8(2) . . . . ?
C19 N1 C7 C14 179.55(17) . . . . ?
C6 N1 C7 C8 -174.25(17) . . . . ?
C19 N1 C7 C8 3.5(3) . . . . ?
N1 C7 C8 C18 -153.69(19) . . . . ?
C14 C7 C8 C18 31.0(3) . . . . ?
N1 C7 C8 C9 29.8(3) . . . . ?
C14 C7 C8 C9 -145.5(2) . . . . ?
C18 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C10 176.90(19) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C10 C11 C17 0.5(4) . . . . ?
C2 C1 C12 C13 0.0(5) . . . . ?
C1 C12 C13 C4 1.0(5) . . . . ?
C3 C4 C13 C12 -1.3(4) . . . . ?
C5 C4 C13 C12 -177.5(2) . . . . ?
N1 C7 C14 C15 -1.5(2) . . . . ?
C8 C7 C14 C15 174.55(18) . . . . ?
N1 C6 C15 C14 0.6(2) . . . . ?
C5 C6 C15 C14 170.1(2) . . . . ?
N1 C6 C15 C16 -176.6(2) . . . . ?
C5 C6 C15 C16 -7.1(4) . . . . ?
C7 C14 C15 C6 0.5(2) . . . . ?
C7 C14 C15 C16 177.9(2) . . . . ?
C10 C11 C17 C18 0.5(4) . . . . ?
C11 C17 C18 C8 -1.1(4) . . . . ?
C9 C8 C18 C17 0.7(3) . . . . ?
C7 C8 C18 C17 -176.1(2) . . . . ?
C7 N1 C19 C20 -109.5(2) . . . . ?
C6 N1 C19 C20 67.9(2) . . . . ?
C7 N1 C19 C24 72.9(2) . . . . ?
C6 N1 C19 C24 -109.7(2) . . . . ?
C24 C19 C20 C21 0.8(3) . . . . ?
N1 C19 C20 C21 -176.81(18) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 -1.7(3) . . . . ?
C20 C21 C22 Cl1 176.87(16) . . . . ?
C21 C22 C23 C24 1.6(3) . . . . ?
Cl1 C22 C23 C24 -176.94(17) . . . . ?
C22 C23 C24 C19 -0.3(3) . . . . ?
C20 C19 C24 C23 -0.9(3) . . . . ?
N1 C19 C24 C23 176.72(19) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.032

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_d18758
_database_code_depnum_ccdc_archive 'CCDC 1580644'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.6383(14)
_cell_length_b                   9.7333(11)
_cell_length_c                   10.4533(14)
_cell_angle_alpha                80.286(4)
_cell_angle_beta                 71.715(4)
_cell_angle_gamma                74.791(4)
_cell_volume                     894.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2671
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9917
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18760
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_sigmaI/netI    0.0700
_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       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3156
_reflns_number_gt                2233
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0403P)²+0.2952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3156
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4669(3) 0.3566(3) 0.4255(2) 0.0299(6) Uani 1 1 d . . .
C2 C 0.3311(3) 0.3148(2) 0.5239(2) 0.0280(6) Uani 1 1 d . . .
C3 C 0.2014(3) 0.4201(3) 0.5621(3) 0.0337(6) Uani 1 1 d . . .
H3 H 0.2015 0.5171 0.5286 0.040 Uiso 1 1 calc R . .
C4 C 0.0726(3) 0.3844(3) 0.6483(3) 0.0433(7) Uani 1 1 d . . .
H4 H -0.0153 0.4573 0.6750 0.052 Uiso 1 1 calc R . .
C5 C 0.0693(3) 0.2442(3) 0.6965(3) 0.0442(7) Uani 1 1 d . . .
H5 H -0.0199 0.2208 0.7568 0.053 Uiso 1 1 calc R . .
C6 C 0.1967(3) 0.1379(3) 0.6566(3) 0.0423(7) Uani 1 1 d . . .
H6 H 0.1949 0.0407 0.6875 0.051 Uiso 1 1 calc R . .
C7 C 0.3270(3) 0.1738(3) 0.5712(3) 0.0363(7) Uani 1 1 d . . .
H7 H 0.4148 0.1007 0.5448 0.044 Uiso 1 1 calc R . .
C8 C 0.6158(3) 0.2742(2) 0.4309(2) 0.0280(6) Uani 1 1 d . . .
C9 C 0.6700(3) 0.2120(2) 0.5409(2) 0.0303(6) Uani 1 1 d . . .
C10 C 0.5850(3) 0.1993(3) 0.6886(3) 0.0424(7) Uani 1 1 d . . .
H10A H 0.5113 0.2889 0.7112 0.064 Uiso 1 1 calc R . .
H10B H 0.6551 0.1799 0.7434 0.064 Uiso 1 1 calc R . .
H10C H 0.5332 0.1207 0.7074 0.064 Uiso 1 1 calc R . .
C11 C 0.8261(3) 0.1730(3) 0.4914(3) 0.0318(6) Uani 1 1 d . . .
H11 H 0.8928 0.1290 0.5443 0.038 Uiso 1 1 calc R . .
C12 C 0.8679(3) 0.2084(2) 0.3536(3) 0.0281(6) Uani 1 1 d . . .
C13 C 1.0197(3) 0.1823(2) 0.2588(3) 0.0303(6) Uani 1 1 d . . .
C14 C 1.1362(3) 0.2026(3) 0.3005(3) 0.0380(7) Uani 1 1 d . . .
H14 H 1.1154 0.2339 0.3873 0.046 Uiso 1 1 calc R . .
C15 C 1.2811(3) 0.1777(3) 0.2175(3) 0.0477(8) Uani 1 1 d . . .
H15 H 1.3594 0.1921 0.2473 0.057 Uiso 1 1 calc R . .
C16 C 1.3131(3) 0.1322(3) 0.0920(3) 0.0509(8) Uani 1 1 d . . .
H16 H 1.4130 0.1163 0.0344 0.061 Uiso 1 1 calc R . .
C17 C 1.1993(4) 0.1096(3) 0.0499(3) 0.0494(8) Uani 1 1 d . . .
H17 H 1.2214 0.0770 -0.0366 0.059 Uiso 1 1 calc R . .
C18 C 1.0531(3) 0.1340(3) 0.1328(3) 0.0418(7) Uani 1 1 d . . .
H18 H 0.9756 0.1177 0.1033 0.050 Uiso 1 1 calc R . .
C19 C 0.7321(3) 0.3265(3) 0.1816(2) 0.0268(6) Uani 1 1 d . . .
C20 C 0.7967(3) 0.4394(3) 0.1161(3) 0.0357(7) Uani 1 1 d . . .
H20 H 0.8459 0.4815 0.1598 0.043 Uiso 1 1 calc R . .
C21 C 0.7890(3) 0.4907(3) -0.0133(3) 0.0453(8) Uani 1 1 d . . .
H21 H 0.8355 0.5668 -0.0599 0.054 Uiso 1 1 calc R . .
C22 C 0.7147(3) 0.4325(3) -0.0755(3) 0.0483(8) Uani 1 1 d . . .
H22 H 0.7069 0.4704 -0.1635 0.058 Uiso 1 1 calc R . .
C23 C 0.6516(3) 0.3196(3) -0.0101(3) 0.0472(8) Uani 1 1 d . . .
H23 H 0.6006 0.2790 -0.0532 0.057 Uiso 1 1 calc R . .
C24 C 0.6621(3) 0.2648(3) 0.1185(3) 0.0361(7) Uani 1 1 d . . .
H24 H 0.6210 0.1848 0.1627 0.043 Uiso 1 1 calc R . .
N1 N 0.7392(2) 0.2718(2) 0.31656(19) 0.0269(5) Uani 1 1 d . . .
O1 O 0.4509(2) 0.45860(18) 0.34132(18) 0.0420(5) 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 O1 1.223(3) . ?
C1 C8 1.461(3) . ?
C1 C2 1.494(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.393(3) . ?
C8 N1 1.395(3) . ?
C9 C11 1.397(3) . ?
C9 C10 1.505(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 N1 1.374(3) . ?
C12 C13 1.473(4) . ?
C13 C18 1.386(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.370(3) . ?
C19 C20 1.379(3) . ?
C19 N1 1.437(3) . ?
C20 C21 1.379(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8 121.4(2) . . ?
O1 C1 C2 119.1(2) . . ?
C8 C1 C2 119.5(2) . . ?
C7 C2 C3 118.9(2) . . ?
C7 C2 C1 122.3(2) . . ?
C3 C2 C1 118.7(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 N1 107.3(2) . . ?
C9 C8 C1 130.7(2) . . ?
N1 C8 C1 120.8(2) . . ?
C8 C9 C11 106.9(2) . . ?
C8 C9 C10 128.7(2) . . ?
C11 C9 C10 124.1(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 109.3(2) . . ?
C12 C11 H11 125.4 . . ?
C9 C11 H11 125.4 . . ?
N1 C12 C11 107.3(2) . . ?
N1 C12 C13 124.5(2) . . ?
C11 C12 C13 128.2(2) . . ?
C18 C13 C14 118.6(3) . . ?
C18 C13 C12 123.5(2) . . ?
C14 C13 C12 117.9(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C24 C19 C20 120.5(2) . . ?
C24 C19 N1 119.5(2) . . ?
C20 C19 N1 120.0(2) . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 119.6(3) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C12 N1 C8 109.2(2) . . ?
C12 N1 C19 125.7(2) . . ?
C8 N1 C19 125.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
