# 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_b141218a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1493851'
_audit_update_record             
;
2016-07-15 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Br N O3'
_chemical_formula_sum            'C15 H14 Br N O3'
_chemical_formula_weight         336.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   10.1366(8)
_cell_length_b                   13.6377(10)
_cell_length_c                   10.5947(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.508(2)
_cell_angle_gamma                90.00
_cell_volume                     1452.05(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6614
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_T_max  0.6005
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24186
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         30.08
_reflns_number_total             4250
_reflns_number_gt                2620
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+1.0065P] 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         4250
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.084
_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
Br1 Br 0.29217(4) 0.37452(2) 0.36598(4) 0.05452(16) Uani 1 1 d . . .
O1 O 0.5494(2) 0.74955(17) 0.2718(2) 0.0473(6) Uani 1 1 d . . .
O2 O 0.5688(2) 0.60958(16) 0.0316(2) 0.0424(6) Uani 1 1 d . . .
N1 N 0.3954(3) 0.74311(17) 0.4119(2) 0.0330(6) Uani 1 1 d . . .
O3 O 0.3541(2) 0.64967(18) 0.0139(2) 0.0470(6) Uani 1 1 d . . .
C1 C 0.4701(3) 0.7045(2) 0.3253(3) 0.0324(7) Uani 1 1 d . . .
C2 C 0.3151(3) 0.6706(2) 0.4579(3) 0.0289(6) Uani 1 1 d . . .
C3 C 0.2274(3) 0.6811(2) 0.5456(3) 0.0357(7) Uani 1 1 d . . .
H3 H 0.2158 0.7424 0.5853 0.043 Uiso 1 1 calc R . .
C4 C 0.1571(3) 0.5993(3) 0.5737(3) 0.0415(8) Uani 1 1 d . . .
H4 H 0.0944 0.6050 0.6325 0.050 Uiso 1 1 calc R . .
C5 C 0.1753(3) 0.5099(3) 0.5191(3) 0.0389(8) Uani 1 1 d . . .
H5 H 0.1263 0.4544 0.5409 0.047 Uiso 1 1 calc R . .
C6 C 0.2653(3) 0.5010(2) 0.4322(3) 0.0319(7) Uani 1 1 d . . .
C7 C 0.3365(3) 0.5811(2) 0.3993(3) 0.0260(6) Uani 1 1 d . . .
C8 C 0.4361(3) 0.5982(2) 0.3120(3) 0.0261(6) Uani 1 1 d . . .
C9 C 0.5444(3) 0.5278(2) 0.2844(3) 0.0369(7) Uani 1 1 d . . .
H9A H 0.6328 0.5556 0.2751 0.044 Uiso 1 1 calc R . .
H9B H 0.5467 0.4623 0.3250 0.044 Uiso 1 1 calc R . .
C10 C 0.4337(3) 0.5487(2) 0.1826(3) 0.0292(6) Uani 1 1 d . . .
H10 H 0.3669 0.4949 0.1644 0.035 Uiso 1 1 calc R . .
C11 C 0.4628(3) 0.6061(2) 0.0695(3) 0.0317(7) Uani 1 1 d . . .
C12 C 0.3704(5) 0.7055(3) -0.1004(3) 0.0641(11) Uani 1 1 d . . .
H12A H 0.4337 0.7591 -0.0784 0.096 Uiso 1 1 calc R . .
H12B H 0.2843 0.7327 -0.1368 0.096 Uiso 1 1 calc R . .
H12C H 0.4041 0.6623 -0.1628 0.096 Uiso 1 1 calc R . .
C13 C 0.4030(4) 0.8448(2) 0.4540(3) 0.0421(8) Uani 1 1 d . B .
H13A H 0.3127 0.8677 0.4659 0.051 Uiso 1 1 calc R . .
H13B H 0.4346 0.8857 0.3868 0.051 Uiso 1 1 calc R . .
C14 C 0.4934(4) 0.8591(3) 0.5750(4) 0.0576(11) Uani 1 1 d . . .
H14 H 0.5821 0.8357 0.5790 0.069 Uiso 1 1 calc R A 1
C15 C 0.4596(9) 0.9009(5) 0.6738(6) 0.0998(19) Uani 1 1 d D B 1
H15A H 0.526(5) 0.910(5) 0.745(4) 0.14(3) Uiso 1 1 d D . .
H15 H 0.368(3) 0.917(7) 0.663(9) 0.22(5) Uiso 1 1 d 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
Br1 C6 1.895(3) . ?
O1 C1 1.210(3) . ?
O2 C11 1.196(4) . ?
N1 C1 1.369(4) . ?
N1 C2 1.408(4) . ?
N1 C13 1.457(4) . ?
O3 C11 1.321(4) . ?
O3 C12 1.458(4) . ?
C1 C8 1.492(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C7 C8 1.474(4) . ?
C8 C9 1.515(4) . ?
C8 C10 1.525(4) . ?
C9 C10 1.478(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.493(4) . ?
C10 H10 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.487(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.278(7) . ?
C14 H14 0.9500 . ?
C15 H15A 0.951(10) . ?
C15 H15 0.950(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.0(2) . . ?
C1 N1 C13 124.1(3) . . ?
C2 N1 C13 124.9(3) . . ?
C11 O3 C12 115.3(3) . . ?
O1 C1 N1 125.3(3) . . ?
O1 C1 C8 127.5(3) . . ?
N1 C1 C8 107.2(2) . . ?
C3 C2 C7 122.8(3) . . ?
C3 C2 N1 128.0(3) . . ?
C7 C2 N1 109.2(2) . . ?
C2 C3 C4 117.5(3) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 Br1 121.5(2) . . ?
C5 C6 Br1 117.7(2) . . ?
C6 C7 C2 117.5(3) . . ?
C6 C7 C8 135.1(3) . . ?
C2 C7 C8 107.4(2) . . ?
C7 C8 C1 105.2(2) . . ?
C7 C8 C9 126.4(2) . . ?
C1 C8 C9 118.0(3) . . ?
C7 C8 C10 124.2(2) . . ?
C1 C8 C10 119.4(2) . . ?
C9 C8 C10 58.18(19) . . ?
C10 C9 C8 61.24(18) . . ?
C10 C9 H9A 117.6 . . ?
C8 C9 H9A 117.6 . . ?
C10 C9 H9B 117.6 . . ?
C8 C9 H9B 117.6 . . ?
H9A C9 H9B 114.8 . . ?
C9 C10 C11 118.4(3) . . ?
C9 C10 C8 60.59(19) . . ?
C11 C10 C8 120.5(2) . . ?
C9 C10 H10 115.4 . . ?
C11 C10 H10 115.4 . . ?
C8 C10 H10 115.4 . . ?
O2 C11 O3 124.5(3) . . ?
O2 C11 C10 124.8(3) . . ?
O3 C11 C10 110.7(3) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 113.0(3) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 124.3(5) . . ?
C15 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C14 C15 H15A 118(4) . . ?
C14 C15 H15 112(6) . . ?
H15A C15 H15 131(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.08
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_b140420a_0m
_database_code_depnum_ccdc_archive 'CCDC 1494266'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Cl N O3'
_chemical_formula_sum            'C15 H14 Cl N O3'
_chemical_formula_weight         291.72

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'
Cl Cl 0.1484 0.1585 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.8908(4)
_cell_length_b                   11.0249(4)
_cell_length_c                   13.2194(5)
_cell_angle_alpha                88.096(2)
_cell_angle_beta                 71.104(2)
_cell_angle_gamma                72.794(2)
_cell_volume                     1431.07(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    8085
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9374
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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            37254
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.55
_reflns_number_total             6586
_reflns_number_gt                4222
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0342P)²+0.5836P] 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         6586
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.56412(6) 1.34296(5) 0.15081(5) 0.03733(16) Uani 1 1 d . . .
Cl2 Cl 0.16857(6) 0.17524(5) 0.43766(4) 0.03379(15) Uani 1 1 d . . .
O1 O 0.75372(15) 0.67697(12) -0.08571(11) 0.0269(3) Uani 1 1 d . . .
O2 O 1.04324(15) 0.66964(13) -0.04492(11) 0.0292(4) Uani 1 1 d . . .
O3 O 1.06285(18) 0.66995(15) -0.21781(13) 0.0468(5) Uani 1 1 d . . .
O4 O 0.18460(16) 0.84204(13) 0.30881(12) 0.0334(4) Uani 1 1 d . . .
O5 O -0.11916(14) 0.82027(13) 0.27689(12) 0.0310(4) Uani 1 1 d . . .
O6 O 0.04626(15) 0.85172(13) 0.13574(12) 0.0310(4) Uani 1 1 d . . .
N1 N 0.60543(17) 0.81432(15) 0.05937(13) 0.0222(4) Uani 1 1 d . . .
N2 N 0.18915(18) 0.70015(15) 0.44027(13) 0.0246(4) Uani 1 1 d . . .
C1 C 0.5768(2) 1.18346(18) 0.13190(17) 0.0241(5) Uani 1 1 d . . .
C2 C 0.4796(2) 1.1358(2) 0.20052(17) 0.0272(5) Uani 1 1 d . . .
H2 H 0.4105 1.1883 0.2596 0.033 Uiso 1 1 calc R . .
C3 C 0.4823(2) 1.01089(19) 0.18369(16) 0.0246(5) Uani 1 1 d . . .
H3 H 0.4162 0.9764 0.2304 0.029 Uiso 1 1 calc R . .
C4 C 0.5845(2) 0.93935(18) 0.09673(16) 0.0210(5) Uani 1 1 d . . .
C5 C 0.68499(19) 0.98671(18) 0.02894(15) 0.0191(4) Uani 1 1 d . . .
C6 C 0.6825(2) 1.11034(18) 0.04594(16) 0.0227(5) Uani 1 1 d . . .
H6 H 0.7502 1.1441 0.0007 0.027 Uiso 1 1 calc R . .
C7 C 0.7741(2) 0.88638(18) -0.05660(15) 0.0196(4) Uani 1 1 d . . .
C8 C 0.9286(2) 0.85771(18) -0.10352(16) 0.0222(5) Uani 1 1 d . . .
H8 H 0.9676 0.9171 -0.0776 0.027 Uiso 1 1 calc R . .
C9 C 0.8438(2) 0.91240(19) -0.17062(16) 0.0251(5) Uani 1 1 d . . .
H9A H 0.8472 0.8562 -0.2290 0.030 Uiso 1 1 calc R . .
H9B H 0.8332 1.0023 -0.1874 0.030 Uiso 1 1 calc R . .
C10 C 1.0172(2) 0.72301(19) -0.13027(17) 0.0241(5) Uani 1 1 d . . .
C11 C 1.1377(2) 0.5420(2) -0.0675(2) 0.0394(6) Uani 1 1 d . . .
H11A H 1.1005 0.4868 -0.0976 0.059 Uiso 1 1 calc R . .
H11B H 1.1515 0.5089 -0.0010 0.059 Uiso 1 1 calc R . .
H11C H 1.2249 0.5440 -0.1191 0.059 Uiso 1 1 calc R . .
C12 C 0.7145(2) 0.77861(18) -0.03347(16) 0.0217(5) Uani 1 1 d . . .
C13 C 0.5180(2) 0.7371(2) 0.10798(17) 0.0265(5) Uani 1 1 d . . .
H13A H 0.5343 0.6677 0.0551 0.032 Uiso 1 1 calc R . .
H13B H 0.4220 0.7902 0.1254 0.032 Uiso 1 1 calc R . .
C14 C 0.5387(2) 0.6797(2) 0.20761(17) 0.0286(5) Uani 1 1 d . . .
H14 H 0.4807 0.6312 0.2440 0.034 Uiso 1 1 calc R . .
C15 C 0.6289(2) 0.6901(2) 0.24926(18) 0.0369(6) Uani 1 1 d . . .
H15A H 0.6891 0.7378 0.2158 0.044 Uiso 1 1 calc R . .
H15B H 0.6343 0.6501 0.3131 0.044 Uiso 1 1 calc R . .
C16 C 0.1772(2) 0.33093(19) 0.44150(16) 0.0231(5) Uani 1 1 d . . .
C17 C 0.1910(2) 0.3775(2) 0.53133(16) 0.0254(5) Uani 1 1 d . . .
H17 H 0.1974 0.3245 0.5887 0.031 Uiso 1 1 calc R . .
C18 C 0.1957(2) 0.5012(2) 0.53872(16) 0.0261(5) Uani 1 1 d . . .
H18 H 0.2041 0.5347 0.6006 0.031 Uiso 1 1 calc R . .
C19 C 0.1878(2) 0.57333(18) 0.45252(16) 0.0216(5) Uani 1 1 d . . .
C20 C 0.17536(19) 0.52537(18) 0.36104(15) 0.0199(4) Uani 1 1 d . . .
C21 C 0.16927(19) 0.40325(19) 0.35460(16) 0.0218(5) Uani 1 1 d . . .
H21 H 0.1600 0.3697 0.2931 0.026 Uiso 1 1 calc R . .
C22 C 0.1703(2) 0.62779(18) 0.28589(16) 0.0207(4) Uani 1 1 d . . .
C23 C 0.0796(2) 0.65075(18) 0.21512(15) 0.0214(5) Uani 1 1 d . . .
H23 H 0.0311 0.5862 0.2166 0.026 Uiso 1 1 calc R . .
C24 C 0.2292(2) 0.60542(19) 0.16512(15) 0.0227(5) Uani 1 1 d . . .
H24A H 0.2745 0.6664 0.1249 0.027 Uiso 1 1 calc R . .
H24B H 0.2711 0.5162 0.1347 0.027 Uiso 1 1 calc R . .
C25 C 0.0044(2) 0.78481(19) 0.20251(16) 0.0209(5) Uani 1 1 d . . .
C26 C -0.1971(2) 0.9519(2) 0.2790(2) 0.0419(6) Uani 1 1 d . . .
H26A H -0.1465 1.0070 0.2911 0.063 Uiso 1 1 calc R . .
H26B H -0.2846 0.9695 0.3370 0.063 Uiso 1 1 calc R . .
H26C H -0.2131 0.9685 0.2104 0.063 Uiso 1 1 calc R . .
C27 C 0.1812(2) 0.73836(19) 0.34199(16) 0.0239(5) Uani 1 1 d . . .
C28 C 0.1981(2) 0.7821(2) 0.52033(17) 0.0313(5) Uani 1 1 d . . .
H28A H 0.1437 0.7657 0.5925 0.038 Uiso 1 1 calc R . .
H28B H 0.1588 0.8722 0.5080 0.038 Uiso 1 1 calc R . .
C29 C 0.3405(3) 0.7604(3) 0.5165(2) 0.0490(7) Uani 1 1 d . . .
H29 H 0.4025 0.7776 0.4525 0.059 Uiso 1 1 calc R . .
C30 C 0.3866(3) 0.7196(3) 0.5941(3) 0.0720(10) Uani 1 1 d . . .
H30A H 0.3276 0.7013 0.6594 0.086 Uiso 1 1 calc R . .
H30B H 0.4794 0.7078 0.5859 0.086 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.743(2) . ?
Cl2 C16 1.750(2) . ?
O1 C12 1.222(2) . ?
O2 C10 1.328(2) . ?
O2 C11 1.449(2) . ?
O3 C10 1.195(2) . ?
O4 C27 1.217(2) . ?
O5 C25 1.337(2) . ?
O5 C26 1.444(2) . ?
O6 C25 1.194(2) . ?
N1 C12 1.373(3) . ?
N1 C4 1.408(2) . ?
N1 C13 1.447(2) . ?
N2 C27 1.374(3) . ?
N2 C19 1.406(3) . ?
N2 C28 1.459(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.380(3) . ?
C5 C7 1.477(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.493(3) . ?
C7 C9 1.513(3) . ?
C7 C8 1.530(3) . ?
C8 C9 1.473(3) . ?
C8 C10 1.493(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.496(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.304(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C16 C17 1.378(3) . ?
C16 C21 1.388(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(3) . ?
C20 C21 1.374(3) . ?
C20 C22 1.480(3) . ?
C21 H21 0.9500 . ?
C22 C27 1.501(3) . ?
C22 C24 1.513(3) . ?
C22 C23 1.533(3) . ?
C23 C24 1.478(3) . ?
C23 C25 1.496(3) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 C29 1.482(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.295(4) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9500 . ?
C30 H30B 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
C10 O2 C11 114.16(17) . . ?
C25 O5 C26 115.34(17) . . ?
C12 N1 C4 110.95(16) . . ?
C12 N1 C13 124.38(17) . . ?
C4 N1 C13 124.54(17) . . ?
C27 N2 C19 111.22(16) . . ?
C27 N2 C28 123.59(17) . . ?
C19 N2 C28 125.19(17) . . ?
C2 C1 C6 122.54(19) . . ?
C2 C1 Cl1 118.87(16) . . ?
C6 C1 Cl1 118.56(16) . . ?
C1 C2 C3 120.23(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 117.39(19) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 122.30(18) . . ?
C3 C4 N1 128.44(19) . . ?
C5 C4 N1 109.24(17) . . ?
C6 C5 C4 120.21(18) . . ?
C6 C5 C7 132.14(18) . . ?
C4 C5 C7 107.53(16) . . ?
C5 C6 C1 117.28(19) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
C5 C7 C12 105.18(16) . . ?
C5 C7 C9 124.03(17) . . ?
C12 C7 C9 120.95(17) . . ?
C5 C7 C8 124.08(17) . . ?
C12 C7 C8 119.32(17) . . ?
C9 C7 C8 57.91(13) . . ?
C9 C8 C10 117.94(17) . . ?
C9 C8 C7 60.48(13) . . ?
C10 C8 C7 119.70(17) . . ?
C9 C8 H8 115.8 . . ?
C10 C8 H8 115.8 . . ?
C7 C8 H8 115.8 . . ?
C8 C9 C7 61.61(13) . . ?
C8 C9 H9A 117.6 . . ?
C7 C9 H9A 117.6 . . ?
C8 C9 H9B 117.6 . . ?
C7 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
O3 C10 O2 123.67(19) . . ?
O3 C10 C8 124.78(19) . . ?
O2 C10 C8 111.52(17) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 N1 125.42(19) . . ?
O1 C12 C7 127.55(19) . . ?
N1 C12 C7 107.03(16) . . ?
N1 C13 C14 114.04(17) . . ?
N1 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 126.1(2) . . ?
C15 C14 H14 116.9 . . ?
C13 C14 H14 116.9 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C17 C16 C21 122.33(19) . . ?
C17 C16 Cl2 118.58(16) . . ?
C21 C16 Cl2 119.09(16) . . ?
C16 C17 C18 120.58(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 117.22(19) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C20 122.07(19) . . ?
C18 C19 N2 128.42(19) . . ?
C20 C19 N2 109.51(17) . . ?
C21 C20 C19 120.47(18) . . ?
C21 C20 C22 132.30(18) . . ?
C19 C20 C22 107.23(17) . . ?
C20 C21 C16 117.32(19) . . ?
C20 C21 H21 121.3 . . ?
C16 C21 H21 121.3 . . ?
C20 C22 C27 105.39(16) . . ?
C20 C22 C24 124.27(17) . . ?
C27 C22 C24 120.83(17) . . ?
C20 C22 C23 122.73(17) . . ?
C27 C22 C23 120.10(16) . . ?
C24 C22 C23 58.02(13) . . ?
C24 C23 C25 119.00(17) . . ?
C24 C23 C22 60.32(13) . . ?
C25 C23 C22 118.67(16) . . ?
C24 C23 H23 115.8 . . ?
C25 C23 H23 115.8 . . ?
C22 C23 H23 115.8 . . ?
C23 C24 C22 61.65(13) . . ?
C23 C24 H24A 117.6 . . ?
C22 C24 H24A 117.6 . . ?
C23 C24 H24B 117.6 . . ?
C22 C24 H24B 117.6 . . ?
H24A C24 H24B 114.7 . . ?
O6 C25 O5 123.94(19) . . ?
O6 C25 C23 125.85(19) . . ?
O5 C25 C23 110.20(17) . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O4 C27 N2 125.21(19) . . ?
O4 C27 C22 128.17(19) . . ?
N2 C27 C22 106.62(17) . . ?
N2 C28 C29 111.96(19) . . ?
N2 C28 H28A 109.2 . . ?
C29 C28 H28A 109.2 . . ?
N2 C28 H28B 109.2 . . ?
C29 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 C28 124.7(3) . . ?
C30 C29 H29 117.7 . . ?
C28 C29 H29 117.7 . . ?
C29 C30 H30A 120.0 . . ?
C29 C30 H30B 120.0 . . ?
H30A C30 H30B 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
C6 C1 C2 C3 -1.8(3) . . . . ?
Cl1 C1 C2 C3 176.16(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C2 C3 C4 N1 -176.44(19) . . . . ?
C12 N1 C4 C3 176.59(19) . . . . ?
C13 N1 C4 C3 0.7(3) . . . . ?
C12 N1 C4 C5 -2.0(2) . . . . ?
C13 N1 C4 C5 -177.92(17) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
N1 C4 C5 C6 176.88(17) . . . . ?
C3 C4 C5 C7 -178.28(18) . . . . ?
N1 C4 C5 C7 0.4(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C7 C5 C6 C1 175.28(19) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
Cl1 C1 C6 C5 -175.99(15) . . . . ?
C6 C5 C7 C12 -174.7(2) . . . . ?
C4 C5 C7 C12 1.1(2) . . . . ?
C6 C5 C7 C9 -29.0(3) . . . . ?
C4 C5 C7 C9 146.86(19) . . . . ?
C6 C5 C7 C8 42.5(3) . . . . ?
C4 C5 C7 C8 -141.63(18) . . . . ?
C5 C7 C8 C9 -111.9(2) . . . . ?
C12 C7 C8 C9 110.1(2) . . . . ?
C5 C7 C8 C10 140.81(19) . . . . ?
C12 C7 C8 C10 2.8(3) . . . . ?
C9 C7 C8 C10 -107.3(2) . . . . ?
C10 C8 C9 C7 110.1(2) . . . . ?
C5 C7 C9 C8 112.0(2) . . . . ?
C12 C7 C9 C8 -107.3(2) . . . . ?
C11 O2 C10 O3 2.7(3) . . . . ?
C11 O2 C10 C8 -175.32(18) . . . . ?
C9 C8 C10 O3 27.7(3) . . . . ?
C7 C8 C10 O3 97.9(3) . . . . ?
C9 C8 C10 O2 -154.30(18) . . . . ?
C7 C8 C10 O2 -84.2(2) . . . . ?
C4 N1 C12 O1 -177.52(18) . . . . ?
C13 N1 C12 O1 -1.6(3) . . . . ?
C4 N1 C12 C7 2.7(2) . . . . ?
C13 N1 C12 C7 178.60(17) . . . . ?
C5 C7 C12 O1 177.88(19) . . . . ?
C9 C7 C12 O1 30.9(3) . . . . ?
C8 C7 C12 O1 -37.2(3) . . . . ?
C5 C7 C12 N1 -2.3(2) . . . . ?
C9 C7 C12 N1 -149.33(18) . . . . ?
C8 C7 C12 N1 142.62(17) . . . . ?
C12 N1 C13 C14 106.9(2) . . . . ?
C4 N1 C13 C14 -77.7(2) . . . . ?
N1 C13 C14 C15 -2.6(3) . . . . ?
C21 C16 C17 C18 0.9(3) . . . . ?
Cl2 C16 C17 C18 -178.81(16) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C17 C18 C19 N2 179.45(19) . . . . ?
C27 N2 C19 C18 179.1(2) . . . . ?
C28 N2 C19 C18 -0.7(3) . . . . ?
C27 N2 C19 C20 -1.4(2) . . . . ?
C28 N2 C19 C20 178.72(19) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
N2 C19 C20 C21 -178.86(17) . . . . ?
C18 C19 C20 C22 -179.76(18) . . . . ?
N2 C19 C20 C22 0.7(2) . . . . ?
C19 C20 C21 C16 -0.6(3) . . . . ?
C22 C20 C21 C16 180.0(2) . . . . ?
C17 C16 C21 C20 -0.2(3) . . . . ?
Cl2 C16 C21 C20 179.52(15) . . . . ?
C21 C20 C22 C27 179.6(2) . . . . ?
C19 C20 C22 C27 0.1(2) . . . . ?
C21 C20 C22 C24 -34.2(3) . . . . ?
C19 C20 C22 C24 146.30(19) . . . . ?
C21 C20 C22 C23 36.9(3) . . . . ?
C19 C20 C22 C23 -142.59(19) . . . . ?
C20 C22 C23 C24 -112.8(2) . . . . ?
C27 C22 C23 C24 109.7(2) . . . . ?
C20 C22 C23 C25 138.25(19) . . . . ?
C27 C22 C23 C25 0.7(3) . . . . ?
C24 C22 C23 C25 -108.9(2) . . . . ?
C25 C23 C24 C22 108.39(19) . . . . ?
C20 C22 C24 C23 110.2(2) . . . . ?
C27 C22 C24 C23 -108.4(2) . . . . ?
C26 O5 C25 O6 -5.9(3) . . . . ?
C26 O5 C25 C23 174.67(17) . . . . ?
C24 C23 C25 O6 19.1(3) . . . . ?
C22 C23 C25 O6 89.1(3) . . . . ?
C24 C23 C25 O5 -161.45(17) . . . . ?
C22 C23 C25 O5 -91.5(2) . . . . ?
C19 N2 C27 O4 -177.6(2) . . . . ?
C28 N2 C27 O4 2.3(3) . . . . ?
C19 N2 C27 C22 1.4(2) . . . . ?
C28 N2 C27 C22 -178.70(18) . . . . ?
C20 C22 C27 O4 178.1(2) . . . . ?
C24 C22 C27 O4 30.4(3) . . . . ?
C23 C22 C27 O4 -38.1(3) . . . . ?
C20 C22 C27 N2 -0.9(2) . . . . ?
C24 C22 C27 N2 -148.54(18) . . . . ?
C23 C22 C27 N2 142.98(18) . . . . ?
C27 N2 C28 C29 -97.0(3) . . . . ?
C19 N2 C28 C29 82.9(3) . . . . ?
N2 C28 C29 C30 -117.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_b150617c_0m
_database_code_depnum_ccdc_archive 'CCDC 1493852'
_audit_update_record             
;
2016-07-15 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 N O3'
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.9666(5)
_cell_length_b                   17.1779(8)
_cell_length_c                   11.1475(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.554(2)
_cell_angle_gamma                90.00
_cell_volume                     1775.05(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9581
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38999
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.59
_reflns_number_total             4104
_reflns_number_gt                3295
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.6940P] 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         4104
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48879(11) 0.08926(6) 0.09212(9) 0.0250(2) Uani 1 1 d . . .
O2 O 0.74990(10) 0.16919(6) 0.32271(9) 0.0235(2) Uani 1 1 d . . .
O3 O 0.64156(11) 0.25451(6) 0.16293(11) 0.0339(3) Uani 1 1 d . . .
N1 N 0.40766(12) 0.00893(6) 0.21740(10) 0.0175(2) Uani 1 1 d . . .
C1 C 0.41840(13) 0.13991(7) 0.26463(12) 0.0163(3) Uani 1 1 d . . .
C2 C 0.51869(14) 0.21046(7) 0.29958(12) 0.0182(3) Uani 1 1 d . . .
H2 H 0.5376 0.2330 0.3850 0.022 Uiso 1 1 calc R . .
C3 C 0.36964(14) 0.22042(7) 0.20405(12) 0.0183(3) Uani 1 1 d . . .
H3 H 0.3661 0.2239 0.1152 0.022 Uiso 1 1 calc R . .
C4 C 0.36543(13) 0.09741(7) 0.35390(11) 0.0153(3) Uani 1 1 d . . .
C5 C 0.32631(14) 0.12011(7) 0.45542(12) 0.0188(3) Uani 1 1 d . . .
H5 H 0.3278 0.1724 0.4776 0.023 Uiso 1 1 calc R . .
C6 C 0.28463(14) 0.06335(8) 0.52415(12) 0.0208(3) Uani 1 1 d . . .
H6 H 0.2570 0.0779 0.5921 0.025 Uiso 1 1 calc R . .
C7 C 0.28403(14) -0.01455(8) 0.49190(12) 0.0204(3) Uani 1 1 d . . .
H7 H 0.2574 -0.0517 0.5397 0.025 Uiso 1 1 calc R . .
C8 C 0.32240(13) -0.03861(7) 0.38970(12) 0.0182(3) Uani 1 1 d . . .
H8 H 0.3214 -0.0909 0.3679 0.022 Uiso 1 1 calc R . .
C9 C 0.36198(13) 0.01842(7) 0.32220(12) 0.0157(3) Uani 1 1 d . . .
C10 C 0.44411(14) 0.07880(7) 0.17926(12) 0.0179(3) Uani 1 1 d . . .
C11 C 0.42281(15) -0.06483(8) 0.16023(13) 0.0214(3) Uani 1 1 d . . .
H11A H 0.4692 -0.1018 0.2288 0.026 Uiso 1 1 calc R . .
H11B H 0.4856 -0.0575 0.1122 0.026 Uiso 1 1 calc R . .
C12 C 0.28349(17) -0.09882(9) 0.07218(14) 0.0290(3) Uani 1 1 d . . .
H12 H 0.2889 -0.1458 0.0328 0.035 Uiso 1 1 calc R . .
C13 C 0.15453(17) -0.06925(10) 0.04468(15) 0.0363(4) Uani 1 1 d . . .
H13A H 0.1433 -0.0223 0.0815 0.044 Uiso 1 1 calc R . .
H13B H 0.0742 -0.0952 -0.0117 0.044 Uiso 1 1 calc R . .
C14 C 0.64108(14) 0.21477(8) 0.25144(13) 0.0209(3) Uani 1 1 d . . .
C15 C 0.87392(15) 0.16177(9) 0.28382(14) 0.0287(3) Uani 1 1 d . . .
H15A H 0.9513 0.1956 0.3360 0.034 Uiso 1 1 calc R . .
H15B H 0.8474 0.1766 0.1941 0.034 Uiso 1 1 calc R . .
C16 C 0.92230(19) 0.07891(11) 0.30205(18) 0.0424(4) Uani 1 1 d . . .
H16A H 0.9475 0.0646 0.3909 0.064 Uiso 1 1 calc R . .
H16B H 1.0049 0.0728 0.2781 0.064 Uiso 1 1 calc R . .
H16C H 0.8457 0.0460 0.2489 0.064 Uiso 1 1 calc R . .
C17 C 0.25434(14) 0.26696(7) 0.22546(12) 0.0181(3) Uani 1 1 d . . .
C18 C 0.28138(14) 0.31573(8) 0.33107(13) 0.0208(3) Uani 1 1 d . . .
H18 H 0.3731 0.3174 0.3949 0.025 Uiso 1 1 calc R . .
C19 C 0.17205(16) 0.36208(8) 0.34202(14) 0.0271(3) Uani 1 1 d . . .
H19 H 0.1910 0.3946 0.4130 0.033 Uiso 1 1 calc R . .
C20 C 0.03516(16) 0.35999(9) 0.24773(15) 0.0306(3) Uani 1 1 d . . .
H20 H -0.0376 0.3912 0.2552 0.037 Uiso 1 1 calc R . .
C21 C 0.00668(15) 0.31129(9) 0.14235(14) 0.0288(3) Uani 1 1 d . . .
H21 H -0.0854 0.3096 0.0791 0.035 Uiso 1 1 calc R . .
C22 C 0.11552(15) 0.26511(8) 0.13131(13) 0.0239(3) Uani 1 1 d . . .
H22 H 0.0959 0.2325 0.0603 0.029 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.2215(15) . ?
O2 C14 1.3369(16) . ?
O2 C15 1.4579(16) . ?
O3 C14 1.2013(16) . ?
N1 C10 1.3663(17) . ?
N1 C9 1.4105(16) . ?
N1 C11 1.4509(16) . ?
C1 C4 1.4792(17) . ?
C1 C10 1.5008(17) . ?
C1 C2 1.5276(17) . ?
C1 C3 1.5376(17) . ?
C2 C3 1.4859(18) . ?
C2 C14 1.5041(18) . ?
C2 H2 0.9800 . ?
C3 C17 1.4893(18) . ?
C3 H3 0.9800 . ?
C4 C5 1.3817(17) . ?
C4 C9 1.3995(17) . ?
C5 C6 1.3943(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.3850(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.3911(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.3782(17) . ?
C8 H8 0.9300 . ?
C11 C12 1.4936(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.309(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C15 C16 1.493(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.3884(18) . ?
C17 C22 1.3964(18) . ?
C18 C19 1.3907(19) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9300 . ?
C22 H22 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
C14 O2 C15 117.76(11) . . ?
C10 N1 C9 111.09(10) . . ?
C10 N1 C11 123.23(10) . . ?
C9 N1 C11 125.60(11) . . ?
C4 C1 C10 105.53(10) . . ?
C4 C1 C2 125.58(11) . . ?
C10 C1 C2 117.93(11) . . ?
C4 C1 C3 127.31(11) . . ?
C10 C1 C3 116.79(10) . . ?
C2 C1 C3 57.99(8) . . ?
C3 C2 C14 117.84(11) . . ?
C3 C2 C1 61.34(8) . . ?
C14 C2 C1 119.24(11) . . ?
C3 C2 H2 115.8 . . ?
C14 C2 H2 115.8 . . ?
C1 C2 H2 115.8 . . ?
C2 C3 C17 125.04(11) . . ?
C2 C3 C1 60.67(8) . . ?
C17 C3 C1 123.40(11) . . ?
C2 C3 H3 112.7 . . ?
C17 C3 H3 112.7 . . ?
C1 C3 H3 112.7 . . ?
C5 C4 C9 119.50(11) . . ?
C5 C4 C1 133.60(12) . . ?
C9 C4 C1 106.88(10) . . ?
C4 C5 C6 118.90(12) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.45(12) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.55(12) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 117.13(12) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C8 C9 C4 122.46(11) . . ?
C8 C9 N1 127.90(11) . . ?
C4 C9 N1 109.62(11) . . ?
O1 C10 N1 126.36(12) . . ?
O1 C10 C1 126.76(12) . . ?
N1 C10 C1 106.87(10) . . ?
N1 C11 C12 114.10(11) . . ?
N1 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 126.72(14) . . ?
C13 C12 H12 116.6 . . ?
C11 C12 H12 116.6 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O3 C14 O2 125.01(12) . . ?
O3 C14 C2 124.72(12) . . ?
O2 C14 C2 110.27(11) . . ?
O2 C15 C16 108.04(12) . . ?
O2 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O2 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.76(12) . . ?
C18 C17 C3 122.61(12) . . ?
C22 C17 C3 118.50(12) . . ?
C17 C18 C19 120.38(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.28(13) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.88(13) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 119.89(14) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 120.80(13) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?

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
C4 C1 C2 C3 -115.57(14) . . . . ?
C10 C1 C2 C3 105.67(12) . . . . ?
C4 C1 C2 C14 136.74(13) . . . . ?
C10 C1 C2 C14 -2.02(17) . . . . ?
C3 C1 C2 C14 -107.69(13) . . . . ?
C14 C2 C3 C17 -137.91(13) . . . . ?
C1 C2 C3 C17 112.15(13) . . . . ?
C14 C2 C3 C1 109.93(12) . . . . ?
C4 C1 C3 C2 112.73(14) . . . . ?
C10 C1 C3 C2 -107.65(12) . . . . ?
C4 C1 C3 C17 -2.0(2) . . . . ?
C10 C1 C3 C17 137.62(12) . . . . ?
C2 C1 C3 C17 -114.73(14) . . . . ?
C10 C1 C4 C5 178.39(13) . . . . ?
C2 C1 C4 C5 35.6(2) . . . . ?
C3 C1 C4 C5 -38.5(2) . . . . ?
C10 C1 C4 C9 0.26(13) . . . . ?
C2 C1 C4 C9 -142.54(12) . . . . ?
C3 C1 C4 C9 143.38(12) . . . . ?
C9 C4 C5 C6 0.18(18) . . . . ?
C1 C4 C5 C6 -177.76(13) . . . . ?
C4 C5 C6 C7 0.69(19) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C9 0.39(19) . . . . ?
C7 C8 C9 C4 0.51(18) . . . . ?
C7 C8 C9 N1 178.65(12) . . . . ?
C5 C4 C9 C8 -0.81(18) . . . . ?
C1 C4 C9 C8 177.64(11) . . . . ?
C5 C4 C9 N1 -179.25(11) . . . . ?
C1 C4 C9 N1 -0.80(13) . . . . ?
C10 N1 C9 C8 -177.24(12) . . . . ?
C11 N1 C9 C8 -0.5(2) . . . . ?
C10 N1 C9 C4 1.10(14) . . . . ?
C11 N1 C9 C4 177.86(11) . . . . ?
C9 N1 C10 O1 179.23(12) . . . . ?
C11 N1 C10 O1 2.4(2) . . . . ?
C9 N1 C10 C1 -0.89(14) . . . . ?
C11 N1 C10 C1 -177.74(11) . . . . ?
C4 C1 C10 O1 -179.75(12) . . . . ?
C2 C1 C10 O1 -33.57(19) . . . . ?
C3 C1 C10 O1 32.58(19) . . . . ?
C4 C1 C10 N1 0.37(13) . . . . ?
C2 C1 C10 N1 146.56(11) . . . . ?
C3 C1 C10 N1 -147.29(11) . . . . ?
C10 N1 C11 C12 -105.53(14) . . . . ?
C9 N1 C11 C12 78.08(16) . . . . ?
N1 C11 C12 C13 -0.7(2) . . . . ?
C15 O2 C14 O3 -5.5(2) . . . . ?
C15 O2 C14 C2 175.62(11) . . . . ?
C3 C2 C14 O3 32.15(19) . . . . ?
C1 C2 C14 O3 103.12(16) . . . . ?
C3 C2 C14 O2 -148.97(11) . . . . ?
C1 C2 C14 O2 -77.99(14) . . . . ?
C14 O2 C15 C16 -140.16(13) . . . . ?
C2 C3 C17 C18 10.02(19) . . . . ?
C1 C3 C17 C18 85.28(16) . . . . ?
C2 C3 C17 C22 -174.13(12) . . . . ?
C1 C3 C17 C22 -98.86(15) . . . . ?
C22 C17 C18 C19 -0.36(19) . . . . ?
C3 C17 C18 C19 175.49(12) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C20 C21 C22 C17 0.0(2) . . . . ?
C18 C17 C22 C21 0.3(2) . . . . ?
C3 C17 C22 C21 -175.68(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058
