# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2213723'
loop_
_audit_author_name
_audit_author_address
'Hou Zhong-Wei'
;Taizhou University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 Br N O2'
_chemical_formula_weight         326.23

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'
Br Br -0.2901 2.4595 '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                   7.079(2)
_cell_length_b                   9.363(3)
_cell_length_c                   11.864(3)
_cell_angle_alpha                93.881(5)
_cell_angle_beta                 97.142(5)
_cell_angle_gamma                100.629(4)
_cell_volume                     763.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1768
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.12

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    2.690
_shelx_estimated_absorpt_T_min   0.541
_shelx_estimated_absorpt_T_max   0.565
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3901
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2672
_reflns_number_gt                2034
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0663P)²+0.3324P] 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         2672
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
Br1 Br 0.17186(6) 0.58524(4) 0.41155(4) 0.0644(2) Uani 1 1 d . . . . .
O2 O 0.5477(4) 1.0367(3) 0.3552(3) 0.0619(8) Uani 1 1 d . . . . .
N1 N 0.7379(4) 0.9158(3) 0.2557(2) 0.0370(6) Uani 1 1 d . . . . .
C4 C 0.5460(5) 0.6772(3) 0.2470(3) 0.0362(8) Uani 1 1 d . . . . .
C8 C 0.5166(5) 0.7737(3) 0.3540(3) 0.0345(7) Uani 1 1 d . . . . .
C7 C 0.7424(5) 0.7641(3) 0.2210(3) 0.0395(8) Uani 1 1 d . . . . .
H7A H 0.8507 0.7332 0.2644 0.047 Uiso 1 1 calc R U . . .
H7B H 0.7530 0.7509 0.1404 0.047 Uiso 1 1 calc R U . . .
O1 O 0.1973(6) 0.3172(4) 0.0540(3) 0.0976(13) Uani 1 1 d . . . . .
C11 C 0.5997(5) 0.9257(4) 0.3227(3) 0.0408(8) Uani 1 1 d . . . . .
C3 C 0.5589(5) 0.5243(4) 0.2666(3) 0.0450(9) Uani 1 1 d . . . . .
H3 H 0.6494 0.5082 0.3258 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3953(5) 0.6859(4) 0.1492(3) 0.0475(9) Uani 1 1 d . . . . .
H5 H 0.3786 0.7780 0.1305 0.057 Uiso 1 1 calc R U . . .
C12 C 0.8553(5) 1.0397(4) 0.2092(3) 0.0402(8) Uani 1 1 d . . . . .
C9 C 0.3079(5) 0.7711(4) 0.3734(4) 0.0497(9) Uani 1 1 d . . . . .
H9A H 0.2372 0.7970 0.3048 0.060 Uiso 1 1 calc R U . . .
H9B H 0.3072 0.8451 0.4345 0.060 Uiso 1 1 calc R U . . .
C10 C 0.6393(6) 0.7485(4) 0.4639(3) 0.0496(9) Uani 1 1 d . . . . .
H10A H 0.5888 0.6542 0.4869 0.074 Uiso 1 1 calc R U . . .
H10B H 0.6350 0.8226 0.5230 0.074 Uiso 1 1 calc R U . . .
H10C H 0.7712 0.7528 0.4506 0.074 Uiso 1 1 calc R U . . .
C2 C 0.4473(6) 0.4088(4) 0.2039(4) 0.0574(11) Uani 1 1 d . . . . .
H2 H 0.4637 0.3157 0.2203 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2844(6) 0.5717(5) 0.0877(3) 0.0635(12) Uani 1 1 d . . . . .
H6 H 0.1932 0.5863 0.0283 0.076 Uiso 1 1 calc R U . . .
C1 C 0.3008(7) 0.4239(5) 0.1105(4) 0.0649(13) Uani 1 1 d . . . . .
C14 C 0.7319(7) 1.0831(5) 0.1088(4) 0.0721(13) Uani 1 1 d . . . . .
H14A H 0.6885 1.0008 0.0529 0.108 Uiso 1 1 calc R U . . .
H14B H 0.8073 1.1612 0.0757 0.108 Uiso 1 1 calc R U . . .
H14C H 0.6216 1.1148 0.1342 0.108 Uiso 1 1 calc R U . . .
C15 C 1.0301(6) 0.9934(5) 0.1670(5) 0.0773(15) Uani 1 1 d . . . . .
H15A H 1.1094 0.9639 0.2295 0.116 Uiso 1 1 calc R U . . .
H15B H 1.1043 1.0737 0.1356 0.116 Uiso 1 1 calc R U . . .
H15C H 0.9875 0.9131 0.1092 0.116 Uiso 1 1 calc R U . . .
C13 C 0.9226(9) 1.1690(6) 0.2991(5) 0.104(2) Uani 1 1 d . . . . .
H13A H 0.8116 1.2014 0.3231 0.156 Uiso 1 1 calc R U . . .
H13B H 1.0007 1.2471 0.2675 0.156 Uiso 1 1 calc R U . . .
H13C H 0.9978 1.1400 0.3636 0.156 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
Br1 C9 1.938(4) . ?
O2 C11 1.219(4) . ?
N1 C11 1.347(4) . ?
N1 C7 1.459(4) . ?
N1 C12 1.478(4) . ?
C4 C3 1.483(5) . ?
C4 C5 1.492(5) . ?
C4 C7 1.553(5) . ?
C4 C8 1.566(5) . ?
C8 C9 1.519(5) . ?
C8 C11 1.525(5) . ?
C8 C10 1.532(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1 C1 1.225(5) . ?
C3 C2 1.334(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.317(5) . ?
C5 H5 0.9300 . ?
C12 C14 1.511(5) . ?
C12 C15 1.514(6) . ?
C12 C13 1.522(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 C1 1.453(6) . ?
C2 H2 0.9300 . ?
C6 C1 1.451(6) . ?
C6 H6 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C11 N1 C7 111.5(3) . . ?
C11 N1 C12 125.5(3) . . ?
C7 N1 C12 122.5(3) . . ?
C3 C4 C5 112.2(3) . . ?
C3 C4 C7 111.3(3) . . ?
C5 C4 C7 107.5(3) . . ?
C3 C4 C8 115.1(3) . . ?
C5 C4 C8 109.9(3) . . ?
C7 C4 C8 100.1(2) . . ?
C9 C8 C11 107.8(3) . . ?
C9 C8 C10 110.6(3) . . ?
C11 C8 C10 107.4(3) . . ?
C9 C8 C4 116.2(3) . . ?
C11 C8 C4 100.7(3) . . ?
C10 C8 C4 113.2(3) . . ?
N1 C7 C4 104.3(3) . . ?
N1 C7 H7A 110.9 . . ?
C4 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C4 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O2 C11 N1 126.7(3) . . ?
O2 C11 C8 124.2(3) . . ?
N1 C11 C8 109.0(3) . . ?
C2 C3 C4 123.4(4) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C6 C5 C4 124.4(4) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N1 C12 C14 108.2(3) . . ?
N1 C12 C15 109.9(3) . . ?
C14 C12 C15 108.2(3) . . ?
N1 C12 C13 111.0(3) . . ?
C14 C12 C13 109.9(4) . . ?
C15 C12 C13 109.5(4) . . ?
C8 C9 Br1 114.7(2) . . ?
C8 C9 H9A 108.6 . . ?
Br1 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
Br1 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O1 C1 C6 121.9(5) . . ?
O1 C1 C2 121.6(5) . . ?
C6 C1 C2 116.5(3) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C8 C9 -88.4(4) . . . . ?
C5 C4 C8 C9 39.4(4) . . . . ?
C7 C4 C8 C9 152.2(3) . . . . ?
C3 C4 C8 C11 155.5(3) . . . . ?
C5 C4 C8 C11 -76.7(3) . . . . ?
C7 C4 C8 C11 36.1(3) . . . . ?
C3 C4 C8 C10 41.1(4) . . . . ?
C5 C4 C8 C10 168.9(3) . . . . ?
C7 C4 C8 C10 -78.2(3) . . . . ?
C11 N1 C7 C4 16.0(4) . . . . ?
C12 N1 C7 C4 -156.7(3) . . . . ?
C3 C4 C7 N1 -154.6(3) . . . . ?
C5 C4 C7 N1 82.2(3) . . . . ?
C8 C4 C7 N1 -32.5(3) . . . . ?
C7 N1 C11 O2 -171.9(4) . . . . ?
C12 N1 C11 O2 0.6(6) . . . . ?
C7 N1 C11 C8 8.7(4) . . . . ?
C12 N1 C11 C8 -178.8(3) . . . . ?
C9 C8 C11 O2 29.2(5) . . . . ?
C10 C8 C11 O2 -89.9(4) . . . . ?
C4 C8 C11 O2 151.4(4) . . . . ?
C9 C8 C11 N1 -151.4(3) . . . . ?
C10 C8 C11 N1 89.5(3) . . . . ?
C4 C8 C11 N1 -29.2(3) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C7 C4 C3 C2 -120.7(4) . . . . ?
C8 C4 C3 C2 126.4(4) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C7 C4 C5 C6 123.3(4) . . . . ?
C8 C4 C5 C6 -128.7(4) . . . . ?
C11 N1 C12 C14 -77.9(4) . . . . ?
C7 N1 C12 C14 93.8(4) . . . . ?
C11 N1 C12 C15 164.1(4) . . . . ?
C7 N1 C12 C15 -24.2(5) . . . . ?
C11 N1 C12 C13 42.8(5) . . . . ?
C7 N1 C12 C13 -145.5(4) . . . . ?
C11 C8 C9 Br1 178.8(2) . . . . ?
C10 C8 C9 Br1 -64.1(4) . . . . ?
C4 C8 C9 Br1 66.8(4) . . . . ?
C4 C3 C2 C1 -0.6(6) . . . . ?
C4 C5 C6 C1 -0.3(7) . . . . ?
C5 C6 C1 O1 179.6(4) . . . . ?
C5 C6 C1 C2 -0.6(6) . . . . ?
C3 C2 C1 O1 -179.2(4) . . . . ?
C3 C2 C1 C6 1.0(6) . . . . ?

_refine_diff_density_max         0.663
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2213724'
loop_
_audit_author_name
_audit_author_address
'Hou Zhong-Wei'
;Taizhou University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.35

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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                   6.6760(17)
_cell_length_b                   23.100(6)
_cell_length_c                   9.948(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.562(4)
_cell_angle_gamma                90.00
_cell_volume                     1529.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            7387
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2683
_reflns_number_gt                2181
_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)+(0.0500P)²+0.4000P] 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     SHELXL
_refine_ls_extinction_coef       0.0175(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2683
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
N1 N 0.74217(18) 0.21004(5) 0.33245(13) 0.0443(3) Uani 1 1 d . . .
O1 O 0.40222(17) 0.20431(5) 0.36190(15) 0.0681(4) Uani 1 1 d . . .
O2 O 0.6398(2) -0.05108(5) 0.18367(15) 0.0735(4) Uani 1 1 d . . .
O3 O 0.91177(16) 0.08551(5) 0.08149(10) 0.0476(3) Uani 1 1 d . . .
C1 C 0.7119(3) 0.29775(8) 0.47007(19) 0.0673(5) Uani 1 1 d . . .
H1A H 0.5756 0.2878 0.4843 0.101 Uiso 1 1 calc R . .
H1B H 0.7270 0.3391 0.4720 0.101 Uiso 1 1 calc R . .
H1C H 0.8006 0.2808 0.5399 0.101 Uiso 1 1 calc R . .
C2 C 0.7637(2) 0.27475(6) 0.33323(16) 0.0458(4) Uani 1 1 d . . .
C3 C 0.6261(3) 0.30029(8) 0.2190(2) 0.0709(6) Uani 1 1 d . . .
H3A H 0.4891 0.2906 0.2321 0.106 Uiso 1 1 calc R . .
H3B H 0.6611 0.2847 0.1345 0.106 Uiso 1 1 calc R . .
H3C H 0.6411 0.3416 0.2183 0.106 Uiso 1 1 calc R . .
C4 C 0.9809(3) 0.29114(8) 0.3117(3) 0.0753(6) Uani 1 1 d . . .
H4A H 1.0691 0.2752 0.3832 0.113 Uiso 1 1 calc R . .
H4B H 0.9939 0.3325 0.3116 0.113 Uiso 1 1 calc R . .
H4C H 1.0160 0.2760 0.2268 0.113 Uiso 1 1 calc R . .
C5 C 0.5677(2) 0.18201(7) 0.35179(16) 0.0468(4) Uani 1 1 d . . .
C6 C 0.6086(2) 0.11692(7) 0.36618(15) 0.0430(4) Uani 1 1 d . . .
C7 C 0.8141(2) 0.11129(6) 0.30309(14) 0.0365(3) Uani 1 1 d . . .
C8 C 0.9139(2) 0.17025(6) 0.32773(16) 0.0422(4) Uani 1 1 d . . .
H8A H 0.9971 0.1706 0.4122 0.051 Uiso 1 1 calc R . .
H8B H 0.9959 0.1804 0.2549 0.051 Uiso 1 1 calc R . .
C9 C 0.6120(3) 0.10231(9) 0.51728(18) 0.0649(5) Uani 1 1 d . . .
H9A H 0.4796 0.1069 0.5469 0.097 Uiso 1 1 calc R . .
H9B H 0.7033 0.1279 0.5676 0.097 Uiso 1 1 calc R . .
H9C H 0.6553 0.0630 0.5316 0.097 Uiso 1 1 calc R . .
C10 C 0.4613(2) 0.07824(7) 0.27650(18) 0.0513(4) Uani 1 1 d . . .
H10A H 0.4058 0.0479 0.3298 0.062 Uiso 1 1 calc R . .
H10B H 0.3518 0.1012 0.2346 0.062 Uiso 1 1 calc R . .
C11 C 0.5893(2) 0.05187(6) 0.16775(16) 0.0446(4) Uani 1 1 d . . .
H11A H 0.5087 0.0449 0.0826 0.054 Uiso 1 1 calc R . .
C12 C 0.7451(2) 0.09993(6) 0.15399(14) 0.0381(3) Uani 1 1 d . . .
H12A H 0.6787 0.1345 0.1146 0.046 Uiso 1 1 calc R . .
C13 C 0.9297(2) 0.05896(7) 0.35531(15) 0.0451(4) Uani 1 1 d . . .
H13A H 1.0430 0.0637 0.4150 0.054 Uiso 1 1 calc R . .
C14 C 0.8619(3) 0.07675(9) -0.05893(18) 0.0696(6) Uani 1 1 d . . .
H14A H 0.9810 0.0667 -0.1019 0.104 Uiso 1 1 calc R . .
H14B H 0.8054 0.1117 -0.0982 0.104 Uiso 1 1 calc R . .
H14C H 0.7657 0.0459 -0.0714 0.104 Uiso 1 1 calc R . .
C15 C 0.8715(3) 0.00579(7) 0.31686(16) 0.0516(4) Uani 1 1 d . . .
H15A H 0.9425 -0.0262 0.3518 0.062 Uiso 1 1 calc R . .
C16 C 0.6966(3) -0.00271(7) 0.22013(16) 0.0492(4) 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
N1 C5 1.359(2) . ?
N1 C8 1.4732(19) . ?
N1 C2 1.5017(19) . ?
O1 C5 1.2305(18) . ?
O2 C16 1.226(2) . ?
O3 C12 1.4132(18) . ?
O3 C14 1.425(2) . ?
C1 C2 1.526(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.523(2) . ?
C2 C4 1.530(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.533(2) . ?
C6 C9 1.539(2) . ?
C6 C10 1.556(2) . ?
C6 C7 1.559(2) . ?
C7 C13 1.504(2) . ?
C7 C8 1.528(2) . ?
C7 C12 1.540(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.555(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.522(2) . ?
C11 C12 1.535(2) . ?
C11 H11A 0.9800 . ?
C12 H12A 0.9800 . ?
C13 C15 1.335(2) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.466(2) . ?
C15 H15A 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
C5 N1 C8 112.65(12) . . ?
C5 N1 C2 123.79(12) . . ?
C8 N1 C2 123.14(12) . . ?
C12 O3 C14 113.69(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 109.27(13) . . ?
N1 C2 C1 108.83(13) . . ?
C3 C2 C1 111.40(15) . . ?
N1 C2 C4 109.69(13) . . ?
C3 C2 C4 108.78(16) . . ?
C1 C2 C4 108.85(15) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N1 126.66(15) . . ?
O1 C5 C6 123.89(14) . . ?
N1 C5 C6 109.40(12) . . ?
C5 C6 C9 107.17(13) . . ?
C5 C6 C10 114.20(13) . . ?
C9 C6 C10 113.17(14) . . ?
C5 C6 C7 101.55(11) . . ?
C9 C6 C7 115.46(13) . . ?
C10 C6 C7 104.92(12) . . ?
C13 C7 C8 117.10(12) . . ?
C13 C7 C12 107.55(11) . . ?
C8 C7 C12 113.56(12) . . ?
C13 C7 C6 111.84(12) . . ?
C8 C7 C6 104.34(11) . . ?
C12 C7 C6 101.34(11) . . ?
N1 C8 C7 103.32(11) . . ?
N1 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
N1 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 105.47(12) . . ?
C11 C10 H10A 110.6 . . ?
C6 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C6 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C16 C11 C12 109.01(13) . . ?
C16 C11 C10 110.87(13) . . ?
C12 C11 C10 101.08(12) . . ?
C16 C11 H11A 111.8 . . ?
C12 C11 H11A 111.8 . . ?
C10 C11 H11A 111.8 . . ?
O3 C12 C11 116.22(12) . . ?
O3 C12 C7 110.13(11) . . ?
C11 C12 C7 100.97(11) . . ?
O3 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C7 C12 H12A 109.7 . . ?
C15 C13 C7 120.69(14) . . ?
C15 C13 H13A 119.7 . . ?
C7 C13 H13A 119.7 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 120.67(14) . . ?
C13 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
O2 C16 C15 121.88(16) . . ?
O2 C16 C11 121.84(16) . . ?
C15 C16 C11 116.28(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.036
