# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ram114
_database_code_depnum_ccdc_archive 'CCDC 1408099'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.31

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0589(4)
_cell_length_b                   8.0710(5)
_cell_length_c                   15.6647(10)
_cell_angle_alpha                100.410(4)
_cell_angle_beta                 96.485(4)
_cell_angle_gamma                93.141(4)
_cell_volume                     746.38(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2516
_cell_measurement_theta_min      1.34
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9216
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9021
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_av_R_equivalents  0.1788
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.332
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             2516
_reflns_number_gt                2008
_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       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'

_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)+(0.0671P)²+0.3494P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2516
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1884
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C1 C 0.6185(6) 0.8025(4) 0.81716(17) 0.0508(8) Uani 1 1 d . . . . .
H1 H 0.7146 0.8669 0.7915 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6190(7) 0.8345(4) 0.90702(18) 0.0622(9) Uani 1 1 d . . . . .
H2 H 0.7156 0.9205 0.9415 0.075 Uiso 1 1 calc R U . . .
C3 C 0.4794(7) 0.7413(5) 0.94518(19) 0.0681(10) Uani 1 1 d . . . . .
H3 H 0.4820 0.7627 1.0057 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3347(7) 0.6157(5) 0.89456(19) 0.0653(10) Uani 1 1 d . . . . .
H4 H 0.2374 0.5535 0.9207 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3329(5) 0.5812(4) 0.80487(18) 0.0500(8) Uani 1 1 d . . . . .
H5 H 0.2359 0.4948 0.7710 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4745(4) 0.6745(3) 0.76521(15) 0.0370(6) Uani 1 1 d . . . . .
C7 C 0.4706(4) 0.6318(3) 0.66746(15) 0.0350(6) Uani 1 1 d . . . . .
C8 C 0.6290(4) 0.7314(3) 0.62399(15) 0.0367(6) Uani 1 1 d . . . . .
H8 H 0.6437 0.8495 0.6544 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3697(5) 0.8068(3) 0.51222(15) 0.0353(6) Uani 1 1 d . . . . .
C10 C 0.1084(5) 0.8495(4) 0.39672(16) 0.0435(7) Uani 1 1 d . . . . .
H10A H 0.1203 0.9689 0.4224 0.052 Uiso 1 1 calc R U . . .
H10B H -0.0210 0.7963 0.4151 0.052 Uiso 1 1 calc R U . . .
C11 C 0.0845(5) 0.8262(3) 0.29831(16) 0.0387(6) Uani 1 1 d . . . . .
C12 C -0.0927(5) 0.8948(4) 0.25658(18) 0.0508(8) Uani 1 1 d . . . . .
H12 H -0.1918 0.9539 0.2893 0.061 Uiso 1 1 calc R U . . .
C13 C -0.1225(6) 0.8755(4) 0.16595(19) 0.0603(9) Uani 1 1 d . . . . .
H13 H -0.2402 0.9233 0.1384 0.072 Uiso 1 1 calc R U . . .
C14 C 0.0206(6) 0.7863(4) 0.11686(19) 0.0602(9) Uani 1 1 d . . . . .
H14 H -0.0004 0.7725 0.0562 0.072 Uiso 1 1 calc R U . . .
C15 C 0.1939(6) 0.7182(4) 0.15784(19) 0.0601(9) Uani 1 1 d . . . . .
H15 H 0.2905 0.6571 0.1246 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2291(6) 0.7385(4) 0.24884(18) 0.0508(8) Uani 1 1 d . . . . .
H16 H 0.3497 0.6929 0.2759 0.061 Uiso 1 1 calc R U . . .
C17 C 0.8587(5) 0.6606(4) 0.63120(19) 0.0485(7) Uani 1 1 d . . . . .
H17A H 0.8479 0.5470 0.5987 0.073 Uiso 1 1 calc R U . . .
H17B H 0.9098 0.6610 0.6915 0.073 Uiso 1 1 calc R U . . .
H17C H 0.9621 0.7296 0.6079 0.073 Uiso 1 1 calc R U . . .
N1 N 0.5484(4) 0.7251(3) 0.53294(13) 0.0414(6) Uani 1 1 d . . . . .
O1 O 0.3446(3) 0.5164(2) 0.62517(11) 0.0465(6) Uani 1 1 d . . . . .
O2 O 0.2790(4) 0.8998(2) 0.56403(12) 0.0499(6) Uani 1 1 d . . . . .
O3 O 0.3053(3) 0.7736(2) 0.42514(11) 0.0435(5) Uani 1 1 d . . . . .
H1N H 0.602(5) 0.650(3) 0.4907(18) 0.042(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(4) . ?
C1 C6 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(3) . ?
C7 O1 1.214(3) . ?
C7 C8 1.514(4) . ?
C8 N1 1.445(3) . ?
C8 C17 1.533(4) . ?
C8 H8 0.9800 . ?
C9 O2 1.205(3) . ?
C9 N1 1.337(3) . ?
C9 O3 1.350(3) . ?
C10 O3 1.433(3) . ?
C10 C11 1.508(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.375(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 H1N 0.91(3) . ?

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
C2 C1 C6 120.1(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 118.9(2) . . ?
C1 C6 C7 122.3(3) . . ?
O1 C7 C6 119.7(2) . . ?
O1 C7 C8 121.2(2) . . ?
C6 C7 C8 119.0(2) . . ?
N1 C8 C7 111.5(2) . . ?
N1 C8 C17 109.5(2) . . ?
C7 C8 C17 109.6(2) . . ?
N1 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C17 C8 H8 108.7 . . ?
O2 C9 N1 124.7(2) . . ?
O2 C9 O3 124.0(2) . . ?
N1 C9 O3 111.2(2) . . ?
O3 C10 C11 108.3(2) . . ?
O3 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O3 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 119.1(2) . . ?
C16 C11 C10 122.7(2) . . ?
C12 C11 C10 118.2(2) . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 119.7(3) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 N1 C8 119.4(2) . . ?
C9 N1 H1N 119.9(18) . . ?
C8 N1 H1N 119.7(18) . . ?
C9 O3 C10 115.42(18) . . ?

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 0.0(6) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C1 C6 C7 -178.6(3) . . . . ?
C5 C6 C7 O1 -0.3(4) . . . . ?
C1 C6 C7 O1 178.5(3) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C1 C6 C7 C8 0.1(4) . . . . ?
O1 C7 C8 N1 24.9(3) . . . . ?
C6 C7 C8 N1 -156.7(2) . . . . ?
O1 C7 C8 C17 -96.5(3) . . . . ?
C6 C7 C8 C17 81.9(3) . . . . ?
O3 C10 C11 C16 2.6(4) . . . . ?
O3 C10 C11 C12 -178.1(2) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 -179.5(3) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C12 C11 C16 C15 -0.8(5) . . . . ?
C10 C11 C16 C15 178.4(3) . . . . ?
C14 C15 C16 C11 1.2(5) . . . . ?
O2 C9 N1 C8 7.0(4) . . . . ?
O3 C9 N1 C8 -173.9(2) . . . . ?
C7 C8 N1 C9 70.1(3) . . . . ?
C17 C8 N1 C9 -168.5(2) . . . . ?
O2 C9 O3 C10 -3.7(4) . . . . ?
N1 C9 O3 C10 177.3(2) . . . . ?
C11 C10 O3 C9 170.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17A O3 0.96 2.65 3.515(4) 150.5 2_666
C17 H17C O2 0.96 2.53 3.481(4) 171.2 1_655
N1 H1N O1 0.91(3) 2.12(3) 3.018(3) 166(3) 2_666

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.064

_shelxl_version_number           2012-9


####################################################################### 
# 
# 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_ram061
_database_code_depnum_ccdc_archive 'CCDC 1408100'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-07-28 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         'C12 H12 Cl3 N O3'
_chemical_formula_sum            'C12 H12 Cl3 N O3'
_chemical_formula_weight         324.58

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6581(5)
_cell_length_b                   11.8588(8)
_cell_length_c                   14.7395(10)
_cell_angle_alpha                101.560(3)
_cell_angle_beta                 104.761(2)
_cell_angle_gamma                90.004(3)
_cell_volume                     1431.65(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7724
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.23

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.642
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8291
_exptl_absorpt_correction_T_max  0.8599
_exptl_absorpt_process_details   'SADABS (BRUKER 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34468
_diffrn_reflns_av_unetI/netI     0.1220
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         2.436
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             34468
_reflns_number_gt                17691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0209P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         34468
_refine_ls_number_parameters     354
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
C1 C 0.8591(8) 0.8227(7) 1.3143(5) 0.046(2) Uani 1 1 d . . . . .
H1 H 0.9152 0.8836 1.3038 0.055 Uiso 1 1 calc R U . . .
C2 C 0.8677(9) 0.8111(8) 1.4057(6) 0.048(3) Uani 1 1 d . . . . .
H2 H 0.9314 0.8636 1.4572 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7843(9) 0.7237(8) 1.4226(6) 0.050(3) Uani 1 1 d . . . . .
H3 H 0.7891 0.7175 1.4851 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6938(8) 0.6454(7) 1.3472(6) 0.047(2) Uani 1 1 d . . . . .
H4 H 0.6374 0.5852 1.3585 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6851(8) 0.6546(7) 1.2550(5) 0.039(2) Uani 1 1 d . . . . .
H5 H 0.6235 0.6003 1.2040 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7672(7) 0.7440(7) 1.2374(5) 0.0316(18) Uani 1 1 d . . . . .
C7 C 0.7607(8) 0.7605(7) 1.1394(5) 0.037(2) Uani 1 1 d . . . . .
C8 C 0.6919(8) 0.6658(6) 1.0542(5) 0.0346(19) Uani 1 1 d . . . . .
H8 H 0.5965 0.6299 1.0633 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5146(9) 0.6786(7) 0.9009(5) 0.0334(19) Uani 1 1 d . . . . .
C10 C 0.3715(8) 0.6976(6) 0.7470(5) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.2829 0.6676 0.7658 0.050 Uiso 1 1 calc R U . . .
H10B H 0.4046 0.6362 0.7028 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3201(8) 0.7964(7) 0.6991(5) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.8154(8) 0.5757(6) 1.0459(5) 0.053(2) Uani 1 1 d . . . . .
H12A H 0.7690 0.5116 0.9949 0.080 Uiso 1 1 calc R U . . .
H12B H 0.8491 0.5495 1.1051 0.080 Uiso 1 1 calc R U . . .
H12C H 0.9061 0.6090 1.0325 0.080 Uiso 1 1 calc R U . . .
C13 C 1.1877(8) 0.9661(7) 1.2542(5) 0.038(2) Uani 1 1 d . . . . .
H13 H 1.1310 0.9996 1.2047 0.045 Uiso 1 1 calc R U . . .
C14 C 1.1960(8) 1.0162(7) 1.3477(6) 0.047(2) Uani 1 1 d . . . . .
H14 H 1.1434 1.0834 1.3611 0.056 Uiso 1 1 calc R U . . .
C15 C 1.2802(9) 0.9694(8) 1.4217(6) 0.051(3) Uani 1 1 d . . . . .
H15 H 1.2859 1.0050 1.4848 0.061 Uiso 1 1 calc R U . . .
C16 C 1.3558(9) 0.8701(8) 1.4025(6) 0.058(3) Uani 1 1 d . . . . .
H16 H 1.4125 0.8376 1.4526 0.070 Uiso 1 1 calc R U . . .
C17 C 1.3484(8) 0.8180(7) 1.3093(5) 0.051(2) Uani 1 1 d . . . . .
H17 H 1.4005 0.7503 1.2968 0.061 Uiso 1 1 calc R U . . .
C18 C 1.2644(8) 0.8651(7) 1.2340(5) 0.0337(19) Uani 1 1 d . . . . .
C19 C 1.2596(8) 0.8028(7) 1.1356(5) 0.038(2) Uani 1 1 d . . . . .
C20 C 1.1907(8) 0.8583(6) 1.0509(5) 0.0338(19) Uani 1 1 d . . . . .
H20 H 1.0952 0.8982 1.0607 0.041 Uiso 1 1 calc R U . . .
C21 C 1.0129(9) 0.7735(7) 0.8977(5) 0.0343(19) Uani 1 1 d . . . . .
C22 C 0.8689(8) 0.6799(6) 0.7421(5) 0.041(2) Uani 1 1 d . . . . .
H22A H 0.8987 0.7174 0.6958 0.049 Uiso 1 1 calc R U . . .
H22B H 0.7824 0.7204 0.7626 0.049 Uiso 1 1 calc R U . . .
C23 C 0.8161(8) 0.5571(7) 0.6974(5) 0.038(2) Uani 1 1 d . . . . .
C24 C 1.3141(8) 0.9462(6) 1.0451(5) 0.054(2) Uani 1 1 d . . . . .
H24A H 1.4094 0.9083 1.0376 0.081 Uiso 1 1 calc R U . . .
H24B H 1.3392 1.0045 1.1030 0.081 Uiso 1 1 calc R U . . .
H24C H 1.2716 0.9811 0.9912 0.081 Uiso 1 1 calc R U . . .
N1 N 0.6467(8) 0.7149(6) 0.9691(4) 0.0388(17) Uani 1 1 d D . . . .
N2 N 1.1454(7) 0.7697(6) 0.9652(4) 0.0381(17) Uani 1 1 d D . . . .
O1 O 0.8188(6) 0.8477(5) 1.1263(4) 0.0613(16) Uani 1 1 d . . . . .
O2 O 0.4156(5) 0.6064(5) 0.9003(3) 0.0495(15) Uani 1 1 d . . . . .
O3 O 0.5001(5) 0.7362(4) 0.8286(3) 0.0433(14) Uani 1 1 d . . . . .
O4 O 1.3163(6) 0.7093(5) 1.1215(4) 0.0626(17) Uani 1 1 d . . . . .
O5 O 0.9136(5) 0.8436(4) 0.8983(3) 0.0501(15) Uani 1 1 d . . . . .
O6 O 1.0022(5) 0.6827(4) 0.8222(3) 0.0427(14) Uani 1 1 d . . . . .
Cl1 Cl 0.1728(2) 0.7409(3) 0.59168(16) 0.0764(9) Uani 1 1 d . . . . .
Cl2 Cl 0.2391(3) 0.9020(2) 0.77126(17) 0.0746(8) Uani 1 1 d . . . . .
Cl3 Cl 0.4807(2) 0.8593(2) 0.67072(15) 0.0635(7) Uani 1 1 d . . . . .
Cl4 Cl 0.7483(3) 0.4900(2) 0.77658(16) 0.0717(7) Uani 1 1 d . . . . .
Cl5 Cl 0.6550(2) 0.5573(3) 0.59512(15) 0.0617(8) Uani 1 1 d . . . . .
Cl6 Cl 0.9693(2) 0.4803(2) 0.66156(16) 0.0760(8) Uani 1 1 d . . . . .
H2A H 1.210(7) 0.717(5) 0.957(5) 0.05(3) Uiso 1 1 d D . . . .
H1A H 0.704(7) 0.770(5) 0.964(4) 0.04(3) 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
C1 C2 1.365(10) . ?
C1 C6 1.380(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(9) . ?
C7 O1 1.221(8) . ?
C7 C8 1.498(9) . ?
C8 N1 1.452(8) . ?
C8 C12 1.522(8) . ?
C8 H8 0.9800 . ?
C9 O2 1.209(8) . ?
C9 N1 1.321(8) . ?
C9 O3 1.357(8) . ?
C10 O3 1.412(7) . ?
C10 C11 1.496(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 Cl2 1.743(8) . ?
C11 Cl3 1.757(7) . ?
C11 Cl1 1.766(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.371(9) . ?
C13 C18 1.386(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.481(9) . ?
C19 O4 1.214(8) . ?
C19 C20 1.516(9) . ?
C20 N2 1.438(8) . ?
C20 C24 1.521(8) . ?
C20 H20 0.9800 . ?
C21 O5 1.197(8) . ?
C21 N2 1.320(8) . ?
C21 O6 1.369(8) . ?
C22 O6 1.420(7) . ?
C22 C23 1.491(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 Cl6 1.742(7) . ?
C23 Cl4 1.750(7) . ?
C23 Cl5 1.775(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1A 0.85(4) . ?
N2 H2A 0.85(4) . ?

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
C2 C1 C6 120.0(8) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.9(8) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.5(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.6(8) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.2(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.8(7) . . ?
C5 C6 C7 123.1(7) . . ?
C1 C6 C7 118.1(7) . . ?
O1 C7 C6 121.3(7) . . ?
O1 C7 C8 118.4(7) . . ?
C6 C7 C8 120.1(7) . . ?
N1 C8 C7 108.9(6) . . ?
N1 C8 C12 111.6(6) . . ?
C7 C8 C12 109.0(6) . . ?
N1 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C12 C8 H8 109.1 . . ?
O2 C9 N1 127.0(7) . . ?
O2 C9 O3 122.6(7) . . ?
N1 C9 O3 110.4(7) . . ?
O3 C10 C11 109.1(6) . . ?
O3 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
O3 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 Cl2 111.4(5) . . ?
C10 C11 Cl3 111.3(5) . . ?
Cl2 C11 Cl3 108.9(4) . . ?
C10 C11 Cl1 107.3(5) . . ?
Cl2 C11 Cl1 109.2(4) . . ?
Cl3 C11 Cl1 108.7(4) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.5(7) . . ?
C14 C13 H13 120.2 . . ?
C18 C13 H13 120.2 . . ?
C15 C14 C13 121.3(8) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.6(8) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.2(8) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.6(8) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 118.8(7) . . ?
C17 C18 C19 117.5(7) . . ?
C13 C18 C19 123.7(7) . . ?
O4 C19 C18 121.0(7) . . ?
O4 C19 C20 118.9(7) . . ?
C18 C19 C20 120.0(7) . . ?
N2 C20 C19 108.9(6) . . ?
N2 C20 C24 112.2(6) . . ?
C19 C20 C24 109.0(6) . . ?
N2 C20 H20 108.9 . . ?
C19 C20 H20 108.9 . . ?
C24 C20 H20 108.9 . . ?
O5 C21 N2 127.7(8) . . ?
O5 C21 O6 122.6(7) . . ?
N2 C21 O6 109.8(7) . . ?
O6 C22 C23 108.5(6) . . ?
O6 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
O6 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 Cl6 111.5(5) . . ?
C22 C23 Cl4 110.9(5) . . ?
Cl6 C23 Cl4 109.5(4) . . ?
C22 C23 Cl5 107.1(5) . . ?
Cl6 C23 Cl5 109.0(4) . . ?
Cl4 C23 Cl5 108.7(4) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C8 121.5(7) . . ?
C9 N1 H1A 119(4) . . ?
C8 N1 H1A 119(4) . . ?
C21 N2 C20 121.5(7) . . ?
C21 N2 H2A 121(5) . . ?
C20 N2 H2A 118(5) . . ?
C9 O3 C10 115.8(6) . . ?
C21 O6 C22 115.6(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
C6 C1 C2 C3 -1.2(12) . . . . ?
C1 C2 C3 C4 1.4(12) . . . . ?
C2 C3 C4 C5 -0.6(12) . . . . ?
C3 C4 C5 C6 -0.5(11) . . . . ?
C4 C5 C6 C1 0.7(10) . . . . ?
C4 C5 C6 C7 -178.8(6) . . . . ?
C2 C1 C6 C5 0.1(10) . . . . ?
C2 C1 C6 C7 179.6(6) . . . . ?
C5 C6 C7 O1 171.0(7) . . . . ?
C1 C6 C7 O1 -8.5(10) . . . . ?
C5 C6 C7 C8 -13.2(10) . . . . ?
C1 C6 C7 C8 167.3(6) . . . . ?
O1 C7 C8 N1 -24.3(9) . . . . ?
C6 C7 C8 N1 159.8(6) . . . . ?
O1 C7 C8 C12 97.6(8) . . . . ?
C6 C7 C8 C12 -78.3(7) . . . . ?
O3 C10 C11 Cl2 -66.0(7) . . . . ?
O3 C10 C11 Cl3 55.7(7) . . . . ?
O3 C10 C11 Cl1 174.5(4) . . . . ?
C18 C13 C14 C15 0.8(11) . . . . ?
C13 C14 C15 C16 -0.9(13) . . . . ?
C14 C15 C16 C17 0.5(13) . . . . ?
C15 C16 C17 C18 -0.1(13) . . . . ?
C16 C17 C18 C13 0.1(11) . . . . ?
C16 C17 C18 C19 -178.9(7) . . . . ?
C14 C13 C18 C17 -0.4(11) . . . . ?
C14 C13 C18 C19 178.5(7) . . . . ?
C17 C18 C19 O4 5.8(11) . . . . ?
C13 C18 C19 O4 -173.1(7) . . . . ?
C17 C18 C19 C20 -171.1(6) . . . . ?
C13 C18 C19 C20 10.0(10) . . . . ?
O4 C19 C20 N2 24.0(9) . . . . ?
C18 C19 C20 N2 -159.0(6) . . . . ?
O4 C19 C20 C24 -98.6(8) . . . . ?
C18 C19 C20 C24 78.3(8) . . . . ?
O6 C22 C23 Cl6 -58.5(7) . . . . ?
O6 C22 C23 Cl4 63.8(6) . . . . ?
O6 C22 C23 Cl5 -177.7(4) . . . . ?
O2 C9 N1 C8 2.3(12) . . . . ?
O3 C9 N1 C8 -179.1(6) . . . . ?
C7 C8 N1 C9 -140.9(7) . . . . ?
C12 C8 N1 C9 98.7(8) . . . . ?
O5 C21 N2 C20 -2.8(12) . . . . ?
O6 C21 N2 C20 177.0(6) . . . . ?
C19 C20 N2 C21 140.4(7) . . . . ?
C24 C20 N2 C21 -98.8(8) . . . . ?
O2 C9 O3 C10 -7.1(10) . . . . ?
N1 C9 O3 C10 174.1(6) . . . . ?
C11 C10 O3 C9 151.8(6) . . . . ?
O5 C21 O6 C22 3.1(10) . . . . ?
N2 C21 O6 C22 -176.8(6) . . . . ?
C23 C22 O6 C21 -146.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.85(4) 2.43(5) 3.246(8) 161(6) 1_655
N1 H1A O5 0.85(4) 2.50(5) 3.260(8) 150(6) .

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.455
_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_ram139
_database_code_depnum_ccdc_archive 'CCDC 1408101'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl3 N O3'
_chemical_formula_weight         364.64

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      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                   6.0347(2)
_cell_length_b                   11.3911(4)
_cell_length_c                   13.0283(4)
_cell_angle_alpha                67.611(2)
_cell_angle_beta                 89.839(2)
_cell_angle_gamma                85.877(2)
_cell_volume                     825.64(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2871
_cell_measurement_theta_min      1.691
_cell_measurement_theta_max      27.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.565
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8012
_exptl_absorpt_correction_T_max  0.8823
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11909
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             2871
_reflns_number_gt                2550
_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       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'

_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)+(0.0317P)²+0.5977P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.3022(4) 0.4772(2) 0.15300(19) 0.0491(5) Uani 1 1 d . . . . .
H1 H 0.1923 0.4576 0.1135 0.059 Uiso 1 1 calc R U . . .
C2 C 0.2673(5) 0.5813(2) 0.1821(2) 0.0606(6) Uani 1 1 d . . . . .
H2 H 0.1352 0.6326 0.1609 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4268(5) 0.6096(2) 0.2425(2) 0.0618(7) Uani 1 1 d . . . . .
H3 H 0.4021 0.6794 0.2627 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6225(5) 0.5345(3) 0.2729(2) 0.0608(7) Uani 1 1 d . . . . .
H4 H 0.7298 0.5530 0.3144 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6606(4) 0.4326(2) 0.24234(19) 0.0508(6) Uani 1 1 d . . . . .
H5 H 0.7951 0.3835 0.2620 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5006(3) 0.4016(2) 0.18238(16) 0.0388(5) Uani 1 1 d . . . . .
C7 C 0.5529(3) 0.2881(2) 0.15337(16) 0.0396(5) Uani 1 1 d . . . . .
C8 C 0.3676(3) 0.20653(19) 0.14441(15) 0.0346(4) Uani 1 1 d . . . . .
C9 C 0.4554(4) 0.0748(2) 0.1489(2) 0.0515(6) Uani 1 1 d . . . . .
H9A H 0.5927 0.0798 0.1091 0.062 Uiso 1 1 calc R U . . .
H9B H 0.4811 0.0153 0.2250 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2712(5) 0.0355(3) 0.0929(2) 0.0627(7) Uani 1 1 d . . . . .
H10A H 0.3266 -0.0300 0.0669 0.075 Uiso 1 1 calc R U . . .
H10B H 0.1513 0.0038 0.1435 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1942(5) 0.1558(3) -0.0027(2) 0.0725(8) Uani 1 1 d . . . . .
H11A H 0.0360 0.1578 -0.0168 0.087 Uiso 1 1 calc R U . . .
H11B H 0.2720 0.1609 -0.0693 0.087 Uiso 1 1 calc R U . . .
C12 C 0.2447(3) 0.2660(2) 0.02953(16) 0.0416(5) Uani 1 1 d . . . . .
H12A H 0.1082 0.3139 0.0343 0.050 Uiso 1 1 calc R U . . .
H12B H 0.3378 0.3229 -0.0251 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2844(3) 0.15492(18) 0.33797(16) 0.0362(4) Uani 1 1 d . . . . .
C14 C 0.1700(4) 0.1183(2) 0.52096(17) 0.0472(5) Uani 1 1 d . . . . .
H14A H 0.3305 0.1110 0.5306 0.057 Uiso 1 1 calc R U . . .
H14B H 0.1140 0.0384 0.5688 0.057 Uiso 1 1 calc R U . . .
C15 C 0.0700(3) 0.2257(2) 0.55119(16) 0.0411(5) Uani 1 1 d . . . . .
Cl1 Cl -0.22004(11) 0.24284(11) 0.53487(7) 0.0963(3) Uani 1 1 d . . . . .
Cl2 Cl 0.14028(12) 0.18860(6) 0.69296(5) 0.06045(19) Uani 1 1 d . . . . .
Cl3 Cl 0.18185(13) 0.36941(6) 0.46865(6) 0.0669(2) Uani 1 1 d . . . . .
N1 N 0.2097(3) 0.19328(17) 0.23261(13) 0.0355(4) Uani 1 1 d . . . . .
O1 O 0.7435(2) 0.26013(19) 0.13531(15) 0.0614(5) Uani 1 1 d . . . . .
O2 O 0.4770(3) 0.13246(15) 0.36830(12) 0.0493(4) Uani 1 1 d . . . . .
O3 O 0.1109(2) 0.14492(15) 0.40756(11) 0.0457(4) Uani 1 1 d . . . . .
H1N H 0.084(4) 0.207(2) 0.2190(19) 0.039(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.493(3) . ?
C7 O1 1.217(2) . ?
C7 C8 1.536(3) . ?
C8 N1 1.460(2) . ?
C8 C9 1.534(3) . ?
C8 C12 1.553(3) . ?
C9 C10 1.514(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.503(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.517(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.206(2) . ?
C13 N1 1.340(3) . ?
C13 O3 1.365(2) . ?
C14 O3 1.431(2) . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 Cl1 1.752(2) . ?
C15 Cl3 1.762(2) . ?
C15 Cl2 1.776(2) . ?
N1 H1N 0.77(2) . ?

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
C2 C1 C6 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 123.75(19) . . ?
C5 C6 C7 117.73(19) . . ?
O1 C7 C6 120.04(19) . . ?
O1 C7 C8 119.35(19) . . ?
C6 C7 C8 120.61(17) . . ?
N1 C8 C9 110.17(17) . . ?
N1 C8 C7 109.37(15) . . ?
C9 C8 C7 113.10(17) . . ?
N1 C8 C12 109.84(15) . . ?
C9 C8 C12 102.69(16) . . ?
C7 C8 C12 111.50(16) . . ?
C10 C9 C8 103.67(19) . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 104.1(2) . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 109.0 . . ?
C10 C11 C12 107.0(2) . . ?
C10 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
C10 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 C8 106.39(19) . . ?
C11 C12 H12A 110.5 . . ?
C8 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
C8 C12 H12B 110.5 . . ?
H12A C12 H12B 108.6 . . ?
O2 C13 N1 125.47(19) . . ?
O2 C13 O3 124.10(18) . . ?
N1 C13 O3 110.43(18) . . ?
O3 C14 C15 108.37(18) . . ?
O3 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O3 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 Cl1 111.69(16) . . ?
C14 C15 Cl3 109.96(15) . . ?
Cl1 C15 Cl3 109.65(12) . . ?
C14 C15 Cl2 107.47(15) . . ?
Cl1 C15 Cl2 108.67(11) . . ?
Cl3 C15 Cl2 109.34(11) . . ?
C13 N1 C8 119.60(17) . . ?
C13 N1 H1N 120.0(17) . . ?
C8 N1 H1N 120.4(17) . . ?
C13 O3 C14 115.73(17) . . ?

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 -1.3(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -179.4(2) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C1 C6 C7 O1 147.4(2) . . . . ?
C5 C6 C7 O1 -32.7(3) . . . . ?
C1 C6 C7 C8 -31.8(3) . . . . ?
C5 C6 C7 C8 148.1(2) . . . . ?
O1 C7 C8 N1 141.3(2) . . . . ?
C6 C7 C8 N1 -39.5(2) . . . . ?
O1 C7 C8 C9 18.1(3) . . . . ?
C6 C7 C8 C9 -162.73(18) . . . . ?
O1 C7 C8 C12 -97.0(2) . . . . ?
C6 C7 C8 C12 82.1(2) . . . . ?
N1 C8 C9 C10 79.8(2) . . . . ?
C7 C8 C9 C10 -157.42(18) . . . . ?
C12 C8 C9 C10 -37.1(2) . . . . ?
C8 C9 C10 C11 40.0(3) . . . . ?
C9 C10 C11 C12 -26.8(3) . . . . ?
C10 C11 C12 C8 3.5(3) . . . . ?
N1 C8 C12 C11 -96.5(2) . . . . ?
C9 C8 C12 C11 20.7(2) . . . . ?
C7 C8 C12 C11 142.1(2) . . . . ?
O3 C14 C15 Cl1 59.6(2) . . . . ?
O3 C14 C15 Cl3 -62.4(2) . . . . ?
O3 C14 C15 Cl2 178.67(14) . . . . ?
O2 C13 N1 C8 2.1(3) . . . . ?
O3 C13 N1 C8 -178.11(16) . . . . ?
C9 C8 N1 C13 73.8(2) . . . . ?
C7 C8 N1 C13 -51.1(2) . . . . ?
C12 C8 N1 C13 -173.75(17) . . . . ?
O2 C13 O3 C14 6.4(3) . . . . ?
N1 C13 O3 C14 -173.37(17) . . . . ?
C15 C14 O3 C13 120.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A O1 0.97 2.55 3.315(2) 135.5 1_455
C14 H14B O3 0.97 2.49 3.365(3) 149.6 2_556
N1 H1N O1 0.77(2) 2.26(2) 3.014(2) 166(2) 1_455

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.039

_shelxl_version_number           2012-9


####################################################################### 
# 
# 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_ram010
_database_code_depnum_ccdc_archive 'CCDC 1408102'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   11.5083(8)
_cell_length_b                   13.3657(9)
_cell_length_c                   9.5834(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1474.08(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2467
_cell_measurement_theta_min      1.52
_cell_measurement_theta_max      25.5

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8801
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9969
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.524
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             2467
_reflns_number_gt                1741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.893
_reflns_Friedel_fraction_full    0.875

_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       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'

_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)+(0.0541P)²+0.0972P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 610 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2467
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.2789(5) 0.4313(4) 0.1923(6) 0.0830(16) Uani 1 1 d . . . . .
H1 H 0.2196 0.4437 0.2560 0.100 Uiso 1 1 calc R U . . .
C2 C 0.3069(7) 0.3345(4) 0.1571(10) 0.115(3) Uani 1 1 d . . . . .
H2 H 0.2656 0.2811 0.1946 0.139 Uiso 1 1 calc R U . . .
C3 C 0.3975(8) 0.3177(5) 0.0650(9) 0.125(3) Uani 1 1 d . . . . .
H3 H 0.4170 0.2522 0.0417 0.151 Uiso 1 1 calc R U . . .
C4 C 0.4587(6) 0.3947(5) 0.0077(6) 0.096(2) Uani 1 1 d . . . . .
H4 H 0.5194 0.3811 -0.0534 0.115 Uiso 1 1 calc R U . . .
C5 C 0.4312(4) 0.4935(4) 0.0397(5) 0.0634(13) Uani 1 1 d . . . . .
C6 C 0.4971(4) 0.5779(4) -0.0244(5) 0.0706(15) Uani 1 1 d . . . . .
H6A H 0.4685 0.5889 -0.1184 0.085 Uiso 1 1 calc R U . . .
H6B H 0.5784 0.5594 -0.0311 0.085 Uiso 1 1 calc R U . . .
C7 C 0.4871(4) 0.6752(3) 0.0575(5) 0.0573(11) Uani 1 1 d . . . . .
H7A H 0.5284 0.6692 0.1454 0.069 Uiso 1 1 calc R U . . .
H7B H 0.5216 0.7295 0.0048 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3594(3) 0.6971(3) 0.0848(4) 0.0460(10) Uani 1 1 d . . . . .
H8 H 0.3197 0.6977 -0.0056 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3062(4) 0.6144(3) 0.1709(5) 0.0506(11) Uani 1 1 d . . . . .
C10 C 0.3395(4) 0.5108(3) 0.1325(5) 0.0560(11) Uani 1 1 d . . . . .
N2 N 0.3421(3) 0.7945(2) 0.1485(3) 0.0460(8) Uani 1 1 d . . . . .
C12 C 0.2386(4) 0.8423(3) 0.1355(4) 0.0426(9) Uani 1 1 d . . . . .
C13 C 0.1199(3) 0.9763(3) 0.2379(4) 0.0448(9) Uani 1 1 d . . . . .
C14 C 0.1410(4) 1.0378(4) 0.3680(5) 0.0662(14) Uani 1 1 d . . . . .
H14A H 0.1494 0.9941 0.4468 0.099 Uiso 1 1 calc R U . . .
H14B H 0.0764 1.0820 0.3830 0.099 Uiso 1 1 calc R U . . .
H14C H 0.2107 1.0765 0.3566 0.099 Uiso 1 1 calc R U . . .
C15 C 0.1202(4) 1.0424(4) 0.1109(5) 0.0719(14) Uani 1 1 d . . . . .
H15A H 0.1926 1.0780 0.1060 0.108 Uiso 1 1 calc R U . . .
H15B H 0.0573 1.0893 0.1169 0.108 Uiso 1 1 calc R U . . .
H15C H 0.1111 1.0020 0.0288 0.108 Uiso 1 1 calc R U . . .
C16 C 0.0121(4) 0.9153(4) 0.2503(6) 0.0756(14) Uani 1 1 d . . . . .
H16A H -0.0005 0.8792 0.1650 0.113 Uiso 1 1 calc R U . . .
H16B H -0.0529 0.9585 0.2678 0.113 Uiso 1 1 calc R U . . .
H16C H 0.0203 0.8688 0.3260 0.113 Uiso 1 1 calc R U . . .
O4 O 0.2248(2) 0.91089(19) 0.2344(3) 0.0493(7) Uani 1 1 d . . . . .
O1 O 0.2394(3) 0.6334(2) 0.2649(4) 0.0770(10) Uani 1 1 d . . . . .
O2 O 0.1722(2) 0.8251(2) 0.0392(3) 0.0566(8) Uani 1 1 d . . . . .
O5 O 0.4078(2) 0.8080(2) 0.2712(3) 0.0480(7) Uani 1 1 d . . . . .
H1O H 0.361(3) 0.805(3) 0.342(5) 0.052(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(8) . ?
C1 C10 1.395(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(7) . ?
C4 H4 0.9300 . ?
C5 C10 1.400(6) . ?
C5 C6 1.492(7) . ?
C6 C7 1.523(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.521(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.451(5) . ?
C8 C9 1.509(6) . ?
C8 H8 0.9800 . ?
C9 O1 1.211(5) . ?
C9 C10 1.483(6) . ?
N2 C12 1.358(5) . ?
N2 O5 1.410(4) . ?
C12 O2 1.220(5) . ?
C12 O4 1.328(4) . ?
C13 C16 1.489(6) . ?
C13 O4 1.490(4) . ?
C13 C15 1.504(6) . ?
C13 C14 1.513(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O5 H1O 0.86(4) . ?

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
C2 C1 C10 119.9(6) . . ?
C2 C1 H1 120.0 . . ?
C10 C1 H1 120.0 . . ?
C1 C2 C3 119.1(7) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.7(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C10 117.9(6) . . ?
C4 C5 C6 120.8(5) . . ?
C10 C5 C6 121.3(4) . . ?
C5 C6 C7 113.3(4) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 109.0(4) . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C9 111.8(3) . . ?
N2 C8 C7 112.2(3) . . ?
C9 C8 C7 110.2(3) . . ?
N2 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C7 C8 H8 107.5 . . ?
O1 C9 C10 122.9(4) . . ?
O1 C9 C8 120.7(4) . . ?
C10 C9 C8 116.3(4) . . ?
C1 C10 C5 120.8(5) . . ?
C1 C10 C9 118.7(5) . . ?
C5 C10 C9 120.5(4) . . ?
C12 N2 O5 119.1(3) . . ?
C12 N2 C8 120.3(3) . . ?
O5 N2 C8 113.1(3) . . ?
O2 C12 O4 126.5(4) . . ?
O2 C12 N2 122.0(3) . . ?
O4 C12 N2 111.4(3) . . ?
C16 C13 O4 110.8(3) . . ?
C16 C13 C15 112.8(4) . . ?
O4 C13 C15 108.9(3) . . ?
C16 C13 C14 111.5(4) . . ?
O4 C13 C14 102.0(3) . . ?
C15 C13 C14 110.3(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 O4 C13 121.2(3) . . ?
N2 O5 H1O 108(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
C10 C1 C2 C3 1.7(10) . . . . ?
C1 C2 C3 C4 -0.6(11) . . . . ?
C2 C3 C4 C5 -0.4(10) . . . . ?
C3 C4 C5 C10 0.3(8) . . . . ?
C3 C4 C5 C6 -179.2(5) . . . . ?
C4 C5 C6 C7 -159.3(5) . . . . ?
C10 C5 C6 C7 21.3(6) . . . . ?
C5 C6 C7 C8 -51.2(5) . . . . ?
C6 C7 C8 N2 -173.4(3) . . . . ?
C6 C7 C8 C9 61.4(4) . . . . ?
N2 C8 C9 O1 13.1(5) . . . . ?
C7 C8 C9 O1 138.5(4) . . . . ?
N2 C8 C9 C10 -167.5(3) . . . . ?
C7 C8 C9 C10 -42.0(5) . . . . ?
C2 C1 C10 C5 -1.9(8) . . . . ?
C2 C1 C10 C9 179.1(5) . . . . ?
C4 C5 C10 C1 0.9(7) . . . . ?
C6 C5 C10 C1 -179.7(4) . . . . ?
C4 C5 C10 C9 179.9(4) . . . . ?
C6 C5 C10 C9 -0.6(6) . . . . ?
O1 C9 C10 C1 10.0(7) . . . . ?
C8 C9 C10 C1 -169.5(4) . . . . ?
O1 C9 C10 C5 -169.1(4) . . . . ?
C8 C9 C10 C5 11.5(6) . . . . ?
C9 C8 N2 C12 -79.3(4) . . . . ?
C7 C8 N2 C12 156.3(4) . . . . ?
C9 C8 N2 O5 70.2(4) . . . . ?
C7 C8 N2 O5 -54.2(4) . . . . ?
O5 N2 C12 O2 -171.8(3) . . . . ?
C8 N2 C12 O2 -24.1(6) . . . . ?
O5 N2 C12 O4 11.5(5) . . . . ?
C8 N2 C12 O4 159.2(3) . . . . ?
O2 C12 O4 C13 0.7(6) . . . . ?
N2 C12 O4 C13 177.3(3) . . . . ?
C16 C13 O4 C12 59.6(5) . . . . ?
C15 C13 O4 C12 -65.1(5) . . . . ?
C14 C13 O4 C12 178.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.98 2.46 3.379(5) 156.6 4_554
C15 H15B O5 0.96 2.65 3.512(5) 149.5 3_475
C15 H15C O2 0.96 2.47 3.043(6) 118.3 .
C16 H16A O2 0.96 2.43 2.989(6) 116.6 .
O5 H1O O2 0.86(4) 1.95(5) 2.738(4) 151(4) 4

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034

_shelxl_version_number           2012-9


