# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data_mo_wdd45_0m
_database_code_depnum_ccdc_archive 'CCDC 905935'
#TrackingRef 'CCDC_deposition_wdd45_wdd58_wdd76_wdd65_wdd34_cif.txt'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cl N O3'
_chemical_formula_sum            'C16 H16 Cl N O3'
_chemical_formula_weight         305.75
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'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   7.7450(2)
_cell_length_b                   9.8432(2)
_cell_length_c                   10.1768(2)
_cell_angle_alpha                84.638(1)
_cell_angle_beta                 73.912(1)
_cell_angle_gamma                75.135(1)
_cell_volume                     720.29(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      37.51
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8797
_exptl_absorpt_correction_T_max  0.9446
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature      100.0(1)
_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 SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22351
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         32.50
_reflns_number_total             5147
_reflns_number_gt                4734
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0504P)^2^+0.1840P] where P=(Fo^2^+2Fc^2^)/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         5147
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
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
Cl1A Cl 0.2682(9) 0.6463(7) 0.4722(6) 0.0272(8) Uani 0.27(3) 1 d P A 1
Cl1B Cl 0.2351(11) 0.6432(3) 0.4693(3) 0.0414(6) Uani 0.73(3) 1 d P A 2
O1 O 0.43081(7) 0.37603(5) 0.84772(6) 0.01548(10) Uani 1 1 d . . .
O2 O 0.15487(8) 1.06666(6) 1.03584(6) 0.02006(12) Uani 1 1 d . . .
O3 O 0.67130(8) 0.45230(6) 0.86713(6) 0.01851(11) Uani 1 1 d . . .
N1 N 0.30080(9) 0.83698(6) 0.98632(6) 0.01436(11) Uani 1 1 d . . .
C1 C 0.41721(9) 0.85495(7) 0.85552(7) 0.01351(12) Uani 1 1 d . . .
C2 C 0.47468(10) 0.98010(8) 0.81459(8) 0.01717(13) Uani 1 1 d . . .
H2A H 0.4357 1.0544 0.8744 0.021 Uiso 1 1 calc R . .
C3 C 0.58977(11) 0.99302(8) 0.68466(9) 0.01950(14) Uani 1 1 d . . .
H3A H 0.6240 1.0773 0.6572 0.023 Uiso 1 1 calc R . .
C4 C 0.65452(11) 0.88152(9) 0.59504(8) 0.02043(14) Uani 1 1 d . . .
H4A H 0.7328 0.8905 0.5087 0.025 Uiso 1 1 calc R . .
C5 C 0.60054(11) 0.75658(8) 0.63633(8) 0.01846(14) Uani 1 1 d . . .
H5A H 0.6456 0.6811 0.5777 0.022 Uiso 1 1 calc R . .
C6 C 0.47943(9) 0.74267(7) 0.76468(7) 0.01379(12) Uani 1 1 d . . .
C7 C 0.41342(9) 0.61173(7) 0.79617(7) 0.01282(12) Uani 1 1 d . . .
C8 C 0.25520(9) 0.58753(7) 0.78273(7) 0.01255(11) Uani 1 1 d . . .
C9 C 0.26208(9) 0.43749(7) 0.81189(7) 0.01341(12) Uani 1 1 d . . .
C10 C 0.52331(10) 0.47817(7) 0.83940(7) 0.01404(12) Uani 1 1 d . . .
C11 C 0.17877(10) 0.94120(7) 1.06822(7) 0.01470(12) Uani 1 1 d . . .
C12 C 0.07038(11) 0.89180(8) 1.20295(8) 0.01753(13) Uani 1 1 d . . .
H12A H 0.0783 0.9434 1.2757 0.026 Uiso 1 1 calc R . .
H12B H 0.1206 0.7933 1.2167 0.026 Uiso 1 1 calc R . .
H12C H -0.0569 0.9071 1.2023 0.026 Uiso 1 1 calc R . .
C13 C 0.09478(10) 0.68832(7) 0.74453(8) 0.01539(12) Uani 1 1 d . A .
H13A H 0.0366 0.7576 0.8153 0.018 Uiso 1 1 calc R . .
H13B H 0.0043 0.6372 0.7415 0.018 Uiso 1 1 calc R . .
C14 C 0.14676(11) 0.76436(8) 0.60797(8) 0.01917(14) Uani 1 1 d . . .
H14A H 0.2235 0.8260 0.6145 0.023 Uiso 0.27(3) 1 calc PR A 1
H14B H 0.0351 0.8222 0.5874 0.023 Uiso 0.27(3) 1 calc PR A 1
H14C H 0.2405 0.8119 0.6083 0.023 Uiso 0.73(3) 1 d PR A 2
H14D H 0.0402 0.8337 0.5946 0.023 Uiso 0.73(3) 1 d PR A 2
C15 C 0.19995(11) 0.34808(8) 0.73006(8) 0.01754(13) Uani 1 1 d . . .
H15A H 0.1365 0.3951 0.6624 0.021 Uiso 1 1 calc R . .
H15B H 0.2781 0.2551 0.7057 0.021 Uiso 1 1 calc R . .
C16 C 0.10123(11) 0.37389(8) 0.87839(8) 0.01754(13) Uani 1 1 d . . .
H16A H -0.0217 0.4363 0.8999 0.021 Uiso 1 1 calc R . .
H16B H 0.1198 0.2963 0.9432 0.021 Uiso 1 1 calc R . .
H1N1 H 0.3047(18) 0.7500(14) 1.0158(14) 0.026(3) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1A 0.0400(16) 0.0248(8) 0.0114(8) 0.0001(5) -0.0017(9) -0.0043(9)
Cl1B 0.0681(14) 0.0299(5) 0.0156(3) -0.0016(2) -0.0104(6) 0.0063(6)
O1 0.0171(2) 0.0106(2) 0.0188(2) 0.00176(17) -0.00663(18) -0.00216(17)
O2 0.0254(3) 0.0106(2) 0.0225(3) 0.00005(19) -0.0054(2) -0.00243(19)
O3 0.0168(2) 0.0173(2) 0.0213(3) 0.0010(2) -0.0077(2) -0.00146(18)
N1 0.0175(3) 0.0095(2) 0.0154(3) 0.00083(19) -0.0042(2) -0.00270(19)
C1 0.0138(3) 0.0118(3) 0.0156(3) 0.0017(2) -0.0055(2) -0.0032(2)
C2 0.0185(3) 0.0133(3) 0.0216(3) 0.0020(2) -0.0068(3) -0.0063(2)
C3 0.0186(3) 0.0178(3) 0.0243(4) 0.0062(3) -0.0074(3) -0.0089(3)
C4 0.0186(3) 0.0225(3) 0.0201(3) 0.0051(3) -0.0033(3) -0.0087(3)
C5 0.0186(3) 0.0183(3) 0.0173(3) 0.0008(2) -0.0019(2) -0.0059(2)
C6 0.0141(3) 0.0121(3) 0.0153(3) 0.0017(2) -0.0044(2) -0.0036(2)
C7 0.0147(3) 0.0105(3) 0.0125(3) 0.0003(2) -0.0034(2) -0.0021(2)
C8 0.0146(3) 0.0104(3) 0.0114(3) -0.0003(2) -0.0025(2) -0.0019(2)
C9 0.0150(3) 0.0108(3) 0.0142(3) 0.0003(2) -0.0039(2) -0.0029(2)
C10 0.0161(3) 0.0117(3) 0.0135(3) 0.0000(2) -0.0037(2) -0.0021(2)
C11 0.0171(3) 0.0122(3) 0.0159(3) -0.0009(2) -0.0065(2) -0.0030(2)
C12 0.0206(3) 0.0156(3) 0.0160(3) -0.0003(2) -0.0041(2) -0.0045(2)
C13 0.0147(3) 0.0134(3) 0.0165(3) 0.0003(2) -0.0042(2) -0.0007(2)
C14 0.0216(3) 0.0158(3) 0.0183(3) 0.0023(2) -0.0068(3) -0.0006(2)
C15 0.0219(3) 0.0144(3) 0.0173(3) -0.0022(2) -0.0050(2) -0.0057(2)
C16 0.0193(3) 0.0155(3) 0.0179(3) 0.0004(2) -0.0023(2) -0.0074(2)
_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
Cl1A C14 1.779(7) . ?
Cl1B C14 1.800(3) . ?
O1 C10 1.3606(8) . ?
O1 C9 1.4227(8) . ?
O2 C11 1.2282(9) . ?
O3 C10 1.2142(9) . ?
N1 C11 1.3660(9) . ?
N1 C1 1.4102(9) . ?
N1 H1N1 0.877(14) . ?
C1 C2 1.4043(9) . ?
C1 C6 1.4068(10) . ?
C2 C3 1.3902(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.3924(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3906(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3994(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.4817(9) . ?
C7 C8 1.3513(9) . ?
C7 C10 1.4737(9) . ?
C8 C9 1.4692(9) . ?
C8 C13 1.4974(10) . ?
C9 C16 1.5018(10) . ?
C9 C15 1.5086(10) . ?
C11 C12 1.5060(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.5178(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9601 . ?
C15 C16 1.5034(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
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 O1 C9 108.18(5) . . ?
C11 N1 C1 126.38(6) . . ?
C11 N1 H1N1 117.4(9) . . ?
C1 N1 H1N1 116.2(9) . . ?
C2 C1 C6 119.37(7) . . ?
C2 C1 N1 122.03(7) . . ?
C6 C1 N1 118.59(6) . . ?
C3 C2 C1 120.04(7) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.92(7) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 119.11(7) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 121.06(7) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C1 119.44(6) . . ?
C5 C6 C7 117.98(6) . . ?
C1 C6 C7 122.48(6) . . ?
C8 C7 C10 107.64(6) . . ?
C8 C7 C6 128.49(6) . . ?
C10 C7 C6 123.72(6) . . ?
C7 C8 C9 108.09(6) . . ?
C7 C8 C13 129.18(6) . . ?
C9 C8 C13 122.72(6) . . ?
O1 C9 C8 107.07(5) . . ?
O1 C9 C16 116.68(6) . . ?
C8 C9 C16 126.72(6) . . ?
O1 C9 C15 116.38(6) . . ?
C8 C9 C15 123.89(6) . . ?
C16 C9 C15 59.92(5) . . ?
O3 C10 O1 120.87(6) . . ?
O3 C10 C7 130.13(7) . . ?
O1 C10 C7 108.99(6) . . ?
O2 C11 N1 123.55(7) . . ?
O2 C11 C12 121.28(7) . . ?
N1 C11 C12 115.17(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 C14 114.03(6) . . ?
C8 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C8 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 Cl1A 112.4(2) . . ?
C13 C14 Cl1B 111.18(12) . . ?
C13 C14 H14A 109.1 . . ?
Cl1A C14 H14A 109.1 . . ?
Cl1B C14 H14A 117.0 . . ?
C13 C14 H14B 109.1 . . ?
Cl1A C14 H14B 109.1 . . ?
Cl1B C14 H14B 102.1 . . ?
H14A C14 H14B 107.9 . . ?
C13 C14 H14C 109.5 . . ?
Cl1A C14 H14C 100.4 . . ?
Cl1B C14 H14C 108.6 . . ?
H14B C14 H14C 116.2 . . ?
C13 C14 H14D 109.4 . . ?
Cl1A C14 H14D 116.6 . . ?
Cl1B C14 H14D 110.1 . . ?
H14A C14 H14D 99.3 . . ?
C16 C15 C9 59.82(5) . . ?
C16 C15 H15A 117.8 . . ?
C9 C15 H15A 117.8 . . ?
C16 C15 H15B 117.8 . . ?
C9 C15 H15B 117.8 . . ?
H15A C15 H15B 114.9 . . ?
C9 C16 C15 60.26(5) . . ?
C9 C16 H16A 117.7 . . ?
C15 C16 H16A 117.7 . . ?
C9 C16 H16B 117.7 . . ?
C15 C16 H16B 117.7 . . ?
H16A C16 H16B 114.9 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 25.07(11) . . . . ?
C11 N1 C1 C6 -155.96(7) . . . . ?
C6 C1 C2 C3 0.94(11) . . . . ?
N1 C1 C2 C3 179.90(7) . . . . ?
C1 C2 C3 C4 -2.08(11) . . . . ?
C2 C3 C4 C5 0.88(12) . . . . ?
C3 C4 C5 C6 1.47(12) . . . . ?
C4 C5 C6 C1 -2.58(11) . . . . ?
C4 C5 C6 C7 174.02(7) . . . . ?
C2 C1 C6 C5 1.35(10) . . . . ?
N1 C1 C6 C5 -177.64(6) . . . . ?
C2 C1 C6 C7 -175.10(6) . . . . ?
N1 C1 C6 C7 5.91(10) . . . . ?
C5 C6 C7 C8 -95.10(9) . . . . ?
C1 C6 C7 C8 81.39(10) . . . . ?
C5 C6 C7 C10 79.86(9) . . . . ?
C1 C6 C7 C10 -103.65(8) . . . . ?
C10 C7 C8 C9 -2.03(8) . . . . ?
C6 C7 C8 C9 173.57(7) . . . . ?
C10 C7 C8 C13 178.36(7) . . . . ?
C6 C7 C8 C13 -6.04(12) . . . . ?
C10 O1 C9 C8 -0.98(7) . . . . ?
C10 O1 C9 C16 -149.67(6) . . . . ?
C10 O1 C9 C15 142.48(6) . . . . ?
C7 C8 C9 O1 1.92(8) . . . . ?
C13 C8 C9 O1 -178.44(6) . . . . ?
C7 C8 C9 C16 146.52(7) . . . . ?
C13 C8 C9 C16 -33.84(10) . . . . ?
C7 C8 C9 C15 -138.10(7) . . . . ?
C13 C8 C9 C15 41.54(10) . . . . ?
C9 O1 C10 O3 178.97(7) . . . . ?
C9 O1 C10 C7 -0.23(7) . . . . ?
C8 C7 C10 O3 -177.64(8) . . . . ?
C6 C7 C10 O3 6.50(12) . . . . ?
C8 C7 C10 O1 1.47(8) . . . . ?
C6 C7 C10 O1 -174.39(6) . . . . ?
C1 N1 C11 O2 0.48(12) . . . . ?
C1 N1 C11 C12 179.52(6) . . . . ?
C7 C8 C13 C14 56.98(10) . . . . ?
C9 C8 C13 C14 -122.58(7) . . . . ?
C8 C13 C14 Cl1A 54.7(3) . . . . ?
C8 C13 C14 Cl1B 64.1(3) . . . . ?
O1 C9 C15 C16 106.98(7) . . . . ?
C8 C9 C15 C16 -116.31(8) . . . . ?
O1 C9 C16 C15 -106.47(7) . . . . ?
C8 C9 C16 C15 111.83(8) . . . . ?
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        32.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N1 H1N1 O3 0.876(13) 2.216(13) 3.0738(8) 166.3(12) 2_667 yes
C13 H13A O2 0.9700 2.3300 3.2819(9) 168.00 2_577 yes
C16 H16A O3 0.9700 2.4600 3.2516(11) 139.00 1_455 yes
C16 H16B O2 0.9700 2.3500 3.2717(10) 160.00 1_545 yes


data_mo_wdd58_0m
_database_code_depnum_ccdc_archive 'CCDC 905936'
#TrackingRef 'CCDC_deposition_wdd45_wdd58_wdd76_wdd65_wdd34_cif.txt'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
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'
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a                   9.2655(7)
_cell_length_b                   9.3737(7)
_cell_length_c                   33.083(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2873.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5719
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.10
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      297(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 SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         30.35
_reflns_number_total             4316
_reflns_number_gt                3062
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0751P)^2^+0.6267P] where P=(Fo^2^+2Fc^2^)/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         4316
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
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 0.00099(18) 0.50220(13) 0.15793(4) 0.0704(4) Uani 1 1 d . . .
O2 O 0.05920(12) 0.35407(11) 0.20793(3) 0.0478(3) Uani 1 1 d . . .
O3 O 0.16721(12) -0.07283(10) 0.06160(4) 0.0509(3) Uani 1 1 d . . .
N1 N 0.16474(13) 0.16848(12) 0.06431(3) 0.0371(3) Uani 1 1 d . . .
C1 C -0.18562(17) 0.27317(19) 0.10939(5) 0.0553(4) Uani 1 1 d . . .
H1A H -0.2223 0.3075 0.1337 0.066 Uiso 1 1 calc R . .
C2 C -0.27646(19) 0.2572(2) 0.07676(7) 0.0690(5) Uani 1 1 d . . .
H2A H -0.3730 0.2835 0.0788 0.083 Uiso 1 1 calc R . .
C3 C -0.2239(2) 0.2021(2) 0.04104(6) 0.0641(5) Uani 1 1 d . . .
H3A H -0.2861 0.1874 0.0194 0.077 Uiso 1 1 calc R . .
C4 C -0.07990(18) 0.16857(17) 0.03729(5) 0.0494(4) Uani 1 1 d . . .
H4A H -0.0446 0.1327 0.0130 0.059 Uiso 1 1 calc R . .
C5 C 0.01279(15) 0.18850(13) 0.06988(4) 0.0359(3) Uani 1 1 d . . .
C6 C -0.03929(14) 0.23867(14) 0.10661(4) 0.0387(3) Uani 1 1 d . . .
C7 C 0.05769(14) 0.25145(14) 0.14296(4) 0.0373(3) Uani 1 1 d . . .
H7A H 0.1575 0.2538 0.1332 0.045 Uiso 1 1 calc R . .
C8 C 0.03385(17) 0.38498(16) 0.16843(4) 0.0454(3) Uani 1 1 d . . .
C9 C 0.10512(15) 0.20730(16) 0.21146(4) 0.0403(3) Uani 1 1 d . . .
C10 C 0.11652(19) 0.1483(2) 0.25268(5) 0.0545(4) Uani 1 1 d . . .
H10A H 0.0934 0.0483 0.2565 0.065 Uiso 1 1 calc R . .
H10B H 0.0906 0.2099 0.2751 0.065 Uiso 1 1 calc R . .
C11 C 0.25138(18) 0.1845(2) 0.22905(5) 0.0527(4) Uani 1 1 d . . .
H11A H 0.3060 0.2680 0.2372 0.063 Uiso 1 1 calc R . .
H11B H 0.3088 0.1063 0.2186 0.063 Uiso 1 1 calc R . .
C12 C 0.04787(16) 0.13453(15) 0.17474(4) 0.0412(3) Uani 1 1 d . . .
C13 C 0.0679(2) -0.02001(18) 0.16611(6) 0.0616(5) Uani 1 1 d . . .
H13A H 0.1203 -0.0765 0.1858 0.074 Uiso 1 1 calc R . .
H13B H 0.0827 -0.0482 0.1382 0.074 Uiso 1 1 calc R . .
C14 C -0.0788(2) 0.03439(18) 0.17780(6) 0.0585(4) Uani 1 1 d . . .
H14A H -0.1145 0.0111 0.2046 0.070 Uiso 1 1 calc R . .
H14B H -0.1521 0.0395 0.1569 0.070 Uiso 1 1 calc R . .
C15 C 0.23108(15) 0.04251(13) 0.05968(4) 0.0373(3) Uani 1 1 d . . .
C16 C 0.39078(18) 0.05212(17) 0.05264(6) 0.0531(4) Uani 1 1 d . . .
H16A H 0.4299 -0.0421 0.0496 0.080 Uiso 1 1 calc R . .
H16B H 0.4357 0.0983 0.0753 0.080 Uiso 1 1 calc R . .
H16C H 0.4089 0.1063 0.0285 0.080 Uiso 1 1 calc R . .
H1N1 H 0.2172(19) 0.245(2) 0.0631(5) 0.052(5) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.1115(11) 0.0412(6) 0.0587(7) -0.0052(5) -0.0194(7) 0.0131(7)
O2 0.0607(7) 0.0444(6) 0.0383(5) -0.0086(4) -0.0050(5) 0.0069(5)
O3 0.0494(6) 0.0281(5) 0.0752(8) -0.0029(4) 0.0039(5) -0.0013(4)
N1 0.0409(6) 0.0269(5) 0.0434(6) -0.0031(4) 0.0043(5) -0.0025(4)
C1 0.0412(8) 0.0652(10) 0.0594(9) -0.0165(8) -0.0023(7) 0.0100(7)
C2 0.0406(8) 0.0819(13) 0.0844(13) -0.0172(10) -0.0156(8) 0.0089(8)
C3 0.0563(10) 0.0730(12) 0.0630(10) -0.0077(9) -0.0244(8) 0.0002(9)
C4 0.0577(9) 0.0481(8) 0.0424(7) -0.0073(6) -0.0086(7) -0.0023(7)
C5 0.0408(7) 0.0267(6) 0.0403(6) -0.0022(5) -0.0028(5) -0.0006(5)
C6 0.0390(7) 0.0357(7) 0.0414(7) -0.0057(5) -0.0035(5) 0.0014(5)
C7 0.0372(6) 0.0391(7) 0.0357(6) -0.0049(5) -0.0002(5) 0.0013(5)
C8 0.0548(8) 0.0399(7) 0.0415(7) -0.0050(6) -0.0067(6) 0.0021(6)
C9 0.0406(7) 0.0431(7) 0.0373(6) 0.0002(5) 0.0019(5) 0.0018(6)
C10 0.0567(10) 0.0654(10) 0.0412(7) 0.0090(7) 0.0028(7) -0.0031(8)
C11 0.0442(8) 0.0644(10) 0.0494(8) 0.0062(7) -0.0017(7) 0.0017(7)
C12 0.0442(7) 0.0387(7) 0.0406(6) -0.0029(5) 0.0018(6) 0.0026(6)
C13 0.0896(14) 0.0390(8) 0.0563(9) -0.0024(7) 0.0038(9) 0.0093(8)
C14 0.0664(11) 0.0489(9) 0.0603(10) -0.0019(7) 0.0034(8) -0.0162(8)
C15 0.0442(7) 0.0301(6) 0.0376(6) -0.0024(5) 0.0020(5) 0.0006(5)
C16 0.0464(8) 0.0431(8) 0.0700(10) 0.0016(7) 0.0104(7) 0.0007(6)
_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 C8 1.1919(19) . ?
O2 C8 1.3590(17) . ?
O2 C9 1.4447(17) . ?
O3 C15 1.2342(16) . ?
N1 C15 1.3400(16) . ?
N1 C5 1.4323(18) . ?
N1 H1N1 0.867(18) . ?
C1 C2 1.377(2) . ?
C1 C6 1.397(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3911(19) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3893(18) . ?
C6 C7 1.5061(18) . ?
C7 C12 1.522(2) . ?
C7 C8 1.5250(19) . ?
C7 H7A 0.9800 . ?
C9 C10 1.475(2) . ?
C9 C11 1.490(2) . ?
C9 C12 1.4907(19) . ?
C10 C11 1.513(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.488(2) . ?
C12 C14 1.506(2) . ?
C13 C14 1.502(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.501(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C8 O2 C9 109.37(10) . . ?
C15 N1 C5 125.53(11) . . ?
C15 N1 H1N1 117.8(12) . . ?
C5 N1 H1N1 116.6(12) . . ?
C2 C1 C6 121.09(16) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 C3 119.80(16) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 120.33(15) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 119.87(15) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C6 C5 C4 120.59(13) . . ?
C6 C5 N1 119.89(11) . . ?
C4 C5 N1 119.30(12) . . ?
C5 C6 C1 118.24(13) . . ?
C5 C6 C7 121.20(12) . . ?
C1 C6 C7 120.53(13) . . ?
C6 C7 C12 117.31(11) . . ?
C6 C7 C8 114.85(11) . . ?
C12 C7 C8 101.57(11) . . ?
C6 C7 H7A 107.5 . . ?
C12 C7 H7A 107.5 . . ?
C8 C7 H7A 107.5 . . ?
O1 C8 O2 121.40(13) . . ?
O1 C8 C7 129.24(14) . . ?
O2 C8 C7 109.35(12) . . ?
O2 C9 C10 116.92(13) . . ?
O2 C9 C11 115.84(13) . . ?
C10 C9 C11 61.33(10) . . ?
O2 C9 C12 105.38(11) . . ?
C10 C9 C12 127.38(14) . . ?
C11 C9 C12 125.18(13) . . ?
C9 C10 C11 59.81(10) . . ?
C9 C10 H10A 117.8 . . ?
C11 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
C11 C10 H10B 117.8 . . ?
H10A C10 H10B 114.9 . . ?
C9 C11 C10 58.86(10) . . ?
C9 C11 H11A 117.9 . . ?
C10 C11 H11A 117.9 . . ?
C9 C11 H11B 117.9 . . ?
C10 C11 H11B 117.9 . . ?
H11A C11 H11B 115.0 . . ?
C13 C12 C9 123.88(14) . . ?
C13 C12 C14 60.23(12) . . ?
C9 C12 C14 120.51(13) . . ?
C13 C12 C7 124.13(13) . . ?
C9 C12 C7 102.25(11) . . ?
C14 C12 C7 122.82(13) . . ?
C12 C13 C14 60.48(11) . . ?
C12 C13 H13A 117.7 . . ?
C14 C13 H13A 117.7 . . ?
C12 C13 H13B 117.7 . . ?
C14 C13 H13B 117.7 . . ?
H13A C13 H13B 114.8 . . ?
C13 C14 C12 59.29(11) . . ?
C13 C14 H14A 117.8 . . ?
C12 C14 H14A 117.8 . . ?
C13 C14 H14B 117.8 . . ?
C12 C14 H14B 117.8 . . ?
H14A C14 H14B 115.0 . . ?
O3 C15 N1 123.10(13) . . ?
O3 C15 C16 122.23(13) . . ?
N1 C15 C16 114.66(12) . . ?
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 . . ?
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 2.1(3) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C3 C4 C5 N1 -173.09(15) . . . . ?
C15 N1 C5 C6 112.32(15) . . . . ?
C15 N1 C5 C4 -72.94(18) . . . . ?
C4 C5 C6 C1 -2.3(2) . . . . ?
N1 C5 C6 C1 172.42(13) . . . . ?
C4 C5 C6 C7 175.85(13) . . . . ?
N1 C5 C6 C7 -9.47(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C7 -177.70(17) . . . . ?
C5 C6 C7 C12 -100.90(15) . . . . ?
C1 C6 C7 C12 77.17(17) . . . . ?
C5 C6 C7 C8 139.90(13) . . . . ?
C1 C6 C7 C8 -42.03(19) . . . . ?
C9 O2 C8 O1 -176.56(16) . . . . ?
C9 O2 C8 C7 2.23(16) . . . . ?
C6 C7 C8 O1 -34.7(2) . . . . ?
C12 C7 C8 O1 -162.39(19) . . . . ?
C6 C7 C8 O2 146.60(12) . . . . ?
C12 C7 C8 O2 18.94(15) . . . . ?
C8 O2 C9 C10 -171.06(13) . . . . ?
C8 O2 C9 C11 119.54(13) . . . . ?
C8 O2 C9 C12 -23.31(15) . . . . ?
O2 C9 C10 C11 -106.23(15) . . . . ?
C12 C9 C10 C11 114.12(17) . . . . ?
O2 C9 C11 C10 107.97(14) . . . . ?
C12 C9 C11 C10 -117.46(17) . . . . ?
O2 C9 C12 C13 -179.05(15) . . . . ?
C10 C9 C12 C13 -35.8(2) . . . . ?
C11 C9 C12 C13 42.6(2) . . . . ?
O2 C9 C12 C14 -106.42(15) . . . . ?
C10 C9 C12 C14 36.8(2) . . . . ?
C11 C9 C12 C14 115.26(17) . . . . ?
O2 C9 C12 C7 34.08(14) . . . . ?
C10 C9 C12 C7 177.30(14) . . . . ?
C11 C9 C12 C7 -104.24(15) . . . . ?
C6 C7 C12 C13 55.8(2) . . . . ?
C8 C7 C12 C13 -178.18(16) . . . . ?
C6 C7 C12 C9 -157.47(12) . . . . ?
C8 C7 C12 C9 -31.43(13) . . . . ?
C6 C7 C12 C14 -18.17(19) . . . . ?
C8 C7 C12 C14 107.88(15) . . . . ?
C9 C12 C13 C14 108.69(17) . . . . ?
C7 C12 C13 C14 -111.50(17) . . . . ?
C9 C12 C14 C13 -114.10(16) . . . . ?
C7 C12 C14 C13 113.60(16) . . . . ?
C5 N1 C15 O3 -3.5(2) . . . . ?
C5 N1 C15 C16 177.58(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.039
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N1 H1N1 O3 0.867(18) 2.016(19) 2.8832(15) 177.6(18) 8_665 yes
C10 H10A O2 0.97 2.59 3.458(2) 149.2 3_545 yes


data_mo_wdd76_0m
_database_code_depnum_ccdc_archive 'CCDC 905937'
#TrackingRef 'CCDC_deposition_wdd45_wdd58_wdd76_wdd65_wdd34_cif.txt'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 Cl I N O2'
_chemical_formula_sum            'C14 H13 Cl I N O2'
_chemical_formula_weight         389.60
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
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                   9.6909(5)
_cell_length_b                   15.7393(8)
_cell_length_c                   9.9721(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.376(1)
_cell_angle_gamma                90.00
_cell_volume                     1416.39(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5971
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.68
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3234
_exptl_absorpt_correction_T_max  0.8436
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      297(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 SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15558
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         2.26
_diffrn_reflns_theta_max         30.45
_reflns_number_total             4266
_reflns_number_gt                3406
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0407P)^2^+2.7106P] where P=(Fo^2^+2Fc^2^)/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         4266
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
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
I1 I 1.15919(3) 0.16121(2) 0.33776(3) 0.06186(12) Uani 1 1 d . . .
Cl1 Cl 0.84237(12) -0.05104(6) 0.21437(11) 0.0597(3) Uani 1 1 d . . .
O1 O 0.4190(3) 0.21843(19) 0.1542(3) 0.0576(7) Uani 1 1 d . . .
O2 O 0.7863(3) 0.22662(15) 0.2167(2) 0.0430(5) Uani 1 1 d . . .
N1 N 0.4836(3) 0.17607(19) -0.0353(3) 0.0424(6) Uani 1 1 d . . .
C1 C 0.6512(3) 0.07170(18) 0.0653(3) 0.0314(5) Uani 1 1 d . . .
C2 C 0.7550(3) 0.0121(2) 0.0645(3) 0.0382(6) Uani 1 1 d . . .
C3 C 0.7914(4) 0.0012(3) -0.0576(4) 0.0503(8) Uani 1 1 d . . .
H3A H 0.8623 -0.0387 -0.0575 0.060 Uiso 1 1 calc R . .
C4 C 0.7217(5) 0.0497(3) -0.1777(4) 0.0572(10) Uani 1 1 d . . .
H4A H 0.7469 0.0422 -0.2584 0.069 Uiso 1 1 calc R . .
C5 C 0.6153(5) 0.1093(2) -0.1824(4) 0.0510(9) Uani 1 1 d . . .
H5A H 0.5676 0.1414 -0.2648 0.061 Uiso 1 1 calc R . .
C6 C 0.5833(4) 0.11915(19) -0.0594(3) 0.0365(6) Uani 1 1 d . . .
C7 C 0.4865(3) 0.1721(2) 0.1007(4) 0.0398(7) Uani 1 1 d . . .
C8 C 0.5876(3) 0.09805(19) 0.1766(3) 0.0326(5) Uani 1 1 d . . .
H8A H 0.5246 0.0517 0.1867 0.039 Uiso 1 1 calc R . .
C9 C 0.6943(3) 0.12116(19) 0.3254(3) 0.0324(5) Uani 1 1 d . . .
C10 C 0.6331(4) 0.1249(3) 0.4470(4) 0.0480(8) Uani 1 1 d . . .
H10A H 0.6734 0.1676 0.5211 0.058 Uiso 1 1 calc R . .
H10B H 0.5287 0.1126 0.4229 0.058 Uiso 1 1 calc R . .
C11 C 0.7316(5) 0.0534(2) 0.4421(4) 0.0536(9) Uani 1 1 d . . .
H11A H 0.6868 -0.0022 0.4153 0.064 Uiso 1 1 calc R . .
H11B H 0.8314 0.0528 0.5135 0.064 Uiso 1 1 calc R . .
C12 C 0.8026(3) 0.1885(2) 0.3267(3) 0.0340(6) Uani 1 1 d . . .
C13 C 0.9281(4) 0.2121(3) 0.4649(4) 0.0583(11) Uani 1 1 d . . .
H13A H 0.8921 0.2530 0.5172 0.070 Uiso 1 1 calc R . .
H13B H 0.9594 0.1618 0.5245 0.070 Uiso 1 1 calc R . .
C14 C 1.0584(4) 0.2490(3) 0.4397(4) 0.0516(9) Uani 1 1 d . . .
H14A H 1.1316 0.2665 0.5312 0.062 Uiso 1 1 calc R . .
H14B H 1.0270 0.2991 0.3797 0.062 Uiso 1 1 calc R . .
H1N1 H 0.437(5) 0.209(3) -0.090(5) 0.054(12) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04574(15) 0.0755(2) 0.06283(19) -0.01323(13) 0.01802(12) 0.00735(11)
Cl1 0.0657(6) 0.0542(5) 0.0484(5) 0.0008(4) 0.0081(4) 0.0243(4)
O1 0.0398(13) 0.0672(17) 0.0617(16) -0.0104(14) 0.0136(12) 0.0149(12)
O2 0.0425(12) 0.0474(13) 0.0371(11) 0.0022(10) 0.0123(9) -0.0092(10)
N1 0.0403(14) 0.0368(14) 0.0407(15) 0.0023(11) 0.0036(12) 0.0045(11)
C1 0.0333(13) 0.0308(13) 0.0287(12) -0.0027(10) 0.0097(10) -0.0042(10)
C2 0.0391(15) 0.0374(15) 0.0362(15) -0.0067(12) 0.0116(12) -0.0007(12)
C3 0.0525(19) 0.052(2) 0.054(2) -0.0148(16) 0.0288(17) -0.0022(16)
C4 0.075(3) 0.063(2) 0.047(2) -0.0100(17) 0.037(2) -0.012(2)
C5 0.070(2) 0.050(2) 0.0329(16) 0.0022(14) 0.0179(16) -0.0126(17)
C6 0.0416(15) 0.0355(14) 0.0289(13) -0.0009(11) 0.0087(11) -0.0065(12)
C7 0.0268(12) 0.0431(16) 0.0427(16) -0.0039(13) 0.0044(12) -0.0006(11)
C8 0.0312(13) 0.0340(13) 0.0328(13) -0.0004(11) 0.0120(11) -0.0032(10)
C9 0.0349(13) 0.0362(14) 0.0273(12) 0.0000(10) 0.0128(11) 0.0005(11)
C10 0.057(2) 0.058(2) 0.0400(17) -0.0030(15) 0.0299(16) -0.0059(16)
C11 0.077(3) 0.049(2) 0.0360(17) 0.0090(14) 0.0219(17) 0.0022(18)
C12 0.0291(12) 0.0452(15) 0.0283(13) -0.0069(11) 0.0111(10) -0.0012(11)
C13 0.0421(18) 0.101(3) 0.0309(16) -0.0190(18) 0.0122(14) -0.0205(19)
C14 0.0392(16) 0.064(2) 0.052(2) -0.0197(17) 0.0159(15) -0.0154(15)
_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
I1 C14 2.149(4) . ?
Cl1 C2 1.736(3) . ?
O1 C7 1.224(4) . ?
O2 C12 1.209(4) . ?
N1 C7 1.347(5) . ?
N1 C6 1.401(5) . ?
N1 H1N1 0.78(5) . ?
C1 C2 1.378(4) . ?
C1 C6 1.393(4) . ?
C1 C8 1.511(4) . ?
C2 C3 1.395(5) . ?
C3 C4 1.373(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5A 0.9300 . ?
C7 C8 1.534(4) . ?
C8 C9 1.511(4) . ?
C8 H8A 0.9800 . ?
C9 C12 1.488(4) . ?
C9 C11 1.521(4) . ?
C9 C10 1.533(4) . ?
C10 C11 1.487(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.515(4) . ?
C13 C14 1.492(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 112.3(3) . . ?
C7 N1 H1N1 122(3) . . ?
C6 N1 H1N1 125(3) . . ?
C2 C1 C6 117.9(3) . . ?
C2 C1 C8 133.3(3) . . ?
C6 C1 C8 108.8(3) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 Cl1 120.8(2) . . ?
C3 C2 Cl1 118.8(3) . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H4A 118.9 . . ?
C5 C4 H4A 118.9 . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 H5A 121.6 . . ?
C4 C5 H5A 121.6 . . ?
C5 C6 C1 123.2(3) . . ?
C5 C6 N1 128.1(3) . . ?
C1 C6 N1 108.7(3) . . ?
O1 C7 N1 126.4(3) . . ?
O1 C7 C8 125.7(3) . . ?
N1 C7 C8 107.9(3) . . ?
C1 C8 C9 118.1(2) . . ?
C1 C8 C7 101.8(2) . . ?
C9 C8 C7 112.8(2) . . ?
C1 C8 H8A 107.9 . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8A 107.9 . . ?
C12 C9 C8 114.1(2) . . ?
C12 C9 C11 121.5(3) . . ?
C8 C9 C11 118.0(3) . . ?
C12 C9 C10 116.1(3) . . ?
C8 C9 C10 117.5(3) . . ?
C11 C9 C10 58.3(2) . . ?
C11 C10 C9 60.5(2) . . ?
C11 C10 H10A 117.7 . . ?
C9 C10 H10A 117.7 . . ?
C11 C10 H10B 117.7 . . ?
C9 C10 H10B 117.7 . . ?
H10A C10 H10B 114.8 . . ?
C10 C11 C9 61.3(2) . . ?
C10 C11 H11A 117.6 . . ?
C9 C11 H11A 117.6 . . ?
C10 C11 H11B 117.6 . . ?
C9 C11 H11B 117.6 . . ?
H11A C11 H11B 114.7 . . ?
O2 C12 C9 119.1(3) . . ?
O2 C12 C13 120.0(3) . . ?
C9 C12 C13 120.8(3) . . ?
C14 C13 C12 113.0(3) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 I1 112.9(3) . . ?
C13 C14 H14A 109.0 . . ?
I1 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
I1 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
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 0.9(5) . . . . ?
C8 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 Cl1 -178.8(2) . . . . ?
C8 C1 C2 Cl1 -0.4(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
Cl1 C2 C3 C4 179.1(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C5 C6 N1 178.3(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C8 C1 C6 C5 -179.0(3) . . . . ?
C2 C1 C6 N1 -179.4(3) . . . . ?
C8 C1 C6 N1 1.8(3) . . . . ?
C7 N1 C6 C5 -176.1(3) . . . . ?
C7 N1 C6 C1 3.1(4) . . . . ?
C6 N1 C7 O1 174.7(3) . . . . ?
C6 N1 C7 C8 -6.4(4) . . . . ?
C2 C1 C8 C9 52.3(4) . . . . ?
C6 C1 C8 C9 -129.1(3) . . . . ?
C2 C1 C8 C7 176.3(3) . . . . ?
C6 C1 C8 C7 -5.1(3) . . . . ?
O1 C7 C8 C1 -174.2(3) . . . . ?
N1 C7 C8 C1 6.9(3) . . . . ?
O1 C7 C8 C9 -46.7(4) . . . . ?
N1 C7 C8 C9 134.4(3) . . . . ?
C1 C8 C9 C12 54.7(4) . . . . ?
C7 C8 C9 C12 -63.6(3) . . . . ?
C1 C8 C9 C11 -97.6(3) . . . . ?
C7 C8 C9 C11 144.1(3) . . . . ?
C1 C8 C9 C10 -164.3(3) . . . . ?
C7 C8 C9 C10 77.4(3) . . . . ?
C12 C9 C10 C11 -112.4(3) . . . . ?
C8 C9 C10 C11 107.4(3) . . . . ?
C12 C9 C11 C10 103.2(3) . . . . ?
C8 C9 C11 C10 -106.6(3) . . . . ?
C8 C9 C12 O2 9.6(4) . . . . ?
C11 C9 C12 O2 160.8(3) . . . . ?
C10 C9 C12 O2 -131.9(3) . . . . ?
C8 C9 C12 C13 -173.0(3) . . . . ?
C11 C9 C12 C13 -21.8(5) . . . . ?
C10 C9 C12 C13 45.4(4) . . . . ?
O2 C12 C13 C14 -28.3(5) . . . . ?
C9 C12 C13 C14 154.4(3) . . . . ?
C12 C13 C14 I1 -62.9(5) . . . . ?
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C5 H5A O1 0.93 2.60 3.371(5) 140.9 4_565 yes
C10 H10A O2 0.97 2.49 3.463(4) 177.5 4_566 yes
C13 H13A O2 0.97 2.57 3.412(4) 145.4 4_566 yes
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.45
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.657
_refine_diff_density_min         -1.548
_refine_diff_density_rms         0.092


data_mo_wdd34_0m
_database_code_depnum_ccdc_archive 'CCDC 905938'
#TrackingRef 'CCDC_deposition_wdd45_wdd58_wdd76_wdd65_wdd34_cif.txt'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N O4'
_chemical_formula_sum            'C17 H19 N O4'
_chemical_formula_weight         301.33
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           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a                   13.3795(7)
_cell_length_b                   12.7454(8)
_cell_length_c                   17.2339(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2938.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    6028
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.10
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature      100.0(1)
_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 SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20908
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         32.14
_reflns_number_total             5116
_reflns_number_gt                4180
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0590P)^2^+0.6742P] where P=(Fo^2^+2Fc^2^)/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         5116
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
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 0.48543(6) 0.32573(6) 0.25189(5) 0.03228(18) Uani 1 1 d . . .
O2 O 0.46040(5) 0.69019(6) 0.13529(4) 0.01902(14) Uani 1 1 d . . .
O3 O 0.40078(6) 0.50951(6) 0.05437(4) 0.02365(15) Uani 1 1 d . . .
O4 O 0.25286(5) 0.58773(5) 0.04356(4) 0.01999(14) Uani 1 1 d . . .
N1 N 0.48205(6) 0.49392(7) 0.20751(5) 0.02058(16) Uani 1 1 d . . .
C1 C 0.40227(7) 0.53318(7) 0.25300(5) 0.01791(17) Uani 1 1 d . . .
C2 C 0.38686(8) 0.49606(8) 0.32848(5) 0.02357(19) Uani 1 1 d . . .
H2A H 0.4303 0.4466 0.3494 0.028 Uiso 1 1 calc R . .
C3 C 0.30728(9) 0.53264(9) 0.37211(5) 0.0260(2) Uani 1 1 d . . .
H3A H 0.2972 0.5073 0.4221 0.031 Uiso 1 1 calc R . .
C4 C 0.24249(8) 0.60691(8) 0.34159(5) 0.02389(19) Uani 1 1 d . . .
H4A H 0.1884 0.6305 0.3706 0.029 Uiso 1 1 calc R . .
C5 C 0.25896(7) 0.64609(7) 0.26708(5) 0.01903(17) Uani 1 1 d . . .
H5A H 0.2160 0.6968 0.2472 0.023 Uiso 1 1 calc R . .
C6 C 0.33855(7) 0.61078(7) 0.22175(5) 0.01586(16) Uani 1 1 d . . .
C7 C 0.35910(6) 0.65811(7) 0.14104(5) 0.01497(15) Uani 1 1 d . . .
C8 C 0.34332(7) 0.57558(7) 0.07625(5) 0.01714(16) Uani 1 1 d . . .
C9 C 0.19922(7) 0.67758(7) 0.07738(5) 0.01781(16) Uani 1 1 d . . .
C10 C 0.10612(7) 0.63473(8) 0.12018(6) 0.02262(19) Uani 1 1 d . . .
H10A H 0.0816 0.6803 0.1610 0.027 Uiso 1 1 calc R . .
H10B H 0.1133 0.5631 0.1384 0.027 Uiso 1 1 calc R . .
C11 C 0.04821(8) 0.64482(9) 0.04275(6) 0.0289(2) Uani 1 1 d . . .
H11A H 0.0449 0.5802 0.0132 0.035 Uiso 1 1 calc R . .
H11B H -0.0174 0.6763 0.0481 0.035 Uiso 1 1 calc R . .
C12 C 0.12959(8) 0.72172(8) 0.01438(6) 0.0256(2) Uani 1 1 d . . .
H12A H 0.1523 0.7084 -0.0382 0.031 Uiso 1 1 calc R . .
H12B H 0.1125 0.7951 0.0215 0.031 Uiso 1 1 calc R . .
C13 C 0.28216(7) 0.73962(7) 0.11513(5) 0.01593(15) Uani 1 1 d . . .
C14 C 0.31740(8) 0.83967(7) 0.07690(6) 0.02233(18) Uani 1 1 d . . .
H14A H 0.3887 0.8536 0.0762 0.027 Uiso 1 1 calc R . .
H14B H 0.2813 0.8641 0.0316 0.027 Uiso 1 1 calc R . .
C15 C 0.26457(7) 0.84338(7) 0.15395(5) 0.02048(18) Uani 1 1 d . . .
H15A H 0.3041 0.8598 0.1995 0.025 Uiso 1 1 calc R . .
H15B H 0.1968 0.8703 0.1549 0.025 Uiso 1 1 calc R . .
C16 C 0.51473(7) 0.39299(8) 0.20581(6) 0.02240(19) Uani 1 1 d . . .
C17 C 0.58852(8) 0.36904(9) 0.14246(7) 0.0293(2) Uani 1 1 d . . .
H17A H 0.5934 0.2944 0.1357 0.044 Uiso 1 1 calc R . .
H17B H 0.6528 0.3967 0.1563 0.044 Uiso 1 1 calc R . .
H17C H 0.5665 0.4007 0.0949 0.044 Uiso 1 1 calc R . .
H1O2 H 0.4712(11) 0.7298(13) 0.1738(10) 0.038(4) Uiso 1 1 d . . .
H1N1 H 0.4988(11) 0.5344(13) 0.1700(9) 0.037(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0338(4) 0.0216(4) 0.0415(4) 0.0104(3) -0.0033(3) 0.0047(3)
O2 0.0170(3) 0.0187(3) 0.0213(3) -0.0003(2) 0.0034(2) -0.0036(2)
O3 0.0285(3) 0.0213(3) 0.0211(3) -0.0047(3) 0.0032(3) 0.0042(3)
O4 0.0244(3) 0.0170(3) 0.0185(3) -0.0037(2) -0.0027(2) 0.0009(3)
N1 0.0224(4) 0.0173(3) 0.0220(4) 0.0027(3) 0.0000(3) 0.0008(3)
C1 0.0207(4) 0.0163(4) 0.0168(3) 0.0004(3) -0.0017(3) -0.0030(3)
C2 0.0310(5) 0.0220(4) 0.0178(4) 0.0042(3) -0.0051(3) -0.0037(4)
C3 0.0370(5) 0.0261(5) 0.0149(3) 0.0023(3) 0.0005(4) -0.0090(4)
C4 0.0297(5) 0.0256(5) 0.0164(4) -0.0023(3) 0.0058(3) -0.0064(4)
C5 0.0219(4) 0.0185(4) 0.0167(3) -0.0013(3) 0.0023(3) -0.0026(3)
C6 0.0194(4) 0.0144(3) 0.0138(3) 0.0000(3) 0.0001(3) -0.0034(3)
C7 0.0167(3) 0.0134(3) 0.0148(3) -0.0003(3) 0.0021(3) -0.0018(3)
C8 0.0218(4) 0.0157(4) 0.0140(3) 0.0007(3) 0.0026(3) -0.0015(3)
C9 0.0213(4) 0.0146(4) 0.0176(3) -0.0011(3) -0.0019(3) 0.0004(3)
C10 0.0201(4) 0.0224(4) 0.0253(4) -0.0023(4) -0.0004(3) -0.0034(4)
C11 0.0240(5) 0.0307(5) 0.0321(5) -0.0056(4) -0.0080(4) -0.0010(4)
C12 0.0303(5) 0.0221(4) 0.0243(4) 0.0008(4) -0.0084(4) 0.0019(4)
C13 0.0198(4) 0.0124(3) 0.0155(3) 0.0004(3) 0.0007(3) -0.0006(3)
C14 0.0282(5) 0.0151(4) 0.0236(4) 0.0039(3) 0.0027(3) -0.0019(4)
C15 0.0242(4) 0.0139(4) 0.0234(4) -0.0027(3) 0.0008(3) 0.0003(3)
C16 0.0185(4) 0.0194(4) 0.0293(4) 0.0017(4) -0.0077(3) 0.0016(3)
C17 0.0254(5) 0.0241(5) 0.0384(5) -0.0028(4) -0.0012(4) 0.0054(4)
_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 C16 1.2325(13) . ?
O2 C7 1.4192(11) . ?
O2 H1O2 0.846(17) . ?
O3 C8 1.2010(11) . ?
O4 C8 1.3439(11) . ?
O4 C9 1.4718(11) . ?
N1 C16 1.3590(13) . ?
N1 C1 1.4156(12) . ?
N1 H1N1 0.857(17) . ?
C1 C2 1.3996(13) . ?
C1 C6 1.4125(13) . ?
C2 C3 1.3843(15) . ?
C2 H2A 0.9300 . ?
C3 C4 1.3871(16) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3953(12) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3952(12) . ?
C5 H5A 0.9300 . ?
C6 C7 1.5408(11) . ?
C7 C13 1.5291(12) . ?
C7 C8 1.5485(12) . ?
C9 C13 1.5099(12) . ?
C9 C12 1.5372(13) . ?
C9 C10 1.5472(13) . ?
C10 C11 1.5484(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5444(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.5008(12) . ?
C13 C14 1.5108(12) . ?
C14 C15 1.5050(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.5034(15) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C7 O2 H1O2 106.3(10) . . ?
C8 O4 C9 111.27(7) . . ?
C16 N1 C1 126.09(9) . . ?
C16 N1 H1N1 118.0(11) . . ?
C1 N1 H1N1 113.7(10) . . ?
C2 C1 C6 120.14(9) . . ?
C2 C1 N1 120.42(9) . . ?
C6 C1 N1 119.44(8) . . ?
C3 C2 C1 120.28(9) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 120.30(9) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.64(9) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 121.35(9) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C1 118.24(8) . . ?
C5 C6 C7 121.02(8) . . ?
C1 C6 C7 120.70(8) . . ?
O2 C7 C13 115.26(7) . . ?
O2 C7 C6 110.26(7) . . ?
C13 C7 C6 114.18(7) . . ?
O2 C7 C8 105.99(7) . . ?
C13 C7 C8 99.15(7) . . ?
C6 C7 C8 111.14(7) . . ?
O3 C8 O4 121.72(8) . . ?
O3 C8 C7 127.98(8) . . ?
O4 C8 C7 110.29(7) . . ?
O4 C9 C13 102.69(7) . . ?
O4 C9 C12 107.49(7) . . ?
C13 C9 C12 123.92(8) . . ?
O4 C9 C10 107.86(7) . . ?
C13 C9 C10 124.82(7) . . ?
C12 C9 C10 88.74(7) . . ?
C9 C10 C11 87.86(7) . . ?
C9 C10 H10A 114.0 . . ?
C11 C10 H10A 114.0 . . ?
C9 C10 H10B 114.0 . . ?
C11 C10 H10B 114.0 . . ?
H10A C10 H10B 111.2 . . ?
C12 C11 C10 88.44(7) . . ?
C12 C11 H11A 113.9 . . ?
C10 C11 H11A 113.9 . . ?
C12 C11 H11B 113.9 . . ?
C10 C11 H11B 113.9 . . ?
H11A C11 H11B 111.1 . . ?
C9 C12 C11 88.36(7) . . ?
C9 C12 H12A 113.9 . . ?
C11 C12 H12A 113.9 . . ?
C9 C12 H12B 113.9 . . ?
C11 C12 H12B 113.9 . . ?
H12A C12 H12B 111.1 . . ?
C15 C13 C9 122.57(8) . . ?
C15 C13 C14 59.97(6) . . ?
C9 C13 C14 118.92(7) . . ?
C15 C13 C7 125.03(7) . . ?
C9 C13 C7 105.36(7) . . ?
C14 C13 C7 119.39(8) . . ?
C15 C14 C13 59.69(6) . . ?
C15 C14 H14A 117.8 . . ?
C13 C14 H14A 117.8 . . ?
C15 C14 H14B 117.8 . . ?
C13 C14 H14B 117.8 . . ?
H14A C14 H14B 114.9 . . ?
C13 C15 C14 60.35(6) . . ?
C13 C15 H15A 117.7 . . ?
C14 C15 H15A 117.7 . . ?
C13 C15 H15B 117.7 . . ?
C14 C15 H15B 117.7 . . ?
H15A C15 H15B 114.9 . . ?
O1 C16 N1 122.84(10) . . ?
O1 C16 C17 122.37(10) . . ?
N1 C16 C17 114.78(9) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C16 N1 C1 C2 37.78(14) . . . . ?
C16 N1 C1 C6 -142.63(10) . . . . ?
C6 C1 C2 C3 2.05(14) . . . . ?
N1 C1 C2 C3 -178.36(9) . . . . ?
C1 C2 C3 C4 -0.42(15) . . . . ?
C2 C3 C4 C5 -1.17(15) . . . . ?
C3 C4 C5 C6 1.13(15) . . . . ?
C4 C5 C6 C1 0.48(13) . . . . ?
C4 C5 C6 C7 -177.14(8) . . . . ?
C2 C1 C6 C5 -2.06(13) . . . . ?
N1 C1 C6 C5 178.35(8) . . . . ?
C2 C1 C6 C7 175.57(8) . . . . ?
N1 C1 C6 C7 -4.02(12) . . . . ?
C5 C6 C7 O2 128.15(8) . . . . ?
C1 C6 C7 O2 -49.41(11) . . . . ?
C5 C6 C7 C13 -3.48(11) . . . . ?
C1 C6 C7 C13 178.96(8) . . . . ?
C5 C6 C7 C8 -114.61(9) . . . . ?
C1 C6 C7 C8 67.83(10) . . . . ?
C9 O4 C8 O3 -176.60(8) . . . . ?
C9 O4 C8 C7 2.17(9) . . . . ?
O2 C7 C8 O3 37.54(12) . . . . ?
C13 C7 C8 O3 157.26(9) . . . . ?
C6 C7 C8 O3 -82.27(11) . . . . ?
O2 C7 C8 O4 -141.13(7) . . . . ?
C13 C7 C8 O4 -21.41(8) . . . . ?
C6 C7 C8 O4 99.06(8) . . . . ?
C8 O4 C9 C13 18.55(9) . . . . ?
C8 O4 C9 C12 150.68(8) . . . . ?
C8 O4 C9 C10 -114.88(8) . . . . ?
O4 C9 C10 C11 -88.72(8) . . . . ?
C13 C9 C10 C11 150.93(9) . . . . ?
C12 C9 C10 C11 19.26(8) . . . . ?
C9 C10 C11 C12 -19.17(8) . . . . ?
O4 C9 C12 C11 89.03(8) . . . . ?
C13 C9 C12 C11 -151.66(9) . . . . ?
C10 C9 C12 C11 -19.31(8) . . . . ?
C10 C11 C12 C9 19.30(8) . . . . ?
O4 C9 C13 C15 176.32(7) . . . . ?
C12 C9 C13 C15 54.81(12) . . . . ?
C10 C9 C13 C15 -61.02(12) . . . . ?
O4 C9 C13 C14 105.33(9) . . . . ?
C12 C9 C13 C14 -16.19(13) . . . . ?
C10 C9 C13 C14 -132.02(9) . . . . ?
O4 C9 C13 C7 -31.82(8) . . . . ?
C12 C9 C13 C7 -153.33(8) . . . . ?
C10 C9 C13 C7 90.84(10) . . . . ?
O2 C7 C13 C15 -64.57(11) . . . . ?
C6 C7 C13 C15 64.59(11) . . . . ?
C8 C7 C13 C15 -177.19(8) . . . . ?
O2 C7 C13 C9 144.46(7) . . . . ?
C6 C7 C13 C9 -86.37(8) . . . . ?
C8 C7 C13 C9 31.85(8) . . . . ?
O2 C7 C13 C14 7.56(11) . . . . ?
C6 C7 C13 C14 136.73(8) . . . . ?
C8 C7 C13 C14 -105.05(8) . . . . ?
C9 C13 C14 C15 113.02(9) . . . . ?
C7 C13 C14 C15 -115.81(9) . . . . ?
C9 C13 C15 C14 -107.06(9) . . . . ?
C7 C13 C15 C14 106.67(10) . . . . ?
C1 N1 C16 O1 -9.30(16) . . . . ?
C1 N1 C16 C17 169.84(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        32.14
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.048
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
O2 H1O2 O1 0.846(17) 1.863(17) 2.7000(11) 169.6(15) 3_655 yes
N1 H1N1 O2 0.857(16) 2.137(16) 2.8090(12) 135.1(14) . yes
C3 H3A O4 0.9300 2.5100 3.4252(12) 168.00 2_565 yes
C10 H10A O1 0.97 2.59 3.5466(14) 170.3 8_665 yes
###############################################################################