# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_macrocycle_12a

_audit_creation_date             2013-06-13
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_formula_moiety         'C29 H37 N O5'
_chemical_formula_sum            'C29 H37 N O5'
_chemical_formula_weight         479.60
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   8.8916(3)
_cell_length_b                   34.6623(15)
_cell_length_c                   8.5392(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.831(2)
_cell_angle_gamma                90
_cell_volume                     2613.13(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296.15
_cell_measurement_reflns_used    6556
_cell_measurement_theta_max      23.81
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2190
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29330
_diffrn_reflns_theta_full        29.3367
_diffrn_reflns_theta_max         29.34
_diffrn_reflns_theta_min         1.17
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9700
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              47
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                4125
_reflns_number_total             6948
_reflns_threshold_expression     I>=2u(I)
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         1.2580
_refine_diff_density_min         -0.5915
_refine_diff_density_rms         0.0713
_refine_ls_d_res_high            0.7253
_refine_ls_d_res_low             17.3312
_refine_ls_goodness_of_fit_ref   1.6651
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0848
_refine_ls_restrained_S_all      1.6651
_refine_ls_shift/su_max          0.119
_refine_ls_shift/su_mean         0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2800
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C11(H11a,H11b), C17(H17a,H17b), C19(H19a,H19b), C21(H21a,H21b),
 C22(H22a,H22b), C25(H25a,H25b), C27(H27a,H27b), C28(H28a,H28b), C29(H29a,H29b),
  C30(H30a,H30b), C32(H32a,H32b), C34(H34a,H34b), C35(H35a,H35b)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C8(H8), C12(H12), C13(H13), C26(H26), C24(H24), C33(H33), C14(H14)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.8044(2) 0.52466(5) 0.4399(2) 0.0625(5) Uani 1.000000 .
O2 O 0.8574(2) 0.76637(5) 0.4283(2) 0.0630(5) Uani 1.000000 .
N3 N 0.5099(2) 0.56263(6) 0.1917(2) 0.0489(5) Uani 1.000000 .
O4 O 1.1110(3) 0.76620(6) 0.6428(2) 0.0769(6) Uani 1.000000 .
O5 O 0.5016(3) 0.55960(7) 0.4594(2) 0.0853(7) Uani 1.000000 .
C6 C 0.9763(3) 0.82245(7) 0.5454(3) 0.0532(6) Uani 1.000000 .
C7 C 0.6108(3) 0.68976(7) 0.2240(3) 0.0583(7) Uani 1.000000 .
C8 C 0.7798(3) 0.50358(8) -0.0897(3) 0.0631(7) Uani 1.000000 .
C9 C 0.6973(3) 0.51912(6) 0.1582(3) 0.0479(6) Uani 1.000000 .
C10 C 0.6751(3) 0.51817(7) 0.3299(3) 0.0533(6) Uani 1.000000 .
C11 C 0.7471(3) 0.74944(8) 0.3127(4) 0.0648(7) Uani 1.000000 .
C12 C 0.6744(3) 0.52883(8) -0.1646(3) 0.0606(7) Uani 1.000000 .
C13 C 0.5793(3) 0.54958(7) -0.0799(3) 0.0543(6) Uani 1.000000 .
C14 C 0.9838(3) 0.86268(8) 0.5496(4) 0.0674(8) Uani 1.000000 .
C15 C 0.5524(3) 0.54902(8) 0.3398(3) 0.0578(6) Uani 1.000000 .
C16 C 0.8747(3) 0.80524(7) 0.4254(3) 0.0544(6) Uani 1.000000 .
C17 C 0.8771(3) 0.56114(8) 0.4213(3) 0.0669(8) Uani 1.000000 .
C18 C 0.5937(2) 0.54486(6) 0.0804(3) 0.0437(5) Uani 1.000000 .
C19 C 1.0918(3) 0.60301(8) 0.5377(3) 0.0640(7) Uani 1.000000 .
C20 C 1.0767(3) 0.80239(8) 0.6684(4) 0.0643(7) Uani 1.000000 .
C21 C 0.3948(3) 0.59232(7) 0.1543(4) 0.0587(7) Uani 1.000000 .
C22 C 1.2277(3) 0.60582(8) 0.6605(4) 0.0669(8) Uani 1.000000 .
C23 C 0.7916(3) 0.49855(7) 0.0726(3) 0.0583(7) Uani 1.000000 .
C24 C 0.8066(4) 0.86860(9) 0.3240(4) 0.0761(9) Uani 1.000000 .
C25 C 1.0104(3) 0.56430(8) 0.5424(3) 0.0649(7) Uani 1.000000 .
C26 C 0.7923(3) 0.82948(9) 0.3142(4) 0.0670(8) Uani 1.000000 .
C27 C 0.4595(3) 0.63156(7) 0.1209(3) 0.0585(7) Uani 1.000000 .
C28 C 0.5659(3) 0.64858(8) 0.2555(3) 0.0624(7) Uani 1.000000 .
C29 C 0.7216(3) 0.70782(8) 0.3505(3) 0.0668(8) Uani 1.000000 .
C30 C 1.3135(4) 0.64351(10) 0.6536(4) 0.0812(9) Uani 1.000000 .
O31 O 1.1304(4) 0.81839(8) 0.7863(4) 0.1362(12) Uani 1.000000 .
C32 C 1.2169(4) 0.74881(11) 0.7656(5) 0.0934(11) Uani 1.000000 .
C33 C 0.9002(4) 0.88587(9) 0.4422(4) 0.0761(9) Uani 1.000000 .
C34 C 1.2110(4) 0.68265(12) 0.6910(5) 0.1032(14) Uani 1.000000 .
C35 C 1.3038(4) 0.71569(13) 0.7150(5) 0.1065(13) Uani 1.000000 .
H23 H 0.8623(3) 0.48150(7) 0.1228(3) 0.0699(8) Uiso 1.000000 R
H8 H 0.8433(3) 0.48984(8) -0.1485(3) 0.0757(9) Uiso 1.000000 R
H12 H 0.6676(3) 0.53187(8) -0.2735(3) 0.0727(8) Uiso 1.000000 R
H13 H 0.5074(3) 0.56632(7) -0.1302(3) 0.0651(7) Uiso 1.000000 R
H26 H 0.7271(3) 0.81866(9) 0.2328(4) 0.0804(9) Uiso 1.000000 R
H24 H 0.7513(4) 0.88391(9) 0.2485(4) 0.0914(10) Uiso 1.000000 R
H33 H 0.9069(4) 0.91260(9) 0.4495(4) 0.0913(10) Uiso 1.000000 R
H14 H 1.0487(3) 0.87431(8) 0.6292(4) 0.0808(9) Uiso 1.000000 R
H7a H 0.6547(3) 0.69037(7) 0.1253(3) 0.0699(8) Uiso 1.000000 R
H7b H 0.5199(3) 0.70546(7) 0.2105(3) 0.0699(8) Uiso 1.000000 R
H10 H 0.6324(3) 0.49302(7) 0.3529(3) 0.0640(7) Uiso 1.000000 R
H11a H 0.6524(3) 0.76345(8) 0.3097(4) 0.0777(9) Uiso 1.000000 R
H11b H 0.7817(3) 0.75136(8) 0.2094(4) 0.0777(9) Uiso 1.000000 R
H17a H 0.9089(3) 0.56290(8) 0.3168(3) 0.0803(9) Uiso 1.000000 R
H17b H 0.8069(3) 0.58204(8) 0.4336(3) 0.0803(9) Uiso 1.000000 R
H19a H 1.0215(3) 0.62359(8) 0.5545(3) 0.0768(9) Uiso 1.000000 R
H19b H 1.1240(3) 0.60656(8) 0.4341(3) 0.0768(9) Uiso 1.000000 R
H21a H 0.3271(3) 0.58416(7) 0.0629(4) 0.0704(8) Uiso 1.000000 R
H21b H 0.3355(3) 0.59469(7) 0.2421(4) 0.0704(8) Uiso 1.000000 R
H22a H 1.1946(3) 0.60320(8) 0.7642(4) 0.0803(9) Uiso 1.000000 R
H22b H 1.2957(3) 0.58458(8) 0.6463(4) 0.0803(9) Uiso 1.000000 R
H25a H 0.9778(3) 0.56085(8) 0.6459(3) 0.0778(9) Uiso 1.000000 R
H25b H 1.0810(3) 0.54373(8) 0.5265(3) 0.0778(9) Uiso 1.000000 R
H27a H 0.5136(3) 0.62939(7) 0.0291(3) 0.0701(8) Uiso 1.000000 R
H27b H 0.3762(3) 0.64937(7) 0.0946(3) 0.0701(8) Uiso 1.000000 R
H28a H 0.6565(3) 0.63280(8) 0.2726(3) 0.0748(8) Uiso 1.000000 R
H28b H 0.5170(3) 0.64789(8) 0.3511(3) 0.0748(8) Uiso 1.000000 R
H29a H 0.6825(3) 0.70593(8) 0.4514(3) 0.0802(9) Uiso 1.000000 R
H29b H 0.8171(3) 0.69401(8) 0.3581(3) 0.0802(9) Uiso 1.000000 R
H30a H 1.4036(4) 0.64254(10) 0.7297(4) 0.0974(11) Uiso 1.000000 R
H30b H 1.3460(4) 0.64618(10) 0.5497(4) 0.0974(11) Uiso 1.000000 R
H32a H 1.2879(4) 0.76847(11) 0.8083(5) 0.1121(14) Uiso 1.000000 R
H32b H 1.1609(4) 0.74037(11) 0.8502(5) 0.1121(14) Uiso 1.000000 R
H34a H 1.1334(4) 0.68711(12) 0.6030(5) 0.1238(16) Uiso 1.000000 R
H34b H 1.1611(4) 0.67800(12) 0.7842(5) 0.1238(16) Uiso 1.000000 R
H35a H 1.3445(4) 0.72212(13) 0.6178(5) 0.1278(15) Uiso 1.000000 R
H35b H 1.3882(4) 0.71024(13) 0.7948(5) 0.1278(15) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.413(3) .
O1 C17 1.438(3) .
O2 C11 1.432(3) .
O2 C16 1.357(3) .
N3 C15 1.360(3) .
N3 C18 1.416(3) .
N3 C21 1.460(3) .
O4 C20 1.316(3) .
O4 C32 1.454(4) .
O5 C15 1.222(3) .
C6 C14 1.396(4) .
C6 C16 1.415(4) .
C6 C20 1.470(4) .
C7 C28 1.515(4) .
C7 C29 1.509(4) .
C8 C12 1.382(4) .
C8 C23 1.389(4) .
C9 C10 1.503(4) .
C9 C18 1.393(3) .
C9 C23 1.375(3) .
C10 C15 1.537(4) .
C11 C29 1.501(4) .
C12 C13 1.379(4) .
C13 C18 1.369(3) .
C14 C33 1.370(4) .
C16 C26 1.406(4) .
C17 C25 1.481(4) .
C19 C22 1.506(4) .
C19 C25 1.527(4) .
C20 O31 1.198(4) .
C21 C27 1.517(4) .
C22 C30 1.518(4) .
C24 C26 1.364(4) .
C24 C33 1.367(5) .
C27 C28 1.518(4) .
C30 C34 1.686(5) .
C32 C35 1.477(5) .
C34 C35 1.413(5) .

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
C17 O1 C10 114.07(18) . .
C16 O2 C11 117.7(2) . .
C18 N3 C15 111.3(2) . .
C21 N3 C15 123.9(2) . .
C21 N3 C18 124.8(2) . .
C32 O4 C20 114.7(3) . .
C16 C6 C14 117.6(3) . .
C20 C6 C14 115.5(2) . .
C20 C6 C16 126.8(2) . .
C29 C7 C28 115.3(2) . .
C23 C8 C12 120.5(2) . .
C18 C9 C10 108.9(2) . .
C23 C9 C10 131.8(2) . .
C23 C9 C18 119.2(2) . .
C9 C10 O1 117.0(2) . .
C15 C10 O1 112.3(2) . .
C15 C10 C9 102.36(19) . .
C29 C11 O2 110.7(2) . .
C13 C12 C8 120.8(3) . .
C18 C13 C12 118.2(3) . .
C33 C14 C6 123.3(3) . .
O5 C15 N3 125.7(3) . .
C10 C15 N3 108.1(2) . .
C10 C15 O5 126.2(3) . .
C6 C16 O2 118.0(2) . .
C26 C16 O2 123.7(2) . .
C26 C16 C6 118.3(2) . .
C25 C17 O1 108.7(2) . .
C9 C18 N3 109.2(2) . .
C13 C18 N3 128.7(2) . .
C13 C18 C9 122.1(2) . .
C25 C19 C22 112.5(2) . .
C6 C20 O4 117.7(3) . .
O31 C20 O4 120.3(3) . .
O31 C20 C6 122.0(3) . .
C27 C21 N3 113.7(2) . .
C30 C22 C19 113.2(3) . .
C9 C23 C8 119.2(3) . .
C33 C24 C26 121.7(3) . .
C19 C25 C17 112.9(2) . .
C24 C26 C16 121.0(3) . .
C28 C27 C21 114.9(2) . .
C27 C28 C7 112.7(2) . .
C11 C29 C7 110.3(3) . .
C34 C30 C22 113.5(3) . .
C35 C32 O4 115.3(3) . .
C24 C33 C14 118.1(3) . .
C35 C34 C30 111.1(3) . .
C34 C35 C32 110.8(3) . .

_database_code_depnum_ccdc_archive 'CCDC 1005105'
#######################################################################
#
#                 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_macrocycle_19a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            macrocycle
_chemical_melting_point          ?
_chemical_formula_moiety         C22H22N2O4
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.42

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.9479(2)
_cell_length_b                   9.0065(2)
_cell_length_c                   14.4450(3)
_cell_angle_alpha                75.8000(10)
_cell_angle_beta                 77.8030(10)
_cell_angle_gamma                72.6440(10)
_cell_volume                     946.06(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21898
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         30.74
_reflns_number_total             5847
_reflns_number_gt                3812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1793P)²+0.0702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5847
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.2239
_refine_ls_wR_factor_gt          0.1785
_refine_ls_goodness_of_fit_ref   0.844
_refine_ls_restrained_S_all      0.844
_refine_ls_shift/su_max          0.139
_refine_ls_shift/su_mean         0.025

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
C13 C -0.3063(3) 0.4669(2) 0.0659(2) 0.0705(6) Uani 1 1 d . . .
H13 H -0.3801 0.5331 0.0221 0.085 Uiso 1 1 calc R . .
O2 O 0.72618(15) 0.91196(18) 0.65110(9) 0.0566(4) Uani 1 1 d . . .
O4 O -0.1475(2) 0.29695(16) -0.11988(10) 0.0707(5) Uani 1 1 d . . .
O3 O 0.2407(3) 0.1613(2) -0.10236(10) 0.0794(5) Uani 1 1 d . . .
C11 C 0.7572(2) 0.8647(2) 0.32531(11) 0.0485(4) Uani 1 1 d . . .
H11A H 0.8200 0.7769 0.2929 0.058 Uiso 1 1 calc R . .
H11B H 0.8070 0.9537 0.2939 0.058 Uiso 1 1 calc R . .
C10 C 0.4397(2) 1.0896(2) 0.68533(12) 0.0509(4) Uani 1 1 d . . .
H10A H 0.4924 1.1749 0.6492 0.061 Uiso 1 1 calc R . .
H10B H 0.4505 1.0756 0.7528 0.061 Uiso 1 1 calc R . .
C9 C 0.5391(2) 0.9405(2) 0.64987(14) 0.0540(4) Uani 1 1 d . . .
H9A H 0.4968 0.8521 0.6908 0.065 Uiso 1 1 calc R . .
H9B H 0.5185 0.9496 0.5846 0.065 Uiso 1 1 calc R . .
C20 C 0.2714(2) 0.0806(2) 0.10018(14) 0.0507(4) Uani 1 1 d . . .
H20A H 0.2918 0.1245 0.1506 0.061 Uiso 1 1 calc R . .
H20B H 0.3794 0.0668 0.0534 0.061 Uiso 1 1 calc R . .
C22 C -0.2355(3) 0.0800(2) -0.14424(14) 0.0531(4) Uani 1 1 d . . .
H22A H -0.1323 0.0674 -0.1942 0.064 Uiso 1 1 calc R . .
H22B H -0.3369 0.1489 -0.1744 0.064 Uiso 1 1 calc R . .
C21 C -0.2026(3) 0.1574(2) -0.07070(14) 0.0651(6) Uani 1 1 d . . .
H21A H -0.3108 0.1848 -0.0256 0.078 Uiso 1 1 calc R . .
H21B H -0.1107 0.0846 -0.0347 0.078 Uiso 1 1 calc R . .
O1 O 0.80908(18) 1.05774(15) 0.44454(11) 0.0587(4) Uani 1 1 d . . .
N2 N 0.12562(17) 0.19345(15) 0.05267(8) 0.0400(3) Uani 1 1 d . . .
C17 C -0.0341(2) 0.27607(17) 0.10077(10) 0.0383(3) Uani 1 1 d . . .
C19 C 0.1237(3) 0.2236(2) -0.04462(11) 0.0498(4) Uani 1 1 d . . .
C12 C -0.1441(2) 0.37179(19) 0.03412(13) 0.0472(4) Uani 1 1 d . . .
C18 C -0.0533(3) 0.3469(2) -0.06510(12) 0.0546(5) Uani 1 1 d . . .
H18 H -0.0261 0.4461 -0.1019 0.065 Uiso 1 1 calc R . .
C16 C -0.0827(3) 0.2705(2) 0.19937(12) 0.0534(4) Uani 1 1 d . . .
H16 H -0.0076 0.2066 0.2432 0.064 Uiso 1 1 calc R . .
C15 C -0.2500(4) 0.3655(3) 0.22942(18) 0.0768(7) Uani 1 1 d . . .
H15 H -0.2889 0.3628 0.2951 0.092 Uiso 1 1 calc R . .
C14 C -0.3585(3) 0.4630(3) 0.1642(3) 0.0847(8) Uani 1 1 d . . .
H14 H -0.4681 0.5270 0.1862 0.102 Uiso 1 1 calc R . .
N1 N 0.78565(15) 0.81909(15) 0.42611(8) 0.0380(3) Uani 1 1 d . . .
C6 C 0.77532(18) 0.67202(18) 0.48669(11) 0.0400(3) Uani 1 1 d . . .
C7 C 0.80906(18) 0.91975(19) 0.47638(11) 0.0401(3) Uani 1 1 d . . .
C1 C 0.79956(19) 0.6711(2) 0.57898(11) 0.0436(4) Uani 1 1 d . . .
C8 C 0.83329(19) 0.8260(2) 0.57947(11) 0.0432(4) Uani 1 1 d . . .
H8 H 0.9585 0.8057 0.5867 0.052 Uiso 1 1 calc R . .
C5 C 0.7464(2) 0.5433(2) 0.46259(16) 0.0574(5) Uani 1 1 d . . .
H5 H 0.7301 0.5457 0.4003 0.069 Uiso 1 1 calc R . .
C2 C 0.7957(2) 0.5373(3) 0.65047(15) 0.0655(6) Uani 1 1 d . . .
H2 H 0.8123 0.5348 0.7127 0.079 Uiso 1 1 calc R . .
C4 C 0.7426(3) 0.4106(2) 0.5349(2) 0.0744(7) Uani 1 1 d . . .
H4 H 0.7234 0.3218 0.5211 0.089 Uiso 1 1 calc R . .
C3 C 0.7669(3) 0.4081(3) 0.6275(2) 0.0807(8) Uani 1 1 d . . .
H3 H 0.7637 0.3177 0.6749 0.097 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 C12 1.375(3) . ?
C13 C14 1.388(4) . ?
O2 C8 1.4223(19) . ?
O2 C9 1.4344(19) . ?
O4 C18 1.4192(19) . ?
O4 C21 1.427(2) . ?
O3 C19 1.210(2) . ?
C11 N1 1.4597(19) . ?
C11 C10 1.526(2) 2_676 ?
C10 C9 1.492(3) . ?
C10 C11 1.526(2) 2_676 ?
C20 N2 1.462(2) . ?
C20 C22 1.516(2) 2 ?
C22 C21 1.507(2) . ?
C22 C20 1.516(2) 2 ?
O1 C7 1.2149(19) . ?
N2 C19 1.3667(19) . ?
N2 C17 1.402(2) . ?
C17 C12 1.390(2) . ?
C17 C16 1.387(2) . ?
C19 C18 1.544(3) . ?
C12 C18 1.500(3) . ?
C16 C15 1.396(3) . ?
C15 C14 1.373(4) . ?
N1 C7 1.3654(19) . ?
N1 C6 1.412(2) . ?
C6 C5 1.382(2) . ?
C6 C1 1.384(2) . ?
C7 C8 1.541(2) . ?
C1 C2 1.384(2) . ?
C1 C8 1.499(2) . ?
C5 C4 1.384(3) . ?
C2 C3 1.378(4) . ?
C4 C3 1.385(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
C12 C13 C14 119.2(2) . . ?
C8 O2 C9 112.39(12) . . ?
C18 O4 C21 113.17(12) . . ?
N1 C11 C10 112.54(12) . 2_676 ?
C9 C10 C11 111.78(15) . 2_676 ?
O2 C9 C10 109.75(15) . . ?
N2 C20 C22 113.24(13) . 2 ?
C21 C22 C20 112.55(15) . 2 ?
O4 C21 C22 108.72(15) . . ?
C19 N2 C17 111.33(14) . . ?
C19 N2 C20 123.72(15) . . ?
C17 N2 C20 124.82(13) . . ?
C12 C17 C16 122.44(17) . . ?
C12 C17 N2 109.89(14) . . ?
C16 C17 N2 127.67(16) . . ?
O3 C19 N2 125.0(2) . . ?
O3 C19 C18 127.49(16) . . ?
N2 C19 C18 107.53(14) . . ?
C13 C12 C17 119.46(18) . . ?
C13 C12 C18 131.87(18) . . ?
C17 C12 C18 108.67(15) . . ?
O4 C18 C12 116.68(17) . . ?
O4 C18 C19 112.20(15) . . ?
C12 C18 C19 102.48(12) . . ?
C15 C16 C17 116.6(2) . . ?
C14 C15 C16 121.5(2) . . ?
C15 C14 C13 120.7(2) . . ?
C7 N1 C6 111.16(13) . . ?
C7 N1 C11 123.79(14) . . ?
C6 N1 C11 124.78(14) . . ?
C5 C6 C1 122.29(17) . . ?
C5 C6 N1 127.85(16) . . ?
C1 C6 N1 109.86(14) . . ?
O1 C7 N1 125.48(15) . . ?
O1 C7 C8 127.23(14) . . ?
N1 C7 C8 107.28(13) . . ?
C2 C1 C6 119.71(18) . . ?
C2 C1 C8 131.70(17) . . ?
C6 C1 C8 108.56(13) . . ?
O2 C8 C1 117.37(13) . . ?
O2 C8 C7 112.09(13) . . ?
C1 C8 C7 102.78(12) . . ?
C6 C5 C4 117.3(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C4 C5 120.9(2) . . ?
C2 C3 C4 121.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.74
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 1005106'
