# 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_mo_130319lt_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3aa
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   11.2184(5)
_cell_length_b                   11.0939(5)
_cell_length_c                   15.1186(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1300(10)
_cell_angle_gamma                90.00
_cell_volume                     1832.41(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4573
_cell_measurement_theta_min      2.7548
_cell_measurement_theta_max      26.4120

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8897
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14922
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         26.42
_reflns_number_total             3747
_reflns_number_gt                3079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.8975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3747
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30391(9) 0.74232(11) 0.94203(8) 0.0311(3) Uani 1 1 d . . .
O2 O 0.91866(8) 0.81941(9) 0.94170(6) 0.0183(2) Uani 1 1 d . . .
O3 O 1.00387(9) 0.63044(9) 1.06129(6) 0.0221(2) Uani 1 1 d . . .
N1 N 0.42309(11) 0.70810(12) 0.98610(9) 0.0244(3) Uani 1 1 d . . .
C1 C 0.22566(14) 0.72322(15) 1.00370(12) 0.0316(4) Uani 1 1 d . . .
H1A H 0.2323 0.6392 1.0243 0.047 Uiso 1 1 calc R . .
H1B H 0.1407 0.7405 0.9728 0.047 Uiso 1 1 calc R . .
H1C H 0.2504 0.7769 1.0562 0.047 Uiso 1 1 calc R . .
C2 C 0.49820(13) 0.73835(13) 0.93737(10) 0.0220(3) Uani 1 1 d . . .
H2 H 0.4699 0.7790 0.8812 0.026 Uiso 1 1 calc R . .
C3 C 0.62785(13) 0.70935(13) 0.96968(9) 0.0184(3) Uani 1 1 d . . .
C4 C 0.72089(12) 0.77594(13) 0.94159(9) 0.0174(3) Uani 1 1 d . . .
C5 C 0.72350(12) 0.88098(12) 0.88513(9) 0.0175(3) Uani 1 1 d . . .
C6 C 0.84410(13) 0.90366(13) 0.88812(9) 0.0174(3) Uani 1 1 d . . .
C7 C 0.91029(13) 0.99743(12) 0.85035(9) 0.0186(3) Uani 1 1 d . . .
C8 C 1.03811(13) 1.00201(14) 0.87567(9) 0.0215(3) Uani 1 1 d . . .
H8 H 1.0816 0.9440 0.9169 0.026 Uiso 1 1 calc R . .
C9 C 1.10204(14) 1.09082(14) 0.84092(10) 0.0246(3) Uani 1 1 d . . .
H9 H 1.1889 1.0929 0.8584 0.030 Uiso 1 1 calc R . .
C10 C 1.04003(14) 1.17636(14) 0.78097(10) 0.0246(3) Uani 1 1 d . . .
H10 H 1.0842 1.2366 0.7572 0.030 Uiso 1 1 calc R . .
C11 C 0.66699(13) 0.61492(13) 1.02997(9) 0.0211(3) Uani 1 1 d . . .
H11 H 0.6069 0.5683 1.0497 0.025 Uiso 1 1 calc R . .
C12 C 0.78995(13) 0.58535(13) 1.06286(9) 0.0205(3) Uani 1 1 d . . .
H12 H 0.8114 0.5208 1.1047 0.025 Uiso 1 1 calc R . .
C13 C 0.88140(13) 0.64945(13) 1.03502(9) 0.0191(3) Uani 1 1 d . . .
C14 C 0.84237(13) 0.74369(12) 0.97419(9) 0.0175(3) Uani 1 1 d . . .
C15 C 0.61394(12) 0.94895(13) 0.83679(9) 0.0178(3) Uani 1 1 d . . .
C16 C 0.55958(13) 0.92360(13) 0.74610(9) 0.0222(3) Uani 1 1 d . . .
H16 H 0.5953 0.8651 0.7141 0.027 Uiso 1 1 calc R . .
C17 C 0.45377(14) 0.98319(14) 0.70234(10) 0.0262(3) Uani 1 1 d . . .
H17 H 0.4173 0.9655 0.6406 0.031 Uiso 1 1 calc R . .
C18 C 0.40127(14) 1.06867(14) 0.74876(10) 0.0264(3) Uani 1 1 d . . .
H18 H 0.3289 1.1095 0.7188 0.032 Uiso 1 1 calc R . .
C19 C 0.45450(13) 1.09447(14) 0.83890(10) 0.0250(3) Uani 1 1 d . . .
H19 H 0.4186 1.1532 0.8706 0.030 Uiso 1 1 calc R . .
C20 C 0.56003(13) 1.03465(13) 0.88287(10) 0.0206(3) Uani 1 1 d . . .
H20 H 0.5958 1.0522 0.9447 0.025 Uiso 1 1 calc R . .
C21 C 0.91307(14) 1.17354(13) 0.75580(10) 0.0242(3) Uani 1 1 d . . .
H21 H 0.8703 1.2326 0.7152 0.029 Uiso 1 1 calc R . .
C22 C 0.84832(13) 1.08480(13) 0.78980(9) 0.0209(3) Uani 1 1 d . . .
H22 H 0.7615 1.0832 0.7719 0.025 Uiso 1 1 calc R . .
C23 C 1.04326(14) 0.53997(14) 1.12954(10) 0.0245(3) Uani 1 1 d . . .
H23A H 1.0116 0.5591 1.1832 0.037 Uiso 1 1 calc R . .
H23B H 1.1329 0.5379 1.1464 0.037 Uiso 1 1 calc R . .
H23C H 1.0121 0.4611 1.1056 0.037 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4039(16) . ?
O1 C1 1.4341(18) . ?
O2 C14 1.3675(16) . ?
O2 C6 1.3863(16) . ?
O3 C13 1.3572(17) . ?
O3 C23 1.4353(17) . ?
N1 C2 1.2836(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.461(2) . ?
C2 H2 0.9500 . ?
C3 C11 1.393(2) . ?
C3 C4 1.4202(19) . ?
C4 C14 1.387(2) . ?
C4 C5 1.4487(19) . ?
C5 C6 1.3667(19) . ?
C5 C15 1.4850(19) . ?
C6 C7 1.4671(19) . ?
C7 C8 1.399(2) . ?
C7 C22 1.404(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C21 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3898(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C15 C20 1.3952(19) . ?
C15 C16 1.3968(19) . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
N1 O1 C1 108.01(11) . . ?
C14 O2 C6 106.27(10) . . ?
C13 O3 C23 116.42(11) . . ?
C2 N1 O1 109.60(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 118.95(13) . . ?
N1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C11 C3 C4 116.30(13) . . ?
C11 C3 C2 121.76(12) . . ?
C4 C3 C2 121.94(13) . . ?
C14 C4 C3 119.30(13) . . ?
C14 C4 C5 105.49(12) . . ?
C3 C4 C5 135.17(13) . . ?
C6 C5 C4 106.32(12) . . ?
C6 C5 C15 128.70(13) . . ?
C4 C5 C15 124.97(12) . . ?
C5 C6 O2 110.89(12) . . ?
C5 C6 C7 134.62(13) . . ?
O2 C6 C7 114.46(12) . . ?
C8 C7 C22 118.58(13) . . ?
C8 C7 C6 119.83(13) . . ?
C22 C7 C6 121.59(13) . . ?
C9 C8 C7 120.48(14) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.48(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C21 119.68(14) . . ?
C9 C10 H10 120.2 . . ?
C21 C10 H10 120.2 . . ?
C3 C11 C12 123.33(13) . . ?
C3 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C13 C12 C11 120.65(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O3 C13 C12 126.85(13) . . ?
O3 C13 C14 117.03(12) . . ?
C12 C13 C14 116.12(13) . . ?
O2 C14 C4 111.02(12) . . ?
O2 C14 C13 124.65(12) . . ?
C4 C14 C13 124.28(12) . . ?
C20 C15 C16 119.02(13) . . ?
C20 C15 C5 120.30(12) . . ?
C16 C15 C5 120.59(12) . . ?
C17 C16 C15 120.49(13) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.97(14) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.01(14) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.11(14) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.40(13) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C10 C21 C22 120.29(14) . . ?
C10 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C7 120.48(14) . . ?
C21 C22 H22 119.8 . . ?
C7 C22 H22 119.8 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1016939'
#######################################################################
#
#                 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_130931lt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Br N O2'
_chemical_formula_weight         406.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   17.3636(16)
_cell_length_b                   10.3459(9)
_cell_length_c                   9.9494(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.111(2)
_cell_angle_gamma                90.00
_cell_volume                     1786.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4651
_cell_measurement_theta_min      2.8414
_cell_measurement_theta_max      26.2192

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    2.317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7854
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14119
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         26.42
_reflns_number_total             3664
_reflns_number_gt                3021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3664
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.422874(12) 0.52683(2) 0.30604(2) 0.02432(9) Uani 1 1 d . . .
O1 O 0.41059(9) 1.18129(15) 0.35423(16) 0.0251(4) Uani 1 1 d . . .
O2 O 0.22143(8) 0.72068(15) -0.05069(14) 0.0211(3) Uani 1 1 d . . .
N1 N 0.39642(11) 1.04807(18) 0.33981(19) 0.0222(4) Uani 1 1 d . . .
C1 C 0.45212(15) 1.2012(3) 0.4794(2) 0.0317(6) Uani 1 1 d . . .
H1A H 0.4191 1.1790 0.5538 0.048 Uiso 1 1 calc R . .
H1B H 0.4676 1.2921 0.4870 0.048 Uiso 1 1 calc R . .
H1C H 0.4981 1.1463 0.4832 0.048 Uiso 1 1 calc R . .
C2 C 0.35843(12) 1.0253(2) 0.2300(2) 0.0204(5) Uani 1 1 d . . .
H2 H 0.3414 1.0947 0.1739 0.025 Uiso 1 1 calc R . .
C3 C 0.34141(12) 0.8920(2) 0.1910(2) 0.0188(5) Uani 1 1 d . . .
C4 C 0.28569(12) 0.8615(2) 0.0881(2) 0.0177(5) Uani 1 1 d . . .
C5 C 0.22972(12) 0.9328(2) 0.0068(2) 0.0180(5) Uani 1 1 d . . .
C6 C 0.19309(12) 0.8445(2) -0.0744(2) 0.0198(5) Uani 1 1 d . . .
C7 C 0.13059(12) 0.8510(2) -0.1775(2) 0.0192(5) Uani 1 1 d . . .
C8 C 0.11608(13) 0.7446(2) -0.2611(2) 0.0241(5) Uani 1 1 d . . .
H8 H 0.1465 0.6687 -0.2503 0.029 Uiso 1 1 calc R . .
C9 C 0.05752(13) 0.7489(2) -0.3599(2) 0.0267(5) Uani 1 1 d . . .
H9 H 0.0481 0.6759 -0.4159 0.032 Uiso 1 1 calc R . .
C10 C 0.01289(13) 0.8587(2) -0.3772(2) 0.0255(5) Uani 1 1 d . . .
H10 H -0.0268 0.8617 -0.4455 0.031 Uiso 1 1 calc R . .
C11 C 0.27697(12) 0.7321(2) 0.0503(2) 0.0199(5) Uani 1 1 d . . .
C12 C 0.21211(12) 1.0735(2) 0.0203(2) 0.0174(5) Uani 1 1 d . . .
C13 C 0.16008(13) 1.1126(2) 0.1164(2) 0.0229(5) Uani 1 1 d . . .
H13 H 0.1357 1.0497 0.1698 0.027 Uiso 1 1 calc R . .
C14 C 0.14373(13) 1.2425(2) 0.1343(2) 0.0248(5) Uani 1 1 d . . .
H14 H 0.1085 1.2681 0.2000 0.030 Uiso 1 1 calc R . .
C15 C 0.17863(12) 1.3346(2) 0.0567(2) 0.0228(5) Uani 1 1 d . . .
H15 H 0.1676 1.4236 0.0690 0.027 Uiso 1 1 calc R . .
C16 C 0.22961(13) 1.2967(2) -0.0389(2) 0.0251(5) Uani 1 1 d . . .
H16 H 0.2535 1.3601 -0.0924 0.030 Uiso 1 1 calc R . .
C17 C 0.24629(13) 1.1667(2) -0.0577(2) 0.0238(5) Uani 1 1 d . . .
H17 H 0.2812 1.1417 -0.1243 0.029 Uiso 1 1 calc R . .
C18 C 0.08487(13) 0.9615(2) -0.1949(2) 0.0224(5) Uani 1 1 d . . .
H18 H 0.0938 1.0347 -0.1387 0.027 Uiso 1 1 calc R . .
C19 C 0.02643(13) 0.9645(2) -0.2941(2) 0.0242(5) Uani 1 1 d . . .
H19 H -0.0045 1.0398 -0.3052 0.029 Uiso 1 1 calc R . .
C20 C 0.31589(12) 0.6296(2) 0.1093(2) 0.0213(5) Uani 1 1 d . . .
H20 H 0.3080 0.5428 0.0806 0.026 Uiso 1 1 calc R . .
C21 C 0.36728(12) 0.6623(2) 0.2133(2) 0.0208(5) Uani 1 1 d . . .
C22 C 0.38130(12) 0.7897(2) 0.2524(2) 0.0205(5) Uani 1 1 d . . .
H22 H 0.4187 0.8072 0.3222 0.025 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
Br1 C21 1.919(2) . ?
O1 N1 1.407(2) . ?
O1 C1 1.431(3) . ?
O2 C11 1.372(2) . ?
O2 C6 1.389(3) . ?
N1 C2 1.277(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.460(3) . ?
C2 H2 0.9500 . ?
C3 C22 1.393(3) . ?
C3 C4 1.418(3) . ?
C4 C11 1.397(3) . ?
C4 C5 1.444(3) . ?
C5 C6 1.362(3) . ?
C5 C12 1.494(3) . ?
C6 C7 1.468(3) . ?
C7 C8 1.397(3) . ?
C7 C18 1.399(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C19 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C20 1.377(3) . ?
C12 C17 1.385(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C1 108.10(17) . . ?
C11 O2 C6 106.24(16) . . ?
C2 N1 O1 110.54(18) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.6(2) . . ?
N1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C22 C3 C4 117.6(2) . . ?
C22 C3 C2 120.56(19) . . ?
C4 C3 C2 121.9(2) . . ?
C11 C4 C3 118.2(2) . . ?
C11 C4 C5 105.98(18) . . ?
C3 C4 C5 135.8(2) . . ?
C6 C5 C4 106.2(2) . . ?
C6 C5 C12 127.91(19) . . ?
C4 C5 C12 125.69(18) . . ?
C5 C6 O2 111.31(18) . . ?
C5 C6 C7 134.5(2) . . ?
O2 C6 C7 114.16(18) . . ?
C8 C7 C18 118.8(2) . . ?
C8 C7 C6 119.5(2) . . ?
C18 C7 C6 121.71(19) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C19 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
C19 C10 H10 120.2 . . ?
O2 C11 C20 124.5(2) . . ?
O2 C11 C4 110.24(19) . . ?
C20 C11 C4 125.2(2) . . ?
C17 C12 C13 118.8(2) . . ?
C17 C12 C5 122.3(2) . . ?
C13 C12 C5 118.9(2) . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.2(2) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C7 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C7 C18 H18 119.9 . . ?
C10 C19 C18 120.6(2) . . ?
C10 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C11 C20 C21 115.0(2) . . ?
C11 C20 H20 122.5 . . ?
C21 C20 H20 122.5 . . ?
C20 C21 C22 122.8(2) . . ?
C20 C21 Br1 118.68(17) . . ?
C22 C21 Br1 118.49(16) . . ?
C3 C22 C21 121.11(19) . . ?
C3 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 1016940'
#######################################################################
#
#                 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_130940lt_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H30 N2 O4'
_chemical_formula_weight         650.70

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_hall  '-C 2yc'

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

_cell_length_a                   25.919(3)
_cell_length_b                   11.2554(14)
_cell_length_c                   11.6261(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.271(2)
_cell_angle_gamma                90.00
_cell_volume                     3326.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2150
_cell_measurement_theta_min      2.5589
_cell_measurement_theta_max      26.3069

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8035
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13500
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.48
_reflns_number_total             3428
_reflns_number_gt                2535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0707P)²+2.5441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3428
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18654(5) 0.14585(12) 0.39458(11) 0.0235(3) Uani 1 1 d . . .
O2 O 0.01972(5) 0.36779(13) -0.01938(12) 0.0292(3) Uani 1 1 d . . .
N1 N 0.04993(7) 0.33383(14) 0.08710(14) 0.0246(4) Uani 1 1 d . . .
C1 C 0.33602(8) -0.01766(18) 0.23811(19) 0.0306(5) Uani 1 1 d . . .
H1A H 0.3685 -0.0529 0.2308 0.037 Uiso 1 1 calc R . .
C2 C 0.33382(8) 0.0607(2) 0.3282(2) 0.0315(5) Uani 1 1 d . . .
H2 H 0.3650 0.0797 0.3831 0.038 Uiso 1 1 calc R . .
C3 C 0.28641(8) 0.11195(19) 0.33915(18) 0.0275(5) Uani 1 1 d . . .
H3 H 0.2854 0.1663 0.4012 0.033 Uiso 1 1 calc R . .
C4 C 0.24027(7) 0.08461(17) 0.26006(17) 0.0225(4) Uani 1 1 d . . .
C5 C 0.18985(8) 0.13414(17) 0.27720(16) 0.0223(4) Uani 1 1 d . . .
C6 C 0.14451(7) 0.16692(17) 0.20494(17) 0.0211(4) Uani 1 1 d . . .
C7 C 0.10851(7) 0.20061(16) 0.28064(16) 0.0201(4) Uani 1 1 d . . .
C8 C 0.05582(7) 0.23930(16) 0.26691(16) 0.0189(4) Uani 1 1 d . . .
C9 C 0.02364(7) 0.27610(15) 0.15294(16) 0.0192(4) Uani 1 1 d . . .
C10 C 0.03298(7) 0.24679(16) 0.36724(16) 0.0200(4) Uani 1 1 d . . .
C11 C 0.24273(8) 0.00561(18) 0.16865(18) 0.0289(5) Uani 1 1 d . . .
H11 H 0.2117 -0.0138 0.1136 0.035 Uiso 1 1 calc R . .
C12 C 0.29052(9) -0.0445(2) 0.1584(2) 0.0337(5) Uani 1 1 d . . .
H12 H 0.2920 -0.0980 0.0959 0.040 Uiso 1 1 calc R . .
C13 C 0.13645(7) 0.18293(16) 0.39496(17) 0.0215(4) Uani 1 1 d . . .
C14 C 0.13485(8) 0.16077(17) 0.07512(17) 0.0241(4) Uani 1 1 d . . .
C15 C 0.16991(9) 0.2135(2) 0.0131(2) 0.0360(5) Uani 1 1 d . . .
H15 H 0.1992 0.2574 0.0539 0.043 Uiso 1 1 calc R . .
C16 C 0.16204(11) 0.2020(2) -0.1077(2) 0.0481(7) Uani 1 1 d . . .
H16 H 0.1861 0.2373 -0.1495 0.058 Uiso 1 1 calc R . .
C17 C 0.11947(12) 0.1395(3) -0.1674(2) 0.0489(7) Uani 1 1 d . . .
H17 H 0.1145 0.1312 -0.2501 0.059 Uiso 1 1 calc R . .
C18 C 0.08392(10) 0.0887(2) -0.1074(2) 0.0403(6) Uani 1 1 d . . .
H18 H 0.0541 0.0472 -0.1490 0.048 Uiso 1 1 calc R . .
C19 C 0.09185(8) 0.09852(18) 0.01391(18) 0.0276(5) Uani 1 1 d . . .
H19 H 0.0678 0.0625 0.0552 0.033 Uiso 1 1 calc R . .
C20 C 0.06325(7) 0.22518(17) 0.48014(17) 0.0222(4) Uani 1 1 d . . .
H20 H 0.0473 0.2316 0.5468 0.027 Uiso 1 1 calc R . .
C21 C 0.11574(8) 0.19481(17) 0.49500(17) 0.0233(4) Uani 1 1 d . . .
H21 H 0.1367 0.1826 0.5708 0.028 Uiso 1 1 calc R . .
C22 C 0.05308(9) 0.4305(2) -0.08402(19) 0.0328(5) Uani 1 1 d . . .
H22A H 0.0653 0.5045 -0.0431 0.049 Uiso 1 1 calc R . .
H22B H 0.0333 0.4490 -0.1627 0.049 Uiso 1 1 calc R . .
H22C H 0.0835 0.3809 -0.0903 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.365(2) . ?
O1 C5 1.390(2) . ?
O2 N1 1.383(2) . ?
O2 C22 1.437(2) . ?
N1 C9 1.295(2) . ?
C1 C2 1.380(3) . ?
C1 C12 1.383(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C11 1.397(3) . ?
C4 C5 1.470(3) . ?
C5 C6 1.355(3) . ?
C6 C7 1.453(3) . ?
C6 C14 1.482(3) . ?
C7 C13 1.398(3) . ?
C7 C8 1.412(3) . ?
C8 C10 1.410(3) . ?
C8 C9 1.480(3) . ?
C9 C10 1.478(3) 2 ?
C10 C20 1.412(3) . ?
C10 C9 1.477(3) 2 ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C21 1.379(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C13 O1 C5 105.86(14) . . ?
N1 O2 C22 108.10(15) . . ?
C9 N1 O2 113.36(16) . . ?
C2 C1 C12 119.48(19) . . ?
C2 C1 H1A 120.3 . . ?
C12 C1 H1A 120.3 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.67(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C11 118.81(18) . . ?
C3 C4 C5 119.88(18) . . ?
C11 C4 C5 121.25(18) . . ?
C6 C5 O1 111.74(16) . . ?
C6 C5 C4 134.86(18) . . ?
O1 C5 C4 113.33(16) . . ?
C5 C6 C7 106.10(16) . . ?
C5 C6 C14 124.87(17) . . ?
C7 C6 C14 128.93(17) . . ?
C13 C7 C8 117.46(17) . . ?
C13 C7 C6 105.32(16) . . ?
C8 C7 C6 137.17(18) . . ?
C10 C8 C7 118.55(17) . . ?
C10 C8 C9 118.01(16) . . ?
C7 C8 C9 123.41(16) . . ?
N1 C9 C10 129.75(17) . 2 ?
N1 C9 C8 113.57(16) . . ?
C10 C9 C8 116.62(15) 2 . ?
C8 C10 C20 120.79(17) . . ?
C8 C10 C9 116.52(16) . 2 ?
C20 C10 C9 122.69(16) . 2 ?
C12 C11 C4 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C4 C11 H11 120.0 . . ?
C1 C12 C11 120.8(2) . . ?
C1 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O1 C13 C21 124.03(17) . . ?
O1 C13 C7 110.91(16) . . ?
C21 C13 C7 124.98(18) . . ?
C19 C14 C15 119.2(2) . . ?
C19 C14 C6 120.27(17) . . ?
C15 C14 C6 120.51(19) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C21 C20 C10 120.91(17) . . ?
C21 C20 H20 119.5 . . ?
C10 C20 H20 119.5 . . ?
C13 C21 C20 117.06(18) . . ?
C13 C21 H21 121.5 . . ?
C20 C21 H21 121.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 1016941'
