# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_084mgl11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 Cl N6 O'
_chemical_formula_sum            'C28 H25 Cl N6 O'
_chemical_formula_weight         496.99

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_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                   9.6249(18)
_cell_length_b                   9.9872(19)
_cell_length_c                   26.390(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.252(3)
_cell_angle_gamma                90.00
_cell_volume                     2534.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    278(2)
_cell_measurement_reflns_used    2018
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      19.57

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    .
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   'SHELXTL V 6.12 (Sheldrick, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      278(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 AXS CCD area detector 01-670'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            20525
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_sigmaI/netI    0.1453
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.40
_reflns_number_total             4659
_reflns_number_gt                1494
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_solved_by                       'Simon Hernandez-Ortega'

_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^)+(0.0005P)^2^+0.0000P] 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         4659
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1875
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0581
_refine_ls_wR_factor_gt          0.0416
_refine_ls_goodness_of_fit_ref   0.736
_refine_ls_restrained_S_all      0.736
_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 0.5236(2) 0.6513(2) 0.71988(9) 0.0844(9) Uani 1 1 d . . .
Cl Cl 1.02306(10) 0.75227(12) 0.49323(4) 0.1172(4) Uani 1 1 d . . .
N1 N 0.8650(3) 0.7427(3) 0.82907(10) 0.0677(9) Uani 1 1 d D . .
H1 H 0.828(3) 0.685(2) 0.8506(9) 0.081 Uiso 1 1 d D . .
C2 C 0.7919(4) 0.8028(3) 0.78908(13) 0.0585(10) Uani 1 1 d . . .
C3 C 0.8813(4) 0.8750(3) 0.76150(12) 0.0544(10) Uani 1 1 d . . .
C4 C 1.1461(4) 0.9172(3) 0.77635(13) 0.0702(11) Uani 1 1 d . . .
H4 H 1.1576 0.9741 0.7489 0.084 Uiso 1 1 calc R . .
C5 C 1.2557(4) 0.8851(4) 0.80866(16) 0.0847(13) Uani 1 1 d . . .
H5 H 1.3431 0.9194 0.8023 0.102 Uiso 1 1 calc R . .
C6 C 1.2411(4) 0.8030(4) 0.85064(16) 0.0859(14) Uani 1 1 d . . .
H6 H 1.3178 0.7854 0.8721 0.103 Uiso 1 1 calc R . .
C7 C 1.1152(4) 0.7478(4) 0.86074(13) 0.0767(12) Uani 1 1 d . . .
H7 H 1.1051 0.6916 0.8885 0.092 Uiso 1 1 calc R . .
C8 C 1.0022(4) 0.7785(4) 0.82799(14) 0.0593(10) Uani 1 1 d . . .
C9 C 1.0161(4) 0.8618(4) 0.78585(13) 0.0568(10) Uani 1 1 d . . .
C10 C 0.6364(3) 0.7862(3) 0.78340(11) 0.0708(11) Uani 1 1 d . . .
H10A H 0.5921 0.8680 0.7942 0.085 Uiso 1 1 calc R . .
H10B H 0.6079 0.7147 0.8056 0.085 Uiso 1 1 calc R . .
C11 C 0.5857(3) 0.7542(4) 0.72960(14) 0.0600(11) Uani 1 1 d . . .
N12 N 0.6146(3) 0.8466(3) 0.69389(11) 0.0544(8) Uani 1 1 d . . .
C13 C 0.6909(3) 0.9728(3) 0.70458(11) 0.0608(10) Uani 1 1 d . . .
H13A H 0.6506 1.0161 0.7334 0.073 Uiso 1 1 calc R . .
H13B H 0.6776 1.0319 0.6756 0.073 Uiso 1 1 calc R . .
C14 C 0.8453(3) 0.9557(3) 0.71562(11) 0.0676(10) Uani 1 1 d . . .
H14A H 0.8859 0.9135 0.6866 0.081 Uiso 1 1 calc R . .
H14B H 0.8872 1.0436 0.7196 0.081 Uiso 1 1 calc R . .
C15 C 0.5705(3) 0.8157(3) 0.64148(12) 0.0586(10) Uani 1 1 d . . .
H15 H 0.5305 0.7255 0.6423 0.070 Uiso 1 1 calc R . .
C16 C 0.6899(3) 0.8076(4) 0.60571(13) 0.0549(10) Uani 1 1 d . . .
C17 C 0.7620(4) 0.6891(4) 0.60272(13) 0.0731(11) Uani 1 1 d . . .
H17 H 0.7394 0.6188 0.6240 0.088 Uiso 1 1 calc R . .
C18 C 0.8663(4) 0.6716(4) 0.56924(15) 0.0844(13) Uani 1 1 d . . .
H18 H 0.9141 0.5908 0.5679 0.101 Uiso 1 1 calc R . .
C19 C 0.8986(4) 0.7762(5) 0.53778(14) 0.0734(12) Uani 1 1 d . . .
C20 C 0.8309(4) 0.8943(4) 0.54066(14) 0.0832(13) Uani 1 1 d . . .
H20 H 0.8547 0.9649 0.5197 0.100 Uiso 1 1 calc R . .
C21 C 0.7264(4) 0.9109(4) 0.57459(14) 0.0733(12) Uani 1 1 d . . .
H21 H 0.6805 0.9926 0.5763 0.088 Uiso 1 1 calc R . .
C23 C 0.3136(4) 0.7240(4) 0.58027(16) 0.0621(10) Uani 1 1 d . . .
C24 C 0.2399(4) 0.6493(5) 0.61402(16) 0.0776(12) Uani 1 1 d . . .
C25 C 0.2154(5) 0.5176(5) 0.60131(19) 0.1070(17) Uani 1 1 d . . .
H25 H 0.1671 0.4635 0.6232 0.128 Uiso 1 1 calc R . .
C26 C 0.2605(5) 0.4648(5) 0.5572(2) 0.1179(19) Uani 1 1 d . . .
H26 H 0.2437 0.3751 0.5497 0.141 Uiso 1 1 calc R . .
C27 C 0.3310(4) 0.5433(5) 0.52346(16) 0.0986(15) Uani 1 1 d . . .
H27 H 0.3594 0.5066 0.4932 0.118 Uiso 1 1 calc R . .
C28 C 0.3595(4) 0.6761(4) 0.53456(16) 0.0720(12) Uani 1 1 d . . .
N29 N 0.3461(3) 0.8602(3) 0.59386(10) 0.0599(8) Uani 1 1 d . . .
N30 N 0.2600(3) 0.9632(4) 0.58224(11) 0.0761(10) Uani 1 1 d . . .
N31 N 0.3186(4) 1.0690(3) 0.60158(12) 0.0881(11) Uani 1 1 d . . .
N32 N 0.4413(3) 1.0373(3) 0.62669(11) 0.0773(10) Uani 1 1 d . . .
C33 C 0.4548(4) 0.9062(4) 0.62185(13) 0.0570(10) Uani 1 1 d . . .
C34 C 0.1879(3) 0.7082(4) 0.66254(13) 0.1062(15) Uani 1 1 d . . .
H34A H 0.2647 0.7203 0.6864 0.159 Uiso 1 1 calc R . .
H34B H 0.1213 0.6486 0.6766 0.159 Uiso 1 1 calc R . .
H34C H 0.1447 0.7932 0.6554 0.159 Uiso 1 1 calc R . .
C35 C 0.4325(3) 0.7632(3) 0.49748(11) 0.0913(13) Uani 1 1 d . . .
H35A H 0.5247 0.7831 0.5106 0.137 Uiso 1 1 calc R . .
H35B H 0.3816 0.8451 0.4924 0.137 Uiso 1 1 calc R . .
H35C H 0.4380 0.7171 0.4657 0.137 Uiso 1 1 calc R . .

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 0.080(2) 0.083(2) 0.090(2) 0.0160(17) 0.0028(15) -0.0296(16)
Cl 0.0820(8) 0.1723(12) 0.0993(8) -0.0207(8) 0.0275(6) -0.0097(8)
N1 0.077(2) 0.074(3) 0.052(2) 0.0145(18) 0.0065(19) 0.006(2)
C2 0.055(3) 0.073(3) 0.047(2) 0.011(2) 0.000(2) 0.006(2)
C3 0.056(3) 0.063(3) 0.045(2) 0.011(2) 0.004(2) 0.000(2)
C4 0.062(3) 0.076(3) 0.072(3) -0.009(2) 0.001(2) 0.003(3)
C5 0.059(3) 0.100(4) 0.095(4) -0.024(3) -0.005(3) 0.005(3)
C6 0.073(3) 0.088(4) 0.094(4) -0.024(3) -0.027(3) 0.019(3)
C7 0.086(3) 0.073(3) 0.069(3) -0.012(2) -0.020(3) 0.027(3)
C8 0.058(3) 0.061(3) 0.059(3) -0.006(2) 0.006(2) 0.012(2)
C9 0.054(3) 0.064(3) 0.053(3) -0.005(2) 0.006(2) 0.005(2)
C10 0.065(3) 0.092(3) 0.056(3) 0.017(2) 0.005(2) -0.002(2)
C11 0.050(3) 0.072(3) 0.058(3) 0.015(3) 0.006(2) 0.000(2)
N12 0.0557(19) 0.055(2) 0.053(2) 0.0024(18) -0.0019(17) -0.0020(17)
C13 0.072(3) 0.060(3) 0.050(2) 0.006(2) -0.002(2) -0.001(2)
C14 0.064(3) 0.075(3) 0.064(3) 0.009(2) 0.001(2) -0.007(2)
C15 0.064(3) 0.057(3) 0.055(2) 0.002(2) 0.000(2) -0.002(2)
C16 0.059(3) 0.055(3) 0.051(2) 0.004(2) -0.003(2) 0.004(2)
C17 0.084(3) 0.063(3) 0.073(3) 0.008(2) 0.009(2) 0.014(2)
C18 0.077(3) 0.083(4) 0.094(4) -0.003(3) 0.012(3) 0.014(3)
C19 0.056(3) 0.101(4) 0.063(3) -0.004(3) 0.006(2) -0.003(3)
C20 0.081(3) 0.093(4) 0.076(3) 0.014(3) 0.003(3) -0.009(3)
C21 0.072(3) 0.067(3) 0.082(3) 0.009(3) 0.010(2) 0.008(2)
C23 0.068(3) 0.052(3) 0.065(3) -0.001(3) -0.010(2) 0.003(2)
C24 0.074(3) 0.081(4) 0.076(3) 0.007(3) -0.014(3) -0.016(3)
C25 0.100(4) 0.096(5) 0.124(5) 0.022(4) -0.018(4) -0.028(3)
C26 0.131(5) 0.071(4) 0.149(6) -0.014(4) -0.023(4) -0.026(3)
C27 0.107(4) 0.079(4) 0.109(4) -0.029(3) -0.016(3) 0.005(3)
C28 0.079(3) 0.065(3) 0.071(3) -0.017(3) -0.013(3) 0.005(3)
N29 0.056(2) 0.059(2) 0.063(2) -0.0045(19) -0.0131(17) 0.010(2)
N30 0.077(3) 0.070(2) 0.079(2) -0.013(2) -0.0201(18) 0.024(2)
N31 0.095(3) 0.075(3) 0.091(3) -0.024(2) -0.029(2) 0.027(2)
N32 0.088(3) 0.057(2) 0.085(2) -0.013(2) -0.0228(19) 0.022(2)
C33 0.060(3) 0.057(3) 0.053(3) -0.002(2) -0.001(2) 0.013(2)
C34 0.091(3) 0.147(4) 0.081(3) 0.012(3) 0.012(3) -0.020(3)
C35 0.110(3) 0.097(3) 0.068(3) -0.007(3) 0.004(2) 0.010(3)

_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 C11 1.211(3) . ?
Cl C19 1.728(4) . ?
N1 C8 1.369(4) . ?
N1 C2 1.383(4) . ?
C2 C3 1.356(4) . ?
C2 C10 1.508(3) . ?
C3 C9 1.431(4) . ?
C3 C14 1.484(3) . ?
C4 C5 1.368(4) . ?
C4 C9 1.400(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.367(4) . ?
C7 C8 1.397(4) . ?
C8 C9 1.399(4) . ?
C10 C11 1.517(4) . ?
C11 N12 1.355(3) . ?
N12 C15 1.464(3) . ?
N12 C13 1.480(3) . ?
C13 C14 1.513(3) . ?
C15 C33 1.510(4) . ?
C15 C16 1.518(4) . ?
C16 C21 1.373(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.351(4) . ?
C20 C21 1.383(4) . ?
C23 C24 1.379(4) . ?
C23 C28 1.386(4) . ?
C23 N29 1.437(4) . ?
C24 C25 1.376(5) . ?
C24 C34 1.512(4) . ?
C25 C26 1.365(5) . ?
C26 C27 1.384(5) . ?
C27 C28 1.383(4) . ?
C28 C35 1.505(4) . ?
N29 C33 1.338(4) . ?
N29 N30 1.349(3) . ?
N30 N31 1.293(3) . ?
N31 N32 1.368(3) . ?
N32 C33 1.322(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
C8 N1 C2 109.4(3) . . ?
C3 C2 N1 109.0(3) . . ?
C3 C2 C10 130.8(3) . . ?
N1 C2 C10 120.1(3) . . ?
C2 C3 C9 107.0(3) . . ?
C2 C3 C14 126.4(3) . . ?
C9 C3 C14 126.5(3) . . ?
C5 C4 C9 117.9(4) . . ?
C4 C5 C6 122.4(4) . . ?
C7 C6 C5 120.8(4) . . ?
C6 C7 C8 117.7(4) . . ?
N1 C8 C7 131.1(4) . . ?
N1 C8 C9 107.1(3) . . ?
C7 C8 C9 121.7(4) . . ?
C4 C9 C8 119.5(4) . . ?
C4 C9 C3 133.2(4) . . ?
C8 C9 C3 107.3(3) . . ?
C2 C10 C11 113.4(3) . . ?
O1 C11 N12 122.9(4) . . ?
O1 C11 C10 121.0(3) . . ?
N12 C11 C10 116.1(3) . . ?
C11 N12 C15 117.0(3) . . ?
C11 N12 C13 124.1(3) . . ?
C15 N12 C13 118.9(3) . . ?
N12 C13 C14 114.6(3) . . ?
C3 C14 C13 114.5(3) . . ?
N12 C15 C33 112.4(3) . . ?
N12 C15 C16 113.6(3) . . ?
C33 C15 C16 112.7(3) . . ?
C21 C16 C17 118.1(3) . . ?
C21 C16 C15 123.3(4) . . ?
C17 C16 C15 118.5(4) . . ?
C18 C17 C16 122.0(4) . . ?
C17 C18 C19 118.6(4) . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 Cl 120.5(4) . . ?
C18 C19 Cl 118.9(4) . . ?
C19 C20 C21 120.4(4) . . ?
C16 C21 C20 120.5(4) . . ?
C24 C23 C28 124.4(4) . . ?
C24 C23 N29 117.6(4) . . ?
C28 C23 N29 118.1(4) . . ?
C25 C24 C23 116.6(4) . . ?
C25 C24 C34 121.3(5) . . ?
C23 C24 C34 122.1(4) . . ?
C26 C25 C24 121.4(5) . . ?
C25 C26 C27 120.7(5) . . ?
C28 C27 C26 120.4(5) . . ?
C27 C28 C23 116.6(4) . . ?
C27 C28 C35 120.7(4) . . ?
C23 C28 C35 122.6(4) . . ?
C33 N29 N30 108.8(3) . . ?
C33 N29 C23 128.4(3) . . ?
N30 N29 C23 122.6(3) . . ?
N31 N30 N29 106.2(3) . . ?
N30 N31 N32 110.9(3) . . ?
C33 N32 N31 105.6(3) . . ?
N32 C33 N29 108.4(3) . . ?
N32 C33 C15 129.3(4) . . ?
N29 C33 C15 122.2(4) . . ?

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
N1 H1 N31 0.893(10) 2.250(13) 3.121(4) 165(3) 2_646

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.027
_database_code_depnum_ccdc_archive 'CCDC 948622'