# Electronic Supplementary Material (ESI) for ChemComm.
# 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.
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data_mo_dm12001_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H34 Cl N2 O3'
_chemical_formula_weight         458.00

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'
Cl Cl 0.1484 0.1585 '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   P2(1)/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                   15.6872(18)
_cell_length_b                   19.328(2)
_cell_length_c                   8.3731(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.034(2)
_cell_angle_gamma                90.00
_cell_volume                     2528.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    132(2)
_cell_measurement_reflns_used    5751
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      132(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 ?
_diffrn_reflns_number            17326
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4959
_reflns_number_gt                3953
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0446P)²+1.2118P] 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         4959
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
N1 N 0.35122(8) 0.55831(6) 1.07707(14) 0.0182(3) Uani 1 1 d . . .
N2 N 0.71701(9) 0.56435(7) 1.63479(17) 0.0283(3) Uani 1 1 d . . .
C1 C 0.06800(10) 0.45757(8) 0.54064(18) 0.0210(3) Uani 1 1 d . . .
H1A H 0.1157 0.4285 0.5697 0.025 Uiso 1 1 calc R . .
C2 C 0.06320(10) 0.52107(8) 0.61868(18) 0.0195(3) Uani 1 1 d . . .
C3 C -0.00652(10) 0.56534(8) 0.57771(18) 0.0198(3) Uani 1 1 d . . .
C4 C -0.01921(11) 0.63260(8) 0.6675(2) 0.0250(4) Uani 1 1 d . . .
H4 H 0.0386 0.6513 0.7047 0.030 Uiso 1 1 calc R . .
C5 C -0.06628(14) 0.61770(11) 0.8147(2) 0.0436(5) Uani 1 1 d . . .
H5A H -0.0716 0.6605 0.8758 0.065 Uiso 1 1 calc R . .
H5B H -0.0342 0.5834 0.8820 0.065 Uiso 1 1 calc R . .
H5C H -0.1234 0.5996 0.7812 0.065 Uiso 1 1 calc R . .
C6 C -0.06708(15) 0.68794(10) 0.5649(3) 0.0455(5) Uani 1 1 d . . .
H6A H -0.1261 0.6728 0.5370 0.068 Uiso 1 1 calc R . .
H6B H -0.0386 0.6951 0.4667 0.068 Uiso 1 1 calc R . .
H6C H -0.0672 0.7314 0.6253 0.068 Uiso 1 1 calc R . .
C7 C 0.13346(10) 0.53714(8) 0.74574(18) 0.0198(3) Uani 1 1 d . . .
C8 C 0.14934(11) 0.49070(8) 0.87213(19) 0.0247(4) Uani 1 1 d . . .
H8 H 0.1116 0.4528 0.8817 0.030 Uiso 1 1 calc R . .
C9 C 0.21934(11) 0.49871(8) 0.98463(19) 0.0246(4) Uani 1 1 d . . .
H9 H 0.2295 0.4669 1.0707 0.030 Uiso 1 1 calc R . .
C10 C 0.27370(10) 0.55395(8) 0.96830(17) 0.0195(3) Uani 1 1 d . . .
C11 C 0.25858(10) 0.60258(8) 0.84784(18) 0.0202(3) Uani 1 1 d . . .
H11 H 0.2955 0.6412 0.8413 0.024 Uiso 1 1 calc R . .
C12 C 0.18825(10) 0.59373(8) 0.73653(18) 0.0208(3) Uani 1 1 d . . .
H12 H 0.1773 0.6267 0.6530 0.025 Uiso 1 1 calc R . .
C13 C 0.37709(10) 0.61895(8) 1.14512(18) 0.0194(3) Uani 1 1 d . . .
H13 H 0.3443 0.6596 1.1224 0.023 Uiso 1 1 calc R . .
C14 C 0.45070(10) 0.62217(8) 1.24723(18) 0.0195(3) Uani 1 1 d . . .
H14 H 0.4690 0.6653 1.2923 0.023 Uiso 1 1 calc R . .
C15 C 0.49872(9) 0.56262(8) 1.28523(17) 0.0177(3) Uani 1 1 d . . .
C16 C 0.47078(10) 0.50103(8) 1.21018(18) 0.0197(3) Uani 1 1 d . . .
H16 H 0.5024 0.4596 1.2310 0.024 Uiso 1 1 calc R . .
C17 C 0.39809(10) 0.50000(8) 1.10679(18) 0.0207(3) Uani 1 1 d . . .
H17 H 0.3803 0.4580 1.0553 0.025 Uiso 1 1 calc R . .
C18 C 0.57536(10) 0.56402(8) 1.40309(17) 0.0188(3) Uani 1 1 d . . .
C19 C 0.63413(10) 0.50968(8) 1.41513(19) 0.0244(3) Uani 1 1 d . . .
H19 H 0.6271 0.4712 1.3445 0.029 Uiso 1 1 calc R . .
C20 C 0.70308(11) 0.51218(9) 1.5311(2) 0.0281(4) Uani 1 1 d . . .
H20 H 0.7425 0.4747 1.5370 0.034 Uiso 1 1 calc R . .
C21 C 0.66041(11) 0.61614(8) 1.6221(2) 0.0273(4) Uani 1 1 d . . .
H21 H 0.6691 0.6538 1.6947 0.033 Uiso 1 1 calc R . .
C22 C 0.58986(10) 0.61865(8) 1.51023(19) 0.0233(3) Uani 1 1 d . . .
H22 H 0.5520 0.6571 1.5068 0.028 Uiso 1 1 calc R . .
C23 C 0.90978(16) 0.14376(17) 0.3168(3) 0.0743(9) Uani 1 1 d . . .
H23A H 0.8840 0.1234 0.4083 0.111 Uiso 1 1 calc R . .
H23B H 0.9586 0.1727 0.3557 0.111 Uiso 1 1 calc R . .
H23C H 0.9294 0.1068 0.2488 0.111 Uiso 1 1 calc R . .
C24 C 0.84481(17) 0.18710(14) 0.2216(3) 0.0666(8) Uani 1 1 d . . .
H24A H 0.8225 0.2230 0.2911 0.080 Uiso 1 1 calc R . .
H24B H 0.8715 0.2105 0.1334 0.080 Uiso 1 1 calc R . .
C25 C 0.74886(14) 0.68247(11) 0.2092(3) 0.0481(5) Uani 1 1 d . . .
H25A H 0.7388 0.6454 0.2851 0.072 Uiso 1 1 calc R . .
H25B H 0.7731 0.7228 0.2680 0.072 Uiso 1 1 calc R . .
H25C H 0.7890 0.6664 0.1339 0.072 Uiso 1 1 calc R . .
C26 C 0.66648(14) 0.70210(10) 0.1191(3) 0.0429(5) Uani 1 1 d . . .
H26A H 0.6272 0.7214 0.1940 0.051 Uiso 1 1 calc R . .
H26B H 0.6768 0.7382 0.0391 0.051 Uiso 1 1 calc R . .
Cl1 Cl 0.46674(3) 0.68633(2) 0.81933(5) 0.03029(12) Uani 1 1 d . . .
O1 O 0.77801(9) 0.14464(7) 0.15900(18) 0.0444(4) Uani 1 1 d . . .
H1 H 0.7419 0.1685 0.1032 0.067 Uiso 1 1 calc R . .
O2 O 0.62882(10) 0.64403(7) 0.04122(19) 0.0477(4) Uani 1 1 d . . .
H2 H 0.5846 0.6562 -0.0157 0.072 Uiso 1 1 calc R . .
O3 O 0.65576(9) 0.22351(7) 0.98641(18) 0.0373(3) Uani 1 1 d . . .
H1S H 0.6203(16) 0.2496(13) 1.042(3) 0.054(7) Uiso 1 1 d . . .
H2S H 0.6255(18) 0.2090(14) 0.908(3) 0.065(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.3499(19) . ?
N1 C17 1.3565(19) . ?
N1 C10 1.4564(18) . ?
N2 C21 1.336(2) . ?
N2 C20 1.336(2) . ?
C1 C3 1.393(2) 3_566 ?
C1 C2 1.396(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.407(2) . ?
C2 C7 1.496(2) . ?
C3 C1 1.393(2) 3_566 ?
C3 C4 1.524(2) . ?
C4 C5 1.518(3) . ?
C4 C6 1.527(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.393(2) . ?
C7 C12 1.397(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(2) . ?
C15 C18 1.487(2) . ?
C16 C17 1.370(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C22 1.391(2) . ?
C18 C19 1.395(2) . ?
C19 C20 1.390(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.494(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O1 1.397(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.487(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O2 1.402(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O1 H1 0.8400 . ?
O2 H2 0.8400 . ?
O3 H1S 0.91(3) . ?
O3 H2S 0.82(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C17 120.39(13) . . ?
C13 N1 C10 121.17(12) . . ?
C17 N1 C10 118.43(12) . . ?
C21 N2 C20 116.37(14) . . ?
C3 C1 C2 123.38(14) 3_566 . ?
C3 C1 H1A 118.3 3_566 . ?
C2 C1 H1A 118.3 . . ?
C1 C2 C3 119.56(14) . . ?
C1 C2 C7 116.68(13) . . ?
C3 C2 C7 123.75(14) . . ?
C1 C3 C2 117.06(14) 3_566 . ?
C1 C3 C4 120.66(14) 3_566 . ?
C2 C3 C4 122.07(13) . . ?
C5 C4 C3 109.43(14) . . ?
C5 C4 C6 109.82(16) . . ?
C3 C4 C6 113.52(14) . . ?
C5 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C6 C4 H4 108.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.44(14) . . ?
C8 C7 C2 118.55(13) . . ?
C12 C7 C2 122.80(13) . . ?
C9 C8 C7 121.37(15) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 118.47(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 121.97(14) . . ?
C9 C10 N1 118.16(13) . . ?
C11 C10 N1 119.79(13) . . ?
C10 C11 C12 118.69(14) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 120.99(14) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
N1 C13 C14 120.41(14) . . ?
N1 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 120.68(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 117.23(13) . . ?
C14 C15 C18 121.62(13) . . ?
C16 C15 C18 121.13(13) . . ?
C17 C16 C15 120.46(14) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
N1 C17 C16 120.77(13) . . ?
N1 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C22 C18 C19 117.07(14) . . ?
C22 C18 C15 121.24(14) . . ?
C19 C18 C15 121.65(14) . . ?
C20 C19 C18 119.55(15) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N2 C20 C19 123.59(16) . . ?
N2 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
N2 C21 C22 124.43(15) . . ?
N2 C21 H21 117.8 . . ?
C22 C21 H21 117.8 . . ?
C21 C22 C18 118.99(15) . . ?
C21 C22 H22 120.5 . . ?
C18 C22 H22 120.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 C23 109.0(2) . . ?
O1 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
O1 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 C25 110.10(17) . . ?
O2 C26 H26A 109.6 . . ?
C25 C26 H26A 109.6 . . ?
O2 C26 H26B 109.6 . . ?
C25 C26 H26B 109.6 . . ?
H26A C26 H26B 108.2 . . ?
C24 O1 H1 109.5 . . ?
C26 O2 H2 109.5 . . ?
H1S O3 H2S 105(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.84 1.92 2.7575(19) 176.7 1_554

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 997000'
