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


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# 
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# 
#  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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data_121212_mzn
_database_code_depnum_ccdc_archive 'CCDC 930399'
#TrackingRef '18723_web_deposit_cif_file_0_ZhenniMa_1363835385.121212_mzn.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O'
_chemical_formula_sum            'C18 H18 O'
_chemical_formula_weight         250.32
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'
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 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   11.3820(9)
_cell_length_b                   5.6425(6)
_cell_length_c                   11.8926(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.817(8)
_cell_angle_gamma                90.00
_cell_volume                     731.11(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    865
_cell_measurement_theta_min      2.9323
_cell_measurement_theta_max      29.4110
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011)
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3015
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.34
_reflns_number_total             1479
_reflns_number_gt                986
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0245P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration unk
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_number_reflns         1479
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_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 0.64896(19) 0.5825(4) 0.6673(2) 0.0862(7) Uani 1 1 d . . .
C1 C 0.6874(2) 0.1223(6) 0.4729(2) 0.0694(9) Uani 1 1 d . . .
H1 H 0.6307 0.0129 0.4841 0.083 Uiso 1 1 calc R . .
C2 C 0.7472(3) 0.0787(7) 0.3885(3) 0.0795(10) Uani 1 1 d . . .
H2 H 0.7294 -0.0570 0.3423 0.095 Uiso 1 1 calc R . .
C3 C 0.8324(3) 0.2370(8) 0.3739(3) 0.0794(10) Uani 1 1 d . . .
H3 H 0.8727 0.2087 0.3174 0.095 Uiso 1 1 calc R . .
C4 C 0.8588(3) 0.4352(7) 0.4413(3) 0.0820(11) Uani 1 1 d . . .
H4 H 0.9181 0.5404 0.4318 0.098 Uiso 1 1 calc R . .
C5 C 0.7977(2) 0.4808(6) 0.5237(2) 0.0683(9) Uani 1 1 d . . .
H5 H 0.8155 0.6183 0.5686 0.082 Uiso 1 1 calc R . .
C6 C 0.7106(2) 0.3252(6) 0.5406(2) 0.0549(8) Uani 1 1 d . . .
C7 C 0.6467(2) 0.3803(6) 0.6305(3) 0.0595(8) Uani 1 1 d . . .
C8 C 0.5811(2) 0.1853(5) 0.6744(2) 0.0607(8) Uani 1 1 d . . .
H8A H 0.6285 0.0405 0.6802 0.073 Uiso 1 1 calc R . .
H8B H 0.5022 0.1586 0.6169 0.073 Uiso 1 1 calc R . .
C9 C 0.5601(2) 0.2345(6) 0.7930(2) 0.0616(8) Uani 1 1 d . . .
H9 H 0.5201 0.3892 0.7898 0.074 Uiso 1 1 calc R . .
C10 C 0.4762(2) 0.0440(7) 0.8203(3) 0.0895(12) Uani 1 1 d . . .
H10A H 0.4632 0.0768 0.8950 0.134 Uiso 1 1 calc R . .
H10B H 0.5142 -0.1086 0.8228 0.134 Uiso 1 1 calc R . .
H10C H 0.3989 0.0445 0.7603 0.134 Uiso 1 1 calc R . .
C11 C 0.6803(2) 0.2397(6) 0.8884(2) 0.0615(8) Uani 1 1 d . . .
H11 H 0.7280 0.1032 0.8994 0.074 Uiso 1 1 calc R . .
C12 C 0.7235(2) 0.4197(6) 0.9574(2) 0.0598(8) Uani 1 1 d . . .
H12 H 0.6741 0.5540 0.9459 0.072 Uiso 1 1 calc R . .
C13 C 0.8409(2) 0.4363(6) 1.0512(2) 0.0517(7) Uani 1 1 d . . .
C14 C 0.9313(2) 0.2642(6) 1.0699(2) 0.0562(8) Uani 1 1 d . . .
H14 H 0.9183 0.1306 1.0221 0.067 Uiso 1 1 calc R . .
C15 C 1.0406(2) 0.2872(6) 1.1584(2) 0.0621(9) Uani 1 1 d . . .
H15 H 1.1000 0.1692 1.1699 0.075 Uiso 1 1 calc R . .
C16 C 1.0615(2) 0.4833(7) 1.2290(2) 0.0677(9) Uani 1 1 d . . .
H16 H 1.1350 0.4988 1.2885 0.081 Uiso 1 1 calc R . .
C17 C 0.9740(3) 0.6563(6) 1.2118(2) 0.0692(9) Uani 1 1 d . . .
H17 H 0.9881 0.7901 1.2595 0.083 Uiso 1 1 calc R . .
C18 C 0.8647(2) 0.6331(6) 1.1239(2) 0.0623(8) Uani 1 1 d . . .
H18 H 0.8059 0.7519 1.1132 0.075 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 0.1212(17) 0.0422(15) 0.1034(16) -0.0057(16) 0.0452(13) -0.0013(14)
C1 0.0664(18) 0.061(3) 0.075(2) -0.004(2) 0.0116(16) -0.0113(17)
C2 0.100(2) 0.064(3) 0.074(2) -0.009(2) 0.0254(19) -0.005(2)
C3 0.093(2) 0.077(3) 0.071(2) 0.007(2) 0.0271(17) 0.005(2)
C4 0.089(2) 0.083(3) 0.075(2) 0.002(2) 0.0248(18) -0.016(2)
C5 0.0837(19) 0.049(2) 0.0639(19) 0.0007(18) 0.0082(16) -0.0072(18)
C6 0.0531(15) 0.048(2) 0.0535(16) 0.0060(16) -0.0016(13) 0.0017(15)
C7 0.0581(16) 0.048(2) 0.0637(19) 0.0015(19) 0.0038(14) 0.0023(15)
C8 0.0539(14) 0.050(2) 0.0714(18) -0.0004(18) 0.0081(12) -0.0002(15)
C9 0.0512(14) 0.058(2) 0.0723(18) -0.0056(18) 0.0124(12) 0.0002(15)
C10 0.0687(17) 0.094(3) 0.107(2) 0.002(3) 0.0277(17) -0.020(2)
C11 0.0562(15) 0.059(2) 0.0699(18) -0.0009(19) 0.0186(13) 0.0024(16)
C12 0.0599(15) 0.058(2) 0.0648(18) -0.0015(18) 0.0237(14) 0.0034(15)
C13 0.0571(15) 0.050(2) 0.0503(16) -0.0010(16) 0.0197(13) -0.0044(15)
C14 0.0615(15) 0.053(2) 0.0553(16) -0.0053(16) 0.0188(13) -0.0045(15)
C15 0.0570(15) 0.065(3) 0.0635(18) 0.006(2) 0.0158(13) 0.0004(16)
C16 0.0686(17) 0.072(3) 0.0574(18) 0.005(2) 0.0097(14) -0.0160(19)
C17 0.094(2) 0.054(3) 0.0603(18) -0.0068(18) 0.0225(17) -0.0184(19)
C18 0.0766(18) 0.046(2) 0.0672(17) 0.0008(19) 0.0251(15) 0.0002(15)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.219(4) . ?
C1 C6 1.380(4) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.490(4) . ?
C7 C8 1.505(4) . ?
C8 C9 1.524(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.504(3) . ?
C9 C10 1.533(4) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.309(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.475(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.385(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
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
C6 C1 C2 121.1(3) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 122.7(3) . . ?
C5 C6 C7 119.4(3) . . ?
O1 C7 C6 119.3(3) . . ?
O1 C7 C8 121.4(3) . . ?
C6 C7 C8 119.3(3) . . ?
C7 C8 C9 114.5(3) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C11 C9 C8 110.5(2) . . ?
C11 C9 C10 109.9(3) . . ?
C8 C9 C10 110.0(3) . . ?
C11 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 125.7(3) . . ?
C12 C11 H11 117.2 . . ?
C9 C11 H11 117.2 . . ?
C11 C12 C13 128.1(3) . . ?
C11 C12 H12 115.9 . . ?
C13 C12 H12 115.9 . . ?
C18 C13 C14 117.3(2) . . ?
C18 C13 C12 119.6(3) . . ?
C14 C13 C12 123.1(3) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.023