# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2012


data_global

_journal_coden_Cambridge         1326
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Brogaard, Rasmus'
'Schalk, Oliver'
'Boguslavskiy, Andrey'
'Enright, Gary'
'Hopf, Henning'
'Raev, Vitaly'
'Tarcoveanu, Eliza'
'Solling, Theis'
'Stolow, Albert'

_publ_contact_author_name        'Mr Rasmus Brogaard'
_publ_contact_author_email       albert.stolow@nrc.ca

_publ_section_title              
;

;

# Attachment '- GEM.cif'

data_os3_0m
_database_code_depnum_ccdc_archive 'CCDC 853857'
#TrackingRef '- GEM.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

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 2(1)/n'

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

_cell_length_a                   7.5369(7)
_cell_length_b                   10.9410(9)
_cell_length_c                   16.6813(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.521(4)
_cell_angle_gamma                90.00
_cell_volume                     1342.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(1)
_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 Kappa APEXII CCD'
_diffrn_measurement_method       ' \f & \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33602
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.93
_reflns_number_total             3124
_reflns_number_gt                2459
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0897P)^2^+1.0107P] 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       ?
_refine_ls_number_reflns         3124
_refine_ls_number_parameters     194
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 1.0773(2) 0.62299(15) 0.12249(11) 0.0179(4) Uani 1 1 d . . .
C2 C 0.9423(2) 0.53877(15) 0.13303(11) 0.0184(4) Uani 1 1 d . . .
C3 C 0.9719(2) 0.47488(16) 0.20719(12) 0.0211(4) Uani 1 1 d . . .
H3 H 0.9003 0.4048 0.2117 0.025 Uiso 1 1 calc R . .
C4 C 1.1035(2) 0.51161(16) 0.27426(11) 0.0219(4) Uani 1 1 d . . .
H4 H 1.1202 0.4670 0.3242 0.026 Uiso 1 1 calc R . .
C5 C 1.2120(2) 0.61375(16) 0.26918(11) 0.0197(4) Uani 1 1 d . . .
C6 C 1.2102(2) 0.65823(16) 0.19112(11) 0.0185(4) Uani 1 1 d . . .
H6 H 1.3017 0.7143 0.1840 0.022 Uiso 1 1 calc R . .
C7 C 0.7554(2) 0.53324(17) 0.07689(12) 0.0227(4) Uani 1 1 d . . .
H7A H 0.7101 0.4481 0.0752 0.027 Uiso 1 1 calc R . .
H7B H 0.7654 0.5559 0.0206 0.027 Uiso 1 1 calc R . .
C8 C 0.6125(3) 0.62057(19) 0.10471(14) 0.0337(5) Uani 1 1 d . . .
H8A H 0.5521 0.6710 0.0573 0.040 Uiso 1 1 calc R . .
H8B H 0.5181 0.5702 0.1219 0.040 Uiso 1 1 calc R . .
C9 C 0.6986(2) 0.70402(17) 0.17480(13) 0.0242(4) Uani 1 1 d . A .
C10 C 0.7133(2) 0.66310(16) 0.25486(13) 0.0251(4) Uani 1 1 d . . .
H10 H 0.6280 0.6050 0.2659 0.030 Uiso 1 1 calc R . .
C11 C 0.8486(2) 0.70443(16) 0.31910(12) 0.0228(4) Uani 1 1 d . . .
H11 H 0.8533 0.6761 0.3734 0.027 Uiso 1 1 calc R . .
C12 C 0.9778(2) 0.78765(15) 0.30413(11) 0.0194(4) Uani 1 1 d . . .
C13 C 0.9396(2) 0.84701(15) 0.22891(11) 0.0204(4) Uani 1 1 d . A .
H13 H 1.0116 0.9154 0.2210 0.025 Uiso 1 1 calc R . .
C14 C 0.7990(3) 0.81000(16) 0.16431(11) 0.0230(4) Uani 1 1 d D . .
C15 C 1.2942(2) 0.68756(18) 0.34444(11) 0.0238(4) Uani 1 1 d . . .
H15A H 1.4113 0.7225 0.3378 0.029 Uiso 1 1 calc R . .
H15B H 1.3192 0.6331 0.3930 0.029 Uiso 1 1 calc R . .
C16 C 1.1641(3) 0.79518(18) 0.35984(12) 0.0248(4) Uani 1 1 d . . .
H16A H 1.1516 0.7924 0.4177 0.030 Uiso 1 1 calc R . .
H16B H 1.2202 0.8745 0.3510 0.030 Uiso 1 1 calc R . .
C17 C 1.0730(3) 0.68316(18) 0.04283(12) 0.0253(4) Uani 1 1 d . . .
H17 H 0.9834 0.6561 -0.0029 0.030 Uiso 1 1 calc R . .
C18 C 1.1776(3) 0.7670(2) 0.03033(12) 0.0318(5) Uani 1 1 d . . .
H18A H 1.2692 0.7968 0.0743 0.038 Uiso 1 1 calc R . .
H18B H 1.1650 0.8005 -0.0231 0.038 Uiso 1 1 calc R . .
C19A C 0.777(3) 0.882(2) 0.0886(9) 0.0366(9) Uani 0.602(6) 1 d PD A 1
H19A H 0.8749 0.9362 0.0867 0.044 Uiso 0.602(6) 1 calc PR A 1
O20A O 0.6523(6) 0.8847(4) 0.0276(2) 0.0756(16) Uani 0.602(6) 1 d PD A 1
C19B C 0.752(4) 0.873(3) 0.0855(13) 0.0366(9) Uani 0.398(6) 1 d PD A 2
H19B H 0.6524 0.8430 0.0457 0.044 Uiso 0.398(6) 1 calc PR A 2
O20B O 0.8323(10) 0.9621(6) 0.0669(4) 0.087(3) Uani 0.398(6) 1 d PD A 2

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
C1 0.0171(8) 0.0166(8) 0.0206(9) -0.0027(6) 0.0056(7) 0.0049(6)
C2 0.0181(8) 0.0167(8) 0.0209(9) -0.0062(6) 0.0054(7) 0.0027(6)
C3 0.0207(9) 0.0139(8) 0.0307(10) -0.0018(7) 0.0099(8) 0.0007(6)
C4 0.0218(9) 0.0205(9) 0.0242(10) 0.0026(7) 0.0072(7) 0.0065(7)
C5 0.0138(8) 0.0216(9) 0.0229(9) -0.0010(7) 0.0024(7) 0.0061(6)
C6 0.0143(8) 0.0179(8) 0.0238(10) -0.0021(7) 0.0056(7) 0.0021(6)
C7 0.0195(9) 0.0232(9) 0.0249(10) -0.0069(7) 0.0037(7) -0.0014(7)
C8 0.0181(9) 0.0324(11) 0.0460(13) -0.0176(9) -0.0034(9) 0.0043(8)
C9 0.0138(8) 0.0202(9) 0.0371(11) -0.0098(8) 0.0019(8) 0.0050(7)
C10 0.0171(9) 0.0161(9) 0.0442(12) -0.0052(8) 0.0111(8) -0.0002(7)
C11 0.0223(9) 0.0183(9) 0.0304(10) -0.0003(7) 0.0116(8) 0.0026(7)
C12 0.0191(8) 0.0162(8) 0.0240(9) -0.0064(7) 0.0069(7) 0.0006(6)
C13 0.0217(9) 0.0136(8) 0.0278(10) -0.0040(7) 0.0095(7) 0.0004(6)
C14 0.0229(9) 0.0200(9) 0.0261(10) -0.0041(7) 0.0057(8) 0.0072(7)
C15 0.0187(9) 0.0304(10) 0.0201(10) -0.0011(7) -0.0008(7) 0.0022(7)
C16 0.0226(9) 0.0276(10) 0.0232(10) -0.0063(7) 0.0028(8) -0.0024(7)
C17 0.0255(10) 0.0287(10) 0.0213(10) -0.0007(7) 0.0038(8) 0.0059(8)
C18 0.0405(12) 0.0393(12) 0.0148(9) 0.0080(8) 0.0042(8) -0.0183(9)
C19A 0.041(5) 0.039(3) 0.0283(15) -0.0016(19) 0.0051(15) 0.0178(19)
O20A 0.065(3) 0.107(4) 0.047(2) 0.023(2) -0.0048(18) 0.000(2)
C19B 0.041(5) 0.039(3) 0.0283(15) -0.0016(19) 0.0051(15) 0.0178(19)
O20B 0.115(6) 0.061(4) 0.086(5) 0.026(3) 0.026(4) -0.013(4)

_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
C1 C6 1.402(2) . ?
C1 C2 1.412(2) . ?
C1 C17 1.477(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.515(2) . ?
C3 C4 1.384(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.387(3) . ?
C5 C15 1.508(3) . ?
C7 C8 1.582(3) . ?
C8 C9 1.514(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.416(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.395(2) . ?
C12 C13 1.387(3) . ?
C12 C16 1.509(3) . ?
C13 C14 1.397(3) . ?
C14 C19B 1.461(5) . ?
C14 C19A 1.469(4) . ?
C15 C16 1.589(3) . ?
C17 C18 1.256(3) . ?
C19A O20A 1.227(5) . ?
C19B O20B 1.217(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
_geom_angle_publ_flag
C6 C1 C2 118.97(16) . . ?
C6 C1 C17 118.99(16) . . ?
C2 C1 C17 121.82(16) . . ?
C3 C2 C1 117.13(16) . . ?
C3 C2 C7 118.46(16) . . ?
C1 C2 C7 123.23(16) . . ?
C4 C3 C2 121.32(16) . . ?
C3 C4 C5 120.60(17) . . ?
C6 C5 C4 116.75(16) . . ?
C6 C5 C15 120.82(16) . . ?
C4 C5 C15 121.17(16) . . ?
C5 C6 C1 122.02(16) . . ?
C2 C7 C8 113.29(15) . . ?
C9 C8 C7 112.70(15) . . ?
C10 C9 C14 116.67(17) . . ?
C10 C9 C8 118.64(18) . . ?
C14 C9 C8 123.32(19) . . ?
C11 C10 C9 122.03(17) . . ?
C10 C11 C12 120.00(17) . . ?
C13 C12 C11 116.85(16) . . ?
C13 C12 C16 120.99(16) . . ?
C11 C12 C16 121.21(17) . . ?
C12 C13 C14 122.42(16) . . ?
C13 C14 C9 118.57(16) . . ?
C13 C14 C19B 123.4(4) . . ?
C9 C14 C19B 118.0(4) . . ?
C13 C14 C19A 115.6(3) . . ?
C9 C14 C19A 125.7(4) . . ?
C19B C14 C19A 8.1(7) . . ?
C5 C15 C16 112.03(14) . . ?
C12 C16 C15 112.62(15) . . ?
C18 C17 C1 125.65(19) . . ?
O20A C19A C14 130.4(6) . . ?
O20B C19B C14 124.9(7) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.060