# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Enders, Dieter'
_publ_contact_author_email       enders@rwth-aachen.de

_publ_section_title              
;
N-Heterocyclic Carbene Catalysed Asymmetric Cross-Benzoin-Reactions
of Heteroatomic Aldehydes with Trifluoromethyl Ketones
;
_publ_author_name                D.Enders

# Attachment 'gr0654.cif'

########################################
# #
# CIF generated by the Xtal System #
# #
########################################

data_gr0654
_database_code_depnum_ccdc_archive 'CCDC 781144'
#TrackingRef 'gr0654.cif'

# 2. EXPERIMENTAL DATA
#---------------------

_publ_section_exptl_prep         #<< material & crystal preparation text
; ?
;

_publ_section_exptl_refinement   #<< crystallographic methods used
; ?
;

_chemical_formula_sum            'C13 H9 F3 O3'
_chemical_formula_moiety         ?
_chemical_formula_weight         270.21
_chemical_melting_point          ?

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P_21_21_21
_symmetry_space_group_name_Hall  p_2ac_2ab

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

_cell_length_a                   7.7030(2)
_cell_length_b                   7.9309(2)
_cell_length_c                   20.1220(5)
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_volume                     1229.29(5)
_cell_formula_units_Z            4

_exptl_crystal_density_diffrn    1.46
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    293

_exptl_absorpt_coefficient_mu    1.165
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_diffrn_reflns_number            24112
_reflns_number_total             2185
_reflns_Friedel_coverage         .695
_reflns_number_gt                2173
_reflns_threshold_expression     'F > .00 sig(F )'

_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_full        ?
_diffrn_measured_fraction_theta_max ?
_diffrn_measured_fraction_theta_full ?
_diffrn_reflns_av_R_equivalents  .016
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ? #<< do not append units
_diffrn_standards_decay_%        ? #<< do not append %

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           .025
_refine_ls_wR_factor_ref         .032
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     209
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_shift/su_max          .001
_refine_diff_density_min         -.107
_refine_diff_density_max         .13

_refine_ls_extinction_method     Zachariasen
_refine_ls_extinction_coef       3334(337)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?

# 3. Information for the "methods" section
#-----------------------------------------

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_structure_solution    xtal
_computing_structure_refinement  'xtal CRYLSQ'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'

# 4. Supplementary data for validation and tables
#------------------------------------------------

loop_
_atom_type_symbol
_atom_type_description
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? 0 52 .017 .009 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H ? 0 36 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O ? 0 12 .047 .032 'Int Tables Vol IV Tables 2.2B and 2.3.1'
F ? 0 12 .069 .053 'Int Tables Vol IV Tables 2.2B and 2.3.1'

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 .67141(14) -.02059(14) 1.06841(4) .0543(6) Uani ? ? 1.00000 ? ?
C9 .64595(18) -.02715(18) 1.00100(6) .0444(7) Uani ? ? 1.00000 ? ?
C1 .68097(16) -.18839(17) .97115(5) .0380(6) Uani ? ? 1.00000 ? ?
C2 .63121(16) -.20950(17) .89668(5) .0393(6) Uani ? ? 1.00000 ? ?
C8 .93380(18) -.11360(18) .86459(5) .0437(6) Uani ? ? 1.00000 ? ?
C3 .75620(17) -.10767(18) .85349(5) .0392(6) Uani ? ? 1.00000 ? ?
C7 1.0455(2) -.0222(2) .82449(6) .0517(8) Uani ? ? 1.00000 ? ?
C10 .6005(3) .1272(2) .97888(8) .0687(11) Uani ? ? 1.00000 ? ?
C5 .8064(3) .0811(3) .76239(8) .0720(11) Uani ? ? 1.00000 ? ?
C6 .9823(2) .0757(2) .77364(7) .0631(9) Uani ? ? 1.00000 ? ?
C12 .6408(3) .1411(2) 1.08633(8) .0669(10) Uani ? ? 1.00000 ? ?
C13 .64154(19) -.3965(2) .87676(6) .0497(7) Uani ? ? 1.00000 ? ?
O1 .74607(15) -.30418(13) 1.00188(4) .0548(6) Uani ? ? 1.00000 ? ?
C11 .5990(3) .2350(3) 1.03401(10) .0793(12) Uani ? ? 1.00000 ? ?
F1 .79800(11) -.46288(11) .88117(4) .0596(5) Uani ? ? 1.00000 ? ?
F2 .53436(14) -.49172(14) .91308(5) .0732(6) Uani ? ? 1.00000 ? ?
C4 .6921(2) -.0108(3) .80165(7) .0602(9) Uani ? ? 1.00000 ? ?
O3 .46030(13) -.15445(14) .88519(4) .0495(5) Uani ? ? 1.00000 ? ?
F3 .59198(15) -.41418(15) .81320(4) .0777(6) Uani ? ? 1.00000 ? ?
H7 1.164(3) -.023(3) .8320(9) .066(5) Uiso ? ? 1.00000 ? ?
H8 .984(2) -.183(2) .8982(8) .048(4) Uiso ? ? 1.00000 ? ?
H5 .760(3) .151(3) .7288(12) .086(6) Uiso ? ? 1.00000 ? ?
H12 .647(3) .163(3) 1.1304(11) .064(5) Uiso ? ? 1.00000 ? ?
H4 .568(3) -.009(2) .7941(8) .058(4) Uiso ? ? 1.00000 ? ?
H6 1.058(3) .140(3) .7460(10) .074(6) Uiso ? ? 1.00000 ? ?
H10 .570(3) .149(3) .9339(11) .080(6) Uiso ? ? 1.00000 ? ?
H13 .393(3) -.187(3) .9129(10) .061(5) Uiso ? ? 1.00000 ? ?
H11 .580(3) .342(3) 1.0331(11) .078(6) Uiso ? ? 1.00000 ? ?

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 .0641(7) .0648(6) .0339(4) .0038(5) .0005(4) -.0024(4)
C9 .0460(7) .0553(8) .0319(5) .0017(6) .0004(5) .0047(5)
C1 .0347(6) .0508(7) .0284(5) .0010(5) .0014(4) .0088(5)
C2 .0352(6) .0535(7) .0293(5) .0018(5) -.0022(4) .0084(5)
C8 .0437(7) .0513(7) .0360(5) .0022(6) -.0018(5) .0001(5)
C3 .0414(7) .0513(7) .0250(5) .0006(6) -.0000(5) .0022(5)
C7 .0420(7) .0633(9) .0498(7) -.0041(7) .0066(6) -.0034(6)
C10 .1013(15) .0550(9) .0498(8) .0129(9) -.0030(8) .0034(7)
C5 .0699(11) .0985(14) .0476(7) -.0051(10) -.0002(7) .0360(8)
C6 .0640(10) .0788(11) .0464(7) -.0132(9) .0146(7) .0104(7)
C12 .0781(12) .0696(11) .0530(8) .0008(9) .0065(7) -.0173(8)
C13 .0477(8) .0576(8) .0439(6) -.0064(7) -.0067(6) -.0004(6)
O1 .0723(7) .0579(6) .0342(4) .0167(5) -.0091(5) .0075(4)
C11 .1124(17) .0520(10) .0737(10) .0124(10) .0081(11) -.0075(8)
F1 .0576(5) .0550(5) .0661(5) .0080(4) -.0027(4) -.0079(4)
F2 .0658(6) .0640(6) .0896(6) -.0180(5) .0024(5) .0144(5)
C4 .0494(8) .0892(12) .0420(6) -.0005(8) -.0026(6) .0262(7)
O3 .0353(5) .0770(7) .0362(4) .0050(5) -.0005(4) .0176(4)
F3 .0916(8) .0872(7) .0543(5) -.0074(6) -.0256(5) -.0164(5)

# 5. Molecular Geometry
#----------------------

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag #<< enter y(es) for value to be published
O2 C12 '4 656' '4 656' 1.353(2) ?
O2 C9 '4 656' '4 656' 1.3716(15) ?
C9 C10 '4 656' '4 656' 1.349(2) ?
C9 C1 '4 656' '4 656' 1.4383(19) ?
C1 O1 '4 656' '4 656' 1.2153(16) ?
C1 C2 '4 656' '4 656' 1.5558(15) ?
C2 O3 '4 656' '4 656' 1.4062(16) ?
C2 C3 '4 656' '4 656' 1.5279(17) ?
C2 C13 '4 656' '4 656' 1.538(2) ?
C8 H8 '4 656' '4 656' .953(17) ?
C8 C7 '4 656' '4 656' 1.385(2) ?
C8 C3 '4 656' '4 656' 1.3869(19) ?
C3 C4 '4 656' '4 656' 1.387(2) ?
C7 H7 '4 656' '4 656' .93(2) ?
C7 C6 '4 656' '4 656' 1.374(2) ?
C10 H10 '4 656' '4 656' .95(2) ?
C10 C11 '4 656' '4 656' 1.401(3) ?
C5 H5 '4 656' '4 656' .94(2) ?
C5 C6 '4 656' '4 656' 1.374(3) ?
C5 C4 '4 656' '4 656' 1.389(3) ?
C6 H6 '4 656' '4 656' .96(2) ?
C12 H12 '4 656' '4 656' .90(2) ?
C12 C11 '4 656' '4 656' 1.329(3) ?
C13 F1 '4 656' '4 656' 1.3183(17) ?
C13 F2 '4 656' '4 656' 1.3366(18) ?
C13 F3 '4 656' '4 656' 1.3421(15) ?
C11 H11 '4 656' '4 656' .86(3) ?
C4 H4 '4 656' '4 656' .97(2) ?
O3 H13 '4 656' '4 656' .80(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag #<< enter yes for value to be published
C12 O2 C9 '4 656' '4 656' '4 656' 105.94(11) ?
C10 C9 O2 '4 656' '4 656' '4 656' 109.21(12) ?
C10 C9 C1 '4 656' '4 656' '4 656' 135.87(12) ?
O2 C9 C1 '4 656' '4 656' '4 656' 114.83(11) ?
O1 C1 C9 '4 656' '4 656' '4 656' 122.46(10) ?
O1 C1 C2 '4 656' '4 656' '4 656' 120.69(11) ?
C9 C1 C2 '4 656' '4 656' '4 656' 116.85(11) ?
O3 C2 C3 '4 656' '4 656' '4 656' 109.41(10) ?
O3 C2 C13 '4 656' '4 656' '4 656' 107.75(11) ?
O3 C2 C1 '4 656' '4 656' '4 656' 110.83(9) ?
C3 C2 C13 '4 656' '4 656' '4 656' 109.19(10) ?
C3 C2 C1 '4 656' '4 656' '4 656' 109.62(10) ?
C13 C2 C1 '4 656' '4 656' '4 656' 110.00(10) ?
H8 C8 C7 '4 656' '4 656' '4 656' 117.6(10) ?
H8 C8 C3 '4 656' '4 656' '4 656' 122.2(10) ?
C7 C8 C3 '4 656' '4 656' '4 656' 120.10(11) ?
C4 C3 C8 '4 656' '4 656' '4 656' 119.43(12) ?
C4 C3 C2 '4 656' '4 656' '4 656' 119.76(12) ?
C8 C3 C2 '4 656' '4 656' '4 656' 120.80(10) ?
H7 C7 C6 '4 656' '4 656' '4 656' 118.3(12) ?
H7 C7 C8 '4 656' '4 656' '4 656' 121.1(12) ?
C6 C7 C8 '4 656' '4 656' '4 656' 120.62(14) ?
H10 C10 C9 '4 656' '4 656' '4 656' 122.8(14) ?
H10 C10 C11 '4 656' '4 656' '4 656' 129.9(14) ?
C9 C10 C11 '4 656' '4 656' '4 656' 107.15(15) ?
H5 C5 C6 '4 656' '4 656' '4 656' 120.6(14) ?
H5 C5 C4 '4 656' '4 656' '4 656' 118.4(14) ?
C6 C5 C4 '4 656' '4 656' '4 656' 120.96(16) ?
H6 C6 C7 '4 656' '4 656' '4 656' 121.2(13) ?
H6 C6 C5 '4 656' '4 656' '4 656' 119.5(13) ?
C7 C6 C5 '4 656' '4 656' '4 656' 119.36(16) ?
H12 C12 C11 '4 656' '4 656' '4 656' 133.2(13) ?
H12 C12 O2 '4 656' '4 656' '4 656' 115.5(13) ?
C11 C12 O2 '4 656' '4 656' '4 656' 111.25(15) ?
F1 C13 F2 '4 656' '4 656' '4 656' 107.58(12) ?
F1 C13 F3 '4 656' '4 656' '4 656' 106.40(11) ?
F1 C13 C2 '4 656' '4 656' '4 656' 114.52(12) ?
F2 C13 F3 '4 656' '4 656' '4 656' 106.63(12) ?
F2 C13 C2 '4 656' '4 656' '4 656' 111.75(11) ?
F3 C13 C2 '4 656' '4 656' '4 656' 109.55(11) ?
H11 C11 C12 '4 656' '4 656' '4 656' 127.6(14) ?
H11 C11 C10 '4 656' '4 656' '4 656' 125.9(14) ?
C12 C11 C10 '4 656' '4 656' '4 656' 106.45(18) ?
H4 C4 C3 '4 656' '4 656' '4 656' 118.5(10) ?
H4 C4 C5 '4 656' '4 656' '4 656' 121.9(10) ?
C3 C4 C5 '4 656' '4 656' '4 656' 119.52(15) ?
H13 O3 C2 '4 656' '4 656' '4 656' 112.9(15) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag #<< enter yes for value to be published
C12 O2 C9 C1 '4 656' '4 656' '4 656' '4 656' 176.97(13) ?
C12 O2 C9 C10 '4 656' '4 656' '4 656' '4 656' -.18(19) ?
C9 O2 C12 C11 '4 656' '4 656' '4 656' '4 656' -.4(2) ?
C9 O2 C12 H12 '4 656' '4 656' '4 656' '4 656' 176.8(14) ?
O2 C9 C1 C2 '4 656' '4 656' '4 656' '4 656' 172.21(11) ?
O2 C9 C1 O1 '4 656' '4 656' '4 656' '4 656' -7.7(2) ?
C10 C9 C1 C2 '4 656' '4 656' '4 656' '4 656' -11.7(3) ?
C10 C9 C1 O1 '4 656' '4 656' '4 656' '4 656' 168.4(2) ?
O2 C9 C10 C11 '4 656' '4 656' '4 656' '4 656' .6(2) ?
O2 C9 C10 H10 '4 656' '4 656' '4 656' '4 656' -176.1(16) ?
C1 C9 C10 C11 '4 656' '4 656' '4 656' '4 656' -175.64(18) ?
C1 C9 C10 H10 '4 656' '4 656' '4 656' '4 656' 7.6(17) ?
C9 C1 C2 C3 '4 656' '4 656' '4 656' '4 656' 71.56(14) ?
C9 C1 C2 C13 '4 656' '4 656' '4 656' '4 656' -168.37(11) ?
C9 C1 C2 O3 '4 656' '4 656' '4 656' '4 656' -49.31(15) ?
O1 C1 C2 C3 '4 656' '4 656' '4 656' '4 656' -108.53(14) ?
O1 C1 C2 C13 '4 656' '4 656' '4 656' '4 656' 11.55(17) ?
O1 C1 C2 O3 '4 656' '4 656' '4 656' '4 656' 130.60(13) ?
C1 C2 C3 C8 '4 656' '4 656' '4 656' '4 656' 45.57(16) ?
C1 C2 C3 C4 '4 656' '4 656' '4 656' '4 656' -135.79(13) ?
C13 C2 C3 C8 '4 656' '4 656' '4 656' '4 656' -74.99(14) ?
C13 C2 C3 C4 '4 656' '4 656' '4 656' '4 656' 103.65(15) ?
O3 C2 C3 C8 '4 656' '4 656' '4 656' '4 656' 167.30(11) ?
O3 C2 C3 C4 '4 656' '4 656' '4 656' '4 656' -14.06(17) ?
C1 C2 C13 F1 '4 656' '4 656' '4 656' '4 656' -62.94(13) ?
C1 C2 C13 F2 '4 656' '4 656' '4 656' '4 656' 59.70(14) ?
C1 C2 C13 F3 '4 656' '4 656' '4 656' '4 656' 177.64(11) ?
C3 C2 C13 F1 '4 656' '4 656' '4 656' '4 656' 57.39(13) ?
C3 C2 C13 F2 '4 656' '4 656' '4 656' '4 656' -179.97(10) ?
C3 C2 C13 F3 '4 656' '4 656' '4 656' '4 656' -62.03(14) ?
O3 C2 C13 F1 '4 656' '4 656' '4 656' '4 656' 176.14(9) ?
O3 C2 C13 F2 '4 656' '4 656' '4 656' '4 656' -61.22(12) ?
O3 C2 C13 F3 '4 656' '4 656' '4 656' '4 656' 56.72(13) ?
C1 C2 O3 H13 '4 656' '4 656' '4 656' '4 656' -44.5(16) ?
C3 C2 O3 H13 '4 656' '4 656' '4 656' '4 656' -165.5(16) ?
C13 C2 O3 H13 '4 656' '4 656' '4 656' '4 656' 75.9(16) ?
C7 C8 C3 C2 '4 656' '4 656' '4 656' '4 656' 179.19(12) ?
C7 C8 C3 C4 '4 656' '4 656' '4 656' '4 656' .5(2) ?
H8 C8 C3 C2 '4 656' '4 656' '4 656' '4 656' 1.8(12) ?
H8 C8 C3 C4 '4 656' '4 656' '4 656' '4 656' -176.9(12) ?
C3 C8 C7 C6 '4 656' '4 656' '4 656' '4 656' .3(2) ?
C3 C8 C7 H7 '4 656' '4 656' '4 656' '4 656' 178.3(15) ?
H8 C8 C7 C6 '4 656' '4 656' '4 656' '4 656' 177.8(12) ?
H8 C8 C7 H7 '4 656' '4 656' '4 656' '4 656' -4.2(19) ?
C2 C3 C4 C5 '4 656' '4 656' '4 656' '4 656' -179.78(15) ?
C2 C3 C4 H4 '4 656' '4 656' '4 656' '4 656' .5(12) ?
C8 C3 C4 C5 '4 656' '4 656' '4 656' '4 656' -1.1(2) ?
C8 C3 C4 H4 '4 656' '4 656' '4 656' '4 656' 179.2(12) ?
C8 C7 C6 C5 '4 656' '4 656' '4 656' '4 656' -.6(2) ?
C8 C7 C6 H6 '4 656' '4 656' '4 656' '4 656' 179.3(15) ?
H7 C7 C6 C5 '4 656' '4 656' '4 656' '4 656' -178.6(14) ?
H7 C7 C6 H6 '4 656' '4 656' '4 656' '4 656' 1(2) ?
C9 C10 C11 C12 '4 656' '4 656' '4 656' '4 656' -.9(3) ?
C9 C10 C11 H11 '4 656' '4 656' '4 656' '4 656' 175.9(18) ?
H10 C10 C11 C12 '4 656' '4 656' '4 656' '4 656' 175.5(18) ?
H10 C10 C11 H11 '4 656' '4 656' '4 656' '4 656' -8(3) ?
C4 C5 C6 C7 '4 656' '4 656' '4 656' '4 656' .0(3) ?
C4 C5 C6 H6 '4 656' '4 656' '4 656' '4 656' -179.9(15) ?
H5 C5 C6 C7 '4 656' '4 656' '4 656' '4 656' 177.5(18) ?
H5 C5 C6 H6 '4 656' '4 656' '4 656' '4 656' -2(2) ?
C6 C5 C4 C3 '4 656' '4 656' '4 656' '4 656' .9(3) ?
C6 C5 C4 H4 '4 656' '4 656' '4 656' '4 656' -179.5(13) ?
H5 C5 C4 C3 '4 656' '4 656' '4 656' '4 656' -176.7(18) ?
H5 C5 C4 H4 '4 656' '4 656' '4 656' '4 656' 3(2) ?
O2 C12 C11 C10 '4 656' '4 656' '4 656' '4 656' .8(3) ?
O2 C12 C11 H11 '4 656' '4 656' '4 656' '4 656' -175.9(19) ?
H12 C12 C11 C10 '4 656' '4 656' '4 656' '4 656' -175.7(17) ?
H12 C12 C11 H11 '4 656' '4 656' '4 656' '4 656' 8(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag #<< enter yes for value to be published
? ? ? ? ? ? ? ? ? ? ?

#--------------------------------------------------------------------------
# Special items requested by author for inclusion in paper
#--------------------------------------------------------------------------

loop_
_publ_manuscript_incl_extra_item
_publ_manuscript_incl_extra_defn
? ?

#--------------------------------------------------------------------------
# Items which are non-mandatory for Acta C submissions
#--------------------------------------------------------------------------

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
C2 H13 1.87(2) '4 656' '4 656' ?
O2 H12 1.92(2) '4 656' '4 656' ?
C12 H11 1.98(3) '4 656' '4 656' ?
C6 H7 1.99(2) '4 656' '4 656' ?
C7 H8 2.012(17) '4 656' '4 656' ?
C4 H5 2.02(3) '4 656' '4 656' ?
C5 H6 2.02(2) '4 656' '4 656' ?
C6 H5 2.02(2) '4 656' '4 656' ?
C8 H7 2.02(2) '4 656' '4 656' ?
C9 H10 2.03(2) '4 656' '4 656' ?
C10 H11 2.03(3) '4 656' '4 656' ?
C3 H4 2.036(19) '4 656' '4 656' ?
C7 H6 2.04(2) '4 656' '4 656' ?
C11 H12 2.06(2) '4 656' '4 656' ?
O1 H13 2.06(2) '4 656' '2 554' ?
C3 H8 2.060(16) '4 656' '4 656' ?
C5 H4 2.07(2) '4 656' '4 656' ?
F1 F3 2.1303(13) '4 656' '4 656' ?
C11 H10 2.14(2) '4 656' '4 656' ?
F1 F2 2.1421(14) '4 656' '4 656' ?
F2 F3 2.1481(13) '4 656' '4 656' ?
C9 C12 2.175(2) '4 656' '4 656' ?
C10 C12 2.187(2) '4 656' '4 656' ?
C9 C11 2.212(3) '4 656' '4 656' ?
O2 C11 2.213(2) '4 656' '4 656' ?
O2 C10 2.217(2) '4 656' '4 656' ?
H7 H8 2.31(3) '4 656' '4 656' ?
H7 H6 2.31(3) '4 656' '4 656' ?
O3 H4 2.319(17) '4 656' '4 656' ?
H5 H6 2.32(3) '4 656' '4 656' ?
C9 O1 2.3285(18) '4 656' '4 656' ?
H5 H4 2.35(3) '4 656' '4 656' ?
C2 F3 2.3554(16) '4 656' '4 656' ?
O2 C1 2.3678(14) '4 656' '4 656' ?
C7 C5 2.372(2) '4 656' '4 656' ?
C13 O3 2.3795(19) '4 656' '4 656' ?
C2 F2 2.3823(17) '4 656' '4 656' ?
C8 C4 2.395(2) '4 656' '4 656' ?
C3 O3 2.3958(16) '4 656' '4 656' ?
C8 C6 2.396(2) '4 656' '4 656' ?
C3 C5 2.398(2) '4 656' '4 656' ?
C3 C7 2.401(2) '4 656' '4 656' ?
C6 C4 2.405(2) '4 656' '4 656' ?
C2 F1 2.4055(16) '4 656' '4 656' ?
C2 O1 2.4139(14) '4 656' '4 656' ?
C1 O3 2.4400(14) '4 656' '4 656' ?
H12 H11 2.48(3) '4 656' '4 656' ?
C3 C13 2.499(2) '4 656' '4 656' ?
C1 H13 2.51(2) '4 656' '4 656' ?
H10 H11 2.52(3) '4 656' '4 656' ?
C1 C3 2.5201(15) '4 656' '4 656' ?
C2 C4 2.522(2) '4 656' '4 656' ?
C1 C13 2.5343(18) '4 656' '4 656' ?
C2 C8 2.5354(18) '4 656' '4 656' ?
C9 C2 2.5516(17) '4 656' '4 656' ?
C1 C10 2.583(2) '4 656' '4 656' ?
F3 H4 2.597(17) '4 656' . ?
C13 H13 2.64(2) '4 656' '4 656' ?
C2 H4 2.651(17) '4 656' '4 656' ?
F2 H13 2.65(2) '4 656' '4 656' ?
F1 H8 2.665(17) '4 656' '4 656' ?
O2 O1 2.6799(14) '4 656' '4 656' ?
C4 O3 2.7040(19) '4 656' '4 656' ?
O3 F3 2.7149(15) '4 656' '4 656' ?
C2 H8 2.725(15) '4 656' '4 656' ?
O3 H7 2.73(2) '4 656' '4 756' ?
H7 H13 2.73(3) '4 656' '4 556' ?
O3 H10 2.73(2) '4 656' '4 656' ?
C13 O1 2.7426(15) '4 656' '4 656' ?
C8 C5 2.753(2) '4 656' '4 656' ?
C1 H8 2.757(16) '4 656' '4 656' ?
C7 C4 2.763(2) '4 656' '4 656' ?
O1 F1 2.7647(12) '4 656' '4 656' ?
F2 H11 2.77(2) '4 656' '4 646' ?
C3 C6 2.780(2) '4 656' '4 656' ?
F2 O3 2.7920(16) '4 656' '4 656' ?
O2 F2 2.8222(15) '4 656' '2 554' ?
O1 O3 2.8275(13) '4 656' '2 554' ?
O1 F2 2.8398(15) '4 656' '4 656' ?
O2 H8 2.841(17) '4 656' '2 654' ?
O1 H8 2.851(16) '4 656' '2 654' ?
C3 F3 2.8577(18) '4 656' '4 656' ?
F3 H5 2.89(2) '4 656' . ?
C3 F1 2.8896(17) '4 656' '4 656' ?
F2 H10 2.90(2) '4 656' '4 646' ?
C1 F2 2.9031(17) '4 656' '4 656' ?
C1 H10 2.91(2) '4 656' '4 656' ?
F1 H6 2.91(2) '4 656' '1 455' ?
O2 H13 2.91(2) '4 656' '2 554' ?
C9 O3 2.9145(16) '4 656' '4 656' ?
H7 H5 2.92(3) '4 656' '1 455' ?
C9 H13 2.92(2) '4 656' '4 656' ?
O1 H8 2.938(16) '4 656' '4 656' ?
C1 C8 2.9568(16) '4 656' '4 656' ?
H7 H12 2.96(3) '4 656' '2 564' ?
C8 H6 2.96(2) '4 656' '1 455' ?
C3 H10 2.97(2) '4 656' '4 656' ?
C1 F1 2.9715(15) '4 656' '4 656' ?
C2 H10 2.98(2) '4 656' '4 656' ?
F3 H6 2.98(2) '4 656' '1 455' ?
C8 F1 2.9798(17) '4 656' '4 656' ?
C9 H12 3.01(2) '4 656' '4 656' ?
C1 H13 3.02(2) '4 656' '2 554' ?
H12 H6 3.02(3) '4 656' '2 664' ?
H10 H13 3.02(3) '4 656' '4 656' ?
C9 H11 3.04(3) '4 656' '4 656' ?
O2 H11 3.04(3) '4 656' '4 656' ?
O2 F1 3.0529(13) '4 656' '2 654' ?
C12 F1 3.066(2) '4 656' '2 654' ?
H4 H10 3.08(3) '4 656' '4 656' ?
H4 H13 3.08(3) '4 656' '4 656' ?
C10 H12 3.08(2) '4 656' '4 656' ?
C4 H10 3.09(2) '4 656' '4 656' ?
C7 H12 3.09(2) '4 656' '2 564' ?
F3 H13 3.10(2) '4 656' '4 656' ?
C3 H13 3.10(2) '4 656' '4 656' ?
C6 H12 3.11(2) '4 656' '2 564' ?
C12 H10 3.12(2) '4 656' '4 656' ?
C10 O3 3.116(2) '4 656' '4 656' ?
O2 H10 3.12(2) '4 656' '4 656' ?
H8 H11 3.12(3) '4 656' '2 564' ?
F1 H12 3.13(2) '4 656' '2 554' ?
C7 H6 3.13(2) '4 656' '1 455' ?
H7 H11 3.14(3) '4 656' '2 564' ?
O1 H11 3.15(3) '4 656' '4 646' ?
C2 C10 3.150(2) '4 656' '4 656' ?
C9 C3 3.1526(16) '4 656' '4 656' ?
C13 H8 3.164(16) '4 656' '4 656' ?
H8 H13 3.17(3) '4 656' '4 556' ?
C3 H6 3.17(2) '4 656' '1 455' ?
C7 H5 3.18(3) '4 656' '1 455' ?
C8 H11 3.19(2) '4 656' '2 564' ?
C8 C13 3.188(2) '4 656' '4 656' ?
C5 H7 3.20(2) '4 656' '4 656' ?
C1 H8 3.202(16) '4 656' '2 654' ?
H7 H4 3.20(3) '4 656' '4 556' ?
C7 H11 3.21(2) '4 656' '2 564' ?
C7 H5 3.23(2) '4 656' '4 656' ?
C6 H8 3.239(17) '4 656' '4 656' ?
C3 H5 3.24(3) '4 656' '4 656' ?
H8 H6 3.24(3) '4 656' '1 455' ?
F3 H4 3.24(2) '4 656' '4 656' ?
C10 H13 3.24(2) '4 656' '4 656' ?
C3 H7 3.24(2) '4 656' '4 656' ?
O3 H5 3.24(2) '4 656' . ?
C12 F2 3.255(2) '4 656' '2 554' ?
H5 H12 3.26(3) '4 656' '3 457' ?
C4 H6 3.26(2) '4 656' '4 656' ?
C8 H4 3.26(2) '4 656' '4 656' ?
C8 H6 3.27(2) '4 656' '4 656' ?
C4 H8 3.270(16) '4 656' '4 656' ?
C4 F3 3.2735(18) '4 656' '1 565' ?
C6 H4 3.29(2) '4 656' '4 656' ?
C11 F2 3.296(2) '4 656' '4 666' ?
C4 F3 3.299(2) '4 656' '4 656' ?
C5 H12 3.30(2) '4 656' '3 457' ?
C9 H8 3.311(17) '4 656' '2 654' ?
C10 F2 3.339(2) '4 656' '4 666' ?
H5 H13 3.34(3) '4 656' '1 565' ?
C3 C10 3.358(2) '4 656' '4 656' ?
C9 O1 3.3587(18) '4 656' '2 654' ?
C3 O1 3.3689(14) '4 656' '4 656' ?
O1 H13 3.39(2) '4 656' '4 656' ?
F2 H12 3.39(2) '4 656' '2 654' ?
C1 O1 3.3942(17) '4 656' '2 654' ?
C13 H6 3.40(2) '4 656' '1 455' ?
C5 F3 3.425(2) '4 656' '1 565' ?
O1 O3 3.4305(14) '4 656' '4 656' ?
O2 H5 3.43(2) '4 656' '3 456' ?
C9 H13 3.43(2) '4 656' '2 554' ?
C13 C4 3.434(2) '4 656' '4 656' ?
C12 H7 3.45(2) '4 656' '2 664' ?
C9 F2 3.4588(17) '4 656' '2 554' ?
C8 O1 3.4650(15) '4 656' '4 656' ?
C7 H13 3.47(2) '4 656' '4 556' ?
H8 H5 3.49(3) '4 656' '1 455' ?
C6 H6 3.49(2) '4 656' '1 455' ?
C4 H13 3.50(2) '4 656' '4 656' ?
C4 H6 3.50(2) '4 656' '1 455' ?
C1 C12 3.506(2) '4 656' '4 656' ?
O2 O3 3.5307(15) '4 656' '2 554' ?
C13 H4 3.540(19) '4 656' '4 656' ?
H7 H6 3.54(3) '4 656' '1 455' ?
C8 H5 3.55(2) '4 656' '1 455' ?
C9 H8 3.546(16) '4 656' '4 656' ?
C6 F1 3.5585(17) '4 656' '1 465' ?
C11 H7 3.57(2) '4 656' '2 664' ?
F1 O3 3.5717(14) '4 656' '4 656' ?
C7 O3 3.5775(18) '4 656' '4 556' ?
F3 H7 3.579(19) '4 656' '1 455' ?
C9 F1 3.5793(16) '4 656' '2 654' ?
C6 H12 3.59(2) '4 656' '3 457' ?
C7 C12 3.591(2) '4 656' '2 564' ?
C9 C8 3.5945(17) '4 656' '4 656' ?
C11 F1 3.598(2) '4 656' '2 654' ?
C2 O1 3.6027(16) '4 656' '2 654' ?
C10 O1 3.630(2) '4 656' '4 656' ?
C1 C11 3.643(3) '4 656' '4 656' ?
C5 H6 3.65(2) '4 656' '1 455' ?
O1 F2 3.6561(15) '4 656' '2 554' ?
C8 O1 3.6648(15) '4 656' '2 554' ?
O1 H7 3.668(19) '4 656' '2 654' ?
C7 C11 3.669(3) '4 656' '2 564' ?
C5 H7 3.68(2) '4 656' '1 465' ?
C8 O3 3.6851(17) '4 656' '4 656' ?
O2 C8 3.6857(17) '4 656' '2 654' ?
O3 H8 3.686(15) '4 656' '4 756' ?
C4 H7 3.69(2) '4 656' '4 656' ?
C1 C4 3.6911(18) '4 656' '4 656' ?
C3 F2 3.6925(17) '4 656' '4 656' ?
C8 H5 3.70(2) '4 656' '4 656' ?
C8 F3 3.6993(18) '4 656' '4 656' ?
F1 H10 3.70(2) '4 656' '4 646' ?
C5 H8 3.705(17) '4 656' '4 656' ?
C1 F3 3.7119(14) '4 656' '4 656' ?
C10 H11 3.71(2) '4 656' '2 564' ?
C8 H13 3.72(2) '4 656' '4 556' ?
C6 F3 3.717(2) '4 656' '1 465' ?
C9 H11 3.72(2) '4 656' '2 564' ?
C12 H10 3.72(2) '4 656' '2 564' ?
C7 H4 3.73(2) '4 656' '4 656' ?
C3 H6 3.74(2) '4 656' '4 656' ?
C7 C6 3.757(2) '4 656' '1 455' ?
C8 H10 3.76(2) '4 656' '4 656' ?
C10 O1 3.764(2) '4 656' '2 654' ?
C12 H5 3.76(3) '4 656' '3 456' ?
C8 C6 3.772(2) '4 656' '1 455' ?
C13 H5 3.77(2) '4 656' . ?
C7 C5 3.775(3) '4 656' '1 455' ?
O2 C2 3.7791(14) '4 656' '4 656' ?
C10 C4 3.796(2) '4 656' '4 656' ?
C13 H11 3.80(2) '4 656' '4 646' ?
C11 H10 3.80(2) '4 656' '2 564' ?
C2 C5 3.799(2) '4 656' '4 656' ?
C6 C12 3.805(2) '4 656' '2 564' ?
C2 C7 3.808(2) '4 656' '4 656' ?
C1 O3 3.8130(14) '4 656' '2 554' ?
F1 H11 3.81(2) '4 656' '4 646' ?
F2 H5 3.82(2) '4 656' . ?
C13 H10 3.83(2) '4 656' '4 646' ?
O2 O1 3.8297(15) '4 656' '2 654' ?
O2 C13 3.8425(18) '4 656' '2 554' ?
C12 H8 3.843(17) '4 656' '2 654' ?
C12 H6 3.85(2) '4 656' '2 664' ?
C8 C11 3.847(3) '4 656' '2 564' ?
C9 C13 3.851(2) '4 656' '4 656' ?
C4 H12 3.85(2) '4 656' '3 457' ?
C1 F2 3.8571(16) '4 656' '2 554' ?
F1 H13 3.86(2) '4 656' '4 656' ?
C10 H4 3.880(16) '4 656' '4 656' ?
C10 F1 3.880(2) '4 656' '2 654' ?
O1 C11 3.880(2) '4 656' '4 646' ?
C13 H4 3.901(17) '4 656' . ?
C11 H8 3.906(17) '4 656' '2 664' ?
C6 H5 3.91(3) '4 656' '1 455' ?
O1 H10 3.92(2) '4 656' '2 554' ?
C2 H6 3.92(2) '4 656' '1 455' ?
F3 H8 3.926(16) '4 656' '4 656' ?
C1 H4 3.934(16) '4 656' '4 656' ?
O2 C5 3.9364(18) '4 656' '3 456' ?
C8 H12 3.94(2) '4 656' '2 564' ?
C5 H10 3.94(2) '4 656' '4 656' ?
C8 C10 3.940(2) '4 656' '4 656' ?
O1 O1 3.9469(16) '4 656' '2 654' ?
O1 O1 3.9469(16) '4 656' '2 554' ?
C5 H12 3.96(2) '4 656' '2 564' ?
C6 H8 3.962(17) '4 656' '1 465' ?
C5 C12 3.978(2) '4 656' '3 457' ?
C3 H11 3.99(2) '4 656' '2 564' ?
C6 H7 3.99(2) '4 656' '1 465' ?
C11 H11 3.99(2) '4 656' '2 564' ?
C10 C11 4.001(3) '4 656' '2 564' ?
C12 O1 4.002(2) '4 656' '4 656' ?
C1 H11 4.00(3) '4 656' '4 646' ?
F1 C4 4.010(2) '4 656' '4 656' ?
C11 F2 4.013(3) '4 656' '2 554' ?
C6 H11 4.02(2) '4 656' '2 564' ?
C10 H11 4.02(2) '4 656' '2 664' ?
C10 C11 4.023(3) '4 656' '2 664' ?
C7 F3 4.0259(17) '4 656' '1 465' ?
C9 C4 4.0291(19) '4 656' '4 656' ?
C8 C5 4.049(2) '4 656' '1 455' ?
O2 F3 4.0543(14) '4 656' '2 554' ?
C7 O1 4.0605(16) '4 656' '2 554' ?
O1 F3 4.0723(12) '4 656' '4 656' ?
C5 O3 4.087(2) '4 656' '4 656' ?
C6 C6 4.087(3) '4 656' '1 465' ?
C6 C6 4.087(3) '4 656' '1 455' ?
C8 O3 4.0896(17) '4 656' '4 556' ?
C10 F1 4.093(2) '4 656' '4 666' ?
C11 C11 4.094(4) '4 656' '2 664' ?
C11 C11 4.094(4) '4 656' '2 564' ?
C3 C6 4.112(2) '4 656' '1 455' ?
C1 C8 4.1249(16) '4 656' '2 654' ?
C10 F2 4.129(2) '4 656' '2 554' ?
C1 C1 4.1396(17) '4 656' '2 554' ?
C1 C1 4.1396(17) '4 656' '2 654' ?
C7 F1 4.1413(18) '4 656' '4 656' ?
O2 O3 4.1670(12) '4 656' '4 656' ?
C5 O3 4.176(2) '4 656' '1 565' ?
C9 F2 4.1766(18) '4 656' '4 656' ?
C9 O3 4.1814(17) '4 656' '2 554' ?
C11 F1 4.189(2) '4 656' '4 666' ?
C8 C12 4.191(2) '4 656' '2 564' ?
C6 C13 4.196(2) '4 656' '1 465' ?
O2 C2 4.1976(17) '4 656' '2 554' ?
C10 C12 4.200(3) '4 656' '2 664' ?
C5 F1 4.214(2) '4 656' '1 465' ?
C13 O1 4.2161(17) '4 656' '2 654' ?
C6 C11 4.248(3) '4 656' '2 564' ?
C9 C11 4.248(3) '4 656' '2 564' ?
C6 C12 4.250(2) '4 656' '3 457' ?
C9 C8 4.2547(18) '4 656' '2 654' ?
C9 C1 4.2699(19) '4 656' '2 654' ?
O2 C13 4.2789(18) '4 656' '2 654' ?
C1 C7 4.2816(18) '4 656' '4 656' ?
C2 C6 4.308(2) '4 656' '4 656' ?
C5 C6 4.308(3) '4 656' '1 465' ?
C10 C13 4.312(2) '4 656' '4 666' ?
O2 C6 4.3181(17) '4 656' '3 456' ?
C13 C11 4.320(3) '4 656' '4 646' ?
O2 C7 4.3279(19) '4 656' '2 654' ?
C5 F1 4.335(2) '4 656' '4 666' ?
C7 F1 4.3360(15) '4 656' '1 465' ?
C1 F1 4.3557(14) '4 656' '2 654' ?
C12 C13 4.371(3) '4 656' '2 654' ?
C9 F1 4.3735(16) '4 656' '4 656' ?
C12 C13 4.381(3) '4 656' '2 554' ?
C5 F3 4.382(2) '4 656' '4 656' ?
C1 O1 4.3871(17) '4 656' '2 554' ?
C5 C6 4.387(3) '4 656' '1 455' ?
C12 C11 4.392(3) '4 656' '2 564' ?
C6 C4 4.398(3) '4 656' '1 465' ?
C10 C10 4.399(3) '4 656' '2 664' ?
C10 C10 4.399(3) '4 656' '2 564' ?
C7 C13 4.427(2) '4 656' '4 656' ?

_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   ?

_geom_special_details            ?

_cell_special_details            
; ?
;

_exptl_special_details           
; ?
;

_diffrn_special_details          
; ?
;

_chemical_compound_source        ?
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_analytical     ?
_chemical_formula_structural     ?

_exptl_crystal_F_000             552

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
? ?

_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              23
_reflns_number_observed          ?
_reflns_d_resolution_high        .837
_reflns_d_resolution_low         7.368

_diffrn_reflns_av_sigmaI/netI    .011
_diffrn_reflns_theta_min         6.
_diffrn_reflns_reduction_process ?

_diffrn_ambient_temperature      293
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_diffrn_radiation_detector       ?

_refine_ls_extinction_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970'
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          .025
_refine_ls_wR_factor_all         .032
_refine_ls_goodness_of_fit_all   1.022
_refine_ls_shift/su_mean         .

#==========================================================================
# Structure Factor lists should be submitted as separate files
#==========================================================================

#data_<structure> # but for xtal use the refln data is needed in same block

loop_
_refln_index_h
_refln_index_k
_refln_index_l
_refln_F_meas
_refln_F_calc
_refln_F_sigma
_refln_F_squared_meas
_refln_F_squared_calc
_refln_F_squared_sigma
_refln_observed_status
_refln_F_meas_friedel
_refln_F_sigma_friedel
_refln_F_squared_meas_friedel
_refln_F_squared_sigma_friedel
? ? ? ? ? ? ? ? ? ? ? ? ? ?

#-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end