# Supplementary Material for PCCP # This journal is © The Owner Societies 2011 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Desiraju, Gautam' _publ_contact_author_email 'gautam desiraju@yahoo.com' _publ_section_title ; Thakur, Tejender; Kirchner, Michael; Blaser, Dieter; Boese, Roland; Desiraju, Gautam ; loop_ _publ_author_name T.Thakur M.Kirchner D.Blaser R.Boese G.Desiraju # Attachment '- Formaldehyde_779999.txt' data_formaldehyd_0m _database_code_depnum_ccdc_archive 'CCDC 779999' #TrackingRef '- Formaldehyde_779999.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; formaldehyde ; _chemical_name_common formaldehyde _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H2 O' _chemical_formula_weight 30.03 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 tetragonal _symmetry_space_group_name_H-M P-421c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 8.7411(10) _cell_length_b 8.7411(10) _cell_length_c 4.4740(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 341.84(9) _cell_formula_units_Z 8 _cell_measurement_temperature 148(2) _cell_measurement_reflns_used 542 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 27.04 _exptl_crystal_description cylindric _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 128 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystallization was performed on the diffractometer at a temperature of 148 K with a miniature zone melting procedure using focussed infrared-laser- radiation according to: R. Boese, M. Nussbaumer, "In Situ Crystallisation Techniques", in: "Organic Crystal Chemistry", Ed. D.W. Jones, Oxford University Press, Oxford, England, (1994) 20-37 ; _diffrn_ambient_temperature 148(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 ; Siemens SMART three axis goniometer with APEX II area detector system ; _diffrn_measurement_method ; Data collection strategy APEX 2 / COSMO with chi = 0 ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1492 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 31.70 _reflns_number_total 436 _reflns_number_gt 352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_cell_refinement 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_data_reduction 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_structure_solution 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_structure_refinement 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _computing_molecular_graphics 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _computing_publication_material 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _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. Hydrogen atoms position taken froma Fourier-map and were refined without constraints. ; _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^)+(0.0235P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(14) _chemical_absolute_configuration unk _refine_ls_number_reflns 436 _refine_ls_number_parameters 27 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 0.24394(7) 0.04398(7) 0.37503(18) 0.0438(3) Uani 1 1 d . . . C1 C 0.24702(9) 0.01339(10) 0.6352(3) 0.0419(3) Uani 1 1 d . . . H1 H 0.3253(10) -0.0578(12) 0.723(2) 0.042(3) Uiso 1 1 d . . . H2 H 0.1698(13) 0.0648(13) 0.788(3) 0.062(4) Uiso 1 1 d . . . 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 0.0497(3) 0.0533(3) 0.0285(7) 0.0024(3) 0.0020(6) -0.0063(3) C1 0.0441(4) 0.0444(4) 0.0371(9) -0.0028(6) -0.0036(12) -0.0017(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 O1 C1 1.1948(13) . ? C1 H1 1.004(10) . ? C1 H2 1.059(12) . ? 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 O1 C1 H1 122.3(5) . . ? O1 C1 H2 121.2(6) . . ? H1 C1 H2 116.5(8) . . ? _diffrn_measured_fraction_theta_max 0.770 _diffrn_reflns_theta_full 31.70 _diffrn_measured_fraction_theta_full 0.770 _refine_diff_density_max 0.066 _refine_diff_density_min -0.057 _refine_diff_density_rms 0.016 _vrf_PLAT029_formaldehyd_0m ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.77 RESPONSE: The low coverage resulted from the orientation of the cylindric crystal and the chosen scan mode, both due to the in situ crystal growing technique. Any other mounting of the crystal / scan mode would lead to a melting of the crystal. ; # Attachment '- N-Methylformamide_780001.txt' data_me_formamid _database_code_depnum_ccdc_archive 'CCDC 780000' #TrackingRef '- N-Methylformamide_780001.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-methylformamide ; _chemical_name_common N-methylformamide _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H5 N O' _chemical_formula_weight 59.07 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' _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 8.7855(6) _cell_length_b 8.5307(6) _cell_length_c 8.6148(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.207(4) _cell_angle_gamma 90.00 _cell_volume 645.64(8) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 6044 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.33 _exptl_crystal_description cylindric _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystallization was performed on the diffractometer at a temperature of 250 K with a miniature zone melting procedure using focussed infrared-laser- radiation according to: R. Boese, M. Nussbaumer, "In Situ Crystallisation Techniques", in: "Organic Crystal Chemistry", Ed. D.W. Jones, Oxford University Press, Oxford, England, (1994) 20-37 ; _diffrn_ambient_temperature 203(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 ; Siemens SMART three axis goniometer with APEX II area detector system ; _diffrn_measurement_method ; Data collection strategy APEX 2 / COSMO with chi = 0 ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9778 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.46 _reflns_number_total 1035 _reflns_number_gt 940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_cell_refinement 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_data_reduction 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_structure_solution 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_structure_refinement 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _computing_molecular_graphics 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _computing_publication_material 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _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. Treatment of hydrogen Riding model on idealized geometrics with the 1.2 fold (1.5 fold for methyl groups) isotropic displacement parameters of the equivalent Uij of the corresponding carbon atom, the other hydrogen atoms taken from a Fourier-map and were refined without constraints. ; _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^)+(0.0425P)^2^+0.2134P] 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 SHELXL _refine_ls_extinction_coef 0.067(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1035 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.51890(10) 0.25031(12) 0.61542(13) 0.0371(4) Uani 1 1 d . . . N1 N 0.31339(14) 0.38821(14) 0.53443(17) 0.0338(4) Uani 1 1 d . . . H1N H 0.269(2) 0.422(2) 0.456(2) 0.043(5) Uiso 1 1 d . . . C1 C 0.44022(15) 0.30871(16) 0.5120(2) 0.0320(4) Uani 1 1 d . . . H1 H 0.4691(17) 0.2994(19) 0.403(2) 0.039(5) Uiso 1 1 d . . . C2 C 0.25501(17) 0.4194(2) 0.6872(2) 0.0431(5) Uani 1 1 d . . . H2A H 0.2432 0.3214 0.7430 0.065 Uiso 1 1 d R . . H2B H 0.1571 0.4712 0.6787 0.065 Uiso 1 1 d R . . H2C H 0.3256 0.4866 0.7428 0.065 Uiso 1 1 d R . . O11 O 0.16275(11) 0.50899(13) 0.26291(13) 0.0414(4) Uani 1 1 d . . . N11 N 0.21030(14) 0.65226(15) 0.04792(17) 0.0349(4) Uani 1 1 d . . . H11N H 0.276(2) 0.680(2) -0.012(2) 0.042(5) Uiso 1 1 d . . . C11 C 0.24934(16) 0.55785(17) 0.1623(2) 0.0342(4) Uani 1 1 d . . . H11 H 0.3573(19) 0.5319(19) 0.157(2) 0.042(4) Uiso 1 1 d . . . C12 C 0.05767(17) 0.71437(19) 0.0309(2) 0.0440(5) Uani 1 1 d . . . H12A H -0.0122 0.6296 0.0073 0.066 Uiso 1 1 d R . . H12B H 0.0556 0.7905 -0.0527 0.066 Uiso 1 1 d R . . H12C H 0.0274 0.7646 0.1270 0.066 Uiso 1 1 d 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 0.0343(5) 0.0493(7) 0.0278(8) 0.0014(5) 0.0011(4) 0.0047(4) N1 0.0357(6) 0.0413(7) 0.0243(10) 0.0051(6) -0.0039(6) -0.0001(5) C1 0.0345(7) 0.0379(8) 0.0235(12) -0.0012(6) 0.0025(6) -0.0075(6) C2 0.0410(8) 0.0555(10) 0.0328(13) 0.0023(7) 0.0035(7) 0.0109(7) O11 0.0418(6) 0.0492(7) 0.0331(9) 0.0092(5) -0.0009(5) -0.0006(5) N11 0.0345(6) 0.0433(7) 0.0269(10) 0.0012(6) 0.0046(6) -0.0061(5) C11 0.0317(7) 0.0398(8) 0.0310(11) -0.0048(7) -0.0023(6) -0.0002(6) C12 0.0421(8) 0.0449(9) 0.0450(13) 0.0118(7) -0.0046(7) -0.0019(6) _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 C1 1.2309(19) . ? N1 C1 1.3193(19) . ? N1 C2 1.439(2) . ? N1 H1N 0.82(2) . ? C1 H1 0.98(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? O11 C11 1.2282(19) . ? N11 C11 1.317(2) . ? N11 C12 1.449(2) . ? N11 H11N 0.811(19) . ? C11 H11 0.975(17) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? 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 C1 N1 C2 122.21(14) . . ? C1 N1 H1N 117.0(13) . . ? C2 N1 H1N 120.8(13) . . ? O1 C1 N1 125.07(17) . . ? O1 C1 H1 121.1(9) . . ? N1 C1 H1 113.8(9) . . ? N1 C2 H2A 109.4 . . ? N1 C2 H2B 109.6 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.4 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C11 N11 C12 122.53(14) . . ? C11 N11 H11N 117.8(13) . . ? C12 N11 H11N 119.6(13) . . ? O11 C11 N11 125.11(13) . . ? O11 C11 H11 124.1(10) . . ? N11 C11 H11 110.8(10) . . ? N11 C12 H12A 109.5 . . ? N11 C12 H12B 109.6 . . ? H12A C12 H12B 109.5 . . ? N11 C12 H12C 109.3 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 25.46 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 0.190 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032 _vrf_PLAT029_me_formamid ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.86 RESPONSE: The low coverage resulted from the orientation of the cylindric crystal and the chosen scan mode, both due to the in situ crystal growing technique. Any other mounting of the crystal / scan mode would lead to a melting of the crystal. ; # Attachment '- Acrolein_780000.txt' data_propenal _database_code_depnum_ccdc_archive 'CCDC 780001' #TrackingRef '- Acrolein_780000.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H4 O' _chemical_formula_weight 56.06 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.134(8) _cell_length_b 9.694(11) _cell_length_c 9.930(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 686.7(13) _cell_formula_units_Z 8 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 328 _cell_measurement_theta_min 4.19 _cell_measurement_theta_max 20.51 _exptl_crystal_description cylindric _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystallization was performed on the diffractometer at a temperature of 133 K with a miniature zone melting procedure using focussed infrared-laser- radiation according to: R. Boese, M. Nussbaumer, "In Situ Crystallisation Techniques", in: "Organic Crystal Chemistry", Ed. D.W. Jones, Oxford University Press, Oxford, England, (1994) 20-37 ; _diffrn_ambient_temperature 133(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 ; Siemens SMART three axis goniometer with APEX II area detector system ; _diffrn_measurement_method ; Data collection strategy APEX 2 / COSMO with chi = 0 ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1891 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.40 _reflns_number_total 506 _reflns_number_gt 291 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_cell_refinement 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_data_reduction 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_structure_solution 'BRUKER AXS SMART APEX 2 Vers. 3.0-2009' _computing_structure_refinement 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _computing_molecular_graphics 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _computing_publication_material 'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4' _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. Hydrogen atoms position taken froma Fourier-map and were refined without constraints. ; _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^)+(0.0345P)^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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 506 _refine_ls_number_parameters 54 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _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 0.11114(19) 0.49323(15) 0.30514(19) 0.0679(7) Uani 1 1 d . . . C1 C 0.1420(3) 0.5380(2) 0.1938(3) 0.0498(7) Uani 1 1 d . . . H1 H 0.215(2) 0.4853(18) 0.1245(18) 0.055(6) Uiso 1 1 d . . . C2 C 0.0805(3) 0.6710(2) 0.1433(3) 0.0454(7) Uani 1 1 d . . . H2 H 0.015(3) 0.725(2) 0.204(2) 0.067(7) Uiso 1 1 d . . . C3 C 0.1197(3) 0.7123(2) 0.0210(3) 0.0542(7) Uani 1 1 d . . . H3A H 0.080(2) 0.802(2) -0.0093(19) 0.053(6) Uiso 1 1 d . . . H3B H 0.194(3) 0.658(2) -0.033(2) 0.060(7) Uiso 1 1 d . . . 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 0.0821(11) 0.0567(10) 0.0650(17) 0.0190(9) -0.0054(9) -0.0055(7) C1 0.0475(12) 0.0433(12) 0.059(2) -0.0071(12) -0.0059(12) -0.0004(9) C2 0.0535(12) 0.0404(12) 0.042(2) -0.0034(11) 0.0020(10) 0.0025(10) C3 0.0576(14) 0.0518(15) 0.053(2) -0.0017(13) -0.0021(12) -0.0048(12) _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 C1 1.208(3) . ? C1 C2 1.451(3) . ? C2 C3 1.310(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 O1 C1 C2 125.5(2) . . ? C3 C2 C1 121.8(2) . . ? _diffrn_measured_fraction_theta_max 0.799 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.799 _refine_diff_density_max 0.106 _refine_diff_density_min -0.093 _refine_diff_density_rms 0.027 _vrf_PLAT029_propenal ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.80 RESPONSE: The low coverage resulted from the orientation of the cylindric crystal and the chosen scan mode, both due to the in situ crystal growing technique. Any other mounting of the crystal / scan mode would lead to a melting of the crystal. ;