# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mhmd_jida@yahoo.com _publ_contact_author_name 'Mouhamad Jida' loop_ _publ_author_name 'Mouhamad Jida' 'Mohamad Soueidan' 'Benoit Depreza' 'Guillaume Laconde' 'Rebecca Deprez-Poulain' data_moj246-12-ok _database_code_depnum_ccdc_archive 'CCDC 856036' #TrackingRef 'moj246-12-ok.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 8.715(4) _cell_length_b 11.090(4) _cell_length_c 13.771(7) _cell_angle_alpha 90 _cell_angle_beta 90.303(6) _cell_angle_gamma 90 _cell_volume 1330.9(10) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C15 N2 O2 # Dc = 1.20 Fooo = 544.00 Mu = 0.83 M = 240.18 # Found Formula = C16 H18 N2 O1 # Dc = 1.27 FOOO = 544.00 Mu = 0.80 M = 254.33 _chemical_formula_sum 'C16 H18 N2 O1' _chemical_formula_moiety 'C16 H18 N2 O1' _chemical_compound_source ? _chemical_formula_weight 254.33 _cell_measurement_reflns_used 2690 _cell_measurement_theta_min 2 _cell_measurement_theta_max 22 _cell_measurement_temperature 293 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_min 0.120 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_max 0.600 _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.080 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 31806 _reflns_number_total 3310 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3310 # Theoretical number of reflections is about 6043 _diffrn_reflns_theta_min 2.337 _diffrn_reflns_theta_max 28.296 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.296 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 4.36 _oxford_diffrn_Wilson_scale 39.88 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.14 _refine_diff_density_max 0.21 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 1281 _refine_ls_number_restraints 0 _refine_ls_number_parameters 173 _oxford_refine_ls_R_factor_ref 0.0470 _refine_ls_wR_factor_ref 0.0447 _refine_ls_goodness_of_fit_ref 1.0510 _refine_ls_shift/su_max 0.0001383 _refine_ls_shift/su_mean 0.0000265 # The values computed from all data _oxford_reflns_number_all 3299 _refine_ls_R_factor_all 0.1130 _refine_ls_wR_factor_all 0.1143 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2128 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_gt 0.0602 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.338 0.389 0.155 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.6651(3) 0.09096(18) 0.61691(15) 0.0887 1.0000 Uani . . . . . . . C2 C 0.6691(3) 0.1161(3) 0.5291(2) 0.0647 1.0000 Uani . . . . . . . N3 N 0.6303(2) 0.22605(19) 0.49728(15) 0.0578 1.0000 Uani . . . . . . . C4 C 0.6358(3) 0.2650(2) 0.39388(17) 0.0532 1.0000 Uani . . . . . . . C5 C 0.7026(3) 0.3910(2) 0.39602(18) 0.0536 1.0000 Uani . . . . . . . N6 N 0.7404(2) 0.4514(2) 0.31184(15) 0.0631 1.0000 Uani . . . . . . . C7 C 0.8100(3) 0.5589(2) 0.3377(2) 0.0592 1.0000 Uani . . . . . . . C8 C 0.8143(3) 0.5644(2) 0.4391(2) 0.0594 1.0000 Uani . . . . . . . C9 C 0.7433(3) 0.4568(2) 0.47388(18) 0.0553 1.0000 Uani . . . . . . . C10 C 0.7074(3) 0.4154(2) 0.57451(18) 0.0648 1.0000 Uani . . . . . . . C11 C 0.5856(3) 0.3185(3) 0.56739(19) 0.0686 1.0000 Uani . . . . . . . C12 C 0.8810(3) 0.6647(3) 0.4829(2) 0.0733 1.0000 Uani . . . . . . . C13 C 0.9376(3) 0.7546(3) 0.4248(3) 0.0850 1.0000 Uani . . . . . . . C14 C 0.9308(3) 0.7480(3) 0.3251(3) 0.0854 1.0000 Uani . . . . . . . C15 C 0.8663(3) 0.6492(3) 0.2783(3) 0.0754 1.0000 Uani . . . . . . . C16 C 0.4734(3) 0.2637(3) 0.3509(2) 0.0684 1.0000 Uani . . . . . . . C17 C 0.7428(3) 0.1827(2) 0.3381(2) 0.0655 1.0000 Uani . . . . . . . C18 C 0.7034(4) 0.0516(3) 0.3527(2) 0.0752 1.0000 Uani . . . . . . . C19 C 0.7216(4) 0.0229(3) 0.4594(2) 0.0763 1.0000 Uani . . . . . . . H102 H 0.7996 0.3828 0.6049 0.0786 1.0000 Uiso R . . . . . . H101 H 0.6698 0.4826 0.6130 0.0790 1.0000 Uiso R . . . . . . H112 H 0.5656 0.2812 0.6295 0.0830 1.0000 Uiso R . . . . . . H111 H 0.4904 0.3548 0.5434 0.0828 1.0000 Uiso R . . . . . . H121 H 0.8879 0.6675 0.5506 0.0901 1.0000 Uiso R . . . . . . H131 H 0.9796 0.8211 0.4536 0.1011 1.0000 Uiso R . . . . . . H141 H 0.9691 0.8119 0.2885 0.1029 1.0000 Uiso R . . . . . . H151 H 0.8599 0.6449 0.2113 0.0921 1.0000 Uiso R . . . . . . H161 H 0.4757 0.3059 0.2900 0.1058 1.0000 Uiso R . . . . . . H163 H 0.4030 0.3020 0.3955 0.1057 1.0000 Uiso R . . . . . . H162 H 0.4419 0.1811 0.3394 0.1059 1.0000 Uiso R . . . . . . H172 H 0.8475 0.1954 0.3619 0.0821 1.0000 Uiso R . . . . . . H171 H 0.7342 0.2054 0.2675 0.0815 1.0000 Uiso R . . . . . . H182 H 0.7783 0.0021 0.3150 0.0946 1.0000 Uiso R . . . . . . H181 H 0.5997 0.0320 0.3305 0.0953 1.0000 Uiso R . . . . . . H192 H 0.8289 0.0093 0.4721 0.0912 1.0000 Uiso R . . . . . . H191 H 0.6642 -0.0496 0.4712 0.0915 1.0000 Uiso R . . . . . . H61 H 0.7255 0.4260 0.2531 0.0758 1.0000 Uiso 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 0.1165(18) 0.0838(15) 0.0658(14) 0.0200(11) -0.0077(11) 0.0015(12) C2 0.0664(17) 0.0688(18) 0.0588(18) 0.0126(16) -0.0052(13) 0.0001(15) N3 0.0582(13) 0.0658(14) 0.0493(13) 0.0032(11) 0.0045(10) 0.0111(11) C4 0.0503(14) 0.0618(16) 0.0476(15) 0.0033(12) 0.0042(10) 0.0081(13) C5 0.0479(14) 0.0637(16) 0.0492(16) 0.0070(14) 0.0040(11) 0.0111(13) N6 0.0660(14) 0.0722(15) 0.0510(14) 0.0026(12) 0.0012(10) 0.0026(12) C7 0.0482(15) 0.0569(16) 0.0724(19) 0.0015(15) 0.0013(12) 0.0073(13) C8 0.0462(14) 0.0610(17) 0.0708(18) -0.0082(15) -0.0011(12) 0.0137(14) C9 0.0545(15) 0.0584(16) 0.0531(16) -0.0024(13) 0.0008(11) 0.0148(13) C10 0.0711(18) 0.0729(18) 0.0503(17) -0.0086(13) -0.0004(12) 0.0248(16) C11 0.0674(17) 0.086(2) 0.0530(17) 0.0034(15) 0.0114(13) 0.0164(17) C12 0.0538(17) 0.0736(19) 0.092(2) -0.0147(19) -0.0018(15) 0.0118(16) C13 0.0523(19) 0.064(2) 0.139(4) -0.014(2) 0.0052(19) 0.0088(15) C14 0.0528(18) 0.068(2) 0.136(4) 0.014(2) 0.0122(18) 0.0095(16) C15 0.0564(17) 0.076(2) 0.094(2) 0.0155(18) 0.0040(15) 0.0064(17) C16 0.0586(17) 0.0767(19) 0.0698(19) 0.0034(14) -0.0084(13) 0.0055(15) C17 0.0695(17) 0.0685(18) 0.0587(16) -0.0042(14) 0.0056(13) 0.0116(15) C18 0.086(2) 0.0655(18) 0.074(2) -0.0070(15) -0.0022(15) 0.0100(16) C19 0.087(2) 0.0621(18) 0.079(2) 0.0029(16) -0.0048(16) 0.0056(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2000(6) loop_ _oxford_twin_element_scale_factors 0.9214(14) 0.0786(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.242(3) yes C2 . N3 . 1.339(3) yes C2 . C19 . 1.484(4) yes N3 . C4 . 1.489(3) yes N3 . C11 . 1.463(3) yes C4 . C5 . 1.514(4) yes C4 . C16 . 1.532(4) yes C4 . C17 . 1.516(4) yes C5 . N6 . 1.380(3) yes C5 . C9 . 1.343(3) yes N6 . C7 . 1.383(3) yes N6 . H61 . 0.865 no C7 . C8 . 1.399(4) yes C7 . C15 . 1.385(4) yes C8 . C9 . 1.428(4) yes C8 . C12 . 1.392(4) yes C9 . C10 . 1.495(4) yes C10 . C11 . 1.513(4) yes C10 . H102 . 0.973 no C10 . H101 . 0.973 no C11 . H112 . 0.967 no C11 . H111 . 0.978 no C12 . C13 . 1.372(4) yes C12 . H121 . 0.934 no C13 . C14 . 1.376(5) yes C13 . H131 . 0.913 no C14 . C15 . 1.389(5) yes C14 . H141 . 0.933 no C15 . H151 . 0.925 no C16 . H161 . 0.961 no C16 . H163 . 0.969 no C16 . H162 . 0.969 no C17 . C18 . 1.508(4) yes C17 . H172 . 0.979 no C17 . H171 . 1.007 no C18 . C19 . 1.511(4) yes C18 . H182 . 1.000 no C18 . H181 . 0.977 no C19 . H192 . 0.962 no C19 . H191 . 0.961 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C2 . N3 . 121.0(3) yes O1 . C2 . C19 . 119.0(3) yes N3 . C2 . C19 . 120.1(3) yes C2 . N3 . C4 . 124.6(2) yes C2 . N3 . C11 . 119.4(2) yes C4 . N3 . C11 . 116.0(2) yes N3 . C4 . C5 . 105.28(19) yes N3 . C4 . C16 . 109.4(2) yes C5 . C4 . C16 . 111.8(2) yes N3 . C4 . C17 . 109.5(2) yes C5 . C4 . C17 . 109.1(2) yes C16 . C4 . C17 . 111.6(2) yes C4 . C5 . N6 . 121.7(2) yes C4 . C5 . C9 . 128.1(2) yes N6 . C5 . C9 . 110.1(2) yes C5 . N6 . C7 . 108.0(2) yes C5 . N6 . H61 . 126.3 no C7 . N6 . H61 . 125.7 no N6 . C7 . C8 . 107.7(2) yes N6 . C7 . C15 . 128.9(3) yes C8 . C7 . C15 . 123.4(3) yes C7 . C8 . C9 . 106.8(2) yes C7 . C8 . C12 . 118.5(3) yes C9 . C8 . C12 . 134.7(3) yes C8 . C9 . C5 . 107.4(2) yes C8 . C9 . C10 . 131.4(2) yes C5 . C9 . C10 . 121.2(2) yes C9 . C10 . C11 . 107.9(2) yes C9 . C10 . H102 . 109.6 no C11 . C10 . H102 . 110.0 no C9 . C10 . H101 . 110.0 no C11 . C10 . H101 . 110.0 no H102 . C10 . H101 . 109.3 no C10 . C11 . N3 . 110.6(2) yes C10 . C11 . H112 . 112.1 no N3 . C11 . H112 . 109.5 no C10 . C11 . H111 . 108.9 no N3 . C11 . H111 . 107.1 no H112 . C11 . H111 . 108.5 no C8 . C12 . C13 . 118.6(3) yes C8 . C12 . H121 . 118.9 no C13 . C12 . H121 . 122.5 no C12 . C13 . C14 . 122.0(3) yes C12 . C13 . H131 . 118.6 no C14 . C13 . H131 . 119.4 no C13 . C14 . C15 . 121.4(3) yes C13 . C14 . H141 . 119.1 no C15 . C14 . H141 . 119.6 no C14 . C15 . C7 . 116.1(3) yes C14 . C15 . H151 . 121.7 no C7 . C15 . H151 . 122.2 no C4 . C16 . H161 . 108.0 no C4 . C16 . H163 . 109.8 no H161 . C16 . H163 . 110.9 no C4 . C16 . H162 . 109.4 no H161 . C16 . H162 . 108.9 no H163 . C16 . H162 . 109.8 no C4 . C17 . C18 . 111.8(2) yes C4 . C17 . H172 . 108.6 no C18 . C17 . H172 . 107.9 no C4 . C17 . H171 . 107.3 no C18 . C17 . H171 . 110.7 no H172 . C17 . H171 . 110.6 no C17 . C18 . C19 . 108.1(2) yes C17 . C18 . H182 . 108.1 no C19 . C18 . H182 . 108.8 no C17 . C18 . H181 . 112.6 no C19 . C18 . H181 . 110.5 no H182 . C18 . H181 . 108.7 no C18 . C19 . C2 . 116.8(2) yes C18 . C19 . H192 . 107.9 no C2 . C19 . H192 . 107.1 no C18 . C19 . H191 . 106.8 no C2 . C19 . H191 . 108.1 no H192 . C19 . H191 . 110.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N6 . H61 . O1 3_554 165 0.87 1.95 2.800(4) yes