# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2012
data_global
#TrackingRef '- 3a.cif'
_audit_update_record
;
2011-11-04 # Formatted by publCIF
;
_journal_name_full 'Green Chemistry'
_journal_coden_Cambridge 1048
loop_
_publ_author_name
'Liupan Yang'
'Daxin Shi'
'Shu Chen'
'Hongxin Chai'
'Danfei Huang'
'Qi Zhang'
'Jiarong Li'
_publ_contact_author_name 'Jiarong Li'
_publ_contact_author_email jrli@bit.edu.cn
data_I
_database_code_depnum_ccdc_archive 'CCDC 792400'
_chemical_name_systematic
;
Spiro[cyclopentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-
4'(3'H)-one
;
_chemical_name_common ?
_chemical_formula_moiety 'C11 H13 N3 O'
_chemical_formula_sum 'C11 H13 N3 O'
_chemical_formula_iupac 'C11 H13 N3 O'
_chemical_formula_weight 203.24
_chemical_melting_point ?
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_space_group_name_Hall '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
_cell_length_a 10.4000(10)
_cell_length_b 12.1650(15)
_cell_length_c 15.370(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1944.6(4)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 9441
_cell_measurement_theta_min 1.30
_cell_measurement_theta_max 35.60
_cell_measurement_temperature 113(2)
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.28
_exptl_crystal_density_diffrn 1.388
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 864
_exptl_absorpt_coefficient_mu 0.093
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(CrystalClear-SM Expert; Rigaku/MSC, 2009)'
_exptl_absorpt_correction_T_min 0.9709
_exptl_absorpt_correction_T_max 0.9744
_exptl_special_details
;
;
_diffrn_ambient_temperature 113(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_source 'rotating anode'
_diffrn_radiation_monochromator 'graphite multilayer'
_diffrn_measurement_device_type 'Rigaku Saturn724 CCD'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number 21571
_diffrn_reflns_av_R_equivalents 0.0365
_diffrn_reflns_av_sigmaI/netI 0.0190
_diffrn_reflns_theta_min 2.65
_diffrn_reflns_theta_max 27.88
_diffrn_reflns_theta_full 27.88
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_reflns_number_total 2314
_reflns_number_gt 2168
_reflns_threshold_expression I>2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0427
_refine_ls_R_factor_gt 0.0395
_refine_ls_wR_factor_gt 0.0999
_refine_ls_wR_factor_ref 0.1026
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_refine_ls_number_reflns 2314
_refine_ls_number_parameters 144
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.6834P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.404
_refine_diff_density_min -0.203
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_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^ >
\s(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.
;
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'
_computing_data_collection 'Crystal Clear-SM Expert (Rigaku/MSC, 2009)'
_computing_cell_refinement 'Crystal Clear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_reduction 'Crystal Clear-SM Expert (Rigaku/MSC, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'CrystalStructure (Rigaku/MSC, 2009)'
_computing_publication_material 'CrystalStructure (Rigaku/MSC, 2009)'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.59391(7) 0.42006(6) 0.57792(5) 0.01563(19) Uani d . 1 2 . .
N N1 0.94264(9) 0.63850(8) 0.68372(6) 0.0171(2) Uani d . 1 2 . .
N N2 0.80796(9) 0.69549(8) 0.57226(6) 0.0155(2) Uani d . 1 2 . .
N N3 0.64694(9) 0.58137(7) 0.51402(6) 0.0146(2) Uani d . 1 2 . .
C C1 0.84778(10) 0.61467(9) 0.62723(7) 0.0137(2) Uani d . 1 2 . .
C C2 0.78414(10) 0.51204(9) 0.62574(7) 0.0137(2) Uani d . 1 2 . .
C C3 0.82323(11) 0.43170(9) 0.68436(7) 0.0164(2) Uani d . 1 2 . .
H H3 0.7818 0.3621 0.6855 0.020 Uiso calc R 1 2 . .
C C4 0.92347(11) 0.45420(9) 0.74123(7) 0.0185(2) Uani d . 1 2 . .
H H4 0.9539 0.4001 0.7808 0.022 Uiso calc R 1 2 . .
C C5 0.97766(11) 0.55837(9) 0.73836(7) 0.0184(2) Uani d . 1 2 . .
H H5 1.0449 0.5740 0.7783 0.022 Uiso calc R 1 2 . .
C C6 0.66943(10) 0.49939(9) 0.57020(7) 0.0130(2) Uani d . 1 2 . .
C C7 0.74197(10) 0.66576(8) 0.49201(7) 0.0134(2) Uani d . 1 2 . .
C C8 0.83702(11) 0.62728(9) 0.42121(7) 0.0168(2) Uani d . 1 2 . .
H H8A 0.9065 0.5818 0.4465 0.020 Uiso calc R 1 2 . .
H H8B 0.7924 0.5845 0.3755 0.020 Uiso calc R 1 2 . .
C C9 0.88986(11) 0.73498(9) 0.38493(7) 0.0193(2) Uani d . 1 2 . .
H H9A 0.9265 0.7242 0.3261 0.023 Uiso calc R 1 2 . .
H H9B 0.9571 0.7656 0.4235 0.023 Uiso calc R 1 2 . .
C C10 0.77185(12) 0.81065(10) 0.38176(8) 0.0231(3) Uani d . 1 2 . .
H H10A 0.7316 0.8083 0.3234 0.028 Uiso calc R 1 2 . .
H H10B 0.7969 0.8875 0.3947 0.028 Uiso calc R 1 2 . .
C C11 0.67779(10) 0.76755(9) 0.45118(7) 0.0160(2) Uani d . 1 2 . .
H H11A 0.5946 0.7474 0.4242 0.019 Uiso calc R 1 2 . .
H H11B 0.6620 0.8244 0.4960 0.019 Uiso calc R 1 2 . .
H H1 0.8471(15) 0.7598(14) 0.5750(10) 0.030(4) Uiso d . 1 2 . .
H H2 0.5769(16) 0.5770(12) 0.4815(10) 0.024(4) Uiso d . 1 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0148(4) 0.0129(4) 0.0193(4) -0.0014(3) 0.0001(3) 0.0009(3)
N1 0.0166(4) 0.0201(5) 0.0147(4) -0.0014(4) -0.0011(3) -0.0010(4)
N2 0.0177(5) 0.0121(5) 0.0166(4) -0.0029(4) -0.0033(4) 0.0003(3)
N3 0.0123(4) 0.0140(4) 0.0175(4) -0.0023(3) -0.0029(4) 0.0020(3)
C1 0.0134(5) 0.0147(5) 0.0131(5) 0.0007(4) 0.0024(4) -0.0013(4)
C2 0.0135(5) 0.0146(5) 0.0130(5) 0.0008(4) 0.0008(4) -0.0010(4)
C3 0.0185(5) 0.0146(5) 0.0161(5) 0.0016(4) 0.0010(4) -0.0001(4)
C4 0.0201(5) 0.0205(5) 0.0147(5) 0.0049(4) -0.0008(4) 0.0019(4)
C5 0.0162(5) 0.0249(6) 0.0142(5) 0.0009(4) -0.0018(4) -0.0007(4)
C6 0.0130(5) 0.0121(5) 0.0139(5) 0.0016(4) 0.0021(4) -0.0016(4)
C7 0.0129(5) 0.0122(5) 0.0152(5) -0.0014(4) -0.0008(4) 0.0011(4)
C8 0.0179(5) 0.0153(5) 0.0171(5) 0.0017(4) 0.0006(4) 0.0003(4)
C9 0.0182(5) 0.0191(6) 0.0206(5) 0.0000(4) 0.0036(4) 0.0028(4)
C10 0.0252(6) 0.0196(6) 0.0246(6) 0.0040(5) 0.0057(5) 0.0082(5)
C11 0.0147(5) 0.0138(5) 0.0195(5) 0.0010(4) -0.0011(4) 0.0030(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.2500(13) ?
N1 C5 . 1.3372(14) ?
N1 C1 . 1.3458(14) ?
N2 C1 . 1.3609(14) ?
N2 C7 . 1.4571(13) ?
N2 H1 . 0.882(17) ?
N3 C6 . 1.3397(14) ?
N3 C7 . 1.4646(13) ?
N3 H2 . 0.885(16) ?
C1 C2 . 1.4132(15) ?
C2 C3 . 1.3900(15) ?
C2 C6 . 1.4750(14) ?
C3 C4 . 1.3878(16) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3876(16) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C7 C11 . 1.5404(14) ?
C7 C8 . 1.5428(15) ?
C8 C9 . 1.5262(16) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5349(16) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5397(15) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
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_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 116.60(10) ?
C1 N2 C7 . . 119.32(9) ?
C1 N2 H1 . . 118.1(10) ?
C7 N2 H1 . . 118.5(10) ?
C6 N3 C7 . . 123.56(9) ?
C6 N3 H2 . . 117.6(9) ?
C7 N3 H2 . . 117.8(9) ?
N1 C1 N2 . . 117.90(10) ?
N1 C1 C2 . . 122.96(10) ?
N2 C1 C2 . . 119.05(10) ?
C3 C2 C1 . . 118.28(10) ?
C3 C2 C6 . . 122.57(10) ?
C1 C2 C6 . . 118.70(9) ?
C4 C3 C2 . . 119.29(10) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C5 C4 C3 . . 117.72(10) ?
C5 C4 H4 . . 121.1 ?
C3 C4 H4 . . 121.1 ?
N1 C5 C4 . . 125.11(10) ?
N1 C5 H5 . . 117.4 ?
C4 C5 H5 . . 117.4 ?
O1 C6 N3 . . 121.75(10) ?
O1 C6 C2 . . 122.26(10) ?
N3 C6 C2 . . 115.89(9) ?
N2 C7 N3 . . 107.23(8) ?
N2 C7 C11 . . 110.45(9) ?
N3 C7 C11 . . 111.42(9) ?
N2 C7 C8 . . 111.75(9) ?
N3 C7 C8 . . 112.50(9) ?
C11 C7 C8 . . 103.55(8) ?
C9 C8 C7 . . 103.17(9) ?
C9 C8 H8A . . 111.1 ?
C7 C8 H8A . . 111.1 ?
C9 C8 H8B . . 111.1 ?
C7 C8 H8B . . 111.1 ?
H8A C8 H8B . . 109.1 ?
C8 C9 C10 . . 103.80(9) ?
C8 C9 H9A . . 111.0 ?
C10 C9 H9A . . 111.0 ?
C8 C9 H9B . . 111.0 ?
C10 C9 H9B . . 111.0 ?
H9A C9 H9B . . 109.0 ?
C9 C10 C11 . . 106.36(9) ?
C9 C10 H10A . . 110.5 ?
C11 C10 H10A . . 110.5 ?
C9 C10 H10B . . 110.5 ?
C11 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.6 ?
C10 C11 C7 . . 106.30(9) ?
C10 C11 H11A . . 110.5 ?
C7 C11 H11A . . 110.5 ?
C10 C11 H11B . . 110.5 ?
C7 C11 H11B . . 110.5 ?
H11A C11 H11B . . 108.7 ?
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
C5 N1 C1 N2 . . . . 178.43(10) ?
C5 N1 C1 C2 . . . . 1.72(16) ?
C7 N2 C1 N1 . . . . 158.25(10) ?
C7 N2 C1 C2 . . . . -24.91(15) ?
N1 C1 C2 C3 . . . . -1.20(16) ?
N2 C1 C2 C3 . . . . -177.86(10) ?
N1 C1 C2 C6 . . . . 171.29(10) ?
N2 C1 C2 C6 . . . . -5.38(15) ?
C1 C2 C3 C4 . . . . -0.71(16) ?
C6 C2 C3 C4 . . . . -172.89(10) ?
C2 C3 C4 C5 . . . . 1.92(16) ?
C1 N1 C5 C4 . . . . -0.39(17) ?
C3 C4 C5 N1 . . . . -1.43(17) ?
C7 N3 C6 O1 . . . . -169.27(9) ?
C7 N3 C6 C2 . . . . 14.28(15) ?
C3 C2 C6 O1 . . . . 6.53(16) ?
C1 C2 C6 O1 . . . . -165.62(10) ?
C3 C2 C6 N3 . . . . -177.04(10) ?
C1 C2 C6 N3 . . . . 10.81(14) ?
C1 N2 C7 N3 . . . . 44.94(13) ?
C1 N2 C7 C11 . . . . 166.52(9) ?
C1 N2 C7 C8 . . . . -78.77(12) ?
C6 N3 C7 N2 . . . . -40.32(13) ?
C6 N3 C7 C11 . . . . -161.29(10) ?
C6 N3 C7 C8 . . . . 82.94(12) ?
N2 C7 C8 C9 . . . . -79.95(10) ?
N3 C7 C8 C9 . . . . 159.36(9) ?
C11 C7 C8 C9 . . . . 38.94(10) ?
C7 C8 C9 C10 . . . . -39.83(11) ?
C8 C9 C10 C11 . . . . 25.43(12) ?
C9 C10 C11 C7 . . . . -1.25(12) ?
N2 C7 C11 C10 . . . . 96.69(10) ?
N3 C7 C11 C10 . . . . -144.24(9) ?
C8 C7 C11 C10 . . . . -23.09(11) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1 O1 2_655 0.88(2) 2.05(2) 2.9180(10) 170(2)
N3 H2 O1 5_666 0.89(2) 2.00(2) 2.8760(10) 172.0(10)
# Attachment '- 4b.cif'
# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is ?The Royal Society of Chemistry 2011
# Attachment '- 4b.cif'
data_bo1423
_database_code_depnum_ccdc_archive 'CCDC 854865'
#TrackingRef '- 4b.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C12 H14 Br N3 O'
_chemical_formula_weight 296.17
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'
Br Br -0.2901 2.4595 '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 10.591(3)
_cell_length_b 12.359(3)
_cell_length_c 9.116(3)
_cell_angle_alpha 90.00
_cell_angle_beta 97.951(4)
_cell_angle_gamma 90.00
_cell_volume 1181.7(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 153(2)
_cell_measurement_reflns_used 3621
_cell_measurement_theta_min 2.547
_cell_measurement_theta_max 29.122
_exptl_crystal_description Platelet
_exptl_crystal_colour Colorless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.665
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 600
_exptl_absorpt_coefficient_mu 3.465
_exptl_absorpt_correction_type Multi-scans
_exptl_absorpt_correction_T_min 0.3350
_exptl_absorpt_correction_T_max 0.7572
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 153(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Rotating Anode'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type AFC10/Saturn724+
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 10128
_diffrn_reflns_av_R_equivalents 0.0458
_diffrn_reflns_av_sigmaI/netI 0.0513
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.55
_diffrn_reflns_theta_max 29.10
_reflns_number_total 3160
_reflns_number_gt 2283
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_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^)+(0.0295P)^2^+0.1260P] 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 none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3160
_refine_ls_number_parameters 162
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0555
_refine_ls_R_factor_gt 0.0345
_refine_ls_wR_factor_ref 0.0739
_refine_ls_wR_factor_gt 0.0685
_refine_ls_goodness_of_fit_ref 0.999
_refine_ls_restrained_S_all 0.999
_refine_ls_shift/su_max 0.001
_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
Br1 Br 0.99820(2) 0.65490(2) 0.61599(3) 0.03640(10) Uani 1 1 d . . .
O1 O 0.58435(14) 0.40734(11) 0.39085(16) 0.0171(3) Uani 1 1 d . . .
N1 N 0.45035(17) 0.52063(14) 0.2500(2) 0.0151(4) Uani 1 1 d . . .
N2 N 0.49356(17) 0.71034(14) 0.2458(2) 0.0188(4) Uani 1 1 d . . .
N3 N 0.68151(16) 0.78374(13) 0.3597(2) 0.0176(4) Uani 1 1 d . . .
C1 C 0.2735(2) 0.64979(16) 0.2411(2) 0.0150(4) Uani 1 1 d . . .
H1A H 0.2814 0.6418 0.3501 0.018 Uiso 1 1 calc R . .
H1B H 0.2496 0.7257 0.2164 0.018 Uiso 1 1 calc R . .
C2 C 0.1676(2) 0.57477(17) 0.1687(2) 0.0179(5) Uani 1 1 d . . .
H2A H 0.1865 0.4994 0.2015 0.021 Uiso 1 1 calc R . .
H2B H 0.0855 0.5960 0.2005 0.021 Uiso 1 1 calc R . .
C3 C 0.1565(2) 0.58081(18) -0.0002(2) 0.0194(5) Uani 1 1 d . . .
H3A H 0.0902 0.5296 -0.0448 0.023 Uiso 1 1 calc R . .
H3B H 0.1303 0.6547 -0.0336 0.023 Uiso 1 1 calc R . .
C4 C 0.2831(2) 0.55308(17) -0.0524(2) 0.0172(5) Uani 1 1 d . . .
H4A H 0.2751 0.5617 -0.1613 0.021 Uiso 1 1 calc R . .
H4B H 0.3046 0.4765 -0.0285 0.021 Uiso 1 1 calc R . .
C5 C 0.3902(2) 0.62565(16) 0.0209(2) 0.0160(4) Uani 1 1 d . . .
H5A H 0.3743 0.7006 -0.0152 0.019 Uiso 1 1 calc R . .
H5B H 0.4717 0.6014 -0.0098 0.019 Uiso 1 1 calc R . .
C6 C 0.40340(19) 0.62564(15) 0.1905(2) 0.0129(4) Uani 1 1 d . . .
C7 C 0.55747(19) 0.49967(15) 0.3433(2) 0.0127(4) Uani 1 1 d . . .
C8 C 0.64262(19) 0.59204(16) 0.3832(2) 0.0125(4) Uani 1 1 d . . .
C9 C 0.6063(2) 0.69577(16) 0.3293(2) 0.0139(4) Uani 1 1 d . . .
C10 C 0.7594(2) 0.57798(17) 0.4683(2) 0.0174(5) Uani 1 1 d . . .
H10 H 0.7863 0.5086 0.5051 0.021 Uiso 1 1 calc R . .
C11 C 0.8365(2) 0.66793(17) 0.4987(3) 0.0203(5) Uani 1 1 d . . .
C12 C 0.7942(2) 0.76778(17) 0.4435(3) 0.0203(5) Uani 1 1 d . . .
H12 H 0.8482 0.8286 0.4665 0.024 Uiso 1 1 calc R . .
H1N H 0.408(2) 0.4668(17) 0.220(2) 0.015(6) Uiso 1 1 d . . .
H2N H 0.474(2) 0.7700(19) 0.208(3) 0.026(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
Br1 0.02057(13) 0.02781(14) 0.05373(19) 0.01191(13) -0.01997(11) -0.00860(11)
O1 0.0199(8) 0.0096(7) 0.0194(8) 0.0021(6) -0.0054(6) 0.0000(6)
N1 0.0143(9) 0.0080(8) 0.0209(10) -0.0002(7) -0.0049(7) -0.0027(7)
N2 0.0163(10) 0.0070(9) 0.0298(11) 0.0047(8) -0.0085(8) -0.0006(7)
N3 0.0143(10) 0.0111(9) 0.0259(11) 0.0016(8) -0.0027(8) -0.0045(7)
C1 0.0165(11) 0.0128(10) 0.0153(10) -0.0012(8) 0.0011(8) 0.0017(9)
C2 0.0133(11) 0.0189(11) 0.0216(12) -0.0022(9) 0.0031(9) -0.0025(9)
C3 0.0130(11) 0.0208(11) 0.0227(12) -0.0027(10) -0.0029(9) -0.0036(9)
C4 0.0194(11) 0.0184(10) 0.0131(10) -0.0017(9) -0.0003(8) 0.0000(9)
C5 0.0167(11) 0.0145(10) 0.0175(11) 0.0026(9) 0.0050(9) 0.0032(8)
C6 0.0117(10) 0.0070(9) 0.0182(11) 0.0004(8) -0.0042(8) 0.0004(8)
C7 0.0135(10) 0.0112(10) 0.0132(10) -0.0005(8) 0.0013(8) 0.0009(8)
C8 0.0129(10) 0.0113(10) 0.0130(10) -0.0005(8) 0.0006(8) -0.0002(8)
C9 0.0137(10) 0.0111(9) 0.0165(11) -0.0003(8) 0.0010(8) -0.0006(8)
C10 0.0153(11) 0.0151(10) 0.0204(11) 0.0041(9) -0.0020(9) -0.0008(9)
C11 0.0120(10) 0.0200(11) 0.0262(12) 0.0027(10) -0.0064(9) -0.0040(9)
C12 0.0161(11) 0.0148(10) 0.0281(13) -0.0019(10) -0.0034(9) -0.0052(9)
_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
Br1 C11 1.896(2) . ?
O1 C7 1.240(2) . ?
N1 C7 1.346(2) . ?
N1 C6 1.467(2) . ?
N1 H1N 0.83(2) . ?
N2 C9 1.336(3) . ?
N2 C6 1.459(3) . ?
N2 H2N 0.83(2) . ?
N3 C12 1.339(3) . ?
N3 C9 1.354(3) . ?
C1 C2 1.533(3) . ?
C1 C6 1.539(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.530(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.533(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.469(3) . ?
C8 C10 1.377(3) . ?
C8 C9 1.407(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
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
C7 N1 C6 128.11(17) . . ?
C7 N1 H1N 115.1(15) . . ?
C6 N1 H1N 116.7(15) . . ?
C9 N2 C6 126.21(17) . . ?
C9 N2 H2N 120.3(17) . . ?
C6 N2 H2N 112.6(17) . . ?
C12 N3 C9 116.82(17) . . ?
C2 C1 C6 112.62(16) . . ?
C2 C1 H1A 109.1 . . ?
C6 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C6 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 110.73(17) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 110.80(17) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 111.35(17) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 113.60(18) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N2 C6 N1 109.55(16) . . ?
N2 C6 C5 108.24(17) . . ?
N1 C6 C5 110.62(17) . . ?
N2 C6 C1 109.04(16) . . ?
N1 C6 C1 109.38(17) . . ?
C5 C6 C1 109.98(16) . . ?
O1 C7 N1 122.07(18) . . ?
O1 C7 C8 121.69(18) . . ?
N1 C7 C8 116.22(17) . . ?
C10 C8 C9 119.49(18) . . ?
C10 C8 C7 120.94(18) . . ?
C9 C8 C7 119.53(18) . . ?
N2 C9 N3 117.56(18) . . ?
N2 C9 C8 120.06(18) . . ?
N3 C9 C8 122.37(18) . . ?
C8 C10 C11 118.05(19) . . ?
C8 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 Br1 120.17(16) . . ?
C10 C11 Br1 120.42(16) . . ?
N3 C12 C11 123.84(19) . . ?
N3 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -56.1(2) . . . . ?
C1 C2 C3 C4 56.8(2) . . . . ?
C2 C3 C4 C5 -55.7(2) . . . . ?
C3 C4 C5 C6 54.2(2) . . . . ?
C9 N2 C6 N1 4.4(3) . . . . ?
C9 N2 C6 C5 -116.3(2) . . . . ?
C9 N2 C6 C1 124.1(2) . . . . ?
C7 N1 C6 N2 1.1(3) . . . . ?
C7 N1 C6 C5 120.3(2) . . . . ?
C7 N1 C6 C1 -118.4(2) . . . . ?
C4 C5 C6 N2 -170.86(16) . . . . ?
C4 C5 C6 N1 69.1(2) . . . . ?
C4 C5 C6 C1 -51.8(2) . . . . ?
C2 C1 C6 N2 171.29(17) . . . . ?
C2 C1 C6 N1 -68.9(2) . . . . ?
C2 C1 C6 C5 52.7(2) . . . . ?
C6 N1 C7 O1 176.9(2) . . . . ?
C6 N1 C7 C8 -4.5(3) . . . . ?
O1 C7 C8 C10 3.8(3) . . . . ?
N1 C7 C8 C10 -174.77(19) . . . . ?
O1 C7 C8 C9 -178.41(19) . . . . ?
N1 C7 C8 C9 3.0(3) . . . . ?
C6 N2 C9 N3 174.7(2) . . . . ?
C6 N2 C9 C8 -5.9(3) . . . . ?
C12 N3 C9 N2 180.0(2) . . . . ?
C12 N3 C9 C8 0.6(3) . . . . ?
C10 C8 C9 N2 179.6(2) . . . . ?
C7 C8 C9 N2 1.8(3) . . . . ?
C10 C8 C9 N3 -1.0(3) . . . . ?
C7 C8 C9 N3 -178.8(2) . . . . ?
C9 C8 C10 C11 0.6(3) . . . . ?
C7 C8 C10 C11 178.3(2) . . . . ?
C8 C10 C11 C12 0.2(3) . . . . ?
C8 C10 C11 Br1 179.67(16) . . . . ?
C9 N3 C12 C11 0.3(3) . . . . ?
C10 C11 C12 N3 -0.6(4) . . . . ?
Br1 C11 C12 N3 179.88(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 29.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.545
_refine_diff_density_min -0.664
_refine_diff_density_rms 0.081
# Attachment '- 4e.cif'
# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is ?The Royal Society of Chemistry 2011
# Attachment '- 4e.cif'
data_bo1428
_database_code_depnum_ccdc_archive 'CCDC 854866'
#TrackingRef '- 4e.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C23 H28 Cl N3 O2'
_chemical_formula_weight 413.93
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.355(2)
_cell_length_b 10.746(3)
_cell_length_c 12.843(4)
_cell_angle_alpha 98.611(2)
_cell_angle_beta 99.924(3)
_cell_angle_gamma 110.707(3)
_cell_volume 1034.3(5)
_cell_formula_units_Z 2
_cell_measurement_temperature 153(2)
_cell_measurement_reflns_used 3355
_cell_measurement_theta_min 2.683
_cell_measurement_theta_max 29.120
_exptl_crystal_description Block
_exptl_crystal_colour Colorless
_exptl_crystal_size_max 0.33
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.329
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 440
_exptl_absorpt_coefficient_mu 0.210
_exptl_absorpt_correction_type Multi-scans
_exptl_absorpt_correction_T_min 0.9346
_exptl_absorpt_correction_T_max 0.9796
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 153(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Rotating Anode'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type AFC10/Saturn724+
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 11424
_diffrn_reflns_av_R_equivalents 0.0299
_diffrn_reflns_av_sigmaI/netI 0.0481
_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 -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.34
_diffrn_reflns_theta_max 29.14
_reflns_number_total 5406
_reflns_number_gt 4046
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_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^)+(0.0536P)^2^+0.2960P] 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 none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5406
_refine_ls_number_parameters 272
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0662
_refine_ls_R_factor_gt 0.0464
_refine_ls_wR_factor_ref 0.1160
_refine_ls_wR_factor_gt 0.1083
_refine_ls_goodness_of_fit_ref 1.001
_refine_ls_restrained_S_all 1.001
_refine_ls_shift/su_max 0.001
_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
Cl1 Cl 0.47155(5) 0.94837(4) 0.86693(3) 0.02674(12) Uani 1 1 d . . .
O1 O 0.79191(15) 0.90076(13) 0.52609(9) 0.0309(3) Uani 1 1 d . . .
O2 O 0.31427(19) 0.50545(13) 0.98262(10) 0.0347(3) Uani 1 1 d . . .
H2 H 0.3669 0.5054 1.0446 0.042 Uiso 1 1 calc R . .
N1 N 0.44526(16) 0.53913(13) 0.21298(10) 0.0172(3) Uani 1 1 d . . .
N2 N 0.74050(17) 0.66897(14) 0.23332(11) 0.0203(3) Uani 1 1 d . . .
N3 N 0.90071(18) 0.85539(15) 0.38323(11) 0.0263(3) Uani 1 1 d . . .
C1 C 0.30338(19) 0.50079(15) 0.25546(12) 0.0164(3) Uani 1 1 d . . .
C2 C 0.1437(2) 0.38199(17) 0.18348(13) 0.0221(3) Uani 1 1 d . . .
H2A H 0.1830 0.3164 0.1437 0.051 Uiso 1 1 calc R . .
H2B H 0.0807 0.4159 0.1292 0.051 Uiso 1 1 calc R . .
C3 C 0.0171(2) 0.30833(18) 0.24700(14) 0.0277(4) Uani 1 1 d . . .
H3A H -0.0929 0.2406 0.1961 0.064 Uiso 1 1 calc R . .
H3B H 0.0712 0.2590 0.2913 0.064 Uiso 1 1 calc R . .
C4 C -0.0250(2) 0.41052(19) 0.32024(14) 0.0288(4) Uani 1 1 d . . .
H4A H -0.1146 0.3615 0.3571 0.066 Uiso 1 1 calc R . .
H4B H -0.0748 0.4622 0.2760 0.066 Uiso 1 1 calc R . .
C5 C 0.1414(2) 0.50988(17) 0.40530(13) 0.0221(3) Uani 1 1 d . . .
H5A H 0.1176 0.5879 0.4403 0.051 Uiso 1 1 calc R . .
H5B H 0.1698 0.4628 0.4622 0.051 Uiso 1 1 calc R . .
C6 C 0.30015(19) 0.56401(15) 0.35775(12) 0.0158(3) Uani 1 1 d . . .
C7 C 0.45316(19) 0.67574(15) 0.41848(11) 0.0146(3) Uani 1 1 d . . .
C8 C 0.60154(19) 0.71667(15) 0.37576(11) 0.0162(3) Uani 1 1 d . . .
C9 C 0.59371(19) 0.64248(15) 0.27332(12) 0.0159(3) Uani 1 1 d . . .
C10 C 0.7697(2) 0.83111(16) 0.43461(12) 0.0206(3) Uani 1 1 d . . .
C11 C 0.88819(19) 0.80214(15) 0.26948(12) 0.0175(3) Uani 1 1 d . . .
C12 C 1.0627(2) 0.78831(17) 0.26423(13) 0.0225(3) Uani 1 1 d . . .
H12A H 1.1610 0.8748 0.3051 0.052 Uiso 1 1 calc R . .
H12B H 1.0714 0.7151 0.3006 0.052 Uiso 1 1 calc R . .
C13 C 1.0842(2) 0.75558(19) 0.14924(14) 0.0300(4) Uani 1 1 d . . .
H13A H 1.2038 0.7565 0.1521 0.069 Uiso 1 1 calc R . .
H13B H 0.9973 0.6629 0.1109 0.069 Uiso 1 1 calc R . .
C14 C 1.0572(2) 0.8594(2) 0.08717(15) 0.0355(5) Uani 1 1 d . . .
H14A H 1.1508 0.9508 0.1217 0.082 Uiso 1 1 calc R . .
H14B H 1.0660 0.8341 0.0116 0.082 Uiso 1 1 calc R . .
C15 C 0.8780(3) 0.8646(2) 0.08627(15) 0.0330(4) Uani 1 1 d . . .
H15A H 0.7843 0.7746 0.0480 0.076 Uiso 1 1 calc R . .
H15B H 0.8631 0.9335 0.0465 0.076 Uiso 1 1 calc R . .
C16 C 0.8598(2) 0.90153(18) 0.20187(15) 0.0276(4) Uani 1 1 d . . .
H16A H 0.7406 0.9014 0.1992 0.064 Uiso 1 1 calc R . .
H16B H 0.9470 0.9950 0.2376 0.064 Uiso 1 1 calc R . .
C17 C 0.45493(18) 0.74436(15) 0.52921(12) 0.0158(3) Uani 1 1 d . . .
C18 C 0.3998(2) 0.85132(16) 0.54471(13) 0.0213(3) Uani 1 1 d . . .
H18 H 0.3580 0.8816 0.4838 0.026 Uiso 1 1 calc R . .
C19 C 0.4050(2) 0.91522(17) 0.64851(13) 0.0232(3) Uani 1 1 d . . .
H19 H 0.3686 0.9896 0.6589 0.028 Uiso 1 1 calc R . .
C20 C 0.4638(2) 0.86884(16) 0.73632(12) 0.0185(3) Uani 1 1 d . . .
C21 C 0.5142(2) 0.75973(18) 0.72245(13) 0.0235(3) Uani 1 1 d . . .
H21 H 0.5521 0.7276 0.7833 0.028 Uiso 1 1 calc R . .
C22 C 0.5089(2) 0.69730(17) 0.61844(13) 0.0215(3) Uani 1 1 d . . .
H22 H 0.5426 0.6215 0.6082 0.026 Uiso 1 1 calc R . .
C23 C 0.3592(3) 0.6407(2) 0.97101(16) 0.0354(4) Uani 1 1 d . . .
H23A H 0.3591 0.6981 1.0379 0.042 Uiso 1 1 calc R . .
H23B H 0.2729 0.6434 0.9101 0.042 Uiso 1 1 calc R . .
H23C H 0.4769 0.6748 0.9570 0.042 Uiso 1 1 calc R . .
H3N H 0.996(3) 0.926(2) 0.4156(17) 0.037(6) Uiso 1 1 d . . .
H2N H 0.723(3) 0.621(2) 0.1703(18) 0.037(6) 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
Cl1 0.0278(2) 0.0350(2) 0.01447(18) -0.00310(16) 0.00581(14) 0.01207(18)
O1 0.0215(6) 0.0325(7) 0.0195(6) -0.0107(5) 0.0082(5) -0.0067(5)
O2 0.0462(8) 0.0288(7) 0.0160(6) 0.0007(5) 0.0045(5) 0.0024(6)
N1 0.0160(6) 0.0174(6) 0.0131(6) -0.0001(5) 0.0027(5) 0.0024(5)
N2 0.0172(6) 0.0201(7) 0.0155(6) -0.0041(5) 0.0071(5) -0.0005(5)
N3 0.0175(7) 0.0280(8) 0.0174(7) -0.0082(6) 0.0068(5) -0.0056(6)
C1 0.0145(7) 0.0161(7) 0.0149(7) 0.0020(6) 0.0024(5) 0.0027(6)
C2 0.0159(7) 0.0225(8) 0.0179(7) -0.0028(6) 0.0026(6) -0.0007(6)
C3 0.0208(8) 0.0230(9) 0.0267(9) -0.0027(7) 0.0062(6) -0.0031(7)
C4 0.0169(8) 0.0318(10) 0.0272(9) -0.0013(7) 0.0077(6) -0.0007(7)
C5 0.0170(7) 0.0231(8) 0.0192(8) 0.0002(6) 0.0073(6) 0.0002(6)
C6 0.0151(7) 0.0156(7) 0.0146(7) 0.0030(6) 0.0041(5) 0.0036(6)
C7 0.0163(7) 0.0142(7) 0.0119(6) 0.0020(5) 0.0036(5) 0.0048(6)
C8 0.0145(7) 0.0165(7) 0.0127(7) 0.0005(5) 0.0027(5) 0.0019(6)
C9 0.0154(7) 0.0155(7) 0.0145(7) 0.0020(6) 0.0043(5) 0.0034(6)
C10 0.0166(7) 0.0204(8) 0.0170(7) -0.0012(6) 0.0047(6) 0.0001(6)
C11 0.0146(7) 0.0178(8) 0.0147(7) -0.0020(6) 0.0050(5) 0.0015(6)
C12 0.0158(7) 0.0264(9) 0.0226(8) 0.0017(7) 0.0049(6) 0.0066(6)
C13 0.0192(8) 0.0363(10) 0.0286(9) -0.0055(8) 0.0106(7) 0.0068(7)
C14 0.0298(9) 0.0410(11) 0.0209(9) 0.0027(8) 0.0111(7) -0.0041(8)
C15 0.0352(10) 0.0321(10) 0.0262(9) 0.0132(8) 0.0044(7) 0.0054(8)
C16 0.0294(9) 0.0218(8) 0.0309(9) 0.0041(7) 0.0067(7) 0.0100(7)
C17 0.0132(6) 0.0162(7) 0.0143(7) 0.0013(6) 0.0050(5) 0.0014(6)
C18 0.0266(8) 0.0219(8) 0.0159(7) 0.0037(6) 0.0049(6) 0.0104(7)
C19 0.0286(8) 0.0232(8) 0.0197(8) 0.0017(6) 0.0066(6) 0.0133(7)
C20 0.0171(7) 0.0217(8) 0.0124(7) -0.0016(6) 0.0049(5) 0.0043(6)
C21 0.0286(8) 0.0316(9) 0.0141(7) 0.0063(6) 0.0058(6) 0.0153(7)
C22 0.0280(8) 0.0232(8) 0.0190(7) 0.0051(6) 0.0075(6) 0.0156(7)
C23 0.0419(11) 0.0360(11) 0.0300(10) 0.0065(8) 0.0069(8) 0.0185(9)
_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
Cl1 C20 1.7442(16) . ?
O1 C10 1.2401(19) . ?
O2 C23 1.405(2) . ?
O2 H2 0.8400 . ?
N1 C9 1.3450(18) . ?
N1 C1 1.3481(19) . ?
N2 C9 1.365(2) . ?
N2 C11 1.4631(19) . ?
N2 H2N 0.85(2) . ?
N3 C10 1.342(2) . ?
N3 C11 1.4585(19) . ?
N3 H3N 0.86(2) . ?
C1 C6 1.395(2) . ?
C1 C2 1.511(2) . ?
C2 C3 1.519(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.531(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4052(19) . ?
C7 C8 1.397(2) . ?
C7 C17 1.496(2) . ?
C8 C9 1.411(2) . ?
C8 C10 1.480(2) . ?
C11 C12 1.528(2) . ?
C11 C16 1.529(2) . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.382(2) . ?
C17 C22 1.389(2) . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(2) . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
C23 O2 H2 109.5 . . ?
C9 N1 C1 118.31(13) . . ?
C9 N2 C11 121.34(13) . . ?
C9 N2 H2N 114.5(14) . . ?
C11 N2 H2N 119.1(14) . . ?
C10 N3 C11 127.65(13) . . ?
C10 N3 H3N 115.6(14) . . ?
C11 N3 H3N 114.6(14) . . ?
N1 C1 C6 123.80(13) . . ?
N1 C1 C2 114.91(13) . . ?
C6 C1 C2 121.29(13) . . ?
C1 C2 C3 112.60(13) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 109.83(15) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 110.56(14) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 113.04(13) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C1 C6 C7 117.62(13) . . ?
C1 C6 C5 121.61(13) . . ?
C7 C6 C5 120.68(13) . . ?
C8 C7 C6 119.31(13) . . ?
C8 C7 C17 121.71(12) . . ?
C6 C7 C17 118.93(13) . . ?
C7 C8 C9 118.67(13) . . ?
C7 C8 C10 123.20(13) . . ?
C9 C8 C10 118.08(13) . . ?
N1 C9 N2 116.92(13) . . ?
N1 C9 C8 122.15(13) . . ?
N2 C9 C8 120.87(13) . . ?
O1 C10 N3 120.94(14) . . ?
O1 C10 C8 123.29(14) . . ?
N3 C10 C8 115.76(14) . . ?
N3 C11 N2 107.79(12) . . ?
N3 C11 C12 106.90(13) . . ?
N2 C11 C12 111.08(13) . . ?
N3 C11 C16 109.86(14) . . ?
N2 C11 C16 111.01(13) . . ?
C12 C11 C16 110.08(13) . . ?
C13 C12 C11 113.88(13) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 110.65(15) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 110.50(14) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 110.67(15) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C11 112.35(15) . . ?
C15 C16 H16A 109.1 . . ?
C11 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C11 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C22 119.09(14) . . ?
C18 C17 C7 121.61(13) . . ?
C22 C17 C7 119.28(14) . . ?
C17 C18 C19 120.77(15) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.00(15) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 121.20(14) . . ?
C21 C20 Cl1 119.33(12) . . ?
C19 C20 Cl1 119.47(13) . . ?
C20 C21 C22 119.14(15) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C17 120.75(15) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C6 1.4(2) . . . . ?
C9 N1 C1 C2 -178.65(14) . . . . ?
N1 C1 C2 C3 157.81(15) . . . . ?
C6 C1 C2 C3 -22.2(2) . . . . ?
C1 C2 C3 C4 51.1(2) . . . . ?
C2 C3 C4 C5 -63.6(2) . . . . ?
C3 C4 C5 C6 45.3(2) . . . . ?
N1 C1 C6 C7 1.3(2) . . . . ?
C2 C1 C6 C7 -178.63(14) . . . . ?
N1 C1 C6 C5 -175.25(15) . . . . ?
C2 C1 C6 C5 4.8(2) . . . . ?
C4 C5 C6 C1 -16.4(2) . . . . ?
C4 C5 C6 C7 167.19(15) . . . . ?
C1 C6 C7 C8 -1.4(2) . . . . ?
C5 C6 C7 C8 175.22(14) . . . . ?
C1 C6 C7 C17 -179.03(14) . . . . ?
C5 C6 C7 C17 -2.4(2) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
C17 C7 C8 C9 176.48(14) . . . . ?
C6 C7 C8 C10 -178.65(14) . . . . ?
C17 C7 C8 C10 -1.1(2) . . . . ?
C1 N1 C9 N2 172.93(14) . . . . ?
C1 N1 C9 C8 -4.1(2) . . . . ?
C11 N2 C9 N1 158.74(14) . . . . ?
C11 N2 C9 C8 -24.2(2) . . . . ?
C7 C8 C9 N1 4.0(2) . . . . ?
C10 C8 C9 N1 -178.35(14) . . . . ?
C7 C8 C9 N2 -172.91(14) . . . . ?
C10 C8 C9 N2 4.7(2) . . . . ?
C11 N3 C10 O1 -167.31(17) . . . . ?
C11 N3 C10 C8 13.4(3) . . . . ?
C7 C8 C10 O1 -0.7(3) . . . . ?
C9 C8 C10 O1 -178.28(16) . . . . ?
C7 C8 C10 N3 178.55(16) . . . . ?
C9 C8 C10 N3 1.0(2) . . . . ?
C10 N3 C11 N2 -29.2(2) . . . . ?
C10 N3 C11 C12 -148.67(18) . . . . ?
C10 N3 C11 C16 91.9(2) . . . . ?
C9 N2 C11 N3 33.4(2) . . . . ?
C9 N2 C11 C12 150.18(14) . . . . ?
C9 N2 C11 C16 -86.99(18) . . . . ?
N3 C11 C12 C13 -170.69(14) . . . . ?
N2 C11 C12 C13 71.96(18) . . . . ?
C16 C11 C12 C13 -51.41(18) . . . . ?
C11 C12 C13 C14 54.01(19) . . . . ?
C12 C13 C14 C15 -56.51(19) . . . . ?
C13 C14 C15 C16 58.4(2) . . . . ?
C14 C15 C16 C11 -57.0(2) . . . . ?
N3 C11 C16 C15 169.89(14) . . . . ?
N2 C11 C16 C15 -70.98(18) . . . . ?
C12 C11 C16 C15 52.43(18) . . . . ?
C8 C7 C17 C18 93.25(19) . . . . ?
C6 C7 C17 C18 -89.15(18) . . . . ?
C8 C7 C17 C22 -88.44(19) . . . . ?
C6 C7 C17 C22 89.17(18) . . . . ?
C22 C17 C18 C19 2.7(2) . . . . ?
C7 C17 C18 C19 -179.02(14) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C18 C19 C20 Cl1 179.81(13) . . . . ?
C19 C20 C21 C22 1.3(2) . . . . ?
Cl1 C20 C21 C22 -179.58(13) . . . . ?
C20 C21 C22 C17 0.5(2) . . . . ?
C18 C17 C22 C21 -2.4(2) . . . . ?
C7 C17 C22 C21 179.20(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full 29.14
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max 0.400
_refine_diff_density_min -0.321
_refine_diff_density_rms 0.058