#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:45:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178442 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/63/4026384.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4026384
loop_
_publ_author_name
'Jason C. Morris'
'John C. McMurtrie'
'Steven E. Bottle'
'Kathryn E. Fairfull-Smith'
_publ_section_title
;
 Generation of Profluorescent Isoindoline Nitroxides Using Click Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4964
_journal_page_last               4972
_journal_paper_doi               10.1021/jo200613r
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C23 H21 N4 O3'
_chemical_formula_sum            'C23 H21 N4 O3'
_chemical_formula_weight         401.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.916(7)
_cell_angle_beta                 99.112(4)
_cell_angle_gamma                95.001(5)
_cell_formula_units_Z            2
_cell_length_a                   5.8079(2)
_cell_length_b                   12.9919(11)
_cell_length_c                   14.7368(9)
_cell_measurement_reflns_used    3149
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.6945
_cell_measurement_theta_min      3.1439
_cell_volume                     997.65(13)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_molecular_graphics
;ORTEPIII (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;
_computing_publication_material  'enCIFer 1.0 (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6999
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.76
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prism
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0250P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                2942
_reflns_number_total             4461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200613r_si_001.cif
_cod_data_source_block           10
_cod_original_cell_volume        997.66(13)
_cod_database_code               4026384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.8829(2) 0.92646(11) 0.22684(10) 0.0250(3) Uani 1 1 d .
C2 C 1.1534(2) 1.09253(10) 0.34794(9) 0.0229(3) Uani 1 1 d .
C3 C 1.3635(2) 1.16290(11) 0.36611(10) 0.0276(3) Uani 1 1 d .
H3 H 1.4496 1.1531 0.3144 0.033 Uiso 1 1 calc R
C4 C 1.4449(2) 1.24784(11) 0.46146(10) 0.0310(3) Uani 1 1 d .
H4 H 1.5897 1.2967 0.4756 0.037 Uiso 1 1 calc R
C5 C 1.3184(2) 1.26298(11) 0.53706(10) 0.0298(3) Uani 1 1 d .
H5 H 1.3768 1.3222 0.6021 0.036 Uiso 1 1 calc R
C6 C 1.1083(2) 1.19228(10) 0.51800(9) 0.0264(3) Uani 1 1 d .
H6 H 1.0218 1.2031 0.5697 0.032 Uiso 1 1 calc R
C7 C 1.0229(2) 1.10447(10) 0.42225(9) 0.0230(3) Uani 1 1 d .
C8 C 0.8161(2) 1.02190(10) 0.39828(9) 0.0245(3) Uani 1 1 d .
H8 H 0.7245 1.0276 0.4475 0.029 Uiso 1 1 calc R
C9 C 0.7526(2) 0.93666(10) 0.30636(9) 0.0226(3) Uani 1 1 d .
C10 C 0.5155(2) 0.73981(11) 0.21613(9) 0.0270(3) Uani 1 1 d .
H10 H 0.6103 0.7023 0.1704 0.032 Uiso 1 1 calc R
C11 C 0.3107(2) 0.69370(11) 0.23053(9) 0.0247(3) Uani 1 1 d .
C12 C 0.1932(2) 0.57508(11) 0.18832(9) 0.0242(3) Uani 1 1 d .
C13 C 0.0668(2) 0.53781(10) 0.24618(9) 0.0243(3) Uani 1 1 d .
H13 H 0.0448 0.5902 0.3092 0.029 Uiso 1 1 calc R
C14 C -0.0262(2) 0.42391(10) 0.21100(9) 0.0221(3) Uani 1 1 d .
C15 C 0.0032(2) 0.34607(10) 0.11862(9) 0.0231(3) Uani 1 1 d .
C16 C 0.1226(2) 0.38280(11) 0.05914(9) 0.0276(3) Uani 1 1 d .
H16 H 0.1394 0.3305 -0.0049 0.033 Uiso 1 1 calc R
C17 C 0.2170(2) 0.49662(11) 0.09437(9) 0.0283(3) Uani 1 1 d .
H17 H 0.2992 0.5217 0.0540 0.034 Uiso 1 1 calc R
C18 C -0.1531(2) 0.36784(10) 0.26572(9) 0.0234(3) Uani 1 1 d .
C19 C -0.3915(2) 0.40442(12) 0.28129(11) 0.0348(3) Uani 1 1 d .
H19A H -0.4841 0.3984 0.2172 0.052 Uiso 1 1 calc R
H19B H -0.3664 0.4831 0.3311 0.052 Uiso 1 1 calc R
H19C H -0.4771 0.3553 0.3055 0.052 Uiso 1 1 calc R
C20 C -0.0003(2) 0.38102(12) 0.36489(10) 0.0346(3) Uani 1 1 d .
H20A H -0.0823 0.3350 0.3930 0.052 Uiso 1 1 calc R
H20B H 0.0291 0.4608 0.4125 0.052 Uiso 1 1 calc R
H20C H 0.1506 0.3558 0.3530 0.052 Uiso 1 1 calc R
C21 C -0.0970(2) 0.22660(11) 0.09839(9) 0.0246(3) Uani 1 1 d .
C22 C 0.0910(2) 0.15051(11) 0.09351(10) 0.0299(3) Uani 1 1 d .
H22A H 0.1497 0.1344 0.0314 0.045 Uiso 1 1 calc R
H22B H 0.0217 0.0794 0.0942 0.045 Uiso 1 1 calc R
H22C H 0.2221 0.1890 0.1518 0.045 Uiso 1 1 calc R
C23 C -0.3007(2) 0.17163(12) 0.00621(10) 0.0378(4) Uani 1 1 d .
H23A H -0.4182 0.2222 0.0111 0.057 Uiso 1 1 calc R
H23B H -0.3746 0.0995 0.0036 0.057 Uiso 1 1 calc R
H23C H -0.2396 0.1579 -0.0551 0.057 Uiso 1 1 calc R
N1 N 0.55411(18) 0.85065(9) 0.28126(8) 0.0247(2) Uani 1 1 d .
N2 N 0.38034(18) 0.87311(9) 0.33477(8) 0.0291(3) Uani 1 1 d .
N3 N 0.23207(18) 0.77797(9) 0.30309(8) 0.0291(3) Uani 1 1 d .
N4 N -0.19076(18) 0.24770(9) 0.19176(8) 0.0299(3) Uani 1 1 d .
O1 O 0.83479(16) 0.85345(8) 0.14214(7) 0.0363(2) Uani 1 1 d .
O2 O 1.07807(14) 1.00678(7) 0.25241(6) 0.0259(2) Uani 1 1 d .
O3 O -0.28635(16) 0.16750(8) 0.21021(7) 0.0380(2) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 117.86(11)
O1 C1 C9 125.92(12)
O2 C1 C9 116.21(11)
O2 C2 C3 117.02(11)
O2 C2 C7 120.63(11)
C3 C2 C7 122.33(12)
C4 C3 C2 118.17(12)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C5 121.09(13)
C3 C4 H4 119.5
C5 C4 H4 119.5
C6 C5 C4 120.26(12)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 119.88(12)
C5 C6 H6 120.1
C7 C6 H6 120.1
C2 C7 C6 118.26(12)
C2 C7 C8 118.17(11)
C6 C7 C8 123.45(12)
C9 C8 C7 119.98(12)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 N1 121.49(11)
C8 C9 C1 122.06(12)
N1 C9 C1 116.45(11)
N1 C10 C11 105.17(11)
N1 C10 H10 127.4
C11 C10 H10 127.4
N3 C11 C10 107.98(11)
N3 C11 C12 121.71(11)
C10 C11 C12 130.04(11)
C17 C12 C13 119.00(12)
C17 C12 C11 121.70(11)
C13 C12 C11 119.17(11)
C14 C13 C12 119.63(11)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C15 120.96(11)
C13 C14 C18 126.83(11)
C15 C14 C18 112.12(11)
C14 C15 C16 119.86(12)
C14 C15 C21 112.17(11)
C16 C15 C21 127.93(11)
C17 C16 C15 119.30(11)
C17 C16 H16 120.4
C15 C16 H16 120.4
C16 C17 C12 121.22(12)
C16 C17 H17 119.4
C12 C17 H17 119.4
N4 C18 C14 99.92(9)
N4 C18 C20 109.75(10)
C14 C18 C20 112.65(10)
N4 C18 C19 109.54(10)
C14 C18 C19 113.59(10)
C20 C18 C19 110.82(10)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
N4 C21 C15 99.88(9)
N4 C21 C22 109.02(10)
C15 C21 C22 113.19(10)
N4 C21 C23 109.36(10)
C15 C21 C23 113.57(11)
C22 C21 C23 111.14(11)
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C21 C23 H23A 109.5
C21 C23 H23B 109.5
H23A C23 H23B 109.5
C21 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C10 N1 N2 110.47(10)
C10 N1 C9 129.92(10)
N2 N1 C9 119.22(10)
N3 N2 N1 106.89(9)
N2 N3 C11 109.48(10)
O3 N4 C18 121.45(10)
O3 N4 C21 122.54(10)
C18 N4 C21 115.90(10)
C1 O2 C2 122.82(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2071(14)
C1 O2 1.3666(14)
C1 C9 1.4635(16)
C2 O2 1.3831(14)
C2 C3 1.3812(17)
C2 C7 1.3960(16)
C3 C4 1.3809(18)
C3 H3 0.9500
C4 C5 1.3903(17)
C4 H4 0.9500
C5 C6 1.3810(18)
C5 H5 0.9500
C6 C7 1.4017(17)
C6 H6 0.9500
C7 C8 1.4363(17)
C8 C9 1.3416(16)
C8 H8 0.9500
C9 N1 1.4257(15)
C10 N1 1.3580(15)
C10 C11 1.3689(17)
C10 H10 0.9500
C11 N3 1.3714(15)
C11 C12 1.4707(17)
C12 C17 1.4002(16)
C12 C13 1.3997(16)
C13 C14 1.3874(17)
C13 H13 0.9500
C14 C15 1.3918(16)
C14 C18 1.5086(17)
C15 C16 1.3920(17)
C15 C21 1.5046(17)
C16 C17 1.3883(17)
C16 H16 0.9500
C17 H17 0.9500
C18 N4 1.4874(15)
C18 C20 1.5233(17)
C18 C19 1.5249(16)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 N4 1.4948(15)
C21 C22 1.5270(17)
C21 C23 1.5306(17)
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
N1 N2 1.3601(13)
N2 N3 1.3133(14)
N4 O3 1.2788(13)
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
O2 C2 C3 C4 -178.78(11)
C7 C2 C3 C4 -0.13(18)
C2 C3 C4 C5 -0.52(19)
C3 C4 C5 C6 0.39(19)
C4 C5 C6 C7 0.39(19)
O2 C2 C7 C6 179.49(10)
C3 C2 C7 C6 0.88(18)
O2 C2 C7 C8 3.28(16)
C3 C2 C7 C8 -175.32(11)
C5 C6 C7 C2 -1.00(18)
C5 C6 C7 C8 174.99(12)
C2 C7 C8 C9 -0.37(17)
C6 C7 C8 C9 -176.37(12)
C7 C8 C9 N1 177.41(11)
C7 C8 C9 C1 -2.27(18)
O1 C1 C9 C8 -178.83(12)
O2 C1 C9 C8 2.01(17)
O1 C1 C9 N1 1.48(19)
O2 C1 C9 N1 -177.69(10)
N1 C10 C11 N3 0.35(14)
N1 C10 C11 C12 -173.61(12)
N3 C11 C12 C17 158.32(12)
C10 C11 C12 C17 -28.4(2)
N3 C11 C12 C13 -25.80(17)
C10 C11 C12 C13 147.45(13)
C17 C12 C13 C14 1.89(17)
C11 C12 C13 C14 -174.10(11)
C12 C13 C14 C15 -0.35(18)
C12 C13 C14 C18 175.87(11)
C13 C14 C15 C16 -1.56(18)
C18 C14 C15 C16 -178.29(10)
C13 C14 C15 C21 176.13(11)
C18 C14 C15 C21 -0.60(14)
C14 C15 C16 C17 1.87(18)
C21 C15 C16 C17 -175.41(12)
C15 C16 C17 C12 -0.31(19)
C13 C12 C17 C16 -1.57(18)
C11 C12 C17 C16 174.32(12)
C13 C14 C18 N4 -176.37(12)
C15 C14 C18 N4 0.13(12)
C13 C14 C18 C20 -59.96(16)
C15 C14 C18 C20 116.54(12)
C13 C14 C18 C19 67.09(16)
C15 C14 C18 C19 -116.41(12)
C14 C15 C21 N4 0.76(13)
C16 C15 C21 N4 178.22(12)
C14 C15 C21 C22 -114.99(12)
C16 C15 C21 C22 62.46(17)
C14 C15 C21 C23 117.06(12)
C16 C15 C21 C23 -65.48(17)
C11 C10 N1 N2 0.21(14)
C11 C10 N1 C9 172.92(12)
C8 C9 N1 C10 -149.00(13)
C1 C9 N1 C10 30.69(18)
C8 C9 N1 N2 23.17(17)
C1 C9 N1 N2 -157.14(11)
C10 N1 N2 N3 -0.71(13)
C9 N1 N2 N3 -174.31(10)
N1 N2 N3 C11 0.92(13)
C10 C11 N3 N2 -0.81(14)
C12 C11 N3 N2 173.76(11)
C14 C18 N4 O3 176.79(11)
C20 C18 N4 O3 58.22(14)
C19 C18 N4 O3 -63.65(14)
C14 C18 N4 C21 0.39(12)
C20 C18 N4 C21 -118.18(11)
C19 C18 N4 C21 119.95(11)
C15 C21 N4 O3 -177.06(11)
C22 C21 N4 O3 -58.19(15)
C23 C21 N4 O3 63.51(15)
C15 C21 N4 C18 -0.71(13)
C22 C21 N4 C18 118.16(11)
C23 C21 N4 C18 -120.14(12)
O1 C1 O2 C2 -178.26(11)
C9 C1 O2 C2 0.98(16)
C3 C2 O2 C1 175.04(11)
C7 C2 O2 C1 -3.63(16)
