#------------------------------------------------------------------------------
#$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $
#$Revision: 88064 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104986.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2104986
loop_
_publ_author_name
'Liu, Xiaogang'
'Cole, Jacqueline M.'
'Waddell, Paul G.'
'Lin, Tze-Chia'
_publ_section_title
;
 Molecular origins of commercial laser dye functionality in azacoumarins
 and 2-quinolones: LD 425, LD 489 and LD 473
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              560
_journal_page_last               568
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_name_common            'LD 425'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.481(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.061(5)
_cell_length_b                   24.489(15)
_cell_length_c                   13.930(9)
_cell_measurement_reflns_used    6908
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      33.1
_cell_measurement_theta_min      1.7
_cell_volume                     2342(3)
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r4
;
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r4
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r4
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r4
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.1242
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14043
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.028
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0624
_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/[\s^2^(Fo^2^)+(0.0464P)^2^+0.1911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                4634
_reflns_number_total             5763
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL shelx_sortav_075 in P2(1)/c
CELL 0.71073   7.0608  24.4894  13.9300  90.000 103.481  90.000
ZERR    8.00   0.0046   0.0152   0.0085   0.000   0.008   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 104 112 16 24
OMIT    0   2   0
OMIT    0   2   1
OMIT    0   1   1
OMIT    0  1  2
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 10
CONF
WGHT  0.046400  0.191100
FVAR  0.203840
TEMP -93
MOLE 1
C1     1   0.946098  0.327486  0.511501 11.000000  0.047790  0.031470 =
           0.029680 -0.006510  0.007670 -0.003470
C2     1   1.023929  0.318568  0.792813 11.000000  0.034730  0.021730 =
           0.031040  0.001410  0.009370  0.002700
C3     1   0.999898  0.339073  0.693540 11.000000  0.032230  0.022620 =
           0.031860 -0.001640  0.009790 -0.000710
C4     1   0.973062  0.305700  0.614494 11.000000  0.026270  0.024930 =
           0.029700 -0.003920  0.007120 -0.001990
C5     1   0.946598  0.207560  0.556535 11.000000  0.031940  0.026860 =
           0.028860  0.002110  0.008730  0.000350
C6     1   0.945600  0.153003  0.580361 11.000000  0.033960  0.025380 =
           0.031160  0.004900  0.010250  0.001060
C7     1   0.965287  0.138181  0.680338 11.000000  0.028460  0.022120 =
           0.033060  0.001060  0.010380 -0.000320
C8     1   0.991240  0.227653  0.726411 11.000000  0.026660  0.023200 =
           0.027330  0.000930  0.008600 -0.000260
C9     1   0.968918  0.247461  0.630576 11.000000  0.026370  0.023210 =
           0.026630  0.000030  0.005950 -0.000940
C10    1   0.856314 -0.009600  0.672485 11.000000  0.037670  0.024230 =
           0.049580  0.002770  0.008110  0.002690
C11    1   0.962725  0.039165  0.642436 11.000000  0.040830  0.022660 =
           0.041680  0.005280  0.014590  0.000720
C12    1   1.023176  0.070016  0.813798 11.000000  0.050570  0.024050 =
           0.036020 -0.001590  0.010460  0.004280
C13    1   0.913206  0.020281  0.835918 11.000000  0.049420  0.025680 =
           0.045740 -0.003340  0.017490  0.001040
N1     3   0.990267  0.175788  0.753023 11.000000  0.033890  0.021250 =
           0.030410 -0.000470  0.009690  0.000930
N2     3   0.956477  0.084693  0.709333 11.000000  0.040280  0.020420 =
           0.034110  0.001150  0.011020  0.001220
O1     4   1.017841  0.262664  0.805814 11.000000  0.044370  0.020830 =
           0.026470 -0.000160  0.010040  0.001690
O2     4   1.047426  0.346281  0.867193 11.000000  0.059660  0.025700 =
           0.032380  0.004130  0.014210  0.005080
O3     4   0.933472 -0.024384  0.772984 11.000000  0.043720  0.021330 =
           0.052450 -0.002700  0.011000  0.000680
H3     2   1.006570  0.379393  0.689461 11.000000  0.033080
H5     2   0.932463  0.217838  0.485894 11.000000  0.039900
H6     2   0.932908  0.126895  0.532130 11.000000  0.044260
H10A   2   0.717918 -0.001143  0.664145 11.000000  0.040420
H11A   2   0.893724  0.049245  0.569924 11.000000  0.041030
H12A   2   0.994118  0.100175  0.852217 11.000000  0.049340
H13A   2   0.766934  0.029366  0.826668 11.000000  0.046810
H10B   2   0.873269 -0.042359  0.632924 11.000000  0.032220
H11B   2   1.095913  0.030273  0.643912 11.000000  0.039490
H12B   2   1.163305  0.063478  0.830218 11.000000  0.034340
H13B   2   0.975127  0.006999  0.904563 11.000000  0.042010
H1A    2   0.812803  0.314836  0.469346 11.000000  0.051960
H1B    2   0.951793  0.369400  0.513862 11.000000  0.042840
H1C    2   1.043814  0.312880  0.481373 11.000000  0.049680
MOLE 2
C1'    1   0.572322  0.608395  0.955170 11.000000  0.044060  0.028020 =
           0.032380  0.005370  0.007160 -0.000260
C2'    1   0.505601  0.634468  0.678421 11.000000  0.033820  0.024060 =
           0.034550 -0.001360  0.006460  0.002460
C3'    1   0.535101  0.608399  0.773388 11.000000  0.032890  0.020000 =
           0.034650  0.001090  0.005590 -0.000130
C4'    1   0.548233  0.636852  0.857646 11.000000  0.024670  0.024190 =
           0.033520  0.001690  0.004790 -0.001550
C5'    1   0.551003  0.731475  0.933490 11.000000  0.031700  0.026170 =
           0.030020  0.001580  0.008400 -0.001840
C6'    1   0.539258  0.786918  0.919304 11.000000  0.034380  0.025700 =
           0.031390 -0.003390  0.010860 -0.001530
C7'    1   0.512882  0.807473  0.821810 11.000000  0.026740  0.022780 =
           0.033750  0.000520  0.009320  0.000130
C8'    1   0.510507  0.720946  0.760772 11.000000  0.027690  0.023720 =
           0.029000 -0.002060  0.007150 -0.000510
C9'    1   0.535851  0.695744  0.852976 11.000000  0.025140  0.023250 =
           0.029840  0.001800  0.005950 -0.001340
C10'   1   0.430501  0.954328  0.849899 11.000000  0.044500  0.023640 =
           0.050310 -0.003690  0.019750  0.000420
C11'   1   0.558382  0.904238  0.875928 11.000000  0.044090  0.023450 =
           0.038450 -0.002250  0.013920 -0.001490
C12'   1   0.481108  0.881379  0.700146 11.000000  0.043720  0.023800 =
           0.036880  0.002740  0.014400  0.003190
C13'   1   0.355579  0.932315  0.681804 11.000000  0.039920  0.024610 =
           0.046650  0.002190  0.009940  0.002240
N1'    3   0.499099  0.774057  0.743471 11.000000  0.032720  0.022970 =
           0.029550  0.001460  0.007380  0.001750
N2'    3   0.493200  0.862042  0.801123 11.000000  0.045220  0.020350 =
           0.033570  0.000510  0.013170  0.000880
O1'    4   0.494929  0.690943  0.675962 11.000000  0.041350  0.022710 =
           0.029330  0.000400  0.007270  0.002390
O2'    4   0.487529  0.611799  0.599272 11.000000  0.060250  0.028860 =
           0.032720 -0.003830  0.007950  0.005590
O3'    4   0.427895  0.973856  0.752816 11.000000  0.045690  0.020870 =
           0.050690  0.000790  0.013720 -0.001130
H3'    2   0.538351  0.569518  0.772056 11.000000  0.039150
H5'    2   0.565894  0.717545  1.001271 11.000000  0.036280
H6'    2   0.546963  0.810540  0.972516 11.000000  0.037180
H10C   2   0.288504  0.945662  0.853597 11.000000  0.044480
H11C   2   0.553878  0.892209  0.940099 11.000000  0.040500
H12C   2   0.419339  0.854002  0.657939 11.000000  0.043180
H13C   2   0.215204  0.923324  0.683396 11.000000  0.037320
H10D   2   0.481780  0.982228  0.895513 11.000000  0.039200
H11D   2   0.695749  0.914753  0.876230 11.000000  0.045950
H12D   2   0.615739  0.889559  0.692764 11.000000  0.031940
H13D   2   0.366295  0.948615  0.612780 11.000000  0.044150
H1D    2   0.459018  0.617186  0.984296 11.000000  0.043400
H1E    2   0.588419  0.568218  0.948565 11.000000  0.043680
H1F    2   0.683591  0.621975  1.003310 11.000000  0.040830
HKLF 4
END
;
_[local]_cod_data_source_file    bk5105.cif
_[local]_cod_data_source_block   ld425
_[local]_cod_cif_authors_sg_H-M  P2(1)/c
_cod_database_code               2104986
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'
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_occupancy
_atom_site_symmetry_multiplicity
C C1 0.9461(3) 0.32749(8) 0.51150(14) 0.0365(4) Uani d 1 1
C C2 1.0239(3) 0.31857(6) 0.79281(13) 0.0289(4) Uani d 1 1
C C3 0.9999(3) 0.33907(6) 0.69354(13) 0.0285(3) Uani d 1 1
C C4 0.9731(3) 0.30570(6) 0.61449(12) 0.0269(3) Uani d 1 1
C C5 0.9466(3) 0.20756(7) 0.55654(13) 0.0289(3) Uani d 1 1
C C6 0.9456(3) 0.15300(7) 0.58036(13) 0.0297(4) Uani d 1 1
C C7 0.9653(3) 0.13818(6) 0.68034(13) 0.0274(3) Uani d 1 1
C C8 0.9912(2) 0.22765(6) 0.72641(12) 0.0253(3) Uani d 1 1
C C9 0.9689(3) 0.24746(6) 0.63058(12) 0.0254(3) Uani d 1 1
C C10 0.8563(3) -0.00960(7) 0.67249(16) 0.0375(4) Uani d 1 1
C C11 0.9627(3) 0.03917(7) 0.64244(15) 0.0342(4) Uani d 1 1
C C12 1.0232(3) 0.07002(7) 0.81380(14) 0.0368(4) Uani d 1 1
C C13 0.9132(4) 0.02028(7) 0.83592(16) 0.0392(4) Uani d 1 1
N N1 0.9903(2) 0.17579(5) 0.75302(10) 0.0282(3) Uani d 1 1
N N2 0.9565(2) 0.08469(5) 0.70933(11) 0.0312(3) Uani d 1 1
O O1 1.0178(2) 0.26266(4) 0.80581(9) 0.0303(3) Uani d 1 1
O O2 1.0474(2) 0.34628(5) 0.86719(9) 0.0387(3) Uani d 1 1
O O3 0.9335(2) -0.02438(5) 0.77298(11) 0.0392(3) Uani d 1 1
H H3 1.007(3) 0.3794(9) 0.6895(15) 0.033(5) Uiso d 1 1
H H5 0.932(3) 0.2178(9) 0.4859(16) 0.040(6) Uiso d 1 1
H H6 0.933(4) 0.1269(10) 0.5321(17) 0.044(6) Uiso d 1 1
H H10A 0.718(4) -0.0011(9) 0.6641(16) 0.040(6) Uiso d 1 1
H H11A 0.894(4) 0.0492(9) 0.5699(17) 0.041(6) Uiso d 1 1
H H12A 0.994(4) 0.1002(10) 0.8522(18) 0.049(7) Uiso d 1 1
H H13A 0.767(4) 0.0294(9) 0.8267(17) 0.047(7) Uiso d 1 1
H H10B 0.873(3) -0.0424(8) 0.6329(15) 0.032(5) Uiso d 1 1
H H11B 1.096(4) 0.0303(9) 0.6439(16) 0.039(6) Uiso d 1 1
H H12B 1.163(3) 0.0635(9) 0.8302(16) 0.034(6) Uiso d 1 1
H H13B 0.975(3) 0.0070(9) 0.9046(17) 0.042(6) Uiso d 1 1
H H1A 0.813(4) 0.3148(10) 0.4693(17) 0.052(7) Uiso d 1 1
H H1B 0.952(4) 0.3694(9) 0.5139(16) 0.043(6) Uiso d 1 1
H H1C 1.044(4) 0.3129(10) 0.4814(17) 0.050(7) Uiso d 1 1
C C1' 0.5723(3) 0.60840(7) 0.95517(14) 0.0351(4) Uani d 1 1
C C2' 0.5056(3) 0.63447(7) 0.67842(13) 0.0311(4) Uani d 1 1
C C3' 0.5351(3) 0.60840(6) 0.77339(13) 0.0296(4) Uani d 1 1
C C4' 0.5482(3) 0.63685(6) 0.85765(13) 0.0278(3) Uani d 1 1
C C5' 0.5510(3) 0.73147(7) 0.93349(13) 0.0291(4) Uani d 1 1
C C6' 0.5393(3) 0.78692(7) 0.91930(13) 0.0300(4) Uani d 1 1
C C7' 0.5129(3) 0.80747(6) 0.82181(13) 0.0274(3) Uani d 1 1
C C8' 0.5105(3) 0.72095(6) 0.76077(12) 0.0267(3) Uani d 1 1
C C9' 0.5359(2) 0.69574(6) 0.85298(12) 0.0262(3) Uani d 1 1
C C10' 0.4305(3) 0.95433(7) 0.84990(16) 0.0381(4) Uani d 1 1
C C11' 0.5584(3) 0.90424(7) 0.87593(15) 0.0346(4) Uani d 1 1
C C12' 0.4811(3) 0.88138(7) 0.70015(14) 0.0340(4) Uani d 1 1
C C13' 0.3556(3) 0.93232(7) 0.68180(16) 0.0371(4) Uani d 1 1
N N1' 0.4991(2) 0.77406(6) 0.74347(10) 0.0284(3) Uani d 1 1
N N2' 0.4932(3) 0.86204(5) 0.80112(11) 0.0324(3) Uani d 1 1
O O1' 0.4949(2) 0.69094(5) 0.67596(9) 0.0313(3) Uani d 1 1
O O2' 0.4875(2) 0.61180(5) 0.59927(10) 0.0411(3) Uani d 1 1
O O3' 0.4279(2) 0.97386(5) 0.75282(11) 0.0387(3) Uani d 1 1
H H3' 0.538(3) 0.5695(10) 0.7721(16) 0.039(6) Uiso d 1 1
H H5' 0.566(3) 0.7175(9) 1.0013(15) 0.036(6) Uiso d 1 1
H H6' 0.547(3) 0.8105(9) 0.9725(15) 0.037(6) Uiso d 1 1
H H10C 0.289(4) 0.9457(9) 0.8536(17) 0.044(6) Uiso d 1 1
H H11C 0.554(4) 0.8922(9) 0.9401(17) 0.040(6) Uiso d 1 1
H H12C 0.419(4) 0.8540(9) 0.6579(16) 0.043(6) Uiso d 1 1
H H13C 0.215(3) 0.9233(9) 0.6834(16) 0.037(6) Uiso d 1 1
H H10D 0.482(3) 0.9822(9) 0.8955(16) 0.039(6) Uiso d 1 1
H H11D 0.696(4) 0.9148(10) 0.8762(17) 0.046(6) Uiso d 1 1
H H12D 0.616(3) 0.8896(9) 0.6928(15) 0.032(5) Uiso d 1 1
H H13D 0.366(4) 0.9486(9) 0.6128(17) 0.044(6) Uiso d 1 1
H H1D 0.459(4) 0.6172(9) 0.9843(17) 0.043(6) Uiso d 1 1
H H1E 0.588(4) 0.5682(10) 0.9486(17) 0.044(6) Uiso d 1 1
H H1F 0.684(4) 0.6220(9) 1.0033(17) 0.041(6) Uiso d 1 1
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
C1 0.0478(12) 0.0315(8) 0.0297(9) 0.0035(8) 0.0077(8) 0.0065(7)
C2 0.0347(9) 0.0217(7) 0.0310(8) -0.0027(6) 0.0094(7) -0.0014(6)
C3 0.0322(9) 0.0226(7) 0.0319(8) 0.0007(6) 0.0098(7) 0.0016(6)
C4 0.0263(8) 0.0249(7) 0.0297(8) 0.0020(6) 0.0071(7) 0.0039(6)
C5 0.0319(9) 0.0269(7) 0.0289(8) -0.0004(6) 0.0087(7) -0.0021(6)
C6 0.0340(9) 0.0254(7) 0.0312(8) -0.0011(7) 0.0102(7) -0.0049(6)
C7 0.0285(8) 0.0221(7) 0.0331(8) 0.0003(6) 0.0104(7) -0.0011(6)
C8 0.0267(8) 0.0232(7) 0.0273(8) 0.0003(6) 0.0086(6) -0.0009(6)
C9 0.0264(8) 0.0232(7) 0.0266(8) 0.0009(6) 0.0060(6) 0.0000(6)
C10 0.0377(10) 0.0242(7) 0.0496(11) -0.0027(7) 0.0081(9) -0.0028(7)
C11 0.0408(10) 0.0227(7) 0.0417(10) -0.0007(7) 0.0146(8) -0.0053(7)
C12 0.0506(12) 0.0240(7) 0.0360(9) -0.0043(8) 0.0105(9) 0.0016(7)
C13 0.0494(12) 0.0257(8) 0.0457(11) -0.0010(8) 0.0175(10) 0.0033(7)
N1 0.0339(8) 0.0213(6) 0.0304(7) -0.0009(5) 0.0097(6) 0.0005(5)
N2 0.0403(9) 0.0204(6) 0.0341(7) -0.0012(6) 0.0110(7) -0.0011(5)
O1 0.0444(8) 0.0208(5) 0.0265(6) -0.0017(5) 0.0100(5) 0.0002(4)
O2 0.0597(10) 0.0257(5) 0.0324(7) -0.0051(6) 0.0142(7) -0.0041(5)
O3 0.0437(8) 0.0213(5) 0.0524(8) -0.0007(5) 0.0110(7) 0.0027(5)
C1' 0.0441(11) 0.0280(8) 0.0324(9) -0.0003(8) 0.0072(8) 0.0054(7)
C2' 0.0338(9) 0.0241(7) 0.0346(9) 0.0025(6) 0.0065(7) -0.0014(6)
C3' 0.0329(9) 0.0200(7) 0.0347(9) -0.0001(6) 0.0056(7) 0.0011(6)
C4' 0.0247(8) 0.0242(7) 0.0335(8) -0.0015(6) 0.0048(7) 0.0017(6)
C5' 0.0317(9) 0.0262(7) 0.0300(8) -0.0018(6) 0.0084(7) 0.0016(6)
C6' 0.0344(9) 0.0257(7) 0.0314(8) -0.0015(7) 0.0109(7) -0.0034(6)
C7' 0.0267(8) 0.0228(7) 0.0337(8) 0.0001(6) 0.0093(7) 0.0005(6)
C8' 0.0277(8) 0.0237(7) 0.0290(8) -0.0005(6) 0.0071(7) -0.0021(6)
C9' 0.0251(8) 0.0232(7) 0.0298(8) -0.0013(6) 0.0059(7) 0.0018(6)
C10' 0.0445(11) 0.0236(7) 0.0503(11) 0.0004(8) 0.0197(9) -0.0037(7)
C11' 0.0441(11) 0.0235(7) 0.0385(9) -0.0015(7) 0.0139(8) -0.0023(7)
C12' 0.0437(11) 0.0238(7) 0.0369(9) 0.0032(7) 0.0144(8) 0.0027(7)
C13' 0.0399(11) 0.0246(7) 0.0466(11) 0.0022(7) 0.0099(9) 0.0022(7)
N1' 0.0327(8) 0.0230(6) 0.0295(7) 0.0018(5) 0.0074(6) 0.0015(5)
N2' 0.0452(9) 0.0204(6) 0.0336(7) 0.0009(6) 0.0132(7) 0.0005(5)
O1' 0.0413(7) 0.0227(5) 0.0293(6) 0.0024(5) 0.0073(5) 0.0004(4)
O2' 0.0603(10) 0.0289(6) 0.0327(7) 0.0056(6) 0.0079(7) -0.0038(5)
O3' 0.0457(8) 0.0209(5) 0.0507(8) -0.0011(5) 0.0137(7) 0.0008(5)
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
C4 C1 H1A 109.4(13)
C4 C1 H1B 109.2(12)
H1A C1 H1B 109.9(19)
C4 C1 H1C 110.0(15)
H1A C1 H1C 107.0(19)
H1B C1 H1C 111(2)
O2 C2 O1 116.28(15)
O2 C2 C3 125.72(16)
O1 C2 C3 118.00(14)
C4 C3 C2 122.28(15)
C4 C3 H3 123.8(12)
C2 C3 H3 113.9(12)
C3 C4 C9 118.40(15)
C3 C4 C1 121.83(16)
C9 C4 C1 119.77(15)
C6 C5 C9 120.31(16)
C6 C5 H5 118.5(13)
C9 C5 H5 121.2(13)
C5 C6 C7 118.78(15)
C5 C6 H6 120.3(15)
C7 C6 H6 120.9(15)
N1 C7 N2 115.86(15)
N1 C7 C6 121.96(15)
N2 C7 C6 122.17(15)
N1 C8 O1 112.40(14)
N1 C8 C9 126.53(15)
O1 C8 C9 121.07(14)
C8 C9 C5 115.46(15)
C8 C9 C4 119.34(15)
C5 C9 C4 125.20(15)
O3 C10 C11 111.69(16)
O3 C10 H10A 108.2(13)
C11 C10 H10A 110.2(13)
O3 C10 H10B 105.7(12)
C11 C10 H10B 110.4(12)
H10A C10 H10B 110.5(18)
N2 C11 C10 109.48(16)
N2 C11 H11A 111.1(13)
C10 C11 H11A 107.6(13)
N2 C11 H11B 109.5(13)
C10 C11 H11B 111.1(14)
H11A C11 H11B 107.9(18)
N2 C12 C13 109.75(17)
N2 C12 H12A 107.7(15)
C13 C12 H12A 108.6(15)
N2 C12 H12B 110.3(13)
C13 C12 H12B 111.1(13)
H12A C12 H12B 109(2)
O3 C13 C12 111.18(17)
O3 C13 H13A 109.1(13)
C12 C13 H13A 110.2(13)
O3 C13 H13B 104.6(13)
C12 C13 H13B 108.8(13)
H13A C13 H13B 112.8(19)
C8 N1 C7 116.94(15)
C7 N2 C11 121.95(16)
C7 N2 C12 119.91(14)
C11 N2 C12 113.31(15)
C8 O1 C2 120.91(13)
C10 O3 C13 109.75(15)
C4' C1' H1D 109.5(13)
C4' C1' H1E 111.5(13)
H1D C1' H1E 111.6(19)
C4' C1' H1F 111.8(14)
H1D C1' H1F 104.0(19)
H1E C1' H1F 108.2(19)
O2' C2' O1' 116.13(16)
O2' C2' C3' 126.42(16)
O1' C2' C3' 117.45(15)
C4' C3' C2' 122.42(15)
C4' C3' H3' 122.4(13)
C2' C3' H3' 115.1(13)
C3' C4' C9' 119.01(15)
C3' C4' C1' 121.19(15)
C9' C4' C1' 119.80(15)
C6' C5' C9' 120.66(16)
C6' C5' H5' 118.0(12)
C9' C5' H5' 121.3(12)
C5' C6' C7' 118.61(16)
C5' C6' H6' 120.6(13)
C7' C6' H6' 120.7(13)
N1' C7' N2' 115.96(15)
N1' C7' C6' 121.83(15)
N2' C7' C6' 122.17(15)
N1' C8' O1' 112.35(15)
N1' C8' C9' 126.23(15)
O1' C8' C9' 121.42(15)
C8' C9' C5' 115.30(15)
C8' C9' C4' 118.37(15)
C5' C9' C4' 126.31(15)
O3' C10' C11' 111.85(16)
O3' C10' H10C 108.4(13)
C11' C10' H10C 110.6(13)
O3' C10' H10D 108.2(14)
C11' C10' H10D 108.1(14)
H10C C10' H10D 109.7(19)
N2' C11' C10' 109.27(17)
N2' C11' H11C 112.2(14)
C10' C11' H11C 109.1(14)
N2' C11' H11D 109.1(14)
C10' C11' H11D 108.4(14)
H11C C11' H11D 108.7(19)
N2' C12' C13' 109.14(16)
N2' C12' H12C 106.7(14)
C13' C12' H12C 108.5(15)
N2' C12' H12D 108.6(12)
C13' C12' H12D 110.5(12)
H12C C12' H12D 113.3(19)
O3' C13' C12' 111.63(17)
O3' C13' H13C 109.3(12)
C12' C13' H13C 110.6(12)
O3' C13' H13D 105.7(12)
C12' C13' H13D 107.5(13)
H13C C13' H13D 112.1(18)
C8' N1' C7' 117.35(15)
C7' N2' C11' 122.71(16)
C7' N2' C12' 119.85(15)
C11' N2' C12' 113.14(14)
C8' O1' C2' 121.32(14)
C13' O3' C10' 109.91(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C7 1.414(3)
C7 N1 1.350(2)
C8 N1 1.324(2)
C8 C9 1.394(2)
C5 C9 1.403(2)
C5 C6 1.377(2)
C8 O1 1.377(2)
C2 O1 1.383(2)
C2 C3 1.444(2)
C3 C4 1.349(2)
C4 C9 1.445(2)
C2 O2 1.217(2)
C6' C7' 1.419(2)
C7' N1' 1.349(2)
C8' N1' 1.322(2)
C8' C9' 1.398(2)
C5' C9' 1.407(2)
C5' C6' 1.372(2)
C8' O1' 1.374(2)
C2' O1' 1.385(2)
C2' C3' 1.440(2)
C3' C4' 1.349(2)
C4' C9' 1.445(2)
C2' O2' 1.214(2)
C7 N2 1.376(2)
C7' N2' 1.367(2)
C1 C4 1.501(2)
C1 H1A 1.03(3)
C1 H1B 1.03(2)
C1 H1C 0.96(3)
C3 H3 0.99(2)
C5 H5 1.00(2)
C6 H6 0.92(2)
C10 O3 1.426(3)
C10 C11 1.521(3)
C10 H10A 0.98(2)
C10 H10B 1.00(2)
C11 N2 1.460(2)
C11 H11A 1.04(2)
C11 H11B 0.96(2)
C12 N2 1.466(2)
C12 C13 1.514(3)
C12 H12A 0.96(3)
C12 H12B 0.98(2)
C13 O3 1.430(2)
C13 H13A 1.03(3)
C13 H13B 1.01(2)
C1' C4' 1.501(2)
C1' H1D 1.00(3)
C1' H1E 1.00(2)
C1' H1F 0.97(2)
C3' H3' 0.95(2)
C5' H5' 0.99(2)
C6' H6' 0.93(2)
C10' O3' 1.431(3)
C10' C11' 1.516(3)
C10' H10C 1.04(3)
C10' H10D 0.95(2)
C11' N2' 1.464(2)
C11' H11C 0.95(2)
C11' H11D 1.00(3)
C12' N2' 1.468(2)
C12' C13' 1.517(3)
C12' H12C 0.93(2)
C12' H12D 1.00(2)
C13' O3' 1.428(2)
C13' H13C 1.02(2)
C13' H13D 1.06(2)
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
C6 C7 N2 C11 11.6(3)
N1 C7 N2 C12 -15.8(3)
C6' C7' N2' C11' 20.3(3)
N1' C7' N2' C12' -6.8(3)
O2 C2 C3 C4 -179.52(19)
O1 C2 C3 C4 -0.3(3)
C2 C3 C4 C9 -0.1(3)
C2 C3 C4 C1 179.33(18)
C9 C5 C6 C7 0.7(3)
C5 C6 C7 N1 -1.8(3)
C5 C6 C7 N2 176.89(18)
N1 C8 C9 C5 -1.1(3)
O1 C8 C9 C5 178.85(15)
N1 C8 C9 C4 179.81(18)
O1 C8 C9 C4 -0.2(3)
C6 C5 C9 C8 0.7(3)
C6 C5 C9 C4 179.70(18)
C3 C4 C9 C8 0.4(3)
C1 C4 C9 C8 -179.06(17)
C3 C4 C9 C5 -178.56(17)
C1 C4 C9 C5 1.9(3)
O3 C10 C11 N2 -55.6(2)
N2 C12 C13 O3 56.2(2)
O1 C8 N1 C7 -179.92(15)
C9 C8 N1 C7 0.0(3)
N2 C7 N1 C8 -177.33(17)
C6 C7 N1 C8 1.5(3)
N1 C7 N2 C11 -169.55(17)
C6 C7 N2 C12 165.38(18)
C10 C11 N2 C7 -152.67(18)
C10 C11 N2 C12 52.0(2)
C13 C12 N2 C7 151.52(18)
C13 C12 N2 C11 -52.6(2)
N1 C8 O1 C2 179.71(16)
C9 C8 O1 C2 -0.2(3)
O2 C2 O1 C8 179.79(16)
C3 C2 O1 C8 0.5(3)
C11 C10 O3 C13 60.5(2)
C12 C13 O3 C10 -60.7(2)
O2' C2' C3' C4' -178.1(2)
O1' C2' C3' C4' 1.4(3)
C2' C3' C4' C9' -1.2(3)
C2' C3' C4' C1' 177.93(18)
C9' C5' C6' C7' -0.4(3)
C5' C6' C7' N1' 0.0(3)
C5' C6' C7' N2' 177.74(18)
N1' C8' C9' C5' -0.3(3)
O1' C8' C9' C5' 179.55(16)
N1' C8' C9' C4' -179.00(17)
O1' C8' C9' C4' 0.9(3)
C6' C5' C9' C8' 0.5(3)
C6' C5' C9' C4' 179.12(18)
C3' C4' C9' C8' 0.0(3)
C1' C4' C9' C8' -179.06(16)
C3' C4' C9' C5' -178.50(17)
C1' C4' C9' C5' 2.4(3)
O3' C10' C11' N2' -55.8(2)
N2' C12' C13' O3' 56.4(2)
O1' C8' N1' C7' -179.94(15)
C9' C8' N1' C7' -0.1(3)
N2' C7' N1' C8' -177.62(17)
C6' C7' N1' C8' 0.2(3)
N1' C7' N2' C11' -161.88(18)
C6' C7' N2' C12' 175.38(17)
C10' C11' N2' C7' -150.07(18)
C10' C11' N2' C12' 53.3(2)
C13' C12' N2' C7' 149.04(18)
C13' C12' N2' C11' -53.6(2)
N1' C8' O1' C2' 179.24(16)
C9' C8' O1' C2' -0.6(3)
O2' C2' O1' C8' 179.05(17)
C3' C2' O1' C8' -0.4(3)
C12' C13' O3' C10' -59.9(2)
C11' C10' O3' C13' 59.7(2)
_cod_database_fobs_code 2104986