##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2012-01-04
_journal_date_accepted     2012-03-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o998
_journal_page_last     o999
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812009312
_journal_coeditor_code     NR2019
_publ_contact_author_name     'Xiu-Rong Hu'
_publ_contact_author_address
;
Center of Analysis and Measurement
Zhejiang University
Hangzhou, 310028
People's Republic of China
People's Republic of China
People's Republic of China
;
_publ_contact_author_email     'huxiurong@yahoo.com.cn'
_publ_contact_author_fax     '86-571-88273690'
_publ_contact_author_phone     '86-571-88273491'
_publ_section_title
;
Marbofloxacin
;
loop_
    _publ_author_name
    _publ_author_address
    'Jin Shen'
;
College of Pharmaceutical Science
Zhejiang Chinese Medical University
Hangzhou, Zhejiang 310053
People's Republic of China
;
    'Jing-Jing Qian'
;
College of Pharmaceutical Science
Zhejiang Chinese Medical University
Hangzhou, Zhejiang 310053
People's Republic of China
;
    'Jian-Ming Gu'
;
Center of Analysis and Measurement
Zhejiang University
Hangzhou, Zhejiang 310028
People's Republic of China
;
    'Xiu-Rong Hu'
;
Center of Analysis and Measurement
Zhejiang University
Hangzhou, Zhejiang 310028
People's Republic of China
;
_chemical_name_systematic
;
9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-piperazino)-7-oxo-7H
-pyrido(1,2,3-ij)(1,2,4)benzoxadiazine-6-carboxylic acid
;
data_I
_chemical_name_systematic
;
7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1,2-
diazatricyclo[7.3.1.0^5,13^]trideca-5,7,9(13),11-tetraene-11-carboxylic acid
;
_chemical_name_common
;
9-fluoro-2,3-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-
7-oxo-7<i>H</i>-pyrido[1,2,3-<i>ij</i>][1,2,4]benzoxadiazine-6-carboxylic acid
;
_chemical_formula_moiety     'C17 H19 F N4 O4'
_chemical_formula_sum     'C17 H19 F N4 O4'
_chemical_formula_weight     362.36
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.0145(5)
_cell_length_b     8.9218(6)
_cell_length_c     13.0874(8)
_cell_angle_alpha     91.65(3)
_cell_angle_beta     99.65(3)
_cell_angle_gamma     115.091(10)
_cell_volume     830.26(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4017
_cell_measurement_theta_min     3.1
_cell_measurement_theta_max     27.4
_cell_measurement_temperature     296.0(10)
_exptl_crystal_description     'plates'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.449
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     380
_exptl_absorpt_coefficient_mu     0.113
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.9559
_exptl_absorpt_correction_T_max     0.9965
_exptl_special_details     ?
_diffrn_ambient_temperature     296.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rolling anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     6601
_diffrn_reflns_av_R_equivalents     0.0523
_diffrn_reflns_av_sigmaI/netI     0.0758
_diffrn_reflns_theta_min     3.14
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2925
_reflns_number_gt     1428
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1267
_refine_ls_R_factor_gt     0.0554
_refine_ls_wR_factor_gt     0.1241
_refine_ls_wR_factor_ref     0.2025
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     1.000
_refine_ls_number_reflns     2925
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.8525P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_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     0.286
_refine_diff_density_min     -0.337
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'PROCESS-AUTO  (Rigaku, 2006)'
_computing_cell_refinement     'PROCESS-AUTO  (Rigaku, 2006)'
_computing_data_reduction     'CrystalStructure (Rigaku, 2007)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Ortep3 for windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    F F1 0.2105(3) 0.1945(3) 0.64667(19) 0.0642(7) Uani d . 1 1 . .
    O O1 0.2871(5) 0.7762(4) 1.0967(2) 0.0680(9) Uani d D 1 1 . .
    H H1 0.230(6) 0.693(4) 1.053(3) 0.09(2) Uiso d D 1 1 . .
    O O2 0.5831(5) 0.9686(4) 1.1352(2) 0.0732(10) Uani d . 1 1 . .
    O O3 0.1921(4) 0.5352(4) 0.9550(2) 0.0594(8) Uani d . 1 1 . .
    O O4 0.8358(3) 0.6152(3) 0.7475(2) 0.0539(8) Uani d . 1 1 . .
    N N1 0.9081(4) 0.8423(4) 0.8761(3) 0.0499(9) Uani d . 1 1 . .
    N N2 0.7233(4) 0.7572(4) 0.8983(2) 0.0455(8) Uani d . 1 1 . .
    N N3 0.5854(4) 0.3404(4) 0.6136(2) 0.0494(9) Uani d . 1 1 . .
    N N4 0.7031(5) 0.1924(4) 0.4634(3) 0.0551(9) Uani d . 1 1 . .
    C C1 0.4644(7) 0.8439(6) 1.0818(3) 0.0576(11) Uani d . 1 1 . .
    C C2 0.5010(5) 0.7549(5) 0.9964(3) 0.0451(10) Uani d . 1 1 . .
    C C3 0.3568(6) 0.6070(5) 0.9367(3) 0.0467(10) Uani d . 1 1 . .
    C C4 0.4097(5) 0.5369(4) 0.8514(3) 0.0414(9) Uani d . 1 1 . .
    C C5 0.2802(5) 0.3970(5) 0.7853(3) 0.0475(10) Uani d . 1 1 . .
    H H5 0.1554 0.3464 0.7926 0.057 Uiso calc R 1 1 . .
    C C6 0.3386(5) 0.3344(5) 0.7091(3) 0.0484(10) Uani d . 1 1 . .
    C C7 0.5238(5) 0.4014(4) 0.6918(3) 0.0436(9) Uani d . 1 1 . .
    C C8 0.6516(5) 0.5420(5) 0.7594(3) 0.0441(9) Uani d . 1 1 . .
    C C9 0.9600(5) 0.7160(5) 0.8421(3) 0.0557(11) Uani d . 1 1 . .
    H H9A 0.9574 0.6446 0.8969 0.067 Uiso calc R 1 1 . .
    H H9B 1.0876 0.7688 0.8302 0.067 Uiso calc R 1 1 . .
    C C10 0.6778(5) 0.8265(5) 0.9749(3) 0.0463(10) Uani d . 1 1 . .
    H H10 0.7678 0.9247 1.0140 0.056 Uiso calc R 1 1 . .
    C C11 0.5951(5) 0.6118(4) 0.8364(3) 0.0400(9) Uani d . 1 1 . .
    C C12 0.9089(7) 0.9603(5) 0.7983(4) 0.0665(13) Uani d . 1 1 . .
    H H12A 0.8252 0.8996 0.7343 0.100 Uiso calc R 1 1 . .
    H H12B 1.0339 1.0196 0.7856 0.100 Uiso calc R 1 1 . .
    H H12C 0.8681 1.0380 0.8246 0.100 Uiso calc R 1 1 . .
    C C13 0.4605(6) 0.2587(6) 0.5132(3) 0.0628(12) Uani d . 1 1 . .
    H H13A 0.3799 0.3129 0.4920 0.075 Uiso calc R 1 1 . .
    H H13B 0.3817 0.1428 0.5190 0.075 Uiso calc R 1 1 . .
    C C14 0.5809(7) 0.2709(6) 0.4340(3) 0.0684(13) Uani d . 1 1 . .
    H H14A 0.5007 0.2181 0.3667 0.082 Uiso calc R 1 1 . .
    H H14B 0.6560 0.3872 0.4272 0.082 Uiso calc R 1 1 . .
    C C15 0.8245(6) 0.2699(6) 0.5640(3) 0.0651(13) Uani d . 1 1 . .
    H H15A 0.9056 0.3855 0.5587 0.078 Uiso calc R 1 1 . .
    H H15B 0.9034 0.2138 0.5841 0.078 Uiso calc R 1 1 . .
    C C16 0.7106(6) 0.2613(5) 0.6461(3) 0.0546(11) Uani d . 1 1 . .
    H H16A 0.6367 0.1459 0.6557 0.065 Uiso calc R 1 1 . .
    H H16B 0.7939 0.3180 0.7120 0.065 Uiso calc R 1 1 . .
    C C17 0.8116(7) 0.1965(6) 0.3831(4) 0.0840(17) Uani d . 1 1 . .
    H H17A 0.7272 0.1399 0.3185 0.126 Uiso calc R 1 1 . .
    H H17B 0.8906 0.1422 0.4042 0.126 Uiso calc R 1 1 . .
    H H17C 0.8881 0.3101 0.3740 0.126 Uiso calc R 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
    F1 0.0504(14) 0.0478(13) 0.0771(17) 0.0064(11) 0.0123(12) -0.0136(12)
    O1 0.077(2) 0.081(2) 0.0573(19) 0.0394(19) 0.0278(17) 0.0012(18)
    O2 0.084(2) 0.072(2) 0.0611(19) 0.0311(18) 0.0186(17) -0.0087(17)
    O3 0.0514(17) 0.0659(18) 0.0658(19) 0.0245(15) 0.0267(15) 0.0086(15)
    O4 0.0438(15) 0.0543(16) 0.0548(17) 0.0115(13) 0.0164(13) -0.0057(13)
    N1 0.0444(19) 0.0450(18) 0.056(2) 0.0129(15) 0.0172(16) 0.0015(16)
    N2 0.0415(18) 0.0460(18) 0.0441(18) 0.0137(15) 0.0112(14) 0.0023(15)
    N3 0.053(2) 0.060(2) 0.0391(17) 0.0302(17) 0.0041(15) -0.0071(15)
    N4 0.067(2) 0.0451(19) 0.052(2) 0.0196(17) 0.0221(17) -0.0016(16)
    C1 0.066(3) 0.068(3) 0.051(3) 0.038(2) 0.020(2) 0.010(2)
    C2 0.059(3) 0.048(2) 0.036(2) 0.029(2) 0.0121(18) 0.0061(17)
    C3 0.051(2) 0.053(2) 0.044(2) 0.0278(19) 0.0146(19) 0.0114(19)
    C4 0.049(2) 0.0373(19) 0.040(2) 0.0200(17) 0.0092(17) 0.0053(16)
    C5 0.042(2) 0.045(2) 0.055(2) 0.0169(18) 0.0115(18) 0.0051(19)
    C6 0.042(2) 0.038(2) 0.056(2) 0.0102(17) 0.0063(18) -0.0031(18)
    C7 0.051(2) 0.0363(19) 0.046(2) 0.0205(17) 0.0110(18) 0.0056(17)
    C8 0.042(2) 0.046(2) 0.044(2) 0.0186(17) 0.0121(17) 0.0003(18)
    C9 0.042(2) 0.057(2) 0.059(3) 0.0149(19) 0.0090(19) -0.007(2)
    C10 0.054(2) 0.048(2) 0.038(2) 0.0236(19) 0.0104(18) -0.0031(17)
    C11 0.041(2) 0.0352(18) 0.0396(19) 0.0131(16) 0.0082(16) 0.0025(16)
    C12 0.069(3) 0.058(3) 0.068(3) 0.018(2) 0.025(2) 0.010(2)
    C13 0.066(3) 0.068(3) 0.052(3) 0.031(2) 0.001(2) -0.010(2)
    C14 0.083(3) 0.070(3) 0.049(3) 0.032(3) 0.010(2) -0.001(2)
    C15 0.063(3) 0.079(3) 0.057(3) 0.034(2) 0.015(2) -0.005(2)
    C16 0.063(3) 0.061(3) 0.053(2) 0.038(2) 0.015(2) 0.005(2)
    C17 0.098(4) 0.073(3) 0.074(3) 0.021(3) 0.048(3) -0.007(3)
_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
    F1 C6 . 1.361(4) ?
    O1 C1 . 1.339(5) ?
    O1 H1 . 0.83(3) ?
    O2 C1 . 1.210(5) ?
    O3 C3 . 1.267(4) ?
    O4 C8 . 1.377(4) ?
    O4 C9 . 1.448(4) ?
    N1 N2 . 1.434(4) ?
    N1 C9 . 1.439(5) ?
    N1 C12 . 1.484(6) ?
    N2 C10 . 1.341(4) ?
    N2 C11 . 1.387(4) ?
    N3 C7 . 1.397(4) ?
    N3 C13 . 1.465(5) ?
    N3 C16 . 1.470(5) ?
    N4 C14 . 1.438(6) ?
    N4 C15 . 1.451(5) ?
    N4 C17 . 1.464(5) ?
    C1 C2 . 1.491(5) ?
    C2 C10 . 1.368(5) ?
    C2 C3 . 1.425(5) ?
    C3 C4 . 1.470(5) ?
    C4 C5 . 1.387(5) ?
    C4 C11 . 1.399(5) ?
    C5 C6 . 1.368(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.407(5) ?
    C7 C8 . 1.395(5) ?
    C8 C11 . 1.401(5) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10 . 0.9300 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 C14 . 1.507(6) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.506(5) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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
    C1 O1 H1 . . 106(4) ?
    C8 O4 C9 . . 111.3(3) ?
    N2 N1 C9 . . 106.7(3) ?
    N2 N1 C12 . . 109.9(3) ?
    C9 N1 C12 . . 113.8(3) ?
    C10 N2 C11 . . 122.3(3) ?
    C10 N2 N1 . . 118.4(3) ?
    C11 N2 N1 . . 119.1(3) ?
    C7 N3 C13 . . 121.3(3) ?
    C7 N3 C16 . . 117.4(3) ?
    C13 N3 C16 . . 110.8(3) ?
    C14 N4 C15 . . 110.1(3) ?
    C14 N4 C17 . . 111.2(4) ?
    C15 N4 C17 . . 111.6(4) ?
    O2 C1 O1 . . 120.9(4) ?
    O2 C1 C2 . . 123.9(4) ?
    O1 C1 C2 . . 115.2(4) ?
    C10 C2 C3 . . 121.6(3) ?
    C10 C2 C1 . . 116.6(3) ?
    C3 C2 C1 . . 121.7(4) ?
    O3 C3 C2 . . 123.6(3) ?
    O3 C3 C4 . . 120.3(3) ?
    C2 C3 C4 . . 116.0(3) ?
    C5 C4 C11 . . 118.8(3) ?
    C5 C4 C3 . . 121.6(4) ?
    C11 C4 C3 . . 119.6(3) ?
    C6 C5 C4 . . 119.0(4) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    F1 C6 C5 . . 118.2(3) ?
    F1 C6 C7 . . 117.0(3) ?
    C5 C6 C7 . . 124.8(3) ?
    N3 C7 C8 . . 119.3(3) ?
    N3 C7 C6 . . 125.6(3) ?
    C8 C7 C6 . . 115.1(3) ?
    O4 C8 C7 . . 118.6(3) ?
    O4 C8 C11 . . 119.9(3) ?
    C7 C8 C11 . . 121.5(3) ?
    N1 C9 O4 . . 112.4(3) ?
    N1 C9 H9A . . 109.1 ?
    O4 C9 H9A . . 109.1 ?
    N1 C9 H9B . . 109.1 ?
    O4 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.9 ?
    N2 C10 C2 . . 121.0(3) ?
    N2 C10 H10 . . 119.5 ?
    C2 C10 H10 . . 119.5 ?
    N2 C11 C4 . . 119.3(3) ?
    N2 C11 C8 . . 120.0(3) ?
    C4 C11 C8 . . 120.7(3) ?
    N1 C12 H12A . . 109.5 ?
    N1 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N1 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N3 C13 C14 . . 108.0(4) ?
    N3 C13 H13A . . 110.1 ?
    C14 C13 H13A . . 110.1 ?
    N3 C13 H13B . . 110.1 ?
    C14 C13 H13B . . 110.1 ?
    H13A C13 H13B . . 108.4 ?
    N4 C14 C13 . . 111.6(4) ?
    N4 C14 H14A . . 109.3 ?
    C13 C14 H14A . . 109.3 ?
    N4 C14 H14B . . 109.3 ?
    C13 C14 H14B . . 109.3 ?
    H14A C14 H14B . . 108.0 ?
    N4 C15 C16 . . 111.0(4) ?
    N4 C15 H15A . . 109.4 ?
    C16 C15 H15A . . 109.4 ?
    N4 C15 H15B . . 109.4 ?
    C16 C15 H15B . . 109.4 ?
    H15A C15 H15B . . 108.0 ?
    N3 C16 C15 . . 109.4(4) ?
    N3 C16 H16A . . 109.8 ?
    C15 C16 H16A . . 109.8 ?
    N3 C16 H16B . . 109.8 ?
    C15 C16 H16B . . 109.8 ?
    H16A C16 H16B . . 108.2 ?
    N4 C17 H17A . . 109.5 ?
    N4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    N4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C9 N1 N2 C10 . . . . 147.4(4) ?
    C12 N1 N2 C10 . . . . -88.8(4) ?
    C9 N1 N2 C11 . . . . -36.1(5) ?
    C12 N1 N2 C11 . . . . 87.7(4) ?
    O2 C1 C2 C10 . . . . -3.8(7) ?
    O1 C1 C2 C10 . . . . 176.1(4) ?
    O2 C1 C2 C3 . . . . 179.1(4) ?
    O1 C1 C2 C3 . . . . -1.0(6) ?
    C10 C2 C3 O3 . . . . 178.9(4) ?
    C1 C2 C3 O3 . . . . -4.2(6) ?
    C10 C2 C3 C4 . . . . 0.0(6) ?
    C1 C2 C3 C4 . . . . 177.0(4) ?
    O3 C3 C4 C5 . . . . 3.6(6) ?
    C2 C3 C4 C5 . . . . -177.5(4) ?
    O3 C3 C4 C11 . . . . -176.1(4) ?
    C2 C3 C4 C11 . . . . 2.8(5) ?
    C11 C4 C5 C6 . . . . 1.5(6) ?
    C3 C4 C5 C6 . . . . -178.2(4) ?
    C4 C5 C6 F1 . . . . 178.3(4) ?
    C4 C5 C6 C7 . . . . 0.2(7) ?
    C13 N3 C7 C8 . . . . -148.1(4) ?
    C16 N3 C7 C8 . . . . 70.4(5) ?
    C13 N3 C7 C6 . . . . 30.9(6) ?
    C16 N3 C7 C6 . . . . -110.7(5) ?
    F1 C6 C7 N3 . . . . 2.7(6) ?
    C5 C6 C7 N3 . . . . -179.2(4) ?
    F1 C6 C7 C8 . . . . -178.3(3) ?
    C5 C6 C7 C8 . . . . -0.2(6) ?
    C9 O4 C8 C7 . . . . -159.0(4) ?
    C9 O4 C8 C11 . . . . 22.7(5) ?
    N3 C7 C8 O4 . . . . -0.8(6) ?
    C6 C7 C8 O4 . . . . -179.9(4) ?
    N3 C7 C8 C11 . . . . 177.4(4) ?
    C6 C7 C8 C11 . . . . -1.6(6) ?
    N2 N1 C9 O4 . . . . 62.1(4) ?
    C12 N1 C9 O4 . . . . -59.3(4) ?
    C8 O4 C9 N1 . . . . -56.7(4) ?
    C11 N2 C10 C2 . . . . 0.7(6) ?
    N1 N2 C10 C2 . . . . 177.0(4) ?
    C3 C2 C10 N2 . . . . -1.8(6) ?
    C1 C2 C10 N2 . . . . -178.9(4) ?
    C10 N2 C11 C4 . . . . 2.2(6) ?
    N1 N2 C11 C4 . . . . -174.1(3) ?
    C10 N2 C11 C8 . . . . -178.1(4) ?
    N1 N2 C11 C8 . . . . 5.6(5) ?
    C5 C4 C11 N2 . . . . 176.4(4) ?
    C3 C4 C11 N2 . . . . -3.9(6) ?
    C5 C4 C11 C8 . . . . -3.3(6) ?
    C3 C4 C11 C8 . . . . 176.4(4) ?
    O4 C8 C11 N2 . . . . 2.0(6) ?
    C7 C8 C11 N2 . . . . -176.2(4) ?
    O4 C8 C11 C4 . . . . -178.3(3) ?
    C7 C8 C11 C4 . . . . 3.4(6) ?
    C7 N3 C13 C14 . . . . 157.3(4) ?
    C16 N3 C13 C14 . . . . -58.9(5) ?
    C15 N4 C14 C13 . . . . -59.0(5) ?
    C17 N4 C14 C13 . . . . 176.7(3) ?
    N3 C13 C14 N4 . . . . 59.4(5) ?
    C14 N4 C15 C16 . . . . 57.3(5) ?
    C17 N4 C15 C16 . . . . -178.7(4) ?
    C7 N3 C16 C15 . . . . -156.2(3) ?
    C13 N3 C16 C15 . . . . 58.4(5) ?
    N4 C15 C16 N3 . . . . -56.9(5) ?
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
    O1 H1 O3 . 0.83(3) 1.77(2) 2.560(4) 159(5)
    C12 H12B F1 1_665 0.96 2.62 3.422(3) 140(4)
    C15 H15B F1 1_655 0.97 2.54 3.446(3) 155(5)
_iucr_refine_instructions_details
;
TITL marbo in P -1
CELL  0.71073   8.0145   8.9218  13.0874   91.655   99.646  115.091
ZERR     2.00   0.0005   0.0006   0.0008    0.027    0.030    0.010
LATT   1
SFAC  C    H    N    O    F
UNIT  34   38   8    8    2
MERG   2
OMIT    -3.00  50.02
HTAB   O1  O3
DFIX  0.82  0.01  O1 H1
FMAP   2
PLAN    3
SIZE     0.03   0.13   0.31
ACTA
BOND   $H
CONF
L.S.    15
TEMP    23.00
WGHT    0.072000    0.852500
FVAR       0.61141
F1    5    0.210519    0.194512    0.646671    11.00000    0.05036    0.04781 =
         0.07712   -0.01356    0.01228    0.00639
O1    4    0.287115    0.776204    1.096702    11.00000    0.07654    0.08081 =
         0.05729    0.00119    0.02782    0.03944
O2    4    0.583115    0.968559    1.135170    11.00000    0.08393    0.07207 =
         0.06107   -0.00869    0.01856    0.03110
O3    4    0.192130    0.535178    0.954998    11.00000    0.05138    0.06585 =
         0.06578    0.00863    0.02668    0.02451
O4    4    0.835825    0.615157    0.747473    11.00000    0.04383    0.05425 =
         0.05483   -0.00572    0.01644    0.01152
N1    3    0.908119    0.842330    0.876106    11.00000    0.04445    0.04496 =
         0.05574    0.00146    0.01718    0.01294
N2    3    0.723287    0.757193    0.898256    11.00000    0.04152    0.04597 =
         0.04414    0.00228    0.01119    0.01370
N3    3    0.585450    0.340434    0.613625    11.00000    0.05266    0.05984 =
         0.03906   -0.00713    0.00407    0.03017
N4    3    0.703072    0.192437    0.463365    11.00000    0.06654    0.04513 =
         0.05206   -0.00160    0.02210    0.01958
C1    1    0.464411    0.843914    1.081843    11.00000    0.06641    0.06837 =
         0.05092    0.01011    0.01978    0.03818
C2    1    0.501013    0.754882    0.996386    11.00000    0.05886    0.04832 =
         0.03585    0.00612    0.01213    0.02948
C3    1    0.356775    0.606979    0.936745    11.00000    0.05056    0.05309 =
         0.04444    0.01143    0.01461    0.02783
C4    1    0.409718    0.536869    0.851430    11.00000    0.04888    0.03732 =
         0.03951    0.00533    0.00921    0.01998
C5    1    0.280187    0.396966    0.785288    11.00000    0.04178    0.04452 =
         0.05483    0.00508    0.01152    0.01687
AFIX  43
H5    2    0.155413    0.346389    0.792637    11.00000   -1.20000
AFIX   0
C6    1    0.338580    0.334389    0.709051    11.00000    0.04164    0.03848 =
         0.05567   -0.00310    0.00626    0.01020
C7    1    0.523843    0.401395    0.691810    11.00000    0.05055    0.03628 =
         0.04622    0.00556    0.01102    0.02054
C8    1    0.651569    0.542012    0.759360    11.00000    0.04235    0.04609 =
         0.04438    0.00030    0.01213    0.01864
C9    1    0.959983    0.715999    0.842149    11.00000    0.04217    0.05744 =
         0.05888   -0.00744    0.00895    0.01489
AFIX  23
H9A   2    0.957406    0.644567    0.896936    11.00000   -1.20000
H9B   2    1.087573    0.768781    0.830246    11.00000   -1.20000
AFIX   0
C10   1    0.677798    0.826480    0.974867    11.00000    0.05416    0.04842 =
         0.03766   -0.00307    0.01036    0.02358
AFIX  43
H10   2    0.767832    0.924731    1.013977    11.00000   -1.20000
AFIX   0
C11   1    0.595074    0.611789    0.836370    11.00000    0.04133    0.03524 =
         0.03959    0.00253    0.00820    0.01313
C12   1    0.908908    0.960286    0.798293    11.00000    0.06864    0.05782 =
         0.06783    0.01023    0.02454    0.01849
AFIX 137
H12A  2    0.825220    0.899573    0.734327    11.00000   -1.50000
H12B  2    1.033876    1.019593    0.785650    11.00000   -1.50000
H12C  2    0.868138    1.037985    0.824574    11.00000   -1.50000
AFIX   0
C13   1    0.460514    0.258679    0.513215    11.00000    0.06552    0.06801 =
         0.05151   -0.01012    0.00089    0.03081
AFIX  23
H13A  2    0.379942    0.312907    0.491977    11.00000   -1.20000
H13B  2    0.381665    0.142777    0.519038    11.00000   -1.20000
AFIX   0
C14   1    0.580921    0.270877    0.433990    11.00000    0.08324    0.07014 =
         0.04889   -0.00107    0.00961    0.03224
AFIX  23
H14A  2    0.500663    0.218108    0.366671    11.00000   -1.20000
H14B  2    0.656031    0.387225    0.427232    11.00000   -1.20000
AFIX   0
C15   1    0.824452    0.269923    0.563951    11.00000    0.06308    0.07872 =
         0.05681   -0.00515    0.01495    0.03371
AFIX  23
H15A  2    0.905577    0.385472    0.558686    11.00000   -1.20000
H15B  2    0.903441    0.213837    0.584071    11.00000   -1.20000
AFIX   0
C16   1    0.710598    0.261288    0.646133    11.00000    0.06344    0.06082 =
         0.05276    0.00549    0.01538    0.03821
AFIX  23
H16A  2    0.636702    0.145933    0.655689    11.00000   -1.20000
H16B  2    0.793904    0.318013    0.712029    11.00000   -1.20000
AFIX   0
C17   1    0.811559    0.196488    0.383109    11.00000    0.09783    0.07309 =
         0.07447   -0.00703    0.04813    0.02069
AFIX 137
H17A  2    0.727179    0.139879    0.318490    11.00000   -1.50000
H17B  2    0.890587    0.142178    0.404209    11.00000   -1.50000
H17C  2    0.888070    0.310065    0.373987    11.00000   -1.50000
AFIX   0
H1    2    0.229663    0.693249    1.053364    11.00000    0.09161
HKLF    4
REM  marbo in P -1
REM R1 =  0.0554 for   1428 Fo > 4sig(Fo)  and  0.1267 for all   2925 data
REM    241 parameters refined using      1 restraints
END
WGHT      0.1063      0.0000
REM Highest difference peak  0.286,  deepest hole -0.337,  1-sigma level  0.074
Q1    1   0.6590  1.0344  0.7613  11.00000  0.05    0.29
Q2    1   0.4935  0.1385  0.2465  11.00000  0.05    0.27
Q3    1   0.8353  0.4662  0.6954  11.00000  0.05    0.26
;