# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sh3811
_database_code_depnum_ccdc_archive 'CCDC 1831467'
_audit_update_record             
;
2018-03-21 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Pyxidicycline A'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N O7, C H2 O2'
_chemical_formula_sum            'C22 H17 N O9'
_chemical_formula_weight         439.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.0231(8)
_cell_length_b                   17.534(2)
_cell_length_c                   14.6817(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1807.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    152(2)
_cell_measurement_reflns_used    3294
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.55

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      152(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15148
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.161
_diffrn_reflns_theta_max         27.705
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4084
_reflns_number_gt                3158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.948

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1244 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.8(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4084
_refine_ls_number_parameters     346
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0951(4) 0.18353(16) 0.5287(2) 0.0204(6) Uani 1 1 d . . . . .
O1 O 0.1925(3) 0.11605(14) 0.4044(2) 0.0314(7) Uani 1 1 d . . . . .
O2 O 0.1993(4) 0.38236(15) 0.2963(2) 0.0342(6) Uani 1 1 d . . . . .
O3 O 0.0117(3) 0.68649(14) 0.63760(19) 0.0271(6) Uani 1 1 d . . . . .
H16 H -0.027(7) 0.637(3) 0.659(4) 0.065(16) Uiso 1 1 d . . . . .
O4 O -0.0047(3) 0.53896(13) 0.64370(19) 0.0254(6) Uani 1 1 d . . . . .
H17 H -0.0349 0.4955 0.6630 0.030 Uiso 1 1 calc R U . . .
O5 O -0.0269(3) 0.39927(13) 0.64717(18) 0.0236(6) Uani 1 1 d . . . . .
O6 O 0.3284(3) 0.13364(17) 0.6796(2) 0.0374(7) Uani 1 1 d . . . . .
O7 O 0.6321(4) 0.09599(19) 0.6715(3) 0.0515(9) Uani 1 1 d . . . . .
C1 C 0.1570(5) 0.17947(19) 0.4375(3) 0.0229(8) Uani 1 1 d . . . . .
C2 C 0.1757(5) 0.24925(19) 0.3914(3) 0.0219(8) Uani 1 1 d . . . . .
H1 H 0.201(5) 0.247(2) 0.330(3) 0.020(10) Uiso 1 1 d . . . . .
C3 C 0.1381(4) 0.31653(18) 0.4327(2) 0.0175(7) Uani 1 1 d . . . . .
C4 C 0.1620(5) 0.38682(19) 0.3769(2) 0.0197(7) Uani 1 1 d . . . . .
C5 C 0.1381(4) 0.46035(18) 0.4232(2) 0.0187(7) Uani 1 1 d . . . . .
C6 C 0.1716(4) 0.52625(18) 0.3746(2) 0.0193(7) Uani 1 1 d . . . . .
H2 H 0.2109 0.5233 0.3128 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1474(4) 0.59898(18) 0.4170(3) 0.0194(7) Uani 1 1 d . . . . .
C8 C 0.1841(4) 0.66552(19) 0.3674(3) 0.0221(7) Uani 1 1 d . . . . .
H3 H 0.2232 0.6626 0.3056 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1629(5) 0.7353(2) 0.4092(3) 0.0243(8) Uani 1 1 d . . . . .
H4 H 0.179(5) 0.782(2) 0.369(3) 0.029(11) Uiso 1 1 d . . . . .
C10 C 0.1063(5) 0.7407(2) 0.4996(3) 0.0243(9) Uani 1 1 d . . . . .
H5 H 0.091(5) 0.788(2) 0.529(3) 0.030(11) Uiso 1 1 d . . . . .
C11 C 0.0672(4) 0.67620(19) 0.5503(3) 0.0209(8) Uani 1 1 d . . . . .
C12 C 0.0880(4) 0.60315(18) 0.5097(3) 0.0182(7) Uani 1 1 d . . . . .
C13 C 0.0530(4) 0.53363(17) 0.5580(3) 0.0177(7) Uani 1 1 d . . . . .
C14 C 0.0785(4) 0.46247(18) 0.5158(2) 0.0168(7) Uani 1 1 d . . . . .
C15 C 0.0395(4) 0.39391(19) 0.5677(2) 0.0178(7) Uani 1 1 d . . . . .
C16 C 0.0795(4) 0.31911(18) 0.5256(2) 0.0179(7) Uani 1 1 d . . . . .
C17 C 0.0581(4) 0.25037(18) 0.5729(2) 0.0175(7) Uani 1 1 d . . . . .
C18 C -0.0029(5) 0.2472(2) 0.6700(3) 0.0228(7) Uani 1 1 d . . . . .
H7 H -0.137(7) 0.259(3) 0.671(3) 0.052(13) Uiso 1 1 d . . . . .
H8 H 0.067(6) 0.286(3) 0.705(4) 0.049(13) Uiso 1 1 d . . . . .
H9 H 0.018(5) 0.204(2) 0.693(3) 0.025(10) Uiso 1 1 d . . . . .
C19 C 0.0802(5) 0.1079(2) 0.5735(3) 0.0261(8) Uani 1 1 d . . . . .
H10 H -0.017(5) 0.1134(17) 0.618(3) 0.008(8) Uiso 1 1 d . . . . .
H11 H 0.035(7) 0.077(3) 0.527(4) 0.052(14) Uiso 1 1 d . . . . .
C20 C 0.2705(5) 0.0813(2) 0.6083(3) 0.0290(9) Uani 1 1 d . . . . .
H12 H 0.256(5) 0.033(2) 0.633(3) 0.028(10) Uiso 1 1 d . . . . .
H13 H 0.356(5) 0.0813(19) 0.559(3) 0.011(8) Uiso 1 1 d . . . . .
C21 C 0.5108(5) 0.1344(3) 0.7039(3) 0.0373(10) Uani 1 1 d . . . . .
H14 H 0.528(6) 0.176(3) 0.755(3) 0.046(14) Uiso 1 1 d . . . . .
O8 O 0.6595(5) 0.07592(19) 0.4422(3) 0.0595(10) Uani 1 1 d . . . . .
O9 O 0.4950(5) 0.06921(18) 0.3115(2) 0.0453(8) Uani 1 1 d . . . . .
C22 C 0.6458(6) 0.0580(2) 0.3644(4) 0.0415(11) Uani 1 1 d . . . . .
H15 H 0.388(10) 0.089(3) 0.353(5) 0.082(19) Uiso 1 1 d . . . . .
H18 H 0.734(8) 0.028(3) 0.316(4) 0.062(15) Uiso 1 1 d . . . . .


_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
N1 C17 1.365(4) . ?
N1 C1 1.410(5) . ?
N1 C19 1.484(4) . ?
O1 C1 1.239(4) . ?
O2 C4 1.215(5) . ?
O3 C11 1.351(5) . ?
O3 H16 0.96(6) . ?
O4 C13 1.326(4) . ?
O4 H17 0.8400 . ?
O5 C15 1.261(4) . ?
O6 C21 1.330(5) . ?
O6 C20 1.449(5) . ?
O7 C21 1.185(5) . ?
C1 C2 1.404(5) . ?
C2 C3 1.353(5) . ?
C2 H1 0.92(4) . ?
C3 C16 1.424(5) . ?
C3 C4 1.490(5) . ?
C4 C5 1.467(5) . ?
C5 C6 1.378(5) . ?
C5 C14 1.424(5) . ?
C6 C7 1.429(5) . ?
C6 H2 0.9500 . ?
C7 C8 1.399(5) . ?
C7 C12 1.425(5) . ?
C8 C9 1.376(5) . ?
C8 H3 0.9500 . ?
C9 C10 1.390(6) . ?
C9 H4 1.01(4) . ?
C10 C11 1.381(5) . ?
C10 H5 0.95(4) . ?
C11 C12 1.421(5) . ?
C12 C13 1.431(4) . ?
C13 C14 1.404(4) . ?
C14 C15 1.449(5) . ?
C15 C16 1.477(5) . ?
C16 C17 1.399(5) . ?
C17 C18 1.489(5) . ?
C18 H7 0.97(5) . ?
C18 H8 0.98(5) . ?
C18 H9 0.85(4) . ?
C19 C20 1.505(5) . ?
C19 H10 0.95(4) . ?
C19 H11 0.94(5) . ?
C20 H12 0.92(4) . ?
C20 H13 0.94(4) . ?
C21 H14 1.06(5) . ?
O8 C22 1.188(6) . ?
O9 C22 1.328(6) . ?
O9 H15 1.03(7) . ?
C22 H18 1.07(5) . ?

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
C17 N1 C1 123.7(3) . . ?
C17 N1 C19 122.9(3) . . ?
C1 N1 C19 113.4(3) . . ?
C11 O3 H16 105(3) . . ?
C13 O4 H17 109.5 . . ?
C21 O6 C20 118.1(3) . . ?
O1 C1 C2 125.1(3) . . ?
O1 C1 N1 118.7(3) . . ?
C2 C1 N1 116.2(3) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H1 121(2) . . ?
C1 C2 H1 117(2) . . ?
C2 C3 C16 120.9(3) . . ?
C2 C3 C4 116.9(3) . . ?
C16 C3 C4 122.2(3) . . ?
O2 C4 C5 122.2(3) . . ?
O2 C4 C3 120.5(3) . . ?
C5 C4 C3 117.4(3) . . ?
C6 C5 C14 121.5(3) . . ?
C6 C5 C4 118.6(3) . . ?
C14 C5 C4 119.9(3) . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H2 119.9 . . ?
C7 C6 H2 119.9 . . ?
C8 C7 C12 120.5(3) . . ?
C8 C7 C6 119.7(3) . . ?
C12 C7 C6 119.8(3) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H3 120.3 . . ?
C7 C8 H3 120.3 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H4 116(2) . . ?
C10 C9 H4 123(2) . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H5 117(3) . . ?
C9 C10 H5 122(3) . . ?
O3 C11 C10 117.3(3) . . ?
O3 C11 C12 123.2(3) . . ?
C10 C11 C12 119.4(3) . . ?
C11 C12 C7 118.5(3) . . ?
C11 C12 C13 122.8(3) . . ?
C7 C12 C13 118.6(3) . . ?
O4 C13 C14 121.3(3) . . ?
O4 C13 C12 117.6(3) . . ?
C14 C13 C12 121.1(3) . . ?
C13 C14 C5 118.8(3) . . ?
C13 C14 C15 118.8(3) . . ?
C5 C14 C15 122.4(3) . . ?
O5 C15 C14 119.6(3) . . ?
O5 C15 C16 121.6(3) . . ?
C14 C15 C16 118.8(3) . . ?
C17 C16 C3 118.6(3) . . ?
C17 C16 C15 122.5(3) . . ?
C3 C16 C15 118.9(3) . . ?
N1 C17 C16 118.9(3) . . ?
N1 C17 C18 118.6(3) . . ?
C16 C17 C18 122.6(3) . . ?
C17 C18 H7 107(3) . . ?
C17 C18 H8 109(3) . . ?
H7 C18 H8 110(4) . . ?
C17 C18 H9 111(3) . . ?
H7 C18 H9 111(4) . . ?
H8 C18 H9 109(4) . . ?
N1 C19 C20 111.4(3) . . ?
N1 C19 H10 105.3(18) . . ?
C20 C19 H10 116(2) . . ?
N1 C19 H11 103(3) . . ?
C20 C19 H11 112(3) . . ?
H10 C19 H11 109(3) . . ?
O6 C20 C19 107.4(3) . . ?
O6 C20 H12 109(3) . . ?
C19 C20 H12 109(2) . . ?
O6 C20 H13 112(2) . . ?
C19 C20 H13 108(2) . . ?
H12 C20 H13 112(3) . . ?
O7 C21 O6 125.4(5) . . ?
O7 C21 H14 126(2) . . ?
O6 C21 H14 108(2) . . ?
C22 O9 H15 107(4) . . ?
O8 C22 O9 126.0(4) . . ?
O8 C22 H18 135(3) . . ?
O9 C22 H18 99(3) . . ?

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6


_chemical_compound_source        'Pyxidicoccus fallax'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sh3817
_database_code_depnum_ccdc_archive 'CCDC 1831468'
_audit_update_record             
;
2018-03-21 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_sh3817              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.931 Why?
RESPONSE: The crystal used for acquisition of X-ray diffraction data of Pyxidicycline B (sh3817) was very small leading to peak broadening. Additionally, the side chain of the molecule as well as the formate counter ion are not well localised in the unit cell leading to some uncertainty in these areas as the main driving force for crystal formation are pi-stacking forces of the aromatic core structure. Still, additional structure information about these areas of the molecule are available in the NMR analysis data available in the supplementary information of the paper corresponding to this crystal structure..
;
_vrf_PLAT414_sh3817              
;
PROBLEM: Short Intra D-H..H-X       H5       ..H18A             1.40 Ang.
RESPONSE: The molecule?s side chain and the counter ion do not crystallise as well as the aromatic core structure of Pyxidicycline B (sh3817) and show a significantly higher flexibility. The crystal structure shows thus some insecurity in these areas due to averaging of all the different positions that leads to a shortened D-H..H-X distance. Still, additional structure information about these areas of the molecule are available in the NMR analysis data available in the supplementary information of the paper corresponding to this crystal structure.
;
_vrf_PLAT430_sh3817              
;
PROBLEM: Short Inter D...A Contact  O1       ..O8A              2.50 Ang.
RESPONSE: The molecule?s side chain and the counter ion do not crystallise as well as the aromatic core structure of Pyxidicycline B (sh3817) and show a significantly higher flexibility. The crystal structure shows thus some insecurity in these areas due to averaging of all the different positions that leads to a close D..A contact. Still, additional structure information about these areas of the molecule are available in the NMR analysis data available in the supplementary information of the paper corresponding to this crystal structure.
;
# Added during the CSD deposition process: Wednesday 21 March 2018 01:09 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Pyxidicycline B'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N O7, C H2 O2'
_chemical_formula_sum            'C22 H17 N O9'
_chemical_formula_weight         439.36

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0902(12)
_cell_length_b                   7.9097(15)
_cell_length_c                   17.330(3)
_cell_angle_alpha                89.561(13)
_cell_angle_beta                 84.797(11)
_cell_angle_gamma                74.655(12)
_cell_volume                     933.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1183
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      21.45

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19696
_diffrn_reflns_av_unetI/netI     0.1460
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.180
_diffrn_reflns_theta_max         26.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             3546
_reflns_number_gt                1264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3546
_refine_ls_number_parameters     270
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2936
_refine_ls_R_factor_gt           0.1357
_refine_ls_wR_factor_ref         0.3784
_refine_ls_wR_factor_gt          0.3337
_refine_ls_goodness_of_fit_ref   1.614
_refine_ls_restrained_S_all      1.613
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1924(9) 0.1200(8) 0.1896(3) 0.066(2) Uani 1 1 d . . . . .
O2 O 0.4364(8) 0.1588(7) 0.5903(3) 0.0537(17) Uani 1 1 d . . . . .
O3 O 0.2204(8) 0.9208(7) 0.6772(3) 0.0516(17) Uani 1 1 d . . . . .
H3 H 0.1821 0.9436 0.6329 0.077 Uiso 1 1 calc R U . . .
O4 O 0.1603(7) 0.8506(7) 0.5380(3) 0.0374(14) Uani 1 1 d . . . . .
O5 O 0.0952(7) 0.7853(7) 0.4050(3) 0.0421(15) Uani 1 1 d . . . . .
H5 H 0.1532 0.8156 0.3650 0.063 Uiso 1 1 calc R U . . .
N1 N 0.1302(8) 0.4089(9) 0.2279(4) 0.0407(19) Uani 1 1 d . . . . .
C1 C 0.1909(12) 0.2248(14) 0.2430(6) 0.055(3) Uani 1 1 d . . . . .
C2 C 0.2472(11) 0.1804(11) 0.3168(5) 0.044(2) Uani 1 1 d . . . . .
H2 H 0.2913 0.0600 0.3293 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2407(10) 0.3094(10) 0.3738(5) 0.035(2) Uani 1 1 d . . . . .
C4 C 0.3025(10) 0.2570(12) 0.4475(5) 0.043(2) Uani 1 1 d . . . . .
H4 H 0.3471 0.1357 0.4582 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2990(9) 0.3783(11) 0.5036(4) 0.032(2) Uani 1 1 d . . . . .
C6 C 0.3651(10) 0.3167(11) 0.5781(4) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.3500(10) 0.4478(11) 0.6402(4) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.4022(11) 0.3886(12) 0.7124(5) 0.044(2) Uani 1 1 d . . . . .
H8 H 0.4414 0.2665 0.7220 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3968(11) 0.5079(13) 0.7701(5) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.4370 0.4683 0.8194 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3345(10) 0.6815(12) 0.7571(4) 0.047(2) Uani 1 1 d . . . . .
H10 H 0.3279 0.7620 0.7982 0.056 Uiso 1 1 calc R U . . .
C11 C 0.2798(10) 0.7457(11) 0.6853(4) 0.037(2) Uani 1 1 d . . . . .
C12 C 0.2849(9) 0.6283(10) 0.6253(4) 0.0263(18) Uani 1 1 d . . . . .
C13 C 0.2217(10) 0.6858(11) 0.5500(4) 0.036(2) Uani 1 1 d . . . . .
C14 C 0.2291(9) 0.5609(10) 0.4887(4) 0.0303(19) Uani 1 1 d . . . . .
C15 C 0.1678(10) 0.6143(10) 0.4157(4) 0.031(2) Uani 1 1 d . . . . .
C16 C 0.1755(10) 0.4910(10) 0.3545(4) 0.0323(19) Uani 1 1 d . . . . .
C17 C 0.1252(10) 0.5381(10) 0.2808(4) 0.033(2) Uani 1 1 d . . . . .
C18 C 0.0738(11) 0.7251(10) 0.2521(4) 0.048(2) Uani 1 1 d . . . . .
H18A H 0.0747 0.8057 0.2946 0.072 Uiso 1 1 calc R U . . .
H18B H 0.1706 0.7367 0.2097 0.072 Uiso 1 1 calc R U . . .
H18C H -0.0571 0.7536 0.2334 0.072 Uiso 1 1 calc R U . . .
C19 C 0.0615(12) 0.4465(13) 0.1507(5) 0.069(3) Uani 1 1 d . . . . .
H19A H -0.0214 0.5687 0.1505 0.083 Uiso 1 1 calc R U . . .
H19B H -0.0218 0.3682 0.1402 0.083 Uiso 1 1 calc R U . . .
C20 C 0.2269(18) 0.4228(18) 0.0853(7) 0.114(4) Uiso 1 1 d . . . . .
H20A H 0.3308 0.3148 0.0941 0.136 Uiso 1 1 calc R U . . .
H20B H 0.1747 0.4080 0.0354 0.136 Uiso 1 1 calc R U . . .
O6 O 0.3079(12) 0.5635(13) 0.0806(5) 0.125(3) Uiso 1 1 d . . . . .
C21 C 0.276(4) 0.691(4) 0.0179(15) 0.271(12) Uiso 1 1 d D . . . .
H21A H 0.2717 0.8123 0.0151 0.325 Uiso 0.67(2) 1 calc R U P A 1
H21B H 0.3826 0.7411 0.0046 0.325 Uiso 0.33(2) 1 calc R U P A 2
O7A O 0.256(3) 0.577(3) -0.0324(12) 0.220(9) Uiso 0.67(2) 1 d D U P A 1
O7B O 0.125(5) 0.748(6) -0.023(2) 0.226(11) Uiso 0.33(2) 1 d D U P A 2
O8A O 0.536(2) 1.132(2) -0.1343(9) 0.104(5) Uiso 0.5 1 d . . P . .
C22 C 0.392(4) 1.107(3) -0.1139(11) 0.148(6) Uiso 1 1 d . . . . .
O9A O 0.243(5) 1.145(4) -0.1026(16) 0.210(9) Uiso 0.48(2) 1 d . U P . .
O9B O 0.389(4) 1.002(4) -0.0719(16) 0.205(9) Uiso 0.52(2) 1 d . U P . .
O8B O 0.010(2) 0.999(2) -0.0868(9) 0.127(6) Uiso 0.5 1 d . . P . .


_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
O1 C1 1.245(10) . ?
O2 C6 1.242(8) . ?
O3 C11 1.347(9) . ?
O3 H3 0.8400 . ?
O4 C13 1.282(8) . ?
O5 C15 1.332(8) . ?
O5 H5 0.8400 . ?
N1 C17 1.369(9) . ?
N1 C1 1.434(11) . ?
N1 C19 1.467(9) . ?
C1 C2 1.389(11) . ?
C2 C3 1.415(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(10) . ?
C3 C16 1.434(10) . ?
C4 C5 1.365(11) . ?
C4 H4 0.9500 . ?
C5 C14 1.427(10) . ?
C5 C6 1.450(10) . ?
C6 C7 1.478(11) . ?
C7 C8 1.380(9) . ?
C7 C12 1.409(10) . ?
C8 C9 1.371(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.350(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(10) . ?
C12 C13 1.449(10) . ?
C13 C14 1.445(10) . ?
C14 C15 1.400(9) . ?
C15 C16 1.434(10) . ?
C16 C17 1.379(9) . ?
C17 C18 1.518(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.530(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O6 1.380(13) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
O6 C21 1.47(3) . ?
C21 O7A 1.30(2) . ?
C21 O7B 1.31(2) . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
O8A C22 1.12(2) . ?
C22 O9A 1.02(3) . ?
C22 O9B 1.10(3) . ?
O9A O9B 1.45(3) . ?

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
C11 O3 H3 109.5 . . ?
C15 O5 H5 109.5 . . ?
C17 N1 C1 124.3(7) . . ?
C17 N1 C19 122.7(7) . . ?
C1 N1 C19 112.9(8) . . ?
O1 C1 C2 125.9(9) . . ?
O1 C1 N1 118.2(8) . . ?
C2 C1 N1 115.8(9) . . ?
C1 C2 C3 121.8(8) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 119.5(7) . . ?
C4 C3 C16 121.5(8) . . ?
C2 C3 C16 119.0(7) . . ?
C5 C4 C3 120.9(8) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C14 120.1(7) . . ?
C4 C5 C6 118.4(8) . . ?
C14 C5 C6 121.5(8) . . ?
O2 C6 C5 122.0(8) . . ?
O2 C6 C7 119.7(7) . . ?
C5 C6 C7 118.3(7) . . ?
C8 C7 C12 121.4(8) . . ?
C8 C7 C6 118.3(8) . . ?
C12 C7 C6 120.3(7) . . ?
C9 C8 C7 119.3(8) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.3(8) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 122.0(8) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
O3 C11 C10 118.2(8) . . ?
O3 C11 C12 122.6(7) . . ?
C10 C11 C12 119.3(8) . . ?
C11 C12 C7 117.8(7) . . ?
C11 C12 C13 122.3(7) . . ?
C7 C12 C13 119.9(7) . . ?
O4 C13 C14 119.9(7) . . ?
O4 C13 C12 119.0(7) . . ?
C14 C13 C12 121.1(7) . . ?
C15 C14 C5 119.4(7) . . ?
C15 C14 C13 121.8(7) . . ?
C5 C14 C13 118.8(7) . . ?
O5 C15 C14 117.7(7) . . ?
O5 C15 C16 120.2(7) . . ?
C14 C15 C16 122.1(7) . . ?
C17 C16 C15 123.9(7) . . ?
C17 C16 C3 120.2(7) . . ?
C15 C16 C3 115.9(7) . . ?
N1 C17 C16 118.8(7) . . ?
N1 C17 C18 116.7(6) . . ?
C16 C17 C18 124.4(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 114.0(7) . . ?
N1 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
N1 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
O6 C20 C19 112.2(11) . . ?
O6 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
O6 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 O6 C21 123.1(15) . . ?
O7A C21 O6 93(2) . . ?
O7B C21 O6 131(3) . . ?
O7A C21 H21A 133.3 . . ?
O6 C21 H21A 133.3 . . ?
O7B C21 H21B 114.7 . . ?
O6 C21 H21B 114.7 . . ?
O9A C22 O9B 86(3) . . ?
O9A C22 O8A 152(3) . . ?
O9B C22 O8A 119(3) . . ?
C22 O9A O9B 49.1(19) . . ?
C22 O9B O9A 44.6(18) . . ?

_refine_diff_density_max         0.840
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.106

_shelxl_version_number           2014/6


_chemical_compound_source        'Pyxidicoccus fallax'
