# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1-137e
_audit_block_doi                 10.5517/ccdc.csd.cc2bhpxg
_database_code_depnum_ccdc_archive 'CCDC 2160046'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2020-09-11
_audit_creation_method           'CRYSTALS_ver_14.61_build_7491 '

_oxford_structure_analysis_title 7330
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   5.6288(6)
_cell_length_b                   8.6039(6)
_cell_length_c                   13.5334(10)
_cell_angle_alpha                101.322(6)
_cell_angle_beta                 97.846(7)
_cell_angle_gamma                91.464(7)
_cell_volume                     635.72(10)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C19 H26 Br1 N1 O4 Si1 
# Dc =      2.30 Fooo =    456.00 Mu =     56.26 M =    440.41
# Found Formula = C13 H12 Br1 N1 O4 
# Dc =      1.70 FOOO =    328.00 Mu =     45.19 M =    326.15

_chemical_formula_sum            'C13 H12 Br N O4'
_chemical_formula_moiety         'C13 H12 Br N O4'
_chemical_compound_source        .
_chemical_formula_weight         326.15


_cell_measurement_reflns_used    2697
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      74.44
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_max          0.08

_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    4.519

# Sheldrick geometric approximatio 0.91 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            7325
_diffrn_reflns_av_unetI/netI     0.074
_reflns_number_total             2615
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_av_sigmaI/netI    0.0743
# Number of reflections without Friedels Law is 4244 
# Number of reflections with Friedels Law is 2615 
# Theoretical number of reflections is about 2709 

_diffrn_reflns_theta_min         3.366
_diffrn_reflns_theta_max         77.668
_diffrn_measured_fraction_theta_max 0.970

_diffrn_reflns_theta_full        69.901
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.89
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.74
_refine_diff_density_max         0.97


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         9950
_oxford_refine_ls_R_factor_ref   0.0596
_refine_ls_R_factor_all          0.0596
_refine_ls_wR_factor_ref         0.1485 #Calculated Oxford way 
_refine_ls_wR_factor_all         0.1485
_refine_ls_goodness_of_fit_ref   0.9995
_refine_ls_shift/su_max          0.0002191
_refine_ls_shift/su_mean         0.0000163


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        2614
_oxford_refine_ls_R_factor_all   0.0596
_oxford_refine_ls_wR_factor_all  0.1485

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2255
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_gt          0.1396


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.10P)² + 0.63P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.8236(5) 0.4998(3) 0.6190(2) 0.0324 1.0000 Uani . . . . . .
C2 C 0.6628(7) 0.3996(4) 0.5899(3) 0.0259 1.0000 Uani . . . . . .
C3 C 0.6061(7) 0.2858(4) 0.4908(3) 0.0257 1.0000 Uani . . . . . .
C4 C 0.7259(7) 0.2653(4) 0.4073(3) 0.0272 1.0000 Uani . . . . . .
C5 C 0.6232(7) 0.1504(4) 0.3230(3) 0.0259 1.0000 Uani . . . . . .
C6 C 0.4102(7) 0.0634(4) 0.3218(3) 0.0285 1.0000 Uani . . . . . .
C7 C 0.2932(7) 0.0842(4) 0.4074(3) 0.0286 1.0000 Uani . . . . . .
C8 C 0.3146(7) 0.2497(4) 0.5926(3) 0.0273 1.0000 Uani . . . . . .
N9 N 0.4838(6) 0.3685(4) 0.6466(3) 0.0280 1.0000 Uani . . . . . .
Br10 Br 0.77669(8) 0.11300(6) 0.20524(3) 0.0386 1.0000 Uani . . . . . .
O11 O 0.1415(5) 0.2027(3) 0.6245(2) 0.0325 1.0000 Uani . . . . . .
C12 C 0.4610(8) 0.4610(4) 0.7479(3) 0.0295 1.0000 Uani . . . . . .
C13 C 0.5590(7) 0.3761(5) 0.8328(3) 0.0301 1.0000 Uani . . . . . .
C14 C 0.8323(7) 0.3599(5) 0.8417(3) 0.0295 1.0000 Uani . . . . . .
C15 C 0.9190(8) 0.2669(5) 0.9216(3) 0.0314 1.0000 Uani . . . . . .
O16 O 0.8037(7) 0.1643(5) 0.9448(4) 0.0608 1.0000 Uani . . . . . .
O17 O 1.1475(6) 0.3071(3) 0.9619(2) 0.0349 1.0000 Uani . . . . . .
C18 C 1.2551(9) 0.2140(5) 1.0327(3) 0.0367 1.0000 Uani . . . . . .
C19 C 0.3955(6) 0.1976(4) 0.4911(3) 0.0246 1.0000 Uani . . . . . .
H41 H 0.8682 0.3225 0.4061 0.0328 1.0000 Uiso R . . . . .
H61 H 0.3461 -0.0090 0.2627 0.0343 1.0000 Uiso R . . . . .
H71 H 0.1545 0.0242 0.4083 0.0342 1.0000 Uiso R . . . . .
H122 H 0.5491 0.5633 0.7579 0.0351 1.0000 Uiso R . . . . .
H121 H 0.2917 0.4775 0.7510 0.0348 1.0000 Uiso R . . . . .
H131 H 0.5253 0.4390 0.8965 0.0359 1.0000 Uiso R . . . . .
H132 H 0.4789 0.2715 0.8215 0.0360 1.0000 Uiso R . . . . .
H142 H 0.9159 0.4645 0.8583 0.0348 1.0000 Uiso R . . . . .
H141 H 0.8692 0.3037 0.7769 0.0350 1.0000 Uiso R . . . . .
H183 H 1.4220 0.2404 1.0466 0.0550 1.0000 Uiso R . . . . .
H182 H 1.1865 0.2379 1.0943 0.0545 1.0000 Uiso R . . . . .
H181 H 1.2302 0.1035 1.0038 0.0546 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.203(5) yes
C2 . C3 . 1.486(5) yes
C2 . N9 . 1.397(5) yes
C3 . C4 . 1.378(5) yes
C3 . C19 . 1.392(5) yes
C4 . C5 . 1.401(5) yes
C4 . H41 . 0.934 no
C5 . C6 . 1.394(6) yes
C5 . Br10 . 1.891(4) yes
C6 . C7 . 1.393(6) yes
C6 . H61 . 0.934 no
C7 . C19 . 1.388(5) yes
C7 . H71 . 0.927 no
C8 . N9 . 1.397(5) yes
C8 . O11 . 1.210(5) yes
C8 . C19 . 1.495(5) yes
N9 . C12 . 1.468(5) yes
C12 . C13 . 1.527(5) yes
C12 . H122 . 0.976 no
C12 . H121 . 0.973 no
C13 . C14 . 1.539(6) yes
C13 . H131 . 0.970 no
C13 . H132 . 0.971 no
C14 . C15 . 1.505(5) yes
C14 . H142 . 0.976 no
C14 . H141 . 0.966 no
C15 . O16 . 1.198(5) yes
C15 . O17 . 1.336(5) yes
O17 . C18 . 1.446(5) yes
C18 . H183 . 0.945 no
C18 . H182 . 0.955 no
C18 . H181 . 0.953 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . C3 . 129.9(4) yes
O1 . C2 . N9 . 124.9(4) yes
C3 . C2 . N9 . 105.3(3) yes
C2 . C3 . C4 . 129.3(3) yes
C2 . C3 . C19 . 108.7(3) yes
C4 . C3 . C19 . 121.9(4) yes
C3 . C4 . C5 . 116.0(4) yes
C3 . C4 . H41 . 123.0 no
C5 . C4 . H41 . 121.0 no
C4 . C5 . C6 . 122.6(4) yes
C4 . C5 . Br10 . 118.9(3) yes
C6 . C5 . Br10 . 118.5(3) yes
C5 . C6 . C7 . 120.6(3) yes
C5 . C6 . H61 . 119.2 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C19 . 116.7(3) yes
C6 . C7 . H71 . 121.4 no
C19 . C7 . H71 . 121.9 no
N9 . C8 . O11 . 125.4(4) yes
N9 . C8 . C19 . 105.4(3) yes
O11 . C8 . C19 . 129.2(4) yes
C2 . N9 . C8 . 112.7(3) yes
C2 . N9 . C12 . 123.8(3) yes
C8 . N9 . C12 . 123.2(3) yes
N9 . C12 . C13 . 112.1(3) yes
N9 . C12 . H122 . 109.0 no
C13 . C12 . H122 . 109.0 no
N9 . C12 . H121 . 108.2 no
C13 . C12 . H121 . 108.9 no
H122 . C12 . H121 . 109.6 no
C12 . C13 . C14 . 113.0(3) yes
C12 . C13 . H131 . 107.5 no
C14 . C13 . H131 . 107.7 no
C12 . C13 . H132 . 109.7 no
C14 . C13 . H132 . 109.4 no
H131 . C13 . H132 . 109.5 no
C13 . C14 . C15 . 111.2(3) yes
C13 . C14 . H142 . 110.3 no
C15 . C14 . H142 . 109.5 no
C13 . C14 . H141 . 108.4 no
C15 . C14 . H141 . 108.3 no
H142 . C14 . H141 . 109.1 no
C14 . C15 . O16 . 125.3(4) yes
C14 . C15 . O17 . 111.9(3) yes
O16 . C15 . O17 . 122.8(4) yes
C15 . O17 . C18 . 116.2(3) yes
O17 . C18 . H183 . 108.4 no
O17 . C18 . H182 . 109.6 no
H183 . C18 . H182 . 109.7 no
O17 . C18 . H181 . 110.5 no
H183 . C18 . H181 . 108.8 no
H182 . C18 . H181 . 109.8 no
C8 . C19 . C3 . 107.8(3) yes
C8 . C19 . C7 . 130.1(3) yes
C3 . C19 . C7 . 122.1(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 . H41 . O1 2_766 168 0.93 2.39 3.303(6) yes
C7 . H71 . O11 2_556 161 0.93 2.46 3.354(6) yes
C18 . H181 . O16 2_757 141 0.95 2.54 3.340(6) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
3 -7 12 x .
####################################################################### 
# 
# 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_2-144a
_audit_block_doi                 10.5517/ccdc.csd.cc2bhpyh
_database_code_depnum_ccdc_archive 'CCDC 2160047'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2018-07-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 6992
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_diffrn_special_details          
;
The crystals were very thin plates.
;

_cell_length_a                   7.6792(3)
_cell_length_b                   7.7206(3)
_cell_length_c                   18.8453(8)
_cell_angle_alpha                93.826(4)
_cell_angle_beta                 92.511(4)
_cell_angle_gamma                114.147(4)
_cell_volume                     1014.16(8)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C38 H54 N2 O8 Si2 
# Dc =      2.37 Fooo =    776.00 Mu =     24.00 M =    723.03
# Found Formula = C19 H27.00 N1 O4 Si1 
# Dc =      1.18 FOOO =    388.00 Mu =     12.00 M =    361.51

_chemical_formula_sum            'C19 H27 N O4 Si'
_chemical_formula_moiety         'C19 H27 N O4 Si'
_chemical_compound_source        .
_chemical_formula_weight         361.51


_cell_measurement_reflns_used    4940
_cell_measurement_theta_min      5
_cell_measurement_theta_max      71
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_max          0.21

_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             387.998
_exptl_absorpt_coefficient_mu    1.200

# Sheldrick geometric approximatio 0.82 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13119
_reflns_number_total             3880
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0537
# Number of reflections with Friedels Law is 3880 
# Theoretical number of reflections is about 7878 

_diffrn_reflns_theta_min         4.718
_diffrn_reflns_theta_max         71.292
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        66.683
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -9
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   2.74
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.40


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3880
_oxford_refine_ls_R_factor_ref   0.0502
_refine_ls_wR_factor_ref         0.1102
_refine_ls_goodness_of_fit_ref   1.0017
_refine_ls_shift/su_max          0.0003227
_refine_ls_shift/su_mean         0.0000243


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3880
_refine_ls_R_factor_all          0.0502
_refine_ls_wR_factor_all         0.1102

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3247
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_gt          0.1012


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.29P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.3166(2) 0.62457(17) 0.32056(7) 0.0416 1.0000 Uani . . . . . .
C2 C 0.3131(2) 0.4652(2) 0.31256(9) 0.0314 1.0000 Uani . . . . . .
N3 N 0.4280(2) 0.41219(19) 0.26987(8) 0.0310 1.0000 Uani . . . . . .
C4 C 0.6255(3) 0.5448(3) 0.25857(10) 0.0389 1.0000 Uani . . . . . .
C5 C 0.7449(3) 0.4303(3) 0.27376(10) 0.0383 1.0000 Uani . . . . . .
C6 C 0.6203(2) 0.2716(2) 0.31826(9) 0.0304 1.0000 Uani . . . . . .
C7 C 0.4174(2) 0.2227(2) 0.28354(8) 0.0280 1.0000 Uani . . . . . .
C8 C 0.2514(2) 0.1488(2) 0.32951(8) 0.0271 1.0000 Uani . . . . . .
C9 C 0.1615(2) -0.0307(2) 0.35320(9) 0.0313 1.0000 Uani . . . . . .
C10 C 0.0105(2) -0.0602(2) 0.39586(10) 0.0373 1.0000 Uani . . . . . .
C11 C -0.0477(2) 0.0842(3) 0.41417(10) 0.0395 1.0000 Uani . . . . . .
C12 C 0.0423(2) 0.2631(3) 0.38992(10) 0.0355 1.0000 Uani . . . . . .
C13 C 0.1914(2) 0.2922(2) 0.34666(9) 0.0292 1.0000 Uani . . . . . .
C21 C 0.6348(2) 0.3441(2) 0.39593(9) 0.0294 1.0000 Uani . . . . . .
O22 O 0.6785(2) 0.50813(17) 0.41675(7) 0.0430 1.0000 Uani . . . . . .
O23 O 0.58934(17) 0.20410(16) 0.43890(6) 0.0320 1.0000 Uani . . . . . .
C24 C 0.5913(3) 0.2620(3) 0.51379(10) 0.0431 1.0000 Uani . . . . . .
O31 O 0.39328(17) 0.10270(16) 0.22130(6) 0.0317 1.0000 Uani . . . . . .
Si32 Si 0.25468(7) 0.07262(7) 0.14698(2) 0.0339 1.0000 Uani . . . . . .
C33 C 0.3794(3) 0.2670(3) 0.08974(11) 0.0501 1.0000 Uani . . . . . .
C34 C 0.0180(3) 0.0704(4) 0.16607(12) 0.0551 1.0000 Uani . . . . . .
C35 C 0.2306(3) -0.1648(3) 0.10472(9) 0.0407 1.0000 Uani . . . . . .
C36 C 0.4298(4) -0.1651(3) 0.10111(13) 0.0571 1.0000 Uani . . . . . .
C37 C 0.1356(4) -0.2008(3) 0.02852(12) 0.0636 1.0000 Uani . . . . . .
C38 C 0.1108(4) -0.3257(3) 0.14878(12) 0.0573 1.0000 Uani . . . . . .
H41 H 0.6621 0.6587 0.2923 0.0460 1.0000 Uiso R . . . . .
H42 H 0.6332 0.5780 0.2096 0.0458 1.0000 Uiso R . . . . .
H52 H 0.8677 0.5125 0.2988 0.0461 1.0000 Uiso R . . . . .
H51 H 0.7637 0.3737 0.2297 0.0455 1.0000 Uiso R . . . . .
H61 H 0.6485 0.1625 0.3145 0.0358 1.0000 Uiso R . . . . .
H91 H 0.2004 -0.1260 0.3420 0.0376 1.0000 Uiso R . . . . .
H101 H -0.0525 -0.1803 0.4126 0.0458 1.0000 Uiso R . . . . .
H111 H -0.1501 0.0613 0.4442 0.0474 1.0000 Uiso R . . . . .
H121 H 0.0050 0.3625 0.4035 0.0429 1.0000 Uiso R . . . . .
H241 H 0.5631 0.1505 0.5386 0.0643 1.0000 Uiso R . . . . .
H243 H 0.7168 0.3570 0.5291 0.0651 1.0000 Uiso R . . . . .
H242 H 0.4992 0.3143 0.5200 0.0648 1.0000 Uiso R . . . . .
H331 H 0.3079 0.2411 0.0442 0.0749 1.0000 Uiso R . . . . .
H332 H 0.3856 0.3818 0.1146 0.0748 1.0000 Uiso R . . . . .
H333 H 0.5070 0.2753 0.0836 0.0746 1.0000 Uiso R . . . . .
H342 H -0.0610 0.0391 0.1238 0.0825 1.0000 Uiso R . . . . .
H341 H 0.0337 0.1940 0.1864 0.0832 1.0000 Uiso R . . . . .
H343 H -0.0456 -0.0223 0.1984 0.0826 1.0000 Uiso R . . . . .
H362 H 0.4196 -0.2821 0.0768 0.0852 1.0000 Uiso R . . . . .
H361 H 0.4873 -0.1528 0.1492 0.0851 1.0000 Uiso R . . . . .
H363 H 0.5124 -0.0596 0.0762 0.0852 1.0000 Uiso R . . . . .
H372 H 0.1282 -0.3206 0.0071 0.0951 1.0000 Uiso R . . . . .
H371 H 0.2082 -0.1003 -0.0011 0.0944 1.0000 Uiso R . . . . .
H373 H 0.0059 -0.2090 0.0296 0.0940 1.0000 Uiso R . . . . .
H382 H 0.1005 -0.4481 0.1273 0.0855 1.0000 Uiso R . . . . .
H381 H 0.1663 -0.3050 0.1972 0.0848 1.0000 Uiso R . . . . .
H383 H -0.0166 -0.3304 0.1506 0.0856 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.219(2) yes
C2 . N3 . 1.381(2) yes
C2 . C13 . 1.488(2) yes
N3 . C4 . 1.477(2) yes
N3 . C7 . 1.4721(19) yes
C4 . C5 . 1.542(3) yes
C4 . H41 . 0.982 no
C4 . H42 . 0.973 no
C5 . C6 . 1.539(2) yes
C5 . H52 . 0.973 no
C5 . H51 . 0.956 no
C6 . C7 . 1.548(2) yes
C6 . C21 . 1.515(2) yes
C6 . H61 . 0.951 no
C7 . C8 . 1.506(2) yes
C7 . O31 . 1.4016(19) yes
C8 . C9 . 1.387(2) yes
C8 . C13 . 1.387(2) yes
C9 . C10 . 1.390(2) yes
C9 . H91 . 0.916 no
C10 . C11 . 1.390(3) yes
C10 . H101 . 0.937 no
C11 . C12 . 1.388(3) yes
C11 . H111 . 0.954 no
C12 . C13 . 1.386(2) yes
C12 . H121 . 0.947 no
C21 . O22 . 1.202(2) yes
C21 . O23 . 1.3340(19) yes
O23 . C24 . 1.449(2) yes
C24 . H241 . 0.957 no
C24 . H243 . 0.959 no
C24 . H242 . 0.954 no
O31 . Si32 . 1.6649(12) yes
Si32 . C33 . 1.861(2) yes
Si32 . C34 . 1.862(2) yes
Si32 . C35 . 1.8827(19) yes
C33 . H331 . 0.961 no
C33 . H332 . 0.957 no
C33 . H333 . 0.968 no
C34 . H342 . 0.934 no
C34 . H341 . 0.961 no
C34 . H343 . 0.960 no
C35 . C36 . 1.535(3) yes
C35 . C37 . 1.536(3) yes
C35 . C38 . 1.533(2) yes
C36 . H362 . 0.956 no
C36 . H361 . 0.971 no
C36 . H363 . 0.970 no
C37 . H372 . 0.963 no
C37 . H371 . 0.978 no
C37 . H373 . 0.973 no
C38 . H382 . 0.974 no
C38 . H381 . 0.965 no
C38 . H383 . 0.966 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 125.42(16) yes
O1 . C2 . C13 . 128.13(16) yes
N3 . C2 . C13 . 106.44(13) yes
C2 . N3 . C4 . 122.16(14) yes
C2 . N3 . C7 . 111.63(13) yes
C4 . N3 . C7 . 111.34(13) yes
N3 . C4 . C5 . 103.85(13) yes
N3 . C4 . H41 . 108.4 no
C5 . C4 . H41 . 112.3 no
N3 . C4 . H42 . 110.1 no
C5 . C4 . H42 . 110.9 no
H41 . C4 . H42 . 111.1 no
C4 . C5 . C6 . 104.94(13) yes
C4 . C5 . H52 . 110.5 no
C6 . C5 . H52 . 112.6 no
C4 . C5 . H51 . 109.3 no
C6 . C5 . H51 . 109.1 no
H52 . C5 . H51 . 110.2 no
C5 . C6 . C7 . 101.44(13) yes
C5 . C6 . C21 . 111.55(14) yes
C7 . C6 . C21 . 110.03(13) yes
C5 . C6 . H61 . 113.1 no
C7 . C6 . H61 . 110.4 no
C21 . C6 . H61 . 110.0 no
C6 . C7 . N3 . 102.08(12) yes
C6 . C7 . C8 . 117.99(13) yes
N3 . C7 . C8 . 102.81(12) yes
C6 . C7 . O31 . 106.91(13) yes
N3 . C7 . O31 . 113.60(13) yes
C8 . C7 . O31 . 113.07(13) yes
C7 . C8 . C9 . 129.27(14) yes
C7 . C8 . C13 . 109.25(13) yes
C9 . C8 . C13 . 121.49(15) yes
C8 . C9 . C10 . 117.23(15) yes
C8 . C9 . H91 . 121.9 no
C10 . C9 . H91 . 120.9 no
C9 . C10 . C11 . 121.40(16) yes
C9 . C10 . H101 . 118.9 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 121.02(16) yes
C10 . C11 . H111 . 119.9 no
C12 . C11 . H111 . 119.1 no
C11 . C12 . C13 . 117.66(16) yes
C11 . C12 . H121 . 121.0 no
C13 . C12 . H121 . 121.4 no
C2 . C13 . C8 . 108.67(14) yes
C2 . C13 . C12 . 130.14(15) yes
C8 . C13 . C12 . 121.18(15) yes
C6 . C21 . O22 . 124.25(15) yes
C6 . C21 . O23 . 112.22(13) yes
O22 . C21 . O23 . 123.52(16) yes
C21 . O23 . C24 . 115.21(13) yes
O23 . C24 . H241 . 106.6 no
O23 . C24 . H243 . 108.1 no
H241 . C24 . H243 . 110.7 no
O23 . C24 . H242 . 109.6 no
H241 . C24 . H242 . 112.0 no
H243 . C24 . H242 . 109.7 no
C7 . O31 . Si32 . 128.83(10) yes
O31 . Si32 . C33 . 109.21(9) yes
O31 . Si32 . C34 . 112.06(8) yes
C33 . Si32 . C34 . 109.73(11) yes
O31 . Si32 . C35 . 102.72(7) yes
C33 . Si32 . C35 . 111.15(9) yes
C34 . Si32 . C35 . 111.80(11) yes
Si32 . C33 . H331 . 109.5 no
Si32 . C33 . H332 . 106.1 no
H331 . C33 . H332 . 111.2 no
Si32 . C33 . H333 . 109.5 no
H331 . C33 . H333 . 110.2 no
H332 . C33 . H333 . 110.4 no
Si32 . C34 . H342 . 109.7 no
Si32 . C34 . H341 . 110.2 no
H342 . C34 . H341 . 108.8 no
Si32 . C34 . H343 . 111.6 no
H342 . C34 . H343 . 107.6 no
H341 . C34 . H343 . 108.8 no
Si32 . C35 . C36 . 109.56(13) yes
Si32 . C35 . C37 . 110.05(14) yes
C36 . C35 . C37 . 108.60(19) yes
Si32 . C35 . C38 . 110.53(14) yes
C36 . C35 . C38 . 108.57(18) yes
C37 . C35 . C38 . 109.51(18) yes
C35 . C36 . H362 . 110.1 no
C35 . C36 . H361 . 109.4 no
H362 . C36 . H361 . 108.9 no
C35 . C36 . H363 . 110.8 no
H362 . C36 . H363 . 109.0 no
H361 . C36 . H363 . 108.6 no
C35 . C37 . H372 . 109.0 no
C35 . C37 . H371 . 111.8 no
H372 . C37 . H371 . 108.6 no
C35 . C37 . H373 . 110.2 no
H372 . C37 . H373 . 108.0 no
H371 . C37 . H373 . 109.3 no
C35 . C38 . H382 . 110.3 no
C35 . C38 . H381 . 111.1 no
H382 . C38 . H381 . 109.4 no
C35 . C38 . H383 . 109.9 no
H382 . C38 . H383 . 108.5 no
H381 . C38 . H383 . 107.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O1 1_545 176 0.92 2.45 3.365(3) yes
C10 . H101 . O22 1_445 155 0.94 2.46 3.328(3) yes
C24 . H241 . O23 2_656 158 0.96 2.57 3.482(3) yes
C24 . H242 . O22 2_666 158 0.95 2.57 3.477(3) yes


####################################################################### 
# 
# 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_3-194f
_audit_block_doi                 10.5517/ccdc.csd.cc2bhpzj
_database_code_depnum_ccdc_archive 'CCDC 2160048'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7273
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   5.58060(10)
_cell_length_b                   13.5108(2)
_cell_length_c                   15.3647(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.2499(17)
_cell_angle_gamma                90
_cell_volume                     1143.41(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C13 H12 F1 N1 O3 
# Dc =      1.45 Fooo =    520.00 Mu =      9.65 M =    249.24
# Found Formula = C13 H12 F1 N1 O3 
# Dc =      1.45 FOOO =    520.00 Mu =      9.65 M =    249.24

_chemical_formula_sum            'C13 H12 F N O3'
_chemical_formula_moiety         'C13 H12 F N O3'
_chemical_compound_source        .
_chemical_formula_weight         249.24


_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      4.34
_cell_measurement_theta_max      74.82
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.965

# Sheldrick geometric approximatio 0.82 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            7130
_diffrn_reflns_av_unetI/netI     0.042
_reflns_number_total             2345
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0417
# Number of reflections with Friedels Law is 2345 
# Theoretical number of reflections is about 4779 

_diffrn_reflns_theta_min         4.383
_diffrn_reflns_theta_max         76.076
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        74.555
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.50
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.30


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2345
_oxford_refine_ls_R_factor_ref   0.0488
_refine_ls_R_factor_all          0.0488
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_all         0.1238
_refine_ls_goodness_of_fit_ref   1.0040
_refine_ls_shift/su_max          0.0003156
_refine_ls_shift/su_mean         0.0000460


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        2345
_oxford_refine_ls_R_factor_all   0.0488
_oxford_refine_ls_wR_factor_all  0.1238

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2123
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_gt          0.1185


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 0.38P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.72009(17) 0.56814(8) 0.57748(6) 0.0385 1.0000 Uani . . . . . .
C2 C 0.5407(3) 0.62351(11) 0.60170(10) 0.0287 1.0000 Uani . . . . . .
C3 C 0.3705(3) 0.66683(12) 0.53770(10) 0.0336 1.0000 Uani . . . . . .
C4 C 0.1845(3) 0.72283(12) 0.56332(10) 0.0336 1.0000 Uani . . . . . .
C5 C 0.1637(3) 0.73511(11) 0.65161(10) 0.0295 1.0000 Uani . . . . . .
C6 C 0.3400(3) 0.69078(10) 0.71388(9) 0.0255 1.0000 Uani . . . . . .
C7 C 0.5290(2) 0.63547(10) 0.69008(9) 0.0246 1.0000 Uani . . . . . .
C8 C 0.6902(2) 0.59862(11) 0.77126(9) 0.0246 1.0000 Uani . . . . . .
C9 C 0.6949(2) 0.48735(11) 0.79548(9) 0.0245 1.0000 Uani . . . . . .
C10 C 0.7577(3) 0.49291(12) 0.89645(9) 0.0308 1.0000 Uani . . . . . .
C11 C 0.6260(3) 0.58508(12) 0.92333(10) 0.0307 1.0000 Uani . . . . . .
N12 N 0.5790(2) 0.64365(9) 0.84199(8) 0.0253 1.0000 Uani . . . . . .
C13 C 0.3603(3) 0.68724(10) 0.81199(9) 0.0255 1.0000 Uani . . . . . .
O14 O 0.2112(2) 0.71373(9) 0.85702(7) 0.0332 1.0000 Uani . . . . . .
C15 C 0.4471(2) 0.44359(10) 0.76417(10) 0.0246 1.0000 Uani . . . . . .
O16 O 0.2857(2) 0.43907(10) 0.80728(8) 0.0373 1.0000 Uani . . . . . .
O17 O 0.42675(18) 0.41492(8) 0.68041(7) 0.0282 1.0000 Uani . . . . . .
C18 C 0.1857(3) 0.38653(14) 0.63865(11) 0.0372 1.0000 Uani . . . . . .
H31 H 0.3789 0.6587 0.4771 0.0401 1.0000 Uiso R . . . . .
H41 H 0.0722 0.7535 0.5196 0.0387 1.0000 Uiso R . . . . .
H51 H 0.0370 0.7717 0.6683 0.0349 1.0000 Uiso R . . . . .
H81 H 0.8587 0.6207 0.7727 0.0295 1.0000 Uiso R . . . . .
H91 H 0.8174 0.4532 0.7690 0.0286 1.0000 Uiso R . . . . .
H101 H 0.9366 0.5008 0.9129 0.0377 1.0000 Uiso R . . . . .
H102 H 0.7045 0.4341 0.9245 0.0375 1.0000 Uiso R . . . . .
H112 H 0.7261 0.6221 0.9707 0.0372 1.0000 Uiso R . . . . .
H111 H 0.4714 0.5702 0.9423 0.0367 1.0000 Uiso R . . . . .
H183 H 0.1927 0.3686 0.5780 0.0560 1.0000 Uiso R . . . . .
H182 H 0.0761 0.4417 0.6377 0.0554 1.0000 Uiso R . . . . .
H181 H 0.1243 0.3326 0.6700 0.0554 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.3492(18) yes
C2 . C3 . 1.383(2) yes
C2 . C7 . 1.379(2) yes
C3 . C4 . 1.391(2) yes
C3 . H31 . 0.946 no
C4 . C5 . 1.390(2) yes
C4 . H41 . 0.938 no
C5 . C6 . 1.393(2) yes
C5 . H51 . 0.932 no
C6 . C7 . 1.388(2) yes
C6 . C13 . 1.494(2) yes
C7 . C8 . 1.5007(19) yes
C8 . C9 . 1.548(2) yes
C8 . N12 . 1.4674(18) yes
C8 . H81 . 0.984 no
C9 . C10 . 1.5364(19) yes
C9 . C15 . 1.5099(19) yes
C9 . H91 . 0.967 no
C10 . C11 . 1.536(2) yes
C10 . H101 . 0.996 no
C10 . H102 . 0.974 no
C11 . N12 . 1.4669(18) yes
C11 . H112 . 0.981 no
C11 . H111 . 0.976 no
N12 . C13 . 1.3663(18) yes
C13 . O14 . 1.2184(18) yes
C15 . O16 . 1.2022(18) yes
C15 . O17 . 1.3312(18) yes
O17 . C18 . 1.4461(18) yes
C18 . H183 . 0.969 no
C18 . H182 . 0.963 no
C18 . H181 . 0.966 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 119.60(14) yes
F1 . C2 . C7 . 119.42(13) yes
C3 . C2 . C7 . 120.97(15) yes
C2 . C3 . C4 . 119.17(14) yes
C2 . C3 . H31 . 120.9 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 121.61(14) yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 119.6 no
C4 . C5 . C6 . 117.29(14) yes
C4 . C5 . H51 . 121.2 no
C6 . C5 . H51 . 121.5 no
C5 . C6 . C7 . 122.22(14) yes
C5 . C6 . C13 . 129.60(14) yes
C7 . C6 . C13 . 108.11(12) yes
C6 . C7 . C2 . 118.72(13) yes
C6 . C7 . C8 . 109.81(12) yes
C2 . C7 . C8 . 131.48(14) yes
C7 . C8 . C9 . 120.46(12) yes
C7 . C8 . N12 . 102.10(11) yes
C9 . C8 . N12 . 102.57(11) yes
C7 . C8 . H81 . 111.2 no
C9 . C8 . H81 . 108.0 no
N12 . C8 . H81 . 112.0 no
C8 . C9 . C10 . 100.81(12) yes
C8 . C9 . C15 . 108.92(11) yes
C10 . C9 . C15 . 112.91(12) yes
C8 . C9 . H91 . 110.4 no
C10 . C9 . H91 . 112.7 no
C15 . C9 . H91 . 110.6 no
C9 . C10 . C11 . 105.66(11) yes
C9 . C10 . H101 . 108.6 no
C11 . C10 . H101 . 110.4 no
C9 . C10 . H102 . 111.8 no
C11 . C10 . H102 . 110.5 no
H101 . C10 . H102 . 109.8 no
C10 . C11 . N12 . 103.67(12) yes
C10 . C11 . H112 . 112.0 no
N12 . C11 . H112 . 111.1 no
C10 . C11 . H111 . 113.5 no
N12 . C11 . H111 . 108.7 no
H112 . C11 . H111 . 107.9 no
C8 . N12 . C11 . 111.60(12) yes
C8 . N12 . C13 . 112.94(11) yes
C11 . N12 . C13 . 123.23(12) yes
C6 . C13 . N12 . 105.84(12) yes
C6 . C13 . O14 . 127.98(13) yes
N12 . C13 . O14 . 126.12(13) yes
C9 . C15 . O16 . 124.98(13) yes
C9 . C15 . O17 . 110.70(11) yes
O16 . C15 . O17 . 124.25(13) yes
C15 . O17 . C18 . 115.77(11) yes
O17 . C18 . H183 . 108.3 no
O17 . C18 . H182 . 110.1 no
H183 . C18 . H182 . 107.6 no
O17 . C18 . H181 . 111.0 no
H183 . C18 . H181 . 111.3 no
H182 . C18 . H181 . 108.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . O14 3_564 124 0.95 2.59 3.211(2) yes
C8 . H81 . O14 1_655 146 0.98 2.51 3.373(2) yes
C9 . H91 . O16 1_655 134 0.97 2.59 3.337(2) yes
C18 . H181 . O14 4_546 137 0.97 2.45 3.226(2) yes


####################################################################### 
# 
# 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_6-171
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq1m
_database_code_depnum_ccdc_archive 'CCDC 2160050'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2019-10-31
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title DIA0413-3_mask250
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_diffrn_special_details          
;
Crystals were thin plates though attempt to collect data 
in-house were made the crystals were too weakly diffracting.
Diamond Light Source, Beamline I19 was used to collect data. 
;


_cell_length_a                   7.5827(2)
_cell_length_b                   14.7561(4)
_cell_length_c                   17.4215(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.342(2)
_cell_angle_gamma                90
_cell_volume                     1911.24(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0028 0.0015 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0164 0.0097 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0056 0.0031 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0101 0.0057 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.0783 0.0668 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C19 H26 F1 N1 O4 Si1 
# Dc =      1.32 Fooo =    808.00 Mu =      1.42 M =    379.50
# Found Formula = C19 H26 F1 N1 O4 Si1 
# Dc =      1.32 FOOO =    808.00 Mu =      1.42 M =    379.50

_chemical_formula_sum            'C19 H26 F N O4 Si'
_chemical_formula_moiety         'C19 H26 F N O4 Si'
_chemical_compound_source        .
_chemical_formula_weight         379.50


_cell_measurement_reflns_used    10607
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      35.27
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.06

_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.142

# Sheldrick geometric approximatio 0.99 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  1.00
_diffrn_source                   Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_monochromator  Synchrotron
_diffrn_detector                 'Pilatus 2M'
_diffrn_measurement_device       
'Pilatus 2M detector on Crystal Logic diffractometer'
_diffrn_measurement_device_type  'Photon counting area detector'
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            36400
_diffrn_reflns_av_unetI/netI     0.189
_reflns_number_total             9263
_diffrn_reflns_av_R_equivalents  0.083
_diffrn_reflns_av_sigmaI/netI    0.1892
# Number of reflections with Friedels Law is 9263 
# Theoretical number of reflections is about 19929 

_diffrn_reflns_theta_min         1.768
_diffrn_reflns_theta_max         36.027
_diffrn_measured_fraction_theta_max 0.931

_diffrn_reflns_theta_full        33.867
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              25
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   2.32
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.79


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3167
_oxford_refine_ls_R_factor_ref   0.0652
_refine_ls_wR_factor_ref         0.1797
_refine_ls_goodness_of_fit_ref   0.9946
_refine_ls_shift/su_max          0.0002055
_refine_ls_shift/su_mean         0.0000140


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        9259
_refine_ls_R_factor_all          0.1155
_refine_ls_wR_factor_all         0.2386

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6786
_refine_ls_R_factor_gt           0.0967
_refine_ls_wR_factor_gt          0.2278


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 6.64P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.2108(3) 0.29905(19) 0.32297(15) 0.0384 1.0000 Uani . . . . . .
C2 C 0.3401(4) 0.3362(2) 0.30531(19) 0.0286 1.0000 Uani . . . . . .
N3 N 0.4956(4) 0.2934(2) 0.29500(17) 0.0280 1.0000 Uani . . . . . .
C4 C 0.5673(5) 0.2132(3) 0.3393(2) 0.0380 1.0000 Uani . . . . . .
C5 C 0.7626(5) 0.2371(3) 0.3738(2) 0.0362 1.0000 Uani . . . . . .
C6 C 0.7794(4) 0.3395(3) 0.3637(2) 0.0312 1.0000 Uani . . . . . .
C7 C 0.6386(4) 0.3579(2) 0.28829(19) 0.0262 1.0000 Uani . . . . . .
C8 C 0.5405(4) 0.4474(2) 0.28328(19) 0.0265 1.0000 Uani . . . . . .
C9 C 0.3651(4) 0.4342(2) 0.29149(19) 0.0278 1.0000 Uani . . . . . .
C10 C 0.2450(5) 0.5049(3) 0.2882(2) 0.0350 1.0000 Uani . . . . . .
C11 C 0.3077(6) 0.5912(3) 0.2760(2) 0.0414 1.0000 Uani . . . . . .
C12 C 0.4823(6) 0.6054(3) 0.2672(2) 0.0405 1.0000 Uani . . . . . .
C13 C 0.5969(5) 0.5336(3) 0.2710(2) 0.0318 1.0000 Uani . . . . . .
F14 F 0.7673(3) 0.54760(16) 0.26238(14) 0.0459 1.0000 Uani . . . . . .
C15 C 0.7252(4) 0.3904(3) 0.4303(2) 0.0303 1.0000 Uani . . . . . .
O16 O 0.6151(3) 0.36386(19) 0.46619(15) 0.0394 1.0000 Uani . . . . . .
O17 O 0.8092(3) 0.47017(19) 0.44304(14) 0.0368 1.0000 Uani . . . . . .
C18 C 0.7514(5) 0.5267(3) 0.5009(2) 0.0438 1.0000 Uani . . . . . .
O19 O 0.7199(3) 0.34076(16) 0.22423(13) 0.0275 1.0000 Uani . . . . . .
Si20 Si 0.62486(12) 0.33095(7) 0.12973(5) 0.0274 1.0000 Uani . . . . . .
C21 C 0.5407(5) 0.2137(3) 0.1090(2) 0.0386 1.0000 Uani . . . . . .
C22 C 0.4343(5) 0.4110(3) 0.1006(2) 0.0402 1.0000 Uani . . . . . .
C23 C 0.8109(5) 0.3590(3) 0.0767(2) 0.0322 1.0000 Uani . . . . . .
C24 C 0.9694(5) 0.2930(3) 0.1008(3) 0.0452 1.0000 Uani . . . . . .
C25 C 0.8772(6) 0.4555(3) 0.0963(2) 0.0419 1.0000 Uani . . . . . .
C26 C 0.7394(6) 0.3511(3) -0.0115(2) 0.0445 1.0000 Uani . . . . . .
H41 H 0.5004 0.2013 0.3801 0.0455 1.0000 Uiso R . . . . .
H42 H 0.5573 0.1619 0.3042 0.0455 1.0000 Uiso R . . . . .
H51 H 0.7926 0.2193 0.4286 0.0429 1.0000 Uiso R . . . . .
H52 H 0.8407 0.2063 0.3450 0.0429 1.0000 Uiso R . . . . .
H61 H 0.8995 0.3570 0.3582 0.0367 1.0000 Uiso R . . . . .
H101 H 0.1197 0.4949 0.2940 0.0386 1.0000 Uiso R . . . . .
H111 H 0.2298 0.6398 0.2734 0.0498 1.0000 Uiso R . . . . .
H121 H 0.5236 0.6632 0.2592 0.0491 1.0000 Uiso R . . . . .
H181 H 0.8249 0.5812 0.5097 0.0658 1.0000 Uiso R . . . . .
H182 H 0.7629 0.4944 0.5497 0.0659 1.0000 Uiso R . . . . .
H183 H 0.6275 0.5434 0.4832 0.0653 1.0000 Uiso R . . . . .
H211 H 0.5010 0.2060 0.0543 0.0579 1.0000 Uiso R . . . . .
H212 H 0.6341 0.1693 0.1271 0.0580 1.0000 Uiso R . . . . .
H213 H 0.4410 0.2018 0.1335 0.0579 1.0000 Uiso R . . . . .
H222 H 0.3855 0.4043 0.0451 0.0596 1.0000 Uiso R . . . . .
H221 H 0.4756 0.4725 0.1106 0.0601 1.0000 Uiso R . . . . .
H223 H 0.3431 0.3990 0.1299 0.0599 1.0000 Uiso R . . . . .
H242 H 1.0609 0.3049 0.0704 0.0684 1.0000 Uiso R . . . . .
H241 H 1.0214 0.2995 0.1557 0.0676 1.0000 Uiso R . . . . .
H243 H 0.9287 0.2313 0.0930 0.0676 1.0000 Uiso R . . . . .
H252 H 0.9756 0.4682 0.0703 0.0630 1.0000 Uiso R . . . . .
H251 H 0.9185 0.4624 0.1523 0.0624 1.0000 Uiso R . . . . .
H253 H 0.7827 0.4982 0.0779 0.0626 1.0000 Uiso R . . . . .
H262 H 0.8296 0.3728 -0.0388 0.0669 1.0000 Uiso R . . . . .
H261 H 0.6314 0.3877 -0.0278 0.0666 1.0000 Uiso R . . . . .
H263 H 0.7131 0.2882 -0.0265 0.0666 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       180(40)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.215(4) yes
C2 . N3 . 1.380(4) yes
C2 . C9 . 1.484(5) yes
N3 . C4 . 1.459(5) yes
N3 . C7 . 1.464(4) yes
C4 . C5 . 1.526(5) yes
C4 . H41 . 0.967 no
C4 . H42 . 0.967 no
C5 . C6 . 1.530(5) yes
C5 . H51 . 0.973 no
C5 . H52 . 0.962 no
C6 . C7 . 1.546(5) yes
C6 . C15 . 1.505(5) yes
C6 . H61 . 0.969 no
C7 . C8 . 1.509(5) yes
C7 . O19 . 1.400(4) yes
C8 . C9 . 1.379(5) yes
C8 . C13 . 1.372(5) yes
C9 . C10 . 1.378(5) yes
C10 . C11 . 1.390(6) yes
C10 . H101 . 0.987 no
C11 . C12 . 1.378(6) yes
C11 . H111 . 0.925 no
C12 . C13 . 1.364(5) yes
C12 . H121 . 0.928 no
C13 . F14 . 1.346(4) yes
C15 . O16 . 1.203(4) yes
C15 . O17 . 1.336(5) yes
O17 . C18 . 1.442(4) yes
C18 . H181 . 0.975 no
C18 . H182 . 0.962 no
C18 . H183 . 0.961 no
O19 . Si20 . 1.669(2) yes
Si20 . C21 . 1.855(4) yes
Si20 . C22 . 1.858(4) yes
Si20 . C23 . 1.878(3) yes
C21 . H211 . 0.947 no
C21 . H212 . 0.970 no
C21 . H213 . 0.956 no
C22 . H222 . 0.969 no
C22 . H221 . 0.965 no
C22 . H223 . 0.954 no
C23 . C24 . 1.540(5) yes
C23 . C25 . 1.525(5) yes
C23 . C26 . 1.531(5) yes
C24 . H242 . 0.969 no
C24 . H241 . 0.964 no
C24 . H243 . 0.961 no
C25 . H252 . 0.965 no
C25 . H251 . 0.970 no
C25 . H253 . 0.961 no
C26 . H262 . 0.960 no
C26 . H261 . 0.975 no
C26 . H263 . 0.975 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 125.4(3) yes
O1 . C2 . C9 . 128.0(3) yes
N3 . C2 . C9 . 106.6(3) yes
C2 . N3 . C4 . 122.8(3) yes
C2 . N3 . C7 . 112.2(3) yes
C4 . N3 . C7 . 111.4(3) yes
N3 . C4 . C5 . 104.6(3) yes
N3 . C4 . H41 . 109.9 no
C5 . C4 . H41 . 111.1 no
N3 . C4 . H42 . 109.1 no
C5 . C4 . H42 . 112.3 no
H41 . C4 . H42 . 109.6 no
C4 . C5 . C6 . 106.2(3) yes
C4 . C5 . H51 . 110.3 no
C6 . C5 . H51 . 111.7 no
C4 . C5 . H52 . 109.5 no
C6 . C5 . H52 . 109.4 no
H51 . C5 . H52 . 109.6 no
C5 . C6 . C7 . 102.2(3) yes
C5 . C6 . C15 . 111.3(3) yes
C7 . C6 . C15 . 108.7(3) yes
C5 . C6 . H61 . 112.0 no
C7 . C6 . H61 . 112.0 no
C15 . C6 . H61 . 110.3 no
C6 . C7 . N3 . 102.5(3) yes
C6 . C7 . C8 . 116.9(3) yes
N3 . C7 . C8 . 102.0(3) yes
C6 . C7 . O19 . 107.9(3) yes
N3 . C7 . O19 . 113.3(3) yes
C8 . C7 . O19 . 113.7(3) yes
C7 . C8 . C9 . 110.2(3) yes
C7 . C8 . C13 . 130.9(3) yes
C9 . C8 . C13 . 118.9(3) yes
C2 . C9 . C8 . 108.1(3) yes
C2 . C9 . C10 . 129.8(3) yes
C8 . C9 . C10 . 122.1(3) yes
C9 . C10 . C11 . 117.2(3) yes
C9 . C10 . H101 . 121.6 no
C11 . C10 . H101 . 121.2 no
C10 . C11 . C12 . 121.4(4) yes
C10 . C11 . H111 . 118.9 no
C12 . C11 . H111 . 119.6 no
C11 . C12 . C13 . 119.5(4) yes
C11 . C12 . H121 . 121.1 no
C13 . C12 . H121 . 119.4 no
C8 . C13 . C12 . 120.9(3) yes
C8 . C13 . F14 . 119.7(3) yes
C12 . C13 . F14 . 119.5(3) yes
C6 . C15 . O16 . 124.1(3) yes
C6 . C15 . O17 . 112.0(3) yes
O16 . C15 . O17 . 123.9(3) yes
C15 . O17 . C18 . 115.2(3) yes
O17 . C18 . H181 . 110.1 no
O17 . C18 . H182 . 110.1 no
H181 . C18 . H182 . 108.7 no
O17 . C18 . H183 . 109.7 no
H181 . C18 . H183 . 109.3 no
H182 . C18 . H183 . 108.9 no
C7 . O19 . Si20 . 129.0(2) yes
O19 . Si20 . C21 . 109.79(15) yes
O19 . Si20 . C22 . 112.11(15) yes
C21 . Si20 . C22 . 108.68(19) yes
O19 . Si20 . C23 . 104.20(14) yes
C21 . Si20 . C23 . 111.90(17) yes
C22 . Si20 . C23 . 110.15(18) yes
Si20 . C21 . H211 . 109.7 no
Si20 . C21 . H212 . 111.4 no
H211 . C21 . H212 . 108.3 no
Si20 . C21 . H213 . 110.8 no
H211 . C21 . H213 . 107.8 no
H212 . C21 . H213 . 108.7 no
Si20 . C22 . H222 . 109.4 no
Si20 . C22 . H221 . 109.9 no
H222 . C22 . H221 . 108.9 no
Si20 . C22 . H223 . 110.0 no
H222 . C22 . H223 . 109.9 no
H221 . C22 . H223 . 108.7 no
Si20 . C23 . C24 . 110.3(3) yes
Si20 . C23 . C25 . 110.0(3) yes
C24 . C23 . C25 . 109.0(3) yes
Si20 . C23 . C26 . 109.0(2) yes
C24 . C23 . C26 . 109.2(3) yes
C25 . C23 . C26 . 109.4(3) yes
C23 . C24 . H242 . 109.9 no
C23 . C24 . H241 . 110.6 no
H242 . C24 . H241 . 109.1 no
C23 . C24 . H243 . 110.4 no
H242 . C24 . H243 . 109.8 no
H241 . C24 . H243 . 107.1 no
C23 . C25 . H252 . 109.1 no
C23 . C25 . H251 . 110.4 no
H252 . C25 . H251 . 109.0 no
C23 . C25 . H253 . 110.3 no
H252 . C25 . H253 . 108.1 no
H251 . C25 . H253 . 109.8 no
C23 . C26 . H262 . 109.0 no
C23 . C26 . H261 . 111.2 no
H262 . C26 . H261 . 108.1 no
C23 . C26 . H263 . 110.8 no
H262 . C26 . H263 . 108.2 no
H261 . C26 . H263 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C18 . H183 . O16 2_666 138 0.96 2.58 3.359(5) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 5 1 x .
-1 7 2 x .
-1 6 1 x .
-1 2 1 x .
####################################################################### 
# 
# 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_7-144f
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq2n
_database_code_depnum_ccdc_archive 'CCDC 2160051'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title 7210
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.6070(3)
_cell_length_b                   7.9569(3)
_cell_length_c                   18.7476(6)
_cell_angle_alpha                92.034(3)
_cell_angle_beta                 92.705(3)
_cell_angle_gamma                115.382(4)
_cell_volume                     1022.12(7)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C19 H26 F1 N1 O4 Si1 
# Dc =      1.23 Fooo =    404.00 Mu =     12.88 M =    379.50
# Found Formula = C19 H26 F1 N1 O4 Si1 
# Dc =      1.23 FOOO =    404.00 Mu =     12.88 M =    379.50

_chemical_formula_sum            'C19 H26 F N O4 Si'
_chemical_formula_moiety         'C19 H26 F N O4 Si'
_chemical_compound_source        .
_chemical_formula_weight         379.50


_cell_measurement_reflns_used    8653
_cell_measurement_theta_min      4.74
_cell_measurement_theta_max      76.96
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.38

_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    1.288

# Sheldrick geometric approximatio 0.82 0.85 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16849
_diffrn_reflns_av_unetI/netI     0.043
_reflns_number_total             4280
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0433
# Number of reflections with Friedels Law is 4280 
# Theoretical number of reflections is about 8643 

_diffrn_reflns_theta_min         4.732
_diffrn_reflns_theta_max         76.982
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        74.673
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   2.67
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.31


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4280
_oxford_refine_ls_R_factor_ref   0.0435
_refine_ls_wR_factor_ref         0.1150
_refine_ls_goodness_of_fit_ref   1.0023
_refine_ls_shift/su_max          0.0003236
_refine_ls_shift/su_mean         0.0000255


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        4280
_refine_ls_R_factor_all          0.0435
_refine_ls_wR_factor_all         0.1150

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3888
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_gt          0.1109


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.22P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.64356(15) 0.33212(17) 0.31627(6) 0.0409 1.0000 Uani . . . . . .
C2 C 0.4789(2) 0.3199(2) 0.30936(7) 0.0312 1.0000 Uani . . . . . .
N3 N 0.42051(16) 0.42743(16) 0.26680(6) 0.0307 1.0000 Uani . . . . . .
C4 C 0.5532(2) 0.6219(2) 0.25441(9) 0.0383 1.0000 Uani . . . . . .
C5 C 0.4337(2) 0.7311(2) 0.27057(8) 0.0372 1.0000 Uani . . . . . .
C6 C 0.27114(19) 0.60489(18) 0.31640(7) 0.0289 1.0000 Uani . . . . . .
C7 C 0.22555(18) 0.40941(18) 0.28185(7) 0.0267 1.0000 Uani . . . . . .
C8 C 0.15190(18) 0.24631(17) 0.32885(7) 0.0267 1.0000 Uani . . . . . .
C9 C -0.03200(19) 0.15378(19) 0.35349(7) 0.0310 1.0000 Uani . . . . . .
C10 C -0.0630(2) 0.0042(2) 0.39577(8) 0.0377 1.0000 Uani . . . . . .
C11 C 0.0841(2) -0.0498(2) 0.41253(9) 0.0401 1.0000 Uani . . . . . .
C12 C 0.2653(2) 0.04662(19) 0.38707(8) 0.0343 1.0000 Uani . . . . . .
C13 C 0.30126(19) 0.19431(18) 0.34422(7) 0.0288 1.0000 Uani . . . . . .
F14 F 0.40917(14) -0.00524(12) 0.40379(6) 0.0446 1.0000 Uani . . . . . .
C21 C 0.34531(18) 0.61911(17) 0.39389(7) 0.0273 1.0000 Uani . . . . . .
O22 O 0.51087(14) 0.65159(14) 0.41294(6) 0.0348 1.0000 Uani . . . . . .
O23 O 0.20431(13) 0.58576(13) 0.43865(5) 0.0297 1.0000 Uani . . . . . .
C24 C 0.2643(2) 0.5934(2) 0.51383(8) 0.0391 1.0000 Uani . . . . . .
O31 O 0.10314(14) 0.38226(14) 0.22012(5) 0.0311 1.0000 Uani . . . . . .
Si32 Si 0.07659(5) 0.25079(6) 0.14588(2) 0.0330 1.0000 Uani . . . . . .
C33 C 0.0706(3) 0.0209(3) 0.16576(10) 0.0522 1.0000 Uani . . . . . .
C34 C 0.2793(2) 0.3756(3) 0.08784(9) 0.0494 1.0000 Uani . . . . . .
C35 C -0.1621(2) 0.2258(2) 0.10307(8) 0.0395 1.0000 Uani . . . . . .
C36 C -0.1605(3) 0.4189(3) 0.09965(11) 0.0558 1.0000 Uani . . . . . .
C37 C -0.1934(3) 0.1374(3) 0.02667(10) 0.0611 1.0000 Uani . . . . . .
C38 C -0.3308(3) 0.1042(3) 0.14701(10) 0.0555 1.0000 Uani . . . . . .
H41 H 0.6717 0.6611 0.2875 0.0449 1.0000 Uiso R . . . . .
H42 H 0.5881 0.6325 0.2047 0.0458 1.0000 Uiso R . . . . .
H51 H 0.5144 0.8524 0.2952 0.0455 1.0000 Uiso R . . . . .
H52 H 0.3724 0.7490 0.2273 0.0452 1.0000 Uiso R . . . . .
H61 H 0.1549 0.6250 0.3139 0.0347 1.0000 Uiso R . . . . .
H91 H -0.1335 0.1855 0.3426 0.0326 1.0000 Uiso R . . . . .
H101 H -0.1861 -0.0619 0.4139 0.0452 1.0000 Uiso R . . . . .
H111 H 0.0601 -0.1511 0.4407 0.0491 1.0000 Uiso R . . . . .
H241 H 0.1513 0.5691 0.5397 0.0584 1.0000 Uiso R . . . . .
H242 H 0.3642 0.7136 0.5263 0.0589 1.0000 Uiso R . . . . .
H243 H 0.3070 0.4973 0.5201 0.0597 1.0000 Uiso R . . . . .
H331 H 0.0324 -0.0585 0.1223 0.0783 1.0000 Uiso R . . . . .
H332 H 0.1955 0.0315 0.1841 0.0786 1.0000 Uiso R . . . . .
H333 H -0.0250 -0.0408 0.2007 0.0774 1.0000 Uiso R . . . . .
H342 H 0.2563 0.3083 0.0425 0.0740 1.0000 Uiso R . . . . .
H341 H 0.3966 0.3856 0.1111 0.0730 1.0000 Uiso R . . . . .
H343 H 0.2893 0.4987 0.0816 0.0737 1.0000 Uiso R . . . . .
H362 H -0.2804 0.4060 0.0758 0.0833 1.0000 Uiso R . . . . .
H361 H -0.1467 0.4760 0.1466 0.0828 1.0000 Uiso R . . . . .
H363 H -0.0529 0.5014 0.0740 0.0836 1.0000 Uiso R . . . . .
H372 H -0.3133 0.1296 0.0044 0.0914 1.0000 Uiso R . . . . .
H371 H -0.0865 0.2103 -0.0028 0.0912 1.0000 Uiso R . . . . .
H373 H -0.2030 0.0140 0.0279 0.0918 1.0000 Uiso R . . . . .
H382 H -0.4550 0.0916 0.1248 0.0824 1.0000 Uiso R . . . . .
H381 H -0.3118 0.1576 0.1961 0.0815 1.0000 Uiso R . . . . .
H383 H -0.3370 -0.0200 0.1481 0.0821 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2143(17) yes
C2 . N3 . 1.3808(18) yes
C2 . C13 . 1.4912(18) yes
N3 . C4 . 1.4752(18) yes
N3 . C7 . 1.4696(15) yes
C4 . C5 . 1.535(2) yes
C4 . H41 . 0.993 no
C4 . H42 . 0.977 no
C5 . C6 . 1.5403(18) yes
C5 . H51 . 0.978 no
C5 . H52 . 0.962 no
C6 . C7 . 1.5505(18) yes
C6 . C21 . 1.5160(18) yes
C6 . H61 . 0.963 no
C7 . C8 . 1.5096(17) yes
C7 . O31 . 1.4004(16) yes
C8 . C9 . 1.3836(18) yes
C8 . C13 . 1.3877(17) yes
C9 . C10 . 1.395(2) yes
C9 . H91 . 0.926 no
C10 . C11 . 1.387(2) yes
C10 . H101 . 0.944 no
C11 . C12 . 1.378(2) yes
C11 . H111 . 0.936 no
C12 . C13 . 1.3833(19) yes
C12 . F14 . 1.3526(16) yes
C21 . O22 . 1.2052(16) yes
C21 . O23 . 1.3348(15) yes
O23 . C24 . 1.4519(16) yes
C24 . H241 . 0.956 no
C24 . H242 . 0.944 no
C24 . H243 . 0.959 no
O31 . Si32 . 1.6617(10) yes
Si32 . C33 . 1.8618(18) yes
Si32 . C34 . 1.8627(16) yes
Si32 . C35 . 1.8766(16) yes
C33 . H331 . 0.965 no
C33 . H332 . 0.962 no
C33 . H333 . 0.980 no
C34 . H342 . 0.955 no
C34 . H341 . 0.945 no
C34 . H343 . 0.961 no
C35 . C36 . 1.534(3) yes
C35 . C37 . 1.535(2) yes
C35 . C38 . 1.534(2) yes
C36 . H362 . 0.960 no
C36 . H361 . 0.955 no
C36 . H363 . 0.965 no
C37 . H372 . 0.961 no
C37 . H371 . 0.981 no
C37 . H373 . 0.954 no
C38 . H382 . 0.977 no
C38 . H381 . 0.978 no
C38 . H383 . 0.970 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 125.29(13) yes
O1 . C2 . C13 . 129.03(13) yes
N3 . C2 . C13 . 105.67(11) yes
C2 . N3 . C4 . 121.67(12) yes
C2 . N3 . C7 . 112.15(10) yes
C4 . N3 . C7 . 111.23(11) yes
N3 . C4 . C5 . 104.05(11) yes
N3 . C4 . H41 . 108.5 no
C5 . C4 . H41 . 112.5 no
N3 . C4 . H42 . 110.3 no
C5 . C4 . H42 . 110.8 no
H41 . C4 . H42 . 110.5 no
C4 . C5 . C6 . 105.20(11) yes
C4 . C5 . H51 . 111.7 no
C6 . C5 . H51 . 112.1 no
C4 . C5 . H52 . 110.9 no
C6 . C5 . H52 . 107.7 no
H51 . C5 . H52 . 109.2 no
C5 . C6 . C7 . 101.13(11) yes
C5 . C6 . C21 . 111.35(11) yes
C7 . C6 . C21 . 109.79(10) yes
C5 . C6 . H61 . 114.9 no
C7 . C6 . H61 . 109.7 no
C21 . C6 . H61 . 109.6 no
C6 . C7 . N3 . 102.26(10) yes
C6 . C7 . C8 . 117.81(11) yes
N3 . C7 . C8 . 102.83(10) yes
C6 . C7 . O31 . 107.12(10) yes
N3 . C7 . O31 . 113.44(11) yes
C8 . C7 . O31 . 113.00(11) yes
C7 . C8 . C9 . 128.70(12) yes
C7 . C8 . C13 . 108.75(11) yes
C9 . C8 . C13 . 122.53(12) yes
C8 . C9 . C10 . 117.21(13) yes
C8 . C9 . H91 . 123.2 no
C10 . C9 . H91 . 119.6 no
C9 . C10 . C11 . 121.50(13) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 118.7 no
C10 . C11 . C12 . 119.38(13) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 120.4 no
C11 . C12 . C13 . 120.88(13) yes
C11 . C12 . F14 . 119.39(13) yes
C13 . C12 . F14 . 119.73(13) yes
C2 . C13 . C8 . 109.29(11) yes
C2 . C13 . C12 . 132.22(12) yes
C8 . C13 . C12 . 118.48(12) yes
C6 . C21 . O22 . 124.10(12) yes
C6 . C21 . O23 . 112.11(11) yes
O22 . C21 . O23 . 123.76(13) yes
C21 . O23 . C24 . 115.09(10) yes
O23 . C24 . H241 . 106.5 no
O23 . C24 . H242 . 108.0 no
H241 . C24 . H242 . 111.6 no
O23 . C24 . H243 . 107.6 no
H241 . C24 . H243 . 110.3 no
H242 . C24 . H243 . 112.5 no
C7 . O31 . Si32 . 128.94(8) yes
O31 . Si32 . C33 . 111.81(7) yes
O31 . Si32 . C34 . 109.65(7) yes
C33 . Si32 . C34 . 109.84(9) yes
O31 . Si32 . C35 . 102.85(6) yes
C33 . Si32 . C35 . 111.86(9) yes
C34 . Si32 . C35 . 110.65(7) yes
Si32 . C33 . H331 . 109.0 no
Si32 . C33 . H332 . 112.4 no
H331 . C33 . H332 . 108.2 no
Si32 . C33 . H333 . 111.1 no
H331 . C33 . H333 . 107.7 no
H332 . C33 . H333 . 108.2 no
Si32 . C34 . H342 . 110.2 no
Si32 . C34 . H341 . 108.2 no
H342 . C34 . H341 . 109.9 no
Si32 . C34 . H343 . 109.4 no
H342 . C34 . H343 . 110.2 no
H341 . C34 . H343 . 108.9 no
Si32 . C35 . C36 . 109.45(11) yes
Si32 . C35 . C37 . 110.15(12) yes
C36 . C35 . C37 . 108.69(16) yes
Si32 . C35 . C38 . 110.30(11) yes
C36 . C35 . C38 . 108.76(15) yes
C37 . C35 . C38 . 109.46(14) yes
C35 . C36 . H362 . 109.1 no
C35 . C36 . H361 . 111.0 no
H362 . C36 . H361 . 109.3 no
C35 . C36 . H363 . 111.3 no
H362 . C36 . H363 . 109.0 no
H361 . C36 . H363 . 107.1 no
C35 . C37 . H372 . 109.8 no
C35 . C37 . H371 . 111.7 no
H372 . C37 . H371 . 108.5 no
C35 . C37 . H373 . 110.0 no
H372 . C37 . H373 . 108.0 no
H371 . C37 . H373 . 108.9 no
C35 . C38 . H382 . 110.3 no
C35 . C38 . H381 . 110.5 no
H382 . C38 . H381 . 110.2 no
C35 . C38 . H383 . 109.8 no
H382 . C38 . H383 . 107.3 no
H381 . C38 . H383 . 108.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O1 1_455 169 0.93 2.48 3.391(2) yes
C10 . H101 . O22 1_445 149 0.94 2.45 3.294(2) yes
C24 . H241 . O23 2_566 156 0.96 2.51 3.401(2) yes
C24 . H243 . O22 2_666 153 0.96 2.50 3.382(2) yes


####################################################################### 
# 
# 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_5-144a
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq0l
_database_code_depnum_ccdc_archive 'CCDC 2160049'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2018-10-19
_audit_creation_method           CRYSTALS_ver_14.61_build_7031

_oxford_structure_analysis_title 7049
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.6071(2)
_cell_length_b                   8.3244(3)
_cell_length_c                   18.1081(6)
_cell_angle_alpha                92.806(3)
_cell_angle_beta                 91.700(3)
_cell_angle_gamma                107.611(3)
_cell_volume                     1090.44(6)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C19 H26 N2 O6 Si1 
# Dc =      1.24 Fooo =    432.00 Mu =     12.59 M =    406.51
# Found Formula = C19 H26 N2 O6 Si1 
# Dc =      1.24 FOOO =    432.00 Mu =     12.59 M =    406.51

_chemical_formula_sum            'C19 H26 N2 O6 Si'
_chemical_formula_moiety         'C19 H26 N2 O6 Si'
_chemical_compound_source        .
_chemical_formula_weight         406.51


_cell_measurement_reflns_used    10146
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    1.259

# Sheldrick geometric approximatio 0.79 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            18400
_diffrn_reflns_av_unetI/netI     0.041
_reflns_number_total             4520
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0413
# Number of reflections with Friedels Law is 4520 
# Theoretical number of reflections is about 9117 

_diffrn_reflns_theta_min         4.896
_diffrn_reflns_theta_max         76.088
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        74.566
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   2.08
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.33


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4520
_oxford_refine_ls_R_factor_ref   0.0354
_refine_ls_wR_factor_ref         0.0855
_refine_ls_goodness_of_fit_ref   0.9943
_refine_ls_shift/su_max          0.0004974
_refine_ls_shift/su_mean         0.0000433


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4520
_refine_ls_R_factor_all          0.0354
_refine_ls_wR_factor_all         0.0855

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4052
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_gt          0.0815


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.29P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.81836(11) 0.66462(11) 0.69145(5) 0.0289 1.0000 Uani . . . . . .
C2 C 0.66669(15) 0.67980(14) 0.70068(6) 0.0219 1.0000 Uani . . . . . .
N3 N 0.53257(13) 0.57992(12) 0.74255(5) 0.0222 1.0000 Uani . . . . . .
C4 C 0.52319(17) 0.40444(15) 0.75605(7) 0.0291 1.0000 Uani . . . . . .
C5 C 0.31749(17) 0.30581(15) 0.74130(7) 0.0284 1.0000 Uani . . . . . .
C6 C 0.24006(15) 0.41675(14) 0.69226(6) 0.0230 1.0000 Uani . . . . . .
C7 C 0.34885(14) 0.59556(14) 0.72527(6) 0.0204 1.0000 Uani . . . . . .
C8 C 0.39096(15) 0.74228(14) 0.67590(6) 0.0197 1.0000 Uani . . . . . .
C9 C 0.27012(15) 0.82045(14) 0.64615(6) 0.0225 1.0000 Uani . . . . . .
C10 C 0.34352(16) 0.95875(15) 0.60439(7) 0.0255 1.0000 Uani . . . . . .
C11 C 0.53290(17) 1.02063(15) 0.59486(7) 0.0262 1.0000 Uani . . . . . .
C12 C 0.64877(15) 0.94091(14) 0.62659(6) 0.0226 1.0000 Uani . . . . . .
C13 C 0.57942(15) 0.79940(14) 0.66659(6) 0.0203 1.0000 Uani . . . . . .
C21 C 0.28327(16) 0.39631(14) 0.61188(7) 0.0235 1.0000 Uani . . . . . .
O22 O 0.41613(13) 0.35981(12) 0.59146(5) 0.0334 1.0000 Uani . . . . . .
O23 O 0.15796(12) 0.42642(12) 0.56630(5) 0.0318 1.0000 Uani . . . . . .
C24 C 0.1883(2) 0.4077(2) 0.48801(7) 0.0404 1.0000 Uani . . . . . .
O31 O 0.25713(10) 0.62612(10) 0.78792(4) 0.0237 1.0000 Uani . . . . . .
Si32 Si 0.33574(4) 0.75098(4) 0.863849(17) 0.0237 1.0000 Uani . . . . . .
C33 C 0.4947(2) 0.96024(18) 0.84195(8) 0.0385 1.0000 Uani . . . . . .
C34 C 0.4574(2) 0.6463(2) 0.92713(8) 0.0409 1.0000 Uani . . . . . .
C35 C 0.11769(18) 0.77002(18) 0.90446(7) 0.0306 1.0000 Uani . . . . . .
C36 C -0.02521(19) 0.5939(2) 0.90244(9) 0.0434 1.0000 Uani . . . . . .
C37 C 0.0394(2) 0.8864(2) 0.85974(9) 0.0465 1.0000 Uani . . . . . .
C38 C 0.1576(2) 0.8419(2) 0.98517(8) 0.0452 1.0000 Uani . . . . . .
N41 N 0.84920(14) 1.01549(13) 0.62130(6) 0.0303 1.0000 Uani . . . . . .
O42 O 0.94603(13) 1.03077(14) 0.67745(6) 0.0448 1.0000 Uani . . . . . .
O43 O 0.90684(15) 1.05982(17) 0.56112(7) 0.0541 1.0000 Uani . . . . . .
H41 H 0.5650 0.3953 0.8074 0.0341 1.0000 Uiso R . . . . .
H42 H 0.6051 0.3699 0.7215 0.0344 1.0000 Uiso R . . . . .
H51 H 0.2531 0.2911 0.7874 0.0335 1.0000 Uiso R . . . . .
H52 H 0.3025 0.1968 0.7172 0.0342 1.0000 Uiso R . . . . .
H61 H 0.1112 0.3966 0.6959 0.0266 1.0000 Uiso R . . . . .
H91 H 0.1428 0.7809 0.6539 0.0269 1.0000 Uiso R . . . . .
H101 H 0.2646 1.0100 0.5821 0.0314 1.0000 Uiso R . . . . .
H111 H 0.5806 1.1176 0.5673 0.0323 1.0000 Uiso R . . . . .
H241 H 0.0888 0.4296 0.4616 0.0610 1.0000 Uiso R . . . . .
H242 H 0.3048 0.4873 0.4767 0.0611 1.0000 Uiso R . . . . .
H243 H 0.1895 0.2951 0.4761 0.0624 1.0000 Uiso R . . . . .
H331 H 0.5179 1.0350 0.8854 0.0589 1.0000 Uiso R . . . . .
H332 H 0.4405 1.0084 0.8026 0.0585 1.0000 Uiso R . . . . .
H333 H 0.6095 0.9478 0.8255 0.0593 1.0000 Uiso R . . . . .
H342 H 0.5008 0.7164 0.9731 0.0619 1.0000 Uiso R . . . . .
H341 H 0.3770 0.5398 0.9387 0.0619 1.0000 Uiso R . . . . .
H343 H 0.5620 0.6288 0.9038 0.0610 1.0000 Uiso R . . . . .
H362 H -0.1342 0.6001 0.9274 0.0646 1.0000 Uiso R . . . . .
H361 H 0.0234 0.5116 0.9274 0.0634 1.0000 Uiso R . . . . .
H363 H -0.0643 0.5508 0.8518 0.0637 1.0000 Uiso R . . . . .
H372 H -0.0780 0.8924 0.8797 0.0691 1.0000 Uiso R . . . . .
H371 H 0.1249 1.0022 0.8633 0.0686 1.0000 Uiso R . . . . .
H373 H 0.0193 0.8475 0.8072 0.0683 1.0000 Uiso R . . . . .
H382 H 0.0433 0.8488 1.0054 0.0680 1.0000 Uiso R . . . . .
H381 H 0.2044 0.7683 1.0162 0.0658 1.0000 Uiso R . . . . .
H383 H 0.2459 0.9554 0.9887 0.0669 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.98(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2135(14) yes
C2 . N3 . 1.3788(15) yes
C2 . C13 . 1.4997(15) yes
N3 . C4 . 1.4737(15) yes
N3 . C7 . 1.4684(13) yes
C4 . C5 . 1.5396(16) yes
C4 . H41 . 0.988 no
C4 . H42 . 0.989 no
C5 . C6 . 1.5384(16) yes
C5 . H51 . 0.974 no
C5 . H52 . 0.961 no
C6 . C7 . 1.5479(15) yes
C6 . C21 . 1.5145(16) yes
C6 . H61 . 0.948 no
C7 . C8 . 1.5103(15) yes
C7 . O31 . 1.4017(13) yes
C8 . C9 . 1.3876(15) yes
C8 . C13 . 1.3855(14) yes
C9 . C10 . 1.3893(16) yes
C9 . H91 . 0.941 no
C10 . C11 . 1.3946(17) yes
C10 . H101 . 0.928 no
C11 . C12 . 1.3816(17) yes
C11 . H111 . 0.952 no
C12 . C13 . 1.3859(16) yes
C12 . N41 . 1.4700(14) yes
C21 . O22 . 1.2031(15) yes
C21 . O23 . 1.3307(14) yes
O23 . C24 . 1.4516(15) yes
C24 . H241 . 0.952 no
C24 . H242 . 0.967 no
C24 . H243 . 0.954 no
O31 . Si32 . 1.6623(8) yes
Si32 . C33 . 1.8642(14) yes
Si32 . C34 . 1.8580(14) yes
Si32 . C35 . 1.8808(13) yes
C33 . H331 . 0.956 no
C33 . H332 . 0.974 no
C33 . H333 . 0.964 no
C34 . H342 . 0.981 no
C34 . H341 . 0.950 no
C34 . H343 . 0.958 no
C35 . C36 . 1.536(2) yes
C35 . C37 . 1.5318(19) yes
C35 . C38 . 1.5376(18) yes
C36 . H362 . 0.970 no
C36 . H361 . 0.992 no
C36 . H363 . 0.972 no
C37 . H372 . 0.987 no
C37 . H371 . 0.984 no
C37 . H373 . 0.983 no
C38 . H382 . 0.970 no
C38 . H381 . 0.985 no
C38 . H383 . 0.978 no
N41 . O42 . 1.2159(16) yes
N41 . O43 . 1.2190(15) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 125.88(11) yes
O1 . C2 . C13 . 128.76(11) yes
N3 . C2 . C13 . 105.25(9) yes
C2 . N3 . C4 . 122.01(10) yes
C2 . N3 . C7 . 112.46(9) yes
C4 . N3 . C7 . 111.59(9) yes
N3 . C4 . C5 . 103.71(9) yes
N3 . C4 . H41 . 111.0 no
C5 . C4 . H41 . 111.5 no
N3 . C4 . H42 . 107.8 no
C5 . C4 . H42 . 113.5 no
H41 . C4 . H42 . 109.2 no
C4 . C5 . C6 . 105.23(9) yes
C4 . C5 . H51 . 110.8 no
C6 . C5 . H51 . 109.1 no
C4 . C5 . H52 . 111.1 no
C6 . C5 . H52 . 111.6 no
H51 . C5 . H52 . 109.0 no
C5 . C6 . C7 . 101.14(9) yes
C5 . C6 . C21 . 111.69(10) yes
C7 . C6 . C21 . 110.37(9) yes
C5 . C6 . H61 . 113.1 no
C7 . C6 . H61 . 110.9 no
C21 . C6 . H61 . 109.4 no
C6 . C7 . N3 . 102.75(9) yes
C6 . C7 . C8 . 119.30(9) yes
N3 . C7 . C8 . 102.64(8) yes
C6 . C7 . O31 . 106.72(9) yes
N3 . C7 . O31 . 113.65(9) yes
C8 . C7 . O31 . 111.62(9) yes
C7 . C8 . C9 . 128.34(10) yes
C7 . C8 . C13 . 109.12(9) yes
C9 . C8 . C13 . 122.45(10) yes
C8 . C9 . C10 . 117.70(10) yes
C8 . C9 . H91 . 121.1 no
C10 . C9 . H91 . 121.1 no
C9 . C10 . C11 . 121.18(10) yes
C9 . C10 . H101 . 119.2 no
C11 . C10 . H101 . 119.6 no
C10 . C11 . C12 . 119.22(11) yes
C10 . C11 . H111 . 119.8 no
C12 . C11 . H111 . 121.0 no
C11 . C12 . C13 . 121.06(10) yes
C11 . C12 . N41 . 118.64(10) yes
C13 . C12 . N41 . 120.18(10) yes
C2 . C13 . C12 . 132.86(10) yes
C2 . C13 . C8 . 108.67(9) yes
C12 . C13 . C8 . 118.35(10) yes
C6 . C21 . O22 . 124.30(11) yes
C6 . C21 . O23 . 111.82(10) yes
O22 . C21 . O23 . 123.87(11) yes
C21 . O23 . C24 . 115.27(10) yes
O23 . C24 . H241 . 107.1 no
O23 . C24 . H242 . 109.6 no
H241 . C24 . H242 . 110.6 no
O23 . C24 . H243 . 109.2 no
H241 . C24 . H243 . 110.3 no
H242 . C24 . H243 . 110.0 no
C7 . O31 . Si32 . 130.52(7) yes
O31 . Si32 . C33 . 111.86(5) yes
O31 . Si32 . C34 . 109.52(6) yes
C33 . Si32 . C34 . 109.70(7) yes
O31 . Si32 . C35 . 102.62(5) yes
C33 . Si32 . C35 . 111.94(7) yes
C34 . Si32 . C35 . 111.03(6) yes
Si32 . C33 . H331 . 109.1 no
Si32 . C33 . H332 . 110.7 no
H331 . C33 . H332 . 109.3 no
Si32 . C33 . H333 . 110.0 no
H331 . C33 . H333 . 109.6 no
H332 . C33 . H333 . 108.1 no
Si32 . C34 . H342 . 110.7 no
Si32 . C34 . H341 . 110.2 no
H342 . C34 . H341 . 109.1 no
Si32 . C34 . H343 . 109.9 no
H342 . C34 . H343 . 108.4 no
H341 . C34 . H343 . 108.5 no
Si32 . C35 . C36 . 108.89(9) yes
Si32 . C35 . C37 . 110.42(10) yes
C36 . C35 . C37 . 109.17(12) yes
Si32 . C35 . C38 . 109.89(9) yes
C36 . C35 . C38 . 109.16(12) yes
C37 . C35 . C38 . 109.30(12) yes
C35 . C36 . H362 . 109.8 no
C35 . C36 . H361 . 112.0 no
H362 . C36 . H361 . 107.8 no
C35 . C36 . H363 . 111.1 no
H362 . C36 . H363 . 107.3 no
H361 . C36 . H363 . 108.6 no
C35 . C37 . H372 . 110.4 no
C35 . C37 . H371 . 110.6 no
H372 . C37 . H371 . 106.8 no
C35 . C37 . H373 . 111.3 no
H372 . C37 . H373 . 109.5 no
H371 . C37 . H373 . 108.1 no
C35 . C38 . H382 . 108.7 no
C35 . C38 . H381 . 111.8 no
H382 . C38 . H381 . 107.4 no
C35 . C38 . H383 . 111.6 no
H382 . C38 . H383 . 107.9 no
H381 . C38 . H383 . 109.2 no
C12 . N41 . O42 . 117.79(10) yes
C12 . N41 . O43 . 117.76(11) yes
O42 . N41 . O43 . 124.43(11) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O1 1_455 172 0.94 2.49 3.4264(19) yes
C24 . H241 . O23 2_566 157 0.95 2.57 3.4635(19) yes
C24 . H242 . O22 2_666 162 0.97 2.51 3.4462(19) yes


####################################################################### 
# 
# 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_9-175La
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq4q
_database_code_depnum_ccdc_archive 'CCDC 2160053'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2018-11-12
_audit_creation_method           CRYSTALS_ver_14.61_build_7031

_oxford_structure_analysis_title 7037-RT-Cu
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_diffrn_special_details          
;
Crystals were first put on at 150K, but all turned out to be
twinned. Further investigations were performed including a 
temperature study that revealed a phase transition between 
200K and 175K.
;

_refine_special_details          
; 
Data were collected at room temperature and during refinement
it became clear that one group in the molecule was disordered.
The disordered group was modelled with appropriate restrains.
;

_cell_length_a                   11.7216(10)
_cell_length_b                   7.9879(6)
_cell_length_c                   13.3513(14)
_cell_angle_alpha                90
_cell_angle_beta                 113.311(12)
_cell_angle_gamma                90
_cell_volume                     1148.1(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C18 H43.50 N1.50 O9 Si1.50 
# Dc =      1.35 Fooo =    510.00 Mu =     15.85 M =    467.18
# Found Formula = C21.00 H29.00 N1 O6 Si1 
# Dc =      1.21 FOOO =    448.00 Mu =     11.97 M =    419.55

_chemical_formula_sum            'C21 H29 N O6 Si'
_chemical_formula_moiety         'C21 H29 N O6 Si'
_chemical_compound_source        .
_chemical_formula_weight         419.55


_cell_measurement_reflns_used    3200
_cell_measurement_theta_min      4
_cell_measurement_theta_max      72
_cell_measurement_temperature    300

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.18

_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             447.997
_exptl_absorpt_coefficient_mu    1.197

# Sheldrick geometric approximatio 0.91 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      300
_diffrn_reflns_number            11442
_diffrn_reflns_av_unetI/netI     0.058
_reflns_number_total             4682
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0581
# Number of reflections without Friedels Law is 4682 
# Number of reflections with Friedels Law is 2552 
# Theoretical number of reflections is about 2399 

_diffrn_reflns_theta_min         3.605
_diffrn_reflns_theta_max         76.050
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        73.769
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              -9
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   5.43
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.15


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     13
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4682
_oxford_refine_ls_R_factor_ref   0.0594
_refine_ls_wR_factor_ref         0.1173
_refine_ls_goodness_of_fit_ref   1.0019
_refine_ls_shift/su_max          0.0004028
_refine_ls_shift/su_mean         0.0000287


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4682
_refine_ls_R_factor_all          0.0594
_refine_ls_wR_factor_all         0.1173

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3525
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_gt          0.1001

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.09(3) # for 1854 Friedel pairs 
_oxford_Bijvoet_difference       -0.05(3) # for 1854 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.08(5) # for 2130 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1854 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.7319(2) 1.2144(3) 0.75474(19) 0.0804 1.0000 Uani . . . . . .
C2 C 0.7016(3) 1.0722(4) 0.7675(2) 0.0603 1.0000 Uani . . . . . .
N3 N 0.61958(19) 1.0311(3) 0.81400(17) 0.0570 1.0000 Uani . . . . . .
C4 C 0.5892(2) 1.1302(4) 0.8919(2) 0.0628 1.0000 Uani . . . . . .
C5 C 0.5727(2) 0.9936(4) 0.9681(3) 0.0672 1.0000 Uani . . . . . .
C6 C 0.6341(2) 0.8343(4) 0.9482(2) 0.0587 1.0000 Uani . . . . . .
C7 C 0.6091(2) 0.8509(4) 0.8274(2) 0.0559 1.0000 Uani . . . . . .
C8 C 0.6939(2) 0.7811(4) 0.77648(19) 0.0544 1.0000 Uani . . . . . .
C9 C 0.7183(2) 0.6172(4) 0.7597(2) 0.0638 1.0000 Uani . . . . . .
C10 C 0.7958(3) 0.5890(4) 0.7044(3) 0.0706 1.0000 Uani . . . . . .
C11 C 0.8452(3) 0.7184(4) 0.6671(3) 0.0723 1.0000 Uani . . . . . .
C12 C 0.8204(3) 0.8831(4) 0.6843(2) 0.0671 1.0000 Uani . . . . . .
C13 C 0.7437(2) 0.9127(4) 0.7392(2) 0.0563 1.0000 Uani . . . . . .
C21 C 0.6880(3) 1.2581(4) 0.9527(2) 0.0673 1.0000 Uani . . . . . .
O22 O 0.6643(2) 1.4015(3) 0.9627(2) 0.0966 1.0000 Uani . . . . . .
O23 O 0.79902(19) 1.1892(3) 0.99580(18) 0.0829 1.0000 Uani . . . . . .
C24 C 0.9017(3) 1.3031(7) 1.0496(3) 0.1186 1.0000 Uani . . . . . .
C31 C 0.7696(3) 0.8168(4) 1.0232(2) 0.0697 1.0000 Uani . . . . . .
O32 O 0.85443(18) 0.8073(5) 0.99746(19) 0.1096 1.0000 Uani . . . . . .
O33 O 0.7825(2) 0.8087(5) 1.12565(17) 0.1025 1.0000 Uani . . . . . .
C34 C 0.9100(4) 0.7907(8) 1.2051(3) 0.1353 1.0000 Uani . . . . . .
O41 O 0.48486(14) 0.7958(3) 0.77120(14) 0.0643 1.0000 Uani . . . . . .
Si42 Si 0.39393(14) 0.7318(4) 0.64994(13) 0.0668 0.544(5) Uani D . P 1 1 .
Si142 Si 0.38369(16) 0.8491(5) 0.64140(15) 0.0667 0.456(5) Uani D . P 1 2 .
C43 C 0.3838(9) 0.5001(10) 0.6499(9) 0.1185 0.544(5) Uani D . P 1 1 .
C143 C 0.3343(12) 1.0698(13) 0.6332(11) 0.1305 0.456(5) Uani D . P 1 2 .
C44 C 0.4596(11) 0.809(3) 0.5524(8) 0.0959 0.544(5) Uani D . P 1 1 .
C144 C 0.4310(14) 0.802(4) 0.5272(10) 0.0959 0.456(5) Uani D . P 1 2 .
C145 C 0.2511(7) 0.7097(11) 0.6249(7) 0.0881 0.456(5) Uani D . P 1 2 .
C45 C 0.2399(5) 0.8297(10) 0.6293(5) 0.0824 0.544(5) Uani D . P 1 1 .
C146 C 0.136(2) 0.743(4) 0.5201(12) 0.1061 0.456(5) Uani D . P 1 2 .
C46 C 0.1465(19) 0.774(4) 0.5154(14) 0.1304 0.544(5) Uani D . P 1 1 .
C48 C 0.2515(9) 1.0211(10) 0.6255(10) 0.1236 0.544(5) Uani D . P 1 1 .
C147 C 0.199(2) 0.746(5) 0.7126(16) 0.1548 0.456(5) Uani D . P 1 2 .
C47 C 0.2096(18) 0.777(4) 0.7271(15) 0.1385 0.544(5) Uani D . P 1 1 .
C148 C 0.2890(12) 0.5250(11) 0.6294(13) 0.1462 0.456(5) Uani D . P 1 2 .
H431 H 0.3246 0.4626 0.5796 0.1781 0.544(5) Uiso R . P 1 1 .
H433 H 0.4640 0.4526 0.6619 0.1778 0.544(5) Uiso R . P 1 1 .
H432 H 0.3583 0.4654 0.7073 0.1780 0.544(5) Uiso R . P 1 1 .
H1432 H 0.2622 1.0855 0.5670 0.1960 0.456(5) Uiso R . P 1 2 .
H1431 H 0.3151 1.0944 0.6954 0.1960 0.456(5) Uiso R . P 1 2 .
H1433 H 0.4010 1.1401 0.6329 0.1961 0.456(5) Uiso R . P 1 2 .
H41 H 0.5094 1.1896 0.8549 0.0746 1.0000 Uiso R . . . . .
H51 H 0.4848 0.9728 0.9504 0.0803 1.0000 Uiso R . . . . .
H52 H 0.6137 1.0282 1.0433 0.0803 1.0000 Uiso R . . . . .
H61 H 0.5915 0.7379 0.9600 0.0706 1.0000 Uiso R . . . . .
H91 H 0.6862 0.5261 0.7858 0.0774 1.0000 Uiso R . . . . .
H101 H 0.8135 0.4772 0.6920 0.0852 1.0000 Uiso R . . . . .
H111 H 0.8965 0.6950 0.6293 0.0873 1.0000 Uiso R . . . . .
H121 H 0.8534 0.9728 0.6581 0.0808 1.0000 Uiso R . . . . .
H242 H 0.9775 1.2372 1.0778 0.1781 1.0000 Uiso R . . . . .
H241 H 0.9065 1.3849 0.9987 0.1780 1.0000 Uiso R . . . . .
H243 H 0.8909 1.3574 1.1105 0.1781 1.0000 Uiso R . . . . .
H343 H 0.9106 0.7427 1.2723 0.2032 1.0000 Uiso R . . . . .
H341 H 0.9557 0.7211 1.1693 0.2030 1.0000 Uiso R . . . . .
H342 H 0.9480 0.9018 1.2190 0.2034 1.0000 Uiso R . . . . .
H1441 H 0.4375 0.6820 0.5227 0.1443 0.456(5) Uiso R . P 1 2 .
H1442 H 0.3680 0.8445 0.4606 0.1438 0.456(5) Uiso R . P 1 2 .
H1443 H 0.5098 0.8548 0.5407 0.1441 0.456(5) Uiso R . P 1 2 .
H443 H 0.4713 0.9298 0.5632 0.1438 0.544(5) Uiso R . P 1 1 .
H441 H 0.3990 0.7848 0.4791 0.1439 0.544(5) Uiso R . P 1 1 .
H442 H 0.5368 0.7521 0.5654 0.1438 0.544(5) Uiso R . P 1 1 .
H1461 H 0.0688 0.6749 0.5209 0.1598 0.456(5) Uiso R . P 1 2 .
H1462 H 0.1545 0.7163 0.4578 0.1599 0.456(5) Uiso R . P 1 2 .
H1463 H 0.1134 0.8598 0.5174 0.1600 0.456(5) Uiso R . P 1 2 .
H462 H 0.0694 0.8302 0.5004 0.1950 0.544(5) Uiso R . P 1 1 .
H463 H 0.1341 0.6550 0.5155 0.1949 0.544(5) Uiso R . P 1 1 .
H461 H 0.1780 0.8032 0.4609 0.1948 0.544(5) Uiso R . P 1 1 .
H481 H 0.1697 1.0673 0.6045 0.1850 0.544(5) Uiso R . P 1 1 .
H482 H 0.2864 1.0510 0.5734 0.1850 0.544(5) Uiso R . P 1 1 .
H483 H 0.3037 1.0593 0.6974 0.1849 0.544(5) Uiso R . P 1 1 .
H1472 H 0.1335 0.6681 0.7043 0.2349 0.456(5) Uiso R . P 1 2 .
H1473 H 0.2632 0.7332 0.7842 0.2349 0.456(5) Uiso R . P 1 2 .
H1471 H 0.1672 0.8585 0.7038 0.2349 0.456(5) Uiso R . P 1 2 .
H471 H 0.1260 0.8091 0.7134 0.2050 0.544(5) Uiso R . P 1 1 .
H473 H 0.2177 0.6573 0.7369 0.2050 0.544(5) Uiso R . P 1 1 .
H472 H 0.2651 0.8332 0.7917 0.2049 0.544(5) Uiso R . P 1 1 .
H1482 H 0.2172 0.4551 0.6141 0.2191 0.456(5) Uiso R . P 1 2 .
H1481 H 0.3247 0.5038 0.5763 0.2190 0.456(5) Uiso R . P 1 2 .
H1483 H 0.3492 0.5002 0.7017 0.2190 0.456(5) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.221(3) yes
C2 . N3 . 1.375(3) yes
C2 . C13 . 1.469(4) yes
N3 . C4 . 1.458(3) yes
N3 . C7 . 1.462(3) yes
C4 . C5 . 1.556(4) yes
C4 . C21 . 1.517(4) yes
C4 . H41 . 0.990 no
C5 . C6 . 1.537(4) yes
C5 . H51 . 0.976 no
C5 . H52 . 0.966 no
C6 . C7 . 1.527(3) yes
C6 . C31 . 1.512(4) yes
C6 . H61 . 0.964 no
C7 . C8 . 1.515(3) yes
C7 . O41 . 1.419(3) yes
C8 . C9 . 1.378(4) yes
C8 . C13 . 1.387(4) yes
C9 . C10 . 1.396(4) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.371(4) yes
C10 . H101 . 0.945 no
C11 . C12 . 1.386(4) yes
C11 . H111 . 0.945 no
C12 . C13 . 1.387(4) yes
C12 . H121 . 0.945 no
C21 . O22 . 1.198(4) yes
C21 . O23 . 1.317(3) yes
O23 . C24 . 1.452(4) yes
C24 . H242 . 0.971 no
C24 . H241 . 0.959 no
C24 . H243 . 0.973 no
C31 . O32 . 1.176(3) yes
C31 . O33 . 1.317(3) yes
O33 . C34 . 1.458(4) yes
C34 . H343 . 0.973 no
C34 . H341 . 1.012 no
C34 . H342 . 0.977 no
O41 . Si42 . 1.629(2) yes
O41 . Si142 . 1.722(3) yes
Si42 . C43 . 1.854(8) yes
Si42 . C44 . 1.860(14) yes
Si42 . C45 . 1.885(6) yes
Si142 . C143 . 1.845(10) yes
Si142 . C144 . 1.855(15) yes
Si142 . C145 . 1.853(8) yes
C43 . H431 . 0.967 no
C43 . H433 . 0.966 no
C43 . H432 . 0.968 no
C143 . H1432 . 0.960 no
C143 . H1431 . 0.962 no
C143 . H1433 . 0.965 no
C44 . H443 . 0.979 no
C44 . H441 . 0.974 no
C44 . H442 . 0.964 no
C144 . H1441 . 0.968 no
C144 . H1442 . 0.964 no
C144 . H1443 . 0.964 no
C145 . C146 . 1.537(9) yes
C145 . C147 . 1.546(9) yes
C145 . C148 . 1.535(9) yes
C45 . C46 . 1.547(9) yes
C45 . C48 . 1.538(8) yes
C45 . C47 . 1.541(9) yes
C146 . H1461 . 0.959 no
C146 . H1462 . 0.967 no
C146 . H1463 . 0.962 no
C46 . H462 . 0.957 no
C46 . H463 . 0.960 no
C46 . H461 . 0.967 no
C48 . H481 . 0.959 no
C48 . H482 . 0.966 no
C48 . H483 . 0.962 no
C147 . H1472 . 0.960 no
C147 . H1473 . 0.958 no
C147 . H1471 . 0.965 no
C47 . H471 . 0.958 no
C47 . H473 . 0.965 no
C47 . H472 . 0.962 no
C148 . H1482 . 0.963 no
C148 . H1481 . 0.970 no
C148 . H1483 . 0.964 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 125.4(2) yes
O1 . C2 . C13 . 128.7(2) yes
N3 . C2 . C13 . 106.0(2) yes
C2 . N3 . C4 . 127.2(2) yes
C2 . N3 . C7 . 113.4(2) yes
C4 . N3 . C7 . 113.0(2) yes
N3 . C4 . C5 . 102.4(2) yes
N3 . C4 . C21 . 113.4(2) yes
C5 . C4 . C21 . 112.9(2) yes
N3 . C4 . H41 . 110.7 no
C5 . C4 . H41 . 108.9 no
C21 . C4 . H41 . 108.4 no
C4 . C5 . C6 . 106.2(2) yes
C4 . C5 . H51 . 110.7 no
C6 . C5 . H51 . 109.8 no
C4 . C5 . H52 . 109.9 no
C6 . C5 . H52 . 110.0 no
H51 . C5 . H52 . 110.1 no
C5 . C6 . C7 . 101.7(2) yes
C5 . C6 . C31 . 113.8(2) yes
C7 . C6 . C31 . 114.84(19) yes
C5 . C6 . H61 . 109.0 no
C7 . C6 . H61 . 110.3 no
C31 . C6 . H61 . 107.1 no
C6 . C7 . N3 . 103.0(2) yes
C6 . C7 . C8 . 123.8(2) yes
N3 . C7 . C8 . 101.89(19) yes
C6 . C7 . O41 . 105.02(18) yes
N3 . C7 . O41 . 111.1(2) yes
C8 . C7 . O41 . 111.5(2) yes
C7 . C8 . C9 . 129.7(2) yes
C7 . C8 . C13 . 109.0(2) yes
C9 . C8 . C13 . 121.2(2) yes
C8 . C9 . C10 . 117.4(3) yes
C8 . C9 . H91 . 122.1 no
C10 . C9 . H91 . 120.5 no
C9 . C10 . C11 . 121.8(3) yes
C9 . C10 . H101 . 118.5 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 120.6(2) yes
C10 . C11 . H111 . 119.6 no
C12 . C11 . H111 . 119.7 no
C11 . C12 . C13 . 118.1(2) yes
C11 . C12 . H121 . 121.0 no
C13 . C12 . H121 . 120.9 no
C2 . C13 . C8 . 109.5(2) yes
C2 . C13 . C12 . 129.6(2) yes
C8 . C13 . C12 . 120.9(2) yes
C4 . C21 . O22 . 122.8(3) yes
C4 . C21 . O23 . 111.4(2) yes
O22 . C21 . O23 . 125.7(3) yes
C21 . O23 . C24 . 115.9(3) yes
O23 . C24 . H242 . 107.7 no
O23 . C24 . H241 . 110.2 no
H242 . C24 . H241 . 110.0 no
O23 . C24 . H243 . 109.6 no
H242 . C24 . H243 . 108.6 no
H241 . C24 . H243 . 110.6 no
C6 . C31 . O32 . 126.9(3) yes
C6 . C31 . O33 . 110.6(2) yes
O32 . C31 . O33 . 122.5(3) yes
C31 . O33 . C34 . 115.0(3) yes
O33 . C34 . H343 . 109.9 no
O33 . C34 . H341 . 107.0 no
H343 . C34 . H341 . 114.0 no
O33 . C34 . H342 . 107.9 no
H343 . C34 . H342 . 110.2 no
H341 . C34 . H342 . 107.6 no
C7 . O41 . Si42 . 138.93(16) yes
C7 . O41 . Si142 . 127.55(18) yes
O41 . Si42 . C43 . 109.3(3) yes
O41 . Si42 . C44 . 107.6(5) yes
C43 . Si42 . C44 . 112.0(9) yes
O41 . Si42 . C45 . 103.1(2) yes
C43 . Si42 . C45 . 110.9(4) yes
C44 . Si42 . C45 . 113.4(6) yes
O41 . Si142 . C143 . 111.8(4) yes
O41 . Si142 . C144 . 117.8(6) yes
C143 . Si142 . C144 . 109.4(11) yes
O41 . Si142 . C145 . 100.5(3) yes
C143 . Si142 . C145 . 109.8(6) yes
C144 . Si142 . C145 . 106.9(9) yes
Si42 . C43 . H431 . 109.3 no
Si42 . C43 . H433 . 109.5 no
H431 . C43 . H433 . 108.5 no
Si42 . C43 . H432 . 109.0 no
H431 . C43 . H432 . 110.6 no
H433 . C43 . H432 . 109.9 no
Si142 . C143 . H1432 . 108.7 no
Si142 . C143 . H1431 . 108.6 no
H1432 . C143 . H1431 . 110.3 no
Si142 . C143 . H1433 . 108.7 no
H1432 . C143 . H1433 . 109.8 no
H1431 . C143 . H1433 . 110.6 no
Si42 . C44 . H443 . 107.3 no
Si42 . C44 . H441 . 107.5 no
H443 . C44 . H441 . 110.2 no
Si42 . C44 . H442 . 109.7 no
H443 . C44 . H442 . 111.7 no
H441 . C44 . H442 . 110.3 no
Si142 . C144 . H1441 . 108.0 no
Si142 . C144 . H1442 . 108.6 no
H1441 . C144 . H1442 . 109.8 no
Si142 . C144 . H1443 . 109.6 no
H1441 . C144 . H1443 . 110.4 no
H1442 . C144 . H1443 . 110.4 no
Si142 . C145 . C146 . 113.4(16) yes
Si142 . C145 . C147 . 111.2(15) yes
C146 . C145 . C147 . 100.9(14) yes
Si142 . C145 . C148 . 110.9(7) yes
C146 . C145 . C148 . 110.0(14) yes
C147 . C145 . C148 . 110.1(16) yes
Si42 . C45 . C46 . 106.8(9) yes
Si42 . C45 . C48 . 109.0(5) yes
C46 . C45 . C48 . 107.0(13) yes
Si42 . C45 . C47 . 106.9(7) yes
C46 . C45 . C47 . 116.3(17) yes
C48 . C45 . C47 . 110.7(14) yes
C145 . C146 . H1461 . 108.6 no
C145 . C146 . H1462 . 109.0 no
H1461 . C146 . H1462 . 110.4 no
C145 . C146 . H1463 . 109.4 no
H1461 . C146 . H1463 . 110.0 no
H1462 . C146 . H1463 . 109.5 no
C45 . C46 . H462 . 108.2 no
C45 . C46 . H463 . 109.4 no
H462 . C46 . H463 . 109.6 no
C45 . C46 . H461 . 109.7 no
H462 . C46 . H461 . 109.8 no
H463 . C46 . H461 . 110.1 no
C45 . C48 . H481 . 107.5 no
C45 . C48 . H482 . 109.8 no
H481 . C48 . H482 . 110.7 no
C45 . C48 . H483 . 108.1 no
H481 . C48 . H483 . 109.7 no
H482 . C48 . H483 . 111.0 no
C145 . C147 . H1472 . 109.3 no
C145 . C147 . H1473 . 110.4 no
H1472 . C147 . H1473 . 108.9 no
C145 . C147 . H1471 . 109.4 no
H1472 . C147 . H1471 . 109.5 no
H1473 . C147 . H1471 . 109.4 no
C45 . C47 . H471 . 109.1 no
C45 . C47 . H473 . 110.1 no
H471 . C47 . H473 . 109.2 no
C45 . C47 . H472 . 109.4 no
H471 . C47 . H472 . 108.8 no
H473 . C47 . H472 . 110.2 no
C145 . C148 . H1482 . 109.5 no
C145 . C148 . H1481 . 110.0 no
H1482 . C148 . H1481 . 109.7 no
C145 . C148 . H1483 . 108.9 no
H1482 . C148 . H1483 . 109.0 no
H1481 . C148 . H1483 . 109.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H51 . O22 2_647 142 0.98 2.52 3.337(13) yes
C10 . H101 . O1 1_545 125 0.95 2.58 3.220(13) yes


####################################################################### 
# 
# 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_8-172
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq3p
_database_code_depnum_ccdc_archive 'CCDC 2160052'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2019-04-23
_audit_creation_method           'CRYSTALS_ver_14.61_build_7212 '

_oxford_structure_analysis_title 7138

_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   8.25810(10)
_cell_length_b                   15.38810(10)
_cell_length_c                   31.9391(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4058.71(6)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C19 H26 N2 O6 Si1 
# Dc =      1.33 Fooo =   1728.00 Mu =     13.53 M =    406.51
# Found Formula = C19 H26 N2 O6 Si1 
# Dc =      1.33 FOOO =   1728.00 Mu =     13.53 M =    406.51

_chemical_formula_sum            'C19 H26 N2 O6 Si'
_chemical_formula_moiety         'C19 H26 N2 O6 Si'
_chemical_compound_source        .
_chemical_formula_weight         406.51


_cell_measurement_reflns_used    7940
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      76.65
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.35

_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    1.353

# Sheldrick geometric approximatio 0.76 0.95 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.95
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            15783
_diffrn_reflns_av_unetI/netI     0.046
_reflns_number_total             4233
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0467
# Number of reflections with Friedels Law is 4233 
# Theoretical number of reflections is about 8542 

_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         76.624
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        75.092
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       39
_reflns_limit_h_min              0
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              39

_oxford_diffrn_Wilson_B_factor   1.60
_oxford_diffrn_Wilson_scale      0.14

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.36


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4233
_oxford_refine_ls_R_factor_ref   0.0375
_refine_ls_wR_factor_ref         0.0932
_refine_ls_goodness_of_fit_ref   0.9967
_refine_ls_shift/su_max          0.0011576
_refine_ls_shift/su_mean         0.0000856


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        4233
_refine_ls_R_factor_all          0.0375
_refine_ls_wR_factor_all         0.0932

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3809
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_gt          0.0881


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.97P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.30847(12) 0.51590(6) 0.68145(3) 0.0279 1.0000 Uani . . . . . .
C2 C 0.40633(15) 0.56842(8) 0.66842(4) 0.0196 1.0000 Uani . . . . . .
N3 N 0.57024(12) 0.55536(6) 0.66423(3) 0.0184 1.0000 Uani . . . . . .
C4 C 0.66279(16) 0.49787(8) 0.69209(4) 0.0236 1.0000 Uani . . . . . .
C5 C 0.81157(16) 0.55252(8) 0.70478(4) 0.0229 1.0000 Uani . . . . . .
C6 C 0.77067(14) 0.64704(8) 0.69297(3) 0.0180 1.0000 Uani . . . . . .
C7 C 0.65945(14) 0.63502(7) 0.65426(3) 0.0168 1.0000 Uani . . . . . .
C8 C 0.52460(14) 0.69995(8) 0.64727(3) 0.0178 1.0000 Uani . . . . . .
C9 C 0.53499(15) 0.78594(8) 0.63430(4) 0.0212 1.0000 Uani . . . . . .
C10 C 0.39112(16) 0.83090(8) 0.62824(4) 0.0227 1.0000 Uani . . . . . .
C11 C 0.24426(15) 0.78909(8) 0.63565(4) 0.0212 1.0000 Uani . . . . . .
C12 C 0.23147(15) 0.70376(8) 0.64948(4) 0.0212 1.0000 Uani . . . . . .
C13 C 0.37683(15) 0.66023(8) 0.65467(3) 0.0189 1.0000 Uani . . . . . .
N15 N 0.09461(14) 0.83801(7) 0.62727(3) 0.0239 1.0000 Uani . . . . . .
O16 O -0.03084(12) 0.81241(7) 0.64375(3) 0.0311 1.0000 Uani . . . . . .
O17 O 0.10300(13) 0.90070(7) 0.60382(3) 0.0346 1.0000 Uani . . . . . .
C21 C 0.67702(15) 0.69408(8) 0.72690(4) 0.0203 1.0000 Uani . . . . . .
O22 O 0.57963(15) 0.66064(7) 0.74964(3) 0.0364 1.0000 Uani . . . . . .
O23 O 0.71204(11) 0.77897(6) 0.72664(3) 0.0244 1.0000 Uani . . . . . .
C24 C 0.6161(2) 0.83346(9) 0.75380(5) 0.0326 1.0000 Uani . . . . . .
O31 O 0.76052(10) 0.62707(6) 0.61907(2) 0.0193 1.0000 Uani . . . . . .
Si32 Si 0.72128(4) 0.58640(2) 0.571671(9) 0.0171 1.0000 Uani . . . . . .
C33 C 0.50474(16) 0.59810(9) 0.55608(4) 0.0271 1.0000 Uani . . . . . .
C34 C 0.77818(18) 0.46985(8) 0.57148(5) 0.0298 1.0000 Uani . . . . . .
C35 C 0.85790(16) 0.65161(8) 0.53634(4) 0.0221 1.0000 Uani . . . . . .
C36 C 0.8223(2) 0.74877(9) 0.54183(4) 0.0321 1.0000 Uani . . . . . .
C37 C 0.8286(2) 0.62660(11) 0.49036(4) 0.0367 1.0000 Uani . . . . . .
C38 C 1.03546(18) 0.63441(11) 0.54772(5) 0.0342 1.0000 Uani . . . . . .
H41 H 0.5991 0.4842 0.7161 0.0289 1.0000 Uiso R . . . . .
H42 H 0.6947 0.4448 0.6779 0.0270 1.0000 Uiso R . . . . .
H51 H 0.8314 0.5468 0.7344 0.0269 1.0000 Uiso R . . . . .
H52 H 0.9065 0.5344 0.6896 0.0272 1.0000 Uiso R . . . . .
H61 H 0.8632 0.6799 0.6856 0.0216 1.0000 Uiso R . . . . .
H91 H 0.6371 0.8121 0.6289 0.0260 1.0000 Uiso R . . . . .
H101 H 0.3897 0.8888 0.6198 0.0279 1.0000 Uiso R . . . . .
H121 H 0.1285 0.6780 0.6544 0.0258 1.0000 Uiso R . . . . .
H241 H 0.6846 0.8775 0.7649 0.0510 1.0000 Uiso R . . . . .
H242 H 0.5694 0.8010 0.7761 0.0500 1.0000 Uiso R . . . . .
H243 H 0.5302 0.8604 0.7378 0.0513 1.0000 Uiso R . . . . .
H331 H 0.4936 0.5767 0.5277 0.0410 1.0000 Uiso R . . . . .
H332 H 0.4689 0.6576 0.5565 0.0418 1.0000 Uiso R . . . . .
H333 H 0.4357 0.5631 0.5740 0.0423 1.0000 Uiso R . . . . .
H342 H 0.7680 0.4446 0.5441 0.0463 1.0000 Uiso R . . . . .
H341 H 0.8881 0.4623 0.5800 0.0473 1.0000 Uiso R . . . . .
H343 H 0.7108 0.4386 0.5908 0.0463 1.0000 Uiso R . . . . .
H362 H 0.8886 0.7817 0.5229 0.0483 1.0000 Uiso R . . . . .
H361 H 0.8442 0.7669 0.5703 0.0473 1.0000 Uiso R . . . . .
H363 H 0.7090 0.7623 0.5355 0.0479 1.0000 Uiso R . . . . .
H372 H 0.9046 0.6594 0.4730 0.0543 1.0000 Uiso R . . . . .
H371 H 0.7176 0.6405 0.4817 0.0535 1.0000 Uiso R . . . . .
H373 H 0.8467 0.5645 0.4858 0.0536 1.0000 Uiso R . . . . .
H382 H 1.1041 0.6706 0.5308 0.0510 1.0000 Uiso R . . . . .
H381 H 1.0566 0.6480 0.5771 0.0508 1.0000 Uiso R . . . . .
H383 H 1.0650 0.5744 0.5429 0.0505 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.71(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2163(16) yes
C2 . N3 . 1.3749(15) yes
C2 . C13 . 1.4994(16) yes
N3 . C4 . 1.4693(14) yes
N3 . C7 . 1.4653(14) yes
C4 . C5 . 1.5431(17) yes
C4 . H41 . 0.952 no
C4 . H42 . 0.971 no
C5 . C6 . 1.5401(16) yes
C5 . H51 . 0.964 no
C5 . H52 . 0.962 no
C6 . C7 . 1.5514(15) yes
C6 . C21 . 1.5154(16) yes
C6 . H61 . 0.946 no
C7 . C8 . 1.5126(15) yes
C7 . O31 . 1.4052(13) yes
C8 . C9 . 1.3893(16) yes
C8 . C13 . 1.3851(16) yes
C9 . C10 . 1.3884(17) yes
C9 . H91 . 0.950 no
C10 . C11 . 1.3930(18) yes
C10 . H101 . 0.932 no
C11 . C12 . 1.3894(17) yes
C11 . N15 . 1.4715(15) yes
C12 . C13 . 1.3847(16) yes
C12 . H121 . 0.951 no
N15 . O16 . 1.2270(15) yes
N15 . O17 . 1.2232(15) yes
C21 . O22 . 1.1995(16) yes
C21 . O23 . 1.3380(15) yes
O23 . C24 . 1.4435(15) yes
C24 . H241 . 0.951 no
C24 . H242 . 0.953 no
C24 . H243 . 0.968 no
O31 . Si32 . 1.6699(8) yes
Si32 . C33 . 1.8650(14) yes
Si32 . C34 . 1.8541(14) yes
Si32 . C35 . 1.8851(13) yes
C33 . H331 . 0.970 no
C33 . H332 . 0.962 no
C33 . H333 . 0.971 no
C34 . H342 . 0.962 no
C34 . H341 . 0.955 no
C34 . H343 . 0.960 no
C35 . C36 . 1.5338(17) yes
C35 . C37 . 1.5371(17) yes
C35 . C38 . 1.5337(19) yes
C36 . H362 . 0.959 no
C36 . H361 . 0.967 no
C36 . H363 . 0.980 no
C37 . H372 . 0.977 no
C37 . H371 . 0.982 no
C37 . H373 . 0.977 no
C38 . H382 . 0.961 no
C38 . H381 . 0.977 no
C38 . H383 . 0.968 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 126.18(12) yes
O1 . C2 . C13 . 128.19(12) yes
N3 . C2 . C13 . 105.62(10) yes
C2 . N3 . C4 . 122.77(10) yes
C2 . N3 . C7 . 113.19(10) yes
C4 . N3 . C7 . 111.96(9) yes
N3 . C4 . C5 . 104.19(9) yes
N3 . C4 . H41 . 109.4 no
C5 . C4 . H41 . 110.4 no
N3 . C4 . H42 . 111.4 no
C5 . C4 . H42 . 111.4 no
H41 . C4 . H42 . 109.9 no
C4 . C5 . C6 . 106.01(9) yes
C4 . C5 . H51 . 110.1 no
C6 . C5 . H51 . 111.3 no
C4 . C5 . H52 . 111.1 no
C6 . C5 . H52 . 109.2 no
H51 . C5 . H52 . 109.2 no
C5 . C6 . C7 . 102.26(9) yes
C5 . C6 . C21 . 112.83(10) yes
C7 . C6 . C21 . 108.95(9) yes
C5 . C6 . H61 . 112.8 no
C7 . C6 . H61 . 110.1 no
C21 . C6 . H61 . 109.6 no
C6 . C7 . N3 . 102.95(9) yes
C6 . C7 . C8 . 118.34(9) yes
N3 . C7 . C8 . 102.38(9) yes
C6 . C7 . O31 . 107.23(9) yes
N3 . C7 . O31 . 113.55(9) yes
C8 . C7 . O31 . 112.14(9) yes
C7 . C8 . C9 . 128.87(11) yes
C7 . C8 . C13 . 109.39(10) yes
C9 . C8 . C13 . 121.71(11) yes
C8 . C9 . C10 . 117.60(11) yes
C8 . C9 . H91 . 120.8 no
C10 . C9 . H91 . 121.6 no
C9 . C10 . C11 . 119.42(11) yes
C9 . C10 . H101 . 121.9 no
C11 . C10 . H101 . 118.7 no
C10 . C11 . C12 . 123.82(11) yes
C10 . C11 . N15 . 117.65(11) yes
C12 . C11 . N15 . 118.51(11) yes
C11 . C12 . C13 . 115.43(11) yes
C11 . C12 . H121 . 121.0 no
C13 . C12 . H121 . 123.6 no
C2 . C13 . C8 . 108.82(10) yes
C2 . C13 . C12 . 129.19(11) yes
C8 . C13 . C12 . 121.99(11) yes
C11 . N15 . O16 . 117.83(11) yes
C11 . N15 . O17 . 117.86(11) yes
O16 . N15 . O17 . 124.31(11) yes
C6 . C21 . O22 . 124.77(11) yes
C6 . C21 . O23 . 110.58(10) yes
O22 . C21 . O23 . 124.58(12) yes
C21 . O23 . C24 . 116.41(10) yes
O23 . C24 . H241 . 108.1 no
O23 . C24 . H242 . 111.6 no
H241 . C24 . H242 . 109.6 no
O23 . C24 . H243 . 109.5 no
H241 . C24 . H243 . 109.1 no
H242 . C24 . H243 . 108.9 no
C7 . O31 . Si32 . 129.97(7) yes
O31 . Si32 . C33 . 113.08(5) yes
O31 . Si32 . C34 . 108.44(6) yes
C33 . Si32 . C34 . 109.60(6) yes
O31 . Si32 . C35 . 103.13(5) yes
C33 . Si32 . C35 . 111.26(6) yes
C34 . Si32 . C35 . 111.18(6) yes
Si32 . C33 . H331 . 107.9 no
Si32 . C33 . H332 . 112.5 no
H331 . C33 . H332 . 107.8 no
Si32 . C33 . H333 . 110.7 no
H331 . C33 . H333 . 107.9 no
H332 . C33 . H333 . 109.9 no
Si32 . C34 . H342 . 111.9 no
Si32 . C34 . H341 . 110.9 no
H342 . C34 . H341 . 107.1 no
Si32 . C34 . H343 . 109.6 no
H342 . C34 . H343 . 109.4 no
H341 . C34 . H343 . 107.8 no
Si32 . C35 . C36 . 109.61(9) yes
Si32 . C35 . C37 . 110.16(9) yes
C36 . C35 . C37 . 108.86(11) yes
Si32 . C35 . C38 . 109.78(9) yes
C36 . C35 . C38 . 108.92(12) yes
C37 . C35 . C38 . 109.48(12) yes
C35 . C36 . H362 . 109.4 no
C35 . C36 . H361 . 110.7 no
H362 . C36 . H361 . 109.4 no
C35 . C36 . H363 . 111.5 no
H362 . C36 . H363 . 107.7 no
H361 . C36 . H363 . 108.1 no
C35 . C37 . H372 . 108.2 no
C35 . C37 . H371 . 111.1 no
H372 . C37 . H371 . 109.1 no
C35 . C37 . H373 . 111.2 no
H372 . C37 . H373 . 108.8 no
H371 . C37 . H373 . 108.3 no
C35 . C38 . H382 . 109.3 no
C35 . C38 . H381 . 111.2 no
H382 . C38 . H381 . 108.2 no
C35 . C38 . H383 . 111.6 no
H382 . C38 . H383 . 108.4 no
H381 . C38 . H383 . 108.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . O16 1_655 145 0.95 2.59 3.4108(18) yes


####################################################################### 
# 
# 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_10-177
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq5r
_database_code_depnum_ccdc_archive 'CCDC 2160054'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2020-02-18
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7272
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   10.47270(10)
_cell_length_b                   8.76000(10)
_cell_length_c                   28.8275(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.2357(9)
_cell_angle_gamma                90
_cell_volume                     2637.44(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C27 H33 N1 O6 Si1 
# Dc =      1.25 Fooo =   1056.00 Mu =     11.25 M =    495.65
# Found Formula = C27 H33 N1 O6 Si1 
# Dc =      1.25 FOOO =   1056.00 Mu =     11.25 M =    495.65

_chemical_formula_sum            'C27 H33 N O6 Si'
_chemical_formula_moiety         'C27 H33 N O6 Si'
_chemical_compound_source        .
_chemical_formula_weight         495.65


_cell_measurement_reflns_used    16952
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      77.02
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.125

# Sheldrick geometric approximatio 0.81 0.82 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.82
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            26682
_diffrn_reflns_av_unetI/netI     0.043
_reflns_number_total             10665
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0429
# Number of reflections without Friedels Law is 10665 
# Number of reflections with Friedels Law is 5918 
# Theoretical number of reflections is about 5589 


_diffrn_reflns_theta_min         1.537
_diffrn_reflns_theta_max         77.185
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        75.641
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -11
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   2.23
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.21


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     632
_refine_ls_number_reflns         10665
_oxford_refine_ls_R_factor_ref   0.0320
_refine_ls_R_factor_all          0.0320
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_all         0.0832
_refine_ls_goodness_of_fit_ref   1.0042
_refine_ls_shift/su_max          0.0019599
_refine_ls_shift/su_mean         0.0001134


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        10665
_oxford_refine_ls_R_factor_all   0.0320
_oxford_refine_ls_wR_factor_all  0.0832

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                10308
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_gt          0.0816

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.005(8) # for 4119 Friedel pairs 
_oxford_Bijvoet_difference       0.003(7) # for 4119 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.001(12) # for 4747 Friedel pairs 
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 4119 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.10P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.82516(10) 0.80454(14) 0.88807(4) 0.0350 1.0000 Uani . . . . . .
C2 C 0.88886(12) 0.69147(17) 0.88099(4) 0.0261 1.0000 Uani . . . . . .
C3 C 0.85083(12) 0.52870(17) 0.88108(4) 0.0256 1.0000 Uani . . . . . .
C4 C 0.73478(13) 0.46339(19) 0.89080(5) 0.0323 1.0000 Uani . . . . . .
C5 C 0.72510(15) 0.3051(2) 0.88878(6) 0.0375 1.0000 Uani . . . . . .
C6 C 0.82939(15) 0.21455(19) 0.87897(5) 0.0348 1.0000 Uani . . . . . .
C7 C 0.94591(13) 0.28155(17) 0.87005(4) 0.0274 1.0000 Uani . . . . . .
C8 C 0.95334(11) 0.43892(16) 0.86990(4) 0.0227 1.0000 Uani . . . . . .
C9 C 1.06767(11) 0.54004(15) 0.86339(4) 0.0215 1.0000 Uani . . . . . .
C10 C 1.13065(11) 0.55942(16) 0.81706(4) 0.0234 1.0000 Uani . . . . . .
C11 C 1.18534(12) 0.72292(16) 0.82320(5) 0.0270 1.0000 Uani . . . . . .
C12 C 1.07956(12) 0.81165(16) 0.84657(4) 0.0250 1.0000 Uani . . . . . .
N13 N 1.01670(10) 0.69247(13) 0.87166(4) 0.0239 1.0000 Uani . . . . . .
O21 O 1.16978(8) 0.50021(12) 0.89620(3) 0.0251 1.0000 Uani . . . . . .
Si22 Si 1.18952(3) 0.53897(5) 0.952976(12) 0.0261 1.0000 Uani . . . . . .
C23 C 1.04339(14) 0.5013(3) 0.98415(5) 0.0447 1.0000 Uani . . . . . .
C24 C 1.2403(2) 0.7414(2) 0.96195(6) 0.0488 1.0000 Uani . . . . . .
C25 C 1.32161(13) 0.4029(2) 0.97264(5) 0.0342 1.0000 Uani . . . . . .
C26 C 1.2741(2) 0.2388(3) 0.96838(8) 0.0566 1.0000 Uani . . . . . .
C27 C 1.36762(17) 0.4353(3) 1.02347(5) 0.0533 1.0000 Uani . . . . . .
C28 C 1.43513(15) 0.4246(3) 0.94274(6) 0.0528 1.0000 Uani . . . . . .
C31 C 1.04894(12) 0.54821(17) 0.77109(4) 0.0272 1.0000 Uani . . . . . .
O32 O 1.08831(12) 0.5883(2) 0.73509(4) 0.0580 1.0000 Uani . . . . . .
O33 O 0.93442(9) 0.48844(12) 0.77466(3) 0.0283 1.0000 Uani . . . . . .
C34 C 0.85118(14) 0.4856(2) 0.73186(5) 0.0380 1.0000 Uani . . . . . .
C41 C 0.98809(12) 0.88503(16) 0.80919(4) 0.0254 1.0000 Uani . . . . . .
O42 O 0.89499(9) 0.82473(13) 0.79045(3) 0.0318 1.0000 Uani . . . . . .
O43 O 1.03111(10) 1.02380(12) 0.79911(3) 0.0296 1.0000 Uani . . . . . .
C44 C 0.95804(15) 1.10523(17) 0.76145(5) 0.0331 1.0000 Uani . . . . . .
C45 C 1.00548(14) 1.06461(17) 0.71511(5) 0.0296 1.0000 Uani . . . . . .
C46 C 0.95041(15) 0.94518(18) 0.68880(5) 0.0339 1.0000 Uani . . . . . .
C47 C 0.99656(17) 0.90843(19) 0.64628(5) 0.0382 1.0000 Uani . . . . . .
C48 C 1.09728(16) 0.9901(2) 0.62983(5) 0.0397 1.0000 Uani . . . . . .
C49 C 1.15149(16) 1.1103(2) 0.65550(6) 0.0433 1.0000 Uani . . . . . .
C50 C 1.10537(16) 1.1478(2) 0.69817(6) 0.0385 1.0000 Uani . . . . . .
O51 O 0.68088(10) 0.75409(13) 0.61452(4) 0.0385 1.0000 Uani . . . . . .
C52 C 0.61384(12) 0.64130(16) 0.61780(5) 0.0258 1.0000 Uani . . . . . .
C53 C 0.64965(12) 0.47794(16) 0.61653(4) 0.0240 1.0000 Uani . . . . . .
C54 C 0.76708(13) 0.41221(18) 0.60888(5) 0.0305 1.0000 Uani . . . . . .
C55 C 0.77526(14) 0.25433(19) 0.61005(5) 0.0326 1.0000 Uani . . . . . .
C56 C 0.66812(14) 0.16473(18) 0.61747(5) 0.0316 1.0000 Uani . . . . . .
C57 C 0.55041(13) 0.23164(16) 0.62467(4) 0.0265 1.0000 Uani . . . . . .
C58 C 0.54387(11) 0.38952(16) 0.62540(4) 0.0218 1.0000 Uani . . . . . .
C59 C 0.43006(10) 0.49267(15) 0.63133(4) 0.0209 1.0000 Uani . . . . . .
C60 C 0.36645(11) 0.51132(16) 0.67785(4) 0.0238 1.0000 Uani . . . . . .
C61 C 0.31671(12) 0.67662(17) 0.67342(5) 0.0275 1.0000 Uani . . . . . .
C62 C 0.42521(12) 0.76330(16) 0.65114(4) 0.0251 1.0000 Uani . . . . . .
N63 N 0.48392(10) 0.64464(13) 0.62417(4) 0.0232 1.0000 Uani . . . . . .
O71 O 0.32834(8) 0.45574(12) 0.59803(3) 0.0243 1.0000 Uani . . . . . .
Si72 Si 0.30879(3) 0.50029(5) 0.541706(11) 0.0236 1.0000 Uani . . . . . .
C73 C 0.26166(17) 0.7044(2) 0.53457(6) 0.0401 1.0000 Uani . . . . . .
C74 C 0.45493(13) 0.4619(2) 0.51069(5) 0.0384 1.0000 Uani . . . . . .
C75 C 0.17391(12) 0.36947(18) 0.52084(4) 0.0272 1.0000 Uani . . . . . .
C76 C 0.21881(16) 0.2038(2) 0.52341(6) 0.0403 1.0000 Uani . . . . . .
C77 C 0.12773(15) 0.4081(2) 0.47037(5) 0.0403 1.0000 Uani . . . . . .
C78 C 0.06083(13) 0.3907(2) 0.55132(5) 0.0370 1.0000 Uani . . . . . .
C81 C 0.45491(12) 0.47976(16) 0.72109(4) 0.0244 1.0000 Uani . . . . . .
O82 O 0.54603(10) 0.39642(12) 0.72271(3) 0.0308 1.0000 Uani . . . . . .
O83 O 0.41448(10) 0.54968(15) 0.75863(3) 0.0376 1.0000 Uani . . . . . .
C84 C 0.49775(15) 0.5292(2) 0.80054(5) 0.0407 1.0000 Uani . . . . . .
C91 C 0.52025(12) 0.82251(16) 0.68947(4) 0.0256 1.0000 Uani . . . . . .
O92 O 0.59791(10) 0.74415(13) 0.71126(4) 0.0365 1.0000 Uani . . . . . .
O93 O 0.50175(10) 0.97021(12) 0.69710(3) 0.0309 1.0000 Uani . . . . . .
C94 C 0.58378(14) 1.03748(17) 0.73476(5) 0.0332 1.0000 Uani . . . . . .
C95 C 0.52302(13) 1.02631(16) 0.78014(5) 0.0291 1.0000 Uani . . . . . .
C96 C 0.40948(15) 1.1034(2) 0.78694(6) 0.0389 1.0000 Uani . . . . . .
C97 C 0.35669(16) 1.0957(2) 0.82991(7) 0.0458 1.0000 Uani . . . . . .
C98 C 0.41629(17) 1.0113(2) 0.86581(5) 0.0444 1.0000 Uani . . . . . .
C99 C 0.52742(17) 0.9323(2) 0.85881(5) 0.0432 1.0000 Uani . . . . . .
C100 C 0.58113(15) 0.9405(2) 0.81618(5) 0.0367 1.0000 Uani . . . . . .
H41 H 0.6675 0.5248 0.8990 0.0383 1.0000 Uiso R . . . . .
H51 H 0.6466 0.2592 0.8943 0.0456 1.0000 Uiso R . . . . .
H61 H 0.8223 0.1096 0.8795 0.0419 1.0000 Uiso R . . . . .
H71 H 1.0168 0.2200 0.8643 0.0334 1.0000 Uiso R . . . . .
H101 H 1.1983 0.4853 0.8153 0.0269 1.0000 Uiso R . . . . .
H111 H 1.2626 0.7233 0.8451 0.0321 1.0000 Uiso R . . . . .
H112 H 1.2030 0.7685 0.7946 0.0329 1.0000 Uiso R . . . . .
H121 H 1.1144 0.8894 0.8679 0.0295 1.0000 Uiso R . . . . .
H231 H 1.0647 0.5018 1.0174 0.0682 1.0000 Uiso R . . . . .
H232 H 1.0074 0.4044 0.9751 0.0658 1.0000 Uiso R . . . . .
H233 H 0.9795 0.5809 0.9774 0.0658 1.0000 Uiso R . . . . .
H241 H 1.2618 0.7609 0.9939 0.0729 1.0000 Uiso R . . . . .
H242 H 1.3114 0.7626 0.9442 0.0728 1.0000 Uiso R . . . . .
H243 H 1.1688 0.8067 0.9512 0.0739 1.0000 Uiso R . . . . .
H261 H 1.3403 0.1673 0.9777 0.0847 1.0000 Uiso R . . . . .
H262 H 1.2044 0.2246 0.9874 0.0845 1.0000 Uiso R . . . . .
H263 H 1.2445 0.2152 0.9362 0.0850 1.0000 Uiso R . . . . .
H273 H 1.4368 0.3623 1.0325 0.0788 1.0000 Uiso R . . . . .
H272 H 1.4033 0.5384 1.0265 0.0803 1.0000 Uiso R . . . . .
H271 H 1.2992 0.4241 1.0439 0.0788 1.0000 Uiso R . . . . .
H281 H 1.5044 0.3553 0.9540 0.0782 1.0000 Uiso R . . . . .
H282 H 1.4644 0.5282 0.9466 0.0784 1.0000 Uiso R . . . . .
H283 H 1.4111 0.4055 0.9100 0.0777 1.0000 Uiso R . . . . .
H341 H 0.7734 0.4318 0.7388 0.0574 1.0000 Uiso R . . . . .
H342 H 0.8321 0.5889 0.7224 0.0569 1.0000 Uiso R . . . . .
H343 H 0.8920 0.4306 0.7075 0.0573 1.0000 Uiso R . . . . .
H441 H 0.9734 1.2137 0.7674 0.0392 1.0000 Uiso R . . . . .
H442 H 0.8661 1.0799 0.7633 0.0391 1.0000 Uiso R . . . . .
H461 H 0.8818 0.8892 0.6997 0.0398 1.0000 Uiso R . . . . .
H471 H 0.9568 0.8263 0.6293 0.0462 1.0000 Uiso R . . . . .
H481 H 1.1270 0.9648 0.6006 0.0477 1.0000 Uiso R . . . . .
H491 H 1.2197 1.1678 0.6447 0.0521 1.0000 Uiso R . . . . .
H501 H 1.1398 1.2298 0.7154 0.0450 1.0000 Uiso R . . . . .
H541 H 0.8360 0.4753 0.6026 0.0370 1.0000 Uiso R . . . . .
H551 H 0.8546 0.2065 0.6054 0.0395 1.0000 Uiso R . . . . .
H561 H 0.6743 0.0598 0.6164 0.0382 1.0000 Uiso R . . . . .
H571 H 0.4793 0.1741 0.6298 0.0321 1.0000 Uiso R . . . . .
H601 H 0.2988 0.4414 0.6780 0.0281 1.0000 Uiso R . . . . .
H611 H 0.2975 0.7241 0.7024 0.0337 1.0000 Uiso R . . . . .
H612 H 0.2426 0.6781 0.6517 0.0333 1.0000 Uiso R . . . . .
H621 H 0.3948 0.8481 0.6318 0.0288 1.0000 Uiso R . . . . .
H731 H 0.2370 0.7245 0.5024 0.0601 1.0000 Uiso R . . . . .
H732 H 0.3316 0.7671 0.5457 0.0607 1.0000 Uiso R . . . . .
H733 H 0.1918 0.7229 0.5520 0.0606 1.0000 Uiso R . . . . .
H741 H 0.4359 0.4651 0.4771 0.0591 1.0000 Uiso R . . . . .
H742 H 0.5222 0.5329 0.5196 0.0583 1.0000 Uiso R . . . . .
H743 H 0.4873 0.3612 0.5186 0.0583 1.0000 Uiso R . . . . .
H761 H 0.1483 0.1364 0.5142 0.0583 1.0000 Uiso R . . . . .
H762 H 0.2524 0.1760 0.5545 0.0589 1.0000 Uiso R . . . . .
H763 H 0.2853 0.1883 0.5024 0.0589 1.0000 Uiso R . . . . .
H773 H 0.0579 0.3390 0.4599 0.0592 1.0000 Uiso R . . . . .
H772 H 0.0964 0.5145 0.4671 0.0593 1.0000 Uiso R . . . . .
H771 H 0.1945 0.3924 0.4493 0.0585 1.0000 Uiso R . . . . .
H781 H -0.0104 0.3253 0.5403 0.0547 1.0000 Uiso R . . . . .
H782 H 0.0862 0.3638 0.5835 0.0558 1.0000 Uiso R . . . . .
H783 H 0.0329 0.4949 0.5500 0.0554 1.0000 Uiso R . . . . .
H841 H 0.4605 0.5889 0.8249 0.0602 1.0000 Uiso R . . . . .
H842 H 0.5824 0.5686 0.7955 0.0608 1.0000 Uiso R . . . . .
H843 H 0.5048 0.4222 0.8080 0.0611 1.0000 Uiso R . . . . .
H941 H 0.5969 1.1415 0.7257 0.0401 1.0000 Uiso R . . . . .
H942 H 0.6666 0.9835 0.7356 0.0398 1.0000 Uiso R . . . . .
H961 H 0.3697 1.1565 0.7624 0.0469 1.0000 Uiso R . . . . .
H971 H 0.2802 1.1485 0.8346 0.0551 1.0000 Uiso R . . . . .
H981 H 0.3806 1.0101 0.8951 0.0536 1.0000 Uiso R . . . . .
H991 H 0.5680 0.8733 0.8829 0.0524 1.0000 Uiso R . . . . .
H1001 H 0.6562 0.8894 0.8111 0.0450 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.39(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2199(18) yes
C2 . C3 . 1.480(2) yes
C2 . N13 . 1.3849(16) yes
C3 . C4 . 1.3903(18) yes
C3 . C8 . 1.3879(17) yes
C4 . C5 . 1.391(2) yes
C4 . H41 . 0.930 no
C5 . C6 . 1.396(2) yes
C5 . H51 . 0.939 no
C6 . C7 . 1.3949(19) yes
C6 . H61 . 0.923 no
C7 . C8 . 1.381(2) yes
C7 . H71 . 0.942 no
C8 . C9 . 1.5122(16) yes
C9 . C10 . 1.5420(15) yes
C9 . N13 . 1.4641(16) yes
C9 . O21 . 1.4178(13) yes
C10 . C11 . 1.5478(18) yes
C10 . C31 . 1.5266(16) yes
C10 . H101 . 0.965 no
C11 . C12 . 1.5477(17) yes
C11 . H111 . 0.989 no
C11 . H112 . 0.945 no
C12 . N13 . 1.4548(16) yes
C12 . C41 . 1.5296(17) yes
C12 . H121 . 0.971 no
O21 . Si22 . 1.6695(9) yes
Si22 . C23 . 1.8606(15) yes
Si22 . C24 . 1.8636(19) yes
Si22 . C25 . 1.8815(15) yes
C23 . H231 . 0.968 no
C23 . H232 . 0.957 no
C23 . H233 . 0.976 no
C24 . H241 . 0.948 no
C24 . H242 . 0.952 no
C24 . H243 . 0.975 no
C25 . C26 . 1.523(3) yes
C25 . C27 . 1.535(2) yes
C25 . C28 . 1.5311(19) yes
C26 . H261 . 0.958 no
C26 . H262 . 0.952 no
C26 . H263 . 0.978 no
C27 . H273 . 0.986 no
C27 . H272 . 0.979 no
C27 . H271 . 0.965 no
C28 . H281 . 0.982 no
C28 . H282 . 0.961 no
C28 . H283 . 0.974 no
C31 . O32 . 1.1975(18) yes
C31 . O33 . 1.3195(16) yes
O33 . C34 . 1.4573(15) yes
C34 . H341 . 0.974 no
C34 . H342 . 0.963 no
C34 . H343 . 0.977 no
C41 . O42 . 1.2016(17) yes
C41 . O43 . 1.3358(17) yes
O43 . C44 . 1.4664(16) yes
C44 . C45 . 1.5019(18) yes
C44 . H441 . 0.977 no
C44 . H442 . 0.993 no
C45 . C46 . 1.392(2) yes
C45 . C50 . 1.393(2) yes
C46 . C47 . 1.388(2) yes
C46 . H461 . 0.943 no
C47 . C48 . 1.387(2) yes
C47 . H471 . 0.948 no
C48 . C49 . 1.385(3) yes
C48 . H481 . 0.945 no
C49 . C50 . 1.393(2) yes
C49 . H491 . 0.946 no
C50 . H501 . 0.931 no
O51 . C52 . 1.2198(18) yes
C52 . C53 . 1.4805(19) yes
C52 . N63 . 1.3866(16) yes
C53 . C54 . 1.3902(17) yes
C53 . C58 . 1.3909(17) yes
C54 . C55 . 1.386(2) yes
C54 . H541 . 0.937 no
C55 . C56 . 1.399(2) yes
C55 . H551 . 0.949 no
C56 . C57 . 1.3943(19) yes
C56 . H561 . 0.922 no
C57 . C58 . 1.385(2) yes
C57 . H571 . 0.920 no
C58 . C59 . 1.5153(16) yes
C59 . C60 . 1.5494(15) yes
C59 . N63 . 1.4664(16) yes
C59 . O71 . 1.4178(13) yes
C60 . C61 . 1.5410(19) yes
C60 . C81 . 1.5224(16) yes
C60 . H601 . 0.937 no
C61 . C62 . 1.5453(18) yes
C61 . H611 . 0.968 no
C61 . H612 . 0.961 no
C62 . N63 . 1.4606(16) yes
C62 . C91 . 1.5226(17) yes
C62 . H621 . 0.969 no
O71 . Si72 . 1.6677(9) yes
Si72 . C73 . 1.8622(17) yes
Si72 . C74 . 1.8593(14) yes
Si72 . C75 . 1.8828(14) yes
C73 . H731 . 0.959 no
C73 . H732 . 0.953 no
C73 . H733 . 0.932 no
C74 . H741 . 0.973 no
C74 . H742 . 0.960 no
C74 . H743 . 0.967 no
C75 . C76 . 1.526(2) yes
C75 . C77 . 1.5367(17) yes
C75 . C78 . 1.5371(17) yes
C76 . H761 . 0.968 no
C76 . H762 . 0.969 no
C76 . H763 . 0.965 no
C77 . H773 . 0.979 no
C77 . H772 . 0.990 no
C77 . H771 . 0.970 no
C78 . H781 . 0.975 no
C78 . H782 . 0.975 no
C78 . H783 . 0.958 no
C81 . O82 . 1.1996(17) yes
C81 . O83 . 1.3392(16) yes
O83 . C84 . 1.4482(15) yes
C84 . H841 . 0.981 no
C84 . H842 . 0.972 no
C84 . H843 . 0.963 no
C91 . O92 . 1.2049(18) yes
C91 . O93 . 1.3290(17) yes
O93 . C94 . 1.4582(16) yes
C94 . C95 . 1.4996(19) yes
C94 . H941 . 0.961 no
C94 . H942 . 0.987 no
C95 . C96 . 1.394(2) yes
C95 . C100 . 1.386(2) yes
C96 . C97 . 1.395(2) yes
C96 . H961 . 0.919 no
C97 . C98 . 1.383(3) yes
C97 . H971 . 0.943 no
C98 . C99 . 1.382(3) yes
C98 . H981 . 0.949 no
C99 . C100 . 1.391(2) yes
C99 . H991 . 0.942 no
C100 . H1001 . 0.925 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . C3 . 129.14(12) yes
O1 . C2 . N13 . 125.16(14) yes
C3 . C2 . N13 . 105.70(11) yes
C2 . C3 . C4 . 129.49(13) yes
C2 . C3 . C8 . 109.42(11) yes
C4 . C3 . C8 . 121.08(14) yes
C3 . C4 . C5 . 117.64(14) yes
C3 . C4 . H41 . 120.2 no
C5 . C4 . H41 . 122.2 no
C4 . C5 . C6 . 121.28(14) yes
C4 . C5 . H51 . 118.8 no
C6 . C5 . H51 . 119.9 no
C5 . C6 . C7 . 120.43(15) yes
C5 . C6 . H61 . 119.8 no
C7 . C6 . H61 . 119.7 no
C6 . C7 . C8 . 118.10(14) yes
C6 . C7 . H71 . 120.2 no
C8 . C7 . H71 . 121.7 no
C3 . C8 . C7 . 121.35(12) yes
C3 . C8 . C9 . 109.27(12) yes
C7 . C8 . C9 . 129.09(12) yes
C8 . C9 . C10 . 124.41(10) yes
C8 . C9 . N13 . 102.27(9) yes
C10 . C9 . N13 . 103.00(10) yes
C8 . C9 . O21 . 109.77(10) yes
C10 . C9 . O21 . 104.78(9) yes
N13 . C9 . O21 . 112.45(10) yes
C9 . C10 . C11 . 100.44(10) yes
C9 . C10 . C31 . 119.77(10) yes
C11 . C10 . C31 . 109.74(11) yes
C9 . C10 . H101 . 109.5 no
C11 . C10 . H101 . 111.2 no
C31 . C10 . H101 . 106.1 no
C10 . C11 . C12 . 104.11(10) yes
C10 . C11 . H111 . 110.7 no
C12 . C11 . H111 . 107.3 no
C10 . C11 . H112 . 112.7 no
C12 . C11 . H112 . 111.0 no
H111 . C11 . H112 . 110.6 no
C11 . C12 . N13 . 102.75(11) yes
C11 . C12 . C41 . 109.60(10) yes
N13 . C12 . C41 . 111.64(10) yes
C11 . C12 . H121 . 112.4 no
N13 . C12 . H121 . 110.5 no
C41 . C12 . H121 . 109.8 no
C9 . N13 . C12 . 112.94(10) yes
C9 . N13 . C2 . 113.27(11) yes
C12 . N13 . C2 . 125.49(11) yes
C9 . O21 . Si22 . 129.54(8) yes
O21 . Si22 . C23 . 113.00(6) yes
O21 . Si22 . C24 . 110.06(7) yes
C23 . Si22 . C24 . 109.75(10) yes
O21 . Si22 . C25 . 101.63(6) yes
C23 . Si22 . C25 . 110.79(8) yes
C24 . Si22 . C25 . 111.41(8) yes
Si22 . C23 . H231 . 109.9 no
Si22 . C23 . H232 . 110.3 no
H231 . C23 . H232 . 109.3 no
Si22 . C23 . H233 . 110.7 no
H231 . C23 . H233 . 107.4 no
H232 . C23 . H233 . 109.2 no
Si22 . C24 . H241 . 110.6 no
Si22 . C24 . H242 . 109.7 no
H241 . C24 . H242 . 110.4 no
Si22 . C24 . H243 . 108.1 no
H241 . C24 . H243 . 108.9 no
H242 . C24 . H243 . 109.1 no
Si22 . C25 . C26 . 110.20(11) yes
Si22 . C25 . C27 . 110.03(12) yes
C26 . C25 . C27 . 109.21(16) yes
Si22 . C25 . C28 . 109.62(11) yes
C26 . C25 . C28 . 109.54(17) yes
C27 . C25 . C28 . 108.21(13) yes
C25 . C26 . H261 . 111.7 no
C25 . C26 . H262 . 109.7 no
H261 . C26 . H262 . 108.8 no
C25 . C26 . H263 . 110.8 no
H261 . C26 . H263 . 107.4 no
H262 . C26 . H263 . 108.3 no
C25 . C27 . H273 . 107.8 no
C25 . C27 . H272 . 110.2 no
H273 . C27 . H272 . 107.8 no
C25 . C27 . H271 . 111.6 no
H273 . C27 . H271 . 109.7 no
H272 . C27 . H271 . 109.6 no
C25 . C28 . H281 . 108.8 no
C25 . C28 . H282 . 107.9 no
H281 . C28 . H282 . 108.9 no
C25 . C28 . H283 . 111.6 no
H281 . C28 . H283 . 110.2 no
H282 . C28 . H283 . 109.4 no
C10 . C31 . O32 . 121.78(12) yes
C10 . C31 . O33 . 114.35(11) yes
O32 . C31 . O33 . 123.86(12) yes
C31 . O33 . C34 . 115.54(11) yes
O33 . C34 . H341 . 107.0 no
O33 . C34 . H342 . 108.9 no
H341 . C34 . H342 . 110.7 no
O33 . C34 . H343 . 110.6 no
H341 . C34 . H343 . 109.0 no
H342 . C34 . H343 . 110.5 no
C12 . C41 . O42 . 125.25(13) yes
C12 . C41 . O43 . 109.39(11) yes
O42 . C41 . O43 . 125.29(13) yes
C41 . O43 . C44 . 115.97(11) yes
O43 . C44 . C45 . 110.75(11) yes
O43 . C44 . H441 . 105.8 no
C45 . C44 . H441 . 109.1 no
O43 . C44 . H442 . 107.9 no
C45 . C44 . H442 . 112.3 no
H441 . C44 . H442 . 110.8 no
C44 . C45 . C46 . 120.78(14) yes
C44 . C45 . C50 . 119.63(14) yes
C46 . C45 . C50 . 119.58(14) yes
C45 . C46 . C47 . 119.88(15) yes
C45 . C46 . H461 . 120.2 no
C47 . C46 . H461 . 119.9 no
C46 . C47 . C48 . 120.37(15) yes
C46 . C47 . H471 . 117.5 no
C48 . C47 . H471 . 122.1 no
C47 . C48 . C49 . 120.11(15) yes
C47 . C48 . H481 . 119.5 no
C49 . C48 . H481 . 120.3 no
C48 . C49 . C50 . 119.73(16) yes
C48 . C49 . H491 . 121.2 no
C50 . C49 . H491 . 119.0 no
C49 . C50 . C45 . 120.31(15) yes
C49 . C50 . H501 . 120.5 no
C45 . C50 . H501 . 119.2 no
O51 . C52 . C53 . 129.25(12) yes
O51 . C52 . N63 . 124.69(13) yes
C53 . C52 . N63 . 106.05(11) yes
C52 . C53 . C54 . 129.26(12) yes
C52 . C53 . C58 . 109.09(11) yes
C54 . C53 . C58 . 121.64(13) yes
C53 . C54 . C55 . 117.60(13) yes
C53 . C54 . H541 . 119.3 no
C55 . C54 . H541 . 123.1 no
C54 . C55 . C56 . 120.99(13) yes
C54 . C55 . H551 . 119.4 no
C56 . C55 . H551 . 119.6 no
C55 . C56 . C57 . 120.99(14) yes
C55 . C56 . H561 . 119.7 no
C57 . C56 . H561 . 119.3 no
C56 . C57 . C58 . 117.86(13) yes
C56 . C57 . H571 . 121.9 no
C58 . C57 . H571 . 120.2 no
C53 . C58 . C57 . 120.82(12) yes
C53 . C58 . C59 . 109.42(11) yes
C57 . C58 . C59 . 129.59(12) yes
C58 . C59 . C60 . 123.54(10) yes
C58 . C59 . N63 . 102.21(9) yes
C60 . C59 . N63 . 102.74(10) yes
C58 . C59 . O71 . 110.21(10) yes
C60 . C59 . O71 . 105.10(9) yes
N63 . C59 . O71 . 112.92(10) yes
C59 . C60 . C61 . 101.05(10) yes
C59 . C60 . C81 . 114.51(10) yes
C61 . C60 . C81 . 114.84(11) yes
C59 . C60 . H601 . 108.0 no
C61 . C60 . H601 . 111.4 no
C81 . C60 . H601 . 106.9 no
C60 . C61 . C62 . 103.99(10) yes
C60 . C61 . H611 . 115.0 no
C62 . C61 . H611 . 110.7 no
C60 . C61 . H612 . 108.6 no
C62 . C61 . H612 . 107.8 no
H611 . C61 . H612 . 110.3 no
C61 . C62 . N63 . 102.88(11) yes
C61 . C62 . C91 . 109.09(10) yes
N63 . C62 . C91 . 110.50(10) yes
C61 . C62 . H621 . 113.3 no
N63 . C62 . H621 . 111.9 no
C91 . C62 . H621 . 109.1 no
C59 . N63 . C62 . 112.94(10) yes
C59 . N63 . C52 . 113.01(11) yes
C62 . N63 . C52 . 122.77(11) yes
C59 . O71 . Si72 . 129.64(8) yes
O71 . Si72 . C73 . 110.16(6) yes
O71 . Si72 . C74 . 112.32(6) yes
C73 . Si72 . C74 . 109.96(8) yes
O71 . Si72 . C75 . 101.76(5) yes
C73 . Si72 . C75 . 111.26(7) yes
C74 . Si72 . C75 . 111.17(7) yes
Si72 . C73 . H731 . 109.5 no
Si72 . C73 . H732 . 109.0 no
H731 . C73 . H732 . 111.4 no
Si72 . C73 . H733 . 108.7 no
H731 . C73 . H733 . 108.8 no
H732 . C73 . H733 . 109.4 no
Si72 . C74 . H741 . 111.0 no
Si72 . C74 . H742 . 111.6 no
H741 . C74 . H742 . 109.8 no
Si72 . C74 . H743 . 109.8 no
H741 . C74 . H743 . 107.6 no
H742 . C74 . H743 . 106.9 no
Si72 . C75 . C76 . 110.01(9) yes
Si72 . C75 . C77 . 110.16(10) yes
C76 . C75 . C77 . 109.25(13) yes
Si72 . C75 . C78 . 109.59(10) yes
C76 . C75 . C78 . 109.58(13) yes
C77 . C75 . C78 . 108.23(11) yes
C75 . C76 . H761 . 109.9 no
C75 . C76 . H762 . 111.9 no
H761 . C76 . H762 . 108.6 no
C75 . C76 . H763 . 109.7 no
H761 . C76 . H763 . 108.2 no
H762 . C76 . H763 . 108.3 no
C75 . C77 . H773 . 109.3 no
C75 . C77 . H772 . 112.1 no
H773 . C77 . H772 . 108.5 no
C75 . C77 . H771 . 111.8 no
H773 . C77 . H771 . 106.0 no
H772 . C77 . H771 . 108.8 no
C75 . C78 . H781 . 110.2 no
C75 . C78 . H782 . 110.3 no
H781 . C78 . H782 . 108.5 no
C75 . C78 . H783 . 109.8 no
H781 . C78 . H783 . 108.8 no
H782 . C78 . H783 . 109.2 no
C60 . C81 . O82 . 125.22(12) yes
C60 . C81 . O83 . 111.65(11) yes
O82 . C81 . O83 . 123.01(12) yes
C81 . O83 . C84 . 114.25(11) yes
O83 . C84 . H841 . 106.6 no
O83 . C84 . H842 . 109.4 no
H841 . C84 . H842 . 109.4 no
O83 . C84 . H843 . 109.8 no
H841 . C84 . H843 . 112.7 no
H842 . C84 . H843 . 108.9 no
C62 . C91 . O92 . 124.35(13) yes
C62 . C91 . O93 . 110.87(11) yes
O92 . C91 . O93 . 124.70(13) yes
C91 . O93 . C94 . 115.57(11) yes
O93 . C94 . C95 . 111.01(11) yes
O93 . C94 . H941 . 105.5 no
C95 . C94 . H941 . 112.2 no
O93 . C94 . H942 . 107.1 no
C95 . C94 . H942 . 112.0 no
H941 . C94 . H942 . 108.6 no
C94 . C95 . C96 . 120.82(14) yes
C94 . C95 . C100 . 119.88(14) yes
C96 . C95 . C100 . 119.29(14) yes
C95 . C96 . C97 . 119.96(16) yes
C95 . C96 . H961 . 118.7 no
C97 . C96 . H961 . 121.4 no
C96 . C97 . C98 . 120.27(16) yes
C96 . C97 . H971 . 120.0 no
C98 . C97 . H971 . 119.7 no
C97 . C98 . C99 . 119.80(15) yes
C97 . C98 . H981 . 119.2 no
C99 . C98 . H981 . 121.0 no
C98 . C99 . C100 . 120.22(16) yes
C98 . C99 . H991 . 120.4 no
C100 . C99 . H991 . 119.4 no
C99 . C100 . C95 . 120.43(15) yes
C99 . C100 . H1001 . 121.2 no
C95 . C100 . H1001 . 118.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . O43 1_545 127 0.94 2.56 3.217(2) yes
C34 . H341 . O82 . 148 0.97 2.41 3.282(2) yes
C44 . H441 . O33 1_565 161 0.98 2.45 3.390(2) yes
C94 . H941 . O82 1_565 154 0.96 2.30 3.185(2) yes


####################################################################### 
# 
# 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_11-189
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq6s
_database_code_depnum_ccdc_archive 'CCDC 2160055'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2021-02-18
_audit_creation_method           'CRYSTALS_ver_14.61_build_7932 '

_oxford_structure_analysis_title 7388
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   12.9946(5)
_cell_length_b                   9.2309(3)
_cell_length_c                   15.3935(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.249(4)
_cell_angle_gamma                90
_cell_volume                     1845.06(12)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C10.50 H7 N1.75 O0.88 
# Dc =      1.24 Fooo =    714.00 Mu =      6.58 M =    171.68
# Found Formula = C12 H8 N2 O1 
# Dc =      1.41 FOOO =    816.00 Mu =      7.52 M =    196.21

_chemical_formula_sum            'C12 H8 N2 O'
_chemical_formula_moiety         'C12 H8 N2 O'
_chemical_compound_source        .
_chemical_formula_weight         196.21


_cell_measurement_reflns_used    4014
_cell_measurement_theta_min      5.74
_cell_measurement_theta_max      75.95
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.21

_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.752

# Sheldrick geometric approximatio 0.89 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            6560
_diffrn_reflns_av_unetI/netI     0.035
_reflns_number_total             1914
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0348
# Number of reflections with Friedels Law is 1914 
# Theoretical number of reflections is about 3852 

_diffrn_reflns_theta_min         5.881
_diffrn_reflns_theta_max         75.999
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        74.479
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.68
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.66


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1914
_refine_ls_R_factor_ref          0.0658
_refine_ls_wR_factor_ref         0.1776
_refine_ls_goodness_of_fit_ref   1.0062
_refine_ls_shift/su_max          0.0002977
_refine_ls_shift/su_mean         0.0000344


# Computed with I/sigma = -10 
_reflns_number_all               1914
_refine_ls_R_factor_all          0.0658
_refine_ls_wR_factor_all         0.1776

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1726
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_gt          0.1721


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.10P)² + 2.93P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.82102(12) 1.03044(18) 0.58648(11) 0.0422 1.0000 Uani . . . . . .
C2 C 0.74538(15) 0.9637(2) 0.55994(13) 0.0332 1.0000 Uani . . . . . .
N3 N 0.69074(13) 0.9877(2) 0.48211(12) 0.0360 1.0000 Uani . . . . . .
C4 C 0.69276(17) 1.0976(2) 0.41423(15) 0.0389 1.0000 Uani . . . . . .
C5 C 0.60951(17) 1.0420(2) 0.34725(15) 0.0374 1.0000 Uani . . . . . .
C6 C 0.55867(15) 0.9186(2) 0.39311(13) 0.0324 1.0000 Uani . . . . . .
C7 C 0.60994(14) 0.8914(2) 0.46871(13) 0.0303 1.0000 Uani . . . . . .
C8 C 0.60975(14) 0.7938(2) 0.54346(13) 0.0312 1.0000 Uani . . . . . .
C9 C 0.54761(16) 0.6785(2) 0.56506(14) 0.0347 1.0000 Uani . . . . . .
C10 C 0.56929(17) 0.6086(2) 0.64416(15) 0.0391 1.0000 Uani . . . . . .
C11 C 0.65118(19) 0.6522(3) 0.69889(14) 0.0421 1.0000 Uani . . . . . .
C12 C 0.71505(16) 0.7663(3) 0.67673(13) 0.0380 1.0000 Uani . . . . . .
C13 C 0.69290(14) 0.8370(2) 0.59935(13) 0.0311 1.0000 Uani . . . . . .
C14 C 0.47147(15) 0.8400(2) 0.36153(13) 0.0358 1.0000 Uani . . . . . .
N15 N 0.40074(17) 0.7796(3) 0.33391(14) 0.0541 1.0000 Uani . . . . . .
H42 H 0.6716 1.1906 0.4392 0.0466 1.0000 Uiso R . . . . .
H41 H 0.7619 1.1055 0.3916 0.0467 1.0000 Uiso R . . . . .
H52 H 0.5614 1.1173 0.3304 0.0452 1.0000 Uiso R . . . . .
H51 H 0.6422 1.0044 0.2940 0.0447 1.0000 Uiso R . . . . .
H91 H 0.4928 0.6502 0.5283 0.0418 1.0000 Uiso R . . . . .
H101 H 0.5291 0.5301 0.6602 0.0472 1.0000 Uiso R . . . . .
H111 H 0.6644 0.6015 0.7505 0.0509 1.0000 Uiso R . . . . .
H121 H 0.7695 0.7924 0.7129 0.0457 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.96(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.217(2) yes
C2 . N3 . 1.386(3) yes
C2 . C13 . 1.495(3) yes
N3 . C4 . 1.457(3) yes
N3 . C7 . 1.385(2) yes
C4 . C5 . 1.552(3) yes
C4 . H42 . 0.983 no
C4 . H41 . 0.980 no
C5 . C6 . 1.506(3) yes
C5 . H52 . 0.964 no
C5 . H51 . 1.000 no
C6 . C7 . 1.342(3) yes
C6 . C14 . 1.415(3) yes
C7 . C8 . 1.461(3) yes
C8 . C9 . 1.384(3) yes
C8 . C13 . 1.412(3) yes
C9 . C10 . 1.397(3) yes
C9 . H91 . 0.930 no
C10 . C11 . 1.391(3) yes
C10 . H101 . 0.932 no
C11 . C12 . 1.391(3) yes
C11 . H111 . 0.933 no
C12 . C13 . 1.379(3) yes
C12 . H121 . 0.915 no
C14 . N15 . 1.143(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 126.0(2) yes
O1 . C2 . C13 . 129.4(2) yes
N3 . C2 . C13 . 104.46(16) yes
C2 . N3 . C4 . 135.07(17) yes
C2 . N3 . C7 . 112.67(17) yes
C4 . N3 . C7 . 112.03(17) yes
N3 . C4 . C5 . 102.36(16) yes
N3 . C4 . H42 . 108.3 no
C5 . C4 . H42 . 110.5 no
N3 . C4 . H41 . 110.4 no
C5 . C4 . H41 . 114.4 no
H42 . C4 . H41 . 110.4 no
C4 . C5 . C6 . 104.24(17) yes
C4 . C5 . H52 . 111.5 no
C6 . C5 . H52 . 112.3 no
C4 . C5 . H51 . 110.6 no
C6 . C5 . H51 . 109.3 no
H52 . C5 . H51 . 108.8 no
C5 . C6 . C7 . 109.62(17) yes
C5 . C6 . C14 . 125.90(18) yes
C7 . C6 . C14 . 124.46(19) yes
N3 . C7 . C6 . 110.91(18) yes
N3 . C7 . C8 . 107.64(17) yes
C6 . C7 . C8 . 141.45(18) yes
C7 . C8 . C9 . 132.99(18) yes
C7 . C8 . C13 . 106.33(17) yes
C9 . C8 . C13 . 120.68(19) yes
C8 . C9 . C10 . 117.70(19) yes
C8 . C9 . H91 . 120.7 no
C10 . C9 . H91 . 121.6 no
C9 . C10 . C11 . 121.2(2) yes
C9 . C10 . H101 . 119.6 no
C11 . C10 . H101 . 119.2 no
C10 . C11 . C12 . 121.3(2) yes
C10 . C11 . H111 . 118.8 no
C12 . C11 . H111 . 119.8 no
C11 . C12 . C13 . 117.63(19) yes
C11 . C12 . H121 . 120.3 no
C13 . C12 . H121 . 122.1 no
C2 . C13 . C8 . 108.89(17) yes
C2 . C13 . C12 . 129.65(18) yes
C8 . C13 . C12 . 121.46(19) yes
C6 . C14 . N15 . 177.9(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 . H41 . N15 3_555 146 0.98 2.60 3.452(3) yes
C11 . H111 . O1 8_646 163 0.93 2.59 3.495(3) yes
C12 . H121 . N15 7_565 148 0.92 2.56 3.376(3) yes


####################################################################### 
# 
# 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_12-196b
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq7t
_database_code_depnum_ccdc_archive 'CCDC 2160056'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_date             2018-12-14
_audit_creation_method           'CRYSTALS_ver_14.61_build_7264 '

_oxford_structure_analysis_title 7089
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   11.4163(2)
_cell_length_b                   12.6752(2)
_cell_length_c                   8.4365(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1220.79(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21 '
_symmetry_space_group_name_Hall  'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z+1/2
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C13 H14 N2 O3 
# Dc =      1.34 Fooo =    520.00 Mu =      7.98 M =    246.27
# Found Formula = C13 H14 N2 O3 
# Dc =      1.34 FOOO =    520.00 Mu =      7.98 M =    246.27

_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_compound_source        .
_chemical_formula_weight         246.27


_cell_measurement_reflns_used    6344
_cell_measurement_theta_min      5
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_intense_yellow
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.798

# Sheldrick geometric approximatio 0.87 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            9744
_diffrn_reflns_av_unetI/netI     0.029
_reflns_number_total             2475
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.0289
# Number of reflections without Friedels Law is 2475 
# Number of reflections with Friedels Law is 1368 
# Theoretical number of reflections is about 1283 

_diffrn_reflns_theta_min         5.214
_diffrn_reflns_theta_max         76.529
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        76.529
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              0
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              -10
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   3.11
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.12


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2475
_oxford_refine_ls_R_factor_ref   0.0302
_refine_ls_wR_factor_ref         0.0774
_refine_ls_goodness_of_fit_ref   1.0046
_refine_ls_shift/su_max          0.0004089
_refine_ls_shift/su_mean         0.0000358


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2475
_refine_ls_R_factor_all          0.0302
_refine_ls_wR_factor_all         0.0774

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2417
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_gt          0.0760

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.05(7) # for 1081 Friedel pairs 
_oxford_Bijvoet_difference       -0.00(7) # for 1081 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.02(19) # for 1107 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.00(7)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1081 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.20P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.34117(9) 0.96677(8) 0.51235(18) 0.0471 1.0000 Uani . . . . . .
C2 C 0.29156(11) 0.89275(10) 0.44384(19) 0.0320 1.0000 Uani . . . . . .
N3 N 0.19478(9) 0.84225(9) 0.49879(17) 0.0344 1.0000 Uani . . . . . .
C4 C 0.16693(14) 0.82676(14) 0.6672(2) 0.0462 1.0000 Uani . . . . . .
C5 C 0.12485(13) 0.71224(15) 0.6763(2) 0.0475 1.0000 Uani . . . . . .
C6 C 0.17134(11) 0.65751(11) 0.5264(2) 0.0379 1.0000 Uani . . . . . .
C7 C 0.16750(11) 0.74835(10) 0.40393(18) 0.0317 1.0000 Uani . . . . . .
C8 C 0.25469(11) 0.75398(10) 0.27058(18) 0.0298 1.0000 Uani . . . . . .
C9 C 0.26998(14) 0.69118(12) 0.1389(2) 0.0409 1.0000 Uani . . . . . .
C10 C 0.35869(14) 0.72155(14) 0.0328(2) 0.0470 1.0000 Uani . . . . . .
C11 C 0.42922(13) 0.80845(13) 0.0578(2) 0.0443 1.0000 Uani . . . . . .
C12 C 0.41519(11) 0.87188(11) 0.1921(2) 0.0346 1.0000 Uani . . . . . .
C13 C 0.32495(11) 0.84239(10) 0.29476(18) 0.0287 1.0000 Uani . . . . . .
N14 N 0.48358(12) 0.95701(10) 0.22560(19) 0.0462 1.0000 Uani . . . . . .
C15 C 0.29372(12) 0.61709(11) 0.55330(19) 0.0361 1.0000 Uani . . . . . .
O16 O 0.37323(10) 0.66844(9) 0.60632(18) 0.0521 1.0000 Uani . . . . . .
O17 O 0.30216(10) 0.51549(9) 0.51654(18) 0.0502 1.0000 Uani . . . . . .
C18 C 0.41365(18) 0.46667(14) 0.5501(3) 0.0629 1.0000 Uani . . . . . .
H41 H 0.1076 0.8761 0.6996 0.0561 1.0000 Uiso R . . . . .
H42 H 0.2391 0.8391 0.7248 0.0549 1.0000 Uiso R . . . . .
H51 H 0.1515 0.6783 0.7724 0.0574 1.0000 Uiso R . . . . .
H52 H 0.0397 0.7098 0.6718 0.0553 1.0000 Uiso R . . . . .
H61 H 0.1209 0.5992 0.4927 0.0464 1.0000 Uiso R . . . . .
H71 H 0.0858 0.7556 0.3643 0.0376 1.0000 Uiso R . . . . .
H91 H 0.2226 0.6318 0.1224 0.0492 1.0000 Uiso R . . . . .
H101 H 0.3694 0.6822 -0.0608 0.0555 1.0000 Uiso R . . . . .
H111 H 0.4881 0.8245 -0.0152 0.0531 1.0000 Uiso R . . . . .
H181 H 0.4063 0.3927 0.5225 0.0935 1.0000 Uiso R . . . . .
H183 H 0.4329 0.4744 0.6618 0.0911 1.0000 Uiso R . . . . .
H182 H 0.4741 0.5004 0.4903 0.0917 1.0000 Uiso R . . . . .
H141 H 0.4621 0.9953 0.3135 0.0563 1.0000 Uiso R . . . . .
H142 H 0.5372 0.9753 0.1581 0.0570 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2389(17) yes
C2 . N3 . 1.3584(17) yes
C2 . C13 . 1.4610(19) yes
N3 . C4 . 1.469(2) yes
N3 . C7 . 1.4677(17) yes
C4 . C5 . 1.531(3) yes
C4 . H41 . 0.961 no
C4 . H42 . 0.969 no
C5 . C6 . 1.537(2) yes
C5 . H51 . 0.967 no
C5 . H52 . 0.973 no
C6 . C7 . 1.5475(19) yes
C6 . C15 . 1.5054(19) yes
C6 . H61 . 0.978 no
C7 . C8 . 1.5038(18) yes
C7 . H71 . 0.995 no
C8 . C9 . 1.378(2) yes
C8 . C13 . 1.3931(17) yes
C9 . C10 . 1.406(2) yes
C9 . H91 . 0.936 no
C10 . C11 . 1.381(2) yes
C10 . H101 . 0.941 no
C11 . C12 . 1.398(2) yes
C11 . H111 . 0.934 no
C12 . C13 . 1.3969(19) yes
C12 . N14 . 1.3617(19) yes
N14 . H141 . 0.919 no
N14 . H142 . 0.868 no
C15 . O16 . 1.2032(18) yes
C15 . O17 . 1.3281(18) yes
O17 . C18 . 1.443(2) yes
C18 . H181 . 0.970 no
C18 . H183 . 0.972 no
C18 . H182 . 0.956 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 124.71(14) yes
O1 . C2 . C13 . 127.82(13) yes
N3 . C2 . C13 . 107.47(11) yes
C2 . N3 . C4 . 124.68(12) yes
C2 . N3 . C7 . 111.63(11) yes
C4 . N3 . C7 . 111.90(12) yes
N3 . C4 . C5 . 104.07(13) yes
N3 . C4 . H41 . 109.9 no
C5 . C4 . H41 . 112.4 no
N3 . C4 . H42 . 106.2 no
C5 . C4 . H42 . 113.3 no
H41 . C4 . H42 . 110.6 no
C4 . C5 . C6 . 106.17(12) yes
C4 . C5 . H51 . 111.4 no
C6 . C5 . H51 . 112.4 no
C4 . C5 . H52 . 110.0 no
C6 . C5 . H52 . 107.4 no
H51 . C5 . H52 . 109.4 no
C5 . C6 . C7 . 101.75(12) yes
C5 . C6 . C15 . 110.48(13) yes
C7 . C6 . C15 . 112.35(11) yes
C5 . C6 . H61 . 112.1 no
C7 . C6 . H61 . 110.6 no
C15 . C6 . H61 . 109.4 no
C6 . C7 . N3 . 103.50(11) yes
C6 . C7 . C8 . 121.06(12) yes
N3 . C7 . C8 . 103.24(10) yes
C6 . C7 . H71 . 108.7 no
N3 . C7 . H71 . 107.9 no
C8 . C7 . H71 . 111.4 no
C7 . C8 . C9 . 131.27(12) yes
C7 . C8 . C13 . 108.04(11) yes
C9 . C8 . C13 . 120.66(13) yes
C8 . C9 . C10 . 116.54(14) yes
C8 . C9 . H91 . 120.7 no
C10 . C9 . H91 . 122.7 no
C9 . C10 . C11 . 122.75(15) yes
C9 . C10 . H101 . 118.9 no
C11 . C10 . H101 . 118.4 no
C10 . C11 . C12 . 121.07(14) yes
C10 . C11 . H111 . 119.5 no
C12 . C11 . H111 . 119.5 no
C11 . C12 . C13 . 115.66(13) yes
C11 . C12 . N14 . 123.93(14) yes
C13 . C12 . N14 . 120.41(14) yes
C2 . C13 . C12 . 127.54(12) yes
C2 . C13 . C8 . 109.10(12) yes
C12 . C13 . C8 . 123.30(13) yes
C12 . N14 . H141 . 115.6 no
C12 . N14 . H142 . 118.7 no
H141 . N14 . H142 . 125.2 no
C6 . C15 . O16 . 124.90(14) yes
C6 . C15 . O17 . 111.23(12) yes
O16 . C15 . O17 . 123.82(14) yes
C15 . O17 . C18 . 115.71(13) yes
O17 . C18 . H181 . 106.9 no
O17 . C18 . H183 . 110.3 no
H181 . C18 . H183 . 110.5 no
O17 . C18 . H182 . 109.9 no
H181 . C18 . H182 . 111.6 no
H183 . C18 . H182 . 107.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H52 . O16 4_465 138 0.97 2.51 3.300(2) yes
C9 . H91 . O1 3_544 159 0.94 2.40 3.293(2) yes
N14 . H141 . O1 . 134 0.92 2.20 2.917(2) yes
N14 . H142 . O1 2_674 174 0.87 1.99 2.859(2) yes




# start Validation Reply Form
_vrf_PLAT922_6-171               
;
PROBLEM: wR2 in the CIF and FCF Differ by ............... 0.0589 Check
RESPONSE: The data are collected at Diamond Light Source, Beamline I19-1.
Data has been truncated as the very high angle are too weak to be
meaningful.
;
_vrf_PLAT992_6-171               
;
PROBLEM: Repd & Actual _reflns_number_gt Values Differ by 3900 Check
RESPONSE: Data has been truncated and hence the difference.
;
_vrf_PLAT921_DIA0413             
;
PROBLEM: R1  in the CIF and FCF Differ by ...............     0.0347 Check 
RESPONSE: It is the correct FCF-file for the CIF. 
;
