# 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_16c
_database_code_depnum_ccdc_archive 'CCDC 2256187'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 
_ccdc_journal_depnumber          xxx

_audit_creation_date             2019-06-12
_audit_creation_method           'CRYSTALS_ver_14.61_build_7212 '

_oxford_structure_analysis_title 7174
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   12.7980(2)
_cell_length_b                   18.4962(3)
_cell_length_c                   8.68800(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.8380(14)
_cell_angle_gamma                90
_cell_volume                     2055.52(5)

_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 = C22 H22 F1 N1 O6 
# Dc =      1.34 Fooo =    872.00 Mu =      8.73 M =    415.42
# Found Formula = C22 H22 F1 N1 O6 
# Dc =      1.34 FOOO =    872.00 Mu =      8.73 M =    415.42

_chemical_formula_sum            'C22 H22 F N O6'
_chemical_formula_moiety         'C22 H22 F N O6'
_chemical_compound_source        .
_chemical_formula_weight         415.42


_cell_measurement_reflns_used    7384
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      75.44
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_yellow
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.39

_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.873

# Sheldrick geometric approximatio 0.84 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.92
_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            15001
_diffrn_reflns_av_unetI/netI     0.045
_reflns_number_total             4254
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0453
# Number of reflections with Friedels Law is 4254 
# Theoretical number of reflections is about 8595 

_diffrn_reflns_theta_min         4.202
_diffrn_reflns_theta_max         76.107
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        74.585
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -15
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   2.95
_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         -0.23
_refine_diff_density_max         0.29


# 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     271
_refine_ls_number_reflns         4254
_oxford_refine_ls_R_factor_ref   0.0436
_refine_ls_wR_factor_ref         0.1043
_refine_ls_goodness_of_fit_ref   0.9978
_refine_ls_shift/su_max          0.0003560
_refine_ls_shift/su_mean         0.0000606


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        4254
_refine_ls_R_factor_all          0.0436
_refine_ls_wR_factor_all         0.1043

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3759
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.0977


_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 + 0.55P] 
 ,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
N1 N 0.36296(8) 0.38795(6) 0.84300(12) 0.0299 1.0000 Uani . . . . . .
C2 C 0.27709(9) 0.40545(7) 0.94337(14) 0.0293 1.0000 Uani . . . . . .
C3 C 0.25103(10) 0.32966(7) 1.00514(15) 0.0305 1.0000 Uani . . . . . .
O4 O 0.35277(7) 0.29728(5) 1.01897(11) 0.0313 1.0000 Uani . . . . . .
C5 C 0.40712(9) 0.31590(7) 0.88464(14) 0.0291 1.0000 Uani . . . . . .
C6 C 0.52225(9) 0.31562(7) 0.92586(14) 0.0290 1.0000 Uani . . . . . .
C7 C 0.56555(10) 0.36747(7) 1.02520(15) 0.0326 1.0000 Uani . . . . . .
C8 C 0.67083(11) 0.36453(8) 1.06783(17) 0.0395 1.0000 Uani . . . . . .
C9 C 0.72949(11) 0.30908(9) 1.00886(19) 0.0451 1.0000 Uani . . . . . .
C10 C 0.68955(12) 0.25706(9) 0.91139(19) 0.0462 1.0000 Uani . . . . . .
C11 C 0.58418(11) 0.26074(8) 0.86912(16) 0.0371 1.0000 Uani . . . . . .
F12 F 0.83291(8) 0.30557(7) 1.05065(16) 0.0690 1.0000 Uani . . . . . .
C13 C 0.39011(10) 0.43222(7) 0.72678(15) 0.0317 1.0000 Uani . . . . . .
O14 O 0.34462(8) 0.48937(6) 0.70220(12) 0.0420 1.0000 Uani . . . . . .
C15 C 0.47959(10) 0.40803(7) 0.62790(15) 0.0323 1.0000 Uani . . . . . .
C16 C 0.58061(10) 0.44505(7) 0.67975(15) 0.0332 1.0000 Uani . . . . . .
O17 O 0.58497(8) 0.50187(6) 0.74680(14) 0.0459 1.0000 Uani . . . . . .
O18 O 0.66303(7) 0.40735(5) 0.63750(12) 0.0389 1.0000 Uani . . . . . .
C19 C 0.76407(12) 0.44120(10) 0.6720(2) 0.0504 1.0000 Uani . . . . . .
C20 C 0.84616(15) 0.39106(14) 0.6187(4) 0.0848 1.0000 Uani . . . . . .
C21 C 0.18248(10) 0.43671(8) 0.85754(15) 0.0336 1.0000 Uani . . . . . .
O22 O 0.13641(8) 0.40723(7) 0.75291(12) 0.0476 1.0000 Uani . . . . . .
O23 O 0.15261(8) 0.49849(6) 0.92181(13) 0.0408 1.0000 Uani . . . . . .
C24 C 0.06435(14) 0.53354(11) 0.8446(3) 0.0615 1.0000 Uani . . . . . .
C31 C 0.19908(10) 0.33002(7) 1.15714(15) 0.0302 1.0000 Uani . . . . . .
C32 C 0.09400(10) 0.31058(8) 1.16419(16) 0.0354 1.0000 Uani . . . . . .
C33 C 0.04339(10) 0.31431(8) 1.30319(17) 0.0383 1.0000 Uani . . . . . .
C34 C 0.09677(11) 0.33823(8) 1.43376(17) 0.0383 1.0000 Uani . . . . . .
C35 C 0.20150(12) 0.35665(8) 1.42751(17) 0.0396 1.0000 Uani . . . . . .
C36 C 0.25252(11) 0.35265(8) 1.29012(16) 0.0359 1.0000 Uani . . . . . .
H21 H 0.2994 0.4381 1.0238 0.0337 1.0000 Uiso R . . . . .
H31 H 0.2072 0.3035 0.9280 0.0343 1.0000 Uiso R . . . . .
H51 H 0.3914 0.2820 0.8015 0.0332 1.0000 Uiso R . . . . .
H71 H 0.5229 0.4052 1.0653 0.0386 1.0000 Uiso R . . . . .
H81 H 0.7010 0.4001 1.1360 0.0476 1.0000 Uiso R . . . . .
H101 H 0.7324 0.2207 0.8746 0.0558 1.0000 Uiso R . . . . .
H111 H 0.5543 0.2246 0.8040 0.0445 1.0000 Uiso R . . . . .
H151 H 0.4644 0.4249 0.5206 0.0395 1.0000 Uiso R . . . . .
H152 H 0.4900 0.3570 0.6281 0.0374 1.0000 Uiso R . . . . .
H191 H 0.7715 0.4506 0.7826 0.0600 1.0000 Uiso R . . . . .
H192 H 0.7681 0.4869 0.6189 0.0606 1.0000 Uiso R . . . . .
H201 H 0.9148 0.4121 0.6419 0.1258 1.0000 Uiso R . . . . .
H203 H 0.8395 0.3434 0.6646 0.1274 1.0000 Uiso R . . . . .
H202 H 0.8348 0.3873 0.5074 0.1263 1.0000 Uiso R . . . . .
H242 H 0.0482 0.5774 0.9036 0.0914 1.0000 Uiso R . . . . .
H241 H 0.0844 0.5453 0.7392 0.0911 1.0000 Uiso R . . . . .
H243 H 0.0061 0.5007 0.8399 0.0907 1.0000 Uiso R . . . . .
H321 H 0.0578 0.2939 1.0734 0.0430 1.0000 Uiso R . . . . .
H331 H -0.0284 0.2998 1.3120 0.0460 1.0000 Uiso R . . . . .
H341 H 0.0610 0.3420 1.5284 0.0453 1.0000 Uiso R . . . . .
H351 H 0.2372 0.3721 1.5172 0.0485 1.0000 Uiso R . . . . .
H361 H 0.3239 0.3674 1.2823 0.0425 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.84(12)
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
N1 . C2 . 1.4609(15) yes
N1 . C5 . 1.4876(15) yes
N1 . C13 . 1.3541(17) yes
C2 . C3 . 1.5414(18) yes
C2 . C21 . 1.5161(17) yes
C2 . H21 . 0.960 no
C3 . O4 . 1.4347(15) yes
C3 . C31 . 1.4974(17) yes
C3 . H31 . 0.987 no
O4 . C5 . 1.4201(15) yes
C5 . C6 . 1.5051(17) yes
C5 . H51 . 0.973 no
C6 . C7 . 1.3932(19) yes
C6 . C11 . 1.3881(18) yes
C7 . C8 . 1.3869(19) yes
C7 . H71 . 0.958 no
C8 . C9 . 1.379(2) yes
C8 . H81 . 0.958 no
C9 . C10 . 1.370(2) yes
C9 . F12 . 1.3628(17) yes
C10 . C11 . 1.388(2) yes
C10 . H101 . 0.930 no
C11 . H111 . 0.947 no
C13 . O14 . 1.2222(17) yes
C13 . C15 . 1.5208(17) yes
C15 . C16 . 1.5185(18) yes
C15 . H151 . 0.997 no
C15 . H152 . 0.954 no
C16 . O17 . 1.2021(18) yes
C16 . O18 . 1.3261(16) yes
O18 . C19 . 1.4590(18) yes
C19 . C20 . 1.486(2) yes
C19 . H191 . 0.979 no
C19 . H192 . 0.965 no
C20 . H201 . 0.976 no
C20 . H203 . 0.972 no
C20 . H202 . 0.975 no
C21 . O22 . 1.1988(18) yes
C21 . O23 . 1.3331(17) yes
O23 . C24 . 1.4485(19) yes
C24 . H242 . 0.985 no
C24 . H241 . 0.983 no
C24 . H243 . 0.961 no
C31 . C32 . 1.3953(18) yes
C31 . C36 . 1.3882(19) yes
C32 . C33 . 1.3902(19) yes
C32 . H321 . 0.953 no
C33 . C34 . 1.378(2) yes
C33 . H331 . 0.962 no
C34 . C35 . 1.386(2) yes
C34 . H341 . 0.957 no
C35 . C36 . 1.381(2) yes
C35 . H351 . 0.936 no
C36 . H361 . 0.958 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
C2 . N1 . C5 . 109.91(10) yes
C2 . N1 . C13 . 121.80(11) yes
C5 . N1 . C13 . 128.21(10) yes
N1 . C2 . C3 . 100.46(10) yes
N1 . C2 . C21 . 113.28(10) yes
C3 . C2 . C21 . 109.86(10) yes
N1 . C2 . H21 . 111.2 no
C3 . C2 . H21 . 112.4 no
C21 . C2 . H21 . 109.4 no
C2 . C3 . O4 . 101.71(9) yes
C2 . C3 . C31 . 114.21(10) yes
O4 . C3 . C31 . 110.82(10) yes
C2 . C3 . H31 . 109.6 no
O4 . C3 . H31 . 110.3 no
C31 . C3 . H31 . 110.0 no
C3 . O4 . C5 . 107.28(9) yes
N1 . C5 . O4 . 102.99(9) yes
N1 . C5 . C6 . 114.99(10) yes
O4 . C5 . C6 . 107.77(10) yes
N1 . C5 . H51 . 109.2 no
O4 . C5 . H51 . 111.0 no
C6 . C5 . H51 . 110.6 no
C5 . C6 . C7 . 120.79(11) yes
C5 . C6 . C11 . 118.93(12) yes
C7 . C6 . C11 . 120.21(12) yes
C6 . C7 . C8 . 120.14(13) yes
C6 . C7 . H71 . 120.4 no
C8 . C7 . H71 . 119.4 no
C7 . C8 . C9 . 117.75(14) yes
C7 . C8 . H81 . 120.5 no
C9 . C8 . H81 . 121.8 no
C8 . C9 . C10 . 123.72(14) yes
C8 . C9 . F12 . 118.16(15) yes
C10 . C9 . F12 . 118.12(15) yes
C9 . C10 . C11 . 117.99(14) yes
C9 . C10 . H101 . 120.5 no
C11 . C10 . H101 . 121.5 no
C6 . C11 . C10 . 120.19(14) yes
C6 . C11 . H111 . 120.2 no
C10 . C11 . H111 . 119.5 no
N1 . C13 . O14 . 121.41(12) yes
N1 . C13 . C15 . 117.33(11) yes
O14 . C13 . C15 . 121.26(12) yes
C13 . C15 . C16 . 110.43(11) yes
C13 . C15 . H151 . 108.0 no
C16 . C15 . H151 . 105.9 no
C13 . C15 . H152 . 113.4 no
C16 . C15 . H152 . 109.2 no
H151 . C15 . H152 . 109.6 no
C15 . C16 . O17 . 124.32(12) yes
C15 . C16 . O18 . 110.98(11) yes
O17 . C16 . O18 . 124.68(13) yes
C16 . O18 . C19 . 115.16(11) yes
O18 . C19 . C20 . 107.40(14) yes
O18 . C19 . H191 . 109.6 no
C20 . C19 . H191 . 111.7 no
O18 . C19 . H192 . 109.7 no
C20 . C19 . H192 . 110.4 no
H191 . C19 . H192 . 108.0 no
C19 . C20 . H201 . 109.1 no
C19 . C20 . H203 . 111.4 no
H201 . C20 . H203 . 111.6 no
C19 . C20 . H202 . 105.6 no
H201 . C20 . H202 . 109.7 no
H203 . C20 . H202 . 109.3 no
C2 . C21 . O22 . 124.41(13) yes
C2 . C21 . O23 . 110.86(11) yes
O22 . C21 . O23 . 124.53(13) yes
C21 . O23 . C24 . 114.80(13) yes
O23 . C24 . H242 . 107.5 no
O23 . C24 . H241 . 107.9 no
H242 . C24 . H241 . 111.6 no
O23 . C24 . H243 . 109.2 no
H242 . C24 . H243 . 111.5 no
H241 . C24 . H243 . 109.0 no
C3 . C31 . C32 . 119.57(12) yes
C3 . C31 . C36 . 120.97(11) yes
C32 . C31 . C36 . 119.40(12) yes
C31 . C32 . C33 . 120.13(13) yes
C31 . C32 . H321 . 119.4 no
C33 . C32 . H321 . 120.5 no
C32 . C33 . C34 . 119.90(12) yes
C32 . C33 . H331 . 121.8 no
C34 . C33 . H331 . 118.2 no
C33 . C34 . C35 . 120.08(13) yes
C33 . C34 . H341 . 119.5 no
C35 . C34 . H341 . 120.4 no
C34 . C35 . C36 . 120.37(13) yes
C34 . C35 . H351 . 119.3 no
C36 . C35 . H351 . 120.3 no
C31 . C36 . C35 . 120.11(13) yes
C31 . C36 . H361 . 118.2 no
C35 . C36 . H361 . 121.7 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
C8 . H81 . O14 2_667 142 0.96 2.56 3.370(2) yes
C34 . H341 . O22 1_556 122 0.96 2.46 3.080(2) yes
C35 . H351 . O22 1_556 120 0.94 2.54 3.117(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_17c
_database_code_depnum_ccdc_archive 'CCDC 2256188'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2019-07-03
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title '7185 - exp_4467 '
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_diffrn_special_details          
;
It was very hard  to find a good crystal of this sample. The
combination of solvent used and dry crystals meant that each 
crystal was coated in something very sticky, which made it 
almost impossible to find a good single crystal.
;

_cell_length_a                   8.2739(4)
_cell_length_b                   10.4856(6)
_cell_length_c                   13.0102(7)
_cell_angle_alpha                85.539(4)
_cell_angle_beta                 72.759(5)
_cell_angle_gamma                69.075(5)
_cell_volume                     1006.41(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'
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            2

# Given Formula = C44 H44 F2 N2 O12 
# Dc =      2.74 Fooo =    872.00 Mu =     17.83 M =    830.84
# Found Formula = C22 H22 F1 N1 O6 
# Dc =      1.37 FOOO =    436.00 Mu =      8.92 M =    415.42

_chemical_formula_sum            'C22 H22 F N O6'
_chemical_formula_moiety         'C22 H22 F N O6'
_chemical_compound_source        .
_chemical_formula_weight         415.42


_cell_measurement_reflns_used    4508
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      76.36
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_yellow
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.892

# Sheldrick geometric approximatio 0.85 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.55
_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            14152
_diffrn_reflns_av_unetI/netI     0.072
_reflns_number_total             4210
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.0721
# Number of reflections with Friedels Law is 4210 
# Theoretical number of reflections is about 8531 

_diffrn_reflns_theta_min         3.559
_diffrn_reflns_theta_max         77.190
_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        74.874
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -9
_reflns_limit_h_max              10
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.63
_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         -0.33
_refine_diff_density_max         0.34


# 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     271
_refine_ls_number_reflns         4199
_oxford_refine_ls_R_factor_ref   0.0604
_refine_ls_wR_factor_ref         0.1121
_refine_ls_goodness_of_fit_ref   0.9969
_refine_ls_shift/su_max          0.0003167
_refine_ls_shift/su_mean         0.0000323


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        4202
_refine_ls_R_factor_all          0.0606
_refine_ls_wR_factor_all         0.1125

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3225
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.0987


_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 + 0.34P] 
 ,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 0.60557(16) 0.32229(13) 0.53566(9) 0.0278 1.0000 Uani . . . . . .
C2 C 0.7456(2) 0.23467(18) 0.58078(13) 0.0254 1.0000 Uani . . . . . .
C3 C 0.8914(2) 0.30074(17) 0.54289(13) 0.0254 1.0000 Uani . . . . . .
N4 N 0.86618(19) 0.35181(15) 0.43876(11) 0.0259 1.0000 Uani . . . . . .
C5 C 0.6937(2) 0.35180(18) 0.42936(13) 0.0261 1.0000 Uani . . . . . .
C6 C 0.7130(2) 0.25157(18) 0.34458(13) 0.0256 1.0000 Uani . . . . . .
C7 C 0.5597(2) 0.26493(19) 0.31432(14) 0.0291 1.0000 Uani . . . . . .
C8 C 0.5698(3) 0.1812(2) 0.23365(15) 0.0350 1.0000 Uani . . . . . .
C9 C 0.7351(3) 0.0855(2) 0.18425(15) 0.0362 1.0000 Uani . . . . . .
C10 C 0.8885(3) 0.0666(2) 0.21342(15) 0.0349 1.0000 Uani . . . . . .
C11 C 0.8758(2) 0.15084(19) 0.29511(14) 0.0300 1.0000 Uani . . . . . .
F12 F 0.74791(19) 0.00487(15) 0.10307(11) 0.0567 1.0000 Uani . . . . . .
C21 C 0.6671(2) 0.23185(19) 0.70077(13) 0.0277 1.0000 Uani . . . . . .
C22 C 0.5898(3) 0.3517(2) 0.76367(15) 0.0394 1.0000 Uani . . . . . .
C23 C 0.5144(3) 0.3471(3) 0.87438(17) 0.0493 1.0000 Uani . . . . . .
C24 C 0.5192(3) 0.2238(3) 0.92213(16) 0.0486 1.0000 Uani . . . . . .
C25 C 0.5957(3) 0.1046(3) 0.86005(16) 0.0441 1.0000 Uani . . . . . .
C26 C 0.6680(2) 0.1091(2) 0.74913(15) 0.0332 1.0000 Uani . . . . . .
C31 C 1.0802(2) 0.19945(18) 0.53132(14) 0.0271 1.0000 Uani . . . . . .
O32 O 1.15992(18) 0.10780(13) 0.46471(11) 0.0364 1.0000 Uani . . . . . .
O33 O 1.14357(17) 0.22289(14) 0.60835(10) 0.0333 1.0000 Uani . . . . . .
C34 C 1.3265(3) 0.1344(2) 0.60365(18) 0.0421 1.0000 Uani . . . . . .
C41 C 0.9802(2) 0.40933(17) 0.37248(13) 0.0267 1.0000 Uani . . . . . .
O42 O 1.11562(16) 0.40861(13) 0.39282(10) 0.0319 1.0000 Uani . . . . . .
C43 C 0.9331(3) 0.47174(19) 0.27125(14) 0.0330 1.0000 Uani . . . . . .
C44 C 1.0376(3) 0.3729(2) 0.17528(14) 0.0332 1.0000 Uani . . . . . .
O45 O 1.18685(19) 0.29059(18) 0.16312(11) 0.0505 1.0000 Uani . . . . . .
O46 O 0.94260(18) 0.39105(14) 0.10565(10) 0.0375 1.0000 Uani . . . . . .
C47 C 1.0304(3) 0.3028(2) 0.00904(16) 0.0410 1.0000 Uani . . . . . .
C48 C 0.8882(3) 0.3149(3) -0.04418(17) 0.0472 1.0000 Uani . . . . . .
H21 H 0.7935 0.1437 0.5478 0.0302 1.0000 Uiso R . . . . .
H31 H 0.8641 0.3784 0.5905 0.0290 1.0000 Uiso R . . . . .
H51 H 0.6199 0.4429 0.4139 0.0290 1.0000 Uiso R . . . . .
H71 H 0.4493 0.3320 0.3472 0.0351 1.0000 Uiso R . . . . .
H81 H 0.4669 0.1898 0.2140 0.0421 1.0000 Uiso R . . . . .
H101 H 0.9990 -0.0018 0.1800 0.0430 1.0000 Uiso R . . . . .
H111 H 0.9791 0.1387 0.3161 0.0344 1.0000 Uiso R . . . . .
H221 H 0.5890 0.4353 0.7321 0.0463 1.0000 Uiso R . . . . .
H231 H 0.4639 0.4280 0.9150 0.0602 1.0000 Uiso R . . . . .
H241 H 0.4694 0.2240 1.0019 0.0565 1.0000 Uiso R . . . . .
H251 H 0.6017 0.0187 0.8930 0.0534 1.0000 Uiso R . . . . .
H261 H 0.7166 0.0265 0.7053 0.0406 1.0000 Uiso R . . . . .
H343 H 1.3490 0.1568 0.6686 0.0625 1.0000 Uiso R . . . . .
H341 H 1.4119 0.1532 0.5396 0.0625 1.0000 Uiso R . . . . .
H342 H 1.3377 0.0385 0.6029 0.0620 1.0000 Uiso R . . . . .
H431 H 0.9724 0.5511 0.2547 0.0403 1.0000 Uiso R . . . . .
H432 H 0.8049 0.5021 0.2784 0.0383 1.0000 Uiso R . . . . .
H472 H 1.1239 0.3345 -0.0384 0.0485 1.0000 Uiso R . . . . .
H471 H 1.0830 0.2077 0.0300 0.0479 1.0000 Uiso R . . . . .
H482 H 0.9410 0.2576 -0.1107 0.0703 1.0000 Uiso R . . . . .
H481 H 0.8350 0.4110 -0.0630 0.0702 1.0000 Uiso R . . . . .
H483 H 0.7950 0.2864 0.0052 0.0708 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.19(18)
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 . 1.446(2) yes
O1 . C5 . 1.4271(19) yes
C2 . C3 . 1.539(2) yes
C2 . C21 . 1.505(2) yes
C2 . H21 . 0.971 no
C3 . N4 . 1.463(2) yes
C3 . C31 . 1.513(2) yes
C3 . H31 . 0.981 no
N4 . C5 . 1.468(2) yes
N4 . C41 . 1.357(2) yes
C5 . C6 . 1.517(2) yes
C5 . H51 . 0.976 no
C6 . C7 . 1.394(2) yes
C6 . C11 . 1.386(2) yes
C7 . C8 . 1.385(3) yes
C7 . H71 . 0.932 no
C8 . C9 . 1.374(3) yes
C8 . H81 . 0.932 no
C9 . C10 . 1.374(3) yes
C9 . F12 . 1.360(2) yes
C10 . C11 . 1.391(2) yes
C10 . H101 . 0.940 no
C11 . H111 . 0.936 no
C21 . C22 . 1.391(3) yes
C21 . C26 . 1.387(3) yes
C22 . C23 . 1.394(3) yes
C22 . H221 . 0.937 no
C23 . C24 . 1.383(4) yes
C23 . H231 . 0.927 no
C24 . C25 . 1.380(3) yes
C24 . H241 . 0.996 no
C25 . C26 . 1.393(3) yes
C25 . H251 . 0.959 no
C26 . H261 . 0.964 no
C31 . O32 . 1.203(2) yes
C31 . O33 . 1.335(2) yes
O33 . C34 . 1.451(2) yes
C34 . H343 . 0.979 no
C34 . H341 . 0.978 no
C34 . H342 . 0.976 no
C41 . O42 . 1.222(2) yes
C41 . C43 . 1.518(2) yes
C43 . C44 . 1.517(3) yes
C43 . H431 . 0.984 no
C43 . H432 . 0.970 no
C44 . O45 . 1.199(2) yes
C44 . O46 . 1.328(2) yes
O46 . C47 . 1.457(2) yes
C47 . C48 . 1.498(3) yes
C47 . H472 . 0.979 no
C47 . H471 . 0.988 no
C48 . H482 . 0.985 no
C48 . H481 . 0.989 no
C48 . H483 . 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
C2 . O1 . C5 . 106.85(12) yes
O1 . C2 . C3 . 102.20(13) yes
O1 . C2 . C21 . 108.83(13) yes
C3 . C2 . C21 . 115.80(14) yes
O1 . C2 . H21 . 109.4 no
C3 . C2 . H21 . 108.8 no
C21 . C2 . H21 . 111.3 no
C2 . C3 . N4 . 100.70(13) yes
C2 . C3 . C31 . 112.78(14) yes
N4 . C3 . C31 . 111.88(14) yes
C2 . C3 . H31 . 110.9 no
N4 . C3 . H31 . 109.0 no
C31 . C3 . H31 . 111.2 no
C3 . N4 . C5 . 110.90(13) yes
C3 . N4 . C41 . 120.39(14) yes
C5 . N4 . C41 . 127.92(14) yes
N4 . C5 . O1 . 103.05(13) yes
N4 . C5 . C6 . 114.21(14) yes
O1 . C5 . C6 . 112.92(14) yes
N4 . C5 . H51 . 110.7 no
O1 . C5 . H51 . 107.1 no
C6 . C5 . H51 . 108.6 no
C5 . C6 . C7 . 117.74(15) yes
C5 . C6 . C11 . 122.87(15) yes
C7 . C6 . C11 . 119.37(16) yes
C6 . C7 . C8 . 120.71(17) yes
C6 . C7 . H71 . 120.2 no
C8 . C7 . H71 . 119.1 no
C7 . C8 . C9 . 118.05(17) yes
C7 . C8 . H81 . 120.5 no
C9 . C8 . H81 . 121.5 no
C8 . C9 . C10 . 123.11(18) yes
C8 . C9 . F12 . 118.66(17) yes
C10 . C9 . F12 . 118.22(18) yes
C9 . C10 . C11 . 118.12(17) yes
C9 . C10 . H101 . 121.4 no
C11 . C10 . H101 . 120.5 no
C10 . C11 . C6 . 120.57(16) yes
C10 . C11 . H111 . 119.0 no
C6 . C11 . H111 . 120.4 no
C2 . C21 . C22 . 120.67(17) yes
C2 . C21 . C26 . 119.84(16) yes
C22 . C21 . C26 . 119.47(17) yes
C21 . C22 . C23 . 119.7(2) yes
C21 . C22 . H221 . 120.3 no
C23 . C22 . H221 . 120.0 no
C22 . C23 . C24 . 120.4(2) yes
C22 . C23 . H231 . 118.4 no
C24 . C23 . H231 . 121.2 no
C23 . C24 . C25 . 120.10(19) yes
C23 . C24 . H241 . 118.0 no
C25 . C24 . H241 . 121.8 no
C24 . C25 . C26 . 119.7(2) yes
C24 . C25 . H251 . 120.4 no
C26 . C25 . H251 . 119.9 no
C25 . C26 . C21 . 120.60(19) yes
C25 . C26 . H261 . 119.8 no
C21 . C26 . H261 . 119.6 no
C3 . C31 . O32 . 125.12(16) yes
C3 . C31 . O33 . 110.27(14) yes
O32 . C31 . O33 . 124.56(16) yes
C31 . O33 . C34 . 115.36(15) yes
O33 . C34 . H343 . 106.0 no
O33 . C34 . H341 . 109.8 no
H343 . C34 . H341 . 109.8 no
O33 . C34 . H342 . 110.6 no
H343 . C34 . H342 . 110.1 no
H341 . C34 . H342 . 110.3 no
N4 . C41 . O42 . 121.39(16) yes
N4 . C41 . C43 . 116.68(15) yes
O42 . C41 . C43 . 121.92(16) yes
C41 . C43 . C44 . 110.99(15) yes
C41 . C43 . H431 . 108.1 no
C44 . C43 . H431 . 106.2 no
C41 . C43 . H432 . 113.3 no
C44 . C43 . H432 . 109.6 no
H431 . C43 . H432 . 108.4 no
C43 . C44 . O45 . 124.67(17) yes
C43 . C44 . O46 . 110.84(16) yes
O45 . C44 . O46 . 124.48(18) yes
C44 . O46 . C47 . 115.88(15) yes
O46 . C47 . C48 . 107.23(17) yes
O46 . C47 . H472 . 108.5 no
C48 . C47 . H472 . 110.5 no
O46 . C47 . H471 . 109.0 no
C48 . C47 . H471 . 110.4 no
H472 . C47 . H471 . 111.2 no
C47 . C48 . H482 . 110.5 no
C47 . C48 . H481 . 109.3 no
H482 . C48 . H481 . 108.5 no
C47 . C48 . H483 . 109.0 no
H482 . C48 . H483 . 109.8 no
H481 . C48 . H483 . 109.6 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
C2 . H21 . O32 2_756 157 0.97 2.54 3.451(3) yes
C3 . H31 . O42 2_766 147 0.98 2.33 3.199(3) yes
C5 . H51 . O1 2_666 154 0.98 2.49 3.398(3) yes
C7 . H71 . O42 1_455 147 0.93 2.48 3.298(3) yes
C8 . H81 . O45 1_455 161 0.93 2.44 3.341(3) yes
C24 . H241 . O45 1_456 146 1.00 2.55 3.426(3) yes
C26 . H261 . O32 2_756 155 0.96 2.46 3.356(3) 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
-4 0 1 x .
-5 0 2 x .
-4 0 2 x .
-6 -1 3 x .
1 8 12 x .
-8 1 3 x .
1 8 11 x .
-8 0 4 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_245d-20d
_database_code_depnum_ccdc_archive 'CCDC 2256191'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2019-07-01
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title 7186
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.7501(2)
_cell_length_b                   11.9848(3)
_cell_length_c                   13.8497(3)
_cell_angle_alpha                99.820(2)
_cell_angle_beta                 100.855(2)
_cell_angle_gamma                94.018(2)
_cell_volume                     1237.92(5)

_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'


_cell_formula_units_Z            2

# Given Formula = C28 H28 F2 N2 O4 
# Dc =      1.33 Fooo =    520.00 Mu =      8.23 M =    494.54
# Found Formula = C28 H28 F2 N2 O4 
# Dc =      1.33 FOOO =    520.00 Mu =      8.23 M =    494.54

_chemical_formula_sum            'C28 H28 F2 N2 O4'
_chemical_formula_moiety         'C28 H28 F2 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         494.54


_cell_measurement_reflns_used    12775
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      76.03
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_max          0.29

_exptl_crystal_density_diffrn    1.327
_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    0.823

# Sheldrick geometric approximatio 0.84 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.82
_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            21587
_diffrn_reflns_av_unetI/netI     0.032
_reflns_number_total             5117
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.0316
# Number of reflections with Friedels Law is 5117 
# Theoretical number of reflections is about 10364 

_diffrn_reflns_theta_min         3.764
_diffrn_reflns_theta_max         76.192
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        73.906
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -15
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.45
_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         -0.22
_refine_diff_density_max         0.29


# 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     325
_refine_ls_number_reflns         5116
_oxford_refine_ls_R_factor_ref   0.0361
_refine_ls_wR_factor_ref         0.0911
_refine_ls_goodness_of_fit_ref   1.0021
_refine_ls_shift/su_max          0.0010395
_refine_ls_shift/su_mean         0.0000896


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        5117
_refine_ls_R_factor_all          0.0361
_refine_ls_wR_factor_all         0.0911

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4718
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0886


_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 + 0.35P] 
 ,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
N1 N 0.69487(12) 0.97687(7) 0.79781(7) 0.0241 1.0000 Uani . . . . . .
C2 C 0.85501(13) 0.92694(8) 0.77689(7) 0.0223 1.0000 Uani . . . . . .
N3 N 0.96988(11) 1.02279(7) 0.76114(6) 0.0211 1.0000 Uani . . . . . .
C4 C 0.94556(13) 1.11735(8) 0.83830(7) 0.0214 1.0000 Uani . . . . . .
C5 C 0.74316(13) 1.09902(8) 0.83585(7) 0.0214 1.0000 Uani . . . . . .
C6 C 0.70278(14) 1.12884(8) 0.94102(7) 0.0226 1.0000 Uani . . . . . .
O7 O 0.81142(11) 1.15096(8) 1.01793(6) 0.0332 1.0000 Uani . . . . . .
O8 O 0.52887(10) 1.12203(6) 0.93467(5) 0.0262 1.0000 Uani . . . . . .
C9 C 0.46704(15) 1.14370(10) 1.02867(8) 0.0284 1.0000 Uani . . . . . .
C10 C 0.47653(17) 1.26909(11) 1.06826(10) 0.0372 1.0000 Uani . . . . . .
C11 C 0.63737(13) 1.16904(9) 0.76775(7) 0.0219 1.0000 Uani . . . . . .
O12 O 0.56260(11) 1.13158(7) 0.68288(6) 0.0298 1.0000 Uani . . . . . .
O13 O 0.64162(10) 1.27631(6) 0.81427(5) 0.0256 1.0000 Uani . . . . . .
C14 C 0.55034(16) 1.35092(10) 0.75414(9) 0.0321 1.0000 Uani . . . . . .
C15 C 0.58150(19) 1.46831(11) 0.81610(11) 0.0419 1.0000 Uani . . . . . .
C21 C 0.80765(13) 0.82890(9) 0.68881(8) 0.0227 1.0000 Uani . . . . . .
C22 C 0.80306(16) 0.71724(10) 0.70378(9) 0.0308 1.0000 Uani . . . . . .
C23 C 0.75538(18) 0.62674(10) 0.62304(10) 0.0372 1.0000 Uani . . . . . .
C24 C 0.71376(16) 0.65135(10) 0.52891(9) 0.0345 1.0000 Uani . . . . . .
C25 C 0.71634(17) 0.76050(11) 0.51089(9) 0.0357 1.0000 Uani . . . . . .
C26 C 0.76350(16) 0.84963(9) 0.59224(8) 0.0300 1.0000 Uani . . . . . .
F27 F 0.66592(13) 0.56340(7) 0.44889(6) 0.0523 1.0000 Uani . . . . . .
C31 C 1.15826(13) 1.00291(9) 0.77624(8) 0.0250 1.0000 Uani . . . . . .
C32 C 1.20200(13) 0.91672(9) 0.69382(8) 0.0240 1.0000 Uani . . . . . .
C33 C 1.22838(15) 0.80652(10) 0.70753(9) 0.0307 1.0000 Uani . . . . . .
C34 C 1.26819(17) 0.72721(11) 0.63165(10) 0.0387 1.0000 Uani . . . . . .
C35 C 1.28440(17) 0.75815(12) 0.54189(10) 0.0406 1.0000 Uani . . . . . .
C36 C 1.26140(18) 0.86798(12) 0.52808(10) 0.0405 1.0000 Uani . . . . . .
C37 C 1.21923(16) 0.94680(10) 0.60327(9) 0.0322 1.0000 Uani . . . . . .
C41 C 1.00995(13) 1.23339(9) 0.82199(8) 0.0235 1.0000 Uani . . . . . .
C42 C 1.06208(14) 1.32249(10) 0.90386(9) 0.0295 1.0000 Uani . . . . . .
C43 C 1.10781(16) 1.43222(10) 0.89039(10) 0.0362 1.0000 Uani . . . . . .
C44 C 1.10040(15) 1.45037(10) 0.79434(11) 0.0357 1.0000 Uani . . . . . .
C45 C 1.05228(16) 1.36477(10) 0.71162(10) 0.0337 1.0000 Uani . . . . . .
C46 C 1.00712(14) 1.25523(9) 0.72621(8) 0.0276 1.0000 Uani . . . . . .
F47 F 1.14362(12) 1.55770(7) 0.78097(8) 0.0537 1.0000 Uani . . . . . .
H21 H 0.9114 0.8995 0.8372 0.0267 1.0000 Uiso R . . . . .
H41 H 1.0058 1.1080 0.9059 0.0253 1.0000 Uiso R . . . . .
H91 H 0.5353 1.1053 1.0773 0.0322 1.0000 Uiso R . . . . .
H92 H 0.3444 1.1095 1.0109 0.0341 1.0000 Uiso R . . . . .
H102 H 0.4264 1.2806 1.1289 0.0562 1.0000 Uiso R . . . . .
H101 H 0.6000 1.3041 1.0858 0.0529 1.0000 Uiso R . . . . .
H103 H 0.4124 1.3081 1.0187 0.0558 1.0000 Uiso R . . . . .
H142 H 0.5981 1.3479 0.6926 0.0382 1.0000 Uiso R . . . . .
H141 H 0.4246 1.3237 0.7371 0.0378 1.0000 Uiso R . . . . .
H151 H 0.5226 1.5203 0.7775 0.0617 1.0000 Uiso R . . . . .
H153 H 0.7087 1.4938 0.8337 0.0612 1.0000 Uiso R . . . . .
H152 H 0.5354 1.4701 0.8768 0.0619 1.0000 Uiso R . . . . .
H221 H 0.8359 0.7033 0.7707 0.0375 1.0000 Uiso R . . . . .
H231 H 0.7540 0.5509 0.6329 0.0466 1.0000 Uiso R . . . . .
H251 H 0.6858 0.7740 0.4439 0.0441 1.0000 Uiso R . . . . .
H261 H 0.7670 0.9266 0.5818 0.0372 1.0000 Uiso R . . . . .
H311 H 1.2279 1.0773 0.7801 0.0293 1.0000 Uiso R . . . . .
H312 H 1.1907 0.9782 0.8412 0.0289 1.0000 Uiso R . . . . .
H331 H 1.2158 0.7858 0.7690 0.0375 1.0000 Uiso R . . . . .
H341 H 1.2863 0.6522 0.6421 0.0469 1.0000 Uiso R . . . . .
H351 H 1.3121 0.7026 0.4891 0.0492 1.0000 Uiso R . . . . .
H361 H 1.2743 0.8894 0.4663 0.0501 1.0000 Uiso R . . . . .
H371 H 1.2038 1.0235 0.5935 0.0396 1.0000 Uiso R . . . . .
H421 H 1.0640 1.3089 0.9705 0.0345 1.0000 Uiso R . . . . .
H431 H 1.1449 1.4937 0.9456 0.0434 1.0000 Uiso R . . . . .
H451 H 1.0505 1.3801 0.6460 0.0411 1.0000 Uiso R . . . . .
H461 H 0.9741 1.1946 0.6704 0.0331 1.0000 Uiso R . . . . .
H11 H 0.6146 0.9685 0.7401 0.0306 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.27(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
N1 . C2 . 1.4706(13) yes
N1 . C5 . 1.4651(12) yes
N1 . H11 . 0.902 no
C2 . N3 . 1.4748(12) yes
C2 . C21 . 1.5117(14) yes
C2 . H21 . 0.986 no
N3 . C4 . 1.4678(12) yes
N3 . C31 . 1.4774(13) yes
C4 . C5 . 1.5617(13) yes
C4 . C41 . 1.5122(14) yes
C4 . H41 . 0.993 no
C5 . C6 . 1.5353(13) yes
C5 . C11 . 1.5301(14) yes
C6 . O7 . 1.2034(13) yes
C6 . O8 . 1.3298(13) yes
O8 . C9 . 1.4591(12) yes
C9 . C10 . 1.5009(16) yes
C9 . H91 . 0.975 no
C9 . H92 . 0.977 no
C10 . H102 . 0.984 no
C10 . H101 . 0.986 no
C10 . H103 . 0.975 no
C11 . O12 . 1.2025(13) yes
C11 . O13 . 1.3313(13) yes
O13 . C14 . 1.4542(13) yes
C14 . C15 . 1.4954(17) yes
C14 . H142 . 0.987 no
C14 . H141 . 0.977 no
C15 . H151 . 0.972 no
C15 . H153 . 0.983 no
C15 . H152 . 0.972 no
C21 . C22 . 1.3878(15) yes
C21 . C26 . 1.3859(15) yes
C22 . C23 . 1.3921(17) yes
C22 . H221 . 0.961 no
C23 . C24 . 1.3699(19) yes
C23 . H231 . 0.941 no
C24 . C25 . 1.3724(18) yes
C24 . F27 . 1.3670(13) yes
C25 . C26 . 1.3870(16) yes
C25 . H251 . 0.958 no
C26 . H261 . 0.958 no
C31 . C32 . 1.5092(14) yes
C31 . H311 . 0.997 no
C31 . H312 . 0.988 no
C32 . C33 . 1.3896(16) yes
C32 . C37 . 1.3897(15) yes
C33 . C34 . 1.3877(17) yes
C33 . H331 . 0.946 no
C34 . C35 . 1.381(2) yes
C34 . H341 . 0.950 no
C35 . C36 . 1.381(2) yes
C35 . H351 . 0.968 no
C36 . C37 . 1.3854(17) yes
C36 . H361 . 0.955 no
C37 . H371 . 0.964 no
C41 . C42 . 1.3940(15) yes
C41 . C46 . 1.3917(15) yes
C42 . C43 . 1.3905(16) yes
C42 . H421 . 0.962 no
C43 . C44 . 1.3754(19) yes
C43 . H431 . 0.952 no
C44 . C45 . 1.3743(19) yes
C44 . F47 . 1.3584(13) yes
C45 . C46 . 1.3926(15) yes
C45 . H451 . 0.955 no
C46 . H461 . 0.947 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
C2 . N1 . C5 . 107.63(8) yes
C2 . N1 . H11 . 109.0 no
C5 . N1 . H11 . 108.0 no
N1 . C2 . N3 . 104.75(8) yes
N1 . C2 . C21 . 110.28(8) yes
N3 . C2 . C21 . 114.46(8) yes
N1 . C2 . H21 . 107.7 no
N3 . C2 . H21 . 109.4 no
C21 . C2 . H21 . 109.9 no
C2 . N3 . C4 . 103.12(7) yes
C2 . N3 . C31 . 113.05(8) yes
C4 . N3 . C31 . 109.51(8) yes
N3 . C4 . C5 . 102.42(8) yes
N3 . C4 . C41 . 113.95(8) yes
C5 . C4 . C41 . 114.62(8) yes
N3 . C4 . H41 . 111.2 no
C5 . C4 . H41 . 106.1 no
C41 . C4 . H41 . 108.3 no
C4 . C5 . N1 . 104.52(8) yes
C4 . C5 . C6 . 111.59(8) yes
N1 . C5 . C6 . 108.90(8) yes
C4 . C5 . C11 . 112.10(8) yes
N1 . C5 . C11 . 110.77(8) yes
C6 . C5 . C11 . 108.88(8) yes
C5 . C6 . O7 . 125.33(9) yes
C5 . C6 . O8 . 109.65(8) yes
O7 . C6 . O8 . 124.97(9) yes
C6 . O8 . C9 . 116.85(8) yes
O8 . C9 . C10 . 111.19(9) yes
O8 . C9 . H91 . 109.8 no
C10 . C9 . H91 . 111.3 no
O8 . C9 . H92 . 104.0 no
C10 . C9 . H92 . 110.6 no
H91 . C9 . H92 . 109.8 no
C9 . C10 . H102 . 109.0 no
C9 . C10 . H101 . 110.9 no
H102 . C10 . H101 . 108.5 no
C9 . C10 . H103 . 111.4 no
H102 . C10 . H103 . 109.7 no
H101 . C10 . H103 . 107.4 no
C5 . C11 . O12 . 123.92(9) yes
C5 . C11 . O13 . 111.18(8) yes
O12 . C11 . O13 . 124.89(10) yes
C11 . O13 . C14 . 115.28(8) yes
O13 . C14 . C15 . 107.34(9) yes
O13 . C14 . H142 . 108.7 no
C15 . C14 . H142 . 111.4 no
O13 . C14 . H141 . 108.2 no
C15 . C14 . H141 . 111.0 no
H142 . C14 . H141 . 110.1 no
C14 . C15 . H151 . 109.2 no
C14 . C15 . H153 . 109.9 no
H151 . C15 . H153 . 108.4 no
C14 . C15 . H152 . 110.8 no
H151 . C15 . H152 . 109.0 no
H153 . C15 . H152 . 109.5 no
C2 . C21 . C22 . 120.49(9) yes
C2 . C21 . C26 . 120.26(9) yes
C22 . C21 . C26 . 119.22(10) yes
C21 . C22 . C23 . 120.67(11) yes
C21 . C22 . H221 . 118.9 no
C23 . C22 . H221 . 120.4 no
C22 . C23 . C24 . 118.05(11) yes
C22 . C23 . H231 . 120.9 no
C24 . C23 . H231 . 121.1 no
C23 . C24 . C25 . 123.11(11) yes
C23 . C24 . F27 . 118.74(11) yes
C25 . C24 . F27 . 118.15(11) yes
C24 . C25 . C26 . 118.07(11) yes
C24 . C25 . H251 . 120.5 no
C26 . C25 . H251 . 121.4 no
C25 . C26 . C21 . 120.88(11) yes
C25 . C26 . H261 . 119.8 no
C21 . C26 . H261 . 119.3 no
N3 . C31 . C32 . 113.93(8) yes
N3 . C31 . H311 . 107.3 no
C32 . C31 . H311 . 108.8 no
N3 . C31 . H312 . 107.9 no
C32 . C31 . H312 . 110.1 no
H311 . C31 . H312 . 108.6 no
C31 . C32 . C33 . 120.72(10) yes
C31 . C32 . C37 . 120.47(10) yes
C33 . C32 . C37 . 118.80(10) yes
C32 . C33 . C34 . 120.70(11) yes
C32 . C33 . H331 . 118.8 no
C34 . C33 . H331 . 120.5 no
C33 . C34 . C35 . 119.89(12) yes
C33 . C34 . H341 . 119.9 no
C35 . C34 . H341 . 120.2 no
C34 . C35 . C36 . 119.88(11) yes
C34 . C35 . H351 . 119.7 no
C36 . C35 . H351 . 120.4 no
C35 . C36 . C37 . 120.28(12) yes
C35 . C36 . H361 . 119.7 no
C37 . C36 . H361 . 120.0 no
C32 . C37 . C36 . 120.42(11) yes
C32 . C37 . H371 . 119.5 no
C36 . C37 . H371 . 120.1 no
C4 . C41 . C42 . 119.45(9) yes
C4 . C41 . C46 . 121.33(9) yes
C42 . C41 . C46 . 119.08(10) yes
C41 . C42 . C43 . 120.72(11) yes
C41 . C42 . H421 . 120.1 no
C43 . C42 . H421 . 119.1 no
C42 . C43 . C44 . 118.28(11) yes
C42 . C43 . H431 . 121.6 no
C44 . C43 . H431 . 120.1 no
C43 . C44 . C45 . 122.94(11) yes
C43 . C44 . F47 . 118.37(12) yes
C45 . C44 . F47 . 118.70(12) yes
C44 . C45 . C46 . 118.18(11) yes
C44 . C45 . H451 . 120.8 no
C46 . C45 . H451 . 121.0 no
C45 . C46 . C41 . 120.79(11) yes
C45 . C46 . H461 . 119.8 no
C41 . C46 . H461 . 119.4 no


####################################################################### 
# 
# 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_245b-20b
_database_code_depnum_ccdc_archive 'CCDC 2256190'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2018-12-11
_audit_creation_method           'CRYSTALS_ver_14.61_build_7247 '

_oxford_structure_analysis_title 7079
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   18.3885(4)
_cell_length_b                   8.14230(10)
_cell_length_c                   19.1867(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.342(3)
_cell_angle_gamma                90
_cell_volume                     2551.78(12)

_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 0.0181 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 = C30 H34 N2 O4 
# Dc =      1.27 Fooo =   1040.00 Mu =      6.71 M =    486.61
# Found Formula = C30 H34 N2 O4 
# Dc =      1.27 FOOO =   1040.00 Mu =      6.71 M =    486.61

_chemical_formula_sum            'C30 H34 N2 O4'
_chemical_formula_moiety         'C30 H34 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         486.61


_cell_measurement_reflns_used    6090
_cell_measurement_theta_min      5
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.671

# Sheldrick geometric approximatio 0.90 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.82
_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            11384
_diffrn_reflns_av_unetI/netI     0.030
_reflns_number_total             5296
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.0305
# Number of reflections with Friedels Law is 5296 
# Theoretical number of reflections is about 10739 

_diffrn_reflns_theta_min         2.756
_diffrn_reflns_theta_max         76.610
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        74.312
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -23
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.30
_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         -0.27
_refine_diff_density_max         0.38


# 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>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5290
_oxford_refine_ls_R_factor_ref   0.0518
_refine_ls_wR_factor_ref         0.1230
_refine_ls_goodness_of_fit_ref   1.0137
_refine_ls_shift/su_max          0.0005164
_refine_ls_shift/su_mean         0.0000464


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5296
_refine_ls_R_factor_all          0.0528
_refine_ls_wR_factor_all         0.1352

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4610
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_gt          0.1312


_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 + 2.30P] 
 ,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
N1 N 0.44120(8) 0.55056(18) 0.73617(8) 0.0229 1.0000 Uani . . . . . .
C2 C 0.46625(9) 0.3855(2) 0.77089(9) 0.0217 1.0000 Uani . . . . . .
N3 N 0.55238(8) 0.40728(17) 0.82814(8) 0.0199 1.0000 Uani . . . . . .
C4 C 0.58440(9) 0.5323(2) 0.79281(9) 0.0195 1.0000 Uani . . . . . .
C5 C 0.51358(9) 0.6558(2) 0.76823(9) 0.0201 1.0000 Uani . . . . . .
C11 C 0.41333(10) 0.3222(2) 0.80659(9) 0.0220 1.0000 Uani . . . . . .
C12 C 0.34688(11) 0.2203(3) 0.76277(10) 0.0304 1.0000 Uani . . . . . .
C13 C 0.29589(11) 0.1662(3) 0.79346(11) 0.0328 1.0000 Uani . . . . . .
C14 C 0.30964(10) 0.2101(2) 0.86860(10) 0.0272 1.0000 Uani . . . . . .
C15 C 0.37617(11) 0.3125(2) 0.91170(10) 0.0268 1.0000 Uani . . . . . .
C16 C 0.42742(10) 0.3677(2) 0.88156(10) 0.0249 1.0000 Uani . . . . . .
C17 C 0.25608(11) 0.1489(3) 0.90324(12) 0.0349 1.0000 Uani . . . . . .
C21 C 0.59761(10) 0.2532(2) 0.85301(9) 0.0223 1.0000 Uani . . . . . .
C22 C 0.68232(10) 0.2739(2) 0.92098(9) 0.0211 1.0000 Uani . . . . . .
C23 C 0.70136(11) 0.4023(2) 0.97401(10) 0.0283 1.0000 Uani . . . . . .
C24 C 0.77953(12) 0.4154(2) 1.03691(11) 0.0335 1.0000 Uani . . . . . .
C25 C 0.83862(11) 0.3000(3) 1.04749(11) 0.0348 1.0000 Uani . . . . . .
C26 C 0.81992(12) 0.1718(3) 0.99520(12) 0.0385 1.0000 Uani . . . . . .
C27 C 0.74218(11) 0.1589(2) 0.93186(11) 0.0317 1.0000 Uani . . . . . .
C31 C 0.60339(9) 0.4687(2) 0.72851(9) 0.0203 1.0000 Uani . . . . . .
C32 C 0.68390(10) 0.4245(2) 0.74857(10) 0.0244 1.0000 Uani . . . . . .
C33 C 0.70517(10) 0.3574(2) 0.69417(10) 0.0268 1.0000 Uani . . . . . .
C34 C 0.64666(11) 0.3318(2) 0.61675(10) 0.0251 1.0000 Uani . . . . . .
C35 C 0.56624(11) 0.3770(2) 0.59616(10) 0.0257 1.0000 Uani . . . . . .
C36 C 0.54441(10) 0.4437(2) 0.65063(10) 0.0235 1.0000 Uani . . . . . .
C37 C 0.67043(12) 0.2544(3) 0.55855(12) 0.0340 1.0000 Uani . . . . . .
C41 C 0.50705(10) 0.7842(2) 0.70726(10) 0.0229 1.0000 Uani . . . . . .
O42 O 0.44402(8) 0.8238(2) 0.65236(8) 0.0411 1.0000 Uani . . . . . .
O43 O 0.57987(7) 0.85015(15) 0.72546(7) 0.0257 1.0000 Uani . . . . . .
C44 C 0.58119(11) 0.9697(2) 0.66954(11) 0.0298 1.0000 Uani . . . . . .
C45 C 0.58185(17) 0.8820(3) 0.60134(14) 0.0524 1.0000 Uani . . . . . .
C51 C 0.52636(10) 0.7555(2) 0.84179(10) 0.0226 1.0000 Uani . . . . . .
O52 O 0.59148(8) 0.8042(2) 0.89069(8) 0.0384 1.0000 Uani . . . . . .
O53 O 0.45555(8) 0.78263(17) 0.84245(8) 0.0326 1.0000 Uani . . . . . .
C54 C 0.45687(12) 0.8788(3) 0.90726(12) 0.0353 1.0000 Uani . . . . . .
C55 C 0.39173(15) 0.8121(3) 0.92522(14) 0.0450 1.0000 Uani . . . . . .
H21 H 0.4611 0.3083 0.7290 0.0248 1.0000 Uiso R . . . . .
H41 H 0.6351 0.5797 0.8354 0.0226 1.0000 Uiso R . . . . .
H121 H 0.3376 0.1857 0.7120 0.0349 1.0000 Uiso R . . . . .
H131 H 0.2525 0.0976 0.7639 0.0390 1.0000 Uiso R . . . . .
H151 H 0.3870 0.3455 0.9640 0.0317 1.0000 Uiso R . . . . .
H161 H 0.4719 0.4359 0.9114 0.0298 1.0000 Uiso R . . . . .
H172 H 0.2827 0.1573 0.9594 0.0521 1.0000 Uiso R . . . . .
H171 H 0.2407 0.0350 0.8879 0.0520 1.0000 Uiso R . . . . .
H173 H 0.2064 0.2093 0.8835 0.0511 1.0000 Uiso R . . . . .
H211 H 0.5655 0.1821 0.8699 0.0264 1.0000 Uiso R . . . . .
H212 H 0.6017 0.1999 0.8087 0.0269 1.0000 Uiso R . . . . .
H231 H 0.6614 0.4808 0.9678 0.0343 1.0000 Uiso R . . . . .
H241 H 0.7916 0.5015 1.0725 0.0402 1.0000 Uiso R . . . . .
H251 H 0.8931 0.3076 1.0916 0.0429 1.0000 Uiso R . . . . .
H261 H 0.8602 0.0945 1.0011 0.0463 1.0000 Uiso R . . . . .
H271 H 0.7293 0.0709 0.8966 0.0386 1.0000 Uiso R . . . . .
H321 H 0.7256 0.4424 0.8018 0.0290 1.0000 Uiso R . . . . .
H331 H 0.7608 0.3297 0.7097 0.0325 1.0000 Uiso R . . . . .
H351 H 0.5257 0.3598 0.5437 0.0319 1.0000 Uiso R . . . . .
H361 H 0.4898 0.4741 0.6354 0.0272 1.0000 Uiso R . . . . .
H371 H 0.6273 0.2657 0.5057 0.0515 1.0000 Uiso R . . . . .
H373 H 0.7184 0.3053 0.5612 0.0520 1.0000 Uiso R . . . . .
H372 H 0.6825 0.1385 0.5704 0.0517 1.0000 Uiso R . . . . .
H442 H 0.6329 1.0313 0.6989 0.0366 1.0000 Uiso R . . . . .
H441 H 0.5348 1.0452 0.6540 0.0355 1.0000 Uiso R . . . . .
H453 H 0.5832 0.9595 0.5638 0.0790 1.0000 Uiso R . . . . .
H451 H 0.6300 0.8111 0.6192 0.0797 1.0000 Uiso R . . . . .
H452 H 0.5327 0.8160 0.5743 0.0783 1.0000 Uiso R . . . . .
H541 H 0.5117 0.8732 0.9518 0.0424 1.0000 Uiso R . . . . .
H542 H 0.4461 0.9914 0.8905 0.0414 1.0000 Uiso R . . . . .
H552 H 0.3877 0.8768 0.9653 0.0668 1.0000 Uiso R . . . . .
H553 H 0.4065 0.7009 0.9463 0.0684 1.0000 Uiso R . . . . .
H551 H 0.3391 0.8115 0.8798 0.0666 1.0000 Uiso R . . . . .
H11 H 0.4045 0.5901 0.7478 0.0278 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       23(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          3.96(6)
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
N1 . C2 . 1.476(2) yes
N1 . C5 . 1.460(2) yes
N1 . H11 . 0.865 no
C2 . N3 . 1.4657(19) yes
C2 . C11 . 1.515(2) yes
C2 . H21 . 0.991 no
N3 . C4 . 1.4865(19) yes
N3 . C21 . 1.459(2) yes
C4 . C5 . 1.538(2) yes
C4 . C31 . 1.519(2) yes
C4 . H41 . 0.993 no
C5 . C41 . 1.532(2) yes
C5 . C51 . 1.550(2) yes
C11 . C12 . 1.395(2) yes
C11 . C16 . 1.390(2) yes
C12 . C13 . 1.388(2) yes
C12 . H121 . 0.952 no
C13 . C14 . 1.391(3) yes
C13 . H131 . 0.925 no
C14 . C15 . 1.395(3) yes
C14 . C17 . 1.504(2) yes
C15 . C16 . 1.388(2) yes
C15 . H151 . 0.966 no
C16 . H161 . 0.935 no
C17 . H172 . 0.960 no
C17 . H171 . 0.975 no
C17 . H173 . 0.950 no
C21 . C22 . 1.513(2) yes
C21 . H211 . 0.982 no
C21 . H212 . 0.988 no
C22 . C23 . 1.387(2) yes
C22 . C27 . 1.386(2) yes
C23 . C24 . 1.393(2) yes
C23 . H231 . 0.939 no
C24 . C25 . 1.379(3) yes
C24 . H241 . 0.932 no
C25 . C26 . 1.378(3) yes
C25 . H251 . 0.972 no
C26 . C27 . 1.391(3) yes
C26 . H261 . 0.938 no
C27 . H271 . 0.938 no
C31 . C32 . 1.395(2) yes
C31 . C36 . 1.401(2) yes
C32 . C33 . 1.384(2) yes
C32 . H321 . 0.965 no
C33 . C34 . 1.393(2) yes
C33 . H331 . 0.951 no
C34 . C35 . 1.393(2) yes
C34 . C37 . 1.511(2) yes
C35 . C36 . 1.391(2) yes
C35 . H351 . 0.949 no
C36 . H361 . 0.940 no
C37 . H371 . 0.963 no
C37 . H373 . 0.954 no
C37 . H372 . 0.972 no
C41 . O42 . 1.198(2) yes
C41 . O43 . 1.332(2) yes
O43 . C44 . 1.457(2) yes
C44 . C45 . 1.496(3) yes
C44 . H442 . 0.991 no
C44 . H441 . 0.980 no
C45 . H453 . 0.966 no
C45 . H451 . 0.977 no
C45 . H452 . 0.972 no
C51 . O52 . 1.200(2) yes
C51 . O53 . 1.326(2) yes
O53 . C54 . 1.460(2) yes
C54 . C55 . 1.492(3) yes
C54 . H541 . 0.979 no
C54 . H542 . 0.962 no
C55 . H552 . 0.962 no
C55 . H553 . 0.978 no
C55 . H551 . 0.959 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
C2 . N1 . C5 . 107.99(12) yes
C2 . N1 . H11 . 109.9 no
C5 . N1 . H11 . 110.0 no
N1 . C2 . N3 . 103.52(12) yes
N1 . C2 . C11 . 112.43(13) yes
N3 . C2 . C11 . 113.56(13) yes
N1 . C2 . H21 . 108.5 no
N3 . C2 . H21 . 110.6 no
C11 . C2 . H21 . 108.1 no
C2 . N3 . C4 . 105.01(12) yes
C2 . N3 . C21 . 113.49(13) yes
C4 . N3 . C21 . 116.89(12) yes
N3 . C4 . C5 . 97.50(12) yes
N3 . C4 . C31 . 115.07(13) yes
C5 . C4 . C31 . 116.88(13) yes
N3 . C4 . H41 . 108.1 no
C5 . C4 . H41 . 110.0 no
C31 . C4 . H41 . 108.7 no
C4 . C5 . N1 . 103.02(13) yes
C4 . C5 . C41 . 116.02(13) yes
N1 . C5 . C41 . 110.01(13) yes
C4 . C5 . C51 . 108.08(12) yes
N1 . C5 . C51 . 114.75(13) yes
C41 . C5 . C51 . 105.29(13) yes
C2 . C11 . C12 . 119.79(15) yes
C2 . C11 . C16 . 121.63(15) yes
C12 . C11 . C16 . 118.54(15) yes
C11 . C12 . C13 . 120.57(16) yes
C11 . C12 . H121 . 119.3 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C14 . 121.43(17) yes
C12 . C13 . H131 . 119.4 no
C14 . C13 . H131 . 119.1 no
C13 . C14 . C15 . 117.41(16) yes
C13 . C14 . C17 . 121.91(17) yes
C15 . C14 . C17 . 120.67(16) yes
C14 . C15 . C16 . 121.67(16) yes
C14 . C15 . H151 . 119.2 no
C16 . C15 . H151 . 119.1 no
C11 . C16 . C15 . 120.37(16) yes
C11 . C16 . H161 . 119.1 no
C15 . C16 . H161 . 120.5 no
C14 . C17 . H172 . 111.9 no
C14 . C17 . H171 . 109.9 no
H172 . C17 . H171 . 109.6 no
C14 . C17 . H173 . 111.0 no
H172 . C17 . H173 . 108.1 no
H171 . C17 . H173 . 106.2 no
N3 . C21 . C22 . 113.11(13) yes
N3 . C21 . H211 . 106.0 no
C22 . C21 . H211 . 108.5 no
N3 . C21 . H212 . 110.7 no
C22 . C21 . H212 . 109.6 no
H211 . C21 . H212 . 108.7 no
C21 . C22 . C23 . 121.97(15) yes
C21 . C22 . C27 . 119.10(15) yes
C23 . C22 . C27 . 118.91(16) yes
C22 . C23 . C24 . 120.38(17) yes
C22 . C23 . H231 . 120.0 no
C24 . C23 . H231 . 119.6 no
C23 . C24 . C25 . 120.33(18) yes
C23 . C24 . H241 . 119.8 no
C25 . C24 . H241 . 119.9 no
C24 . C25 . C26 . 119.54(17) yes
C24 . C25 . H251 . 120.8 no
C26 . C25 . H251 . 119.7 no
C25 . C26 . C27 . 120.39(18) yes
C25 . C26 . H261 . 120.1 no
C27 . C26 . H261 . 119.5 no
C26 . C27 . C22 . 120.45(18) yes
C26 . C27 . H271 . 120.4 no
C22 . C27 . H271 . 119.1 no
C4 . C31 . C32 . 118.33(14) yes
C4 . C31 . C36 . 124.16(14) yes
C32 . C31 . C36 . 117.43(15) yes
C31 . C32 . C33 . 121.70(15) yes
C31 . C32 . H321 . 118.7 no
C33 . C32 . H321 . 119.6 no
C32 . C33 . C34 . 121.06(16) yes
C32 . C33 . H331 . 119.5 no
C34 . C33 . H331 . 119.5 no
C33 . C34 . C35 . 117.53(15) yes
C33 . C34 . C37 . 120.44(16) yes
C35 . C34 . C37 . 122.02(16) yes
C34 . C35 . C36 . 121.68(16) yes
C34 . C35 . H351 . 118.5 no
C36 . C35 . H351 . 119.8 no
C31 . C36 . C35 . 120.60(15) yes
C31 . C36 . H361 . 119.1 no
C35 . C36 . H361 . 120.3 no
C34 . C37 . H371 . 111.2 no
C34 . C37 . H373 . 110.6 no
H371 . C37 . H373 . 107.9 no
C34 . C37 . H372 . 110.2 no
H371 . C37 . H372 . 109.1 no
H373 . C37 . H372 . 107.7 no
C5 . C41 . O42 . 124.06(15) yes
C5 . C41 . O43 . 110.99(13) yes
O42 . C41 . O43 . 124.89(16) yes
C41 . O43 . C44 . 115.54(13) yes
O43 . C44 . C45 . 109.56(16) yes
O43 . C44 . H442 . 104.8 no
C45 . C44 . H442 . 110.3 no
O43 . C44 . H441 . 109.7 no
C45 . C44 . H441 . 112.8 no
H442 . C44 . H441 . 109.3 no
C44 . C45 . H453 . 110.7 no
C44 . C45 . H451 . 110.2 no
H453 . C45 . H451 . 108.5 no
C44 . C45 . H452 . 110.6 no
H453 . C45 . H452 . 107.3 no
H451 . C45 . H452 . 109.3 no
C5 . C51 . O52 . 124.39(15) yes
C5 . C51 . O53 . 110.92(14) yes
O52 . C51 . O53 . 124.68(16) yes
C51 . O53 . C54 . 117.71(14) yes
O53 . C54 . C55 . 107.50(17) yes
O53 . C54 . H541 . 109.0 no
C55 . C54 . H541 . 113.3 no
O53 . C54 . H542 . 107.7 no
C55 . C54 . H542 . 111.2 no
H541 . C54 . H542 . 107.9 no
C54 . C55 . H552 . 110.5 no
C54 . C55 . H553 . 109.4 no
H552 . C55 . H553 . 106.6 no
C54 . C55 . H551 . 111.9 no
H552 . C55 . H551 . 108.2 no
H553 . C55 . H551 . 110.1 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
C36 . H361 . N1 . 122 0.94 2.55 3.149(3) 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
2 3 3 x .
0 1 1 x .
2 4 5 x .
4 0 6 x .
2 4 3 x .
8 4 7 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_245a-20a
_database_code_depnum_ccdc_archive 'CCDC 2256189'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2018-08-16
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 7001
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.8376(4)
_cell_length_b                   16.1029(5)
_cell_length_c                   14.4057(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.348(4)
_cell_angle_gamma                90
_cell_volume                     2412.39(15)

_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 0.0181 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 = C28 H30 N2 O4 
# Dc =      1.26 Fooo =    976.00 Mu =      6.80 M =    458.56
# Found Formula = C28 H30 N2 O4 
# Dc =      1.26 FOOO =    976.00 Mu =      6.80 M =    458.56

_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_moiety         'C28 H30 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         458.56


_cell_measurement_reflns_used    3906
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.19

_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             976.000
_exptl_absorpt_coefficient_mu    0.680

# Sheldrick geometric approximatio 0.90 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97
_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            11762
_reflns_number_total             5007
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0435
# Number of reflections with Friedels Law is 5007 
# Theoretical number of reflections is about 10166 

_diffrn_reflns_theta_min         4.215
_diffrn_reflns_theta_max         76.716
_diffrn_measured_fraction_theta_max 0.984

_diffrn_reflns_theta_full        74.415
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.85
_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         -0.26
_refine_diff_density_max         0.29


# 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>-3.0\s(I)
_refine_ls_number_restraints     48
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5002
_oxford_refine_ls_R_factor_ref   0.0578
_refine_ls_wR_factor_ref         0.1167
_refine_ls_goodness_of_fit_ref   1.0052
_refine_ls_shift/su_max          0.0003116
_refine_ls_shift/su_mean         0.0000351


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5006
_refine_ls_R_factor_all          0.0581
_refine_ls_wR_factor_all         0.1175

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3970
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_gt          0.1043


_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 + 0.62P] 
 ,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
N1 N -0.12373(12) 0.65530(9) 0.21895(9) 0.0327 1.0000 Uani . . . . . .
C2 C -0.15898(15) 0.71979(11) 0.27891(11) 0.0305 1.0000 Uani . . . . . .
N3 N -0.06666(12) 0.70811(9) 0.37384(9) 0.0292 1.0000 Uani . . . . . .
C4 C 0.05762(14) 0.69422(9) 0.35482(10) 0.0260 1.0000 Uani . . . . . .
C5 C 0.01612(14) 0.64512(10) 0.25611(10) 0.0262 1.0000 Uani D . . . . .
C11 C -0.29708(15) 0.70895(10) 0.28137(11) 0.0296 1.0000 Uani . . . . . .
C12 C -0.32745(16) 0.65317(11) 0.34488(13) 0.0358 1.0000 Uani . . . . . .
C13 C -0.45469(17) 0.64075(12) 0.34329(14) 0.0414 1.0000 Uani . . . . . .
C14 C -0.55160(17) 0.68323(13) 0.27826(13) 0.0419 1.0000 Uani . . . . . .
C15 C -0.52254(17) 0.73987(13) 0.21568(13) 0.0418 1.0000 Uani . . . . . .
C16 C -0.39460(16) 0.75326(11) 0.21727(12) 0.0359 1.0000 Uani . . . . . .
C21 C -0.06518(16) 0.77298(11) 0.44649(11) 0.0340 1.0000 Uani . . . . . .
C22 C -0.00739(18) 0.85554(11) 0.43125(12) 0.0370 1.0000 Uani . . . . . .
C23 C -0.0801(2) 0.91768(13) 0.37381(14) 0.0480 1.0000 Uani . . . . . .
C24 C -0.0233(3) 0.99231(14) 0.35990(16) 0.0638 1.0000 Uani . . . . . .
C25 C 0.1057(3) 1.00541(15) 0.4021(2) 0.0722 1.0000 Uani . . . . . .
C26 C 0.1782(3) 0.94511(15) 0.4600(2) 0.0680 1.0000 Uani . . . . . .
C27 C 0.12221(19) 0.87090(13) 0.47501(15) 0.0484 1.0000 Uani . . . . . .
C31 C 0.15151(14) 0.65292(9) 0.44026(10) 0.0259 1.0000 Uani . . . . . .
C32 C 0.11067(15) 0.59611(10) 0.49844(11) 0.0299 1.0000 Uani . . . . . .
C33 C 0.19761(17) 0.56172(11) 0.57894(12) 0.0357 1.0000 Uani . . . . . .
C34 C 0.32650(17) 0.58307(11) 0.60228(12) 0.0385 1.0000 Uani . . . . . .
C35 C 0.36802(16) 0.63957(11) 0.54527(13) 0.0374 1.0000 Uani . . . . . .
C36 C 0.28108(15) 0.67480(10) 0.46499(12) 0.0317 1.0000 Uani . . . . . .
C51 C 0.07757(14) 0.68344(10) 0.18157(11) 0.0273 1.0000 Uani . . . . . .
O52 O 0.14183(11) 0.74526(8) 0.19312(8) 0.0370 1.0000 Uani . . . . . .
O53 O 0.04581(12) 0.63903(8) 0.10029(8) 0.0360 1.0000 Uani . . . . . .
C54 C 0.09480(17) 0.66941(12) 0.02242(12) 0.0386 1.0000 Uani . . . . . .
C55 C 0.0384(2) 0.61658(14) -0.06411(13) 0.0514 1.0000 Uani . . . . . .
C44 C 0.2259(2) 0.45609(12) 0.28876(15) 0.0377 0.898(4) Uani D U P 1 1 .
C45 C 0.2624(2) 0.43250(14) 0.39384(16) 0.0471 0.898(4) Uani D U P 1 1 .
C145 C 0.3191(18) 0.4503(12) 0.3572(14) 0.0471 0.102(4) Uani D U P 1 2 .
C144 C 0.1779(17) 0.4521(11) 0.3031(14) 0.0377 0.102(4) Uani D U P 1 2 .
O143 O 0.1525(19) 0.5386(12) 0.2864(16) 0.0320 0.102(4) Uani D U P 1 2 .
O43 O 0.17676(18) 0.54147(12) 0.27412(15) 0.0320 0.898(4) Uani D U P 1 1 .
C141 C 0.0226(15) 0.5544(8) 0.2470(11) 0.0267 0.102(4) Uani D U P 1 2 .
C41 C 0.05323(18) 0.55310(12) 0.26958(13) 0.0267 0.898(4) Uani D U P 1 1 .
O142 O -0.0587(17) 0.5103(11) 0.2656(18) 0.0391 0.102(4) Uani D . P 1 2 .
O42 O -0.02136(17) 0.49821(11) 0.27213(17) 0.0391 0.898(4) Uani D . P 1 1 .
H21 H -0.1508 0.7751 0.2486 0.0363 1.0000 Uiso R . . . . .
H41 H 0.0958 0.7462 0.3412 0.0317 1.0000 Uiso R . . . . .
H121 H -0.2604 0.6235 0.3911 0.0435 1.0000 Uiso R . . . . .
H131 H -0.4745 0.6014 0.3882 0.0512 1.0000 Uiso R . . . . .
H141 H -0.6381 0.6746 0.2776 0.0507 1.0000 Uiso R . . . . .
H151 H -0.5890 0.7699 0.1707 0.0498 1.0000 Uiso R . . . . .
H161 H -0.3737 0.7918 0.1758 0.0430 1.0000 Uiso R . . . . .
H211 H -0.1549 0.7806 0.4487 0.0411 1.0000 Uiso R . . . . .
H212 H -0.0149 0.7499 0.5095 0.0409 1.0000 Uiso R . . . . .
H231 H -0.1673 0.9076 0.3456 0.0568 1.0000 Uiso R . . . . .
H241 H -0.0714 1.0335 0.3214 0.0768 1.0000 Uiso R . . . . .
H251 H 0.1445 1.0556 0.3901 0.0868 1.0000 Uiso R . . . . .
H261 H 0.2655 0.9547 0.4903 0.0829 1.0000 Uiso R . . . . .
H271 H 0.1724 0.8299 0.5167 0.0576 1.0000 Uiso R . . . . .
H321 H 0.0231 0.5812 0.4833 0.0364 1.0000 Uiso R . . . . .
H331 H 0.1671 0.5240 0.6184 0.0432 1.0000 Uiso R . . . . .
H341 H 0.3859 0.5599 0.6574 0.0465 1.0000 Uiso R . . . . .
H351 H 0.4558 0.6557 0.5621 0.0461 1.0000 Uiso R . . . . .
H361 H 0.3113 0.7151 0.4280 0.0382 1.0000 Uiso R . . . . .
H541 H 0.0696 0.7278 0.0089 0.0463 1.0000 Uiso R . . . . .
H542 H 0.1872 0.6654 0.0417 0.0470 1.0000 Uiso R . . . . .
H551 H 0.0700 0.6333 -0.1174 0.0770 1.0000 Uiso R . . . . .
H552 H -0.0543 0.6236 -0.0831 0.0771 1.0000 Uiso R . . . . .
H553 H 0.0598 0.5582 -0.0490 0.0772 1.0000 Uiso R . . . . .
H441 H 0.3010 0.4560 0.2651 0.0457 0.898(4) Uiso R . P 1 1 .
H442 H 0.1614 0.4183 0.2512 0.0464 0.898(4) Uiso R . P 1 1 .
H453 H 0.2996 0.3762 0.4009 0.0700 0.898(4) Uiso R . P 1 1 .
H452 H 0.3262 0.4716 0.4320 0.0712 0.898(4) Uiso R . P 1 1 .
H451 H 0.1849 0.4341 0.4171 0.0706 0.898(4) Uiso R . P 1 1 .
H1451 H 0.3425 0.3956 0.3832 0.0709 0.102(4) Uiso R . P 1 2 .
H1452 H 0.3372 0.4900 0.4088 0.0709 0.102(4) Uiso R . P 1 2 .
H1453 H 0.3684 0.4641 0.3134 0.0710 0.102(4) Uiso R . P 1 2 .
H1441 H 0.1259 0.4293 0.3420 0.0450 0.102(4) Uiso R . P 1 2 .
H1442 H 0.1613 0.4220 0.2425 0.0451 0.102(4) Uiso R . P 1 2 .
H11 H -0.1580 0.6086 0.2289 0.0401 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.11(12)
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
N1 . C2 . 1.468(2) yes
N1 . C5 . 1.4676(18) yes
N1 . H11 . 0.869 no
C2 . N3 . 1.4616(19) yes
C2 . C11 . 1.517(2) yes
C2 . H21 . 1.007 no
N3 . C4 . 1.4652(18) yes
N3 . C21 . 1.476(2) yes
C4 . C5 . 1.578(2) yes
C4 . C31 . 1.512(2) yes
C4 . H41 . 0.978 no
C5 . C51 . 1.5427(19) yes
C5 . C41 . 1.533(2) yes
C5 . C51 . 1.5427(19) yes
C5 . C141 . 1.470(14) yes
C11 . C12 . 1.386(2) yes
C11 . C16 . 1.389(2) yes
C12 . C13 . 1.387(2) yes
C12 . H121 . 0.963 no
C13 . C14 . 1.376(3) yes
C13 . H131 . 0.972 no
C14 . C15 . 1.380(3) yes
C14 . H141 . 0.945 no
C15 . C16 . 1.397(2) yes
C15 . H151 . 0.954 no
C16 . H161 . 0.933 no
C21 . C22 . 1.512(2) yes
C21 . H211 . 0.990 no
C21 . H212 . 0.990 no
C22 . C23 . 1.393(3) yes
C22 . C27 . 1.390(3) yes
C23 . C24 . 1.391(3) yes
C23 . H231 . 0.932 no
C24 . C25 . 1.375(4) yes
C24 . H241 . 0.926 no
C25 . C26 . 1.374(4) yes
C25 . H251 . 0.949 no
C26 . C27 . 1.385(3) yes
C26 . H261 . 0.937 no
C27 . H271 . 0.954 no
C31 . C32 . 1.394(2) yes
C31 . C36 . 1.393(2) yes
C32 . C33 . 1.387(2) yes
C32 . H321 . 0.943 no
C33 . C34 . 1.385(2) yes
C33 . H331 . 0.952 no
C34 . C35 . 1.383(3) yes
C34 . H341 . 0.947 no
C35 . C36 . 1.391(2) yes
C35 . H351 . 0.949 no
C36 . H361 . 0.953 no
C51 . O52 . 1.1994(19) yes
C51 . O53 . 1.3320(19) yes
O53 . C54 . 1.4543(18) yes
C54 . C55 . 1.491(3) yes
C54 . H541 . 0.983 no
C54 . H542 . 0.963 no
C55 . H551 . 0.963 no
C55 . H552 . 0.971 no
C55 . H553 . 0.977 no
C44 . C45 . 1.502(3) yes
C44 . O43 . 1.468(2) yes
C44 . H441 . 0.967 no
C44 . H442 . 0.968 no
C45 . H453 . 0.986 no
C45 . H452 . 0.981 no
C45 . H451 . 0.989 no
C145 . C144 . 1.510(17) yes
C145 . H1451 . 0.963 no
C145 . H1452 . 0.959 no
C145 . H1453 . 0.960 no
C144 . O143 . 1.426(17) yes
C144 . H1441 . 0.971 no
C144 . H1442 . 0.971 no
O143 . C141 . 1.386(16) yes
O43 . C41 . 1.335(2) yes
C141 . O142 . 1.218(16) yes
C41 . O42 . 1.205(2) 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
C2 . N1 . C5 . 106.10(12) yes
C2 . N1 . H11 . 108.7 no
C5 . N1 . H11 . 106.8 no
N1 . C2 . N3 . 103.68(12) yes
N1 . C2 . C11 . 110.74(13) yes
N3 . C2 . C11 . 112.54(12) yes
N1 . C2 . H21 . 107.5 no
N3 . C2 . H21 . 113.5 no
C11 . C2 . H21 . 108.7 no
C2 . N3 . C4 . 105.54(11) yes
C2 . N3 . C21 . 116.13(13) yes
C4 . N3 . C21 . 114.43(12) yes
N3 . C4 . C5 . 101.60(11) yes
N3 . C4 . C31 . 110.99(12) yes
C5 . C4 . C31 . 117.96(12) yes
N3 . C4 . H41 . 111.8 no
C5 . C4 . H41 . 106.1 no
C31 . C4 . H41 . 108.3 no
C4 . C5 . N1 . 106.02(11) yes
C4 . C5 . C51 . 110.94(12) yes
N1 . C5 . C51 . 107.78(12) yes
C4 . C5 . C41 . 111.84(13) yes
N1 . C5 . C41 . 111.18(13) yes
C51 . C5 . C41 . 108.99(12) yes
C4 . C5 . N1 . 106.02(11) yes
C4 . C5 . C51 . 110.94(12) yes
N1 . C5 . C51 . 107.78(12) yes
C4 . C5 . C141 . 124.7(6) yes
N1 . C5 . C141 . 98.6(6) yes
C51 . C5 . C141 . 107.1(5) yes
C2 . C11 . C12 . 120.59(14) yes
C2 . C11 . C16 . 119.76(15) yes
C12 . C11 . C16 . 119.61(15) yes
C11 . C12 . C13 . 120.13(16) yes
C11 . C12 . H121 . 120.4 no
C13 . C12 . H121 . 119.5 no
C12 . C13 . C14 . 120.27(17) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 120.16(16) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 119.9 no
C14 . C15 . C16 . 119.95(16) yes
C14 . C15 . H151 . 120.8 no
C16 . C15 . H151 . 119.2 no
C15 . C16 . C11 . 119.84(16) yes
C15 . C16 . H161 . 120.7 no
C11 . C16 . H161 . 119.4 no
N3 . C21 . C22 . 116.23(13) yes
N3 . C21 . H211 . 107.3 no
C22 . C21 . H211 . 110.2 no
N3 . C21 . H212 . 106.1 no
C22 . C21 . H212 . 108.6 no
H211 . C21 . H212 . 108.0 no
C21 . C22 . C23 . 121.99(17) yes
C21 . C22 . C27 . 119.84(17) yes
C23 . C22 . C27 . 118.17(19) yes
C22 . C23 . C24 . 120.5(2) yes
C22 . C23 . H231 . 118.0 no
C24 . C23 . H231 . 121.6 no
C23 . C24 . C25 . 120.4(2) yes
C23 . C24 . H241 . 120.5 no
C25 . C24 . H241 . 119.1 no
C24 . C25 . C26 . 119.8(2) yes
C24 . C25 . H251 . 119.8 no
C26 . C25 . H251 . 120.4 no
C25 . C26 . C27 . 120.3(2) yes
C25 . C26 . H261 . 119.8 no
C27 . C26 . H261 . 119.9 no
C22 . C27 . C26 . 120.9(2) yes
C22 . C27 . H271 . 119.1 no
C26 . C27 . H271 . 120.0 no
C4 . C31 . C32 . 121.53(13) yes
C4 . C31 . C36 . 119.71(14) yes
C32 . C31 . C36 . 118.68(15) yes
C31 . C32 . C33 . 120.57(15) yes
C31 . C32 . H321 . 119.8 no
C33 . C32 . H321 . 119.6 no
C32 . C33 . C34 . 120.35(16) yes
C32 . C33 . H331 . 119.0 no
C34 . C33 . H331 . 120.6 no
C33 . C34 . C35 . 119.58(16) yes
C33 . C34 . H341 . 120.5 no
C35 . C34 . H341 . 119.9 no
C34 . C35 . C36 . 120.31(16) yes
C34 . C35 . H351 . 119.9 no
C36 . C35 . H351 . 119.8 no
C31 . C36 . C35 . 120.51(15) yes
C31 . C36 . H361 . 120.6 no
C35 . C36 . H361 . 118.9 no
C5 . C51 . O52 . 125.67(14) yes
C5 . C51 . O53 . 109.98(13) yes
O52 . C51 . O53 . 124.33(14) yes
C51 . O53 . C54 . 115.94(13) yes
O53 . C54 . C55 . 107.47(15) yes
O53 . C54 . H541 . 109.5 no
C55 . C54 . H541 . 110.8 no
O53 . C54 . H542 . 109.3 no
C55 . C54 . H542 . 110.6 no
H541 . C54 . H542 . 109.2 no
C54 . C55 . H551 . 110.6 no
C54 . C55 . H552 . 108.5 no
H551 . C55 . H552 . 108.3 no
C54 . C55 . H553 . 110.3 no
H551 . C55 . H553 . 109.4 no
H552 . C55 . H553 . 109.6 no
C45 . C44 . O43 . 111.33(16) yes
C45 . C44 . H441 . 110.2 no
O43 . C44 . H441 . 104.9 no
C45 . C44 . H442 . 110.4 no
O43 . C44 . H442 . 109.4 no
H441 . C44 . H442 . 110.4 no
C44 . C45 . H453 . 108.7 no
C44 . C45 . H452 . 110.3 no
H453 . C45 . H452 . 109.2 no
C44 . C45 . H451 . 109.1 no
H453 . C45 . H451 . 110.5 no
H452 . C45 . H451 . 109.0 no
C144 . C145 . H1451 . 109.7 no
C144 . C145 . H1452 . 110.1 no
H1451 . C145 . H1452 . 109.5 no
C144 . C145 . H1453 . 109.1 no
H1451 . C145 . H1453 . 109.5 no
H1452 . C145 . H1453 . 109.0 no
C145 . C144 . O143 . 103.0(15) yes
C145 . C144 . H1441 . 111.3 no
O143 . C144 . H1441 . 110.5 no
C145 . C144 . H1442 . 111.0 no
O143 . C144 . H1442 . 111.0 no
H1441 . C144 . H1442 . 109.9 no
C144 . O143 . C141 . 112.0(14) yes
C44 . O43 . C41 . 117.18(16) yes
C5 . C141 . O143 . 102.4(12) yes
C5 . C141 . O142 . 120.3(5) yes
O143 . C141 . O142 . 121.1(5) yes
C5 . C41 . O43 . 111.44(15) yes
C5 . C41 . O42 . 123.94(15) yes
O43 . C41 . O42 . 124.57(17) 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
C33 . H331 . O142 2_566 154 0.95 2.36 3.245(5) yes
C33 . H331 . O42 2_566 147 0.95 2.55 3.390(5) yes
N1 . H11 . O142 . 122 0.87 1.90 2.477(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 9 13 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_247a-21a
_database_code_depnum_ccdc_archive 'CCDC 2256195'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2018-08-14
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 7000
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.45120(10)
_cell_length_b                   11.0365(2)
_cell_length_c                   28.8706(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.6424(14)
_cell_angle_gamma                90
_cell_volume                     3005.36(8)

_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 0.0181 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 = C33 H36 N2 O7 
# Dc =      1.27 Fooo =   1216.00 Mu =      7.27 M =    572.66
# Found Formula = C33 H36 N2 O7 
# Dc =      1.27 FOOO =   1216.00 Mu =      7.27 M =    572.66

_chemical_formula_sum            'C33 H36 N2 O7'
_chemical_formula_moiety         'C33 H36 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         572.66


_cell_measurement_reflns_used    10278
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.727

# Sheldrick geometric approximatio 0.86 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.87
_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            22229
_reflns_number_total             6217
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0438
# Number of reflections with Friedels Law is 6217 
# Theoretical number of reflections is about 12578 


_diffrn_reflns_theta_min         4.290
_diffrn_reflns_theta_max         76.171
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        73.886
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      0.07

_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         0.55


# 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     380
_refine_ls_number_reflns         6217
_oxford_refine_ls_R_factor_ref   0.0417
_refine_ls_wR_factor_ref         0.0927
_refine_ls_goodness_of_fit_ref   1.0011
_refine_ls_shift/su_max          0.0011822
_refine_ls_shift/su_mean         0.0000824


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6217
_refine_ls_R_factor_all          0.0417
_refine_ls_wR_factor_all         0.0927

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5346
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_gt          0.0854


_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 + 0.96P] 
 ,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
N1 N 0.34507(10) 0.54699(9) 0.67957(3) 0.0185 1.0000 Uani . . . . . .
C2 C 0.21577(11) 0.48033(10) 0.66337(4) 0.0185 1.0000 Uani . . . . . .
N3 N 0.18109(10) 0.54215(9) 0.61901(3) 0.0190 1.0000 Uani . . . . . .
C4 C 0.31570(11) 0.56738(10) 0.59883(4) 0.0186 1.0000 Uani . . . . . .
C5 C 0.40667(12) 0.61418(10) 0.64262(4) 0.0185 1.0000 Uani . . . . . .
C11 C 0.41456(12) 0.55029(10) 0.72217(4) 0.0197 1.0000 Uani . . . . . .
O12 O 0.52282(9) 0.61110(8) 0.72853(3) 0.0251 1.0000 Uani . . . . . .
C13 C 0.35587(13) 0.47697(12) 0.76099(4) 0.0261 1.0000 Uani . . . . . .
C14 C 0.45525(13) 0.48926(11) 0.80378(4) 0.0234 1.0000 Uani . . . . . .
O15 O 0.44435(12) 0.56517(9) 0.83309(3) 0.0371 1.0000 Uani . . . . . .
O16 O 0.55731(9) 0.40536(8) 0.80448(3) 0.0253 1.0000 Uani . . . . . .
C17 C 0.66286(14) 0.41089(14) 0.84327(4) 0.0309 1.0000 Uani . . . . . .
C18 C 0.60837(16) 0.35570(14) 0.88642(5) 0.0361 1.0000 Uani . . . . . .
C21 C 0.09323(12) 0.49045(11) 0.69453(4) 0.0197 1.0000 Uani . . . . . .
C22 C 0.03849(12) 0.38765(11) 0.71475(4) 0.0228 1.0000 Uani . . . . . .
C23 C -0.07587(13) 0.39799(12) 0.74278(4) 0.0274 1.0000 Uani . . . . . .
C24 C -0.13646(13) 0.51020(13) 0.74949(4) 0.0301 1.0000 Uani . . . . . .
C25 C -0.08164(14) 0.61315(12) 0.72941(4) 0.0286 1.0000 Uani . . . . . .
C26 C 0.03369(13) 0.60371(11) 0.70224(4) 0.0240 1.0000 Uani . . . . . .
C31 C 0.07211(12) 0.48117(12) 0.58836(4) 0.0238 1.0000 Uani . . . . . .
C32 C 0.11952(12) 0.36992(12) 0.56317(4) 0.0239 1.0000 Uani . . . . . .
C33 C 0.11259(14) 0.25518(13) 0.58250(4) 0.0299 1.0000 Uani . . . . . .
C34 C 0.15927(17) 0.15416(14) 0.55904(5) 0.0379 1.0000 Uani . . . . . .
C35 C 0.21439(16) 0.16722(15) 0.51602(5) 0.0398 1.0000 Uani . . . . . .
C36 C 0.22042(15) 0.28117(15) 0.49588(5) 0.0369 1.0000 Uani . . . . . .
C37 C 0.17218(14) 0.38162(13) 0.51912(4) 0.0299 1.0000 Uani . . . . . .
C41 C 0.30224(12) 0.65328(11) 0.55799(4) 0.0204 1.0000 Uani . . . . . .
C42 C 0.19309(13) 0.73749(12) 0.55324(4) 0.0262 1.0000 Uani . . . . . .
C43 C 0.17890(15) 0.81143(13) 0.51429(5) 0.0332 1.0000 Uani . . . . . .
C44 C 0.27521(16) 0.80278(14) 0.48021(5) 0.0371 1.0000 Uani . . . . . .
C45 C 0.38640(15) 0.72163(14) 0.48535(4) 0.0347 1.0000 Uani . . . . . .
C46 C 0.39987(13) 0.64636(12) 0.52390(4) 0.0260 1.0000 Uani . . . . . .
C51 C 0.38318(12) 0.75074(11) 0.65040(4) 0.0208 1.0000 Uani . . . . . .
O52 O 0.29725(10) 0.78861(8) 0.67574(3) 0.0302 1.0000 Uani . . . . . .
O53 O 0.46032(9) 0.81950(8) 0.62409(3) 0.0269 1.0000 Uani . . . . . .
C54 C 0.42781(16) 0.94835(12) 0.62453(5) 0.0333 1.0000 Uani . . . . . .
C55 C 0.49577(16) 1.00221(14) 0.58383(6) 0.0406 1.0000 Uani . . . . . .
C61 C 0.56213(12) 0.57711(11) 0.63676(4) 0.0207 1.0000 Uani . . . . . .
O62 O 0.65425(10) 0.64072(9) 0.62409(4) 0.0339 1.0000 Uani . . . . . .
O63 O 0.57491(8) 0.45752(8) 0.64399(3) 0.0237 1.0000 Uani . . . . . .
C64 C 0.71348(13) 0.40687(12) 0.63628(4) 0.0265 1.0000 Uani . . . . . .
C65 C 0.70945(16) 0.27603(13) 0.65051(6) 0.0376 1.0000 Uani . . . . . .
H21 H 0.2402 0.3926 0.6588 0.0206 1.0000 Uiso R . . . . .
H41 H 0.3619 0.4925 0.5885 0.0207 1.0000 Uiso R . . . . .
H131 H 0.2636 0.5101 0.7670 0.0335 1.0000 Uiso R . . . . .
H132 H 0.3490 0.3932 0.7517 0.0307 1.0000 Uiso R . . . . .
H171 H 0.6899 0.4972 0.8478 0.0368 1.0000 Uiso R . . . . .
H172 H 0.7441 0.3633 0.8334 0.0372 1.0000 Uiso R . . . . .
H181 H 0.6842 0.3586 0.9106 0.0546 1.0000 Uiso R . . . . .
H182 H 0.5286 0.4027 0.8962 0.0534 1.0000 Uiso R . . . . .
H183 H 0.5821 0.2705 0.8804 0.0532 1.0000 Uiso R . . . . .
H221 H 0.0811 0.3086 0.7099 0.0270 1.0000 Uiso R . . . . .
H231 H -0.1120 0.3275 0.7566 0.0322 1.0000 Uiso R . . . . .
H241 H -0.2179 0.5188 0.7677 0.0372 1.0000 Uiso R . . . . .
H251 H -0.1248 0.6905 0.7337 0.0348 1.0000 Uiso R . . . . .
H261 H 0.0707 0.6741 0.6888 0.0278 1.0000 Uiso R . . . . .
H311 H -0.0060 0.4589 0.6078 0.0286 1.0000 Uiso R . . . . .
H312 H 0.0349 0.5421 0.5659 0.0294 1.0000 Uiso R . . . . .
H331 H 0.0752 0.2457 0.6118 0.0360 1.0000 Uiso R . . . . .
H341 H 0.1543 0.0763 0.5727 0.0453 1.0000 Uiso R . . . . .
H351 H 0.2448 0.0982 0.5001 0.0480 1.0000 Uiso R . . . . .
H361 H 0.2588 0.2916 0.4657 0.0447 1.0000 Uiso R . . . . .
H371 H 0.1750 0.4603 0.5055 0.0367 1.0000 Uiso R . . . . .
H421 H 0.1259 0.7420 0.5763 0.0312 1.0000 Uiso R . . . . .
H431 H 0.1027 0.8679 0.5106 0.0400 1.0000 Uiso R . . . . .
H441 H 0.2647 0.8526 0.4538 0.0445 1.0000 Uiso R . . . . .
H451 H 0.4530 0.7162 0.4621 0.0415 1.0000 Uiso R . . . . .
H461 H 0.4768 0.5877 0.5269 0.0310 1.0000 Uiso R . . . . .
H541 H 0.4673 0.9839 0.6542 0.0397 1.0000 Uiso R . . . . .
H542 H 0.3240 0.9587 0.6215 0.0396 1.0000 Uiso R . . . . .
H553 H 0.4750 1.0894 0.5825 0.0591 1.0000 Uiso R . . . . .
H552 H 0.5989 0.9921 0.5875 0.0607 1.0000 Uiso R . . . . .
H551 H 0.4591 0.9655 0.5552 0.0597 1.0000 Uiso R . . . . .
H641 H 0.7849 0.4519 0.6546 0.0311 1.0000 Uiso R . . . . .
H642 H 0.7288 0.4156 0.6036 0.0306 1.0000 Uiso R . . . . .
H651 H 0.8017 0.2379 0.6459 0.0570 1.0000 Uiso R . . . . .
H652 H 0.6893 0.2693 0.6835 0.0535 1.0000 Uiso R . . . . .
H653 H 0.6355 0.2327 0.6315 0.0545 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       21(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          3.84(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
N1 . C2 . 1.4768(14) yes
N1 . C5 . 1.4513(13) yes
N1 . C11 . 1.3573(14) yes
C2 . N3 . 1.4695(14) yes
C2 . C21 . 1.5151(15) yes
C2 . H21 . 1.006 no
N3 . C4 . 1.4594(14) yes
N3 . C31 . 1.4768(14) yes
C4 . C5 . 1.5704(15) yes
C4 . C41 . 1.5119(15) yes
C4 . H41 . 0.990 no
C5 . C51 . 1.5419(16) yes
C5 . C61 . 1.5448(15) yes
C11 . O12 . 1.2276(14) yes
C11 . C13 . 1.5159(15) yes
C13 . C14 . 1.5096(16) yes
C13 . H131 . 0.971 no
C13 . H132 . 0.964 no
C14 . O15 . 1.1998(16) yes
C14 . O16 . 1.3364(15) yes
O16 . C17 . 1.4528(15) yes
C17 . C18 . 1.5067(17) yes
C17 . H171 . 0.993 no
C17 . H172 . 0.987 no
C18 . H181 . 0.969 no
C18 . H182 . 0.971 no
C18 . H183 . 0.985 no
C21 . C22 . 1.3907(16) yes
C21 . C26 . 1.3945(17) yes
C22 . C23 . 1.3955(17) yes
C22 . H221 . 0.974 no
C23 . C24 . 1.383(2) yes
C23 . H231 . 0.948 no
C24 . C25 . 1.3905(19) yes
C24 . H241 . 0.965 no
C25 . C26 . 1.3868(17) yes
C25 . H251 . 0.957 no
C26 . H261 . 0.944 no
C31 . C32 . 1.5094(17) yes
C31 . H311 . 0.987 no
C31 . H312 . 0.984 no
C32 . C33 . 1.3870(18) yes
C32 . C37 . 1.4008(17) yes
C33 . C34 . 1.391(2) yes
C33 . H331 . 0.943 no
C34 . C35 . 1.385(2) yes
C34 . H341 . 0.948 no
C35 . C36 . 1.388(2) yes
C35 . H351 . 0.943 no
C36 . C37 . 1.388(2) yes
C36 . H361 . 0.971 no
C37 . H371 . 0.954 no
C41 . C42 . 1.3888(17) yes
C41 . C46 . 1.3935(16) yes
C42 . C43 . 1.3888(18) yes
C42 . H421 . 0.949 no
C43 . C44 . 1.386(2) yes
C43 . H431 . 0.953 no
C44 . C45 . 1.382(2) yes
C44 . H441 . 0.941 no
C45 . C46 . 1.3881(18) yes
C45 . H451 . 0.951 no
C46 . H461 . 0.973 no
C51 . O52 . 1.2020(15) yes
C51 . O53 . 1.3248(14) yes
O53 . C54 . 1.4551(15) yes
C54 . C55 . 1.4975(19) yes
C54 . H541 . 0.993 no
C54 . H542 . 0.986 no
C55 . H553 . 0.982 no
C55 . H552 . 0.980 no
C55 . H551 . 0.966 no
C61 . O62 . 1.1937(15) yes
C61 . O63 . 1.3405(15) yes
O63 . C64 . 1.4540(14) yes
C64 . C65 . 1.5024(19) yes
C64 . H641 . 0.969 no
C64 . H642 . 0.967 no
C65 . H651 . 0.984 no
C65 . H652 . 0.985 no
C65 . H653 . 0.985 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
C2 . N1 . C5 . 112.59(8) yes
C2 . N1 . C11 . 130.05(9) yes
C5 . N1 . C11 . 117.31(9) yes
N1 . C2 . N3 . 100.31(8) yes
N1 . C2 . C21 . 115.05(9) yes
N3 . C2 . C21 . 110.29(9) yes
N1 . C2 . H21 . 109.2 no
N3 . C2 . H21 . 111.9 no
C21 . C2 . H21 . 109.8 no
C2 . N3 . C4 . 106.54(8) yes
C2 . N3 . C31 . 114.77(9) yes
C4 . N3 . C31 . 116.12(9) yes
N3 . C4 . C5 . 100.83(8) yes
N3 . C4 . C41 . 113.49(9) yes
C5 . C4 . C41 . 115.86(9) yes
N3 . C4 . H41 . 111.9 no
C5 . C4 . H41 . 106.7 no
C41 . C4 . H41 . 107.8 no
C4 . C5 . N1 . 101.49(8) yes
C4 . C5 . C51 . 111.25(9) yes
N1 . C5 . C51 . 108.91(9) yes
C4 . C5 . C61 . 107.49(9) yes
N1 . C5 . C61 . 111.96(9) yes
C51 . C5 . C61 . 114.94(9) yes
N1 . C11 . O12 . 120.06(10) yes
N1 . C11 . C13 . 118.48(10) yes
O12 . C11 . C13 . 121.45(10) yes
C11 . C13 . C14 . 108.62(10) yes
C11 . C13 . H131 . 107.8 no
C14 . C13 . H131 . 109.8 no
C11 . C13 . H132 . 109.1 no
C14 . C13 . H132 . 110.0 no
H131 . C13 . H132 . 111.4 no
C13 . C14 . O15 . 124.26(12) yes
C13 . C14 . O16 . 111.17(10) yes
O15 . C14 . O16 . 124.56(11) yes
C14 . O16 . C17 . 116.25(10) yes
O16 . C17 . C18 . 111.49(11) yes
O16 . C17 . H171 . 107.5 no
C18 . C17 . H171 . 112.2 no
O16 . C17 . H172 . 105.3 no
C18 . C17 . H172 . 109.6 no
H171 . C17 . H172 . 110.5 no
C17 . C18 . H181 . 107.8 no
C17 . C18 . H182 . 109.6 no
H181 . C18 . H182 . 109.0 no
C17 . C18 . H183 . 109.5 no
H181 . C18 . H183 . 109.0 no
H182 . C18 . H183 . 111.7 no
C2 . C21 . C22 . 120.53(11) yes
C2 . C21 . C26 . 119.49(10) yes
C22 . C21 . C26 . 119.97(11) yes
C21 . C22 . C23 . 119.95(12) yes
C21 . C22 . H221 . 120.1 no
C23 . C22 . H221 . 120.0 no
C22 . C23 . C24 . 119.82(12) yes
C22 . C23 . H231 . 119.3 no
C24 . C23 . H231 . 120.8 no
C23 . C24 . C25 . 120.31(11) yes
C23 . C24 . H241 . 121.1 no
C25 . C24 . H241 . 118.6 no
C24 . C25 . C26 . 120.10(12) yes
C24 . C25 . H251 . 120.1 no
C26 . C25 . H251 . 119.8 no
C21 . C26 . C25 . 119.82(11) yes
C21 . C26 . H261 . 120.5 no
C25 . C26 . H261 . 119.6 no
N3 . C31 . C32 . 116.25(10) yes
N3 . C31 . H311 . 106.9 no
C32 . C31 . H311 . 109.1 no
N3 . C31 . H312 . 106.9 no
C32 . C31 . H312 . 110.0 no
H311 . C31 . H312 . 107.3 no
C31 . C32 . C33 . 121.72(11) yes
C31 . C32 . C37 . 119.72(12) yes
C33 . C32 . C37 . 118.55(12) yes
C32 . C33 . C34 . 120.76(12) yes
C32 . C33 . H331 . 119.5 no
C34 . C33 . H331 . 119.8 no
C33 . C34 . C35 . 120.16(14) yes
C33 . C34 . H341 . 119.8 no
C35 . C34 . H341 . 120.0 no
C34 . C35 . C36 . 119.86(14) yes
C34 . C35 . H351 . 119.7 no
C36 . C35 . H351 . 120.4 no
C35 . C36 . C37 . 119.84(13) yes
C35 . C36 . H361 . 120.7 no
C37 . C36 . H361 . 119.4 no
C32 . C37 . C36 . 120.80(13) yes
C32 . C37 . H371 . 118.6 no
C36 . C37 . H371 . 120.6 no
C4 . C41 . C42 . 121.46(10) yes
C4 . C41 . C46 . 119.32(11) yes
C42 . C41 . C46 . 119.20(11) yes
C41 . C42 . C43 . 120.41(12) yes
C41 . C42 . H421 . 119.4 no
C43 . C42 . H421 . 120.1 no
C42 . C43 . C44 . 120.03(13) yes
C42 . C43 . H431 . 120.6 no
C44 . C43 . H431 . 119.3 no
C43 . C44 . C45 . 119.87(12) yes
C43 . C44 . H441 . 119.7 no
C45 . C44 . H441 . 120.4 no
C44 . C45 . C46 . 120.29(12) yes
C44 . C45 . H451 . 119.9 no
C46 . C45 . H451 . 119.8 no
C41 . C46 . C45 . 120.16(12) yes
C41 . C46 . H461 . 119.9 no
C45 . C46 . H461 . 120.0 no
C5 . C51 . O52 . 122.53(10) yes
C5 . C51 . O53 . 112.75(10) yes
O52 . C51 . O53 . 124.58(11) yes
C51 . O53 . C54 . 115.50(10) yes
O53 . C54 . C55 . 106.24(12) yes
O53 . C54 . H541 . 109.0 no
C55 . C54 . H541 . 111.3 no
O53 . C54 . H542 . 108.8 no
C55 . C54 . H542 . 110.9 no
H541 . C54 . H542 . 110.5 no
C54 . C55 . H553 . 109.0 no
C54 . C55 . H552 . 110.1 no
H553 . C55 . H552 . 108.1 no
C54 . C55 . H551 . 111.0 no
H553 . C55 . H551 . 108.5 no
H552 . C55 . H551 . 110.1 no
C5 . C61 . O62 . 126.51(11) yes
C5 . C61 . O63 . 108.70(9) yes
O62 . C61 . O63 . 124.51(11) yes
C61 . O63 . C64 . 115.33(9) yes
O63 . C64 . C65 . 106.80(10) yes
O63 . C64 . H641 . 108.8 no
C65 . C64 . H641 . 111.9 no
O63 . C64 . H642 . 107.6 no
C65 . C64 . H642 . 111.7 no
H641 . C64 . H642 . 109.8 no
C64 . C65 . H651 . 109.6 no
C64 . C65 . H652 . 110.2 no
H651 . C65 . H652 . 109.0 no
C64 . C65 . H653 . 110.1 no
H651 . C65 . H653 . 108.7 no
H652 . C65 . H653 . 109.1 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
C23 . H231 . O12 4_546 135 0.95 2.56 3.3030(18) yes
C26 . H261 . O52 . 144 0.94 2.54 3.3461(18) yes
C33 . H331 . O15 4_546 134 0.94 2.56 3.2853(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_247c-21c
_database_code_depnum_ccdc_archive 'CCDC 2256196'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2018-10-29
_audit_creation_method           CRYSTALS_ver_14.61_build_7031

_oxford_structure_analysis_title 7053
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.7028(3)
_cell_length_b                   10.3166(2)
_cell_length_c                   17.6915(4)
_cell_angle_alpha                78.751(2)
_cell_angle_beta                 76.109(2)
_cell_angle_gamma                69.254(2)
_cell_volume                     1595.80(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'
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            2

# Given Formula = C35 H40 N2 O9 
# Dc =      1.32 Fooo =    672.00 Mu =      7.84 M =    632.71
# Found Formula = C35 H40.00 N2 O9 
# Dc =      1.32 FOOO =    672.00 Mu =      7.84 M =    632.71

_chemical_formula_sum            'C35 H40 N2 O9'
_chemical_formula_moiety         'C35 H40 N2 O9'
_chemical_compound_source        .
_chemical_formula_weight         632.71


_cell_measurement_reflns_used    17026
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             671.995
_exptl_absorpt_coefficient_mu    0.784

# Sheldrick geometric approximatio 0.80 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.79
_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            29380
_diffrn_reflns_av_unetI/netI     0.034
_reflns_number_total             6615
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0335
# Number of reflections with Friedels Law is 6615 
# Theoretical number of reflections is about 13366 

_diffrn_reflns_theta_min         4.617
_diffrn_reflns_theta_max         76.219
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        74.695
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -11
_reflns_limit_h_max              12
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   1.95
_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         -0.21
_refine_diff_density_max         0.29


# 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     415
_refine_ls_number_reflns         6614
_oxford_refine_ls_R_factor_ref   0.0351
_refine_ls_wR_factor_ref         0.0836
_refine_ls_goodness_of_fit_ref   0.9937
_refine_ls_shift/su_max          0.0004999
_refine_ls_shift/su_mean         0.0000614


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6615
_refine_ls_R_factor_all          0.0351
_refine_ls_wR_factor_all         0.0842

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6043
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0811


_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 + 0.48P] 
 ,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
N1 N 0.74057(9) 0.71040(8) 0.30585(5) 0.0180 1.0000 Uani . . . . . .
C2 C 0.60282(10) 0.75333(10) 0.27219(6) 0.0182 1.0000 Uani . . . . . .
N3 N 0.60977(9) 0.88540(9) 0.22543(5) 0.0191 1.0000 Uani . . . . . .
C4 C 0.76710(10) 0.86641(10) 0.19150(6) 0.0185 1.0000 Uani . . . . . .
C5 C 0.84340(10) 0.78510(10) 0.26377(6) 0.0183 1.0000 Uani . . . . . .
C11 C 0.78313(11) 0.61508(10) 0.36776(6) 0.0196 1.0000 Uani . . . . . .
O12 O 0.90343(8) 0.59700(8) 0.38614(4) 0.0257 1.0000 Uani . . . . . .
C13 C 0.68105(11) 0.53373(10) 0.41448(6) 0.0209 1.0000 Uani . . . . . .
C14 C 0.65397(11) 0.43921(10) 0.36857(6) 0.0215 1.0000 Uani . . . . . .
O15 O 0.71457(10) 0.41715(9) 0.30252(5) 0.0363 1.0000 Uani . . . . . .
O16 O 0.55313(8) 0.38114(8) 0.41225(4) 0.0245 1.0000 Uani . . . . . .
C17 C 0.51807(13) 0.28585(12) 0.37504(7) 0.0292 1.0000 Uani . . . . . .
C18 C 0.38392(14) 0.25386(14) 0.42595(8) 0.0366 1.0000 Uani . . . . . .
C21 C 0.45985(10) 0.77437(10) 0.33247(6) 0.0188 1.0000 Uani . . . . . .
C22 C 0.42689(11) 0.86289(10) 0.38974(6) 0.0209 1.0000 Uani . . . . . .
C23 C 0.30157(11) 0.87538(11) 0.44813(6) 0.0221 1.0000 Uani . . . . . .
C24 C 0.20475(11) 0.80071(11) 0.44974(6) 0.0211 1.0000 Uani . . . . . .
C25 C 0.23167(11) 0.71785(11) 0.39129(6) 0.0216 1.0000 Uani . . . . . .
C26 C 0.36035(11) 0.70484(10) 0.33322(6) 0.0205 1.0000 Uani . . . . . .
O27 O 0.08825(8) 0.81592(9) 0.51202(5) 0.0289 1.0000 Uani . . . . . .
C28 C -0.02069(12) 0.75067(13) 0.51428(7) 0.0289 1.0000 Uani . . . . . .
C31 C 0.50281(11) 0.94361(11) 0.17109(6) 0.0233 1.0000 Uani . . . . . .
C32 C 0.51709(12) 0.85945(11) 0.10662(6) 0.0244 1.0000 Uani . . . . . .
C33 C 0.62692(12) 0.85643(12) 0.03917(6) 0.0273 1.0000 Uani . . . . . .
C34 C 0.63497(14) 0.78565(13) -0.02188(7) 0.0354 1.0000 Uani . . . . . .
C35 C 0.53120(17) 0.71959(15) -0.01683(8) 0.0438 1.0000 Uani . . . . . .
C36 C 0.42028(18) 0.72322(17) 0.04918(9) 0.0474 1.0000 Uani . . . . . .
C37 C 0.41327(15) 0.79225(15) 0.11096(7) 0.0367 1.0000 Uani . . . . . .
C41 C 0.79981(11) 1.00115(10) 0.15843(6) 0.0199 1.0000 Uani . . . . . .
C42 C 0.70771(11) 1.12816(11) 0.18382(6) 0.0225 1.0000 Uani . . . . . .
C43 C 0.74368(12) 1.25039(11) 0.15588(6) 0.0255 1.0000 Uani . . . . . .
C44 C 0.87566(13) 1.24446(12) 0.10226(6) 0.0274 1.0000 Uani . . . . . .
C45 C 0.96995(13) 1.11734(12) 0.07725(7) 0.0303 1.0000 Uani . . . . . .
C46 C 0.93165(12) 0.99745(11) 0.10452(6) 0.0256 1.0000 Uani . . . . . .
O47 O 0.92418(11) 1.35664(9) 0.07113(5) 0.0380 1.0000 Uani . . . . . .
C48 C 0.82821(16) 1.48976(13) 0.09376(9) 0.0408 1.0000 Uani . . . . . .
C51 C 1.00005(11) 0.68649(10) 0.23182(6) 0.0210 1.0000 Uani . . . . . .
O52 O 1.11416(9) 0.71409(8) 0.21636(6) 0.0363 1.0000 Uani . . . . . .
O53 O 0.98867(8) 0.56929(8) 0.21664(5) 0.0278 1.0000 Uani . . . . . .
C54 C 1.12702(13) 0.47079(12) 0.18103(8) 0.0340 1.0000 Uani . . . . . .
C55 C 1.23316(16) 0.40048(14) 0.23701(10) 0.0453 1.0000 Uani . . . . . .
C61 C 0.84445(11) 0.88951(10) 0.31538(6) 0.0192 1.0000 Uani . . . . . .
O62 O 0.74588(8) 0.92687(8) 0.37038(4) 0.0259 1.0000 Uani . . . . . .
O63 O 0.95871(8) 0.93782(8) 0.28944(4) 0.0233 1.0000 Uani . . . . . .
C64 C 0.95348(12) 1.05312(11) 0.32737(7) 0.0263 1.0000 Uani . . . . . .
C65 C 1.08733(14) 1.09638(14) 0.28627(8) 0.0357 1.0000 Uani . . . . . .
H21 H 0.6103 0.6832 0.2388 0.0204 1.0000 Uiso R . . . . .
H41 H 0.8069 0.8016 0.1505 0.0217 1.0000 Uiso R . . . . .
H131 H 0.7286 0.4760 0.4568 0.0258 1.0000 Uiso R . . . . .
H132 H 0.5839 0.5967 0.4368 0.0259 1.0000 Uiso R . . . . .
H171 H 0.6057 0.2022 0.3698 0.0367 1.0000 Uiso R . . . . .
H172 H 0.4983 0.3308 0.3225 0.0358 1.0000 Uiso R . . . . .
H183 H 0.3613 0.1887 0.4012 0.0537 1.0000 Uiso R . . . . .
H182 H 0.4031 0.2098 0.4778 0.0562 1.0000 Uiso R . . . . .
H181 H 0.2957 0.3380 0.4308 0.0543 1.0000 Uiso R . . . . .
H221 H 0.4932 0.9128 0.3891 0.0253 1.0000 Uiso R . . . . .
H231 H 0.2792 0.9331 0.4879 0.0274 1.0000 Uiso R . . . . .
H251 H 0.1650 0.6694 0.3903 0.0268 1.0000 Uiso R . . . . .
H261 H 0.3809 0.6449 0.2938 0.0249 1.0000 Uiso R . . . . .
H281 H -0.0948 0.7761 0.5620 0.0427 1.0000 Uiso R . . . . .
H282 H 0.0234 0.6486 0.5180 0.0414 1.0000 Uiso R . . . . .
H283 H -0.0677 0.7852 0.4682 0.0414 1.0000 Uiso R . . . . .
H311 H 0.5140 1.0346 0.1470 0.0268 1.0000 Uiso R . . . . .
H312 H 0.4022 0.9597 0.2038 0.0279 1.0000 Uiso R . . . . .
H331 H 0.6956 0.9067 0.0342 0.0332 1.0000 Uiso R . . . . .
H341 H 0.7123 0.7851 -0.0674 0.0432 1.0000 Uiso R . . . . .
H351 H 0.5357 0.6725 -0.0587 0.0530 1.0000 Uiso R . . . . .
H361 H 0.3485 0.6779 0.0524 0.0580 1.0000 Uiso R . . . . .
H371 H 0.3353 0.7949 0.1566 0.0437 1.0000 Uiso R . . . . .
H421 H 0.6173 1.1320 0.2213 0.0269 1.0000 Uiso R . . . . .
H431 H 0.6796 1.3361 0.1742 0.0317 1.0000 Uiso R . . . . .
H451 H 1.0614 1.1145 0.0406 0.0369 1.0000 Uiso R . . . . .
H461 H 0.9986 0.9100 0.0867 0.0314 1.0000 Uiso R . . . . .
H483 H 0.8786 1.5562 0.0662 0.0590 1.0000 Uiso R . . . . .
H482 H 0.8138 1.4894 0.1522 0.0598 1.0000 Uiso R . . . . .
H481 H 0.7290 1.5143 0.0781 0.0597 1.0000 Uiso R . . . . .
H541 H 1.1726 0.5202 0.1351 0.0404 1.0000 Uiso R . . . . .
H542 H 1.0934 0.4020 0.1653 0.0410 1.0000 Uiso R . . . . .
H553 H 1.3103 0.3180 0.2169 0.0671 1.0000 Uiso R . . . . .
H552 H 1.2795 0.4656 0.2460 0.0669 1.0000 Uiso R . . . . .
H551 H 1.1784 0.3703 0.2871 0.0680 1.0000 Uiso R . . . . .
H641 H 0.9554 1.0214 0.3822 0.0313 1.0000 Uiso R . . . . .
H642 H 0.8597 1.1288 0.3219 0.0326 1.0000 Uiso R . . . . .
H653 H 1.0806 1.1788 0.3075 0.0547 1.0000 Uiso R . . . . .
H652 H 1.1818 1.0227 0.2953 0.0534 1.0000 Uiso R . . . . .
H651 H 1.0872 1.1218 0.2307 0.0536 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.70(7)
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
N1 . C2 . 1.4823(12) yes
N1 . C5 . 1.4518(12) yes
N1 . C11 . 1.3588(13) yes
C2 . N3 . 1.4643(12) yes
C2 . C21 . 1.5084(13) yes
C2 . H21 . 0.993 no
N3 . C4 . 1.4570(12) yes
N3 . C31 . 1.4745(12) yes
C4 . C5 . 1.5756(13) yes
C4 . C41 . 1.5104(13) yes
C4 . H41 . 0.998 no
C5 . C51 . 1.5431(13) yes
C5 . C61 . 1.5459(13) yes
C11 . O12 . 1.2278(12) yes
C11 . C13 . 1.5145(13) yes
C13 . C14 . 1.5075(14) yes
C13 . H131 . 0.963 no
C13 . H132 . 0.977 no
C14 . O15 . 1.2009(13) yes
C14 . O16 . 1.3360(12) yes
O16 . C17 . 1.4534(12) yes
C17 . C18 . 1.4966(15) yes
C17 . H171 . 0.975 no
C17 . H172 . 0.986 no
C18 . H183 . 0.978 no
C18 . H182 . 0.971 no
C18 . H181 . 0.980 no
C21 . C22 . 1.4005(14) yes
C21 . C26 . 1.3884(13) yes
C22 . C23 . 1.3784(14) yes
C22 . H221 . 0.952 no
C23 . C24 . 1.4027(14) yes
C23 . H231 . 0.946 no
C24 . C25 . 1.3876(14) yes
C24 . O27 . 1.3638(12) yes
C25 . C26 . 1.3970(14) yes
C25 . H251 . 0.953 no
C26 . H261 . 0.961 no
O27 . C28 . 1.4301(13) yes
C28 . H281 . 0.980 no
C28 . H282 . 0.982 no
C28 . H283 . 0.974 no
C31 . C32 . 1.5164(15) yes
C31 . H311 . 0.984 no
C31 . H312 . 0.984 no
C32 . C33 . 1.3931(15) yes
C32 . C37 . 1.3922(15) yes
C33 . C34 . 1.3901(17) yes
C33 . H331 . 0.958 no
C34 . C35 . 1.380(2) yes
C34 . H341 . 0.960 no
C35 . C36 . 1.382(2) yes
C35 . H351 . 0.947 no
C36 . C37 . 1.3928(19) yes
C36 . H361 . 0.953 no
C37 . H371 . 0.962 no
C41 . C42 . 1.3873(14) yes
C41 . C46 . 1.3933(14) yes
C42 . C43 . 1.3935(14) yes
C42 . H421 . 0.958 no
C43 . C44 . 1.3883(15) yes
C43 . H431 . 0.948 no
C44 . C45 . 1.3909(16) yes
C44 . O47 . 1.3701(13) yes
C45 . C46 . 1.3812(15) yes
C45 . H451 . 0.960 no
C46 . H461 . 0.965 no
O47 . C48 . 1.4294(16) yes
C48 . H483 . 0.969 no
C48 . H482 . 1.009 no
C48 . H481 . 0.998 no
C51 . O52 . 1.1956(13) yes
C51 . O53 . 1.3349(12) yes
O53 . C54 . 1.4522(13) yes
C54 . C55 . 1.4994(19) yes
C54 . H541 . 0.970 no
C54 . H542 . 0.986 no
C55 . H553 . 0.974 no
C55 . H552 . 0.984 no
C55 . H551 . 0.974 no
C61 . O62 . 1.2035(12) yes
C61 . O63 . 1.3213(12) yes
O63 . C64 . 1.4561(12) yes
C64 . C65 . 1.4984(15) yes
C64 . H641 . 0.963 no
C64 . H642 . 0.978 no
C65 . H653 . 0.971 no
C65 . H652 . 0.986 no
C65 . H651 . 0.967 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
C2 . N1 . C5 . 112.25(7) yes
C2 . N1 . C11 . 130.60(8) yes
C5 . N1 . C11 . 117.15(8) yes
N1 . C2 . N3 . 100.55(7) yes
N1 . C2 . C21 . 114.23(8) yes
N3 . C2 . C21 . 111.33(8) yes
N1 . C2 . H21 . 109.9 no
N3 . C2 . H21 . 111.7 no
C21 . C2 . H21 . 109.0 no
C2 . N3 . C4 . 107.00(7) yes
C2 . N3 . C31 . 114.50(8) yes
C4 . N3 . C31 . 116.68(8) yes
N3 . C4 . C5 . 100.88(7) yes
N3 . C4 . C41 . 113.92(8) yes
C5 . C4 . C41 . 114.14(8) yes
N3 . C4 . H41 . 112.3 no
C5 . C4 . H41 . 105.9 no
C41 . C4 . H41 . 109.3 no
C4 . C5 . N1 . 101.76(7) yes
C4 . C5 . C51 . 107.78(8) yes
N1 . C5 . C51 . 112.70(8) yes
C4 . C5 . C61 . 110.06(7) yes
N1 . C5 . C61 . 109.30(8) yes
C51 . C5 . C61 . 114.47(8) yes
N1 . C11 . O12 . 119.62(9) yes
N1 . C11 . C13 . 119.95(8) yes
O12 . C11 . C13 . 120.42(9) yes
C11 . C13 . C14 . 114.43(8) yes
C11 . C13 . H131 . 107.1 no
C14 . C13 . H131 . 107.6 no
C11 . C13 . H132 . 110.8 no
C14 . C13 . H132 . 108.2 no
H131 . C13 . H132 . 108.5 no
C13 . C14 . O15 . 125.52(9) yes
C13 . C14 . O16 . 110.26(8) yes
O15 . C14 . O16 . 124.21(9) yes
C14 . O16 . C17 . 115.84(8) yes
O16 . C17 . C18 . 107.92(9) yes
O16 . C17 . H171 . 107.6 no
C18 . C17 . H171 . 111.7 no
O16 . C17 . H172 . 108.6 no
C18 . C17 . H172 . 111.6 no
H171 . C17 . H172 . 109.3 no
C17 . C18 . H183 . 107.8 no
C17 . C18 . H182 . 111.7 no
H183 . C18 . H182 . 108.1 no
C17 . C18 . H181 . 111.6 no
H183 . C18 . H181 . 108.1 no
H182 . C18 . H181 . 109.4 no
C2 . C21 . C22 . 120.20(8) yes
C2 . C21 . C26 . 120.91(9) yes
C22 . C21 . C26 . 118.88(9) yes
C21 . C22 . C23 . 120.50(9) yes
C21 . C22 . H221 . 119.6 no
C23 . C22 . H221 . 119.9 no
C22 . C23 . C24 . 119.96(9) yes
C22 . C23 . H231 . 121.4 no
C24 . C23 . H231 . 118.6 no
C23 . C24 . C25 . 120.31(9) yes
C23 . C24 . O27 . 114.98(9) yes
C25 . C24 . O27 . 124.71(9) yes
C24 . C25 . C26 . 118.90(9) yes
C24 . C25 . H251 . 121.5 no
C26 . C25 . H251 . 119.6 no
C25 . C26 . C21 . 121.33(9) yes
C25 . C26 . H261 . 118.9 no
C21 . C26 . H261 . 119.7 no
C24 . O27 . C28 . 117.82(8) yes
O27 . C28 . H281 . 104.9 no
O27 . C28 . H282 . 111.8 no
H281 . C28 . H282 . 109.1 no
O27 . C28 . H283 . 111.0 no
H281 . C28 . H283 . 110.5 no
H282 . C28 . H283 . 109.4 no
N3 . C31 . C32 . 118.34(8) yes
N3 . C31 . H311 . 105.8 no
C32 . C31 . H311 . 108.9 no
N3 . C31 . H312 . 106.2 no
C32 . C31 . H312 . 108.8 no
H311 . C31 . H312 . 108.5 no
C31 . C32 . C33 . 120.87(9) yes
C31 . C32 . C37 . 120.46(10) yes
C33 . C32 . C37 . 118.48(11) yes
C32 . C33 . C34 . 120.95(11) yes
C32 . C33 . H331 . 119.3 no
C34 . C33 . H331 . 119.7 no
C33 . C34 . C35 . 119.94(12) yes
C33 . C34 . H341 . 118.9 no
C35 . C34 . H341 . 121.1 no
C34 . C35 . C36 . 119.84(12) yes
C34 . C35 . H351 . 120.0 no
C36 . C35 . H351 . 120.2 no
C35 . C36 . C37 . 120.36(12) yes
C35 . C36 . H361 . 119.6 no
C37 . C36 . H361 . 120.0 no
C36 . C37 . C32 . 120.41(12) yes
C36 . C37 . H371 . 119.9 no
C32 . C37 . H371 . 119.7 no
C4 . C41 . C42 . 122.12(9) yes
C4 . C41 . C46 . 119.30(9) yes
C42 . C41 . C46 . 118.43(9) yes
C41 . C42 . C43 . 121.46(9) yes
C41 . C42 . H421 . 119.3 no
C43 . C42 . H421 . 119.2 no
C42 . C43 . C44 . 119.21(10) yes
C42 . C43 . H431 . 120.2 no
C44 . C43 . H431 . 120.5 no
C43 . C44 . C45 . 119.83(10) yes
C43 . C44 . O47 . 124.79(10) yes
C45 . C44 . O47 . 115.38(10) yes
C44 . C45 . C46 . 120.30(10) yes
C44 . C45 . H451 . 119.0 no
C46 . C45 . H451 . 120.7 no
C41 . C46 . C45 . 120.75(10) yes
C41 . C46 . H461 . 120.0 no
C45 . C46 . H461 . 119.2 no
C44 . O47 . C48 . 117.00(10) yes
O47 . C48 . H483 . 106.0 no
O47 . C48 . H482 . 110.5 no
H483 . C48 . H482 . 109.9 no
O47 . C48 . H481 . 110.4 no
H483 . C48 . H481 . 110.1 no
H482 . C48 . H481 . 109.9 no
C5 . C51 . O52 . 125.64(9) yes
C5 . C51 . O53 . 110.06(8) yes
O52 . C51 . O53 . 124.03(9) yes
C51 . O53 . C54 . 115.89(8) yes
O53 . C54 . C55 . 112.58(11) yes
O53 . C54 . H541 . 108.2 no
C55 . C54 . H541 . 111.3 no
O53 . C54 . H542 . 103.8 no
C55 . C54 . H542 . 110.4 no
H541 . C54 . H542 . 110.3 no
C54 . C55 . H553 . 110.4 no
C54 . C55 . H552 . 110.5 no
H553 . C55 . H552 . 110.2 no
C54 . C55 . H551 . 109.4 no
H553 . C55 . H551 . 107.9 no
H552 . C55 . H551 . 108.3 no
C5 . C61 . O62 . 122.37(9) yes
C5 . C61 . O63 . 112.69(8) yes
O62 . C61 . O63 . 124.81(9) yes
C61 . O63 . C64 . 115.55(8) yes
O63 . C64 . C65 . 106.62(9) yes
O63 . C64 . H641 . 108.6 no
C65 . C64 . H641 . 112.2 no
O63 . C64 . H642 . 108.3 no
C65 . C64 . H642 . 111.6 no
H641 . C64 . H642 . 109.5 no
C64 . C65 . H653 . 107.7 no
C64 . C65 . H652 . 111.5 no
H653 . C65 . H652 . 108.4 no
C64 . C65 . H651 . 111.1 no
H653 . C65 . H651 . 107.5 no
H652 . C65 . H651 . 110.5 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
C22 . H221 . O62 . 151 0.95 2.45 3.3141(17) yes
C37 . H371 . O52 1_455 143 0.96 2.50 3.3200(17) 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
10 -2 7 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_245g-20g
_database_code_depnum_ccdc_archive 'CCDC 2256194'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2020-01-21
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7261
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   20.3461(7)
_cell_length_b                   7.4845(2)
_cell_length_c                   20.4659(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.544(4)
_cell_angle_gamma                90
_cell_volume                     2954.74(18)

_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'
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 = C36 H34 N2 O4 
# Dc =      1.26 Fooo =   1184.00 Mu =      6.53 M =    558.68
# Found Formula = C36 H34 N2 O4 
# Dc =      1.26 FOOO =   1184.00 Mu =      6.53 M =    558.68

_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         558.68


_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      75.86
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.653

# Sheldrick geometric approximatio 0.97 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.83
_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            13399
_diffrn_reflns_av_unetI/netI     0.060
_reflns_number_total             6166
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0611
# Number of reflections with Friedels Law is 6166 
# Theoretical number of reflections is about 12538 

_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         77.101
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        74.017
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -25
_reflns_limit_h_max              24
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.79
_oxford_diffrn_Wilson_scale      0.07

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

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.48


# 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     379
_refine_ls_number_reflns         6163
_oxford_refine_ls_R_factor_ref   0.0737
_refine_ls_R_factor_all          0.0737
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_all         0.1504
_refine_ls_goodness_of_fit_ref   1.0153
_refine_ls_shift/su_max          0.0004870
_refine_ls_shift/su_mean         0.0000495


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        6163
_oxford_refine_ls_R_factor_all   0.0737
_oxford_refine_ls_wR_factor_all  0.1504

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4677
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_gt          0.1329


_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 + 1.24P] 
 ,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
C1 C 0.75388(10) 0.5393(3) 0.69481(10) 0.0296 1.0000 Uani . . . . . .
N2 N 0.80439(8) 0.3983(2) 0.69533(8) 0.0290 1.0000 Uani . . . . . .
C3 C 0.83783(9) 0.3484(2) 0.76750(9) 0.0229 1.0000 Uani . . . . . .
C4 C 0.79357(9) 0.4400(2) 0.80930(9) 0.0233 1.0000 Uani . . . . . .
N5 N 0.73108(8) 0.5006(2) 0.75465(8) 0.0258 1.0000 Uani . . . . . .
C6 C 0.70125(10) 0.6571(3) 0.77915(11) 0.0325 1.0000 Uani . . . . . .
C7 C 0.62735(10) 0.6960(3) 0.73530(11) 0.0342 1.0000 Uani . . . . . .
C8 C 0.57466(12) 0.5813(4) 0.73790(15) 0.0516 1.0000 Uani . . . . . .
C9 C 0.50662(14) 0.6133(5) 0.69977(18) 0.0684 1.0000 Uani . . . . . .
C10 C 0.49014(15) 0.7610(6) 0.65717(17) 0.0726 1.0000 Uani . . . . . .
C11 C 0.54182(18) 0.8768(5) 0.65436(16) 0.0689 1.0000 Uani . . . . . .
C12 C 0.61133(14) 0.8463(4) 0.69425(13) 0.0473 1.0000 Uani . . . . . .
C21 C 0.69468(11) 0.5356(3) 0.62679(10) 0.0337 1.0000 Uani . . . . . .
C22 C 0.65194(12) 0.3883(4) 0.61289(12) 0.0442 1.0000 Uani . . . . . .
C23 C 0.59726(14) 0.3722(5) 0.55011(15) 0.0566 1.0000 Uani . . . . . .
C24 C 0.58586(13) 0.5035(5) 0.50171(12) 0.0525 1.0000 Uani . . . . . .
C25 C 0.62824(12) 0.6575(4) 0.51391(11) 0.0449 1.0000 Uani . . . . . .
C26 C 0.61870(16) 0.7934(5) 0.46290(13) 0.0597 1.0000 Uani . . . . . .
C27 C 0.6613(2) 0.9380(5) 0.47326(16) 0.0697 1.0000 Uani . . . . . .
C28 C 0.71506(18) 0.9557(4) 0.53585(15) 0.0607 1.0000 Uani . . . . . .
C29 C 0.72650(13) 0.8288(3) 0.58670(12) 0.0432 1.0000 Uani . . . . . .
C30 C 0.68418(11) 0.6738(3) 0.57706(10) 0.0347 1.0000 Uani . . . . . .
C31 C 0.91334(9) 0.4147(2) 0.79012(9) 0.0237 1.0000 Uani . . . . . .
O32 O 0.93571(7) 0.53851(19) 0.82824(7) 0.0306 1.0000 Uani . . . . . .
O33 O 0.95018(7) 0.31746(19) 0.75965(7) 0.0296 1.0000 Uani . . . . . .
C34 C 1.02466(11) 0.3525(3) 0.78029(13) 0.0385 1.0000 Uani . . . . . .
C35 C 1.06167(12) 0.2402(4) 0.84168(14) 0.0505 1.0000 Uani . . . . . .
C36 C 0.83852(9) 0.1465(3) 0.77671(10) 0.0257 1.0000 Uani . . . . . .
O37 O 0.80188(8) 0.0440(2) 0.73567(8) 0.0368 1.0000 Uani . . . . . .
O38 O 0.88316(7) 0.10400(17) 0.83742(7) 0.0266 1.0000 Uani . . . . . .
C39 C 0.87815(11) -0.0752(3) 0.86305(11) 0.0330 1.0000 Uani . . . . . .
C40 C 0.93245(13) -0.0882(3) 0.93220(12) 0.0437 1.0000 Uani . . . . . .
C41 C 0.77449(9) 0.3185(3) 0.85997(9) 0.0254 1.0000 Uani . . . . . .
C42 C 0.71690(10) 0.2102(3) 0.83676(11) 0.0315 1.0000 Uani . . . . . .
C43 C 0.69949(11) 0.0861(3) 0.88027(13) 0.0413 1.0000 Uani . . . . . .
C44 C 0.73992(12) 0.0711(4) 0.94738(13) 0.0446 1.0000 Uani . . . . . .
C45 C 0.79873(11) 0.1814(3) 0.97417(11) 0.0357 1.0000 Uani . . . . . .
C46 C 0.84098(14) 0.1688(4) 1.04472(12) 0.0476 1.0000 Uani . . . . . .
C47 C 0.89793(14) 0.2739(4) 1.07034(11) 0.0477 1.0000 Uani . . . . . .
C48 C 0.91703(13) 0.3952(3) 1.02715(11) 0.0416 1.0000 Uani . . . . . .
C49 C 0.87782(11) 0.4112(3) 0.95913(10) 0.0320 1.0000 Uani . . . . . .
C50 C 0.81730(10) 0.3074(3) 0.93051(9) 0.0270 1.0000 Uani . . . . . .
H11 H 0.7787 0.6564 0.7015 0.0350 1.0000 Uiso R . . . . .
H41 H 0.8202 0.5438 0.8340 0.0280 1.0000 Uiso R . . . . .
H62 H 0.7024 0.6340 0.8265 0.0387 1.0000 Uiso R . . . . .
H61 H 0.7300 0.7632 0.7792 0.0398 1.0000 Uiso R . . . . .
H81 H 0.5843 0.4775 0.7659 0.0622 1.0000 Uiso R . . . . .
H91 H 0.4713 0.5340 0.7039 0.0822 1.0000 Uiso R . . . . .
H101 H 0.4430 0.7831 0.6301 0.0869 1.0000 Uiso R . . . . .
H111 H 0.5312 0.9776 0.6253 0.0834 1.0000 Uiso R . . . . .
H121 H 0.6461 0.9269 0.6928 0.0572 1.0000 Uiso R . . . . .
H221 H 0.6587 0.2955 0.6458 0.0532 1.0000 Uiso R . . . . .
H231 H 0.5689 0.2664 0.5411 0.0683 1.0000 Uiso R . . . . .
H241 H 0.5498 0.4917 0.4598 0.0630 1.0000 Uiso R . . . . .
H261 H 0.5817 0.7783 0.4213 0.0710 1.0000 Uiso R . . . . .
H271 H 0.6549 1.0268 0.4368 0.0850 1.0000 Uiso R . . . . .
H281 H 0.7453 1.0595 0.5438 0.0741 1.0000 Uiso R . . . . .
H291 H 0.7634 0.8419 0.6304 0.0507 1.0000 Uiso R . . . . .
H341 H 1.0325 0.4775 0.7925 0.0455 1.0000 Uiso R . . . . .
H342 H 1.0382 0.3209 0.7398 0.0464 1.0000 Uiso R . . . . .
H352 H 1.1115 0.2656 0.8553 0.0763 1.0000 Uiso R . . . . .
H353 H 1.0451 0.2675 0.8796 0.0755 1.0000 Uiso R . . . . .
H351 H 1.0548 0.1153 0.8315 0.0755 1.0000 Uiso R . . . . .
H392 H 0.8850 -0.1643 0.8310 0.0396 1.0000 Uiso R . . . . .
H391 H 0.8323 -0.0924 0.8676 0.0407 1.0000 Uiso R . . . . .
H402 H 0.9301 -0.2029 0.9526 0.0657 1.0000 Uiso R . . . . .
H401 H 0.9775 -0.0754 0.9265 0.0660 1.0000 Uiso R . . . . .
H403 H 0.9266 0.0057 0.9626 0.0655 1.0000 Uiso R . . . . .
H421 H 0.6893 0.2207 0.7901 0.0386 1.0000 Uiso R . . . . .
H431 H 0.6601 0.0140 0.8633 0.0499 1.0000 Uiso R . . . . .
H441 H 0.7297 -0.0097 0.9771 0.0541 1.0000 Uiso R . . . . .
H461 H 0.8292 0.0868 1.0728 0.0576 1.0000 Uiso R . . . . .
H471 H 0.9237 0.2668 1.1170 0.0576 1.0000 Uiso R . . . . .
H481 H 0.9580 0.4663 1.0454 0.0504 1.0000 Uiso R . . . . .
H491 H 0.8913 0.4934 0.9307 0.0383 1.0000 Uiso R . . . . .
H21 H 0.7824 0.3062 0.6759 0.0359 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.75(5)
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
C1 . N2 . 1.470(2) yes
C1 . N5 . 1.470(2) yes
C1 . C21 . 1.524(3) yes
C1 . H11 . 0.999 no
N2 . C3 . 1.464(2) yes
N2 . H21 . 0.849 no
C3 . C4 . 1.582(2) yes
C3 . C31 . 1.539(2) yes
C3 . C36 . 1.523(3) yes
C4 . N5 . 1.473(2) yes
C4 . C41 . 1.519(2) yes
C4 . H41 . 0.989 no
N5 . C6 . 1.478(2) yes
C6 . C7 . 1.514(3) yes
C6 . H62 . 0.977 no
C6 . H61 . 0.987 no
C7 . C8 . 1.388(3) yes
C7 . C12 . 1.380(3) yes
C8 . C9 . 1.377(3) yes
C8 . H81 . 0.948 no
C9 . C10 . 1.381(5) yes
C9 . H91 . 0.957 no
C10 . C11 . 1.378(5) yes
C10 . H101 . 0.958 no
C11 . C12 . 1.409(4) yes
C11 . H111 . 0.942 no
C12 . H121 . 0.937 no
C21 . C22 . 1.377(3) yes
C21 . C30 . 1.419(3) yes
C22 . C23 . 1.412(3) yes
C22 . H221 . 0.946 no
C23 . C24 . 1.362(4) yes
C23 . H231 . 0.962 no
C24 . C25 . 1.413(4) yes
C24 . H241 . 0.939 no
C25 . C26 . 1.426(4) yes
C25 . C30 . 1.430(3) yes
C26 . C27 . 1.360(5) yes
C26 . H261 . 0.946 no
C27 . C28 . 1.401(4) yes
C27 . H271 . 0.976 no
C28 . C29 . 1.373(4) yes
C28 . H281 . 0.972 no
C29 . C30 . 1.421(3) yes
C29 . H291 . 0.973 no
C31 . O32 . 1.204(2) yes
C31 . O33 . 1.333(2) yes
O33 . C34 . 1.462(2) yes
C34 . C35 . 1.500(3) yes
C34 . H341 . 0.969 no
C34 . H342 . 0.981 no
C35 . H352 . 0.981 no
C35 . H353 . 0.961 no
C35 . H351 . 0.958 no
C36 . O37 . 1.205(2) yes
C36 . O38 . 1.324(2) yes
O38 . C39 . 1.455(2) yes
C39 . C40 . 1.496(3) yes
C39 . H392 . 0.976 no
C39 . H391 . 0.974 no
C40 . H402 . 0.962 no
C40 . H401 . 0.965 no
C40 . H403 . 0.972 no
C41 . C42 . 1.379(3) yes
C41 . C50 . 1.432(2) yes
C42 . C43 . 1.407(3) yes
C42 . H421 . 0.944 no
C43 . C44 . 1.363(3) yes
C43 . H431 . 0.937 no
C44 . C45 . 1.413(3) yes
C44 . H441 . 0.927 no
C45 . C46 . 1.429(3) yes
C45 . C50 . 1.430(3) yes
C46 . C47 . 1.360(4) yes
C46 . H461 . 0.924 no
C47 . C48 . 1.405(4) yes
C47 . H471 . 0.933 no
C48 . C49 . 1.372(3) yes
C48 . H481 . 0.959 no
C49 . C50 . 1.416(3) yes
C49 . H491 . 0.946 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
N2 . C1 . N5 . 104.94(15) yes
N2 . C1 . C21 . 109.94(16) yes
N5 . C1 . C21 . 112.97(16) yes
N2 . C1 . H11 . 107.9 no
N5 . C1 . H11 . 109.7 no
C21 . C1 . H11 . 111.0 no
C1 . N2 . C3 . 106.84(14) yes
C1 . N2 . H21 . 108.5 no
C3 . N2 . H21 . 105.7 no
N2 . C3 . C4 . 105.85(14) yes
N2 . C3 . C31 . 108.69(14) yes
C4 . C3 . C31 . 112.53(14) yes
N2 . C3 . C36 . 111.16(15) yes
C4 . C3 . C36 . 110.33(15) yes
C31 . C3 . C36 . 108.28(14) yes
C3 . C4 . N5 . 103.01(14) yes
C3 . C4 . C41 . 115.01(15) yes
N5 . C4 . C41 . 110.88(14) yes
C3 . C4 . H41 . 107.7 no
N5 . C4 . H41 . 110.2 no
C41 . C4 . H41 . 109.8 no
C4 . N5 . C1 . 105.57(14) yes
C4 . N5 . C6 . 109.56(14) yes
C1 . N5 . C6 . 113.53(16) yes
N5 . C6 . C7 . 112.89(16) yes
N5 . C6 . H62 . 108.3 no
C7 . C6 . H62 . 109.1 no
N5 . C6 . H61 . 109.4 no
C7 . C6 . H61 . 108.8 no
H62 . C6 . H61 . 108.3 no
C6 . C7 . C8 . 119.5(2) yes
C6 . C7 . C12 . 121.0(2) yes
C8 . C7 . C12 . 119.5(2) yes
C7 . C8 . C9 . 121.3(3) yes
C7 . C8 . H81 . 121.1 no
C9 . C8 . H81 . 117.5 no
C8 . C9 . C10 . 119.7(3) yes
C8 . C9 . H91 . 119.3 no
C10 . C9 . H91 . 120.9 no
C9 . C10 . C11 . 119.6(3) yes
C9 . C10 . H101 . 120.1 no
C11 . C10 . H101 . 120.3 no
C10 . C11 . C12 . 120.8(3) yes
C10 . C11 . H111 . 120.3 no
C12 . C11 . H111 . 118.8 no
C11 . C12 . C7 . 119.0(3) yes
C11 . C12 . H121 . 120.4 no
C7 . C12 . H121 . 120.6 no
C1 . C21 . C22 . 117.8(2) yes
C1 . C21 . C30 . 122.5(2) yes
C22 . C21 . C30 . 119.6(2) yes
C21 . C22 . C23 . 121.3(3) yes
C21 . C22 . H221 . 120.1 no
C23 . C22 . H221 . 118.7 no
C22 . C23 . C24 . 120.2(3) yes
C22 . C23 . H231 . 119.7 no
C24 . C23 . H231 . 120.1 no
C23 . C24 . C25 . 120.5(2) yes
C23 . C24 . H241 . 120.0 no
C25 . C24 . H241 . 119.6 no
C24 . C25 . C26 . 121.3(2) yes
C24 . C25 . C30 . 119.7(2) yes
C26 . C25 . C30 . 119.0(3) yes
C25 . C26 . C27 . 121.4(3) yes
C25 . C26 . H261 . 117.2 no
C27 . C26 . H261 . 121.4 no
C26 . C27 . C28 . 119.4(3) yes
C26 . C27 . H271 . 119.9 no
C28 . C27 . H271 . 120.7 no
C27 . C28 . C29 . 121.5(3) yes
C27 . C28 . H281 . 119.8 no
C29 . C28 . H281 . 118.7 no
C28 . C29 . C30 . 120.7(3) yes
C28 . C29 . H291 . 121.5 no
C30 . C29 . H291 . 117.8 no
C25 . C30 . C29 . 117.9(2) yes
C25 . C30 . C21 . 118.7(2) yes
C29 . C30 . C21 . 123.3(2) yes
C3 . C31 . O32 . 125.36(16) yes
C3 . C31 . O33 . 109.84(15) yes
O32 . C31 . O33 . 124.78(17) yes
C31 . O33 . C34 . 116.89(15) yes
O33 . C34 . C35 . 109.85(19) yes
O33 . C34 . H341 . 108.6 no
C35 . C34 . H341 . 109.1 no
O33 . C34 . H342 . 104.9 no
C35 . C34 . H342 . 111.7 no
H341 . C34 . H342 . 112.6 no
C34 . C35 . H352 . 109.1 no
C34 . C35 . H353 . 110.2 no
H352 . C35 . H353 . 109.0 no
C34 . C35 . H351 . 111.4 no
H352 . C35 . H351 . 108.5 no
H353 . C35 . H351 . 108.6 no
C3 . C36 . O37 . 124.49(18) yes
C3 . C36 . O38 . 109.34(15) yes
O37 . C36 . O38 . 126.11(19) yes
C36 . O38 . C39 . 116.99(15) yes
O38 . C39 . C40 . 106.60(17) yes
O38 . C39 . H392 . 110.3 no
C40 . C39 . H392 . 111.7 no
O38 . C39 . H391 . 109.6 no
C40 . C39 . H391 . 110.0 no
H392 . C39 . H391 . 108.6 no
C39 . C40 . H402 . 110.1 no
C39 . C40 . H401 . 108.8 no
H402 . C40 . H401 . 108.7 no
C39 . C40 . H403 . 110.8 no
H402 . C40 . H403 . 109.5 no
H401 . C40 . H403 . 108.8 no
C4 . C41 . C42 . 119.35(17) yes
C4 . C41 . C50 . 121.17(16) yes
C42 . C41 . C50 . 119.39(18) yes
C41 . C42 . C43 . 121.8(2) yes
C41 . C42 . H421 . 117.8 no
C43 . C42 . H421 . 120.4 no
C42 . C43 . C44 . 120.0(2) yes
C42 . C43 . H431 . 120.2 no
C44 . C43 . H431 . 119.8 no
C43 . C44 . C45 . 120.5(2) yes
C43 . C44 . H441 . 121.7 no
C45 . C44 . H441 . 117.8 no
C44 . C45 . C46 . 121.1(2) yes
C44 . C45 . C50 . 120.1(2) yes
C46 . C45 . C50 . 118.8(2) yes
C45 . C46 . C47 . 121.1(2) yes
C45 . C46 . H461 . 118.7 no
C47 . C46 . H461 . 120.2 no
C46 . C47 . C48 . 120.2(2) yes
C46 . C47 . H471 . 119.7 no
C48 . C47 . H471 . 120.1 no
C47 . C48 . C49 . 120.4(2) yes
C47 . C48 . H481 . 119.6 no
C49 . C48 . H481 . 119.9 no
C48 . C49 . C50 . 121.4(2) yes
C48 . C49 . H491 . 119.5 no
C50 . C49 . H491 . 119.2 no
C41 . C50 . C45 . 118.14(19) yes
C41 . C50 . C49 . 123.73(18) yes
C45 . C50 . C49 . 118.11(18) 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
C29 . H291 . O37 1_565 141 0.97 2.54 3.357(4) yes
C39 . H392 . O32 1_545 142 0.98 2.46 3.282(4) yes
C49 . H491 . O32 . 147 0.95 2.56 3.388(4) 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
-2 1 8 x .
1 0 0 x .
-20 3 18 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_248-26
_database_code_depnum_ccdc_archive 'CCDC 2256199'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2020-03-10
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7292
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.9393(2)
_cell_length_b                   12.8109(7)
_cell_length_c                   13.7065(6)
_cell_angle_alpha                72.892(4)
_cell_angle_beta                 83.254(3)
_cell_angle_gamma                82.124(3)
_cell_volume                     1646.81(13)

_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'


_cell_formula_units_Z            2

# Given Formula = C36 H42 N2 O7 
# Dc =      1.24 Fooo =    656.00 Mu =      6.97 M =    614.74
# Found Formula = C36 H42 N2 O7 
# Dc =      1.24 FOOO =    656.00 Mu =      6.97 M =    614.74

_chemical_formula_sum            'C36 H42 N2 O7'
_chemical_formula_moiety         'C36 H42 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         614.74


_cell_measurement_reflns_used    18481
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      75.75
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             656.000
_exptl_absorpt_coefficient_mu    0.697

# Sheldrick geometric approximatio 0.91 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.92
_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            39272
_diffrn_reflns_av_unetI/netI     0.046
_reflns_number_total             6836
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0458
# Number of reflections with Friedels Law is 6836 
# Theoretical number of reflections is about 13784 

_diffrn_reflns_theta_min         3.631
_diffrn_reflns_theta_max         76.171
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        74.647
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -15
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.58
_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         -0.29
_refine_diff_density_max         0.37


# 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     92
_refine_ls_number_parameters     440
_refine_ls_number_reflns         6836
_oxford_refine_ls_R_factor_ref   0.0465
_refine_ls_R_factor_all          0.0465
_refine_ls_wR_factor_ref         0.1117 #Calculated the Oxford way
_refine_ls_wR_factor_all         0.1117
_refine_ls_goodness_of_fit_ref   1.0023
_refine_ls_shift/su_max          0.0005942
_refine_ls_shift/su_mean         0.0000620


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        6836
_oxford_refine_ls_R_factor_all   0.0465
_oxford_refine_ls_wR_factor_all  0.1117

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6130
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_gt          0.1068


_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 + 0.64P] 
 ,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
N1 N 0.57202(10) 0.91980(9) 0.82872(7) 0.0222 1.0000 Uani . . . . . .
C2 C 0.49718(11) 0.82746(10) 0.83833(9) 0.0227 1.0000 Uani . . . . . .
C3 C 0.58771(12) 0.72582(10) 0.90266(9) 0.0229 1.0000 Uani . . . . . .
N4 N 0.68215(10) 0.77645(9) 0.94405(8) 0.0228 1.0000 Uani . . . . . .
C5 C 0.67817(11) 0.89530(10) 0.90051(9) 0.0209 1.0000 Uani . . . . . .
C6 C 0.81601(12) 0.92999(10) 0.84957(9) 0.0224 1.0000 Uani . . . . . .
C7 C 0.87902(13) 0.89203(12) 0.76814(10) 0.0310 1.0000 Uani . . . . . .
C8 C 1.00921(15) 0.91743(14) 0.72832(11) 0.0383 1.0000 Uani . . . . . .
C9 C 1.07594(13) 0.98310(14) 0.76636(11) 0.0387 1.0000 Uani . . . . . .
C10 C 1.01163(14) 1.02413(14) 0.84401(11) 0.0377 1.0000 Uani . . . . . .
C11 C 0.88240(13) 0.99679(11) 0.88669(10) 0.0287 1.0000 Uani . . . . . .
C12 C 0.51565(12) 1.02206(11) 0.77832(9) 0.0247 1.0000 Uani . U . . . .
O13 O 0.41797(9) 1.03250(8) 0.72817(7) 0.0308 1.0000 Uani . . . . . .
C14 C 0.57413(13) 1.12131(11) 0.78688(10) 0.0298 1.0000 Uani D U . . . .
C15 C 0.65925(16) 1.17882(14) 0.69153(13) 0.0335 0.936(2) Uani D U P 1 1 .
O16 O 0.70043(18) 1.26513(12) 0.68269(14) 0.0682 0.936(2) Uani D U P 1 1 .
O17 O 0.68074(12) 1.12535(10) 0.62095(9) 0.0353 0.936(2) Uani D U P 1 1 .
C18 C 0.75321(17) 1.18026(16) 0.52485(12) 0.0427 0.936(2) Uani D U P 1 1 .
C19 C 0.9019(2) 1.16696(19) 0.53034(16) 0.0492 0.936(2) Uani D U P 1 1 .
C20 C 0.47333(12) 0.82051(11) 0.73101(9) 0.0259 1.0000 Uani . . . . . .
O21 O 0.37104(10) 0.79839(9) 0.70742(7) 0.0360 1.0000 Uani . . . . . .
O22 O 0.58680(9) 0.84081(8) 0.67004(7) 0.0285 1.0000 Uani . . . . . .
C23 C 0.58040(15) 0.84268(14) 0.56418(10) 0.0364 1.0000 Uani . . . . . .
C24 C 0.71594(17) 0.87059(17) 0.51002(12) 0.0492 1.0000 Uani . . . . . .
C25 C 0.36307(12) 0.83788(11) 0.90621(9) 0.0248 1.0000 Uani . . . . . .
O26 O 0.33714(10) 0.90688(8) 0.95109(8) 0.0344 1.0000 Uani . . . . . .
O27 O 0.29030(9) 0.75599(8) 0.91549(7) 0.0310 1.0000 Uani . . . . . .
C28 C 0.16790(14) 0.74903(13) 0.98652(12) 0.0368 1.0000 Uani . . . . . .
C29 C 0.09786(17) 0.65827(16) 0.97549(17) 0.0536 1.0000 Uani . . . . . .
C30 C 0.65428(13) 0.64200(11) 0.84732(9) 0.0262 1.0000 Uani . . . . . .
C31 C 0.79399(14) 0.62389(13) 0.82804(12) 0.0355 1.0000 Uani . . . . . .
C32 C 0.84993(17) 0.54348(15) 0.78076(15) 0.0479 1.0000 Uani . . . . . .
C33 C 0.76679(18) 0.48047(15) 0.75334(14) 0.0476 1.0000 Uani . . . . . .
C34 C 0.62758(17) 0.49668(14) 0.77433(13) 0.0439 1.0000 Uani . . . . . .
C35 C 0.57141(15) 0.57662(12) 0.82161(12) 0.0354 1.0000 Uani . . . . . .
C36 C 0.71421(11) 0.72808(10) 1.04566(9) 0.0223 1.0000 Uani . . . . . .
C37 C 0.75523(13) 0.78824(11) 1.10496(10) 0.0280 1.0000 Uani . . . . . .
C38 C 0.77632(14) 0.73943(12) 1.20751(10) 0.0309 1.0000 Uani . . . . . .
C39 C 0.76033(13) 0.62959(11) 1.25589(10) 0.0289 1.0000 Uani . . . . . .
C40 C 0.72822(14) 0.56860(11) 1.19455(10) 0.0305 1.0000 Uani . . . . . .
C41 C 0.70546(13) 0.61596(11) 1.09187(10) 0.0279 1.0000 Uani . . . . . .
C42 C 0.76694(16) 0.58311(13) 1.37217(11) 0.0377 1.0000 Uani . . . . . .
C43 C 0.6333(2) 0.62734(19) 1.42295(13) 0.0553 1.0000 Uani . . . . . .
C44 C 0.88694(19) 0.62174(17) 1.40750(13) 0.0519 1.0000 Uani . . . . . .
C45 C 0.7794(3) 0.45893(16) 1.40636(15) 0.0748 1.0000 Uani . . . . . .
O116 O 0.726(3) 1.2470(17) 0.7651(19) 0.0682 0.064(2) Uani D U P 1 2 .
O117 O 0.7238(19) 1.1342(14) 0.6539(13) 0.0377 0.064(2) Uani D U P 1 2 .
C115 C 0.6915(19) 1.1833(16) 0.7277(17) 0.0378 0.064(2) Uani D U P 1 2 .
C118 C 0.829(2) 1.1886(18) 0.6020(19) 0.0452 0.064(2) Uani D U P 1 2 .
C119 C 0.927(3) 1.123(3) 0.540(3) 0.0492 0.064(2) Uani D U P 1 2 .
H31 H 0.5266 0.6873 0.9588 0.0257 1.0000 Uiso R . . . . .
H51 H 0.6479 0.9322 0.9550 0.0232 1.0000 Uiso R . . . . .
H71 H 0.8335 0.8483 0.7396 0.0375 1.0000 Uiso R . . . . .
H81 H 1.0532 0.8888 0.6745 0.0474 1.0000 Uiso R . . . . .
H91 H 1.1636 1.0012 0.7397 0.0468 1.0000 Uiso R . . . . .
H101 H 1.0545 1.0711 0.8693 0.0466 1.0000 Uiso R . . . . .
H111 H 0.8374 1.0247 0.9409 0.0336 1.0000 Uiso R . . . . .
H144 H 0.6281 1.1051 0.8445 0.0366 0.936(2) Uiso R . P 1 1 .
H143 H 0.4957 1.1734 0.7967 0.0365 0.936(2) Uiso R . P 1 1 .
H142 H 0.5961 1.1012 0.8576 0.0360 0.064(2) Uiso R . P 1 2 .
H141 H 0.4968 1.1775 0.7769 0.0360 0.064(2) Uiso R . P 1 2 .
H181 H 0.7194 1.2584 0.5078 0.0509 0.936(2) Uiso R . P 1 1 .
H182 H 0.7323 1.1486 0.4723 0.0517 0.936(2) Uiso R . P 1 1 .
H193 H 0.9429 1.2060 0.4624 0.0729 0.936(2) Uiso R . P 1 1 .
H191 H 0.9249 1.1961 0.5847 0.0736 0.936(2) Uiso R . P 1 1 .
H192 H 0.9339 1.0869 0.5446 0.0758 0.936(2) Uiso R . P 1 1 .
H231 H 0.5069 0.8987 0.5336 0.0444 1.0000 Uiso R . . . . .
H232 H 0.5622 0.7708 0.5636 0.0442 1.0000 Uiso R . . . . .
H243 H 0.7152 0.8774 0.4382 0.0732 1.0000 Uiso R . . . . .
H241 H 0.7356 0.9417 0.5173 0.0734 1.0000 Uiso R . . . . .
H242 H 0.7874 0.8130 0.5383 0.0722 1.0000 Uiso R . . . . .
H281 H 0.1951 0.7339 1.0569 0.0454 1.0000 Uiso R . . . . .
H282 H 0.1108 0.8190 0.9690 0.0450 1.0000 Uiso R . . . . .
H291 H 0.0124 0.6535 1.0175 0.0788 1.0000 Uiso R . . . . .
H292 H 0.1557 0.5880 0.9952 0.0793 1.0000 Uiso R . . . . .
H293 H 0.0788 0.6734 0.9039 0.0799 1.0000 Uiso R . . . . .
H311 H 0.8513 0.6662 0.8484 0.0429 1.0000 Uiso R . . . . .
H321 H 0.9472 0.5322 0.7679 0.0575 1.0000 Uiso R . . . . .
H331 H 0.8057 0.4239 0.7223 0.0568 1.0000 Uiso R . . . . .
H341 H 0.5680 0.4516 0.7567 0.0535 1.0000 Uiso R . . . . .
H351 H 0.4741 0.5881 0.8363 0.0423 1.0000 Uiso R . . . . .
H371 H 0.7658 0.8653 1.0765 0.0353 1.0000 Uiso R . . . . .
H381 H 0.8022 0.7845 1.2467 0.0367 1.0000 Uiso R . . . . .
H401 H 0.7200 0.4924 1.2224 0.0375 1.0000 Uiso R . . . . .
H411 H 0.6850 0.5705 1.0533 0.0340 1.0000 Uiso R . . . . .
H431 H 0.6373 0.5969 1.4991 0.0824 1.0000 Uiso R . . . . .
H433 H 0.6230 0.7135 1.4017 0.0830 1.0000 Uiso R . . . . .
H432 H 0.5549 0.5989 1.4030 0.0824 1.0000 Uiso R . . . . .
H442 H 0.8871 0.5911 1.4830 0.0776 1.0000 Uiso R . . . . .
H441 H 0.8767 0.7023 1.3916 0.0772 1.0000 Uiso R . . . . .
H443 H 0.9750 0.5959 1.3722 0.0780 1.0000 Uiso R . . . . .
H453 H 0.7846 0.4333 1.4819 0.1110 1.0000 Uiso R . . . . .
H451 H 0.8700 0.4328 1.3738 0.1085 1.0000 Uiso R . . . . .
H452 H 0.6995 0.4314 1.3849 0.1114 1.0000 Uiso R . . . . .
H1191 H 0.9568 1.1793 0.4706 0.0740 0.064(2) Uiso R . P 1 2 .
H1192 H 1.0100 1.0879 0.5847 0.0740 0.064(2) Uiso R . P 1 2 .
H1193 H 0.8719 1.0637 0.5293 0.0739 0.064(2) Uiso R . P 1 2 .
H1181 H 0.8799 1.2051 0.6509 0.0541 0.064(2) Uiso R . P 1 2 .
H1182 H 0.7924 1.2567 0.5551 0.0540 0.064(2) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.76(10)
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
N1 . C2 . 1.4480(15) yes
N1 . C5 . 1.4666(14) yes
N1 . C12 . 1.3655(16) yes
C2 . C3 . 1.5724(17) yes
C2 . C20 . 1.5469(16) yes
C2 . C25 . 1.5470(16) yes
C3 . N4 . 1.4601(14) yes
C3 . C30 . 1.5274(17) yes
C3 . H31 . 0.976 no
N4 . C5 . 1.4596(15) yes
N4 . C36 . 1.4027(15) yes
C5 . C6 . 1.5237(16) yes
C5 . H51 . 0.994 no
C6 . C7 . 1.3950(17) yes
C6 . C11 . 1.3843(17) yes
C7 . C8 . 1.3868(19) yes
C7 . H71 . 0.955 no
C8 . C9 . 1.383(2) yes
C8 . H81 . 0.953 no
C9 . C10 . 1.377(2) yes
C9 . H91 . 0.937 no
C10 . C11 . 1.3932(18) yes
C10 . H101 . 0.944 no
C11 . H111 . 0.956 no
C12 . O13 . 1.2248(15) yes
C12 . C14 . 1.5081(18) yes
C14 . C15 . 1.520(2) yes
C14 . H144 . 0.963 no
C14 . H143 . 0.978 no
C14 . C115 . 1.517(9) yes
C14 . H142 . 0.971 no
C14 . H141 . 0.971 no
C15 . O16 . 1.199(2) yes
C15 . O17 . 1.324(2) yes
O17 . C18 . 1.4559(18) yes
C18 . C19 . 1.473(3) yes
C18 . H181 . 0.979 no
C18 . H182 . 0.978 no
C19 . H193 . 0.988 no
C19 . H191 . 0.987 no
C19 . H192 . 0.999 no
C20 . O21 . 1.1952(15) yes
C20 . O22 . 1.3301(15) yes
O22 . C23 . 1.4529(15) yes
C23 . C24 . 1.495(2) yes
C23 . H231 . 0.988 no
C23 . H232 . 0.965 no
C24 . H243 . 0.963 no
C24 . H241 . 0.992 no
C24 . H242 . 0.975 no
C25 . O26 . 1.2026(16) yes
C25 . O27 . 1.3221(16) yes
O27 . C28 . 1.4615(15) yes
C28 . C29 . 1.486(2) yes
C28 . H281 . 0.989 no
C28 . H282 . 0.974 no
C29 . H291 . 0.967 no
C29 . H292 . 0.983 no
C29 . H293 . 0.979 no
C30 . C31 . 1.3832(18) yes
C30 . C35 . 1.3910(18) yes
C31 . C32 . 1.393(2) yes
C31 . H311 . 0.952 no
C32 . C33 . 1.382(2) yes
C32 . H321 . 0.961 no
C33 . C34 . 1.380(2) yes
C33 . H331 . 0.960 no
C34 . C35 . 1.389(2) yes
C34 . H341 . 0.976 no
C35 . H351 . 0.964 no
C36 . C37 . 1.3976(17) yes
C36 . C41 . 1.3992(18) yes
C37 . C38 . 1.3881(18) yes
C37 . H371 . 0.964 no
C38 . C39 . 1.3902(19) yes
C38 . H381 . 0.971 no
C39 . C40 . 1.3918(19) yes
C39 . C42 . 1.5344(18) yes
C40 . C41 . 1.3910(18) yes
C40 . H401 . 0.949 no
C41 . H411 . 0.948 no
C42 . C43 . 1.543(2) yes
C42 . C44 . 1.530(2) yes
C42 . C45 . 1.512(2) yes
C43 . H431 . 1.004 no
C43 . H433 . 1.049 no
C43 . H432 . 1.000 no
C44 . H442 . 0.993 no
C44 . H441 . 0.984 no
C44 . H443 . 1.012 no
C45 . H453 . 0.995 no
C45 . H451 . 1.016 no
C45 . H452 . 1.017 no
O116 . C115 . 1.188(10) yes
O117 . C115 . 1.329(10) yes
O117 . C118 . 1.347(10) yes
C118 . C119 . 1.538(10) yes
C118 . H1181 . 0.972 no
C118 . H1182 . 0.971 no
C119 . H1191 . 1.052 no
C119 . H1192 . 1.050 no
C119 . H1193 . 1.053 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
C2 . N1 . C5 . 113.51(10) yes
C2 . N1 . C12 . 117.85(10) yes
C5 . N1 . C12 . 125.96(10) yes
N1 . C2 . C3 . 104.07(9) yes
N1 . C2 . C20 . 110.08(10) yes
C3 . C2 . C20 . 114.35(10) yes
N1 . C2 . C25 . 109.24(10) yes
C3 . C2 . C25 . 105.74(9) yes
C20 . C2 . C25 . 112.88(9) yes
C2 . C3 . N4 . 103.11(9) yes
C2 . C3 . C30 . 116.58(10) yes
N4 . C3 . C30 . 115.17(10) yes
C2 . C3 . H31 . 105.8 no
N4 . C3 . H31 . 109.0 no
C30 . C3 . H31 . 106.7 no
C3 . N4 . C5 . 114.27(9) yes
C3 . N4 . C36 . 118.37(10) yes
C5 . N4 . C36 . 119.68(9) yes
N1 . C5 . N4 . 102.63(9) yes
N1 . C5 . C6 . 113.45(9) yes
N4 . C5 . C6 . 112.17(9) yes
N1 . C5 . H51 . 109.0 no
N4 . C5 . H51 . 109.7 no
C6 . C5 . H51 . 109.6 no
C5 . C6 . C7 . 120.88(11) yes
C5 . C6 . C11 . 119.81(11) yes
C7 . C6 . C11 . 119.27(11) yes
C6 . C7 . C8 . 119.90(13) yes
C6 . C7 . H71 . 120.6 no
C8 . C7 . H71 . 119.5 no
C7 . C8 . C9 . 120.66(13) yes
C7 . C8 . H81 . 119.6 no
C9 . C8 . H81 . 119.8 no
C8 . C9 . C10 . 119.43(12) yes
C8 . C9 . H91 . 121.3 no
C10 . C9 . H91 . 119.2 no
C9 . C10 . C11 . 120.52(13) yes
C9 . C10 . H101 . 120.6 no
C11 . C10 . H101 . 118.9 no
C10 . C11 . C6 . 120.14(13) yes
C10 . C11 . H111 . 120.9 no
C6 . C11 . H111 . 118.9 no
N1 . C12 . O13 . 120.21(12) yes
N1 . C12 . C14 . 118.97(10) yes
O13 . C12 . C14 . 120.81(12) yes
C12 . C14 . C15 . 114.22(12) yes
C12 . C14 . H144 . 113.0 no
C15 . C14 . H144 . 108.0 no
C12 . C14 . H143 . 105.7 no
C15 . C14 . H143 . 107.2 no
H144 . C14 . H143 . 108.3 no
C12 . C14 . C115 . 132.5(6) yes
C12 . C14 . H142 . 104.0 no
C115 . C14 . H142 . 103.9 no
C12 . C14 . H141 . 103.0 no
C115 . C14 . H141 . 103.0 no
H142 . C14 . H141 . 109.4 no
C14 . C15 . O16 . 121.87(16) yes
C14 . C15 . O17 . 113.65(13) yes
O16 . C15 . O17 . 124.48(16) yes
C15 . O17 . C18 . 116.16(13) yes
O17 . C18 . C19 . 112.79(15) yes
O17 . C18 . H181 . 107.7 no
C19 . C18 . H181 . 109.6 no
O17 . C18 . H182 . 107.7 no
C19 . C18 . H182 . 109.0 no
H181 . C18 . H182 . 110.0 no
C18 . C19 . H193 . 107.6 no
C18 . C19 . H191 . 110.3 no
H193 . C19 . H191 . 111.6 no
C18 . C19 . H192 . 107.8 no
H193 . C19 . H192 . 108.7 no
H191 . C19 . H192 . 110.8 no
C2 . C20 . O21 . 125.72(11) yes
C2 . C20 . O22 . 108.54(10) yes
O21 . C20 . O22 . 125.73(11) yes
C20 . O22 . C23 . 115.95(10) yes
O22 . C23 . C24 . 106.57(11) yes
O22 . C23 . H231 . 109.6 no
C24 . C23 . H231 . 110.8 no
O22 . C23 . H232 . 108.0 no
C24 . C23 . H232 . 111.6 no
H231 . C23 . H232 . 110.2 no
C23 . C24 . H243 . 109.9 no
C23 . C24 . H241 . 109.8 no
H243 . C24 . H241 . 108.4 no
C23 . C24 . H242 . 110.3 no
H243 . C24 . H242 . 108.7 no
H241 . C24 . H242 . 109.7 no
C2 . C25 . O26 . 122.86(11) yes
C2 . C25 . O27 . 111.20(10) yes
O26 . C25 . O27 . 125.62(11) yes
C25 . O27 . C28 . 116.97(10) yes
O27 . C28 . C29 . 106.55(13) yes
O27 . C28 . H281 . 108.9 no
C29 . C28 . H281 . 111.5 no
O27 . C28 . H282 . 109.1 no
C29 . C28 . H282 . 111.7 no
H281 . C28 . H282 . 109.0 no
C28 . C29 . H291 . 109.9 no
C28 . C29 . H292 . 110.7 no
H291 . C29 . H292 . 109.9 no
C28 . C29 . H293 . 109.2 no
H291 . C29 . H293 . 108.5 no
H292 . C29 . H293 . 108.6 no
C3 . C30 . C31 . 122.46(11) yes
C3 . C30 . C35 . 118.42(11) yes
C31 . C30 . C35 . 118.98(12) yes
C30 . C31 . C32 . 120.21(13) yes
C30 . C31 . H311 . 119.2 no
C32 . C31 . H311 . 120.6 no
C31 . C32 . C33 . 120.48(15) yes
C31 . C32 . H321 . 119.0 no
C33 . C32 . H321 . 120.6 no
C32 . C33 . C34 . 119.51(14) yes
C32 . C33 . H331 . 120.3 no
C34 . C33 . H331 . 120.1 no
C33 . C34 . C35 . 120.19(14) yes
C33 . C34 . H341 . 120.3 no
C35 . C34 . H341 . 119.5 no
C30 . C35 . C34 . 120.59(13) yes
C30 . C35 . H351 . 119.1 no
C34 . C35 . H351 . 120.3 no
N4 . C36 . C37 . 122.32(11) yes
N4 . C36 . C41 . 120.45(11) yes
C37 . C36 . C41 . 117.23(11) yes
C36 . C37 . C38 . 120.68(12) yes
C36 . C37 . H371 . 120.9 no
C38 . C37 . H371 . 118.4 no
C37 . C38 . C39 . 122.54(12) yes
C37 . C38 . H381 . 118.2 no
C39 . C38 . H381 . 119.2 no
C38 . C39 . C40 . 116.32(12) yes
C38 . C39 . C42 . 120.54(12) yes
C40 . C39 . C42 . 122.96(12) yes
C39 . C40 . C41 . 122.06(12) yes
C39 . C40 . H401 . 120.3 no
C41 . C40 . H401 . 117.6 no
C36 . C41 . C40 . 120.94(12) yes
C36 . C41 . H411 . 120.4 no
C40 . C41 . H411 . 118.7 no
C39 . C42 . C43 . 107.17(12) yes
C39 . C42 . C44 . 110.89(13) yes
C43 . C42 . C44 . 108.80(14) yes
C39 . C42 . C45 . 112.20(13) yes
C43 . C42 . C45 . 108.78(17) yes
C44 . C42 . C45 . 108.92(16) yes
C42 . C43 . H431 . 107.3 no
C42 . C43 . H433 . 110.4 no
H431 . C43 . H433 . 110.5 no
C42 . C43 . H432 . 109.1 no
H431 . C43 . H432 . 108.1 no
H433 . C43 . H432 . 111.4 no
C42 . C44 . H442 . 108.6 no
C42 . C44 . H441 . 110.4 no
H442 . C44 . H441 . 107.8 no
C42 . C44 . H443 . 109.4 no
H442 . C44 . H443 . 110.7 no
H441 . C44 . H443 . 109.9 no
C42 . C45 . H453 . 108.8 no
C42 . C45 . H451 . 106.6 no
H453 . C45 . H451 . 107.2 no
C42 . C45 . H452 . 110.3 no
H453 . C45 . H452 . 111.7 no
H451 . C45 . H452 . 112.0 no
C115 . O117 . C118 . 100.7(16) yes
C14 . C115 . O117 . 100.7(10) yes
C14 . C115 . O116 . 115.2(15) yes
O117 . C115 . O116 . 143.8(16) yes
O117 . C118 . C119 . 114(2) yes
O117 . C118 . H1181 . 108.4 no
C119 . C118 . H1181 . 108.2 no
O117 . C118 . H1182 . 108.4 no
C119 . C118 . H1182 . 108.7 no
H1181 . C118 . H1182 . 109.5 no
C118 . C119 . H1191 . 107.0 no
C118 . C119 . H1192 . 106.9 no
H1191 . C119 . H1192 . 112.2 no
C118 . C119 . H1193 . 106.3 no
H1191 . C119 . H1193 . 111.6 no
H1192 . C119 . H1193 . 112.4 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
C9 . H91 . O13 1_655 161 0.94 2.59 3.494(5) yes
C11 . H111 . O26 2_677 162 0.96 2.39 3.311(5) yes
C33 . H331 . O116 1_545 124 0.96 2.39 3.027(5) yes
C119 . H1192 . C8 . 124 1.05 2.47 3.186(5) yes
C119 . H1192 . C9 . 144 1.05 2.57 3.474(5) 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_245e-20e
_database_code_depnum_ccdc_archive 'CCDC 2256192'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2020-01-23
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7262
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.1492(4)
_cell_length_b                   11.6174(6)
_cell_length_c                   11.7103(5)
_cell_angle_alpha                80.333(4)
_cell_angle_beta                 72.281(4)
_cell_angle_gamma                86.447(4)
_cell_volume                     1296.47(11)

_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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 '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            2

# Given Formula = C28 H28 Cl2 N2 O4 
# Dc =      1.35 Fooo =    552.00 Mu =     25.57 M =    527.45
# Found Formula = C28 H28 Cl2 N2 O4 
# Dc =      1.35 FOOO =    552.00 Mu =     25.57 M =    527.45

_chemical_formula_sum            'C28 H28 Cl2 N2 O4'
_chemical_formula_moiety         'C28 H28 Cl2 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         527.45


_cell_measurement_reflns_used    6185
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      76.99
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    2.557

# Sheldrick geometric approximatio 0.60 0.81 
_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  0.81
_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            10029
_diffrn_reflns_av_unetI/netI     0.032
_reflns_number_total             5401
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.0317
# Number of reflections with Friedels Law is 5401 
# Theoretical number of reflections is about 10975 

_diffrn_reflns_theta_min         3.860
_diffrn_reflns_theta_max         77.075
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        73.992
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.44
_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         -0.29
_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 

# 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     0
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5398
_oxford_refine_ls_R_factor_ref   0.0367
_refine_ls_R_factor_all          0.0367
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_all         0.0890
_refine_ls_goodness_of_fit_ref   0.9936
_refine_ls_shift/su_max          0.0004336
_refine_ls_shift/su_mean         0.0000356


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        5399
_oxford_refine_ls_R_factor_all   0.0367
_oxford_refine_ls_wR_factor_all  0.0890

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4900
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0858


_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 + 0.51P] 
 ,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
C1 C 0.21453(12) 0.20958(10) 0.73454(11) 0.0190 1.0000 Uani . . . . . .
C2 C 0.35963(12) 0.17380(11) 0.65663(11) 0.0193 1.0000 Uani . . . . . .
N3 N 0.43235(11) 0.28438(9) 0.61025(10) 0.0207 1.0000 Uani . . . . . .
C4 C 0.36128(12) 0.36935(11) 0.68990(11) 0.0203 1.0000 Uani . . . . . .
N5 N 0.25825(10) 0.29978(9) 0.79010(9) 0.0200 1.0000 Uani . . . . . .
C6 C 0.14851(13) 0.37326(11) 0.85495(12) 0.0236 1.0000 Uani . . . . . .
C7 C 0.04845(13) 0.30886(11) 0.96769(12) 0.0238 1.0000 Uani . . . . . .
C8 C 0.08381(16) 0.20588(13) 1.03192(13) 0.0308 1.0000 Uani . . . . . .
C9 C -0.01077(19) 0.15357(15) 1.13915(14) 0.0407 1.0000 Uani . . . . . .
C10 C -0.13942(19) 0.20451(16) 1.18338(15) 0.0445 1.0000 Uani . . . . . .
C11 C -0.17455(17) 0.30695(15) 1.11976(16) 0.0429 1.0000 Uani . . . . . .
C12 C -0.08220(15) 0.35795(13) 1.01228(14) 0.0316 1.0000 Uani . . . . . .
C21 C 0.11189(12) 0.25030(10) 0.66441(11) 0.0199 1.0000 Uani . . . . . .
C22 C 0.14822(13) 0.31998(11) 0.55054(12) 0.0227 1.0000 Uani . . . . . .
C23 C 0.05035(14) 0.35450(11) 0.49000(12) 0.0252 1.0000 Uani . . . . . .
C24 C -0.08515(14) 0.31904(12) 0.54517(13) 0.0262 1.0000 Uani . . . . . .
C25 C -0.12542(13) 0.25126(12) 0.65875(13) 0.0278 1.0000 Uani . . . . . .
C26 C -0.02578(13) 0.21728(12) 0.71752(12) 0.0248 1.0000 Uani . . . . . .
Cl27 Cl -0.20773(4) 0.35953(3) 0.46858(4) 0.0391 1.0000 Uani . . . . . .
C31 C 0.35773(12) 0.11042(11) 0.55203(12) 0.0209 1.0000 Uani . . . . . .
O32 O 0.44349(10) 0.12316(9) 0.45436(9) 0.0274 1.0000 Uani . . . . . .
O33 O 0.24975(9) 0.03927(8) 0.58638(9) 0.0257 1.0000 Uani . . . . . .
C34 C 0.23224(15) -0.02434(12) 0.49469(14) 0.0299 1.0000 Uani . . . . . .
C35 C 0.17467(19) 0.05383(15) 0.40436(17) 0.0414 1.0000 Uani . . . . . .
C36 C 0.43310(13) 0.09289(11) 0.73846(11) 0.0220 1.0000 Uani . . . . . .
O37 O 0.54328(10) 0.11477(9) 0.74715(9) 0.0289 1.0000 Uani . . . . . .
O38 O 0.36083(11) -0.00229(9) 0.79378(11) 0.0362 1.0000 Uani . . . . . .
C39 C 0.41902(18) -0.08789(15) 0.87233(18) 0.0450 1.0000 Uani . . . . . .
C40 C 0.3286(3) -0.0911(2) 1.00008(19) 0.0606 1.0000 Uani . . . . . .
C41 C 0.45642(12) 0.43376(11) 0.73424(11) 0.0214 1.0000 Uani . . . . . .
C42 C 0.49030(13) 0.54888(11) 0.68259(12) 0.0241 1.0000 Uani . . . . . .
C43 C 0.57639(14) 0.61102(12) 0.72198(12) 0.0272 1.0000 Uani . . . . . .
C44 C 0.62915(14) 0.55588(13) 0.81291(13) 0.0289 1.0000 Uani . . . . . .
C45 C 0.59755(16) 0.44102(13) 0.86578(14) 0.0339 1.0000 Uani . . . . . .
C46 C 0.51041(15) 0.38069(12) 0.82644(13) 0.0291 1.0000 Uani . . . . . .
Cl47 Cl 0.73817(4) 0.63321(4) 0.86174(4) 0.0436 1.0000 Uani . . . . . .
H11 H 0.1753 0.1430 0.7967 0.0214 1.0000 Uiso R . . . . .
H41 H 0.3138 0.4269 0.6442 0.0219 1.0000 Uiso R . . . . .
H61 H 0.1934 0.4335 0.8793 0.0282 1.0000 Uiso R . . . . .
H62 H 0.0974 0.4129 0.7999 0.0277 1.0000 Uiso R . . . . .
H81 H 0.1711 0.1718 1.0012 0.0372 1.0000 Uiso R . . . . .
H91 H 0.0138 0.0834 1.1812 0.0498 1.0000 Uiso R . . . . .
H101 H -0.2031 0.1696 1.2550 0.0527 1.0000 Uiso R . . . . .
H111 H -0.2642 0.3425 1.1491 0.0523 1.0000 Uiso R . . . . .
H121 H -0.1066 0.4271 0.9681 0.0395 1.0000 Uiso R . . . . .
H221 H 0.2397 0.3437 0.5126 0.0267 1.0000 Uiso R . . . . .
H231 H 0.0753 0.4008 0.4117 0.0308 1.0000 Uiso R . . . . .
H251 H -0.2180 0.2301 0.6958 0.0337 1.0000 Uiso R . . . . .
H261 H -0.0515 0.1675 0.7947 0.0302 1.0000 Uiso R . . . . .
H341 H 0.3197 -0.0563 0.4546 0.0353 1.0000 Uiso R . . . . .
H342 H 0.1679 -0.0864 0.5398 0.0358 1.0000 Uiso R . . . . .
H352 H 0.1508 0.0061 0.3537 0.0619 1.0000 Uiso R . . . . .
H351 H 0.2408 0.1114 0.3553 0.0614 1.0000 Uiso R . . . . .
H353 H 0.0905 0.0943 0.4465 0.0609 1.0000 Uiso R . . . . .
H392 H 0.5144 -0.0722 0.8619 0.0548 1.0000 Uiso R . . . . .
H391 H 0.4191 -0.1642 0.8462 0.0544 1.0000 Uiso R . . . . .
H401 H 0.3621 -0.1511 1.0557 0.0909 1.0000 Uiso R . . . . .
H403 H 0.3385 -0.0156 1.0210 0.0904 1.0000 Uiso R . . . . .
H402 H 0.2297 -0.1043 1.0080 0.0912 1.0000 Uiso R . . . . .
H421 H 0.4526 0.5861 0.6211 0.0289 1.0000 Uiso R . . . . .
H431 H 0.5983 0.6887 0.6870 0.0326 1.0000 Uiso R . . . . .
H451 H 0.6363 0.4050 0.9269 0.0410 1.0000 Uiso R . . . . .
H461 H 0.4875 0.3035 0.8614 0.0352 1.0000 Uiso R . . . . .
H31 H 0.5175 0.2756 0.6096 0.0256 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.82(16)
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
C1 . C2 . 1.5516(16) yes
C1 . N5 . 1.4768(15) yes
C1 . C21 . 1.5207(16) yes
C1 . H11 . 0.979 no
C2 . N3 . 1.4592(15) yes
C2 . C31 . 1.5369(17) yes
C2 . C36 . 1.5503(16) yes
N3 . C4 . 1.4752(16) yes
N3 . H31 . 0.861 no
C4 . N5 . 1.4707(15) yes
C4 . C41 . 1.5123(17) yes
C4 . H41 . 0.981 no
N5 . C6 . 1.4597(15) yes
C6 . C7 . 1.5101(17) yes
C6 . H61 . 0.982 no
C6 . H62 . 0.986 no
C7 . C8 . 1.391(2) yes
C7 . C12 . 1.3932(19) yes
C8 . C9 . 1.396(2) yes
C8 . H81 . 0.939 no
C9 . C10 . 1.385(3) yes
C9 . H91 . 0.940 no
C10 . C11 . 1.382(3) yes
C10 . H101 . 0.935 no
C11 . C12 . 1.383(2) yes
C11 . H111 . 0.963 no
C12 . H121 . 0.942 no
C21 . C22 . 1.3945(18) yes
C21 . C26 . 1.3941(17) yes
C22 . C23 . 1.3906(18) yes
C22 . H221 . 0.935 no
C23 . C24 . 1.3851(19) yes
C23 . H231 . 0.951 no
C24 . C25 . 1.383(2) yes
C24 . Cl27 . 1.7431(13) yes
C25 . C26 . 1.3911(19) yes
C25 . H251 . 0.936 no
C26 . H261 . 0.959 no
C31 . O32 . 1.2003(16) yes
C31 . O33 . 1.3336(15) yes
O33 . C34 . 1.4592(15) yes
C34 . C35 . 1.508(2) yes
C34 . H341 . 0.954 no
C34 . H342 . 0.972 no
C35 . H352 . 0.966 no
C35 . H351 . 0.959 no
C35 . H353 . 0.983 no
C36 . O37 . 1.1994(16) yes
C36 . O38 . 1.3233(16) yes
O38 . C39 . 1.4610(17) yes
C39 . C40 . 1.494(3) yes
C39 . H392 . 0.963 no
C39 . H391 . 0.985 no
C40 . H401 . 0.988 no
C40 . H403 . 0.969 no
C40 . H402 . 0.999 no
C41 . C42 . 1.3898(18) yes
C41 . C46 . 1.3931(18) yes
C42 . C43 . 1.3902(19) yes
C42 . H421 . 0.945 no
C43 . C44 . 1.381(2) yes
C43 . H431 . 0.936 no
C44 . C45 . 1.386(2) yes
C44 . Cl47 . 1.7432(14) yes
C45 . C46 . 1.385(2) yes
C45 . H451 . 0.944 no
C46 . H461 . 0.933 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
C2 . C1 . N5 . 98.25(9) yes
C2 . C1 . C21 . 115.22(10) yes
N5 . C1 . C21 . 115.46(10) yes
C2 . C1 . H11 . 108.6 no
N5 . C1 . H11 . 110.1 no
C21 . C1 . H11 . 108.7 no
C1 . C2 . N3 . 103.79(9) yes
C1 . C2 . C31 . 114.35(10) yes
N3 . C2 . C31 . 110.88(10) yes
C1 . C2 . C36 . 109.66(10) yes
N3 . C2 . C36 . 110.09(10) yes
C31 . C2 . C36 . 108.03(10) yes
C2 . N3 . C4 . 107.77(9) yes
C2 . N3 . H31 . 110.4 no
C4 . N3 . H31 . 110.4 no
N3 . C4 . N5 . 104.32(9) yes
N3 . C4 . C41 . 114.23(10) yes
N5 . C4 . C41 . 112.34(10) yes
N3 . C4 . H41 . 107.9 no
N5 . C4 . H41 . 109.5 no
C41 . C4 . H41 . 108.4 no
C1 . N5 . C4 . 105.16(9) yes
C1 . N5 . C6 . 116.28(10) yes
C4 . N5 . C6 . 111.65(10) yes
N5 . C6 . C7 . 114.23(11) yes
N5 . C6 . H61 . 107.1 no
C7 . C6 . H61 . 108.1 no
N5 . C6 . H62 . 109.8 no
C7 . C6 . H62 . 109.6 no
H61 . C6 . H62 . 107.8 no
C6 . C7 . C8 . 122.68(12) yes
C6 . C7 . C12 . 118.43(12) yes
C8 . C7 . C12 . 118.81(13) yes
C7 . C8 . C9 . 120.07(15) yes
C7 . C8 . H81 . 119.0 no
C9 . C8 . H81 . 121.0 no
C8 . C9 . C10 . 120.43(16) yes
C8 . C9 . H91 . 119.3 no
C10 . C9 . H91 . 120.3 no
C9 . C10 . C11 . 119.54(15) yes
C9 . C10 . H101 . 120.7 no
C11 . C10 . H101 . 119.8 no
C10 . C11 . C12 . 120.25(16) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.5 no
C7 . C12 . C11 . 120.88(15) yes
C7 . C12 . H121 . 118.8 no
C11 . C12 . H121 . 120.4 no
C1 . C21 . C22 . 123.34(11) yes
C1 . C21 . C26 . 118.19(11) yes
C22 . C21 . C26 . 118.47(11) yes
C21 . C22 . C23 . 121.05(12) yes
C21 . C22 . H221 . 120.5 no
C23 . C22 . H221 . 118.4 no
C22 . C23 . C24 . 118.80(12) yes
C22 . C23 . H231 . 121.1 no
C24 . C23 . H231 . 120.0 no
C23 . C24 . C25 . 121.77(12) yes
C23 . C24 . Cl27 . 119.07(11) yes
C25 . C24 . Cl27 . 119.15(10) yes
C24 . C25 . C26 . 118.50(12) yes
C24 . C25 . H251 . 120.7 no
C26 . C25 . H251 . 120.8 no
C21 . C26 . C25 . 121.39(12) yes
C21 . C26 . H261 . 119.2 no
C25 . C26 . H261 . 119.3 no
C2 . C31 . O32 . 123.89(11) yes
C2 . C31 . O33 . 110.40(10) yes
O32 . C31 . O33 . 125.70(12) yes
C31 . O33 . C34 . 116.51(10) yes
O33 . C34 . C35 . 111.35(11) yes
O33 . C34 . H341 . 108.7 no
C35 . C34 . H341 . 110.5 no
O33 . C34 . H342 . 105.1 no
C35 . C34 . H342 . 110.7 no
H341 . C34 . H342 . 110.4 no
C34 . C35 . H352 . 108.5 no
C34 . C35 . H351 . 110.9 no
H352 . C35 . H351 . 110.0 no
C34 . C35 . H353 . 110.4 no
H352 . C35 . H353 . 108.4 no
H351 . C35 . H353 . 108.5 no
C2 . C36 . O37 . 123.02(12) yes
C2 . C36 . O38 . 111.68(10) yes
O37 . C36 . O38 . 125.29(12) yes
C36 . O38 . C39 . 117.72(11) yes
O38 . C39 . C40 . 108.25(15) yes
O38 . C39 . H392 . 111.8 no
C40 . C39 . H392 . 113.3 no
O38 . C39 . H391 . 107.3 no
C40 . C39 . H391 . 110.3 no
H392 . C39 . H391 . 105.8 no
C39 . C40 . H401 . 110.7 no
C39 . C40 . H403 . 105.5 no
H401 . C40 . H403 . 107.7 no
C39 . C40 . H402 . 111.8 no
H401 . C40 . H402 . 110.8 no
H403 . C40 . H402 . 110.1 no
C4 . C41 . C42 . 119.40(11) yes
C4 . C41 . C46 . 121.56(11) yes
C42 . C41 . C46 . 119.03(12) yes
C41 . C42 . C43 . 120.91(12) yes
C41 . C42 . H421 . 119.6 no
C43 . C42 . H421 . 119.5 no
C42 . C43 . C44 . 118.76(12) yes
C42 . C43 . H431 . 120.4 no
C44 . C43 . H431 . 120.8 no
C43 . C44 . C45 . 121.59(13) yes
C43 . C44 . Cl47 . 118.89(11) yes
C45 . C44 . Cl47 . 119.53(11) yes
C44 . C45 . C46 . 118.95(13) yes
C44 . C45 . H451 . 119.9 no
C46 . C45 . H451 . 121.2 no
C41 . C46 . C45 . 120.75(13) yes
C41 . C46 . H461 . 119.1 no
C45 . C46 . H461 . 120.1 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
C22 . H221 . N3 . 122 0.93 2.56 3.156(2) yes
C34 . H341 . O37 2_656 142 0.95 2.53 3.330(2) 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
0 -2 3 x .
-3 -3 2 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_247l-21l
_database_code_depnum_ccdc_archive 'CCDC 2256198'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2020-02-06
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7271
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   11.96040(10)
_cell_length_b                   10.72610(10)
_cell_length_c                   23.5537(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.4393(7)
_cell_angle_gamma                90
_cell_volume                     3008.06(5)

_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 = C33 H34 F2 N2 O7 
# Dc =      1.34 Fooo =   1280.00 Mu =      8.59 M =    608.64
# Found Formula = C33 H34 F2 N2 O7 
# Dc =      1.34 FOOO =   1280.00 Mu =      8.59 M =    608.64

_chemical_formula_sum            'C33 H34 F2 N2 O7'
_chemical_formula_moiety         'C33 H34 F2 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         608.64


_cell_measurement_reflns_used    21017
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      76.07
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.22
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.859

# Sheldrick geometric approximatio 0.81 0.83 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.83
_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            38982
_diffrn_reflns_av_unetI/netI     0.041
_reflns_number_total             6254
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0409
# Number of reflections with Friedels Law is 6254 
# Theoretical number of reflections is about 12588 

_diffrn_reflns_theta_min         3.712
_diffrn_reflns_theta_max         76.165
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.642
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   2.34
_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         -0.27
_refine_diff_density_max         0.44


# 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     0
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6254
_oxford_refine_ls_R_factor_ref   0.0451
_refine_ls_R_factor_all          0.0451
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_all         0.1179
_refine_ls_goodness_of_fit_ref   1.0022
_refine_ls_shift/su_max          0.0003800
_refine_ls_shift/su_mean         0.0000382


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        6254
_oxford_refine_ls_R_factor_all   0.0451
_oxford_refine_ls_wR_factor_all  0.1179

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5857
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_gt          0.1149


_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 + 1.00P] 
 ,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
C1 C 0.11792(9) 0.19020(10) 0.36574(5) 0.0188 1.0000 Uani . . . . . .
N2 N 0.13752(8) 0.29560(9) 0.32833(4) 0.0195 1.0000 Uani . . . . . .
C3 C 0.25792(9) 0.32160(10) 0.33411(5) 0.0190 1.0000 Uani . . . . . .
C4 C 0.29189(9) 0.29670(10) 0.39926(5) 0.0189 1.0000 Uani . . . . . .
N5 N 0.20484(8) 0.21035(9) 0.41339(4) 0.0190 1.0000 Uani . . . . . .
C6 C 0.22493(10) 0.14042(11) 0.46151(5) 0.0228 1.0000 Uani . . . . . .
O7 O 0.30872(8) 0.15918(10) 0.49432(4) 0.0333 1.0000 Uani . . . . . .
C8 C 0.14039(10) 0.04177(12) 0.47419(5) 0.0250 1.0000 Uani . . . . . .
C9 C 0.13778(11) -0.07103(12) 0.43553(6) 0.0282 1.0000 Uani . . . . . .
O10 O 0.20334(11) -0.09342(11) 0.40142(6) 0.0530 1.0000 Uani . . . . . .
O11 O 0.05105(8) -0.14351(9) 0.44466(4) 0.0310 1.0000 Uani . . . . . .
C12 C 0.03757(13) -0.25647(14) 0.41057(7) 0.0370 1.0000 Uani . . . . . .
C13 C -0.05977(17) -0.32652(18) 0.42908(7) 0.0516 1.0000 Uani . . . . . .
C21 C -0.00120(9) 0.19880(11) 0.38294(5) 0.0210 1.0000 Uani . . . . . .
C22 C -0.03368(10) 0.29953(12) 0.41504(5) 0.0239 1.0000 Uani . . . . . .
C23 C -0.14263(11) 0.30942(13) 0.43030(6) 0.0283 1.0000 Uani . . . . . .
C24 C -0.22199(11) 0.21875(14) 0.41284(6) 0.0309 1.0000 Uani . . . . . .
C25 C -0.19169(11) 0.11860(14) 0.38053(6) 0.0311 1.0000 Uani . . . . . .
C26 C -0.08235(10) 0.11070(12) 0.36642(5) 0.0246 1.0000 Uani . . . . . .
F27 F -0.05415(7) 0.01067(8) 0.33523(4) 0.0344 1.0000 Uani . . . . . .
C31 C 0.08917(10) 0.27691(12) 0.26860(5) 0.0231 1.0000 Uani . . . . . .
C32 C 0.15105(10) 0.18557(12) 0.23388(5) 0.0236 1.0000 Uani . . . . . .
C33 C 0.12673(12) 0.05849(13) 0.23282(5) 0.0294 1.0000 Uani . . . . . .
C34 C 0.18843(14) -0.02441(14) 0.20274(6) 0.0365 1.0000 Uani . . . . . .
C35 C 0.27527(13) 0.01854(16) 0.17358(7) 0.0404 1.0000 Uani . . . . . .
C36 C 0.29907(13) 0.14466(17) 0.17329(7) 0.0420 1.0000 Uani . . . . . .
C37 C 0.23716(12) 0.22764(14) 0.20296(6) 0.0325 1.0000 Uani . . . . . .
C41 C 0.28249(10) 0.45074(11) 0.31274(5) 0.0217 1.0000 Uani . . . . . .
C42 C 0.20668(11) 0.54896(12) 0.31414(5) 0.0264 1.0000 Uani . . . . . .
C43 C 0.23171(13) 0.66617(13) 0.29362(6) 0.0332 1.0000 Uani . . . . . .
C44 C 0.33297(13) 0.68623(13) 0.27074(6) 0.0342 1.0000 Uani . . . . . .
C45 C 0.41011(12) 0.59061(14) 0.26924(6) 0.0327 1.0000 Uani . . . . . .
C46 C 0.38332(11) 0.47564(12) 0.29045(5) 0.0263 1.0000 Uani . . . . . .
F47 F 0.45949(7) 0.38184(8) 0.28968(4) 0.0376 1.0000 Uani . . . . . .
C51 C 0.40857(10) 0.23244(11) 0.40456(5) 0.0213 1.0000 Uani . . . . . .
O52 O 0.49646(7) 0.27666(9) 0.42287(4) 0.0301 1.0000 Uani . . . . . .
O53 O 0.39577(7) 0.11954(8) 0.38114(4) 0.0267 1.0000 Uani . . . . . .
C54 C 0.49636(12) 0.04577(14) 0.37978(7) 0.0346 1.0000 Uani . . . . . .
C55 C 0.46258(15) -0.06697(14) 0.34432(8) 0.0440 1.0000 Uani . . . . . .
C61 C 0.28790(10) 0.41621(11) 0.43535(5) 0.0212 1.0000 Uani . . . . . .
O62 O 0.21039(8) 0.44263(9) 0.46194(4) 0.0329 1.0000 Uani . . . . . .
O63 O 0.37669(7) 0.48687(8) 0.43028(4) 0.0252 1.0000 Uani . . . . . .
C64 C 0.38038(12) 0.60712(12) 0.45923(6) 0.0301 1.0000 Uani . . . . . .
C65 C 0.48222(14) 0.67242(14) 0.44157(6) 0.0369 1.0000 Uani . . . . . .
H11 H 0.1301 0.1098 0.3473 0.0223 1.0000 Uiso R . . . . .
H31 H 0.3008 0.2612 0.3134 0.0216 1.0000 Uiso R . . . . .
H81 H 0.1624 0.0128 0.5126 0.0305 1.0000 Uiso R . . . . .
H82 H 0.0669 0.0772 0.4729 0.0298 1.0000 Uiso R . . . . .
H121 H 0.1046 -0.3037 0.4158 0.0464 1.0000 Uiso R . . . . .
H122 H 0.0232 -0.2309 0.3702 0.0438 1.0000 Uiso R . . . . .
H131 H -0.0740 -0.3997 0.4057 0.0749 1.0000 Uiso R . . . . .
H132 H -0.0446 -0.3501 0.4679 0.0767 1.0000 Uiso R . . . . .
H133 H -0.1243 -0.2705 0.4250 0.0775 1.0000 Uiso R . . . . .
H221 H 0.0200 0.3624 0.4269 0.0288 1.0000 Uiso R . . . . .
H231 H -0.1628 0.3780 0.4525 0.0349 1.0000 Uiso R . . . . .
H241 H -0.2963 0.2263 0.4232 0.0384 1.0000 Uiso R . . . . .
H251 H -0.2444 0.0555 0.3677 0.0375 1.0000 Uiso R . . . . .
H311 H 0.0886 0.3581 0.2495 0.0272 1.0000 Uiso R . . . . .
H312 H 0.0105 0.2500 0.2698 0.0279 1.0000 Uiso R . . . . .
H331 H 0.0677 0.0268 0.2532 0.0353 1.0000 Uiso R . . . . .
H341 H 0.1712 -0.1120 0.2022 0.0445 1.0000 Uiso R . . . . .
H351 H 0.3168 -0.0371 0.1538 0.0486 1.0000 Uiso R . . . . .
H361 H 0.3575 0.1741 0.1525 0.0500 1.0000 Uiso R . . . . .
H371 H 0.2529 0.3148 0.2015 0.0387 1.0000 Uiso R . . . . .
H421 H 0.1372 0.5343 0.3294 0.0325 1.0000 Uiso R . . . . .
H431 H 0.1796 0.7336 0.2950 0.0407 1.0000 Uiso R . . . . .
H441 H 0.3498 0.7651 0.2564 0.0405 1.0000 Uiso R . . . . .
H451 H 0.4808 0.6016 0.2540 0.0404 1.0000 Uiso R . . . . .
H541 H 0.5212 0.0209 0.4206 0.0399 1.0000 Uiso R . . . . .
H542 H 0.5541 0.0967 0.3625 0.0417 1.0000 Uiso R . . . . .
H553 H 0.5278 -0.1185 0.3393 0.0668 1.0000 Uiso R . . . . .
H552 H 0.4044 -0.1162 0.3623 0.0654 1.0000 Uiso R . . . . .
H551 H 0.4313 -0.0381 0.3053 0.0655 1.0000 Uiso R . . . . .
H641 H 0.3860 0.5929 0.5001 0.0352 1.0000 Uiso R . . . . .
H642 H 0.3116 0.6543 0.4477 0.0375 1.0000 Uiso R . . . . .
H651 H 0.4868 0.7549 0.4582 0.0546 1.0000 Uiso R . . . . .
H652 H 0.5506 0.6234 0.4539 0.0556 1.0000 Uiso R . . . . .
H653 H 0.4751 0.6786 0.4004 0.0540 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.35(7)
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
C1 . N2 . 1.4658(14) yes
C1 . N5 . 1.4717(14) yes
C1 . C21 . 1.5205(15) yes
C1 . H11 . 0.983 no
N2 . C3 . 1.4604(14) yes
N2 . C31 . 1.4830(14) yes
C3 . C4 . 1.5725(15) yes
C3 . C41 . 1.5121(15) yes
C3 . H31 . 0.984 no
C4 . N5 . 1.4554(14) yes
C4 . C51 . 1.5509(15) yes
C4 . C61 . 1.5414(15) yes
N5 . C6 . 1.3615(16) yes
C6 . O7 . 1.2227(15) yes
C6 . C8 . 1.5128(16) yes
C8 . C9 . 1.5129(18) yes
C8 . H81 . 0.968 no
C8 . H82 . 0.955 no
C9 . O10 . 1.1989(18) yes
C9 . O11 . 1.3300(15) yes
O11 . C12 . 1.4541(16) yes
C12 . C13 . 1.485(2) yes
C12 . H121 . 0.946 no
C12 . H122 . 0.988 no
C13 . H131 . 0.964 no
C13 . H132 . 0.949 no
C13 . H133 . 0.976 no
C21 . C22 . 1.3949(17) yes
C21 . C26 . 1.3837(17) yes
C22 . C23 . 1.3883(17) yes
C22 . H221 . 0.955 no
C23 . C24 . 1.394(2) yes
C23 . H231 . 0.947 no
C24 . C25 . 1.384(2) yes
C24 . H241 . 0.946 no
C25 . C26 . 1.3821(18) yes
C25 . H251 . 0.954 no
C26 . F27 . 1.3608(15) yes
C31 . C32 . 1.5136(17) yes
C31 . H311 . 0.980 no
C31 . H312 . 0.987 no
C32 . C33 . 1.3934(18) yes
C32 . C37 . 1.3918(18) yes
C33 . C34 . 1.392(2) yes
C33 . H331 . 0.953 no
C34 . C35 . 1.378(2) yes
C34 . H341 . 0.962 no
C35 . C36 . 1.383(2) yes
C35 . H351 . 0.930 no
C36 . C37 . 1.388(2) yes
C36 . H361 . 0.945 no
C37 . H371 . 0.955 no
C41 . C42 . 1.3924(17) yes
C41 . C46 . 1.3862(17) yes
C42 . C43 . 1.3897(18) yes
C42 . H421 . 0.949 no
C43 . C44 . 1.388(2) yes
C43 . H431 . 0.957 no
C44 . C45 . 1.382(2) yes
C44 . H441 . 0.939 no
C45 . C46 . 1.3797(18) yes
C45 . H451 . 0.957 no
C46 . F47 . 1.3585(16) yes
C51 . O52 . 1.1958(15) yes
C51 . O53 . 1.3335(15) yes
O53 . C54 . 1.4429(15) yes
C54 . C55 . 1.503(2) yes
C54 . H541 . 1.015 no
C54 . H542 . 0.998 no
C55 . H553 . 0.972 no
C55 . H552 . 0.999 no
C55 . H551 . 1.008 no
C61 . O62 . 1.2008(15) yes
C61 . O63 . 1.3193(14) yes
O63 . C64 . 1.4577(14) yes
C64 . C65 . 1.4978(19) yes
C64 . H641 . 0.970 no
C64 . H642 . 0.982 no
C65 . H651 . 0.967 no
C65 . H652 . 0.992 no
C65 . H653 . 0.967 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
N2 . C1 . N5 . 101.74(8) yes
N2 . C1 . C21 . 108.71(9) yes
N5 . C1 . C21 . 113.57(9) yes
N2 . C1 . H11 . 111.8 no
N5 . C1 . H11 . 110.0 no
C21 . C1 . H11 . 110.7 no
C1 . N2 . C3 . 107.68(9) yes
C1 . N2 . C31 . 113.31(9) yes
C3 . N2 . C31 . 114.00(9) yes
N2 . C3 . C4 . 102.71(8) yes
N2 . C3 . C41 . 111.40(9) yes
C4 . C3 . C41 . 116.10(9) yes
N2 . C3 . H31 . 112.5 no
C4 . C3 . H31 . 105.9 no
C41 . C3 . H31 . 108.1 no
C3 . C4 . N5 . 101.94(8) yes
C3 . C4 . C51 . 107.54(9) yes
N5 . C4 . C51 . 110.89(9) yes
C3 . C4 . C61 . 112.23(9) yes
N5 . C4 . C61 . 110.05(9) yes
C51 . C4 . C61 . 113.57(9) yes
C1 . N5 . C4 . 112.83(9) yes
C1 . N5 . C6 . 127.60(10) yes
C4 . N5 . C6 . 117.86(9) yes
N5 . C6 . O7 . 120.33(11) yes
N5 . C6 . C8 . 118.76(10) yes
O7 . C6 . C8 . 120.90(11) yes
C6 . C8 . C9 . 114.62(10) yes
C6 . C8 . H81 . 106.3 no
C9 . C8 . H81 . 107.0 no
C6 . C8 . H82 . 110.2 no
C9 . C8 . H82 . 109.5 no
H81 . C8 . H82 . 109.0 no
C8 . C9 . O10 . 125.88(12) yes
C8 . C9 . O11 . 109.99(11) yes
O10 . C9 . O11 . 124.13(13) yes
C9 . O11 . C12 . 116.43(11) yes
O11 . C12 . C13 . 107.97(13) yes
O11 . C12 . H121 . 109.0 no
C13 . C12 . H121 . 111.6 no
O11 . C12 . H122 . 107.5 no
C13 . C12 . H122 . 110.7 no
H121 . C12 . H122 . 110.0 no
C12 . C13 . H131 . 110.2 no
C12 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.9 no
C12 . C13 . H133 . 107.1 no
H131 . C13 . H133 . 110.4 no
H132 . C13 . H133 . 109.7 no
C1 . C21 . C22 . 120.50(10) yes
C1 . C21 . C26 . 122.26(11) yes
C22 . C21 . C26 . 117.22(11) yes
C21 . C22 . C23 . 121.07(12) yes
C21 . C22 . H221 . 119.5 no
C23 . C22 . H221 . 119.5 no
C22 . C23 . C24 . 120.00(12) yes
C22 . C23 . H231 . 119.8 no
C24 . C23 . H231 . 120.2 no
C23 . C24 . C25 . 119.82(12) yes
C23 . C24 . H241 . 119.6 no
C25 . C24 . H241 . 120.6 no
C24 . C25 . C26 . 118.86(12) yes
C24 . C25 . H251 . 121.7 no
C26 . C25 . H251 . 119.5 no
C21 . C26 . C25 . 123.03(12) yes
C21 . C26 . F27 . 119.15(11) yes
C25 . C26 . F27 . 117.82(11) yes
N2 . C31 . C32 . 115.68(10) yes
N2 . C31 . H311 . 107.5 no
C32 . C31 . H311 . 108.1 no
N2 . C31 . H312 . 107.5 no
C32 . C31 . H312 . 110.0 no
H311 . C31 . H312 . 107.9 no
C31 . C32 . C33 . 122.07(11) yes
C31 . C32 . C37 . 119.79(11) yes
C33 . C32 . C37 . 118.12(12) yes
C32 . C33 . C34 . 120.95(13) yes
C32 . C33 . H331 . 120.2 no
C34 . C33 . H331 . 118.8 no
C33 . C34 . C35 . 120.10(14) yes
C33 . C34 . H341 . 120.5 no
C35 . C34 . H341 . 119.4 no
C34 . C35 . C36 . 119.67(14) yes
C34 . C35 . H351 . 119.9 no
C36 . C35 . H351 . 120.4 no
C35 . C36 . C37 . 120.33(14) yes
C35 . C36 . H361 . 119.5 no
C37 . C36 . H361 . 120.2 no
C32 . C37 . C36 . 120.81(13) yes
C32 . C37 . H371 . 119.6 no
C36 . C37 . H371 . 119.5 no
C3 . C41 . C42 . 122.52(11) yes
C3 . C41 . C46 . 120.40(11) yes
C42 . C41 . C46 . 117.08(11) yes
C41 . C42 . C43 . 120.92(12) yes
C41 . C42 . H421 . 118.6 no
C43 . C42 . H421 . 120.4 no
C42 . C43 . C44 . 120.00(13) yes
C42 . C43 . H431 . 120.6 no
C44 . C43 . H431 . 119.4 no
C43 . C44 . C45 . 120.26(12) yes
C43 . C44 . H441 . 120.2 no
C45 . C44 . H441 . 119.5 no
C44 . C45 . C46 . 118.39(13) yes
C44 . C45 . H451 . 122.3 no
C46 . C45 . H451 . 119.3 no
C41 . C46 . C45 . 123.34(13) yes
C41 . C46 . F47 . 118.10(11) yes
C45 . C46 . F47 . 118.56(12) yes
C4 . C51 . O52 . 127.32(11) yes
C4 . C51 . O53 . 107.65(9) yes
O52 . C51 . O53 . 124.89(11) yes
C51 . O53 . C54 . 116.35(10) yes
O53 . C54 . C55 . 105.83(11) yes
O53 . C54 . H541 . 107.0 no
C55 . C54 . H541 . 110.7 no
O53 . C54 . H542 . 108.7 no
C55 . C54 . H542 . 111.9 no
H541 . C54 . H542 . 112.3 no
C54 . C55 . H553 . 110.4 no
C54 . C55 . H552 . 110.6 no
H553 . C55 . H552 . 110.4 no
C54 . C55 . H551 . 108.5 no
H553 . C55 . H551 . 107.3 no
H552 . C55 . H551 . 109.6 no
C4 . C61 . O62 . 123.35(10) yes
C4 . C61 . O63 . 111.13(9) yes
O62 . C61 . O63 . 125.42(11) yes
C61 . O63 . C64 . 117.06(10) yes
O63 . C64 . C65 . 105.86(11) yes
O63 . C64 . H641 . 108.7 no
C65 . C64 . H641 . 111.5 no
O63 . C64 . H642 . 109.9 no
C65 . C64 . H642 . 111.4 no
H641 . C64 . H642 . 109.4 no
C64 . C65 . H651 . 109.4 no
C64 . C65 . H652 . 109.9 no
H651 . C65 . H652 . 110.6 no
C64 . C65 . H653 . 108.3 no
H651 . C65 . H653 . 109.9 no
H652 . C65 . H653 . 108.7 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
C22 . H221 . O62 . 155 0.95 2.50 3.3892(19) yes
C24 . H241 . O52 1_455 163 0.95 2.54 3.4543(19) yes
C64 . H641 . O52 2_666 126 0.97 2.60 3.2649(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_245f-20f
_database_code_depnum_ccdc_archive 'CCDC 2256193'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2019-06-06
_audit_creation_method           'CRYSTALS_ver_14.61_build_7212 '

_oxford_structure_analysis_title '7172 '
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.2680(4)
_cell_length_b                   11.6652(4)
_cell_length_c                   11.8384(4)
_cell_angle_alpha                80.247(3)
_cell_angle_beta                 71.111(3)
_cell_angle_gamma                86.325(3)
_cell_volume                     1322.17(9)

_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'


_cell_formula_units_Z            2

# Given Formula = C28 H28 Br2 N2 O4 
# Dc =      1.55 Fooo =    624.00 Mu =     41.90 M =    616.35
# Found Formula = C28 H28 Br2 N2 O4 
# Dc =      1.55 FOOO =    624.00 Mu =     41.90 M =    616.35

_chemical_formula_sum            'C28 H28 Br2 N2 O4'
_chemical_formula_moiety         'C28 H28 Br2 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         616.35


_cell_measurement_reflns_used    8981
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      76.04
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    4.190

# Sheldrick geometric approximatio 0.66 0.72 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.72
_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            14315
_diffrn_reflns_av_unetI/netI     0.033
_reflns_number_total             5458
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0333
# Number of reflections with Friedels Law is 5458 
# Theoretical number of reflections is about 11052 

_diffrn_reflns_theta_min         3.845
_diffrn_reflns_theta_max         76.071
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        74.550
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.31
_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         -0.40
_refine_diff_density_max         0.54


# 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     325
_refine_ls_number_reflns         5458
_oxford_refine_ls_R_factor_ref   0.0274
_refine_ls_wR_factor_ref         0.0665
_refine_ls_goodness_of_fit_ref   1.0078
_refine_ls_shift/su_max          0.0028959
_refine_ls_shift/su_mean         0.0000494


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        5458
_refine_ls_R_factor_all          0.0274
_refine_ls_wR_factor_all         0.0665

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5049
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_gt          0.0644


_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 + 0.45P] 
 ,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
N1 N 0.56599(13) 0.21704(11) 0.88861(11) 0.0178 1.0000 Uani . . . . . .
C2 C 0.63772(15) 0.13268(13) 0.80891(13) 0.0174 1.0000 Uani . . . . . .
N3 N 0.74032(13) 0.20210(11) 0.70813(11) 0.0172 1.0000 Uani . . . . . .
C4 C 0.78302(15) 0.29227(13) 0.76266(13) 0.0165 1.0000 Uani . . . . . .
C5 C 0.63852(15) 0.32713(13) 0.84188(13) 0.0166 1.0000 Uani . . . . . .
C6 C 0.64069(15) 0.39045(13) 0.94537(13) 0.0179 1.0000 Uani . . . . . .
O7 O 0.55532(12) 0.37701(10) 1.04395(10) 0.0242 1.0000 Uani . . . . . .
O8 O 0.74792(11) 0.46108(10) 0.90965(10) 0.0222 1.0000 Uani . . . . . .
C9 C 0.76692(18) 0.52331(15) 1.00023(16) 0.0268 1.0000 Uani . . . . . .
C10 C 0.8244(2) 0.44461(18) 1.08786(19) 0.0370 1.0000 Uani . . . . . .
C11 C 0.56472(16) 0.40786(13) 0.76224(13) 0.0194 1.0000 Uani . . . . . .
O12 O 0.45572(12) 0.38526(11) 0.75557(11) 0.0266 1.0000 Uani . . . . . .
O13 O 0.63640(13) 0.50324(11) 0.70654(12) 0.0321 1.0000 Uani . . . . . .
C14 C 0.5776(2) 0.58800(18) 0.6303(2) 0.0410 1.0000 Uani . . . . . .
C15 C 0.6642(3) 0.5905(3) 0.5019(2) 0.0604 1.0000 Uani . . . . . .
C21 C 0.54356(15) 0.06759(13) 0.76678(13) 0.0184 1.0000 Uani . . . . . .
C22 C 0.51093(16) -0.04742(14) 0.81859(13) 0.0202 1.0000 Uani . . . . . .
C23 C 0.42571(17) -0.11055(14) 0.78152(14) 0.0226 1.0000 Uani . . . . . .
C24 C 0.37294(17) -0.05623(15) 0.69252(15) 0.0239 1.0000 Uani . . . . . .
C25 C 0.4034(2) 0.05892(16) 0.63932(16) 0.0294 1.0000 Uani . . . . . .
C26 C 0.48919(18) 0.11981(15) 0.67662(15) 0.0265 1.0000 Uani . . . . . .
Br27 Br 0.25545(2) -0.141538(18) 0.642387(18) 0.0355 1.0000 Uani . . . . . .
C31 C 0.85059(16) 0.12871(13) 0.64365(14) 0.0207 1.0000 Uani . . . . . .
C32 C 0.95276(17) 0.19254(14) 0.53157(14) 0.0211 1.0000 Uani . . . . . .
C33 C 0.92013(19) 0.29575(15) 0.46748(15) 0.0268 1.0000 Uani . . . . . .
C34 C 1.0169(2) 0.34748(18) 0.36108(16) 0.0353 1.0000 Uani . . . . . .
C35 C 1.1450(2) 0.29621(19) 0.31750(17) 0.0395 1.0000 Uani . . . . . .
C36 C 1.1773(2) 0.19381(18) 0.38079(19) 0.0379 1.0000 Uani . . . . . .
C37 C 1.08237(18) 0.14275(16) 0.48798(16) 0.0284 1.0000 Uani . . . . . .
C41 C 0.88402(15) 0.25201(13) 0.83120(13) 0.0170 1.0000 Uani . . . . . .
C42 C 0.84573(15) 0.18153(13) 0.94437(14) 0.0191 1.0000 Uani . . . . . .
C43 C 0.94147(16) 0.14669(14) 1.00405(14) 0.0210 1.0000 Uani . . . . . .
C44 C 1.07584(16) 0.18375(14) 0.94986(15) 0.0213 1.0000 Uani . . . . . .
C45 C 1.11835(16) 0.25260(15) 0.83714(15) 0.0237 1.0000 Uani . . . . . .
C46 C 1.02088(16) 0.28599(14) 0.77877(14) 0.0213 1.0000 Uani . . . . . .
Br47 Br 1.205109(19) 0.140625(16) 1.034021(18) 0.0317 1.0000 Uani . . . . . .
H21 H 0.6840 0.0755 0.8534 0.0204 1.0000 Uiso R . . . . .
H41 H 0.8239 0.3568 0.7014 0.0188 1.0000 Uiso R . . . . .
H91 H 0.8309 0.5841 0.9549 0.0323 1.0000 Uiso R . . . . .
H92 H 0.6815 0.5585 1.0395 0.0314 1.0000 Uiso R . . . . .
H102 H 0.8444 0.4913 1.1389 0.0559 1.0000 Uiso R . . . . .
H101 H 0.9076 0.4089 1.0440 0.0555 1.0000 Uiso R . . . . .
H103 H 0.7579 0.3850 1.1356 0.0556 1.0000 Uiso R . . . . .
H221 H 0.5453 -0.0825 0.8795 0.0251 1.0000 Uiso R . . . . .
H231 H 0.4040 -0.1861 0.8159 0.0261 1.0000 Uiso R . . . . .
H251 H 0.3675 0.0933 0.5787 0.0356 1.0000 Uiso R . . . . .
H261 H 0.5121 0.1963 0.6420 0.0323 1.0000 Uiso R . . . . .
H312 H 0.9006 0.0898 0.6970 0.0243 1.0000 Uiso R . . . . .
H311 H 0.8069 0.0682 0.6203 0.0245 1.0000 Uiso R . . . . .
H331 H 0.8324 0.3296 0.4933 0.0317 1.0000 Uiso R . . . . .
H341 H 0.9960 0.4182 0.3178 0.0423 1.0000 Uiso R . . . . .
H351 H 1.2097 0.3296 0.2477 0.0467 1.0000 Uiso R . . . . .
H361 H 1.2630 0.1596 0.3518 0.0463 1.0000 Uiso R . . . . .
H371 H 1.1045 0.0753 0.5331 0.0345 1.0000 Uiso R . . . . .
H421 H 0.7539 0.1585 0.9816 0.0224 1.0000 Uiso R . . . . .
H431 H 0.9156 0.1004 1.0798 0.0250 1.0000 Uiso R . . . . .
H451 H 1.2092 0.2760 0.8030 0.0281 1.0000 Uiso R . . . . .
H461 H 1.0458 0.3314 0.7050 0.0257 1.0000 Uiso R . . . . .
H11 H 0.4818 0.2261 0.8884 0.0208 1.0000 Uiso R . . . . .
H142 H 0.5834 0.6629 0.6548 0.0486 1.0000 Uiso R . . . . .
H141 H 0.4834 0.5723 0.6439 0.0490 1.0000 Uiso R . . . . .
H153 H 0.6297 0.6503 0.4532 0.0907 1.0000 Uiso R . . . . .
H152 H 0.7583 0.6049 0.4944 0.0906 1.0000 Uiso R . . . . .
H151 H 0.6579 0.5161 0.4809 0.0903 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.62(6)
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
N1 . C2 . 1.4741(19) yes
N1 . C5 . 1.4578(18) yes
N1 . H11 . 0.864 no
C2 . N3 . 1.4687(18) yes
C2 . C21 . 1.515(2) yes
C2 . H21 . 0.974 no
N3 . C4 . 1.4792(19) yes
N3 . C31 . 1.4612(19) yes
C4 . C5 . 1.5483(19) yes
C4 . C41 . 1.519(2) yes
C4 . H41 . 0.963 no
C5 . C6 . 1.541(2) yes
C5 . C11 . 1.556(2) yes
C6 . O7 . 1.2034(19) yes
C6 . O8 . 1.3292(19) yes
O8 . C9 . 1.4602(19) yes
C9 . C10 . 1.507(3) yes
C9 . H91 . 0.962 no
C9 . H92 . 0.953 no
C10 . H102 . 0.954 no
C10 . H101 . 0.956 no
C10 . H103 . 0.973 no
C11 . O12 . 1.196(2) yes
C11 . O13 . 1.325(2) yes
O13 . C14 . 1.460(2) yes
C14 . C15 . 1.488(4) yes
C14 . H142 . 0.977 no
C14 . H141 . 0.952 no
C15 . H153 . 0.954 no
C15 . H152 . 0.964 no
C15 . H151 . 0.953 no
C21 . C22 . 1.391(2) yes
C21 . C26 . 1.394(2) yes
C22 . C23 . 1.393(2) yes
C22 . H221 . 0.926 no
C23 . C24 . 1.380(2) yes
C23 . H231 . 0.914 no
C24 . C25 . 1.392(2) yes
C24 . Br27 . 1.9014(16) yes
C25 . C26 . 1.384(2) yes
C25 . H251 . 0.931 no
C26 . H261 . 0.927 no
C31 . C32 . 1.510(2) yes
C31 . H312 . 0.976 no
C31 . H311 . 0.981 no
C32 . C33 . 1.393(2) yes
C32 . C37 . 1.390(2) yes
C33 . C34 . 1.395(3) yes
C33 . H331 . 0.937 no
C34 . C35 . 1.385(3) yes
C34 . H341 . 0.946 no
C35 . C36 . 1.381(3) yes
C35 . H351 . 0.919 no
C36 . C37 . 1.390(3) yes
C36 . H361 . 0.926 no
C37 . H371 . 0.932 no
C41 . C42 . 1.397(2) yes
C41 . C46 . 1.393(2) yes
C42 . C43 . 1.390(2) yes
C42 . H421 . 0.937 no
C43 . C44 . 1.383(2) yes
C43 . H431 . 0.931 no
C44 . C45 . 1.386(2) yes
C44 . Br47 . 1.8996(15) yes
C45 . C46 . 1.392(2) yes
C45 . H451 . 0.927 no
C46 . H461 . 0.908 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
C2 . N1 . C5 . 107.66(11) yes
C2 . N1 . H11 . 109.8 no
C5 . N1 . H11 . 109.9 no
N1 . C2 . N3 . 104.43(11) yes
N1 . C2 . C21 . 114.10(12) yes
N3 . C2 . C21 . 112.50(12) yes
N1 . C2 . H21 . 108.1 no
N3 . C2 . H21 . 109.8 no
C21 . C2 . H21 . 107.8 no
C2 . N3 . C4 . 105.05(11) yes
C2 . N3 . C31 . 111.36(12) yes
C4 . N3 . C31 . 115.95(12) yes
N3 . C4 . C5 . 98.25(11) yes
N3 . C4 . C41 . 115.47(12) yes
C5 . C4 . C41 . 114.91(12) yes
N3 . C4 . H41 . 110.3 no
C5 . C4 . H41 . 110.1 no
C41 . C4 . H41 . 107.5 no
C4 . C5 . N1 . 104.01(12) yes
C4 . C5 . C6 . 113.90(12) yes
N1 . C5 . C6 . 111.23(11) yes
C4 . C5 . C11 . 109.94(11) yes
N1 . C5 . C11 . 109.70(12) yes
C6 . C5 . C11 . 108.01(12) yes
C5 . C6 . O7 . 123.64(14) yes
C5 . C6 . O8 . 110.59(12) yes
O7 . C6 . O8 . 125.77(15) yes
C6 . O8 . C9 . 116.77(13) yes
O8 . C9 . C10 . 111.55(14) yes
O8 . C9 . H91 . 105.1 no
C10 . C9 . H91 . 110.4 no
O8 . C9 . H92 . 108.7 no
C10 . C9 . H92 . 112.6 no
H91 . C9 . H92 . 108.2 no
C9 . C10 . H102 . 107.9 no
C9 . C10 . H101 . 109.4 no
H102 . C10 . H101 . 109.1 no
C9 . C10 . H103 . 110.1 no
H102 . C10 . H103 . 110.5 no
H101 . C10 . H103 . 109.8 no
C5 . C11 . O12 . 122.87(14) yes
C5 . C11 . O13 . 111.52(13) yes
O12 . C11 . O13 . 125.60(14) yes
C11 . O13 . C14 . 117.30(14) yes
O13 . C14 . C15 . 108.69(18) yes
O13 . C14 . H142 . 105.3 no
C15 . C14 . H142 . 109.4 no
O13 . C14 . H141 . 111.5 no
C15 . C14 . H141 . 113.0 no
H142 . C14 . H141 . 108.7 no
C14 . C15 . H153 . 108.3 no
C14 . C15 . H152 . 109.0 no
H153 . C15 . H152 . 111.1 no
C14 . C15 . H151 . 107.6 no
H153 . C15 . H151 . 111.0 no
H152 . C15 . H151 . 109.8 no
C2 . C21 . C22 . 119.35(13) yes
C2 . C21 . C26 . 121.68(14) yes
C22 . C21 . C26 . 118.97(14) yes
C21 . C22 . C23 . 121.07(14) yes
C21 . C22 . H221 . 119.6 no
C23 . C22 . H221 . 119.3 no
C22 . C23 . C24 . 118.57(15) yes
C22 . C23 . H231 . 121.0 no
C24 . C23 . H231 . 120.5 no
C23 . C24 . C25 . 121.65(15) yes
C23 . C24 . Br27 . 118.78(12) yes
C25 . C24 . Br27 . 119.57(13) yes
C24 . C25 . C26 . 118.90(15) yes
C24 . C25 . H251 . 120.0 no
C26 . C25 . H251 . 121.1 no
C21 . C26 . C25 . 120.84(15) yes
C21 . C26 . H261 . 118.4 no
C25 . C26 . H261 . 120.7 no
N3 . C31 . C32 . 114.37(13) yes
N3 . C31 . H312 . 110.5 no
C32 . C31 . H312 . 108.5 no
N3 . C31 . H311 . 107.1 no
C32 . C31 . H311 . 108.7 no
H312 . C31 . H311 . 107.4 no
C31 . C32 . C33 . 122.70(15) yes
C31 . C32 . C37 . 118.19(15) yes
C33 . C32 . C37 . 119.03(15) yes
C32 . C33 . C34 . 119.96(17) yes
C32 . C33 . H331 . 120.7 no
C34 . C33 . H331 . 119.3 no
C33 . C34 . C35 . 120.52(19) yes
C33 . C34 . H341 . 120.4 no
C35 . C34 . H341 . 119.1 no
C34 . C35 . C36 . 119.58(17) yes
C34 . C35 . H351 . 121.3 no
C36 . C35 . H351 . 119.1 no
C35 . C36 . C37 . 120.27(19) yes
C35 . C36 . H361 . 119.6 no
C37 . C36 . H361 . 120.1 no
C36 . C37 . C32 . 120.62(18) yes
C36 . C37 . H371 . 121.0 no
C32 . C37 . H371 . 118.4 no
C4 . C41 . C42 . 122.79(13) yes
C4 . C41 . C46 . 118.70(13) yes
C42 . C41 . C46 . 118.51(14) yes
C41 . C42 . C43 . 120.93(14) yes
C41 . C42 . H421 . 119.8 no
C43 . C42 . H421 . 119.2 no
C42 . C43 . C44 . 118.81(14) yes
C42 . C43 . H431 . 120.8 no
C44 . C43 . H431 . 120.4 no
C43 . C44 . C45 . 122.05(14) yes
C43 . C44 . Br47 . 118.77(12) yes
C45 . C44 . Br47 . 119.17(12) yes
C44 . C45 . C46 . 118.15(14) yes
C44 . C45 . H451 . 120.1 no
C46 . C45 . H451 . 121.8 no
C41 . C46 . C45 . 121.53(14) yes
C41 . C46 . H461 . 118.4 no
C45 . C46 . H461 . 120.0 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 . H92 . O12 2_667 141 0.95 2.55 3.343(3) yes
C42 . H421 . N1 . 123 0.94 2.52 3.137(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_247d-21d
_database_code_depnum_ccdc_archive 'CCDC 2256197'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
#============================================================================== 

_ccdc_journal_depnumber          xxx

_audit_creation_date             2019-06-10
_audit_creation_method           'CRYSTALS_ver_14.61_build_7212 '

_oxford_structure_analysis_title 7173
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.71680(10)
_cell_length_b                   11.10410(10)
_cell_length_c                   28.6225(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.0001(10)
_cell_angle_gamma                90
_cell_volume                     3086.38(5)

_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 0.0181 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 = C33 H34 F2 N2 O7 
# Dc =      1.31 Fooo =   1280.00 Mu =      8.37 M =    608.64
# Found Formula = C33 H34 F2 N2 O7 
# Dc =      1.31 FOOO =   1280.00 Mu =      8.37 M =    608.64

_chemical_formula_sum            'C33 H34 F2 N2 O7'
_chemical_formula_moiety         'C33 H34 F2 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         608.64


_cell_measurement_reflns_used    10256
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      76.06
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_max          0.38

_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.837

# Sheldrick geometric approximatio 0.84 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.84
_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            21584
_diffrn_reflns_av_unetI/netI     0.041
_reflns_number_total             6392
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0409
# Number of reflections with Friedels Law is 6392 
# Theoretical number of reflections is about 12939 

_diffrn_reflns_theta_min         4.271
_diffrn_reflns_theta_max         76.307
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        74.781
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   2.61
_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         -0.33
_refine_diff_density_max         0.41


# 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     397
_refine_ls_number_reflns         6392
_oxford_refine_ls_R_factor_ref   0.0437
_refine_ls_wR_factor_ref         0.1018
_refine_ls_goodness_of_fit_ref   1.0056
_refine_ls_shift/su_max          0.0006663
_refine_ls_shift/su_mean         0.0000603


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        6392
_refine_ls_R_factor_all          0.0437
_refine_ls_wR_factor_all         0.1018

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5548
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_gt          0.0950


_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 + 0.98P] 
 ,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
N1 N 0.67308(10) 0.46425(9) 0.32450(3) 0.0223 1.0000 Uani . . . . . .
C2 C 0.61374(12) 0.39558(11) 0.36191(4) 0.0219 1.0000 Uani . . . . . .
C3 C 0.70387(12) 0.43682(11) 0.40572(4) 0.0227 1.0000 Uani . . . . . .
N4 N 0.83191(10) 0.47138(10) 0.38433(3) 0.0233 1.0000 Uani . . . . . .
C5 C 0.79639(12) 0.53296(11) 0.34034(4) 0.0222 1.0000 Uani . . . . . .
C6 C 0.91544(12) 0.52517(12) 0.30781(4) 0.0247 1.0000 Uani . . . . . .
C7 C 0.96679(13) 0.62816(13) 0.28693(5) 0.0292 1.0000 Uani . . . . . .
C8 C 1.07264(14) 0.61862(15) 0.25527(5) 0.0364 1.0000 Uani . . . . . .
C9 C 1.12478(15) 0.50665(16) 0.24653(5) 0.0394 1.0000 Uani . . . . . .
C10 C 1.07856(15) 0.40327(15) 0.26749(5) 0.0372 1.0000 Uani . . . . . .
C11 C 0.97203(14) 0.41307(13) 0.29818(5) 0.0296 1.0000 Uani . . . . . .
F12 F 1.22565(11) 0.49528(11) 0.21513(4) 0.0598 1.0000 Uani . . . . . .
C13 C 0.60689(13) 0.45954(11) 0.28194(4) 0.0249 1.0000 Uani . . . . . .
O14 O 0.50603(10) 0.39472(9) 0.27604(3) 0.0318 1.0000 Uani . . . . . .
C15 C 0.65896(15) 0.53974(14) 0.24367(5) 0.0339 1.0000 Uani . . . . . .
C16 C 0.58873(13) 0.50957(12) 0.19747(4) 0.0286 1.0000 Uani . . . . . .
O17 O 0.61730(12) 0.42283(10) 0.17454(4) 0.0418 1.0000 Uani . . . . . .
O18 O 0.49492(9) 0.59114(9) 0.18458(3) 0.0283 1.0000 Uani . . . . . .
C19 C 0.33033(16) 0.67314(16) 0.13024(6) 0.0451 1.0000 Uani . . . . . .
C20 C 0.46425(12) 0.43385(12) 0.37073(4) 0.0246 1.0000 Uani . . . . . .
O21 O 0.38237(10) 0.37532(10) 0.39082(4) 0.0427 1.0000 Uani . . . . . .
O22 O 0.44288(9) 0.54731(8) 0.35709(3) 0.0292 1.0000 Uani . . . . . .
C23 C 0.30560(14) 0.59357(13) 0.36450(5) 0.0333 1.0000 Uani . . . . . .
C24 C 0.30209(18) 0.72056(15) 0.34705(7) 0.0476 1.0000 Uani . . . . . .
C25 C 0.63414(13) 0.26021(11) 0.35209(4) 0.0246 1.0000 Uani . . . . . .
O26 O 0.72191(11) 0.22422(9) 0.32730(4) 0.0365 1.0000 Uani . . . . . .
O27 O 0.55220(10) 0.19015(8) 0.37603(4) 0.0323 1.0000 Uani . . . . . .
C28 C 0.58115(18) 0.06164(13) 0.37269(6) 0.0400 1.0000 Uani . . . . . .
C29 C 0.50492(19) 0.00154(16) 0.41057(8) 0.0578 1.0000 Uani . . . . . .
C31 C 0.72520(13) 0.34319(12) 0.44366(4) 0.0254 1.0000 Uani . . . . . .
C32 C 0.63307(15) 0.33640(13) 0.47976(5) 0.0321 1.0000 Uani . . . . . .
C33 C 0.65319(17) 0.25366(15) 0.51583(5) 0.0398 1.0000 Uani . . . . . .
C34 C 0.76721(17) 0.18065(14) 0.51530(5) 0.0403 1.0000 Uani . . . . . .
C35 C 0.85947(16) 0.18347(14) 0.48014(5) 0.0381 1.0000 Uani . . . . . .
C36 C 0.83691(14) 0.26531(13) 0.44388(5) 0.0311 1.0000 Uani . . . . . .
F37 F 0.79049(12) 0.10249(10) 0.55128(3) 0.0576 1.0000 Uani . . . . . .
C41 C 0.93275(13) 0.53565(13) 0.41522(4) 0.0288 1.0000 Uani . . . . . .
C42 C 0.87688(13) 0.64246(13) 0.44103(4) 0.0285 1.0000 Uani . . . . . .
C43 C 0.81789(16) 0.62626(14) 0.48445(5) 0.0378 1.0000 Uani . . . . . .
C44 C 0.75897(18) 0.72212(17) 0.50736(6) 0.0482 1.0000 Uani . . . . . .
C45 C 0.76091(18) 0.83572(17) 0.48781(6) 0.0483 1.0000 Uani . . . . . .
C46 C 0.82168(18) 0.85367(15) 0.44526(6) 0.0430 1.0000 Uani . . . . . .
C47 C 0.87885(15) 0.75760(13) 0.42205(5) 0.0332 1.0000 Uani . . . . . .
C26 C 0.42586(15) 0.56966(14) 0.13959(5) 0.0340 1.0000 Uani . . . . . .
H31 H 0.6574 0.5069 0.4189 0.0249 1.0000 Uiso R . . . . .
H51 H 0.7714 0.6184 0.3456 0.0253 1.0000 Uiso R . . . . .
H71 H 0.9291 0.7035 0.2942 0.0340 1.0000 Uiso R . . . . .
H81 H 1.1063 0.6891 0.2406 0.0436 1.0000 Uiso R . . . . .
H101 H 1.1193 0.3290 0.2613 0.0452 1.0000 Uiso R . . . . .
H111 H 0.9359 0.3431 0.3123 0.0362 1.0000 Uiso R . . . . .
H151 H 0.6420 0.6229 0.2518 0.0412 1.0000 Uiso R . . . . .
H152 H 0.7575 0.5272 0.2412 0.0419 1.0000 Uiso R . . . . .
H191 H 0.2831 0.6619 0.1003 0.0674 1.0000 Uiso R . . . . .
H192 H 0.3805 0.7481 0.1287 0.0670 1.0000 Uiso R . . . . .
H193 H 0.2628 0.6789 0.1545 0.0677 1.0000 Uiso R . . . . .
H231 H 0.2893 0.5876 0.3982 0.0407 1.0000 Uiso R . . . . .
H232 H 0.2403 0.5424 0.3475 0.0381 1.0000 Uiso R . . . . .
H243 H 0.2138 0.7576 0.3512 0.0705 1.0000 Uiso R . . . . .
H242 H 0.3734 0.7669 0.3632 0.0692 1.0000 Uiso R . . . . .
H241 H 0.3196 0.7215 0.3143 0.0688 1.0000 Uiso R . . . . .
H281 H 0.6821 0.0495 0.3776 0.0481 1.0000 Uiso R . . . . .
H282 H 0.5511 0.0339 0.3419 0.0489 1.0000 Uiso R . . . . .
H293 H 0.5275 -0.0836 0.4115 0.0847 1.0000 Uiso R . . . . .
H292 H 0.5325 0.0396 0.4401 0.0871 1.0000 Uiso R . . . . .
H291 H 0.4079 0.0114 0.4046 0.0870 1.0000 Uiso R . . . . .
H321 H 0.5556 0.3886 0.4800 0.0377 1.0000 Uiso R . . . . .
H331 H 0.5904 0.2482 0.5398 0.0483 1.0000 Uiso R . . . . .
H351 H 0.9373 0.1314 0.4812 0.0456 1.0000 Uiso R . . . . .
H361 H 0.8996 0.2688 0.4192 0.0376 1.0000 Uiso R . . . . .
H411 H 0.9693 0.4777 0.4381 0.0349 1.0000 Uiso R . . . . .
H412 H 1.0076 0.5629 0.3953 0.0349 1.0000 Uiso R . . . . .
H431 H 0.8183 0.5483 0.4980 0.0452 1.0000 Uiso R . . . . .
H441 H 0.7189 0.7090 0.5364 0.0579 1.0000 Uiso R . . . . .
H451 H 0.7223 0.9023 0.5037 0.0587 1.0000 Uiso R . . . . .
H461 H 0.8241 0.9318 0.4316 0.0522 1.0000 Uiso R . . . . .
H471 H 0.9196 0.7700 0.3928 0.0400 1.0000 Uiso R . . . . .
H261 H 0.4960 0.5633 0.1160 0.0408 1.0000 Uiso R . . . . .
H262 H 0.3765 0.4930 0.1411 0.0396 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.18(5)
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
N1 . C2 . 1.4504(15) yes
N1 . C5 . 1.4783(15) yes
N1 . C13 . 1.3586(15) yes
C2 . C3 . 1.5726(15) yes
C2 . C20 . 1.5427(16) yes
C2 . C25 . 1.5433(17) yes
C3 . N4 . 1.4572(15) yes
C3 . C31 . 1.5123(17) yes
C3 . H31 . 0.982 no
N4 . C5 . 1.4634(15) yes
N4 . C41 . 1.4800(15) yes
C5 . C6 . 1.5125(17) yes
C5 . H51 . 0.992 no
C6 . C7 . 1.3910(18) yes
C6 . C11 . 1.3924(19) yes
C7 . C8 . 1.398(2) yes
C7 . H71 . 0.940 no
C8 . C9 . 1.369(2) yes
C8 . H81 . 0.952 no
C9 . C10 . 1.378(2) yes
C9 . F12 . 1.3586(16) yes
C10 . C11 . 1.385(2) yes
C10 . H101 . 0.935 no
C11 . H111 . 0.948 no
C13 . O14 . 1.2229(16) yes
C13 . C15 . 1.5125(18) yes
C15 . C16 . 1.5044(17) yes
C15 . H151 . 0.968 no
C15 . H152 . 0.973 no
C16 . O17 . 1.2034(18) yes
C16 . O18 . 1.3281(16) yes
O18 . C26 . 1.4510(15) yes
C19 . C26 . 1.495(2) yes
C19 . H191 . 0.966 no
C19 . H192 . 0.966 no
C19 . H193 . 0.974 no
C20 . O21 . 1.1908(16) yes
C20 . O22 . 1.3332(16) yes
O22 . C23 . 1.4518(16) yes
C23 . C24 . 1.496(2) yes
C23 . H231 . 0.984 no
C23 . H232 . 0.970 no
C24 . H243 . 0.962 no
C24 . H242 . 0.967 no
C24 . H241 . 0.960 no
C25 . O26 . 1.1969(16) yes
C25 . O27 . 1.3216(16) yes
O27 . C28 . 1.4582(17) yes
C28 . C29 . 1.492(2) yes
C28 . H281 . 0.995 no
C28 . H282 . 0.968 no
C29 . H293 . 0.971 no
C29 . H292 . 0.973 no
C29 . H291 . 0.958 no
C31 . C32 . 1.3926(18) yes
C31 . C36 . 1.3877(19) yes
C32 . C33 . 1.391(2) yes
C32 . H321 . 0.951 no
C33 . C34 . 1.373(2) yes
C33 . H331 . 0.937 no
C34 . C35 . 1.371(2) yes
C34 . F37 . 1.3597(16) yes
C35 . C36 . 1.3912(19) yes
C35 . H351 . 0.952 no
C36 . H361 . 0.950 no
C41 . C42 . 1.508(2) yes
C41 . H411 . 0.976 no
C41 . H412 . 0.987 no
C42 . C43 . 1.3982(19) yes
C42 . C47 . 1.3895(19) yes
C43 . C44 . 1.385(2) yes
C43 . H431 . 0.948 no
C44 . C45 . 1.380(3) yes
C44 . H441 . 0.942 no
C45 . C46 . 1.386(2) yes
C45 . H451 . 0.952 no
C46 . C47 . 1.383(2) yes
C46 . H461 . 0.952 no
C47 . H471 . 0.949 no
C26 . H261 . 0.978 no
C26 . H262 . 0.979 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
C2 . N1 . C5 . 112.56(9) yes
C2 . N1 . C13 . 116.98(10) yes
C5 . N1 . C13 . 130.41(10) yes
N1 . C2 . C3 . 102.18(9) yes
N1 . C2 . C20 . 112.15(10) yes
C3 . C2 . C20 . 106.89(9) yes
N1 . C2 . C25 . 108.71(10) yes
C3 . C2 . C25 . 110.94(10) yes
C20 . C2 . C25 . 115.20(10) yes
C2 . C3 . N4 . 101.62(9) yes
C2 . C3 . C31 . 115.53(10) yes
N4 . C3 . C31 . 112.65(10) yes
C2 . C3 . H31 . 106.7 no
N4 . C3 . H31 . 111.4 no
C31 . C3 . H31 . 108.8 no
C3 . N4 . C5 . 107.78(9) yes
C3 . N4 . C41 . 115.66(10) yes
C5 . N4 . C41 . 114.83(10) yes
N1 . C5 . N4 . 100.78(9) yes
N1 . C5 . C6 . 114.25(10) yes
N4 . C5 . C6 . 109.90(10) yes
N1 . C5 . H51 . 109.9 no
N4 . C5 . H51 . 111.6 no
C6 . C5 . H51 . 110.1 no
C5 . C6 . C7 . 120.74(12) yes
C5 . C6 . C11 . 119.26(11) yes
C7 . C6 . C11 . 119.99(12) yes
C6 . C7 . C8 . 119.95(13) yes
C6 . C7 . H71 . 119.3 no
C8 . C7 . H71 . 120.8 no
C7 . C8 . C9 . 118.20(13) yes
C7 . C8 . H81 . 119.7 no
C9 . C8 . H81 . 122.1 no
C8 . C9 . C10 . 123.28(13) yes
C8 . C9 . F12 . 119.04(14) yes
C10 . C9 . F12 . 117.67(15) yes
C9 . C10 . C11 . 118.22(14) yes
C9 . C10 . H101 . 120.4 no
C11 . C10 . H101 . 121.4 no
C6 . C11 . C10 . 120.33(13) yes
C6 . C11 . H111 . 119.6 no
C10 . C11 . H111 . 120.1 no
N1 . C13 . O14 . 119.90(11) yes
N1 . C13 . C15 . 117.83(11) yes
O14 . C13 . C15 . 122.23(11) yes
C13 . C15 . C16 . 110.64(11) yes
C13 . C15 . H151 . 108.8 no
C16 . C15 . H151 . 110.4 no
C13 . C15 . H152 . 108.9 no
C16 . C15 . H152 . 108.7 no
H151 . C15 . H152 . 109.3 no
C15 . C16 . O17 . 123.45(13) yes
C15 . C16 . O18 . 112.21(12) yes
O17 . C16 . O18 . 124.31(12) yes
C16 . O18 . C26 . 115.21(11) yes
C26 . C19 . H191 . 109.4 no
C26 . C19 . H192 . 111.0 no
H191 . C19 . H192 . 107.2 no
C26 . C19 . H193 . 110.6 no
H191 . C19 . H193 . 109.2 no
H192 . C19 . H193 . 109.3 no
C2 . C20 . O21 . 125.28(12) yes
C2 . C20 . O22 . 110.51(10) yes
O21 . C20 . O22 . 123.87(12) yes
C20 . O22 . C23 . 115.22(10) yes
O22 . C23 . C24 . 107.16(12) yes
O22 . C23 . H231 . 107.4 no
C24 . C23 . H231 . 112.8 no
O22 . C23 . H232 . 107.9 no
C24 . C23 . H232 . 112.1 no
H231 . C23 . H232 . 109.1 no
C23 . C24 . H243 . 111.8 no
C23 . C24 . H242 . 109.5 no
H243 . C24 . H242 . 109.9 no
C23 . C24 . H241 . 109.5 no
H243 . C24 . H241 . 107.9 no
H242 . C24 . H241 . 108.2 no
C2 . C25 . O26 . 122.13(11) yes
C2 . C25 . O27 . 113.29(11) yes
O26 . C25 . O27 . 124.43(12) yes
C25 . O27 . C28 . 114.89(11) yes
O27 . C28 . C29 . 106.75(14) yes
O27 . C28 . H281 . 108.3 no
C29 . C28 . H281 . 110.3 no
O27 . C28 . H282 . 108.5 no
C29 . C28 . H282 . 112.1 no
H281 . C28 . H282 . 110.6 no
C28 . C29 . H293 . 109.8 no
C28 . C29 . H292 . 107.9 no
H293 . C29 . H292 . 110.1 no
C28 . C29 . H291 . 109.3 no
H293 . C29 . H291 . 109.7 no
H292 . C29 . H291 . 110.1 no
C3 . C31 . C32 . 119.63(12) yes
C3 . C31 . C36 . 121.28(11) yes
C32 . C31 . C36 . 119.08(12) yes
C31 . C32 . C33 . 120.61(14) yes
C31 . C32 . H321 . 120.1 no
C33 . C32 . H321 . 119.3 no
C32 . C33 . C34 . 118.31(14) yes
C32 . C33 . H331 . 120.6 no
C34 . C33 . H331 . 121.1 no
C33 . C34 . C35 . 122.89(13) yes
C33 . C34 . F37 . 118.77(15) yes
C35 . C34 . F37 . 118.33(15) yes
C34 . C35 . C36 . 118.19(15) yes
C34 . C35 . H351 . 120.1 no
C36 . C35 . H351 . 121.7 no
C35 . C36 . C31 . 120.89(13) yes
C35 . C36 . H361 . 119.6 no
C31 . C36 . H361 . 119.5 no
N4 . C41 . C42 . 115.45(10) yes
N4 . C41 . H411 . 107.5 no
C42 . C41 . H411 . 108.6 no
N4 . C41 . H412 . 106.9 no
C42 . C41 . H412 . 109.0 no
H411 . C41 . H412 . 109.3 no
C41 . C42 . C43 . 119.99(13) yes
C41 . C42 . C47 . 121.46(12) yes
C43 . C42 . C47 . 118.53(14) yes
C42 . C43 . C44 . 120.75(15) yes
C42 . C43 . H431 . 119.0 no
C44 . C43 . H431 . 120.2 no
C43 . C44 . C45 . 119.92(15) yes
C43 . C44 . H441 . 119.3 no
C45 . C44 . H441 . 120.8 no
C44 . C45 . C46 . 119.98(16) yes
C44 . C45 . H451 . 120.4 no
C46 . C45 . H451 . 119.6 no
C45 . C46 . C47 . 120.11(16) yes
C45 . C46 . H461 . 120.6 no
C47 . C46 . H461 . 119.3 no
C42 . C47 . C46 . 120.69(14) yes
C42 . C47 . H471 . 119.4 no
C46 . C47 . H471 . 119.9 no
C19 . C26 . O18 . 107.31(12) yes
C19 . C26 . H261 . 112.0 no
O18 . C26 . H261 . 108.2 no
C19 . C26 . H262 . 112.0 no
O18 . C26 . H262 . 108.4 no
H261 . C26 . H262 . 108.9 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
C8 . H81 . O14 4_655 131 0.95 2.57 3.277(2) yes
C11 . H111 . O26 . 145 0.95 2.51 3.338(2) yes
C15 . H152 . C6 . 123 0.97 2.41 3.048(2) yes
C44 . H441 . O21 2_666 167 0.94 2.51 3.439(2) yes
C47 . H471 . O17 4_655 135 0.95 2.58 3.319(2) yes


