# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 2103730'
loop_
_audit_author_name
_audit_author_address
'Peter Knipe'
;Queens University, Belfast
United Kingdom
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-03-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7809 '

_oxford_structure_analysis_title 'xcalibur in C:\Users\peter\Documents\WR-1.13'
_chemical_name_systematic        5a
_chemical_melting_point          'not measured'

_cell_length_a                   9.52763(10)
_cell_length_b                   22.8402(2)
_cell_length_c                   12.17728(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.6178(10)
_cell_angle_gamma                90
_cell_volume                     2637.20(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'
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'
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'


_cell_formula_units_Z            4

# Given Formula = C121 H110 F1 N11 O11 
# Dc =      1.20 Fooo =   1010.00 Mu =      6.33 M =   1913.27
# Found Formula = C132 H92 F12 N8 O12 
# Dc =      1.39 FOOO =   1144.00 Mu =      8.70 M =   2210.20

_chemical_formula_sum            'C33 H23 F3 N2 O3'
_chemical_formula_moiety         'C33 H23 F3 N2 O3'
_chemical_compound_source        .
_chemical_formula_weight         552.53


_cell_measurement_reflns_used    8977
_cell_measurement_theta_min      5.02
_cell_measurement_theta_max      71.19
_cell_measurement_temperature    100

_exptl_crystal_description       plates
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.260

_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    0.870

# Sheldrick geometric approximatio 0.89 0.90 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.89
_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     1.54180
_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      100
_diffrn_ambient_pressure         100
_diffrn_reflns_number            15149
_diffrn_reflns_av_unetI/netI     0.067
_reflns_number_total             5075
_diffrn_reflns_av_R_equivalents  0.069
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5075 
# Theoretical number of reflections is about 10288 


_diffrn_reflns_theta_min         3.871
_diffrn_reflns_theta_max         71.526
_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        69.381
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   1.50
_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         -0.33
_refine_diff_density_max         0.28


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     4
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5074
_oxford_refine_ls_R_factor_ref   0.0489
_refine_ls_R_factor_all          0.0489
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_all         0.1231
_refine_ls_goodness_of_fit_ref   0.9972
_refine_ls_shift/su_max          0.0018421
_refine_ls_shift/su_mean         0.0003162


# Computed with I/sigma = -10 
_oxford_reflns_number_all        5075
_oxford_refine_ls_R_factor_all   0.0489
_oxford_refine_ls_wR_factor_all  0.1231

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4646
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.1176


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 0.90P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.77921(10) 0.11295(4) 0.52105(8) 0.0227 1.0000 Uani . . . . . .
C2 C 0.87389(15) 0.14095(6) 0.59049(12) 0.0139 1.0000 Uani . . . . . .
F3 F 0.82559(11) 0.13816(4) 0.68990(8) 0.0245 1.0000 Uani . . . . . .
F4 F 0.99229(10) 0.10896(4) 0.59680(10) 0.0296 1.0000 Uani . . . . . .
C5 C 0.89984(14) 0.20253(6) 0.55158(11) 0.0106 1.0000 Uani D . . . . .
N6 N 0.76662(12) 0.23517(5) 0.53892(9) 0.0105 1.0000 Uani D . . . . .
C7 C 0.78555(13) 0.29366(5) 0.58794(11) 0.0091 1.0000 Uani D . . . . .
C8 C 0.95147(13) 0.30153(6) 0.60839(11) 0.0099 1.0000 Uani . . . . . .
C9 C 0.99918(13) 0.23758(6) 0.63472(11) 0.0100 1.0000 Uani . . . . . .
C10 C 1.15623(14) 0.22701(6) 0.63324(11) 0.0113 1.0000 Uani . . . . . .
C11 C 1.24164(15) 0.22966(6) 0.73277(12) 0.0152 1.0000 Uani . . . . . .
C12 C 1.38684(15) 0.22135(7) 0.73616(13) 0.0191 1.0000 Uani . . . . . .
C13 C 1.44821(15) 0.20995(6) 0.63965(14) 0.0189 1.0000 Uani . . . . . .
C14 C 1.36393(16) 0.20705(7) 0.54023(13) 0.0186 1.0000 Uani . . . . . .
C15 C 1.21855(15) 0.21522(6) 0.53650(12) 0.0162 1.0000 Uani . . . . . .
C16 C 1.00730(13) 0.32710(6) 0.50429(12) 0.0123 1.0000 Uani . . . . . .
O17 O 1.00186(11) 0.30347(5) 0.41511(8) 0.0163 1.0000 Uani . . . . . .
C18 C 1.06808(14) 0.38562(6) 0.53251(13) 0.0156 1.0000 Uani . . . . . .
C19 C 1.06348(14) 0.39676(6) 0.64450(13) 0.0155 1.0000 Uani . . . . . .
C20 C 1.00367(14) 0.34563(6) 0.69832(12) 0.0124 1.0000 Uani . . . . . .
O21 O 1.00140(11) 0.33914(5) 0.79698(9) 0.0174 1.0000 Uani . . . . . .
C22 C 1.11372(16) 0.44893(7) 0.69298(15) 0.0230 1.0000 Uani . . . . . .
C23 C 1.16874(17) 0.48990(7) 0.62459(17) 0.0281 1.0000 Uani . . . . . .
C24 C 1.17516(16) 0.47877(7) 0.51242(17) 0.0282 1.0000 Uani . . . . . .
C25 C 1.12560(16) 0.42639(7) 0.46443(15) 0.0222 1.0000 Uani . . . . . .
C26 C 0.72150(13) 0.29891(6) 0.70119(11) 0.0100 1.0000 Uani . . . . . .
O27 O 0.74459(10) 0.26704(4) 0.78051(8) 0.0130 1.0000 Uani . . . . . .
N28 N 0.63588(12) 0.34731(5) 0.69520(10) 0.0113 1.0000 Uani . . . . . .
C29 C 0.61628(14) 0.36963(6) 0.58726(11) 0.0110 1.0000 Uani . . . . . .
C30 C 0.70288(13) 0.33971(6) 0.52042(11) 0.0104 1.0000 Uani . . . . . .
C31 C 0.69251(14) 0.35076(6) 0.40818(11) 0.0115 1.0000 Uani . . . . . .
C32 C 0.59577(15) 0.39287(6) 0.36502(12) 0.0140 1.0000 Uani . . . . . .
C33 C 0.51223(15) 0.42310(6) 0.43287(12) 0.0154 1.0000 Uani . . . . . .
C34 C 0.52071(15) 0.41184(6) 0.54635(12) 0.0146 1.0000 Uani . . . . . .
C35 C 0.56446(15) 0.36991(6) 0.78655(12) 0.0157 1.0000 Uani . . . . . .
C36 C 0.60101(16) 0.43366(6) 0.80999(11) 0.0163 1.0000 Uani . . . . . .
C37 C 0.50188(18) 0.47149(7) 0.84778(13) 0.0228 1.0000 Uani . . . . . .
C38 C 0.5382(2) 0.52959(8) 0.87343(13) 0.0301 1.0000 Uani . . . . . .
C39 C 0.6710(2) 0.55036(7) 0.86022(14) 0.0307 1.0000 Uani . . . . . .
C40 C 0.7700(2) 0.51293(7) 0.82227(15) 0.0291 1.0000 Uani . . . . . .
C41 C 0.73519(17) 0.45485(7) 0.79804(13) 0.0215 1.0000 Uani . . . . . .
H51 H 0.9379 0.1989 0.4822 0.0092 1.0000 Uiso R . . . . .
H91 H 0.9719 0.2281 0.7077 0.0097 1.0000 Uiso R . . . . .
H111 H 1.1986 0.2364 0.7986 0.0172 1.0000 Uiso R . . . . .
H121 H 1.4453 0.2223 0.8047 0.0214 1.0000 Uiso R . . . . .
H131 H 1.5480 0.2042 0.6408 0.0219 1.0000 Uiso R . . . . .
H141 H 1.4042 0.1996 0.4738 0.0205 1.0000 Uiso R . . . . .
H151 H 1.1633 0.2111 0.4674 0.0182 1.0000 Uiso R . . . . .
H221 H 1.1112 0.4557 0.7698 0.0262 1.0000 Uiso R . . . . .
H231 H 1.2043 0.5255 0.6552 0.0312 1.0000 Uiso R . . . . .
H241 H 1.2131 0.5077 0.4688 0.0317 1.0000 Uiso R . . . . .
H251 H 1.1308 0.4189 0.3873 0.0252 1.0000 Uiso R . . . . .
H311 H 0.7495 0.3308 0.3619 0.0133 1.0000 Uiso R . . . . .
H321 H 0.5864 0.4017 0.2872 0.0150 1.0000 Uiso R . . . . .
H331 H 0.4462 0.4515 0.4006 0.0170 1.0000 Uiso R . . . . .
H341 H 0.4634 0.4310 0.5931 0.0168 1.0000 Uiso R . . . . .
H351 H 0.5941 0.3464 0.8498 0.0170 1.0000 Uiso R . . . . .
H352 H 0.4619 0.3657 0.7705 0.0164 1.0000 Uiso R . . . . .
H371 H 0.4129 0.4562 0.8557 0.0260 1.0000 Uiso R . . . . .
H381 H 0.4700 0.5545 0.9002 0.0332 1.0000 Uiso R . . . . .
H391 H 0.6935 0.5904 0.8784 0.0356 1.0000 Uiso R . . . . .
H401 H 0.8628 0.5265 0.8151 0.0342 1.0000 Uiso R . . . . .
H411 H 0.8058 0.4290 0.7728 0.0238 1.0000 Uiso R . . . . .
H1 H 0.7384(17) 0.2379(7) 0.4687(12) 0.0127(18) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.88(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
F1 . C2 . 1.3373(17) yes
C2 . F3 . 1.3380(17) yes
C2 . F4 . 1.3399(17) yes
C2 . C5 . 1.5123(18) yes
C5 . N6 . 1.4670(16) yes
C5 . C9 . 1.5408(18) yes
C5 . H51 . 0.955 no
N6 . C7 . 1.4671(16) yes
N6 . H1 . 0.873(14) no
C7 . C8 . 1.5863(17) yes
C7 . C26 . 1.5662(18) yes
C7 . C30 . 1.5086(17) yes
C8 . C9 . 1.5539(17) yes
C8 . C16 . 1.5373(18) yes
C8 . C20 . 1.5344(18) yes
C9 . C10 . 1.5175(18) yes
C9 . H91 . 0.975 no
C10 . C11 . 1.393(2) yes
C10 . C15 . 1.396(2) yes
C11 . C12 . 1.393(2) yes
C11 . H111 . 0.949 no
C12 . C13 . 1.388(2) yes
C12 . H121 . 0.957 no
C13 . C14 . 1.387(2) yes
C13 . H131 . 0.959 no
C14 . C15 . 1.394(2) yes
C14 . H141 . 0.944 no
C15 . H151 . 0.952 no
C16 . O17 . 1.2093(18) yes
C16 . C18 . 1.4834(19) yes
C18 . C19 . 1.392(2) yes
C18 . C25 . 1.394(2) yes
C19 . C20 . 1.4802(19) yes
C19 . C22 . 1.393(2) yes
C20 . O21 . 1.2128(18) yes
C22 . C23 . 1.389(3) yes
C22 . H221 . 0.950 no
C23 . C24 . 1.397(3) yes
C23 . H231 . 0.942 no
C24 . C25 . 1.393(3) yes
C24 . H241 . 0.943 no
C25 . H251 . 0.960 no
C26 . O27 . 1.2124(17) yes
C26 . N28 . 1.3715(17) yes
N28 . C29 . 1.4052(18) yes
N28 . C35 . 1.4543(17) yes
C29 . C30 . 1.3934(19) yes
C29 . C34 . 1.3849(19) yes
C30 . C31 . 1.3839(19) yes
C31 . C32 . 1.3986(19) yes
C31 . H311 . 0.938 no
C32 . C33 . 1.386(2) yes
C32 . H321 . 0.965 no
C33 . C34 . 1.400(2) yes
C33 . H331 . 0.961 no
C34 . H341 . 0.936 no
C35 . C36 . 1.518(2) yes
C35 . H351 . 0.958 no
C35 . H352 . 0.982 no
C36 . C37 . 1.391(2) yes
C36 . C41 . 1.388(2) yes
C37 . C38 . 1.399(3) yes
C37 . H371 . 0.931 no
C38 . C39 . 1.376(3) yes
C38 . H381 . 0.945 no
C39 . C40 . 1.385(3) yes
C39 . H391 . 0.959 no
C40 . C41 . 1.392(2) yes
C40 . H401 . 0.949 no
C41 . H411 . 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
F1 . C2 . F3 . 106.19(12) yes
F1 . C2 . F4 . 106.71(11) yes
F3 . C2 . F4 . 106.51(12) yes
F1 . C2 . C5 . 111.57(12) yes
F3 . C2 . C5 . 114.14(11) yes
F4 . C2 . C5 . 111.26(12) yes
C2 . C5 . N6 . 109.83(11) yes
C2 . C5 . C9 . 112.71(11) yes
N6 . C5 . C9 . 105.94(10) yes
C2 . C5 . H51 . 106.5 no
N6 . C5 . H51 . 110.5 no
C9 . C5 . H51 . 111.4 no
C5 . N6 . C7 . 110.45(10) yes
C5 . N6 . H1 . 108.7(10) no
C7 . N6 . H1 . 110.3(10) no
N6 . C7 . C8 . 104.36(10) yes
N6 . C7 . C26 . 112.64(10) yes
C8 . C7 . C26 . 108.74(10) yes
N6 . C7 . C30 . 112.10(10) yes
C8 . C7 . C30 . 117.75(10) yes
C26 . C7 . C30 . 101.47(10) yes
C7 . C8 . C9 . 101.11(10) yes
C7 . C8 . C16 . 109.49(10) yes
C9 . C8 . C16 . 114.17(11) yes
C7 . C8 . C20 . 115.78(11) yes
C9 . C8 . C20 . 113.70(10) yes
C16 . C8 . C20 . 103.00(11) yes
C5 . C9 . C8 . 101.79(10) yes
C5 . C9 . C10 . 116.91(11) yes
C8 . C9 . C10 . 114.58(11) yes
C5 . C9 . H91 . 106.5 no
C8 . C9 . H91 . 107.3 no
C10 . C9 . H91 . 109.1 no
C9 . C10 . C11 . 118.38(12) yes
C9 . C10 . C15 . 122.82(12) yes
C11 . C10 . C15 . 118.80(13) yes
C10 . C11 . C12 . 120.91(14) yes
C10 . C11 . H111 . 118.6 no
C12 . C11 . H111 . 120.5 no
C11 . C12 . C13 . 120.00(14) yes
C11 . C12 . H121 . 120.9 no
C13 . C12 . H121 . 119.0 no
C12 . C13 . C14 . 119.48(13) yes
C12 . C13 . H131 . 120.9 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 120.69(14) yes
C13 . C14 . H141 . 120.5 no
C15 . C14 . H141 . 118.8 no
C10 . C15 . C14 . 120.10(14) yes
C10 . C15 . H151 . 121.4 no
C14 . C15 . H151 . 118.5 no
C8 . C16 . O17 . 125.66(13) yes
C8 . C16 . C18 . 108.06(12) yes
O17 . C16 . C18 . 126.28(13) yes
C16 . C18 . C19 . 110.04(12) yes
C16 . C18 . C25 . 129.15(15) yes
C19 . C18 . C25 . 120.81(14) yes
C18 . C19 . C20 . 109.87(12) yes
C18 . C19 . C22 . 121.93(14) yes
C20 . C19 . C22 . 128.18(14) yes
C8 . C20 . C19 . 108.29(12) yes
C8 . C20 . O21 . 126.20(13) yes
C19 . C20 . O21 . 125.46(13) yes
C19 . C22 . C23 . 117.14(16) yes
C19 . C22 . H221 . 121.0 no
C23 . C22 . H221 . 121.9 no
C22 . C23 . C24 . 121.26(15) yes
C22 . C23 . H231 . 119.1 no
C24 . C23 . H231 . 119.7 no
C23 . C24 . C25 . 121.40(15) yes
C23 . C24 . H241 . 118.7 no
C25 . C24 . H241 . 119.9 no
C18 . C25 . C24 . 117.44(16) yes
C18 . C25 . H251 . 121.5 no
C24 . C25 . H251 . 121.1 no
C7 . C26 . O27 . 126.84(12) yes
C7 . C26 . N28 . 107.21(11) yes
O27 . C26 . N28 . 125.94(12) yes
C26 . N28 . C29 . 111.47(11) yes
C26 . N28 . C35 . 124.46(12) yes
C29 . N28 . C35 . 123.88(11) yes
N28 . C29 . C30 . 109.66(11) yes
N28 . C29 . C34 . 127.70(13) yes
C30 . C29 . C34 . 122.51(13) yes
C7 . C30 . C29 . 109.33(11) yes
C7 . C30 . C31 . 130.42(12) yes
C29 . C30 . C31 . 119.89(12) yes
C30 . C31 . C32 . 118.51(13) yes
C30 . C31 . H311 . 121.0 no
C32 . C31 . H311 . 120.5 no
C31 . C32 . C33 . 120.95(13) yes
C31 . C32 . H321 . 120.5 no
C33 . C32 . H321 . 118.6 no
C32 . C33 . C34 . 121.04(13) yes
C32 . C33 . H331 . 118.9 no
C34 . C33 . H331 . 120.0 no
C33 . C34 . C29 . 117.08(13) yes
C33 . C34 . H341 . 122.3 no
C29 . C34 . H341 . 120.6 no
N28 . C35 . C36 . 111.62(12) yes
N28 . C35 . H351 . 107.0 no
C36 . C35 . H351 . 110.0 no
N28 . C35 . H352 . 110.1 no
C36 . C35 . H352 . 109.6 no
H351 . C35 . H352 . 108.4 no
C35 . C36 . C37 . 120.50(14) yes
C35 . C36 . C41 . 120.77(13) yes
C37 . C36 . C41 . 118.70(15) yes
C36 . C37 . C38 . 120.14(17) yes
C36 . C37 . H371 . 117.1 no
C38 . C37 . H371 . 122.8 no
C37 . C38 . C39 . 120.73(16) yes
C37 . C38 . H381 . 119.0 no
C39 . C38 . H381 . 120.3 no
C38 . C39 . C40 . 119.37(16) yes
C38 . C39 . H391 . 119.2 no
C40 . C39 . H391 . 121.4 no
C39 . C40 . C41 . 120.18(18) yes
C39 . C40 . H401 . 120.0 no
C41 . C40 . H401 . 119.8 no
C40 . C41 . C36 . 120.86(15) yes
C40 . C41 . H411 . 119.4 no
C36 . C41 . H411 . 119.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H51 . O21 3_554 163 0.96 2.54 3.470(2) yes
C9 . H91 . O27 . 123 0.97 2.58 3.214(2) yes
C31 . H311 . O17 . 124 0.94 2.51 3.132(2) yes
C31 . H311 . O27 3_554 134 0.94 2.44 3.171(2) yes
N6 . H1 . O27 3_554 159.4(14) 0.873(14) 2.301(14) 3.134(2) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            
(2'R,4'S,5'S)-1''-benzyl-4'-phenyl-5'-(trifluoromethyl)dispiro[indene-2,3'-pyrrolidine-2',3''-indoline]-1,2'',3-trione
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, hexane'
####################################################################### 
# 
# 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_global_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2103731'
loop_
_audit_author_name
_audit_author_address
'Peter Knipe'
;Queens University, Belfast
United Kingdom
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_global              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.52 eA-3
RESPONSE: In addition to the N-Bn fragment there is some disorder evident in the oxindole. Attempts to model this disorder anisotropically over two fragments (with refined and complementary occupancies) did not converge, so the single fragment approach was used.
;
_vrf_PLAT331_global              
;
PROBLEM: Small Aver Phenyl C-C Dist C100     --C251     .       1.36 Ang.
RESPONSE: Despite modelling anisotropically over two fragments, there remains some disorder in the N-benzyl substituent (the ADPs remain rather prolate), reducing C-C bond precision.
;
_vrf_DIFMX02_global              
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: 1.145A from N(1)
;
# Added during the CSD deposition process: Tuesday 17 August 2021 01:47 PM
# end Validation Reply Form

_audit_creation_date             2021-08-17
_audit_creation_method           CRYSTALS_ver_14.61_build_6999

_oxford_structure_analysis_title 'P:\X-Ray\WR-2.190-02\WR-2.190-02.cif_od At 1'
_chemical_name_systematic        3d
_chemical_melting_point          'not measured'

_cell_length_a                   11.6334(6)
_cell_length_b                   6.6182(4)
_cell_length_c                   16.7064(9)
_cell_angle_alpha                90.0
_cell_angle_beta                 91.462(5)
_cell_angle_gamma                90.0
_cell_volume                     1285.84(12)

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

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


_cell_formula_units_Z            2

# Given Formula = C66 H60 F1 N6 O6 
# Dc =      1.36 Fooo =    555.00 Mu =      7.26 M =   1052.24
# Found Formula = C62 H42 F6 N8 O2 
# Dc =      1.35 FOOO =    540.00 Mu =      8.23 M =   1045.06

_chemical_formula_sum            'C31 H21 F3 N4 O'
_chemical_formula_moiety         'C31 H21 F3 N4 O'
_chemical_compound_source        .
_chemical_formula_weight         522.52


_cell_measurement_reflns_used    19017
_cell_measurement_theta_min      4
_cell_measurement_theta_max      71
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_max          0.240

_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.823

# Sheldrick geometric approximatio 0.88 0.88 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.88
_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     1.54180
_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    'SHELXT (Sheldrick, 2015)'
_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_ambient_pressure         100
_diffrn_reflns_number            39351
_diffrn_reflns_av_unetI/netI     0.052
_reflns_number_total             4910
_diffrn_reflns_av_R_equivalents  0.108
# Number of reflections without Friedels Law is 4910 
# Number of reflections with Friedels Law is 2759 
# Theoretical number of reflections is about 2631 


_diffrn_reflns_theta_min         3.801
_diffrn_reflns_theta_max         74.523
_diffrn_measured_fraction_theta_max 0.960

_diffrn_reflns_theta_full        69.307
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              -8
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   4.40
_oxford_diffrn_Wilson_scale      0.01

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

_refine_diff_density_min         -0.66
_refine_diff_density_max         1.52


# 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     127
_refine_ls_number_parameters     408
_refine_ls_number_reflns         4910
_oxford_refine_ls_R_factor_ref   0.1160
_refine_ls_wR_factor_ref         0.3538
_refine_ls_goodness_of_fit_ref   1.6196
_refine_ls_shift/su_max          0.0116005
_refine_ls_shift/su_mean         0.0007826


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4910
_refine_ls_R_factor_all          0.1160
_refine_ls_wR_factor_all         0.3538

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4258
_refine_ls_R_factor_gt           0.1081
_refine_ls_wR_factor_gt          0.3428

_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1925 Friedel Pairs 
;

_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,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
F1 F 0.3600(4) 0.1825(10) 0.0336(2) 0.1009 1.0000 Uani . . . . . .
F2 F 0.5255(4) 0.3024(14) 0.0544(2) 0.1203 1.0000 Uani . . . . . .
N3 N 0.5193(4) 0.2451(9) 0.2214(2) 0.0551 1.0000 Uani . . . . . .
O4 O 0.5899(4) 0.6647(10) 0.1747(3) 0.0859 1.0000 Uani . . . . . .
C1 C 0.2315(4) 0.4572(9) 0.1489(3) 0.0453 1.0000 Uani . . . . . .
N6 N 0.2573(4) 0.3108(9) 0.3638(3) 0.0579 1.0000 Uani . . . . . .
C2 C 0.5158(4) 0.4208(9) 0.2727(3) 0.0471 1.0000 Uani . . . . . .
C31 C 0.3142(4) 0.3857(8) 0.3201(3) 0.0403 1.0000 Uani . . . . . .
C30 C 0.3723(6) 0.7113(8) 0.2791(3) 0.0542 1.0000 Uani . . . . . .
C29 C 0.3862(4) 0.4931(7) 0.2635(3) 0.0391 1.0000 Uani . . . . . .
C32 C 0.4488(6) 0.1805(14) 0.0847(3) 0.0742 1.0000 Uani . . . . . .
C3 C 0.4150(4) 0.2325(9) 0.1676(3) 0.0492 1.0000 Uani . . . . . .
C4 C 0.3582(4) 0.4391(8) 0.1728(3) 0.0421 1.0000 Uani . . . . . .
C5 C 0.1519(4) 0.3171(9) 0.1646(3) 0.0473 1.0000 Uani . . . . . .
N1 N 0.6541(5) 0.6742(10) 0.3075(4) 0.0733 1.0000 Uani . . . . . .
C7 C 0.5623(4) 0.3847(10) 0.3569(3) 0.0519 1.0000 Uani . . . . . .
C8 C 0.0055(5) 0.5254(13) 0.1009(3) 0.0642 1.0000 Uani . . . . . .
C9 C 0.0341(5) 0.3442(11) 0.1402(3) 0.0584 1.0000 Uani . . . . . .
N10 N 0.3611(7) 0.8790(10) 0.2914(3) 0.0830 1.0000 Uani . . . . . .
F29 F 0.4995(8) -0.0033(12) 0.0850(3) 0.1616 1.0000 Uani . . . . . .
C28 C 0.5345(5) 0.2401(10) 0.4115(3) 0.0544 1.0000 Uani . . . . . .
C27 C 0.2002(5) 0.6370(10) 0.1088(3) 0.0589 1.0000 Uani . . . . . .
C14 C 0.6380(5) 0.5468(11) 0.3758(4) 0.0638 1.0000 Uani . . . . . .
C15 C 0.0886(6) 0.6674(12) 0.0837(4) 0.0708 1.0000 Uani . . . . . .
C16 C 0.5891(5) 0.6091(15) 0.2447(5) 0.0764 1.0000 Uani . . . . . .
C18 C -0.0492(6) 0.1965(17) 0.1556(4) 0.0830 1.0000 Uani . . . . . .
C19 C -0.1933(6) 0.423(2) 0.0946(4) 0.1098 1.0000 Uani . . . . . .
C20 C -0.1146(6) 0.559(2) 0.0779(4) 0.0963 1.0000 Uani . . . . . .
C21 C 0.5934(6) 0.2510(16) 0.4863(3) 0.0792 1.0000 Uani . . . . . .
C22 C 0.6914(6) 0.5615(16) 0.4508(5) 0.0799 1.0000 Uani . . . . . .
C23 C -0.1637(6) 0.239(2) 0.1317(5) 0.1062 1.0000 Uani . . . . . .
C24 C 0.6683(6) 0.4156(17) 0.5033(4) 0.0851 1.0000 Uani . . . . . .
C26 C 0.7200(5) 0.8576(12) 0.3075(6) 0.0962 1.0000 Uani D . . . . .
C170 C 0.8494(5) 0.7970(11) 0.3331(4) 0.0941 0.561(17) Uani D . P 1 2 .
C171 C 0.8477(8) 0.8511(11) 0.3275(4) 0.1388 0.439(17) Uani D . P 1 1 .
C250 C 0.8992(6) 0.6394(12) 0.3069(5) 0.0898 0.561(17) Uani D . P 1 2 .
C251 C 0.9125(9) 0.7126(15) 0.3033(6) 0.1419 0.439(17) Uani D . P 1 1 .
C100 C 1.0270(9) 0.738(2) 0.3133(6) 0.1402 0.439(17) Uani D . P 1 1 .
C101 C 1.0124(6) 0.6080(13) 0.3299(5) 0.0961 0.561(17) Uani D . P 1 2 .
C110 C 0.9056(7) 0.9477(12) 0.3872(5) 0.1122 0.561(17) Uani D . P 1 2 .
C111 C 0.8892(12) 1.0356(15) 0.3679(5) 0.1433 0.439(17) Uani D . P 1 1 .
C120 C 1.0206(7) 0.9037(15) 0.4077(5) 0.1117 0.561(17) Uani D . P 1 2 .
C121 C 1.0071(13) 1.048(2) 0.3766(6) 0.1388 0.439(17) Uani D . P 1 1 .
C130 C 1.0728(6) 0.7344(16) 0.3789(5) 0.1093 0.561(17) Uani D . P 1 2 .
C131 C 1.0752(10) 0.899(3) 0.3496(7) 0.1391 0.439(17) Uani D . P 1 1 .
H99 H 0.3648 0.1336 0.1883 0.0607 1.0000 Uiso . . . . . .
H41 H 0.4001 0.5307 0.1402 0.0512 1.0000 Uiso . . . . . .
H51 H 0.1738 0.1978 0.1920 0.0560 1.0000 Uiso . . . . . .
H281 H 0.4805 0.1385 0.4001 0.0673 1.0000 Uiso . . . . . .
H271 H 0.2564 0.7364 0.0972 0.0724 1.0000 Uiso . . . . . .
H151 H 0.0668 0.7893 0.0567 0.0875 1.0000 Uiso . . . . . .
H181 H -0.0286 0.0688 0.1799 0.0965 1.0000 Uiso . . . . . .
H191 H -0.2722 0.4524 0.0811 0.1296 1.0000 Uiso . . . . . .
H201 H -0.1388 0.6746 0.0504 0.1137 1.0000 Uiso . . . . . .
H211 H 0.5814 0.1502 0.5249 0.0902 1.0000 Uiso . . . . . .
H221 H 0.7471 0.6703 0.4625 0.0951 1.0000 Uiso . . . . . .
H231 H -0.2220 0.1363 0.1390 0.1221 1.0000 Uiso . . . . . .
H241 H 0.6964 0.4291 0.5580 0.0995 1.0000 Uiso . . . . . .
H261 H 0.6887 0.9397 0.3532 0.1203 0.439(17) Uiso . . P 1 1 .
H264 H 0.7085 0.9252 0.2619 0.1203 0.439(17) Uiso . . P 1 1 .
H263 H 0.6919 0.9451 0.3527 0.1203 0.561(17) Uiso . . P 1 2 .
H262 H 0.7148 0.9270 0.2619 0.1203 0.561(17) Uiso . . P 1 2 .
H2501 H 0.8568 0.5523 0.2687 0.1023 0.561(17) Uiso . . P 1 2 .
H2511 H 0.8781 0.5977 0.2741 0.1477 0.439(17) Uiso . . P 1 1 .
H1001 H 1.0723 0.6265 0.2919 0.1456 0.439(17) Uiso . . P 1 1 .
H1011 H 1.0453 0.4861 0.3065 0.1049 0.561(17) Uiso . . P 1 2 .
H1101 H 0.8693 1.0634 0.4098 0.1192 0.561(17) Uiso . . P 1 2 .
H1111 H 0.8414 1.1398 0.3896 0.1554 0.439(17) Uiso . . P 1 1 .
H1201 H 1.0632 0.9845 0.4448 0.1161 0.561(17) Uiso . . P 1 2 .
H1211 H 1.0423 1.1567 0.4055 0.1503 0.439(17) Uiso . . P 1 1 .
H1301 H 1.1481 0.6877 0.3944 0.1165 0.561(17) Uiso . . P 1 2 .
H1311 H 1.1572 0.8963 0.3554 0.1503 0.439(17) Uiso . . P 1 1 .
H31 H 0.5478 0.1440 0.2318 0.0500 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.4(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
F1 . C32 . 1.324(7) yes
F2 . C32 . 1.314(12) yes
N3 . C2 . 1.445(7) yes
N3 . C3 . 1.494(6) yes
N3 . H31 . 0.764 no
O4 . C16 . 1.227(9) yes
C1 . C4 . 1.522(6) yes
C1 . C5 . 1.341(8) yes
C1 . C27 . 1.409(8) yes
N6 . C31 . 1.114(7) yes
C2 . C29 . 1.586(6) yes
C2 . C7 . 1.514(6) yes
C2 . C16 . 1.586(9) yes
C31 . C29 . 1.464(6) yes
C30 . C29 . 1.477(6) yes
C30 . N10 . 1.137(8) yes
C29 . C4 . 1.583(6) yes
C32 . C3 . 1.490(7) yes
C32 . F29 . 1.352(9) yes
C3 . C4 . 1.522(7) yes
C3 . H99 . 0.948 no
C4 . H41 . 0.956 no
C5 . C9 . 1.431(7) yes
C5 . H51 . 0.944 no
N1 . C14 . 1.435(10) yes
N1 . C16 . 1.347(10) yes
N1 . C26 . 1.436(10) yes
C7 . C28 . 1.366(8) yes
C7 . C14 . 1.419(9) yes
C8 . C9 . 1.404(10) yes
C8 . C15 . 1.384(11) yes
C8 . C20 . 1.456(8) yes
C9 . C18 . 1.404(10) yes
C28 . C21 . 1.412(7) yes
C28 . H281 . 0.937 no
C27 . C15 . 1.369(8) yes
C27 . H271 . 0.951 no
C14 . C22 . 1.387(9) yes
C15 . H151 . 0.955 no
C18 . C23 . 1.411(11) yes
C18 . H181 . 0.965 no
C19 . C20 . 1.320(17) yes
C19 . C23 . 1.403(19) yes
C19 . H191 . 0.959 no
C20 . H201 . 0.930 no
C21 . C24 . 1.419(13) yes
C21 . H211 . 0.940 no
C22 . C24 . 1.337(13) yes
C22 . H221 . 0.986 no
C23 . H231 . 0.971 no
C24 . H241 . 0.967 no
C26 . C171 . 1.516(8) yes
C26 . H261 . 1.012 no
C26 . H264 . 0.891 no
C26 . C170 . 1.606(7) yes
C26 . H263 . 1.011 no
C26 . H262 . 0.891 no
C170 . C250 . 1.276(7) yes
C170 . C110 . 1.485(7) yes
C171 . C251 . 1.260(8) yes
C171 . C111 . 1.470(8) yes
C250 . C101 . 1.378(7) yes
C250 . H2501 . 0.984 no
C251 . C100 . 1.349(8) yes
C251 . H2511 . 0.983 no
C100 . C131 . 1.344(8) yes
C100 . H1001 . 0.978 no
C101 . C130 . 1.354(7) yes
C101 . H1011 . 0.979 no
C110 . C120 . 1.403(7) yes
C110 . H1101 . 0.957 no
C111 . C121 . 1.378(8) yes
C111 . H1111 . 0.962 no
C120 . C130 . 1.368(7) yes
C120 . H1201 . 0.948 no
C121 . C131 . 1.348(8) yes
C121 . H1211 . 0.954 no
C130 . H1301 . 0.958 no
C131 . H1311 . 0.957 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 . N3 . C3 . 111.5(4) yes
C2 . N3 . H31 . 126.1 no
C3 . N3 . H31 . 115.3 no
C4 . C1 . C5 . 124.3(4) yes
C4 . C1 . C27 . 115.3(5) yes
C5 . C1 . C27 . 120.3(4) yes
N3 . C2 . C29 . 103.1(4) yes
N3 . C2 . C7 . 114.1(4) yes
C29 . C2 . C7 . 117.0(4) yes
N3 . C2 . C16 . 115.8(5) yes
C29 . C2 . C16 . 104.6(4) yes
C7 . C2 . C16 . 102.5(4) yes
N6 . C31 . C29 . 177.3(5) yes
C29 . C30 . N10 . 179.6(8) yes
C2 . C29 . C30 . 112.7(4) yes
C2 . C29 . C31 . 110.4(4) yes
C30 . C29 . C31 . 107.1(4) yes
C2 . C29 . C4 . 101.3(3) yes
C30 . C29 . C4 . 111.7(4) yes
C31 . C29 . C4 . 113.7(4) yes
F1 . C32 . F2 . 105.8(6) yes
F1 . C32 . C3 . 112.2(5) yes
F2 . C32 . C3 . 114.5(6) yes
F1 . C32 . F29 . 110.1(7) yes
F2 . C32 . F29 . 104.7(7) yes
C3 . C32 . F29 . 109.2(6) yes
N3 . C3 . C32 . 110.1(4) yes
N3 . C3 . C4 . 105.2(4) yes
C32 . C3 . C4 . 112.7(5) yes
N3 . C3 . H99 . 108.5 no
C32 . C3 . H99 . 111.1 no
C4 . C3 . H99 . 109.1 no
C3 . C4 . C1 . 118.4(4) yes
C3 . C4 . C29 . 100.3(3) yes
C1 . C4 . C29 . 114.0(4) yes
C3 . C4 . H41 . 108.0 no
C1 . C4 . H41 . 107.8 no
C29 . C4 . H41 . 107.8 no
C1 . C5 . C9 . 121.3(5) yes
C1 . C5 . H51 . 119.5 no
C9 . C5 . H51 . 119.2 no
C14 . N1 . C16 . 110.4(6) yes
C14 . N1 . C26 . 125.2(7) yes
C16 . N1 . C26 . 124.0(7) yes
C2 . C7 . C28 . 130.3(5) yes
C2 . C7 . C14 . 107.0(5) yes
C28 . C7 . C14 . 122.5(5) yes
C9 . C8 . C15 . 121.2(5) yes
C9 . C8 . C20 . 118.0(8) yes
C15 . C8 . C20 . 120.8(7) yes
C5 . C9 . C8 . 117.0(6) yes
C5 . C9 . C18 . 121.4(6) yes
C8 . C9 . C18 . 121.6(6) yes
C7 . C28 . C21 . 116.0(6) yes
C7 . C28 . H281 . 122.4 no
C21 . C28 . H281 . 121.6 no
C1 . C27 . C15 . 120.1(6) yes
C1 . C27 . H271 . 120.7 no
C15 . C27 . H271 . 119.2 no
N1 . C14 . C7 . 111.1(5) yes
N1 . C14 . C22 . 127.8(7) yes
C7 . C14 . C22 . 121.0(7) yes
C8 . C15 . C27 . 120.0(6) yes
C8 . C15 . H151 . 119.5 no
C27 . C15 . H151 . 120.4 no
C2 . C16 . N1 . 108.5(6) yes
C2 . C16 . O4 . 122.2(7) yes
N1 . C16 . O4 . 128.9(7) yes
C9 . C18 . C23 . 117.3(9) yes
C9 . C18 . H181 . 121.4 no
C23 . C18 . H181 . 121.2 no
C20 . C19 . C23 . 121.4(7) yes
C20 . C19 . H191 . 118.5 no
C23 . C19 . H191 . 120.1 no
C8 . C20 . C19 . 120.3(10) yes
C8 . C20 . H201 . 122.2 no
C19 . C20 . H201 . 117.4 no
C28 . C21 . C24 . 119.8(7) yes
C28 . C21 . H211 . 119.6 no
C24 . C21 . H211 . 120.6 no
C14 . C22 . C24 . 116.7(8) yes
C14 . C22 . H221 . 120.6 no
C24 . C22 . H221 . 122.6 no
C18 . C23 . C19 . 121.2(9) yes
C18 . C23 . H231 . 118.7 no
C19 . C23 . H231 . 120.0 no
C21 . C24 . C22 . 123.8(6) yes
C21 . C24 . H241 . 116.8 no
C22 . C24 . H241 . 119.0 no
N1 . C26 . C171 . 119.8(6) yes
N1 . C26 . H261 . 104.6 no
C171 . C26 . H261 . 102.6 no
N1 . C26 . H264 . 110.8 no
C171 . C26 . H264 . 109.2 no
H261 . C26 . H264 . 109.1 no
N1 . C26 . C170 . 106.6(6) yes
N1 . C26 . H263 . 107.5 no
C170 . C26 . H263 . 105.2 no
N1 . C26 . H262 . 114.3 no
C170 . C26 . H262 . 113.5 no
H263 . C26 . H262 . 109.1 no
C26 . C170 . C250 . 122.92(8) yes
C26 . C170 . C110 . 112.92(8) yes
C250 . C170 . C110 . 124.10(8) yes
C26 . C171 . C251 . 122.74(9) yes
C26 . C171 . C111 . 112.72(9) yes
C251 . C171 . C111 . 124.02(8) yes
C170 . C250 . C101 . 117.80(9) yes
C170 . C250 . H2501 . 118.5 no
C101 . C250 . H2501 . 123.6 no
C171 . C251 . C100 . 117.84(9) yes
C171 . C251 . H2511 . 118.8 no
C100 . C251 . H2511 . 123.1 no
C251 . C100 . C131 . 123.59(9) yes
C251 . C100 . H1001 . 113.6 no
C131 . C100 . H1001 . 122.8 no
C250 . C101 . C130 . 123.57(9) yes
C250 . C101 . H1011 . 113.1 no
C130 . C101 . H1011 . 123.3 no
C170 . C110 . C120 . 114.31(9) yes
C170 . C110 . H1101 . 125.8 no
C120 . C110 . H1101 . 119.8 no
C171 . C111 . C121 . 114.32(9) yes
C171 . C111 . H1111 . 125.6 no
C121 . C111 . H1111 . 120.1 no
C110 . C120 . C130 . 120.86(9) yes
C110 . C120 . H1201 . 121.5 no
C130 . C120 . H1201 . 117.5 no
C111 . C121 . C131 . 120.85(9) yes
C111 . C121 . H1211 . 120.8 no
C131 . C121 . H1211 . 118.2 no
C120 . C130 . C101 . 119.36(9) yes
C120 . C130 . H1301 . 125.5 no
C101 . C130 . H1301 . 114.9 no
C121 . C131 . C100 . 119.36(9) yes
C121 . C131 . H1311 . 125.0 no
C100 . C131 . H1311 . 115.6 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
C3 . H99 . N10 1_545 140 0.95 2.41 3.195(11) yes
C4 . H41 . O4 . 125 0.96 2.43 3.081(11) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            
(3R,4'S,5'S)-1-benzyl-4'-(naphthalen-2-yl)-2-oxo-5'-(trifluoromethyl)spiro[indoline-3,2'-pyrrolidine]-3',3'-dicarbonitrile
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, hexane'
####################################################################### 
# 
# 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_global_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2114148'
loop_
_audit_author_name
_audit_author_address
'Peter Knipe'
;Queens University, Belfast
United Kingdom
;
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           CRYSTALS_ver_14.61_build_6999

_oxford_structure_analysis_title 'P:\X-Ray\WR 2.166\02\WR-2-166-02.cif_od At 1'
_chemical_name_systematic        
"ethyl (3R,3'S,4'S,5'S)-1-benzyl-3'-cyano-2-oxo-4'-phenyl-5'-(trifluoromethyl)spiro[indoline-3,2'-pyrrolidine]-3'-carboxylate"
_chemical_melting_point          'not measured'

_cell_length_a                   11.847500(10)
_cell_length_b                   13.547100(10)
_cell_length_c                   15.256700(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2448.689(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-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'
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'


_cell_formula_units_Z            4

# Given Formula = C121 H110 F1 N11 O11 
# Dc =      1.30 Fooo =   1010.00 Mu =      6.82 M =   1913.27
# Found Formula = C116 H96 F12 N12 O12 
# Dc =      1.41 FOOO =   1080.00 Mu =      9.06 M =   2078.09

_chemical_formula_sum            'C29 H24 F3 N3 O3'
_chemical_formula_moiety         'C29 H24 F3 N3 O3'
_chemical_compound_source        synthesis
_chemical_formula_weight         519.51


_cell_measurement_reflns_used    18379
_cell_measurement_theta_min      4
_cell_measurement_theta_max      71
_cell_measurement_temperature    100

_exptl_crystal_description       blocks
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.240
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_max          0.360

_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.906

# Sheldrick geometric approximatio 0.78 0.80 
_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  0.80
_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     1.54180
_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    'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_ambient_pressure         100
_diffrn_reflns_number            22989
_diffrn_reflns_av_unetI/netI     0.032
_reflns_number_total             4737
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 4737 
# Number of reflections with Friedels Law is 4737 
# Theoretical number of reflections is about 2387 


_diffrn_reflns_theta_min         4.364
_diffrn_reflns_theta_max         71.496
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        70.066
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.28


# 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     344
_refine_ls_number_reflns         4737
_oxford_refine_ls_R_factor_ref   0.0258
_refine_ls_wR_factor_ref         0.0642
_refine_ls_goodness_of_fit_ref   0.9360
_refine_ls_shift/su_max          0.0007287
_refine_ls_shift/su_mean         0.0001634


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4737
_refine_ls_R_factor_all          0.0258
_refine_ls_wR_factor_all         0.0642

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4681
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_gt          0.0639

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.03(3) # for 2037 Friedel pairs 
_oxford_Bijvoet_difference       0.04(3) # for 2037 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          . # for 0 Friedel pairs 
# NOTE: The Flack parameter was determined before Friedel pairs were merged 
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 2037 Friedel Pairs 
;

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #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 + 0.79P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.91623(6) 0.50673(7) 0.72642(6) 0.0313 1.0000 Uani . . . . . .
C2 C 0.80744(11) 0.51786(11) 0.74930(9) 0.0234 1.0000 Uani . . . . . .
F3 F 0.79358(7) 0.46991(7) 0.82576(5) 0.0340 1.0000 Uani . . . . . .
F4 F 0.79126(8) 0.61347(6) 0.76517(6) 0.0344 1.0000 Uani . . . . . .
C5 C 0.72969(10) 0.47652(9) 0.67970(8) 0.0167 1.0000 Uani . . . . . .
N6 N 0.61291(9) 0.48208(9) 0.70983(7) 0.0197 1.0000 Uani . . . . . .
C7 C 0.53666(9) 0.51070(9) 0.63958(8) 0.0149 1.0000 Uani . . . . . .
C8 C 0.48985(10) 0.61778(9) 0.65186(8) 0.0164 1.0000 Uani . . . . . .
O9 O 0.54366(7) 0.69013(7) 0.67261(6) 0.0226 1.0000 Uani . . . . . .
N10 N 0.37677(9) 0.61469(7) 0.63324(7) 0.0163 1.0000 Uani . . . . . .
C11 C 0.33823(10) 0.51608(9) 0.62733(8) 0.0159 1.0000 Uani . . . . . .
C12 C 0.42950(10) 0.45189(9) 0.63336(8) 0.0159 1.0000 Uani . . . . . .
C13 C 0.41147(11) 0.35089(9) 0.63590(9) 0.0203 1.0000 Uani . . . . . .
C14 C 0.30127(12) 0.31564(10) 0.62887(9) 0.0241 1.0000 Uani . . . . . .
C15 C 0.21148(11) 0.38094(10) 0.61962(9) 0.0240 1.0000 Uani . . . . . .
C16 C 0.22821(10) 0.48304(10) 0.61936(8) 0.0212 1.0000 Uani . . . . . .
C17 C 0.30130(11) 0.69945(10) 0.64307(9) 0.0202 1.0000 Uani . . . . . .
C18 C 0.24067(10) 0.69711(9) 0.73000(8) 0.0166 1.0000 Uani . . . . . .
C19 C 0.30201(10) 0.68757(9) 0.80748(9) 0.0179 1.0000 Uani . . . . . .
C20 C 0.24720(11) 0.68312(9) 0.88742(8) 0.0205 1.0000 Uani . . . . . .
C21 C 0.13030(11) 0.68907(10) 0.89097(9) 0.0222 1.0000 Uani . . . . . .
C22 C 0.06852(11) 0.69934(11) 0.81448(10) 0.0250 1.0000 Uani . . . . . .
C23 C 0.12353(11) 0.70310(10) 0.73422(9) 0.0228 1.0000 Uani . . . . . .
C24 C 0.61467(9) 0.51181(9) 0.55459(8) 0.0140 1.0000 Uani . . . . . .
C25 C 0.73152(10) 0.53765(9) 0.59484(8) 0.0154 1.0000 Uani . . . . . .
C26 C 0.83349(9) 0.52367(9) 0.53663(8) 0.0157 1.0000 Uani . . . . . .
C27 C 0.88996(11) 0.60669(9) 0.50479(9) 0.0195 1.0000 Uani . . . . . .
C28 C 0.98461(11) 0.59751(10) 0.45158(10) 0.0240 1.0000 Uani . . . . . .
C29 C 1.02350(10) 0.50429(11) 0.42900(9) 0.0240 1.0000 Uani . . . . . .
C30 C 0.96884(11) 0.42142(10) 0.46074(10) 0.0235 1.0000 Uani . . . . . .
C31 C 0.87490(10) 0.43077(9) 0.51460(9) 0.0192 1.0000 Uani . . . . . .
C32 C 0.61477(9) 0.41256(9) 0.51494(8) 0.0150 1.0000 Uani . . . . . .
N33 N 0.61571(9) 0.33511(8) 0.48500(8) 0.0213 1.0000 Uani . . . . . .
C34 C 0.57548(10) 0.58745(9) 0.48593(8) 0.0156 1.0000 Uani . . . . . .
O35 O 0.48464(7) 0.55417(7) 0.44452(6) 0.0190 1.0000 Uani . . . . . .
C36 C 0.43198(11) 0.62241(10) 0.38215(9) 0.0220 1.0000 Uani . . . . . .
C37 C 0.31279(13) 0.59106(13) 0.37028(12) 0.0401 1.0000 Uani . . . . . .
O38 O 0.61912(8) 0.66674(6) 0.47571(6) 0.0220 1.0000 Uani . . . . . .
H51 H 0.7551 0.4088 0.6680 0.0178 1.0000 Uiso . . . . . .
H131 H 0.4739 0.3055 0.6419 0.0242 1.0000 Uiso . . . . . .
H141 H 0.2880 0.2454 0.6314 0.0277 1.0000 Uiso . . . . . .
H151 H 0.1371 0.3563 0.6144 0.0273 1.0000 Uiso . . . . . .
H161 H 0.1667 0.5286 0.6139 0.0237 1.0000 Uiso . . . . . .
H171 H 0.3493 0.7596 0.6400 0.0231 1.0000 Uiso . . . . . .
H172 H 0.2468 0.7010 0.5939 0.0246 1.0000 Uiso . . . . . .
H191 H 0.3825 0.6836 0.8042 0.0218 1.0000 Uiso . . . . . .
H201 H 0.2908 0.6767 0.9413 0.0251 1.0000 Uiso . . . . . .
H211 H 0.0949 0.6873 0.9459 0.0276 1.0000 Uiso . . . . . .
H221 H -0.0118 0.7051 0.8159 0.0287 1.0000 Uiso . . . . . .
H231 H 0.0820 0.7098 0.6804 0.0268 1.0000 Uiso . . . . . .
H251 H 0.7241 0.6071 0.6124 0.0168 1.0000 Uiso . . . . . .
H271 H 0.8620 0.6709 0.5194 0.0221 1.0000 Uiso . . . . . .
H281 H 1.0213 0.6561 0.4324 0.0285 1.0000 Uiso . . . . . .
H291 H 1.0868 0.4970 0.3920 0.0282 1.0000 Uiso . . . . . .
H301 H 0.9966 0.3562 0.4465 0.0290 1.0000 Uiso . . . . . .
H311 H 0.8389 0.3736 0.5350 0.0226 1.0000 Uiso . . . . . .
H362 H 0.4381 0.6928 0.4063 0.0274 1.0000 Uiso . . . . . .
H361 H 0.4742 0.6185 0.3272 0.0278 1.0000 Uiso . . . . . .
H371 H 0.2730 0.6375 0.3294 0.0597 1.0000 Uiso . . . . . .
H373 H 0.2735 0.5919 0.4268 0.0592 1.0000 Uiso . . . . . .
H372 H 0.3121 0.5263 0.3462 0.0610 1.0000 Uiso . . . . . .
H61 H 0.5899 0.4279 0.7394 0.0247 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.12(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
F1 . C2 . 1.3439(15) yes
C2 . F3 . 1.3452(17) yes
C2 . F4 . 1.3316(16) yes
C2 . C5 . 1.5131(17) yes
C5 . N6 . 1.4598(15) yes
C5 . C25 . 1.5371(17) yes
C5 . H51 . 0.982 no
N6 . C7 . 1.4543(15) yes
N6 . H61 . 0.903 no
C7 . C8 . 1.5642(16) yes
C7 . C12 . 1.5018(16) yes
C7 . C24 . 1.5924(16) yes
C8 . O9 . 1.2113(16) yes
C8 . N10 . 1.3702(16) yes
N10 . C11 . 1.4145(16) yes
N10 . C17 . 1.4631(16) yes
C11 . C12 . 1.3907(17) yes
C11 . C16 . 1.3835(17) yes
C12 . C13 . 1.3853(17) yes
C13 . C14 . 1.3944(19) yes
C13 . H131 . 0.967 no
C14 . C15 . 1.391(2) yes
C14 . H141 . 0.966 no
C15 . C16 . 1.3973(19) yes
C15 . H151 . 0.945 no
C16 . H161 . 0.958 no
C17 . C18 . 1.5085(18) yes
C17 . H171 . 0.995 no
C17 . H172 . 0.990 no
C18 . C19 . 1.3936(18) yes
C18 . C23 . 1.3917(17) yes
C19 . C20 . 1.3830(18) yes
C19 . H191 . 0.956 no
C20 . C21 . 1.3884(18) yes
C20 . H201 . 0.975 no
C21 . C22 . 1.385(2) yes
C21 . H211 . 0.938 no
C22 . C23 . 1.388(2) yes
C22 . H221 . 0.955 no
C23 . H231 . 0.962 no
C24 . C25 . 1.5543(15) yes
C24 . C32 . 1.4744(16) yes
C24 . C34 . 1.5372(16) yes
C25 . C26 . 1.5113(16) yes
C25 . H251 . 0.983 no
C26 . C27 . 1.3960(17) yes
C26 . C31 . 1.3920(17) yes
C27 . C28 . 1.3899(19) yes
C27 . H271 . 0.957 no
C28 . C29 . 1.388(2) yes
C28 . H281 . 0.950 no
C29 . C30 . 1.3836(19) yes
C29 . H291 . 0.945 no
C30 . C31 . 1.3892(18) yes
C30 . H301 . 0.968 no
C31 . H311 . 0.937 no
C32 . N33 . 1.1444(16) yes
C34 . O35 . 1.3269(15) yes
C34 . O38 . 1.2022(15) yes
O35 . C36 . 1.4661(15) yes
C36 . C37 . 1.4857(19) yes
C36 . H362 . 1.025 no
C36 . H361 . 0.977 no
C37 . H371 . 1.004 no
C37 . H373 . 0.980 no
C37 . H372 . 0.951 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . F3 . 106.75(11) yes
F1 . C2 . F4 . 107.13(11) yes
F3 . C2 . F4 . 107.13(11) yes
F1 . C2 . C5 . 111.10(11) yes
F3 . C2 . C5 . 110.82(11) yes
F4 . C2 . C5 . 113.57(11) yes
C2 . C5 . N6 . 109.69(10) yes
C2 . C5 . C25 . 112.53(10) yes
N6 . C5 . C25 . 104.52(9) yes
C2 . C5 . H51 . 106.7 no
N6 . C5 . H51 . 113.3 no
C25 . C5 . H51 . 110.2 no
C5 . N6 . C7 . 111.75(9) yes
C5 . N6 . H61 . 113.7 no
C7 . N6 . H61 . 113.4 no
N6 . C7 . C8 . 112.29(10) yes
N6 . C7 . C12 . 115.48(10) yes
C8 . C7 . C12 . 101.53(9) yes
N6 . C7 . C24 . 104.01(9) yes
C8 . C7 . C24 . 107.13(9) yes
C12 . C7 . C24 . 116.37(10) yes
C7 . C8 . O9 . 126.52(11) yes
C7 . C8 . N10 . 107.07(10) yes
O9 . C8 . N10 . 126.40(11) yes
C8 . N10 . C11 . 110.96(10) yes
C8 . N10 . C17 . 123.53(10) yes
C11 . N10 . C17 . 123.40(10) yes
N10 . C11 . C12 . 109.60(10) yes
N10 . C11 . C16 . 127.97(11) yes
C12 . C11 . C16 . 122.41(12) yes
C7 . C12 . C11 . 109.25(10) yes
C7 . C12 . C13 . 130.73(12) yes
C11 . C12 . C13 . 119.97(12) yes
C12 . C13 . C14 . 118.72(12) yes
C12 . C13 . H131 . 120.9 no
C14 . C13 . H131 . 120.4 no
C13 . C14 . C15 . 120.40(12) yes
C13 . C14 . H141 . 119.1 no
C15 . C14 . H141 . 120.5 no
C14 . C15 . C16 . 121.43(12) yes
C14 . C15 . H151 . 119.8 no
C16 . C15 . H151 . 118.8 no
C15 . C16 . C11 . 116.98(12) yes
C15 . C16 . H161 . 122.0 no
C11 . C16 . H161 . 121.0 no
N10 . C17 . C18 . 111.38(10) yes
N10 . C17 . H171 . 106.8 no
C18 . C17 . H171 . 109.3 no
N10 . C17 . H172 . 109.7 no
C18 . C17 . H172 . 110.8 no
H171 . C17 . H172 . 108.6 no
C17 . C18 . C19 . 119.96(11) yes
C17 . C18 . C23 . 120.95(12) yes
C19 . C18 . C23 . 119.09(12) yes
C18 . C19 . C20 . 120.48(11) yes
C18 . C19 . H191 . 118.7 no
C20 . C19 . H191 . 120.8 no
C19 . C20 . C21 . 120.02(12) yes
C19 . C20 . H201 . 119.9 no
C21 . C20 . H201 . 120.1 no
C20 . C21 . C22 . 120.02(13) yes
C20 . C21 . H211 . 118.7 no
C22 . C21 . H211 . 121.3 no
C21 . C22 . C23 . 119.93(12) yes
C21 . C22 . H221 . 121.1 no
C23 . C22 . H221 . 119.0 no
C18 . C23 . C22 . 120.46(13) yes
C18 . C23 . H231 . 118.4 no
C22 . C23 . H231 . 121.1 no
C7 . C24 . C25 . 101.39(9) yes
C7 . C24 . C32 . 109.03(9) yes
C25 . C24 . C32 . 111.51(9) yes
C7 . C24 . C34 . 112.70(9) yes
C25 . C24 . C34 . 112.83(10) yes
C32 . C24 . C34 . 109.18(10) yes
C5 . C25 . C24 . 101.47(9) yes
C5 . C25 . C26 . 116.02(10) yes
C24 . C25 . C26 . 116.85(10) yes
C5 . C25 . H251 . 106.6 no
C24 . C25 . H251 . 104.1 no
C26 . C25 . H251 . 110.6 no
C25 . C26 . C27 . 119.12(11) yes
C25 . C26 . C31 . 122.48(11) yes
C27 . C26 . C31 . 118.39(11) yes
C26 . C27 . C28 . 121.18(12) yes
C26 . C27 . H271 . 119.0 no
C28 . C27 . H271 . 119.8 no
C27 . C28 . C29 . 119.63(12) yes
C27 . C28 . H281 . 118.2 no
C29 . C28 . H281 . 122.1 no
C28 . C29 . C30 . 119.74(12) yes
C28 . C29 . H291 . 120.5 no
C30 . C29 . H291 . 119.7 no
C29 . C30 . C31 . 120.53(12) yes
C29 . C30 . H301 . 120.2 no
C31 . C30 . H301 . 119.3 no
C26 . C31 . C30 . 120.50(11) yes
C26 . C31 . H311 . 120.5 no
C30 . C31 . H311 . 119.0 no
C24 . C32 . N33 . 179.13(12) yes
C24 . C34 . O35 . 110.05(10) yes
C24 . C34 . O38 . 123.65(11) yes
O35 . C34 . O38 . 126.20(11) yes
C34 . O35 . C36 . 116.10(10) yes
O35 . C36 . C37 . 107.65(11) yes
O35 . C36 . H362 . 108.8 no
C37 . C36 . H362 . 112.2 no
O35 . C36 . H361 . 107.7 no
C37 . C36 . H361 . 111.5 no
H362 . C36 . H361 . 108.8 no
C36 . C37 . H371 . 110.1 no
C36 . C37 . H373 . 109.9 no
H371 . C37 . H373 . 108.5 no
C36 . C37 . H372 . 108.6 no
H371 . C37 . H372 . 109.5 no
H373 . C37 . H372 . 110.2 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
C17 . H172 . O38 3_466 135 0.99 2.57 3.3509(18) yes
C21 . H211 . N33 2_565 130 0.94 2.58 3.2650(18) yes
C25 . H251 . O9 . 126 0.98 2.58 3.2601(18) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            '(-)-3l (major)'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
