# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_1pyrroloindoline
#==============================================================================

############################################################# 
# ***oxford university chemical crystallography group*** 
# 
# this structure was solved by Russell Driver on 06/02/2014 
############################################################# 


_audit_creation_date             2014-02-06
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 103RWD13
_chemical_name_systematic        .
_chemical_melting_point          'see SI'


_cell_length_a                   13.9144(1)
_cell_length_b                   7.4231(1)
_cell_length_c                   23.8094(1)
_cell_angle_alpha                90
_cell_angle_beta                 97.5321(5)
_cell_angle_gamma                90
_cell_volume                     2438.01(4)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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 = C25 H26 F1 N3 O8 
# Dc =      1.40 Fooo =   1080.00 Mu =      9.37 M =    515.49
# Found Formula = C25 H26 F1 N3 O8 
# Dc =      1.40 FOOO =   1080.00 Mu =      9.37 M =    515.49

_chemical_formula_sum            'C25 H26 F1 N3 O8'
_chemical_formula_moiety         'C25 H26 F1 N3 O8'
_chemical_compound_source        synthesis
_chemical_formula_weight         515.49


_cell_measurement_reflns_used    62668
_cell_measurement_theta_min      3
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.404
_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    0.937

# Sheldrick geometric approximatio 0.91 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_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       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            87116
_reflns_number_total             5116
_diffrn_reflns_av_R_equivalents  0.023
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5116 
# Theoretical number of reflections is about 10280 


_diffrn_reflns_theta_min         3.204
_diffrn_reflns_theta_max         76.757
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        76.757
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   2.30
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.31


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5098
_refine_ls_number_restraints     0
_refine_ls_number_parameters     334
_oxford_refine_ls_R_factor_ref   0.0377
_refine_ls_wR_factor_ref         0.0964
_refine_ls_goodness_of_fit_ref   1.0422
_refine_ls_shift/su_max          0.0004102
_refine_ls_shift/su_mean         0.0000371


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5098
_refine_ls_R_factor_all          0.0377
_refine_ls_wR_factor_all         0.0964

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5083
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0964

# 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 .


_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 + 1.04P] 
 ,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 0.17236(9) 0.37592(17) 0.59285(4) 0.0662 1.0000 Uani . . . . . .
C2 C 0.11118(12) 0.3252(2) 0.54725(6) 0.0408 1.0000 Uani . . . . . .
C3 C 0.15005(10) 0.28959(18) 0.49792(5) 0.0331 1.0000 Uani . . . . . .
C4 C 0.09134(9) 0.23479(15) 0.44937(5) 0.0246 1.0000 Uani . . . . . .
C5 C 0.14123(8) 0.19380(15) 0.39655(4) 0.0209 1.0000 Uani . . . . . .
N6 N 0.24175(7) 0.25763(12) 0.40604(4) 0.0218 1.0000 Uani . . . . . .
C7 C 0.30566(8) 0.14746(14) 0.37823(4) 0.0206 1.0000 Uani . . . . . .
N8 N 0.31626(7) 0.19663(13) 0.31872(4) 0.0222 1.0000 Uani . . . . . .
C9 C 0.37017(8) 0.34654(15) 0.31104(5) 0.0234 1.0000 Uani . . . . . .
O10 O 0.38450(6) 0.36785(11) 0.25698(4) 0.0284 1.0000 Uani . . . . . .
C11 C 0.44196(9) 0.52425(18) 0.24515(6) 0.0319 1.0000 Uani . . . . . .
C12 C 0.44125(11) 0.5272(2) 0.18193(6) 0.0443 1.0000 Uani . . . . . .
O13 O 0.40026(6) 0.44694(11) 0.34960(4) 0.0290 1.0000 Uani . . . . . .
C14 C 0.28923(7) 0.05141(15) 0.28154(5) 0.0218 1.0000 Uani . . . . . .
C15 C 0.25716(7) -0.09143(15) 0.31200(4) 0.0209 1.0000 Uani . . . . . .
C16 C 0.25752(7) -0.04077(14) 0.37359(4) 0.0200 1.0000 Uani . . . . . .
C17 C 0.15407(8) -0.01120(15) 0.38929(5) 0.0226 1.0000 Uani . . . . . .
C18 C 0.30837(8) -0.18659(15) 0.41174(5) 0.0221 1.0000 Uani . . . . . .
O19 O 0.40322(6) -0.15903(11) 0.42373(4) 0.0294 1.0000 Uani . . . . . .
C20 C 0.45713(9) -0.29151(17) 0.46190(6) 0.0353 1.0000 Uani . . . . . .
C21 C 0.55968(11) -0.2864(2) 0.44807(9) 0.0571 1.0000 Uani . . . . . .
C22 C 0.44618(13) -0.24127(19) 0.52219(7) 0.0498 1.0000 Uani . . . . . .
O23 O 0.26560(6) -0.31396(11) 0.42801(4) 0.0299 1.0000 Uani . . . . . .
C24 C 0.22347(8) -0.24919(16) 0.28546(5) 0.0248 1.0000 Uani . . . . . .
C25 C 0.22331(9) -0.26336(17) 0.22709(5) 0.0290 1.0000 Uani . . . . . .
C26 C 0.25490(9) -0.12041(18) 0.19685(5) 0.0299 1.0000 Uani . . . . . .
C27 C 0.28762(8) 0.03958(17) 0.22313(5) 0.0269 1.0000 Uani . . . . . .
C28 C 0.08912(8) 0.29231(15) 0.34444(5) 0.0225 1.0000 Uani . . . . . .
O29 O 0.09174(6) 0.19962(11) 0.29697(3) 0.0261 1.0000 Uani . . . . . .
C30 C 0.05412(10) 0.2903(2) 0.24494(5) 0.0342 1.0000 Uani . . . . . .
O31 O 0.05781(7) 0.44298(12) 0.34657(4) 0.0323 1.0000 Uani . . . . . .
C32 C -0.00772(9) 0.21666(16) 0.45442(5) 0.0281 1.0000 Uani . . . . . .
N33 N -0.07791(7) 0.14365(16) 0.40887(5) 0.0323 1.0000 Uani . . . . . .
O34 O -0.04795(6) 0.08190(14) 0.36693(4) 0.0360 1.0000 Uani . . . . . .
O35 O -0.16400(7) 0.1415(2) 0.41491(5) 0.0577 1.0000 Uani . . . . . .
C36 C -0.04567(10) 0.26043(17) 0.50395(6) 0.0350 1.0000 Uani . . . . . .
C37 C 0.01403(12) 0.31513(18) 0.55136(6) 0.0407 1.0000 Uani . . . . . .
H31 H 0.2175 0.3016 0.4984 0.0399 1.0000 Uiso R . . . . .
H71 H 0.3706 0.1487 0.3998 0.0237 1.0000 Uiso R . . . . .
H111 H 0.5072 0.5071 0.2658 0.0381 1.0000 Uiso R . . . . .
H112 H 0.4132 0.6317 0.2590 0.0362 1.0000 Uiso R . . . . .
H122 H 0.4723 0.6363 0.1706 0.0657 1.0000 Uiso R . . . . .
H121 H 0.4768 0.4219 0.1703 0.0647 1.0000 Uiso R . . . . .
H123 H 0.3728 0.5252 0.1626 0.0650 1.0000 Uiso R . . . . .
H172 H 0.1477 -0.0693 0.4255 0.0275 1.0000 Uiso R . . . . .
H171 H 0.1043 -0.0587 0.3598 0.0267 1.0000 Uiso R . . . . .
H201 H 0.4283 -0.4098 0.4518 0.0386 1.0000 Uiso R . . . . .
H212 H 0.5998 -0.3671 0.4741 0.0850 1.0000 Uiso R . . . . .
H211 H 0.5859 -0.1648 0.4534 0.0850 1.0000 Uiso R . . . . .
H213 H 0.5632 -0.3239 0.4083 0.0845 1.0000 Uiso R . . . . .
H223 H 0.4810 -0.3244 0.5491 0.0733 1.0000 Uiso R . . . . .
H222 H 0.4731 -0.1229 0.5304 0.0742 1.0000 Uiso R . . . . .
H221 H 0.3775 -0.2400 0.5276 0.0739 1.0000 Uiso R . . . . .
H241 H 0.1999 -0.3444 0.3068 0.0293 1.0000 Uiso R . . . . .
H251 H 0.2009 -0.3714 0.2086 0.0349 1.0000 Uiso R . . . . .
H261 H 0.2530 -0.1313 0.1567 0.0363 1.0000 Uiso R . . . . .
H271 H 0.3070 0.1388 0.2022 0.0316 1.0000 Uiso R . . . . .
H302 H 0.0554 0.2076 0.2146 0.0520 1.0000 Uiso R . . . . .
H301 H 0.0930 0.3924 0.2391 0.0525 1.0000 Uiso R . . . . .
H303 H -0.0111 0.3284 0.2470 0.0507 1.0000 Uiso R . . . . .
H361 H -0.1148 0.2533 0.5043 0.0430 1.0000 Uiso R . . . . .
H371 H -0.0098 0.3477 0.5858 0.0497 1.0000 Uiso R . . . . .
H61 H 0.2506 0.3715 0.4032 0.0277 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.98(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
F1 . C2 . 1.3427(17) yes
C2 . C3 . 1.3814(18) yes
C2 . C37 . 1.370(2) yes
C3 . C4 . 1.3862(17) yes
C3 . H31 . 0.942 no
C4 . C5 . 1.5442(15) yes
C4 . C32 . 1.4055(17) yes
C5 . N6 . 1.4660(14) yes
C5 . C17 . 1.5445(15) yes
C5 . C28 . 1.5377(15) yes
N6 . C7 . 1.4326(14) yes
N6 . H61 . 0.858 no
C7 . N8 . 1.4891(13) yes
C7 . C16 . 1.5472(15) yes
C7 . H71 . 0.979 no
N8 . C9 . 1.3676(14) yes
N8 . C14 . 1.4142(14) yes
C9 . O10 . 1.3375(14) yes
C9 . O13 . 1.2137(14) yes
O10 . C11 . 1.4578(14) yes
C11 . C12 . 1.5043(19) yes
C11 . H111 . 0.982 no
C11 . H112 . 0.969 no
C12 . H122 . 0.972 no
C12 . H121 . 0.983 no
C12 . H123 . 1.002 no
C14 . C15 . 1.3908(15) yes
C14 . C27 . 1.3907(16) yes
C15 . C16 . 1.5132(15) yes
C15 . C24 . 1.3830(16) yes
C16 . C17 . 1.5496(14) yes
C16 . C18 . 1.5261(15) yes
C17 . H172 . 0.978 no
C17 . H171 . 0.985 no
C18 . O19 . 1.3290(14) yes
C18 . O23 . 1.2077(14) yes
O19 . C20 . 1.4753(14) yes
C20 . C21 . 1.506(2) yes
C20 . C22 . 1.510(2) yes
C20 . H201 . 0.982 no
C21 . H212 . 0.983 no
C21 . H211 . 0.975 no
C21 . H213 . 0.994 no
C22 . H223 . 0.972 no
C22 . H222 . 0.965 no
C22 . H221 . 0.981 no
C24 . C25 . 1.3933(17) yes
C24 . H241 . 0.954 no
C25 . C26 . 1.3859(18) yes
C25 . H251 . 0.948 no
C26 . C27 . 1.3908(17) yes
C26 . H261 . 0.957 no
C27 . H271 . 0.948 no
C28 . O29 . 1.3277(14) yes
C28 . O31 . 1.2038(14) yes
O29 . C30 . 1.4464(14) yes
C30 . H302 . 0.950 no
C30 . H301 . 0.951 no
C30 . H303 . 0.958 no
C32 . N33 . 1.4650(17) yes
C32 . C36 . 1.3924(17) yes
N33 . O34 . 1.2207(15) yes
N33 . O35 . 1.2252(14) yes
C36 . C37 . 1.372(2) yes
C36 . H361 . 0.964 no
C37 . H371 . 0.955 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 117.63(14) yes
F1 . C2 . C37 . 118.98(12) yes
C3 . C2 . C37 . 123.38(14) yes
C2 . C3 . C4 . 120.76(13) yes
C2 . C3 . H31 . 118.1 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 117.27(10) yes
C3 . C4 . C32 . 115.73(11) yes
C5 . C4 . C32 . 126.96(11) yes
C4 . C5 . N6 . 109.42(9) yes
C4 . C5 . C17 . 110.87(9) yes
N6 . C5 . C17 . 102.34(8) yes
C4 . C5 . C28 . 110.41(9) yes
N6 . C5 . C28 . 108.06(9) yes
C17 . C5 . C28 . 115.30(9) yes
C5 . N6 . C7 . 112.44(8) yes
C5 . N6 . H61 . 116.7 no
C7 . N6 . H61 . 114.9 no
N6 . C7 . N8 . 116.41(9) yes
N6 . C7 . C16 . 105.03(8) yes
N8 . C7 . C16 . 104.44(8) yes
N6 . C7 . H71 . 109.7 no
N8 . C7 . H71 . 107.3 no
C16 . C7 . H71 . 114.0 no
C7 . N8 . C9 . 116.82(9) yes
C7 . N8 . C14 . 110.94(9) yes
C9 . N8 . C14 . 129.94(9) yes
N8 . C9 . O10 . 112.24(10) yes
N8 . C9 . O13 . 122.64(10) yes
O10 . C9 . O13 . 125.11(10) yes
C9 . O10 . C11 . 115.78(9) yes
O10 . C11 . C12 . 105.85(11) yes
O10 . C11 . H111 . 107.1 no
C12 . C11 . H111 . 112.7 no
O10 . C11 . H112 . 109.2 no
C12 . C11 . H112 . 112.3 no
H111 . C11 . H112 . 109.4 no
C11 . C12 . H122 . 110.1 no
C11 . C12 . H121 . 109.4 no
H122 . C12 . H121 . 109.0 no
C11 . C12 . H123 . 109.8 no
H122 . C12 . H123 . 108.5 no
H121 . C12 . H123 . 110.0 no
N8 . C14 . C15 . 109.38(9) yes
N8 . C14 . C27 . 129.96(10) yes
C15 . C14 . C27 . 120.61(10) yes
C14 . C15 . C16 . 110.81(9) yes
C14 . C15 . C24 . 121.33(10) yes
C16 . C15 . C24 . 127.67(10) yes
C7 . C16 . C15 . 103.89(8) yes
C7 . C16 . C17 . 105.19(8) yes
C15 . C16 . C17 . 112.57(9) yes
C7 . C16 . C18 . 115.81(9) yes
C15 . C16 . C18 . 110.05(9) yes
C17 . C16 . C18 . 109.25(9) yes
C5 . C17 . C16 . 106.94(9) yes
C5 . C17 . H172 . 108.1 no
C16 . C17 . H172 . 110.1 no
C5 . C17 . H171 . 110.6 no
C16 . C17 . H171 . 111.5 no
H172 . C17 . H171 . 109.6 no
C16 . C18 . O19 . 112.86(9) yes
C16 . C18 . O23 . 122.45(10) yes
O19 . C18 . O23 . 124.67(10) yes
C18 . O19 . C20 . 116.11(9) yes
O19 . C20 . C21 . 105.56(11) yes
O19 . C20 . C22 . 108.32(11) yes
C21 . C20 . C22 . 114.71(14) yes
O19 . C20 . H201 . 106.7 no
C21 . C20 . H201 . 109.7 no
C22 . C20 . H201 . 111.4 no
C20 . C21 . H212 . 108.8 no
C20 . C21 . H211 . 110.2 no
H212 . C21 . H211 . 108.1 no
C20 . C21 . H213 . 111.5 no
H212 . C21 . H213 . 109.7 no
H211 . C21 . H213 . 108.5 no
C20 . C22 . H223 . 111.5 no
C20 . C22 . H222 . 109.4 no
H223 . C22 . H222 . 107.3 no
C20 . C22 . H221 . 110.4 no
H223 . C22 . H221 . 109.3 no
H222 . C22 . H221 . 108.9 no
C15 . C24 . C25 . 118.41(11) yes
C15 . C24 . H241 . 120.2 no
C25 . C24 . H241 . 121.3 no
C24 . C25 . C26 . 120.08(11) yes
C24 . C25 . H251 . 119.0 no
C26 . C25 . H251 . 120.9 no
C25 . C26 . C27 . 121.83(11) yes
C25 . C26 . H261 . 119.1 no
C27 . C26 . H261 . 119.1 no
C26 . C27 . C14 . 117.72(11) yes
C26 . C27 . H271 . 121.7 no
C14 . C27 . H271 . 120.5 no
C5 . C28 . O29 . 112.20(9) yes
C5 . C28 . O31 . 122.87(10) yes
O29 . C28 . O31 . 124.60(11) yes
C28 . O29 . C30 . 116.14(10) yes
O29 . C30 . H302 . 108.1 no
O29 . C30 . H301 . 110.3 no
H302 . C30 . H301 . 109.7 no
O29 . C30 . H303 . 109.4 no
H302 . C30 . H303 . 110.0 no
H301 . C30 . H303 . 109.4 no
C4 . C32 . N33 . 122.56(11) yes
C4 . C32 . C36 . 122.35(12) yes
N33 . C32 . C36 . 115.04(11) yes
C32 . N33 . O34 . 118.58(10) yes
C32 . N33 . O35 . 119.02(11) yes
O34 . N33 . O35 . 122.36(12) yes
C32 . C36 . C37 . 120.65(13) yes
C32 . C36 . H361 . 118.9 no
C37 . C36 . H361 . 120.4 no
C36 . C37 . C2 . 117.00(12) yes
C36 . C37 . H371 . 122.7 no
C2 . C37 . H371 . 120.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C26 . H261 . O35 4_545 131.26(4) 0.957 2.595 3.3049(18) yes
C37 . H371 . O31 2_566 154.19(4) 0.955 2.395 3.2813(18) yes
N6 . H61 . O23 1_565 160.58(3) 0.858 2.411 3.2329(18) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 06/02/14 at 12:06:45
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) H   ( 123,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 211,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 223,X'S) H   ( 222,X'S) H   ( 221,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,X'S) H   ( 303,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 06/02/14 at 12:06:45
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
# NOTE FO on scale of Fc,      0.20076
# Status flags: 
#    o - used in refinement 
#    < - excluded by I/sigmaI cutoff 
#    l - excluded at low resolution  
#    h - excluded at high resolution  
#    x - excluded for another reason  

_chemical_name_common            pyrroloindoline_1
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes / ethyl acetate'
_database_code_depnum_ccdc_archive 'CCDC 1020472'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2pyrroloindoline
#==============================================================================

############################################################# 
# ***oxford university chemical crystallography group*** 
# 
# this structure was solved by Russell W. Driver on 06/02/2014 
#           The authors would like to thank the 
# Chemical Crystallography Service at the Univeristy of Oxford 
#                   for expertise and 
#  Diamond Light Source for an award of beamtime (MT7768) 
############################################################# 

_audit_creation_date             2014-02-06
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 155RWD14-
_chemical_name_systematic        .
_chemical_melting_point          'see SI'

_cell_length_a                   13.7695(2)
_cell_length_b                   7.3850(2)
_cell_length_c                   24.6016(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.695(1)
_cell_angle_gamma                90
_cell_volume                     2479.15(9)

_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 0.0020 0.0010 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'
O 0.0060 0.0050 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'
N 0.0030 0.0030 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'
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'


_cell_formula_units_Z            4

# Given Formula = C26 H19 N3 O8 
# Dc =      1.34 Fooo =   1080.00 Mu =      1.02 M =    501.45
# Found Formula = C26 H29 N3 O8 
# Dc =      1.37 FOOO =   1080.00 Mu =      1.03 M =    511.53

_chemical_formula_sum            'C26 H29 N3 O8'
_chemical_formula_moiety         'C26 H29 N3 O8'
_chemical_compound_source        synthesis
_chemical_formula_weight         511.53


_cell_measurement_reflns_used    20379
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.010
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_max          0.050

_exptl_crystal_density_diffrn    1.370
_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    0.103

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_detector                 CCD
_diffrn_measurement_device       'CrystalLogic Kappa (3 circle)'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'

_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'

_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100

_diffrn_reflns_number            29024
_reflns_number_total             5174
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5174 
# Theoretical number of reflections is about 11249 


_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         26.468
_diffrn_measured_fraction_theta_max 0.919

_diffrn_reflns_theta_full        25.145
_diffrn_measured_fraction_theta_full 0.950


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   2.00
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_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 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     0
_refine_ls_number_parameters     334
_oxford_refine_ls_R_factor_ref   0.0404
_refine_ls_wR_factor_ref         0.1054
_refine_ls_goodness_of_fit_ref   1.0234
_refine_ls_shift/su_max          0.0008010
_refine_ls_shift/su_mean         0.0000565


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5162
_refine_ls_R_factor_all          0.0406
_refine_ls_wR_factor_all         0.1069

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4891
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_gt          0.0963

# 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 .


_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 + 1.94P] 
 ,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 0.09811(7) -0.16198(14) 0.57564(4) 0.0213 1.0000 Uani . . . . . .
C2 C 0.19424(9) -0.19214(18) 0.58701(5) 0.0173 1.0000 Uani . . . . . .
O3 O 0.23659(7) -0.32059(14) 0.57053(4) 0.0221 1.0000 Uani . . . . . .
C4 C 0.24661(9) -0.04899(18) 0.62510(5) 0.0154 1.0000 Uani . . . . . .
C5 C 0.35234(9) -0.02130(18) 0.61165(5) 0.0171 1.0000 Uani . . . . . .
C6 C 0.36767(9) 0.18393(18) 0.60481(5) 0.0157 1.0000 Uani . . . . . .
N7 N 0.26644(8) 0.25185(16) 0.59506(4) 0.0168 1.0000 Uani . . . . . .
C8 C 0.19968(9) 0.14254(18) 0.62090(5) 0.0158 1.0000 Uani . . . . . .
N9 N 0.18768(8) 0.18944(16) 0.67878(4) 0.0171 1.0000 Uani . . . . . .
C10 C 0.21229(9) 0.04052(19) 0.71421(5) 0.0168 1.0000 Uani . . . . . .
C11 C 0.24449(9) -0.10328(19) 0.68436(5) 0.0160 1.0000 Uani . . . . . .
C12 C 0.27603(9) -0.26462(19) 0.70926(5) 0.0183 1.0000 Uani . . . . . .
C13 C 0.27377(10) -0.2833(2) 0.76564(5) 0.0212 1.0000 Uani . . . . . .
C14 C 0.24148(10) -0.1398(2) 0.79541(5) 0.0206 1.0000 Uani . . . . . .
C15 C 0.21142(10) 0.0244(2) 0.77060(5) 0.0195 1.0000 Uani . . . . . .
C16 C 0.13107(9) 0.33833(19) 0.68640(5) 0.0177 1.0000 Uani . . . . . .
O17 O 0.09979(7) 0.44064(14) 0.64954(4) 0.0215 1.0000 Uani . . . . . .
O18 O 0.11624(7) 0.35575(14) 0.73911(4) 0.0208 1.0000 Uani . . . . . .
C19 C 0.05521(10) 0.5079(2) 0.75139(6) 0.0235 1.0000 Uani . . . . . .
C20 C 0.05659(12) 0.5058(2) 0.81297(6) 0.0304 1.0000 Uani . . . . . .
C21 C 0.41992(9) 0.22382(18) 0.55427(5) 0.0167 1.0000 Uani . . . . . .
C22 C 0.52127(9) 0.20666(18) 0.55111(5) 0.0171 1.0000 Uani . . . . . .
N23 N 0.59044(8) 0.13250(16) 0.59622(4) 0.0185 1.0000 Uani . . . . . .
O24 O 0.67890(7) 0.13516(16) 0.59248(4) 0.0268 1.0000 Uani . . . . . .
O25 O 0.55771(7) 0.06439(15) 0.63575(4) 0.0227 1.0000 Uani . . . . . .
C26 C 0.56191(10) 0.25215(19) 0.50430(5) 0.0202 1.0000 Uani . . . . . .
C27 C 0.50236(10) 0.30745(19) 0.45732(5) 0.0206 1.0000 Uani . . . . . .
C28 C 0.40128(10) 0.31504(19) 0.45723(5) 0.0210 1.0000 Uani . . . . . .
C29 C 0.36292(10) 0.27631(19) 0.50572(5) 0.0186 1.0000 Uani . . . . . .
C30 C 0.33435(11) 0.3645(2) 0.40594(6) 0.0279 1.0000 Uani . . . . . .
C31 C 0.42029(9) 0.28220(19) 0.65559(5) 0.0168 1.0000 Uani . . . . . .
O32 O 0.41408(7) 0.19131(14) 0.70184(4) 0.0195 1.0000 Uani . . . . . .
C33 C 0.45165(11) 0.2837(2) 0.75233(5) 0.0242 1.0000 Uani . . . . . .
O34 O 0.45554(8) 0.43218(14) 0.65376(4) 0.0236 1.0000 Uani . . . . . .
C35 C 0.04216(10) -0.2929(2) 0.53842(6) 0.0238 1.0000 Uani . . . . . .
C36 C 0.05127(13) -0.2391(2) 0.47987(6) 0.0309 1.0000 Uani . . . . . .
C37 C -0.06124(11) -0.2885(2) 0.55269(8) 0.0344 1.0000 Uani . . . . . .
H51 H 0.3999 -0.0722 0.6404 0.0200 1.0000 Uiso R . . . . .
H52 H 0.3592 -0.0805 0.5772 0.0196 1.0000 Uiso R . . . . .
H81 H 0.1343 0.1449 0.5988 0.0182 1.0000 Uiso R . . . . .
H121 H 0.2998 -0.3603 0.6881 0.0219 1.0000 Uiso R . . . . .
H131 H 0.2946 -0.3940 0.7840 0.0247 1.0000 Uiso R . . . . .
H141 H 0.2397 -0.1544 0.8342 0.0255 1.0000 Uiso R . . . . .
H151 H 0.1906 0.1226 0.7912 0.0230 1.0000 Uiso R . . . . .
H191 H 0.0815 0.6201 0.7381 0.0279 1.0000 Uiso R . . . . .
H192 H -0.0114 0.4893 0.7314 0.0278 1.0000 Uiso R . . . . .
H201 H 0.0223 0.6135 0.8242 0.0459 1.0000 Uiso R . . . . .
H202 H 0.1243 0.5090 0.8316 0.0448 1.0000 Uiso R . . . . .
H203 H 0.0241 0.3963 0.8244 0.0461 1.0000 Uiso R . . . . .
H261 H 0.6304 0.2441 0.5050 0.0237 1.0000 Uiso R . . . . .
H271 H 0.5305 0.3431 0.4255 0.0249 1.0000 Uiso R . . . . .
H291 H 0.2932 0.2869 0.5059 0.0219 1.0000 Uiso R . . . . .
H302 H 0.2810 0.4417 0.4145 0.0422 1.0000 Uiso R . . . . .
H301 H 0.3687 0.4261 0.3801 0.0418 1.0000 Uiso R . . . . .
H303 H 0.3061 0.2554 0.3883 0.0435 1.0000 Uiso R . . . . .
H332 H 0.4502 0.1980 0.7816 0.0367 1.0000 Uiso R . . . . .
H331 H 0.5187 0.3213 0.7506 0.0362 1.0000 Uiso R . . . . .
H333 H 0.4109 0.3896 0.7569 0.0368 1.0000 Uiso R . . . . .
H351 H 0.0716 -0.4124 0.5467 0.0272 1.0000 Uiso R . . . . .
H362 H 0.0147 -0.3244 0.4538 0.0452 1.0000 Uiso R . . . . .
H361 H 0.1206 -0.2366 0.4739 0.0455 1.0000 Uiso R . . . . .
H363 H 0.0226 -0.1200 0.4721 0.0454 1.0000 Uiso R . . . . .
H372 H -0.1029 -0.3668 0.5273 0.0509 1.0000 Uiso R . . . . .
H371 H -0.0627 -0.3322 0.5905 0.0518 1.0000 Uiso R . . . . .
H373 H -0.0881 -0.1647 0.5496 0.0507 1.0000 Uiso R . . . . .
H71 H 0.2581 0.3687 0.5960 0.0216 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.3345(16) yes
O1 . C35 . 1.4756(16) yes
C2 . O3 . 1.2114(17) yes
C2 . C4 . 1.5279(18) yes
C4 . C5 . 1.5492(17) yes
C4 . C8 . 1.5528(18) yes
C4 . C11 . 1.5160(17) yes
C5 . C6 . 1.5425(18) yes
C5 . H51 . 0.973 no
C5 . H52 . 0.968 no
C6 . N7 . 1.4706(16) yes
C6 . C21 . 1.5459(17) yes
C6 . C31 . 1.5394(17) yes
N7 . C8 . 1.4342(16) yes
N7 . H71 . 0.871 no
C8 . N9 . 1.4960(15) yes
C8 . H81 . 0.988 no
N9 . C10 . 1.4159(17) yes
N9 . C16 . 1.3751(17) yes
C10 . C11 . 1.3967(19) yes
C10 . C15 . 1.3941(18) yes
C11 . C12 . 1.3828(19) yes
C12 . C13 . 1.3984(18) yes
C12 . H121 . 0.961 no
C13 . C14 . 1.394(2) yes
C13 . H131 . 0.959 no
C14 . C15 . 1.395(2) yes
C14 . H141 . 0.965 no
C15 . H151 . 0.951 no
C16 . O17 . 1.2143(17) yes
C16 . O18 . 1.3455(16) yes
O18 . C19 . 1.4586(16) yes
C19 . C20 . 1.513(2) yes
C19 . H191 . 0.978 no
C19 . H192 . 0.991 no
C20 . H201 . 0.983 no
C20 . H202 . 0.983 no
C20 . H203 . 0.983 no
C21 . C22 . 1.4138(18) yes
C21 . C29 . 1.3935(18) yes
C22 . N23 . 1.4683(16) yes
C22 . C26 . 1.3873(18) yes
N23 . O24 . 1.2339(15) yes
N23 . O25 . 1.2324(15) yes
C26 . C27 . 1.3861(19) yes
C26 . H261 . 0.942 no
C27 . C28 . 1.393(2) yes
C27 . H271 . 0.955 no
C28 . C29 . 1.3974(18) yes
C28 . C30 . 1.5045(19) yes
C29 . H291 . 0.964 no
C30 . H302 . 0.975 no
C30 . H301 . 0.956 no
C30 . H303 . 0.971 no
C31 . O32 . 1.3336(16) yes
C31 . O34 . 1.2125(17) yes
O32 . C33 . 1.4506(16) yes
C33 . H332 . 0.961 no
C33 . H331 . 0.971 no
C33 . H333 . 0.978 no
C35 . C36 . 1.516(2) yes
C35 . C37 . 1.512(2) yes
C35 . H351 . 0.981 no
C36 . H362 . 0.988 no
C36 . H361 . 0.985 no
C36 . H363 . 0.972 no
C37 . H372 . 0.979 no
C37 . H371 . 0.988 no
C37 . H373 . 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 . O1 . C35 . 116.21(10) yes
O1 . C2 . O3 . 124.67(12) yes
O1 . C2 . C4 . 112.74(11) yes
O3 . C2 . C4 . 122.57(11) yes
C2 . C4 . C5 . 109.89(10) yes
C2 . C4 . C8 . 115.55(10) yes
C5 . C4 . C8 . 105.08(10) yes
C2 . C4 . C11 . 109.79(11) yes
C5 . C4 . C11 . 112.33(10) yes
C8 . C4 . C11 . 104.10(10) yes
C4 . C5 . C6 . 107.42(10) yes
C4 . C5 . H51 . 110.7 no
C6 . C5 . H51 . 111.7 no
C4 . C5 . H52 . 109.3 no
C6 . C5 . H52 . 108.5 no
H51 . C5 . H52 . 109.1 no
C5 . C6 . N7 . 102.26(10) yes
C5 . C6 . C21 . 111.11(11) yes
N7 . C6 . C21 . 109.69(10) yes
C5 . C6 . C31 . 115.54(11) yes
N7 . C6 . C31 . 107.72(10) yes
C21 . C6 . C31 . 110.11(10) yes
C6 . N7 . C8 . 112.68(10) yes
C6 . N7 . H71 . 117.3 no
C8 . N7 . H71 . 116.8 no
C4 . C8 . N7 . 104.86(10) yes
C4 . C8 . N9 . 104.21(10) yes
N7 . C8 . N9 . 116.78(11) yes
C4 . C8 . H81 . 113.2 no
N7 . C8 . H81 . 109.8 no
N9 . C8 . H81 . 108.1 no
C8 . N9 . C10 . 110.99(10) yes
C8 . N9 . C16 . 116.86(10) yes
C10 . N9 . C16 . 129.08(11) yes
N9 . C10 . C11 . 109.49(11) yes
N9 . C10 . C15 . 130.22(13) yes
C11 . C10 . C15 . 120.26(12) yes
C4 . C11 . C10 . 110.66(11) yes
C4 . C11 . C12 . 127.49(12) yes
C10 . C11 . C12 . 121.68(12) yes
C11 . C12 . C13 . 118.50(13) yes
C11 . C12 . H121 . 120.2 no
C13 . C12 . H121 . 121.3 no
C12 . C13 . C14 . 119.80(13) yes
C12 . C13 . H131 . 120.5 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 121.84(12) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 119.0 no
C14 . C15 . C10 . 117.90(13) yes
C14 . C15 . H151 . 121.5 no
C10 . C15 . H151 . 120.6 no
N9 . C16 . O17 . 123.13(12) yes
N9 . C16 . O18 . 111.70(11) yes
O17 . C16 . O18 . 125.16(12) yes
C16 . O18 . C19 . 116.06(11) yes
O18 . C19 . C20 . 105.64(12) yes
O18 . C19 . H191 . 109.5 no
C20 . C19 . H191 . 112.8 no
O18 . C19 . H192 . 108.2 no
C20 . C19 . H192 . 112.5 no
H191 . C19 . H192 . 108.1 no
C19 . C20 . H201 . 109.4 no
C19 . C20 . H202 . 110.6 no
H201 . C20 . H202 . 108.1 no
C19 . C20 . H203 . 110.4 no
H201 . C20 . H203 . 109.3 no
H202 . C20 . H203 . 109.0 no
C6 . C21 . C22 . 126.60(11) yes
C6 . C21 . C29 . 118.23(11) yes
C22 . C21 . C29 . 115.13(11) yes
C21 . C22 . N23 . 122.48(11) yes
C21 . C22 . C26 . 122.33(12) yes
N23 . C22 . C26 . 115.14(12) yes
C22 . N23 . O24 . 118.98(11) yes
C22 . N23 . O25 . 118.68(11) yes
O24 . N23 . O25 . 122.29(11) yes
C22 . C26 . C27 . 120.27(13) yes
C22 . C26 . H261 . 118.8 no
C27 . C26 . H261 . 120.9 no
C26 . C27 . C28 . 119.52(12) yes
C26 . C27 . H271 . 120.3 no
C28 . C27 . H271 . 120.1 no
C27 . C28 . C29 . 118.84(12) yes
C27 . C28 . C30 . 120.73(12) yes
C29 . C28 . C30 . 120.43(13) yes
C28 . C29 . C21 . 123.69(12) yes
C28 . C29 . H291 . 118.6 no
C21 . C29 . H291 . 117.7 no
C28 . C30 . H302 . 110.9 no
C28 . C30 . H301 . 111.7 no
H302 . C30 . H301 . 108.6 no
C28 . C30 . H303 . 109.7 no
H302 . C30 . H303 . 108.2 no
H301 . C30 . H303 . 107.6 no
C6 . C31 . O32 . 112.22(11) yes
C6 . C31 . O34 . 123.21(12) yes
O32 . C31 . O34 . 124.27(12) yes
C31 . O32 . C33 . 115.95(11) yes
O32 . C33 . H332 . 106.9 no
O32 . C33 . H331 . 109.2 no
H332 . C33 . H331 . 109.7 no
O32 . C33 . H333 . 109.3 no
H332 . C33 . H333 . 111.7 no
H331 . C33 . H333 . 109.9 no
O1 . C35 . C36 . 108.36(12) yes
O1 . C35 . C37 . 105.76(12) yes
C36 . C35 . C37 . 114.55(13) yes
O1 . C35 . H351 . 107.1 no
C36 . C35 . H351 . 110.4 no
C37 . C35 . H351 . 110.3 no
C35 . C36 . H362 . 110.5 no
C35 . C36 . H361 . 110.6 no
H362 . C36 . H361 . 109.5 no
C35 . C36 . H363 . 109.9 no
H362 . C36 . H363 . 106.9 no
H361 . C36 . H363 . 109.3 no
C35 . C37 . H372 . 109.2 no
C35 . C37 . H371 . 110.5 no
H372 . C37 . H371 . 108.9 no
C35 . C37 . H373 . 111.0 no
H372 . C37 . H373 . 108.5 no
H371 . C37 . H373 . 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
C14 . H141 . O24 4_646 135.06(4) 0.965 2.526 3.280(2) yes
C27 . H271 . O34 2_666 150.84(4) 0.955 2.588 3.453(2) yes
N7 . H71 . O3 1_565 163.16(3) 0.871 2.387 3.231(2) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 06/02/14 at 13:09:55
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE N   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,X'S) H   ( 303,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) H   ( 333,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) H   ( 363,X'S) 
RIDE C   (  37,X'S) H   ( 372,X'S) H   ( 371,X'S) H   ( 373,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 06/02/14 at 13:09:55
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


# NOTE FO on scale of Fc,      0.12478
# Status flags: 
#    o - used in refinement 
#    < - excluded by I/sigmaI cutoff 
#    l - excluded at low resolution  
#    h - excluded at high resolution  
#    x - excluded for another reason  

_chemical_name_common            pyrroloindoline_2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / hexanes'
_database_code_depnum_ccdc_archive 'CCDC 1020473'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1spirocyclicpyrroline
#==============================================================================
############################################################# 
# ***oxford university chemical crystallography group*** 
# 
# this structure was solved by Russell W. Driver on 16/08/2014 
#           The authors would like to thank the 
# Chemical Crystallography Service at the Univeristy of Oxford 
#                   for expertise and 
#  Diamond Light Source for an award of beamtime (MT7768) 
############################################################# 

# start Validation Reply Form _vrf_PLAT029_5  
# PROBLEM: _diffrn_measured_fraction_theta_full Low ..0.905 
# Response:  DATA COLLECTED FROM A SYNCHROTRON LIGHT SOURCE 
# CAUSING A LACK OF HIGH-ANGLE COMPLETENESS DUE TO CRYSTAL 
# DECOMPOSITON IN THE BEAMLINE. 
# end Validation Reply Form

_audit_creation_date             2014-08-16
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 178RWD14-
_chemical_name_systematic        'please see SI'
_chemical_melting_point          'please see SI'


_cell_length_a                   12.7056(3)
_cell_length_b                   26.8163(5)
_cell_length_c                   7.0360(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.887(2)
_cell_angle_gamma                90
_cell_volume                     2384.64(10)

_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 0.0020 0.0020 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 0.0160 0.0090 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 0.0040 0.0030 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 0.0070 0.0060 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 = C27 H21 F1 N4 O6 
# Dc =      1.44 Fooo =   1072.00 Mu =      1.09 M =    516.49
# Found Formula = C27 H21 F1 N4 O6 
# Dc =      1.44 FOOO =   1072.00 Mu =      1.09 M =    516.48

_chemical_formula_sum            'C27 H21 F1 N4 O6'
_chemical_formula_moiety         'C27 H21 F1 N4 O6'
_chemical_compound_source        synthesis
_chemical_formula_weight         516.48


_cell_measurement_reflns_used    9801
_cell_measurement_theta_min      2
_cell_measurement_theta_max      26
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.010
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_max          0.050

_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.109

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_detector                 CCD
_diffrn_measurement_device       'CrystalLogic Kappa (3 circle)'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'

_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'

_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            29242
_reflns_number_total             4802
_diffrn_reflns_av_R_equivalents  0.065
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4802 
# Theoretical number of reflections is about 11089 


_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         26.703
_diffrn_measured_fraction_theta_max 0.865

_diffrn_reflns_theta_full        25.101
_diffrn_measured_fraction_theta_full 0.905


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              34
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   2.70
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.72


# 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_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4790
_refine_ls_number_restraints     0
_refine_ls_number_parameters     343
_oxford_refine_ls_R_factor_ref   0.0894
_refine_ls_wR_factor_ref         0.1726
_refine_ls_goodness_of_fit_ref   0.9780
_refine_ls_shift/su_max          0.0001560
_refine_ls_shift/su_mean         0.0000147


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4790
_refine_ls_R_factor_all          0.0894
_refine_ls_wR_factor_all         0.1726

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3948
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_gt          0.1633

# 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 .


_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 + 4.77P] 
 ,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 -0.10496(15) 0.43851(7) 0.2535(3) 0.0516 1.0000 Uani . . . . . .
C2 C -0.0112(3) 0.46312(11) 0.2603(4) 0.0389 1.0000 Uani . . . . . .
C3 C -0.0138(3) 0.51424(12) 0.2422(5) 0.0443 1.0000 Uani . . . . . .
C4 C 0.0825(3) 0.53850(11) 0.2543(5) 0.0468 1.0000 Uani . . . . . .
C5 C 0.1768(3) 0.51200(11) 0.2859(5) 0.0404 1.0000 Uani . . . . . .
N6 N 0.2747(3) 0.54152(10) 0.3017(4) 0.0506 1.0000 Uani . . . . . .
O7 O 0.3531(2) 0.52485(9) 0.4039(4) 0.0585 1.0000 Uani . . . . . .
O8 O 0.2745(2) 0.58203(9) 0.2234(5) 0.0742 1.0000 Uani . . . . . .
C9 C 0.1791(2) 0.45933(10) 0.3029(4) 0.0341 1.0000 Uani . . . . . .
C10 C 0.0812(2) 0.43583(11) 0.2895(4) 0.0356 1.0000 Uani . . . . . .
C11 C 0.2798(2) 0.42827(10) 0.3459(4) 0.0331 1.0000 Uani . . . . . .
N12 N 0.2581(2) 0.37479(9) 0.2864(4) 0.0384 1.0000 Uani . . . . . .
C13 C 0.2747(2) 0.34628(11) 0.4288(4) 0.0358 1.0000 Uani . . . . . .
C14 C 0.3022(2) 0.37169(10) 0.6236(4) 0.0325 1.0000 Uani . . . . . .
C15 C 0.3188(3) 0.42605(11) 0.5658(4) 0.0389 1.0000 Uani . . . . . .
C16 C 0.3899(2) 0.34419(10) 0.7415(4) 0.0310 1.0000 Uani . . . . . .
C17 C 0.3475(2) 0.31700(10) 0.8855(4) 0.0292 1.0000 Uani . . . . . .
N18 N 0.23592(18) 0.32649(8) 0.8770(3) 0.0290 1.0000 Uani . . . . . .
C19 C 0.2074(2) 0.36205(10) 0.7360(4) 0.0308 1.0000 Uani . . . . . .
O20 O 0.11997(16) 0.38110(7) 0.7008(3) 0.0363 1.0000 Uani . . . . . .
C21 C 0.1674(2) 0.30393(9) 1.0024(4) 0.0296 1.0000 Uani . . . . . .
O22 O 0.19859(15) 0.26938(7) 1.1057(3) 0.0318 1.0000 Uani . . . . . .
N23 N 0.06946(18) 0.32433(8) 0.9869(3) 0.0318 1.0000 Uani . . . . . .
C24 C -0.0100(2) 0.31697(10) 1.1115(4) 0.0306 1.0000 Uani . . . . . .
C25 C -0.1127(2) 0.33202(11) 1.0461(4) 0.0359 1.0000 Uani . . . . . .
C26 C -0.1924(2) 0.32973(11) 1.1658(5) 0.0385 1.0000 Uani . . . . . .
C27 C -0.1734(2) 0.31173(11) 1.3525(5) 0.0370 1.0000 Uani . . . . . .
C28 C -0.0710(2) 0.29671(10) 1.4149(4) 0.0357 1.0000 Uani . . . . . .
C29 C 0.0105(2) 0.29879(10) 1.2985(4) 0.0328 1.0000 Uani . . . . . .
C30 C -0.2602(3) 0.30982(13) 1.4833(5) 0.0472 1.0000 Uani . . . . . .
C31 C 0.4117(2) 0.28809(10) 1.0143(4) 0.0332 1.0000 Uani . . . . . .
C32 C 0.5191(2) 0.28731(11) 0.9923(4) 0.0372 1.0000 Uani . . . . . .
C33 C 0.5622(2) 0.31383(11) 0.8491(4) 0.0376 1.0000 Uani . . . . . .
C34 C 0.4965(2) 0.34278(11) 0.7204(4) 0.0356 1.0000 Uani . . . . . .
C35 C 0.3639(3) 0.44171(11) 0.2112(5) 0.0404 1.0000 Uani . . . . . .
O36 O 0.45978(18) 0.42786(8) 0.2826(3) 0.0444 1.0000 Uani . . . . . .
C37 C 0.5446(3) 0.43529(14) 0.1604(6) 0.0535 1.0000 Uani . . . . . .
O38 O 0.3437(2) 0.46018(10) 0.0551(4) 0.0586 1.0000 Uani . . . . . .
H31 H -0.0789 0.5314 0.2223 0.0530 1.0000 Uiso R . . . . .
H41 H 0.0857 0.5740 0.2408 0.0562 1.0000 Uiso R . . . . .
H101 H 0.0772 0.4009 0.2992 0.0431 1.0000 Uiso R . . . . .
H131 H 0.2673 0.3106 0.4166 0.0425 1.0000 Uiso R . . . . .
H151 H 0.3949 0.4342 0.5812 0.0473 1.0000 Uiso R . . . . .
H152 H 0.2829 0.4486 0.6402 0.0471 1.0000 Uiso R . . . . .
H251 H -0.1267 0.3444 0.9215 0.0426 1.0000 Uiso R . . . . .
H261 H -0.2609 0.3409 1.1186 0.0462 1.0000 Uiso R . . . . .
H281 H -0.0569 0.2847 1.5417 0.0429 1.0000 Uiso R . . . . .
H291 H 0.0794 0.2891 1.3458 0.0388 1.0000 Uiso R . . . . .
H301 H -0.2473 0.2839 1.5767 0.0707 1.0000 Uiso R . . . . .
H303 H -0.2642 0.3414 1.5466 0.0709 1.0000 Uiso R . . . . .
H302 H -0.3257 0.3037 1.4060 0.0714 1.0000 Uiso R . . . . .
H311 H 0.3845 0.2703 1.1123 0.0400 1.0000 Uiso R . . . . .
H321 H 0.5644 0.2680 1.0755 0.0449 1.0000 Uiso R . . . . .
H331 H 0.6356 0.3125 0.8380 0.0449 1.0000 Uiso R . . . . .
H341 H 0.5243 0.3606 0.6225 0.0431 1.0000 Uiso R . . . . .
H372 H 0.6090 0.4203 0.2220 0.0800 1.0000 Uiso R . . . . .
H373 H 0.5544 0.4712 0.1401 0.0793 1.0000 Uiso R . . . . .
H371 H 0.5248 0.4190 0.0402 0.0795 1.0000 Uiso R . . . . .
H231 H 0.0564 0.3460 0.8950 0.0381 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.6(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
F1 . C2 . 1.358(4) yes
C2 . C3 . 1.377(4) yes
C2 . C10 . 1.381(4) yes
C3 . C4 . 1.381(5) yes
C3 . H31 . 0.944 no
C4 . C5 . 1.391(5) yes
C4 . H41 . 0.958 no
C5 . N6 . 1.469(4) yes
C5 . C9 . 1.417(4) yes
N6 . O7 . 1.250(4) yes
N6 . O8 . 1.218(4) yes
C9 . C10 . 1.389(4) yes
C9 . C11 . 1.530(4) yes
C10 . H101 . 0.941 no
C11 . N12 . 1.512(4) yes
C11 . C15 . 1.576(4) yes
C11 . C35 . 1.542(4) yes
N12 . C13 . 1.261(4) yes
C13 . C14 . 1.538(4) yes
C13 . H131 . 0.966 no
C14 . C15 . 1.534(4) yes
C14 . C16 . 1.511(4) yes
C14 . C19 . 1.529(4) yes
C15 . H151 . 0.985 no
C15 . H152 . 0.947 no
C16 . C17 . 1.401(4) yes
C16 . C34 . 1.378(4) yes
C17 . N18 . 1.436(4) yes
C17 . C31 . 1.391(4) yes
N18 . C19 . 1.397(3) yes
N18 . C21 . 1.435(4) yes
C19 . O20 . 1.225(3) yes
C21 . O22 . 1.219(3) yes
C21 . N23 . 1.353(4) yes
N23 . C24 . 1.417(4) yes
N23 . H231 . 0.873 no
C24 . C25 . 1.398(4) yes
C24 . C29 . 1.402(4) yes
C25 . C26 . 1.383(4) yes
C25 . H251 . 0.937 no
C26 . C27 . 1.398(4) yes
C26 . H261 . 0.947 no
C27 . C28 . 1.389(4) yes
C27 . C30 . 1.508(4) yes
C28 . C29 . 1.386(4) yes
C28 . H281 . 0.949 no
C29 . H291 . 0.940 no
C30 . H301 . 0.958 no
C30 . H303 . 0.961 no
C30 . H302 . 0.960 no
C31 . C32 . 1.389(4) yes
C31 . H311 . 0.934 no
C32 . C33 . 1.391(4) yes
C32 . H321 . 0.934 no
C33 . C34 . 1.401(4) yes
C33 . H331 . 0.945 no
C34 . H341 . 0.937 no
C35 . O36 . 1.323(4) yes
C35 . O38 . 1.209(4) yes
O36 . C37 . 1.459(4) yes
C37 . H372 . 0.973 no
C37 . H373 . 0.983 no
C37 . H371 . 0.962 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 117.9(3) yes
F1 . C2 . C10 . 118.5(3) yes
C3 . C2 . C10 . 123.6(3) yes
C2 . C3 . C4 . 116.8(3) yes
C2 . C3 . H31 . 120.7 no
C4 . C3 . H31 . 122.5 no
C3 . C4 . C5 . 120.8(3) yes
C3 . C4 . H41 . 120.5 no
C5 . C4 . H41 . 118.7 no
C4 . C5 . N6 . 116.4(3) yes
C4 . C5 . C9 . 122.2(3) yes
N6 . C5 . C9 . 121.3(3) yes
C5 . N6 . O7 . 118.0(3) yes
C5 . N6 . O8 . 118.9(3) yes
O7 . N6 . O8 . 122.9(3) yes
C5 . C9 . C10 . 115.8(3) yes
C5 . C9 . C11 . 124.7(3) yes
C10 . C9 . C11 . 119.4(2) yes
C9 . C10 . C2 . 120.8(3) yes
C9 . C10 . H101 . 120.1 no
C2 . C10 . H101 . 119.1 no
C9 . C11 . N12 . 109.6(2) yes
C9 . C11 . C15 . 112.8(2) yes
N12 . C11 . C15 . 105.4(2) yes
C9 . C11 . C35 . 111.7(2) yes
N12 . C11 . C35 . 99.8(2) yes
C15 . C11 . C35 . 116.4(2) yes
C11 . N12 . C13 . 110.1(2) yes
N12 . C13 . C14 . 116.3(3) yes
N12 . C13 . H131 . 121.6 no
C14 . C13 . H131 . 122.0 no
C13 . C14 . C15 . 102.1(2) yes
C13 . C14 . C16 . 111.1(2) yes
C15 . C14 . C16 . 119.7(2) yes
C13 . C14 . C19 . 105.5(2) yes
C15 . C14 . C19 . 115.8(2) yes
C16 . C14 . C19 . 102.1(2) yes
C14 . C15 . C11 . 105.0(2) yes
C14 . C15 . H151 . 110.0 no
C11 . C15 . H151 . 107.8 no
C14 . C15 . H152 . 111.9 no
C11 . C15 . H152 . 113.4 no
H151 . C15 . H152 . 108.7 no
C14 . C16 . C17 . 109.6(2) yes
C14 . C16 . C34 . 129.2(3) yes
C17 . C16 . C34 . 121.2(3) yes
C16 . C17 . N18 . 109.2(2) yes
C16 . C17 . C31 . 121.2(3) yes
N18 . C17 . C31 . 129.5(3) yes
C17 . N18 . C19 . 109.5(2) yes
C17 . N18 . C21 . 124.0(2) yes
C19 . N18 . C21 . 126.5(2) yes
C14 . C19 . N18 . 108.8(2) yes
C14 . C19 . O20 . 124.8(2) yes
N18 . C19 . O20 . 126.3(3) yes
N18 . C21 . O22 . 120.4(3) yes
N18 . C21 . N23 . 113.0(2) yes
O22 . C21 . N23 . 126.6(3) yes
C21 . N23 . C24 . 126.9(2) yes
C21 . N23 . H231 . 115.6 no
C24 . N23 . H231 . 117.3 no
N23 . C24 . C25 . 117.1(3) yes
N23 . C24 . C29 . 123.6(2) yes
C25 . C24 . C29 . 119.1(3) yes
C24 . C25 . C26 . 120.3(3) yes
C24 . C25 . H251 . 119.4 no
C26 . C25 . H251 . 120.3 no
C25 . C26 . C27 . 121.4(3) yes
C25 . C26 . H261 . 118.5 no
C27 . C26 . H261 . 120.2 no
C26 . C27 . C28 . 117.6(3) yes
C26 . C27 . C30 . 121.2(3) yes
C28 . C27 . C30 . 121.2(3) yes
C27 . C28 . C29 . 122.3(3) yes
C27 . C28 . H281 . 118.4 no
C29 . C28 . H281 . 119.3 no
C24 . C29 . C28 . 119.3(3) yes
C24 . C29 . H291 . 120.4 no
C28 . C29 . H291 . 120.3 no
C27 . C30 . H301 . 111.0 no
C27 . C30 . H303 . 109.2 no
H301 . C30 . H303 . 109.5 no
C27 . C30 . H302 . 107.8 no
H301 . C30 . H302 . 110.0 no
H303 . C30 . H302 . 109.3 no
C17 . C31 . C32 . 116.9(3) yes
C17 . C31 . H311 . 122.0 no
C32 . C31 . H311 . 121.1 no
C31 . C32 . C33 . 122.5(3) yes
C31 . C32 . H321 . 119.1 no
C33 . C32 . H321 . 118.4 no
C32 . C33 . C34 . 119.9(3) yes
C32 . C33 . H331 . 120.4 no
C34 . C33 . H331 . 119.7 no
C33 . C34 . C16 . 118.2(3) yes
C33 . C34 . H341 . 120.9 no
C16 . C34 . H341 . 120.9 no
C11 . C35 . O36 . 111.7(3) yes
C11 . C35 . O38 . 124.0(3) yes
O36 . C35 . O38 . 124.1(3) yes
C35 . O36 . C37 . 116.4(3) yes
O36 . C37 . H372 . 108.6 no
O36 . C37 . H373 . 109.4 no
H372 . C37 . H373 . 110.8 no
O36 . C37 . H371 . 108.3 no
H372 . C37 . H371 . 109.7 no
H373 . C37 . H371 . 110.0 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
C3 . H31 . O20 2_566 129.08(10) 0.944 2.476 3.157(4) yes
C13 . H131 . O22 1_554 122.22(8) 0.966 2.525 3.147(4) yes
N23 . H231 . O20 . 142.94(9) 0.873 1.905 2.654(4) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 16/08/14 at 14:35:38
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE N   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 303,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  37,X'S) H   ( 372,X'S) H   ( 373,X'S) H   ( 371,X'S) 
END                                                                             
;


# NOTE FO on scale of Fc,      0.11626
# Status flags: 
#    o - used in refinement 
#    < - excluded by I/sigmaI cutoff 
#    l - excluded at low resolution  
#    h - excluded at high resolution  
#    x - excluded for another reason  

_chemical_name_common            'spirocyclic pyrroline_1'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / hexanes'
_database_code_depnum_ccdc_archive 'CCDC 1020474'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2spirocyclicpyrroline
#==============================================================================

############################################################# 
# ***oxford university chemical crystallography group*** 
# 
# this structure was solved by Russell Driver on 05/02/2014 
############################################################# 

_audit_creation_date             2014-02-05
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 125RWD13
_chemical_name_systematic        .
_chemical_melting_point          'See SI'

_cell_length_a                   15.470(2)
_cell_length_b                   9.988(1)
_cell_length_c                   18.047(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.190(6)
_cell_angle_gamma                90
_cell_volume                     2649.20(6)

_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 0.0033 0.0016 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 0.0061 0.0033 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'
F 0.0171 0.0103 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'
O 0.0106 0.0060 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 H17 F7 N4 O6 
# Dc =      1.60 Fooo =   1296.00 Mu =      1.46 M =    638.45
# Found Formula = C28 H17 F7 N4 O6 
# Dc =      1.60 FOOO =   1296.00 Mu =      1.46 M =    638.45

_chemical_formula_sum            'C28 H17 F7 N4 O6'
_chemical_formula_moiety         'C28 H17 F7 N4 O6'
_chemical_compound_source        synthesis
_chemical_formula_weight         638.45


_cell_measurement_reflns_used    6229
_cell_measurement_theta_min      1
_cell_measurement_theta_max      1
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.146

# Sheldrick geometric approximatio 0.96 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  1.0
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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            42456
_reflns_number_total             6016
_diffrn_reflns_av_R_equivalents  0.017
# Number of reflections without Friedels Law is 10615 
# Number of reflections with Friedels Law is 6016 
# Theoretical number of reflections is about 6077 


_diffrn_reflns_theta_min         5.098
_diffrn_reflns_theta_max         27.485
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        26.935
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -20
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   2.52
_oxford_diffrn_Wilson_scale      1.67

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.77
_refine_diff_density_max         1.03


# 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_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         6015
_refine_ls_number_restraints     0
_refine_ls_number_parameters     406
_oxford_refine_ls_R_factor_ref   0.0591
_refine_ls_wR_factor_ref         0.1217
_refine_ls_goodness_of_fit_ref   0.9091
_refine_ls_shift/su_max          0.0003282
_refine_ls_shift/su_mean         0.0000368


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6015
_refine_ls_R_factor_all          0.0591
_refine_ls_wR_factor_all         0.1217

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5062
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_gt          0.1117

# 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 .


_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 67.9 110. 63.8 25.3 5.48 
;

# 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 0.49036(8) 0.36395(14) 0.10713(7) 0.0429 1.0000 Uani . . . . . .
C2 C 0.57334(12) 0.30623(19) 0.12739(11) 0.0295 1.0000 Uani . . . . . .
C3 C 0.61817(11) 0.28926(17) 0.20598(10) 0.0244 1.0000 Uani . . . . . .
C4 C 0.70439(11) 0.23215(16) 0.23081(10) 0.0209 1.0000 Uani . . . . . .
C5 C 0.74191(12) 0.19757(18) 0.17196(10) 0.0257 1.0000 Uani . . . . . .
N6 N 0.83416(11) 0.14299(18) 0.19067(10) 0.0332 1.0000 Uani . . . . . .
O7 O 0.86515(9) 0.08114(14) 0.25202(8) 0.0341 1.0000 Uani . . . . . .
O8 O 0.87600(13) 0.1623(2) 0.14458(11) 0.0671 1.0000 Uani . . . . . .
C9 C 0.69555(13) 0.2152(2) 0.09304(11) 0.0308 1.0000 Uani . . . . . .
C10 C 0.60882(13) 0.2688(2) 0.06976(11) 0.0326 1.0000 Uani . . . . . .
C11 C 0.74605(11) 0.20515(16) 0.31819(9) 0.0204 1.0000 Uani . . . . . .
N12 N 0.70162(10) 0.29363(15) 0.36216(8) 0.0234 1.0000 Uani . . . . . .
C13 C 0.66732(11) 0.22241(17) 0.40361(10) 0.0226 1.0000 Uani . . . . . .
C14 C 0.67491(11) 0.07115(17) 0.39767(9) 0.0210 1.0000 Uani . . . . . .
C15 C 0.72856(11) 0.05846(16) 0.33876(10) 0.0212 1.0000 Uani . . . . . .
C16 C 0.71425(11) 0.00120(17) 0.47450(9) 0.0217 1.0000 Uani . . . . . .
C17 C 0.80227(11) 0.00469(18) 0.52519(10) 0.0245 1.0000 Uani . . . . . .
C18 C 0.82434(12) -0.07674(19) 0.59105(10) 0.0274 1.0000 Uani . . . . . .
C19 C 0.75853(13) -0.15875(19) 0.60482(11) 0.0307 1.0000 Uani . . . . . .
C20 C 0.66944(13) -0.16282(19) 0.55444(11) 0.0290 1.0000 Uani . . . . . .
C21 C 0.64904(11) -0.08118(17) 0.48940(10) 0.0220 1.0000 Uani . . . . . .
N22 N 0.56583(9) -0.07007(15) 0.42587(8) 0.0225 1.0000 Uani . . . . . .
C23 C 0.57846(11) 0.01371(17) 0.36868(10) 0.0217 1.0000 Uani . . . . . .
O24 O 0.52243(8) 0.03989(14) 0.30634(7) 0.0286 1.0000 Uani . . . . . .
C25 C 0.48258(11) -0.13034(18) 0.42625(10) 0.0249 1.0000 Uani . . . . . .
O26 O 0.47635(9) -0.18403(15) 0.48436(8) 0.0348 1.0000 Uani . . . . . .
N27 N 0.41523(10) -0.11777(16) 0.35761(9) 0.0264 1.0000 Uani . . . . . .
C28 C 0.32529(11) -0.16442(18) 0.34228(10) 0.0254 1.0000 Uani . . . . . .
C29 C 0.30305(12) -0.27019(18) 0.38357(11) 0.0260 1.0000 Uani . . . . . .
C30 C 0.21320(12) -0.31240(18) 0.36345(11) 0.0275 1.0000 Uani . . . . . .
C31 C 0.14525(12) -0.25431(19) 0.30259(11) 0.0298 1.0000 Uani . . . . . .
C32 C 0.16850(12) -0.1499(2) 0.26177(11) 0.0286 1.0000 Uani . . . . . .
C33 C 0.25810(12) -0.10413(19) 0.28193(11) 0.0270 1.0000 Uani . . . . . .
C34 C 0.09770(13) -0.0788(2) 0.19764(12) 0.0356 1.0000 Uani . . . . . .
F35 F 0.08209(12) 0.04648(18) 0.21800(9) 0.0656 1.0000 Uani . . . . . .
F36 F 0.12398(9) -0.06102(14) 0.13472(7) 0.0436 1.0000 Uani . . . . . .
F37 F 0.01937(10) -0.1425(2) 0.17430(10) 0.0805 1.0000 Uani . . . . . .
C38 C 0.18797(13) -0.4252(2) 0.40750(12) 0.0332 1.0000 Uani . . . . . .
F39 F 0.15322(9) -0.52965(13) 0.36053(8) 0.0454 1.0000 Uani . . . . . .
F40 F 0.12394(10) -0.39009(14) 0.43908(9) 0.0538 1.0000 Uani . . . . . .
F41 F 0.25822(9) -0.47313(14) 0.46500(8) 0.0503 1.0000 Uani . . . . . .
C42 C 0.84630(11) 0.24481(18) 0.35456(10) 0.0241 1.0000 Uani . . . . . .
O43 O 0.89695(9) 0.19259(15) 0.41163(8) 0.0339 1.0000 Uani . . . . . .
O44 O 0.86736(8) 0.35189(14) 0.31927(8) 0.0308 1.0000 Uani . . . . . .
C45 C 0.95767(14) 0.4052(3) 0.35663(14) 0.0466 1.0000 Uani . . . . . .
H31 H 0.5914 0.3167 0.2434 0.0294 1.0000 Uiso R . . . . .
H91 H 0.7233 0.1918 0.0558 0.0373 1.0000 Uiso R . . . . .
H101 H 0.5756 0.2797 0.0170 0.0389 1.0000 Uiso R . . . . .
H131 H 0.6374 0.2611 0.4368 0.0268 1.0000 Uiso R . . . . .
H152 H 0.7865 0.0122 0.3628 0.0252 1.0000 Uiso R . . . . .
H151 H 0.6933 0.0115 0.2923 0.0246 1.0000 Uiso R . . . . .
H171 H 0.8462 0.0602 0.5145 0.0296 1.0000 Uiso R . . . . .
H181 H 0.8839 -0.0781 0.6256 0.0325 1.0000 Uiso R . . . . .
H191 H 0.7744 -0.2126 0.6499 0.0372 1.0000 Uiso R . . . . .
H201 H 0.6258 -0.2188 0.5643 0.0354 1.0000 Uiso R . . . . .
H291 H 0.3476 -0.3129 0.4235 0.0311 1.0000 Uiso R . . . . .
H311 H 0.0850 -0.2860 0.2900 0.0365 1.0000 Uiso R . . . . .
H331 H 0.2722 -0.0315 0.2542 0.0320 1.0000 Uiso R . . . . .
H452 H 0.9636 0.4834 0.3266 0.0695 1.0000 Uiso R . . . . .
H453 H 1.0017 0.3378 0.3548 0.0694 1.0000 Uiso R . . . . .
H451 H 0.9647 0.4288 0.4105 0.0695 1.0000 Uiso R . . . . .
H2 H 0.4269 -0.0700 0.3231 0.0319 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6961(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
F1 . C2 . 1.349(2) yes
C2 . C3 . 1.381(3) yes
C2 . C10 . 1.371(3) yes
C3 . C4 . 1.390(2) yes
C3 . H31 . 0.937 no
C4 . C5 . 1.403(2) yes
C4 . C11 . 1.530(2) yes
C5 . N6 . 1.465(2) yes
C5 . C9 . 1.391(3) yes
N6 . O7 . 1.227(2) yes
N6 . O8 . 1.218(2) yes
C9 . C10 . 1.383(3) yes
C9 . H91 . 0.933 no
C10 . H101 . 0.936 no
C11 . N12 . 1.491(2) yes
C11 . C15 . 1.556(2) yes
C11 . C42 . 1.535(2) yes
N12 . C13 . 1.263(2) yes
C13 . C14 . 1.522(2) yes
C13 . H131 . 0.946 no
C14 . C15 . 1.545(2) yes
C14 . C16 . 1.501(2) yes
C14 . C23 . 1.530(2) yes
C15 . H152 . 0.981 no
C15 . H151 . 0.967 no
C16 . C17 . 1.384(2) yes
C16 . C21 . 1.392(2) yes
C17 . C18 . 1.392(3) yes
C17 . H171 . 0.942 no
C18 . C19 . 1.388(3) yes
C18 . H181 . 0.937 no
C19 . C20 . 1.395(3) yes
C19 . H191 . 0.941 no
C20 . C21 . 1.382(2) yes
C20 . H201 . 0.935 no
C21 . N22 . 1.436(2) yes
N22 . C23 . 1.389(2) yes
N22 . C25 . 1.424(2) yes
C23 . O24 . 1.215(2) yes
C25 . O26 . 1.208(2) yes
C25 . N27 . 1.353(2) yes
N27 . C28 . 1.410(2) yes
N27 . H2 . 0.847 no
C28 . C29 . 1.396(2) yes
C28 . C33 . 1.387(3) yes
C29 . C30 . 1.388(2) yes
C29 . H291 . 0.930 no
C30 . C31 . 1.388(3) yes
C30 . C38 . 1.499(3) yes
C31 . C32 . 1.387(3) yes
C31 . H311 . 0.943 no
C32 . C33 . 1.396(2) yes
C32 . C34 . 1.501(3) yes
C33 . H331 . 0.945 no
C34 . F35 . 1.347(3) yes
C34 . F36 . 1.332(2) yes
C34 . F37 . 1.316(2) yes
C38 . F39 . 1.346(2) yes
C38 . F40 . 1.335(2) yes
C38 . F41 . 1.335(2) yes
C42 . O43 . 1.201(2) yes
C42 . O44 . 1.336(2) yes
O44 . C45 . 1.450(2) yes
C45 . H452 . 0.971 no
C45 . H453 . 0.966 no
C45 . H451 . 0.972 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 117.45(17) yes
F1 . C2 . C10 . 118.91(17) yes
C3 . C2 . C10 . 123.64(17) yes
C2 . C3 . C4 . 120.34(17) yes
C2 . C3 . H31 . 120.8 no
C4 . C3 . H31 . 118.9 no
C3 . C4 . C5 . 116.04(15) yes
C3 . C4 . C11 . 117.24(15) yes
C5 . C4 . C11 . 126.59(15) yes
C4 . C5 . N6 . 121.36(15) yes
C4 . C5 . C9 . 122.73(16) yes
N6 . C5 . C9 . 115.90(16) yes
C5 . N6 . O7 . 118.25(14) yes
C5 . N6 . O8 . 118.06(17) yes
O7 . N6 . O8 . 123.69(17) yes
C5 . C9 . C10 . 120.08(17) yes
C5 . C9 . H91 . 120.0 no
C10 . C9 . H91 . 119.9 no
C9 . C10 . C2 . 117.10(17) yes
C9 . C10 . H101 . 121.7 no
C2 . C10 . H101 . 121.2 no
C4 . C11 . N12 . 109.16(13) yes
C4 . C11 . C15 . 111.31(13) yes
N12 . C11 . C15 . 106.73(12) yes
C4 . C11 . C42 . 116.07(13) yes
N12 . C11 . C42 . 101.03(13) yes
C15 . C11 . C42 . 111.63(13) yes
C11 . N12 . C13 . 109.28(14) yes
N12 . C13 . C14 . 117.48(15) yes
N12 . C13 . H131 . 121.6 no
C14 . C13 . H131 . 120.9 no
C13 . C14 . C15 . 101.53(13) yes
C13 . C14 . C16 . 114.51(14) yes
C15 . C14 . C16 . 116.58(14) yes
C13 . C14 . C23 . 107.93(13) yes
C15 . C14 . C23 . 114.20(13) yes
C16 . C14 . C23 . 102.25(13) yes
C14 . C15 . C11 . 104.94(13) yes
C14 . C15 . H152 . 110.3 no
C11 . C15 . H152 . 110.2 no
C14 . C15 . H151 . 111.0 no
C11 . C15 . H151 . 110.1 no
H152 . C15 . H151 . 110.2 no
C14 . C16 . C17 . 129.07(15) yes
C14 . C16 . C21 . 110.14(14) yes
C17 . C16 . C21 . 120.69(16) yes
C16 . C17 . C18 . 118.57(16) yes
C16 . C17 . H171 . 120.2 no
C18 . C17 . H171 . 121.2 no
C17 . C18 . C19 . 119.97(17) yes
C17 . C18 . H181 . 120.3 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . C20 . 122.08(17) yes
C18 . C19 . H191 . 119.0 no
C20 . C19 . H191 . 119.0 no
C19 . C20 . C21 . 116.97(16) yes
C19 . C20 . H201 . 121.2 no
C21 . C20 . H201 . 121.8 no
C16 . C21 . C20 . 121.72(16) yes
C16 . C21 . N22 . 108.86(14) yes
C20 . C21 . N22 . 129.32(15) yes
C21 . N22 . C23 . 109.93(13) yes
C21 . N22 . C25 . 123.38(14) yes
C23 . N22 . C25 . 126.56(14) yes
C14 . C23 . N22 . 108.67(14) yes
C14 . C23 . O24 . 124.99(15) yes
N22 . C23 . O24 . 126.33(15) yes
N22 . C25 . O26 . 120.62(16) yes
N22 . C25 . N27 . 113.30(15) yes
O26 . C25 . N27 . 126.07(16) yes
C25 . N27 . C28 . 125.41(15) yes
C25 . N27 . H2 . 116.4 no
C28 . N27 . H2 . 117.7 no
N27 . C28 . C29 . 122.53(17) yes
N27 . C28 . C33 . 117.54(16) yes
C29 . C28 . C33 . 119.90(16) yes
C28 . C29 . C30 . 118.93(17) yes
C28 . C29 . H291 . 120.9 no
C30 . C29 . H291 . 120.1 no
C29 . C30 . C31 . 121.94(17) yes
C29 . C30 . C38 . 119.65(18) yes
C31 . C30 . C38 . 118.40(16) yes
C30 . C31 . C32 . 118.46(16) yes
C30 . C31 . H311 . 119.9 no
C32 . C31 . H311 . 121.7 no
C31 . C32 . C33 . 120.58(18) yes
C31 . C32 . C34 . 121.17(16) yes
C33 . C32 . C34 . 118.19(17) yes
C32 . C33 . C28 . 120.17(17) yes
C32 . C33 . H331 . 119.2 no
C28 . C33 . H331 . 120.6 no
C32 . C34 . F35 . 112.29(17) yes
C32 . C34 . F36 . 112.14(16) yes
F35 . C34 . F36 . 103.74(18) yes
C32 . C34 . F37 . 113.27(18) yes
F35 . C34 . F37 . 108.13(19) yes
F36 . C34 . F37 . 106.68(18) yes
C30 . C38 . F39 . 111.57(16) yes
C30 . C38 . F40 . 112.33(17) yes
F39 . C38 . F40 . 105.59(15) yes
C30 . C38 . F41 . 113.47(15) yes
F39 . C38 . F41 . 106.23(17) yes
F40 . C38 . F41 . 107.14(17) yes
C11 . C42 . O43 . 123.78(15) yes
C11 . C42 . O44 . 111.52(14) yes
O43 . C42 . O44 . 124.43(15) yes
C42 . O44 . C45 . 114.55(14) yes
O44 . C45 . H452 . 106.3 no
O44 . C45 . H453 . 108.4 no
H452 . C45 . H453 . 110.5 no
O44 . C45 . H451 . 110.2 no
H452 . C45 . H451 . 111.3 no
H453 . C45 . H451 . 110.0 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
C15 . H151 . O44 4_645 166.54(5) 0.967 2.509 3.457(3) yes
C17 . H171 . O43 . 147.68(5) 0.942 2.593 3.427(3) yes
C45 . H452 . O24 4_655 139.25(7) 0.971 2.538 3.334(3) yes
N27 . H2 . O24 . 141.36(6) 0.847 1.939 2.654(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 05/02/14 at 18:05:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE N   (  27,X'S) H   (   2,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  45,X'S) H   ( 452,X'S) H   ( 453,X'S) H   ( 451,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 05/02/14 at 18:05:59
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
3 7 17 x .



# NOTE FO on scale of Fc,      1.43651
# Status flags: 
#    o - used in refinement 
#    < - excluded by I/sigmaI cutoff 
#    l - excluded at low resolution  
#    h - excluded at high resolution  
#    x - excluded for another reason  

_chemical_name_common            'spirocyclic pyrroline_2'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / hexanes'
_database_code_depnum_ccdc_archive 'CCDC 1020475'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3spirocyclicpyrroline
#==============================================================================

############################################################# 
# ***oxford university chemical crystallography group*** 
# 
# this structure was solved by Russell Driver on 06/02/2014 
############################################################# 

_audit_creation_date             2014-02-06
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 129RWD13
_chemical_name_systematic        .
_chemical_melting_point          'see SI'

_cell_length_a                   7.9955(4)
_cell_length_b                   10.0717(5)
_cell_length_c                   16.9314(9)
_cell_angle_alpha                76.919(5)
_cell_angle_beta                 89.286(4)
_cell_angle_gamma                83.437(4)
_cell_volume                     1319.25(12)

_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'
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 = C28 H17 F7 N4 O6 
# Dc =      1.61 Fooo =    648.00 Mu =     12.93 M =    638.45
# Found Formula = C28 H17 F7 N4 O6 
# Dc =      1.61 FOOO =    648.00 Mu =     12.93 M =    638.45

_chemical_formula_sum            'C28 H17 F7 N4 O6'
_chemical_formula_moiety         'C28 H17 F7 N4 O6'
_chemical_compound_source        synthesis
_chemical_formula_weight         638.45


_cell_measurement_reflns_used    5314
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.150

_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    1.293

# Sheldrick geometric approximatio 0.88 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_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       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            12422
_reflns_number_total             5433
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5433 
# Theoretical number of reflections is about 11101 


_diffrn_reflns_theta_min         4.537
_diffrn_reflns_theta_max         76.583
_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        73.520
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   2.79
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.40


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5411
_refine_ls_number_restraints     0
_refine_ls_number_parameters     406
_oxford_refine_ls_R_factor_ref   0.0501
_refine_ls_wR_factor_ref         0.1135
_refine_ls_goodness_of_fit_ref   0.9706
_refine_ls_shift/su_max          0.0002843
_refine_ls_shift/su_mean         0.0000257


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5413
_refine_ls_R_factor_all          0.0503
_refine_ls_wR_factor_all         0.1138

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4600
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_gt          0.1056

# 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 .


_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 + 0.50P] 
 ,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 0.48139(16) 1.14718(15) -0.46612(7) 0.0516 1.0000 Uani . . . . . .
C2 C 0.3491(2) 1.12641(19) -0.41664(11) 0.0358 1.0000 Uani . . . . . .
C3 C 0.3773(2) 1.09892(17) -0.33382(10) 0.0308 1.0000 Uani . . . . . .
C4 C 0.24522(19) 1.07194(15) -0.28060(10) 0.0254 1.0000 Uani . . . . . .
C5 C 0.28217(19) 1.03938(15) -0.18940(9) 0.0246 1.0000 Uani . . . . . .
N6 N 0.44897(17) 1.08263(13) -0.17411(8) 0.0268 1.0000 Uani . . . . . .
C7 C 0.54141(19) 0.98218(16) -0.13157(10) 0.0260 1.0000 Uani . . . . . .
C8 C 0.47336(19) 0.84380(15) -0.11329(9) 0.0241 1.0000 Uani . . . . . .
C9 C 0.29413(19) 0.88237(15) -0.15024(9) 0.0253 1.0000 Uani . . . . . .
C10 C 0.47237(19) 0.78246(15) -0.02211(9) 0.0240 1.0000 Uani . . . . . .
O11 O 0.38237(15) 0.82665(12) 0.02658(7) 0.0301 1.0000 Uani . . . . . .
N12 N 0.59276(16) 0.66739(13) -0.00453(8) 0.0250 1.0000 Uani . . . . . .
C13 C 0.66629(19) 0.64275(15) -0.07804(10) 0.0256 1.0000 Uani . . . . . .
C14 C 0.59552(19) 0.74221(15) -0.14352(9) 0.0248 1.0000 Uani . . . . . .
C15 C 0.6506(2) 0.74498(16) -0.22141(10) 0.0290 1.0000 Uani . . . . . .
C16 C 0.7766(2) 0.64446(18) -0.23350(11) 0.0336 1.0000 Uani . . . . . .
C17 C 0.8452(2) 0.54469(19) -0.16813(12) 0.0361 1.0000 Uani . . . . . .
C18 C 0.7920(2) 0.54155(17) -0.08898(11) 0.0329 1.0000 Uani . . . . . .
C19 C 0.6269(2) 0.57800(16) 0.07319(10) 0.0271 1.0000 Uani . . . . . .
O20 O 0.70871(18) 0.46713(12) 0.07909(8) 0.0376 1.0000 Uani . . . . . .
N21 N 0.56101(19) 0.63079(14) 0.13491(8) 0.0304 1.0000 Uani . . . . . .
C22 C 0.5634(2) 0.56152(16) 0.21701(10) 0.0286 1.0000 Uani . . . . . .
C23 C 0.6907(2) 0.45947(16) 0.25108(10) 0.0296 1.0000 Uani . . . . . .
C24 C 0.6799(2) 0.39430(16) 0.33234(10) 0.0304 1.0000 Uani . . . . . .
C25 C 0.5466(2) 0.42795(17) 0.37989(10) 0.0318 1.0000 Uani . . . . . .
C26 C 0.4224(2) 0.53129(17) 0.34516(10) 0.0316 1.0000 Uani . . . . . .
C27 C 0.4309(2) 0.59947(16) 0.26473(10) 0.0313 1.0000 Uani . . . . . .
C28 C 0.2755(3) 0.56767(19) 0.39531(11) 0.0381 1.0000 Uani . . . . . .
F29 F 0.30005(18) 0.67224(14) 0.42913(8) 0.0529 1.0000 Uani . . . . . .
F30 F 0.24641(19) 0.46386(14) 0.45591(9) 0.0620 1.0000 Uani . . . . . .
F31 F 0.13319(15) 0.60625(14) 0.35117(8) 0.0494 1.0000 Uani . . . . . .
C32 C 0.8194(2) 0.28768(18) 0.37006(11) 0.0357 1.0000 Uani . . . . . .
F33 F 0.89954(15) 0.22496(12) 0.31620(7) 0.0440 1.0000 Uani . . . . . .
F34 F 0.76612(18) 0.19089(13) 0.42893(8) 0.0554 1.0000 Uani . . . . . .
F35 F 0.93893(17) 0.34154(14) 0.40392(9) 0.0561 1.0000 Uani . . . . . .
C36 C 0.1600(2) 1.13417(16) -0.14926(10) 0.0280 1.0000 Uani . . . . . .
O37 O 0.16061(16) 1.08978(12) -0.06912(7) 0.0328 1.0000 Uani . . . . . .
C38 C 0.0534(2) 1.1750(2) -0.02618(12) 0.0365 1.0000 Uani . . . . . .
O39 O 0.08428(19) 1.23873(14) -0.18577(9) 0.0436 1.0000 Uani . . . . . .
C40 C 0.0861(2) 1.07555(16) -0.31594(10) 0.0295 1.0000 Uani . . . . . .
N41 N -0.06160(18) 1.04133(15) -0.26662(10) 0.0339 1.0000 Uani . . . . . .
O42 O -0.20018(18) 1.0717(2) -0.29856(11) 0.0673 1.0000 Uani . . . . . .
O43 O -0.04118(16) 0.97981(15) -0.19546(8) 0.0403 1.0000 Uani . . . . . .
C44 C 0.0591(2) 1.10855(18) -0.39933(11) 0.0352 1.0000 Uani . . . . . .
C45 C 0.1919(3) 1.1348(2) -0.45108(11) 0.0398 1.0000 Uani . . . . . .
H1 H 0.2100 0.8626 -0.1084 0.0291 1.0000 Uiso R . . . . .
H2 H 0.7801 0.4349 0.2198 0.0353 1.0000 Uiso R . . . . .
H3 H 0.5368 0.3811 0.4350 0.0372 1.0000 Uiso R . . . . .
H4 H 0.6038 0.8150 -0.2655 0.0343 1.0000 Uiso R . . . . .
H5 H 0.3449 0.6703 0.2420 0.0360 1.0000 Uiso R . . . . .
H6 H 0.2727 0.8313 -0.1905 0.0306 1.0000 Uiso R . . . . .
H7 H 0.4977 0.7084 0.1219 0.0369 1.0000 Uiso R . . . . .
H8 H 0.6514 0.9915 -0.1142 0.0307 1.0000 Uiso R . . . . .
H9 H 0.4852 1.1002 -0.3141 0.0375 1.0000 Uiso R . . . . .
H10 H 0.8363 0.4724 -0.0446 0.0405 1.0000 Uiso R . . . . .
H11 H -0.0495 1.1114 -0.4191 0.0423 1.0000 Uiso R . . . . .
H12 H 0.8148 0.6455 -0.2865 0.0398 1.0000 Uiso R . . . . .
H13 H 0.1785 1.1570 -0.5073 0.0485 1.0000 Uiso R . . . . .
H14 H -0.0618 1.1753 -0.0411 0.0546 1.0000 Uiso R . . . . .
H15 H 0.0848 1.2658 -0.0391 0.0540 1.0000 Uiso R . . . . .
H16 H 0.0687 1.1359 0.0318 0.0543 1.0000 Uiso R . . . . .
H17 H 0.9263 0.4769 -0.1775 0.0442 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.26(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 . 1.346(2) yes
C2 . C3 . 1.382(2) yes
C2 . C45 . 1.378(3) yes
C3 . C4 . 1.390(2) yes
C3 . H9 . 0.931 no
C4 . C5 . 1.530(2) yes
C4 . C40 . 1.406(2) yes
C5 . N6 . 1.4926(19) yes
C5 . C9 . 1.563(2) yes
C5 . C36 . 1.546(2) yes
N6 . C7 . 1.265(2) yes
C7 . C8 . 1.519(2) yes
C7 . H8 . 0.952 no
C8 . C9 . 1.543(2) yes
C8 . C10 . 1.528(2) yes
C8 . C14 . 1.503(2) yes
C9 . H1 . 0.975 no
C9 . H6 . 0.969 no
C10 . O11 . 1.214(2) yes
C10 . N12 . 1.3980(19) yes
N12 . C13 . 1.430(2) yes
N12 . C19 . 1.426(2) yes
C13 . C14 . 1.391(2) yes
C13 . C18 . 1.389(2) yes
C14 . C15 . 1.380(2) yes
C15 . C16 . 1.392(2) yes
C15 . H4 . 0.950 no
C16 . C17 . 1.386(3) yes
C16 . H12 . 0.943 no
C17 . C18 . 1.395(3) yes
C17 . H17 . 0.926 no
C18 . H10 . 0.943 no
C19 . O20 . 1.212(2) yes
C19 . N21 . 1.351(2) yes
N21 . C22 . 1.406(2) yes
N21 . H7 . 0.866 no
C22 . C23 . 1.390(2) yes
C22 . C27 . 1.395(2) yes
C23 . C24 . 1.390(2) yes
C23 . H2 . 0.929 no
C24 . C25 . 1.385(3) yes
C24 . C32 . 1.496(2) yes
C25 . C26 . 1.385(2) yes
C25 . H3 . 0.952 no
C26 . C27 . 1.384(2) yes
C26 . C28 . 1.500(3) yes
C27 . H5 . 0.949 no
C28 . F29 . 1.341(2) yes
C28 . F30 . 1.328(2) yes
C28 . F31 . 1.339(2) yes
C32 . F33 . 1.339(2) yes
C32 . F34 . 1.330(2) yes
C32 . F35 . 1.345(2) yes
C36 . O37 . 1.329(2) yes
C36 . O39 . 1.194(2) yes
O37 . C38 . 1.448(2) yes
C38 . H14 . 0.958 no
C38 . H15 . 0.953 no
C38 . H16 . 0.976 no
C40 . N41 . 1.466(2) yes
C40 . C44 . 1.389(2) yes
N41 . O42 . 1.215(2) yes
N41 . O43 . 1.227(2) yes
C44 . C45 . 1.379(3) yes
C44 . H11 . 0.930 no
C45 . H13 . 0.932 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 118.49(17) yes
F1 . C2 . C45 . 118.34(17) yes
C3 . C2 . C45 . 123.17(17) yes
C2 . C3 . C4 . 120.28(16) yes
C2 . C3 . H9 . 119.3 no
C4 . C3 . H9 . 120.4 no
C3 . C4 . C5 . 118.68(14) yes
C3 . C4 . C40 . 116.36(15) yes
C5 . C4 . C40 . 124.96(14) yes
C4 . C5 . N6 . 109.85(12) yes
C4 . C5 . C9 . 112.53(12) yes
N6 . C5 . C9 . 105.97(12) yes
C4 . C5 . C36 . 109.35(12) yes
N6 . C5 . C36 . 102.07(12) yes
C9 . C5 . C36 . 116.36(13) yes
C5 . N6 . C7 . 109.81(13) yes
N6 . C7 . C8 . 117.11(14) yes
N6 . C7 . H8 . 121.6 no
C8 . C7 . H8 . 121.2 no
C7 . C8 . C9 . 101.62(12) yes
C7 . C8 . C10 . 111.26(12) yes
C9 . C8 . C10 . 112.38(12) yes
C7 . C8 . C14 . 108.95(12) yes
C9 . C8 . C14 . 120.15(13) yes
C10 . C8 . C14 . 102.60(12) yes
C8 . C9 . C5 . 105.23(12) yes
C8 . C9 . H1 . 110.6 no
C5 . C9 . H1 . 111.2 no
C8 . C9 . H6 . 112.6 no
C5 . C9 . H6 . 110.7 no
H1 . C9 . H6 . 106.6 no
C8 . C10 . O11 . 125.63(14) yes
C8 . C10 . N12 . 108.36(12) yes
O11 . C10 . N12 . 126.01(14) yes
C10 . N12 . C13 . 109.73(12) yes
C10 . N12 . C19 . 126.07(13) yes
C13 . N12 . C19 . 123.90(13) yes
N12 . C13 . C14 . 109.45(13) yes
N12 . C13 . C18 . 129.28(15) yes
C14 . C13 . C18 . 121.24(15) yes
C8 . C14 . C13 . 109.60(13) yes
C8 . C14 . C15 . 129.20(15) yes
C13 . C14 . C15 . 120.91(15) yes
C14 . C15 . C16 . 118.63(16) yes
C14 . C15 . H4 . 120.3 no
C16 . C15 . H4 . 121.1 no
C15 . C16 . C17 . 120.17(16) yes
C15 . C16 . H12 . 119.2 no
C17 . C16 . H12 . 120.6 no
C16 . C17 . C18 . 121.81(16) yes
C16 . C17 . H17 . 119.0 no
C18 . C17 . H17 . 119.2 no
C17 . C18 . C13 . 117.23(16) yes
C17 . C18 . H10 . 122.0 no
C13 . C18 . H10 . 120.8 no
N12 . C19 . O20 . 120.28(15) yes
N12 . C19 . N21 . 113.36(13) yes
O20 . C19 . N21 . 126.36(15) yes
C19 . N21 . C22 . 125.67(14) yes
C19 . N21 . H7 . 116.8 no
C22 . N21 . H7 . 116.7 no
N21 . C22 . C23 . 122.77(16) yes
N21 . C22 . C27 . 117.17(15) yes
C23 . C22 . C27 . 120.06(15) yes
C22 . C23 . C24 . 118.61(16) yes
C22 . C23 . H2 . 120.4 no
C24 . C23 . H2 . 121.0 no
C23 . C24 . C25 . 122.01(16) yes
C23 . C24 . C32 . 118.84(16) yes
C25 . C24 . C32 . 119.13(15) yes
C24 . C25 . C26 . 118.50(16) yes
C24 . C25 . H3 . 122.1 no
C26 . C25 . H3 . 119.4 no
C25 . C26 . C27 . 120.82(17) yes
C25 . C26 . C28 . 119.29(16) yes
C27 . C26 . C28 . 119.88(16) yes
C22 . C27 . C26 . 119.94(16) yes
C22 . C27 . H5 . 120.4 no
C26 . C27 . H5 . 119.7 no
C26 . C28 . F29 . 111.96(17) yes
C26 . C28 . F30 . 112.38(16) yes
F29 . C28 . F30 . 106.33(16) yes
C26 . C28 . F31 . 112.09(15) yes
F29 . C28 . F31 . 106.43(15) yes
F30 . C28 . F31 . 107.26(17) yes
C24 . C32 . F33 . 112.71(15) yes
C24 . C32 . F34 . 112.53(16) yes
F33 . C32 . F34 . 107.48(15) yes
C24 . C32 . F35 . 112.07(15) yes
F33 . C32 . F35 . 105.56(16) yes
F34 . C32 . F35 . 105.99(16) yes
C5 . C36 . O37 . 111.38(13) yes
C5 . C36 . O39 . 123.66(15) yes
O37 . C36 . O39 . 124.77(16) yes
C36 . O37 . C38 . 115.17(14) yes
O37 . C38 . H14 . 109.5 no
O37 . C38 . H15 . 109.4 no
H14 . C38 . H15 . 110.5 no
O37 . C38 . H16 . 108.1 no
H14 . C38 . H16 . 109.3 no
H15 . C38 . H16 . 110.0 no
C4 . C40 . N41 . 121.76(15) yes
C4 . C40 . C44 . 122.48(16) yes
N41 . C40 . C44 . 115.75(15) yes
C40 . N41 . O42 . 118.50(16) yes
C40 . N41 . O43 . 119.18(14) yes
O42 . N41 . O43 . 122.28(16) yes
C40 . C44 . C45 . 120.21(17) yes
C40 . C44 . H11 . 118.5 no
C45 . C44 . H11 . 121.2 no
C44 . C45 . C2 . 117.41(17) yes
C44 . C45 . H13 . 122.5 no
C2 . C45 . H13 . 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
N21 . H7 . N6 2_675 122.92(4) 0.866 2.540 3.097(2) yes
N21 . H7 . O11 . 138.90(5) 0.866 1.947 2.661(2) yes
C3 . H9 . O42 1_655 161.96(7) 0.931 2.509 3.407(2) yes
C38 . H14 . O11 2_575 159.38(5) 0.958 2.574 3.487(2) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 06/02/14 at 11:55:44
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (   9,X'S) 
RIDE C   (   7,X'S) H   (   8,X'S) 
RIDE C   (   9,X'S) H   (   1,X'S) H   (   6,X'S) 
RIDE C   (  15,X'S) H   (   4,X'S) 
RIDE C   (  16,X'S) H   (  12,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  18,X'S) H   (  10,X'S) 
RIDE N   (  21,X'S) H   (   7,X'S) 
RIDE C   (  23,X'S) H   (   2,X'S) 
RIDE C   (  25,X'S) H   (   3,X'S) 
RIDE C   (  27,X'S) H   (   5,X'S) 
RIDE C   (  38,X'S) H   (  14,X'S) H   (  15,X'S) H   (  16,X'S) 
RIDE C   (  44,X'S) H   (  11,X'S) 
RIDE C   (  45,X'S) H   (  13,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 06/02/14 at 11:55:44
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;



# NOTE FO on scale of Fc,      0.18995
# Status flags: 
#    o - used in refinement 
#    < - excluded by I/sigmaI cutoff 
#    l - excluded at low resolution  
#    h - excluded at high resolution  
#    x - excluded for another reason  


_chemical_name_common            'spirocyclic pyrroline_3'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl aceate /  hexanes'
_database_code_depnum_ccdc_archive 'CCDC 1020476'
