# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

#######################################################################
#
#                 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_ravdino

_audit_creation_date             12-10-02

_audit_creation_method           CRYSTALS_ver_12.84



_chemical_name_systematic        ?

_chemical_melting_point          ?



_cell_length_a                   8.6143(5)

_cell_length_b                   9.1073(7)

_cell_length_c                   11.3382(9)

_cell_angle_alpha                90

_cell_angle_beta                 101.959(4)

_cell_angle_gamma                90

_cell_volume                     870.21(11)



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   'P 1 21/a 1 '

_symmetry_space_group_name_Hall  ?

loop_

_symmetry_equiv_pos_as_xyz




x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,z



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'
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'
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'





_cell_formula_units_Z            4



# Given Formula = C10 H13 N1 O1 

# Dc =      1.25 Fooo =    352.00 Mu =      0.81 M =    163.22

# Found Formula = C10 H13 N1 O1 

# Dc =      1.25 FOOO =    352.00 Mu =      0.81 M =    163.22



_chemical_formula_sum            'C10 H13 N1 O1'

_chemical_formula_moiety         'C10 H13 N1 O1'

_chemical_compound_source        ?

_chemical_formula_weight         163.22





_cell_measurement_reflns_used    0

_cell_measurement_theta_min      0

_cell_measurement_theta_max      0

_cell_measurement_temperature    120



_exptl_crystal_description       plate

_exptl_crystal_colour            black

_exptl_crystal_size_min          0.09

_exptl_crystal_size_mid          0.16

_exptl_crystal_size_max          0.41



_exptl_crystal_density_diffrn    1.246

_exptl_crystal_density_meas      ?

# Non-dispersive F(000): 

_exptl_crystal_F_000             352

_exptl_absorpt_coefficient_mu    0.081



# Sheldrick geometric approximatio 0.99 0.99 

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SORTAV (Blessing)'

_exptl_absorpt_correction_T_min  0.96

_exptl_absorpt_correction_T_max  0.99

# 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_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073

_diffrn_measurement_method       'φ & ω scans'



# If a reference occurs more than once, delete the author 

# and date from subsequent references. 

_computing_data_collection       'COLLECT (Nonius, 1997-2001).'

_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'

_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      120

_diffrn_reflns_number            6606

_reflns_number_total             1987

_diffrn_reflns_av_R_equivalents  0.056

# Number of reflections with Friedels Law is 1987 

# Number of reflections without Friedels Law is 0 

# Theoretical number of reflections is about 2000 





_diffrn_reflns_theta_min         3.519

_diffrn_reflns_theta_max         27.647

_diffrn_measured_fraction_theta_max 0.981



_diffrn_reflns_theta_full        25.989

_diffrn_measured_fraction_theta_full 0.995





_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       0

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       0

_diffrn_reflns_limit_l_max       14

_reflns_limit_h_min              -11

_reflns_limit_h_max              10

_reflns_limit_k_min              0

_reflns_limit_k_max              11

_reflns_limit_l_min              0

_reflns_limit_l_max              14





_atom_sites_solution_primary     direct #heavy,direct,difmap,geom

# _atom_sites_solution_secondary  difmap

_atom_sites_solution_hydrogens   geom



_refine_diff_density_min         -0.42

_refine_diff_density_max         0.49





_refine_ls_number_reflns         1764

_refine_ls_number_restraints     0

_refine_ls_number_parameters     109



#_refine_ls_R_factor_ref 0.0577 

_refine_ls_wR_factor_ref         0.0582

_refine_ls_goodness_of_fit_ref   0.8373



#_reflns_number_all 1987 

_refine_ls_R_factor_all          0.0680

_refine_ls_wR_factor_all         0.4001



# The I/u(I) cutoff below was used for refinement as 

# well as the _gt R-factors:

_reflns_threshold_expression     I>2.5σ(I)

_reflns_number_gt                1764

_refine_ls_R_factor_gt           0.0577

_refine_ls_wR_factor_gt          0.0582



_refine_ls_shift/su_max          0.000305



# 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 F

_refine_ls_matrix_type           full

_refine_ls_hydrogen_treatment    constr # none, 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: 

 1.72 1.93 0.775 

;



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



# Replace last . with number of unfound hydrogen atomsattached 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 0.51045(8) 0.65395(7) 0.37863(7) 0.0289 1.0000 Uani . . . . . .
N1 N 0.50243(8) 0.54121(8) 0.30968(7) 0.0190 1.0000 Uani . . . . . .
C1 C 0.07271(10) 0.50280(8) 0.04619(8) 0.0195 1.0000 Uani . . . . . .
C2 C 0.19972(10) 0.40640(10) 0.04645(7) 0.0216 1.0000 Uani . . . . . .
C3 C 0.34181(10) 0.41406(9) 0.13088(8) 0.0203 1.0000 Uani . . . . . .
C4 C 0.36127(10) 0.52051(9) 0.22266(8) 0.0191 1.0000 Uani . . . . . .
C5 C 0.23335(10) 0.61473(10) 0.22730(8) 0.0211 1.0000 Uani . . . . . .
C6 C 0.09464(10) 0.60664(10) 0.14114(8) 0.0220 1.0000 Uani . . . . . .
C7 C 0.64630(10) 0.44429(9) 0.32473(8) 0.0194 1.0000 Uani . . . . . .
C8 C 0.72243(11) 0.46508(10) 0.21477(9) 0.0249 1.0000 Uani . . . . . .
C9 C 0.60404(11) 0.28422(10) 0.34467(8) 0.0254 1.0000 Uani . . . . . .
C10 C 0.76438(11) 0.49576(10) 0.43607(9) 0.0271 1.0000 Uani . . . . . .
H21 H 0.1887 0.3340 -0.0151 0.0345 1.0000 Uiso R . . . . .
H31 H 0.4274 0.3495 0.1274 0.0320 1.0000 Uiso R . . . . .
H51 H 0.2441 0.6857 0.2899 0.0284 1.0000 Uiso R . . . . .
H61 H 0.0126 0.6746 0.1462 0.0307 1.0000 Uiso R . . . . .
H81 H 0.8130 0.4034 0.2231 0.0319 1.0000 Uiso R . . . . .
H82 H 0.7538 0.5647 0.2113 0.0319 1.0000 Uiso R . . . . .
H83 H 0.6490 0.4405 0.1427 0.0319 1.0000 Uiso R . . . . .
H91 H 0.6970 0.2257 0.3534 0.0376 1.0000 Uiso R . . . . .
H92 H 0.5630 0.2782 0.4161 0.0376 1.0000 Uiso R . . . . .
H93 H 0.5267 0.2496 0.2782 0.0376 1.0000 Uiso R . . . . .
H101 H 0.8565 0.4357 0.4479 0.0345 1.0000 Uiso R . . . . .
H102 H 0.7929 0.5948 0.4251 0.0345 1.0000 Uiso R . . . . .
H103 H 0.7174 0.4891 0.5046 0.0345 1.0000 Uiso R . . . . .

loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12












O1 0.0301(4) 0.0240(4) 0.0312(4) -0.0103(3) 0.0031(3) 0.0030(2)
N1 0.0207(4) 0.0161(4) 0.0198(4) -0.0022(3) 0.0034(3) 0.0023(2)
C1 0.0249(5) 0.0131(4) 0.0212(4) 0.0014(3) 0.0063(4) 0.0009(3)
C2 0.0280(5) 0.0189(4) 0.0181(4) -0.0005(3) 0.0049(3) 0.0016(3)
C3 0.0209(4) 0.0174(4) 0.0227(4) 0.0002(3) 0.0046(3) 0.0028(3)
C4 0.0217(4) 0.0171(4) 0.0184(4) -0.0004(3) 0.0037(3) 0.0012(3)
C5 0.0227(4) 0.0181(4) 0.0231(4) 0.0001(3) 0.0062(3) 0.0002(3)
C6 0.0239(4) 0.0177(4) 0.0248(4) 0.0008(3) 0.0061(4) 0.0048(3)
C7 0.0195(4) 0.0171(4) 0.0217(4) -0.0003(3) 0.0047(3) 0.0018(3)
C8 0.0256(4) 0.0226(5) 0.0288(5) 0.0017(3) 0.0111(4) 0.0015(3)
C9 0.0291(5) 0.0204(5) 0.0258(4) 0.0026(3) 0.0035(4) -0.0009(3)
C10 0.0242(5) 0.0252(5) 0.0288(5) -0.0036(4) -0.0017(4) 0.0030(3)



_refine_ls_extinction_method     
None

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 . N1 . 1.2837(10) yes
N1 . C4 . 1.4108(11) yes
N1 . C7 . 1.5022(10) yes
C1 . C1 2_565 1.4577(17) yes
C1 . C2 . 1.4023(12) yes
C1 . C6 . 1.4159(12) yes
C2 . C3 . 1.3907(12) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.4066(12) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.4062(12) yes
C5 . C6 . 1.3798(12) yes
C5 . H51 . 0.950 no
C6 . H61 . 0.950 no
C7 . C8 . 1.5360(12) yes
C7 . C9 . 1.5307(12) yes
C7 . C10 . 1.5219(13) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C8 . H83 . 0.950 no
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C9 . H93 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no

loop_

_geom_angle_atom_site_label_1

_geom_angle_site_symmetry_1

_geom_angle_atom_site_label_2

_geom_angle_site_symmetry_2

_geom_angle_atom_site_label_3

_geom_angle_site_symmetry_3

_geom_angle

_geom_angle_publ_flag













































O1 . N1 . C4 . 117.55(7) yes
O1 . N1 . C7 . 117.50(7) yes
C4 . N1 . C7 . 124.90(7) yes
C1 2_565 C1 . C2 . 122.24(9) yes
C1 2_565 C1 . C6 . 121.94(9) yes
C2 . C1 . C6 . 115.81(8) yes
C1 . C2 . C3 . 123.03(8) yes
C1 . C2 . H21 . 118.3 no
C3 . C2 . H21 . 118.7 no
C2 . C3 . C4 . 119.79(8) yes
C2 . C3 . H31 . 121.4 no
C4 . C3 . H31 . 118.8 no
N1 . C4 . C3 . 124.25(8) yes
N1 . C4 . C5 . 117.44(8) yes
C3 . C4 . C5 . 118.30(8) yes
C4 . C5 . C6 . 120.75(8) yes
C4 . C5 . H51 . 119.2 no
C6 . C5 . H51 . 120.1 no
C1 . C6 . C5 . 122.24(8) yes
C1 . C6 . H61 . 119.8 no
C5 . C6 . H61 . 117.9 no
N1 . C7 . C8 . 108.44(7) yes
N1 . C7 . C9 . 111.13(7) yes
C8 . C7 . C9 . 113.08(7) yes
N1 . C7 . C10 . 107.88(7) yes
C8 . C7 . C10 . 108.12(7) yes
C9 . C7 . C10 . 108.02(7) yes
C7 . C8 . H81 . 109.0 no
C7 . C8 . H82 . 109.0 no
H81 . C8 . H82 . 109.5 no
C7 . C8 . H83 . 110.4 no
H81 . C8 . H83 . 109.5 no
H82 . C8 . H83 . 109.5 no
C7 . C9 . H91 . 109.2 no
C7 . C9 . H92 . 108.8 no
H91 . C9 . H92 . 109.5 no
C7 . C9 . H93 . 110.4 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
C7 . C10 . H101 . 109.6 no
C7 . C10 . H102 . 109.3 no
H101 . C10 . H102 . 109.5 no
C7 . C10 . H103 . 109.5 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no

_database_code_depnum_ccdc_archive 'CCDC 1001620'
#######################################################################
#
#                 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_ravdipyrad
_audit_creation_date             14-03-21
_audit_creation_method           CRYSTALS_ver_14.40

_chemical_name_systematic        ?
_chemical_melting_point          ?

#_publ_section_title 
# Title of paper - generally just the systematic or trivial name 
#; ? 
#; 

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary. 
#loop_ 
# _publ_author_name 
# _publ_author_address 
# _publ_author_footnote 
# 'Volker Enkelmann' # Author 1 
#; 
# Max-Planck-Institute for Polymer Research 
# Ackermannweg 10 
# D-55021 Mainz 
# Germany 
#; 

#; 
# ve@mpip-mainz.mpg.de 
#; 
# 'Martin Baumgarten' # Author 2 
#; 
# Max-Planck-Institute for Polymer Research 
# Ackermannweg 10 
# D-55021 Mainz 
# Germany 
#; 

#; 
# baumgart@mpip-mainz.mpg.de
#; 

_cell_length_a                   18.1306(8)
_cell_length_b                   11.2298(3)
_cell_length_c                   17.6135(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.4267(18)
_cell_angle_gamma                90
_cell_volume                     3290.6(2)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 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'
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'
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'


_cell_formula_units_Z            4

# Given Formula = C40 H43 N2 O6 
# Dc =      1.31 Fooo =   1376.00 Mu =      0.88 M =    323.90
# Found Formula = C40 H42 N2 O6 
# Dc =      1.31 FOOO =   1376.00 Mu =      0.88 M =    323.39

_chemical_formula_sum            'C40 H42 N2 O6'
_chemical_formula_moiety         'C40 H42 N2 O6'
_chemical_compound_source        ?
_chemical_formula_weight         646.78


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.130
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.390

_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.088

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
# 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       'φ & ω scans'

# 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    'SHELXS 86 (Sheldrick, 1986)'
_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      120
_diffrn_reflns_number            13979
_reflns_number_total             4234
_diffrn_reflns_av_R_equivalents  0.088
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4234 
# Theoretical number of reflections is about 8452 


_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         28.653
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        28.653
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -24
_reflns_limit_h_max              22
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              23


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

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.54


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


# The values actually used during refinement 
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_number_parameters     218
_refine_ls_wR_factor_ref         0.0934
_refine_ls_goodness_of_fit_ref   0.9132
_refine_ls_shift/su_max          0.0003641
_refine_ls_shift/su_mean         0.0000642


# The values computed with all filters except I/sigma 
_refine_ls_R_factor_all          0.1027
_refine_ls_wR_factor_all         0.1024

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3411
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_gt          0.0947

# 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 F
_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: 
 5.75 4.55 4.88 1.62 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.24533(16) 0.9536(2) 0.18086(14) 0.0357 1.0000 Uani . . . . . .
O1 O 0.45989(11) 1.23163(15) 0.66464(12) 0.0278 1.0000 Uani . . . . . .
O2 O 0.45899(12) 0.58238(16) 0.66448(11) 0.0300 1.0000 Uani . . . . . .
O3 O 0.2472(2) 1.0601(2) 0.15709(16) 0.0775 1.0000 Uani . . . . . .
C1 C 0.47893(15) 0.9064(2) 0.70588(15) 0.0237 1.0000 Uani . . . . . .
C2 C 0.45867(16) 1.0162(2) 0.66229(16) 0.0254 1.0000 Uani . . . . . .
C3 C 0.41811(16) 1.0145(2) 0.57631(16) 0.0272 1.0000 Uani . . . . . .
C4 C 0.39920(16) 0.9076(2) 0.53203(15) 0.0268 1.0000 Uani . . . . . .
C5 C 0.41786(16) 0.7993(2) 0.57541(15) 0.0259 1.0000 Uani . . . . . .
C6 C 0.45704(15) 0.7981(2) 0.66196(15) 0.0243 1.0000 Uani . . . . . .
C7 C 0.47871(16) 0.6881(2) 0.70810(16) 0.0256 1.0000 Uani . . . . . .
C8 C 0.48109(16) 1.1261(2) 0.70833(17) 0.0266 1.0000 Uani . . . . . .
C9 C 0.36103(16) 0.9124(2) 0.44060(15) 0.0273 1.0000 Uani . . . . . .
C10 C 0.37977(17) 1.0041(2) 0.39765(17) 0.0293 1.0000 Uani . . . . . .
C11 C 0.34301(17) 1.0134(2) 0.31292(17) 0.0310 1.0000 Uani . . . . . .
C12 C 0.28529(17) 0.9312(2) 0.26713(16) 0.0289 1.0000 Uani . . . . . .
C13 C 0.26849(17) 0.8341(2) 0.30746(17) 0.0297 1.0000 Uani . . . . . .
C14 C 0.30576(16) 0.8267(2) 0.39373(16) 0.0291 1.0000 Uani . . . . . .
C15 C 0.20145(18) 0.8625(3) 0.11527(17) 0.0322 1.0000 Uani . . . . . .
C16 C 0.1894(2) 0.9180(3) 0.03195(19) 0.0411 1.0000 Uani . . . . . .
C17 C 0.11995(18) 0.8364(3) 0.11672(19) 0.0387 1.0000 Uani . . . . . .
C18 C 0.25463(19) 0.7523(3) 0.12860(19) 0.0349 1.0000 Uani . . . . . .
C19 C 0.52474(19) 1.2827(3) 0.6483(2) 0.0351 1.0000 Uani . . . . . .
C20 C 0.39577(18) 0.5181(3) 0.6751(2) 0.0361 1.0000 Uani . . . . . .
H31 H 0.4042 1.0878 0.5468 0.0317 1.0000 Uiso R . . . . .
H51 H 0.4038 0.7267 0.5453 0.0329 1.0000 Uiso R . . . . .
H101 H 0.4199 1.0616 0.4282 0.0302 1.0000 Uiso R . . . . .
H111 H 0.3584 1.0754 0.2847 0.0337 1.0000 Uiso R . . . . .
H131 H 0.2332 0.7727 0.2766 0.0319 1.0000 Uiso R . . . . .
H141 H 0.2932 0.7619 0.4217 0.0358 1.0000 Uiso R . . . . .
H161 H 0.1633 0.8652 -0.0111 0.0684 1.0000 Uiso R . . . . .
H162 H 0.1577 0.9900 0.0240 0.0684 1.0000 Uiso R . . . . .
H163 H 0.2403 0.9411 0.0315 0.0684 1.0000 Uiso R . . . . .
H171 H 0.0920 0.7780 0.0763 0.0585 1.0000 Uiso R . . . . .
H172 H 0.0895 0.9074 0.1061 0.0585 1.0000 Uiso R . . . . .
H173 H 0.1272 0.8067 0.1702 0.0585 1.0000 Uiso R . . . . .
H181 H 0.2285 0.6934 0.0872 0.0567 1.0000 Uiso R . . . . .
H182 H 0.3046 0.7724 0.1253 0.0567 1.0000 Uiso R . . . . .
H183 H 0.2658 0.7181 0.1816 0.0567 1.0000 Uiso R . . . . .
H191 H 0.5065 1.3544 0.6174 0.0604 1.0000 Uiso R . . . . .
H192 H 0.5688 1.2996 0.6983 0.0604 1.0000 Uiso R . . . . .
H193 H 0.5407 1.2281 0.6163 0.0604 1.0000 Uiso R . . . . .
H201 H 0.3861 0.4460 0.6449 0.0585 1.0000 Uiso R . . . . .
H202 H 0.4105 0.5014 0.7322 0.0585 1.0000 Uiso R . . . . .
H203 H 0.3484 0.5656 0.6554 0.0585 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0531(16) 0.0273(11) 0.0225(11) 0.0008(9) 0.0106(10) 0.0027(11)
O1 0.0313(10) 0.0198(8) 0.0320(10) 0.0047(7) 0.0122(8) 0.0042(7)
O2 0.0433(11) 0.0243(9) 0.0254(9) -0.0022(7) 0.0169(8) -0.0036(8)
O3 0.136(3) 0.0318(12) 0.0341(13) 0.0066(10) 0.0011(16) -0.0056(15)
C1 0.0306(12) 0.0198(10) 0.0212(12) 0.0011(9) 0.0107(10) 0.0004(10)
C2 0.0283(13) 0.0217(11) 0.0274(13) 0.0026(9) 0.0121(10) 0.0043(9)
C3 0.0294(13) 0.0217(11) 0.0270(13) 0.0024(9) 0.0075(11) 0.0035(9)
C4 0.0287(13) 0.0272(11) 0.0227(11) -0.0024(10) 0.0082(10) 0.0027(11)
C5 0.0302(13) 0.0240(11) 0.0231(12) -0.0019(9) 0.0101(10) 0.002(1)
C6 0.0254(12) 0.0224(11) 0.0235(12) -0.0016(9) 0.0081(10) 0.0011(9)
C7 0.0355(13) 0.0193(11) 0.0236(12) -0.0009(9) 0.0135(10) 0.0008(10)
C8 0.0282(12) 0.0225(11) 0.0295(13) 0.0018(10) 0.0118(10) 0.0039(9)
C9 0.0313(13) 0.0264(12) 0.0227(12) 0.0000(9) 0.0090(10) 0.0052(10)
C10 0.0289(13) 0.0296(12) 0.0290(13) -0.0019(10) 0.0110(10) -0.0021(10)
C11 0.0357(14) 0.0280(12) 0.0297(13) -0.0002(10) 0.0135(11) 0.0010(11)
C12 0.0341(14) 0.0271(12) 0.0217(12) -0.0016(9) 0.0071(10) 0.0064(10)
C13 0.0345(14) 0.0258(12) 0.0260(12) -0.0018(10) 0.0090(11) 0.0031(11)
C14 0.0310(13) 0.0295(12) 0.0275(13) 0.0026(10) 0.0122(11) 0.0028(11)
C15 0.0344(14) 0.0358(14) 0.0237(13) -0.0045(10) 0.0088(11) 0.0017(11)
C16 0.0460(17) 0.0514(18) 0.0260(13) -0.0003(13) 0.0146(12) 0.0012(15)
C17 0.0357(15) 0.0429(16) 0.0397(16) 0.0038(13) 0.0172(13) 0.0078(13)
C18 0.0337(14) 0.0375(14) 0.0348(15) -0.0080(12) 0.0149(12) -0.0012(12)
C19 0.0384(15) 0.0297(13) 0.0430(16) 0.0105(11) 0.0223(13) 0.0037(11)
C20 0.0356(15) 0.0352(14) 0.0393(16) -0.0122(12) 0.0168(12) -0.0059(12)

_refine_ls_extinction_method     None

loop_
_oxford_twin_element_scale_factors
0.708(4)
0.292(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . O3 . 1.273(3) yes
N1 . C12 . 1.422(3) yes
N1 . C15 . 1.511(4) yes
O1 . C8 . 1.381(3) yes
O1 . C19 . 1.436(3) yes
O2 . C7 . 1.382(3) yes
O2 . C20 . 1.428(3) yes
C1 . C1 5_656 1.433(5) yes
C1 . C2 . 1.421(3) yes
C1 . C6 . 1.411(3) yes
C2 . C3 . 1.396(4) yes
C2 . C8 . 1.444(3) yes
C3 . C4 . 1.398(3) yes
C3 . H31 . 0.953 no
C4 . C5 . 1.404(3) yes
C4 . C9 . 1.480(3) yes
C5 . C6 . 1.403(4) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.444(3) yes
C7 . C7 5_656 1.367(5) yes
C8 . C8 5_656 1.351(5) yes
C9 . C10 . 1.397(4) yes
C9 . C14 . 1.398(4) yes
C10 . C11 . 1.375(4) yes
C10 . H101 . 0.961 no
C11 . C12 . 1.388(4) yes
C11 . H111 . 0.959 no
C12 . C13 . 1.399(4) yes
C13 . C14 . 1.399(4) yes
C13 . H131 . 0.951 no
C14 . H141 . 0.955 no
C15 . C16 . 1.528(4) yes
C15 . C17 . 1.517(4) yes
C15 . C18 . 1.529(4) yes
C16 . H161 . 0.930 no
C16 . H162 . 0.969 no
C16 . H163 . 0.962 no
C17 . H171 . 0.952 no
C17 . H172 . 0.946 no
C17 . H173 . 0.958 no
C18 . H181 . 0.959 no
C18 . H182 . 0.958 no
C18 . H183 . 0.954 no
C19 . H191 . 0.955 no
C19 . H192 . 0.944 no
C19 . H193 . 0.952 no
C20 . H201 . 0.945 no
C20 . H202 . 0.952 no
C20 . H203 . 0.952 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
O3 . N1 . C12 . 116.7(2) yes
O3 . N1 . C15 . 117.4(2) yes
C12 . N1 . C15 . 125.9(2) yes
C8 . O1 . C19 . 112.7(2) yes
C7 . O2 . C20 . 113.9(2) yes
C1 5_656 C1 . C2 . 119.84(14) yes
C1 5_656 C1 . C6 . 120.46(13) yes
C2 . C1 . C6 . 119.7(2) yes
C1 . C2 . C3 . 119.1(2) yes
C1 . C2 . C8 . 118.9(2) yes
C3 . C2 . C8 . 122.0(2) yes
C2 . C3 . C4 . 121.6(2) yes
C2 . C3 . H31 . 119.4 no
C4 . C3 . H31 . 119.0 no
C3 . C4 . C5 . 119.2(2) yes
C3 . C4 . C9 . 118.7(2) yes
C5 . C4 . C9 . 122.1(2) yes
C4 . C5 . C6 . 120.5(2) yes
C4 . C5 . H51 . 119.1 no
C6 . C5 . H51 . 120.4 no
C1 . C6 . C5 . 119.9(2) yes
C1 . C6 . C7 . 118.3(2) yes
C5 . C6 . C7 . 121.8(2) yes
C6 . C7 . O2 . 118.0(2) yes
C6 . C7 . C7 5_656 121.20(13) yes
O2 . C7 . C7 5_656 120.70(13) yes
C2 . C8 . O1 . 117.8(2) yes
C2 . C8 . C8 5_656 121.21(14) yes
O1 . C8 . C8 5_656 120.94(13) yes
C4 . C9 . C10 . 120.5(2) yes
C4 . C9 . C14 . 122.2(2) yes
C10 . C9 . C14 . 117.3(2) yes
C9 . C10 . C11 . 121.8(3) yes
C9 . C10 . H101 . 119.0 no
C11 . C10 . H101 . 119.2 no
C10 . C11 . C12 . 120.5(3) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.3 no
N1 . C12 . C11 . 116.7(2) yes
N1 . C12 . C13 . 124.0(2) yes
C11 . C12 . C13 . 119.3(2) yes
C12 . C13 . C14 . 119.3(2) yes
C12 . C13 . H131 . 120.5 no
C14 . C13 . H131 . 120.2 no
C13 . C14 . C9 . 121.6(2) yes
C13 . C14 . H141 . 119.6 no
C9 . C14 . H141 . 118.8 no
N1 . C15 . C16 . 106.8(2) yes
N1 . C15 . C17 . 109.8(2) yes
C16 . C15 . C17 . 109.1(2) yes
N1 . C15 . C18 . 108.8(2) yes
C16 . C15 . C18 . 108.6(2) yes
C17 . C15 . C18 . 113.6(3) yes
C15 . C16 . H161 . 110.8 no
C15 . C16 . H162 . 109.2 no
H161 . C16 . H162 . 109.5 no
C15 . C16 . H163 . 110.2 no
H161 . C16 . H163 . 110.1 no
H162 . C16 . H163 . 106.9 no
C15 . C17 . H171 . 110.7 no
C15 . C17 . H172 . 109.2 no
H171 . C17 . H172 . 109.7 no
C15 . C17 . H173 . 109.3 no
H171 . C17 . H173 . 108.7 no
H172 . C17 . H173 . 109.2 no
C15 . C18 . H181 . 110.5 no
C15 . C18 . H182 . 110.7 no
H181 . C18 . H182 . 108.1 no
C15 . C18 . H183 . 110.6 no
H181 . C18 . H183 . 108.4 no
H182 . C18 . H183 . 108.5 no
O1 . C19 . H191 . 109.0 no
O1 . C19 . H192 . 110.4 no
H191 . C19 . H192 . 109.6 no
O1 . C19 . H193 . 109.1 no
H191 . C19 . H193 . 108.9 no
H192 . C19 . H193 . 109.8 no
O2 . C20 . H201 . 109.8 no
O2 . C20 . H202 . 109.6 no
H201 . C20 . H202 . 109.7 no
O2 . C20 . H203 . 108.9 no
H201 . C20 . H203 . 109.7 no
H202 . C20 . H203 . 109.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C18 . H183 . C13 . 124.60(9) 0.954 2.554 3.194(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 21/03/14 at 17:18:44
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 21/03/14 at 17:18:44
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1001621'
#######################################################################
#
#                 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_ravterp_120
_audit_creation_date             14-02-12
_audit_creation_method           CRYSTALS_ver_14.40

_chemical_name_systematic        ?
_chemical_melting_point          ?

#_publ_section_title 
# Title of paper - generally just the systematic or trivial name 
#; ? 
#; 

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary. 
#loop_ 
# _publ_author_name 
# _publ_author_address 
# _publ_author_footnote 
# 'Volker Enkelmann' # Author 1 
#; 
# Max-Planck-Institute for Polymer Research 
# Ackermannweg 10 
# D-55021 Mainz 
# Germany 
#; 

#; 
# ve@mpip-mainz.mpg.de 
#; 
# 'Martin Baumgarten' # Author 2 
#; 
# Max-Planck-Institute for Polymer Research 
# Ackermannweg 10 
# D-55021 Mainz 
# Germany 
#; 

#; 
# baumgart@mpip-mainz.mpg.de
#; 

_cell_length_a                   8.8404(2)
_cell_length_b                   8.9886(3)
_cell_length_c                   13.3460(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.802(2)
_cell_angle_gamma                90
_cell_volume                     1056.79(5)

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

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'
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'
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'


_cell_formula_units_Z            2

# Given Formula = C26 H30 N2 O2 
# Dc =      1.26 Fooo =    432.00 Mu =      0.80 M =    201.27
# Found Formula = C26 H30 N2 O2 
# Dc =      1.26 FOOO =    432.00 Mu =      0.80 M =    201.27

_chemical_formula_sum            'C26 H30 N2 O2'
_chemical_formula_moiety         'C26 H30 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         402.54


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_min          0.090
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_max          0.420

_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.080

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
# 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       'φ & ω scans'

# 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    'SHELXS 86 (Sheldrick, 1986)'
_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      120
_diffrn_reflns_number            13179
_reflns_number_total             3090
_diffrn_reflns_av_R_equivalents  0.055
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3090 
# Theoretical number of reflections is about 6187 


_diffrn_reflns_theta_min         3.499
_diffrn_reflns_theta_max         30.038
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        30.038
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              18


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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.31


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


# The values actually used during refinement 
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_number_parameters     136
_refine_ls_wR_factor_ref         0.0574
_refine_ls_goodness_of_fit_ref   1.0718
_refine_ls_shift/su_max          0.0016420
_refine_ls_shift/su_mean         0.0004057


# The values computed with all filters except I/sigma 
_refine_ls_R_factor_all          0.0659
_refine_ls_wR_factor_all         0.0643

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2464
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_gt          0.0579

# 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 F
_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: 
 1.40 0.609 0.891 
;

# 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 1.06551(11) 0.66135(12) 0.59817(7) 0.0274 1.0000 Uani . . . . . .
N1 N 1.08158(11) 0.55079(12) 0.65985(7) 0.0188 1.0000 Uani . . . . . .
C5 C 0.72396(13) 0.61083(14) 0.77868(9) 0.0186 1.0000 Uani . . . . . .
C2 C 0.51601(14) 0.62856(13) 0.94414(8) 0.0189 1.0000 Uani . . . . . .
C9 C 0.87671(14) 0.44248(15) 0.88271(9) 0.0225 1.0000 Uani . . . . . .
C3 C 0.61929(13) 0.51187(13) 0.93490(8) 0.0175 1.0000 Uani . . . . . .
C1 C 0.60067(14) 0.38323(13) 0.99251(9) 0.0190 1.0000 Uani . . . . . .
C6 C 0.83616(13) 0.61845(14) 0.71240(9) 0.0191 1.0000 Uani . . . . . .
C7 C 0.97123(13) 0.53696(13) 0.73001(8) 0.0178 1.0000 Uani . . . . . .
C4 C 0.74089(13) 0.52228(13) 0.86567(8) 0.0177 1.0000 Uani . . . . . .
C8 C 0.99015(14) 0.44802(15) 0.81686(9) 0.0234 1.0000 Uani . . . . . .
C11 C 1.33087(14) 0.46577(15) 0.73997(10) 0.0238 1.0000 Uani . . . . . .
C12 C 1.15436(16) 0.28600(15) 0.64059(11) 0.0287 1.0000 Uani . . . . . .
C10 C 1.21280(13) 0.44603(14) 0.65006(9) 0.0196 1.0000 Uani . . . . . .
C13 C 1.28492(17) 0.48789(17) 0.55391(10) 0.0283 1.0000 Uani . . . . . .
H51 H 0.6332 0.6665 0.7651 0.0249 1.0000 Uiso R . . . . .
H21 H 0.5259 0.7170 0.9062 0.0255 1.0000 Uiso R . . . . .
H91 H 0.8913 0.3825 0.9413 0.0301 1.0000 Uiso R . . . . .
H11 H 0.6693 0.3026 0.9880 0.0258 1.0000 Uiso R . . . . .
H61 H 0.8217 0.6796 0.6543 0.0254 1.0000 Uiso R . . . . .
H81 H 1.0805 0.3917 0.8303 0.0304 1.0000 Uiso R . . . . .
H111 H 1.4136 0.4000 0.7335 0.0317 1.0000 Uiso R . . . . .
H112 H 1.3665 0.5655 0.7420 0.0317 1.0000 Uiso R . . . . .
H113 H 1.2853 0.4440 0.8003 0.0317 1.0000 Uiso R . . . . .
H121 H 1.2372 0.2204 0.6342 0.0393 1.0000 Uiso R . . . . .
H122 H 1.1055 0.2608 0.6990 0.0393 1.0000 Uiso R . . . . .
H123 H 1.0841 0.2774 0.5830 0.0393 1.0000 Uiso R . . . . .
H131 H 1.3683 0.4237 0.5456 0.0375 1.0000 Uiso R . . . . .
H132 H 1.3195 0.5879 0.5586 0.0375 1.0000 Uiso R . . . . .
H133 H 1.2120 0.4780 0.4979 0.0375 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0282(5) 0.0278(5) 0.0264(5) 0.0088(4) 0.0031(4) 0.0018(4)
N1 0.0193(4) 0.0202(5) 0.0167(4) 0.0014(4) 0.0012(3) 0.0000(4)
C5 0.0194(5) 0.0188(5) 0.0174(5) 0.0007(4) 0.0005(4) 0.0013(4)
C2 0.0230(5) 0.0174(5) 0.0162(5) 0.0004(4) 0.0007(4) -0.0003(4)
C9 0.0226(5) 0.0266(6) 0.0183(5) 0.0066(4) 0.0020(4) 0.0038(5)
C3 0.0191(5) 0.0185(5) 0.0146(4) -0.0005(4) 0.0000(4) -0.0013(4)
C1 0.0214(5) 0.0176(5) 0.0178(5) -0.0008(4) 0.0013(4) 0.0012(4)
C6 0.0216(5) 0.0184(5) 0.0171(5) 0.0013(4) 0.0003(4) 0.0000(4)
C7 0.0185(5) 0.0182(5) 0.0167(5) -0.0004(4) 0.0012(4) -0.0006(4)
C4 0.0195(5) 0.0180(5) 0.0154(4) -0.0003(4) 0.0008(4) -0.0002(4)
C8 0.0209(5) 0.0279(6) 0.0215(5) 0.0065(5) 0.0026(4) 0.0046(5)
C11 0.0197(5) 0.0258(6) 0.0251(5) -0.0023(5) -0.0023(4) 0.0010(4)
C12 0.0306(6) 0.0215(6) 0.0339(7) -0.0052(5) 0.0026(5) -0.0026(5)
C10 0.0199(5) 0.0196(5) 0.0192(5) -0.0028(4) 0.0012(4) 0.0004(4)
C13 0.0316(6) 0.0306(7) 0.0238(6) -0.0008(5) 0.0080(5) 0.0023(5)

_refine_ls_extinction_method     None
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 . N1 . 1.2907(14) yes
N1 . C7 . 1.4131(14) yes
N1 . C10 . 1.5083(15) yes
C5 . C6 . 1.3849(16) yes
C5 . C4 . 1.4052(16) yes
C5 . H51 . 0.950 no
C2 . C1 2_667 1.3914(16) yes
C2 . C3 . 1.4028(16) yes
C2 . H21 . 0.950 no
C9 . C4 . 1.4008(16) yes
C9 . C8 . 1.3886(17) yes
C9 . H91 . 0.950 no
C3 . C1 . 1.4059(16) yes
C3 . C4 . 1.4779(16) yes
C1 . H11 . 0.950 no
C6 . C7 . 1.4038(16) yes
C6 . H61 . 0.950 no
C7 . C8 . 1.4065(16) yes
C8 . H81 . 0.950 no
C11 . C10 . 1.5333(16) yes
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . C10 . 1.5300(18) yes
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C10 . C13 . 1.5270(17) yes
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . N1 . C7 . 116.43(10) yes
O1 . N1 . C10 . 118.03(9) yes
C7 . N1 . C10 . 125.53(10) yes
C6 . C5 . C4 . 121.55(11) yes
C6 . C5 . H51 . 119.4 no
C4 . C5 . H51 . 119.1 no
C1 2_667 C2 . C3 . 121.17(11) yes
C1 2_667 C2 . H21 . 119.5 no
C3 . C2 . H21 . 119.3 no
C4 . C9 . C8 . 122.24(11) yes
C4 . C9 . H91 . 118.7 no
C8 . C9 . H91 . 119.1 no
C2 . C3 . C1 . 117.39(10) yes
C2 . C3 . C4 . 121.36(11) yes
C1 . C3 . C4 . 121.24(11) yes
C3 . C1 . C2 2_667 121.44(11) yes
C3 . C1 . H11 . 119.2 no
C2 2_667 C1 . H11 . 119.3 no
C5 . C6 . C7 . 120.79(11) yes
C5 . C6 . H61 . 119.7 no
C7 . C6 . H61 . 119.6 no
N1 . C7 . C6 . 117.90(10) yes
N1 . C7 . C8 . 123.71(10) yes
C6 . C7 . C8 . 118.38(10) yes
C3 . C4 . C5 . 121.31(10) yes
C3 . C4 . C9 . 121.63(10) yes
C5 . C4 . C9 . 117.05(10) yes
C7 . C8 . C9 . 119.97(11) yes
C7 . C8 . H81 . 119.9 no
C9 . C8 . H81 . 120.1 no
C10 . C11 . H111 . 109.6 no
C10 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 109.5 no
C10 . C11 . H113 . 109.2 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C10 . C12 . H121 . 109.5 no
C10 . C12 . H122 . 109.3 no
H121 . C12 . H122 . 109.5 no
C10 . C12 . H123 . 109.7 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
C11 . C10 . C12 . 112.12(11) yes
C11 . C10 . N1 . 109.76(10) yes
C12 . C10 . N1 . 109.72(10) yes
C11 . C10 . C13 . 108.93(10) yes
C12 . C10 . C13 . 108.91(11) yes
N1 . C10 . C13 . 107.29(10) yes
C10 . C13 . H131 . 109.4 no
C10 . C13 . H132 . 109.4 no
H131 . C13 . H132 . 109.5 no
C10 . C13 . H133 . 109.6 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H122 . C8 . 125.25(4) 0.950 2.571 3.2148(18) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 12/02/14 at 18:21:12
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 12/02/14 at 18:21:12
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1001622'
