data_global


data_publication_text

#############################################################



_audit_creation_date             15-08-12
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 024RWD12
_chemical_name_systematic        .
_chemical_melting_point          'see supporting information'

_cell_length_a                   8.61820(10)
_cell_length_b                   12.42540(10)
_cell_length_c                   20.8694(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2234.79(4)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C26 H19 Br1 N2 O2
# Dc = 1.40 Fooo = 1024.00 Mu = 18.64 M = 471.35
# Found Formula = C26 H19 Br1 N2 O2 S1
# Dc = 1.50 FOOO = 1024.00 Mu = 19.59 M = 503.42

_chemical_formula_sum            'C26 H19 Br1 N2 O2 S1'
_chemical_formula_moiety         'C26 H19 Br1 N2 O2 S1'
_chemical_compound_source        synthesis
_chemical_formula_weight         503.42


_cell_measurement_reflns_used    2909
_cell_measurement_theta_min      1
_cell_measurement_theta_max      1
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_max          1.000

_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.959

# Sheldrick geometric approximatio 0.38 0.38
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_T_max  0.38
# 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       \w

# 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    'SIR92 (Altomare et al., 1994)'
_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         'not measured'
_diffrn_standards_decay_%        'not measured'

_diffrn_ambient_temperature      150
_diffrn_reflns_number            5078
_reflns_number_total             5078
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 5078
# Number of reflections with Friedels Law is 2888
# Theoretical number of reflections is about 2568


_diffrn_reflns_theta_min         5.103
_diffrn_reflns_theta_max         27.504
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        26.954
_diffrn_measured_fraction_theta_full 0.990


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   3.50
_oxford_diffrn_Wilson_scale      9.30

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

_refine_diff_density_min         -0.79
_refine_diff_density_max         0.46


# 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         5078
_refine_ls_number_restraints     0
_refine_ls_number_parameters     290
_oxford_refine_ls_R_factor_ref   0.0522
_refine_ls_wR_factor_ref         0.0804
_refine_ls_goodness_of_fit_ref   0.9781
_refine_ls_shift/su_max          0.0003645
_refine_ls_shift/su_mean         0.0000199


# The values computed from all data
_oxford_reflns_number_all        5078
_refine_ls_R_factor_all          0.0522
_refine_ls_wR_factor_all         0.0804

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                4362
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_gt          0.0752

_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_abs_structure_details 'Flack (1983), 2190 Friedel-pairs'
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
41.8 70.1 44.8 20.1 5.07
;

# 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

#Flack Parameter & su 0.0181 0.0071
#Hooft Parameter & su 0.0134 0.0038
# Ton G & su 0.9733 0.0075


#For an enantiopure material, there are 2 choices, P2
#P2(correct) 1.0000 i.e. 0.100000E+01

#If 50:50 twinning is possible, there are 3 choices, P3
#P3(correct) 1.0000 i.e. 0.100000E+01
#P3(rac-twin) 0.0000 i.e. 0.000000E+00
#P3(inverse) 0.0000 i.e. 0.000000E+00
#G 0.9733
#G S.U. 0.0075
#FLEQ 0.0134
#FLEQ S.U. 0.0038 i.e. 0.376650E-02


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
Br1 Br 0.19239(4) 0.65088(4) 0.116128(15) 0.0635 1.0000 Uani . . . . . .
C2 C 0.3013(3) 0.6156(2) 0.19193(13) 0.0395 1.0000 Uani . . . . . .
C3 C 0.3952(3) 0.5255(3) 0.19324(13) 0.0400 1.0000 Uani . . . . . .
C4 C 0.4781(3) 0.5022(2) 0.24803(13) 0.0355 1.0000 Uani . . . . . .
C5 C 0.4652(3) 0.5686(2) 0.30123(12) 0.0326 1.0000 Uani . . . . . .
S6 S 0.57548(7) 0.54161(6) 0.37093(3) 0.0380 1.0000 Uani . . . . . .
O7 O 0.7029(2) 0.47426(19) 0.35285(10) 0.0508 1.0000 Uani . . . . . .
O8 O 0.6019(2) 0.64207(18) 0.40219(9) 0.0463 1.0000 Uani . . . . . .
N9 N 0.4700(2) 0.4694(2) 0.42009(10) 0.0342 1.0000 Uani . . . . . .
C10 C 0.4448(3) 0.3540(2) 0.40791(12) 0.0355 1.0000 Uani . . . . . .
C11 C 0.2643(3) 0.3401(2) 0.40512(11) 0.0282 1.0000 Uani . . . . . .
C12 C 0.2031(3) 0.33311(19) 0.33618(10) 0.0266 1.0000 Uani . . . . . .
C13 C 0.0979(3) 0.4043(2) 0.31197(11) 0.0267 1.0000 Uani . . . . . .
C14 C 0.0446(3) 0.3947(2) 0.24790(12) 0.0281 1.0000 Uani . . . . . .
C15 C -0.0654(3) 0.4675(3) 0.22175(13) 0.0410 1.0000 Uani . . . . . .
C16 C -0.1150(4) 0.4543(4) 0.15975(14) 0.0558 1.0000 Uani . . . . . .
C17 C -0.0584(3) 0.3715(3) 0.12166(13) 0.0530 1.0000 Uani . . . . . .
C18 C 0.0472(4) 0.3008(3) 0.14543(13) 0.0463 1.0000 Uani . . . . . .
C19 C 0.1006(3) 0.3104(2) 0.20894(12) 0.0311 1.0000 Uani . . . . . .
C20 C 0.2103(4) 0.2388(2) 0.23564(13) 0.0414 1.0000 Uani . . . . . .
C21 C 0.2612(3) 0.2490(2) 0.29689(13) 0.0373 1.0000 Uani . . . . . .
C22 C 0.2104(3) 0.4387(2) 0.44205(10) 0.0286 1.0000 Uani . . . . . .
C23 C 0.3292(3) 0.5124(2) 0.44771(11) 0.0298 1.0000 Uani . . . . . .
C24 C 0.3089(3) 0.6084(2) 0.47896(12) 0.0367 1.0000 Uani . . . . . .
C25 C 0.1639(3) 0.6301(2) 0.50412(12) 0.0384 1.0000 Uani . . . . . .
C26 C 0.0412(3) 0.5589(2) 0.49871(11) 0.0328 1.0000 Uani . . . . . .
C27 C 0.0649(3) 0.4609(2) 0.46741(11) 0.0302 1.0000 Uani . . . . . .
C28 C -0.1159(3) 0.5856(3) 0.52620(15) 0.0426 1.0000 Uani . . . . . .
C29 C 0.2210(3) 0.2396(2) 0.43966(12) 0.0335 1.0000 Uani . . . . . .
N30 N 0.1864(3) 0.1628(2) 0.46534(11) 0.0482 1.0000 Uani . . . . . .
C31 C 0.3680(3) 0.6568(3) 0.29989(13) 0.0393 1.0000 Uani . . . . . .
C32 C 0.2849(3) 0.6811(2) 0.24482(14) 0.0429 1.0000 Uani . . . . . .
H31 H 0.4015 0.4810 0.1573 0.0413 1.0000 Uiso R . . . . .
H41 H 0.5439 0.4421 0.2496 0.0406 1.0000 Uiso R . . . . .
H101 H 0.4888 0.3085 0.4419 0.0420 1.0000 Uiso R . . . . .
H102 H 0.4906 0.3325 0.3672 0.0419 1.0000 Uiso R . . . . .
H131 H 0.0603 0.4605 0.3375 0.0318 1.0000 Uiso R . . . . .
H151 H -0.1051 0.5226 0.2476 0.0516 1.0000 Uiso R . . . . .
H161 H -0.1879 0.5032 0.1428 0.0630 1.0000 Uiso R . . . . .
H171 H -0.0921 0.3632 0.0796 0.0669 1.0000 Uiso R . . . . .
H181 H 0.0850 0.2445 0.1193 0.0509 1.0000 Uiso R . . . . .
H201 H 0.2498 0.1832 0.2105 0.0485 1.0000 Uiso R . . . . .
H211 H 0.3345 0.2004 0.3138 0.0444 1.0000 Uiso R . . . . .
H241 H 0.3920 0.6565 0.4831 0.0440 1.0000 Uiso R . . . . .
H251 H 0.1467 0.6962 0.5260 0.0432 1.0000 Uiso R . . . . .
H271 H -0.0155 0.4103 0.4638 0.0376 1.0000 Uiso R . . . . .
H283 H -0.1726 0.5211 0.5347 0.0614 1.0000 Uiso R . . . . .
H281 H -0.1046 0.6245 0.5653 0.0611 1.0000 Uiso R . . . . .
H282 H -0.1745 0.6281 0.4965 0.0611 1.0000 Uiso R . . . . .
H311 H 0.3618 0.7005 0.3367 0.0437 1.0000 Uiso R . . . . .
H321 H 0.2172 0.7399 0.2441 0.0492 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
Br1 0.05539(19) 0.0936(3) 0.04144(15) 0.01414(18) -0.01344(14) -0.00183(18)
C2 0.0336(13) 0.0519(17) 0.0330(12) 0.0057(11) -0.0016(12) -0.0090(13)
C3 0.0429(15) 0.0453(17) 0.0319(12) -0.0036(12) 0.0031(11) -0.0071(13)
C4 0.0356(13) 0.0337(14) 0.0370(13) 0.0007(11) 0.0039(11) 0.0026(11)
C5 0.0254(12) 0.0406(15) 0.0318(12) 0.0046(11) 0.0026(9) -0.0031(11)
S6 0.0241(3) 0.0581(4) 0.0319(3) 0.0068(3) 0.0016(2) -0.0058(3)
O7 0.0234(9) 0.0811(15) 0.0478(11) 0.0179(11) 0.0078(8) 0.0060(10)
O8 0.0429(10) 0.0604(13) 0.0358(9) -0.0006(10) -0.0006(8) -0.0234(10)
N9 0.0256(10) 0.0452(13) 0.0318(11) 0.0039(10) 0.0016(8) 0.0001(9)
C10 0.0272(12) 0.0431(15) 0.0362(12) 0.0070(12) -0.0011(9) 0.0060(12)
C11 0.0275(11) 0.0318(13) 0.0253(9) 0.0030(10) 0.0025(8) 0.0039(10)
C12 0.0268(11) 0.0291(13) 0.0240(9) 0.0002(9) 0.0041(9) 0.0021(11)
C13 0.0242(12) 0.0284(12) 0.0275(11) -0.0005(10) 0.0020(9) 0.0017(10)
C14 0.0211(11) 0.0344(13) 0.0288(11) 0.0000(10) 0.0004(9) -0.0011(10)
C15 0.0383(14) 0.0518(18) 0.0329(13) 0.0020(12) -0.0028(11) 0.0162(14)
C16 0.0409(16) 0.091(3) 0.0353(14) 0.0048(17) -0.0051(12) 0.0241(17)
C17 0.0370(14) 0.094(2) 0.0277(12) -0.0035(15) -0.0052(11) 0.0072(15)
C18 0.0425(15) 0.066(2) 0.0299(13) -0.0143(13) 0.0019(11) 0.0015(15)
C19 0.0295(12) 0.0339(14) 0.0298(12) -0.0045(10) 0.0038(9) -0.0019(10)
C20 0.0500(17) 0.0403(16) 0.0339(13) -0.0063(11) 0.0083(12) 0.0147(14)
C21 0.0443(15) 0.0347(15) 0.0330(13) 0.0016(11) 0.0048(11) 0.0189(12)
C22 0.0305(12) 0.0354(14) 0.0197(10) 0.0004(9) -0.0011(9) 0.0019(11)
C23 0.0257(12) 0.0392(15) 0.0246(10) 0.0006(10) 0.0021(9) -0.0003(10)
C24 0.0348(13) 0.0438(15) 0.0314(11) -0.0004(10) 0.0017(11) -0.0076(13)
C25 0.0408(15) 0.0409(16) 0.0334(12) -0.0063(11) 0.0045(10) -0.0028(12)
C26 0.0327(13) 0.0376(14) 0.0280(12) -0.0027(11) 0.0058(9) -0.0014(11)
C27 0.0299(12) 0.0336(13) 0.0271(11) -0.0023(11) 0.0042(9) -0.0031(11)
C28 0.0392(16) 0.0451(17) 0.0433(15) -0.0074(13) 0.0123(12) 0.0014(12)
C29 0.0332(13) 0.0400(16) 0.0272(12) 0.0056(11) 0.0062(10) 0.0042(12)
N30 0.0558(14) 0.0480(15) 0.0408(11) 0.0098(12) 0.0097(11) 0.0036(14)
C31 0.0361(13) 0.0464(17) 0.0354(13) -0.0047(13) 0.0036(10) 0.0022(12)
C32 0.0371(15) 0.0447(17) 0.0468(15) 0.0023(12) 0.0021(12) 0.0056(12)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3364(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.891(3) yes
C2 . C3 . 1.382(4) yes
C2 . C32 . 1.379(4) yes
C3 . C4 . 1.379(4) yes
C3 . H31 . 0.934 no
C4 . C5 . 1.387(4) yes
C4 . H41 . 0.939 no
C5 . S6 . 1.770(3) yes
C5 . C31 . 1.380(4) yes
S6 . O7 . 1.431(2) yes
S6 . O8 . 1.427(2) yes
S6 . N9 . 1.639(2) yes
N9 . C10 . 1.472(4) yes
N9 . C23 . 1.446(3) yes
C10 . C11 . 1.567(3) yes
C10 . H101 . 0.983 no
C10 . H102 . 0.974 no
C11 . C12 . 1.535(3) yes
C11 . C22 . 1.520(4) yes
C11 . C29 . 1.490(4) yes
C12 . C13 . 1.364(3) yes
C12 . C21 . 1.419(4) yes
C13 . C14 . 1.419(3) yes
C13 . H131 . 0.936 no
C14 . C15 . 1.420(4) yes
C14 . C19 . 1.411(4) yes
C15 . C16 . 1.372(4) yes
C15 . H151 . 0.936 no
C16 . C17 . 1.389(5) yes
C16 . H161 . 0.943 no
C17 . C18 . 1.358(4) yes
C17 . H171 . 0.930 no
C18 . C19 . 1.408(4) yes
C18 . H181 . 0.946 no
C19 . C20 . 1.412(4) yes
C20 . C21 . 1.358(4) yes
C20 . H201 . 0.932 no
C21 . H211 . 0.943 no
C22 . C23 . 1.379(3) yes
C22 . C27 . 1.389(3) yes
C23 . C24 . 1.370(4) yes
C24 . C25 . 1.382(4) yes
C24 . H241 . 0.936 no
C25 . C26 . 1.383(4) yes
C25 . H251 . 0.952 no
C26 . C27 . 1.397(4) yes
C26 . C28 . 1.507(4) yes
C27 . H271 . 0.939 no
C28 . H283 . 0.955 no
C28 . H281 . 0.954 no
C28 . H282 . 0.958 no
C29 . N30 . 1.134(4) yes
C31 . C32 . 1.388(4) yes
C31 . H311 . 0.941 no
C32 . H321 . 0.935 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
Br1 . C2 . C3 . 119.7(2) yes
Br1 . C2 . C32 . 118.8(2) yes
C3 . C2 . C32 . 121.5(3) yes
C2 . C3 . C4 . 119.3(3) yes
C2 . C3 . H31 . 119.9 no
C4 . C3 . H31 . 120.8 no
C3 . C4 . C5 . 119.8(3) yes
C3 . C4 . H41 . 120.6 no
C5 . C4 . H41 . 119.5 no
C4 . C5 . S6 . 120.1(2) yes
C4 . C5 . C31 . 120.3(2) yes
S6 . C5 . C31 . 119.5(2) yes
C5 . S6 . O7 . 107.83(12) yes
C5 . S6 . O8 . 107.20(13) yes
O7 . S6 . O8 . 120.64(13) yes
C5 . S6 . N9 . 108.68(11) yes
O7 . S6 . N9 . 105.69(13) yes
O8 . S6 . N9 . 106.35(12) yes
S6 . N9 . C10 . 120.47(17) yes
S6 . N9 . C23 . 120.83(19) yes
C10 . N9 . C23 . 107.81(19) yes
N9 . C10 . C11 . 105.1(2) yes
N9 . C10 . H101 . 112.3 no
C11 . C10 . H101 . 110.3 no
N9 . C10 . H102 . 111.0 no
C11 . C10 . H102 . 109.8 no
H101 . C10 . H102 . 108.4 no
C10 . C11 . C12 . 112.47(19) yes
C10 . C11 . C22 . 101.3(2) yes
C12 . C11 . C22 . 114.6(2) yes
C10 . C11 . C29 . 108.9(2) yes
C12 . C11 . C29 . 108.7(2) yes
C22 . C11 . C29 . 110.74(19) yes
C11 . C12 . C13 . 122.6(2) yes
C11 . C12 . C21 . 117.5(2) yes
C13 . C12 . C21 . 119.9(2) yes
C12 . C13 . C14 . 120.7(2) yes
C12 . C13 . H131 . 120.2 no
C14 . C13 . H131 . 119.1 no
C13 . C14 . C15 . 121.7(2) yes
C13 . C14 . C19 . 119.7(2) yes
C15 . C14 . C19 . 118.7(2) yes
C14 . C15 . C16 . 119.6(3) yes
C14 . C15 . H151 . 119.2 no
C16 . C15 . H151 . 121.1 no
C15 . C16 . C17 . 121.3(3) yes
C15 . C16 . H161 . 119.0 no
C17 . C16 . H161 . 119.7 no
C16 . C17 . C18 . 120.3(3) yes
C16 . C17 . H171 . 120.8 no
C18 . C17 . H171 . 118.8 no
C17 . C18 . C19 . 120.5(3) yes
C17 . C18 . H181 . 119.9 no
C19 . C18 . H181 . 119.6 no
C14 . C19 . C18 . 119.6(3) yes
C14 . C19 . C20 . 118.0(2) yes
C18 . C19 . C20 . 122.5(3) yes
C19 . C20 . C21 . 122.0(2) yes
C19 . C20 . H201 . 119.3 no
C21 . C20 . H201 . 118.8 no
C12 . C21 . C20 . 119.9(2) yes
C12 . C21 . H211 . 119.4 no
C20 . C21 . H211 . 120.7 no
C11 . C22 . C23 . 110.6(2) yes
C11 . C22 . C27 . 129.0(2) yes
C23 . C22 . C27 . 120.4(2) yes
N9 . C23 . C22 . 110.0(2) yes
N9 . C23 . C24 . 128.2(2) yes
C22 . C23 . C24 . 121.6(2) yes
C23 . C24 . C25 . 117.8(3) yes
C23 . C24 . H241 . 120.1 no
C25 . C24 . H241 . 122.1 no
C24 . C25 . C26 . 122.4(3) yes
C24 . C25 . H251 . 119.5 no
C26 . C25 . H251 . 118.1 no
C25 . C26 . C27 . 118.9(2) yes
C25 . C26 . C28 . 121.0(2) yes
C27 . C26 . C28 . 120.1(2) yes
C26 . C27 . C22 . 118.9(2) yes
C26 . C27 . H271 . 120.9 no
C22 . C27 . H271 . 120.2 no
C26 . C28 . H283 . 110.2 no
C26 . C28 . H281 . 110.2 no
H283 . C28 . H281 . 108.5 no
C26 . C28 . H282 . 110.4 no
H283 . C28 . H282 . 108.2 no
H281 . C28 . H282 . 109.2 no
C11 . C29 . N30 . 179.0(3) yes
C5 . C31 . C32 . 120.2(3) yes
C5 . C31 . H311 . 118.4 no
C32 . C31 . H311 . 121.4 no
C31 . C32 . C2 . 118.8(3) yes
C31 . C32 . H321 . 120.4 no
C2 . C32 . H321 . 120.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C25 . H251 . O8 2_466 172.42(8) 0.952 2.536 3.482(4) yes
C28 . H283 . N30 2_456 168.72(8) 0.955 2.588 3.530(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/08/12 at 17:07:20
#
#LIST 12
BLOCK SCALE X'S, U'S
CONT ENANTIO
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) H ( 102,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 20,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
RIDE C ( 24,X'S) H ( 241,X'S)
RIDE C ( 25,X'S) H ( 251,X'S)
RIDE C ( 27,X'S) H ( 271,X'S)
RIDE C ( 28,X'S) H ( 283,X'S) H ( 281,X'S) H ( 282,X'S)
RIDE C ( 31,X'S) H ( 311,X'S)
RIDE C ( 32,X'S) H ( 321,X'S)
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/08/12 at 17:07:20
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;



data_publication_text

data_036RWD12
#TrackingRef '13682_web_deposit_cif_file_0_RussellW.Driver_1346671791.036RWD12-Final.cif'


_audit_creation_date             12-06-28
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 036RWD12
_chemical_name_systematic        .
_chemical_melting_point          'see supporting information'


_cell_length_a                   12.6892(3)
_cell_length_b                   9.9361(3)
_cell_length_c                   16.3936(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.5148(17)
_cell_angle_gamma                90
_cell_volume                     2017.81(9)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_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 0.0033 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'


_cell_formula_units_Z            4

# Given Formula = C27 H18 N3
# Dc = 1.27 Fooo = 808.00 Mu = 0.75 M = 384.46
# Found Formula = C27 H19 N3
# Dc = 1.27 FOOO = 808.00 Mu = 0.76 M = 385.47

_chemical_formula_sum            'C27 H19 N3'
_chemical_formula_moiety         'C27 H19 N3'
_chemical_compound_source        syn
_chemical_formula_weight         385.47


_cell_measurement_reflns_used    4823
_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          0.220
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.076

# Sheldrick geometric approximatio 0.98 0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98
# 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       \w

# 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    'SIR92 (Altomare et al., 1994)'
_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_%        'not measured'

_diffrn_ambient_temperature      150
_diffrn_reflns_number            31133
_reflns_number_total             4579
_diffrn_reflns_av_R_equivalents  0.038
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 4579
# Theoretical number of reflections is about 9246


_diffrn_reflns_theta_min         5.243
_diffrn_reflns_theta_max         27.473
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        26.924
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   3.15
_oxford_diffrn_Wilson_scale      3.30

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

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.28


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


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     0
_refine_ls_number_parameters     271
_oxford_refine_ls_R_factor_ref   0.0687
_refine_ls_wR_factor_ref         0.1380
_refine_ls_goodness_of_fit_ref   0.9481
_refine_ls_shift/su_max          0.0002937
_refine_ls_shift/su_mean         0.0000400


# The values computed from all data
_oxford_reflns_number_all        4579
_refine_ls_R_factor_all          0.0687
_refine_ls_wR_factor_all         0.1380

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                3521
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_gt          0.1216

# 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 'not applicable, racemic'


_refine_ls_structure_factor_coef Fsqd
_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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
26.0 40.1 19.9 5.14
;

# 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 0.60457(10) 0.67869(15) 0.38434(8) 0.0388 1.0000 Uani . . . . . .
C2 C 0.70210(13) 0.64054(16) 0.36558(10) 0.0368 1.0000 Uani . . . . . .
C3 C 0.78211(12) 0.62906(15) 0.43814(9) 0.0345 1.0000 Uani . . . . . .
C4 C 0.88725(13) 0.59624(16) 0.43616(10) 0.0385 1.0000 Uani . . . . . .
C5 C 0.91174(14) 0.57059(18) 0.35862(11) 0.0441 1.0000 Uani . . . . . .
C6 C 0.83195(15) 0.58105(18) 0.28599(11) 0.0451 1.0000 Uani . . . . . .
C7 C 0.72652(15) 0.61709(17) 0.28769(10) 0.0425 1.0000 Uani . . . . . .
C8 C 0.73270(12) 0.65741(15) 0.51365(9) 0.0323 1.0000 Uani . . . . . .
C9 C 0.60834(12) 0.64153(16) 0.47196(9) 0.0336 1.0000 Uani . . . . . .
C10 C 0.53008(11) 0.72249(16) 0.50817(10) 0.0351 1.0000 Uani . . . . . .
C11 C 0.50035(11) 0.70388(16) 0.58757(9) 0.0350 1.0000 Uani . . . . . .
C12 C 0.53273(12) 0.61658(17) 0.65557(10) 0.0382 1.0000 Uani . . . . . .
C13 C 0.48310(13) 0.62545(18) 0.72276(11) 0.0430 1.0000 Uani . . . . . .
C14 C 0.40126(14) 0.7204(2) 0.72385(11) 0.0464 1.0000 Uani . . . . . .
C15 C 0.36842(13) 0.80934(19) 0.65863(11) 0.0441 1.0000 Uani . . . . . .
C16 C 0.41849(12) 0.79979(17) 0.59063(10) 0.0380 1.0000 Uani . . . . . .
N17 N 0.40077(11) 0.87244(14) 0.51745(9) 0.0423 1.0000 Uani . . . . . .
C18 C 0.46805(12) 0.82549(17) 0.46868(10) 0.0391 1.0000 Uani . . . . . .
C19 C 0.75318(12) 0.79997(16) 0.53846(9) 0.0355 1.0000 Uani . . . . . .
N20 N 0.76642(12) 0.91187(15) 0.55518(10) 0.0456 1.0000 Uani . . . . . .
C21 C 0.77274(11) 0.56161(15) 0.58627(9) 0.0322 1.0000 Uani . . . . . .
C22 C 0.81739(12) 0.60528(16) 0.66537(9) 0.0361 1.0000 Uani . . . . . .
C23 C 0.85527(13) 0.51291(17) 0.73150(10) 0.0388 1.0000 Uani . . . . . .
C24 C 0.84714(12) 0.37307(17) 0.71511(10) 0.0392 1.0000 Uani . . . . . .
C25 C 0.80034(13) 0.33006(17) 0.63276(11) 0.0421 1.0000 Uani . . . . . .
C26 C 0.76461(12) 0.42070(17) 0.57020(10) 0.0385 1.0000 Uani . . . . . .
C27 C 0.88855(15) 0.2817(2) 0.78069(12) 0.0501 1.0000 Uani . . . . . .
C28 C 0.93493(18) 0.3276(2) 0.85842(13) 0.0617 1.0000 Uani . . . . . .
C29 C 0.9424(2) 0.4656(3) 0.87429(13) 0.0723 1.0000 Uani . . . . . .
C30 C 0.90284(18) 0.5573(2) 0.81307(11) 0.0594 1.0000 Uani . . . . . .
H171 H 0.3507 0.9335 0.5030 0.0515 1.0000 Uiso R . . . . .
H41 H 0.9434 0.5883 0.4873 0.0463 1.0000 Uiso R . . . . .
H51 H 0.9845 0.5450 0.3566 0.0542 1.0000 Uiso R . . . . .
H61 H 0.8492 0.5640 0.2327 0.0542 1.0000 Uiso R . . . . .
H71 H 0.6713 0.6249 0.2372 0.0513 1.0000 Uiso R . . . . .
H91 H 0.5931 0.5435 0.4754 0.0382 1.0000 Uiso R . . . . .
H121 H 0.5880 0.5513 0.6557 0.0452 1.0000 Uiso R . . . . .
H131 H 0.5053 0.5649 0.7700 0.0528 1.0000 Uiso R . . . . .
H141 H 0.3670 0.7243 0.7718 0.0545 1.0000 Uiso R . . . . .
H151 H 0.3155 0.8773 0.6591 0.0536 1.0000 Uiso R . . . . .
H181 H 0.4687 0.8629 0.4151 0.0466 1.0000 Uiso R . . . . .
H221 H 0.8243 0.7002 0.6771 0.0430 1.0000 Uiso R . . . . .
H251 H 0.7961 0.2371 0.6211 0.0508 1.0000 Uiso R . . . . .
H261 H 0.7334 0.3889 0.5151 0.0468 1.0000 Uiso R . . . . .
H271 H 0.8831 0.1857 0.7690 0.0604 1.0000 Uiso R . . . . .
H281 H 0.9619 0.2663 0.9028 0.0745 1.0000 Uiso R . . . . .
H291 H 0.9749 0.4975 0.9283 0.0879 1.0000 Uiso R . . . . .
H301 H 0.9058 0.6517 0.8249 0.0711 1.0000 Uiso R . . . . .
H11 H 0.5476 0.6531 0.3491 0.0484 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 0.0350(7) 0.0499(8) 0.0301(6) 0.0009(6) 0.0037(5) 0.0030(6)
C2 0.0405(8) 0.0360(8) 0.0350(8) 0.0016(6) 0.0108(6) 0.0015(6)
C3 0.0370(7) 0.0319(7) 0.0356(8) 0.0008(6) 0.0101(6) 0.0016(6)
C4 0.0366(8) 0.0364(8) 0.0441(8) 0.0024(7) 0.0119(6) 0.0028(6)
C5 0.0458(9) 0.0394(8) 0.0522(10) 0.0051(7) 0.0216(8) 0.0059(7)
C6 0.0604(10) 0.0392(9) 0.0415(8) 0.0030(7) 0.0239(7) 0.0032(8)
C7 0.0520(9) 0.0418(9) 0.0353(8) 0.0018(7) 0.0132(7) 0.0006(7)
C8 0.0318(7) 0.0325(7) 0.0322(7) -0.0013(6) 0.0061(5) 0.0021(6)
C9 0.0317(7) 0.0374(8) 0.0308(7) 0.0002(6) 0.0050(5) 0.0009(6)
C10 0.0306(7) 0.0382(8) 0.0355(7) -0.0018(6) 0.0049(6) 0.0001(6)
C11 0.0304(7) 0.0390(8) 0.0351(7) -0.0040(6) 0.0062(5) -0.0003(6)
C12 0.0345(7) 0.0421(8) 0.0374(8) -0.0006(6) 0.0062(6) 0.0011(6)
C13 0.0408(8) 0.0516(10) 0.0369(8) -0.0005(7) 0.0090(6) -0.0018(7)
C14 0.0405(8) 0.0615(11) 0.0390(8) -0.0078(8) 0.0126(7) -0.0014(8)
C15 0.0353(8) 0.0494(10) 0.0485(9) -0.0102(8) 0.0114(7) 0.0017(7)
C16 0.0336(7) 0.0387(8) 0.0410(8) -0.0042(6) 0.0064(6) -0.0001(6)
N17 0.0375(7) 0.0405(7) 0.0484(8) 0.0010(6) 0.0086(6) 0.0079(6)
C18 0.0356(8) 0.0395(8) 0.0418(8) 0.0029(6) 0.0076(6) 0.0043(6)
C19 0.0324(7) 0.0382(8) 0.0343(7) 0.0024(6) 0.0038(6) 0.0043(6)
N20 0.0442(7) 0.0386(8) 0.0506(8) 0.0005(6) 0.0029(6) 0.0032(6)
C21 0.0296(6) 0.0347(7) 0.0324(7) 0.0016(6) 0.0067(5) 0.0023(6)
C22 0.0379(7) 0.0352(8) 0.0348(7) -0.0003(6) 0.0072(6) 0.0047(6)
C23 0.0388(8) 0.0450(9) 0.0328(8) 0.0037(6) 0.0087(6) 0.0075(7)
C24 0.0337(7) 0.0429(9) 0.0422(8) 0.0079(7) 0.0111(6) 0.0030(6)
C25 0.0420(8) 0.0332(8) 0.0504(10) 0.0045(7) 0.0088(7) -0.0003(6)
C26 0.0383(8) 0.0366(8) 0.0388(8) 0.0000(6) 0.0041(6) -0.0004(6)
C27 0.0474(9) 0.0497(10) 0.0536(10) 0.0158(8) 0.0119(8) 0.0061(8)
C28 0.0667(13) 0.0682(14) 0.0476(11) 0.0225(10) 0.0066(9) 0.0162(11)
C29 0.0975(17) 0.0755(15) 0.0356(9) 0.0063(10) -0.0041(10) 0.0208(13)
C30 0.0804(14) 0.0555(12) 0.0361(9) -0.0004(8) -0.0012(9) 0.0143(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5659(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.391(2) yes
N1 . C9 . 1.4738(19) yes
N1 . H11 . 0.861 no
C2 . C3 . 1.391(2) yes
C2 . C7 . 1.397(2) yes
C3 . C4 . 1.381(2) yes
C3 . C8 . 1.530(2) yes
C4 . C5 . 1.396(2) yes
C4 . H41 . 0.979 no
C5 . C6 . 1.390(3) yes
C5 . H51 . 0.965 no
C6 . C7 . 1.391(2) yes
C6 . H61 . 0.961 no
C7 . H71 . 0.965 no
C8 . C9 . 1.586(2) yes
C8 . C19 . 1.481(2) yes
C8 . C21 . 1.523(2) yes
C9 . C10 . 1.497(2) yes
C9 . H91 . 0.997 no
C10 . C11 . 1.443(2) yes
C10 . C18 . 1.366(2) yes
C11 . C12 . 1.402(2) yes
C11 . C16 . 1.419(2) yes
C12 . C13 . 1.385(2) yes
C12 . H121 . 0.955 no
C13 . C14 . 1.406(3) yes
C13 . H131 . 0.973 no
C14 . C15 . 1.380(3) yes
C14 . H141 . 0.978 no
C15 . C16 . 1.401(2) yes
C15 . H151 . 0.953 no
C16 . N17 . 1.376(2) yes
N17 . C18 . 1.372(2) yes
N17 . H171 . 0.873 no
C18 . H181 . 0.955 no
C19 . N20 . 1.149(2) yes
C21 . C22 . 1.368(2) yes
C21 . C26 . 1.424(2) yes
C22 . C23 . 1.422(2) yes
C22 . H221 . 0.963 no
C23 . C24 . 1.415(2) yes
C23 . C30 . 1.413(2) yes
C24 . C25 . 1.418(2) yes
C24 . C27 . 1.418(2) yes
C25 . C26 . 1.366(2) yes
C25 . H251 . 0.943 no
C26 . H261 . 0.958 no
C27 . C28 . 1.361(3) yes
C27 . H271 . 0.972 no
C28 . C29 . 1.395(4) yes
C28 . H281 . 0.954 no
C29 . C30 . 1.368(3) yes
C29 . H291 . 0.947 no
C30 . H301 . 0.956 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C9 . 107.74(12) yes
C2 . N1 . H11 . 115.4 no
C9 . N1 . H11 . 115.2 no
N1 . C2 . C3 . 110.65(13) yes
N1 . C2 . C7 . 129.17(15) yes
C3 . C2 . C7 . 120.16(15) yes
C2 . C3 . C4 . 121.96(14) yes
C2 . C3 . C8 . 109.00(13) yes
C4 . C3 . C8 . 129.04(14) yes
C3 . C4 . C5 . 118.12(15) yes
C3 . C4 . H41 . 121.8 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 120.13(15) yes
C4 . C5 . H51 . 118.8 no
C6 . C5 . H51 . 121.0 no
C5 . C6 . C7 . 121.83(15) yes
C5 . C6 . H61 . 119.9 no
C7 . C6 . H61 . 118.3 no
C2 . C7 . C6 . 117.77(16) yes
C2 . C7 . H71 . 120.5 no
C6 . C7 . H71 . 121.7 no
C3 . C8 . C9 . 100.19(11) yes
C3 . C8 . C19 . 108.66(12) yes
C9 . C8 . C19 . 108.21(12) yes
C3 . C8 . C21 . 113.05(12) yes
C9 . C8 . C21 . 114.01(12) yes
C19 . C8 . C21 . 111.98(12) yes
C8 . C9 . N1 . 102.37(11) yes
C8 . C9 . C10 . 117.34(12) yes
N1 . C9 . C10 . 111.56(13) yes
C8 . C9 . H91 . 105.1 no
N1 . C9 . H91 . 109.5 no
C10 . C9 . H91 . 110.5 no
C9 . C10 . C11 . 127.89(14) yes
C9 . C10 . C18 . 125.34(14) yes
C11 . C10 . C18 . 106.69(13) yes
C10 . C11 . C12 . 135.03(14) yes
C10 . C11 . C16 . 106.39(13) yes
C12 . C11 . C16 . 118.57(14) yes
C11 . C12 . C13 . 119.18(15) yes
C11 . C12 . H121 . 120.7 no
C13 . C12 . H121 . 120.2 no
C12 . C13 . C14 . 121.15(16) yes
C12 . C13 . H131 . 119.4 no
C14 . C13 . H131 . 119.5 no
C13 . C14 . C15 . 121.30(16) yes
C13 . C14 . H141 . 119.7 no
C15 . C14 . H141 . 119.0 no
C14 . C15 . C16 . 117.41(16) yes
C14 . C15 . H151 . 122.9 no
C16 . C15 . H151 . 119.7 no
C11 . C16 . C15 . 122.38(15) yes
C11 . C16 . N17 . 107.71(14) yes
C15 . C16 . N17 . 129.91(15) yes
C16 . N17 . C18 . 108.96(13) yes
C16 . N17 . H171 . 125.0 no
C18 . N17 . H171 . 125.8 no
N17 . C18 . C10 . 110.25(15) yes
N17 . C18 . H181 . 122.2 no
C10 . C18 . H181 . 127.5 no
C8 . C19 . N20 . 177.55(16) yes
C8 . C21 . C22 . 122.82(14) yes
C8 . C21 . C26 . 118.13(13) yes
C22 . C21 . C26 . 119.05(14) yes
C21 . C22 . C23 . 121.32(15) yes
C21 . C22 . H221 . 120.1 no
C23 . C22 . H221 . 118.6 no
C22 . C23 . C24 . 119.36(15) yes
C22 . C23 . C30 . 121.62(17) yes
C24 . C23 . C30 . 119.01(16) yes
C23 . C24 . C25 . 118.37(15) yes
C23 . C24 . C27 . 119.00(16) yes
C25 . C24 . C27 . 122.61(16) yes
C24 . C25 . C26 . 121.23(16) yes
C24 . C25 . H251 . 118.8 no
C26 . C25 . H251 . 119.9 no
C21 . C26 . C25 . 120.68(15) yes
C21 . C26 . H261 . 119.8 no
C25 . C26 . H261 . 119.5 no
C24 . C27 . C28 . 120.63(19) yes
C24 . C27 . H271 . 118.6 no
C28 . C27 . H271 . 120.7 no
C27 . C28 . C29 . 120.12(18) yes
C27 . C28 . H281 . 120.7 no
C29 . C28 . H281 . 119.1 no
C28 . C29 . C30 . 121.2(2) yes
C28 . C29 . H291 . 120.1 no
C30 . C29 . H291 . 118.6 no
C23 . C30 . C29 . 120.0(2) yes
C23 . C30 . H301 . 119.2 no
C29 . C30 . H301 . 120.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N17 . H171 . N20 2_676 169.72(5) 0.873 2.205 3.069(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 28/06/12 at 18:14:36
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE N ( 1,X'S) H ( 11,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S)
RIDE C ( 6,X'S) H ( 61,X'S)
RIDE C ( 7,X'S) H ( 71,X'S)
RIDE C ( 9,X'S) H ( 91,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 N ( 17,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 22,X'S) H ( 221,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 ( 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)
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 28/06/12 at 18:14:36
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
#end of refcif
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).