# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_audit_block_doi                 10.5517/ccs3sbz
_database_code_depnum_ccdc_archive 'CCDC 718621'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'

_chemical_absolute_configuration syn

_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrogen atoms attached to the strained ring-junctions C2 and C3 were
located in a difference Fourier map and its coordinates and isotropic
displacement parameter subsequently refined. Other hydrogens were positioned
geometrically.

The large displacement parameters of the phenyl carbons C20-C25 suggest that
there is unresolved disorder of this group. Attempts to model this led to no
improvement in the agreement with the X-ray data and were abandoned.
;

#=============================================================

_cell_length_a                   9.1864(3)
_cell_angle_alpha                90
_cell_length_b                   11.0253(3)
_cell_angle_beta                 90
_cell_length_c                   18.9835(6)
_cell_angle_gamma                90
_cell_volume                     1922.70(10)

_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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B


_cell_formula_units_Z            4
_chemical_formula_sum            ' C25 H21 N1 O2 '
_chemical_formula_moiety         ' C25 H21 N1 O2 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         367.45


_cell_measurement_reflns_used    13281
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' plate '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_max          0.42

_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.080

_diffrn_measurement_method       ω

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13281
_reflns_number_total             2455
# 2475 unique reflections including absences
_diffrn_reflns_av_R_equivalents  0.056

_diffrn_reflns_theta_min         5.177
_diffrn_reflns_theta_max         27.468
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        27.468
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              0
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              24


_refine_diff_density_min         -0.13
_refine_diff_density_max         0.18


_refine_ls_number_reflns         1756
_refine_ls_number_restraints     0
_refine_ls_number_parameters     261

#_refine_ls_R_factor_ref 0.0332
_refine_ls_wR_factor_ref         0.0365
_refine_ls_goodness_of_fit_ref   1.1585

#_reflns_number_all 2455
_refine_ls_R_factor_all          0.0534
_refine_ls_wR_factor_all         0.0560

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1756
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0365


_refine_ls_shift/su_max          0.005945
_refine_ls_structure_factor_coef F
_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:
0.309 0.140 0.103
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

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

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
N1 N 0.5570(2) 0.51014(16) 0.28333(10) 0.0259 1.0000 Uani
C1 C 0.5388(3) 0.61868(19) 0.31843(11) 0.0246 1.0000 Uani
C2 C 0.3825(2) 0.6311(2) 0.33823(11) 0.0237 1.0000 Uani
C3 C 0.3032(3) 0.5310(2) 0.29775(11) 0.0248 1.0000 Uani
C4 C 0.4177(2) 0.4606(2) 0.25804(11) 0.0254 1.0000 Uani
C5 C 0.4327(3) 0.4860(2) 0.17960(12) 0.0334 1.0000 Uani
O1 O 0.58409(19) 0.46036(17) 0.16675(8) 0.0377 1.0000 Uani
C6 C 0.6656(3) 0.4974(2) 0.22788(13) 0.0332 1.0000 Uani
O2 O 0.63584(17) 0.69247(15) 0.32816(9) 0.0332 1.0000 Uani
C7 C 0.3084(2) 0.52602(19) 0.37677(10) 0.0223 1.0000 Uani
C8 C 0.1694(2) 0.55872(18) 0.41492(11) 0.0234 1.0000 Uani
C9 C 0.0348(3) 0.5208(2) 0.39017(12) 0.0298 1.0000 Uani
C10 C -0.0920(3) 0.5482(2) 0.42674(13) 0.0357 1.0000 Uani
C11 C -0.0847(3) 0.6138(2) 0.48895(13) 0.0354 1.0000 Uani
C12 C 0.0489(3) 0.6533(2) 0.51383(12) 0.0339 1.0000 Uani
C13 C 0.1754(3) 0.6252(2) 0.47734(12) 0.0291 1.0000 Uani
C14 C 0.3974(2) 0.4311(2) 0.41389(11) 0.0244 1.0000 Uani
C15 C 0.3655(2) 0.3082(2) 0.40397(12) 0.0277 1.0000 Uani
C16 C 0.4440(3) 0.2195(2) 0.43930(13) 0.0361 1.0000 Uani
C17 C 0.5541(3) 0.2519(2) 0.48486(14) 0.0413 1.0000 Uani
C18 C 0.5862(3) 0.3734(3) 0.49601(14) 0.0399 1.0000 Uani
C19 C 0.5084(3) 0.4629(2) 0.46052(12) 0.0320 1.0000 Uani
C20 C 0.7821(3) 0.4048(2) 0.24260(15) 0.0393 1.0000 Uani
C21 C 0.8973(3) 0.3935(3) 0.1952(2) 0.0628 1.0000 Uani
C22 C 1.0058(4) 0.3076(5) 0.2076(3) 0.0905 1.0000 Uani
C23 C 1.0003(4) 0.2365(4) 0.2654(4) 0.0972 1.0000 Uani
C24 C 0.8862(4) 0.2455(3) 0.3135(2) 0.0702 1.0000 Uani
C25 C 0.7763(3) 0.3302(2) 0.30157(18) 0.0480 1.0000 Uani
H21 H 0.344(3) 0.713(2) 0.3441(12) 0.026(6) 1.0000 Uiso
H31 H 0.210(3) 0.546(2) 0.2734(14) 0.036(7) 1.0000 Uiso
H41 H 0.3919 0.3734 0.2653 0.0305 1.0000 Uiso
H51 H 0.4091 0.5724 0.1685 0.0401 1.0000 Uiso
H52 H 0.3685 0.4313 0.1513 0.0401 1.0000 Uiso
H61 H 0.7193 0.5757 0.2225 0.0399 1.0000 Uiso
H91 H 0.0290 0.4732 0.3454 0.0358 1.0000 Uiso
H101 H -0.1884 0.5206 0.4082 0.0429 1.0000 Uiso
H111 H -0.1757 0.6325 0.5158 0.0425 1.0000 Uiso
H121 H 0.0543 0.7021 0.5581 0.0407 1.0000 Uiso
H131 H 0.2716 0.6529 0.4960 0.0349 1.0000 Uiso
H151 H 0.2854 0.2841 0.3711 0.0332 1.0000 Uiso
H161 H 0.4207 0.1319 0.4317 0.0433 1.0000 Uiso
H171 H 0.6110 0.1878 0.5100 0.0496 1.0000 Uiso
H181 H 0.6653 0.3967 0.5296 0.0479 1.0000 Uiso
H191 H 0.5322 0.5503 0.4685 0.0384 1.0000 Uiso
H211 H 0.9021 0.4466 0.1525 0.0754 1.0000 Uiso
H221 H 1.0881 0.2987 0.1735 0.1086 1.0000 Uiso
H231 H 1.0796 0.1761 0.2739 0.1167 1.0000 Uiso
H241 H 0.8833 0.1920 0.3561 0.0843 1.0000 Uiso
H251 H 0.6933 0.3373 0.3354 0.0575 1.0000 Uiso
_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
N1 . C1 . 1.380(3) yes
N1 . C4 . 1.472(3) yes
N1 . C6 . 1.457(3) yes
C1 . C2 . 1.491(3) yes
C1 . O2 . 1.221(3) yes
C2 . C3 . 1.529(3) yes
C2 . C7 . 1.530(3) yes
C2 . H21 . 0.98(2) no
C3 . C4 . 1.509(3) yes
C3 . C7 . 1.502(3) yes
C3 . H31 . 0.99(3) no
C4 . C5 . 1.522(3) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.440(3) yes
C5 . H51 . 1.000 no
C5 . H52 . 1.000 no
O1 . C6 . 1.440(3) yes
C6 . C20 . 1.505(3) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.511(3) yes
C7 . C14 . 1.503(3) yes
C8 . C9 . 1.387(3) yes
C8 . C13 . 1.394(3) yes
C9 . C10 . 1.390(3) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.387(4) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.386(4) yes
C11 . H111 . 1.000 no
C12 . C13 . 1.387(3) yes
C12 . H121 . 1.000 no
C13 . H131 . 1.000 no
C14 . C15 . 1.399(3) yes
C14 . C19 . 1.395(3) yes
C15 . C16 . 1.388(3) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.378(4) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.388(4) yes
C17 . H171 . 1.000 no
C18 . C19 . 1.392(3) yes
C18 . H181 . 1.000 no
C19 . H191 . 1.000 no
C20 . C21 . 1.396(4) yes
C20 . C25 . 1.390(4) yes
C21 . C22 . 1.394(6) yes
C21 . H211 . 1.000 no
C22 . C23 . 1.351(7) yes
C22 . H221 . 1.000 no
C23 . C24 . 1.394(7) yes
C23 . H231 . 1.000 no
C24 . C25 . 1.394(4) yes
C24 . H241 . 1.000 no
C25 . H251 . 1.000 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
C1 . N1 . C4 . 111.97(17) yes
C1 . N1 . C6 . 121.04(18) yes
C4 . N1 . C6 . 108.90(17) yes
N1 . C1 . C2 . 108.54(18) yes
N1 . C1 . O2 . 124.2(2) yes
C2 . C1 . O2 . 127.1(2) yes
C1 . C2 . C3 . 105.42(18) yes
C1 . C2 . C7 . 118.65(19) yes
C3 . C2 . C7 . 58.81(13) yes
C1 . C2 . H21 . 117.4(14) no
C3 . C2 . H21 . 123.7(14) no
C7 . C2 . H21 . 119.2(14) no
C2 . C3 . C4 . 106.87(18) yes
C2 . C3 . C7 . 60.62(14) yes
C4 . C3 . C7 . 117.2(2) yes
C2 . C3 . H31 . 122.1(16) no
C4 . C3 . H31 . 117.1(15) no
C7 . C3 . H31 . 120.0(15) no
N1 . C4 . C3 . 104.61(17) yes
N1 . C4 . C5 . 99.90(18) yes
C3 . C4 . C5 . 117.24(19) yes
N1 . C4 . H41 . 121.188 no
C3 . C4 . H41 . 105.125 no
C5 . C4 . H41 . 109.458 no
C4 . C5 . O1 . 102.57(19) yes
C4 . C5 . H51 . 111.170 no
O1 . C5 . H51 . 111.170 no
C4 . C5 . H52 . 111.170 no
O1 . C5 . H52 . 111.170 no
H51 . C5 . H52 . 109.466 no
C5 . O1 . C6 . 108.07(17) yes
N1 . C6 . O1 . 104.68(18) yes
N1 . C6 . C20 . 114.7(2) yes
O1 . C6 . C20 . 109.11(19) yes
N1 . C6 . H61 . 109.142 no
O1 . C6 . H61 . 114.762 no
C20 . C6 . H61 . 104.718 no
C2 . C7 . C3 . 60.57(15) yes
C2 . C7 . C8 . 115.10(18) yes
C3 . C7 . C8 . 116.28(19) yes
C2 . C7 . C14 . 120.61(18) yes
C3 . C7 . C14 . 120.75(19) yes
C8 . C7 . C14 . 113.64(17) yes
C7 . C8 . C9 . 121.24(18) yes
C7 . C8 . C13 . 120.0(2) yes
C9 . C8 . C13 . 118.8(2) yes
C8 . C9 . C10 . 120.9(2) yes
C8 . C9 . H91 . 119.567 no
C10 . C9 . H91 . 119.567 no
C9 . C10 . C11 . 119.9(2) yes
C9 . C10 . H101 . 120.066 no
C11 . C10 . H101 . 120.066 no
C10 . C11 . C12 . 119.8(2) yes
C10 . C11 . H111 . 120.095 no
C12 . C11 . H111 . 120.095 no
C11 . C12 . C13 . 120.1(2) yes
C11 . C12 . H121 . 119.953 no
C13 . C12 . H121 . 119.954 no
C8 . C13 . C12 . 120.6(2) yes
C8 . C13 . H131 . 119.700 no
C12 . C13 . H131 . 119.700 no
C7 . C14 . C15 . 119.8(2) yes
C7 . C14 . C19 . 121.4(2) yes
C15 . C14 . C19 . 118.8(2) yes
C14 . C15 . C16 . 120.6(2) yes
C14 . C15 . H151 . 119.714 no
C16 . C15 . H151 . 119.715 no
C15 . C16 . C17 . 120.1(2) yes
C15 . C16 . H161 . 119.945 no
C17 . C16 . H161 . 119.945 no
C16 . C17 . C18 . 120.1(2) yes
C16 . C17 . H171 . 119.930 no
C18 . C17 . H171 . 119.930 no
C17 . C18 . C19 . 120.1(2) yes
C17 . C18 . H181 . 119.967 no
C19 . C18 . H181 . 119.967 no
C14 . C19 . C18 . 120.3(2) yes
C14 . C19 . H191 . 119.836 no
C18 . C19 . H191 . 119.836 no
C6 . C20 . C21 . 118.7(3) yes
C6 . C20 . C25 . 121.6(2) yes
C21 . C20 . C25 . 119.7(3) yes
C20 . C21 . C22 . 119.6(4) yes
C20 . C21 . H211 . 120.204 no
C22 . C21 . H211 . 120.205 no
C21 . C22 . C23 . 120.3(4) yes
C21 . C22 . H221 . 119.828 no
C23 . C22 . H221 . 119.833 no
C22 . C23 . C24 . 121.3(3) yes
C22 . C23 . H231 . 119.349 no
C24 . C23 . H231 . 119.352 no
C23 . C24 . C25 . 119.1(4) yes
C23 . C24 . H241 . 120.473 no
C25 . C24 . H241 . 120.475 no
C20 . C25 . C24 . 120.0(3) yes
C20 . C25 . H251 . 120.002 no
C24 . C25 . H251 . 120.002 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_audit_block_doi                 10.5517/ccs3sc0
_database_code_depnum_ccdc_archive 'CCDC 718622'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_chemical_absolute_configuration syn

_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrogen atoms attached to the strained ring-junctions C2 and C3 were
located in a difference Fourier map and their coordinates and isotropic
displacement parameter subsequently refined. Other hydrogens were positioned
geometrically.
;

#=============================================================

_cell_length_a                   6.2814(2)
_cell_angle_alpha                90
_cell_length_b                   10.6745(4)
_cell_angle_beta                 90.9240(13)
_cell_length_c                   13.5929(5)
_cell_angle_gamma                90
_cell_volume                     911.30(6)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B


_cell_formula_units_Z            2
_chemical_formula_sum            ' C25 H19 N O2 '
_chemical_formula_moiety         ' C25 H19 N O2 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         365.43


_cell_measurement_reflns_used    6503
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' fragment '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.14
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.084


_diffrn_measurement_method       ω

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            6503
_reflns_number_total             2174
#2180 unique reflections including absences
_diffrn_reflns_av_R_equivalents  0.035

_diffrn_reflns_theta_min         5.218
_diffrn_reflns_theta_max         27.473
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        27.473
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              17


_refine_diff_density_min         -0.15
_refine_diff_density_max         0.14


_refine_ls_number_reflns         1743
_refine_ls_number_restraints     1
_refine_ls_number_parameters     261

#_refine_ls_R_factor_ref 0.0305
_refine_ls_wR_factor_ref         0.0338
_refine_ls_goodness_of_fit_ref   1.1466

#_reflns_number_all 2174
_refine_ls_R_factor_all          0.0427
_refine_ls_wR_factor_all         0.0465

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1743
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0338


_refine_ls_shift/su_max          0.002680
_refine_ls_structure_factor_coef F
_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:
0.353 0.142 0.0939
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073


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

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
N1 N 0.0730(3) 0.31776(18) 0.28741(12) 0.0220 1.0000 Uani
C1 C 0.1503(3) 0.2325(2) 0.22013(15) 0.0221 1.0000 Uani
C2 C 0.0440(3) 0.2564(2) 0.12301(15) 0.0212 1.0000 Uani
C3 C -0.1234(3) 0.3556(2) 0.13975(15) 0.0218 1.0000 Uani
C4 C -0.1124(3) 0.3872(2) 0.24901(16) 0.0234 1.0000 Uani
C5 C -0.2866(3) 0.3321(3) 0.31372(16) 0.0304 1.0000 Uani
O1 O -0.1772(2) 0.31950(18) 0.40718(11) 0.0307 1.0000 Uani
C6 C 0.0348(3) 0.2794(2) 0.38997(15) 0.0241 1.0000 Uani
O2 O 0.2798(2) 0.15146(16) 0.23975(12) 0.0288 1.0000 Uani
C7 C 0.0644(3) 0.3886(2) 0.07707(15) 0.0215 1.0000 Uani
C8 C 0.2492(3) 0.4756(2) 0.09663(15) 0.0214 1.0000 Uani
C9 C 0.3401(3) 0.5239(2) 0.18262(16) 0.0250 1.0000 Uani
C10 C 0.5171(3) 0.6021(2) 0.17666(16) 0.0271 1.0000 Uani
C11 C 0.6066(3) 0.6320(2) 0.08646(18) 0.0284 1.0000 Uani
C12 C 0.5155(4) 0.5854(2) -0.00059(19) 0.0270 1.0000 Uani
C13 C 0.3364(3) 0.5095(2) 0.00463(15) 0.0222 1.0000 Uani
C14 C 0.2049(3) 0.4562(2) -0.07448(15) 0.0221 1.0000 Uani
C15 C 0.2236(4) 0.4631(2) -0.17663(16) 0.0278 1.0000 Uani
C16 C 0.0706(4) 0.4042(2) -0.23536(16) 0.0318 1.0000 Uani
C17 C -0.0975(4) 0.3402(2) -0.19341(16) 0.0309 1.0000 Uani
C18 C -0.1169(3) 0.3309(2) -0.09132(16) 0.0273 1.0000 Uani
C19 C 0.0370(3) 0.3893(2) -0.03269(14) 0.0215 1.0000 Uani
C20 C 0.1839(3) 0.3389(2) 0.46419(14) 0.0235 1.0000 Uani
C21 C 0.1879(4) 0.4682(2) 0.47744(18) 0.0306 1.0000 Uani
C22 C 0.3346(4) 0.5219(2) 0.54212(19) 0.0366 1.0000 Uani
C23 C 0.4802(4) 0.4473(3) 0.59290(17) 0.0380 1.0000 Uani
C24 C 0.4748(4) 0.3188(3) 0.58102(17) 0.0356 1.0000 Uani
C25 C 0.3245(3) 0.2647(2) 0.51711(16) 0.0276 1.0000 Uani
H21 H 0.030(4) 0.184(3) 0.0802(19) 0.027(6) 1.0000 Uiso
H31 H -0.262(4) 0.354(2) 0.1061(17) 0.022(6) 1.0000 Uiso
H41 H -0.1171 0.4808 0.2520 0.0281 1.0000 Uiso
H51 H -0.4109 0.3903 0.3184 0.0365 1.0000 Uiso
H52 H -0.3363 0.2491 0.2883 0.0365 1.0000 Uiso
H61 H 0.0588 0.1873 0.3979 0.0289 1.0000 Uiso
H91 H 0.2790 0.5028 0.2480 0.0300 1.0000 Uiso
H101 H 0.5813 0.6375 0.2384 0.0324 1.0000 Uiso
H111 H 0.7357 0.6866 0.0841 0.0341 1.0000 Uiso
H121 H 0.5784 0.6064 -0.0657 0.0325 1.0000 Uiso
H151 H 0.3445 0.5094 -0.2068 0.0334 1.0000 Uiso
H161 H 0.0817 0.4081 -0.3086 0.0382 1.0000 Uiso
H171 H -0.2071 0.2997 -0.2371 0.0370 1.0000 Uiso
H181 H -0.2375 0.2839 -0.0615 0.0328 1.0000 Uiso
H211 H 0.0848 0.5224 0.4402 0.0368 1.0000 Uiso
H221 H 0.3354 0.6147 0.5522 0.0441 1.0000 Uiso
H231 H 0.5887 0.4864 0.6379 0.0457 1.0000 Uiso
H241 H 0.5782 0.2646 0.6181 0.0427 1.0000 Uiso
H251 H 0.3189 0.1716 0.5097 0.0332 1.0000 Uiso
_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
N1 . C1 . 1.384(3) yes
N1 . C4 . 1.469(3) yes
N1 . C6 . 1.476(3) yes
C1 . C2 . 1.492(3) yes
C1 . O2 . 1.214(3) yes
C2 . C3 . 1.512(3) yes
C2 . C7 . 1.550(3) yes
C2 . H21 . 0.97(3) no
C3 . C4 . 1.524(3) yes
C3 . C7 . 1.508(3) yes
C3 . H31 . 0.98(2) no
C4 . C5 . 1.533(3) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.441(3) yes
C5 . H51 . 1.000 no
C5 . H52 . 1.000 no
O1 . C6 . 1.422(2) yes
C6 . C20 . 1.506(3) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.507(3) yes
C7 . C19 . 1.499(3) yes
C8 . C9 . 1.391(3) yes
C8 . C13 . 1.420(3) yes
C9 . C10 . 1.393(3) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.394(3) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.397(3) yes
C11 . H111 . 1.000 no
C12 . C13 . 1.389(3) yes
C12 . H121 . 1.000 no
C13 . C14 . 1.461(3) yes
C14 . C15 . 1.397(3) yes
C14 . C19 . 1.402(3) yes
C15 . C16 . 1.390(3) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.388(3) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.399(3) yes
C17 . H171 . 1.000 no
C18 . C19 . 1.390(3) yes
C18 . H181 . 1.000 no
C20 . C21 . 1.392(3) yes
C20 . C25 . 1.380(3) yes
C21 . C22 . 1.387(4) yes
C21 . H211 . 1.000 no
C22 . C23 . 1.388(4) yes
C22 . H221 . 1.000 no
C23 . C24 . 1.381(4) yes
C23 . H231 . 1.000 no
C24 . C25 . 1.398(3) yes
C24 . H241 . 1.000 no
C25 . H251 . 1.000 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
C1 . N1 . C4 . 112.45(16) yes
C1 . N1 . C6 . 120.36(18) yes
C4 . N1 . C6 . 109.63(15) yes
N1 . C1 . C2 . 108.36(18) yes
N1 . C1 . O2 . 124.4(2) yes
C2 . C1 . O2 . 127.3(2) yes
C1 . C2 . C3 . 106.82(18) yes
C1 . C2 . C7 . 118.30(18) yes
C3 . C2 . C7 . 59.00(13) yes
C1 . C2 . H21 . 115.4(15) no
C3 . C2 . H21 . 126.1(15) no
C7 . C2 . H21 . 119.4(15) no
C2 . C3 . C4 . 106.32(17) yes
C2 . C3 . C7 . 61.74(13) yes
C4 . C3 . C7 . 118.37(17) yes
C2 . C3 . H31 . 122.0(15) no
C4 . C3 . H31 . 119.2(14) no
C7 . C3 . H31 . 116.0(14) no
N1 . C4 . C3 . 104.95(16) yes
N1 . C4 . C5 . 99.89(16) yes
C3 . C4 . C5 . 116.92(18) yes
N1 . C4 . H41 . 120.877 no
C3 . C4 . H41 . 105.086 no
C5 . C4 . H41 . 109.746 no
C4 . C5 . O1 . 101.95(16) yes
C4 . C5 . H51 . 111.319 no
O1 . C5 . H51 . 111.320 no
C4 . C5 . H52 . 111.320 no
O1 . C5 . H52 . 111.320 no
H51 . C5 . H52 . 109.467 no
C5 . O1 . C6 . 108.54(15) yes
N1 . C6 . O1 . 103.80(16) yes
N1 . C6 . C20 . 114.03(17) yes
O1 . C6 . C20 . 109.68(17) yes
N1 . C6 . H61 . 110.377 no
O1 . C6 . H61 . 114.680 no
C20 . C6 . H61 . 104.573 no
C2 . C7 . C3 . 59.25(13) yes
C2 . C7 . C8 . 123.96(18) yes
C3 . C7 . C8 . 130.69(18) yes
C2 . C7 . C19 . 113.34(18) yes
C3 . C7 . C19 . 119.01(17) yes
C8 . C7 . C19 . 104.40(17) yes
C7 . C8 . C9 . 132.92(19) yes
C7 . C8 . C13 . 107.98(18) yes
C9 . C8 . C13 . 119.10(19) yes
C8 . C9 . C10 . 119.34(19) yes
C8 . C9 . H91 . 120.331 no
C10 . C9 . H91 . 120.331 no
C9 . C10 . C11 . 121.4(2) yes
C9 . C10 . H101 . 119.282 no
C11 . C10 . H101 . 119.283 no
C10 . C11 . C12 . 119.9(2) yes
C10 . C11 . H111 . 120.056 no
C12 . C11 . H111 . 120.056 no
C11 . C12 . C13 . 119.0(2) yes
C11 . C12 . H121 . 120.501 no
C13 . C12 . H121 . 120.501 no
C8 . C13 . C12 . 121.2(2) yes
C8 . C13 . C14 . 109.10(18) yes
C12 . C13 . C14 . 129.7(2) yes
C13 . C14 . C15 . 130.94(19) yes
C13 . C14 . C19 . 108.71(17) yes
C15 . C14 . C19 . 120.4(2) yes
C14 . C15 . C16 . 118.6(2) yes
C14 . C15 . H151 . 120.705 no
C16 . C15 . H151 . 120.705 no
C15 . C16 . C17 . 120.7(2) yes
C15 . C16 . H161 . 119.651 no
C17 . C16 . H161 . 119.650 no
C16 . C17 . C18 . 121.4(2) yes
C16 . C17 . H171 . 119.292 no
C18 . C17 . H171 . 119.292 no
C17 . C18 . C19 . 117.8(2) yes
C17 . C18 . H181 . 121.102 no
C19 . C18 . H181 . 121.102 no
C7 . C19 . C14 . 109.29(18) yes
C7 . C19 . C18 . 129.51(19) yes
C14 . C19 . C18 . 121.13(18) yes
C6 . C20 . C21 . 121.0(2) yes
C6 . C20 . C25 . 119.5(2) yes
C21 . C20 . C25 . 119.4(2) yes
C20 . C21 . C22 . 120.2(2) yes
C20 . C21 . H211 . 119.911 no
C22 . C21 . H211 . 119.911 no
C21 . C22 . C23 . 120.2(2) yes
C21 . C22 . H221 . 119.904 no
C23 . C22 . H221 . 119.904 no
C22 . C23 . C24 . 119.8(2) yes
C22 . C23 . H231 . 120.094 no
C24 . C23 . H231 . 120.094 no
C23 . C24 . C25 . 119.9(2) yes
C23 . C24 . H241 . 120.066 no
C25 . C24 . H241 . 120.066 no
C20 . C25 . C24 . 120.5(2) yes
C20 . C25 . H251 . 119.759 no
C24 . C25 . H251 . 119.759 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8b
_audit_block_doi                 10.5517/ccs3sd1
_database_code_depnum_ccdc_archive 'CCDC 718623'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_chemical_absolute_configuration unk

_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_diffrn_special_details          
;
Examination of the diffraction pattern showed the crystal to be a twin, the
two components of which were related by a rotation of 180/% about the
direct c axis, or by the reflection resulting from combination of this
with an inversion. See comments under '_refine_special_details' concerning
absolute structure.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed

_refine_special_details          
;
In addition to the twinning described above, as the structure is
non-centrosymmetric, it was also necessary to consider the possiblity of the
primary component of the crystal being itself a racemic twin ('conglomerate').

An attempt was made to treat the crystal as a four-component twin with the
following twin laws:
1(Identity)

2(Inversion) (h') (-1 0 0) (h)
(k')=(0 -1 0).(k)
(l') (0 0 -1) (l)

3(Rotation about c) (h') (-1 0 -0.403) (h)
(k')=(0 -1 0).(k)
(l') (0 0 1) (l)

4(Reflection abount (0 0 1)) (h') (1 0 0.403) (h)
(k')=(0 1 0).(k)
(l') (0 0 -1) (l)
(Component 2 is distinguishable from the primary component only as a result
of anomalous scattering, and similarly components 3 and 4 are distinguishable
as a result of anomalous scattering,)

Refinement of the relative contributions of the four components to the
diffraction pattern converged readily, giving values of ca. 0.8, 0, 0.2, 0
respectively. It was therefore concluded that the crystal is twinned purely
by rotation and that each component is a single enantiomer. Note that the
Flack or Rogers parameters conventionally used as measures of correctness
of absolute structure are inappropriate in this context.

Subsequent refinement of the structure assumed a two-component twin (primary
and rotation about c only), with final partial contributions to the
intensities of the diffracted peaks of 0.8322(13)and 0.1678(13) respectively.

The hydrogen atom H31 attached to the strained ring-junction C3 was located in
a difference Fourier map and its coordinates and isotropic displacement
parameter subsequently refined. Other hydrogens were positioned geometrically.

The large displacement parameters of some of the atoms of the phenyl group
C23-C28 suggest that it may be disordered. Attempts to model this did not
lead to an improvement in the agreement with the diffraction data and were
abandoned.
;

#=============================================================

_cell_length_a                   12.6544(2)
_cell_angle_alpha                90
_cell_length_b                   6.3405(2)
_cell_angle_beta                 105.6186(7)
_cell_length_c                   16.9101(4)
_cell_angle_gamma                90
_cell_volume                     1306.69(6)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'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_IV_Table_2.2B
'I ' -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 International_Tables_Vol_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B


_cell_formula_units_Z            2
_chemical_formula_sum            ' C28 H23 I2 N O4 '
_chemical_formula_moiety         ' C28 H23 I2 N O4 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         691.30


_cell_measurement_reflns_used    12998
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' prism '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    2.441

_diffrn_measurement_method       ω

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.86

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            12998
_reflns_number_total             5271
#5279 unique reflcetions including absences
_diffrn_reflns_av_R_equivalents  0.037

_diffrn_reflns_theta_min         5.220
_diffrn_reflns_theta_max         27.481
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.481
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              -7
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              21


_refine_diff_density_min         -0.99
_refine_diff_density_max         0.71


_refine_ls_number_reflns         4506
_refine_ls_number_restraints     1
_refine_ls_number_parameters     321

#_refine_ls_R_factor_ref 0.0303
_refine_ls_wR_factor_ref         0.0310
_refine_ls_goodness_of_fit_ref   1.1045

#_reflns_number_all 5271
_refine_ls_R_factor_all          0.0393
_refine_ls_wR_factor_all         0.0402

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                4506
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0310


_refine_ls_shift/su_max          0.003822
_refine_ls_structure_factor_coef F
_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:
0.369 0.0586 0.0711
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073


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

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
N1 N 0.3813(2) 0.3549(5) 0.13205(19) 0.0198 1.0000 Uani
C1 C 0.2937(3) 0.4784(6) 0.1335(2) 0.0203 1.0000 Uani
C2 C 0.2103(3) 0.3363(6) 0.1545(2) 0.0188 1.0000 Uani
C3 C 0.2520(3) 0.1122(7) 0.1525(2) 0.0191 1.0000 Uani
C4 C 0.3588(3) 0.1279(6) 0.1290(2) 0.0197 1.0000 Uani
C5 C 0.3601(4) 0.0822(7) 0.0409(3) 0.0260 1.0000 Uani
O1 O 0.4461(3) 0.2201(5) 0.02918(19) 0.0324 1.0000 Uani
C6 C 0.4577(3) 0.3981(7) 0.0828(2) 0.0243 1.0000 Uani
O2 O 0.2869(3) 0.6665(5) 0.1198(2) 0.0302 1.0000 Uani
C7 C 0.2515(3) 0.2046(6) 0.2345(2) 0.0170 1.0000 Uani
C8 C 0.1650(3) 0.1309(6) 0.2745(2) 0.0197 1.0000 Uani
C9 C 0.1228(3) -0.0726(8) 0.2649(2) 0.0256 1.0000 Uani
C10 C 0.0453(3) -0.1325(7) 0.3049(3) 0.0313 1.0000 Uani
C11 C 0.0098(3) 0.0060(7) 0.3540(2) 0.0289 1.0000 Uani
C12 C 0.0485(3) 0.2131(8) 0.3633(3) 0.0297 1.0000 Uani
C13 C 0.1271(4) 0.2729(8) 0.3239(3) 0.0287 1.0000 Uani
I1 I -0.10414(2) -0.09036(12) 0.417267(17) 0.0482 1.0000 Uani
C14 C 0.3580(3) 0.2653(6) 0.2960(2) 0.0201 1.0000 Uani
C15 C 0.4370(3) 0.1113(7) 0.3257(3) 0.0258 1.0000 Uani
C16 C 0.5347(3) 0.1602(8) 0.3836(3) 0.0319 1.0000 Uani
C17 C 0.5533(3) 0.3648(8) 0.4127(2) 0.0310 1.0000 Uani
C18 C 0.4750(4) 0.5203(8) 0.3859(3) 0.0342 1.0000 Uani
C19 C 0.3773(3) 0.4712(7) 0.3266(2) 0.0274 1.0000 Uani
I2 I 0.70102(2) 0.44474(11) 0.498565(18) 0.0510 1.0000 Uani
C20 C 0.0909(3) 0.3923(7) 0.1252(2) 0.0233 1.0000 Uani
O3 O 0.0538(3) 0.5654(6) 0.1275(2) 0.0391 1.0000 Uani
O4 O 0.0318(2) 0.2209(5) 0.09660(19) 0.0285 1.0000 Uani
C21 C -0.0877(3) 0.2455(9) 0.0698(3) 0.0353 1.0000 Uani
C22 C -0.1333(4) 0.0264(9) 0.0730(3) 0.0382 1.0000 Uani
C23 C 0.5729(3) 0.4175(8) 0.1375(2) 0.0267 1.0000 Uani
C24 C 0.6431(4) 0.2479(9) 0.1583(3) 0.0395 1.0000 Uani
C25 C 0.7436(5) 0.2724(11) 0.2162(4) 0.0493 1.0000 Uani
C26 C 0.7736(4) 0.4653(13) 0.2521(4) 0.0633 1.0000 Uani
C27 C 0.7044(7) 0.6324(12) 0.2307(6) 0.0802 1.0000 Uani
C28 C 0.6044(5) 0.6129(9) 0.1720(4) 0.0538 1.0000 Uani
H31 H 0.205(4) -0.002(8) 0.133(3) 0.033(13) 1.0000 Uiso
H41 H 0.4083 0.0239 0.1656 0.0243 1.0000 Uiso
H51 H 0.3781 -0.0691 0.0340 0.0322 1.0000 Uiso
H52 H 0.2879 0.1174 0.0016 0.0322 1.0000 Uiso
H61 H 0.4422 0.5336 0.0515 0.0304 1.0000 Uiso
H91 H 0.1482 -0.1757 0.2292 0.0302 1.0000 Uiso
H101 H 0.0150 -0.2790 0.2977 0.0367 1.0000 Uiso
H121 H 0.0204 0.3161 0.3976 0.0359 1.0000 Uiso
H131 H 0.1569 0.4198 0.3310 0.0341 1.0000 Uiso
H151 H 0.4234 -0.0367 0.3050 0.0304 1.0000 Uiso
H161 H 0.5911 0.0484 0.4042 0.0370 1.0000 Uiso
H181 H 0.4881 0.6665 0.4086 0.0402 1.0000 Uiso
H191 H 0.3211 0.5835 0.3061 0.0322 1.0000 Uiso
H211 H -0.1131 0.3425 0.1075 0.0406 1.0000 Uiso
H212 H -0.1111 0.3024 0.0126 0.0406 1.0000 Uiso
H221 H -0.2153 0.0318 0.0553 0.0454 1.0000 Uiso
H222 H -0.1084 -0.0287 0.1305 0.0454 1.0000 Uiso
H223 H -0.1064 -0.0688 0.0355 0.0454 1.0000 Uiso
H241 H 0.6217 0.1076 0.1318 0.0483 1.0000 Uiso
H251 H 0.7944 0.1492 0.2317 0.0584 1.0000 Uiso
H261 H 0.8459 0.4829 0.2938 0.0702 1.0000 Uiso
H271 H 0.7260 0.7719 0.2579 0.0848 1.0000 Uiso
H281 H 0.5559 0.7385 0.1549 0.0578 1.0000 Uiso
_refine_ls_extinction_method     None

loop_
_oxford_twin_element_scale_factors
0.8322(13)0.1678(13)

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 . C1 . 1.363(5) yes
N1 . C4 . 1.466(5) yes
N1 . C6 . 1.462(4) yes
C1 . C2 . 1.501(5) yes
C1 . O2 . 1.214(5) yes
C2 . C3 . 1.519(6) yes
C2 . C7 . 1.556(5) yes
C2 . C20 . 1.500(5) yes
C3 . C4 . 1.511(5) yes
C3 . C7 . 1.508(5) yes
C3 . H31 . 0.94(5) no
C4 . C5 . 1.523(5) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.451(5) yes
C5 . H51 . 1.000 no
C5 . H52 . 1.000 no
O1 . C6 . 1.430(5) yes
C6 . C23 . 1.507(5) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.507(5) yes
C7 . C14 . 1.514(5) yes
C8 . C9 . 1.389(6) yes
C8 . C13 . 1.398(6) yes
C9 . C10 . 1.386(5) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.365(6) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.395(7) yes
C11 . I1 . 2.104(4) yes
C12 . C13 . 1.391(6) yes
C12 . H121 . 1.000 no
C13 . H131 . 1.000 no
C14 . C15 . 1.391(6) yes
C14 . C19 . 1.401(6) yes
C15 . C16 . 1.390(6) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.384(7) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.385(7) yes
C17 . I2 . 2.098(4) yes
C18 . C19 . 1.401(6) yes
C18 . H181 . 1.000 no
C19 . H191 . 1.000 no
C20 . O3 . 1.199(6) yes
C20 . O4 . 1.334(5) yes
O4 . C21 . 1.465(5) yes
C21 . C22 . 1.511(8) yes
C21 . H211 . 1.000 no
C21 . H212 . 1.000 no
C22 . H221 . 1.000 no
C22 . H222 . 1.000 no
C22 . H223 . 1.000 no
C23 . C24 . 1.379(7) yes
C23 . C28 . 1.382(8) yes
C24 . C25 . 1.390(8) yes
C24 . H241 . 1.000 no
C25 . C26 . 1.373(10) yes
C25 . H251 . 1.000 no
C26 . C27 . 1.359(11) yes
C26 . H261 . 1.000 no
C27 . C28 . 1.388(9) yes
C27 . H271 . 1.000 no
C28 . H281 . 1.000 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
C1 . N1 . C4 . 114.4(3) yes
C1 . N1 . C6 . 124.7(3) yes
C4 . N1 . C6 . 108.4(3) yes
N1 . C1 . C2 . 106.7(3) yes
N1 . C1 . O2 . 125.3(4) yes
C2 . C1 . O2 . 128.1(4) yes
C1 . C2 . C3 . 106.6(3) yes
C1 . C2 . C7 . 115.8(3) yes
C3 . C2 . C7 . 58.7(2) yes
C1 . C2 . C20 . 119.3(3) yes
C3 . C2 . C20 . 122.6(3) yes
C7 . C2 . C20 . 119.1(3) yes
C2 . C3 . C4 . 106.6(3) yes
C2 . C3 . C7 . 61.9(3) yes
C4 . C3 . C7 . 116.3(3) yes
C2 . C3 . H31 . 122(3) no
C4 . C3 . H31 . 119(3) no
C7 . C3 . H31 . 118(3) no
N1 . C4 . C3 . 103.6(3) yes
N1 . C4 . C5 . 99.7(3) yes
C3 . C4 . C5 . 119.4(3) yes
N1 . C4 . H41 . 122.856 no
C3 . C4 . H41 . 104.441 no
C5 . C4 . H41 . 108.045 no
C4 . C5 . O1 . 103.0(3) yes
C4 . C5 . H51 . 111.065 no
O1 . C5 . H51 . 111.065 no
C4 . C5 . H52 . 111.065 no
O1 . C5 . H52 . 111.065 no
H51 . C5 . H52 . 109.467 no
C5 . O1 . C6 . 110.0(3) yes
N1 . C6 . O1 . 104.1(3) yes
N1 . C6 . C23 . 110.1(3) yes
O1 . C6 . C23 . 111.8(4) yes
N1 . C6 . H61 . 113.360 no
O1 . C6 . H61 . 111.777 no
C23 . C6 . H61 . 105.876 no
C2 . C7 . C3 . 59.4(2) yes
C2 . C7 . C8 . 116.3(3) yes
C3 . C7 . C8 . 118.4(3) yes
C2 . C7 . C14 . 119.3(3) yes
C3 . C7 . C14 . 120.5(3) yes
C8 . C7 . C14 . 113.0(3) yes
C7 . C8 . C9 . 122.6(3) yes
C7 . C8 . C13 . 118.4(4) yes
C9 . C8 . C13 . 119.0(4) yes
C8 . C9 . C10 . 119.9(4) yes
C8 . C9 . H91 . 120.067 no
C10 . C9 . H91 . 120.068 no
C9 . C10 . C11 . 120.8(4) yes
C9 . C10 . H101 . 119.578 no
C11 . C10 . H101 . 119.578 no
C10 . C11 . C12 . 120.7(4) yes
C10 . C11 . I1 . 120.4(3) yes
C12 . C11 . I1 . 118.9(3) yes
C11 . C12 . C13 . 118.5(4) yes
C11 . C12 . H121 . 120.766 no
C13 . C12 . H121 . 120.766 no
C8 . C13 . C12 . 121.0(4) yes
C8 . C13 . H131 . 119.479 no
C12 . C13 . H131 . 119.478 no
C7 . C14 . C15 . 119.3(4) yes
C7 . C14 . C19 . 121.7(3) yes
C15 . C14 . C19 . 118.9(3) yes
C14 . C15 . C16 . 120.9(4) yes
C14 . C15 . H151 . 119.540 no
C16 . C15 . H151 . 119.540 no
C15 . C16 . C17 . 119.5(4) yes
C15 . C16 . H161 . 120.225 no
C17 . C16 . H161 . 120.225 no
C16 . C17 . C18 . 120.9(4) yes
C16 . C17 . I2 . 120.4(3) yes
C18 . C17 . I2 . 118.7(3) yes
C17 . C18 . C19 . 119.5(4) yes
C17 . C18 . H181 . 120.275 no
C19 . C18 . H181 . 120.274 no
C14 . C19 . C18 . 120.2(4) yes
C14 . C19 . H191 . 119.880 no
C18 . C19 . H191 . 119.881 no
C2 . C20 . O3 . 125.0(4) yes
C2 . C20 . O4 . 110.1(3) yes
O3 . C20 . O4 . 124.9(3) yes
C20 . O4 . C21 . 117.2(3) yes
O4 . C21 . C22 . 105.3(4) yes
O4 . C21 . H211 . 110.511 no
C22 . C21 . H211 . 110.510 no
O4 . C21 . H212 . 110.511 no
C22 . C21 . H212 . 110.510 no
H211 . C21 . H212 . 109.467 no
C21 . C22 . H221 . 109.467 no
C21 . C22 . H222 . 109.466 no
H221 . C22 . H222 . 109.475 no
C21 . C22 . H223 . 109.467 no
H221 . C22 . H223 . 109.476 no
H222 . C22 . H223 . 109.476 no
C6 . C23 . C24 . 122.9(5) yes
C6 . C23 . C28 . 117.0(4) yes
C24 . C23 . C28 . 119.9(4) yes
C23 . C24 . C25 . 119.8(5) yes
C23 . C24 . H241 . 120.090 no
C25 . C24 . H241 . 120.091 no
C24 . C25 . C26 . 120.2(5) yes
C24 . C25 . H251 . 119.912 no
C26 . C25 . H251 . 119.914 no
C25 . C26 . C27 . 119.7(5) yes
C25 . C26 . H261 . 120.164 no
C27 . C26 . H261 . 120.166 no
C26 . C27 . C28 . 121.2(7) yes
C26 . C27 . H271 . 119.378 no
C28 . C27 . H271 . 119.378 no
C23 . C28 . C27 . 119.1(6) yes
C23 . C28 . H281 . 120.453 no
C27 . C28 . H281 . 120.453 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8c
_audit_block_doi                 10.5517/ccs3sf2
_database_code_depnum_ccdc_archive 'CCDC 718624'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_chemical_absolute_configuration syn

_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrogen atom H31 attached to the strained ring-junction C3 was located in
a difference Fourier map and its coordinates and isotropic displacement
parameter subsequently refined. Other hydrogens were positioned geometrically.
;
#=============================================================

_cell_length_a                   10.5459(2)
_cell_angle_alpha                90
_cell_length_b                   12.5242(2)
_cell_angle_beta                 90
_cell_length_c                   17.0855(3)
_cell_angle_gamma                90
_cell_volume                     2256.64(7)

_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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B


_cell_formula_units_Z            4
_chemical_formula_sum            ' C28 H25 N1 O4 '
_chemical_formula_moiety         ' C28 H25 N1 O4 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         439.51


_cell_measurement_reflns_used    15417
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' fragment '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_max          0.24

_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.086

_diffrn_measurement_method       ω

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            15417
_reflns_number_total             2849
#2914 unique reflections including absences
_diffrn_reflns_av_R_equivalents  0.042

_diffrn_reflns_theta_min         5.150
_diffrn_reflns_theta_max         27.480
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              0
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              22


_refine_diff_density_min         -0.18
_refine_diff_density_max         0.15


_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_number_parameters     302

#_refine_ls_R_factor_ref 0.0353
_refine_ls_wR_factor_ref         0.0389
_refine_ls_goodness_of_fit_ref   1.1344

#_reflns_number_all 2894
_refine_ls_R_factor_all          0.0547
_refine_ls_wR_factor_all         0.0546

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                2039
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_gt          0.0389


_refine_ls_shift/su_max          0.011648
_refine_ls_structure_factor_coef F
_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:
0.382 0.161 0.151
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

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
N1 N 0.16374(19) 0.69971(15) 0.22027(10) 0.0305 1.0000 Uani
C1 C 0.1231(2) 0.77315(18) 0.27467(12) 0.0286 1.0000 Uani
C2 C -0.0020(2) 0.73467(17) 0.30681(12) 0.0277 1.0000 Uani
C3 C -0.0413(2) 0.64123(18) 0.25453(13) 0.0286 1.0000 Uani
C4 C 0.0629(2) 0.62703(18) 0.19453(13) 0.0312 1.0000 Uani
C5 C 0.0402(3) 0.6691(2) 0.11236(15) 0.0426 1.0000 Uani
O1 O 0.1622(2) 0.70061(18) 0.08621(10) 0.0519 1.0000 Uani
C6 C 0.2381(3) 0.7309(2) 0.15204(14) 0.0383 1.0000 Uani
O2 O 0.17830(18) 0.85578(13) 0.29088(10) 0.0381 1.0000 Uani
C7 C -0.0088(2) 0.61818(16) 0.33843(12) 0.0255 1.0000 Uani
C8 C -0.1178(2) 0.59552(17) 0.39295(13) 0.0298 1.0000 Uani
C9 C -0.2179(2) 0.5314(2) 0.36958(16) 0.0369 1.0000 Uani
C10 C -0.3182(3) 0.5116(2) 0.4208(2) 0.0509 1.0000 Uani
C11 C -0.3182(3) 0.5560(2) 0.49518(19) 0.0504 1.0000 Uani
C12 C -0.2174(3) 0.6178(2) 0.51900(15) 0.0448 1.0000 Uani
C13 C -0.1169(3) 0.63723(19) 0.46862(13) 0.0349 1.0000 Uani
C14 C 0.1107(2) 0.55970(17) 0.36046(12) 0.0260 1.0000 Uani
C15 C 0.1247(2) 0.45338(18) 0.33745(13) 0.0311 1.0000 Uani
C16 C 0.2301(2) 0.39527(19) 0.36059(15) 0.0368 1.0000 Uani
C17 C 0.3213(2) 0.4415(2) 0.40825(14) 0.0376 1.0000 Uani
C18 C 0.3076(3) 0.5471(2) 0.43153(15) 0.0391 1.0000 Uani
C19 C 0.2029(2) 0.60542(19) 0.40773(13) 0.0329 1.0000 Uani
C20 C -0.0902(2) 0.81468(18) 0.34127(13) 0.0302 1.0000 Uani
O3 O -0.05695(18) 0.88570(14) 0.38428(10) 0.0395 1.0000 Uani
O4 O -0.20938(16) 0.79712(13) 0.31976(10) 0.0361 1.0000 Uani
C21 C -0.3051(3) 0.8654(2) 0.35738(19) 0.0510 1.0000 Uani
C22 C -0.4306(3) 0.8188(3) 0.3394(3) 0.0727 1.0000 Uani
C23 C 0.3666(3) 0.67855(19) 0.14703(15) 0.0370 1.0000 Uani
C24 C 0.4308(4) 0.6770(3) 0.07652(19) 0.0646 1.0000 Uani
C25 C 0.5519(4) 0.6330(3) 0.0720(2) 0.0677 1.0000 Uani
C26 C 0.6078(3) 0.5903(3) 0.1367(2) 0.0609 1.0000 Uani
C27 C 0.5434(3) 0.5888(4) 0.2066(2) 0.0704 1.0000 Uani
C28 C 0.4224(3) 0.6335(3) 0.21194(17) 0.0554 1.0000 Uani
H31 H -0.130(3) 0.636(2) 0.2385(14) 0.029(6) 1.0000 Uiso
H41 H 0.0765 0.5481 0.1917 0.0374 1.0000 Uiso
H51 H -0.0190 0.7315 0.1133 0.0511 1.0000 Uiso
H52 H 0.0046 0.6120 0.0779 0.0511 1.0000 Uiso
H61 H 0.2571 0.8090 0.1546 0.0459 1.0000 Uiso
H91 H -0.2182 0.4993 0.3160 0.0443 1.0000 Uiso
H101 H -0.3904 0.4653 0.4038 0.0611 1.0000 Uiso
H111 H -0.3911 0.5431 0.5314 0.0605 1.0000 Uiso
H121 H -0.2167 0.6489 0.5729 0.0537 1.0000 Uiso
H131 H -0.0434 0.6813 0.4866 0.0419 1.0000 Uiso
H151 H 0.0583 0.4190 0.3041 0.0373 1.0000 Uiso
H161 H 0.2405 0.3197 0.3428 0.0442 1.0000 Uiso
H171 H 0.3965 0.3991 0.4257 0.0451 1.0000 Uiso
H181 H 0.3733 0.5810 0.4655 0.0469 1.0000 Uiso
H191 H 0.1937 0.6814 0.4248 0.0394 1.0000 Uiso
H211 H -0.2997 0.9396 0.3362 0.0612 1.0000 Uiso
H212 H -0.2913 0.8668 0.4153 0.0612 1.0000 Uiso
H221 H -0.4984 0.8633 0.3642 0.0873 1.0000 Uiso
H222 H -0.4433 0.8173 0.2814 0.0873 1.0000 Uiso
H223 H -0.4349 0.7445 0.3606 0.0873 1.0000 Uiso
H241 H 0.3903 0.7076 0.0286 0.0775 1.0000 Uiso
H251 H 0.5981 0.6327 0.0209 0.0812 1.0000 Uiso
H261 H 0.6954 0.5602 0.1333 0.0731 1.0000 Uiso
H271 H 0.5833 0.5555 0.2537 0.0844 1.0000 Uiso
H281 H 0.3763 0.6328 0.2631 0.0664 1.0000 Uiso
_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
N1 . C1 . 1.376(3) yes
N1 . C4 . 1.468(3) yes
N1 . C6 . 1.458(3) yes
C1 . C2 . 1.508(3) yes
C1 . O2 . 1.219(3) yes
C2 . C3 . 1.529(3) yes
C2 . C7 . 1.557(3) yes
C2 . C20 . 1.488(3) yes
C3 . C4 . 1.513(3) yes
C3 . C7 . 1.502(3) yes
C3 . H31 . 0.98(3) no
C4 . C5 . 1.519(3) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.417(4) yes
C5 . H51 . 1.000 no
C5 . H52 . 1.000 no
O1 . C6 . 1.432(3) yes
C6 . C23 . 1.508(4) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.507(3) yes
C7 . C14 . 1.505(3) yes
C8 . C9 . 1.385(3) yes
C8 . C13 . 1.394(3) yes
C9 . C10 . 1.395(4) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.387(5) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.376(4) yes
C11 . H111 . 1.000 no
C12 . C13 . 1.387(4) yes
C12 . H121 . 1.000 no
C13 . H131 . 1.000 no
C14 . C15 . 1.396(3) yes
C14 . C19 . 1.388(3) yes
C15 . C16 . 1.387(3) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.387(4) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.389(4) yes
C17 . H171 . 1.000 no
C18 . C19 . 1.385(4) yes
C18 . H181 . 1.000 no
C19 . H191 . 1.000 no
C20 . O3 . 1.206(3) yes
C20 . O4 . 1.328(3) yes
O4 . C21 . 1.471(3) yes
C21 . C22 . 1.478(5) yes
C21 . H211 . 1.000 no
C21 . H212 . 1.000 no
C22 . H221 . 1.000 no
C22 . H222 . 1.000 no
C22 . H223 . 1.000 no
C23 . C24 . 1.382(4) yes
C23 . C28 . 1.377(4) yes
C24 . C25 . 1.392(5) yes
C24 . H241 . 1.000 no
C25 . C26 . 1.361(5) yes
C25 . H251 . 1.000 no
C26 . C27 . 1.374(5) yes
C26 . H261 . 1.000 no
C27 . C28 . 1.396(4) yes
C27 . H271 . 1.000 no
C28 . H281 . 1.000 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
C1 . N1 . C4 . 113.01(19) yes
C1 . N1 . C6 . 121.9(2) yes
C4 . N1 . C6 . 108.44(18) yes
N1 . C1 . C2 . 107.76(19) yes
N1 . C1 . O2 . 124.9(2) yes
C2 . C1 . O2 . 127.3(2) yes
C1 . C2 . C3 . 105.59(18) yes
C1 . C2 . C7 . 117.74(19) yes
C3 . C2 . C7 . 58.22(14) yes
C1 . C2 . C20 . 118.39(19) yes
C3 . C2 . C20 . 125.2(2) yes
C7 . C2 . C20 . 117.71(19) yes
C2 . C3 . C4 . 106.79(19) yes
C2 . C3 . C7 . 61.82(14) yes
C4 . C3 . C7 . 117.3(2) yes
C2 . C3 . H31 . 118.1(15) no
C4 . C3 . H31 . 120.0(14) no
C7 . C3 . H31 . 118.2(15) no
N1 . C4 . C3 . 104.51(17) yes
N1 . C4 . C5 . 100.1(2) yes
C3 . C4 . C5 . 118.1(2) yes
N1 . C4 . H41 . 121.516 no
C3 . C4 . H41 . 104.672 no
C5 . C4 . H41 . 108.758 no
C4 . C5 . O1 . 104.2(2) yes
C4 . C5 . H51 . 110.772 no
O1 . C5 . H51 . 110.772 no
C4 . C5 . H52 . 110.772 no
O1 . C5 . H52 . 110.773 no
H51 . C5 . H52 . 109.467 no
C5 . O1 . C6 . 109.47(18) yes
N1 . C6 . O1 . 104.9(2) yes
N1 . C6 . C23 . 114.3(2) yes
O1 . C6 . C23 . 110.0(2) yes
N1 . C6 . H61 . 109.580 no
O1 . C6 . H61 . 113.910 no
C23 . C6 . H61 . 104.355 no
C2 . C7 . C3 . 59.96(13) yes
C2 . C7 . C8 . 115.19(18) yes
C3 . C7 . C8 . 116.8(2) yes
C2 . C7 . C14 . 120.30(19) yes
C3 . C7 . C14 . 121.57(19) yes
C8 . C7 . C14 . 113.12(17) yes
C7 . C8 . C9 . 120.8(2) yes
C7 . C8 . C13 . 119.8(2) yes
C9 . C8 . C13 . 119.3(2) yes
C8 . C9 . C10 . 120.0(2) yes
C8 . C9 . H91 . 119.994 no
C10 . C9 . H91 . 119.995 no
C9 . C10 . C11 . 120.2(3) yes
C9 . C10 . H101 . 119.904 no
C11 . C10 . H101 . 119.904 no
C10 . C11 . C12 . 119.8(3) yes
C10 . C11 . H111 . 120.107 no
C12 . C11 . H111 . 120.107 no
C11 . C12 . C13 . 120.4(3) yes
C11 . C12 . H121 . 119.821 no
C13 . C12 . H121 . 119.822 no
C8 . C13 . C12 . 120.3(2) yes
C8 . C13 . H131 . 119.870 no
C12 . C13 . H131 . 119.871 no
C7 . C14 . C15 . 118.8(2) yes
C7 . C14 . C19 . 122.1(2) yes
C15 . C14 . C19 . 118.9(2) yes
C14 . C15 . C16 . 120.3(2) yes
C14 . C15 . H151 . 119.834 no
C16 . C15 . H151 . 119.834 no
C15 . C16 . C17 . 120.3(2) yes
C15 . C16 . H161 . 119.850 no
C17 . C16 . H161 . 119.850 no
C16 . C17 . C18 . 119.6(2) yes
C16 . C17 . H171 . 120.220 no
C18 . C17 . H171 . 120.218 no
C17 . C18 . C19 . 120.1(2) yes
C17 . C18 . H181 . 119.943 no
C19 . C18 . H181 . 119.943 no
C14 . C19 . C18 . 120.8(2) yes
C14 . C19 . H191 . 119.613 no
C18 . C19 . H191 . 119.611 no
C2 . C20 . O3 . 123.8(2) yes
C2 . C20 . O4 . 111.7(2) yes
O3 . C20 . O4 . 124.5(2) yes
C20 . O4 . C21 . 115.6(2) yes
O4 . C21 . C22 . 107.1(2) yes
O4 . C21 . H211 . 110.053 no
C22 . C21 . H211 . 110.053 no
O4 . C21 . H212 . 110.052 no
C22 . C21 . H212 . 110.051 no
H211 . C21 . H212 . 109.468 no
C21 . C22 . H221 . 109.468 no
C21 . C22 . H222 . 109.467 no
H221 . C22 . H222 . 109.474 no
C21 . C22 . H223 . 109.469 no
H221 . C22 . H223 . 109.476 no
H222 . C22 . H223 . 109.475 no
C6 . C23 . C24 . 119.7(3) yes
C6 . C23 . C28 . 121.1(2) yes
C24 . C23 . C28 . 119.1(3) yes
C23 . C24 . C25 . 120.2(3) yes
C23 . C24 . H241 . 119.902 no
C25 . C24 . H241 . 119.902 no
C24 . C25 . C26 . 120.5(3) yes
C24 . C25 . H251 . 119.751 no
C26 . C25 . H251 . 119.752 no
C25 . C26 . C27 . 119.8(3) yes
C25 . C26 . H261 . 120.092 no
C27 . C26 . H261 . 120.092 no
C26 . C27 . C28 . 120.2(3) yes
C26 . C27 . H271 . 119.918 no
C28 . C27 . H271 . 119.919 no
C23 . C28 . C27 . 120.2(3) yes
C23 . C28 . H281 . 119.918 no
C27 . C28 . H281 . 119.919 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8d
_audit_block_doi                 10.5517/ccs3sg3
_database_code_depnum_ccdc_archive 'CCDC 718625'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             08-02-19
_audit_creation_method           CRYSTALS_ver_12.85

_oxford_structure_analysis_title 5726
_chemical_name_systematic        ?
_chemical_melting_point          'not measured'

_cell_length_a                   12.4892(2)
_cell_length_b                   6.37210(10)
_cell_length_c                   16.0608(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.7444(7)
_cell_angle_gamma                90
_cell_volume                     1241.56(4)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 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'
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            2

# Given Formula = C29 H30 N1 O6
# Dc = 1.31 Fooo = 528.00 Mu = 0.91 M = 488.56
# Found Formula = C30 H29 N1 O6
# Dc = 1.34 FOOO = 528.00 Mu = 0.93 M = 499.56

_chemical_formula_sum            'C30 H29 N1 O6'
_chemical_formula_moiety         'C30 H29 N1 O6'
_chemical_compound_source        .
_chemical_formula_weight         499.56


_cell_measurement_reflns_used    3049
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.093

# 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  0.83
_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       'Nonius KappaCCD'
_diffrn_measurement_device_type  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, 1997-2001).'
_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_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            19857
_reflns_number_total             3072
_diffrn_reflns_av_R_equivalents  0.053
# Number of reflections with Friedels Law is 3072
# Number of reflections without Friedels Law is 5629
# Theoretical number of reflections is about 2858


_diffrn_reflns_theta_min         5.502
_diffrn_reflns_theta_max         27.520
_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        26.969
_diffrn_measured_fraction_theta_full 0.984


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.78
_oxford_diffrn_Wilson_scale      1.50

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

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.15


# 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         3072
_refine_ls_number_restraints     1
_refine_ls_number_parameters     334
_oxford_refine_ls_R_factor_ref   0.0405
_refine_ls_wR_factor_ref         0.0903
_refine_ls_goodness_of_fit_ref   0.9835
_refine_ls_shift/su_max          0.000360


# The values computed from all data
_oxford_reflns_number_all        3072
_refine_ls_R_factor_all          0.0405
_refine_ls_wR_factor_all         0.0903

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2794
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0880

# 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 unk


_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= Modified Sheldrick
w=1/[σ²(F²) + ( 0.06P)² + 0.15P]
,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 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
N1 N 0.62545(12) 0.7806(2) 0.86313(10) 0.0272 1.0000 Uani . . . . . . .
C2 C 0.54463(14) 0.8290(3) 0.91245(11) 0.0302 1.0000 Uani . . . . . . .
O3 O 0.54794(11) 0.6499(2) 0.96664(8) 0.0350 1.0000 Uani . . . . . . .
C4 C 0.63910(15) 0.5156(3) 0.95995(12) 0.0320 1.0000 Uani . . . . . . .
C5 C 0.64914(15) 0.5557(3) 0.86912(11) 0.0270 1.0000 Uani . . . . . . .
C6 C 0.75988(14) 0.5384(3) 0.84608(11) 0.0265 1.0000 Uani . . . . . . .
C7 C 0.80070(14) 0.7613(3) 0.84070(11) 0.0268 1.0000 Uani . . . . . . .
C8 C 0.71395(14) 0.9041(3) 0.86011(11) 0.0273 1.0000 Uani . . . . . . .
C9 C 0.76379(13) 0.6228(3) 0.75940(11) 0.0258 1.0000 Uani . . . . . . .
C10 C 0.85296(14) 0.5478(3) 0.71762(11) 0.0272 1.0000 Uani . . . . . . .
C11 C 0.89139(15) 0.3432(3) 0.72531(12) 0.0327 1.0000 Uani . . . . . . .
C12 C 0.97064(15) 0.2773(3) 0.68345(13) 0.0344 1.0000 Uani . . . . . . .
C13 C 1.01327(15) 0.4170(3) 0.63316(12) 0.0312 1.0000 Uani . . . . . . .
O14 O 1.09063(11) 0.3362(3) 0.59373(9) 0.0395 1.0000 Uani . . . . . . .
C15 C 1.14175(18) 0.4790(4) 0.54665(15) 0.0444 1.0000 Uani . . . . . . .
C16 C 0.97668(15) 0.6228(3) 0.62508(12) 0.0310 1.0000 Uani . . . . . . .
C17 C 0.89680(15) 0.6863(3) 0.66754(11) 0.0307 1.0000 Uani . . . . . . .
C18 C 0.65615(14) 0.6711(3) 0.69569(11) 0.0269 1.0000 Uani . . . . . . .
C19 C 0.62816(14) 0.8710(3) 0.66367(11) 0.0298 1.0000 Uani . . . . . . .
C20 C 0.52680(15) 0.9102(3) 0.60662(12) 0.0331 1.0000 Uani . . . . . . .
C21 C 0.45274(15) 0.7469(3) 0.58221(12) 0.0333 1.0000 Uani . . . . . . .
O22 O 0.35071(11) 0.7674(3) 0.52766(10) 0.0442 1.0000 Uani . . . . . . .
C23 C 0.30539(17) 0.9740(4) 0.51467(14) 0.0447 1.0000 Uani . . . . . . .
C24 C 0.48093(15) 0.5444(3) 0.61202(12) 0.0337 1.0000 Uani . . . . . . .
C25 C 0.58207(15) 0.5073(3) 0.66815(11) 0.0303 1.0000 Uani . . . . . . .
C26 C 0.91985(15) 0.8187(3) 0.87190(11) 0.0292 1.0000 Uani . . . . . . .
O27 O 0.95666(12) 0.9927(3) 0.87234(11) 0.0452 1.0000 Uani . . . . . . .
O28 O 0.97904(10) 0.6477(2) 0.89976(9) 0.0351 1.0000 Uani . . . . . . .
C29 C 1.09789(15) 0.6701(4) 0.92846(14) 0.0403 1.0000 Uani . . . . . . .
C30 C 1.14569(17) 0.4557(4) 0.92315(14) 0.0438 1.0000 Uani . . . . . . .
C31 C 0.43205(15) 0.8611(3) 0.85376(12) 0.0313 1.0000 Uani . . . . . . .
C32 C 0.40482(18) 1.0596(4) 0.81989(14) 0.0409 1.0000 Uani . . . . . . .
C33 C 0.30587(19) 1.0928(4) 0.75992(15) 0.0494 1.0000 Uani . . . . . . .
C34 C 0.23478(18) 0.9287(4) 0.73367(14) 0.0461 1.0000 Uani . . . . . . .
C35 C 0.26012(18) 0.7311(4) 0.76803(15) 0.0460 1.0000 Uani . . . . . . .
C36 C 0.35926(17) 0.6971(4) 0.82832(13) 0.0394 1.0000 Uani . . . . . . .
O37 O 0.71848(12) 1.0933(2) 0.87195(9) 0.0353 1.0000 Uani . . . . . . .
H21 H 0.5682 0.9571 0.9479 0.0354 1.0000 Uiso R . . . . . .
H42 H 0.7078 0.5570 1.0030 0.0384 1.0000 Uiso R . . . . . .
H41 H 0.6200 0.3679 0.9701 0.0393 1.0000 Uiso R . . . . . .
H51 H 0.5923 0.4782 0.8293 0.0332 1.0000 Uiso R . . . . . .
H61 H 0.8102 0.4281 0.8714 0.0316 1.0000 Uiso R . . . . . .
H111 H 0.8606 0.2486 0.7595 0.0407 1.0000 Uiso R . . . . . .
H121 H 0.9966 0.1380 0.6899 0.0421 1.0000 Uiso R . . . . . .
H151 H 1.1915 0.3963 0.5204 0.0690 1.0000 Uiso R . . . . . .
H153 H 1.1842 0.5839 0.5852 0.0697 1.0000 Uiso R . . . . . .
H152 H 1.0853 0.5496 0.5017 0.0693 1.0000 Uiso R . . . . . .
H161 H 1.0053 0.7199 0.5908 0.0390 1.0000 Uiso R . . . . . .
H171 H 0.8707 0.8289 0.6615 0.0370 1.0000 Uiso R . . . . . .
H191 H 0.6762 0.9841 0.6805 0.0356 1.0000 Uiso R . . . . . .
H201 H 0.5091 1.0483 0.5852 0.0396 1.0000 Uiso R . . . . . .
H231 H 0.2307 0.9537 0.4814 0.0656 1.0000 Uiso R . . . . . .
H233 H 0.3071 1.0360 0.5715 0.0645 1.0000 Uiso R . . . . . .
H232 H 0.3482 1.0597 0.4826 0.0653 1.0000 Uiso R . . . . . .
H241 H 0.4300 0.4319 0.5949 0.0397 1.0000 Uiso R . . . . . .
H251 H 0.6012 0.3642 0.6880 0.0364 1.0000 Uiso R . . . . . .
H292 H 1.1140 0.7230 0.9870 0.0472 1.0000 Uiso R . . . . . .
H291 H 1.1235 0.7694 0.8919 0.0468 1.0000 Uiso R . . . . . .
H301 H 1.2263 0.4587 0.9430 0.0640 1.0000 Uiso R . . . . . .
H303 H 1.1170 0.3564 0.9591 0.0634 1.0000 Uiso R . . . . . .
H302 H 1.1250 0.4068 0.8643 0.0633 1.0000 Uiso R . . . . . .
H321 H 0.4540 1.1727 0.8374 0.0491 1.0000 Uiso R . . . . . .
H331 H 0.2877 1.2292 0.7384 0.0576 1.0000 Uiso R . . . . . .
H341 H 0.1664 0.9482 0.6919 0.0551 1.0000 Uiso R . . . . . .
H351 H 0.2102 0.6181 0.7521 0.0548 1.0000 Uiso R . . . . . .
H361 H 0.3773 0.5592 0.8522 0.0473 1.0000 Uiso R . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.814(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
N1 . C2 . 1.456(2) yes
N1 . C5 . 1.462(2) yes
N1 . C8 . 1.367(2) yes
C2 . O3 . 1.430(2) yes
C2 . C31 . 1.509(2) yes
C2 . H21 . 0.999 no
O3 . C4 . 1.449(2) yes
C4 . C5 . 1.515(3) yes
C4 . H42 . 1.001 no
C4 . H41 . 0.994 no
C5 . C6 . 1.518(2) yes
C5 . H51 . 0.970 no
C6 . C7 . 1.518(3) yes
C6 . C9 . 1.504(2) yes
C6 . H61 . 0.965 no
C7 . C8 . 1.503(3) yes
C7 . C9 . 1.552(2) yes
C7 . C26 . 1.498(2) yes
C8 . O37 . 1.220(2) yes
C9 . C10 . 1.508(2) yes
C9 . C18 . 1.515(2) yes
C10 . C11 . 1.385(3) yes
C10 . C17 . 1.391(3) yes
C11 . C12 . 1.387(3) yes
C11 . H111 . 0.956 no
C12 . C13 . 1.390(3) yes
C12 . H121 . 0.942 no
C13 . O14 . 1.375(2) yes
C13 . C16 . 1.384(3) yes
O14 . C15 . 1.427(3) yes
C15 . H151 . 0.982 no
C15 . H153 . 0.977 no
C15 . H152 . 0.989 no
C16 . C17 . 1.396(3) yes
C16 . H161 . 0.952 no
C17 . H171 . 0.962 no
C18 . C19 . 1.387(3) yes
C18 . C25 . 1.395(3) yes
C19 . C20 . 1.398(2) yes
C19 . H191 . 0.936 no
C20 . C21 . 1.385(3) yes
C20 . H201 . 0.952 no
C21 . O22 . 1.370(2) yes
C21 . C24 . 1.392(3) yes
O22 . C23 . 1.429(3) yes
C23 . H231 . 0.967 no
C23 . H233 . 0.990 no
C23 . H232 . 0.990 no
C24 . C25 . 1.387(2) yes
C24 . H241 . 0.955 no
C25 . H251 . 0.977 no
C26 . O27 . 1.200(3) yes
C26 . O28 . 1.333(2) yes
O28 . C29 . 1.453(2) yes
C29 . C30 . 1.502(3) yes
C29 . H292 . 0.974 no
C29 . H291 . 0.967 no
C30 . H301 . 0.981 no
C30 . H303 . 0.980 no
C30 . H302 . 0.970 no
C31 . C32 . 1.387(3) yes
C31 . C36 . 1.381(3) yes
C32 . C33 . 1.391(3) yes
C32 . H321 . 0.945 no
C33 . C34 . 1.372(4) yes
C33 . H331 . 0.943 no
C34 . C35 . 1.381(4) yes
C34 . H341 . 0.961 no
C35 . C36 . 1.396(3) yes
C35 . H351 . 0.947 no
C36 . H361 . 0.963 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 109.10(15) yes
C2 . N1 . C8 . 124.62(16) yes
C5 . N1 . C8 . 114.45(15) yes
N1 . C2 . O3 . 103.81(15) yes
N1 . C2 . C31 . 110.62(14) yes
O3 . C2 . C31 . 112.09(15) yes
N1 . C2 . H21 . 109.5 no
O3 . C2 . H21 . 110.1 no
C31 . C2 . H21 . 110.5 no
C2 . O3 . C4 . 109.63(13) yes
O3 . C4 . C5 . 102.58(14) yes
O3 . C4 . H42 . 110.7 no
C5 . C4 . H42 . 111.5 no
O3 . C4 . H41 . 108.9 no
C5 . C4 . H41 . 113.4 no
H42 . C4 . H41 . 109.7 no
C4 . C5 . N1 . 99.63(15) yes
C4 . C5 . C6 . 120.71(15) yes
N1 . C5 . C6 . 103.72(15) yes
C4 . C5 . H51 . 109.5 no
N1 . C5 . H51 . 110.5 no
C6 . C5 . H51 . 111.6 no
C5 . C6 . C7 . 106.46(15) yes
C5 . C6 . C9 . 115.55(15) yes
C7 . C6 . C9 . 61.81(12) yes
C5 . C6 . H61 . 119.3 no
C7 . C6 . H61 . 120.7 no
C9 . C6 . H61 . 119.3 no
C6 . C7 . C8 . 106.63(14) yes
C6 . C7 . C9 . 58.64(11) yes
C8 . C7 . C9 . 115.72(14) yes
C6 . C7 . C26 . 121.98(15) yes
C8 . C7 . C26 . 119.35(16) yes
C9 . C7 . C26 . 119.54(15) yes
C7 . C8 . N1 . 106.71(15) yes
C7 . C8 . O37 . 128.45(18) yes
N1 . C8 . O37 . 124.84(18) yes
C7 . C9 . C6 . 59.55(12) yes
C7 . C9 . C10 . 116.82(14) yes
C6 . C9 . C10 . 119.24(15) yes
C7 . C9 . C18 . 119.42(15) yes
C6 . C9 . C18 . 118.63(14) yes
C10 . C9 . C18 . 113.23(14) yes
C9 . C10 . C11 . 122.39(16) yes
C9 . C10 . C17 . 119.35(16) yes
C11 . C10 . C17 . 118.24(17) yes
C10 . C11 . C12 . 120.94(18) yes
C10 . C11 . H111 . 117.8 no
C12 . C11 . H111 . 121.3 no
C11 . C12 . C13 . 120.22(19) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 119.8 no
C12 . C13 . O14 . 115.82(18) yes
C12 . C13 . C16 . 119.84(17) yes
O14 . C13 . C16 . 124.34(18) yes
C13 . O14 . C15 . 117.17(17) yes
O14 . C15 . H151 . 107.1 no
O14 . C15 . H153 . 110.1 no
H151 . C15 . H153 . 109.6 no
O14 . C15 . H152 . 110.2 no
H151 . C15 . H152 . 110.1 no
H153 . C15 . H152 . 109.6 no
C13 . C16 . C17 . 119.17(18) yes
C13 . C16 . H161 . 120.6 no
C17 . C16 . H161 . 120.2 no
C16 . C17 . C10 . 121.58(19) yes
C16 . C17 . H171 . 119.3 no
C10 . C17 . H171 . 119.2 no
C9 . C18 . C19 . 122.82(16) yes
C9 . C18 . C25 . 118.51(17) yes
C19 . C18 . C25 . 118.67(16) yes
C18 . C19 . C20 . 121.09(17) yes
C18 . C19 . H191 . 120.8 no
C20 . C19 . H191 . 118.1 no
C19 . C20 . C21 . 119.41(19) yes
C19 . C20 . H201 . 119.9 no
C21 . C20 . H201 . 120.6 no
C20 . C21 . O22 . 124.48(19) yes
C20 . C21 . C24 . 120.10(16) yes
O22 . C21 . C24 . 115.41(17) yes
C21 . O22 . C23 . 117.21(17) yes
O22 . C23 . H231 . 104.7 no
O22 . C23 . H233 . 108.2 no
H231 . C23 . H233 . 111.7 no
O22 . C23 . H232 . 109.8 no
H231 . C23 . H232 . 110.9 no
H233 . C23 . H232 . 111.3 no
C21 . C24 . C25 . 119.90(18) yes
C21 . C24 . H241 . 120.0 no
C25 . C24 . H241 . 120.1 no
C18 . C25 . C24 . 120.77(19) yes
C18 . C25 . H251 . 120.2 no
C24 . C25 . H251 . 119.1 no
C7 . C26 . O27 . 125.20(17) yes
C7 . C26 . O28 . 109.89(16) yes
O27 . C26 . O28 . 124.91(16) yes
C26 . O28 . C29 . 118.01(16) yes
O28 . C29 . C30 . 106.41(18) yes
O28 . C29 . H292 . 107.5 no
C30 . C29 . H292 . 112.1 no
O28 . C29 . H291 . 109.3 no
C30 . C29 . H291 . 111.6 no
H292 . C29 . H291 . 109.8 no
C29 . C30 . H301 . 110.8 no
C29 . C30 . H303 . 110.4 no
H301 . C30 . H303 . 108.1 no
C29 . C30 . H302 . 109.3 no
H301 . C30 . H302 . 109.7 no
H303 . C30 . H302 . 108.5 no
C2 . C31 . C32 . 118.27(18) yes
C2 . C31 . C36 . 122.17(19) yes
C32 . C31 . C36 . 119.40(18) yes
C31 . C32 . C33 . 120.3(2) yes
C31 . C32 . H321 . 119.8 no
C33 . C32 . H321 . 119.9 no
C32 . C33 . C34 . 120.0(2) yes
C32 . C33 . H331 . 119.4 no
C34 . C33 . H331 . 120.5 no
C33 . C34 . C35 . 120.15(19) yes
C33 . C34 . H341 . 121.3 no
C35 . C34 . H341 . 118.5 no
C34 . C35 . C36 . 120.0(2) yes
C34 . C35 . H351 . 120.8 no
C36 . C35 . H351 . 119.2 no
C35 . C36 . C31 . 120.1(2) yes
C35 . C36 . H361 . 120.1 no
C31 . C36 . H361 . 119.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C2 . H21 . O3 2_657 125 1.00 2.54 3.218(3) yes
C11 . H111 . O27 1_545 129 0.96 2.52 3.212(3) yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11
_audit_block_doi                 10.5517/ccs3sh4
_database_code_depnum_ccdc_archive 'CCDC 718626'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_chemical_absolute_configuration syn

_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrogen atom H31 attached to the strained ring-junction C3 was located in
a difference Fourier map and its coordinates and isotropic displacement
parameter subsequently refined. Other hydrogens were positioned geometrically.
;
#=============================================================

_cell_length_a                   11.1613(3)
_cell_angle_alpha                90
_cell_length_b                   13.6123(4)
_cell_angle_beta                 90
_cell_length_c                   14.3173(5)
_cell_angle_gamma                90
_cell_volume                     2175.24(12)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2yb'
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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B
'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_IV_Table_2.2B


_cell_formula_units_Z            4
_chemical_formula_sum            ' C28 H23 N O4 '
_chemical_formula_moiety         ' C28 H23 N O4 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         437.49


_cell_measurement_reflns_used    15297
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' prism '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.14
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.089

_diffrn_measurement_method       ω

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            15297
_reflns_number_total             2785
#2803 unique reflections including absences
_diffrn_reflns_av_R_equivalents  0.070

_diffrn_reflns_theta_min         5.218
_diffrn_reflns_theta_max         27.476
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.476
_diffrn_measured_fraction_theta_full 0.997


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


_refine_diff_density_min         -0.19
_refine_diff_density_max         0.19


_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_number_parameters     302

#_refine_ls_R_factor_ref 0.0360
_refine_ls_wR_factor_ref         0.0344
_refine_ls_goodness_of_fit_ref   1.1777

#_reflns_number_all 2785
_refine_ls_R_factor_all          0.0690
_refine_ls_wR_factor_all         0.0650

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.00u(I)
_reflns_number_gt                1884
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_gt          0.0344


_refine_ls_shift/su_max          0.005109
_refine_ls_structure_factor_coef F
_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:
0.190 0.0111 0.0347
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073


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

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
N1 N 0.6251(2) 0.69724(16) 0.41458(14) 0.0223 1.0000 Uani
C1 C 0.6995(2) 0.66229(19) 0.48300(19) 0.0225 1.0000 Uani
C2 C 0.6403(2) 0.67637(19) 0.57591(18) 0.0210 1.0000 Uani
C3 C 0.5310(3) 0.7394(2) 0.5581(2) 0.0247 1.0000 Uani
C4 C 0.5277(3) 0.7580(2) 0.45342(19) 0.0240 1.0000 Uani
C5 C 0.5674(3) 0.8587(2) 0.4206(2) 0.0311 1.0000 Uani
O1 O 0.6130(2) 0.83865(14) 0.32813(13) 0.0319 1.0000 Uani
C6 C 0.6738(3) 0.7458(2) 0.33066(19) 0.0253 1.0000 Uani
O2 O 0.80016(17) 0.62978(14) 0.46981(14) 0.0282 1.0000 Uani
C7 C 0.5118(2) 0.6351(2) 0.59177(19) 0.0230 1.0000 Uani
C8 C 0.4594(3) 0.5465(2) 0.5429(2) 0.0258 1.0000 Uani
C9 C 0.4536(3) 0.5204(2) 0.4485(2) 0.0297 1.0000 Uani
C10 C 0.4008(3) 0.4314(2) 0.4243(2) 0.0362 1.0000 Uani
C11 C 0.3543(3) 0.3688(2) 0.4916(3) 0.0409 1.0000 Uani
C12 C 0.3569(3) 0.3950(2) 0.5854(2) 0.0380 1.0000 Uani
C13 C 0.4090(3) 0.4841(2) 0.6104(2) 0.0300 1.0000 Uani
C14 C 0.4778(2) 0.6206(2) 0.69311(19) 0.0250 1.0000 Uani
C15 C 0.4942(3) 0.6815(2) 0.7693(2) 0.0281 1.0000 Uani
C16 C 0.4547(3) 0.6501(2) 0.8568(2) 0.0330 1.0000 Uani
C17 C 0.4000(3) 0.5587(3) 0.8671(2) 0.0396 1.0000 Uani
C18 C 0.3814(3) 0.4976(2) 0.7902(2) 0.0366 1.0000 Uani
C19 C 0.4205(3) 0.5295(2) 0.7031(2) 0.0280 1.0000 Uani
C20 C 0.7247(2) 0.6860(2) 0.65732(18) 0.0230 1.0000 Uani
O3 O 0.7587(2) 0.76275(13) 0.68900(14) 0.0322 1.0000 Uani
O4 O 0.75779(19) 0.59718(14) 0.68582(13) 0.0269 1.0000 Uani
C21 C 0.8421(3) 0.5910(2) 0.7639(2) 0.0281 1.0000 Uani
C22 C 0.7777(3) 0.5987(3) 0.8549(2) 0.0541 1.0000 Uani
C23 C 0.6514(3) 0.6916(2) 0.24078(19) 0.0241 1.0000 Uani
C24 C 0.5352(3) 0.6749(2) 0.2083(2) 0.0280 1.0000 Uani
C25 C 0.5183(3) 0.6256(2) 0.1245(2) 0.0317 1.0000 Uani
C26 C 0.6156(3) 0.5916(2) 0.0735(2) 0.0315 1.0000 Uani
C27 C 0.7305(3) 0.6065(2) 0.1064(2) 0.0311 1.0000 Uani
C28 C 0.7483(3) 0.6561(2) 0.18974(19) 0.0284 1.0000 Uani
H31 H 0.504(3) 0.791(2) 0.5990(19) 0.022(7) 1.0000 Uiso
H41 H 0.4426 0.7462 0.4346 0.0288 1.0000 Uiso
H51 H 0.6315 0.8859 0.4620 0.0373 1.0000 Uiso
H52 H 0.4985 0.9055 0.4183 0.0373 1.0000 Uiso
H61 H 0.7631 0.7499 0.3352 0.0304 1.0000 Uiso
H91 H 0.4868 0.5649 0.3994 0.0356 1.0000 Uiso
H101 H 0.3964 0.4122 0.3570 0.0434 1.0000 Uiso
H111 H 0.3186 0.3045 0.4725 0.0490 1.0000 Uiso
H121 H 0.3219 0.3507 0.6340 0.0456 1.0000 Uiso
H151 H 0.5337 0.7470 0.7618 0.0338 1.0000 Uiso
H161 H 0.4657 0.6935 0.9126 0.0396 1.0000 Uiso
H171 H 0.3737 0.5366 0.9305 0.0476 1.0000 Uiso
H181 H 0.3410 0.4325 0.7976 0.0439 1.0000 Uiso
H211 H 0.9013 0.6459 0.7589 0.0337 1.0000 Uiso
H212 H 0.8852 0.5267 0.7610 0.0337 1.0000 Uiso
H221 H 0.8368 0.5943 0.9073 0.0649 1.0000 Uiso
H222 H 0.7347 0.6630 0.8582 0.0649 1.0000 Uiso
H223 H 0.7185 0.5438 0.8603 0.0649 1.0000 Uiso
H241 H 0.4646 0.6982 0.2451 0.0335 1.0000 Uiso
H251 H 0.4352 0.6144 0.1006 0.0381 1.0000 Uiso
H261 H 0.6025 0.5564 0.0131 0.0378 1.0000 Uiso
H271 H 0.8008 0.5815 0.0701 0.0373 1.0000 Uiso
H281 H 0.8316 0.6664 0.2135 0.0341 1.0000 Uiso
_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
N1 . C1 . 1.369(3) yes
N1 . C4 . 1.475(3) yes
N1 . C6 . 1.475(3) yes
C1 . C2 . 1.498(4) yes
C1 . O2 . 1.222(3) yes
C2 . C3 . 1.513(4) yes
C2 . C7 . 1.556(4) yes
C2 . C20 . 1.505(4) yes
C3 . C4 . 1.520(4) yes
C3 . C7 . 1.514(4) yes
C3 . H31 . 0.96(3) no
C4 . C5 . 1.515(4) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.444(3) yes
C5 . H51 . 1.000 no
C5 . H52 . 1.000 no
O1 . C6 . 1.436(3) yes
C6 . C23 . 1.504(4) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.513(4) yes
C7 . C14 . 1.513(4) yes
C8 . C9 . 1.398(4) yes
C8 . C13 . 1.405(4) yes
C9 . C10 . 1.391(4) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.387(5) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.390(5) yes
C11 . H111 . 1.000 no
C12 . C13 . 1.392(4) yes
C12 . H121 . 1.000 no
C13 . C19 . 1.469(4) yes
C14 . C15 . 1.383(4) yes
C14 . C19 . 1.402(4) yes
C15 . C16 . 1.395(4) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.395(4) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.395(5) yes
C17 . H171 . 1.000 no
C18 . C19 . 1.392(4) yes
C18 . H181 . 1.000 no
C20 . O3 . 1.200(3) yes
C20 . O4 . 1.328(3) yes
O4 . C21 . 1.463(3) yes
C21 . C22 . 1.492(4) yes
C21 . H211 . 1.000 no
C21 . H212 . 1.000 no
C22 . H221 . 1.000 no
C22 . H222 . 1.000 no
C22 . H223 . 1.000 no
C23 . C24 . 1.397(4) yes
C23 . C28 . 1.392(4) yes
C24 . C25 . 1.387(4) yes
C24 . H241 . 1.000 no
C25 . C26 . 1.387(4) yes
C25 . H251 . 1.000 no
C26 . C27 . 1.382(5) yes
C26 . H261 . 1.000 no
C27 . C28 . 1.385(4) yes
C27 . H271 . 1.000 no
C28 . H281 . 1.000 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
C1 . N1 . C4 . 111.8(2) yes
C1 . N1 . C6 . 121.0(2) yes
C4 . N1 . C6 . 109.1(2) yes
N1 . C1 . C2 . 108.9(2) yes
N1 . C1 . O2 . 124.9(3) yes
C2 . C1 . O2 . 126.1(3) yes
C1 . C2 . C3 . 106.2(2) yes
C1 . C2 . C7 . 119.3(2) yes
C3 . C2 . C7 . 59.08(18) yes
C1 . C2 . C20 . 115.0(2) yes
C3 . C2 . C20 . 125.9(2) yes
C7 . C2 . C20 . 119.7(2) yes
C2 . C3 . C4 . 106.3(2) yes
C2 . C3 . C7 . 61.90(18) yes
C4 . C3 . C7 . 117.8(2) yes
C2 . C3 . H31 . 124.1(17) no
C4 . C3 . H31 . 118.2(16) no
C7 . C3 . H31 . 116.4(16) no
N1 . C4 . C3 . 105.1(2) yes
N1 . C4 . C5 . 100.0(2) yes
C3 . C4 . C5 . 116.7(2) yes
N1 . C4 . H41 . 120.611 no
C3 . C4 . H41 . 105.175 no
C5 . C4 . H41 . 109.829 no
C4 . C5 . O1 . 102.5(2) yes
C4 . C5 . H51 . 111.186 no
O1 . C5 . H51 . 111.185 no
C4 . C5 . H52 . 111.187 no
O1 . C5 . H52 . 111.186 no
H51 . C5 . H52 . 109.467 no
C5 . O1 . C6 . 108.0(2) yes
N1 . C6 . O1 . 103.9(2) yes
N1 . C6 . C23 . 114.6(2) yes
O1 . C6 . C23 . 109.3(2) yes
N1 . C6 . H61 . 109.808 no
O1 . C6 . H61 . 115.022 no
C23 . C6 . H61 . 104.449 no
C2 . C7 . C3 . 59.02(18) yes
C2 . C7 . C8 . 125.2(2) yes
C3 . C7 . C8 . 130.9(2) yes
C2 . C7 . C14 . 114.7(2) yes
C3 . C7 . C14 . 117.6(2) yes
C8 . C7 . C14 . 104.0(2) yes
C7 . C8 . C9 . 131.9(3) yes
C7 . C8 . C13 . 108.5(2) yes
C9 . C8 . C13 . 119.6(3) yes
C8 . C9 . C10 . 118.8(3) yes
C8 . C9 . H91 . 120.595 no
C10 . C9 . H91 . 120.595 no
C9 . C10 . C11 . 121.3(3) yes
C9 . C10 . H101 . 119.329 no
C11 . C10 . H101 . 119.328 no
C10 . C11 . C12 . 120.4(3) yes
C10 . C11 . H111 . 119.799 no
C12 . C11 . H111 . 119.799 no
C11 . C12 . C13 . 118.7(3) yes
C11 . C12 . H121 . 120.643 no
C13 . C12 . H121 . 120.642 no
C8 . C13 . C12 . 121.1(3) yes
C8 . C13 . C19 . 109.4(2) yes
C12 . C13 . C19 . 129.4(3) yes
C7 . C14 . C15 . 130.2(3) yes
C7 . C14 . C19 . 109.1(2) yes
C15 . C14 . C19 . 120.7(3) yes
C14 . C15 . C16 . 118.9(3) yes
C14 . C15 . H151 . 120.556 no
C16 . C15 . H151 . 120.556 no
C15 . C16 . C17 . 120.4(3) yes
C15 . C16 . H161 . 119.796 no
C17 . C16 . H161 . 119.797 no
C16 . C17 . C18 . 121.0(3) yes
C16 . C17 . H171 . 119.516 no
C18 . C17 . H171 . 119.516 no
C17 . C18 . C19 . 118.3(3) yes
C17 . C18 . H181 . 120.836 no
C19 . C18 . H181 . 120.836 no
C13 . C19 . C14 . 108.7(3) yes
C13 . C19 . C18 . 130.6(3) yes
C14 . C19 . C18 . 120.7(3) yes
C2 . C20 . O3 . 124.5(2) yes
C2 . C20 . O4 . 109.4(2) yes
O3 . C20 . O4 . 126.0(2) yes
C20 . O4 . C21 . 117.7(2) yes
O4 . C21 . C22 . 110.7(2) yes
O4 . C21 . H211 . 109.162 no
C22 . C21 . H211 . 109.161 no
O4 . C21 . H212 . 109.163 no
C22 . C21 . H212 . 109.162 no
H211 . C21 . H212 . 109.467 no
C21 . C22 . H221 . 109.467 no
C21 . C22 . H222 . 109.467 no
H221 . C22 . H222 . 109.475 no
C21 . C22 . H223 . 109.467 no
H221 . C22 . H223 . 109.475 no
H222 . C22 . H223 . 109.476 no
C6 . C23 . C24 . 121.3(2) yes
C6 . C23 . C28 . 119.4(3) yes
C24 . C23 . C28 . 119.3(2) yes
C23 . C24 . C25 . 119.5(3) yes
C23 . C24 . H241 . 120.240 no
C25 . C24 . H241 . 120.240 no
C24 . C25 . C26 . 120.7(3) yes
C24 . C25 . H251 . 119.666 no
C26 . C25 . H251 . 119.666 no
C25 . C26 . C27 . 119.9(3) yes
C25 . C26 . H261 . 120.042 no
C27 . C26 . H261 . 120.044 no
C26 . C27 . C28 . 119.9(3) yes
C26 . C27 . H271 . 120.073 no
C28 . C27 . H271 . 120.073 no
C23 . C28 . C27 . 120.7(3) yes
C23 . C28 . H281 . 119.662 no
C27 . C28 . H281 . 119.662 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_audit_block_doi                 10.5517/ccs3sj5
_database_code_depnum_ccdc_archive 'CCDC 718627'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             08-02-12
_audit_creation_method           CRYSTALS_ver_12.85

_oxford_structure_analysis_title 5717
_chemical_name_systematic        ?
_chemical_melting_point          'not measured'

_cell_length_a                   9.34010(10)
_cell_length_b                   9.96030(10)
_cell_length_c                   26.3001(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2446.70(5)

_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'
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'
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'
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 H21 Br2 N1 O4
# Dc = 1.62 Fooo = 1192.00 Mu = 33.49 M = 595.29
# Found Formula = C28 H21 Br2 N1 O4
# Dc = 1.62 FOOO = 1192.00 Mu = 33.49 M = 595.29

_chemical_formula_sum            'C28 H21 Br2 N1 O4'
_chemical_formula_moiety         'C28 H21 Br2 N1 O4'
_chemical_compound_source        .
_chemical_formula_weight         595.29


_cell_measurement_reflns_used    3163
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.19
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_max          0.26

_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    3.349

# Sheldrick geometric approximatio 0.45 0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.53
# 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       'Nonius KappaCCD'
_diffrn_measurement_device_type  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, 1997-2001).'
_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_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            30902
_reflns_number_total             5549
_diffrn_reflns_av_R_equivalents  0.059
# Number of reflections with Friedels Law is 3144
# Number of reflections without Friedels Law is 5549
# Theoretical number of reflections is about 2800


_diffrn_reflns_theta_min         5.136
_diffrn_reflns_theta_max         27.462
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        26.913
_diffrn_measured_fraction_theta_full 0.989


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_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              34

_oxford_diffrn_Wilson_B_factor   3.08
_oxford_diffrn_Wilson_scale      13.03

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

_refine_diff_density_min         -0.82
_refine_diff_density_max         1.16


# 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         5525
_refine_ls_number_restraints     0
_refine_ls_number_parameters     317
_oxford_refine_ls_R_factor_ref   0.0461
_refine_ls_wR_factor_ref         0.0908
_refine_ls_goodness_of_fit_ref   0.9917
_refine_ls_shift/su_max          0.001822


# The values computed from all data
_oxford_reflns_number_all        5525
_refine_ls_R_factor_all          0.0461
_refine_ls_wR_factor_all         0.0908

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4924
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.0862

_refine_ls_abs_structure_Flack   0.010(9)
_refine_ls_abs_structure_details 'Flack (1983), 2405 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= Modified Sheldrick
w=1/[σ²(F²) + ( 0.04P)² + 3.99P]
,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 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Br1 Br 1.17222(5) 0.55216(4) 0.584379(17) 0.0454 1.0000 Uani . . . . . . .
C2 C 1.1387(4) 0.3814(4) 0.61426(13) 0.0303 1.0000 Uani . . . . . . .
C3 C 1.0039(4) 0.3221(4) 0.60847(14) 0.0270 1.0000 Uani . . . . . . .
C4 C 0.9821(3) 0.1954(4) 0.62908(13) 0.0242 1.0000 Uani . . . . . . .
C5 C 0.8545(3) 0.1022(3) 0.62920(12) 0.0210 1.0000 Uani . . . . . . .
C6 C 0.7351(3) 0.0864(4) 0.59035(12) 0.0215 1.0000 Uani . . . . . . .
C7 C 0.6990(3) 0.1464(3) 0.64121(12) 0.0202 1.0000 Uani . . . . . . .
C8 C 0.6568(3) 0.2896(3) 0.63112(12) 0.0207 1.0000 Uani . . . . . . .
O9 O 0.6021(3) 0.3667(2) 0.66117(9) 0.0268 1.0000 Uani . . . . . . .
N10 N 0.6855(3) 0.3172(3) 0.58083(10) 0.0215 1.0000 Uani . . . . . . .
C11 C 0.7072(4) 0.1942(4) 0.55127(13) 0.0245 1.0000 Uani . . . . . . .
C12 C 0.5598(4) 0.1848(4) 0.52572(16) 0.0338 1.0000 Uani . . . . . . .
O13 O 0.5179(3) 0.3208(3) 0.51755(10) 0.0350 1.0000 Uani . . . . . . .
C14 C 0.5965(4) 0.4081(4) 0.55050(13) 0.0270 1.0000 Uani . . . . . . .
C15 C 0.6858(4) 0.5075(3) 0.52101(13) 0.0272 1.0000 Uani . . . . . . .
C16 C 0.7583(5) 0.6072(4) 0.54733(16) 0.0445 1.0000 Uani . . . . . . .
C17 C 0.8466(6) 0.6964(4) 0.52203(19) 0.0514 1.0000 Uani . . . . . . .
C18 C 0.8621(5) 0.6876(4) 0.46992(19) 0.0471 1.0000 Uani . . . . . . .
C19 C 0.7892(5) 0.5904(5) 0.44329(16) 0.0463 1.0000 Uani . . . . . . .
C20 C 0.7004(4) 0.5013(4) 0.46863(14) 0.0363 1.0000 Uani . . . . . . .
C21 C 0.6148(3) 0.0746(3) 0.68158(12) 0.0212 1.0000 Uani . . . . . . .
O22 O 0.5259(3) -0.0088(3) 0.67239(10) 0.0335 1.0000 Uani . . . . . . .
O23 O 0.6487(3) 0.1192(3) 0.72738(9) 0.0346 1.0000 Uani . . . . . . .
C24 C 0.5648(5) 0.0604(5) 0.76932(14) 0.0454 1.0000 Uani . . . . . . .
C25 C 0.5601(5) 0.1605(5) 0.81090(17) 0.0472 1.0000 Uani . . . . . . .
C26 C 0.9083(4) -0.0223(4) 0.65448(12) 0.0242 1.0000 Uani . . . . . . .
C27 C 0.8414(4) -0.1453(3) 0.66155(12) 0.0267 1.0000 Uani . . . . . . .
C28 C 0.9199(4) -0.2460(4) 0.68625(14) 0.0310 1.0000 Uani . . . . . . .
Br29 Br 0.83598(5) -0.41649(4) 0.693961(15) 0.0391 1.0000 Uani . . . . . . .
C30 C 1.0581(4) -0.2255(4) 0.70352(15) 0.0357 1.0000 Uani . . . . . . .
C31 C 1.1239(4) -0.1043(4) 0.69528(15) 0.0350 1.0000 Uani . . . . . . .
C32 C 1.0498(4) -0.0021(4) 0.67051(13) 0.0277 1.0000 Uani . . . . . . .
C33 C 1.0951(4) 0.1312(4) 0.65521(13) 0.0289 1.0000 Uani . . . . . . .
C34 C 1.2275(4) 0.1937(5) 0.66051(16) 0.0369 1.0000 Uani . . . . . . .
C35 C 1.2491(4) 0.3198(4) 0.64006(16) 0.0361 1.0000 Uani . . . . . . .
H31 H 0.9324 0.3655 0.5915 0.0326 1.0000 Uiso R . . . . . .
H61 H 0.7030 -0.0044 0.5828 0.0259 1.0000 Uiso R . . . . . .
H111 H 0.7843 0.2034 0.5274 0.0299 1.0000 Uiso R . . . . . .
H122 H 0.5663 0.1375 0.4931 0.0409 1.0000 Uiso R . . . . . .
H121 H 0.4907 0.1410 0.5481 0.0402 1.0000 Uiso R . . . . . .
H141 H 0.5292 0.4562 0.5732 0.0329 1.0000 Uiso R . . . . . .
H161 H 0.7483 0.6136 0.5826 0.0542 1.0000 Uiso R . . . . . .
H171 H 0.8965 0.7603 0.5401 0.0622 1.0000 Uiso R . . . . . .
H181 H 0.9210 0.7474 0.4533 0.0575 1.0000 Uiso R . . . . . .
H191 H 0.7982 0.5848 0.4079 0.0564 1.0000 Uiso R . . . . . .
H201 H 0.6517 0.4367 0.4507 0.0447 1.0000 Uiso R . . . . . .
H242 H 0.4691 0.0389 0.7579 0.0554 1.0000 Uiso R . . . . . .
H241 H 0.6108 -0.0220 0.7796 0.0551 1.0000 Uiso R . . . . . .
H252 H 0.5051 0.1251 0.8393 0.0703 1.0000 Uiso R . . . . . .
H251 H 0.5171 0.2427 0.7993 0.0709 1.0000 Uiso R . . . . . .
H253 H 0.6568 0.1790 0.8217 0.0711 1.0000 Uiso R . . . . . .
H271 H 0.7493 -0.1623 0.6505 0.0318 1.0000 Uiso R . . . . . .
H301 H 1.1056 -0.2940 0.7199 0.0432 1.0000 Uiso R . . . . . .
H311 H 1.2181 -0.0908 0.7065 0.0419 1.0000 Uiso R . . . . . .
H341 H 1.3007 0.1502 0.6774 0.0449 1.0000 Uiso R . . . . . .
H351 H 1.3357 0.3629 0.6441 0.0440 1.0000 Uiso R . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2759(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
Br1 . C2 . 1.900(4) yes
C2 . C3 . 1.399(5) yes
C2 . C35 . 1.378(5) yes
C3 . C4 . 1.388(5) yes
C3 . H31 . 0.911 no
C4 . C5 . 1.511(5) yes
C4 . C33 . 1.413(5) yes
C5 . C6 . 1.521(4) yes
C5 . C7 . 1.550(4) yes
C5 . C26 . 1.494(4) yes
C6 . C7 . 1.504(4) yes
C6 . C11 . 1.509(5) yes
C6 . H61 . 0.972 no
C7 . C8 . 1.503(4) yes
C7 . C21 . 1.503(4) yes
C8 . O9 . 1.215(4) yes
C8 . N10 . 1.377(4) yes
N10 . C11 . 1.465(4) yes
N10 . C14 . 1.466(4) yes
C11 . C12 . 1.535(5) yes
C11 . H111 . 0.961 no
C12 . O13 . 1.426(5) yes
C12 . H122 . 0.980 no
C12 . H121 . 0.976 no
O13 . C14 . 1.431(4) yes
C14 . C15 . 1.509(5) yes
C14 . H141 . 0.991 no
C15 . C16 . 1.387(5) yes
C15 . C20 . 1.386(5) yes
C16 . C17 . 1.383(6) yes
C16 . H161 . 0.935 no
C17 . C18 . 1.381(7) yes
C17 . H171 . 0.921 no
C18 . C19 . 1.375(7) yes
C18 . H181 . 0.921 no
C19 . C20 . 1.385(6) yes
C19 . H191 . 0.936 no
C20 . H201 . 0.919 no
C21 . O22 . 1.199(4) yes
C21 . O23 . 1.322(4) yes
O23 . C24 . 1.474(4) yes
C24 . C25 . 1.481(6) yes
C24 . H242 . 0.967 no
C24 . H241 . 0.964 no
C25 . H252 . 0.973 no
C25 . H251 . 0.962 no
C25 . H253 . 0.964 no
C26 . C27 . 1.387(5) yes
C26 . C32 . 1.402(5) yes
C27 . C28 . 1.402(5) yes
C27 . H271 . 0.923 no
C28 . Br29 . 1.882(4) yes
C28 . C30 . 1.383(6) yes
C30 . C31 . 1.372(6) yes
C30 . H301 . 0.921 no
C31 . C32 . 1.393(5) yes
C31 . H311 . 0.937 no
C32 . C33 . 1.450(5) yes
C33 . C34 . 1.391(5) yes
C34 . C35 . 1.381(6) yes
C34 . H341 . 0.923 no
C35 . H351 . 0.922 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 . 118.8(3) yes
Br1 . C2 . C35 . 118.6(3) yes
C3 . C2 . C35 . 122.6(4) yes
C2 . C3 . C4 . 118.2(3) yes
C2 . C3 . H31 . 120.8 no
C4 . C3 . H31 . 121.0 no
C3 . C4 . C5 . 132.4(3) yes
C3 . C4 . C33 . 119.5(3) yes
C5 . C4 . C33 . 108.1(3) yes
C4 . C5 . C6 . 129.9(3) yes
C4 . C5 . C7 . 124.4(3) yes
C6 . C5 . C7 . 58.62(19) yes
C4 . C5 . C26 . 104.2(3) yes
C6 . C5 . C26 . 117.3(3) yes
C7 . C5 . C26 . 117.4(3) yes
C5 . C6 . C7 . 61.7(2) yes
C5 . C6 . C11 . 120.7(3) yes
C7 . C6 . C11 . 106.5(3) yes
C5 . C6 . H61 . 117.3 no
C7 . C6 . H61 . 118.9 no
C11 . C6 . H61 . 118.0 no
C5 . C7 . C6 . 59.7(2) yes
C5 . C7 . C8 . 118.6(3) yes
C6 . C7 . C8 . 106.2(3) yes
C5 . C7 . C21 . 119.9(3) yes
C6 . C7 . C21 . 123.8(3) yes
C8 . C7 . C21 . 116.0(3) yes
C7 . C8 . O9 . 126.5(3) yes
C7 . C8 . N10 . 107.9(3) yes
O9 . C8 . N10 . 125.5(3) yes
C8 . N10 . C11 . 111.7(3) yes
C8 . N10 . C14 . 122.4(3) yes
C11 . N10 . C14 . 107.8(3) yes
C6 . C11 . N10 . 104.9(3) yes
C6 . C11 . C12 . 114.2(3) yes
N10 . C11 . C12 . 99.2(3) yes
C6 . C11 . H111 . 112.7 no
N10 . C11 . H111 . 111.8 no
C12 . C11 . H111 . 113.1 no
C11 . C12 . O13 . 104.8(3) yes
C11 . C12 . H122 . 110.9 no
O13 . C12 . H122 . 110.0 no
C11 . C12 . H121 . 110.9 no
O13 . C12 . H121 . 109.5 no
H122 . C12 . H121 . 110.6 no
C12 . O13 . C14 . 110.2(3) yes
N10 . C14 . O13 . 104.2(3) yes
N10 . C14 . C15 . 111.8(3) yes
O13 . C14 . C15 . 111.8(3) yes
N10 . C14 . H141 . 109.3 no
O13 . C14 . H141 . 109.5 no
C15 . C14 . H141 . 110.1 no
C14 . C15 . C16 . 118.9(3) yes
C14 . C15 . C20 . 122.4(3) yes
C16 . C15 . C20 . 118.7(3) yes
C15 . C16 . C17 . 120.7(4) yes
C15 . C16 . H161 . 119.7 no
C17 . C16 . H161 . 119.6 no
C16 . C17 . C18 . 119.9(4) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 120.2 no
C17 . C18 . C19 . 119.9(4) yes
C17 . C18 . H181 . 119.4 no
C19 . C18 . H181 . 120.7 no
C18 . C19 . C20 . 120.1(4) yes
C18 . C19 . H191 . 120.2 no
C20 . C19 . H191 . 119.6 no
C15 . C20 . C19 . 120.6(4) yes
C15 . C20 . H201 . 119.5 no
C19 . C20 . H201 . 119.9 no
C7 . C21 . O22 . 123.4(3) yes
C7 . C21 . O23 . 111.0(3) yes
O22 . C21 . O23 . 125.6(3) yes
C21 . O23 . C24 . 114.9(3) yes
O23 . C24 . C25 . 107.5(3) yes
O23 . C24 . H242 . 110.2 no
C25 . C24 . H242 . 110.6 no
O23 . C24 . H241 . 108.1 no
C25 . C24 . H241 . 112.3 no
H242 . C24 . H241 . 108.1 no
C24 . C25 . H252 . 109.8 no
C24 . C25 . H251 . 110.6 no
H252 . C25 . H251 . 109.4 no
C24 . C25 . H253 . 108.5 no
H252 . C25 . H253 . 109.7 no
H251 . C25 . H253 . 108.8 no
C5 . C26 . C27 . 129.9(3) yes
C5 . C26 . C32 . 109.3(3) yes
C27 . C26 . C32 . 120.7(3) yes
C26 . C27 . C28 . 117.3(3) yes
C26 . C27 . H271 . 122.6 no
C28 . C27 . H271 . 120.1 no
C27 . C28 . Br29 . 118.5(3) yes
C27 . C28 . C30 . 122.3(4) yes
Br29 . C28 . C30 . 119.1(3) yes
C28 . C30 . C31 . 119.7(4) yes
C28 . C30 . H301 . 119.6 no
C31 . C30 . H301 . 120.6 no
C30 . C31 . C32 . 119.6(3) yes
C30 . C31 . H311 . 119.8 no
C32 . C31 . H311 . 120.6 no
C26 . C32 . C31 . 120.3(4) yes
C26 . C32 . C33 . 108.9(3) yes
C31 . C32 . C33 . 130.8(3) yes
C32 . C33 . C4 . 109.4(3) yes
C32 . C33 . C34 . 129.9(4) yes
C4 . C33 . C34 . 120.6(4) yes
C33 . C34 . C35 . 119.9(4) yes
C33 . C34 . H341 . 119.8 no
C35 . C34 . H341 . 120.4 no
C34 . C35 . C2 . 119.1(3) yes
C34 . C35 . H351 . 120.4 no
C2 . C35 . H351 . 120.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . N10 . 132 0.91 2.37 3.061(5) yes
C11 . H111 . O13 2_556 163 0.96 2.49 3.423(5) yes
C35 . H351 . O9 1_655 153 0.92 2.53 3.376(5) yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_15b
_audit_block_doi                 10.5517/ccs3sk6
_database_code_depnum_ccdc_archive 'CCDC 718628'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetasy.2009.02.037 2009
_audit_update_record             
;
2009-01-29 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             08-10-02
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 5995
_chemical_name_systematic        ?
_chemical_melting_point          'not measured'

_cell_length_a                   11.2503(2)
_cell_length_b                   13.2299(2)
_cell_length_c                   14.4055(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2144.12(6)

_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'
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'
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 = C27 H22 N2 O4
# Dc = 1.36 Fooo = 920.00 Mu = 0.92 M = 438.48
# Found Formula = C27 H22 N2 O4
# Dc = 1.36 FOOO = 920.00 Mu = 0.92 M = 438.48

_chemical_formula_sum            'C27 H22 N2 O4'
_chemical_formula_moiety         'C27 H22 N2 O4'
_chemical_compound_source        .
_chemical_formula_weight         438.48


_cell_measurement_reflns_used    2776
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_max          0.26

_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.092

# 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  0.93
_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       'Nonius KappaCCD'
_diffrn_measurement_device_type  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, 1997-2001).'
_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_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            34418
_reflns_number_total             2756
_diffrn_reflns_av_R_equivalents  0.052
# Number of reflections with Friedels Law is 2756
# Number of reflections without Friedels Law is 4913
# Theoretical number of reflections is about 2461


_diffrn_reflns_theta_min         5.164
_diffrn_reflns_theta_max         27.493
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        26.943
_diffrn_measured_fraction_theta_full 0.990


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

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.21


# 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         2756
_refine_ls_number_restraints     0
_refine_ls_number_parameters     299
_oxford_refine_ls_R_factor_ref   0.0442
_refine_ls_wR_factor_ref         0.0875
_refine_ls_goodness_of_fit_ref   0.9761
_refine_ls_shift/su_max          0.000260


# The values computed from all data
_oxford_reflns_number_all        2756
_refine_ls_R_factor_all          0.0442
_refine_ls_wR_factor_all         0.0875

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2376
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0842

# 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 unk


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[σ²(F²) + ( 0.05P)² + 0.37P]
,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 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.78240(13) 0.26703(10) 0.67187(10) 0.0324 1.0000 Uani . . . . . . .
C2 C 0.73548(16) 0.18779(14) 0.65320(13) 0.0255 1.0000 Uani . . . . . . .
O3 O 0.75568(12) 0.10028(11) 0.69401(10) 0.0310 1.0000 Uani . . . . . . .
C4 C 0.84401(18) 0.09860(17) 0.76857(14) 0.0336 1.0000 Uani . . . . . . .
C5 C 0.7933(2) 0.1384(3) 0.85787(16) 0.0537 1.0000 Uani . . . . . . .
C6 C 0.64868(16) 0.17614(14) 0.57447(12) 0.0249 1.0000 Uani . . . . . . .
C7 C 0.52078(16) 0.13558(15) 0.59042(13) 0.0270 1.0000 Uani . . . . . . .
C8 C 0.54238(16) 0.24274(15) 0.55694(13) 0.0269 1.0000 Uani . . . . . . .
C9 C 0.53892(17) 0.26236(15) 0.45305(13) 0.0281 1.0000 Uani . . . . . . .
N10 N 0.63336(14) 0.19767(11) 0.41393(10) 0.0257 1.0000 Uani . . . . . . .
C11 C 0.70712(17) 0.15987(14) 0.48148(13) 0.0253 1.0000 Uani . . . . . . .
O12 O 0.80591(12) 0.12541(11) 0.46891(10) 0.0320 1.0000 Uani . . . . . . .
C13 C 0.68299(18) 0.24661(14) 0.33012(14) 0.0289 1.0000 Uani . . . . . . .
O14 O 0.62644(14) 0.34316(10) 0.32826(9) 0.0349 1.0000 Uani . . . . . . .
C15 C 0.5822(2) 0.36498(15) 0.41993(14) 0.0351 1.0000 Uani . . . . . . .
C16 C 0.65760(19) 0.19157(14) 0.24087(13) 0.0280 1.0000 Uani . . . . . . .
C17 C 0.75178(19) 0.15587(15) 0.18773(14) 0.0322 1.0000 Uani . . . . . . .
C18 C 0.7305(2) 0.10581(16) 0.10400(15) 0.0350 1.0000 Uani . . . . . . .
C19 C 0.6147(2) 0.09193(15) 0.07390(14) 0.0353 1.0000 Uani . . . . . . .
C20 C 0.5198(2) 0.12683(16) 0.12737(15) 0.0348 1.0000 Uani . . . . . . .
C21 C 0.54153(19) 0.17581(16) 0.21069(14) 0.0312 1.0000 Uani . . . . . . .
C22 C 0.46553(16) 0.04780(15) 0.54018(14) 0.0289 1.0000 Uani . . . . . . .
C23 C 0.41144(17) -0.01522(15) 0.60630(15) 0.0327 1.0000 Uani . . . . . . .
N24 N 0.35623(18) -0.10287(14) 0.58773(15) 0.0443 1.0000 Uani . . . . . . .
C25 C 0.3523(2) -0.12783(17) 0.49701(17) 0.0435 1.0000 Uani . . . . . . .
C26 C 0.3983(2) -0.06936(17) 0.42634(17) 0.0402 1.0000 Uani . . . . . . .
C27 C 0.45656(18) 0.02056(16) 0.44720(15) 0.0337 1.0000 Uani . . . . . . .
C28 C 0.42251(18) 0.02967(16) 0.69891(15) 0.0331 1.0000 Uani . . . . . . .
C29 C 0.48500(16) 0.12075(16) 0.69027(14) 0.0286 1.0000 Uani . . . . . . .
C30 C 0.50484(18) 0.18143(16) 0.76717(14) 0.0316 1.0000 Uani . . . . . . .
C31 C 0.46287(19) 0.14937(18) 0.85326(15) 0.0377 1.0000 Uani . . . . . . .
C32 C 0.4023(2) 0.05776(18) 0.86154(16) 0.0415 1.0000 Uani . . . . . . .
C33 C 0.3805(2) -0.00235(18) 0.78464(16) 0.0410 1.0000 Uani . . . . . . .
H41 H 0.9150 0.1416 0.7480 0.0423 1.0000 Uiso R . . . . . .
H42 H 0.8638 0.0266 0.7765 0.0424 1.0000 Uiso R . . . . . .
H52 H 0.8571 0.1295 0.9054 0.0829 1.0000 Uiso R . . . . . .
H53 H 0.7764 0.2133 0.8506 0.0835 1.0000 Uiso R . . . . . .
H51 H 0.7197 0.1001 0.8680 0.0843 1.0000 Uiso R . . . . . .
H81 H 0.5195 0.2981 0.5974 0.0338 1.0000 Uiso R . . . . . .
H91 H 0.4561 0.2501 0.4283 0.0329 1.0000 Uiso R . . . . . .
H131 H 0.7739 0.2518 0.3389 0.0351 1.0000 Uiso R . . . . . .
H152 H 0.6475 0.3952 0.4605 0.0451 1.0000 Uiso R . . . . . .
H151 H 0.5175 0.4150 0.4152 0.0442 1.0000 Uiso R . . . . . .
H171 H 0.8338 0.1637 0.2081 0.0390 1.0000 Uiso R . . . . . .
H181 H 0.7952 0.0783 0.0681 0.0443 1.0000 Uiso R . . . . . .
H191 H 0.6010 0.0566 0.0155 0.0419 1.0000 Uiso R . . . . . .
H201 H 0.4394 0.1151 0.1072 0.0451 1.0000 Uiso R . . . . . .
H211 H 0.4767 0.2013 0.2471 0.0400 1.0000 Uiso R . . . . . .
H251 H 0.3108 -0.1914 0.4817 0.0505 1.0000 Uiso R . . . . . .
H261 H 0.3862 -0.0916 0.3625 0.0515 1.0000 Uiso R . . . . . .
H271 H 0.4902 0.0618 0.4009 0.0442 1.0000 Uiso R . . . . . .
H301 H 0.5440 0.2408 0.7624 0.0402 1.0000 Uiso R . . . . . .
H311 H 0.4759 0.1920 0.9099 0.0491 1.0000 Uiso R . . . . . .
H321 H 0.3754 0.0325 0.9225 0.0504 1.0000 Uiso R . . . . . .
H331 H 0.3389 -0.0652 0.7897 0.0496 1.0000 Uiso R . . . . . .

_refine_ls_extinction_coef       330(80)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.4523(9)
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 . 1.204(2) yes
C2 . O3 . 1.318(2) yes
C2 . C6 . 1.505(3) yes
O3 . C4 . 1.463(2) yes
C4 . C5 . 1.503(3) yes
C4 . H41 . 1.024 no
C4 . H42 . 0.986 no
C5 . H52 . 0.999 no
C5 . H53 . 1.013 no
C5 . H51 . 0.981 no
C6 . C7 . 1.553(3) yes
C6 . C8 . 1.507(3) yes
C6 . C11 . 1.508(2) yes
C7 . C8 . 1.517(3) yes
C7 . C22 . 1.503(3) yes
C7 . C29 . 1.507(3) yes
C8 . C9 . 1.519(3) yes
C8 . H81 . 0.972 no
C9 . N10 . 1.476(2) yes
C9 . C15 . 1.519(3) yes
C9 . H91 . 1.010 no
N10 . C11 . 1.373(2) yes
N10 . C13 . 1.479(2) yes
C11 . O12 . 1.215(2) yes
C13 . O14 . 1.427(2) yes
C13 . C16 . 1.505(3) yes
C13 . H131 . 1.033 no
O14 . C15 . 1.441(2) yes
C15 . H152 . 1.021 no
C15 . H151 . 0.986 no
C16 . C17 . 1.390(3) yes
C16 . C21 . 1.392(3) yes
C17 . C18 . 1.397(3) yes
C17 . H171 . 0.974 no
C18 . C19 . 1.386(3) yes
C18 . H181 . 0.965 no
C19 . C20 . 1.394(3) yes
C19 . H191 . 0.975 no
C20 . C21 . 1.386(3) yes
C20 . H201 . 0.963 no
C21 . H211 . 0.960 no
C22 . C23 . 1.404(3) yes
C22 . C27 . 1.391(3) yes
C23 . N24 . 1.342(3) yes
C23 . C28 . 1.466(3) yes
N24 . C25 . 1.349(3) yes
C25 . C26 . 1.379(3) yes
C25 . H251 . 0.987 no
C26 . C27 . 1.391(3) yes
C26 . H261 . 0.975 no
C27 . H271 . 0.942 no
C28 . C29 . 1.401(3) yes
C28 . C33 . 1.389(3) yes
C29 . C30 . 1.386(3) yes
C30 . C31 . 1.393(3) yes
C30 . H301 . 0.904 no
C31 . C32 . 1.396(3) yes
C31 . H311 . 1.002 no
C32 . C33 . 1.386(3) yes
C32 . H321 . 0.987 no
C33 . H331 . 0.957 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . O3 . 126.12(17) yes
O1 . C2 . C6 . 122.83(17) yes
O3 . C2 . C6 . 110.98(16) yes
C2 . O3 . C4 . 117.24(16) yes
O3 . C4 . C5 . 111.41(17) yes
O3 . C4 . H41 . 108.0 no
C5 . C4 . H41 . 110.5 no
O3 . C4 . H42 . 104.7 no
C5 . C4 . H42 . 109.0 no
H41 . C4 . H42 . 113.2 no
C4 . C5 . H52 . 105.8 no
C4 . C5 . H53 . 109.0 no
H52 . C5 . H53 . 108.7 no
C4 . C5 . H51 . 105.4 no
H52 . C5 . H51 . 116.3 no
H53 . C5 . H51 . 111.3 no
C2 . C6 . C7 . 121.69(15) yes
C2 . C6 . C8 . 125.56(16) yes
C7 . C6 . C8 . 59.43(12) yes
C2 . C6 . C11 . 113.66(15) yes
C7 . C6 . C11 . 119.09(15) yes
C8 . C6 . C11 . 106.30(15) yes
C6 . C7 . C8 . 58.78(12) yes
C6 . C7 . C22 . 125.38(16) yes
C8 . C7 . C22 . 129.44(17) yes
C6 . C7 . C29 . 115.71(15) yes
C8 . C7 . C29 . 117.91(16) yes
C22 . C7 . C29 . 104.40(16) yes
C7 . C8 . C6 . 61.80(12) yes
C7 . C8 . C9 . 117.95(16) yes
C6 . C8 . C9 . 106.58(15) yes
C7 . C8 . H81 . 118.1 no
C6 . C8 . H81 . 123.4 no
C9 . C8 . H81 . 117.1 no
C8 . C9 . N10 . 104.98(14) yes
C8 . C9 . C15 . 116.99(16) yes
N10 . C9 . C15 . 99.66(15) yes
C8 . C9 . H91 . 110.1 no
N10 . C9 . H91 . 115.9 no
C15 . C9 . H91 . 109.1 no
C9 . N10 . C11 . 112.06(15) yes
C9 . N10 . C13 . 109.24(14) yes
C11 . N10 . C13 . 120.64(16) yes
C6 . C11 . N10 . 108.31(15) yes
C6 . C11 . O12 . 125.80(17) yes
N10 . C11 . O12 . 125.73(18) yes
N10 . C13 . O14 . 103.81(15) yes
N10 . C13 . C16 . 114.44(15) yes
O14 . C13 . C16 . 109.41(16) yes
N10 . C13 . H131 . 107.7 no
O14 . C13 . H131 . 112.6 no
C16 . C13 . H131 . 108.9 no
C13 . O14 . C15 . 108.44(15) yes
C9 . C15 . O14 . 102.68(15) yes
C9 . C15 . H152 . 113.6 no
O14 . C15 . H152 . 110.8 no
C9 . C15 . H151 . 112.7 no
O14 . C15 . H151 . 109.0 no
H152 . C15 . H151 . 107.9 no
C13 . C16 . C17 . 119.36(18) yes
C13 . C16 . C21 . 121.15(18) yes
C17 . C16 . C21 . 119.49(18) yes
C16 . C17 . C18 . 120.4(2) yes
C16 . C17 . H171 . 121.4 no
C18 . C17 . H171 . 118.2 no
C17 . C18 . C19 . 119.6(2) yes
C17 . C18 . H181 . 120.9 no
C19 . C18 . H181 . 119.4 no
C18 . C19 . C20 . 120.2(2) yes
C18 . C19 . H191 . 118.9 no
C20 . C19 . H191 . 121.0 no
C19 . C20 . C21 . 119.9(2) yes
C19 . C20 . H201 . 119.9 no
C21 . C20 . H201 . 120.2 no
C16 . C21 . C20 . 120.38(19) yes
C16 . C21 . H211 . 119.3 no
C20 . C21 . H211 . 120.2 no
C7 . C22 . C23 . 108.14(17) yes
C7 . C22 . C27 . 133.95(19) yes
C23 . C22 . C27 . 117.90(19) yes
C22 . C23 . N24 . 125.3(2) yes
C22 . C23 . C28 . 109.88(17) yes
N24 . C23 . C28 . 124.8(2) yes
C23 . N24 . C25 . 114.8(2) yes
N24 . C25 . C26 . 124.5(2) yes
N24 . C25 . H251 . 116.1 no
C26 . C25 . H251 . 119.4 no
C25 . C26 . C27 . 119.8(2) yes
C25 . C26 . H261 . 118.3 no
C27 . C26 . H261 . 121.8 no
C26 . C27 . C22 . 117.6(2) yes
C26 . C27 . H271 . 122.1 no
C22 . C27 . H271 . 120.2 no
C23 . C28 . C29 . 108.08(17) yes
C23 . C28 . C33 . 131.07(19) yes
C29 . C28 . C33 . 120.8(2) yes
C7 . C29 . C28 . 109.33(17) yes
C7 . C29 . C30 . 130.14(18) yes
C28 . C29 . C30 . 120.53(19) yes
C29 . C30 . C31 . 118.7(2) yes
C29 . C30 . H301 . 121.4 no
C31 . C30 . H301 . 119.8 no
C30 . C31 . C32 . 120.4(2) yes
C30 . C31 . H311 . 120.3 no
C32 . C31 . H311 . 119.3 no
C31 . C32 . C33 . 121.1(2) yes
C31 . C32 . H321 . 121.3 no
C33 . C32 . H321 . 117.6 no
C28 . C33 . C32 . 118.4(2) yes
C28 . C33 . H331 . 119.9 no
C32 . C33 . H331 . 121.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O1 2_456 164 1.01 2.44 3.423(3) yes
C21 . H211 . O1 2_456 167 0.96 2.51 3.454(3) yes
C27 . H271 . N10 . 130 0.94 2.42 3.111(3) yes


#==============================================================================
# start Validation Reply Form
_vrf_PLAT220_8b                  
;
PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.73 Ratio
RESPONSE: The large displacement parameters of some of the atoms of the
phenyl group suggest that it may be disordered. Attempts to model this did not
lead to an improvement in the agreement with the difraction data and were
abadoned.
;
_vrf_PLAT034_8b                  
;
PROBLEM: No Flack Parameter Given. Z .GT. Si, NonCentro . ?
RESPONSE: Examination of the diffraction pattern showed the crystal to be
a twin, the two components of which were related by a rotation of 180/%
about thedirect c axis, or by the reflection resulting from combination of
this with an inversion. In addition to this twinning, as the structure is
non-centrosymmetric, it was also necessary to consider the possiblity of the
primary component of the crystal being itself a racemic twin ('conglomerate').
An attempt was made to treat the crystal as a four-component twin and
refinement of the relative contributions of the four components to the
diffraction pattern converged readily, giving values of ca. 0.8, 0, 0.2, 0
respectively. It was therefore concluded that the crystal is twinned purely
by rotation and that each component is a single enantiomer. The Flack or
Rogers parameters conventionally used as measures of correctness of
absolute structure are inappropriate in this context.
;
# end Validation Reply Form
#==============================================================================




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_00000001
_database_code_depnum_ccdc_archive 'CCDC 1033820'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
_cell_length_a                   5.982
_cell_length_b                   9.172
_cell_length_c                   16.283
_cell_angle_alpha                85.32
_cell_angle_beta                 87.21
_cell_angle_gamma                89.85
_cell_volume                     889.363
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N1 N 1.02344 0.0130394 0.281562
O11 O 0.452676 -0.0663078 0.219562
O12 O 1.23402 0.168552 0.350657
O13 O 0.707292 0.336639 0.389338
O14 O 0.870162 0.255788 0.505134
C11 C 0.660151 0.00519899 0.217403
C12 C 0.802096 -0.0559409 0.287361
C13 C 0.700479 -0.0122741 0.369165
C14 C 0.858799 0.0964359 0.400011
C15 C 1.06236 0.0990978 0.342391
C16 C 0.800977 0.241452 0.430857
C17 C 0.801258 0.389944 0.541717
C18 C 0.82297 0.363836 0.631047
C19 C 0.808956 -0.0507889 0.450043
C11 C 0.988282 -0.161136 0.472746
C11 C 1.1591 -0.222254 0.425675
C11 C 1.30769 -0.318927 0.465404
C11 C 1.2901 -0.350009 0.549922
C11 C 1.11695 -0.291626 0.597055
C11 C 0.965932 -0.198439 0.558066
C11 C 0.770166 -0.124363 0.592428
C11 C 0.678213 -0.127889 0.673368
C11 C 0.485808 -0.0497308 0.688544
C11 C 0.382285 0.0299507 0.62457
C12 C 0.472743 0.0373194 0.543445
C12 C 0.669111 -0.0405656 0.528639
N2 N -0.202382 0.523637 0.20599
O21 O 0.367813 0.428919 0.269902
O22 O -0.410785 0.6994 0.135784
O23 O 0.116003 0.877978 0.0988923
O24 O -0.0425396 0.829893 -0.0179524
C21 C 0.15798 0.498538 0.271753
C22 C 0.0186999 0.456409 0.201178
C23 C 0.123325 0.523224 0.119868
C24 C -0.0356437 0.640835 0.0884046
C25 C -0.239811 0.626921 0.144668
C26 C 0.0241858 0.795115 0.0574353
C27 C 0.0286528 0.972492 -0.0548442
C28 C -0.0183134 0.97534 -0.144668
C29 C 0.0181737 0.508432 0.0381873
C21 C -0.157341 0.403139 0.014621
C21 C -0.331472 0.330005 0.0604582
C21 C -0.476697 0.243774 0.0196797
C21 C -0.45216 0.234553 -0.0643448
C21 C -0.278544 0.306906 -0.110059
C21 C -0.128419 0.389436 -0.0708224
C21 C 0.0682557 0.472643 -0.104136
C21 C 0.167149 0.491664 -0.183657
C21 C 0.360836 0.574589 -0.196921
C21 C 0.455812 0.637926 -0.132021
C22 C 0.357927 0.621649 -0.0526233
C22 C 0.163267 0.539414 -0.0396063

#END
_exptl_crystal_description       Triclinic
_diffrn_ambient_temperature      150(2)
_chemical_formula_moiety         C21H19NO4
_chemical_compound_source        Synthetic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_00000001
_database_code_depnum_ccdc_archive 'CCDC 1033821'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
_cell_length_a                   19.109
_cell_length_b                   6.594
_cell_length_c                   16.222
_cell_angle_alpha                90
_cell_angle_beta                 117.68
_cell_angle_gamma                90
_cell_volume                     1810.12
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N1 N -0.274241 -0.0917513 -0.421685
O1 O -0.360706 -0.405071 -0.567305
O2 O -0.25448 0.248563 -0.390153
O3 O -0.369392 0.374891 -0.318596
O4 O -0.453293 0.116471 -0.343446
C1 C -0.385157 -0.331063 -0.50257
C2 C -0.316978 -0.267368 -0.410757
C3 C -0.348027 -0.185019 -0.3463
C4 C -0.331004 0.0410985 -0.335511
C5 C -0.282221 0.0837136 -0.384723
C6 C -0.385447 0.196848 -0.332239
C7 C -0.504293 0.248866 -0.322285
C8 C -0.580703 0.139523 -0.350964
C9 C -0.291871 -0.107372 -0.252329
C10 C -0.203954 -0.144982 -0.209729
C11 C -0.150972 0.0147105 -0.181538
C12 C -0.0704217 -0.0216867 -0.135457
C13 C -0.0421636 -0.218687 -0.118473
C14 C -0.0942311 -0.377924 -0.146734
C15 C -0.175476 -0.342134 -0.192188
C16 C -0.320173 -0.101002 -0.17931
C17 C -0.305158 0.0668799 -0.121327
C18 C -0.326904 0.0664249 -0.0503962
C19 C -0.3626 -0.102822 -0.0364746
C20 C -0.376636 -0.270553 -0.092509
C21 C -0.356167 -0.270249 -0.164553

#END
_exptl_crystal_description       triclinic
_diffrn_ambient_temperature      15-(2)
_chemical_formula_moiety         C21H21NO4
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_compound_source        Synthetic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_00000001
_database_code_depnum_ccdc_archive 'CCDC 1033822'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
_cell_length_a                   10.161
_cell_length_b                   14.765
_cell_length_c                   24.975
_cell_angle_alpha                90
_cell_angle_beta                 98.27
_cell_angle_gamma                90
_cell_volume                     3707.97
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N11 N 0.575322 0.330648 0.244749
N12 N 0.814399 0.313919 0.294394
O11 O 0.411625 0.429531 0.260528
O12 O 0.487642 0.206841 0.28877
O13 O 0.903608 0.29123 0.211813
O14 O 0.955954 0.426822 0.330971
O15 O 0.449583 0.588556 0.196114
O16 O 0.571898 0.564919 0.129516
O17 O 0.735899 0.425061 0.433175
O18 O 0.945414 0.397767 0.467122
C10 C 0.48799 0.369795 0.131579
C10 C 0.518201 0.43881 0.178635
C10 C 0.492946 0.402237 0.232489
C10 C 0.672211 0.315951 0.207848
C10 C 0.627563 0.37948 0.161156
C10 C 0.57882 0.277888 0.294192
C10 C 0.811322 0.338369 0.237789
C10 C 0.722974 0.246665 0.311388
C10 C 0.883606 0.361464 0.335948
C11 C 0.855852 0.320557 0.388021
C11 C 0.757345 0.244837 0.372444
C11 C 0.896499 0.220251 0.397772
C11 C 0.508701 0.538438 0.169855
C11 C 0.552949 0.660077 0.113493
C11 C 0.609064 0.671455 0.0620267
C11 C 0.837174 0.386253 0.4318
C11 C 0.933164 0.454929 0.513774
C11 C 0.900973 0.398918 0.559697
C11 C 0.455487 0.407384 0.0749742
C12 C 0.542474 0.399866 0.0373455
C12 C 0.506904 0.431224 -0.0148492
C12 C 0.382274 0.469355 -0.0305481
C12 C 0.295863 0.478227 0.00704021
C12 C 0.331224 0.447208 0.0594777
C12 C 0.409716 0.28527 0.140116
C12 C 0.295953 0.286964 0.164636
C12 C 0.228996 0.207451 0.17289
C12 C 0.272262 0.126245 0.154966
C12 C 0.383104 0.123942 0.128585
C13 C 0.451459 0.203184 0.121221
C13 C 0.915853 0.189909 0.456157
C13 C 0.816507 0.148324 0.479422
C13 C 0.839349 0.12103 0.533195
C13 C 0.961314 0.134779 0.564188
C13 C 1.06267 0.175212 0.541044
C13 C 1.0408 0.202304 0.487515
C13 C 0.986722 0.175686 0.362895
C13 C 0.949249 0.0913651 0.340682
C13 C 1.02808 0.047071 0.308111
C14 C 1.14481 0.0869628 0.297833
C14 C 1.18401 0.169794 0.319925
C14 C 1.10486 0.214291 0.352699
N21 N 0.554313 0.38693 0.740032
N22 N 0.789823 0.338708 0.787938
O21 O 0.445223 0.523131 0.729876
O22 O 0.450194 0.345345 0.816624
O23 O 0.841162 0.251 0.713489
O24 O 0.987545 0.414495 0.798538
O25 O 0.438316 0.581919 0.612863
O26 O 0.624277 0.517781 0.591297
O27 O 1.02796 0.492247 0.911222
O28 O 0.834787 0.478295 0.944967
C20 C 0.450833 0.351779 0.625446
C20 C 0.510265 0.440706 0.65215
C20 C 0.495891 0.457232 0.710617
C20 C 0.625048 0.322927 0.709605
C20 C 0.593154 0.355301 0.651382
C20 C 0.563913 0.38097 0.798943
C20 C 0.77466 0.326855 0.729714
C20 C 0.679901 0.316561 0.817757
C20 C 0.893924 0.381241 0.817393
C21 C 0.872225 0.379548 0.875738
C21 C 0.740126 0.331529 0.876223
C21 C 0.866556 0.282832 0.898962
C21 C 0.518972 0.521506 0.617192
C21 C 0.641339 0.592552 0.554639
C21 C 0.565119 0.575011 0.49937
C21 C 0.922194 0.456013 0.91187
C21 C 0.873136 0.55029 0.984416
C21 C 0.906232 0.512227 1.03908
C21 C 0.425473 0.352253 0.564269
C22 C 0.308706 0.389842 0.537403
C22 C 0.282493 0.390791 0.481607
C22 C 0.373361 0.353337 0.451342
C22 C 0.488171 0.315274 0.477683
C22 C 0.513626 0.313987 0.533559
C22 C 0.350518 0.297935 0.65126
C22 C 0.36088 0.204132 0.651341
C22 C 0.266694 0.151237 0.672219
C22 C 0.162454 0.19228 0.692773
C22 C 0.151925 0.285135 0.693056
C23 C 0.245945 0.337827 0.672543
C23 C 0.893868 0.272402 0.959816
C23 C 0.79624 0.240299 0.988219
C23 C 0.823352 0.227295 1.04377
C23 C 0.94801 0.24653 1.07125
C23 C 1.04649 0.277278 1.04276
C23 C 1.01968 0.289266 0.987491
C23 C 0.920816 0.206435 0.868981
C23 C 0.845654 0.128819 0.857085
C23 C 0.892162 0.0589234 0.82856
C24 C 1.01604 0.0645448 0.812335
C24 C 1.09419 0.140603 0.825162
C24 C 1.04717 0.211515 0.85308
O1S O 0.251455 0.46475 0.826537
C1S C 0.241811 0.559772 0.819578
O2S O 0.31803 0.601154 0.293383
C2S C 0.317643 0.56133 0.344364
O3S O 0.130803 0.381986 0.257898

#END
_exptl_crystal_description       Triclinic
_chemical_formula_moiety         C86H86N4O19
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_compound_source        Synthetic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_00000001
_database_code_depnum_ccdc_archive 'CCDC 1033823'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
_cell_length_a                   6.519
_cell_length_b                   10.968
_cell_length_c                   10.869
_cell_angle_alpha                90
_cell_angle_beta                 105.04
_cell_angle_gamma                90
_cell_volume                     750.517
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N1 N 1.01469 0.867127 0.480818
O1 O 1.42012 0.737026 0.621624
O2 O 0.772618 1.02175 0.449951
O3 O 1.162 1.18805 0.38374
C1 C 1.39489 0.815433 0.513971
C2 C 1.1735 0.812789 0.424514
C3 C 1.16159 0.892108 0.308668
C4 C 1.00522 0.993582 0.308192
C5 C 0.914426 0.964407 0.418893
C6 C 1.02264 1.12624 0.278945
C7 C 0.959402 0.894296 0.202254
C8 C 0.978578 0.927756 0.0717368
C9 C 1.13823 0.98802 0.0333438
C10 C 1.11831 1.00343 -0.0964112
C11 C 0.943238 0.957934 -0.186249
C12 C 0.785127 0.895208 -0.148904
C13 C 0.804225 0.879435 -0.0196252
C14 C 0.670808 0.811604 0.0457286
C15 C 0.481386 0.749517 -0.00457286
C16 C 0.387995 0.686518 0.0770718
C17 C 0.485409 0.683053 0.206541
C18 C 0.674529 0.745596 0.258272
C19 C 0.766349 0.812516 0.177961

#END
_exptl_crystal_description       Triclinic
_diffrn_ambient_temperature      150(2)
_chemical_formula_moiety         C19H17NO3
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_compound_source        Synthetic
