# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2018

####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1447029'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cl2 N2 O8'
_chemical_formula_sum            'C36 H26 Cl2 N2 O8'
_chemical_formula_weight         685.49
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4655(15)
_cell_length_b                   10.993(2)
_cell_length_c                   11.026(2)
_cell_angle_alpha                111.90(3)
_cell_angle_beta                 95.16(3)
_cell_angle_gamma                108.53(3)
_cell_volume                     773.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2223
_cell_measurement_theta_min      1.9916
_cell_measurement_theta_max      27.6903

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             354
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

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

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9940
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         29.58
_reflns_number_total             3034
_reflns_number_gt                1806
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-2003 (Sheldrick, 2003)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0820P)²+0.5707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.2218
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.698
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.059

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 


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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2272(2) -0.03527(14) 0.15728(16) 0.1023(6) Uani 1 1 d . . .
N1 N 0.0735(5) 0.5913(3) -0.2471(3) 0.0538(8) Uani 1 1 d . . .
H1N H 0.0522 0.6372 -0.2903 0.065 Uiso 1 1 d R . .
C1 C 0.1972(6) 0.6652(4) -0.1298(4) 0.0560(10) Uani 1 1 d . . .
H1A H 0.2559 0.7631 -0.0980 0.067 Uiso 1 1 calc R . .
C2 C -0.0104(6) 0.4544(4) -0.2910(4) 0.0613(11) Uani 1 1 d . . .
H2A H -0.1003 0.4021 -0.3736 0.074 Uiso 1 1 calc R . .
C3 C 0.2425(5) 0.6000(4) -0.0521(4) 0.0557(10) Uani 1 1 d . . .
H3A H 0.3301 0.6551 0.0313 0.067 Uiso 1 1 calc R . .
C4 C 0.0317(6) 0.3860(4) -0.2171(4) 0.0633(11) Uani 1 1 d . . .
H4A H -0.0306 0.2880 -0.2514 0.076 Uiso 1 1 calc R . .
C5 C 0.1610(6) 0.4565(4) -0.0958(4) 0.0552(10) Uani 1 1 d . . .
C6 C 0.2012(6) 0.3748(4) -0.0212(4) 0.0610(11) Uani 1 1 d . . .
H6A H 0.1441 0.2764 -0.0656 0.073 Uiso 1 1 calc R . .
C7 C 0.3064(6) 0.4280(5) 0.0972(4) 0.0618(11) Uani 1 1 d . . .
H7A H 0.3637 0.5264 0.1402 0.074 Uiso 1 1 calc R . .
C8 C 0.3489(6) 0.3497(4) 0.1757(4) 0.0544(10) Uani 1 1 d . . .
C9 C 0.4732(6) 0.4246(5) 0.2972(4) 0.0625(11) Uani 1 1 d . . .
H9A H 0.5271 0.5229 0.3309 0.075 Uiso 1 1 calc R . .
C10 C 0.2721(6) 0.2060(5) 0.1316(4) 0.0608(11) Uani 1 1 d . . .
H10A H 0.1845 0.1496 0.0483 0.073 Uiso 1 1 calc R . .
C11 C 0.5239(7) 0.3602(5) 0.3743(4) 0.0664(12) Uani 1 1 d . . .
H11A H 0.6113 0.4167 0.4576 0.080 Uiso 1 1 calc R . .
C12 C 0.3245(6) 0.1431(4) 0.2112(4) 0.0631(11) Uani 1 1 d . . .
C13 C 0.4508(6) 0.2186(5) 0.3323(4) 0.0647(12) Uani 1 1 d . . .
H13A H 0.4854 0.1756 0.3838 0.078 Uiso 1 1 calc R . .
C14 C 0.9147(6) 0.1552(4) 0.3484(4) 0.0546(10) Uani 1 1 d . . .
C15 C 0.6306(6) -0.1596(4) 0.3034(5) 0.0680(13) Uani 1 1 d . . .
C16 C 0.8245(5) -0.0685(4) 0.4015(3) 0.0502(9) Uani 1 1 d . . .
C17 C 0.9466(5) 0.0681(4) 0.4234(3) 0.0475(9) Uani 1 1 d . . .
C18 C 1.1196(5) 0.1325(4) 0.5202(4) 0.0526(10) Uani 1 1 d . . .
H18A H 1.2030 0.2224 0.5344 0.063 Uiso 1 1 calc R . .
O1 O 0.5101(5) -0.2532(3) 0.3237(4) 0.0952(12) Uani 1 1 d . . .
O2 O 0.6026(5) -0.1386(3) 0.1949(3) 0.0828(11) Uani 1 1 d . . .
H2O H 0.7084 -0.0432 0.1952 0.099 Uiso 1 1 d R . .
O3 O 0.9947(4) 0.2831(3) 0.4052(3) 0.0660(8) Uani 1 1 d . . .
O4 O 0.8140(4) 0.0976(3) 0.2321(3) 0.0708(9) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.695(4) . ?
N1 C2 1.302(5) . ?
N1 C1 1.308(5) . ?
N1 H1N 0.8501 . ?
C1 C3 1.387(5) . ?
C1 H1A 0.9300 . ?
C2 C4 1.375(5) . ?
C2 H2A 0.9300 . ?
C3 C5 1.364(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.357(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.500(6) . ?
C6 C7 1.272(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.507(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.342(6) . ?
C8 C10 1.365(6) . ?
C9 C11 1.389(6) . ?
C9 H9A 0.9300 . ?
C10 C12 1.402(6) . ?
C10 H10A 0.9300 . ?
C11 C13 1.346(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.346(6) . ?
C13 H13A 0.9300 . ?
C14 O3 1.211(4) . ?
C14 O4 1.237(4) . ?
C14 C17 1.536(5) . ?
C15 O1 1.240(5) . ?
C15 O2 1.312(5) . ?
C15 C16 1.502(5) . ?
C16 C17 1.401(5) . ?
C16 C18 1.410(5) 2_756 ?
C17 C18 1.384(5) . ?
C18 C16 1.410(5) 2_756 ?
C18 H18A 0.9300 . ?
O2 H2O 1.0927 . ?
O4 H2O 1.3707 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 119.5(3) . . ?
C2 N1 H1N 123.7 . . ?
C1 N1 H1N 116.8 . . ?
N1 C1 C3 121.1(4) . . ?
N1 C1 H1A 119.4 . . ?
C3 C1 H1A 119.4 . . ?
N1 C2 C4 121.1(4) . . ?
N1 C2 H2A 119.5 . . ?
C4 C2 H2A 119.5 . . ?
C5 C3 C1 121.2(3) . . ?
C5 C3 H3A 119.4 . . ?
C1 C3 H3A 119.4 . . ?
C5 C4 C2 122.2(4) . . ?
C5 C4 H4A 118.9 . . ?
C2 C4 H4A 118.9 . . ?
C4 C5 C3 114.9(4) . . ?
C4 C5 C6 119.4(4) . . ?
C3 C5 C6 125.7(4) . . ?
C7 C6 C5 125.8(4) . . ?
C7 C6 H6A 117.1 . . ?
C5 C6 H6A 117.1 . . ?
C6 C7 C8 127.4(4) . . ?
C6 C7 H7A 116.3 . . ?
C8 C7 H7A 116.3 . . ?
C9 C8 C10 116.6(4) . . ?
C9 C8 C7 118.7(4) . . ?
C10 C8 C7 124.7(4) . . ?
C8 C9 C11 122.2(4) . . ?
C8 C9 H9A 118.9 . . ?
C11 C9 H9A 118.9 . . ?
C8 C10 C12 120.3(4) . . ?
C8 C10 H10A 119.8 . . ?
C12 C10 H10A 119.8 . . ?
C13 C11 C9 122.2(4) . . ?
C13 C11 H11A 118.9 . . ?
C9 C11 H11A 118.9 . . ?
C13 C12 C10 122.8(4) . . ?
C13 C12 Cl1 116.8(3) . . ?
C10 C12 Cl1 120.4(3) . . ?
C12 C13 C11 115.9(4) . . ?
C12 C13 H13A 122.1 . . ?
C11 C13 H13A 122.1 . . ?
O3 C14 O4 120.3(4) . . ?
O3 C14 C17 118.2(3) . . ?
O4 C14 C17 121.5(3) . . ?
O1 C15 O2 123.2(4) . . ?
O1 C15 C16 120.4(4) . . ?
O2 C15 C16 116.4(4) . . ?
C17 C16 C18 119.1(3) . 2_756 ?
C17 C16 C15 127.8(3) . . ?
C18 C16 C15 113.1(3) 2_756 . ?
C18 C17 C16 117.7(3) . . ?
C18 C17 C14 114.9(3) . . ?
C16 C17 C14 127.4(3) . . ?
C17 C18 C16 123.2(3) . 2_756 ?
C17 C18 H18A 118.4 . . ?
C16 C18 H18A 118.4 2_756 . ?
C15 O2 H2O 116.4 . . ?
C14 O4 H2O 111.2 . . ?

_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.976    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;

#   End of CIF   ============================================================


####################################################################### 
# 
# 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_p-1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1447030'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H24 Cl4 N2 O8'
_chemical_formula_sum            'C36 H24 Cl4 N2 O8'
_chemical_formula_weight         754.37
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5046(15)
_cell_length_b                   9.6822(19)
_cell_length_c                   12.452(3)
_cell_angle_alpha                69.07(3)
_cell_angle_beta                 79.63(3)
_cell_angle_gamma                77.91(3)
_cell_volume                     820.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2300
_cell_measurement_theta_min      1.7625
_cell_measurement_theta_max      27.8764

_exptl_crystal_description       Chip
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             386
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

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

# EXPERIMENTAL DATA


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10192
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.98
_reflns_number_total             3130
_reflns_number_gt                2609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-2003 (Sheldrick, 2003)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.2722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3130
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.791
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 



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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0516(2) 0.2083(2) 1.15004(17) 0.0406(5) Uani 1 1 d . . .
H1B H -0.1124 0.2338 1.2073 0.049 Uiso 1 1 calc R . .
Cl1 Cl 0.58716(8) -0.34621(7) 0.92413(5) 0.0521(2) Uani 1 1 d . . .
Cl2 Cl 0.86796(9) -0.17806(10) 0.47967(6) 0.0675(3) Uani 1 1 d . . .
O1 O 0.3860(3) 0.6650(2) 0.18978(14) 0.0622(6) Uani 1 1 d . . .
H1O H 0.5285 0.5975 0.1940 0.075 Uiso 1 1 d R . .
O2 O 0.1468(3) 0.7018(3) 0.30963(16) 0.0763(7) Uani 1 1 d . . .
O3 O 0.6788(2) 0.4979(2) 0.19819(14) 0.0551(5) Uani 1 1 d . . .
O4 O 0.7787(2) 0.2852(2) 0.32830(15) 0.0575(5) Uani 1 1 d . . .
C1 C -0.0691(3) 0.3012(3) 1.0425(2) 0.0438(6) Uani 1 1 d . . .
H1A H -0.1493 0.3914 1.0302 0.053 Uiso 1 1 calc R . .
C2 C 0.0583(3) 0.0763(3) 1.1707(2) 0.0384(5) Uani 1 1 d . . .
H2A H 0.0650 0.0120 1.2465 0.046 Uiso 1 1 calc R . .
C3 C 0.0301(3) 0.2652(3) 0.9499(2) 0.0427(5) Uani 1 1 d . . .
H3A H 0.0162 0.3306 0.8751 0.051 Uiso 1 1 calc R . .
C4 C 0.1616(3) 0.0346(3) 1.08126(19) 0.0355(5) Uani 1 1 d . . .
H4A H 0.2379 -0.0576 1.0965 0.043 Uiso 1 1 calc R . .
C5 C 0.1519(3) 0.1309(2) 0.96730(19) 0.0336(5) Uani 1 1 d . . .
C6 C 0.2624(3) 0.0960(3) 0.8681(2) 0.0391(5) Uani 1 1 d . . .
H6A H 0.2443 0.1643 0.7948 0.047 Uiso 1 1 calc R . .
C7 C 0.3864(3) -0.0257(2) 0.87453(19) 0.0350(5) Uani 1 1 d . . .
H7A H 0.4012 -0.0946 0.9481 0.042 Uiso 1 1 calc R . .
C8 C 0.5024(3) -0.0623(2) 0.77728(18) 0.0331(5) Uani 1 1 d . . .
C9 C 0.5293(3) 0.0460(3) 0.66813(19) 0.0410(5) Uani 1 1 d . . .
H9A H 0.4685 0.1434 0.6565 0.049 Uiso 1 1 calc R . .
C10 C 0.5994(3) -0.2062(3) 0.78987(19) 0.0357(5) Uani 1 1 d . . .
C11 C 0.6428(3) 0.0134(3) 0.5772(2) 0.0471(6) Uani 1 1 d . . .
H11A H 0.6601 0.0880 0.5059 0.056 Uiso 1 1 calc R . .
C12 C 0.7109(3) -0.2430(3) 0.6997(2) 0.0411(5) Uani 1 1 d . . .
H12A H 0.7712 -0.3403 0.7102 0.049 Uiso 1 1 calc R . .
C13 C 0.7305(3) -0.1319(3) 0.5937(2) 0.0444(6) Uani 1 1 d . . .
C14 C 0.3046(3) 0.6474(3) 0.2941(2) 0.0452(6) Uani 1 1 d . . .
C15 C 0.6855(3) 0.4123(3) 0.30107(19) 0.0389(5) Uani 1 1 d . . .
C16 C 0.6606(3) 0.4039(2) 0.50266(18) 0.0375(5) Uani 1 1 d . . .
H16A H 0.7705 0.3380 0.5043 0.045 Uiso 1 1 calc R . .
C17 C 0.5814(3) 0.4647(2) 0.39945(18) 0.0341(5) Uani 1 1 d . . .
C18 C 0.4149(3) 0.5643(2) 0.39633(18) 0.0348(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.332(3) . ?
N1 C2 1.333(3) . ?
N1 H1B 0.8600 . ?
Cl1 C10 1.737(2) . ?
Cl2 C13 1.736(2) . ?
O1 C14 1.299(3) . ?
O1 H1O 1.1298 . ?
O2 C14 1.203(3) . ?
O3 C15 1.256(3) . ?
O3 H1O 1.3166 . ?
O4 C15 1.243(3) . ?
C1 C3 1.369(3) . ?
C1 H1A 0.9300 . ?
C2 C4 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C5 1.395(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.463(3) . ?
C6 C7 1.327(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.465(3) . ?
C7 H7A 0.9300 . ?
C8 C10 1.399(3) . ?
C8 C9 1.400(3) . ?
C9 C11 1.380(3) . ?
C9 H9A 0.9300 . ?
C10 C12 1.382(3) . ?
C11 C13 1.382(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12A 0.9300 . ?
C14 C18 1.524(3) . ?
C15 C17 1.517(3) . ?
C16 C17 1.392(3) . ?
C16 C18 1.394(3) 2_666 ?
C16 H16A 0.9300 . ?
C17 C18 1.407(3) . ?
C18 C16 1.394(3) 2_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 121.35(19) . . ?
C1 N1 H1B 119.3 . . ?
C2 N1 H1B 119.3 . . ?
C14 O1 H1O 109.5 . . ?
C15 O3 H1O 108.3 . . ?
N1 C1 C3 120.5(2) . . ?
N1 C1 H1A 119.7 . . ?
C3 C1 H1A 119.7 . . ?
N1 C2 C4 120.6(2) . . ?
N1 C2 H2A 119.7 . . ?
C4 C2 H2A 119.7 . . ?
C1 C3 C5 120.3(2) . . ?
C1 C3 H3A 119.9 . . ?
C5 C3 H3A 119.9 . . ?
C2 C4 C5 119.9(2) . . ?
C2 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C3 C5 C4 117.3(2) . . ?
C3 C5 C6 119.9(2) . . ?
C4 C5 C6 122.81(19) . . ?
C7 C6 C5 125.1(2) . . ?
C7 C6 H6A 117.4 . . ?
C5 C6 H6A 117.4 . . ?
C6 C7 C8 126.5(2) . . ?
C6 C7 H7A 116.8 . . ?
C8 C7 H7A 116.8 . . ?
C10 C8 C9 116.16(19) . . ?
C10 C8 C7 121.7(2) . . ?
C9 C8 C7 122.0(2) . . ?
C11 C9 C8 122.4(2) . . ?
C11 C9 H9A 118.8 . . ?
C8 C9 H9A 118.8 . . ?
C12 C10 C8 122.7(2) . . ?
C12 C10 Cl1 117.32(18) . . ?
C8 C10 Cl1 119.93(17) . . ?
C9 C11 C13 118.8(2) . . ?
C9 C11 H11A 120.6 . . ?
C13 C11 H11A 120.6 . . ?
C13 C12 C10 118.4(2) . . ?
C13 C12 H12A 120.8 . . ?
C10 C12 H12A 120.8 . . ?
C12 C13 C11 121.4(2) . . ?
C12 C13 Cl2 118.60(19) . . ?
C11 C13 Cl2 120.00(19) . . ?
O2 C14 O1 120.6(2) . . ?
O2 C14 C18 120.3(2) . . ?
O1 C14 C18 119.0(2) . . ?
O4 C15 O3 123.2(2) . . ?
O4 C15 C17 116.8(2) . . ?
O3 C15 C17 119.9(2) . . ?
C17 C16 C18 124.04(19) . 2_666 ?
C17 C16 H16A 118.0 . . ?
C18 C16 H16A 118.0 2_666 . ?
C16 C17 C18 118.29(19) . . ?
C16 C17 C15 115.12(18) . . ?
C18 C17 C15 126.58(19) . . ?
C16 C18 C17 117.67(19) 2_666 . ?
C16 C18 C14 114.17(18) 2_666 . ?
C17 C18 C14 128.15(19) . . ?




_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.976    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;

#   End of CIF   ============================================================

####################################################################### 
# 
# 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_p-1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1447032'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#=========================================================================
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Br2 N2 O8'
_chemical_formula_sum            'C36 H26 Br2 N2 O8'
_chemical_formula_weight         774.41
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4131(15)
_cell_length_b                   10.094(2)
_cell_length_c                   12.181(2)
_cell_angle_alpha                113.45(3)
_cell_angle_beta                 99.10(3)
_cell_angle_gamma                101.00(3)
_cell_volume                     792.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2018
_cell_measurement_theta_min      1.8872
_cell_measurement_theta_max      27.9123

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             390
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.418
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8668
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.24
_reflns_number_total             2999
_reflns_number_gt                2160
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  "SHELXL-2003 (Sheldrick, 2003)'"
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0555P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.765
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.073

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 


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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.88084(6) 0.82794(4) 0.38491(4) 0.0674(2) Uani 1 1 d . . .
C13 C 0.7384(5) 0.6260(4) 0.2824(3) 0.0490(8) Uani 1 1 d . . .
N1 N -0.0167(4) -0.3370(3) -0.2765(2) 0.0480(7) Uani 1 1 d . . .
H1B H -0.0906 -0.4268 -0.3199 0.058 Uiso 1 1 calc R . .
C8 C 0.5166(5) 0.3322(4) 0.1298(3) 0.0482(8) Uani 1 1 d . . .
C2 C 0.0131(5) -0.2729(4) -0.1535(3) 0.0474(8) Uani 1 1 d . . .
H2A H -0.0445 -0.3267 -0.1155 0.057 Uiso 1 1 calc R . .
C10 C 0.5366(5) 0.3977(4) 0.2571(3) 0.0549(9) Uani 1 1 d . . .
H10A H 0.4754 0.3414 0.2920 0.066 Uiso 1 1 calc R . .
C6 C 0.3432(5) 0.1042(4) -0.0689(3) 0.0514(9) Uani 1 1 d . . .
H6A H 0.3918 0.1518 -0.1138 0.062 Uiso 1 1 calc R . .
C1 C 0.0667(5) -0.2631(4) -0.3323(3) 0.0513(9) Uani 1 1 d . . .
H1A H 0.0461 -0.3098 -0.4180 0.062 Uiso 1 1 calc R . .
C7 C 0.3929(5) 0.1799(4) 0.0543(3) 0.0509(9) Uani 1 1 d . . .
H7A H 0.3428 0.1295 0.0970 0.061 Uiso 1 1 calc R . .
C5 C 0.2169(5) -0.0488(4) -0.1377(3) 0.0424(8) Uani 1 1 d . . .
C4 C 0.1268(5) -0.1299(4) -0.0830(3) 0.0475(8) Uani 1 1 d . . .
H4A H 0.1442 -0.0862 0.0024 0.057 Uiso 1 1 calc R . .
C12 C 0.6440(5) 0.5431(4) 0.3323(3) 0.0550(9) Uani 1 1 d . . .
H12A H 0.6527 0.5851 0.4168 0.066 Uiso 1 1 calc R . .
C9 C 0.6179(5) 0.4193(4) 0.0822(3) 0.0535(9) Uani 1 1 d . . .
H9A H 0.6107 0.3780 -0.0022 0.064 Uiso 1 1 calc R . .
C3 C 0.1815(5) -0.1204(4) -0.2663(3) 0.0520(9) Uani 1 1 d . . .
H3A H 0.2371 -0.0699 -0.3072 0.062 Uiso 1 1 calc R . .
C11 C 0.7271(5) 0.5639(4) 0.1571(3) 0.0544(9) Uani 1 1 d . . .
H11A H 0.7933 0.6200 0.1238 0.065 Uiso 1 1 calc R . .
O3 O 0.2139(4) 0.6218(3) 0.2406(2) 0.0582(7) Uani 1 1 d . . .
O1 O 0.1992(4) 0.8089(3) 0.1668(2) 0.0669(8) Uani 1 1 d . . .
H1O H 0.2201 0.7232 0.2003 0.080 Uiso 1 1 d R . .
O2 O 0.2535(4) 1.0542(3) 0.2468(2) 0.0661(7) Uani 1 1 d . . .
O4 O 0.2389(4) 0.6188(3) 0.4215(2) 0.0553(6) Uani 1 1 d . . .
C14 C 0.3859(4) 0.9606(4) 0.3810(3) 0.0371(7) Uani 1 1 d . . .
C15 C 0.5017(4) 1.1052(4) 0.4577(3) 0.0403(7) Uani 1 1 d . . .
H15A H 0.5025 1.1774 0.4284 0.048 Uiso 1 1 calc R . .
C16 C 0.3829(4) 0.8499(4) 0.4243(3) 0.0372(7) Uani 1 1 d . . .
C17 C 0.2700(5) 0.6858(4) 0.3578(3) 0.0445(8) Uani 1 1 d . . .
C18 C 0.2705(5) 0.9432(4) 0.2576(3) 0.0477(8) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.888(4) . ?
C13 C12 1.370(5) . ?
C13 C11 1.381(5) . ?
N1 C1 1.327(4) . ?
N1 C2 1.334(4) . ?
N1 H1B 0.8600 . ?
C8 C10 1.391(5) . ?
C8 C9 1.403(5) . ?
C8 C7 1.456(5) . ?
C2 C4 1.361(5) . ?
C2 H2A 0.9300 . ?
C10 C12 1.371(5) . ?
C10 H10A 0.9300 . ?
C6 C7 1.332(5) . ?
C6 C5 1.461(5) . ?
C6 H6A 0.9300 . ?
C1 C3 1.356(5) . ?
C1 H1A 0.9300 . ?
C7 H7A 0.9300 . ?
C5 C4 1.388(5) . ?
C5 C3 1.393(4) . ?
C4 H4A 0.9300 . ?
C12 H12A 0.9300 . ?
C9 C11 1.369(5) . ?
C9 H9A 0.9300 . ?
C3 H3A 0.9300 . ?
C11 H11A 0.9300 . ?
O3 C17 1.266(4) . ?
O3 H1O 1.2966 . ?
O1 C18 1.300(4) . ?
O1 H1O 1.1184 . ?
O2 C18 1.206(4) . ?
O4 C17 1.237(4) . ?
C14 C15 1.387(4) . ?
C14 C16 1.411(4) . ?
C14 C18 1.532(4) . ?
C15 C16 1.395(4) 2_676 ?
C15 H15A 0.9300 . ?
C16 C15 1.395(4) 2_676 ?
C16 C17 1.513(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C13 C11 120.5(3) . . ?
C12 C13 Br1 119.8(3) . . ?
C11 C13 Br1 119.7(3) . . ?
C1 N1 C2 120.5(3) . . ?
C1 N1 H1B 119.7 . . ?
C2 N1 H1B 119.7 . . ?
C10 C8 C9 117.0(3) . . ?
C10 C8 C7 119.0(3) . . ?
C9 C8 C7 124.0(3) . . ?
N1 C2 C4 120.8(3) . . ?
N1 C2 H2A 119.6 . . ?
C4 C2 H2A 119.6 . . ?
C12 C10 C8 121.8(3) . . ?
C12 C10 H10A 119.1 . . ?
C8 C10 H10A 119.1 . . ?
C7 C6 C5 124.0(3) . . ?
C7 C6 H6A 118.0 . . ?
C5 C6 H6A 118.0 . . ?
N1 C1 C3 121.0(3) . . ?
N1 C1 H1A 119.5 . . ?
C3 C1 H1A 119.5 . . ?
C6 C7 C8 127.5(3) . . ?
C6 C7 H7A 116.2 . . ?
C8 C7 H7A 116.2 . . ?
C4 C5 C3 116.6(3) . . ?
C4 C5 C6 124.0(3) . . ?
C3 C5 C6 119.4(3) . . ?
C2 C4 C5 120.5(3) . . ?
C2 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C10 C12 C13 119.7(3) . . ?
C10 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C11 C9 C8 121.4(3) . . ?
C11 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C1 C3 C5 120.6(3) . . ?
C1 C3 H3A 119.7 . . ?
C5 C3 H3A 119.7 . . ?
C9 C11 C13 119.6(3) . . ?
C9 C11 H11A 120.2 . . ?
C13 C11 H11A 120.2 . . ?
C17 O3 H1O 109.2 . . ?
C18 O1 H1O 109.8 . . ?
C15 C14 C16 118.3(3) . . ?
C15 C14 C18 113.9(3) . . ?
C16 C14 C18 127.8(3) . . ?
C14 C15 C16 124.7(3) . 2_676 ?
C14 C15 H15A 117.7 . . ?
C16 C15 H15A 117.7 2_676 . ?
C15 C16 C14 117.0(3) 2_676 . ?
C15 C16 C17 115.1(3) 2_676 . ?
C14 C16 C17 127.9(3) . . ?
O4 C17 O3 122.6(3) . . ?
O4 C17 C16 117.7(3) . . ?
O3 C17 C16 119.7(3) . . ?
O2 C18 O1 122.2(3) . . ?
O2 C18 C14 119.2(3) . . ?
O1 C18 C14 118.6(3) . . ?



_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.973    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.

#   End of CIF   ============================================================


;
####################################################################### 
# 
# 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_p-1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1447033'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H26 N4 O8'
_chemical_formula_sum            'C38 H26 N4 O8'
_chemical_formula_weight         666.63
_chemical_compound_source        Synthesis


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9462(16)
_cell_length_b                   9.1625(18)
_cell_length_c                   11.719(2)
_cell_angle_alpha                101.68(3)
_cell_angle_beta                 102.13(3)
_cell_angle_gamma                97.57(3)
_cell_volume                     803.3(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4533
_cell_measurement_theta_min      1.8296
_cell_measurement_theta_max      27.7139

_exptl_crystal_description       Platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


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

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9832
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.86
_reflns_number_total             3058
_reflns_number_gt                1972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1174P)²+0.7637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2644
_refine_ls_wR_factor_gt          0.2313
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.799
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.056

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2683(4) 0.1458(3) 0.8051(2) 0.0746(9) Uani 1 1 d . . .
O2 O 0.0823(4) 0.3007(4) 0.7890(2) 0.0839(10) Uani 1 1 d . . .
O3 O -0.0933(5) 0.3875(4) 0.6333(3) 0.0862(11) Uani 1 1 d . . .
H1O H -0.0118 0.3463 0.6959 0.103 Uiso 1 1 d R . .
O4 O -0.1786(4) 0.3266(3) 0.4368(3) 0.0806(10) Uani 1 1 d . . .
N1 N 0.6387(4) 0.6545(4) 0.9777(3) 0.0597(9) Uani 1 1 d . . .
H1N H 0.6895 0.7447 1.0715 0.072 Uiso 1 1 d R . .
N2 N -0.1173(6) 0.2334(6) 0.0714(4) 0.1082(17) Uani 1 1 d . . .
C1 C 0.7170(6) 0.5383(5) 0.9500(4) 0.0679(11) Uani 1 1 d . . .
H1A H 0.8098 0.5243 1.0075 0.081 Uiso 1 1 calc R . .
C2 C 0.5057(6) 0.6784(5) 0.8975(4) 0.0641(11) Uani 1 1 d . . .
H2A H 0.4510 0.7603 0.9174 0.077 Uiso 1 1 calc R . .
C3 C 0.6675(6) 0.4384(5) 0.8408(4) 0.0723(12) Uani 1 1 d . . .
H3A H 0.7248 0.3572 0.8248 0.087 Uiso 1 1 calc R . .
C4 C 0.4488(6) 0.5807(5) 0.7840(4) 0.0701(12) Uani 1 1 d . . .
H4A H 0.3555 0.5971 0.7282 0.084 Uiso 1 1 calc R . .
C5 C 0.5313(6) 0.4584(5) 0.7536(4) 0.0669(12) Uani 1 1 d . . .
C6 C 0.4868(7) 0.3474(6) 0.6348(5) 0.0812(14) Uani 1 1 d . . .
H6A H 0.5441 0.2651 0.6280 0.097 Uiso 1 1 calc R . .
C7 C 0.3786(6) 0.3567(6) 0.5436(4) 0.0766(13) Uani 1 1 d . . .
H7A H 0.3204 0.4385 0.5517 0.092 Uiso 1 1 calc R . .
C8 C 0.3331(5) 0.2485(4) 0.4221(3) 0.0589(10) Uani 1 1 d . . .
C9 C 0.4158(6) 0.1288(5) 0.3867(4) 0.0695(12) Uani 1 1 d . . .
H9A H 0.5101 0.1116 0.4412 0.083 Uiso 1 1 calc R . .
C10 C 0.1962(5) 0.2737(4) 0.3400(3) 0.0555(10) Uani 1 1 d . . .
H10A H 0.1404 0.3545 0.3612 0.067 Uiso 1 1 calc R . .
C11 C 0.3614(6) 0.0345(5) 0.2725(4) 0.0718(12) Uani 1 1 d . . .
H11A H 0.4185 -0.0453 0.2512 0.086 Uiso 1 1 calc R . .
C12 C 0.1397(5) 0.1788(5) 0.2244(3) 0.0571(10) Uani 1 1 d . . .
C13 C 0.2225(6) 0.0592(5) 0.1905(4) 0.0683(12) Uani 1 1 d . . .
H13A H 0.1850 -0.0037 0.1136 0.082 Uiso 1 1 calc R . .
C14 C 0.1449(5) 0.1882(4) 0.7452(3) 0.0574(10) Uani 1 1 d . . .
C15 C -0.1098(5) 0.2962(4) 0.5297(4) 0.0565(10) Uani 1 1 d . . .
C16 C -0.0479(4) 0.1456(4) 0.5240(3) 0.0444(8) Uani 1 1 d . . .
C17 C 0.0645(4) 0.0988(4) 0.6157(3) 0.0437(8) Uani 1 1 d . . .
C18 C 0.1080(4) -0.0435(4) 0.5878(3) 0.0461(8) Uani 1 1 d . . .
H18A H 0.1826 -0.0730 0.6480 0.055 Uiso 1 1 calc R . .
C19 C -0.0054(6) 0.2096(6) 0.1402(4) 0.0774(13) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.236(5) . ?
O2 C14 1.266(5) . ?
O2 H1O 1.3591 . ?
O3 C15 1.299(5) . ?
O3 H1O 1.0379 . ?
O4 C15 1.214(5) . ?
N1 C1 1.321(5) . ?
N1 C2 1.332(5) . ?
N1 H1N 1.1883 . ?
N2 C19 1.144(6) . ?
C1 C3 1.361(6) . ?
C1 H1A 0.9300 . ?
C2 C4 1.390(6) . ?
C2 H2A 0.9300 . ?
C3 C5 1.383(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.394(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.491(6) . ?
C6 C7 1.248(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.503(6) . ?
C7 H7A 0.9300 . ?
C8 C10 1.371(6) . ?
C8 C9 1.388(6) . ?
C9 C11 1.384(6) . ?
C9 H9A 0.9300 . ?
C10 C12 1.398(5) . ?
C10 H10A 0.9300 . ?
C11 C13 1.379(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.385(6) . ?
C12 C19 1.450(6) . ?
C13 H13A 0.9300 . ?
C14 C17 1.528(5) . ?
C15 C16 1.519(5) . ?
C16 C18 1.394(5) 2_556 ?
C16 C17 1.421(5) . ?
C17 C18 1.385(5) . ?
C18 C16 1.394(5) 2_556 ?
C18 H18A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 H1O 107.7 . . ?
C15 O3 H1O 106.3 . . ?
C1 N1 C2 120.4(3) . . ?
C1 N1 H1N 121.5 . . ?
C2 N1 H1N 118.0 . . ?
N1 C1 C3 122.6(4) . . ?
N1 C1 H1A 118.7 . . ?
C3 C1 H1A 118.7 . . ?
N1 C2 C4 120.0(4) . . ?
N1 C2 H2A 120.0 . . ?
C4 C2 H2A 120.0 . . ?
C1 C3 C5 119.5(4) . . ?
C1 C3 H3A 120.2 . . ?
C5 C3 H3A 120.2 . . ?
C2 C4 C5 120.1(4) . . ?
C2 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C3 C5 C4 117.4(4) . . ?
C3 C5 C6 116.9(4) . . ?
C4 C5 C6 125.8(4) . . ?
C7 C6 C5 125.0(5) . . ?
C7 C6 H6A 117.5 . . ?
C5 C6 H6A 117.5 . . ?
C6 C7 C8 126.3(5) . . ?
C6 C7 H7A 116.8 . . ?
C8 C7 H7A 116.8 . . ?
C10 C8 C9 118.3(4) . . ?
C10 C8 C7 115.3(4) . . ?
C9 C8 C7 126.4(4) . . ?
C11 C9 C8 121.7(4) . . ?
C11 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C8 C10 C12 120.6(4) . . ?
C8 C10 H10A 119.7 . . ?
C12 C10 H10A 119.7 . . ?
C13 C11 C9 119.9(4) . . ?
C13 C11 H11A 120.1 . . ?
C9 C11 H11A 120.1 . . ?
C13 C12 C10 120.6(4) . . ?
C13 C12 C19 120.6(4) . . ?
C10 C12 C19 118.8(4) . . ?
C11 C13 C12 119.0(4) . . ?
C11 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
O1 C14 O2 121.9(3) . . ?
O1 C14 C17 118.4(3) . . ?
O2 C14 C17 119.8(3) . . ?
O4 C15 O3 121.3(4) . . ?
O4 C15 C16 119.0(3) . . ?
O3 C15 C16 119.6(4) . . ?
C18 C16 C17 117.3(3) 2_556 . ?
C18 C16 C15 114.1(3) 2_556 . ?
C17 C16 C15 128.6(3) . . ?
C18 C17 C16 118.1(3) . . ?
C18 C17 C14 114.6(3) . . ?
C16 C17 C14 127.3(3) . . ?
C17 C18 C16 124.6(3) . 2_556 ?
C17 C18 H18A 117.7 . . ?
C16 C18 H18A 117.7 2_556 . ?
N2 C19 C12 178.1(5) . . ?


_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.973    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;
#   End of CIF   ============================================================



####################################################################### 
# 
# 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_p-1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1447031'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

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

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Br2 N2 O8'
_chemical_formula_sum            'C36 H26 Br2 N2 O8'
_chemical_formula_weight         774.41
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8733(16)
_cell_length_b                   9.936(2)
_cell_length_c                   11.490(2)
_cell_angle_alpha                106.03(3)
_cell_angle_beta                 108.74(3)
_cell_angle_gamma                96.25(3)
_cell_volume                     798.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4917
_cell_measurement_theta_min      1.9830
_cell_measurement_theta_max      27.9123

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             390
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


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

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9943
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.06
_reflns_number_total             3049
_reflns_number_gt                2162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.2184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3049
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.784
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.068


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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.96538(6) 0.38251(6) -0.39861(4) 0.0902(3) Uani 1 1 d . . .
N1 N 0.6892(4) -0.0850(3) 0.2313(3) 0.0594(8) Uani 1 1 d . . .
H1N H 0.6291 -0.1480 0.2627 0.071 Uiso 1 1 d R . .
O1 O 0.3845(4) 0.1063(3) 0.2947(2) 0.0743(8) Uani 1 1 d . . .
H1O H 0.3594 0.1219 0.3802 0.089 Uiso 1 1 d R . .
O2 O 0.5238(4) 0.2420(3) 0.2166(2) 0.0716(8) Uani 1 1 d . . .
O3 O 0.6671(4) 0.8722(3) 0.5041(3) 0.0741(8) Uani 1 1 d . . .
O4 O 0.5341(4) 0.7208(3) 0.3035(2) 0.0707(8) Uani 1 1 d . . .
C1 C 0.6423(5) -0.1079(4) 0.1041(4) 0.0560(9) Uani 1 1 d . . .
H1A H 0.5493 -0.1860 0.0452 0.067 Uiso 1 1 calc R . .
C2 C 0.8211(6) 0.0258(4) 0.3188(4) 0.0643(10) Uani 1 1 d . . .
H2A H 0.8511 0.0406 0.4072 0.077 Uiso 1 1 calc R . .
C3 C 0.7275(5) -0.0197(3) 0.0590(3) 0.0496(8) Uani 1 1 d . . .
H3A H 0.6927 -0.0373 -0.0302 0.059 Uiso 1 1 calc R . .
C4 C 0.9118(5) 0.1170(4) 0.2791(3) 0.0613(10) Uani 1 1 d . . .
H4A H 1.0048 0.1935 0.3409 0.074 Uiso 1 1 calc R . .
C5 C 0.8678(5) 0.0979(3) 0.1467(3) 0.0484(8) Uani 1 1 d . . .
C6 C 0.9643(5) 0.1983(4) 0.1059(3) 0.0527(9) Uani 1 1 d . . .
H6A H 1.0569 0.2723 0.1715 0.063 Uiso 1 1 calc R . .
C7 C 0.9335(5) 0.1949(4) -0.0152(3) 0.0517(8) Uani 1 1 d . . .
H7A H 0.8415 0.1206 -0.0810 0.062 Uiso 1 1 calc R . .
C8 C 1.0305(4) 0.2968(3) -0.0550(3) 0.0472(8) Uani 1 1 d . . .
C9 C 0.9676(5) 0.2899(4) -0.1849(3) 0.0525(8) Uani 1 1 d . . .
H9A H 0.8655 0.2202 -0.2458 0.063 Uiso 1 1 calc R . .
C10 C 1.1846(5) 0.4016(4) 0.0327(3) 0.0525(8) Uani 1 1 d . . .
H10A H 1.2287 0.4075 0.1198 0.063 Uiso 1 1 calc R . .
C11 C 1.0571(5) 0.3870(4) -0.2232(3) 0.0537(9) Uani 1 1 d . . .
C12 C 1.2734(5) 0.4971(4) -0.0079(4) 0.0558(9) Uani 1 1 d . . .
H12A H 1.3762 0.5666 0.0522 0.067 Uiso 1 1 calc R . .
C13 C 1.2103(5) 0.4902(4) -0.1370(3) 0.0562(9) Uani 1 1 d . . .
H13A H 1.2701 0.5538 -0.1647 0.067 Uiso 1 1 calc R . .
C14 C 0.4645(5) 0.2309(4) 0.2997(3) 0.0549(9) Uani 1 1 d . . .
C15 C 0.4791(4) 0.3646(3) 0.4091(3) 0.0443(7) Uani 1 1 d . . .
C16 C 0.5178(4) 0.4911(4) 0.3854(3) 0.0461(8) Uani 1 1 d . . .
H16A H 0.5303 0.4849 0.3065 0.055 Uiso 1 1 calc R . .
C17 C 0.5393(4) 0.6271(3) 0.4712(3) 0.0437(7) Uani 1 1 d . . .
C18 C 0.5813(5) 0.7496(4) 0.4232(3) 0.0530(9) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.895(4) . ?
N1 C2 1.330(5) . ?
N1 C1 1.332(5) . ?
O1 C14 1.303(4) . ?
O2 C14 1.215(4) . ?
O3 C18 1.263(4) . ?
O4 C18 1.243(4) . ?
C1 C3 1.354(5) . ?
C2 C4 1.354(5) . ?
C3 C5 1.398(5) . ?
C4 C5 1.400(5) . ?
C5 C6 1.453(5) . ?
C6 C7 1.324(5) . ?
C7 C8 1.460(5) . ?
C8 C10 1.390(5) . ?
C8 C9 1.393(5) . ?
C9 C11 1.380(5) . ?
C10 C12 1.384(5) . ?
C11 C13 1.375(5) . ?
C12 C13 1.384(5) . ?
C14 C15 1.520(5) . ?
C15 C16 1.380(5) . ?
C15 C17 1.410(4) 2_666 ?
C16 C17 1.391(4) . ?
C17 C15 1.410(4) 2_666 ?
C17 C18 1.514(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 121.2(3) . . ?
N1 C1 C3 121.3(3) . . ?
N1 C2 C4 120.0(3) . . ?
C1 C3 C5 119.8(3) . . ?
C2 C4 C5 121.1(3) . . ?
C3 C5 C4 116.6(3) . . ?
C3 C5 C6 123.1(3) . . ?
C4 C5 C6 120.3(3) . . ?
C7 C6 C5 126.5(3) . . ?
C6 C7 C8 126.1(3) . . ?
C10 C8 C9 118.4(3) . . ?
C10 C8 C7 122.2(3) . . ?
C9 C8 C7 119.4(3) . . ?
C11 C9 C8 119.8(3) . . ?
C12 C10 C8 120.9(3) . . ?
C13 C11 C9 122.0(3) . . ?
C13 C11 Br1 118.3(3) . . ?
C9 C11 Br1 119.8(3) . . ?
C13 C12 C10 120.6(3) . . ?
C11 C13 C12 118.4(3) . . ?
O2 C14 O1 121.0(3) . . ?
O2 C14 C15 119.5(3) . . ?
O1 C14 C15 119.5(3) . . ?
C16 C15 C17 118.1(3) . 2_666 ?
C16 C15 C14 114.0(3) . . ?
C17 C15 C14 127.9(3) 2_666 . ?
C15 C16 C17 124.7(3) . . ?
C16 C17 C15 117.2(3) . 2_666 ?
C16 C17 C18 114.9(3) . . ?
C15 C17 C18 127.9(3) 2_666 . ?
O4 C18 O3 123.3(3) . . ?
O4 C18 C17 116.7(3) . . ?
O3 C18 C17 120.0(3) . . ?

_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.975    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;
#   End of CIF   ============================================================

####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1447034'


_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H26 N4 O8'
_chemical_formula_sum            'C38 H26 N4 O8'
_chemical_formula_weight         666.63
_chemical_compound_source        Synthesis


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.513(3)
_cell_length_b                   6.4340(13)
_cell_length_c                   18.566(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.85(3)
_cell_angle_gamma                90.00
_cell_volume                     1579.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9294
_cell_measurement_theta_min      3.0794
_cell_measurement_theta_max      55.499

_exptl_crystal_description       Platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


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

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18641
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         28.05
_reflns_number_total             3094
_reflns_number_gt                2277
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.7343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3094
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.806
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.046
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.88182(15) -0.1956(3) 0.14921(10) 0.0455(5) Uani 1 1 d . . .
H1N H 0.9186 -0.3371 0.1414 0.055 Uiso 1 1 d R . .
N2 N 0.3901(2) 0.2596(6) 0.02330(18) 0.1043(11) Uani 1 1 d . . .
O1 O 1.14614(16) -0.9128(3) 0.18690(10) 0.0705(6) Uani 1 1 d . . .
O2 O 1.17950(13) -0.6477(3) 0.12086(9) 0.0559(5) Uani 1 1 d . . .
H1O H 1.1542 -0.5887 0.0683 0.067 Uiso 1 1 d R . .
O3 O 0.96692(13) -0.5545(3) 0.11830(9) 0.0519(5) Uani 1 1 d . . .
O4 O 0.86082(13) -0.5157(3) 0.01046(9) 0.0521(5) Uani 1 1 d . . .
C1 C 0.90746(19) -0.0801(4) 0.21032(13) 0.0508(6) Uani 1 1 d . . .
H1A H 0.9620 -0.1198 0.2469 0.061 Uiso 1 1 calc R . .
C2 C 0.80349(19) -0.1408(4) 0.09603(13) 0.0494(6) Uani 1 1 d . . .
H2A H 0.7863 -0.2230 0.0541 0.059 Uiso 1 1 calc R . .
C3 C 0.85451(18) 0.0947(4) 0.21944(13) 0.0483(6) Uani 1 1 d . . .
H3A H 0.8731 0.1731 0.2622 0.058 Uiso 1 1 calc R . .
C4 C 0.74850(19) 0.0330(4) 0.10219(13) 0.0501(6) Uani 1 1 d . . .
H4A H 0.6947 0.0692 0.0644 0.060 Uiso 1 1 calc R . .
C5 C 0.77255(17) 0.1571(4) 0.16497(12) 0.0429(5) Uani 1 1 d . . .
C6 C 0.71399(18) 0.3427(4) 0.17561(13) 0.0488(6) Uani 1 1 d . . .
H6A H 0.7418 0.4336 0.2133 0.059 Uiso 1 1 calc R . .
C7 C 0.62461(19) 0.3889(4) 0.13535(14) 0.0516(6) Uani 1 1 d . . .
H7A H 0.5996 0.2994 0.0966 0.062 Uiso 1 1 calc R . .
C8 C 0.5604(2) 0.5657(4) 0.14492(14) 0.0518(6) Uani 1 1 d . . .
C9 C 0.5946(2) 0.7331(4) 0.19059(16) 0.0609(7) Uani 1 1 d . . .
H9A H 0.6613 0.7361 0.2163 0.073 Uiso 1 1 calc R . .
C10 C 0.4586(2) 0.5674(5) 0.10734(15) 0.0608(7) Uani 1 1 d . . .
C11 C 0.5303(3) 0.8955(5) 0.19828(19) 0.0764(9) Uani 1 1 d . . .
H11A H 0.5543 1.0068 0.2289 0.092 Uiso 1 1 calc R . .
C12 C 0.3951(3) 0.7319(6) 0.11522(19) 0.0796(10) Uani 1 1 d . . .
H12A H 0.3284 0.7317 0.0894 0.096 Uiso 1 1 calc R . .
C13 C 0.4303(3) 0.8935(6) 0.1607(2) 0.0877(11) Uani 1 1 d . . .
H13A H 0.3874 1.0024 0.1665 0.105 Uiso 1 1 calc R . .
C14 C 0.4197(2) 0.3973(6) 0.06052(18) 0.0728(9) Uani 1 1 d . . .
C15 C 1.12942(18) -0.8194(4) 0.12877(12) 0.0467(6) Uani 1 1 d . . .
C16 C 0.93033(17) -0.6098(4) 0.05357(12) 0.0417(5) Uani 1 1 d . . .
C17 C 1.05891(17) -0.9062(3) 0.06239(11) 0.0390(5) Uani 1 1 d . . .
C18 C 0.96973(16) -0.8086(3) 0.02585(11) 0.0386(5) Uani 1 1 d . . .
C19 C 1.08653(17) -1.0952(4) 0.03641(12) 0.0403(5) Uiso 1 1 d . . .
H19A H 1.1449 -1.1602 0.0616 0.048 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.338(3) . ?
N1 C1 1.341(3) . ?
N1 H1N 1.0607 . ?
N2 C14 1.144(4) . ?
O1 C15 1.215(3) . ?
O2 C15 1.319(3) . ?
O2 H1O 1.0371 . ?
O3 C16 1.254(3) . ?
O4 C16 1.257(3) . ?
C1 C3 1.362(3) . ?
C1 H1A 0.9300 . ?
C2 C4 1.360(3) . ?
C2 H2A 0.9300 . ?
C3 C5 1.396(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.468(3) . ?
C6 C7 1.317(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.463(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.390(4) . ?
C8 C10 1.409(4) . ?
C9 C11 1.385(4) . ?
C9 H9A 0.9300 . ?
C10 C12 1.389(4) . ?
C10 C14 1.429(5) . ?
C11 C13 1.388(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.362(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C15 C17 1.502(3) . ?
C16 C18 1.516(3) . ?
C17 C19 1.387(3) . ?
C17 C18 1.404(3) . ?
C18 C19 1.392(3) 3_735 ?
C19 C18 1.392(3) 3_735 ?
C19 H19A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 120.4(2) . . ?
C2 N1 H1N 116.6 . . ?
C1 N1 H1N 122.9 . . ?
C15 O2 H1O 109.5 . . ?
N1 C1 C3 120.8(2) . . ?
N1 C1 H1A 119.6 . . ?
C3 C1 H1A 119.6 . . ?
N1 C2 C4 121.2(2) . . ?
N1 C2 H2A 119.4 . . ?
C4 C2 H2A 119.4 . . ?
C1 C3 C5 120.4(2) . . ?
C1 C3 H3A 119.8 . . ?
C5 C3 H3A 119.8 . . ?
C2 C4 C5 120.2(2) . . ?
C2 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C3 117.1(2) . . ?
C4 C5 C6 122.6(2) . . ?
C3 C5 C6 120.4(2) . . ?
C7 C6 C5 124.3(2) . . ?
C7 C6 H6A 117.8 . . ?
C5 C6 H6A 117.8 . . ?
C6 C7 C8 127.2(2) . . ?
C6 C7 H7A 116.4 . . ?
C8 C7 H7A 116.4 . . ?
C9 C8 C10 117.7(3) . . ?
C9 C8 C7 123.1(2) . . ?
C10 C8 C7 119.3(2) . . ?
C11 C9 C8 120.7(3) . . ?
C11 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C12 C10 C8 121.0(3) . . ?
C12 C10 C14 119.3(3) . . ?
C8 C10 C14 119.7(3) . . ?
C9 C11 C13 120.5(3) . . ?
C9 C11 H11A 119.7 . . ?
C13 C11 H11A 119.7 . . ?
C13 C12 C10 120.2(3) . . ?
C13 C12 H12A 119.9 . . ?
C10 C12 H12A 119.9 . . ?
C12 C13 C11 119.9(3) . . ?
C12 C13 H13A 120.0 . . ?
C11 C13 H13A 120.0 . . ?
N2 C14 C10 178.9(3) . . ?
O1 C15 O2 120.5(2) . . ?
O1 C15 C17 121.0(2) . . ?
O2 C15 C17 118.3(2) . . ?
O3 C16 O4 124.8(2) . . ?
O3 C16 C18 117.90(19) . . ?
O4 C16 C18 117.30(19) . . ?
C19 C17 C18 119.3(2) . . ?
C19 C17 C15 116.15(19) . . ?
C18 C17 C15 124.5(2) . . ?
C19 C18 C17 118.1(2) 3_735 . ?
C19 C18 C16 119.17(19) 3_735 . ?
C17 C18 C16 122.68(19) . . ?
C17 C19 C18 122.6(2) . 3_735 ?
C17 C19 H19A 118.7 . . ?
C18 C19 H19A 118.7 3_735 . ?

_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.977    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;


#   End of CIF   ============================================================

####################################################################### 
# 
# 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_p-1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1447035'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cl2 N2 O8'
_chemical_formula_sum            'C36 H26 Cl2 N2 O8'
_chemical_formula_weight         685.49
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9176(18)
_cell_length_b                   9.7483(19)
_cell_length_c                   10.094(2)
_cell_angle_alpha                64.40(3)
_cell_angle_beta                 89.60(3)
_cell_angle_gamma                88.69(3)
_cell_volume                     791.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2052
_cell_measurement_theta_min      4.5688
_cell_measurement_theta_max      56.3252

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             354
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9839
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         28.16
_reflns_number_total             3033
_reflns_number_gt                2320
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-2003 (Sheldrick, 2003)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0607P)²+0.5609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3033
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_measured_fraction_theta_max 0.783
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.055

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 


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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.28667(12) 0.68337(10) 0.92622(10) 0.0636(3) Uani 1 1 d . . .
N1 N -0.0492(3) 1.4605(3) 0.7145(3) 0.0414(6) Uani 1 1 d . . .
H1B H -0.1045 1.5369 0.6588 0.050 Uiso 1 1 calc R . .
O1 O -0.1513(2) 1.8178(2) 0.6924(2) 0.0403(5) Uani 1 1 d . . .
O2 O -0.2314(2) 1.6879(2) 0.5709(3) 0.0502(6) Uani 1 1 d . . .
O3 O -0.8878(2) 1.9369(2) 0.6197(2) 0.0370(5) Uani 1 1 d . . .
H1O H -0.9874 1.8845 0.6481 0.044 Uiso 1 1 d R . .
O4 O -0.8143(2) 1.7408(2) 0.5749(3) 0.0537(6) Uani 1 1 d . . .
C1 C -0.0350(4) 1.3397(3) 0.6856(4) 0.0468(8) Uani 1 1 d . . .
H1A H -0.0839 1.3389 0.6049 0.056 Uiso 1 1 calc R . .
C2 C 0.0207(4) 1.4642(3) 0.8278(4) 0.0485(8) Uani 1 1 d . . .
H2A H 0.0120 1.5511 0.8438 0.058 Uiso 1 1 calc R . .
C3 C 0.0521(4) 1.2161(3) 0.7750(4) 0.0507(8) Uani 1 1 d . . .
H3A H 0.0630 1.1329 0.7532 0.061 Uiso 1 1 calc R . .
C4 C 0.1054(4) 1.3432(4) 0.9222(4) 0.0508(8) Uani 1 1 d . . .
H4A H 0.1509 1.3470 1.0031 0.061 Uiso 1 1 calc R . .
C5 C 0.1233(3) 1.2144(3) 0.8967(3) 0.0421(7) Uani 1 1 d . . .
C6 C 0.2153(4) 1.0867(3) 1.0015(4) 0.0491(8) Uani 1 1 d . . .
H6A H 0.2479 1.0938 1.0856 0.059 Uiso 1 1 calc R . .
C7 C 0.2553(4) 0.9644(3) 0.9866(4) 0.0481(8) Uani 1 1 d . . .
H7A H 0.2204 0.9564 0.9037 0.058 Uiso 1 1 calc R . .
C8 C 0.3499(3) 0.8385(3) 1.0885(3) 0.0409(7) Uani 1 1 d . . .
C9 C 0.3751(4) 0.7067(3) 1.0693(3) 0.0420(7) Uani 1 1 d . . .
C10 C 0.4233(4) 0.8439(4) 1.2080(4) 0.0560(9) Uani 1 1 d . . .
H10A H 0.4092 0.9292 1.2259 0.067 Uiso 1 1 calc R . .
C11 C 0.4663(4) 0.5884(3) 1.1615(4) 0.0509(8) Uani 1 1 d . . .
H11A H 0.4794 0.5015 1.1460 0.061 Uiso 1 1 calc R . .
C12 C 0.5161(4) 0.7266(4) 1.3002(4) 0.0580(9) Uani 1 1 d . . .
H12A H 0.5639 0.7338 1.3784 0.070 Uiso 1 1 calc R . .
C13 C 0.5377(4) 0.5993(4) 1.2763(4) 0.0533(9) Uani 1 1 d . . .
H13A H 0.6007 0.5205 1.3380 0.064 Uiso 1 1 calc R . .
C14 C -0.2385(3) 1.7961(3) 0.6074(3) 0.0333(6) Uani 1 1 d . . .
C15 C -0.7898(3) 1.8619(3) 0.5749(3) 0.0341(6) Uani 1 1 d . . .
C16 C -0.6431(3) 1.9380(3) 0.5316(3) 0.0303(6) Uani 1 1 d . . .
C17 C -0.5142(3) 1.8455(3) 0.5764(3) 0.0339(6) Uani 1 1 d . . .
H17A H -0.5243 1.7408 0.6278 0.041 Uiso 1 1 calc R . .
C18 C -0.3715(3) 1.9046(3) 0.5466(3) 0.0300(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.751(3) . ?
N1 C2 1.320(4) . ?
N1 C1 1.334(4) . ?
N1 H1B 0.8600 . ?
O1 C14 1.249(3) . ?
O2 C14 1.259(3) . ?
O3 C15 1.324(3) . ?
O3 H1O 1.0115 . ?
O4 C15 1.206(3) . ?
C1 C3 1.377(4) . ?
C1 H1A 0.9300 . ?
C2 C4 1.366(4) . ?
C2 H2A 0.9300 . ?
C3 C5 1.381(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.392(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.473(4) . ?
C6 C7 1.306(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.466(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.394(4) . ?
C8 C10 1.398(4) . ?
C9 C11 1.378(4) . ?
C10 C12 1.381(4) . ?
C10 H10A 0.9300 . ?
C11 C13 1.371(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.371(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C18 1.515(3) . ?
C15 C16 1.486(4) . ?
C16 C17 1.395(3) . ?
C16 C18 1.398(4) 2_496 ?
C17 C18 1.386(4) . ?
C17 H17A 0.9300 . ?
C18 C16 1.398(4) 2_496 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 120.7(2) . . ?
C2 N1 H1B 119.6 . . ?
C1 N1 H1B 119.6 . . ?
C15 O3 H1O 112.6 . . ?
N1 C1 C3 120.1(3) . . ?
N1 C1 H1A 119.9 . . ?
C3 C1 H1A 119.9 . . ?
N1 C2 C4 121.6(3) . . ?
N1 C2 H2A 119.2 . . ?
C4 C2 H2A 119.2 . . ?
C1 C3 C5 120.6(3) . . ?
C1 C3 H3A 119.7 . . ?
C5 C3 H3A 119.7 . . ?
C2 C4 C5 119.8(3) . . ?
C2 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C3 C5 C4 117.1(3) . . ?
C3 C5 C6 125.0(3) . . ?
C4 C5 C6 117.9(3) . . ?
C7 C6 C5 125.7(3) . . ?
C7 C6 H6A 117.1 . . ?
C5 C6 H6A 117.1 . . ?
C6 C7 C8 126.1(3) . . ?
C6 C7 H7A 116.9 . . ?
C8 C7 H7A 116.9 . . ?
C9 C8 C10 115.8(3) . . ?
C9 C8 C7 121.5(3) . . ?
C10 C8 C7 122.7(3) . . ?
C11 C9 C8 122.6(3) . . ?
C11 C9 Cl1 116.9(2) . . ?
C8 C9 Cl1 120.4(2) . . ?
C12 C10 C8 122.0(3) . . ?
C12 C10 H10A 119.0 . . ?
C8 C10 H10A 119.0 . . ?
C13 C11 C9 119.7(3) . . ?
C13 C11 H11A 120.2 . . ?
C9 C11 H11A 120.2 . . ?
C13 C12 C10 120.0(3) . . ?
C13 C12 H12A 120.0 . . ?
C10 C12 H12A 120.0 . . ?
C12 C13 C11 119.9(3) . . ?
C12 C13 H13A 120.0 . . ?
C11 C13 H13A 120.0 . . ?
O1 C14 O2 126.5(2) . . ?
O1 C14 C18 117.9(2) . . ?
O2 C14 C18 115.5(2) . . ?
O4 C15 O3 123.6(3) . . ?
O4 C15 C16 123.0(3) . . ?
O3 C15 C16 113.3(2) . . ?
C17 C16 C18 119.2(2) . 2_496 ?
C17 C16 C15 117.1(2) . . ?
C18 C16 C15 123.6(2) 2_496 . ?
C18 C17 C16 122.1(2) . . ?
C18 C17 H17A 119.0 . . ?
C16 C17 H17A 119.0 . . ?
C17 C18 C16 118.7(2) . 2_496 ?
C17 C18 C14 118.2(2) . . ?
C16 C18 C14 123.0(2) 2_496 . ?

_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.977    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;

#   End of CIF   ============================================================
####################################################################### 
# 
# 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_p21c_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1447038'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H26 N4 O8'
_chemical_formula_sum            'C38 H26 N4 O8'
_chemical_formula_weight         666.63
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8116(18)
_cell_length_b                   11.811(2)
_cell_length_c                   15.299(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.37(3)
_cell_angle_gamma                90.00
_cell_volume                     1519.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8471
_cell_measurement_theta_min      1.7241
_cell_measurement_theta_max      27.9564

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17995
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.98
_reflns_number_total             3133
_reflns_number_gt                2168
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXS-2003 (Sheldrick, 2003)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0815P)²+0.5866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1863
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.855
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.071

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 


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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6711(3) 0.5105(2) 0.65370(16) 0.0549(7) Uani 1 1 d . . .
H1A H 0.6455 0.5183 0.7034 0.066 Uiso 1 1 calc R . .
N2 N 1.1184(3) 0.3348(3) 0.00817(17) 0.0667(8) Uani 1 1 d . . .
C1 C 0.6428(4) 0.5948(3) 0.5936(2) 0.0574(8) Uani 1 1 d . . .
H1 H 0.5972 0.6614 0.6062 0.069 Uiso 1 1 calc R . .
C2 C 0.7378(4) 0.4146(3) 0.6392(2) 0.0531(8) Uani 1 1 d . . .
H3 H 0.7577 0.3570 0.6826 0.064 Uiso 1 1 calc R . .
C3 C 0.6796(4) 0.5847(3) 0.5136(2) 0.0516(7) Uani 1 1 d . . .
H4 H 0.6583 0.6439 0.4715 0.062 Uiso 1 1 calc R . .
C4 C 0.7773(4) 0.4010(3) 0.5600(2) 0.0495(7) Uani 1 1 d . . .
H5 H 0.8237 0.3336 0.5497 0.059 Uiso 1 1 calc R . .
C5 C 0.7490(3) 0.4860(2) 0.49506(18) 0.0420(7) Uani 1 1 d . . .
C6 C 0.7879(4) 0.4784(3) 0.4087(2) 0.0524(8) Uani 1 1 d . . .
H6 H 0.7556 0.5380 0.3676 0.063 Uiso 1 1 calc R . .
C7 C 0.8638(4) 0.3954(3) 0.3844(2) 0.0513(8) Uani 1 1 d . . .
H7 H 0.8910 0.3346 0.4247 0.062 Uiso 1 1 calc R . .
C8 C 0.9112(3) 0.3872(3) 0.30015(18) 0.0454(7) Uani 1 1 d . . .
C9 C 0.8663(4) 0.4645(3) 0.2294(2) 0.0505(7) Uani 1 1 d . . .
H8 H 0.7993 0.5240 0.2329 0.061 Uiso 1 1 calc R . .
C10 C 1.0092(4) 0.2985(3) 0.2938(2) 0.0551(8) Uani 1 1 d . . .
H9 H 1.0387 0.2453 0.3406 0.066 Uiso 1 1 calc R . .
C11 C 0.9196(4) 0.4545(3) 0.15281(19) 0.0491(7) Uani 1 1 d . . .
H10 H 0.8884 0.5067 0.1052 0.059 Uiso 1 1 calc R . .
C12 C 1.0635(4) 0.2879(3) 0.2189(2) 0.0527(8) Uani 1 1 d . . .
H11 H 1.1301 0.2281 0.2154 0.063 Uiso 1 1 calc R . .
C13 C 1.0193(3) 0.3664(2) 0.14846(18) 0.0427(7) Uani 1 1 d . . .
C14 C 1.0751(4) 0.3511(3) 0.0698(2) 0.0509(7) Uani 1 1 d . . .
O1 O 0.7153(3) 0.1325(2) 0.35282(15) 0.0695(7) Uani 1 1 d . . .
O2 O 0.4568(2) 0.16781(16) 0.29628(13) 0.0517(6) Uani 1 1 d . . .
H45 H 0.4860 0.2038 0.2509 0.078 Uiso 1 1 d R . .
O3 O 0.5406(3) -0.07672(17) 0.27669(13) 0.0634(7) Uani 1 1 d . . .
O4 O 0.5015(3) -0.23392(15) 0.34287(12) 0.0537(6) Uani 1 1 d . . .
C57 C 0.5807(3) 0.1207(2) 0.35469(17) 0.0368(6) Uani 1 1 d . . .
C58 C 0.5384(3) 0.05572(19) 0.42854(16) 0.0315(6) Uani 1 1 d . . .
C59 C 0.5275(3) 0.1141(2) 0.50507(16) 0.0335(6) Uani 1 1 d . . .
H46 H 0.5460 0.1917 0.5083 0.040 Uiso 1 1 calc R . .
C60 C 0.5096(3) -0.06140(19) 0.42329(15) 0.0313(6) Uani 1 1 d . . .
C61 C 0.5189(3) -0.1285(2) 0.34101(16) 0.0364(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.325(4) . ?
N1 C1 1.328(4) . ?
N1 H1A 0.8600 . ?
N2 C14 1.134(3) . ?
C1 C3 1.362(4) . ?
C1 H1 0.9300 . ?
C2 C4 1.365(4) . ?
C2 H3 0.9300 . ?
C3 C5 1.384(4) . ?
C3 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H5 0.9300 . ?
C5 C6 1.464(4) . ?
C6 C7 1.302(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.472(4) . ?
C7 H7 0.9300 . ?
C8 C10 1.380(4) . ?
C8 C9 1.380(4) . ?
C9 C11 1.391(4) . ?
C9 H8 0.9300 . ?
C10 C12 1.372(4) . ?
C10 H9 0.9300 . ?
C11 C13 1.376(4) . ?
C11 H10 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H11 0.9300 . ?
C13 C14 1.441(4) . ?
O1 C57 1.203(3) . ?
O2 C57 1.311(3) . ?
O2 H45 0.9148 . ?
O3 C61 1.222(3) . ?
O4 C61 1.255(3) . ?
C57 C58 1.502(3) . ?
C58 C59 1.386(3) . ?
C58 C60 1.404(3) . ?
C59 C60 1.382(3) 3_656 ?
C59 H46 0.9300 . ?
C60 C59 1.382(3) 3_656 ?
C60 C61 1.510(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 121.7(2) . . ?
C2 N1 H1A 119.1 . . ?
C1 N1 H1A 119.1 . . ?
N1 C1 C3 120.8(3) . . ?
N1 C1 H1 119.6 . . ?
C3 C1 H1 119.6 . . ?
N1 C2 C4 119.5(3) . . ?
N1 C2 H3 120.2 . . ?
C4 C2 H3 120.2 . . ?
C1 C3 C5 119.7(3) . . ?
C1 C3 H4 120.2 . . ?
C5 C3 H4 120.2 . . ?
C2 C4 C5 120.9(3) . . ?
C2 C4 H5 119.6 . . ?
C5 C4 H5 119.6 . . ?
C4 C5 C3 117.4(2) . . ?
C4 C5 C6 124.3(3) . . ?
C3 C5 C6 118.2(3) . . ?
C7 C6 C5 125.6(3) . . ?
C7 C6 H6 117.2 . . ?
C5 C6 H6 117.2 . . ?
C6 C7 C8 127.1(3) . . ?
C6 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C10 C8 C9 119.1(3) . . ?
C10 C8 C7 117.3(3) . . ?
C9 C8 C7 123.6(3) . . ?
C8 C9 C11 121.0(3) . . ?
C8 C9 H8 119.5 . . ?
C11 C9 H8 119.5 . . ?
C12 C10 C8 120.6(3) . . ?
C12 C10 H9 119.7 . . ?
C8 C10 H9 119.7 . . ?
C13 C11 C9 119.0(3) . . ?
C13 C11 H10 120.5 . . ?
C9 C11 H10 120.5 . . ?
C10 C12 C13 120.1(3) . . ?
C10 C12 H11 120.0 . . ?
C13 C12 H11 120.0 . . ?
C11 C13 C12 120.2(2) . . ?
C11 C13 C14 121.2(3) . . ?
C12 C13 C14 118.6(3) . . ?
N2 C14 C13 177.4(3) . . ?
C57 O2 H45 110.4 . . ?
O1 C57 O2 124.1(2) . . ?
O1 C57 C58 123.0(3) . . ?
O2 C57 C58 112.7(2) . . ?
C59 C58 C60 118.8(2) . . ?
C59 C58 C57 118.5(2) . . ?
C60 C58 C57 122.8(2) . . ?
C60 C59 C58 122.6(2) 3_656 . ?
C60 C59 H46 118.7 3_656 . ?
C58 C59 H46 118.7 . . ?
C59 C60 C58 118.7(2) 3_656 . ?
C59 C60 C61 120.6(2) 3_656 . ?
C58 C60 C61 120.8(2) . . ?
O3 C61 O4 124.4(2) . . ?
O3 C61 C60 118.0(2) . . ?
O4 C61 C60 117.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C3 1.0(5) . . . . ?
C1 N1 C2 C4 -0.7(5) . . . . ?
N1 C1 C3 C5 -0.7(5) . . . . ?
N1 C2 C4 C5 0.2(5) . . . . ?
C2 C4 C5 C3 0.0(4) . . . . ?
C2 C4 C5 C6 179.9(3) . . . . ?
C1 C3 C5 C4 0.2(4) . . . . ?
C1 C3 C5 C6 -179.7(3) . . . . ?
C4 C5 C6 C7 -5.3(5) . . . . ?
C3 C5 C6 C7 174.5(3) . . . . ?
C5 C6 C7 C8 -177.0(3) . . . . ?
C6 C7 C8 C10 171.6(3) . . . . ?
C6 C7 C8 C9 -6.7(5) . . . . ?
C10 C8 C9 C11 -0.7(4) . . . . ?
C7 C8 C9 C11 177.7(3) . . . . ?
C9 C8 C10 C12 1.1(5) . . . . ?
C7 C8 C10 C12 -177.4(3) . . . . ?
C8 C9 C11 C13 -0.4(4) . . . . ?
C8 C10 C12 C13 -0.4(5) . . . . ?
C9 C11 C13 C12 1.0(4) . . . . ?
C9 C11 C13 C14 178.7(3) . . . . ?
C10 C12 C13 C11 -0.7(5) . . . . ?
C10 C12 C13 C14 -178.4(3) . . . . ?
C11 C13 C14 N2 -141(7) . . . . ?
C12 C13 C14 N2 37(8) . . . . ?
O1 C57 C58 C59 91.5(3) . . . . ?
O2 C57 C58 C59 -84.8(3) . . . . ?
O1 C57 C58 C60 -88.4(3) . . . . ?
O2 C57 C58 C60 95.3(3) . . . . ?
C60 C58 C59 C60 0.3(4) . . . 3_656 ?
C57 C58 C59 C60 -179.5(2) . . . 3_656 ?
C59 C58 C60 C59 -0.3(4) . . . 3_656 ?
C57 C58 C60 C59 179.5(2) . . . 3_656 ?
C59 C58 C60 C61 179.6(2) . . . . ?
C57 C58 C60 C61 -0.6(4) . . . . ?
C59 C60 C61 O3 174.7(3) 3_656 . . . ?
C58 C60 C61 O3 -5.2(4) . . . . ?
C59 C60 C61 O4 -4.4(4) 3_656 . . . ?
C58 C60 C61 O4 175.7(2) . . . . ?

#   End of CIF   ============================================================
####################################################################### 
# 
# 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_p21c_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1447039'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

#========================================================================== 
_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N4'
_chemical_formula_sum            'C28 H20 N4'
_chemical_formula_weight         412.48
_chemical_compound_source        Synthesis


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1413(16)
_cell_length_b                   11.929(2)
_cell_length_c                   11.410(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.94(3)
_cell_angle_gamma                90.00
_cell_volume                     1054.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3217
_cell_measurement_theta_min      2.5767
_cell_measurement_theta_max      27.2838

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


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

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11710
_diffrn_reflns_av_R_equivalents  0.1376
_diffrn_reflns_av_sigmaI/netI    0.1489
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         28.10
_reflns_number_total             2178
_reflns_number_gt                889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.9134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2178
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2381
_refine_ls_R_factor_gt           0.0984
_refine_ls_wR_factor_ref         0.2226
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049


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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4553(6) 0.0154(4) 0.3993(4) 0.0451(13) Uani 1 1 d . . .
H9A H 0.4494 0.0923 0.3681 0.054 Uiso 1 1 calc R . .
C11 C 0.3399(7) -0.1737(4) 0.3008(4) 0.0533(14) Uani 1 1 d . . .
H11A H 0.3222 -0.1977 0.3735 0.064 Uiso 1 1 calc R . .
C8 C 0.3637(6) 0.0067(4) 0.4995(4) 0.0485(13) Uani 1 1 d . . .
H8A H 0.2926 -0.0612 0.4869 0.058 Uiso 1 1 calc R . .
C7 C 0.2625(6) 0.1058(4) 0.5228(4) 0.0459(13) Uani 1 1 d . . .
C5 C 0.2608(7) 0.2109(5) 0.4724(4) 0.0589(15) Uani 1 1 d . . .
H5A H 0.3183 0.2228 0.4146 0.071 Uiso 1 1 calc R . .
C2 C 0.0939(6) 0.2837(4) 0.5946(4) 0.0514(14) Uani 1 1 d . . .
C4 C 0.0919(7) 0.1782(5) 0.6446(4) 0.0564(14) Uani 1 1 d . . .
H4A H 0.0351 0.1667 0.7029 0.068 Uiso 1 1 calc R . .
N2 N 0.3290(6) -0.2171(4) 0.0934(4) 0.0686(14) Uani 1 1 d . . .
C1 C 0.0101(8) 0.3765(5) 0.6365(5) 0.0636(16) Uani 1 1 d . . .
C6 C 0.1733(7) 0.0914(4) 0.6082(4) 0.0560(14) Uani 1 1 d . . .
H6A H 0.1692 0.0206 0.6412 0.067 Uiso 1 1 calc R . .
C3 C 0.1745(7) 0.2992(5) 0.5067(4) 0.0602(15) Uani 1 1 d . . .
H3A H 0.1714 0.3691 0.4699 0.072 Uiso 1 1 calc R . .
N1 N -0.0517(7) 0.4497(5) 0.6715(5) 0.0862(17) Uani 1 1 d . . .
C12 C 0.4269(7) -0.0382(5) 0.1824(4) 0.0637(16) Uani 1 1 d . . .
H12A H 0.4701 0.0322 0.1726 0.076 Uiso 1 1 calc R . .
C13 C 0.3047(7) -0.2445(5) 0.2006(5) 0.0594(15) Uani 1 1 d . . .
H13A H 0.2615 -0.3154 0.2079 0.071 Uiso 1 1 calc R . .
C14 C 0.3874(8) -0.1147(5) 0.0871(5) 0.0695(18) Uani 1 1 d . . .
H14A H 0.4032 -0.0926 0.0131 0.083 Uiso 1 1 calc R . .
C10 C 0.4012(6) -0.0675(4) 0.2930(4) 0.0490(13) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C10 1.521(6) . ?
C9 C8 1.549(6) . ?
C9 C8 1.590(6) 3_656 ?
C9 H9A 0.9800 . ?
C11 C10 1.374(7) . ?
C11 C13 1.379(6) . ?
C11 H11A 0.9300 . ?
C8 C7 1.511(6) . ?
C8 C9 1.590(6) 3_656 ?
C8 H8A 0.9800 . ?
C7 C5 1.377(6) . ?
C7 C6 1.394(6) . ?
C5 C3 1.388(7) . ?
C5 H5A 0.9300 . ?
C2 C3 1.370(7) . ?
C2 C4 1.383(7) . ?
C2 C1 1.457(7) . ?
C4 C6 1.361(6) . ?
C4 H4A 0.9300 . ?
N2 C14 1.321(7) . ?
N2 C13 1.338(6) . ?
C1 N1 1.140(6) . ?
C6 H6A 0.9300 . ?
C3 H3A 0.9300 . ?
C12 C14 1.380(7) . ?
C12 C10 1.386(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C9 C8 117.3(4) . . ?
C10 C9 C8 116.6(4) . 3_656 ?
C8 C9 C8 90.1(3) . 3_656 ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 3_656 . ?
C10 C11 C13 119.8(5) . . ?
C10 C11 H11A 120.1 . . ?
C13 C11 H11A 120.1 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 C9 115.8(4) . 3_656 ?
C9 C8 C9 89.9(3) . 3_656 ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 3_656 . ?
C5 C7 C6 117.6(5) . . ?
C5 C7 C8 125.1(4) . . ?
C6 C7 C8 117.1(4) . . ?
C7 C5 C3 120.9(5) . . ?
C7 C5 H5A 119.5 . . ?
C3 C5 H5A 119.5 . . ?
C3 C2 C4 119.6(5) . . ?
C3 C2 C1 121.1(5) . . ?
C4 C2 C1 119.3(5) . . ?
C6 C4 C2 119.8(5) . . ?
C6 C4 H4A 120.1 . . ?
C2 C4 H4A 120.1 . . ?
C14 N2 C13 115.6(5) . . ?
N1 C1 C2 178.3(7) . . ?
C4 C6 C7 121.8(5) . . ?
C4 C6 H6A 119.1 . . ?
C7 C6 H6A 119.1 . . ?
C2 C3 C5 120.1(5) . . ?
C2 C3 H3A 119.9 . . ?
C5 C3 H3A 119.9 . . ?
C14 C12 C10 119.1(5) . . ?
C14 C12 H12A 120.4 . . ?
C10 C12 H12A 120.4 . . ?
N2 C13 C11 123.9(5) . . ?
N2 C13 H13A 118.1 . . ?
C11 C13 H13A 118.1 . . ?
N2 C14 C12 124.7(5) . . ?
N2 C14 H14A 117.7 . . ?
C12 C14 H14A 117.7 . . ?
C11 C10 C12 116.9(4) . . ?
C11 C10 C9 124.7(4) . . ?
C12 C10 C9 118.3(5) . . ?



#   End of CIF   ============================================================


####################################################################### 
# 
# 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_p21c_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1447037'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'


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


_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cl2 N2 O8'
_chemical_formula_sum            'C36 H26 Cl2 N2 O8'
_chemical_formula_weight         685.49
_chemical_compound_source        Synthesis


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.773(2)
_cell_length_b                   10.033(2)
_cell_length_c                   16.112(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.83(3)
_cell_angle_gamma                90.00
_cell_volume                     1565.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9485
_cell_measurement_theta_min      2.1054
_cell_measurement_theta_max      27.9966

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


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

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19445
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.09
_reflns_number_total             3202
_reflns_number_gt                2435
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.5588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.839
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.048

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 



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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8036(2) 0.09461(18) 0.34695(11) 0.0460(5) Uani 1 1 d . . .
H1N H 0.8350 0.0952 0.2930 0.055 Uiso 1 1 d R . .
Cl1 Cl 0.66365(7) -0.15017(8) 0.94402(4) 0.0682(2) Uani 1 1 d . . .
O1 O -0.0173(2) 0.24781(15) 0.65939(10) 0.0600(5) Uani 1 1 d . . .
O2 O -0.14259(18) 0.41866(15) 0.69221(10) 0.0511(4) Uani 1 1 d . . .
O3 O -0.05632(17) 0.36923(14) 0.28949(9) 0.0470(4) Uani 1 1 d . . .
H1O H -0.0439 0.3140 0.2367 0.056 Uiso 1 1 d R . .
O4 O 0.1115(2) 0.24757(16) 0.35921(10) 0.0620(5) Uani 1 1 d . . .
C1 C 0.7124(3) 0.1858(2) 0.36267(15) 0.0533(6) Uani 1 1 d . . .
H1A H 0.6834 0.2502 0.3226 0.064 Uiso 1 1 calc R . .
C2 C 0.8460(3) -0.0003(2) 0.40290(14) 0.0490(6) Uani 1 1 d . . .
H2A H 0.9092 -0.0640 0.3902 0.059 Uiso 1 1 calc R . .
C3 C 0.6608(3) 0.1857(2) 0.43716(15) 0.0537(6) Uani 1 1 d . . .
H3A H 0.5978 0.2509 0.4477 0.064 Uiso 1 1 calc R . .
C4 C 0.7974(2) -0.0047(2) 0.47857(14) 0.0464(5) Uani 1 1 d . . .
H4A H 0.8285 -0.0704 0.5173 0.056 Uiso 1 1 calc R . .
C5 C 0.7012(2) 0.0895(2) 0.49756(14) 0.0420(5) Uani 1 1 d . . .
C6 C 0.6402(3) 0.0909(2) 0.57494(15) 0.0508(6) Uani 1 1 d . . .
H6A H 0.5709 0.1534 0.5782 0.061 Uiso 1 1 calc R . .
C7 C 0.6718(2) 0.0137(2) 0.64114(14) 0.0447(5) Uani 1 1 d . . .
H7A H 0.7436 -0.0469 0.6399 0.054 Uiso 1 1 calc R . .
C8 C 0.6030(2) 0.0158(2) 0.71637(13) 0.0419(5) Uani 1 1 d . . .
C9 C 0.4831(3) 0.0883(2) 0.72076(15) 0.0495(6) Uani 1 1 d . . .
H9A H 0.4456 0.1394 0.6751 0.059 Uiso 1 1 calc R . .
C10 C 0.6585(2) -0.0588(2) 0.78600(14) 0.0450(5) Uani 1 1 d . . .
H10A H 0.7392 -0.1076 0.7849 0.054 Uiso 1 1 calc R . .
C11 C 0.4186(3) 0.0857(3) 0.79177(16) 0.0561(6) Uani 1 1 d . . .
H11A H 0.3384 0.1349 0.7934 0.067 Uiso 1 1 calc R . .
C12 C 0.5925(3) -0.0593(2) 0.85650(14) 0.0482(6) Uani 1 1 d . . .
C13 C 0.4719(3) 0.0111(2) 0.86011(15) 0.0531(6) Uani 1 1 d . . .
H13A H 0.4278 0.0081 0.9077 0.064 Uiso 1 1 calc R . .
C14 C -0.0662(2) 0.36268(19) 0.64790(12) 0.0352(5) Uani 1 1 d . . .
C15 C -0.0303(2) 0.43569(17) 0.57233(11) 0.0300(4) Uani 1 1 d . . .
C16 C -0.0111(2) 0.36394(18) 0.50140(12) 0.0327(4) Uani 1 1 d . . .
H16A H -0.0179 0.2715 0.5024 0.033(5) Uiso 1 1 calc R . .
C17 C 0.0179(2) 0.42614(17) 0.42907(11) 0.0304(4) Uani 1 1 d . . .
C18 C 0.0313(2) 0.34040(18) 0.35479(12) 0.0357(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.325(3) . ?
N1 C2 1.338(3) . ?
N1 H1N 0.9605 . ?
Cl1 C12 1.743(2) . ?
O1 C14 1.252(2) . ?
O2 C14 1.236(2) . ?
O3 C18 1.296(3) . ?
O3 H1O 1.0356 . ?
O4 C18 1.213(2) . ?
C1 C3 1.364(3) . ?
C1 H1A 0.9300 . ?
C2 C4 1.368(3) . ?
C2 H2A 0.9300 . ?
C3 C5 1.389(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.453(3) . ?
C6 C7 1.320(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.465(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.389(3) . ?
C8 C10 1.395(3) . ?
C9 C11 1.379(3) . ?
C9 H9A 0.9300 . ?
C10 C12 1.381(3) . ?
C10 H10A 0.9300 . ?
C11 C13 1.374(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.503(2) . ?
C15 C16 1.385(3) . ?
C15 C17 1.392(3) 3_566 ?
C16 C17 1.385(2) . ?
C16 H16A 0.9300 . ?
C17 C15 1.392(3) 3_566 ?
C17 C18 1.494(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 121.1(2) . . ?
C1 N1 H1N 118.4 . . ?
C2 N1 H1N 120.4 . . ?
C18 O3 H1O 114.1 . . ?
N1 C1 C3 120.4(2) . . ?
N1 C1 H1A 119.8 . . ?
C3 C1 H1A 119.8 . . ?
N1 C2 C4 120.7(2) . . ?
N1 C2 H2A 119.7 . . ?
C4 C2 H2A 119.7 . . ?
C1 C3 C5 120.9(2) . . ?
C1 C3 H3A 119.6 . . ?
C5 C3 H3A 119.6 . . ?
C2 C4 C5 119.9(2) . . ?
C2 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C3 C5 C4 116.9(2) . . ?
C3 C5 C6 118.9(2) . . ?
C4 C5 C6 124.2(2) . . ?
C7 C6 C5 127.5(2) . . ?
C7 C6 H6A 116.2 . . ?
C5 C6 H6A 116.2 . . ?
C6 C7 C8 125.2(2) . . ?
C6 C7 H7A 117.4 . . ?
C8 C7 H7A 117.4 . . ?
C9 C8 C10 118.6(2) . . ?
C9 C8 C7 122.4(2) . . ?
C10 C8 C7 119.0(2) . . ?
C11 C9 C8 121.1(2) . . ?
C11 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C12 C10 C8 119.3(2) . . ?
C12 C10 H10A 120.4 . . ?
C8 C10 H10A 120.4 . . ?
C13 C11 C9 120.6(2) . . ?
C13 C11 H11A 119.7 . . ?
C9 C11 H11A 119.7 . . ?
C10 C12 C13 122.0(2) . . ?
C10 C12 Cl1 119.18(19) . . ?
C13 C12 Cl1 118.83(18) . . ?
C11 C13 C12 118.5(2) . . ?
C11 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
O2 C14 O1 125.56(18) . . ?
O2 C14 C15 118.20(17) . . ?
O1 C14 C15 116.23(17) . . ?
C16 C15 C17 118.85(16) . 3_566 ?
C16 C15 C14 119.20(16) . . ?
C17 C15 C14 121.93(16) 3_566 . ?
C15 C16 C17 121.75(17) . . ?
C15 C16 H16A 119.1 . . ?
C17 C16 H16A 119.1 . . ?
C16 C17 C15 119.39(16) . 3_566 ?
C16 C17 C18 117.70(16) . . ?
C15 C17 C18 122.90(16) 3_566 . ?
O4 C18 O3 124.70(18) . . ?
O4 C18 C17 121.44(19) . . ?
O3 C18 C17 113.67(17) . . ?

#   End of CIF   ============================================================

####################################################################### 
# 
# 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_p-1_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1447036'

_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-97
_audit_creation_date             '12 January 2016'

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

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cl N O4'
_chemical_formula_sum            'C18 H13 Cl N O4'
_chemical_formula_weight         342.74
_chemical_compound_source        Synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc '


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6552(19)
_cell_length_b                   12.927(3)
_cell_length_c                   13.746(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.53(2)
_cell_angle_gamma                90.00
_cell_volume                     1560.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3417
_cell_measurement_theta_min      4.532
_cell_measurement_theta_max      56.219

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19264
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.11
_reflns_number_total             3041
_reflns_number_gt                1802
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXL-2003 (Sheldrick, 2003)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_computing_publication_material  
; 
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0712P)²+1.3698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3041
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1969
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.798
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.055

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 


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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0669(4) 0.2226(2) 0.3669(2) 0.0648(8) Uani 1 1 d . . .
H1 H 0.0482 0.2699 0.2944 0.097 Uiso 1 1 d R . .
O2 O 0.0500(3) 0.0897(2) 0.2598(2) 0.0573(8) Uani 1 1 d . . .
O3 O 0.1647(3) -0.1220(2) 0.3298(2) 0.0613(8) Uani 1 1 d . . .
O4 O -0.0859(3) -0.1505(2) 0.2600(2) 0.0589(8) Uani 1 1 d . . .
C1 C 0.0505(4) 0.1250(3) 0.3423(3) 0.0423(9) Uani 1 1 d . . .
C2 C 0.0357(5) -0.1103(3) 0.3271(3) 0.0444(9) Uani 1 1 d . . .
C3 C 0.0124(4) 0.1055(3) 0.5102(3) 0.0416(8) Uani 1 1 d . . .
H2 H 0.0212 0.1770 0.5170 0.050 Uiso 1 1 calc R . .
C4 C 0.0168(4) -0.0491(3) 0.4143(3) 0.0381(8) Uani 1 1 d . . .
C5 C 0.0287(4) 0.0578(3) 0.4243(3) 0.0381(8) Uani 1 1 d . . .
Cl1 Cl 0.3881(2) 0.29150(13) 0.12321(13) 0.1147(7) Uani 1 1 d . . .
N1 N 0.8169(4) 0.0501(5) -0.1467(3) 0.0828(14) Uani 1 1 d . . .
H1A H 0.8370 0.0481 -0.2020 0.099 Uiso 1 1 calc R . .
C21 C 0.7852(6) 0.1400(5) -0.1150(4) 0.0905(19) Uani 1 1 d . . .
H9 H 0.7873 0.2000 -0.1516 0.109 Uiso 1 1 calc R . .
C22 C 0.8185(5) -0.0367(5) -0.0957(4) 0.0750(14) Uani 1 1 d . . .
H11 H 0.8453 -0.0985 -0.1181 0.090 Uiso 1 1 calc R . .
C23 C 0.7487(5) 0.1458(4) -0.0274(4) 0.0760(14) Uani 1 1 d . . .
H12 H 0.7295 0.2094 -0.0039 0.091 Uiso 1 1 calc R . .
C24 C 0.7811(5) -0.0359(4) -0.0103(3) 0.0650(12) Uani 1 1 d . . .
H13 H 0.7824 -0.0975 0.0251 0.078 Uiso 1 1 calc R . .
C25 C 0.7411(4) 0.0555(3) 0.0245(3) 0.0532(10) Uani 1 1 d . . .
C26 C 0.6920(4) 0.0537(3) 0.1121(3) 0.0561(10) Uani 1 1 d . . .
H14 H 0.7093 -0.0065 0.1525 0.067 Uiso 1 1 calc R . .
C27 C 0.6252(4) 0.1310(3) 0.1377(3) 0.0571(11) Uani 1 1 d . . .
H15 H 0.6101 0.1914 0.0978 0.068 Uiso 1 1 calc R . .
C28 C 0.5723(4) 0.1306(3) 0.2236(3) 0.0520(10) Uani 1 1 d . . .
C29 C 0.6248(5) 0.0611(4) 0.3073(4) 0.0698(13) Uani 1 1 d . . .
H16 H 0.6956 0.0115 0.3091 0.084 Uiso 1 1 calc R . .
C30 C 0.4663(5) 0.2031(3) 0.2254(3) 0.0593(11) Uani 1 1 d . . .
C31 C 0.5760(6) 0.0625(5) 0.3884(4) 0.0843(16) Uani 1 1 d . . .
H17 H 0.6140 0.0149 0.4440 0.101 Uiso 1 1 calc R . .
C32 C 0.4144(5) 0.2051(4) 0.3057(4) 0.0709(13) Uani 1 1 d . . .
H18 H 0.3423 0.2536 0.3041 0.085 Uiso 1 1 calc R . .
C33 C 0.4702(6) 0.1354(4) 0.3862(4) 0.0801(15) Uani 1 1 d . . .
H19 H 0.4369 0.1366 0.4407 0.096 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.298(4) . ?
O1 H1 1.1181 . ?
O2 C1 1.220(4) . ?
O3 C2 1.241(4) . ?
O4 C2 1.265(5) . ?
C1 C5 1.505(5) . ?
C2 C4 1.509(5) . ?
C3 C4 1.389(4) 3_556 ?
C3 C5 1.397(4) . ?
C3 H2 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C3 1.389(4) 3_556 ?
Cl1 C30 1.724(5) . ?
N1 C22 1.318(7) . ?
N1 C21 1.322(7) . ?
N1 H1A 0.8600 . ?
C21 C23 1.390(7) . ?
C21 H9 0.9300 . ?
C22 C24 1.365(6) . ?
C22 H11 0.9300 . ?
C23 C25 1.385(6) . ?
C23 H12 0.9300 . ?
C24 C25 1.388(6) . ?
C24 H13 0.9300 . ?
C25 C26 1.466(5) . ?
C26 C27 1.313(5) . ?
C26 H14 0.9300 . ?
C27 C28 1.468(5) . ?
C27 H15 0.9300 . ?
C28 C29 1.380(6) . ?
C28 C30 1.396(5) . ?
C29 C31 1.379(6) . ?
C29 H16 0.9300 . ?
C30 C32 1.388(6) . ?
C31 C33 1.381(7) . ?
C31 H17 0.9300 . ?
C32 C33 1.354(7) . ?
C32 H18 0.9300 . ?
C33 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 110.0 . . ?
O2 C1 O1 123.9(3) . . ?
O2 C1 C5 122.2(3) . . ?
O1 C1 C5 113.9(3) . . ?
O3 C2 O4 126.0(3) . . ?
O3 C2 C4 119.5(4) . . ?
O4 C2 C4 114.3(3) . . ?
C4 C3 C5 121.9(3) 3_556 . ?
C4 C3 H2 119.0 3_556 . ?
C5 C3 H2 119.0 . . ?
C5 C4 C3 118.8(3) . 3_556 ?
C5 C4 C2 124.6(3) . . ?
C3 C4 C2 116.6(3) 3_556 . ?
C4 C5 C3 119.2(3) . . ?
C4 C5 C1 122.1(3) . . ?
C3 C5 C1 118.6(3) . . ?
C22 N1 C21 121.7(4) . . ?
C22 N1 H1A 119.1 . . ?
C21 N1 H1A 119.1 . . ?
N1 C21 C23 120.7(5) . . ?
N1 C21 H9 119.7 . . ?
C23 C21 H9 119.7 . . ?
N1 C22 C24 120.1(5) . . ?
N1 C22 H11 119.9 . . ?
C24 C22 H11 119.9 . . ?
C25 C23 C21 119.1(5) . . ?
C25 C23 H12 120.4 . . ?
C21 C23 H12 120.4 . . ?
C22 C24 C25 120.9(5) . . ?
C22 C24 H13 119.6 . . ?
C25 C24 H13 119.6 . . ?
C24 C25 C23 117.3(4) . . ?
C24 C25 C26 120.1(4) . . ?
C23 C25 C26 122.7(4) . . ?
C27 C26 C25 124.8(4) . . ?
C27 C26 H14 117.6 . . ?
C25 C26 H14 117.6 . . ?
C26 C27 C28 125.9(4) . . ?
C26 C27 H15 117.1 . . ?
C28 C27 H15 117.1 . . ?
C29 C28 C30 116.1(4) . . ?
C29 C28 C27 122.9(4) . . ?
C30 C28 C27 121.0(4) . . ?
C31 C29 C28 122.4(4) . . ?
C31 C29 H16 118.8 . . ?
C28 C29 H16 118.8 . . ?
C32 C30 C28 122.5(4) . . ?
C32 C30 Cl1 117.1(3) . . ?
C28 C30 Cl1 120.4(3) . . ?
C29 C31 C33 119.3(5) . . ?
C29 C31 H17 120.3 . . ?
C33 C31 H17 120.3 . . ?
C33 C32 C30 119.0(4) . . ?
C33 C32 H18 120.5 . . ?
C30 C32 H18 120.5 . . ?
C32 C33 C31 120.8(4) . . ?
C32 C33 H19 119.6 . . ?
C31 C33 H19 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C4 C5 73.6(5) . . . . ?
O4 C2 C4 C5 -110.3(4) . . . . ?
O3 C2 C4 C3 -105.4(4) . . . 3_556 ?
O4 C2 C4 C3 70.7(4) . . . 3_556 ?
C3 C4 C5 C3 0.5(6) 3_556 . . . ?
C2 C4 C5 C3 -178.5(3) . . . . ?
C3 C4 C5 C1 -176.2(3) 3_556 . . . ?
C2 C4 C5 C1 4.9(6) . . . . ?
C4 C3 C5 C4 -0.5(6) 3_556 . . . ?
C4 C3 C5 C1 176.3(3) 3_556 . . . ?
O2 C1 C5 C4 4.3(6) . . . . ?
O1 C1 C5 C4 -176.8(3) . . . . ?
O2 C1 C5 C3 -172.4(3) . . . . ?
O1 C1 C5 C3 6.5(5) . . . . ?
C22 N1 C21 C23 -1.5(8) . . . . ?
C21 N1 C22 C24 2.6(8) . . . . ?
N1 C21 C23 C25 -2.0(8) . . . . ?
N1 C22 C24 C25 -0.1(7) . . . . ?
C22 C24 C25 C23 -3.3(6) . . . . ?
C22 C24 C25 C26 176.1(4) . . . . ?
C21 C23 C25 C24 4.3(7) . . . . ?
C21 C23 C25 C26 -175.1(4) . . . . ?
C24 C25 C26 C27 -166.5(4) . . . . ?
C23 C25 C26 C27 12.8(7) . . . . ?
C25 C26 C27 C28 178.8(4) . . . . ?
C26 C27 C28 C29 19.6(7) . . . . ?
C26 C27 C28 C30 -161.5(4) . . . . ?
C30 C28 C29 C31 0.0(7) . . . . ?
C27 C28 C29 C31 179.0(5) . . . . ?
C29 C28 C30 C32 -0.7(6) . . . . ?
C27 C28 C30 C32 -179.7(4) . . . . ?
C29 C28 C30 Cl1 -178.1(3) . . . . ?
C27 C28 C30 Cl1 2.9(6) . . . . ?
C28 C29 C31 C33 0.4(8) . . . . ?
C28 C30 C32 C33 1.1(7) . . . . ?
Cl1 C30 C32 C33 178.5(4) . . . . ?
C30 C32 C33 C31 -0.7(8) . . . . ?
C29 C31 C33 C32 -0.1(8) . . . . ?

_vrf_PLAT029_C                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.977    
RESPONSE: The low completeness ratio is due to the experimental
setup whereby by the equipment has a \c circle and an added 
area detector (four-circle diffractometer modified with a CCD). 
This precludes the collection of some regions of reciprocal 
lattice space and lowers the completeness. In order to 
compensate, additional redundant data were measured.
;

#   End of CIF   ============================================================


