# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_C17H17NO3
_database_code_depnum_ccdc_archive 'CCDC 1833864'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7310(3)
_cell_length_b                   8.2071(3)
_cell_length_c                   11.5044(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.7792(11)
_cell_angle_gamma                90
_cell_volume                     695.08(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7030
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      66.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.755
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6258
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7197
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.035
_diffrn_reflns_theta_max         66.667
_diffrn_reflns_theta_full        66.667
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2444
_reflns_number_gt                2431
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.1273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Flack x determined using 1120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2444
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14133(16) 0.38128(16) 0.11578(12) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.28004(16) 0.62262(16) 0.18206(12) 0.0196(3) Uani 1 1 d . . . . .
O3 O 0.81791(18) 0.91739(16) 0.56173(12) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.45146(19) 0.40439(19) 0.18687(13) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.1043(3) 0.6976(2) 0.1578(2) 0.0251(4) Uani 1 1 d . . . . .
H1A H 0.0437 0.6550 0.2149 0.038 Uiso 1 1 calc R U . . .
H1B H 0.0306 0.6730 0.0739 0.038 Uiso 1 1 calc R U . . .
H1C H 0.1188 0.8159 0.1681 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2781(2) 0.4618(2) 0.15774(15) 0.0162(4) Uani 1 1 d . . . . .
C3 C 0.5009(2) 0.2465(2) 0.15866(15) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.3930(2) 0.1096(2) 0.12110(16) 0.0174(4) Uani 1 1 d . . . . .
H4 H 0.2664 0.1126 0.1109 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4768(3) -0.0325(2) 0.09886(16) 0.0203(4) Uani 1 1 d . . . . .
H5 H 0.4060 -0.1282 0.0741 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6618(3) -0.0371(3) 0.11218(16) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.7158 -0.1349 0.0958 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7676(3) 0.1017(2) 0.14959(17) 0.0210(4) Uani 1 1 d . . . . .
H7 H 0.8939 0.0993 0.1587 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6871(2) 0.2430(2) 0.17331(16) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.7697(2) 0.4082(2) 0.21047(17) 0.0202(4) Uani 1 1 d . . . . .
H9A H 0.8133 0.4559 0.1455 0.024 Uiso 1 1 calc R U . . .
H9B H 0.8729 0.4010 0.2866 0.024 Uiso 1 1 calc R U . . .
C10 C 0.6141(2) 0.5119(2) 0.23052(16) 0.0172(4) Uani 1 1 d . . . . .
H10 H 0.5960 0.6114 0.1781 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6504(2) 0.5622(2) 0.36265(17) 0.0160(4) Uani 1 1 d . . . . .
C12 C 0.7137(2) 0.7195(2) 0.39729(16) 0.0164(4) Uani 1 1 d . . . . .
H12 H 0.7266 0.7949 0.3378 0.020 Uiso 1 1 calc R U . . .
C13 C 0.7579(2) 0.7656(2) 0.51911(17) 0.0174(4) Uani 1 1 d . . . . .
C14 C 0.7396(2) 0.6554(2) 0.60662(16) 0.0187(4) Uani 1 1 d . . . . .
H14 H 0.7717 0.6864 0.6901 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6743(2) 0.5000(2) 0.57101(17) 0.0198(4) Uani 1 1 d . . . . .
H15 H 0.6599 0.4251 0.6303 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6295(2) 0.4529(2) 0.44929(17) 0.0186(4) Uani 1 1 d . . . . .
H16 H 0.5847 0.3462 0.4256 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8308(3) 1.0361(2) 0.47452(19) 0.0249(4) Uani 1 1 d . . . . .
H17A H 0.7118 1.0500 0.4133 0.037 Uiso 1 1 calc R U . . .
H17B H 0.9192 0.9999 0.4344 0.037 Uiso 1 1 calc R U . . .
H17C H 0.8705 1.1402 0.5158 0.037 Uiso 1 1 calc R U . . .


_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 C2 1.215(2) . ?
O2 C2 1.348(2) . ?
O2 C1 1.439(2) . ?
O3 C13 1.367(2) . ?
O3 C17 1.424(3) . ?
N1 C2 1.363(2) . ?
N1 C3 1.417(2) . ?
N1 C10 1.492(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.387(3) . ?
C3 C8 1.397(3) . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.504(3) . ?
C9 C10 1.547(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(2) . ?
C10 H10 1.0000 . ?
C11 C16 1.387(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O2 C1 115.36(14) . . ?
C13 O3 C17 117.39(14) . . ?
C2 N1 C3 125.04(15) . . ?
C2 N1 C10 122.89(15) . . ?
C3 N1 C10 111.05(14) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.64(16) . . ?
O1 C2 N1 125.50(17) . . ?
O2 C2 N1 109.85(15) . . ?
C4 C3 C8 121.39(17) . . ?
C4 C3 N1 129.28(16) . . ?
C8 C3 N1 109.32(15) . . ?
C3 C4 C5 117.71(17) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 121.45(18) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 119.92(19) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.38(17) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C3 120.15(17) . . ?
C7 C8 C9 129.42(16) . . ?
C3 C8 C9 110.38(16) . . ?
C8 C9 C10 104.85(14) . . ?
C8 C9 H9A 110.8 . . ?
C10 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
N1 C10 C11 112.16(14) . . ?
N1 C10 C9 103.80(14) . . ?
C11 C10 C9 112.64(14) . . ?
N1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C16 C11 C12 120.07(17) . . ?
C16 C11 C10 121.21(16) . . ?
C12 C11 C10 118.66(16) . . ?
C13 C12 C11 119.76(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O3 C13 C12 124.15(17) . . ?
O3 C13 C14 115.53(16) . . ?
C12 C13 C14 120.31(17) . . ?
C15 C14 C13 119.47(17) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.64(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.73(17) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C1 O2 C2 O1 1.6(2) . . . . ?
C1 O2 C2 N1 -178.63(15) . . . . ?
C3 N1 C2 O1 8.5(3) . . . . ?
C10 N1 C2 O1 175.86(17) . . . . ?
C3 N1 C2 O2 -171.35(15) . . . . ?
C10 N1 C2 O2 -3.9(2) . . . . ?
C2 N1 C3 C4 -14.6(3) . . . . ?
C10 N1 C3 C4 176.70(16) . . . . ?
C2 N1 C3 C8 164.99(16) . . . . ?
C10 N1 C3 C8 -3.69(19) . . . . ?
C8 C3 C4 C5 0.3(3) . . . . ?
N1 C3 C4 C5 179.87(16) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
C6 C7 C8 C9 -177.83(17) . . . . ?
C4 C3 C8 C7 0.4(3) . . . . ?
N1 C3 C8 C7 -179.24(16) . . . . ?
C4 C3 C8 C9 178.13(16) . . . . ?
N1 C3 C8 C9 -1.52(19) . . . . ?
C7 C8 C9 C10 -176.76(18) . . . . ?
C3 C8 C9 C10 5.79(19) . . . . ?
C2 N1 C10 C11 76.2(2) . . . . ?
C3 N1 C10 C11 -114.83(16) . . . . ?
C2 N1 C10 C9 -161.93(16) . . . . ?
C3 N1 C10 C9 7.04(18) . . . . ?
C8 C9 C10 N1 -7.46(18) . . . . ?
C8 C9 C10 C11 114.09(16) . . . . ?
N1 C10 C11 C16 39.9(2) . . . . ?
C9 C10 C11 C16 -76.7(2) . . . . ?
N1 C10 C11 C12 -142.93(16) . . . . ?
C9 C10 C11 C12 100.40(19) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C12 C13 -176.32(15) . . . . ?
C17 O3 C13 C12 1.7(2) . . . . ?
C17 O3 C13 C14 -177.28(16) . . . . ?
C11 C12 C13 O3 -178.84(15) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
O3 C13 C14 C15 178.04(16) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C10 C11 C16 C15 176.17(16) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_C34H51N3O4
_database_code_depnum_ccdc_archive 'CCDC 1833867'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H51 N3 O4'
_chemical_formula_sum            'C34 H51 N3 O4'
_chemical_formula_weight         565.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.4518(5)
_cell_length_b                   15.8358(5)
_cell_length_c                   14.1208(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.9460(10)
_cell_angle_gamma                90
_cell_volume                     3223.97(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      66.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.599
_shelx_estimated_absorpt_T_min   0.734
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43406
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         66.691
_diffrn_reflns_theta_full        66.691
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5693
_reflns_number_gt                5504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+1.2405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5693
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44524(5) 0.39460(5) 0.43399(5) 0.02035(17) Uani 1 1 d . . . . .
O2 O 0.40407(5) 0.29148(5) 0.32791(5) 0.02102(17) Uani 1 1 d . . . . .
O3 O 0.25910(5) 0.59410(4) 0.40511(5) 0.01818(16) Uani 1 1 d . . . . .
O4 O 0.23017(5) 0.20846(4) 0.49106(5) 0.01552(16) Uani 1 1 d . . . . .
N1 N 0.30868(6) 0.33165(5) 0.44346(6) 0.01501(18) Uani 1 1 d . . . . .
N2 N 0.26132(6) 0.62568(5) 0.30848(6) 0.01682(19) Uani 1 1 d . . . . .
N3 N 0.25285(6) 0.12283(5) 0.46110(6) 0.01538(19) Uani 1 1 d . . . . .
C1 C 0.53163(7) 0.40516(8) 0.38995(9) 0.0246(2) Uani 1 1 d . . . . .
H1A H 0.5718 0.3564 0.4049 0.037 Uiso 1 1 calc R U . . .
H1B H 0.5624 0.4568 0.4140 0.037 Uiso 1 1 calc R U . . .
H1C H 0.5193 0.4094 0.3210 0.037 Uiso 1 1 calc R U . . .
C2 C 0.38790(7) 0.33486(6) 0.39535(7) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.29419(7) 0.38882(6) 0.52072(7) 0.0151(2) Uani 1 1 d . . . . .
C4 C 0.30968(7) 0.35996(7) 0.61331(8) 0.0184(2) Uani 1 1 d . . . . .
H4 H 0.3317 0.3041 0.6248 0.022 Uiso 1 1 calc R U . . .
C5 C 0.29317(7) 0.41241(7) 0.68917(8) 0.0211(2) Uani 1 1 d . . . . .
H5 H 0.3038 0.3928 0.7526 0.025 Uiso 1 1 calc R U . . .
C6 C 0.26100(7) 0.49372(7) 0.67124(8) 0.0207(2) Uani 1 1 d . . . . .
H6 H 0.2491 0.5299 0.7227 0.025 Uiso 1 1 calc R U . . .
C7 C 0.24600(7) 0.52273(7) 0.57883(8) 0.0180(2) Uani 1 1 d . . . . .
H7 H 0.2237 0.5786 0.5677 0.022 Uiso 1 1 calc R U . . .
C8 C 0.26310(7) 0.47122(7) 0.50203(7) 0.0158(2) Uani 1 1 d . . . . .
C9 C 0.24795(8) 0.50415(7) 0.40208(7) 0.0192(2) Uani 1 1 d . . . . .
H9A H 0.2935 0.4787 0.3613 0.023 Uiso 1 1 calc R U . . .
H9B H 0.1848 0.4894 0.3755 0.023 Uiso 1 1 calc R U . . .
C10 C 0.17816(8) 0.68043(7) 0.28976(8) 0.0207(2) Uani 1 1 d . . . . .
C11 C 0.18397(8) 0.71573(7) 0.18911(8) 0.0247(2) Uani 1 1 d . . . . .
H11A H 0.1744 0.6690 0.1430 0.030 Uiso 1 1 calc R U . . .
H11B H 0.1332 0.7570 0.1762 0.030 Uiso 1 1 calc R U . . .
C12 C 0.27590(9) 0.75862(7) 0.17354(9) 0.0297(3) Uani 1 1 d . . . . .
H12A H 0.2773 0.7755 0.1062 0.036 Uiso 1 1 calc R U . . .
H12B H 0.2823 0.8102 0.2130 0.036 Uiso 1 1 calc R U . . .
C13 C 0.35617(8) 0.69915(7) 0.19963(8) 0.0257(3) Uani 1 1 d . . . . .
H13A H 0.4152 0.7297 0.1934 0.031 Uiso 1 1 calc R U . . .
H13B H 0.3539 0.6515 0.1541 0.031 Uiso 1 1 calc R U . . .
C14 C 0.35497(8) 0.66392(7) 0.30070(8) 0.0213(2) Uani 1 1 d . . . . .
C15 C 0.23728(7) 0.26856(6) 0.41623(7) 0.0153(2) Uani 1 1 d . . . . .
H15 H 0.2549 0.2384 0.3579 0.018 Uiso 1 1 calc R U . . .
C16 C 0.14508(7) 0.31279(6) 0.39474(7) 0.0157(2) Uani 1 1 d . . . . .
C17 C 0.08918(7) 0.33755(7) 0.46635(8) 0.0200(2) Uani 1 1 d . . . . .
H17 H 0.1057 0.3223 0.5304 0.024 Uiso 1 1 calc R U . . .
C18 C 0.00938(8) 0.38442(7) 0.44430(8) 0.0237(2) Uani 1 1 d . . . . .
H18 H -0.0280 0.4019 0.4935 0.028 Uiso 1 1 calc R U . . .
C19 C -0.01616(7) 0.40584(7) 0.35098(8) 0.0232(2) Uani 1 1 d . . . . .
H19 H -0.0703 0.4387 0.3363 0.028 Uiso 1 1 calc R U . . .
C20 C 0.03757(7) 0.37919(7) 0.27934(8) 0.0211(2) Uani 1 1 d . . . . .
H20 H 0.0194 0.3924 0.2151 0.025 Uiso 1 1 calc R U . . .
C21 C 0.11805(7) 0.33306(7) 0.30112(7) 0.0180(2) Uani 1 1 d . . . . .
H21 H 0.1549 0.3152 0.2516 0.022 Uiso 1 1 calc R U . . .
C22 C 0.33500(7) 0.09455(7) 0.52357(8) 0.0185(2) Uani 1 1 d . . . . .
C23 C 0.35333(8) 0.00207(7) 0.49754(8) 0.0221(2) Uani 1 1 d . . . . .
H23A H 0.3729 -0.0003 0.4318 0.027 Uiso 1 1 calc R U . . .
H23B H 0.4049 -0.0200 0.5402 0.027 Uiso 1 1 calc R U . . .
C24 C 0.26899(8) -0.05407(7) 0.50499(8) 0.0224(2) Uani 1 1 d . . . . .
H24A H 0.2836 -0.1124 0.4858 0.027 Uiso 1 1 calc R U . . .
H24B H 0.2512 -0.0554 0.5714 0.027 Uiso 1 1 calc R U . . .
C25 C 0.18945(8) -0.01946(7) 0.44068(8) 0.0208(2) Uani 1 1 d . . . . .
H25A H 0.1339 -0.0550 0.4472 0.025 Uiso 1 1 calc R U . . .
H25B H 0.2060 -0.0234 0.3740 0.025 Uiso 1 1 calc R U . . .
C26 C 0.16516(7) 0.07267(7) 0.46252(7) 0.0176(2) Uani 1 1 d . . . . .
C27 C 0.41791(7) 0.14712(7) 0.49655(8) 0.0232(2) Uani 1 1 d . . . . .
H27A H 0.4212 0.1462 0.4275 0.035 Uiso 1 1 calc R U . . .
H27B H 0.4751 0.1234 0.5270 0.035 Uiso 1 1 calc R U . . .
H27C H 0.4105 0.2055 0.5179 0.035 Uiso 1 1 calc R U . . .
C28 C 0.32592(8) 0.10369(7) 0.63085(8) 0.0231(2) Uani 1 1 d . . . . .
H28A H 0.2970 0.1581 0.6438 0.035 Uiso 1 1 calc R U . . .
H28B H 0.3876 0.1010 0.6642 0.035 Uiso 1 1 calc R U . . .
H28C H 0.2873 0.0578 0.6530 0.035 Uiso 1 1 calc R U . . .
C29 C 0.11503(8) 0.07872(7) 0.55465(8) 0.0219(2) Uani 1 1 d . . . . .
H29A H 0.1497 0.0469 0.6049 0.033 Uiso 1 1 calc R U . . .
H29B H 0.0525 0.0551 0.5442 0.033 Uiso 1 1 calc R U . . .
H29C H 0.1109 0.1380 0.5737 0.033 Uiso 1 1 calc R U . . .
C30 C 0.09911(8) 0.10484(7) 0.38135(8) 0.0218(2) Uani 1 1 d . . . . .
H30A H 0.0756 0.1607 0.3976 0.033 Uiso 1 1 calc R U . . .
H30B H 0.0471 0.0655 0.3710 0.033 Uiso 1 1 calc R U . . .
H30C H 0.1323 0.1090 0.3233 0.033 Uiso 1 1 calc R U . . .
C31 C 0.09320(8) 0.62324(8) 0.28994(8) 0.0262(3) Uani 1 1 d . . . . .
H31A H 0.1007 0.5755 0.2470 0.039 Uiso 1 1 calc R U . . .
H31B H 0.0377 0.6554 0.2686 0.039 Uiso 1 1 calc R U . . .
H31C H 0.0866 0.6021 0.3544 0.039 Uiso 1 1 calc R U . . .
C32 C 0.16610(9) 0.75192(8) 0.36194(9) 0.0295(3) Uani 1 1 d . . . . .
H32A H 0.1792 0.7302 0.4265 0.044 Uiso 1 1 calc R U . . .
H32B H 0.1023 0.7731 0.3550 0.044 Uiso 1 1 calc R U . . .
H32C H 0.2092 0.7980 0.3503 0.044 Uiso 1 1 calc R U . . .
C33 C 0.38395(9) 0.73199(8) 0.37463(9) 0.0304(3) Uani 1 1 d . . . . .
H33A H 0.3518 0.7850 0.3578 0.046 Uiso 1 1 calc R U . . .
H33B H 0.4511 0.7409 0.3756 0.046 Uiso 1 1 calc R U . . .
H33C H 0.3674 0.7135 0.4375 0.046 Uiso 1 1 calc R U . . .
C34 C 0.42567(8) 0.59223(8) 0.31136(9) 0.0267(3) Uani 1 1 d . . . . .
H34A H 0.4291 0.5714 0.3769 0.040 Uiso 1 1 calc R U . . .
H34B H 0.4867 0.6131 0.2961 0.040 Uiso 1 1 calc R U . . .
H34C H 0.4065 0.5462 0.2680 0.040 Uiso 1 1 calc R U . . .


_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 C2 1.3481(13) . ?
O1 C1 1.4423(13) . ?
O2 C2 1.2100(13) . ?
O3 C9 1.4338(12) . ?
O3 N2 1.4556(11) . ?
O4 C15 1.4310(12) . ?
O4 N3 1.4642(10) . ?
N1 C2 1.3718(13) . ?
N1 C3 1.4439(13) . ?
N1 C15 1.4683(13) . ?
N2 C10 1.4907(13) . ?
N2 C14 1.4937(14) . ?
N3 C26 1.4969(13) . ?
N3 C22 1.4981(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.3886(15) . ?
C3 C8 1.3993(15) . ?
C4 C5 1.3891(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3864(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3864(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3927(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.5065(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C31 1.5257(16) . ?
C10 C11 1.5349(15) . ?
C10 C32 1.5412(15) . ?
C11 C12 1.5215(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5196(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5336(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C34 1.5279(16) . ?
C14 C33 1.5385(15) . ?
C15 C16 1.5173(14) . ?
C15 H15 1.0000 . ?
C16 C21 1.3902(15) . ?
C16 C17 1.3933(15) . ?
C17 C18 1.3886(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3860(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3830(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.3898(15) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.5288(15) . ?
C22 C28 1.5363(15) . ?
C22 C23 1.5373(15) . ?
C23 C24 1.5183(16) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5175(16) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5368(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C30 1.5277(15) . ?
C26 C29 1.5351(15) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

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 O1 C1 115.66(8) . . ?
C9 O3 N2 108.85(7) . . ?
C15 O4 N3 111.95(7) . . ?
C2 N1 C3 121.34(8) . . ?
C2 N1 C15 119.40(8) . . ?
C3 N1 C15 119.25(8) . . ?
O3 N2 C10 107.25(8) . . ?
O3 N2 C14 106.66(7) . . ?
C10 N2 C14 118.34(8) . . ?
O4 N3 C26 106.33(7) . . ?
O4 N3 C22 106.90(7) . . ?
C26 N3 C22 118.09(8) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.77(9) . . ?
O2 C2 N1 125.57(10) . . ?
O1 C2 N1 109.65(9) . . ?
C4 C3 C8 120.89(10) . . ?
C4 C3 N1 118.86(9) . . ?
C8 C3 N1 120.24(9) . . ?
C3 C4 C5 120.28(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.19(10) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 120.56(10) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.94(10) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C3 118.12(10) . . ?
C7 C8 C9 120.31(9) . . ?
C3 C8 C9 121.58(9) . . ?
O3 C9 C8 107.89(8) . . ?
O3 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O3 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C31 107.06(9) . . ?
N2 C10 C11 106.33(9) . . ?
C31 C10 C11 108.24(9) . . ?
N2 C10 C32 115.87(9) . . ?
C31 C10 C32 107.90(10) . . ?
C11 C10 C32 111.15(9) . . ?
C12 C11 C10 113.60(9) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 110.36(9) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 113.19(10) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
N2 C14 C34 107.14(9) . . ?
N2 C14 C13 106.51(8) . . ?
C34 C14 C13 108.16(10) . . ?
N2 C14 C33 116.09(10) . . ?
C34 C14 C33 107.75(9) . . ?
C13 C14 C33 110.89(9) . . ?
O4 C15 N1 110.12(8) . . ?
O4 C15 C16 110.37(8) . . ?
N1 C15 C16 109.27(8) . . ?
O4 C15 H15 109.0 . . ?
N1 C15 H15 109.0 . . ?
C16 C15 H15 109.0 . . ?
C21 C16 C17 119.09(10) . . ?
C21 C16 C15 118.83(9) . . ?
C17 C16 C15 121.99(9) . . ?
C18 C17 C16 120.12(10) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.45(10) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.64(10) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.13(10) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.53(10) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
N3 C22 C27 107.05(8) . . ?
N3 C22 C28 115.75(9) . . ?
C27 C22 C28 108.45(9) . . ?
N3 C22 C23 106.66(8) . . ?
C27 C22 C23 107.95(9) . . ?
C28 C22 C23 110.70(9) . . ?
C24 C23 C22 112.89(9) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 109.00(9) . . ?
C25 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C24 C25 C26 113.38(9) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
N3 C26 C30 107.39(8) . . ?
N3 C26 C29 115.31(8) . . ?
C30 C26 C29 107.94(9) . . ?
N3 C26 C25 107.21(8) . . ?
C30 C26 C25 107.79(9) . . ?
C29 C26 C25 110.91(9) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C10 C31 H31A 109.5 . . ?
C10 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C10 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C10 C32 H32A 109.5 . . ?
C10 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C10 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C14 C33 H33A 109.5 . . ?
C14 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C14 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C14 C34 H34A 109.5 . . ?
C14 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C14 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
C9 O3 N2 C10 115.50(9) . . . . ?
C9 O3 N2 C14 -116.77(9) . . . . ?
C15 O4 N3 C26 -113.97(8) . . . . ?
C15 O4 N3 C22 119.04(8) . . . . ?
C1 O1 C2 O2 -0.40(15) . . . . ?
C1 O1 C2 N1 -179.77(8) . . . . ?
C3 N1 C2 O2 -177.24(10) . . . . ?
C15 N1 C2 O2 3.05(15) . . . . ?
C3 N1 C2 O1 2.13(13) . . . . ?
C15 N1 C2 O1 -177.58(8) . . . . ?
C2 N1 C3 C4 -100.90(11) . . . . ?
C15 N1 C3 C4 78.80(12) . . . . ?
C2 N1 C3 C8 80.50(12) . . . . ?
C15 N1 C3 C8 -99.79(11) . . . . ?
C8 C3 C4 C5 0.92(15) . . . . ?
N1 C3 C4 C5 -177.67(9) . . . . ?
C3 C4 C5 C6 0.08(15) . . . . ?
C4 C5 C6 C7 -0.43(16) . . . . ?
C5 C6 C7 C8 -0.21(16) . . . . ?
C6 C7 C8 C3 1.17(15) . . . . ?
C6 C7 C8 C9 -178.99(9) . . . . ?
C4 C3 C8 C7 -1.52(14) . . . . ?
N1 C3 C8 C7 177.04(9) . . . . ?
C4 C3 C8 C9 178.64(9) . . . . ?
N1 C3 C8 C9 -2.80(14) . . . . ?
N2 O3 C9 C8 169.93(8) . . . . ?
C7 C8 C9 O3 26.60(13) . . . . ?
C3 C8 C9 O3 -153.56(9) . . . . ?
O3 N2 C10 C31 -66.63(10) . . . . ?
C14 N2 C10 C31 172.79(9) . . . . ?
O3 N2 C10 C11 177.83(8) . . . . ?
C14 N2 C10 C11 57.26(11) . . . . ?
O3 N2 C10 C32 53.78(12) . . . . ?
C14 N2 C10 C32 -66.80(13) . . . . ?
N2 C10 C11 C12 -53.05(12) . . . . ?
C31 C10 C11 C12 -167.79(10) . . . . ?
C32 C10 C11 C12 73.89(12) . . . . ?
C10 C11 C12 C13 54.42(13) . . . . ?
C11 C12 C13 C14 -54.56(13) . . . . ?
O3 N2 C14 C34 65.85(10) . . . . ?
C10 N2 C14 C34 -173.27(9) . . . . ?
O3 N2 C14 C13 -178.57(8) . . . . ?
C10 N2 C14 C13 -57.69(11) . . . . ?
O3 N2 C14 C33 -54.56(11) . . . . ?
C10 N2 C14 C33 66.32(12) . . . . ?
C12 C13 C14 N2 53.57(12) . . . . ?
C12 C13 C14 C34 168.46(9) . . . . ?
C12 C13 C14 C33 -73.59(12) . . . . ?
N3 O4 C15 N1 -118.08(8) . . . . ?
N3 O4 C15 C16 121.20(8) . . . . ?
C2 N1 C15 O4 113.49(9) . . . . ?
C3 N1 C15 O4 -66.22(11) . . . . ?
C2 N1 C15 C16 -125.12(9) . . . . ?
C3 N1 C15 C16 55.17(11) . . . . ?
O4 C15 C16 C21 -143.27(9) . . . . ?
N1 C15 C16 C21 95.49(11) . . . . ?
O4 C15 C16 C17 40.16(13) . . . . ?
N1 C15 C16 C17 -81.07(11) . . . . ?
C21 C16 C17 C18 -2.26(16) . . . . ?
C15 C16 C17 C18 174.30(10) . . . . ?
C16 C17 C18 C19 1.00(17) . . . . ?
C17 C18 C19 C20 0.98(17) . . . . ?
C18 C19 C20 C21 -1.68(17) . . . . ?
C19 C20 C21 C16 0.40(16) . . . . ?
C17 C16 C21 C20 1.56(15) . . . . ?
C15 C16 C21 C20 -175.10(9) . . . . ?
O4 N3 C22 C27 -69.35(9) . . . . ?
C26 N3 C22 C27 170.97(8) . . . . ?
O4 N3 C22 C28 51.67(11) . . . . ?
C26 N3 C22 C28 -68.01(12) . . . . ?
O4 N3 C22 C23 175.30(8) . . . . ?
C26 N3 C22 C23 55.62(11) . . . . ?
N3 C22 C23 C24 -55.25(11) . . . . ?
C27 C22 C23 C24 -169.99(9) . . . . ?
C28 C22 C23 C24 71.46(12) . . . . ?
C22 C23 C24 C25 57.85(12) . . . . ?
C23 C24 C25 C26 -56.75(12) . . . . ?
O4 N3 C26 C30 69.77(9) . . . . ?
C22 N3 C26 C30 -170.25(9) . . . . ?
O4 N3 C26 C29 -50.58(11) . . . . ?
C22 N3 C26 C29 69.41(12) . . . . ?
O4 N3 C26 C25 -174.63(7) . . . . ?
C22 N3 C26 C25 -54.64(11) . . . . ?
C24 C25 C26 N3 53.23(11) . . . . ?
C24 C25 C26 C30 168.57(9) . . . . ?
C24 C25 C26 C29 -73.46(11) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_C16H14ClNO2
_database_code_depnum_ccdc_archive 'CCDC 1833865'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl N O2'
_chemical_formula_sum            'C16 H14 Cl N O2'
_chemical_formula_weight         287.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.0463(3)
_cell_length_b                   10.3570(5)
_cell_length_c                   13.2269(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.007(2)
_cell_angle_gamma                90
_cell_volume                     690.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      69.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.452
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11978
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.343
_diffrn_reflns_theta_max         69.790
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2589
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.0832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2589
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.16868(8) 0.64084(4) 0.91668(3) 0.02157(14) Uani 1 1 d . . . . .
O1 O 0.7560(3) 0.29565(14) 0.54008(10) 0.0237(3) Uani 1 1 d . . . . .
O2 O 1.0232(3) 0.45907(13) 0.59523(10) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.7366(3) 0.37521(15) 0.70099(11) 0.0174(3) Uani 1 1 d . . . . .
C1 C 1.1362(4) 0.4637(2) 0.49635(15) 0.0263(4) Uani 1 1 d . . . . .
H1A H 1.2625 0.3926 0.4898 0.039 Uiso 1 1 calc R U . . .
H1B H 1.2281 0.5462 0.4881 0.039 Uiso 1 1 calc R U . . .
H1C H 0.9945 0.4555 0.4441 0.039 Uiso 1 1 calc R U . . .
C2 C 0.8329(4) 0.36956(18) 0.60609(15) 0.0173(4) Uani 1 1 d . . . . .
C3 C 0.5426(4) 0.29082(17) 0.73825(14) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.3718(4) 0.20763(17) 0.68476(15) 0.0197(4) Uani 1 1 d . . . . .
H4 H 0.3784 0.1989 0.6134 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1908(4) 0.1377(2) 0.74036(15) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.0710 0.0807 0.7059 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1813(4) 0.1492(2) 0.84457(15) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.0561 0.1003 0.8805 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3547(4) 0.23217(18) 0.89673(15) 0.0193(4) Uani 1 1 d . . . . .
H7 H 0.3495 0.2399 0.9682 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5347(4) 0.30330(18) 0.84309(14) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.7376(4) 0.39972(18) 0.88111(13) 0.0173(4) Uani 1 1 d . . . . .
H9A H 0.8778 0.3571 0.9234 0.021 Uiso 1 1 calc R U . . .
H9B H 0.6540 0.4682 0.9214 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8535(4) 0.45665(18) 0.78281(13) 0.0155(4) Uani 1 1 d . . . . .
H10 H 1.0506 0.4460 0.7853 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7851(4) 0.59840(17) 0.77071(14) 0.0160(4) Uani 1 1 d . . . . .
C12 C 0.9176(4) 0.69025(19) 0.83047(14) 0.0178(4) Uani 1 1 d . . . . .
C13 C 0.8560(4) 0.8203(2) 0.82602(17) 0.0245(4) Uani 1 1 d . . . . .
H13 H 0.9504 0.8806 0.8678 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6544(5) 0.8615(2) 0.75974(17) 0.0276(5) Uani 1 1 d . . . . .
H14 H 0.6103 0.9506 0.7557 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5178(4) 0.7733(2) 0.69955(16) 0.0254(4) Uani 1 1 d . . . . .
H15 H 0.3792 0.8016 0.6544 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5833(4) 0.6425(2) 0.70500(13) 0.0198(4) Uani 1 1 d . . . . .
H16 H 0.4885 0.5825 0.6632 0.024 Uiso 1 1 calc R U . . .


_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 1.751(2) . ?
O1 C2 1.214(2) . ?
O2 C2 1.346(2) . ?
O2 C1 1.446(2) . ?
N1 C2 1.363(3) . ?
N1 C3 1.414(2) . ?
N1 C10 1.478(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.394(3) . ?
C3 C8 1.395(3) . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.504(3) . ?
C9 C10 1.560(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.515(2) . ?
C10 H10 1.0000 . ?
C11 C16 1.393(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 O2 C1 115.14(15) . . ?
C2 N1 C3 124.60(16) . . ?
C2 N1 C10 123.55(15) . . ?
C3 N1 C10 111.16(15) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.64(18) . . ?
O1 C2 N1 125.04(18) . . ?
O2 C2 N1 110.32(16) . . ?
C4 C3 C8 121.55(18) . . ?
C4 C3 N1 128.95(17) . . ?
C8 C3 N1 109.48(16) . . ?
C3 C4 C5 117.26(17) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 121.70(18) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.20(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.13(17) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 120.16(18) . . ?
C7 C8 C9 129.29(17) . . ?
C3 C8 C9 110.56(16) . . ?
C8 C9 C10 104.06(15) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
N1 C10 C11 113.07(15) . . ?
N1 C10 C9 104.05(14) . . ?
C11 C10 C9 111.32(15) . . ?
N1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C16 C11 C12 117.14(18) . . ?
C16 C11 C10 122.86(17) . . ?
C12 C11 C10 119.92(17) . . ?
C13 C12 C11 122.58(19) . . ?
C13 C12 Cl1 117.95(16) . . ?
C11 C12 Cl1 119.47(15) . . ?
C12 C13 C14 119.01(19) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.12(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.99(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 121.2(2) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?

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
C1 O2 C2 O1 0.3(3) . . . . ?
C1 O2 C2 N1 -178.77(16) . . . . ?
C3 N1 C2 O1 3.6(3) . . . . ?
C10 N1 C2 O1 173.28(17) . . . . ?
C3 N1 C2 O2 -177.29(15) . . . . ?
C10 N1 C2 O2 -7.6(2) . . . . ?
C2 N1 C3 C4 -15.5(3) . . . . ?
C10 N1 C3 C4 173.77(18) . . . . ?
C2 N1 C3 C8 166.27(17) . . . . ?
C10 N1 C3 C8 -4.5(2) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
N1 C3 C4 C5 -177.68(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C6 C7 C8 C9 179.05(18) . . . . ?
C4 C3 C8 C7 0.1(3) . . . . ?
N1 C3 C8 C7 178.49(16) . . . . ?
C4 C3 C8 C9 -179.55(16) . . . . ?
N1 C3 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C10 -173.75(18) . . . . ?
C3 C8 C9 C10 5.81(19) . . . . ?
C2 N1 C10 C11 76.0(2) . . . . ?
C3 N1 C10 C11 -113.09(16) . . . . ?
C2 N1 C10 C9 -163.03(16) . . . . ?
C3 N1 C10 C9 7.85(19) . . . . ?
C8 C9 C10 N1 -7.94(18) . . . . ?
C8 C9 C10 C11 114.15(16) . . . . ?
N1 C10 C11 C16 15.0(2) . . . . ?
C9 C10 C11 C16 -101.8(2) . . . . ?
N1 C10 C11 C12 -168.34(16) . . . . ?
C9 C10 C11 C12 74.9(2) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
C10 C11 C12 C13 -177.11(18) . . . . ?
C16 C11 C12 Cl1 178.63(13) . . . . ?
C10 C11 C12 Cl1 1.8(2) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
Cl1 C12 C13 C14 -178.77(15) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C10 C11 C16 C15 176.86(17) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_C112H88CoN8O8
_database_code_depnum_ccdc_archive 'CCDC 1833868'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C112 H88 Co N8 O8'
_chemical_formula_sum            'C112 H88 Co N8 O8'
_chemical_formula_weight         1732.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.7206(3)
_cell_length_b                   36.0918(7)
_cell_length_c                   22.8341(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10483.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      66.52

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_F_000             3628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.730
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2013). TWINABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34025
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_full        66.601
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8791
_reflns_number_gt                7633
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.003(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8791
_refine_ls_number_parameters     639
_refine_ls_number_restraints     562
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.31202(2) 0.2500 0.01774(14) Uani 1 2 d S TU P . .
O1 O 0.9989(2) 0.25071(6) 0.34751(11) 0.0485(6) Uani 1 1 d . U . . .
O2 O 0.7751(5) 0.44900(14) 0.4144(4) 0.071(2) Uani 0.88(3) 1 d D U P . .
O2X O 0.806(3) 0.4544(9) 0.388(3) 0.080(13) Uiso 0.12(3) 1 d D . P . .
O3 O 0.28727(18) 0.35952(6) 0.44096(8) 0.0323(5) Uani 1 1 d . U . . .
O4 O 0.28009(18) 0.23179(5) 0.40666(9) 0.0335(5) Uani 1 1 d . U . . .
N1 N 0.52694(16) 0.31330(6) 0.33411(8) 0.0199(5) Uani 1 1 d . U . . .
N2 N 0.34953(18) 0.31156(6) 0.26622(8) 0.0222(5) Uani 1 1 d . U . . .
N3 N 0.8509(2) 0.27532(7) 0.38721(10) 0.0311(6) Uani 1 1 d . U . . .
H3N H 0.7887 0.2697 0.4015 0.037 Uiso 1 1 calc R U . . .
N4 N 0.7595(2) 0.40223(7) 0.34764(12) 0.0384(6) Uani 1 1 d . U . . .
H4N H 0.7284 0.3958 0.3148 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7152(2) 0.32707(7) 0.33233(11) 0.0245(6) Uani 1 1 d . U . . .
C2 C 0.6196(2) 0.32258(7) 0.36063(11) 0.0222(6) Uani 1 1 d . U . . .
C3 C 0.6071(2) 0.32371(7) 0.42312(11) 0.0235(6) Uani 1 1 d . U . . .
H3 H 0.6591 0.3305 0.4510 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5079(2) 0.31325(7) 0.43451(10) 0.0241(5) Uani 1 1 d . U . . .
H4 H 0.4775 0.3102 0.4722 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4560(2) 0.30754(7) 0.37930(10) 0.0212(5) Uani 1 1 d . U . . .
C6 C 0.3499(2) 0.30105(7) 0.37249(11) 0.0238(6) Uani 1 1 d . U . . .
C7 C 0.3001(2) 0.30464(8) 0.31851(11) 0.0245(6) Uani 1 1 d . U . . .
C8 C 0.1886(2) 0.30698(9) 0.31112(11) 0.0292(6) Uani 1 1 d . U . . .
H8 H 0.1369 0.3022 0.3402 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1705(2) 0.31718(8) 0.25564(12) 0.0324(6) Uani 1 1 d . U . . .
H9 H 0.1039 0.3221 0.2385 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2706(2) 0.31938(8) 0.22685(11) 0.0249(6) Uani 1 1 d . U . . .
C11 C 0.8098(2) 0.33918(8) 0.36570(11) 0.0275(6) Uani 1 1 d . U . . .
C12 C 0.8805(2) 0.31305(9) 0.38878(11) 0.0286(6) Uani 1 1 d . U . . .
C13 C 0.9739(2) 0.32429(10) 0.41426(12) 0.0360(7) Uani 1 1 d . U . . .
H13 H 1.0216 0.3066 0.4298 0.043 Uiso 1 1 calc R U . . .
C14 C 0.9971(3) 0.36181(10) 0.41681(13) 0.0433(8) Uani 1 1 d . U . . .
H14 H 1.0620 0.3696 0.4333 0.052 Uiso 1 1 calc R U . . .
C15 C 0.9276(3) 0.38813(10) 0.39580(15) 0.0439(8) Uani 1 1 d . U . . .
H15 H 0.9441 0.4137 0.3986 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8338(3) 0.37685(9) 0.37069(13) 0.0353(7) Uani 1 1 d . U . . .
C17 C 0.9097(2) 0.24674(9) 0.36565(12) 0.0326(7) Uani 1 1 d . U . . .
C18 C 0.8515(3) 0.21118(9) 0.36653(13) 0.0349(7) Uani 1 1 d . U . . .
H18 H 0.8128 0.2062 0.4038 0.042 Uiso 1 1 calc R U . . .
C19 C 0.8884(3) 0.17714(9) 0.33509(15) 0.0432(8) Uani 1 1 d . U . . .
H19A H 0.8756 0.1529 0.3541 0.052 Uiso 1 1 calc R U . . .
H19B H 0.9552 0.1788 0.3130 0.052 Uiso 1 1 calc R U . . .
C20 C 0.7951(3) 0.19746(9) 0.31100(12) 0.0363(7) Uani 1 1 d D U . . .
C21 C 0.6842(4) 0.1855(3) 0.3193(3) 0.0367(15) Uani 0.804(18) 1 d D U P A 1
C22 C 0.6588(6) 0.1487(3) 0.3265(3) 0.0578(18) Uani 0.804(18) 1 d D U P A 1
H22 H 0.7138 0.1309 0.3269 0.069 Uiso 0.804(18) 1 calc R U P A 1
C23 C 0.5561(7) 0.1366(3) 0.3330(4) 0.076(3) Uani 0.804(18) 1 d D U P A 1
H23 H 0.5405 0.1111 0.3378 0.091 Uiso 0.804(18) 1 calc R U P A 1
C24 C 0.4764(5) 0.1630(3) 0.3324(3) 0.069(3) Uani 0.804(18) 1 d D U P A 1
H24 H 0.4053 0.1554 0.3366 0.082 Uiso 0.804(18) 1 calc R U P A 1
C25 C 0.4997(4) 0.2003(3) 0.3258(2) 0.059(2) Uani 0.804(18) 1 d D U P A 1
H25 H 0.4448 0.2181 0.3258 0.071 Uiso 0.804(18) 1 calc R U P A 1
C26 C 0.6028(4) 0.2114(3) 0.3194(2) 0.0433(16) Uani 0.804(18) 1 d D U P A 1
H26 H 0.6185 0.2370 0.3149 0.052 Uiso 0.804(18) 1 calc R U P A 1
C21X C 0.6953(16) 0.1754(6) 0.3226(15) 0.031(8) Uiso 0.196(18) 1 d D . P A 2
C22X C 0.685(2) 0.1379(6) 0.3367(11) 0.042(7) Uiso 0.196(18) 1 d D . P A 2
H22X H 0.7451 0.1225 0.3364 0.051 Uiso 0.196(18) 1 calc R U P A 2
C23X C 0.590(2) 0.1229(7) 0.3509(13) 0.068(9) Uiso 0.196(18) 1 d D . P A 2
H23X H 0.5857 0.0982 0.3651 0.081 Uiso 0.196(18) 1 calc R U P A 2
C24X C 0.498(2) 0.1441(7) 0.3445(10) 0.045(6) Uiso 0.196(18) 1 d D . P A 2
H24X H 0.4313 0.1323 0.3487 0.053 Uiso 0.196(18) 1 calc R U P A 2
C25X C 0.5012(17) 0.1821(7) 0.3322(11) 0.036(6) Uiso 0.196(18) 1 d D . P A 2
H25X H 0.4402 0.1973 0.3321 0.043 Uiso 0.196(18) 1 calc R U P A 2
C26X C 0.6024(15) 0.1959(6) 0.3200(9) 0.027(6) Uiso 0.196(18) 1 d D . P A 2
H26X H 0.6078 0.2213 0.3092 0.032 Uiso 0.196(18) 1 calc R U P A 2
C27 C 0.8120(3) 0.21836(9) 0.25421(14) 0.0431(8) Uani 1 1 d . U . . .
H27A H 0.8012 0.2016 0.2210 0.065 Uiso 1 1 calc R U . . .
H27B H 0.8838 0.2281 0.2531 0.065 Uiso 1 1 calc R U . . .
H27C H 0.7618 0.2389 0.2518 0.065 Uiso 1 1 calc R U . . .
C28 C 0.7311(3) 0.43550(10) 0.37078(18) 0.0506(9) Uani 1 1 d D U . . .
C29 C 0.6381(3) 0.45202(9) 0.34225(18) 0.0531(9) Uani 1 1 d . U . . .
H29 H 0.6269 0.4450 0.3003 0.064 Uiso 1 1 calc R U . . .
C30 C 0.6037(4) 0.49062(11) 0.3589(2) 0.0707(13) Uani 1 1 d . U . . .
H30A H 0.6452 0.5037 0.3892 0.085 Uiso 1 1 calc R U . . .
H30B H 0.5756 0.5067 0.3275 0.085 Uiso 1 1 calc R U . . .
C31 C 0.5381(4) 0.45876(9) 0.37805(16) 0.0512(10) Uani 1 1 d . U . . .
C32 C 0.4366(3) 0.45048(9) 0.34783(15) 0.0434(8) Uani 1 1 d . U . . .
C33 C 0.4042(3) 0.41410(9) 0.33880(16) 0.0489(9) Uani 1 1 d . U . . .
H33 H 0.4496 0.3943 0.3492 0.059 Uiso 1 1 calc R U . . .
C34 C 0.3070(4) 0.40653(11) 0.31492(15) 0.0516(9) Uani 1 1 d . U . . .
H34 H 0.2855 0.3816 0.3093 0.062 Uiso 1 1 calc R U . . .
C35 C 0.2410(4) 0.43510(11) 0.29919(16) 0.0551(10) Uani 1 1 d . U . . .
H35 H 0.1734 0.4299 0.2835 0.066 Uiso 1 1 calc R U . . .
C36 C 0.2734(4) 0.47103(11) 0.30636(18) 0.0594(11) Uani 1 1 d . U . . .
H36 H 0.2289 0.4907 0.2942 0.071 Uiso 1 1 calc R U . . .
C37 C 0.3687(4) 0.47884(10) 0.33063(17) 0.0533(10) Uani 1 1 d . U . . .
H37 H 0.3892 0.5039 0.3359 0.064 Uiso 1 1 calc R U . . .
C38 C 0.5370(4) 0.44833(13) 0.44283(17) 0.0690(13) Uani 1 1 d . U . . .
H38A H 0.4776 0.4605 0.4622 0.104 Uiso 1 1 calc R U . . .
H38B H 0.6029 0.4564 0.4612 0.104 Uiso 1 1 calc R U . . .
H38C H 0.5299 0.4214 0.4467 0.104 Uiso 1 1 calc R U . . .
C39 C 0.2830(2) 0.29538(8) 0.42576(11) 0.0230(6) Uani 1 1 d . U . . .
C40 C 0.2528(2) 0.32569(8) 0.46040(11) 0.0273(6) Uani 1 1 d . U . . .
C41 C 0.1881(2) 0.32124(9) 0.50884(11) 0.0294(7) Uani 1 1 d . U . . .
H41 H 0.1694 0.3419 0.5323 0.035 Uiso 1 1 calc R U . . .
C42 C 0.1515(2) 0.28638(9) 0.52225(11) 0.0293(6) Uani 1 1 d . U . . .
H42 H 0.1056 0.2833 0.5547 0.035 Uiso 1 1 calc R U . . .
C43 C 0.1801(2) 0.25552(9) 0.48938(12) 0.0286(6) Uani 1 1 d . U . . .
H43 H 0.1549 0.2316 0.4994 0.034 Uiso 1 1 calc R U . . .
C44 C 0.2464(2) 0.26046(8) 0.44150(12) 0.0266(6) Uani 1 1 d . U . . .
C45 C 0.2908(3) 0.38887(9) 0.48033(13) 0.0350(7) Uani 1 1 d . U . . .
C46 C 0.3553(14) 0.3882(2) 0.5282(5) 0.044(4) Uani 0.843(17) 1 d D U P B 1
H46 H 0.3995 0.3675 0.5356 0.053 Uiso 0.843(17) 1 calc R U P B 1
C47 C 0.3549(8) 0.41858(16) 0.5661(2) 0.0550(18) Uani 0.843(17) 1 d D U P B 1
H47 H 0.3969 0.4182 0.6005 0.066 Uiso 0.843(17) 1 calc R U P B 1
C48 C 0.2943(9) 0.44868(15) 0.5537(2) 0.075(3) Uani 0.843(17) 1 d D U P B 1
H48 H 0.2962 0.4696 0.5788 0.090 Uiso 0.843(17) 1 calc R U P B 1
C49 C 0.2298(8) 0.44896(17) 0.5046(3) 0.083(3) Uani 0.843(17) 1 d D U P B 1
H49 H 0.1865 0.4698 0.4967 0.099 Uiso 0.843(17) 1 calc R U P B 1
C50 C 0.2287(7) 0.41848(19) 0.4667(2) 0.0526(17) Uani 0.843(17) 1 d D U P B 1
H50 H 0.1860 0.4184 0.4326 0.063 Uiso 0.843(17) 1 calc R U P B 1
C46X C 0.348(6) 0.3850(10) 0.532(3) 0.024(11) Uiso 0.157(17) 1 d D . P B 2
H46X H 0.3572 0.3606 0.5471 0.029 Uiso 0.157(17) 1 calc R U P B 2
C47X C 0.392(3) 0.4144(8) 0.5642(15) 0.044(10) Uiso 0.157(17) 1 d D . P B 2
H47X H 0.4440 0.4102 0.5935 0.052 Uiso 0.157(17) 1 calc R U P B 2
C48X C 0.358(3) 0.4487(6) 0.5510(10) 0.048(8) Uiso 0.157(17) 1 d D . P B 2
H48X H 0.3787 0.4690 0.5750 0.057 Uiso 0.157(17) 1 calc R U P B 2
C49X C 0.293(3) 0.4552(6) 0.5030(10) 0.044(8) Uiso 0.157(17) 1 d D . P B 2
H49X H 0.2656 0.4794 0.4968 0.052 Uiso 0.157(17) 1 calc R U P B 2
C50X C 0.268(3) 0.4272(7) 0.4640(10) 0.032(7) Uiso 0.157(17) 1 d D . P B 2
H50X H 0.2366 0.4328 0.4273 0.038 Uiso 0.157(17) 1 calc R U P B 2
C51 C 0.2504(2) 0.19579(8) 0.42201(12) 0.0296(6) Uani 1 1 d . U . . .
C52 C 0.1554(3) 0.18209(9) 0.40282(12) 0.0344(7) Uani 1 1 d . U . . .
H52 H 0.1078 0.1974 0.3818 0.041 Uiso 1 1 calc R U . . .
C53 C 0.1312(3) 0.14562(9) 0.41497(14) 0.0431(8) Uani 1 1 d . U . . .
H53 H 0.0663 0.1356 0.4018 0.052 Uiso 1 1 calc R U . . .
C54 C 0.2006(3) 0.12332(9) 0.44630(14) 0.0434(8) Uani 1 1 d . U . . .
H54 H 0.1830 0.0983 0.4545 0.052 Uiso 1 1 calc R U . . .
C55 C 0.2946(3) 0.13770(9) 0.46531(14) 0.0426(8) Uani 1 1 d . U . . .
H55 H 0.3421 0.1225 0.4866 0.051 Uiso 1 1 calc R U . . .
C56 C 0.3204(3) 0.17427(9) 0.45348(12) 0.0338(7) Uani 1 1 d . U . . .
H56 H 0.3850 0.1844 0.4668 0.041 Uiso 1 1 calc R U . . .


_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
Co1 N2 1.950(2) . ?
Co1 N2 1.950(2) 3_655 ?
Co1 N1 1.9515(19) . ?
Co1 N1 1.9515(19) 3_655 ?
O1 C17 1.216(4) . ?
O2 C28 1.241(5) . ?
O3 C40 1.371(4) . ?
O3 C45 1.390(3) . ?
O4 C44 1.374(3) . ?
O4 C51 1.398(3) . ?
N1 C2 1.367(3) . ?
N1 C5 1.386(3) . ?
N2 C7 1.373(3) . ?
N2 C10 1.377(3) . ?
N3 C17 1.365(4) . ?
N3 C12 1.413(4) . ?
N3 H3N 0.8800 . ?
N4 C28 1.361(5) . ?
N4 C16 1.417(4) . ?
N4 H4N 0.8800 . ?
C1 C2 1.386(4) . ?
C1 C10 1.391(4) 3_655 ?
C1 C11 1.491(4) . ?
C2 C3 1.436(4) . ?
C3 C4 1.343(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.438(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C6 C7 1.392(4) . ?
C6 C39 1.499(4) . ?
C7 C8 1.431(4) . ?
C8 C9 1.339(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.434(4) . ?
C9 H9 0.9500 . ?
C10 C1 1.391(4) 3_655 ?
C11 C16 1.398(4) . ?
C11 C12 1.406(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C17 C18 1.482(5) . ?
C18 C19 1.498(5) . ?
C18 C20 1.539(4) . ?
C18 H18 1.0000 . ?
C19 C20 1.499(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.488(6) . ?
C20 C27 1.515(4) . ?
C21 C22 1.377(8) . ?
C21 C26 1.395(9) . ?
C22 C23 1.385(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.477(6) . ?
C29 C30 1.509(5) . ?
C29 C31 1.531(6) . ?
C29 H29 1.0000 . ?
C30 C31 1.487(6) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.495(6) . ?
C31 C38 1.526(5) . ?
C32 C33 1.391(5) . ?
C32 C37 1.395(5) . ?
C33 C34 1.379(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.371(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.362(6) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C44 1.391(4) . ?
C39 C40 1.403(4) . ?
C40 C41 1.388(4) . ?
C41 C42 1.376(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.392(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(4) . ?
C43 H43 0.9500 . ?
C45 C50 1.365(6) . ?
C45 C46 1.367(10) . ?
C46 C47 1.396(10) . ?
C46 H46 0.9500 . ?
C47 C48 1.362(9) . ?
C47 H47 0.9500 . ?
C48 C49 1.390(9) . ?
C48 H48 0.9500 . ?
C49 C50 1.399(7) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.377(4) . ?
C51 C56 1.382(4) . ?
C52 C53 1.380(5) . ?
C52 H52 0.9500 . ?
C53 C54 1.392(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.374(6) . ?
C54 H54 0.9500 . ?
C55 C56 1.387(5) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?

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
N2 Co1 N2 179.00(14) . 3_655 ?
N2 Co1 N1 89.18(8) . . ?
N2 Co1 N1 90.84(8) 3_655 . ?
N2 Co1 N1 90.85(8) . 3_655 ?
N2 Co1 N1 89.18(8) 3_655 3_655 ?
N1 Co1 N1 177.29(13) . 3_655 ?
C40 O3 C45 118.7(2) . . ?
C44 O4 C51 118.1(2) . . ?
C2 N1 C5 105.6(2) . . ?
C2 N1 Co1 126.38(17) . . ?
C5 N1 Co1 127.92(17) . . ?
C7 N2 C10 105.7(2) . . ?
C7 N2 Co1 128.08(18) . . ?
C10 N2 Co1 126.17(17) . . ?
C17 N3 C12 126.2(3) . . ?
C17 N3 H3N 116.9 . . ?
C12 N3 H3N 116.9 . . ?
C28 N4 C16 127.1(3) . . ?
C28 N4 H4N 116.5 . . ?
C16 N4 H4N 116.5 . . ?
C2 C1 C10 122.9(3) . 3_655 ?
C2 C1 C11 120.3(2) . . ?
C10 C1 C11 116.7(3) 3_655 . ?
N1 C2 C1 125.3(2) . . ?
N1 C2 C3 110.6(2) . . ?
C1 C2 C3 123.8(2) . . ?
C4 C3 C2 106.7(2) . . ?
C4 C3 H3 126.6 . . ?
C2 C3 H3 126.6 . . ?
C3 C4 C5 107.6(2) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
C6 C5 N1 125.4(2) . . ?
C6 C5 C4 124.9(2) . . ?
N1 C5 C4 109.4(2) . . ?
C5 C6 C7 122.0(2) . . ?
C5 C6 C39 119.2(2) . . ?
C7 C6 C39 118.2(2) . . ?
N2 C7 C6 125.3(3) . . ?
N2 C7 C8 109.9(2) . . ?
C6 C7 C8 124.1(2) . . ?
C9 C8 C7 107.3(2) . . ?
C9 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
C8 C9 C10 107.3(3) . . ?
C8 C9 H9 126.4 . . ?
C10 C9 H9 126.4 . . ?
N2 C10 C1 125.4(3) . 3_655 ?
N2 C10 C9 109.7(2) . . ?
C1 C10 C9 124.9(3) 3_655 . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C1 120.2(3) . . ?
C12 C11 C1 120.8(3) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 N3 121.5(3) . . ?
C11 C12 N3 117.8(3) . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 N4 122.6(3) . . ?
C11 C16 N4 116.9(3) . . ?
O1 C17 N3 123.0(3) . . ?
O1 C17 C18 124.9(3) . . ?
N3 C17 C18 112.1(3) . . ?
C17 C18 C19 123.2(3) . . ?
C17 C18 C20 120.0(2) . . ?
C19 C18 C20 59.1(2) . . ?
C17 C18 H18 114.5 . . ?
C19 C18 H18 114.5 . . ?
C20 C18 H18 114.5 . . ?
C18 C19 C20 61.8(2) . . ?
C18 C19 H19A 117.6 . . ?
C20 C19 H19A 117.6 . . ?
C18 C19 H19B 117.6 . . ?
C20 C19 H19B 117.6 . . ?
H19A C19 H19B 114.7 . . ?
C21 C20 C19 124.2(5) . . ?
C21 C20 C27 112.8(4) . . ?
C19 C20 C27 116.5(3) . . ?
C21 C20 C18 115.5(3) . . ?
C19 C20 C18 59.1(2) . . ?
C27 C20 C18 118.6(3) . . ?
C22 C21 C26 118.2(5) . . ?
C22 C21 C20 121.2(6) . . ?
C26 C21 C20 120.6(6) . . ?
C21 C22 C23 122.5(7) . . ?
C21 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C22 C23 C24 118.1(7) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 120.7(6) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 119.8(7) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.7(7) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O2 C28 N4 122.6(4) . . ?
O2 C28 C29 123.8(4) . . ?
N4 C28 C29 113.4(3) . . ?
C28 C29 C30 119.6(4) . . ?
C28 C29 C31 119.6(3) . . ?
C30 C29 C31 58.6(3) . . ?
C28 C29 H29 115.7 . . ?
C30 C29 H29 115.7 . . ?
C31 C29 H29 115.7 . . ?
C31 C30 C29 61.5(3) . . ?
C31 C30 H30A 117.6 . . ?
C29 C30 H30A 117.6 . . ?
C31 C30 H30B 117.6 . . ?
C29 C30 H30B 117.6 . . ?
H30A C30 H30B 114.7 . . ?
C30 C31 C32 120.3(4) . . ?
C30 C31 C38 118.8(4) . . ?
C32 C31 C38 113.0(4) . . ?
C30 C31 C29 60.0(3) . . ?
C32 C31 C29 116.1(3) . . ?
C38 C31 C29 119.1(4) . . ?
C33 C32 C37 117.9(4) . . ?
C33 C32 C31 120.8(3) . . ?
C37 C32 C31 121.2(3) . . ?
C34 C33 C32 120.7(4) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 120.1(4) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 119.6(4) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C37 C36 C35 120.8(4) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C32 120.9(4) . . ?
C36 C37 H37 119.6 . . ?
C32 C37 H37 119.6 . . ?
C31 C38 H38A 109.5 . . ?
C31 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C31 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C44 C39 C40 118.0(2) . . ?
C44 C39 C6 121.6(2) . . ?
C40 C39 C6 120.4(3) . . ?
O3 C40 C41 123.4(3) . . ?
O3 C40 C39 115.1(2) . . ?
C41 C40 C39 121.4(3) . . ?
C42 C41 C40 118.9(3) . . ?
C42 C41 H41 120.5 . . ?
C40 C41 H41 120.5 . . ?
C41 C42 C43 121.5(3) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 H42 119.2 . . ?
C42 C43 C44 118.7(3) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
O4 C44 C39 115.4(2) . . ?
O4 C44 C43 123.2(3) . . ?
C39 C44 C43 121.4(3) . . ?
C50 C45 C46 122.8(6) . . ?
C50 C45 O3 115.5(3) . . ?
C46 C45 O3 121.6(5) . . ?
C45 C46 C47 118.8(10) . . ?
C45 C46 H46 120.6 . . ?
C47 C46 H46 120.6 . . ?
C48 C47 C46 119.9(7) . . ?
C48 C47 H47 120.1 . . ?
C46 C47 H47 120.1 . . ?
C47 C48 C49 120.5(5) . . ?
C47 C48 H48 119.7 . . ?
C49 C48 H48 119.7 . . ?
C48 C49 C50 119.9(5) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C45 C50 C49 118.0(5) . . ?
C45 C50 H50 121.0 . . ?
C49 C50 H50 121.0 . . ?
C52 C51 C56 121.9(3) . . ?
C52 C51 O4 119.4(3) . . ?
C56 C51 O4 118.6(3) . . ?
C51 C52 C53 118.3(3) . . ?
C51 C52 H52 120.8 . . ?
C53 C52 H52 120.8 . . ?
C52 C53 C54 120.9(3) . . ?
C52 C53 H53 119.6 . . ?
C54 C53 H53 119.6 . . ?
C55 C54 C53 119.7(3) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C54 C55 C56 120.3(3) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C51 C56 C55 118.9(3) . . ?
C51 C56 H56 120.5 . . ?
C55 C56 H56 120.5 . . ?

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
C5 N1 C2 C1 173.0(3) . . . . ?
Co1 N1 C2 C1 -10.8(4) . . . . ?
C5 N1 C2 C3 -1.5(3) . . . . ?
Co1 N1 C2 C3 174.68(17) . . . . ?
C10 C1 C2 N1 -5.7(4) 3_655 . . . ?
C11 C1 C2 N1 176.8(3) . . . . ?
C10 C1 C2 C3 168.1(3) 3_655 . . . ?
C11 C1 C2 C3 -9.3(4) . . . . ?
N1 C2 C3 C4 3.1(3) . . . . ?
C1 C2 C3 C4 -171.6(3) . . . . ?
C2 C3 C4 C5 -3.2(3) . . . . ?
C2 N1 C5 C6 173.5(3) . . . . ?
Co1 N1 C5 C6 -2.6(4) . . . . ?
C2 N1 C5 C4 -0.5(3) . . . . ?
Co1 N1 C5 C4 -176.59(18) . . . . ?
C3 C4 C5 C6 -171.6(3) . . . . ?
C3 C4 C5 N1 2.4(3) . . . . ?
N1 C5 C6 C7 -9.0(4) . . . . ?
C4 C5 C6 C7 164.1(3) . . . . ?
N1 C5 C6 C39 -179.9(2) . . . . ?
C4 C5 C6 C39 -6.8(4) . . . . ?
C10 N2 C7 C6 -169.7(3) . . . . ?
Co1 N2 C7 C6 8.5(4) . . . . ?
C10 N2 C7 C8 1.9(3) . . . . ?
Co1 N2 C7 C8 -179.84(19) . . . . ?
C5 C6 C7 N2 6.0(4) . . . . ?
C39 C6 C7 N2 177.0(3) . . . . ?
C5 C6 C7 C8 -164.5(3) . . . . ?
C39 C6 C7 C8 6.5(4) . . . . ?
N2 C7 C8 C9 -3.2(3) . . . . ?
C6 C7 C8 C9 168.5(3) . . . . ?
C7 C8 C9 C10 3.1(3) . . . . ?
C7 N2 C10 C1 -178.1(3) . . . 3_655 ?
Co1 N2 C10 C1 3.6(4) . . . 3_655 ?
C7 N2 C10 C9 0.0(3) . . . . ?
Co1 N2 C10 C9 -178.3(2) . . . . ?
C8 C9 C10 N2 -2.0(3) . . . . ?
C8 C9 C10 C1 176.1(3) . . . 3_655 ?
C2 C1 C11 C16 -91.0(3) . . . . ?
C10 C1 C11 C16 91.4(3) 3_655 . . . ?
C2 C1 C11 C12 93.8(3) . . . . ?
C10 C1 C11 C12 -83.8(3) 3_655 . . . ?
C16 C11 C12 C13 -2.2(4) . . . . ?
C1 C11 C12 C13 173.1(3) . . . . ?
C16 C11 C12 N3 175.3(2) . . . . ?
C1 C11 C12 N3 -9.5(4) . . . . ?
C17 N3 C12 C13 -53.9(4) . . . . ?
C17 N3 C12 C11 128.7(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
N3 C12 C13 C14 -177.3(3) . . . . ?
C12 C13 C14 C15 1.7(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C11 -0.9(5) . . . . ?
C14 C15 C16 N4 -179.2(3) . . . . ?
C12 C11 C16 C15 2.6(4) . . . . ?
C1 C11 C16 C15 -172.7(3) . . . . ?
C12 C11 C16 N4 -179.0(2) . . . . ?
C1 C11 C16 N4 5.7(4) . . . . ?
C28 N4 C16 C15 -39.9(5) . . . . ?
C28 N4 C16 C11 141.8(3) . . . . ?
C12 N3 C17 O1 3.8(5) . . . . ?
C12 N3 C17 C18 -175.5(2) . . . . ?
O1 C17 C18 C19 -11.6(5) . . . . ?
N3 C17 C18 C19 167.7(3) . . . . ?
O1 C17 C18 C20 -82.4(4) . . . . ?
N3 C17 C18 C20 97.0(3) . . . . ?
C17 C18 C19 C20 -107.8(3) . . . . ?
C18 C19 C20 C21 -101.5(4) . . . . ?
C18 C19 C20 C27 109.0(3) . . . . ?
C17 C18 C20 C21 -130.8(5) . . . . ?
C19 C18 C20 C21 116.1(5) . . . . ?
C17 C18 C20 C19 113.0(3) . . . . ?
C17 C18 C20 C27 7.7(4) . . . . ?
C19 C18 C20 C27 -105.4(3) . . . . ?
C19 C20 C21 C22 -28.7(8) . . . . ?
C27 C20 C21 C22 121.7(6) . . . . ?
C18 C20 C21 C22 -97.4(6) . . . . ?
C19 C20 C21 C26 152.0(5) . . . . ?
C27 C20 C21 C26 -57.6(6) . . . . ?
C18 C20 C21 C26 83.3(6) . . . . ?
C26 C21 C22 C23 0.8(10) . . . . ?
C20 C21 C22 C23 -178.6(6) . . . . ?
C21 C22 C23 C24 -0.2(10) . . . . ?
C22 C23 C24 C25 -0.4(9) . . . . ?
C23 C24 C25 C26 0.4(8) . . . . ?
C24 C25 C26 C21 0.1(7) . . . . ?
C22 C21 C26 C25 -0.7(8) . . . . ?
C20 C21 C26 C25 178.7(4) . . . . ?
C16 N4 C28 O2 5.7(8) . . . . ?
C16 N4 C28 C29 -169.3(3) . . . . ?
O2 C28 C29 C30 11.3(8) . . . . ?
N4 C28 C29 C30 -173.8(4) . . . . ?
O2 C28 C29 C31 -57.2(7) . . . . ?
N4 C28 C29 C31 117.8(4) . . . . ?
C28 C29 C30 C31 -108.6(4) . . . . ?
C29 C30 C31 C32 -104.5(4) . . . . ?
C29 C30 C31 C38 108.8(4) . . . . ?
C28 C29 C31 C30 108.5(4) . . . . ?
C28 C29 C31 C32 -140.0(3) . . . . ?
C30 C29 C31 C32 111.4(4) . . . . ?
C28 C29 C31 C38 0.2(5) . . . . ?
C30 C29 C31 C38 -108.3(4) . . . . ?
C30 C31 C32 C33 143.2(4) . . . . ?
C38 C31 C32 C33 -68.3(4) . . . . ?
C29 C31 C32 C33 74.3(4) . . . . ?
C30 C31 C32 C37 -40.3(5) . . . . ?
C38 C31 C32 C37 108.2(4) . . . . ?
C29 C31 C32 C37 -109.2(4) . . . . ?
C37 C32 C33 C34 -1.6(5) . . . . ?
C31 C32 C33 C34 175.1(3) . . . . ?
C32 C33 C34 C35 0.6(6) . . . . ?
C33 C34 C35 C36 1.3(6) . . . . ?
C34 C35 C36 C37 -2.2(6) . . . . ?
C35 C36 C37 C32 1.2(6) . . . . ?
C33 C32 C37 C36 0.7(5) . . . . ?
C31 C32 C37 C36 -175.9(4) . . . . ?
C5 C6 C39 C44 -105.4(3) . . . . ?
C7 C6 C39 C44 83.4(3) . . . . ?
C5 C6 C39 C40 76.5(3) . . . . ?
C7 C6 C39 C40 -94.7(3) . . . . ?
C45 O3 C40 C41 23.4(4) . . . . ?
C45 O3 C40 C39 -159.9(3) . . . . ?
C44 C39 C40 O3 -177.0(3) . . . . ?
C6 C39 C40 O3 1.2(4) . . . . ?
C44 C39 C40 C41 -0.2(4) . . . . ?
C6 C39 C40 C41 177.9(3) . . . . ?
O3 C40 C41 C42 175.2(3) . . . . ?
C39 C40 C41 C42 -1.2(4) . . . . ?
C40 C41 C42 C43 1.7(4) . . . . ?
C41 C42 C43 C44 -0.8(4) . . . . ?
C51 O4 C44 C39 176.7(2) . . . . ?
C51 O4 C44 C43 -3.3(4) . . . . ?
C40 C39 C44 O4 -178.8(3) . . . . ?
C6 C39 C44 O4 3.1(4) . . . . ?
C40 C39 C44 C43 1.2(4) . . . . ?
C6 C39 C44 C43 -176.9(3) . . . . ?
C42 C43 C44 O4 179.3(3) . . . . ?
C42 C43 C44 C39 -0.8(4) . . . . ?
C40 O3 C45 C50 -118.6(5) . . . . ?
C40 O3 C45 C46 63.5(9) . . . . ?
C50 C45 C46 C47 2.4(18) . . . . ?
O3 C45 C46 C47 -179.9(9) . . . . ?
C45 C46 C47 C48 -2.7(18) . . . . ?
C46 C47 C48 C49 2.3(14) . . . . ?
C47 C48 C49 C50 -1.5(12) . . . . ?
C46 C45 C50 C49 -1.7(12) . . . . ?
O3 C45 C50 C49 -179.5(6) . . . . ?
C48 C49 C50 C45 1.1(11) . . . . ?
C44 O4 C51 C52 86.2(3) . . . . ?
C44 O4 C51 C56 -97.2(3) . . . . ?
C56 C51 C52 C53 -1.0(4) . . . . ?
O4 C51 C52 C53 175.4(3) . . . . ?
C51 C52 C53 C54 0.6(5) . . . . ?
C52 C53 C54 C55 -0.2(5) . . . . ?
C53 C54 C55 C56 0.1(5) . . . . ?
C52 C51 C56 C55 0.9(4) . . . . ?
O4 C51 C56 C55 -175.5(2) . . . . ?
C54 C55 C56 C51 -0.5(4) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.035

# SQUEEZE RESULTS (Version =  50315)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.032 0.000 0.236 1035 300 ' '
2 -0.001 0.500 0.251 1035 300 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
 Solvents used for crystallization are chloroform and hexane. Both solvents are
 present in the system but are severely disordered and can not be satisfactorily 
 refined. Program SQUEEZE is used to deal with the disordered solvents. there are
 roughly half chloroform molecule and one hexane in the asymmtric unit.
 PART 1 10.25
 C1S   1    0.932062    0.487115    0.584401    10.25000    0.04872
 CL1S  6    1.049426    0.503401    0.618493    10.25000    0.06829
 CL2S  6    0.945660    0.451582    0.540470    10.25000    0.06618
 CL3S  6    0.878596    0.461954    0.653190    10.25000    0.11106
 PART 2 10.25
 C1X   1    0.941035    0.486629    0.610319    10.25000    0.05918
 CL1X  6    1.056545    0.509953    0.598962    10.25000    0.04730
 CL2X  6    0.919338    0.447894    0.575612    10.25000    0.09223
 CL3X  6    0.914775    0.490404    0.680716    10.25000    0.17920
 PART 0
 PART 1 10.50000
 C1X   1    1.074573    0.476711    0.597861    10.50000    0.13978
 C2X   1    0.957514    0.482198    0.513488    10.50000    0.21060
 C3X   1    0.896159    0.460681    0.532634    10.50000    0.09442
 C4X   1    1.046409    0.516453    0.568888    10.50000    0.06461
 C2S   1    0.259529    0.086750    0.289274    10.50000    0.12623
 C3S   1    0.136799    0.089555    0.251317    10.50000    0.10002
 C4S   1    0.015123    0.076565    0.266061    10.50000    0.09003
 C5S   1   -0.078811    0.093205    0.231466    10.50000    0.07068
 C6S   1   -0.196098    0.073396    0.238683    10.50000    0.09114 
 PART 0
;


