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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1053588'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl2 Cu N2 O6'
_chemical_formula_sum            'C16 H12 Cl2 Cu N2 O6'
_chemical_formula_weight         462.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 '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

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

_cell_length_a                   7.1589(12)
_cell_length_b                   10.1414(12)
_cell_length_c                   12.8984(16)
_cell_angle_alpha                67.555(12)
_cell_angle_beta                 73.912(13)
_cell_angle_gamma                78.022(12)
_cell_volume                     826.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4797
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      27.49

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             466
_exptl_absorpt_coefficient_mu    1.685
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.904

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            4797
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_sigmaI/netI    0.1244
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3797
_reflns_number_gt                2620
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)

_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)+(0.1420P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3579
_refine_ls_number_parameters     252
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2511
_refine_ls_wR_factor_gt          0.2181
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.014
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.17827(11) 0.31367(8) 0.40858(6) 0.0205(3) Uani 1 1 d D . .
O11 O 0.1216(6) 0.2965(5) 0.5653(4) 0.0225(10) Uani 1 1 d . . .
C12 C 0.1576(8) 0.1815(7) 0.6531(5) 0.0176(12) Uani 1 1 d . . .
C13 C 0.1352(9) 0.1921(7) 0.7604(6) 0.0227(13) Uani 1 1 d . . .
H13 H 0.1020 0.2825 0.7673 0.027 Uiso 1 1 calc R . .
C14 C 0.1596(9) 0.0758(7) 0.8561(5) 0.0220(13) Uani 1 1 d . . .
H14 H 0.1420 0.0872 0.9265 0.026 Uiso 1 1 calc R . .
C15 C 0.2116(9) -0.0604(7) 0.8467(6) 0.0232(13) Uani 1 1 d . . .
Cl15 Cl 0.2402(3) -0.20847(18) 0.96975(14) 0.0294(4) Uani 1 1 d . . .
C16 C 0.2385(9) -0.0791(7) 0.7443(5) 0.0231(14) Uani 1 1 d . . .
H16 H 0.2737 -0.1704 0.7393 0.028 Uiso 1 1 calc R . .
C17 C 0.2124(9) 0.0413(7) 0.6461(5) 0.0210(13) Uani 1 1 d . . .
C18 C 0.2411(8) 0.0112(6) 0.5418(5) 0.0178(12) Uani 1 1 d . . .
H18 H 0.2735 -0.0843 0.5466 0.021 Uiso 1 1 calc R . .
C20 C 0.2585(8) 0.0642(7) 0.3458(5) 0.0163(12) Uani 1 1 d . . .
N19 N 0.2258(7) 0.1053(6) 0.4423(5) 0.0210(11) Uani 1 1 d . . .
C21 C 0.2947(9) -0.0732(7) 0.3428(6) 0.0233(14) Uani 1 1 d . . .
H21 H 0.3015 -0.1518 0.4098 0.028 Uiso 1 1 calc R . .
C22 C 0.3215(10) -0.0939(8) 0.2371(6) 0.0258(14) Uani 1 1 d . . .
H22 H 0.3476 -0.1869 0.2354 0.031 Uiso 1 1 calc R . .
C23 C 0.3101(10) 0.0198(8) 0.1367(6) 0.0276(15) Uani 1 1 d . . .
H23 H 0.3271 0.0039 0.0682 0.033 Uiso 1 1 calc R . .
C24 C 0.2720(9) 0.1628(7) 0.1390(6) 0.0229(13) Uani 1 1 d . . .
C25 C 0.2614(10) 0.2870(8) 0.0372(6) 0.0279(15) Uani 1 1 d . . .
H25 H 0.2729 0.2776 -0.0333 0.033 Uiso 1 1 calc R . .
C26 C 0.2342(10) 0.4184(7) 0.0474(6) 0.0290(15) Uani 1 1 d U . .
H26 H 0.2326 0.5006 -0.0175 0.035 Uiso 1 1 calc R . .
C27 C 0.2087(10) 0.4312(7) 0.1546(6) 0.0252(14) Uani 1 1 d . . .
H27 H 0.1860 0.5227 0.1592 0.030 Uiso 1 1 calc R . .
N28 N 0.2153(8) 0.3184(6) 0.2505(5) 0.0114(10) Uani 1 1 d U . .
C29 C 0.2478(9) 0.1842(7) 0.2419(5) 0.0232(14) Uani 1 1 d . . .
Cl2 Cl -0.3352(2) 0.43436(17) 0.34910(14) 0.0236(4) Uani 1 1 d . . .
O21 O -0.1948(7) 0.3858(6) 0.4213(4) 0.0319(12) Uani 1 1 d . . .
O22 O -0.4597(7) 0.3228(5) 0.3840(5) 0.0341(12) Uani 1 1 d . . .
O23 O -0.4541(7) 0.5630(5) 0.3629(5) 0.0382(13) Uani 1 1 d . . .
O24 O -0.2343(8) 0.4631(7) 0.2323(5) 0.0481(16) Uani 1 1 d . . .
O1 O 0.1671(6) 0.5264(5) 0.3634(4) 0.0214(10) Uani 1 1 d D . .
H1 H 0.266(5) 0.551(3) 0.370(5) 0.026 Uiso 1 1 d D . .
H2 H 0.059(4) 0.563(3) 0.394(5) 0.026 Uiso 1 1 d 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
Cu1 O11 1.894(5) . ?
Cu1 N19 1.963(5) . ?
Cu1 N28 1.964(6) . ?
Cu1 O1 1.998(4) . ?
O11 C12 1.318(7) . ?
C12 C13 1.391(8) . ?
C12 C17 1.426(9) . ?
C13 C14 1.367(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.398(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(9) . ?
C15 Cl15 1.746(7) . ?
C16 C17 1.410(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.441(8) . ?
C18 N19 1.292(8) . ?
C18 H18 0.9300 . ?
C20 C21 1.377(9) . ?
C20 N19 1.404(8) . ?
C20 C29 1.434(9) . ?
C21 C22 1.413(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.429(10) . ?
C23 H23 0.9300 . ?
C24 C29 1.383(9) . ?
C24 C25 1.439(9) . ?
C25 C26 1.358(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.396(9) . ?
C26 H26 0.9300 . ?
C27 N28 1.331(8) . ?
C27 H27 0.9300 . ?
N28 C29 1.374(9) . ?
Cl2 O24 1.424(5) . ?
Cl2 O23 1.446(5) . ?
Cl2 O22 1.444(5) . ?
Cl2 O21 1.443(5) . ?
O1 H1 0.833(18) . ?
O1 H2 0.846(18) . ?

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
O11 Cu1 N19 93.7(2) . . ?
O11 Cu1 N28 173.96(19) . . ?
N19 Cu1 N28 82.8(2) . . ?
O11 Cu1 O1 89.64(18) . . ?
N19 Cu1 O1 172.4(2) . . ?
N28 Cu1 O1 94.4(2) . . ?
C12 O11 Cu1 127.5(4) . . ?
O11 C12 C13 120.2(5) . . ?
O11 C12 C17 123.2(5) . . ?
C13 C12 C17 116.6(6) . . ?
C14 C13 C12 123.0(6) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C13 C14 C15 119.1(6) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.3(6) . . ?
C16 C15 Cl15 120.0(5) . . ?
C14 C15 Cl15 118.7(5) . . ?
C15 C16 C17 119.3(6) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C12 120.7(6) . . ?
C16 C17 C18 115.5(6) . . ?
C12 C17 C18 123.7(6) . . ?
N19 C18 C17 125.7(6) . . ?
N19 C18 H18 117.1 . . ?
C17 C18 H18 117.1 . . ?
C21 C20 N19 127.5(6) . . ?
C21 C20 C29 119.6(6) . . ?
N19 C20 C29 112.9(5) . . ?
C18 N19 C20 121.0(6) . . ?
C18 N19 Cu1 124.5(5) . . ?
C20 N19 Cu1 114.3(4) . . ?
C20 C21 C22 119.4(6) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 121.7(6) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 119.2(6) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C29 C24 C23 119.4(6) . . ?
C29 C24 C25 118.2(6) . . ?
C23 C24 C25 122.4(6) . . ?
C26 C25 C24 117.8(6) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
C25 C26 C27 120.6(6) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
N28 C27 C26 123.0(6) . . ?
N28 C27 H27 118.5 . . ?
C26 C27 H27 118.5 . . ?
C27 N28 C29 117.5(6) . . ?
C27 N28 Cu1 129.1(5) . . ?
C29 N28 Cu1 113.3(4) . . ?
N28 C29 C24 122.9(6) . . ?
N28 C29 C20 116.6(6) . . ?
C24 C29 C20 120.5(6) . . ?
O24 Cl2 O23 109.8(4) . . ?
O24 Cl2 O22 110.3(4) . . ?
O23 Cl2 O22 109.0(3) . . ?
O24 Cl2 O21 109.4(3) . . ?
O23 Cl2 O21 110.0(3) . . ?
O22 Cl2 O21 108.4(3) . . ?
Cu1 O1 H1 113(2) . . ?
Cu1 O1 H2 112(2) . . ?
H1 O1 H2 114(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O23 0.833(18) 2.01(2) 2.810(7) 161(4) 1_655
O1 H2 O11 0.846(18) 1.844(17) 2.648(6) 158(3) 2_566

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         2.261
_refine_diff_density_min         -1.822
_refine_diff_density_rms         0.218
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1053589'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 Cl Cu N5 O'
_chemical_formula_sum            'C16 H10 Cl Cu N5 O'
_chemical_formula_weight         387.29

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'
Cu Cu 0.3201 1.2651 '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

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

_cell_length_a                   7.8516(2)
_cell_length_b                   9.3769(2)
_cell_length_c                   11.8132(3)
_cell_angle_alpha                97.9650(10)
_cell_angle_beta                 108.6330(10)
_cell_angle_gamma                111.1070(10)
_cell_volume                     736.53(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      25.710

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             390
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11132
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.71
_reflns_number_total             2810
_reflns_number_gt                2614
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0340P)²+0.3089P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2798
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31399(3) 0.47543(2) 0.28882(2) 0.03186(9) Uani 1 1 d . . .
Cl15 Cl 0.14498(9) 0.58461(7) 0.85528(5) 0.05264(15) Uani 1 1 d . . .
O11 O 0.3319(2) 0.63343(15) 0.41571(12) 0.0382(3) Uani 1 1 d . . .
N19 N 0.2324(2) 0.30547(18) 0.36668(14) 0.0294(3) Uani 1 1 d . . .
N28 N 0.2794(2) 0.29758(19) 0.15740(14) 0.0339(3) Uani 1 1 d . . .
N1 N 0.4247(3) 0.6340(2) 0.20946(17) 0.0474(4) Uani 1 1 d . . .
N2 N 0.5542(3) 0.7627(2) 0.27152(17) 0.0423(4) Uani 1 1 d . . .
N3 N 0.6817(3) 0.8875(2) 0.3266(2) 0.0600(5) Uani 1 1 d . . .
C18 C 0.2039(3) 0.3227(2) 0.46905(17) 0.0321(4) Uani 1 1 d . . .
H10 H 0.1638 0.2328 0.4964 0.039 Uiso 1 1 calc R . .
C17 C 0.2292(3) 0.4684(2) 0.54284(17) 0.0301(4) Uani 1 1 d . . .
C12 C 0.2885(3) 0.6152(2) 0.51213(17) 0.0312(4) Uani 1 1 d . . .
C13 C 0.3012(3) 0.7491(2) 0.59180(18) 0.0363(4) Uani 1 1 d . . .
H13 H 0.3400 0.8463 0.5738 0.044 Uiso 1 1 calc R . .
C14 C 0.2579(3) 0.7399(2) 0.69485(18) 0.0378(4) Uani 1 1 d . . .
H14 H 0.2665 0.8298 0.7453 0.045 Uiso 1 1 calc R . .
C15 C 0.2009(3) 0.5954(2) 0.72380(17) 0.0359(4) Uani 1 1 d . . .
C16 C 0.1865(3) 0.4626(2) 0.65030(17) 0.0351(4) Uani 1 1 d . . .
H16 H 0.1481 0.3671 0.6709 0.042 Uiso 1 1 calc R . .
C20 C 0.2138(3) 0.1576(2) 0.30246(17) 0.0306(4) Uani 1 1 d . . .
C29 C 0.2404(3) 0.1580(2) 0.18916(17) 0.0308(4) Uani 1 1 d . . .
C27 C 0.3080(3) 0.3035(3) 0.05320(19) 0.0452(5) Uani 1 1 d . . .
H27 H 0.3347 0.3981 0.0311 0.054 Uiso 1 1 calc R . .
C26 C 0.2993(4) 0.1720(3) -0.0247(2) 0.0532(6) Uani 1 1 d . . .
H26 H 0.3171 0.1795 -0.0982 0.064 Uiso 1 1 calc R . .
C25 C 0.2651(3) 0.0346(3) 0.0064(2) 0.0470(5) Uani 1 1 d . . .
H25 H 0.2617 -0.0521 -0.0448 0.056 Uiso 1 1 calc R . .
C24 C 0.2345(3) 0.0223(2) 0.11699(18) 0.0377(4) Uani 1 1 d . . .
C23 C 0.2054(3) -0.1132(3) 0.1605(2) 0.0449(5) Uani 1 1 d . . .
H23 H 0.2007 -0.2042 0.1141 0.054 Uiso 1 1 calc R . .
C22 C 0.1841(4) -0.1111(2) 0.2710(2) 0.0473(5) Uani 1 1 d . . .
H22 H 0.1673 -0.2007 0.2997 0.057 Uiso 1 1 calc R . .
C21 C 0.1869(3) 0.0234(2) 0.3421(2) 0.0413(5) Uani 1 1 d . . .
H21 H 0.1705 0.0216 0.4166 0.050 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
Cu1 O11 1.8873(13) . ?
Cu1 N1 1.9550(17) . ?
Cu1 N19 1.9606(15) . ?
Cu1 N28 1.9880(16) . ?
Cl15 C15 1.7501(19) . ?
O11 C12 1.305(2) . ?
N19 C18 1.297(2) . ?
N19 C20 1.418(2) . ?
N28 C27 1.325(3) . ?
N28 C29 1.367(2) . ?
N1 N2 1.193(3) . ?
N2 N3 1.150(3) . ?
C18 C17 1.424(3) . ?
C18 H10 0.9300 . ?
C17 C16 1.416(3) . ?
C17 C12 1.424(3) . ?
C12 C13 1.413(3) . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C16 H16 0.9300 . ?
C20 C21 1.372(3) . ?
C20 C29 1.420(3) . ?
C29 C24 1.407(3) . ?
C27 C26 1.399(3) . ?
C27 H27 0.9300 . ?
C26 C25 1.346(3) . ?
C26 H26 0.9300 . ?
C25 C24 1.415(3) . ?
C25 H25 0.9300 . ?
C24 C23 1.407(3) . ?
C23 C22 1.367(3) . ?
C23 H23 0.9300 . ?
C22 C21 1.404(3) . ?
C22 H22 0.9300 . ?
C21 H21 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
O11 Cu1 N1 91.70(7) . . ?
O11 Cu1 N19 93.75(6) . . ?
N1 Cu1 N19 171.55(7) . . ?
O11 Cu1 N28 175.84(6) . . ?
N1 Cu1 N28 92.07(7) . . ?
N19 Cu1 N28 82.71(6) . . ?
C12 O11 Cu1 127.82(12) . . ?
C18 N19 C20 121.47(16) . . ?
C18 N19 Cu1 125.20(13) . . ?
C20 N19 Cu1 113.28(12) . . ?
C27 N28 C29 118.51(17) . . ?
C27 N28 Cu1 128.24(14) . . ?
C29 N28 Cu1 112.90(12) . . ?
N2 N1 Cu1 120.28(14) . . ?
N3 N2 N1 176.7(2) . . ?
N19 C18 C17 125.25(17) . . ?
N19 C18 H10 117.4 . . ?
C17 C18 H10 117.4 . . ?
C16 C17 C18 116.95(17) . . ?
C16 C17 C12 119.35(17) . . ?
C18 C17 C12 123.67(17) . . ?
O11 C12 C13 118.29(17) . . ?
O11 C12 C17 124.22(16) . . ?
C13 C12 C17 117.49(17) . . ?
C14 C13 C12 121.91(18) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.84(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.72(18) . . ?
C16 C15 Cl15 119.78(16) . . ?
C14 C15 Cl15 119.50(15) . . ?
C15 C16 C17 120.69(18) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C21 C20 N19 127.22(17) . . ?
C21 C20 C29 118.75(17) . . ?
N19 C20 C29 113.88(16) . . ?
N28 C29 C24 122.43(17) . . ?
N28 C29 C20 116.70(16) . . ?
C24 C29 C20 120.83(17) . . ?
N28 C27 C26 122.2(2) . . ?
N28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C25 C26 C27 120.1(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C23 C24 C29 118.69(19) . . ?
C23 C24 C25 124.49(19) . . ?
C29 C24 C25 116.79(19) . . ?
C22 C23 C24 119.96(19) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C20 C21 C22 120.39(19) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.71
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_sb1
_database_code_depnum_ccdc_archive 'CCDC 1053590'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Cl Cu N2 O3'
_chemical_formula_weight         408.34

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.2712(4)
_cell_length_b                   10.8166(4)
_cell_length_c                   18.3726(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.640(2)
_cell_angle_gamma                90.00
_cell_volume                     3397.96(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            Green
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1672
_exptl_absorpt_coefficient_mu    1.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26030
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.44
_reflns_number_total             3505
_reflns_number_gt                3148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0431P)²+3.4163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3505
_refine_ls_number_parameters     233
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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
Cu1 Cu 0.033788(12) 0.592290(19) 0.390085(12) 0.03182(8) Uani 1 1 d . . .
Cl1 Cl -0.06256(3) 0.73750(4) 0.32813(3) 0.04230(13) Uani 1 1 d . . .
O1 O -0.02784(7) 0.45536(11) 0.33684(7) 0.0352(3) Uani 1 1 d . . .
O2 O 0.10828(8) 0.56163(14) 0.31526(8) 0.0418(3) Uani 1 1 d D . .
N1 N 0.08616(8) 0.49425(14) 0.48528(8) 0.0312(3) Uani 1 1 d . . .
O77 O -0.11060(8) 0.29670(12) 0.23467(7) 0.0417(3) Uani 1 1 d . . .
N34 N 0.10702(8) 0.72274(14) 0.45141(9) 0.0331(3) Uani 1 1 d . . .
C2 C 0.14982(9) 0.68652(17) 0.52544(10) 0.0320(4) Uani 1 1 d . . .
C3 C 0.13931(10) 0.56322(18) 0.54651(10) 0.0329(4) Uani 1 1 d . . .
C4 C 0.07529(10) 0.37704(17) 0.49269(10) 0.0341(4) Uani 1 1 d . . .
H4 H 0.1025 0.3415 0.5408 0.041 Uiso 1 1 calc R . .
C5 C 0.02578(10) 0.29789(16) 0.43435(10) 0.0329(4) Uani 1 1 d . . .
C6 C 0.02623(11) 0.17062(18) 0.45344(12) 0.0423(4) Uani 1 1 d . . .
H6 H 0.0563 0.1443 0.5032 0.051 Uiso 1 1 calc R . .
C7 C -0.01616(13) 0.08695(18) 0.40081(13) 0.0471(5) Uani 1 1 d . . .
H7 H -0.0150 0.0039 0.4143 0.056 Uiso 1 1 calc R . .
C8 C -0.06201(12) 0.12629(19) 0.32556(13) 0.0446(5) Uani 1 1 d . . .
H8 H -0.0902 0.0685 0.2889 0.054 Uiso 1 1 calc R . .
C9 C -0.06572(10) 0.24927(17) 0.30551(11) 0.0350(4) Uani 1 1 d . . .
C10 C -0.15925(14) 0.2126(2) 0.17933(12) 0.0522(5) Uani 1 1 d . . .
H10A H -0.1895 0.1637 0.2028 0.063 Uiso 1 1 calc R . .
H10B H -0.1275 0.1570 0.1614 0.063 Uiso 1 1 calc R . .
C11 C -0.21272(14) 0.2854(2) 0.11246(13) 0.0605(6) Uani 1 1 d . . .
H11A H -0.2464 0.3359 0.1300 0.091 Uiso 1 1 calc R . .
H11B H -0.2438 0.2299 0.0728 0.091 Uiso 1 1 calc R . .
H11C H -0.1823 0.3373 0.0916 0.091 Uiso 1 1 calc R . .
C12 C -0.02160(9) 0.34062(16) 0.35936(10) 0.0310(4) Uani 1 1 d . . .
C13 C 0.17937(11) 0.52452(19) 0.62092(11) 0.0397(4) Uani 1 1 d . . .
H13 H 0.1721 0.4446 0.6358 0.048 Uiso 1 1 calc R . .
C14 C 0.23132(12) 0.6046(2) 0.67481(12) 0.0473(5) Uani 1 1 d . . .
H14 H 0.2581 0.5769 0.7251 0.057 Uiso 1 1 calc R . .
C15 C 0.24329(11) 0.7220(2) 0.65498(12) 0.0464(5) Uani 1 1 d . . .
H15 H 0.2785 0.7731 0.6914 0.056 Uiso 1 1 calc R . .
C16 C 0.20241(10) 0.76655(18) 0.57926(11) 0.0385(4) Uani 1 1 d . . .
C17 C 0.21133(12) 0.88584(19) 0.55291(13) 0.0463(5) Uani 1 1 d . . .
H17 H 0.2462 0.9413 0.5862 0.056 Uiso 1 1 calc R . .
C18 C 0.16902(12) 0.92003(19) 0.47879(14) 0.0473(5) Uani 1 1 d . . .
H18 H 0.1748 0.9987 0.4612 0.057 Uiso 1 1 calc R . .
C19 C 0.11665(11) 0.83583(18) 0.42916(12) 0.0404(4) Uani 1 1 d . . .
H19 H 0.0876 0.8604 0.3787 0.048 Uiso 1 1 calc R . .
H@2 H 0.0993(15) 0.6189(15) 0.2850(12) 0.061 Uiso 1 1 d D . .
H@1 H 0.0925(14) 0.4991(13) 0.2912(12) 0.061 Uiso 1 1 d 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
Cu1 O1 1.9084(12) . ?
Cu1 N1 1.9797(14) . ?
Cu1 N34 1.9970(15) . ?
Cu1 O2 2.2742(14) . ?
Cu1 Cl1 2.3343(5) . ?
O1 C12 1.300(2) . ?
O2 H@2 0.810(9) . ?
O2 H@1 0.803(9) . ?
N1 C4 1.298(2) . ?
N1 C3 1.412(2) . ?
O77 C9 1.370(2) . ?
O77 C10 1.419(2) . ?
N34 C19 1.321(2) . ?
N34 C2 1.366(2) . ?
C2 C16 1.407(2) . ?
C2 C3 1.421(3) . ?
C3 C13 1.369(3) . ?
C4 C5 1.420(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.420(3) . ?
C5 C12 1.421(2) . ?
C6 C7 1.351(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C12 1.429(2) . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.404(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.412(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.408(3) . ?
C17 C18 1.359(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(3) . ?
C18 H18 0.9300 . ?
C19 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
O1 Cu1 N1 92.94(5) . . ?
O1 Cu1 N34 173.99(6) . . ?
N1 Cu1 N34 82.01(6) . . ?
O1 Cu1 O2 87.00(5) . . ?
N1 Cu1 O2 104.48(6) . . ?
N34 Cu1 O2 91.11(5) . . ?
O1 Cu1 Cl1 93.72(4) . . ?
N1 Cu1 Cl1 146.91(4) . . ?
N34 Cu1 Cl1 92.28(4) . . ?
O2 Cu1 Cl1 108.21(4) . . ?
C12 O1 Cu1 127.44(11) . . ?
Cu1 O2 H@2 106.5(18) . . ?
Cu1 O2 H@1 106.2(18) . . ?
H@2 O2 H@1 108.7(19) . . ?
C4 N1 C3 121.34(15) . . ?
C4 N1 Cu1 124.87(12) . . ?
C3 N1 Cu1 113.78(12) . . ?
C9 O77 C10 117.04(15) . . ?
C19 N34 C2 118.80(16) . . ?
C19 N34 Cu1 127.99(13) . . ?
C2 N34 Cu1 113.19(12) . . ?
N34 C2 C16 122.19(17) . . ?
N34 C2 C3 117.11(16) . . ?
C16 C2 C3 120.69(17) . . ?
C13 C3 N1 127.54(18) . . ?
C13 C3 C2 118.89(17) . . ?
N1 C3 C2 113.57(15) . . ?
N1 C4 C5 126.16(16) . . ?
N1 C4 H4 116.9 . . ?
C5 C4 H4 116.9 . . ?
C4 C5 C6 116.84(16) . . ?
C4 C5 C12 122.95(16) . . ?
C6 C5 C12 120.21(17) . . ?
C7 C6 C5 121.37(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.56(18) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.79(19) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
O77 C9 C8 124.96(17) . . ?
O77 C9 C12 113.66(15) . . ?
C8 C9 C12 121.38(17) . . ?
O77 C10 C11 108.28(18) . . ?
O77 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O77 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C5 125.01(16) . . ?
O1 C12 C9 118.35(15) . . ?
C5 C12 C9 116.64(16) . . ?
C3 C13 C14 120.41(19) . . ?
C3 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 121.35(19) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.23(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C2 C16 C17 117.09(18) . . ?
C2 C16 C15 118.40(18) . . ?
C17 C16 C15 124.51(19) . . ?
C18 C17 C16 120.01(19) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.48(19) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
N34 C19 C18 122.40(19) . . ?
N34 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.069
